RU2003136151A - 2, 5-диарилпиразины, 2, 5-диарилпиридины и 2, 5-диарилпиримидины в качестве модуляторов рецептора кортикотропин-рилизинг-фактора 1 (крф1) - Google Patents
2, 5-диарилпиразины, 2, 5-диарилпиридины и 2, 5-диарилпиримидины в качестве модуляторов рецептора кортикотропин-рилизинг-фактора 1 (крф1) Download PDFInfo
- Publication number
- RU2003136151A RU2003136151A RU2003136151/04A RU2003136151A RU2003136151A RU 2003136151 A RU2003136151 A RU 2003136151A RU 2003136151/04 A RU2003136151/04 A RU 2003136151/04A RU 2003136151 A RU2003136151 A RU 2003136151A RU 2003136151 A RU2003136151 A RU 2003136151A
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- phenyl
- alkoxy
- amino
- mono
- Prior art date
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- 229910052736 halogen Inorganic materials 0.000 claims 50
- 150000001875 compounds Chemical class 0.000 claims 46
- -1 pyridisinyl Chemical group 0.000 claims 40
- 150000002367 halogens Chemical class 0.000 claims 39
- 150000003839 salts Chemical class 0.000 claims 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 23
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 150000002431 hydrogen Chemical class 0.000 claims 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 229910052757 nitrogen Inorganic materials 0.000 claims 14
- 125000004076 pyridyl group Chemical group 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 125000004043 oxo group Chemical group O=* 0.000 claims 10
- 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 9
- 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 9
- 238000000034 method Methods 0.000 claims 9
- 239000000523 sample Substances 0.000 claims 9
- 108010056643 Corticotropin-Releasing Hormone Receptors Proteins 0.000 claims 8
- 239000012472 biological sample Substances 0.000 claims 8
- 125000002541 furyl group Chemical group 0.000 claims 8
- 125000002883 imidazolyl group Chemical group 0.000 claims 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims 8
- 102000012289 Corticotropin-Releasing Hormone Human genes 0.000 claims 7
- 108010022152 Corticotropin-Releasing Hormone Proteins 0.000 claims 7
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 108091005471 CRHR1 Proteins 0.000 claims 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 5
- 125000000842 isoxazolyl group Chemical group 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000002971 oxazolyl group Chemical group 0.000 claims 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims 5
- 125000000335 thiazolyl group Chemical group 0.000 claims 5
- 125000001544 thienyl group Chemical group 0.000 claims 5
- 125000001425 triazolyl group Chemical group 0.000 claims 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 238000000338 in vitro Methods 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 210000004027 cell Anatomy 0.000 claims 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 3
- 238000011534 incubation Methods 0.000 claims 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 125000004193 piperazinyl group Chemical group 0.000 claims 3
- 125000003386 piperidinyl group Chemical group 0.000 claims 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 3
- 238000001525 receptor binding assay Methods 0.000 claims 3
- 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 3
- 238000005406 washing Methods 0.000 claims 3
- 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 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
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 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
- 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
- LHNUBEVQAMLATC-UHFFFAOYSA-N 2-(2,5-dimethylphenyl)-5-[4-(1,3-dioxolan-2-yl)-2,6-dimethoxyphenyl]-3,6-diethylpyrazine Chemical compound CCC1=NC(C=2C(=CC(=CC=2OC)C2OCCO2)OC)=C(CC)N=C1C1=CC(C)=CC=C1C LHNUBEVQAMLATC-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
- 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
- 239000000443 aerosol Substances 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 238000000376 autoradiography Methods 0.000 claims 1
- 210000001124 body fluid Anatomy 0.000 claims 1
- 239000010839 body fluid Substances 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000000499 gel Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 210000002569 neuron Anatomy 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0455—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0459—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with two nitrogen atoms as the only ring hetero atoms, e.g. piperazine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0463—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Optics & Photonics (AREA)
- Physics & Mathematics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29748301P | 2001-06-12 | 2001-06-12 | |
| US60/297,483 | 2001-06-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2003136151A true RU2003136151A (ru) | 2005-05-20 |
Family
ID=23146501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2003136151/04A RU2003136151A (ru) | 2001-06-12 | 2002-05-22 | 2, 5-диарилпиразины, 2, 5-диарилпиридины и 2, 5-диарилпиримидины в качестве модуляторов рецептора кортикотропин-рилизинг-фактора 1 (крф1) |
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 |
Family Cites Families (15)
| 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
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0400179A2 (hu) | 2004-08-30 |
| US6887875B2 (en) | 2005-05-03 |
| IS7060A (is) | 2003-11-28 |
| CA2450262A1 (en) | 2002-12-19 |
| MXPA03011391A (es) | 2004-07-01 |
| TNSN03133A1 (en) | 2005-12-23 |
| JP2005500286A (ja) | 2005-01-06 |
| BG108427A (en) | 2005-01-31 |
| US20050176721A1 (en) | 2005-08-11 |
| PL367476A1 (en) | 2005-02-21 |
| US20030119844A1 (en) | 2003-06-26 |
| AP2003002924A0 (en) | 2003-12-31 |
| IL159058A0 (en) | 2004-05-12 |
| WO2002100838A1 (en) | 2002-12-19 |
| EP1399428A1 (en) | 2004-03-24 |
| HUP0400179A3 (en) | 2004-10-28 |
| HRP20031096A2 (en) | 2005-08-31 |
| ECSP034898A (es) | 2004-01-28 |
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Legal Events
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| FA93 | Acknowledgement of application withdrawn (no request for examination) |
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