NO313520B1 - Indolderivater som 5-HT-reseptor-agonister, fremgangsmåte ved fremstilling derav og farmasöytiske preparater inneholdende dem - Google Patents
Indolderivater som 5-HT-reseptor-agonister, fremgangsmåte ved fremstilling derav og farmasöytiske preparater inneholdende dem Download PDFInfo
- Publication number
- NO313520B1 NO313520B1 NO19973543A NO973543A NO313520B1 NO 313520 B1 NO313520 B1 NO 313520B1 NO 19973543 A NO19973543 A NO 19973543A NO 973543 A NO973543 A NO 973543A NO 313520 B1 NO313520 B1 NO 313520B1
- Authority
- NO
- Norway
- Prior art keywords
- trifluoromethyl
- indoline
- methoxy
- phenylcarbamoyl
- pyrid
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 75
- 238000002360 preparation method Methods 0.000 title claims description 12
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 4
- 150000002475 indoles Chemical class 0.000 title description 2
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 title 1
- 102000014630 G protein-coupled serotonin receptor activity proteins Human genes 0.000 title 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 239000000018 receptor agonist Substances 0.000 title 1
- 229940044601 receptor agonist Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 175
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- -1 C-j.6alkylthio Chemical group 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 230000008878 coupling Effects 0.000 claims description 5
- 238000010168 coupling process Methods 0.000 claims description 5
- 238000005859 coupling reaction Methods 0.000 claims description 5
- 125000000524 functional group Chemical group 0.000 claims description 5
- AQKLFYUGEBTKMZ-UHFFFAOYSA-N 5-methoxy-n-(3-phenyl-5-pyridin-3-ylphenyl)-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=1)=CC(C=2C=CC=CC=2)=CC=1C1=CC=CN=C1 AQKLFYUGEBTKMZ-UHFFFAOYSA-N 0.000 claims description 4
- GSQYHDORJZCDFN-UHFFFAOYSA-N 5-methylsulfanyl-n-[3-(2-pyridin-3-yl-1,3-thiazol-4-yl)phenyl]-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(SC)=CC=2CCN1C(=O)NC(C=1)=CC=CC=1C(N=1)=CSC=1C1=CC=CN=C1 GSQYHDORJZCDFN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- FNWNLUXEHHLLML-UHFFFAOYSA-N n-(3-bromo-5-pyridin-3-ylphenyl)-5-methoxy-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=1)=CC(Br)=CC=1C1=CC=CN=C1 FNWNLUXEHHLLML-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- XCBITNZSYILANP-UHFFFAOYSA-N 5-methoxy-n-(1-pyridin-3-ylindol-5-yl)-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=C1C=C2)=CC=C1N2C1=CC=CN=C1 XCBITNZSYILANP-UHFFFAOYSA-N 0.000 claims description 3
- PTSQKGMZHRDEEV-UHFFFAOYSA-N 5-methoxy-n-(2-pyrazin-2-yl-1,3-thiazol-4-yl)-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(N=1)=CSC=1C1=CN=CC=N1 PTSQKGMZHRDEEV-UHFFFAOYSA-N 0.000 claims description 3
- DMRXJAXJPGLFQM-UHFFFAOYSA-N 5-methoxy-n-(2-pyridin-3-yl-1,3-thiazol-4-yl)-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(N=1)=CSC=1C1=CC=CN=C1 DMRXJAXJPGLFQM-UHFFFAOYSA-N 0.000 claims description 3
- DMEXMJLHCOAJSO-UHFFFAOYSA-N 5-methoxy-n-(3-pyrimidin-5-ylphenyl)-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=1)=CC=CC=1C1=CN=CN=C1 DMEXMJLHCOAJSO-UHFFFAOYSA-N 0.000 claims description 3
- RCKUMMWWCMFKRU-UHFFFAOYSA-N 5-methoxy-n-(4-methoxy-3-pyridin-3-ylphenyl)-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound COC1=CC=C(NC(=O)N2C3=CC(=C(OC)C=C3CC2)C(F)(F)F)C=C1C1=CC=CN=C1 RCKUMMWWCMFKRU-UHFFFAOYSA-N 0.000 claims description 3
- VMBKNKMDWXZGME-UHFFFAOYSA-N 5-methoxy-n-(5-phenylpyridin-3-yl)-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=1)=CN=CC=1C1=CC=CC=C1 VMBKNKMDWXZGME-UHFFFAOYSA-N 0.000 claims description 3
- CYMQBSJAKOLDKP-UHFFFAOYSA-N 5-methoxy-n-(5-pyridin-2-ylthiophen-2-yl)-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(S1)=CC=C1C1=CC=CC=N1 CYMQBSJAKOLDKP-UHFFFAOYSA-N 0.000 claims description 3
- UIOUZAKDFIQYKJ-UHFFFAOYSA-N 5-methoxy-n-(5-pyridin-4-ylpyridin-3-yl)-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=1)=CN=CC=1C1=CC=NC=C1 UIOUZAKDFIQYKJ-UHFFFAOYSA-N 0.000 claims description 3
- GYCWCSSBHBSLLK-UHFFFAOYSA-N 5-methoxy-n-(6-pyridin-3-yloxypyridin-3-yl)-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=N1)=CC=C1OC1=CC=CN=C1 GYCWCSSBHBSLLK-UHFFFAOYSA-N 0.000 claims description 3
- UFWHHDBSWOBBQO-UHFFFAOYSA-N 5-methoxy-n-(6-pyridin-3-ylpyridin-3-yl)-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=N1)=CC=C1C1=CC=CN=C1 UFWHHDBSWOBBQO-UHFFFAOYSA-N 0.000 claims description 3
- TUKXLWDAMSYWIT-UHFFFAOYSA-N 5-methoxy-n-(6-pyridin-3-ylsulfanylpyridin-3-yl)-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=N1)=CC=C1SC1=CC=CN=C1 TUKXLWDAMSYWIT-UHFFFAOYSA-N 0.000 claims description 3
- VSGPZSVKVXFLOY-UHFFFAOYSA-N 5-methoxy-n-[3-(4-methylpyridin-3-yl)phenyl]-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=1)=CC=CC=1C1=CN=CC=C1C VSGPZSVKVXFLOY-UHFFFAOYSA-N 0.000 claims description 3
- WJLZRVFPCNRCKU-UHFFFAOYSA-N 6-chloro-5-methyl-n-[4-methyl-3-(4-methylpyridin-3-yl)phenyl]-2,3-dihydroindole-1-carboxamide Chemical compound CC1=CC=NC=C1C1=CC(NC(=O)N2C3=CC(Cl)=C(C)C=C3CC2)=CC=C1C WJLZRVFPCNRCKU-UHFFFAOYSA-N 0.000 claims description 3
- WHIABSZOSLXOTJ-UHFFFAOYSA-N n-(3-ethyl-5-pyridin-3-ylphenyl)-5-methoxy-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C=1C(CC)=CC(NC(=O)N2C3=CC(=C(OC)C=C3CC2)C(F)(F)F)=CC=1C1=CC=CN=C1 WHIABSZOSLXOTJ-UHFFFAOYSA-N 0.000 claims description 3
- XTUFMBUGWUNIJA-UHFFFAOYSA-N n-(3-fluoro-4-methoxy-5-pyridin-3-ylphenyl)-5-methoxy-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=1)=CC(F)=C(OC)C=1C1=CC=CN=C1 XTUFMBUGWUNIJA-UHFFFAOYSA-N 0.000 claims description 3
- QFHSLRKLLUGFLN-UHFFFAOYSA-N n-(3-isoquinolin-4-ylphenyl)-5-methoxy-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=CC=C2C(C=3C=CC=C(C=3)NC(=O)N3CCC=4C=C(C(=CC=43)C(F)(F)F)OC)=CN=CC2=C1 QFHSLRKLLUGFLN-UHFFFAOYSA-N 0.000 claims description 3
- QODRLEBXZLZSBQ-UHFFFAOYSA-N n-(4-chloro-3-pyridin-3-ylphenyl)-5-methoxy-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=1)=CC=C(Cl)C=1C1=CC=CN=C1 QODRLEBXZLZSBQ-UHFFFAOYSA-N 0.000 claims description 3
- FTJNHAUXWUOACE-UHFFFAOYSA-N n-[6-(2-methylpyridin-3-yl)oxypyridin-3-yl]-5-methylsulfanyl-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(SC)=CC=2CCN1C(=O)NC(C=N1)=CC=C1OC1=CC=CN=C1C FTJNHAUXWUOACE-UHFFFAOYSA-N 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- SXBHICYVWPUTOA-UHFFFAOYSA-N 5-methoxy-n-(7-pyridin-3-yl-2,3-dihydro-1-benzofuran-5-yl)-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=1)=CC=2CCOC=2C=1C1=CC=CN=C1 SXBHICYVWPUTOA-UHFFFAOYSA-N 0.000 claims description 2
- UAJJQZFBNVGDRP-UHFFFAOYSA-N 5-methoxy-n-[1-(pyridin-3-ylmethyl)indol-5-yl]-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=C1C=C2)=CC=C1N2CC1=CC=CN=C1 UAJJQZFBNVGDRP-UHFFFAOYSA-N 0.000 claims description 2
- GYURQQHRPNRXRZ-UHFFFAOYSA-N 5-methoxy-n-[1-(pyridin-4-ylmethyl)indol-5-yl]-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=C1C=C2)=CC=C1N2CC1=CC=NC=C1 GYURQQHRPNRXRZ-UHFFFAOYSA-N 0.000 claims description 2
- ROWMRXQBMZAMHD-UHFFFAOYSA-N 5-methoxy-n-[3-(pyridin-3-ylcarbamoyl)phenyl]-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=1)=CC=CC=1C(=O)NC1=CC=CN=C1 ROWMRXQBMZAMHD-UHFFFAOYSA-N 0.000 claims description 2
- PUOBHTVELJDWIM-UHFFFAOYSA-N 5-methoxy-n-[3-(pyridine-3-carbonyl)phenyl]-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=1)=CC=CC=1C(=O)C1=CC=CN=C1 PUOBHTVELJDWIM-UHFFFAOYSA-N 0.000 claims description 2
- XCORDYHGLWTUMS-UHFFFAOYSA-N 5-methoxy-n-[4-(pyridin-4-ylmethoxy)phenyl]-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=C1)=CC=C1OCC1=CC=NC=C1 XCORDYHGLWTUMS-UHFFFAOYSA-N 0.000 claims description 2
- XNHDZDVZRORPIP-UHFFFAOYSA-N 5-methoxy-n-[4-(pyridin-4-ylsulfanylmethyl)phenyl]-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=C1)=CC=C1CSC1=CC=NC=C1 XNHDZDVZRORPIP-UHFFFAOYSA-N 0.000 claims description 2
- IVIDCGBGPDBYIQ-UHFFFAOYSA-N 5-methoxy-n-[6-(4-methylpyridin-3-yl)oxypyridin-3-yl]-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=N1)=CC=C1OC1=CN=CC=C1C IVIDCGBGPDBYIQ-UHFFFAOYSA-N 0.000 claims description 2
- DLUDXFQJJRMRFQ-UHFFFAOYSA-N 5-methylsulfanyl-n-[4-(2-pyridin-4-yl-1,3-thiazol-4-yl)phenyl]-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(SC)=CC=2CCN1C(=O)NC(C=C1)=CC=C1C(N=1)=CSC=1C1=CC=NC=C1 DLUDXFQJJRMRFQ-UHFFFAOYSA-N 0.000 claims description 2
- WJPGCLNEQWALCN-UHFFFAOYSA-N 5-methylsulfanyl-n-[4-(pyridin-3-ylcarbamoyl)phenyl]-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(SC)=CC=2CCN1C(=O)NC(C=C1)=CC=C1C(=O)NC1=CC=CN=C1 WJPGCLNEQWALCN-UHFFFAOYSA-N 0.000 claims description 2
- RECDLRRCAGXVMZ-UHFFFAOYSA-N 6-chloro-5-methyl-n-(4-methyl-3-pyridin-3-ylphenyl)-2,3-dihydroindole-1-carboxamide Chemical compound CC1=CC=C(NC(=O)N2C3=CC(Cl)=C(C)C=C3CC2)C=C1C1=CC=CN=C1 RECDLRRCAGXVMZ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
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- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 claims description 2
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- 125000002541 furyl group Chemical group 0.000 claims description 2
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 2
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- JPJZJSNUFFGCEC-UHFFFAOYSA-N n-[4-chloro-3-(4-methylpyridin-3-yl)phenyl]-5-methoxy-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(OC)=CC=2CCN1C(=O)NC(C=1)=CC=C(Cl)C=1C1=CN=CC=C1C JPJZJSNUFFGCEC-UHFFFAOYSA-N 0.000 description 1
- MLUDIKJNCMCLCZ-UHFFFAOYSA-N n-[6-(6-methylpyridin-3-yl)oxypyridin-3-yl]-5-methylsulfanyl-6-(trifluoromethyl)-2,3-dihydroindole-1-carboxamide Chemical compound C1=2C=C(C(F)(F)F)C(SC)=CC=2CCN1C(=O)NC(C=N1)=CC=C1OC1=CC=C(C)N=C1 MLUDIKJNCMCLCZ-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- WXRFKWWSNPJOJB-UHFFFAOYSA-N phenyl n-[5-methyl-2-(1,2,4-oxadiazol-3-yl)phenyl]carbamate Chemical compound C=1C=CC=CC=1OC(=O)NC1=CC(C)=CC=C1C=1N=CON=1 WXRFKWWSNPJOJB-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229960004838 phosphoric acid Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 1
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
- XQWBMZWDJAZPPX-UHFFFAOYSA-N pyridine-3-carbothioamide Chemical compound NC(=S)C1=CC=CN=C1 XQWBMZWDJAZPPX-UHFFFAOYSA-N 0.000 description 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
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- 238000007789 sealing Methods 0.000 description 1
- 239000002891 serotonin 2B antagonist Substances 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001391 thioamide group Chemical group 0.000 description 1
- 238000006365 thiocyanation reaction Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 231100000759 toxicological effect Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- DLTHSKKNYFFRAQ-UHFFFAOYSA-N tributyl-(2,6-difluorophenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=C(F)C=CC=C1F DLTHSKKNYFFRAQ-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/08—Antiepileptics; Anticonvulsants
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- 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
- C07D401/14—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 three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Addiction (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9502052.5A GB9502052D0 (en) | 1995-02-02 | 1995-02-02 | Novel compounds |
GBGB9508327.5A GB9508327D0 (en) | 1995-04-25 | 1995-04-25 | Novel compounds |
GBGB9508967.8A GB9508967D0 (en) | 1995-05-03 | 1995-05-03 | Novel compounds |
GBGB9516845.6A GB9516845D0 (en) | 1995-08-17 | 1995-08-17 | Novel compounds |
GBGB9517542.8A GB9517542D0 (en) | 1995-08-26 | 1995-08-26 | Novel compounds |
GBGB9518574.0A GB9518574D0 (en) | 1995-09-12 | 1995-09-12 | Novel compounds |
PCT/EP1996/000368 WO1996023783A1 (en) | 1995-02-02 | 1996-01-26 | Indole derivatives as 5-ht receptor antagonist |
Publications (3)
Publication Number | Publication Date |
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NO973543D0 NO973543D0 (no) | 1997-08-01 |
NO973543L NO973543L (no) | 1997-10-01 |
NO313520B1 true NO313520B1 (no) | 2002-10-14 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO19973543A NO313520B1 (no) | 1995-02-02 | 1997-08-01 | Indolderivater som 5-HT-reseptor-agonister, fremgangsmåte ved fremstilling derav og farmasöytiske preparater inneholdende dem |
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US (3) | US5990133A (pt) |
EP (1) | EP0808312B1 (pt) |
JP (1) | JPH10513442A (pt) |
KR (1) | KR19980701879A (pt) |
CN (1) | CN1151147C (pt) |
AP (1) | AP657A (pt) |
AR (1) | AR002705A1 (pt) |
AT (1) | ATE197300T1 (pt) |
AU (1) | AU699727B2 (pt) |
BG (1) | BG101806A (pt) |
BR (1) | BR9607016A (pt) |
CA (1) | CA2212061A1 (pt) |
CZ (1) | CZ294097B6 (pt) |
DE (1) | DE69610822T2 (pt) |
DK (1) | DK0808312T3 (pt) |
EA (1) | EA000304B1 (pt) |
ES (1) | ES2151652T3 (pt) |
FI (1) | FI973205A (pt) |
GR (1) | GR3035075T3 (pt) |
HK (1) | HK1003883A1 (pt) |
HU (1) | HU223601B1 (pt) |
IL (1) | IL116998A (pt) |
MA (1) | MA23792A1 (pt) |
MY (1) | MY132229A (pt) |
NO (1) | NO313520B1 (pt) |
NZ (1) | NZ301265A (pt) |
OA (1) | OA10502A (pt) |
PL (1) | PL184490B1 (pt) |
PT (1) | PT808312E (pt) |
RO (1) | RO115522B1 (pt) |
SI (1) | SI0808312T1 (pt) |
SK (1) | SK103897A3 (pt) |
TR (1) | TR199700749T1 (pt) |
WO (1) | WO1996023783A1 (pt) |
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CZ294097B6 (cs) * | 1995-02-02 | 2004-10-13 | Smithklineábeechamáplc | Indolový derivátŹ způsob jeho přípravy a farmaceutická kompozice s jeho obsahem |
GB9517559D0 (en) * | 1995-08-26 | 1995-10-25 | Smithkline Beecham Plc | Novel compounds |
GB9607219D0 (en) * | 1996-04-04 | 1996-06-12 | Smithkline Beecham Plc | Novel compounds |
GB9612885D0 (en) * | 1996-06-20 | 1996-08-21 | Smithkline Beecham Plc | Novel compounds |
GB9612883D0 (en) * | 1996-06-20 | 1996-08-21 | Smithkline Beecham Plc | Novel compounds |
US6191131B1 (en) | 1997-07-23 | 2001-02-20 | Dupont Pharmaceuticals Company | Azolo triazines and pyrimidines |
US6060478A (en) * | 1996-07-24 | 2000-05-09 | Dupont Pharmaceuticals | Azolo triazines and pyrimidines |
US7094782B1 (en) | 1996-07-24 | 2006-08-22 | Bristol-Myers Squibb Company | Azolo triazines and pyrimidines |
US6313124B1 (en) | 1997-07-23 | 2001-11-06 | Dupont Pharmaceuticals Company | Tetrazine bicyclic compounds |
US6124289A (en) * | 1996-07-24 | 2000-09-26 | Dupont Pharmaceuticals Co. | Azolo triazines and pyrimidines |
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GB9710523D0 (en) * | 1997-05-23 | 1997-07-16 | Smithkline Beecham Plc | Novel compounds |
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CA2325559A1 (en) * | 1998-04-14 | 1999-10-21 | Arena Pharmaceuticals, Inc. | Non-endogenous, constitutively activated human serotonin receptors and small molecule modulators thereof |
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NL242547A (pt) * | 1958-08-22 | |||
SE370866B (pt) * | 1968-03-21 | 1974-11-04 | Ciba Geigy Ag | |
KR930702334A (ko) * | 1990-09-13 | 1993-09-08 | 데이비드 로버트 | 5 하이드록시트립타민 수용체 길항제로서의 인돌우레아 |
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GB9306460D0 (en) * | 1993-03-29 | 1993-05-19 | Smithkline Beecham Plc | Novel compounds |
GB9313913D0 (en) * | 1993-07-06 | 1993-08-18 | Smithkline Beecham Plc | Novel compounds |
CZ294097B6 (cs) * | 1995-02-02 | 2004-10-13 | Smithklineábeechamáplc | Indolový derivátŹ způsob jeho přípravy a farmaceutická kompozice s jeho obsahem |
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