JP2006507247A5 - - Google Patents
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- Publication number
- JP2006507247A5 JP2006507247A5 JP2004535518A JP2004535518A JP2006507247A5 JP 2006507247 A5 JP2006507247 A5 JP 2006507247A5 JP 2004535518 A JP2004535518 A JP 2004535518A JP 2004535518 A JP2004535518 A JP 2004535518A JP 2006507247 A5 JP2006507247 A5 JP 2006507247A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- group
- phenyl
- methylsulfonyl
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 97
- 229910052799 carbon Inorganic materials 0.000 claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 16
- 125000001153 fluoro group Chemical group F* 0.000 claims 15
- 125000003545 alkoxy group Chemical group 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- -1 alkyl OCOC Chemical compound 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 2
- 102100038280 Prostaglandin G/H synthase 2 Human genes 0.000 claims 2
- 108050003267 Prostaglandin G/H synthase 2 Proteins 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- KJROYZQXANQCCB-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-6-(pyridin-2-ylmethoxy)-4-(trifluoromethyl)pyridine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C(F)(F)F)=CC(OCC=2N=CC=CC=2)=N1 KJROYZQXANQCCB-UHFFFAOYSA-N 0.000 claims 1
- UEGXVPGOZGJIMA-UHFFFAOYSA-N 4-ethyl-2-[(1-methylpyrazol-4-yl)methylamino]-6-(4-methylsulfonylphenyl)pyridine-3-carbonitrile Chemical compound N#CC=1C(CC)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=NC=1NCC=1C=NN(C)C=1 UEGXVPGOZGJIMA-UHFFFAOYSA-N 0.000 claims 1
- GJGCELHMLIVVEN-UHFFFAOYSA-N 4-ethyl-2-[(5-methylpyridin-2-yl)methylamino]-6-(4-methylsulfonylphenyl)pyridine-3-carbonitrile Chemical compound N#CC=1C(CC)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=NC=1NCC1=CC=C(C)C=N1 GJGCELHMLIVVEN-UHFFFAOYSA-N 0.000 claims 1
- OTZWQZBSAJYZDR-UHFFFAOYSA-N 4-ethyl-2-[(6-methylpyridin-3-yl)methoxy]-6-(4-methylsulfonylphenyl)pyridine-3-carbonitrile Chemical compound N#CC=1C(CC)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=NC=1OCC1=CC=C(C)N=C1 OTZWQZBSAJYZDR-UHFFFAOYSA-N 0.000 claims 1
- CXVYZIFUAOQBKB-UHFFFAOYSA-N 4-ethyl-2-[(6-methylpyridin-3-yl)methylamino]-6-(4-methylsulfonylphenyl)pyridine-3-carbonitrile Chemical compound N#CC=1C(CC)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=NC=1NCC1=CC=C(C)N=C1 CXVYZIFUAOQBKB-UHFFFAOYSA-N 0.000 claims 1
- QLEFRAISEMFOGS-UHFFFAOYSA-N 4-ethyl-6-(4-methylsulfonylphenyl)-2-(pyridin-2-ylmethoxy)pyridine-3-carbonitrile Chemical compound N#CC=1C(CC)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=NC=1OCC1=CC=CC=N1 QLEFRAISEMFOGS-UHFFFAOYSA-N 0.000 claims 1
- LLQNNOXVGDGVCI-UHFFFAOYSA-N 4-ethyl-6-(4-methylsulfonylphenyl)-2-(pyridin-2-ylmethylamino)pyridine-3-carbonitrile Chemical compound N#CC=1C(CC)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=NC=1NCC1=CC=CC=N1 LLQNNOXVGDGVCI-UHFFFAOYSA-N 0.000 claims 1
- JPRMYQBDXDYHMB-UHFFFAOYSA-N 4-ethyl-6-(4-methylsulfonylphenyl)-2-[(4-methyl-1,3-thiazol-2-yl)methylamino]pyridine-3-carbonitrile Chemical compound N#CC=1C(CC)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=NC=1NCC1=NC(C)=CS1 JPRMYQBDXDYHMB-UHFFFAOYSA-N 0.000 claims 1
- LSJNJEUKEDFUOS-UHFFFAOYSA-N 4-ethyl-6-(4-methylsulfonylphenyl)-n-(oxan-4-ylmethyl)pyridin-2-amine Chemical compound N=1C(C=2C=CC(=CC=2)S(C)(=O)=O)=CC(CC)=CC=1NCC1CCOCC1 LSJNJEUKEDFUOS-UHFFFAOYSA-N 0.000 claims 1
- WOPITVVKVRKXAR-UHFFFAOYSA-N 4-ethyl-n-[(2-ethyl-1,2,4-triazol-3-yl)methyl]-6-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound N=1C(C=2C=CC(=CC=2)S(C)(=O)=O)=CC(CC)=CC=1NCC1=NC=NN1CC WOPITVVKVRKXAR-UHFFFAOYSA-N 0.000 claims 1
- ZYYZFEFYWDMJKQ-UHFFFAOYSA-N 4-methyl-n-[(1-methylpyrazol-3-yl)methyl]-6-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound N=1C(C=2C=CC(=CC=2)S(C)(=O)=O)=CC(C)=CC=1NCC=1C=CN(C)N=1 ZYYZFEFYWDMJKQ-UHFFFAOYSA-N 0.000 claims 1
- TXHSNZYVIKJKHL-UHFFFAOYSA-N 4-methyl-n-[(1-methylpyrazol-4-yl)methyl]-6-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound N=1C(C=2C=CC(=CC=2)S(C)(=O)=O)=CC(C)=CC=1NCC=1C=NN(C)C=1 TXHSNZYVIKJKHL-UHFFFAOYSA-N 0.000 claims 1
- RHAKELPGMNNZMY-UHFFFAOYSA-N 4-methyl-n-[(2-methylpyrazol-3-yl)methyl]-6-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound N=1C(C=2C=CC(=CC=2)S(C)(=O)=O)=CC(C)=CC=1NCC1=CC=NN1C RHAKELPGMNNZMY-UHFFFAOYSA-N 0.000 claims 1
- PKHKNWQIBCZJMC-UHFFFAOYSA-N 4-methyl-n-[(3-methyl-1,2-oxazol-4-yl)methyl]-6-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound CC1=NOC=C1CNC1=CC(C)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=N1 PKHKNWQIBCZJMC-UHFFFAOYSA-N 0.000 claims 1
- JQYGMWSNHGUYFH-UHFFFAOYSA-N 6-(4-methylsulfonylphenyl)-n-(pyridin-2-ylmethyl)-4-(trifluoromethyl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C(F)(F)F)=CC(NCC=2N=CC=CC=2)=N1 JQYGMWSNHGUYFH-UHFFFAOYSA-N 0.000 claims 1
- VFQRMDNTBZLTOG-UHFFFAOYSA-N 6-(4-methylsulfonylphenyl)-n-[(2-methyl-1,2,4-triazol-3-yl)methyl]-4-(trifluoromethyl)pyridin-2-amine Chemical compound CN1N=CN=C1CNC1=CC(C(F)(F)F)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=N1 VFQRMDNTBZLTOG-UHFFFAOYSA-N 0.000 claims 1
- ZRBRLFRIMWOPNI-UHFFFAOYSA-N 6-(4-methylsulfonylphenyl)-n-pentan-3-yl-4-(trifluoromethyl)pyridin-2-amine Chemical compound CCC(CC)NC1=CC(C(F)(F)F)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=N1 ZRBRLFRIMWOPNI-UHFFFAOYSA-N 0.000 claims 1
- IFLNYNOUGIZZSM-AKAXFMLLSA-N C1C[C@@H](C)CC[C@H]1NC1=CC(C(F)(F)F)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=N1 Chemical compound C1C[C@@H](C)CC[C@H]1NC1=CC(C(F)(F)F)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=N1 IFLNYNOUGIZZSM-AKAXFMLLSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- IMXXUEDKOYSPGU-UHFFFAOYSA-N n-(cyclohexylmethyl)-6-(4-methylsulfonylphenyl)-4-(trifluoromethyl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C(F)(F)F)=CC(NCC2CCCCC2)=N1 IMXXUEDKOYSPGU-UHFFFAOYSA-N 0.000 claims 1
- KTOVEMBDIBZSDA-UHFFFAOYSA-N n-(cyclopentylmethyl)-6-(4-methylsulfonylphenyl)-4-(trifluoromethyl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C(F)(F)F)=CC(NCC2CCCC2)=N1 KTOVEMBDIBZSDA-UHFFFAOYSA-N 0.000 claims 1
- CREBKKWJYADUSK-UHFFFAOYSA-N n-[(1,3-dimethylpyrazol-4-yl)methyl]-4-methyl-6-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound CC1=NN(C)C=C1CNC1=CC(C)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=N1 CREBKKWJYADUSK-UHFFFAOYSA-N 0.000 claims 1
- RULFYBHOHILGIR-UHFFFAOYSA-N n-[(1,3-dimethylpyrazol-4-yl)methyl]-6-(4-methylsulfonylphenyl)-4-(trifluoromethyl)pyridin-2-amine Chemical compound CC1=NN(C)C=C1CNC1=CC(C(F)(F)F)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=N1 RULFYBHOHILGIR-UHFFFAOYSA-N 0.000 claims 1
- ZPHKVHNHVVZLMJ-UHFFFAOYSA-N n-[(1,5-dimethylpyrazol-4-yl)methyl]-4-methyl-6-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound C1=NN(C)C(C)=C1CNC1=CC(C)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=N1 ZPHKVHNHVVZLMJ-UHFFFAOYSA-N 0.000 claims 1
- JVSGYWWKSKBLRR-UHFFFAOYSA-N n-[(1,5-dimethylpyrazol-4-yl)methyl]-6-(4-methylsulfonylphenyl)-4-(trifluoromethyl)pyridin-2-amine Chemical compound C1=NN(C)C(C)=C1CNC1=CC(C(F)(F)F)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=N1 JVSGYWWKSKBLRR-UHFFFAOYSA-N 0.000 claims 1
- JOPYSMUAZPPAPM-UHFFFAOYSA-N n-[(2-ethyl-1,2,4-triazol-3-yl)methyl]-4-methyl-6-(4-methylsulfonylphenyl)pyridin-2-amine Chemical compound CCN1N=CN=C1CNC1=CC(C)=CC(C=2C=CC(=CC=2)S(C)(=O)=O)=N1 JOPYSMUAZPPAPM-UHFFFAOYSA-N 0.000 claims 1
- JBPUBVBADITRBO-UHFFFAOYSA-N n-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-(4-methylsulfonylphenyl)-4-(trifluoromethyl)pyridin-2-amine Chemical compound CC1=NOC(CNC=2N=C(C=C(C=2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 JBPUBVBADITRBO-UHFFFAOYSA-N 0.000 claims 1
- UVKYPAUEYUYGBR-UHFFFAOYSA-N n-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-6-(4-methylsulfonylphenyl)-4-(trifluoromethyl)pyridin-2-amine Chemical compound O1C(C)=NC(CNC=2N=C(C=C(C=2)C(F)(F)F)C=2C=CC(=CC=2)S(C)(=O)=O)=N1 UVKYPAUEYUYGBR-UHFFFAOYSA-N 0.000 claims 1
- VKISWSRIBFIRHN-UHFFFAOYSA-N n-cycloheptyl-6-(4-methylsulfonylphenyl)-4-(trifluoromethyl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C(F)(F)F)=CC(NC2CCCCCC2)=N1 VKISWSRIBFIRHN-UHFFFAOYSA-N 0.000 claims 1
- HOGXDMUYFQWDIN-UHFFFAOYSA-N n-cyclohexyl-6-(4-methylsulfonylphenyl)-4-(trifluoromethyl)pyridin-2-amine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=CC(C(F)(F)F)=CC(NC2CCCCC2)=N1 HOGXDMUYFQWDIN-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0221443.5A GB0221443D0 (en) | 2002-09-16 | 2002-09-16 | Pyridine derivates |
| PCT/EP2003/011065 WO2004024691A1 (en) | 2002-09-16 | 2003-09-12 | Cox-2 inhibiting pyridine derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2006507247A JP2006507247A (ja) | 2006-03-02 |
| JP2006507247A5 true JP2006507247A5 (enExample) | 2006-09-28 |
| JP4630063B2 JP4630063B2 (ja) | 2011-02-09 |
Family
ID=9944138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004535518A Expired - Fee Related JP4630063B2 (ja) | 2002-09-16 | 2003-09-12 | Ｃｏｘ−２阻害性ピリジン誘導体 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US7446117B2 (enExample) |
| EP (1) | EP1546107B1 (enExample) |
| JP (1) | JP4630063B2 (enExample) |
| KR (1) | KR20050046782A (enExample) |
| CN (1) | CN1681788A (enExample) |
| AR (1) | AR041246A1 (enExample) |
| AT (1) | ATE462694T1 (enExample) |
| AU (1) | AU2003276063A1 (enExample) |
| BR (1) | BR0313718A (enExample) |
| CA (1) | CA2493497A1 (enExample) |
| DE (1) | DE60331931D1 (enExample) |
| ES (1) | ES2343316T3 (enExample) |
| GB (1) | GB0221443D0 (enExample) |
| IL (1) | IL166460A0 (enExample) |
| IS (1) | IS7659A (enExample) |
| MA (1) | MA27436A1 (enExample) |
| MX (1) | MXPA05002886A (enExample) |
| NO (1) | NO20050662L (enExample) |
| NZ (1) | NZ538201A (enExample) |
| PL (1) | PL376023A1 (enExample) |
| RU (1) | RU2005103618A (enExample) |
| TW (1) | TW200404541A (enExample) |
| WO (1) | WO2004024691A1 (enExample) |
| ZA (1) | ZA200501174B (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003258630A1 (en) | 2002-08-19 | 2004-03-11 | Glaxo Group Limited | Pyrimidine derivatives as selective cox-2 inhibitors |
| GB0221443D0 (en) | 2002-09-16 | 2002-10-23 | Glaxo Group Ltd | Pyridine derivates |
| WO2005007627A1 (ja) * | 2003-07-18 | 2005-01-27 | Nihon Nohyaku Co., Ltd. | フェニルピリジン誘導体、その中間体及びこれを有効成分とする除草剤 |
| EP2774925B1 (en) | 2005-11-08 | 2016-12-28 | Vertex Pharmaceuticals Incorporated | Heterocyclic modulators of ATP-binding cassette transporters |
| WO2008141119A2 (en) | 2007-05-09 | 2008-11-20 | Vertex Pharmaceuticals Incorporated | Modulators of cftr |
| EP2227467B1 (en) * | 2007-12-04 | 2014-12-31 | F. Hoffmann-La Roche AG | Isoxazolo-pyridine derivatives |
| PL2231606T3 (pl) * | 2007-12-07 | 2013-07-31 | Vertex Pharma | Sposoby wytwarzania kwasów cykloalkilokarboksyamidopirydynobenzoesowych |
| HUE031913T2 (en) | 2007-12-07 | 2017-08-28 | Vertex Pharma | Solid forms of 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl) cyclopropanecarboxamido)-3-methylpyridin-2-yl) benzoic acid |
| JP5523352B2 (ja) | 2008-02-28 | 2014-06-18 | バーテックス ファーマシューティカルズ インコーポレイテッド | Ｃｆｔｒ修飾因子としてのへテロアリール誘導体 |
| US8012976B2 (en) | 2008-08-06 | 2011-09-06 | Biomarin Pharmaceutical Inc. | Dihydropyridophthalazinone inhibitors of poly(ADP-ribose)polymerase (PARP) |
| WO2010046780A2 (en) * | 2008-10-22 | 2010-04-29 | Institut Pasteur Korea | Anti viral compounds |
| US8541403B2 (en) | 2010-02-03 | 2013-09-24 | Biomarin Pharmaceutical Inc. | Dihydropyridophthalazinone inhibitors of poly(ADP-ribose)polymerase (PARP) for use in treatment of diseases associated with a PTEN deficiency |
| DK2533640T3 (en) | 2010-02-08 | 2017-01-23 | Medivation Technologies Inc | METHODS OF SYNTHESIS OF DIHYDROPYRIDOPHTHALAZINE DERIVATIVES |
| RS62767B1 (sr) | 2010-04-07 | 2022-01-31 | Vertex Pharma | Farmaceutski sastavi 3-(6-(1-(2,2-difluorobenzo[d][1,3]dioksol-5-il) ciklopropankarboksamido)-3-metilpiriodin-2-il)benzojeve kiseline i njihova primena |
| PL2630146T3 (pl) | 2010-10-21 | 2020-11-02 | Medivation Technologies Llc | Krystaliczna sól tosylanowa (8S,9R)-5-fluoro-8-(4-fluorofenylo)-9-(1-metylo-1H-1,2,4-triazol-5-ilo)-8,9-dihydro-2H-pirydo[4,3,2-de]ftalazyno-3(7H)-onu |
| CN102464652B (zh) * | 2010-11-02 | 2013-08-28 | 北京欧博方医药科技有限公司 | 咪唑衍生物、制备方法及用途 |
| US8604062B2 (en) | 2011-10-20 | 2013-12-10 | Hoffman-La Roche Inc. | Process for the preparation of isoxazolyl-methoxy nicotinic acids |
| MX355183B (es) | 2012-01-25 | 2018-04-09 | Vertex Pharma | Formulaciones de acido 3- (6- (1- (2.2- difluorobenzo [d] [1,3] dioxol-5-il) ciclopropancarboxamido) -3- metilpiridin-2-il) benzoico. |
| EP3066084A1 (en) * | 2013-11-07 | 2016-09-14 | Medivation Technologies, Inc. | Triazole intermediates useful in the synthesis of protected n-alkyltriazolecarbaldehydes |
| HRP20210516T2 (hr) | 2013-11-12 | 2021-10-01 | Vertex Pharmaceuticals Incorporated | Postupak proizvodnje farmaceutskih pripravaka za liječenje bolesti koje su posredovane putem cftr |
| KR102576006B1 (ko) | 2014-11-18 | 2023-09-06 | 버텍스 파마슈티칼스 인코포레이티드 | 고처리량 시험 고성능 액체 크로마토그래피의 수행 방법 |
| WO2021050700A1 (en) * | 2019-09-13 | 2021-03-18 | The Broad Institute, Inc. | Cyclooxygenase-2 inhibitors and uses thereof |
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-
2002
- 2002-09-16 GB GBGB0221443.5A patent/GB0221443D0/en not_active Ceased
-
2003
- 2003-09-12 DE DE60331931T patent/DE60331931D1/de not_active Expired - Lifetime
- 2003-09-12 AU AU2003276063A patent/AU2003276063A1/en not_active Abandoned
- 2003-09-12 BR BR0313718-0A patent/BR0313718A/pt not_active IP Right Cessation
- 2003-09-12 PL PL03376023A patent/PL376023A1/xx not_active Application Discontinuation
- 2003-09-12 AT AT03795019T patent/ATE462694T1/de not_active IP Right Cessation
- 2003-09-12 MX MXPA05002886A patent/MXPA05002886A/es not_active Application Discontinuation
- 2003-09-12 EP EP03795019A patent/EP1546107B1/en not_active Expired - Lifetime
- 2003-09-12 CA CA002493497A patent/CA2493497A1/en not_active Abandoned
- 2003-09-12 KR KR1020057004428A patent/KR20050046782A/ko not_active Withdrawn
- 2003-09-12 AR ARP030103312A patent/AR041246A1/es not_active Application Discontinuation
- 2003-09-12 US US10/527,799 patent/US7446117B2/en not_active Expired - Fee Related
- 2003-09-12 CN CNA038218496A patent/CN1681788A/zh active Pending
- 2003-09-12 WO PCT/EP2003/011065 patent/WO2004024691A1/en not_active Ceased
- 2003-09-12 JP JP2004535518A patent/JP4630063B2/ja not_active Expired - Fee Related
- 2003-09-12 RU RU2005103618/04A patent/RU2005103618A/ru not_active Application Discontinuation
- 2003-09-12 ES ES03795019T patent/ES2343316T3/es not_active Expired - Lifetime
- 2003-09-12 NZ NZ538201A patent/NZ538201A/en unknown
- 2003-09-15 TW TW092125337A patent/TW200404541A/zh unknown
-
2005
- 2005-01-20 IS IS7659A patent/IS7659A/is unknown
- 2005-01-24 IL IL16646005A patent/IL166460A0/xx unknown
- 2005-02-08 NO NO20050662A patent/NO20050662L/no not_active Application Discontinuation
- 2005-02-09 ZA ZA200501174A patent/ZA200501174B/xx unknown
- 2005-03-16 MA MA28149A patent/MA27436A1/fr unknown
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