AU2012324029B2 - Polymorphs of CDDO ethyl ester and uses thereof - Google Patents
Polymorphs of CDDO ethyl ester and uses thereof Download PDFInfo
- Publication number
- AU2012324029B2 AU2012324029B2 AU2012324029A AU2012324029A AU2012324029B2 AU 2012324029 B2 AU2012324029 B2 AU 2012324029B2 AU 2012324029 A AU2012324029 A AU 2012324029A AU 2012324029 A AU2012324029 A AU 2012324029A AU 2012324029 B2 AU2012324029 B2 AU 2012324029B2
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- Prior art keywords
- polymorph
- compound
- formula
- crystalline form
- ray powder
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 238000000034 method Methods 0.000 claims abstract description 30
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- 239000007787 solid Substances 0.000 claims description 52
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 45
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 37
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 20
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- 238000004519 manufacturing process Methods 0.000 claims description 14
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- 239000003814 drug Substances 0.000 claims description 10
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 8
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- 230000002093 peripheral effect Effects 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 10
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- -1 CDDO ETHYL ESTER Chemical class 0.000 abstract description 2
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- 239000000243 solution Substances 0.000 description 27
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- 125000004494 ethyl ester group Chemical group 0.000 description 8
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- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 4
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- MIJYXULNPSFWEK-GTOFXWBISA-N 3beta-hydroxyolean-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MIJYXULNPSFWEK-GTOFXWBISA-N 0.000 description 3
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/57—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and carboxyl groups, other than cyano groups, bound to the carbon skeleton
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Applications Claiming Priority (3)
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| CN2012082278 | 2012-09-28 | ||
| CNPCT/CN2012/082278 | 2012-09-28 | ||
| PCT/CN2012/086045 WO2014048033A1 (en) | 2012-09-28 | 2012-12-06 | Polymorphs of cddo ethyl ester and uses thereof |
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| AU2012324029A1 AU2012324029A1 (en) | 2014-04-17 |
| AU2012324029B2 true AU2012324029B2 (en) | 2015-05-14 |
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| AU (1) | AU2012324029B2 (enExample) |
| WO (1) | WO2014048033A1 (enExample) |
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| KR101735807B1 (ko) | 2008-04-18 | 2017-05-15 | 리타 파마슈티컬스 잉크. | Ｃ-17에 아미노 및 기타 변형을 갖는 올레아놀산 유도체를 포함하는 항산화 염증 조절제 |
| ME02926B (me) | 2012-04-27 | 2018-04-20 | Reata Pharmaceuticals Inc | 2,2-difluoropropionamidni derivati bardoksolon metila, polimorfni oblici i postupci za njihovu upotrebu |
| US9556222B2 (en) | 2012-06-15 | 2017-01-31 | Reata Pharmaceuticals, Inc. | A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof |
| CR20150117A (es) | 2012-09-10 | 2016-10-10 | Reata Pharmaceuticals Inc | Derivados c17-alcandilo y alquendilo del ácido oleanólico y sus métodos de uso |
| US9512094B2 (en) | 2012-09-10 | 2016-12-06 | Reata Pharmaceuticals, Inc. | C17-heteroaryl derivatives of oleanolic acid and methods of use thereof |
| US9278912B2 (en) | 2012-09-10 | 2016-03-08 | Reata Pharmaceuticals, Inc. | C13-hydroxy derivatives of oleanolic acid and methods of use thereof |
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| US8088824B2 (en) | 2007-08-15 | 2012-01-03 | Reata Pharmaceuticals Inc. | Forms of CDDO methyl ester |
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2012
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- 2012-12-06 US US14/007,925 patent/US9656951B2/en not_active Expired - Fee Related
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Non-Patent Citations (2)
| Title |
|---|
| HONDA, T. ET AL, J. Med. Chem., 2000, Vol. 43, pages 4233-4246 * |
| HONDA, T. ET AL., Bioorganic & Medicinal Chemistry Letters, 2002, Vol. 12, pages 1027-1030 * |
Also Published As
| Publication number | Publication date |
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| WO2014048033A1 (en) | 2014-04-03 |
| KR20140051813A (ko) | 2014-05-02 |
| US20140315997A1 (en) | 2014-10-23 |
| US20170355666A1 (en) | 2017-12-14 |
| JP5972986B2 (ja) | 2016-08-17 |
| JP2016145212A (ja) | 2016-08-12 |
| JP2014534208A (ja) | 2014-12-18 |
| US9656951B2 (en) | 2017-05-23 |
| KR101545068B1 (ko) | 2015-08-17 |
| EP2739639A1 (en) | 2014-06-11 |
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