JP2005500286A5 - - Google Patents
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- JP2005500286A5 JP2005500286A5 JP2003503606A JP2003503606A JP2005500286A5 JP 2005500286 A5 JP2005500286 A5 JP 2005500286A5 JP 2003503606 A JP2003503606 A JP 2003503606A JP 2003503606 A JP2003503606 A JP 2003503606A JP 2005500286 A5 JP2005500286 A5 JP 2005500286A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- phenyl
- amino
- alkoxy
- dimethoxy
- 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.)
- Pending
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- -1 tri-substituted phenyl Chemical group 0.000 claims 32
- 229910052736 halogen Inorganic materials 0.000 claims 28
- 150000002367 halogens Chemical class 0.000 claims 27
- 125000000217 alkyl group Chemical group 0.000 claims 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000003545 alkoxy group Chemical group 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- 125000001475 halogen functional group Chemical group 0.000 claims 8
- 125000004043 oxo group Chemical group O=* 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000002541 furyl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000001425 triazolyl group Chemical group 0.000 claims 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 2
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- LEUCFGXBIMXSTR-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-5-[2-methoxy-4-(trifluoromethoxy)phenyl]-3,6-dimethylpyrazine Chemical compound COC1=CC(OC)=CC=C1C1=NC(C)=C(C=2C(=CC(OC(F)(F)F)=CC=2)OC)N=C1C LEUCFGXBIMXSTR-UHFFFAOYSA-N 0.000 claims 2
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims 2
- 108010056643 Corticotropin-Releasing Hormone Receptors Proteins 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000000524 functional group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 2
- LIUBIORPMLRDJF-UHFFFAOYSA-N 1-[4-[5-(2,5-dimethylphenyl)-3,6-diethylpyrazin-2-yl]-3,5-dimethoxyphenyl]ethanol Chemical compound CCC1=NC(C=2C(=CC(=CC=2OC)C(C)O)OC)=C(CC)N=C1C1=CC(C)=CC=C1C LIUBIORPMLRDJF-UHFFFAOYSA-N 0.000 claims 1
- WUZIDBVQKLRIPB-UHFFFAOYSA-N 1-[4-[5-(2,5-dimethylphenyl)-3,6-diethylpyrazin-2-yl]-3,5-dimethoxyphenyl]ethanone Chemical compound CCC1=NC(C=2C(=CC(=CC=2OC)C(C)=O)OC)=C(CC)N=C1C1=CC(C)=CC=C1C WUZIDBVQKLRIPB-UHFFFAOYSA-N 0.000 claims 1
- BGZZRIMFHBIIEI-UHFFFAOYSA-N 2,5-bis(2,4-dimethoxyphenyl)-3,6-diethylpyrazine Chemical compound CCC1=NC(C=2C(=CC(OC)=CC=2)OC)=C(CC)N=C1C1=CC=C(OC)C=C1OC BGZZRIMFHBIIEI-UHFFFAOYSA-N 0.000 claims 1
- DGDWIDICUIAHMN-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-3,6-diethyl-5-(2,3,5-trichlorophenyl)pyrazine Chemical compound CCC1=NC(C=2C(=C(Cl)C=C(Cl)C=2)Cl)=C(CC)N=C1C1=CC=C(OC)C=C1OC DGDWIDICUIAHMN-UHFFFAOYSA-N 0.000 claims 1
- ZMTFJCIBWVYKMK-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-3,6-diethyl-5-(2,4,6-trimethylphenyl)pyrazine Chemical compound CCC1=NC(C=2C(=CC(C)=CC=2C)C)=C(CC)N=C1C1=CC=C(OC)C=C1OC ZMTFJCIBWVYKMK-UHFFFAOYSA-N 0.000 claims 1
- FHNRZIJAXCKDNH-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-3,6-diethyl-5-(2-methoxy-5-propan-2-ylphenyl)pyrazine Chemical compound CCC1=NC(C=2C(=CC=C(C=2)C(C)C)OC)=C(CC)N=C1C1=CC=C(OC)C=C1OC FHNRZIJAXCKDNH-UHFFFAOYSA-N 0.000 claims 1
- HHLZPPDELXXHLI-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-3,6-diethyl-5-(2-methylphenyl)pyrazine Chemical compound CCC1=NC(C=2C(=CC(OC)=CC=2)OC)=C(CC)N=C1C1=CC=CC=C1C HHLZPPDELXXHLI-UHFFFAOYSA-N 0.000 claims 1
- AKDXVUVTVXZOFF-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-3,6-diethyl-5-(3-methylphenyl)pyrazine Chemical compound CCC1=NC(C=2C(=CC(OC)=CC=2)OC)=C(CC)N=C1C1=CC=CC(C)=C1 AKDXVUVTVXZOFF-UHFFFAOYSA-N 0.000 claims 1
- HULSIAJKZKUTPU-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-3,6-diethyl-5-(4-fluoro-3-methylphenyl)pyrazine Chemical compound CCC1=NC(C=2C(=CC(OC)=CC=2)OC)=C(CC)N=C1C1=CC=C(F)C(C)=C1 HULSIAJKZKUTPU-UHFFFAOYSA-N 0.000 claims 1
- WBGBGXMECPELHI-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-3,6-diethyl-5-(5-fluoro-2-methoxyphenyl)pyrazine Chemical compound CCC1=NC(C=2C(=CC=C(F)C=2)OC)=C(CC)N=C1C1=CC=C(OC)C=C1OC WBGBGXMECPELHI-UHFFFAOYSA-N 0.000 claims 1
- XJYPDMJBVJECPV-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-3,6-diethyl-5-[2-(trifluoromethyl)phenyl]pyrazine Chemical compound CCC1=NC(C=2C(=CC=CC=2)C(F)(F)F)=C(CC)N=C1C1=CC=C(OC)C=C1OC XJYPDMJBVJECPV-UHFFFAOYSA-N 0.000 claims 1
- QKYNPRQCZBBACO-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-3,6-diethyl-5-[3-(trifluoromethoxy)phenyl]pyrazine Chemical compound CCC1=NC(C=2C(=CC(OC)=CC=2)OC)=C(CC)N=C1C1=CC=CC(OC(F)(F)F)=C1 QKYNPRQCZBBACO-UHFFFAOYSA-N 0.000 claims 1
- QFLCTLQRAGZVPR-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-3,6-diethyl-5-[3-(trifluoromethyl)phenyl]pyrazine Chemical compound CCC1=NC(C=2C(=CC(OC)=CC=2)OC)=C(CC)N=C1C1=CC=CC(C(F)(F)F)=C1 QFLCTLQRAGZVPR-UHFFFAOYSA-N 0.000 claims 1
- FTLCVJIYNXJAKB-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-3,6-diethyl-5-naphthalen-1-ylpyrazine Chemical compound CCC1=NC(C=2C3=CC=CC=C3C=CC=2)=C(CC)N=C1C1=CC=C(OC)C=C1OC FTLCVJIYNXJAKB-UHFFFAOYSA-N 0.000 claims 1
- BVCPGUGHWQTKEJ-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-3,6-diethyl-5-naphthalen-2-ylpyrazine Chemical compound CCC=1N=C(C=2C=C3C=CC=CC3=CC=2)C(CC)=NC=1C1=CC=C(OC)C=C1OC BVCPGUGHWQTKEJ-UHFFFAOYSA-N 0.000 claims 1
- BGHCMPVFVKWWBZ-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-3,6-diethyl-5-phenylpyrazine Chemical compound CCC1=NC(C=2C(=CC(OC)=CC=2)OC)=C(CC)N=C1C1=CC=CC=C1 BGHCMPVFVKWWBZ-UHFFFAOYSA-N 0.000 claims 1
- ULBLIKCTKCWWID-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-3,6-dimethyl-5-(2-methylphenyl)pyrazine Chemical compound COC1=CC(OC)=CC=C1C1=NC(C)=C(C=2C(=CC=CC=2)C)N=C1C ULBLIKCTKCWWID-UHFFFAOYSA-N 0.000 claims 1
- NMYQXTOJTJXABZ-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-5-(2,3-dimethylphenyl)-3,6-diethylpyrazine Chemical compound CCC1=NC(C=2C(=CC(OC)=CC=2)OC)=C(CC)N=C1C1=CC=CC(C)=C1C NMYQXTOJTJXABZ-UHFFFAOYSA-N 0.000 claims 1
- LVZNFDXIXYQITO-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-5-(2,5-dimethoxyphenyl)-3,6-diethylpyrazine Chemical compound CCC1=NC(C=2C(=CC=C(OC)C=2)OC)=C(CC)N=C1C1=CC=C(OC)C=C1OC LVZNFDXIXYQITO-UHFFFAOYSA-N 0.000 claims 1
- KMMOUEUBVQKIOZ-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-5-(2,5-dimethylphenyl)-3,6-diethylpyrazine Chemical compound CCC1=NC(C=2C(=CC=C(C)C=2)C)=C(CC)N=C1C1=CC=C(OC)C=C1OC KMMOUEUBVQKIOZ-UHFFFAOYSA-N 0.000 claims 1
- VILHKICPLHVTHQ-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-5-(2,6-dimethylphenyl)-3,6-diethylpyrazine Chemical compound CCC1=NC(C=2C(=CC=CC=2C)C)=C(CC)N=C1C1=CC=C(OC)C=C1OC VILHKICPLHVTHQ-UHFFFAOYSA-N 0.000 claims 1
- JTJFDQBQZILVDR-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-5-(3,5-dimethylphenyl)-3,6-diethylpyrazine Chemical compound CCC1=NC(C=2C(=CC(OC)=CC=2)OC)=C(CC)N=C1C1=CC(C)=CC(C)=C1 JTJFDQBQZILVDR-UHFFFAOYSA-N 0.000 claims 1
- QJAMUCWIAHNPRS-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)-5-(2,4-dimethoxyphenyl)-3,6-diethylpyrazine Chemical compound CCC1=NC(C=2C(=CC(OC)=CC=2)OC)=C(CC)N=C1C1=CC(Cl)=CC=C1Cl QJAMUCWIAHNPRS-UHFFFAOYSA-N 0.000 claims 1
- GGPSFFARPDXADE-UHFFFAOYSA-N 2-(2,5-dimethylphenyl)-3,6-diethyl-5-[4-(1-fluoroethyl)-2,6-dimethoxyphenyl]pyrazine Chemical compound CCC1=NC(C=2C(=CC(=CC=2OC)C(C)F)OC)=C(CC)N=C1C1=CC(C)=CC=C1C GGPSFFARPDXADE-UHFFFAOYSA-N 0.000 claims 1
- GVJILNWFSKAYCX-UHFFFAOYSA-N 2-(2,5-dimethylphenyl)-3,6-diethyl-5-[4-(2-fluoropropan-2-yl)-2,6-dimethoxyphenyl]pyrazine Chemical compound CCC1=NC(C=2C(=CC(=CC=2OC)C(C)(C)F)OC)=C(CC)N=C1C1=CC(C)=CC=C1C GVJILNWFSKAYCX-UHFFFAOYSA-N 0.000 claims 1
- OTAJFFMNPOIMMD-UHFFFAOYSA-N 2-(5-chloro-2-methoxyphenyl)-5-(2,4-dimethoxyphenyl)-3,6-diethylpyrazine Chemical compound CCC1=NC(C=2C(=CC=C(Cl)C=2)OC)=C(CC)N=C1C1=CC=C(OC)C=C1OC OTAJFFMNPOIMMD-UHFFFAOYSA-N 0.000 claims 1
- CDCSWCQJUWIEQB-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-5-(2,4-dimethoxyphenyl)-3,6-diethylpyrazine Chemical compound CCC1=NC(C=2C(=CC(OC)=CC=2)OC)=C(CC)N=C1C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CDCSWCQJUWIEQB-UHFFFAOYSA-N 0.000 claims 1
- TYYCKFPMBRRBJO-UHFFFAOYSA-N 2-[4-(difluoromethyl)-2,6-dimethoxyphenyl]-5-(2,5-dimethylphenyl)-3,6-diethylpyrazine Chemical compound CCC1=NC(C=2C(=CC(=CC=2OC)C(F)F)OC)=C(CC)N=C1C1=CC(C)=CC=C1C TYYCKFPMBRRBJO-UHFFFAOYSA-N 0.000 claims 1
- AVFGIQIAGRLQIT-UHFFFAOYSA-N 2-[4-[5-(2,5-dimethylphenyl)-3,6-diethylpyrazin-2-yl]-3,5-dimethoxyphenyl]propan-2-ol Chemical compound CCC1=NC(C=2C(=CC(=CC=2OC)C(C)(C)O)OC)=C(CC)N=C1C1=CC(C)=CC=C1C AVFGIQIAGRLQIT-UHFFFAOYSA-N 0.000 claims 1
- BOJORVHSOBCQLB-UHFFFAOYSA-N 2-methoxy-6-[2-methoxy-4-(trifluoromethoxy)phenyl]-5-methyl-3-(5-propyltetrazol-1-yl)pyridine Chemical compound CCCC1=NN=NN1C1=CC(C)=C(C=2C(=CC(OC(F)(F)F)=CC=2)OC)N=C1OC BOJORVHSOBCQLB-UHFFFAOYSA-N 0.000 claims 1
- FWFQNYFIVKWSFP-UHFFFAOYSA-N 3-(3,5-diethylpyrazol-1-yl)-2-methoxy-6-[2-methoxy-4-(trifluoromethoxy)phenyl]-5-methylpyridine Chemical compound N1=C(CC)C=C(CC)N1C1=CC(C)=C(C=2C(=CC(OC(F)(F)F)=CC=2)OC)N=C1OC FWFQNYFIVKWSFP-UHFFFAOYSA-N 0.000 claims 1
- CJTVOBMYVFONBL-UHFFFAOYSA-N 4-[5-(2,5-dimethylphenyl)-3,6-diethylpyrazin-2-yl]-3,5-dimethoxybenzaldehyde Chemical compound CCC1=NC(C=2C(=CC(C=O)=CC=2OC)OC)=C(CC)N=C1C1=CC(C)=CC=C1C CJTVOBMYVFONBL-UHFFFAOYSA-N 0.000 claims 1
- JSXKXOSIJYZLNF-UHFFFAOYSA-N 5-(5-fluoro-2-methoxyphenyl)-4-methoxy-2-(2-methoxy-4,6-dimethylphenyl)-6-methylpyrimidine Chemical compound COC1=CC=C(F)C=C1C1=C(C)N=C(C=2C(=CC(C)=CC=2C)OC)N=C1OC JSXKXOSIJYZLNF-UHFFFAOYSA-N 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- JEXZKUACIJIPLM-UHFFFAOYSA-N [3-[2-methoxy-6-[2-methoxy-4-(trifluoromethoxy)phenyl]-5-methylpyridin-3-yl]imidazol-4-yl]-morpholin-4-ylmethanone Chemical compound COC1=CC(OC(F)(F)F)=CC=C1C1=NC(OC)=C(N2C(=CN=C2)C(=O)N2CCOCC2)C=C1C JEXZKUACIJIPLM-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000001525 receptor binding assay Methods 0.000 claims 1
- 0 CC(*)=*C(*)=C(C=C)c1nc(*I)c(C)c(*)n1 Chemical compound CC(*)=*C(*)=C(C=C)c1nc(*I)c(C)c(*)n1 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29748301P | 2001-06-12 | 2001-06-12 | |
| PCT/US2002/016518 WO2002100838A1 (en) | 2001-06-12 | 2002-05-22 | 2,5-diarylpyrazines, 2,5-diarylpyridines and 2,5-diarylpyrimidines as crf1 receptor modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005500286A JP2005500286A (ja) | 2005-01-06 |
| JP2005500286A5 true JP2005500286A5 (OSRAM) | 2006-01-05 |
Family
ID=23146501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003503606A Pending JP2005500286A (ja) | 2001-06-12 | 2002-05-22 | Ｃｒｆ１受容体モジュレータとしての２，５−ジアリールピラジン、２，５−ジアリールピリジンおよび２，５−ジアリールピリミジン |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US6887875B2 (OSRAM) |
| EP (1) | EP1399428A1 (OSRAM) |
| JP (1) | JP2005500286A (OSRAM) |
| AP (1) | AP2003002924A0 (OSRAM) |
| BG (1) | BG108427A (OSRAM) |
| CA (1) | CA2450262A1 (OSRAM) |
| EC (1) | ECSP034898A (OSRAM) |
| HR (1) | HRP20031096A2 (OSRAM) |
| HU (1) | HUP0400179A3 (OSRAM) |
| IL (1) | IL159058A0 (OSRAM) |
| IS (1) | IS7060A (OSRAM) |
| MX (1) | MXPA03011391A (OSRAM) |
| PL (1) | PL367476A1 (OSRAM) |
| RU (1) | RU2003136151A (OSRAM) |
| TN (1) | TNSN03133A1 (OSRAM) |
| WO (1) | WO2002100838A1 (OSRAM) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL146531A0 (en) * | 2000-03-16 | 2002-07-25 | Neurogen Corp | 5-substituted arylpyrimidines |
| US6964965B2 (en) | 2002-04-26 | 2005-11-15 | Pharmacia & Upjohn | Substituted pyrazine derivatives |
| ATE325115T1 (de) | 2002-08-19 | 2006-06-15 | Glaxo Group Ltd | Pyrimidinderivate als selektive cox-2-inhibitoren |
| GB0221443D0 (en) | 2002-09-16 | 2002-10-23 | Glaxo Group Ltd | Pyridine derivates |
| GB0225548D0 (en) | 2002-11-01 | 2002-12-11 | Glaxo Group Ltd | Compounds |
| AU2003278542A1 (en) * | 2002-11-21 | 2004-06-15 | Pharmacia & Upjohn Company Llc | Pyrazine compounds as crf modulators |
| JP2007512275A (ja) | 2003-11-24 | 2007-05-17 | エフ．ホフマン−ラ ロシュ アーゲー | ピラゾリルおよびイミダゾリルピリミジン |
| US20080132522A1 (en) * | 2004-07-14 | 2008-06-05 | Basf Aktiengesellschaft | 2-Substituted Pyrimidines, Method for Their Production and Their Use for Controlling Pathogenic Fungi |
| TW200637556A (en) * | 2005-01-31 | 2006-11-01 | Basf Ag | Substituted 5-phenyl pyrimidines I in therapy |
| KR20080040692A (ko) * | 2005-08-02 | 2008-05-08 | 렉시컨 파마슈티컬스 인코퍼레이티드 | 단백질 키나제 억제제로서의 2-아미노아릴 피리딘 |
| TW200908984A (en) * | 2007-08-07 | 2009-03-01 | Piramal Life Sciences Ltd | Pyridyl derivatives, their preparation and use |
| US7932256B2 (en) * | 2008-07-31 | 2011-04-26 | Bristol-Myers Squibb Company | (S)-4-(1-cyclopropyl-2-methoxyethyl)-6-(6-(difluoromethoxy)-2,5-dimethylpyridin-3-ylamino)-5-oxo-4,5-dihydropyrazine-2-carbonitrile: a pyrazinone modulator of corticotropin-releasing factor receptor activity |
| WO2011051478A1 (en) * | 2009-10-30 | 2011-05-05 | Domain Therapeutics | Novel oxime derivatives and their use as allosteric modulators of metabotropic glutamate receptors |
| US9357781B2 (en) | 2013-05-03 | 2016-06-07 | Inscent, Inc. | Honeybee repellents and uses thereof |
| US9351494B2 (en) | 2013-05-03 | 2016-05-31 | Inscent, Inc. | Honeybee repellents and uses thereof |
| CN105254576A (zh) * | 2014-02-26 | 2016-01-20 | 中国科学院长春应用化学研究所 | 一种谷氨酸二酮哌嗪的制备方法 |
| KR102708681B1 (ko) | 2018-02-13 | 2024-09-26 | 길리애드 사이언시즈, 인코포레이티드 | Pd-1/pd-l1 억제제 |
| CN118221646A (zh) | 2018-07-13 | 2024-06-21 | 吉利德科学公司 | Pd-1/pd-l1抑制剂 |
| JP2022074173A (ja) * | 2019-03-18 | 2022-05-18 | 住友化学株式会社 | ２，５－ジクロロピラジンの製造方法 |
| CN112142716B (zh) * | 2020-10-29 | 2021-08-31 | 山东新时代药业有限公司 | 一种5元杂芳基取代的吡嗪衍生物及其应用 |
| CN113429354A (zh) * | 2021-07-22 | 2021-09-24 | 广东嘉博制药有限公司 | 一种盐酸甲氧明聚合物杂质及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1463813A (fr) * | 1964-02-26 | 1966-07-22 | Ciba Geigy | Nouvelles amino-phénylcétones et procédé pour leur préparation |
| US3660404A (en) * | 1969-02-24 | 1972-05-02 | Du Pont | U.v.-absorbing ortho-hydroxyphenyl substituted bipyrimidyls |
| DE2064380C3 (de) * | 1970-12-30 | 1981-01-22 | Hoechst Ag, 6000 Frankfurt | Lichtempfindliches Gemisch |
| JPS625970A (ja) | 1985-03-15 | 1987-01-12 | Terumo Corp | ピラジン誘導体およびこれを含有する血小板凝集抑制剤 |
| DE68926635T2 (de) * | 1988-04-25 | 1997-01-02 | Dainippon Ink & Chemicals | 2,5-Disubstituierte Pyrazin-Derivate, Pyrimidin-Derivate und sie enthaltende Flüssigkristalle |
| JPH02209873A (ja) * | 1989-02-08 | 1990-08-21 | Dainippon Ink & Chem Inc | 光学活性２，５―ジ置換ピリミジン誘導体 |
| JP2770385B2 (ja) * | 1989-03-16 | 1998-07-02 | セイコーエプソン株式会社 | ピリミジン誘導体 |
| WO1995010506A1 (en) * | 1993-10-12 | 1995-04-20 | The Du Pont Merck Pharmaceutical Company | 1n-alkyl-n-arylpyrimidinamines and derivatives thereof |
| JPH0948760A (ja) * | 1995-08-03 | 1997-02-18 | Dainippon Ink & Chem Inc | ピリミジン化合物 |
| JP4044175B2 (ja) * | 1996-07-26 | 2008-02-06 | 株式会社半導体エネルギー研究所 | 光学活性化合物及び該化合物を含有する反強誘電性液晶組成物 |
| US6686486B1 (en) * | 1997-05-07 | 2004-02-03 | Padma Marwah | Process for effecting allylic oxidation |
| SE9702651D0 (sv) * | 1997-07-09 | 1997-07-09 | Astra Pharma Prod | Novel compounds |
| WO1999038829A1 (en) * | 1998-01-28 | 1999-08-05 | Shionogi & Co., Ltd. | Novel tricyclic compound |
| CO5210940A1 (es) * | 1999-05-04 | 2002-10-30 | Novartis Ag | Compuestos plaguicidas derivados de pirimidina y composiciones que los contienen |
| NZ520484A (en) * | 2000-02-16 | 2005-03-24 | Neurogen Corp | Substituted arylpyrazines that are modulators of CRF (corticotropin releasing factor) receptor and methods of treatment using them |
-
2002
- 2002-05-22 HR HR20031096A patent/HRP20031096A2/xx not_active Application Discontinuation
- 2002-05-22 JP JP2003503606A patent/JP2005500286A/ja active Pending
- 2002-05-22 RU RU2003136151/04A patent/RU2003136151A/ru not_active Application Discontinuation
- 2002-05-22 EP EP02737167A patent/EP1399428A1/en not_active Withdrawn
- 2002-05-22 CA CA002450262A patent/CA2450262A1/en not_active Abandoned
- 2002-05-22 HU HU0400179A patent/HUP0400179A3/hu unknown
- 2002-05-22 IL IL15905802A patent/IL159058A0/xx unknown
- 2002-05-22 WO PCT/US2002/016518 patent/WO2002100838A1/en not_active Ceased
- 2002-05-22 AP APAP/P/2003/002924A patent/AP2003002924A0/en unknown
- 2002-05-22 US US10/154,482 patent/US6887875B2/en not_active Expired - Fee Related
- 2002-05-22 PL PL02367476A patent/PL367476A1/xx not_active Application Discontinuation
- 2002-05-22 MX MXPA03011391A patent/MXPA03011391A/es unknown
-
2003
- 2003-07-08 TN TNPCT/US2002/016518A patent/TNSN03133A1/en unknown
- 2003-11-28 IS IS7060A patent/IS7060A/is unknown
- 2003-12-08 BG BG108427A patent/BG108427A/xx unknown
- 2003-12-12 EC EC2003004898A patent/ECSP034898A/es unknown
-
2005
- 2005-04-04 US US11/098,885 patent/US20050176721A1/en not_active Abandoned
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