Stockholders' Equity | 8. Stockholders’ Equity At-The-Market Sales Facility In October 2020, the Company entered into an at-the-market sales agreement (the 2020 Sales Agreement) with Cowen and Company, LLC (Cowen). The 2020 Sales Agreement was terminated in April 2022. There were no shares sold under the 2020 Sales Agreement from January 2022 until April 2022. During the nine months ended September 30, 2021, the Company issued and sold In March 2022, the Company filed a shelf registration statement with the SEC, which was declared effective on April 22, 2022. On April 28, 2022, the Company entered into a new at-the-market sales agreement (the 2022 Sales Agreement) with Cowen. Under the 2022 Sales Agreement, the Company may sell up to 2003 Stock Incentive Plan The 2003 Stock Incentive Plan (the 2003 Plan) provided for the grant of incentives and nonqualified stock options and restricted stock awards. The exercise price for incentive stock options must be at least equal to the fair value of the common stock on the grant date. Unless otherwise stated in a stock option agreement, 25% of the shares subject to an option grant will vest upon the first anniversary of the vesting start date and thereafter at the rate of one forty A summary of the Company’s stock option activity under the 2003 Plan for the nine months ended September 30, 2022 is as follows: WEIGHTED- AGGREGATE WEIGHTED- AVERAGE INTRINSIC AVERAGE REMAINING VALUE OUTSTANDING EXERCISE CONTRACTUAL (IN OPTIONS PRICE TERM (YEARS) THOUSANDS) Outstanding as of December 31, 2021 93,465 $ 2.00 0.3 Options forfeited (92,465) 1.98 Outstanding, Vested and Exercisable as of September 30, 2022 1,000 3.73 0.1 $ — As of September 30, 2022, outstanding options under the 2003 Plan were fully expensed and all shares underlying outstanding options were fully vested. There were no options exercised during the nine months ended September 30, 2022. Total intrinsic value for the 3,785 options exercised during the nine months ended September 30, 2021 was $8,668 and total cash received for options exercised was $4,239. 2013 Equity Incentive Plan The Company’s board of directors adopted, and its stockholders approved, its 2013 Equity Incentive Plan effective on January 9, 2014, and the 2013 Equity Incentive Plan was amended and restated in May 2022 (as amended and restated, the 2013 Plan). The 2013 Plan provides for the grant of incentive stock options within the meaning of Section 422 of the Internal Revenue Code to the Company’s employees and its parent and subsidiary corporations’ employees, and for the grant of nonstatutory stock options, restricted stock awards, RSU awards, stock appreciation rights, performance stock awards and other forms of stock compensation to its employees, including officers, consultants and directors. The 2013 Plan also provides for the grant of performance cash awards to the Company’s employees, consultants and directors. Unless otherwise stated in a stock option agreement, 25% of the shares subject to an option grant will typically vest upon the first anniversary of the vesting start date, with the balance of the shares vesting in a series of thirty-six successive equal monthly installments as of the first day of each month measured from the first anniversary of the vesting start date. Upon termination of employment by reasons other than death, cause, or disability, any vested options will terminate 90 days after the termination date, unless otherwise set forth in a stock option agreement. Stock options generally terminate 10 years from the date of grant. Authorized Shares The maximum number of shares of common stock that initially could be issued under the 2013 Plan was shares, plus any shares subject to stock options or similar awards granted under the 2003 Plan that expire or terminate without having been exercised in full or are forfeited or repurchased by the Company. In May 2022, the 2013 Plan was amended to increase the existing share reserve by Shares issued under the 2013 Plan may be authorized but unissued or reacquired shares of common stock. Shares subject to stock awards granted under the 2013 Plan that expire or terminate without being exercised in full, or that are paid out in cash rather than in shares, will not reduce the number of shares available for issuance under the 2013 Plan. Additionally, shares issued pursuant to stock awards under the 2013 Plan that the Company repurchases or that are forfeited, as well as shares reacquired by the Company as consideration for the exercise or purchase price of a stock award or to satisfy tax withholding obligations related to a stock award, will become available for future grant under the 2013 Plan. A summary of the Company’s stock option activity under the 2013 Plan for the nine months ended September 30, 2022 is as follows: WEIGHTED- AGGREGATE WEIGHTED- AVERAGE INTRINSIC AVERAGE REMAINING VALUE OUTSTANDING EXERCISE CONTRACTUAL (IN OPTIONS PRICE TERM (YEARS) THOUSANDS) Outstanding as of December 31, 2021 5,655,457 $ 8.30 6.0 Options granted 2,020,800 1.06 Options forfeited (747,359) 6.07 Outstanding as of September 30, 2022 6,928,898 6.42 6.2 $ — Vested or expected to vest as of September 30, 2022 6,739,298 6.57 6.1 — Exercisable as of September 30, 2022 4,509,213 8.81 4.7 — As of September 30, 2022, there was $3,303,583 of total unrecognized compensation expense related to unvested options under the 2013 Plan that will be recognized over a weighted-average period of approximately 2.0 years. There were no options exercised under the 2013 Plan during the nine months ended September 30, 2022 and 2021. The total fair value of shares underlying options which vested in the nine months ended September 30, 2022 and 2021 was $2,699,940 and $4,844,743, respectively. In January 2022, the Company granted stock options to purchase an aggregate of 189,600 shares to certain employees under the 2013 Plan that are subject to performance vesting conditions. The shares will vest upon achievement of milestones as follows: (i) one one An RSU is a stock award that entitles the holder to receive shares of the Company’s common stock as the award vests. The fair value of each RSU is based on the closing price of the Company’s common stock on the date of grant. In January 2021, the Company awarded RSUs under the 2013 Plan to its employees. The RSUs granted vest over four years in equal installments on each anniversary of the grant date, provided that the employee remains employed by the Company at the applicable vesting date. Compensation expense is recognized on a straight-line basis. As of September 30, 2022, there was $601,408 of total unrecognized compensation expense associated with outstanding RSU grants that will be recognized over a weighted-average period of approximately 2.3 years. The following is a summary of RSU activity under the 2013 Plan for the nine months ended September 30, 2022: Weighted-Average Number of Shares Grant Date Underlying RSUs Fair Value Unvested at December 31, 2021 345,600 $ 3.70 Forfeited (30,147) 3.81 Vested (110,050) 3.45 Unvested at September 30, 2022 205,403 3.81 Inducement Plan In January 2020, the Company’s board of directors adopted the GlycoMimetics, Inc. Inducement Plan (the Inducement Plan). The Inducement Plan provides for the grant of nonstatutory stock options, restricted stock awards, RSU awards, stock appreciation rights and other forms of stock awards to individuals not previously an employee or director of the Company as an inducement for such individuals to join the Company. Unless otherwise stated in an applicable stock option agreement, one A summary of the Company’s stock option activity under the Inducement Plan for the nine months ended September 30, 2022 is as follows: WEIGHTED- AGGREGATE WEIGHTED- AVERAGE INTRINSIC AVERAGE REMAINING VALUE OUTSTANDING EXERCISE CONTRACTUAL (IN OPTIONS PRICE TERM (YEARS) THOUSANDS) Outstanding as of December 31, 2021 1,813,600 $ 2.08 9.6 Options granted 535,000 0.98 Options forfeited (12,200) 3.69 Outstanding as of September 30, 2022 2,336,400 1.82 9.0 $ — Vested or expected to vest as of September 30, 2022 1,752,200 1.77 9.0 — Exercisable as of September 30, 2022 326,383 2.17 8.8 — As of September 30, 2022, there was $1,620,031 of total unrecognized compensation expense related to unvested options under the Inducement Plan that will be recognized over a weighted-average period of approximately 3.0 years. There were no options exercised under the Inducement Plan during the nine months ended September 30, 2022 and 10,092 options exercised during the nine months ended September 30, 2021. Total intrinsic value of options exercised during the nine months ended September 30, 2021 was $1,944 and total cash received for options exercised was $20,790 during the nine months ended September 30, 2021. The total fair value of shares underlying options that vested in the nine months ended September 30, 2022 and 2021 was $460,950 and $62,667, respectively. During 2021 and the nine months ended September 30, 2022, the Company granted stock options to purchase an aggregate of 584,200 shares to certain newly hired employees under the Inducement Plan which options were subject to the same performance vesting conditions described above with respect to the stock options granted in January 2022 under the 2013 Plan. The maximum fair value of $825,353 associated with the performance-based options is excluded from the unrecognized compensation expense under the Inducement Plan as the completion of the performance milestones were not probable as of September 30, 2022. The Company will reevaluate at the end of each reporting period the probability that the performance conditions will be achieved and will record any adjustments to the compensation cost at that time. The weighted-average fair value of the options granted under all equity incentive plans during the nine months ended September 30, 2022 and 2021 was $0.76 per share and $1.87 per share, respectively, applying the Black-Scholes-Merton option pricing model utilizing the following weighted-average assumptions: 2022 2021 Expected term 6.25 years 6.25 years Expected volatility 84.66% 84.17% Risk-free interest rate 1.90% 0.75% Expected dividend yield 0% 0% Stock-based compensation expense was classified on the statements of operations as follows for the three and nine months ended September 30, 2022 and 2021: Three Months Ended September 30, Nine Months Ended September 30, 2022 2021 2022 2021 Research and development expense $ 242,627 $ 586,001 $ 831,502 $ 1,884,294 General and administrative expense 671,352 1,004,858 2,126,877 2,882,911 Total stock-based compensation expense $ 913,979 $ 1,590,859 $ 2,958,379 $ 4,767,205 |