DE60206636T2 - THERAPEUTISCHE 1H-PYRIDO[4,3-b]INDOLE - Google Patents
THERAPEUTISCHE 1H-PYRIDO[4,3-b]INDOLE Download PDFInfo
- Publication number
- DE60206636T2 DE60206636T2 DE60206636T DE60206636T DE60206636T2 DE 60206636 T2 DE60206636 T2 DE 60206636T2 DE 60206636 T DE60206636 T DE 60206636T DE 60206636 T DE60206636 T DE 60206636T DE 60206636 T2 DE60206636 T2 DE 60206636T2
- Authority
- DE
- Germany
- Prior art keywords
- pyrido
- indole
- hexahydro
- dichlorophenyl
- alkyl
- 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
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- 230000001225 therapeutic effect Effects 0.000 title description 4
- WYZFLCYTROCEOJ-UHFFFAOYSA-N 1h-pyrido[4,3-b]indole Chemical compound C1=CC=CC2=C3CN=CC=C3N=C21 WYZFLCYTROCEOJ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 96
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 24
- 201000010099 disease Diseases 0.000 claims abstract description 8
- -1 C 2 -8- alkynyl Chemical group 0.000 claims description 88
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 57
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 27
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 208000035475 disorder Diseases 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 210000003169 central nervous system Anatomy 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 208000019901 Anxiety disease Diseases 0.000 claims description 7
- 208000008589 Obesity Diseases 0.000 claims description 7
- 230000036506 anxiety Effects 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 235000020824 obesity Nutrition 0.000 claims description 7
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 5
- OGVIBOYOTLEICI-UHFFFAOYSA-N 8-(2,4-dichlorophenyl)-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound ClC1=CC(Cl)=CC=C1C1=CC=C(NC2C3CNCC2)C3=C1 OGVIBOYOTLEICI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 4
- PMZMPGDSRIYTDF-UHFFFAOYSA-N 6-bromo-8-(2,4-dichlorophenyl)-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound ClC1=CC(Cl)=CC=C1C(C=C1Br)=CC2=C1NC1CCNCC12 PMZMPGDSRIYTDF-UHFFFAOYSA-N 0.000 claims description 3
- OGVIBOYOTLEICI-YOEHRIQHSA-N (4as,9br)-8-(2,4-dichlorophenyl)-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound ClC1=CC(Cl)=CC=C1C1=CC=C(N[C@@H]2[C@H]3CNCC2)C3=C1 OGVIBOYOTLEICI-YOEHRIQHSA-N 0.000 claims description 2
- ZTYHSDRSYGQVQL-LRDDRELGSA-N (4as,9br)-8-(2,6-difluorophenyl)-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound FC1=CC=CC(F)=C1C1=CC=C(N[C@@H]2[C@H]3CNCC2)C3=C1 ZTYHSDRSYGQVQL-LRDDRELGSA-N 0.000 claims description 2
- ZQDRUWSNYLOVNO-LRDDRELGSA-N (4as,9br)-8-(2-chloro-6-fluorophenyl)-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound FC1=CC=CC(Cl)=C1C1=CC=C(N[C@@H]2[C@H]3CNCC2)C3=C1 ZQDRUWSNYLOVNO-LRDDRELGSA-N 0.000 claims description 2
- MVTKBQFDSSHVNM-YOEHRIQHSA-N (4as,9br)-8-(2-chlorophenyl)-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound ClC1=CC=CC=C1C1=CC=C(N[C@@H]2[C@H]3CNCC2)C3=C1 MVTKBQFDSSHVNM-YOEHRIQHSA-N 0.000 claims description 2
- WPAKFBKGXAFMTH-WMZOPIPTSA-N (4as,9br)-8-(2-ethoxyphenyl)-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound CCOC1=CC=CC=C1C1=CC=C(N[C@@H]2[C@H]3CNCC2)C3=C1 WPAKFBKGXAFMTH-WMZOPIPTSA-N 0.000 claims description 2
- LABIXCLHTUFPJV-YOEHRIQHSA-N (4as,9br)-8-(2-fluorophenyl)-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound FC1=CC=CC=C1C1=CC=C(N[C@@H]2[C@H]3CNCC2)C3=C1 LABIXCLHTUFPJV-YOEHRIQHSA-N 0.000 claims description 2
- KKROTHWXTSLHRO-WMZOPIPTSA-N (4as,9br)-8-(2-methylphenyl)-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound CC1=CC=CC=C1C1=CC=C(N[C@@H]2[C@H]3CNCC2)C3=C1 KKROTHWXTSLHRO-WMZOPIPTSA-N 0.000 claims description 2
- DRFSSWQOSCBTHN-HKUYNNGSSA-N (4as,9br)-8-(4-methoxy-2-methylphenyl)-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound CC1=CC(OC)=CC=C1C1=CC=C(N[C@@H]2[C@H]3CNCC2)C3=C1 DRFSSWQOSCBTHN-HKUYNNGSSA-N 0.000 claims description 2
- ICBBYUYDXRQZBG-YOEHRIQHSA-N (4as,9br)-8-[2-(trifluoromethyl)phenyl]-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound FC(F)(F)C1=CC=CC=C1C1=CC=C(N[C@@H]2[C@H]3CNCC2)C3=C1 ICBBYUYDXRQZBG-YOEHRIQHSA-N 0.000 claims description 2
- UAAXYVDHKWEKNN-RDJZCZTQSA-N (4as,9br)-8-phenyl-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound N([C@H]1CCNC[C@H]1C1=C2)C1=CC=C2C1=CC=CC=C1 UAAXYVDHKWEKNN-RDJZCZTQSA-N 0.000 claims description 2
- GOLLOHUQKXWFKV-UHFFFAOYSA-N 8-(2,4-dichlorophenyl)-5,6-diethyl-1,2,3,4,4a,9b-hexahydropyrido[4,3-b]indole Chemical compound C=1C(CC)=C2N(CC)C3CCNCC3C2=CC=1C1=CC=C(Cl)C=C1Cl GOLLOHUQKXWFKV-UHFFFAOYSA-N 0.000 claims description 2
- GCJDLXQTLDPCFC-UHFFFAOYSA-N 8-(2,4-dichlorophenyl)-5,6-dimethyl-1,2,3,4,4a,9b-hexahydropyrido[4,3-b]indole Chemical compound C=1C(C)=C2N(C)C3CCNCC3C2=CC=1C1=CC=C(Cl)C=C1Cl GCJDLXQTLDPCFC-UHFFFAOYSA-N 0.000 claims description 2
- PFRFFSFEQVUOPW-UHFFFAOYSA-N 8-(2,4-dichlorophenyl)-5-ethyl-1,2,3,4,4a,9b-hexahydropyrido[4,3-b]indole Chemical compound C=1C=C2N(CC)C3CCNCC3C2=CC=1C1=CC=C(Cl)C=C1Cl PFRFFSFEQVUOPW-UHFFFAOYSA-N 0.000 claims description 2
- BKUCPVOMSOXIQM-UHFFFAOYSA-N 8-(2,4-dichlorophenyl)-5-ethyl-6-ethylsulfanyl-1,2,3,4,4a,9b-hexahydropyrido[4,3-b]indole Chemical compound C=1C=2C3CNCCC3N(CC)C=2C(SCC)=CC=1C1=CC=C(Cl)C=C1Cl BKUCPVOMSOXIQM-UHFFFAOYSA-N 0.000 claims description 2
- ZLWRJYNAJAAJLC-UHFFFAOYSA-N 8-(2,4-dichlorophenyl)-5-ethyl-6-methyl-1,2,3,4,4a,9b-hexahydropyrido[4,3-b]indole Chemical compound C=1C(C)=C2N(CC)C3CCNCC3C2=CC=1C1=CC=C(Cl)C=C1Cl ZLWRJYNAJAAJLC-UHFFFAOYSA-N 0.000 claims description 2
- JWLDTNNDEQVTJW-UHFFFAOYSA-N 8-(2,4-dichlorophenyl)-5-ethyl-6-methylsulfanyl-1,2,3,4,4a,9b-hexahydropyrido[4,3-b]indole Chemical compound C=1C(SC)=C2N(CC)C3CCNCC3C2=CC=1C1=CC=C(Cl)C=C1Cl JWLDTNNDEQVTJW-UHFFFAOYSA-N 0.000 claims description 2
- XDSDUPZHGOCMLH-UHFFFAOYSA-N 8-(2,4-dichlorophenyl)-5-methyl-1,2,3,4,4a,9b-hexahydropyrido[4,3-b]indole Chemical compound C=1C=C2N(C)C3CCNCC3C2=CC=1C1=CC=C(Cl)C=C1Cl XDSDUPZHGOCMLH-UHFFFAOYSA-N 0.000 claims description 2
- GHKAKMOGXIBCFD-UHFFFAOYSA-N 8-(2,4-dichlorophenyl)-5-methyl-6-methylsulfanyl-1,2,3,4,4a,9b-hexahydropyrido[4,3-b]indole Chemical compound C=1C=2C3CNCCC3N(C)C=2C(SC)=CC=1C1=CC=C(Cl)C=C1Cl GHKAKMOGXIBCFD-UHFFFAOYSA-N 0.000 claims description 2
- MSNUFJDXDJRDCQ-UHFFFAOYSA-N 8-(2,4-dichlorophenyl)-6-ethyl-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound C=1C=2C3CNCCC3NC=2C(CC)=CC=1C1=CC=C(Cl)C=C1Cl MSNUFJDXDJRDCQ-UHFFFAOYSA-N 0.000 claims description 2
- MRAWTCZLQZPPBQ-UHFFFAOYSA-N 8-(2,4-dichlorophenyl)-6-ethyl-5-methyl-1,2,3,4,4a,9b-hexahydropyrido[4,3-b]indole Chemical compound C=1C=2C3CNCCC3N(C)C=2C(CC)=CC=1C1=CC=C(Cl)C=C1Cl MRAWTCZLQZPPBQ-UHFFFAOYSA-N 0.000 claims description 2
- YIDOGYZMYJLNBP-UHFFFAOYSA-N 8-(2,4-dichlorophenyl)-6-ethylsulfanyl-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound C=1C=2C3CNCCC3NC=2C(SCC)=CC=1C1=CC=C(Cl)C=C1Cl YIDOGYZMYJLNBP-UHFFFAOYSA-N 0.000 claims description 2
- YUZGGVHIVJQNQJ-UHFFFAOYSA-N 8-(2,4-dichlorophenyl)-6-ethylsulfanyl-5-methyl-1,2,3,4,4a,9b-hexahydropyrido[4,3-b]indole Chemical compound C=1C=2C3CNCCC3N(C)C=2C(SCC)=CC=1C1=CC=C(Cl)C=C1Cl YUZGGVHIVJQNQJ-UHFFFAOYSA-N 0.000 claims description 2
- RRWZBKYLHRWWFI-UHFFFAOYSA-N 8-(2,4-dichlorophenyl)-6-methyl-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound C=1C=2C3CNCCC3NC=2C(C)=CC=1C1=CC=C(Cl)C=C1Cl RRWZBKYLHRWWFI-UHFFFAOYSA-N 0.000 claims description 2
- LRANPAICFTUZGK-UHFFFAOYSA-N 8-(2,4-dichlorophenyl)-6-methylsulfanyl-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical compound C=1C=2C3CNCCC3NC=2C(SC)=CC=1C1=CC=C(Cl)C=C1Cl LRANPAICFTUZGK-UHFFFAOYSA-N 0.000 claims description 2
- 238000003745 diagnosis Methods 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract description 38
- 230000000694 effects Effects 0.000 abstract description 9
- 239000003446 ligand Substances 0.000 abstract description 6
- BPPMRCNUQCVVFJ-UHFFFAOYSA-N 2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3-b]indole Chemical class N1C2=CC=CC=C2C2C1CCNC2 BPPMRCNUQCVVFJ-UHFFFAOYSA-N 0.000 abstract description 2
- 150000008591 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indoles Chemical class 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 35
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
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- 239000000203 mixture Substances 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 4
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- 229940076279 serotonin Drugs 0.000 description 1
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- 230000000697 serotonin reuptake Effects 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
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- 230000011273 social behavior Effects 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- 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
-
- 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
- A61P25/22—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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31089001P | 2001-08-08 | 2001-08-08 | |
| US310890P | 2001-08-08 | ||
| PCT/US2002/025130 WO2003014118A1 (en) | 2001-08-08 | 2002-08-06 | THERAPEUTIC 1H-PYRIDO[4,3-b]INDOLES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60206636D1 DE60206636D1 (de) | 2006-02-23 |
| DE60206636T2 true DE60206636T2 (de) | 2006-06-22 |
Family
ID=23204521
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60206636T Expired - Fee Related DE60206636T2 (de) | 2001-08-08 | 2002-08-06 | THERAPEUTISCHE 1H-PYRIDO[4,3-b]INDOLE |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6849640B2 (https=) |
| EP (1) | EP1414819B1 (https=) |
| JP (1) | JP2005526691A (https=) |
| AT (1) | ATE306486T1 (https=) |
| BR (1) | BR0211608A (https=) |
| CA (1) | CA2453537A1 (https=) |
| DE (1) | DE60206636T2 (https=) |
| ES (1) | ES2250689T3 (https=) |
| MX (1) | MXPA04001203A (https=) |
| WO (1) | WO2003014118A1 (https=) |
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| WO2002066494A2 (en) * | 2001-02-16 | 2002-08-29 | Bristol-Myers Squibb Company | Identification and cloning of a novel human gene, ret16, involved in the intracellular signaling cascade |
| WO2004056324A2 (en) * | 2002-12-19 | 2004-07-08 | Bristol-Myers Squibb Company | Substituted tricyclic gamma-carbolines as serotonin receptor agonists and antagonists |
| CL2004000826A1 (es) | 2003-04-25 | 2005-03-04 | Pfizer | Uso de un agonista para el receptor 5-ht2c para preparar un medicamento util en el tratamiento de la incontinencia urinaria provocada por estres, con la condicion de que el agonista no sea 1-[6-cloro-5-(trifluorometil)-2-piridinil]piperazina (org-129 |
| US20080075885A1 (en) * | 2003-08-19 | 2008-03-27 | Heng-Yong Nie | Method of Controllable Morphology of Self-Assembled Monolayers on Substrates |
| WO2005095396A1 (en) * | 2004-03-05 | 2005-10-13 | Pharma C S.A. | 8-phenoxy-ϝ carboline derivatives |
| US7592454B2 (en) | 2004-04-14 | 2009-09-22 | Bristol-Myers Squibb Company | Substituted hexahydro-pyridoindole derivatives as serotonin receptor agonists and antagonists |
| JP5173190B2 (ja) | 2004-08-25 | 2013-03-27 | 武田薬品工業株式会社 | 腹圧性尿失禁の予防・治療剤及びそのスクリーニング方法 |
| KR20080034171A (ko) * | 2005-07-28 | 2008-04-18 | 브리스톨-마이어스 스큅 컴퍼니 | 세로토닌 수용체 효능제 및 길항제로서의 치환된테트라히드로-1ｈ-피리도[4,3,ｂ]인돌 |
| US20070117834A1 (en) * | 2005-10-04 | 2007-05-24 | David Hung | Methods and compositions for treating Huntington's disease |
| RU2338537C2 (ru) * | 2006-01-25 | 2008-11-20 | Сергей Олегович Бачурин | СРЕДСТВО ДЛЯ ЛЕЧЕНИЯ ШИЗОФРЕНИИ НА ОСНОВЕ ГИДРИРОВАННЫХ ПИРИДО(4,3-b)ИНДОЛОВ (ВАРИАНТЫ), ФАРМАКОЛОГИЧЕСКОЕ СРЕДСТВО НА ЕГО ОСНОВЕ И СПОСОБ ЕГО ПРИМЕНЕНИЯ |
| EP2727585A1 (en) | 2006-05-16 | 2014-05-07 | Takeda Pharmaceutical Company Limited | In-vivo screening method |
| RU2329044C1 (ru) * | 2006-11-16 | 2008-07-20 | Андрей Александрович Иващенко | Лиганды 5-ht6 рецепторов, фармацевтическая композиция, способ ее получения и лекарственное средство |
| KR102107954B1 (ko) * | 2007-03-12 | 2020-05-07 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 치환된 헤테로환 융합 감마-카르볼린 합성 |
| RU2338745C1 (ru) * | 2007-03-21 | 2008-11-20 | Андрей Александрович Иващенко | ЗАМЕЩЕННЫЕ 2,3,4,5-ТЕТРАГИДРО-1Н-ПИРИДО[4,3-b]ИНДОЛЫ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ |
| MX2009012788A (es) * | 2007-05-25 | 2010-01-14 | Medivation Neurology Inc | Metodos y composiciones para estimular celulas. |
| MX2010001218A (es) * | 2007-08-01 | 2010-04-07 | Medivation Neurology Inc | Metodos y composiciones para tratamiento contra esquizofrenia mediante uso de terapia combinada de agentes antipsicoticos. |
| RU2007139634A (ru) | 2007-10-25 | 2009-04-27 | Сергей Олегович Бачурин (RU) | Новые тиазол-, триазол- или оксадиазол-содержащие тетрациклические соединения |
| EP2789338A3 (en) | 2007-11-15 | 2015-01-14 | Takeda Pharmaceutical Company Limited | Condensed pyridine derivate and use thereof |
| KR101614723B1 (ko) | 2008-01-11 | 2016-04-22 | 알바니 몰레큘라 리써치, 인크. | Ｍｃｈ 길항물질로서 (1-아지논)-치환된 피리도인돌 |
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| CA2748813C (en) * | 2009-01-09 | 2018-07-10 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| US9162980B2 (en) | 2009-01-09 | 2015-10-20 | Board Of Regents Of The University Of Texas System | Anti-depression compounds |
| US8362277B2 (en) | 2009-01-09 | 2013-01-29 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| US9962368B2 (en) | 2009-01-09 | 2018-05-08 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
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| EP2510949A4 (en) | 2009-12-11 | 2013-11-13 | Astellas Pharma Inc | THERAPEUTICS FOR FIBROMYALGIA |
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| CA2804161A1 (en) | 2010-07-07 | 2012-01-12 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
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| KR20140146192A (ko) | 2012-04-14 | 2014-12-24 | 인트라-셀룰라 써래피스, 인코퍼레이티드. | 유기 화합물 |
| CA2882826A1 (en) | 2012-08-24 | 2014-02-27 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
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| EP3525763B1 (en) | 2016-10-12 | 2025-03-05 | Intra-Cellular Therapies, Inc. | Amorphous solid dispersions |
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| WO2018126140A1 (en) | 2016-12-29 | 2018-07-05 | Intra-Cellular Therapies, Inc. | Organic compounds |
| RU2767410C2 (ru) | 2017-03-24 | 2022-03-17 | Интра-Селлулар Терапиз, Инк. | Новые композиции и способы |
| EP3658144B1 (en) | 2017-07-26 | 2022-01-26 | Intra-Cellular Therapies, Inc. | Pyridopyrroloquinoxaline compounds, their compositions and uses in therapy |
| WO2019023062A1 (en) | 2017-07-26 | 2019-01-31 | Intra-Cellular Therapies, Inc. | ORGANIC COMPOUNDS |
| US20210052600A1 (en) | 2017-12-27 | 2021-02-25 | Takeda Pharmaceutical Company Limited | Therapeutic agents for stress urinary incontinence and incotinence of feces |
| CN112040940A (zh) | 2018-03-23 | 2020-12-04 | 细胞内治疗公司 | 有机化合物 |
| EP3801527B1 (en) | 2018-06-08 | 2025-02-19 | Intra-Cellular Therapies, Inc. | Fused gamma-carbolines for acute treatment of anxiety or depression |
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| WO2020047408A1 (en) | 2018-08-31 | 2020-03-05 | Intra-Cellular Therapies, Inc. | Novel methods |
| BR112021003655A2 (pt) | 2018-08-31 | 2021-05-18 | Intra-Cellular Therapies, Inc. | métodos novos |
| US12195463B2 (en) | 2018-12-21 | 2025-01-14 | Intra-Cellular Therapies, Inc. | Organic compounds |
| WO2021007245A1 (en) | 2019-07-07 | 2021-01-14 | Intra-Cellular Therapies, Inc. | Novel methods |
| EP4072554A4 (en) | 2019-12-11 | 2023-12-20 | Intra-Cellular Therapies, Inc. | ORGANIC CONNECTION |
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| US57325A (en) * | 1866-08-21 | Improvement in mite ring-machines | ||
| US337250A (en) * | 1886-03-02 | Weather-strip for doors | ||
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| GB9226537D0 (en) | 1992-12-21 | 1993-02-17 | Smithkline Beecham Plc | Compounds |
| GB9418326D0 (en) * | 1994-09-12 | 1994-11-02 | Lilly Industries Ltd | Pharmaceutical compounds |
| DE69531476T2 (de) | 1994-09-12 | 2004-06-09 | Lilly Industries Ltd., Basingstoke | Serotonergische Modulatoren |
| TW470745B (en) | 1996-05-23 | 2002-01-01 | Janssen Pharmaceutica Nv | Hexahydro-pyrido[4,3-b]indole derivatives |
| ATE252572T1 (de) | 1998-06-30 | 2003-11-15 | Lilly Co Eli | 5-ht1f agonisten |
| WO2002024700A2 (en) * | 2000-09-20 | 2002-03-28 | Pharmacia & Upjohn Company | SUBSTITUTED AZEPINO[4,5b]INDOLINE DERIVATIVES |
-
2002
- 2002-08-06 CA CA002453537A patent/CA2453537A1/en not_active Abandoned
- 2002-08-06 US US10/214,405 patent/US6849640B2/en not_active Expired - Fee Related
- 2002-08-06 WO PCT/US2002/025130 patent/WO2003014118A1/en not_active Ceased
- 2002-08-06 DE DE60206636T patent/DE60206636T2/de not_active Expired - Fee Related
- 2002-08-06 MX MXPA04001203A patent/MXPA04001203A/es unknown
- 2002-08-06 EP EP02757023A patent/EP1414819B1/en not_active Expired - Lifetime
- 2002-08-06 JP JP2003519067A patent/JP2005526691A/ja not_active Withdrawn
- 2002-08-06 ES ES02757023T patent/ES2250689T3/es not_active Expired - Lifetime
- 2002-08-06 BR BRPI0211608-1A patent/BR0211608A/pt not_active IP Right Cessation
- 2002-08-06 AT AT02757023T patent/ATE306486T1/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2453537A1 (en) | 2003-02-20 |
| DE60206636D1 (de) | 2006-02-23 |
| EP1414819B1 (en) | 2005-10-12 |
| BR0211608A (pt) | 2006-04-04 |
| WO2003014118A1 (en) | 2003-02-20 |
| EP1414819A1 (en) | 2004-05-06 |
| MXPA04001203A (es) | 2004-05-20 |
| JP2005526691A (ja) | 2005-09-08 |
| US6849640B2 (en) | 2005-02-01 |
| US20030060464A1 (en) | 2003-03-27 |
| ES2250689T3 (es) | 2006-04-16 |
| ATE306486T1 (de) | 2005-10-15 |
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| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |