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Stockholders' Equity | 12 Months Ended
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Dec. 31, 2022
Stockholders' Equity |
Stockholders' Equity | 8. Stockholders’ Equity Common Stock At-The-Market Equity Offerings On September 28, 2017, the Company entered into an at-the-market sales agreement (the 2017 Sales Agreement) with Cowen and Company, LLC (Cowen) to sell up to $100.0 million of the Company’s common stock registered under a shelf registration statement filed with the U.S. Securities and Exchange Commission in September 2017. During the year ended December 31, 2020, the Company issued and sold 4,136,742 shares of common stock under the 2017 Sales Agreement at a weighted average price per share of $3.52, for aggregate net proceeds of $14.1 million, after deducting commissions and offering expenses. The shelf registration statement, under which the shares that could be sold under the 2017 Sales Agreement were registered, expired on October 6, 2020. ​ On October 7, 2020, the Company filed a prospectus supplement to a shelf registration statement that it filed in May 2019 and entered into a new at-the-market sales agreement (the 2020 Sales Agreement) with Cowen. Under the 2020 Sales Agreement, the Company may sell up to $100.0 million of the Company’s common stock registered under the shelf registration statement that was filed in May 2019. The 2020 Sales Agreement replaced the 2017 Sales Agreement between the Company and Cowen, and the $100.0 million that may be sold under the 2020 Sales Agreement excludes any amounts that were sold under the 2017 Sales Agreement. During the year ended December 31, 2020, the Company issued and sold 1,024,760 shares of common stock under the 2020 Sales Agreement at a weighted average price per share of $3.74, for aggregate net proceeds of $3.7 million, after deducting commissions and offering expenses. During the year ended December 31, 2021, the Company issued and sold an additional 3,092,603 shares of common stock under the 2020 Sales Agreement at a weighted average price per share of $3.57, for aggregate net proceeds of $10.7 million, after deducting commissions and offering expenses. There were no shares sold under the 2020 Sales Agreement in the year ended December 31, 2022. ​ In March 2022, the Company filed a shelf registration statement with the SEC, which was declared effective on April 22, 2022. Upon the effectiveness of the new registration statement, the prior shelf registration statement, under which the shares that could be sold under the 2020 Sales Agreement were registered, was deemed to be terminated. 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 $100.0 million in shares of its 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. As of December 31, 2022, approximately $95.7 million remained available to be sold under the terms of the 2022 Sales Agreement. ​ Subsequent to December 31, 2022 and through the date these financial statements were issued, 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. As of the date these financial statements were issued, approximately $66.0 million remained available to be sold under the terms of the 2022 Sales Agreement. ​ 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-eighth of the option shares per month as of the first day of each month after the first anniversary. Compensation expense is recognized on a straight-line basis. Upon termination of employment by reasons other than death, cause, or disability, any vested options shall terminate 60 days after the termination date. Stock options terminate 10 years from the date of grant. The 2003 Plan expired on May 21, 2013. A summary of the Company’s stock option activity under the 2003 Plan for the year ended December 31, 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 | ​ | (93,465) | ​ |  | 2.00 | ​ | ​ | ​ | ​ | ​
Outstanding, Vested and Exercisable as of December 31, 2022 | ​ | — | ​ |  | — |  | — | ​ | $ | —
​ The 2003 Plan had no options outstanding as of December 31, 2022. There were no options granted under the 2003 Plan in 2022, 2021 and 2020. During 2021 and 2020, the Company issued 3,785 and 285,087 shares of common stock, respectively, in conjunction with exercises of stock options granted under the 2003 Plan. The Company received cash proceeds from the exercise of these stock options of $4,239 and $319,297 during 2021 and 2020, respectively. Total intrinsic value of the options exercised during the years ended December 31, 2021 and 2020 was $8,668 and $921,168, respectively. There were no options exercised under the 2003 Plan in 2022. ​ 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. 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, 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 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. In May 2022, the 2013 Plan was amended to increase the existing share reserve by 2,619,622 shares, and provide that, 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. As of December 31, 2022, the total number of shares reserved for issuance under the 2013 Plan was 9,506,767 shares, of which 1,976,154 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. Stock Options A summary of the Company’s stock option activity under the 2013 Plan for the year ended December 31, 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 | ​ | (901,465) | ​ | ​ | 6.56 | ​ | ​ | ​ | ​ | ​
Outstanding as of December 31, 2022 | ​ | 6,774,792 | ​ | ​ | 6.37 | ​ | 6.1 | ​ | $ | 3,506
Vested or expected to vest as of December 31, 2022 | ​ | 6,585,192 | ​ | ​ | 6.52 | ​ | 6.0 | ​ | ​ | 3,142
Exercisable as of December 31, 2022 | ​ | 4,449,925 | ​ | ​ | 8.72 | ​ | 4.7 | ​ | ​ | 37
​ As of December 31, 2022, there was $2,589,179 of total unrecognized compensation expense related to unvested options that will be recognized over a weighted-average period of approximately 2.0 years. The total fair value of options that vested in the years ended December 31, 2022, 2021 and 2020 was $3,306,412, $5,936,641 and $7,347,548, respectively. There were no options exercised under the 2013 Plan during the years ended December 31, 2022, 2021 or 2020. ​ 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-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 $151,680 associated with the performance-based options granted in January 2022 is excluded from the unrecognized compensation expense under the 2013 Plan as the achievement of the performance milestones was not deemed to be probable as of December 31, 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. ​ Restricted Stock Units (RSUs) A restricted stock unit (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. Compensation expense is recognized on a straight-line basis. As of December 31, 2022, there was $534,083 of total unrecognized compensation expense associated with these RSU grants that will be recognized over a weighted-average period of approximately 2.1 years. The following is a summary of RSU activity for the 2013 Plan for the year ended December 31, 2022: ​
​ | ​ | ​ | ​ | ​ | ​ | ​
​ |  | ​ | ​ | Weighted-Average |
​ | ​ | Number of Shares | ​ | Grant Date |
​ | ​ | Underlying RSUs |  | Fair Value |
Unvested at December 31, 2021 | ​ | 345,600 | ​ | $ | 3.70 | ​
Forfeited | ​ | (30,765) | ​ |  | 3.81 | ​
Vested | ​ | (110,050) | ​ |  | 3.45 | ​
Unvested at December 31, 2022 | ​ | 204,785 | ​ |  | 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, restricted stock unit 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. There were 500,000 shares of common stock reserved under the Inducement Plan at its adoption date. In August 2021, the Company’s board of directors adopted an amendment to the Inducement Plan to increase the number of shares reserved to 2,000,000 shares, and in January 2022 the Company’s board of directors adopted an amendment to the Inducement Plan to further increase the number of shares reserved to 3,000,000 shares. As of December 31, 2022, there were 656,383 shares available for future grants under the Inducement Plan. ​ A summary of the Company’s stock option activity under the Inducement Plan for the year ended December 31, 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 | ​ | (15,075) | ​ | ​ | 3.67 | ​ | ​ | ​ | ​ | ​
Outstanding as of December 31, 2022 | ​ | 2,333,525 | ​ | ​ | 1.82 | ​ | 8.7 | ​ | $ | 2,867
Vested or expected to vest as of December 31, 2022 | ​ | 1,749,325 | ​ | ​ | 1.76 | ​ | 8.8 | ​ | ​ | 2,249
Exercisable as of December 31, 2022 | ​ | 425,104 | ​ | ​ | 2.13 | ​ | 8.5 | ​ | ​ | 402
​ As of December 31, 2022, there was $1,473,466 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. The total fair value of options that vested in the years ended December 31, 2022 and 2021 was $604,440 and $73,334, respectively. During the year ended December 31, 2021, the Company received cash of $20,790 and issued 10,092 shares of common stock in conjunction with exercises of stock options granted under the Inducement Plan. The intrinsic value of the options exercised for the year ended December 31, 2021 was $1,944. There were no options exercised under the Inducement Plan during the years ended December 31, 2022 or 2020. During the years ended December 31, 2022 and 2021, 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 achievement of the performance milestones was not deemed to be probable as of December 31, 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 years ended December 31, 2022, 2021 and 2020 was $0.76, $1.85 and $3.17 per share, respectively, applying the Black-Scholes-Merton option pricing model utilizing the following weighted-average assumptions: ​
​ | ​ | ​ | ​ | ​ | ​ | ​
​ |  | 2022 | ​ | 2021 | ​ | 2020
Expected term |  | 6.25 years | ​ | 6.25 years | ​ | 6.25 years
Expected volatility |  | 84.66% | ​ | 84.19% | ​ | 84.40%
Risk-free interest rate |  | 1.90% | ​ | 0.78% | ​ | 1.41%
Expected dividend yield |  | 0% | ​ | 0% | ​ | 0%
​ Total stock-based compensation expense associated with stock options and RSUs was classified as follows on the statement of operations for the years ended December 31: ​
​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​ | ​
​ | ​ | ​ | ​ | ​ | ​ | ​ | ​
​ |  |  | 2022 |  | 2021 |  | 2020
Research and development expense | ​ | ​ | $ | 1,059,591 | ​ | $ | 2,214,848 | ​ | $ | 2,946,952
General and administrative expense | ​ | ​ |  | 2,797,989 | ​ |  | 3,872,438 | ​ |  | 3,954,806
Total stock-based compensation expense | ​ | ​ | $ | 3,857,580 | ​ | $ | 6,087,286 | ​ | $ | 6,901,758
​

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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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