ZA200307982B - Optical resolution of (1-benzyl-4-methylpiperidin-3-yl)-methylamine and the use thereof for the preparation of pyrrolo 2,3-pyrimidine derivatives as protein kinases inhibitors. - Google Patents
Optical resolution of (1-benzyl-4-methylpiperidin-3-yl)-methylamine and the use thereof for the preparation of pyrrolo 2,3-pyrimidine derivatives as protein kinases inhibitors. Download PDFInfo
- Publication number
- ZA200307982B ZA200307982B ZA200307982A ZA200307982A ZA200307982B ZA 200307982 B ZA200307982 B ZA 200307982B ZA 200307982 A ZA200307982 A ZA 200307982A ZA 200307982 A ZA200307982 A ZA 200307982A ZA 200307982 B ZA200307982 B ZA 200307982B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- amino
- alkoxy
- alkylamino
- cyano
- Prior art date
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- 102000001253 Protein Kinase Human genes 0.000 title claims description 7
- 108060006633 protein kinase Proteins 0.000 title claims description 7
- 239000003112 inhibitor Substances 0.000 title description 5
- 230000003287 optical effect Effects 0.000 title description 5
- 238000002360 preparation method Methods 0.000 title description 2
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 2
- NVKDDQBZODSEIN-UHFFFAOYSA-N 1-benzyl-n,4-dimethylpiperidin-3-amine Chemical compound C1CC(C)C(NC)CN1CC1=CC=CC=C1 NVKDDQBZODSEIN-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 206
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 55
- -1 amina Chemical group 0.000 claims description 50
- 125000003545 alkoxy group Chemical group 0.000 claims description 45
- 125000003282 alkyl amino group Chemical group 0.000 claims description 40
- 125000004442 acylamino group Chemical group 0.000 claims description 37
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 37
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 35
- 125000002252 acyl group Chemical group 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 27
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 24
- 229910052805 deuterium Inorganic materials 0.000 claims description 24
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 23
- 125000000304 alkynyl group Chemical group 0.000 claims description 22
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 22
- 229910052792 caesium Inorganic materials 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000004423 acyloxy group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 230000000707 stereoselective effect Effects 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000002244 precipitate Substances 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 8
- 238000001556 precipitation Methods 0.000 claims description 8
- 108010019421 Janus Kinase 3 Proteins 0.000 claims description 7
- 102000006500 Janus Kinase 3 Human genes 0.000 claims description 7
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 7
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical group N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 5
- 239000006184 cosolvent Substances 0.000 claims description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 5
- 150000003892 tartrate salts Chemical class 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
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- 150000002431 hydrogen Chemical class 0.000 claims description 4
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- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
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- 239000011975 tartaric acid Substances 0.000 claims description 3
- CMIBUZBMZCBCAT-HZPDHXFCSA-N (2r,3r)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid Chemical group C1=CC(C)=CC=C1C(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(=O)C1=CC=C(C)C=C1 CMIBUZBMZCBCAT-HZPDHXFCSA-N 0.000 claims description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- OOKSMYZBWRKRGU-UHFFFAOYSA-N 2-benzoyl-2,3-dihydroxybutanedioic acid Chemical class OC(=O)C(O)C(O)(C(O)=O)C(=O)C1=CC=CC=C1 OOKSMYZBWRKRGU-UHFFFAOYSA-N 0.000 claims description 2
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- 125000005425 toluyl group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 14
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
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- PSZSDCWNBXVDFG-UHFFFAOYSA-N 2-hydroxy-5,5-dimethyl-4-phenyl-1,3,2$l^{5}-dioxaphosphinane 2-oxide Chemical compound CC1(C)COP(O)(=O)OC1C1=CC=CC=C1 PSZSDCWNBXVDFG-UHFFFAOYSA-N 0.000 claims 1
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- 239000013078 crystal Substances 0.000 claims 1
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- 125000005956 isoquinolyl group Chemical group 0.000 description 1
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- 125000003965 isoxazolidinyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 125000003386 piperidinyl group Chemical group 0.000 description 1
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- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
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- 150000003230 pyrimidines Chemical class 0.000 description 1
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- 150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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Classifications
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- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Health & Medical Sciences (AREA)
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- Transplantation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Hydrogenated Pyridines (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29477501P | 2001-05-31 | 2001-05-31 | |
| US34104801P | 2001-12-06 | 2001-12-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200307982B true ZA200307982B (en) | 2004-10-14 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200307982A ZA200307982B (en) | 2001-05-31 | 2003-10-14 | Optical resolution of (1-benzyl-4-methylpiperidin-3-yl)-methylamine and the use thereof for the preparation of pyrrolo 2,3-pyrimidine derivatives as protein kinases inhibitors. |
Country Status (52)
Families Citing this family (123)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PA8474101A1 (es) | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| DK1235830T3 (da) | 1999-12-10 | 2004-03-29 | Pfizer Prod Inc | Pyrrolo[2,3-d]pyrimidin-forbindelser som proteinkinaseinhibitorer |
| YU83302A (sh) * | 2000-06-26 | 2005-09-19 | Pfizer Products Inc. | Jedinjenja pirolo (2,3-d) pirimidina kao imunosupresivni agensi |
| GT200200234A (es) | 2001-12-06 | 2003-06-27 | Compuestos cristalinos novedosos | |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| CN103169708B (zh) | 2002-07-29 | 2018-02-02 | 里格尔药品股份有限公司 | 用2,4‑嘧啶二胺化合物治疗或者预防自体免疫性疾病的方法 |
| CA2496688C (en) * | 2002-08-27 | 2012-09-25 | Hans-Peter Buchstaller | Glycinamide derivatives as raf-kinase inhibitors |
| CN1717236A (zh) | 2002-11-26 | 2006-01-04 | 辉瑞产品公司 | 治疗移植排斥的方法 |
| JP4886511B2 (ja) | 2003-07-30 | 2012-02-29 | ライジェル ファーマシューティカルズ， インコーポレイテッド | ２，４−ピリミジンジアミン化合物による自己免疫疾患の治療または予防方法 |
| EP1755680A1 (en) | 2004-05-03 | 2007-02-28 | Novartis AG | Combinations comprising a s1p receptor agonist and a jak3 kinase inhibitor |
| MXPA06015237A (es) | 2004-06-29 | 2007-12-10 | Amgen Inc | Pirrolo[2-3-d]pirimidinas que modulan la actividad de ack1 y lck. |
| MX2007001399A (es) | 2004-08-02 | 2007-04-18 | Osi Pharm Inc | Compuestos que inhiben pirrolopirimidina multi-cinasa aril-amino sustituidas. |
| MX2007006204A (es) * | 2004-11-24 | 2007-06-20 | Novartis Ag | Combinaciones que comprenden inhibidores de jak y cuando menos uno de entre inhibidores de bcr-abl, flt-3, fak o raf cinasa. |
| AR054416A1 (es) * | 2004-12-22 | 2007-06-27 | Incyte Corp | Pirrolo [2,3-b]piridin-4-il-aminas y pirrolo [2,3-b]pirimidin-4-il-aminas como inhibidores de las quinasas janus. composiciones farmaceuticas. |
| SG137989A1 (en) | 2005-06-08 | 2008-01-28 | Rigel Pharmaceuticals Inc | Compositions and methods for inhibition of the JAK pathway |
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| EP2251341A1 (en) | 2005-07-14 | 2010-11-17 | Astellas Pharma Inc. | Heterocyclic Janus kinase 3 inhibitors |
| US8163767B2 (en) | 2005-07-14 | 2012-04-24 | Astellas Pharma Inc. | Heterocyclic Janus Kinase 3 inhibitors |
| DK1913000T3 (da) * | 2005-07-29 | 2012-03-12 | Pfizer Prod Inc | Pyrrolo[2,3-D]pyrimidinderivater; deres mellemprodukter og syntese |
| US20070149506A1 (en) | 2005-09-22 | 2007-06-28 | Arvanitis Argyrios G | Azepine inhibitors of Janus kinases |
| EA019504B1 (ru) | 2005-12-13 | 2014-04-30 | Инсайт Корпорейшн | ГЕТЕРОАРИЛЗАМЕЩЕННЫЕ ПИРРОЛО[2,3-b]ПИРИДИНЫ И ПИРРОЛО[2,3-b]ПИРИМИДИНЫ В КАЧЕСТВЕ ИНГИБИТОРОВ ЯНУС-КИНАЗЫ |
| ES2622493T3 (es) | 2006-02-24 | 2017-07-06 | Rigel Pharmaceuticals, Inc. | Composiciones y métodos para la inhibición de la ruta de JAK |
| GB0605691D0 (en) * | 2006-03-21 | 2006-05-03 | Novartis Ag | Organic Compounds |
| EP2121692B1 (en) | 2006-12-22 | 2013-04-10 | Incyte Corporation | Substituted heterocycles as janus kinase inhibitors |
| CL2008001709A1 (es) | 2007-06-13 | 2008-11-03 | Incyte Corp | Compuestos derivados de pirrolo [2,3-b]pirimidina, moduladores de quinasas jak; composicion farmaceutica; y uso en el tratamiento de enfermedades tales como cancer, psoriasis, artritis reumatoide, entre otras. |
| EP4606378A2 (en) | 2007-06-13 | 2025-08-27 | Incyte Holdings Corporation | Salts of the janus kinase inhibitor (r)-3-( 4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)-1h-pyrazol-1-yl)-3- cyclopentylprop anenitrile |
| BRPI0813553A2 (pt) * | 2007-07-11 | 2017-05-09 | Pfizer | composições farmacêuticas e métodos para tratamento de distúrbios do olho seco |
| AU2009214440B2 (en) | 2008-02-15 | 2014-09-25 | Rigel Pharmaceuticals, Inc. | Pyrimidine-2-amine compounds and their use as inhibitors of JAK kinases |
| EA017218B1 (ru) | 2008-03-11 | 2012-10-30 | Инсайт Корпорейшн | Производные азетидина и циклобутана как ингибиторы jak-киназ |
| US8138339B2 (en) | 2008-04-16 | 2012-03-20 | Portola Pharmaceuticals, Inc. | Inhibitors of protein kinases |
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| KR102635013B1 (ko) | 2010-05-21 | 2024-02-13 | 인사이트 홀딩스 코포레이션 | Ｊａｋ 저해제에 대한 국소 제형 |
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| US9050342B2 (en) | 2011-03-29 | 2015-06-09 | Pfizer Inc. | Beneficial effects of combination therapy on cholesterol |
| KR101593768B1 (ko) | 2011-04-08 | 2016-02-12 | 화이자 인코포레이티드 | 토파시티닙의 결정질 형태 및 비결정질 형태, 및 토파시티닙 및 침투 증진제를 포함하는 제약 조성물 |
| ES2414384T3 (es) | 2011-05-11 | 2013-07-19 | Ratiopharm Gmbh | Composición de liberación modificada que comprende ranolazina |
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