X0303 4 2008-09-04 0 0001261734 AEOLUS PHARMACEUTICALS, INC. AOLS 0001347039 Xmark Opportunity Partners, LLC 90 GROVE STREET RIDGEFIELD CT 06877 0 0 1 0 Senior Convertible Note 0.35 2008-09-04 4 P 0 125000 A 2011-03-04 Common Stock 357142 125000 I See Footnotes Warrants (right to buy) 0.5 2008-09-04 4 P 0 250000 A 2013-09-04 Common Stock 250000 250000 I See Footnotes As of September 4, 2008, Xmark Opportunity Fund, L.P., a Delaware limited partnership ("Opportunity LP"), held (i) 3,056,397 common shares, $0.01 par value per share (the "Common Shares"), of Aeolus Pharmaceuticals, Inc., a Delaware corporation (the "Company"), (ii) warrants to purchase up to 660,000 Common Shares of the Company at an exercise price of $0.35 per share, (iii) a 7% senior convertible note ("Note 1") maturing on February 1, 2011 in the aggregate principal amount of $75,000, which is convertible into 214,285 Common Shares at a conversion price of $0.35 per share subject to certain adjustments, (iv) warrants ("Warrant 1") to purchase 150,000 Common Shares at an exercise price of $0.50 per share subject to certain adjustments, (v) a 7% senior convertible note ("Note 4") maturing on March 4, 2011 in the aggregate principal amount of $18,750, which is convertible into 53,571 Common Shares at a conversion price of $0.35 per share subject to certain adjustments, and (vi) warrants ("Warrant 4") to purchase 37,500 Common Shares at an exercise price of $0.50 per share subject to certain adjustments. As of September 4, 2008, Xmark Opportunity Fund, Ltd., a Cayman Islands exempted company ("Opportunity Ltd"), held (i) 6,512,024 Common Shares of the Company, (ii) warrants to purchase up to 990,000 Common Shares of the Company at an exercise price of $0.35 per share, (iii) a 7% senior convertible note ("Note 2"), in the aggregate principal amount of $175,000, which is convertible into 500,000 Common Shares at a conversion price of $0.35 per share subject to certain adjustments, (iv) warrants ("Warrant 2") to purchase 350,000 Common Shares at an exercise price of $0.50 per share subject to certain adjustments, (v) a 7% senior convertible note ("Note 5"), in the aggregate principal amount of $43,750, which is convertible into 125,000 Common Shares at a conversion price of $0.35 per share subject to certain adjustments, and (vi) warrants ("Warrant 5") to purchase 87,500 Common Shares at an exercise price of $0.50 per share subject to certain adjustments. As of September 4, 2008, Xmark JV Investment Partners, LLC, a Delaware limited liability company ("JV Partners"), held (i) 1,023,731 Common Shares of the Company, (ii) warrants to purchase up to 500,000 Common Shares of the Company at an exercise price of $0.35 per share, (iii) a 7% senior convertible note ("Note 3"), in the aggregate principal amount of $250,000, which is convertible into 714,285 Common Shares at a conversion price of $0.35 per share subject to certain adjustments, and warrants ("Warrant 3") to purchase 500,000 Common shares at an exercise price of $0.50 per share subject to certain adjustments, (v) a 7% senior convertible note ("Note 6"), in the aggregate principal amount of $62,500, which is convertible into 178,571 Common Shares at a conversion price of $0.35 per share subject to certain adjustments, and (vi) warrants ("Warrant 6") to purchase 125,000 Common shares at an exercise price of $0.50 per share subject to certain adjustments. All of the warrants may be exercised within 60 days of this filing. The reporting person, Xmark Opportunity Partners, LLC, a Delaware limited liability company ("Opportunity Partners"), is the sole member of the investment manager of Opportunity LP and Opportunity Ltd, and the investment manager of JV Partners, and, as such, possesses sole power to vote and direct the disposition of all securities of the Company held by Opportunity LP, Opportunity Ltd and JV Partners. Opportunity Partners' interest in the securities reported herein is limited to the extent of its pecuniary interest in Opportunity LP, Opportunity Ltd and JV Partners, if any. Mitchell D. Kaye and David C. Cavalier, the Chief Executive Officer and Chief Operating Officer, respectively, of Xmark Capital Partners, LLC, the Managing Member of Opportunity Partners, share voting and investment power with respect to all securities beneficially owned by Opportunity Partners. On August 1, 2008, the Company entered into a Securities Purchase Agreement ("SPA") with Opportunity LP, Opportunity Ltd and JV Partners (collectively, the "Investors"), pursuant to which, upon the satisfaction of certain conditions the Investors agreed to purchase for an aggregate purchase price of $1,000,000, units comprised of 7% senior convertible notes and warrants to purchase Common Shares from the Company. On August 1, 2008, the Company sold and issued to the Investors under the SPA an aggregate of 500 units ("Units"), collectively comprised of (i) Note 1, Note 2 and Note 3, in the aggregate principal amount of $500,000, and (ii) Warrant 1, Warrant 2 and Warrant 3, which entitles the holder of Warrants to purchase in the aggregate up to 1,000,000 Common Shares at an exercise price of $0.50 per share subject to certain adjustments. On September 4, 2008, the Company sold and issued to the Investors under the SPA an aggregate of 125 units ("Units"), collectively comprised of (i) Note 4, Note 5 and Note 6, in the aggregate principal amount of $125,000, and (ii) Warrant 4, Warrant 5 and Warrant 6, which entitles the holder of Warrants to purchase in the aggregate up to 250,000 Common Shares at an exercise price of $0.50 per share subject to certain adjustments. Each Unit consists of $1,000 in principal amount of 7% senior convertible notes and warrants to purchase up to 2,000 Common Shares at a purchase price of $1,000 per Unit. The Notes are convertible into Common Shares at a conversion price of $0.35 per share subject to certain adjustments. The Notes permit the Company, at its sole option, to pay interest in cash or Common Shares. The Notes and Warrants each contain an issuance limitation prohibiting the Investors from exercising those securities to the extent that such exercise would result in beneficial ownership by the Investors of more than 9.99% of the Common Shares then issued and outstanding, which prohibition cannot be removed by the holder before the 61st day after such holder's notice to the Company of its election to remove such prohibition. Pursuant to the SPA, the Company agreed to sell and issue to the Investors on October 1, 2008, November 3, 2008 and December 1, 2008, upon satisfaction of certain conditions, an additional 125 Units on each date in the aggregate ("Additional Units") comprised of (i) $18,750 in aggregate principal amount of 7% senior convertible notes ("Note A"), which is convertible into approximately 53,571 Common Shares at a conversion price of $0.35 per share subject to certain adjustments, and warrants ("Warrant A") to purchase up to 37,500 Common Shares at an exercise price of $0.50 per share subject to certain adjustments, to be issued to Opportunity LP, (ii) $43,750 in aggregate principal amount of 7% senior convertible notes ("Note B"), which is convertible into 125,000 Common Shares at a conversion price of $0.35 per share subject to certain adjustments, and warrants ("Warrant B") to purchase up to 87,500 Common Shares at an exercise price of $0.50 per share subject to certain adjustments, to be issued to Opportunity Ltd, and (iii) $62,500 in aggregate principal amount of 7% senior convertible notes ("Note C"), which is convertible into approximately 178,571 Common Shares at a conversion price of $0.35 per share subject to certain adjustments, which conversion price is subject to certain adjustments, and warrants ("Warrant C") to purchase 125,000 Common Shares at an exercise price of $0.50 per share subject to certain adjustments, to be issued to JV Partners. Each Unit consists of $1,000 in principal amount of 7% senior convertible notes and warrants to purchase up to 2,000 Common Shares, at a purchase price of $1,000 per Unit. The Notes permit the Company, at its sole option, to pay interest in cash or Common Shares. Note A, Note B, Note C, Warrant A, Warrant B and Warrant C each contain an issuance limitation prohibiting the Investors from exercising those securities to the extent that such exercise would result in beneficial ownership by the Investors of more than 9.99% of the Common Shares then issued and outstanding, which prohibition cannot be removed by the holder before the 61st day after such holder's notice to the Company of its election to remove such prohibition. The conditions precedent to the purchase of the Additional Units to be issued on each Subsequent Closing Date may be waived at the sole discretion of the Investors. These securities are immediately convertible or exercisable into Common Shares. XMARK OPPORTUNITY PARTNERS, LLC By: Xmark Capital Partners, LLC, its Managing Member By: /s/ Mitchell D. Kaye, its Chief Executive Officer 2008-09-10