Stockholders’ Equity | Stockholders’ Equity Common Stock Shares of common stock reserved for future issuance were as follows: December 31, 2022 2021 Shares to be issued upon exercise of outstanding stock options 7,058,140 5,611,743 Shares to be issued upon release of RSUs 178,618 265,566 Shares to be issued upon conversion of common stock warrants 3,656,497 3,666,435 Shares to be issued upon conversion of prefunded warrants 5,182,197 5,182,197 Shares available for future stock grants 314,523 284,906 Shares to be issued under employee stock purchase plan 45,211 45,211 Shares of common stock reserved for future issuance 16,435,186 15,056,058 In January 2023, in connection with the exercise of certain prefunded warrants, we issued 1,708,773 shares of common stock. Securities Offerings In September 2022, we sold an aggregate of 15,509,282 shares of our common stock in an underwritten public offering, including the subsequent partial exercise of the underwriters’ over-allotment option in October 2022, pursuant to our effective shelf registration statement on Form S-3 (File No. 333-256107). We received resulting net proceeds of $106.7 million after deducting underwriting discounts, commissions and offering costs. Offering costs of $448,000 were netted against the proceeds within additional-paid-in-capital on our accompanying Consolidated Balance Sheets . In September 2021, we entered into a securities purchase agreement (the “2021 Securities Purchase Agreement”) for a private placement with a select group of institutional investors, pursuant to which we sold 6,489,357 shares of our common stock (the “Shares”) and prefunded warrants to purchase 3,191,487 Shares (the “Prefunded Warrants”). The purchase price for each Share and for each Prefunded Warrant was $9.40 per share, for an aggregate purchase price of approximately $91.0 million. The Prefunded Warrants became fully exercisable upon the closing date and have an exercise price of $0.001 per share. We incurred $266,000 in financing costs associated with the 2021 Securities Purchase Agreement, which was netted against the proceeds within additional-paid-in-capital on our accompanying Consolidated Balance Sheets . In September 2021, we entered into an exchange agreement (the “Exchange Agreement”) with Frazier Life Sciences VIII, L.P. (the “Exchanging Stockholder”), which Exchanging Stockholder is affiliated with a member of our board of directors, pursuant to which we exchanged an aggregate of 1,200,000 shares of common stock held by the Exchanging Stockholder for Prefunded Warrants (the “Exchange Warrants”) to purchase an aggregate of 1,200,000 shares of common stock. Upon the closing of the exchange, we reclassified 1,200,000 shares of common stock into treasury stock on our accompanying Consolidated Balance Sheets . In July 2020, we entered into a securities purchase agreement (the “2020 Securities Purchase Agreement”) for a private placement with a select group of institutional investors, pursuant to which we sold 5,139,610 units (the “Common Units”) and 790,710 units (the “Prefunded Warrant Units”), for an aggregate purchase price of $60.0 million. Each Common Unit consists of one share of our common stock plus a warrant to purchase 0.3 shares of common stock (the “Common Stock Warrants”), and each Prefunded Warrant Unit consists of one prefunded warrant to purchase one share of common stock plus 0.3 Common Stock Warrants. The Prefunded Warrant Units and the Common Units are collectively referred to as the “Units” and each Unit has a purchase price of $10.1175. Pursuant to the terms of the 2020 Securities Purchase Agreement, we issued warrants to purchase 1,779,096 shares of common stock with an exercise price of $12.74 and a term of 3.5 years. Additionally, we issued 790,710 prefunded warrants, which became fully exercisable upon the closing date and have an exercise price of $0.001 per share. We incurred $3.7 million in financing costs associated with the 2020 Securities Purchase Agreement, which was netted against the proceeds within additional-paid-in-capital on our accompanying Consolidated Balance Sheets . The issuance of the securities sold under the 2021 and 2020 Securities Purchase Agreements have not been registered under the Securities Act of 1933, as amended, or state securities laws and may not be offered or sold in the United States absent registration with the SEC or an applicable exemption from such registration requirements. We filed registration statements for the 2021 and 2020 Securities Purchase Agreements with the SEC, which were declared effective by the SEC in November 2021 and August 2020, respectively, which cover the resale of the shares of common stock issuable in connection with the private placements and upon exercise of the warrants. In May 2021, the registration statement for the 2019 Securities Purchase Agreement was deactivated following the expiration of our obligation to maintain its effectiveness under the related registration rights agreement. Financing Agreements In September 2022, we and Cowen and Company, LLC (“Cowen”) mutually terminated the sales agreement (the “Sales Agreement”) dated July 2, 2021. The Sales Agreement provided that we may sell shares of our common stock from time to time through an “at the market” equity offering for up to $75.0 million in gross cash proceeds, under which Cowen acted as the sales agent. No sales of our common stock were sold under the Sales Agreement. In connection with the termination of the Sales Agreement, we wrote off $488,000 of deferred financing costs to expense, which were previously included within prepaid expenses and other current assets on our accompanying Consolidated Balance Sheets . Common Stock Warrants We have issued warrants in connection with our securities offerings, SVB loans, and to certain non-employee professional advisers. Excluding the prefunded warrants we issued in connection with our securities offerings discussed above, the table below summarizes our common stock warrant activity: Warrants Weighted- Weighted- Outstanding at December 31, 2021 3,666,435 $ 12.64 2.12 Exercised (9,938) 5.02 Outstanding and Exercisable at December 31, 2022 3,656,497 $ 12.66 1.12 Equity Incentive Plans Our board of directors approved an “inducement” grant, pursuant to Rule 5635(c)(4) of the Nasdaq Listing Rules, to our Chief Medical Officer for options to purchase 160,000 shares of our common stock at a per-share exercise price of $8.38, which was set based on our stock price as of the grant date in August 2022. The option grant is exempt from registration under the Securities Act of 1933, as amended, pursuant to Section 4(a)(2) thereof as a transaction by an issuer not involving a public offering. Options granted vest within four years, subject to continued employment, and expire ten years after the date of grant. In June 2018, our stockholders approved the 2018 Equity Incentive Plan (“2018 Plan”). Upon adoption, we ceased granting stock awards under the Nivalis Therapeutics, Inc. 2015 Equity Incentive Plan (the “2015 EIP”) and the Amended and Restated 2015 Stock Plan (the “2015 Plan”), collectively, the “Legacy Plans”. All shares of common stock subject to awards under the Legacy Plans that expire or terminate without having been exercised in full, or are forfeited to or repurchased by the company, will be added to the 2018 Plan, up to a maximum of 1,972,784 shares. In June 2020, in conjunction with our annual meeting of stockholders, our stockholders approved an additional increase of 743,515 shares authorized under our 2018 Plan. Under our 2018 Plan we may issue stock options, stock appreciation rights, restricted stock, RSUs or performance shares. As of December 31, 2022, we have only issued stock options and RSUs. Our 2018 Plan provides for an annual increase in the number of shares reserved for insurance equal to the lesser of (1) 5% of the number of shares of common stock outstanding as of the last day of the preceding calendar year or (2) 1,500,000. However, our board of directors may act prior to January 1 of a given year to provide that there will be no January 1 increase for such year or that the increase for such year will be a lesser number of shares. On January 1, 2023, a total of 1,500,000 additional shares were automatically added to the shares authorized under the 2018 Plan. In July 2017, in connection with the merger, we assumed Nivalis’ Employee Stock Purchase Plan (the “ESPP”) and the 2015 EIP. Upon assumption of the ESPP, there were 45,211 shares available for issuance under the ESPP. As of December 31, 2022, we have not activated the ESPP. Stock options granted under our equity plans generally vest within four years and vested options are exercisable from the grant date until ten years after the date of grant. Vesting of certain employee options may be accelerated in the event of a change in control of the Company. We grant stock options to employees with exercise prices equal to the fair value of our common stock on the date of grant. The term of incentive stock options may not exceed ten years from the date of grant. As of December 31, 2022, a total of 8,116,862 shares of common stock were authorized for issuance under our 2018 Plan, 2015 Plan and 2015 EIP. A summary of stock option activity under our plans is presented below: Options Weighted- Weighted- Aggregate Outstanding at December 31, 2021 5,611,743 $ 7.41 Granted 1,904,650 $ 10.95 Exercised (226,480) $ 3.20 Forfeited/Expired (231,773) $ 11.20 Outstanding at December 31, 2022 7,058,140 $ 8.37 7.12 $ 9,833 Vested and expected to vest after December 31, 2022 6,918,140 $ 8.38 7.11 $ 9,833 Exercisable at December 31, 2022 4,035,424 $ 6.75 5.97 $ 8,865 The aggregate intrinsic value of stock options exercised during the years ended December 31, 2022, 2021 and 2020 was $1.1 million, $546,000 and $104,000, respectively. The fair value of stock options vested during the years ended December 31, 2022, 2021 and 2020 was $8.6 million, $3.4 million and $4.2 million, respectively. A summary of our RSU activity under our plans is presented below: Number of Shares Weighted- Weighted- Aggregate Non-vested at December 31, 2021 265,566 $ 12.00 Granted 3,750 $ 9.00 Released (61,227) $ 12.00 Forfeited (29,471) $ 11.62 Non-vested at December 31, 2022 178,618 $ 12.00 8.90 $ 1,313 The aggregate intrinsic value of RSUs released during the years ended December 31, 2022, 2021 and 2020 was $527,000, $0 and $1.6 million, respectively. The fair value of RSUs vested during the years ended December 31, 2022, 2021 and 2020 was $735,000, $0 and $461,000, respectively. We utilize newly issued shares to satisfy option exercises and RSU releases. As of December 31, 2022, there was $19.6 million of unrecognized stock-based compensation expense related to approximately 3.2 million nonvested stock options and RSU awards that are expected to be recognized over a weighted-average period of 2.5 years. Stock-Based Compensation Expense We use the Black-Scholes option pricing model to estimate the fair value of stock options at the grant date. The fair value of RSUs is equal to the closing stock price on the date of grant. The Black-Scholes option pricing model requires us to make certain estimates and assumptions, including assumptions related to the expected price volatility of our stock, the period during which the options will be outstanding, the rate of return on risk-free investments, and the expected dividend yield of our stock. The fair values of stock options granted to employees were calculated using the following assumptions: Years Ended December 31, 2022 2021 2020 Weighted-average estimated fair value at grant $7.56 $8.44 $3.03 Risk-free interest rate (1) 1.39% - 4.04% 0.25% - 1.3% 0.38% - 1.68% Expected term of options (in years) (2) 5.27 - 6.08 3.49 – 6.08 5.27 – 6.90 Expected stock price volatility (3) 80% - 83% 79% - 83% 73% - 82% Expected dividend yield (4) —% —% —% (1) The risk-free interest rate assumption was based on zero-coupon U.S. Treasury instruments that had terms consistent with the expected term of our stock option grants. (2) We used the “simplified method” for options to determine the expected term of stock options granted, since we do not have sufficient historical exercise data to provide a reasonable basis upon which to estimate expected term due to the limited time our shares have been publicly traded. Under this approach, the weighted-average expected life is presumed to be the average of the vesting term and the contractual term of the option. (3) Volatility is a measure of the amount by which a financial variable, such as share price, has fluctuated or is expected to fluctuate during a period. We analyzed the historical stock price volatility of companies at a similar stage of development to estimate expected volatility of our stock price. (4) We have never declared or paid any cash dividends and do not presently plan to pay cash dividends in the foreseeable future. Stock-based compensation expense is classified in the Consolidated Statements of Operations and Comprehensive Income (Loss) as follows (in thousands): Years Ended December 31, 2022 2021 2020 Research and development $ 5,713 $ 3,347 $ 2,179 General and administrative 3,935 2,893 1,961 Total stock-based compensation expense $ 9,648 $ 6,240 $ 4,140 |