\

                                                                   Exhibit 99.1


                          SECURITIES PURCHASE AGREEMENT

     This Securities Purchase Agreement dated as of February 15, 2002 (this
"AGREEMENT"), by and among I-Many, Inc., a Delaware corporation (the "COMPANY"),
and the purchasers identified on the signature pages hereto (each, including its
respective successors and assigns, a "PURCHASER" and collectively, the
"PURCHASERS").

     WHEREAS, subject to the terms and conditions set forth in this Agreement
and pursuant to Section 4(2) of the Securities Act of 1933, as amended (the
"SECURITIES ACT"), and Rule 506 promulgated thereunder, the Company desires to
issue and sell to the Purchasers, and the Purchasers, severally and not jointly,
desire to purchase from the Company, certain securities of the Company pursuant
to the terms set forth herein.

     NOW, THEREFORE, IN CONSIDERATION of the mutual covenants contained in this
Agreement, and for other good and valuable consideration the receipt and
adequacy of which are hereby acknowledged, the Company and each Purchaser agree
as follows:

                                   ARTICLE I.

                                   DEFINITIONS

     1.1  DEFINITIONS. As used in this Agreement, the following terms shall have
the meanings set forth in this Section 1.1:

     "AFFILIATE" means any Person that, directly or indirectly through one or
more intermediaries, controls or is controlled by or is under common control
with a Person, as such terms are used in and construed under Rule 144.

     "BUSINESS DAY" means any day except Saturday, Sunday and any day which
shall be a federal legal holiday or a day on which banking institutions in the
State of New York or the State of Maine are authorized or required by law or
other governmental action to close.

     "CERTIFICATE OF DESIGNATION" means the Certificate of Designations of the
Rights, Preferences and Privileges of the Series A Convertible Preferred Stock
of the Company, in the form of EXHIBIT A attached hereto.

     "CLOSING" means the closing of the purchase and sale of the Shares and the
Warrants, as contemplated by Section 2.1.

     "CLOSING DATE" means the date of the Closing.

     "COMMISSION" means the Securities and Exchange Commission.

     "COMMON STOCK" means the common stock of the Company, $.0001 par value per
share, and any securities into which such common stock may hereafter be
reclassified.



     "COMMON SHARES" means the shares of Common Stock issuable to the Purchasers
at the Closing.

     "COMPANY OUTSIDE COUNSEL" means Hale and Dorr LLP.

     "EFFECTIVE DATE" means the date that the Registration Statement is first
declared effective by the Commission.

     "ELIGIBLE MARKET" means any of the New York Stock Exchange, the American
Stock Exchange, the Nasdaq National Market or the Nasdaq SmallCap Market.

     "ESCROW AGENT" means the Escrow Agent from time to time under the Escrow
Agreement.

     "ESCROW AGREEMENT" means the Escrow Agreement, dated as of the date of this
Agreement, by and among the Company, the Purchasers and the Escrow Agent, in the
form of EXHIBIT B attached hereto.

     "EXCHANGE ACT" means the Securities Exchange Act of 1934, as amended.

     "PER SHARE PURCHASE PRICE" equals $7.27

     "PERSON" means an individual or corporation, partnership, trust,
incorporated or unincorporated association, joint venture, limited liability
company, joint stock company, government (or an agency or subdivision thereof)
or other entity of any kind.

     "PREFERRED STOCK" means the Company's Series A Convertible Preferred Stock,
$.01 par value per share.

     "PROCEEDING" means an action, claim, suit, investigation or proceeding
(including, without limitation, an investigation or partial proceeding, such as
a deposition), whether commenced or threatened in writing.

     "PURCHASER COUNSEL" means Robinson Silverman Pearce Aronsohn & Berman LLP.

     "REGISTRATION STATEMENT" means one or more registration statements meeting
the requirements set forth in the Registration Rights Agreement and covering the
resale of the Common Shares, the Underlying Shares and the Warrant Shares by the
Purchasers.

     "REGISTRATION RIGHTS AGREEMENT" means the Registration Rights Agreement,
dated as of the date of this Agreement, by and among the Company and the
Purchasers, in the form of EXHIBIT B attached hereto.

     "RULE 144" means Rule 144 promulgated by the Commission pursuant to the
Securities Act, as such rule may be amended from time to time, or any similar
rule or regulation hereafter adopted by the Commission having substantially the
same effect as such Rule.

                                       2



     "SECURITIES" means the Shares, the Underlying Shares, the Warrants and the
Warrant Shares.

     "SETTLEMENT DATE" means the later of the (i) the 110th Business Day after
the Closing Date and (ii) the 30th Trading Day following the Effective Date,
plus in the case of (ii) an additional Trading Day for each Trading Day
following the Effective Date that the Registration Statement is not effective or
the prospectus thereunder not available for use by the Purchaser to resell all
of the Registrable Securities (as defined in the Registration Rights Agreement)
issued or issuable to it under this Agreement, the Certificate of Designation or
the Warrants.

     "SHARES" means the Common Shares and Preferred Stock.

     "SUBSIDIARY" means any subsidiary of the Company that is required to be
listed in Schedule 3.1(a).

     "TRADING DAY" means (i) a day on which the Common Stock is traded on a
Trading Market, or (ii) if the Common Stock is not listed on a Trading Market, a
day on which the Common Stock is traded in the over the counter market, as
reported by the OTC Bulletin Board, or (iii) if the Common Stock is not quoted
on the OTC Bulletin Board, a day on which the Common Stock is quoted in the over
the counter market as reported by the National Quotation Bureau Incorporated (or
any similar organization or agency succeeding its functions of reporting
prices); provided, that in the event that the Common Stock is not listed or
quoted as set forth in (i), (ii) and (iii) hereof, then Trading Day shall mean a
Business Day.

     "TRADING MARKET" means the Nasdaq National Market or any other national
securities exchange, market or trading or quotation facility on which the Common
Stock is then listed or quoted.

     "TRANSACTION DOCUMENTS" means this Agreement, the Escrow Agreement, the
Registration Rights Agreement, the Certificate of Designation, and the Warrants.

     "UNDERLYING SHARES" means the shares of Common Stock issuable upon
conversion of the Preferred Stock.

     "WARRANTS" means, collectively, the Common Stock purchase warrants issuable
to each Purchaser at the Closing, in the forms attached hereto as EXHIBIT C-1
and EXHIBIT C-2.

     "WARRANT SHARES" means the shares of Common Stock issuable upon exercise of
the Warrants.

                                   ARTICLE II.

                                PURCHASE AND SALE

     2.1  CLOSING. Subject to the terms and conditions set forth in this
Agreement the Company shall issue and sell to the Purchasers and the
Purchasers shall, severally and not jointly, purchase from the Company the
Shares and the Warrants. The closing of the purchase and the sale of the
Shares and the Warrants shall take place at the offices of Purchaser Counsel,

                                       3



1290 Avenue of the Americas, New York, New York 10104, immediately following the
execution of this Agreement or such other time or place as the parties shall
agree.

     2.2  CLOSING DELIVERIES.

          (a) At the Closing, the Company shall deliver or cause to be delivered
to each Purchaser the following: (i) a stock certificate, registered in the name
of such Purchaser, evidencing the number of Common Shares equal to the Common
Shares Investment Amount indicated below such Purchaser's name on the signature
page of this Agreement divided by the Per Share Purchase Price; (ii) a Warrant,
in the form of EXHIBIT C-1 attached hereto, registered in the name of such
Purchaser, pursuant to which such Purchaser shall have the right to acquire the
number of shares of Common Stock equal to 15% of the Common Shares issued to
such Purchaser in accordance with Section 2.2(a)(i); (iii) a Warrant, in the
form of EXHIBIT C-2 attached hereto, registered in the name of such Purchaser,
pursuant to which such Purchaser shall have the right to acquire the number of
shares of Common Stock equal to 15% of the number of Common Shares issuable to
such Purchaser under Section 2.2(a)(i), (iv) the Escrow Agreement, executed by
the Company; (v) a legal opinion of Company Outside Counsel, in agreed form;
(vi) reasonably satisfactory evidence that the Certificate of Designation has
been filed on or prior to the Closing Date with the Secretary of State of the
State of Delaware; and (vii) the Registration Rights Agreement, executed by the
Company.

          (b) At the Closing, the Company shall deliver or cause to be delivered
to the Escrow Agent on behalf of each Purchaser, (i) a copy of the Escrow
Agreement, executed by the Company and (ii) an original stock certificate,
registered in the name of such Purchaser, evidencing the number of shares of
Preferred Stock equal to the Preferred Stock Investment Amount indicated below
such Purchaser's name on the signature page of this Agreement divided by
$10,000; and (iii) a Warrant, in the form of EXHIBIT C-1 attached hereto,
registered in the name of such Purchaser, each of (ii) and (iii) to be held in,
and disbursed from, escrow in accordance with the terms and conditions of the
Escrow Agreement. In the event that the Preferred Shares issuable to a Purchaser
are redeemed by the Company pursuant to the terms of the Certificate of
Designation, the Warrant referenced in this paragraph issued or issuable to such
Purchaser shall be void and of no further force or effect.

          (c) At the Closing, each Purchaser shall deliver or cause to be
delivered (i) to the Company, (1) a copy of the Escrow Agreement, this Agreement
and the Registration Rights Agreement, executed by the Purchaser and (2) in
United States dollars in immediately available funds by wire transfer to an
account designated in writing by the Company for such purpose, an amount equal
to the Common Shares Investment Amount indicated below such Purchaser's name on
the signature page of this Agreement and (ii) to the Escrow Agent, (1) the
Escrow Agreement executed by such Purchaser and (2) in United States dollars in
immediately available funds by wire transfer, an amount equal to such
Purchaser's percentage of the amount paid by such Purchaser pursuant to Section
2.2(c)(i)(2) over the aggregate amounts paid by all Purchasers pursuant to
Section 2.2(c)(i)(2), times $17,000,000, such amount to be held in, and
disbursed from, escrow in accordance with the terms and conditions of the Escrow
Agreement. In addition to the foregoing, on the date, if any, on which the
Preferred Stock held by a Purchaser is converted into Underlying Shares, the
Purchaser shall pay to the Company in immediately available funds the shortfall,
if any, between the amount paid to the Company by the escrow

                                       4



agent pursuant to the Escrow Agreement representing the purchase price for such
Preferred Stock and the aggregate Conversion Price of such Underlying Shares.

                                  ARTICLE III.

                         REPRESENTATIONS AND WARRANTIES

     3.1  REPRESENTATIONS AND WARRANTIES OF THE COMPANY. The Company hereby
makes the following representations and warranties to the Purchasers:

          (a) SUBSIDIARIES. The Company has no direct or indirect subsidiaries
other than those listed in SCHEDULE 3.1(a). Except as disclosed in SCHEDULE
3.1(a), the Company owns, directly or indirectly, all of the capital stock of
each Subsidiary free and clear of any lien, charge, security interest,
encumbrance, right of first refusal or other restriction (collectively,
"LIENS"), and all the issued and outstanding shares of capital stock of each
Subsidiary are validly issued and are fully paid, non-assessable and free of
preemptive and similar rights.

          (b) ORGANIZATION AND QUALIFICATION. Each of the Company and the
Subsidiaries is an entity duly incorporated or otherwise organized, validly
existing and in good standing under the laws of the jurisdiction of its
incorporation or organization (as applicable), with the requisite power and
authority to own and use its properties and assets and to carry on its business
as currently conducted. Neither the Company nor any Subsidiary is in violation
of any of the provisions of its respective certificate or articles of
incorporation, bylaws or other organizational or charter documents. Each of the
Company and the Subsidiaries is duly qualified to conduct business and is in
good standing as a foreign corporation or other entity in each jurisdiction in
which the nature of the business conducted or property owned by it makes such
qualification necessary, except where the failure to be so qualified or in good
standing, as the case may be, could not, individually or in the aggregate: (i)
adversely affect the legality, validity or enforceability of any Transaction
Document, (ii) have, or reasonably be expected to result in, a material adverse
effect on the results of operations, assets, prospects, business or condition
(financial or otherwise) of the Company and the Subsidiaries, taken as a whole,
or (iii) adversely impair the Company's ability to perform in all material
respects on a timely basis its obligations under any Transaction Document (any
of (i), (ii) or (iii), a "MATERIAL ADVERSE EFFECT").

          (c) AUTHORIZATION; ENFORCEMENT. The Company has the requisite
corporate power and authority to enter into and to consummate the transactions
contemplated by each of the Transaction Documents and otherwise to carry out its
obligations thereunder. The execution and delivery of each of the Transaction
Documents by the Company and the consummation by it of the transactions
contemplated thereby have been duly authorized by all necessary corporate action
on the part of the Company. Each Transaction Document has been (or upon delivery
will be) duly executed by the Company and, when delivered in accordance with the
terms hereof, will constitute the valid and binding obligation of the Company
enforceable against the Company in accordance with its terms

          (d) NO CONFLICTS. The execution, delivery and performance of the
Transaction Documents by the Company and the consummation by the Company of the
transactions contemplated thereby do not and will not: (i) conflict with or
violate any provision of the

                                       5



Company's or any Subsidiary's certificate or articles of incorporation, bylaws
or other organizational or charter documents, or (ii) subject to obtaining the
Required Approvals (as defined below), conflict with, or constitute a default
(or an event that with notice or lapse of time or both would become a default)
under, or give to others any rights of termination, amendment, acceleration or
cancellation (with or without notice, lapse of time or both) of, any agreement,
credit facility, debt or other instrument (evidencing a Company or Subsidiary
debt or otherwise) or other understanding to which the Company or any Subsidiary
is a party or by which any property or asset of the Company or any Subsidiary is
bound or affected, or (iii) subject to obtaining the Required Approvals, result
in a violation of any law, rule, regulation, order, judgment, injunction, decree
or other restriction of any court or governmental authority to which the Company
or a Subsidiary is subject (including federal and state securities laws and
regulations), or by which any property or asset of the Company or a Subsidiary
is bound or affected; except in the case of each of clauses (ii) and (iii), such
as could not, individually or in the aggregate, have or reasonably be expected
to result in a Material Adverse Effect.

          (e) FILINGS, CONSENTS AND APPROVALS. Neither the Company nor any
Subsidiary is required to obtain any consent, waiver, authorization or order of,
give any notice to, or make any filing or registration with, any court or other
federal, state, local or other governmental authority or other Person in
connection with the execution, delivery and performance by the Company of the
Transaction Documents, other than: (i) the filing of the Certificate of
Designation with the Secretary of State of the State of Delaware, (ii) the
filing with, and declaration of effectiveness by, the Commission of the
Registration Statement and (iii) the application with the Trading Market for the
listing of the Common Shares, Underlying Shares and Warrant Shares for trading
thereon in the time and manner required thereby (collectively, the "REQUIRED
APPROVALS").

          (f) ISSUANCE OF THE SECURITIES. The Securities are duly authorized
and, when issued and paid for in accordance with the Transaction Documents, will
be duly and validly issued, fully paid and non-assessable, free and clear of all
Liens. The Company has reserved from its duly authorized capital stock the
maximum number of shares of Common Stock issuable pursuant to this Agreement,
the Certificate of Designation and the Warrants.

          (g) CAPITALIZATION. The number of shares and type of all authorized,
issued and outstanding capital stock of the Company is set forth in SCHEDULE
3.1(g). No securities of the Company are entitled to preemptive or similar
rights, and no Person has any right of first refusal, preemptive right, right of
participation, or any similar right to participate in the transactions
contemplated by the Transaction Documents. The issuance and sale of the
Securities will not obligate the Company to issue shares of Common Stock or
other securities to any Person (other than the Purchasers) and will not result
in a right of any holder of Company securities to adjust the exercise,
conversion, exchange or reset price under such securities.

          (h) SEC REPORTS; FINANCIAL STATEMENTS. The Company has filed all
reports required to be filed by it under the Exchange Act, including pursuant to
Section 13(a) or 15(d) thereof, for the two years preceding the date hereof (or
such shorter period as the Company was required by law to file such material)
(the foregoing materials being collectively referred to herein as the "SEC
REPORTS" and, together with the Schedules to this Agreement, the "DISCLOSURE
MATERIALS") on a timely basis or has received a valid extension of such time of
filing and has filed

                                       6



any such SEC Reports prior to the expiration of any such extension. As of their
respective dates, the SEC Reports complied in all material respects with the
requirements of the Exchange Act and the rules and regulations of the Commission
promulgated thereunder, and none of the SEC Reports, when filed, contained any
untrue statement of a material fact or omitted to state a material fact required
to be stated therein or necessary in order to make the statements therein, in
light of the circumstances under which they were made, not misleading. The
financial statements of the Company included in the SEC Reports complied in all
material respects with applicable accounting requirements and the rules and
regulations of the Commission with respect thereto as in effect at the time of
filing. Such financial statements have been prepared in accordance with
generally accepted accounting principles applied on a consistent basis during
the periods involved ("GAAP"), except as may be otherwise specified in such
financial statements or the notes thereto, and fairly present in all material
respects the financial position of the Company and its consolidated subsidiaries
as of and for the dates thereof and the results of operations and cash flows for
the periods then ended, subject, in the case of unaudited statements, to normal,
immaterial, year-end audit adjustments.

          (i) MATERIAL CHANGES. Since September 30, 2001, except as specifically
disclosed in the SEC Reports: (i) there has been no event, occurrence or
development relating to the Company or its Subsidiaries and not generally to
market conditions that has had or could reasonably be expected to result in a
Material Adverse Effect, (ii) the Company has not incurred any liabilities
(contingent or otherwise) other than: (A) trade payables and accrued expenses
incurred in the ordinary course of business consistent with past practice and
(B) liabilities not required to be reflected in the Company's financial
statements pursuant to GAAP or required to be disclosed in filings made with the
Commission, (iii) the Company has not altered its method of accounting or the
identity of its auditors, (iv) the Company has not declared or made any dividend
or distribution of cash or other property to its stockholders or purchased,
redeemed or made any agreements to purchase or redeem any shares of its capital
stock and (v) the Company has not issued any equity securities to any officer,
director or Affiliate, except pursuant to existing Company stock option plans.
The Company does not have pending before the Commission any request for
confidential treatment of information.

          (j) LITIGATION. Except as set forth in Schedule 3.1(j), there is no
action, suit, inquiry, notice of violation, proceeding or investigation pending
or, to the knowledge of the Company, threatened against the Company, any
Subsidiary or any of their respective properties before or by any court,
arbitrator, governmental or administrative agency or regulatory authority
(federal, state, county, local or foreign) (collectively, an "ACTION") which:
(i) adversely affects or challenges the legality, validity or enforceability of
any of the Transaction Documents or the Securities or (ii) could, if there were
an unfavorable decision, individually or in the aggregate, have or reasonably be
expected to result in a Material Adverse Effect. Neither the Company nor any
Subsidiary, nor any officer thereof, is or has been, nor any director thereof is
or has been for the last three years, the subject of any Action involving a
claim of violation of or liability under federal or state securities laws or a
claim of breach of fiduciary duty. There has not been, and, to the knowledge of
the Company, there is not pending or contemplated, any investigation by the
Commission involving the Company or any current or former director that was a
director of the Company at any time during the last three years or officer of
the Company. The Commission

                                       7



has not issued any stop order or other order suspending the effectiveness of any
registration statement filed by the Company or any Subsidiary under the Exchange
Act or the Securities Act.

          (k) COMPLIANCE. Neither the Company nor any Subsidiary: (i) is in
default under or in violation of (and no event has occurred that has not been
waived that, with notice or lapse of time or both, has, or could reasonably be
expected to result in, a default by the Company or any Subsidiary under), nor
has the Company or any Subsidiary received notice of a claim that it is in
default under or that it is in violation of, any indenture, loan or credit
agreement or any other agreement or instrument to which it is a party or by
which it or any of its properties is bound (whether or not such default or
violation has been waived), (ii) is in violation of any order of any court,
arbitrator or governmental body, or (iii) is or has been in violation of any
statute, rule or regulation of any governmental authority, including without
limitation all foreign, federal, state and local laws relating to taxes,
environmental protection, occupational health and safety, product quality and
safety and employment and labor matters, except in each case as could not,
individually or in the aggregate, have, or could reasonably be expected to
result in, a Material Adverse Effect.

          (l) PATENTS AND TRADEMARKS. The Company and the Subsidiaries have, or
have rights to use, all patents, patent applications, trademarks, trademark
applications, service marks, trade names, copyrights, licenses and other similar
rights that are necessary and material for use in connection with their
respective businesses as described in the SEC Reports and which the failure to
so have could have, or reasonably be expected to result in, a Material Adverse
Effect (collectively, the "INTELLECTUAL PROPERTY RIGHTS"). Neither the Company
nor any Subsidiary has received a written notice that the Intellectual Property
Rights used by the Company or any Subsidiary violates or infringes upon the
rights of any Person which if determined adversely to the Company would,
individually or in the aggregate have a Material Adverse Effect. To the
knowledge of the Company, (i) all such Intellectual Property Rights are
enforceable and (ii) there is no existing infringement by another Person of any
of the Intellectual Property Rights.

          (m) TRANSACTIONS WITH AFFILIATES AND EMPLOYEES. Except as set forth in
SEC Reports, none of the officers or directors of the Company and is presently a
party to any transaction with the Company or any Subsidiary (other than for
services as employees, officers and directors), including any contract,
agreement or other arrangement providing for the furnishing of services to or
by, providing for rental of real or personal property to or from, or otherwise
requiring payments to or from any officer, director or such employee or, to the
knowledge of the Company, any entity in which any officer, director, or any such
employee has a substantial interest or is an officer, director, trustee or
partner.

          (n) INTERNAL ACCOUNTING CONTROLS. The Company and the Subsidiaries
maintain a system of internal accounting controls which the audit committee of
the board of directors reasonably believes is sufficient to provide reasonable
assurance that: (i) transactions are executed in accordance with management's
general or specific authorizations, (ii) transactions are recorded as necessary
to permit preparation of financial statements in conformity with generally
accepted accounting principles and to maintain asset accountability, (iii)
access to assets is permitted only in accordance with management's general or
specific authorization, and (iv) the recorded accountability for assets is
compared with the existing assets at reasonable intervals and appropriate action
is taken with respect to any differences.

                                       8



          (o) SOLVENCY. Based on the financial condition of the Company as of
the Closing Date: (i) the Company's fair saleable value of its assets exceeds
the amount that will be required to be paid on or in respect of the Company's
existing debts and other liabilities (including known contingent liabilities) as
they mature; (ii) the Company's assets do not constitute unreasonably small
capital to carry on its business for the current fiscal year as now conducted
and as proposed to be conducted including its capital needs taking into account
the particular capital requirements of the business conducted by the Company,
and projected capital requirements and capital availability thereof; and (iii)
the current cash flow of the Company, together with the proceeds the Company
would receive, were it to liquidate all of its assets, after taking into account
all anticipated uses of the cash, would be sufficient to pay all amounts on or
in respect of its debt when such amounts are required to be paid. The Company
does not intend to incur debts beyond its ability to pay such debts as they
mature (taking into account the timing and amounts of cash to be payable on or
in respect of its debt).

          (p) CERTAIN FEES. Except as disclosed in SCHEDULE 3.1(p), the Company
has not engaged any broker, financial advisor or consultant, finder, placement
agent, investment banker, bank or other Person with respect to the transactions
contemplated by this Agreement or otherwise taken any action that would cause a
fee or commission to be paid to any such Person. No Purchaser shall have any
obligation with respect to any fees or with respect to any claims made by or on
behalf of other Persons for fees of a type contemplated in this Section that may
be due in connection with the transactions contemplated by this Agreement,
except to the extent claimed pursuant to a written agreement executed by such
Purchaser.

          (q) PRIVATE PLACEMENT. The Company has not engaged in any general
solicitation of the Securities in a manner that could adversely affect the
ability of the Company to rely on Section 4(2) of the Securities Act or Rule 506
promulgated thereunder with respect to the offer, issuance and sale of the
Securities by the Company to the Purchasers as contemplated hereby. Neither the
Company nor any Affiliate of the Company has offered for sale or solicited
offers to buy or otherwise negotiated in respect of any security (as defined in
Section 2 of the Securities Act) that would be integrated with the offer or sale
of the Securities in a manner that would require the registration under the
Securities Act of the sale of the Securities to the Purchasers, or that would be
integrated with the offer or sale of the Securities for purposes of the rules
and regulations of any Trading Market, if such integration would result in a
violation of any such rule or regulation.

          (r) FORM S-3 ELIGIBILITY. The Company is eligible to utilize Form S-3
to register the resales of its Common Stock.

          (s) LISTING AND MAINTENANCE REQUIREMENTS. The Company has not, in the
two years preceding the date hereof, received notice (written or oral) from any
Eligible Market on which the Common Stock is or has been listed or quoted to the
effect that the Company is not in compliance with the listing or maintenance
requirements of such Eligible Market. The Company is, and has no reason to
believe that it will not in the foreseeable future continue to be, in compliance
with all such listing and maintenance requirements. The issuance and sale of the
Securities hereunder does not contravene the rules and regulations of the
Trading Market and no approval of the shareholders of the Company is required
for the Company to issue and deliver to the Purchasers the maximum number of
shares of Common Stock contemplated by this

                                       9



Agreement, including by reason of the issuance of shares of Common Stock upon
conversion in full of the Preferred Stock and the issuance of the Warrant Shares
upon exercise in full of the Warrants.

          (t) REGISTRATION RIGHTS. Except as described in SCHEDULE 3.1(t), the
Company has not granted or agreed to grant to any Person any rights (including
"piggy back" registration rights) to have any securities of the Company
registered with the Commission or any other governmental authority that have not
been satisfied.

          (u) INVESTMENT COMPANY. The Company is not, and is not an Affiliate
of, an "investment company" within the meaning of the Investment Company Act of
1940, as amended.

          (v) APPLICATION OF TAKEOVER PROTECTIONS. The Company has not adopted
any "poison pill" or other similar rights arrangement.

          (w) DISCLOSURE. The Company confirms that neither it nor any other
Person acting on its behalf has provided any of the Purchasers or their agents
or counsel with any information that constitutes or might constitute material,
non-public information. The Company understands and confirms that the Purchasers
will rely on the foregoing representations in effecting transactions in
securities of the Company. All representations and warranties of the Company set
forth in this Agreement, including the Schedules to this Agreement, and the
other Transaction Documents are true and correct in all material respects and do
not contain any untrue statement of a material fact or omit to state any
material fact necessary in order to make the statements made therein, in light
of the circumstances under which they were made, not misleading.

     3.2  REPRESENTATIONS AND WARRANTIES OF EACH PURCHASER. Each Purchaser
hereby, for itself and for no other Purchaser, represents and warrants to the
Company as follows:

          (a) ORGANIZATION; AUTHORITY. Such Purchaser is an entity duly
organized, validly existing and in good standing under the laws of the
jurisdiction of its organization with the requisite corporate or partnership
power and authority to enter into and to consummate the transactions
contemplated by the Transaction Documents and otherwise to carry out its
obligations thereunder. The purchase by such Purchaser of its Securities
pursuant to the terms hereof has been duly authorized by all necessary corporate
action on the part of such Purchaser. Each of Transaction Document to which such
Purchaser is a party has been duly executed by such Purchaser, and, when
delivered by such Purchaser in accordance with the terms hereof, will constitute
the valid and legally binding obligation of such Purchaser, enforceable against
it in accordance with its terms.

          (b) INVESTMENT INTENT. Such Purchaser is acquiring the Securities as
principal for its own account for investment purposes only and not with a view
to or for distributing or reselling such Securities or any part thereof, without
prejudice, however, to such Purchaser's right, subject to the provisions of this
Agreement, at all times to sell or otherwise dispose of all or any part of such
Securities pursuant to an effective registration statement under the Securities
Act or under an exemption from such registration and in compliance with
applicable federal and

                                       10



state securities laws. Nothing contained herein shall be deemed a representation
or warranty by such Purchaser to hold Securities for any period of time. Such
Purchaser is acquiring the Securities hereunder in the ordinary course of its
business. Such Purchaser does not have any agreement or understanding, directly
or indirectly, with any Person to distribute any of the Securities.

          (c) PURCHASER STATUS. At the time such Purchaser was offered the
Securities, it was, and at the date hereof it is, and on each date on which it
converts the Preferred Stock and exercises the Warrants, it will be, an
"accredited investor" as defined in Rule 501(a) under the Securities Act. Such
Purchaser has not been formed solely for the purpose of acquiring the
Securities. Such Purchaser is not a registered broker-dealer under Section 15 of
the Exchange Act.

          (d) EXPERIENCE OF SUCH PURCHASER. Such Purchaser, either alone or
together with its representatives, has such knowledge, sophistication and
experience in business and financial matters so as to be capable of evaluating
the merits and risks of the prospective investment in the Securities, and has so
evaluated the merits and risks of such investment. Such Purchaser is able to
bear the economic risk of an investment in the Securities and, at the present
time, is able to afford a complete loss of such investment.

          (e) GENERAL SOLICITATION. To the knowledge of such Purchaser, such
Purchaser is not purchasing the Securities as a result of any advertisement,
article, notice or other communication regarding the Securities published in any
newspaper, magazine or similar media or broadcast over television or radio or
presented at any seminar or any other general solicitation or general
advertisement.

          (f) ACCESS TO INFORMATION. Such Purchaser acknowledges that it has
reviewed the Disclosure Materials and has been afforded: (i) the opportunity to
ask such questions as it has deemed necessary of, and to receive answers from,
representatives of the Company concerning the terms and conditions of the
offering of the Securities and the merits and risks of investing in the
Securities; (ii) access to information about the Company and the Subsidiaries
and their respective financial condition, results of operations, business,
properties, management and prospects sufficient to enable it to evaluate its
investment; and (iii) the opportunity to obtain such additional information that
the Company possesses or can acquire without unreasonable effort or expense that
is necessary to make an informed investment decision with respect to the
investment. Neither such inquiries nor any other investigation conducted by or
on behalf of such Purchaser or its representatives or counsel shall modify,
amend or affect such Purchaser's right to rely on the truth, accuracy and
completeness of the Disclosure Materials and the Company's representations and
warranties contained in the Transaction Documents.

          (g) CERTAIN FEES. Such Purchaser has not entered into a written
agreement pursuant to which such Purchaser has agreed to pay a Person any
brokerage or finder's fee or commission with respect to the transactions
contemplated by this Agreement.

     The Company acknowledges and agrees that no Purchaser makes or has made any
representations or warranties with respect to the transactions contemplated
hereby other than those specifically set forth in this Section 3.2.

                                       11



                                   ARTICLE IV.

                         OTHER AGREEMENTS OF THE PARTIES

     4.1  TRANSFER RESTRICTIONS.

          (a) The Securities may only be disposed of in compliance with state
and federal securities laws. In connection with any transfer of the Securities
other than pursuant to an effective registration statement, to the Company, to
an Affiliate of a Purchaser who is an "accredited investor" as defined in Rule
501(a) under the Securities Act or in connection with a pledge as contemplated
in Section 4.1(b), the Company may require the transferor thereof to provide to
the Company an opinion of counsel selected by the transferor, the form and
substance of which opinion shall be reasonably satisfactory to the Company, to
the effect that such transfer does not require registration of such transferred
Securities under the Securities Act. As a condition of transfer, any such
transferee shall agree in writing to be bound by the terms of this Agreement and
shall have the rights of a Purchaser under this Agreement, the Registration
Rights Agreement, and, if such transfer is of all or a portion of the Preferred
Stock or Warrants held by such Purchaser, as a holder of such shares of
Preferred Stock or Warrants, as the case may be.

          (b) The Purchasers agree to the imprinting, so long as is required by
this SECTION 4.1(b), of the following legend on the certificates evidencing the
Securities:

          [NEITHER] THESE SECURITIES [NOR THE SECURITIES INTO WHICH THESE
          SECURITIES ARE [CONVERTIBLE][EXERCISABLE]] HAVE BEEN REGISTERED WITH
          THE SECURITIES AND EXCHANGE COMMISSION OR THE SECURITIES COMMISSION OF
          ANY STATE IN RELIANCE UPON AN EXEMPTION FROM REGISTRATION UNDER THE
          SECURITIES ACT OF 1933, AS AMENDED (THE "SECURITIES ACT"), AND,
          ACCORDINGLY, MAY NOT BE OFFERED OR SOLD EXCEPT PURSUANT TO AN
          EFFECTIVE REGISTRATION STATEMENT UNDER THE SECURITIES ACT OR PURSUANT
          TO AN AVAILABLE EXEMPTION FROM, OR IN A TRANSACTION NOT SUBJECT TO,
          THE REGISTRATION REQUIREMENTS OF THE SECURITIES ACT AND IN ACCORDANCE
          WITH APPLICABLE STATE SECURITIES LAWS AS EVIDENCED BY A LEGAL OPINION
          OF COUNSEL TO THE TRANSFEROR TO SUCH EFFECT, THE SUBSTANCE OF WHICH
          SHALL BE REASONABLY ACCEPTABLE TO THE COMPANY. THESE SECURITIES MAY BE
          PLEDGED IN CONNECTION WITH A BONA FIDE MARGIN ACCOUNT OR OTHER LOAN
          SECURED BY SUCH SECURITIES.

     Notwithstanding anything to the contrary herein, the Company acknowledges
and agrees that a Purchaser may from time to time pledge pursuant to a bona fide
margin agreement or grant a security interest in some or all of the Securities
and, if required under the terms of such arrangement, such Purchaser may
transfer pledged or secured Securities to the pledgees or secured parties. Such
a pledge or transfer would not be subject to approval of the Company and no
legal opinion of the pledgee, secured party or pledgor shall be required in
connection

                                       12



therewith. Further, no notice shall be required of such pledge. At the
appropriate Purchaser's expense, the Company will execute and deliver such
reasonable documentation as a pledgee or secured party of Securities may
reasonably request in connection with a pledge or transfer of the Securities
including the preparation and filing of any required prospectus supplement under
Rule 424(b)(3) of the Securities Act or other applicable provision of the
Securities Act to appropriately amend the list of Selling Stockholders
thereunder.

          (c) Subject to the immediately following sentence, certificates
evidencing Securities shall not be required to contain such legend or any other
legend (i) pursuant to or following any sale of such Securities pursuant to any
effective Registration Statement covering the resale of such Securities under
the Securities Act, (ii) following any sale of such Securities pursuant to Rule
144, (iii) if such Securities are eligible for sale under Rule 144(k), or (iv)
if such legend is not, in the reasonable opinion of the Company Counsel,
required under the circumstances under applicable requirements of the Securities
Act (including judicial interpretations and pronouncements issued by the Staff
of the Commission). Accordingly, at the request of a Purchaser, Common Shares
will be reissued, free of all legends following the Effective Date. The Company
agrees that following the Effective Date or at such time as such legend is no
longer required under this Section 4.1(c), it will, no later than three Trading
Days following the delivery by a Purchaser to the Company or the Company's
transfer agent of a certificate representing Common Shares, Warrant Shares or
Underlying Shares issued with a restrictive legend, deliver or cause to be
delivered to such Purchaser a certificate representing such Common Shares,
Warrant Shares or Underlying Shares that is free from all restrictive and other
legends. Each Purchaser, severally and not jointly, agrees to indemnify the
Company for any losses actually incurred by the Company by reason of such
Purchaser failing to comply with the prospectus delivery requirements of the
Exchange Act in connection with any such re-issued legend-free shares. In
addition, each certificate for shares of Preferred Stock shall bear the
following Legend: "THE NUMBER OF SHARES OF PREFERRED STOCK REPRESENTED BY THIS
CERTIFICATE MAY BE LESS THAN THE NUMBER OF SHARES OF PREFERRED STOCK STATED ON
THE FACE HEREOF PURSUANT TO SECTION 3(c) OF THE CERTIFICATE OF DESIGNATIONS. The
Company may not make any notation on its records or give instructions to any
transfer agent of the Company that enlarge the restrictions on transfer set
forth in this Section.

     4.2  FURNISHING OF INFORMATION. As long as any Purchaser owns
Securities, the Company covenants to timely file (or obtain extensions in
respect thereof and file within the applicable grace period) all reports
required to be filed by the Company after the date hereof pursuant to the
Exchange Act. Upon the request of any such Person, the Company shall deliver
to such Person a written certification of a duly authorized officer as to
whether it has complied with the preceding sentence. As long as any Purchaser
owns Securities, if the Company is not required to file reports pursuant to
such laws, it will prepare and furnish to the Purchasers and make publicly
available in accordance with Rule 144(c) such information as is required for
the Purchasers to sell the Shares or Warrant Shares under Rule 144.

     4.3  INTEGRATION. The Company shall not, and shall use its best efforts
to ensure that no Affiliate of the Company shall, sell, offer for sale or
solicit offers to buy or otherwise negotiate in respect of any security (as
defined in Section 2 of the Securities Act) that would be integrated

                                       13



with the offer or sale of the Securities in a manner that would require the
registration under the Securities Act of the sale of the Securities to the
Purchasers, or that would be integrated with the offer or sale of the Securities
for purposes of the rules and regulations of any Trading Market, if such
integration would result in a violation of any such rule or regulation.

     4.4  INCREASE IN AUTHORIZED SHARES. If on any date the Company would be,
if notice of exercise or conversion were to be delivered on such date,
precluded from issuing the number of Warrant Shares or Underlying Shares, as
the case may be, issuable upon exercise in full of all of the Warrants and
issuable upon conversion in full of the Preferred Stock due to the
unavailability of a sufficient number of authorized but unissued or reserved
shares of Common Stock, then the Board of Directors of the Company shall
promptly prepare and mail to the stockholders of the Company proxy materials
requesting authorization to amend the Company's certificate of incorporation
to increase the number of shares of Common Stock which the Company is
authorized to issue so as to provide enough shares for issuance of the
Warrant Shares and Underlying Shares. In connection therewith, the Board of
Directors shall (a) adopt proper resolutions authorizing such increase, (b)
recommend to and otherwise use its best efforts to promptly and duly obtain
stockholder approval to carry out such resolutions (and hold a special
meeting of the stockholders as soon as practicable, but in any event not
later than the 60th day after delivery of the proxy materials relating to
such meeting) and (c) within five Business Days of obtaining such stockholder
authorization, file an appropriate amendment to the Company's certificate or
articles of incorporation to evidence such increase.

     4.5  REGISTRATION STATEMENTS. From the date hereof through and including
the Effective Date, the Company will not file a registration statement (other
than on a Form S-8 and pursuant to the Registration Rights Agreement) with
the Commission with respect to any securities of the Company or the
Subsidiaries.

     4.6  SECURITIES LAWS DISCLOSURE; PUBLICITY. The Company shall, within
seven days after the Closing Date, issue a press release or file a Current
Report on Form 8-K reasonably acceptable to the Purchasers disclosing all
material terms of the transactions contemplated hereby. The Company and the
Purchasers shall consult with each other in issuing any press releases with
respect to the transactions contemplated hereby. Notwithstanding the
foregoing, other than in any registration statement filed pursuant to the
Registration Rights Agreement and filings related thereto, the Company shall
not publicly disclose the name of any Purchaser, or include the name of any
Purchaser in any filing with the Commission or any regulatory agency or
Trading Market, without the prior written consent of such Purchaser, except
to the extent such disclosure is required by law or Trading Market
regulations, in which case the Company shall provide the Purchasers with
prior notice of such disclosure.

     4.7  INDEMNIFICATION OF PURCHASERS. The Company hereby indemnifies and
holds the Purchasers and their directors, officers, shareholders, partners,
employees and agents (each, a "PURCHASER PARTY") harmless from any and all
losses, liabilities, obligations, claims, contingencies, damages, costs and
expenses, including all judgments, amounts paid in settlements, court costs
and reasonable attorneys' fees and costs of investigation (collectively,
"Losses") that any such Purchaser Party may suffer or incur as a result of or
relating to (a) any misrepresentation, breach or inaccuracy, or any
allegation by a third party that, if true, would constitute a breach or
inaccuracy, of any of the representations, warranties, covenants or

                                       14



agreements made by the Company in this Agreement or in the other Transaction
Documents; or (b) any cause of action, suit or claim brought or made against
such Purchaser Party and solely arising out of or solely resulting from the
execution, delivery, performance or enforcement of this Agreement or any of the
other Transaction Documents (other than due to the gross negligence or willful
misconduct of the Purchaser Party). The Company will reimburse such Purchaser
for its reasonable legal and other expenses (including the cost of any
investigation, preparation and travel in connection therewith) incurred in
connection therewith, as such expenses are incurred. The Purchaser Party may
not, without the prior written consent of the Company, agree to any settlement
of any claim or action with respect to which the Company is required to
indemnify the Purchaser Party pursuant to this Section 4.7.

     4.8  NON-PUBLIC INFORMATION. The Company covenants and agrees that
neither it nor any other Person acting on its behalf will provide any
Purchaser or its agents or counsel with any information that the Company
believes constitutes material non-public information, unless prior thereto
such Purchaser shall have executed a written agreement regarding the
confidentiality and use of such information. The Company understands and
confirms that each Purchaser shall be relying on the foregoing
representations in effecting transactions in securities of the Company.

     4.9  USE OF PROCEEDS. The Company shall use the net proceeds from the
sale of the Securities hereunder for working capital purposes, for capital
expenditures and for acquisitions and not to redeem any Company equity or
equity equivalent securities, to settle any outstanding litigation or to
extend any loans to its directors or senior management.

     4.10 RESTRICTIONS ON SALE OF SECURITIES. Each Purchaser agrees that it
will not, directly or indirectly, prior to the earlier of (i) 120 days after
Closing and (ii) the Settlement Date, engage in any hedging or other
transaction (including any short sale (whether or not against the box) or any
purchase, sale or grant of any right (including any put or call option) with
respect to such Securities) which is designed or could reasonably be expected
to lead to or result in a sale other than a long sale of the Common Shares,
Underlying Shares or Warrant Shares acquired at the Closing by such Purchaser
prior to such date. This provision shall not affect in any way the right of a
Purchaser to engage in any long sales of Common Stock, including any Common
Shares issued to such Purchaser at Closing, beneficially owned by such
Purchaser at the time of such sale. In the event that the Preferred Stock has
not previously been redeemed, the parties hereto agree that the restrictions
set forth in Section 4.10 covers the period during which the conversion price
of the Preferred Stock is established.

                                   ARTICLE V.

                                  MISCELLANEOUS

     5.1 FEES AND EXPENSES. At the Closing, the Company shall pay the
Purchasers, in proportion to their respective purchase prices, an aggregate of
$40,000 for their legal fees and expenses incurred in connection with the
preparation and negotiation of the Transaction Documents, less any previously
delivered amounts. In lieu of the foregoing payment, the Purchasers may retain
their pro-rata portion of such amount at the Closing instead of delivering such
amount at Closing or require the Company to pay such aggregate amount directly
to Purchaser Counsel. Except as expressly set forth in the Transaction
Documents, each party shall

                                       15



pay the fees and expenses of its advisers, counsel, accountants and other
experts, if any, and all other expenses incurred by such party incident to the
negotiation, preparation, execution, delivery and performance of this Agreement.
The Company shall pay all stamp and other taxes and duties levied in connection
with the sale of the Securities.

     5.2  ENTIRE AGREEMENT. The Transaction Documents, together with the
Exhibits and Schedules thereto, contain the entire understanding of the
parties with respect to the subject matter hereof and supersede all prior
agreements and understandings, oral or written, with respect to such matters,
which the parties acknowledge have been merged into such documents, exhibits
and schedules. At or after the Closing, and without further consideration,
the Company will execute and deliver to the Purchasers such further documents
as may be reasonably requested in order to give practical effect to the
intention of the parties under the Transaction Documents.

     5.3  NOTICES. Any and all notices or other communications or deliveries
required or permitted to be provided hereunder shall be in writing and shall
be deemed given and effective on the earliest of (i) the date of
transmission, if such notice or communication is delivered via facsimile at
the facsimile telephone number specified in this Section prior to 6:30 p.m.
(New York City time) on a Trading Day, (ii) the Trading Day after the date of
transmission, if such notice or communication is delivered via facsimile at
the facsimile telephone number specified in this Agreement later than 6:30
p.m. (New York City time) on any date and earlier than 11:59 p.m. (New York
City time) on such date, (iii) the Trading Day following the date of mailing,
if sent by nationally recognized overnight courier service, or (iv) upon
actual receipt by the party to whom such notice is required to be given. The
address for such notices and communications shall be as follows:

     If to the Company:        I-Many, Inc.
                               537 Congress Street, 5TH Floor
                               Portland, Maine 04101-3353
                               Attn: Chief Financial Officer
                               Fax No.: (207) 828-0492

     With a copy to:            Hale and Dorr LLP
                                60 State Street
                                Boston, MA 02109
                                Fax No: (617) 526-5000
                                Attn: Jeffrey A. Stein

     If                         to a Purchaser: To the address set forth
                                under such Purchaser's name on the signature
                                pages hereto.

or such other address as may be designated in writing hereafter, in the same
manner, by such Person.

     5.4  AMENDMENTS; WAIVERS. No provision of this Agreement may be waived
or amended except in a written instrument signed, in the case of an
amendment, by the Company and the Purchasers holding a majority of the Shares
issued at Closing or, in the case of a waiver,

                                       16



by the party against whom enforcement of any such waiver is sought. No waiver of
any default with respect to any provision, condition or requirement of this
Agreement shall be deemed to be a continuing waiver in the future or a waiver of
any subsequent default or a waiver of any other provision, condition or
requirement hereof, nor shall any delay or omission of either party to exercise
any right hereunder in any manner impair the exercise of any such right.

     5.5  CONSTRUCTION. The headings herein are for convenience only, do not
constitute a part of this Agreement and shall not be deemed to limit or
affect any of the provisions hereof. The language used in this Agreement will
be deemed to be the language chosen by the parties to express their mutual
intent, and no rules of strict construction will be applied against any party.

     5.6  SUCCESSORS AND ASSIGNS. This Agreement shall be binding upon and
inure to the benefit of the parties and their successors and permitted
assigns. The Company may not assign this Agreement or any rights or
obligations hereunder without the prior written consent of the Purchasers.
Any Purchaser may assign any or all of its rights under this Agreement and
the registration Rights Agreement to any Person to whom such Purchaser
assigns or transfers any Securities in accordance with the terms of this
Agreement, provided such transferee agrees in writing to be bound, with
respect to the transferred Securities, by the provisions hereof that apply to
the "Purchasers."

     5.7  NO THIRD-PARTY BENEFICIARIES. This Agreement is intended for the
benefit of the parties hereto and their respective successors and permitted
assigns and is not for the benefit of, nor may any provision hereof be
enforced by, any other Person.

     5.8  GOVERNING LAW. All questions concerning the construction, validity,
enforcement and interpretation of this Agreement shall be governed by and
construed and enforced in accordance with the internal laws of the State of
New York, without regard to the principles of conflicts of law thereof. Each
party agrees that all Proceedings concerning the interpretations, enforcement
and defense of the transactions contemplated by this Agreement and any other
Transaction Documents (whether brought against a party hereto or its
respective affiliates, directors, officers, shareholders, employees or
agents) shall be commenced exclusively in the state and federal courts
sitting in the City of New York, Borough of Manhattan. Each party hereto
hereby irrevocably submits to the exclusive jurisdiction of the state and
federal courts sitting in the City of New York, Borough of Manhattan for the
adjudication of any dispute hereunder or in connection herewith or with any
transaction contemplated hereby or discussed herein (including with respect
to the enforcement of the any of the Transaction Documents), and hereby
irrevocably waives, and agrees not to assert in any Proceeding, any claim
that it is not personally subject to the jurisdiction of any such court, that
such Proceeding is improper. Each party hereto hereby irrevocably waives
personal service of process and consents to process being served in any such
Proceeding by mailing a copy thereof via registered or certified mail or
overnight delivery (with evidence of delivery) to such party at the address
in effect for notices to it under this Agreement and agrees that such service
shall constitute good and sufficient service of process and notice thereof.
Nothing contained herein shall be deemed to limit in any way any right to
serve process in any manner permitted by law. Each party hereto hereby
irrevocably waives, to the fullest extent permitted by applicable law, any
and all right to trial by jury in any legal proceeding arising out of or
relating to this Agreement or the transactions contemplated hereby. If either
party shall commence a Proceeding to enforce any provisions of a Transaction

                                       17



Document, then the prevailing party in such Proceeding shall be reimbursed by
the other party for its attorneys fees and other costs and expenses incurred
with the investigation, preparation and prosecution of such Proceeding.

     5.9  SURVIVAL. The representations, warranties, agreements and covenants
contained herein shall survive the Closing.

     5.10  EXECUTION. This Agreement may be executed in two or more
counterparts, all of which when taken together shall be considered one and
the same agreement and shall become effective when counterparts have been
signed by each party and delivered to the other party, it being understood
that both parties need not sign the same counterpart. In the event that any
signature is delivered by facsimile transmission, such signature shall create
a valid and binding obligation of the party executing (or on whose behalf
such signature is executed) with the same force and effect as if such
facsimile signature page were an original thereof.

     5.11  SEVERABILITY. If any provision of this Agreement is held to be
invalid or unenforceable in any respect, the validity and enforceability of
the remaining terms and provisions of this Agreement shall not in any way be
affected or impaired thereby and the parties will attempt to agree upon a
valid and enforceable provision that is a reasonable substitute therefor, and
upon so agreeing, shall incorporate such substitute provision in this
Agreement.

     5.12  RESCISSION AND WITHDRAWAL RIGHT. Notwithstanding anything to the
contrary contained in (and without limiting any similar provisions of) the
Transaction Documents, whenever any Purchaser exercises a right, election,
demand or option under a Transaction Document and the Company does not timely
perform its related obligations within the periods therein provided, then
such Purchaser may rescind or withdraw, in its sole discretion from time to
time upon written notice to the Company, any relevant notice, demand or
election in whole or in part without prejudice to its future actions and
rights.

     5.13  REPLACEMENT OF SECURITIES. If any certificate or instrument
evidencing any Securities is mutilated, lost, stolen or destroyed, the
Company shall issue or cause to be issued in exchange and substitution for
and upon cancellation thereof, or in lieu of and substitution therefor, a new
certificate or instrument, but only upon receipt of evidence reasonably
satisfactory to the Company of such loss, theft or destruction and customary
and reasonable indemnity, if requested. The applicants for a new certificate
or instrument under such circumstances shall also pay any reasonable
third-party costs associated with the issuance of such replacement Securities.

     5.14  REMEDIES. In addition to being entitled to exercise all rights
provided herein or granted by law, including recovery of damages, each of the
Purchasers and the Company will be entitled to specific performance under the
Transaction Documents. The parties agree that monetary damages may not be
adequate compensation for any loss incurred by reason of any breach of
obligations described in the foregoing sentence and hereby agrees to waive in
any action for specific performance of any such obligation the defense that a
remedy at law would be adequate.

                                       18



     5.15  PAYMENT SET ASIDE. To the extent that the Company makes a payment
or payments to any Purchaser pursuant to any Transaction Document or a
Purchaser enforces or exercises its rights thereunder, and such payment or
payments or the proceeds of such enforcement or exercise or any part thereof
are subsequently invalidated, declared to be fraudulent or preferential, set
aside, recovered from, disgorged by or are required to be refunded, repaid or
otherwise restored to the Company, a trustee, receiver or any other person
under any law (including, without limitation, any bankruptcy law, state or
federal law, common law or equitable cause of action), then to the extent of
any such restoration the obligation or part thereof originally intended to be
satisfied shall be revived and continued in full force and effect as if such
payment had not been made or such enforcement or setoff had not occurred.

     5.16  INDEPENDENT NATURE OF PURCHASERS' OBLIGATIONS AND RIGHTS. The
obligations of each Purchaser under any Transaction Document are several and
not joint with the obligations of any other Purchaser, and no Purchaser shall
be responsible in any way for the performance of the obligations of any other
Purchaser under any Transaction Document. Nothing contained herein or in any
Transaction Document, and no action taken by any Purchaser pursuant thereto,
shall be deemed to constitute the Purchasers as a partnership, an
association, a joint venture or any other kind of entity, or create a
presumption that the Purchasers are in any way acting in concert or as a
group with respect to such obligations or the transactions contemplated by
the Transaction Document. Each Purchaser shall be entitled to independently
protect and enforce its rights, including without limitation the rights
arising out of this Agreement or out of the other Transaction Documents, and
it shall not be necessary for any other Purchaser to be joined as an
additional party in any proceeding for such purpose.

                   [REMAINDER OF PAGE INTENTIONALLY LEFT BLANK

                             SIGNATURE PAGES FOLLOW]


                                       19




     IN WITNESS WHEREOF, the parties hereto have caused this Securities Purchase
Agreement to be duly executed by their respective authorized signatories as of
the date first indicated above.



                            I-MANY, INC.


                            By: /s/ A. LEIGH POWELL
                                ---------------------------------------------
                                Name:  A. Leigh Powell
                                Title: CEO



                   [REMAINDER OF PAGE INTENTIONALLY LEFT BLANK
                     SIGNATURE PAGES FOR PURCHASERS FOLLOWS]



                                       20




     IN WITNESS WHEREOF, the parties hereto have caused this Securities
Purchase Agreement to be duly executed by their respective authorized persons
as of the day and year first above written.

                             FIRST INVESTORS HOLDING CO., INC.

                             By: /s/ KENNETH L. HENDERSON
                                 --------------------------------------------
                                 Name:  Kenneth L. Henderson
                                 Title: Attorney-in-fact


                             Common Shares Investment Amount:    $4,325,000
                             Preferred Stock Investment Amount:  $9,190,000


                             Address for Notice:

                             c/o Cavallo Capital Corp.
                             660 Madison Avenue, 18th Floor
                             New York, New York 10021
                             Attention: Eldad Gal
                             Facsimile: (212) 651-9010

                             With a copy to:

                             Robinson Silverman Pearce Aronsohn & Berman LLP
                             1290 Avenue of the Americas
                             New York, NY  10104
                             Facsimile No.: (212) 541-4630 and (212) 541-1432
                             Attn: Eric L. Cohen, Esq.



                                       21




     IN WITNESS WHEREOF, the parties hereto have caused this Securities Purchase
Agreement to be duly executed by their respective authorized persons as of
the day and year first above written.

                             PINE RIDGE FINANCIAL INC.

                             By: /s/ KENNETH L. HENDERSON
                                 --------------------------------------------
                                 Name:  Kenneth L. Henderson
                                 Title: Attorney-in-fact


                             Common Shares Investment Amount:    $3,675,000
                             Preferred Stock Investment Amount:  $7,810,000


                             Address for Notice:

                             c/o Cavallo Capital Corp.
                             660 Madison Avenue, 18th Floor
                             New York, New York 10021
                             Attention: Eldad Gal
                             Facsimile: (212) 651-9010

                             With a copy to:

                             Robinson Silverman Pearce Aronsohn & Berman LLP
                             1290 Avenue of the Americas
                             New York, NY  10104
                             Facsimile No.: (212) 541-4630 and (212) 541-1432
                             Attn: Eric L. Cohen, Esq.



                                       22