Stockholders' Equity | 8. Stockholders’ Equity During February 2014, the Company increased its authorized number of shares of convertible preferred stock to 30,233,694 shares. During March 2014, the Company increased its authorized number of shares of convertible preferred stock to 60,503,445 shares and increased its authorized number of shares of common stock to 25,000,000 shares. Immediately following the Stock Conversion and the one-for- four reverse stock split effected in September 2014, the Company reestablished its authorized number of shares of convertible preferred stock to 8,866,753 shares and its authorized number of shares of common stock to 15,742,382 shares. During November 2014, the Company increased its authorized number of shares of convertible preferred stock to 23,228,986 shares and increased its authorized number of shares of common stock to 35,000,000 shares. Concurrent with the Company’s initial public offering completed in June 2015 (the “IPO”), the Company increased its authorized number of shares of common stock to 2 00 , 000 , 000 shares , eliminated its authorized shares of convertible preferred s tock and authorized 10 ,000,000 shares of preferred stock for future issuance . Convertible Preferred Stock Immediately prior to the Stock Conversion, the Company had six series of outstanding convertible preferred stock: Series A-1 convertible preferred stock, Series A-2 convertible preferred stock, Series C-1 convertible preferred stock, Series C-2 convertible preferred stock, Series D convertible preferred stock and Series E convertible preferred stock. The convertible preferred stock was initially recorded at the issuance price on the date of issuance, net of issuance costs. As a result of the Stock Conversion o n September 23, 2014 , all outstanding preferred stock was converted into shares of common stock on an 11.556 -for-1 basis. Concurrent with the Stock Conversion, a newly created Series 1 convertible preferred stock was issued in the settlement of the 2014 Notes. In November and December 2014, the Company raised $31.0 million gross proceeds in a private placement of Series 2 convertible preferred stock . On June 22, 2015, prior to the closing of the Company’s IPO, all outstanding shares of convertible preferred stock, amounting to 19,978,986 shares, were automatically converted into 6,915,525 shares of common stock in accordance with the terms of the Company’s amended and restated certificate of incorporation then in existence. As of December 31, 2015, the Company had no preferred stock or convertible preferred stock outstanding . Common Stock On June 22, 2015, the Company completed its IPO of 6,325,000 shares of its common stock, including 875,000 shares from the exercise of the underwriters’ over-allotment option , at a price to the public of $14.00 per share for aggregate gross proceeds of $88.6 million. The Company received proceeds of $78.8 million from its IPO, net of $3.6 million in expenses and $6.2 million in underwriters’ discounts and commissions relating to the issuance and distribution of the securities. At December 31, 2015, shares of common stock have been reserved for issuance as follows: Options to purchase common stock - issued Options to purchase common stock - unissued Employee stock purchase plan Common stock warrants - issued Total Stock-Based Compensation Restricted Stock Prior to the Company Conversion on August 1, 2012, the Company issued Class B units to employees, which were considered profits interest. The fair value of these units was recorded as stock-based compensation expense on a straight-line basis over the requisite service period of each award, generally four years. As a result of the Company Conversion on August 1, 2012, the Company converted the vested and unvested Class B units into 171,415 shares of common stock subject to stock restriction agreements. These shares vest over the same vesting period of the original Class B unit grants and any unvested shares would be forfeited upon the termination of the employee. Stock Options In August 2012, the Company adopted the 2012 Stock Incentive Plan (the “2012 Plan”). A total of 147,109 shares of common stock were originally reserved for issuance under the 2012 Plan. On November 17, 2014, and December 12, 2014, the Company’s Board of Directors approved an increase of 623,052 and 519,210 shares, respectively, to the total number of shares that may be issued under the 2012 Plan, which after these increases totaled 1,289,371 shares. As of December 31, 2015, 1,288,174 accumulated shares had been granted under the 2012 Plan to employees and directors , while 685 shares had been exercised and 512 shares were terminated upon the termination of the 2012 Plan effective with the closing of the Company’s IPO. In May 2015, the Company’s Board of Directors and its s tockholders approved the 2015 Equity Incentive Plan (the “2015 Plan”). Effective with the Company’s IPO closing, a total of 1,081,700 shares of common stock were originally reserved for issuance under the 2015 Plan. The 2015 Plan provides that an additional number of shares will automatically be added to the shares authorized for issuance under the 2015 Plan on January 1 of each calendar year, from January 1, 2016 through January 1, 2025. The number of shares added each year will be equal to: (a) 5% of the total number of shares of Common Stock issued and outstanding on December 31 of the preceding calendar year; or (b) such lesser number of shares of Common Stock approved by the Board of Directors on or prior to such immediately preceding December 31. The 2015 Plan provides for the granting of incentive and nonqualified stock options, stock appreciation rights, restricted stock, restricted stock units, performance-based awards and other share-based awards to its employees, directors and consultants. Stock options granted vest over either a one -year period or three -year period for Board of Director grants or over a four -year period for employee grants and expire 10 years from the date of grant. The fair value of each option grant for the year ended December 31, 2015, 2014 and 2013, was estimated at the date of grant using the Black-Scholes option-pricing model with the following assumptions: 2015 2014 2013 Estimated dividend yield – * – Weighted-average expected stock price volatility % * % Weighted-average risk-free interest rate % * % Weighted-average expected life of option (in years) * Weighted-average fair value per option $ * $ * There were no options granted during 2014 Due to limited historical data, the Company estimates stock price volatility based on the actual volatility of comparable publicly traded companies over the expected life of the option. The expected term represents the average time that options that vest are expected to be outstanding. The Company does not have sufficient history of exercise of stock options to estimate the expected term for employee stock options and, thus, continues to calculate expected life based on the midpoint between the average vesting date and the contractual term, which is in accordance with the simplified method. The risk-free rate is based on the United States Treasury yield curve for the expected life of the option. The fair value of the common stock utilized in the fair value estimation of option and restricted stock arrangements prior to the Company’s IPO of June 2015 has been determined utilizing contemporaneous valuations primarily based on an option pricing methodology. The tables below summarize the stock option activity for the year ended December 31, 2015: Weighted Available for Options Average Grant Outstanding Exercise Price Balance as of January 1, 2015 $ Additional authorized – Granted Exercised – Cancelled Shares terminated from the 2012 Plan – Balance as of December 31, 2015 $ Weighted- Average Remaining Weighted- Contractual Aggregate Number of Average Life Intrinsic Options Exercise Price (In Years) Value As of December 31, 2015: Options outstanding $ $ Options expected to vest, net of estimated forfeitures $ $ Options exercisable $ $ During 2015, 2014 and 2013, the Company recorded approximately $1.3 million, $66,000 and $91,000 , respectively, in employee stock-based compensation expense for the vesting of stock options. No stock options have been granted to consultants. As of December 31, 2015, there was approximately $7.1 million of total unrecognized stock-based compensation expense related to nonvested stock options, which is expected to be recognized over a weighted-average period of 3.3 years. The Company did not recognize a tax benefit related to share-based compensation expense during the years ended December 31, 2015, 2014 and 2013 as the Company maintains net operating loss carryforwards and has established a valuation allowance against the entire net deferred tax asset as of December 31, 2015. Employee Stock Purchase Plan In May 2015, the Company’s Board of Directors and its s tockholders approved the Nivalis Therapeutics, Inc. Employee Stock Purchase Plan (the “Purchase Plan”). Effective on the closing of the Company’s IPO, a total of 231,800 shares of common stock were made available for sale under the Purchase Plan. The Purchase Plan may be amended, suspended or terminated at any time by the Board of Directors, however s tockholder approval is required to increase the number of common stock available under the Purchase Plan or to change the employees eligible to participate in the Purchase Plan. The Purchase Plan provides for a series of successive six -month offering periods, from January to June and July to December of each calendar year during which participating employees may elect to have up to 15% of their compensation withheld and applied to the purchase of common stock at the end of each offering period. The purchase price of the common stock is 85% of the lower of the fair value of a share of common stock on the first trading date of each offering period or the fair value of a share of common stock on the last trading day of the offering period. The Company sold 8,924 shares to employees on December 31, 2015. There were 222,876 shares available for sale under the Purchase Plan as of December 31, 2015. The weighted-average estimated grant date fair value of purchase awards under the Purchase Plan during the year ended December 31, 2015 was $5.18 . The total share-based compensation expense recorded as a result of the Purchase Plan was approximately $22,000 during the year ended December 31, 2015. The fair value of purchase awards granted to our employees during the year ended December 31, 2015 was estimated using the Black-Scholes option pricing model using the weighted-average assumptions provided in the following table: Estimated dividend yield – Expected stock price volatility % Risk-free interest rate % Expected life of option (in years) Due to limited historical data, the Company estimates stock price volatility based on the actual volatility of comparable publicly traded companies over the expected life of the purchase right. The risk-free rate is based on the U.S. Treasury yield in effect at the time of grant with terms similar to the contractual term of the purchase right. The expected term represents the six-month offering period for the Purchase Plan. |