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Stock-based Compensation | 3 Months Ended
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Mar. 31, 2024
Stock-based Compensation |
Stock-based Compensation | 8. Stock-based Compensation 2013 Equity Incentive Plan ​ The Company’s board of directors adopted, and its stockholders approved, its 2013 Equity Incentive Plan effective in January 2014, and the 2013 Equity Incentive Plan was amended and restated by approval of the board of directors in April 2022 and by approval of the stockholders in May 2022 (as so 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 (the Code), to the Company’s employees and its parent and subsidiary corporations’ employees, and for the grant of nonstatutory stock options, restricted stock awards, restricted stock unit awards (RSUs), 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 and thereafter at the rate of one forty-eighth of the option shares per month as of the first day of each month after the first anniversary. Upon termination of employment by reasons other than death, cause, or disability, any vested options shall 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 may be issued under the 2013 Plan was originally 1,000,000 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 to or repurchased by the Company. Upon the amendment and restatement of the 2013 Plan in May 2022, the existing share reserve was increased by 2,619,622. Beginning on January 1, 2023 and ending on (and including) January 1, 2029, the maximum number of shares of common stock that may be issued under the 2013 Plan will cumulatively be increased by 4% of the number of shares of common stock issued and outstanding on the immediately preceding December 31, or such lesser number of shares as determined by the board of directors or the compensation committee thereof. The maximum number of shares that may be issued pursuant to exercise of incentive stock options under the 2013 Plan is 20,000,000 shares. As of March 31, 2024, the total number of shares reserved for issuance under the 2013 Plan was 14,257,627 shares, of which 2,597,377 shares were available for future grants. ​ 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 three months ended March 31, 2024 is as follows:
​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​
​ | ​ | ​ | ​ | ​ | ​ | ​ | WEIGHTED- | ​ | ​ | ​
​ |  | ​ | ​ | WEIGHTED- | ​ | AVERAGE | ​ | ​ | AGGEGATE
​ |  | ​ | ​ | AVERAGE | ​ | REMAINING | ​ | ​ | INTRINSIC
​ |  | OUTSTANDING | ​ | EXERCISE | ​ | CONTRACTUAL | ​ | ​ | VALUE
​ |  | OPTIONS |  | PRICE |  | TERM (YEARS) |  | ​ | (IN THOUSANDS)
Outstanding as of December 31, 2023 | ​ | 8,273,800 | ​ | $ | 5.29 | ​ | 6.3 | ​ | ​ | ​
Options granted | ​ | 3,094,500 | ​ | ​ | 3.10 | ​ | ​ | ​ | ​ | ​
Options exercised | ​ | (2,800) | ​ | ​ | 1.75 | ​ | ​ | ​ | ​ | ​
Options forfeited | ​ | (597,642) | ​ | ​ | 8.21 | ​ | ​ | ​ | ​ | ​
Outstanding as of March 31, 2024 | ​ | 10,767,858 | ​ | ​ | 4.50 | ​ | 7.5 | ​ | $ | 4,028
Vested or expected to vest as of March 31, 2024 | ​ | 10,615,958 | ​ | ​ | 4.55 | ​ | 7.6 | ​ | ​ | 3,756
Exercisable as of March 31, 2024 | ​ | 5,118,477 | ​ | ​ | 6.52 | ​ | 5.3 | ​ | ​ | 1,758
​ As of March 31, 2024, there was $10,785,346 of total unrecognized compensation expense related to unvested options under the 2013 Plan that will be recognized over a weighted-average period of approximately 3.5 years. Total intrinsic value of the options exercised during the three months ended March 31, 2024 and 2023 was $3,758 and $23,760, respectively and total cash received for options exercised was $4,898 and $33,768, respectively. The total fair value of stock options which vested in the three months ended March 31, 2024 and 2023 was $1,394,896 and $704,311, respectively. ​ The Company has granted stock options to purchase an aggregate of 151,900 shares to certain employees under the 2013 Plan, the vesting of which is subject to performance vesting conditions relating to the achievement of specified regulatory or commercial milestones. The maximum fair value of $133,820 associated with performance-based options granted has been excluded from the unrecognized compensation expense under the 2013 Plan as the completion of the performance milestones was not deemed to be probable as of March 31, 2024. 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. ​ 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 all of 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 March 31, 2024, there was $179,660 of total unrecognized compensation expense associated with outstanding RSU grants that will be recognized over a weighted-average period of approximately 0.8 years. ​ The following is a summary of RSU activity under the 2013 Plan for the three months ended March 31, 2024: ​
​ | ​ | ​ | ​ | ​ | ​ | ​
​ |  | ​ | ​ | Weighted-Average |
​ | ​ | Number of Shares | ​ | Grant Date |
​ | ​ | Underlying RSUs |  | Fair Value |
Unvested at December 31, 2023 | ​ | 117,157 | ​ | $ | 3.81 | ​
Vested | ​ | (58,581) | ​ |  | 3.81 | ​
Unvested at March 31, 2024 | ​ | 58,576 | ​ |  | 3.81 | ​
​ Issuance of Shares to Directors in Lieu of Cash Retainers for Service In March 2023, the Company’s board of directors amended the Company’s Non-Employee Director Compensation Policy to include an election to receive unrestricted shares of common stock in lieu of quarterly board and committee retainer cash payments. The number of shares to be issued to an electing director is determined on the last day of each fiscal quarter by dividing the dollar amount of the compensation to be paid for such quarter that is subject to the election by the closing price of a share of common stock on the last trading day of the fiscal quarter, rounded up to the nearest whole share. Non-employee directors who made such an election will receive 13,127 shares of common stock in lieu of cash compensation earned for the quarter ended March 31, 2024. All shares of common stock issued pursuant to such an election are fully vested upon issuance and are classified as “Other Awards” under the 2013 Plan. Inducement Plan ​ The Company’s board of directors previously adopted the GlycoMimetics, Inc. Inducement Plan (as amended to date, 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-fourth of the shares subject to an option grant under the Inducement Plan 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, subject to the new employee’s continued service with the Company through the applicable vesting dates. 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. The Inducement Plan was amended by the board of directors on multiple occasions to increase the number of shares reserved for issuance to 3,000,000 shares as of March 31, 2024. As of March 31, 2024, there were 269,508 shares available for future grants under the Inducement Plan. ​ A summary of the Company’s stock option activity under the Inducement Plan for the three months ended March 31, 2024 is as follows: ​
​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​
​ | ​ | ​ | ​ | ​ | ​ | ​ | WEIGHTED- | ​ | ​
​ |  | ​ | ​ | WEIGHTED- | ​ | AVERAGE | ​ | ​ | AGGEGATE
​ |  | ​ | ​ | AVERAGE | ​ | REMAINING | ​ | ​ | INTRINSIC
​ |  | OUTSTANDING | ​ | EXERCISE | ​ | CONTRACTUAL | ​ | ​ | VALUE
​ |  | OPTIONS |  | PRICE |  | TERM (YEARS) |  | ​ | (IN THOUSANDS)
Outstanding as of December 31, 2023 | ​ | 2,590,400 | ​ | $ | 1.97 | ​ | 8.0 | ​ | ​ | ​
Options granted | ​ | 130,000 | ​ | ​ | 3.20 | ​ | ​ | ​ | ​ | ​
Outstanding as of March 31, 2024 | ​ | 2,720,400 | ​ | ​ | 2.03 | ​ | 7.8 | ​ | $ | 2,784
Vested or expected to vest as of March 31, 2024 | ​ | 2,136,200 | ​ | ​ | 2.04 | ​ | 7.9 | ​ | ​ | 2,184
Exercisable as of March 31, 2024 | ​ | 1,060,375 | ​ | ​ | 1.98 | ​ | 7.5 | ​ | ​ | 1,135
​ As of March 31, 2024, there was $1,621,972 of total unrecognized compensation expense related to unvested options under the Inducement Plan that will be recognized over a weighted-average period of approximately 2.5 years. The total fair value of stock options which vested in the three months ended March 31, 2024 and 2023 was $305,219 and $181,032, respectively. There were no options exercised under the Inducement Plan during the three months ended March 31, 2024 and 2023. ​ The Company has granted stock options to purchase an aggregate of 584,200 shares to certain newly hired employees under the Inducement Plan which options are subject to performance-based vesting conditions. The maximum fair value of $825,353 associated with the performance-based options has been excluded from the unrecognized compensation expense under the Inducement Plan as the completion of the performance milestones was not deemed to be probable as of March 31, 2024. 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 three months ended March 31, 2024 and 2023 was $2.44 per share and $2.04 per share, respectively, applying the Black-Scholes-Merton option pricing model utilizing the following weighted-average assumptions: ​
​ | ​ | ​ | ​ | ​
​ |  | 2024 | ​ | 2023
Expected term |  | 6.25 years | ​ | 6.25 years
Expected volatility |  | 90.37% | ​ | 79.56%
Risk-free interest rate |  | 3.89% | ​ | 3.52%
Expected dividend yield |  | 0% | ​ | 0%
​ Stock-based compensation expense was classified on the statements of operations as follows for the three months ended March 31, 2024 and 2023: ​
​ | ​ | ​ | ​ | ​ | ​ | ​
​ | ​ | Three Months Ended March 31,
​ |  | 2024 | ​ | 2023
Research and development expense | ​ | $ | 348,242 | ​ | $ | 237,931
General and administrative expense | ​ |  | 843,838 | ​ |  | 632,249
Total stock-based compensation expense | ​ | $ | 1,192,080 | ​ | $ | 870,180
​

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