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Stockholders' Equity

12 Months Ended

Dec. 31, 2021

Stockholders' Equity

Stockholders' Equity

9. 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. There were no shares sold under the 2017 Sales Agreement during the year ended December 31, 2019. 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. As of December 31, 2021, approximately $85.1 million remained available to be sold under the terms of the 2020 Sales Agreement. Subsequent to December 31, 2021 and through the date these financial statements were issued, there have been no additional sales under the 2020 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. 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, 2021 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, 2020		97,250		$	1.96		1.3
Options exercised		(3,785)			1.12
Options forfeited		—			—
Outstanding, Vested and Exercisable as of December 31, 2021		93,465			2.00		0.3		$	—

During 2021, 2020 and 2019 the Company issued 3,785, 285,087 and 284,743 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, $319,297 and $318,912 during 2021, 2020 and 2019, respectively. Total intrinsic value of the options exercised during the years ended December 31, 2021, 2020 and 2019 was $8,668, $921,168 and $924,688, respectively.

As of December 31, 2021, the options under the 2003 Plan were fully expensed and all options outstanding under the 2003 Plan were fully vested. There were no options granted under the 2003 Plan in 2021, 2020 and 2019.

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. The number of shares of common stock reserved for issuance under the 2013 Plan will automatically increase on January 1 of each year, beginning on January 1, 2015 and ending on January 1, 2023, by 3% of the total number of shares of common stock outstanding on December 31 of the preceding calendar year, or a lesser number of shares as may be determined by the Company’s board of directors. 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 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, 2021 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, 2020		5,753,211		$	8.93		6.6
Options granted		898,100			3.70
Options exercised		—			—
Options forfeited		(995,854)			7.89
Outstanding as of December 31, 2021		5,655,457			8.30		6.0		$	—
Vested or expected to vest as of December 31, 2021		5,655,457			8.30		6.0			—
Exercisable as of December 31, 2021		4,118,394			9.43		5.1			—

As of December 31, 2021, there was $4,936,519 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, 2021, 2020 and 2019 was $5,936,641, $7,347,548 and $6,159,610, respectively. There were no options exercised under the 2013 Plan during the years ended December 31, 2021 or 2020. During the year ended December 31, 2019, the Company received cash of $94,001 and issued 16,606 shares of common stock in conjunction with exercises of stock options granted under the 2013 Plan. The intrinsic value of the options exercised for the year ended December 31, 2019 was $97,429.

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. In September 2019, the Company granted an aggregate of 332,106 RSUs with service conditions to the Company’s non-executive employees. The RSUs granted in September 2019 vested over a two-year period, with one-third vesting on the first anniversary of the date of grant and the remaining two-thirds vesting on the second anniversary of the date of grant, provided that the employee remained employed with the Company at the applicable vesting date. Compensation expense is recognized on a straight-line basis. As of December 31, 2021, there was $943,458 of total unrecognized compensation expense associated with these RSU grants that will be recognized over a weighted-average period of approximately 3.0 years.

The following is a summary of RSU activity for the 2013 Plan for the year ended December 31, 2021:


				Weighted-Average
		Number of Shares		Grant Date
		Underlying RSUs		Fair Value
Unvested at December 31, 2020		192,533		$	4.53
Granted		444,613			3.72
Forfeited		(101,754)			3.84
Vested		(189,792)			4.53
Unvested at December 31, 2021		345,600			3.70

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.

.

A summary of the Company’s stock option activity under the Inducement Plan for the year ended December 31, 2021 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, 2020		100,600		$	3.09		9.5
Options granted		1,747,600			2.02
Options exercised		(10,092)			2.06
Options forfeited		(24,508)			2.06
Outstanding as of December 31, 2021		1,813,600			2.08		9.6		$	—
Vested or expected to vest as of December 31, 2021		1,264,400			2.10		9.6			—
Exercisable as of December 31, 2021		22,879			3.58		8.6			—

As of December 31, 2021, there was $1,672,270 of total unrecognized compensation expense related to unvested options under the Inducement Plan that will be recognized over a weighted-average period of approximately 3.6 years. In August 2021, the Company granted stock options to purchase an aggregate of 1,647,600 shares to its new Chief Executive Officer under the Inducement Plan. This consisted of (a) an option to purchase 1,098,400 shares, subject to vesting as to 25% of the underlying shares on August 3, 2022 and as to the remaining underlying shares in equal monthly installments over 36 months thereafter, subject to the officer’s continued service through each such vesting date, and (b) an option to purchase 549,200 shares that is subject to performance vesting conditions and will vest upon achievement of milestones as follows: (i) one-half of the shares will vest upon FDA approval of uproleselan in 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 $798,053 associated with the performance-based option is excluded from the unrecognized compensation expense under the Inducement Plan as the completion of the performance milestones are not probable as of December 31, 2021. The Company will reevaluate at the end of each reporting period the probability that the performance conditions will be achieved and record any compensation cost at that time.

The total fair value of options that vested in the year ended December 31, 2021 was $73,334. 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 vested or exercised under the Inducement Plan during the year ended December 31, 2020.

The weighted-average fair value of the options granted under all equity incentive plans during the years ended December 31, 2021, 2020 and 2019 was $1.85, $3.17 and $7.17 per share, respectively, applying the Black-Scholes-Merton option pricing model utilizing the following weighted-average assumptions:


		2021		2020		2019
Expected term		6.25 years		6.25 years		6.25 years
Expected volatility		84.19%		84.40%		71.15%
Risk-free interest rate		0.78%		1.41%		2.54%
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:



			2021			2020			2019
Research and development expense			$	2,214,848		$	2,946,952		$	2,402,242
General and administrative expense				3,872,438			3,954,806			3,812,848
Total stock-based compensation expense			$	6,087,286		$	6,901,758		$	6,215,090