DE69911243T2 - Benzofuranderivate, ihre herstellung und verwendung - Google Patents
Benzofuranderivate, ihre herstellung und verwendung Download PDFInfo
- Publication number
- DE69911243T2 DE69911243T2 DE69911243T DE69911243T DE69911243T2 DE 69911243 T2 DE69911243 T2 DE 69911243T2 DE 69911243 T DE69911243 T DE 69911243T DE 69911243 T DE69911243 T DE 69911243T DE 69911243 T2 DE69911243 T2 DE 69911243T2
- Authority
- DE
- Germany
- Prior art keywords
- propyl
- dihydroisobenzofuran
- fluorophenyl
- carbonitrile
- indol
- 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.)
- Expired - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical class C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title 1
- -1 hydroxy, formyl Chemical group 0.000 claims description 89
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 72
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 65
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
- 208000019901 Anxiety disease Diseases 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000004754 (C2-C12) dialkylamino group Chemical group 0.000 claims description 5
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims description 5
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 206010012289 Dementia Diseases 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 5
- 230000016571 aggressive behavior Effects 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 208000019906 panic disease Diseases 0.000 claims description 5
- WZGZPDVROXULRH-UHFFFAOYSA-N 1-(4-fluorophenyl)-1-[3-[2-(5-methyl-1h-indol-3-yl)ethyl-prop-2-enylamino]propyl]-3h-2-benzofuran-5-carbonitrile Chemical compound C12=CC(C)=CC=C2NC=C1CCN(CC=C)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 WZGZPDVROXULRH-UHFFFAOYSA-N 0.000 claims description 4
- UKBJVXWHRGAUDI-UHFFFAOYSA-N 1-[4-[2-(5-tert-butyl-1h-indol-3-yl)ethyl-methylamino]butyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=C(C(C)(C)C)C=C2C=1CCN(C)CCCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 UKBJVXWHRGAUDI-UHFFFAOYSA-N 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- 208000007848 Alcoholism Diseases 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
- 208000028017 Psychotic disease Diseases 0.000 claims description 4
- 206010041250 Social phobia Diseases 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 206010001584 alcohol abuse Diseases 0.000 claims description 4
- 208000025746 alcohol use disease Diseases 0.000 claims description 4
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical group C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 claims description 4
- UONNNPVVNJUDLU-PMERELPUSA-N (1s)-1-(4-fluorophenyl)-1-[3-[3-(1h-indol-3-yl)propyl-methylamino]propyl]-3h-2-benzofuran-5-carbonitrile Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(CCCC=2C3=CC=CC=C3NC=2)C)=CC=C(F)C=C1 UONNNPVVNJUDLU-PMERELPUSA-N 0.000 claims description 3
- FCAPIVXOAVLTBT-HKBQPEDESA-N (1s)-1-(4-fluorophenyl)-1-[3-[4-(1h-indol-3-yl)butyl-methylamino]propyl]-3h-2-benzofuran-5-carbonitrile Chemical compound C1([C@]2(C3=CC=C(C=C3CO2)C#N)CCCN(CCCCC=2C3=CC=CC=C3NC=2)C)=CC=C(F)C=C1 FCAPIVXOAVLTBT-HKBQPEDESA-N 0.000 claims description 3
- 125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- SVJOCTDSPDUOHD-UHFFFAOYSA-N 1-(4-fluorophenyl)-1-[3-[2-(2-methoxyphenoxy)ethyl-methylamino]propyl]-3h-2-benzofuran-5-carbonitrile Chemical compound COC1=CC=CC=C1OCCN(C)CCCC1(C=2C=CC(F)=CC=2)C2=CC=C(C#N)C=C2CO1 SVJOCTDSPDUOHD-UHFFFAOYSA-N 0.000 claims description 3
- WKWPYKFOCBDZQY-UHFFFAOYSA-N 1-(4-fluorophenyl)-1-[3-[2-(3-methoxyphenyl)ethyl-methylamino]propyl]-3h-2-benzofuran-5-carbonitrile Chemical compound COC1=CC=CC(CCN(C)CCCC2(C3=CC=C(C=C3CO2)C#N)C=2C=CC(F)=CC=2)=C1 WKWPYKFOCBDZQY-UHFFFAOYSA-N 0.000 claims description 3
- ASVVLILWDXJMCX-UHFFFAOYSA-N 1-(4-fluorophenyl)-1-[3-[2-(5-methyl-1h-indol-3-yl)ethyl-(2-phenoxyethyl)amino]propyl]-3h-2-benzofuran-5-carbonitrile Chemical compound C12=CC(C)=CC=C2NC=C1CCN(CCOC=1C=CC=CC=1)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 ASVVLILWDXJMCX-UHFFFAOYSA-N 0.000 claims description 3
- GKUGRYRUPDJTJW-UHFFFAOYSA-N 1-(4-fluorophenyl)-1-[3-[2-phenylmethoxyethyl(prop-2-enyl)amino]propyl]-3h-2-benzofuran-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1(CCCN(CCOCC=2C=CC=CC=2)CC=C)C2=CC=C(C#N)C=C2CO1 GKUGRYRUPDJTJW-UHFFFAOYSA-N 0.000 claims description 3
- HQWMGBRNFBXIEC-UHFFFAOYSA-N 1-(4-fluorophenyl)-1-[3-[3-(1h-indol-3-yl)propyl-(2-phenoxyethyl)amino]propyl]-3h-2-benzofuran-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1(CCCN(CCCC=2C3=CC=CC=C3NC=2)CCOC=2C=CC=CC=2)C2=CC=C(C#N)C=C2CO1 HQWMGBRNFBXIEC-UHFFFAOYSA-N 0.000 claims description 3
- BIZVPVITTYLSLH-UHFFFAOYSA-N 1-(4-fluorophenyl)-1-[3-[3-(3-methoxyphenoxy)propyl-methylamino]propyl]-3h-2-benzofuran-5-carbonitrile Chemical compound COC1=CC=CC(OCCCN(C)CCCC2(C3=CC=C(C=C3CO2)C#N)C=2C=CC(F)=CC=2)=C1 BIZVPVITTYLSLH-UHFFFAOYSA-N 0.000 claims description 3
- UBGTYXCJSAMGTE-UHFFFAOYSA-N 1-(4-fluorophenyl)-1-[3-[methyl(2-phenylmethoxyethyl)amino]propyl]-3h-2-benzofuran-5-carbonitrile Chemical compound C=1C=CC=CC=1COCCN(C)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 UBGTYXCJSAMGTE-UHFFFAOYSA-N 0.000 claims description 3
- UNEUEYLBXCIZPB-UHFFFAOYSA-N 1-(4-fluorophenyl)-1-[3-[methyl-[2-(5-methyl-1h-indol-3-yl)ethyl]amino]propyl]-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=C(C)C=C2C=1CCN(C)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 UNEUEYLBXCIZPB-UHFFFAOYSA-N 0.000 claims description 3
- LCVOPOSTPVKXFV-UHFFFAOYSA-N 1-(4-fluorophenyl)-1-[3-[methyl-[3-(5-methyl-1h-indol-3-yl)propyl]amino]propyl]-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=C(C)C=C2C=1CCCN(C)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 LCVOPOSTPVKXFV-UHFFFAOYSA-N 0.000 claims description 3
- DFSXWFHBHABHDD-UHFFFAOYSA-N 1-(4-fluorophenyl)-1-[3-[methyl-[4-(5-methyl-1h-indol-3-yl)butyl]amino]propyl]-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=C(C)C=C2C=1CCCCN(C)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 DFSXWFHBHABHDD-UHFFFAOYSA-N 0.000 claims description 3
- YNLNPGVFXQLKCK-UHFFFAOYSA-N 1-(4-fluorophenyl)-1-[4-[2-(5-iodo-1h-indol-3-yl)ethyl-methylamino]butyl]-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=C(I)C=C2C=1CCN(C)CCCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 YNLNPGVFXQLKCK-UHFFFAOYSA-N 0.000 claims description 3
- IKJNOGVMEYKYCO-UHFFFAOYSA-N 1-(4-fluorophenyl)-1-[4-[methyl-[2-(5-methyl-1h-indol-3-yl)ethyl]amino]butyl]-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=C(C)C=C2C=1CCN(C)CCCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 IKJNOGVMEYKYCO-UHFFFAOYSA-N 0.000 claims description 3
- XHCRYKJILOTDDE-UHFFFAOYSA-N 1-[2-[4-(5-chloro-1h-indol-3-yl)butyl-methylamino]ethyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=C(Cl)C=C2C=1CCCCN(C)CCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 XHCRYKJILOTDDE-UHFFFAOYSA-N 0.000 claims description 3
- JHMGREPAFKQTBP-UHFFFAOYSA-N 1-[3-[2-(2,5-dimethoxyphenyl)ethyl-methylamino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound COC1=CC=C(OC)C(CCN(C)CCCC2(C3=CC=C(C=C3CO2)C#N)C=2C=CC(F)=CC=2)=C1 JHMGREPAFKQTBP-UHFFFAOYSA-N 0.000 claims description 3
- JBVQOCXFSUXPLG-UHFFFAOYSA-N 1-[3-[2-(2,5-dimethoxyphenyl)ethyl-prop-2-enylamino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound COC1=CC=C(OC)C(CCN(CCCC2(C3=CC=C(C=C3CO2)C#N)C=2C=CC(F)=CC=2)CC=C)=C1 JBVQOCXFSUXPLG-UHFFFAOYSA-N 0.000 claims description 3
- YQWAHZJAIDRDOF-UHFFFAOYSA-N 1-[3-[2-(4-chloro-7-methyl-1h-indol-3-yl)ethyl-prop-2-enylamino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC=2C(C)=CC=C(Cl)C=2C=1CCN(CC=C)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 YQWAHZJAIDRDOF-UHFFFAOYSA-N 0.000 claims description 3
- UAUSUCBKHILGHR-UHFFFAOYSA-N 1-[3-[2-(5-bromo-1h-indol-3-yl)ethyl-methylamino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=C(Br)C=C2C=1CCN(C)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 UAUSUCBKHILGHR-UHFFFAOYSA-N 0.000 claims description 3
- HSKQIGAPQKPCNF-UHFFFAOYSA-N 1-[3-[2-(5-chloro-1h-indol-3-yl)ethyl-ethylamino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=C(Cl)C=C2C=1CCN(CC)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 HSKQIGAPQKPCNF-UHFFFAOYSA-N 0.000 claims description 3
- MSRCAALQWGGVES-UHFFFAOYSA-N 1-[3-[2-(5-chloro-1h-indol-3-yl)ethyl-methylamino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=C(Cl)C=C2C=1CCN(C)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 MSRCAALQWGGVES-UHFFFAOYSA-N 0.000 claims description 3
- SFYPCNNFUSTCJZ-UHFFFAOYSA-N 1-[3-[2-(5-chloro-1h-indol-3-yl)ethyl-prop-2-enylamino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1(CCCN(CCC=2C3=CC(Cl)=CC=C3NC=2)CC=C)C2=CC=C(C#N)C=C2CO1 SFYPCNNFUSTCJZ-UHFFFAOYSA-N 0.000 claims description 3
- WNSKRQGBKPVBQW-UHFFFAOYSA-N 1-[3-[2-(5-fluoro-1h-indol-3-yl)ethyl-prop-2-enylamino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1(CCCN(CCC=2C3=CC(F)=CC=C3NC=2)CC=C)C2=CC=C(C#N)C=C2CO1 WNSKRQGBKPVBQW-UHFFFAOYSA-N 0.000 claims description 3
- TYFGIRXQGFDWGT-UHFFFAOYSA-N 1-[3-[2-(7-chloro-1h-indol-3-yl)ethyl-ethylamino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=C(Cl)C=CC=C2C=1CCN(CC)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 TYFGIRXQGFDWGT-UHFFFAOYSA-N 0.000 claims description 3
- AGSSTGHQQNRMCH-UHFFFAOYSA-N 1-[3-[2-(7-fluoro-1h-indol-3-yl)ethyl-prop-2-enylamino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1(CCCN(CCC=2C3=CC=CC(F)=C3NC=2)CC=C)C2=CC=C(C#N)C=C2CO1 AGSSTGHQQNRMCH-UHFFFAOYSA-N 0.000 claims description 3
- JIGRSENDWILVPL-UHFFFAOYSA-N 1-[3-[3-(5-chloro-1h-indol-3-yl)propyl-methylamino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=C(Cl)C=C2C=1CCCN(C)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 JIGRSENDWILVPL-UHFFFAOYSA-N 0.000 claims description 3
- YZJJJYFDTRQNID-UHFFFAOYSA-N 1-[3-[3-(5-chloro-1h-indol-3-yl)propyl-prop-2-enylamino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1(CCCN(CCCC=2C3=CC(Cl)=CC=C3NC=2)CC=C)C2=CC=C(C#N)C=C2CO1 YZJJJYFDTRQNID-UHFFFAOYSA-N 0.000 claims description 3
- IUBRWTOJFBFRDS-UHFFFAOYSA-N 1-[3-[3-(5-fluoro-1h-indol-3-yl)propyl-(2-phenoxyethyl)amino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1(CCCN(CCCC=2C3=CC(F)=CC=C3NC=2)CCOC=2C=CC=CC=2)C2=CC=C(C#N)C=C2CO1 IUBRWTOJFBFRDS-UHFFFAOYSA-N 0.000 claims description 3
- YWXMNVUEOCLGAI-UHFFFAOYSA-N 1-[3-[3-(7-fluoro-1h-indol-3-yl)propyl-methylamino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=C(F)C=CC=C2C=1CCCN(C)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 YWXMNVUEOCLGAI-UHFFFAOYSA-N 0.000 claims description 3
- ZBELYGWERKCIGD-UHFFFAOYSA-N 1-[3-[4-(5-bromo-1h-indol-3-yl)butyl-methylamino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=C(Br)C=C2C=1CCCCN(C)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 ZBELYGWERKCIGD-UHFFFAOYSA-N 0.000 claims description 3
- RLGLAMNRHNSGQR-UHFFFAOYSA-N 1-[3-[4-(5-chloro-1h-indol-3-yl)butyl-methylamino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=C(Cl)C=C2C=1CCCCN(C)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 RLGLAMNRHNSGQR-UHFFFAOYSA-N 0.000 claims description 3
- FAJANOFMOOZJPI-UHFFFAOYSA-N 1-[3-[ethyl-[2-(7-fluoro-1h-indol-3-yl)ethyl]amino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=C(F)C=CC=C2C=1CCN(CC)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 FAJANOFMOOZJPI-UHFFFAOYSA-N 0.000 claims description 3
- BORVSTSZIJNJIK-UHFFFAOYSA-N 1-[3-[ethyl-[3-(1h-indol-3-yl)propyl]amino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=CC=C2C=1CCCN(CC)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 BORVSTSZIJNJIK-UHFFFAOYSA-N 0.000 claims description 3
- PAAXJTGWGMXUAL-UHFFFAOYSA-N 1-[3-[ethyl-[3-(5-fluoro-1h-indol-3-yl)propyl]amino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=C(F)C=C2C=1CCCN(CC)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 PAAXJTGWGMXUAL-UHFFFAOYSA-N 0.000 claims description 3
- UNWMGUHLBVBQGZ-UHFFFAOYSA-N 1-[3-[ethyl-[3-(5-iodo-1h-indol-3-yl)propyl]amino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=C(I)C=C2C=1CCCN(CC)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 UNWMGUHLBVBQGZ-UHFFFAOYSA-N 0.000 claims description 3
- FBQZMJLDKJXVSG-UHFFFAOYSA-N 1-[3-[ethyl-[3-(5-methyl-1h-indol-3-yl)propyl]amino]propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C=1NC2=CC=C(C)C=C2C=1CCCN(CC)CCCC1(C2=CC=C(C=C2CO1)C#N)C1=CC=C(F)C=C1 FBQZMJLDKJXVSG-UHFFFAOYSA-N 0.000 claims description 3
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- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 208000023589 ischemic disease Diseases 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WZHJKEUHNJHDLS-QTGUNEKASA-N metergoline Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4N(C)C=C(C=34)C2)C1)C)NC(=O)OCC1=CC=CC=C1 WZHJKEUHNJHDLS-QTGUNEKASA-N 0.000 description 1
- 229960004650 metergoline Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical compound [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- LLHOUTQMZLNJMX-UHFFFAOYSA-N n-[3-[1-(3-chlorophenyl)-3h-2-benzofuran-1-yl]propyl]-3-(2,3-dihydro-1,4-benzodioxin-5-yl)-n-methylpropan-1-amine Chemical compound C=1C=CC=2OCCOC=2C=1CCCN(C)CCCC1(C2=CC=CC=C2CO1)C1=CC=CC(Cl)=C1 LLHOUTQMZLNJMX-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 101150006061 neur gene Proteins 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000002414 normal-phase solid-phase extraction Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 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
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 1
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 1
- SFLGSKRGOWRGBR-UHFFFAOYSA-N phthalane Chemical class C1=CC=C2COCC2=C1 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 238000011808 rodent model Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 1
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 239000003723 serotonin 1A agonist Substances 0.000 description 1
- 229940126570 serotonin reuptake inhibitor Drugs 0.000 description 1
- 230000013275 serotonin uptake Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D405/02—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 two hetero rings
- C07D405/12—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 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
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11136098P | 1998-12-08 | 1998-12-08 | |
| US111360P | 1998-12-08 | ||
| DK163198 | 1998-12-09 | ||
| DKPA199801631 | 1998-12-09 | ||
| PCT/DK1999/000676 WO2000034263A1 (en) | 1998-12-08 | 1999-12-03 | Benzofuran derivatives, their preparation and use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69911243D1 DE69911243D1 (de) | 2003-10-16 |
| DE69911243T2 true DE69911243T2 (de) | 2004-07-15 |
Family
ID=43768792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69911243T Expired - Fee Related DE69911243T2 (de) | 1998-12-08 | 1999-12-03 | Benzofuranderivate, ihre herstellung und verwendung |
Country Status (18)
| Country | Link |
|---|---|
| EP (1) | EP1137644B9 (enExample) |
| JP (1) | JP2002531556A (enExample) |
| AR (1) | AR021509A1 (enExample) |
| AT (1) | ATE249451T1 (enExample) |
| AU (1) | AU759248B2 (enExample) |
| CA (1) | CA2353618A1 (enExample) |
| CZ (1) | CZ20012041A3 (enExample) |
| DE (1) | DE69911243T2 (enExample) |
| DK (1) | DK1137644T3 (enExample) |
| ES (1) | ES2204175T3 (enExample) |
| HU (1) | HUP0104510A3 (enExample) |
| IL (1) | IL143082A (enExample) |
| ME (1) | MEP38508A (enExample) |
| PT (1) | PT1137644E (enExample) |
| RS (1) | RS50065B (enExample) |
| SE (1) | SE1137644T5 (enExample) |
| SI (1) | SI1137644T1 (enExample) |
| WO (1) | WO2000034263A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR021155A1 (es) | 1999-07-08 | 2002-06-12 | Lundbeck & Co As H | Tratamiento de desordenes neuroticos |
| EA008373B1 (ru) * | 2000-07-07 | 2007-04-27 | Х. Лундбекк А/С | Применение эсциталопрама для лечения расстройства, связанного с посттравматическим стрессом |
| EA008372B1 (ru) * | 2000-07-07 | 2007-04-27 | Х.Лундбекк А/С | Применение эсциталопрама для лечения расстройства, связанного с социальной тревогой |
| HUP0302778A3 (en) * | 2000-07-21 | 2005-02-28 | Lundbeck & Co As H | Novel compounds and their use as glycine transport inhibitors |
| AU2001288605A1 (en) * | 2000-09-06 | 2002-03-22 | Chugai Seiyaku Kabushiki Kaisha | A traceless solid-phase synthesis of 2-imidazolones |
| US7235569B2 (en) | 2003-05-02 | 2007-06-26 | Wyeth | Piperidinyl indole and tetrohydropyridinyl indole derivatives and method of their use |
| US7276603B2 (en) | 2003-05-02 | 2007-10-02 | Wyeth | Benzofuranyl-and benzothienyl-piperazinyl quinolines and methods of their use |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| JP6064062B2 (ja) | 2013-03-15 | 2017-01-18 | ファイザー・インク | Ａｍｐｋを活性化させるインダゾール化合物 |
| KR20240017363A (ko) * | 2021-06-02 | 2024-02-07 | 세인트 조셉스 유니버시티 | 플루오린화 트립타민 화합물, 이의 유사체 및 이를 사용하는 방법 |
| WO2025104490A1 (en) * | 2023-11-14 | 2025-05-22 | Mindset Pharma Inc. | Indole derivatives as serotonergic agents useful for the treatment of disorders related thereto |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1143703A (enExample) * | 1965-03-18 | |||
| GB1173312A (en) * | 1966-03-17 | 1969-12-10 | Kefalas As | Heterocyclic Compounds |
| GB1526331A (en) * | 1976-01-14 | 1978-09-27 | Kefalas As | Phthalanes |
| DE69419778T2 (de) * | 1993-12-28 | 1999-12-09 | Pharmacia & Upjohn Co., Kalamazoo | Heterozyklische verbindungen für die behandlung von kardiovaskular- und zentralnervensystem störungen |
| ZA954689B (en) * | 1994-06-08 | 1996-01-29 | Lundbeck & Co As H | 4-Aryl-1-(indanmethyl dihydrobenzofuranmethyl or dihydrobenzothiophenemethyl) piperidines tetrahydropyridines or piperazines |
-
1999
- 1999-12-01 AR ARP990106110A patent/AR021509A1/es unknown
- 1999-12-03 ES ES99957263T patent/ES2204175T3/es not_active Expired - Lifetime
- 1999-12-03 SE SE99957263T patent/SE1137644T5/xx unknown
- 1999-12-03 SI SI9930412T patent/SI1137644T1/xx unknown
- 1999-12-03 DE DE69911243T patent/DE69911243T2/de not_active Expired - Fee Related
- 1999-12-03 WO PCT/DK1999/000676 patent/WO2000034263A1/en not_active Ceased
- 1999-12-03 PT PT99957263T patent/PT1137644E/pt unknown
- 1999-12-03 CA CA002353618A patent/CA2353618A1/en not_active Abandoned
- 1999-12-03 RS YUP-384/01A patent/RS50065B/sr unknown
- 1999-12-03 HU HU0104510A patent/HUP0104510A3/hu unknown
- 1999-12-03 ME MEP-385/08A patent/MEP38508A/xx unknown
- 1999-12-03 CZ CZ20012041A patent/CZ20012041A3/cs unknown
- 1999-12-03 AT AT99957263T patent/ATE249451T1/de not_active IP Right Cessation
- 1999-12-03 DK DK99957263T patent/DK1137644T3/da active
- 1999-12-03 IL IL14308299A patent/IL143082A/en not_active IP Right Cessation
- 1999-12-03 EP EP99957263A patent/EP1137644B9/en not_active Expired - Lifetime
- 1999-12-03 AU AU15036/00A patent/AU759248B2/en not_active Ceased
- 1999-12-03 JP JP2000586710A patent/JP2002531556A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1137644B1 (en) | 2003-09-10 |
| DK1137644T3 (da) | 2003-12-08 |
| IL143082A0 (en) | 2002-04-21 |
| WO2000034263A1 (en) | 2000-06-15 |
| DE69911243D1 (de) | 2003-10-16 |
| ATE249451T1 (de) | 2003-09-15 |
| AU1503600A (en) | 2000-06-26 |
| PT1137644E (pt) | 2004-01-30 |
| JP2002531556A (ja) | 2002-09-24 |
| CZ20012041A3 (cs) | 2001-10-17 |
| HUP0104510A2 (hu) | 2002-04-29 |
| SE1137644T5 (enExample) | 2004-05-11 |
| MEP38508A (en) | 2011-02-10 |
| EP1137644B9 (en) | 2004-03-17 |
| RS50065B (sr) | 2009-01-22 |
| YU38401A (sh) | 2005-06-10 |
| EP1137644A1 (en) | 2001-10-04 |
| CA2353618A1 (en) | 2000-06-15 |
| IL143082A (en) | 2004-06-20 |
| SI1137644T1 (en) | 2003-12-31 |
| ES2204175T3 (es) | 2004-04-16 |
| SE1137644T3 (enExample) | 2003-12-02 |
| AR021509A1 (es) | 2002-07-24 |
| HUP0104510A3 (en) | 2003-01-28 |
| AU759248B2 (en) | 2003-04-10 |
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