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Stockholders' Equity | 6 Months Ended
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Jun. 30, 2023
Stockholders' Equity |
Stockholders' Equity | 7. Stockholders’ Equity ​ At-The-Market Sales Facility ​ 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 terminated an at-the-market sales agreement previously entered into with Cowen and Company, LLC (Cowen) in 2020 and 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 $100.0 million worth of shares of common stock. During the year ended December 31, 2022, the Company issued and sold 1,953,854 shares of common stock under the 2022 Sales Agreement at a weighted average price per share of $2.22, for aggregate net proceeds of $4.2 million, after deducting commissions and offering expenses. ​ During the quarter ended March 31, 2023, the Company issued and sold 9,822,930 shares of common stock under the 2022 Sales Agreement at a weighted average price per share of $3.01, for aggregate net proceeds of $28.7 million, after deducting commissions and offering expenses. There were no sales during the quarter ended June 30, 2023. As of June 30, 2023, approximately $66.0 million remained available to be sold under the terms of the 2022 Sales Agreement. ​ 2013 Equity Incentive Plan ​ The Company’s board of directors adopted, and its stockholders approved, its 2013 Equity Incentive Plan (the 2013 Plan) effective on January 9, 2014. In April 2022, the Company’s board of directors approved an amendment and restatement of the 2013 Plan, which was approved by the Company’s stockholders at the Company’s annual meeting of stockholders held in May 2022 (as so amended, the Amended 2013 Plan). ​ The Amended 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 Amended 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 1,000,000 shares, plus any shares subject to stock options or similar awards granted under the Company’s prior 2003 Equity Incentive Plan that expired or terminated without having been exercised in full or were forfeited or repurchased by the Company. The number of shares of common stock reserved for issuance under the 2013 Plan automatically increased on January 1 of each year, through January 1, 2022, by 3% of the total number of shares of common stock outstanding on December 31 of the preceding calendar year. ​ Following the approval of the Amended 2013 Plan by the Company’s stockholders, the share reserve under the Amended 2013 Plan was increased by 2,619,622 shares, and 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 Amended 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 Amended 2013 Plan is 20,000,000 shares. As of June 30, 2023, the total number of shares reserved for issuance under the Amended 2013 Plan was 11,681,878 shares, of which 2,128,873 shares were available for future grants. ​ Shares issued under the Amended 2013 Plan may be authorized but unissued or reacquired shares of common stock. Shares subject to stock awards granted under the Amended 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 Amended 2013 Plan. Additionally, shares issued pursuant to stock awards under the Amended 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 Amended 2013 Plan. ​ A summary of the Company’s stock option activity under the Amended 2013 Plan for the six months ended June 30, 2023 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, 2022 | ​ | 6,774,792 | ​ | $ | 6.37 | ​ | 6.1 | ​ | ​ | ​
Options granted | ​ | 2,451,050 | ​ | ​ | 2.55 | ​ | ​ | ​ | ​ | ​
Options exercised | ​ | (44,550) | ​ | ​ | 1.21 | ​ | ​ | ​ | ​ | ​
Options forfeited | ​ | (409,085) | ​ | ​ | 2.97 | ​ | ​ | ​ | ​ | ​
Outstanding as of June 30, 2023 | ​ | 8,772,207 | ​ | ​ | 5.49 | ​ | 6.3 | ​ | $ | 1,037
Vested or expected to vest as of June 30, 2023 | ​ | 8,630,307 | ​ | ​ | 5.56 | ​ | 6.3 | ​ | ​ | 948
Exercisable as of June 30, 2023 | ​ | 5,155,455 | ​ | ​ | 7.72 | ​ | 4.4 | ​ | ​ | 430
​ As of June 30, 2023, there was $5,623,046 of total unrecognized compensation expense related to unvested options under the Amended 2013 Plan that will be recognized over a weighted-average period of approximately 2.9 years. Total intrinsic value of the options exercised during the six months ended June 30, 2023 was $54,083 and total cash received for options exercised was $53,882. There were no options exercised under the Amended 2013 Plan during the six months ended June 30, 2022. The total fair value of stock options which vested in the six months ended June 30, 2023 and 2022 was $1,090,699 and $2,060,622, respectively. ​ In January 2022, the Company granted stock options to purchase an aggregate of 141,900 shares to certain employees under the 2013 Plan which were subject to performance vesting conditions. The shares will vest upon achievement of milestones as follows: (i) one-half of the shares will vest upon FDA approval of uproleselan for patients with relapsed/refractory acute myeloid leukemia and (ii) one-half of the shares will vest upon the first commercial sale of uproleselan in the United States or abroad. The maximum fair value of $113,520 associated with the performance-based options granted in January 2022 is excluded from the unrecognized compensation expense under the 2013 Plan as the completion of the performance milestones was not probable as of June 30, 2023. 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 June 30, 2023, there was $347,710 of total unrecognized compensation expense associated with outstanding RSU grants that will be recognized over a weighted-average period of approximately 1.6 years. ​ The following is a summary of RSU activity under the Amended 2013 Plan for the six months ended June 30, 2023: ​
​ | ​ | ​ | ​ | ​ | ​ | ​
​ |  | ​ | ​ | Weighted-Average |
​ | ​ | Number of Shares | ​ | Grant Date |
​ | ​ | Underlying RSUs |  | Fair Value |
Unvested at December 31, 2022 | ​ | 204,785 | ​ | $ | 3.81 | ​
Forfeited | ​ | (19,573) | ​ |  | 3.81 | ​
Vested | ​ | (68,055) | ​ |  | 3.81 | ​
Unvested at June 30, 2023 | ​ | 117,157 | ​ |  | 3.81 | ​
​ Other Awards ​ In March 2023, the Company’s board of directors amended the Company’s Non-Employee Director Compensation Policy to include an election to receive shares in lieu of cash compensation, effective with the third quarter 2023 quarterly payment (the Amended Policy). In the Amended Policy, non-employee directors may make an election to receive all or a portion of their cash compensation payable in the form of unrestricted shares of the Company’s common stock. The number of shares of Common Stock to be issued in lieu of cash compensation shall be determined on a quarterly basis, 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. All shares of Common Stock issued pursuant to such an election will be fully vested upon issuance and will be issued as “Other Awards” under the Amended 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 through January 2022 to increase the number of shares reserved for issuance to 3,000,000 shares. As of June 30, 2023, there were 409,508 shares available for future grants under the Inducement Plan. ​ A summary of the Company’s stock option activity under the Inducement Plan for the six months ended June 30, 2023 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, 2022 | ​ | 2,333,525 | ​ | $ | 1.82 | ​ | 8.7 | ​ | ​ | ​
Options granted | ​ | 250,000 | ​ | ​ | 3.25 | ​ | ​ | ​ | ​ | ​
Options forfeited | ​ | (3,125) | ​ | ​ | 3.58 | ​ | ​ | ​ | ​ | ​
Outstanding as of June 30, 2023 | ​ | 2,580,400 | ​ | ​ | 1.95 | ​ | 8.4 | ​ | $ | 405
Vested or expected to vest as of June 30, 2023 | ​ | 1,996,200 | ​ | ​ | 1.95 | ​ | 8.5 | ​ | ​ | 382
Exercisable as of June 30, 2023 | ​ | 675,671 | ​ | ​ | 1.97 | ​ | 8.1 | ​ | ​ | 59
​ As of June 30, 2023, there was $1,759,353 of total unrecognized compensation expense related to unvested options under the Inducement Plan that will be recognized over a weighted-average period of approximately 2.7 years. There were no options exercised under the Inducement Plan during the six months ended June 30, 2023 or 2022. The total fair value of stock options which vested in the six months ended June 30, 2023 and 2022 was $312,314 and $20,002, respectively. ​ During 2021 and the six months ended June 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 June 30, 2023. 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 six months ended June 30, 2023 and 2022 was $2.00 per share and $0.78 per share, respectively, applying the Black-Scholes-Merton option pricing model utilizing the following weighted-average assumptions: ​
​ | ​ | ​ | ​ | ​
​ | ​ | Six Months Ended June 30,
​ |  | 2023 | ​ | 2022
Expected term |  | 6.25 years | ​ | 6.25 years
Expected volatility |  | 81.26% | ​ | 84.54%
Risk-free interest rate |  | 3.54% | ​ | 1.74%
Expected dividend yield |  | 0% | ​ | 0%
​ Stock-based compensation expense was classified on the statements of operations as follows for the three and six months ended June 30, 2023 and 2022: ​
​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​
​ | ​ | Three Months Ended June 30, | ​ | Six Months Ended June 30, | ​
​ |  | 2023 | ​ | 2022 |  | 2023 | ​ | 2022 |
Research and development expense | ​ | $ | 229,422 | ​ | $ | 270,050 | ​ | $ | 467,353 | ​ | $ | 588,875 | ​
General and administrative expense | ​ |  | 628,666 | ​ |  | 693,708 | ​ |  | 1,260,915 | ​ |  | 1,455,525 | ​
Total stock-based compensation expense | ​ | $ | 858,088 | ​ | $ | 963,758 | ​ | $ | 1,728,268 | ​ | $ | 2,044,400 | ​
​

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- Definition This note contains 1) the entire disclosure for shareholders' equity comprised of portions attributable to the parent entity and noncontrolling interest, including other comprehensive income. Includes, but is not limited to, balances of common stock, preferred stock, additional paid-in capital, other capital and retained earnings, accumulated balance for each classification of other comprehensive income and amount of comprehensive income and 2) the entire disclosure for compensation-related costs for equity-based compensation, which may include disclosure of policies, compensation plan details, allocation of equity compensation, incentive distributions, equity-based arrangements to obtain goods and services, deferred compensation arrangements, employee stock ownership plan details and employee stock purchase plan details. + References No definition available. + Details
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