Patents by Inventor Herbert R. Brinkman
Herbert R. Brinkman has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Publication number: 20230181591Abstract: The disclosure relates to stable topical pharmaceutical compositions of SHR0302 (also known as ARQ-250). In certain embodiments, pharmaceutical compositions of SHR0302 having a pH of less than about 4.6 have improved stability and do not exhibit crystal formation of the API. In certain embodiments, pharmaceutical compositions of SHR0302 comprising about 20% to about 30% dimethyl sulfoxide (DMSO) have improved stability and do not exhibit crystal formation of the API. The improved formulations of SHR0302 can exhibit acceptable commercial product shelf life and do not exhibit loss of potency of the API after prolonged storage.Type: ApplicationFiled: December 14, 2022Publication date: June 15, 2023Applicant: ARCUTIS BIOTHERAPEUTICS, INC.Inventors: Herbert R. BRINKMAN, Jason Michael Carbol
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Patent number: 11584715Abstract: A cocrystal containing the 1?R-diastereomer and the 1?S-diastereomer of sofpironium bromide at a ratio of 1:3 (Form CO), a crystal mixture (for example, Form B) containing Form CO and a crystalline form of the 1?R-diastereomer (Form MN), and a method for preparing sofpironium bromide, which is suitable for manufacture of the crystal mixture are provided. Form CO and a crystalline form of sofpironium bromide containing Form CO (for example, Form B) have superior stability without hygroscopic property, and accordingly they can be preferably used as a raw material of medicaments.Type: GrantFiled: June 30, 2021Date of Patent: February 21, 2023Assignee: Botanix SB, Inc.Inventors: Kazuyoshi Marubayashi, Masahito Watanabe, Herbert R. Brinkman
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Patent number: 11566000Abstract: A cocrystal containing the 1?R-diastereomer and the 1'S-diastereomer of sofpironium bromide at a ratio of 1:3 (Form CO), a crystal mixture (for example, Form B) containing Form CO and a crystalline form of the 1?R-diastereomer (Form MN), and a method for preparing sofpironium bromide, which is suitable for manufacture of the crystal mixture are provided. Form CO and a crystalline form of sofpironium bromide containing Form CO (for example, Form B) have superior stability without hygroscopic property, and accordingly they can be preferably used as a raw material of medicaments.Type: GrantFiled: November 25, 2020Date of Patent: January 31, 2023Assignee: Botanix SB, Inc.Inventors: Kazuyoshi Marubayashi, Masahito Watanabe, Herbert R. Brinkman
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Publication number: 20220298108Abstract: A cocrystal containing the 1?R-diastereomer and the 1?S-diastereomer of sofpironium bromide at a ratio of 1:3 (Form CO), a crystal mixture (for example, Form B) containing Form CO and a crystalline form of the 1?R-diastereomer (Form MN), and a method for preparing sofpironium bromide, which is suitable for manufacture of the crystal mixture are provided. Form CO and a crystalline form of sofpironium bromide containing Form CO (for example, Form B) have superior stability without hygroscopic property, and accordingly they can be preferably used as a raw material of medicaments.Type: ApplicationFiled: May 22, 2020Publication date: September 22, 2022Applicants: Kaken Pharmaceutical Co., Ltd., Brickell Biotech, Inc.Inventors: Kazuyoshi MARUBAYASHI, Masahito WATANABE, Herbert R. BRINKMAN
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Publication number: 20210395197Abstract: A cocrystal containing the 1?R-diastereomer and the 1?S-diastereomer of sofpironium bromide at a ratio of 1:3 (Form CO), a crystal mixture (for example, Form B) containing Form CO and a crystalline form of the 1?R-diastereomer (Form MN), and a method for preparing sofpironium bromide, which is suitable for manufacture of the crystal mixture are provided. Form CO and a crystalline form of sofpironium bromide containing Form CO (for example, Form B) have superior stability without hygroscopic property, and accordingly they can be preferably used as a raw material of medicaments.Type: ApplicationFiled: June 30, 2021Publication date: December 23, 2021Applicants: Kaken Pharmaceutical Co., Ltd., Brickell Biotech, Inc.Inventors: Kazuyoshi MARUBAYASHI, Masahito WATANABE, Herbert R. BRINKMAN
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Publication number: 20210171460Abstract: A cocrystal containing the 1?R-diastereomer and the 1'S-diastereomer of sofpironium bromide at a ratio of 1:3 (Form CO), a crystal mixture (for example, Form B) containing Form CO and a crystalline form of the 1?R-diastereomer (Form MN), and a method for preparing sofpironium bromide, which is suitable for manufacture of the crystal mixture are provided. Form CO and a crystalline form of sofpironium bromide containing Form CO (for example, Form B) have superior stability without hygroscopic property, and accordingly they can be preferably used as a raw material of medicaments.Type: ApplicationFiled: November 25, 2020Publication date: June 10, 2021Applicants: Kaken Pharmaceutical Co., Ltd., Brickell Biotech, Inc.Inventors: Kazuyoshi MARUBAYASHI, Masahito WATANABE, Herbert R. BRINKMAN
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Patent number: 6653501Abstract: A method is provided for processing a solution having optical isomers to obtain a (2R,3S) target isomer: wherein P1 is H or a hydroxyl protecting group, R1 is H, an alkyl group, an olefinic group or an aromatic group, and R2 is H or R3CO, where R3 is an alkyl group, an olefinic group, an aromatic group, an O-alkyl group, an O-olefinic group or an O-aromatic group, provided that R1 is not H when R3 is Ph and P1 is H. The method includes passing the solution through a chromatographic stationary phase, such as S,S Whelk-O, that has a greater affinity for one of the target isomer and an optical isomer thereof. A portion of the solution with the target isomer is then collected. The solution may be a racemic mixture of (±)-N-CBZ-3-phenylisoserine ethyl ester.Type: GrantFiled: June 27, 2001Date of Patent: November 25, 2003Assignee: NaPro BioTherapeutics, Inc.Inventors: James D. McChesney, Herbert R. Brinkman, Siead Zegar, David Baehr
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Publication number: 20030045743Abstract: A method is provided for processing a solution having optical isomers to obtain a (2R,3S) target isomer: 1Type: ApplicationFiled: June 27, 2001Publication date: March 6, 2003Inventors: James D. McChesney, Herbert R. Brinkman, Siead Zegar, David Baehr
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Patent number: 6448417Abstract: The present invention relates to a method of producing paclitaxel or a paclitaxel analog comprising the esterification of C-7, C-10 di-CBZ 10-deacetylbaccatin III with an N-carbamate protected, C-2-protected 3-phenyl isoserine side chain. The C-7, C-10 carbobenzyloxy groups are then replaced with hydrogen and an acyl group is substituted at the C-3′ nitrogen. The resulting compound is acylated at the C-10 hydroxyl position, and deprotected at the C-2′ position by replacing the hydroxyl protecting group with hydrogen to produce paclitaxel or a paclitaxel analog. The present invention also relates to alternative methods of acylating a 10-hydroxy paclitaxel analog. The first method comprises dissolving a 10-hydroxy paclitaxel analog in an acceptable ether solvent therefor to form a first solution at a first temperature.Type: GrantFiled: January 11, 2001Date of Patent: September 10, 2002Assignee: NaPro BioTherapeutics, Inc.Inventors: Nicholas J. Sisti, Herbert R. Brinkman, James D. McChesney, Medhavi C. Chander, Xian Liang, Jan Zygmunt
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Patent number: 6066749Abstract: A method of acylating C-2' O-protected-10-hydroxy taxol selectively at the C-10 hydroxyl position over the C-7 hydroxy position thereof to produce C-2' O-protected taxol is accomplished first by dissolving C-2' O-protected-10-hydroxy taxol in an acceptable ether solvent therefor, such as tetrahydrofuran, to form a first solution at a first temperature. The first solution is then cooled to a second temperature, and a lithium base, preferably n-butyl lithium, is added to form an intermediate compound having a lithium alkoxide at the C-10 position thereof. An acylating agent, such as acetyl chloride, is then added. The resulting solution may be quenched, for example with ammonium chloride, to eliminate excess of the acylating agent and the lithium base. The result is a solution containing C-2' O-protected taxol. This solution may then be washed, concentrated and purified. The present invention is also directed to C-10 lithium alkoxide intermediate compounds for the production of paclitaxel.Type: GrantFiled: May 1, 1998Date of Patent: May 23, 2000Assignee: NaPro BioTherapeutics, Inc.Inventors: Nicholas J. Sisti, Herbert R. Brinkman, James D. McChesney, Madhavi C. Chander, Xian Liang, Jan Zygmunt
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Patent number: 6048990Abstract: A method of acylating C-2' O-protected-10-hydroxy taxol selectively at the C-10 hydroxyl position over the C-7 hydroxy position thereof to produce C-2' O-protected taxol is accomplished first by dissolving C-2' O-protected-10-hydroxy taxol in an acceptable ether solvent therefor, such as tetrahydrofuran. A lithium salt, preferably lithium chloride, is added. A trialkylamine base or pyridine is next added, followed by the addition of an acylating agent, such as acetyl chloride. The resulting solution may be quenched, for example with ammonium chloride, to eliminate excess of the acylating agent. This solution may then be diluted with ethyl acetate to form an organic phase and an aqueous phase, with the organic phase being washed and thereafter reduced. Recrystallization and column chromatography may be employed to purify the C-2' O-protected taxol.Type: GrantFiled: May 1, 1998Date of Patent: April 11, 2000Assignee: NaPro BioTherapeutics, Inc.Inventors: Xian Liang, Jan Zygmunt, Nicholas J. Sisti, Madhavi C. Chander, Herbert R. Brinkman, James D. McChesney
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Patent number: 5914411Abstract: A method of acylating 10-deacetylbaccatin III at the C-10 position over the C-7 hydroxy position thereof to produce baccatin IIII is accomplished first by dissolving 10-deacetylbaccatin III in an acceptable ether solvent therefor, such as tetrahydrofuran. A lithium salt, preferably lithium chloride, is added. A trialkylamine base or pyridine is next added, followed by the addition of an acylating agent, such as acetyl chloride. The resulting solution may be quenched, for example with ammonium chloride, to eliminate excess of the acylating agent. The result is baccatin III in solution. This solution may then be diluted with ethyl acetate to form an organic phase and an aqueous phase, with the organic phase being washed and thereafter reduced. Recrystallization and column chromatography may be employed to purify the baccatin III.Type: GrantFiled: January 21, 1998Date of Patent: June 22, 1999Assignee: NaPro BioTherapeutics, Inc.Inventors: Nicholas J. Sisti, Jan Zygmunt, Herbert R. Brinkman, Madhavi C. Chander, Xian Liang, James D. McChesney
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Patent number: 5476932Abstract: A process for preparing N4-acyl-5'-deoxy-5-fluorocytidine derivatives of formula III: ##STR1## by selective deacylation, wherein R is alkyl, cycloalkyl, alkenyl, aralkyl or aryl,which comprises reacting a compound of formula II, ##STR2## wherein R is as defined above, with a base in an aqueous or inert organic solvent.Type: GrantFiled: August 26, 1994Date of Patent: December 19, 1995Assignee: Hoffmann-La Roche Inc.Inventors: Herbert R. Brinkman, Panayiotis Kalaritis, John F. Morrissey