DE60305339T2 - 3-(cyclopenten-1-yl)-benzyl- oder 3-(cyclopenten-1-yl)heteroarylmethylaminderivate und deren verwendung als arzneimittel zur behandlung von schizophrenie - Google Patents
3-(cyclopenten-1-yl)-benzyl- oder 3-(cyclopenten-1-yl)heteroarylmethylaminderivate und deren verwendung als arzneimittel zur behandlung von schizophrenie Download PDFInfo
- Publication number
- DE60305339T2 DE60305339T2 DE60305339T DE60305339T DE60305339T2 DE 60305339 T2 DE60305339 T2 DE 60305339T2 DE 60305339 T DE60305339 T DE 60305339T DE 60305339 T DE60305339 T DE 60305339T DE 60305339 T2 DE60305339 T2 DE 60305339T2
- Authority
- DE
- Germany
- Prior art keywords
- cyclopenten
- ethyl
- yloxy
- formula
- benzyl
- 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 - Lifetime
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- -1 3- (CYCLOPENTEN-1-YL) -BENZYL Chemical class 0.000 title claims abstract description 20
- 238000011282 treatment Methods 0.000 title claims description 16
- 239000003814 drug Substances 0.000 title claims description 13
- 201000000980 schizophrenia Diseases 0.000 title claims description 13
- 229940079593 drug Drugs 0.000 title claims description 11
- 239000000203 mixture Substances 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 75
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 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 6
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 5
- 101150065749 Churc1 gene Proteins 0.000 claims description 5
- 102100038239 Protein Churchill Human genes 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- RAIDOKRWKAIHOH-UHFFFAOYSA-N n-[[3-(cyclopenten-1-yl)phenyl]methyl]-2-[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxy]ethanamine Chemical compound C=12OC(C)(C)CC2=CC=CC=1OCCNCC(C=1)=CC=CC=1C1=CCCC1 RAIDOKRWKAIHOH-UHFFFAOYSA-N 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000011161 development Methods 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 239000003981 vehicle Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000006519 CCH3 Chemical group 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 125000005241 heteroarylamino group Chemical group 0.000 abstract 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 abstract 1
- 101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 abstract 1
- IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 44
- 239000000243 solution Substances 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- 239000000047 product Substances 0.000 description 31
- 238000005160 1H NMR spectroscopy Methods 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 230000002829 reductive effect Effects 0.000 description 22
- 102000005962 receptors Human genes 0.000 description 21
- 108020003175 receptors Proteins 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 12
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 12
- 239000012074 organic phase Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- KRVOJOCLBAAKSJ-RDTXWAMCSA-N (2R,3R)-nemonapride Chemical compound C1=C(Cl)C(NC)=CC(OC)=C1C(=O)N[C@H]1[C@@H](C)N(CC=2C=CC=CC=2)CC1 KRVOJOCLBAAKSJ-RDTXWAMCSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 208000009132 Catalepsy Diseases 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 206010047853 Waxy flexibility Diseases 0.000 description 9
- 150000001299 aldehydes Chemical class 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 229950011108 nemonapride Drugs 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000005557 antagonist Substances 0.000 description 7
- 238000001727 in vivo Methods 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- ZVCTTWIXJJEXFX-UHFFFAOYSA-N 3-(cyclopenten-1-yl)benzaldehyde Chemical compound O=CC1=CC=CC(C=2CCCC=2)=C1 ZVCTTWIXJJEXFX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 210000003169 central nervous system Anatomy 0.000 description 6
- 230000003291 dopaminomimetic effect Effects 0.000 description 6
- MSQDSRPMVCUXIA-UHFFFAOYSA-N ethyl 3-(2-oxocyclopentyl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C2C(CCC2)=O)=C1 MSQDSRPMVCUXIA-UHFFFAOYSA-N 0.000 description 6
- WLIUSEQCIVNQPG-UHFFFAOYSA-N ethyl 3-(6-oxabicyclo[3.1.0]hexan-1-yl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C23C(CCC2)O3)=C1 WLIUSEQCIVNQPG-UHFFFAOYSA-N 0.000 description 6
- QMHGNFRDMQXGMK-UHFFFAOYSA-N ethyl 3-(cyclopenten-1-yl)benzoate Chemical compound CCOC(=O)C1=CC=CC(C=2CCCC=2)=C1 QMHGNFRDMQXGMK-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 6
- 229960003878 haloperidol Drugs 0.000 description 6
- 238000010606 normalization Methods 0.000 description 6
- 230000002295 serotoninergic effect Effects 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- SZPVIOGPECKSPN-UHFFFAOYSA-N 2-[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxy]ethanamine Chemical compound C1=CC(OCCN)=C2OC(C)(C)CC2=C1 SZPVIOGPECKSPN-UHFFFAOYSA-N 0.000 description 5
- RTQGRVSXMXBTBH-UHFFFAOYSA-N 3-bromo-5-(cyclopenten-1-yl)pyridine Chemical compound BrC1=CN=CC(C=2CCCC=2)=C1 RTQGRVSXMXBTBH-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- ULFFNRHERYUHCY-UHFFFAOYSA-N [7-[tert-butyl(dimethyl)silyl]oxy-1-benzofuran-2-yl]methanol Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1OC(CO)=C2 ULFFNRHERYUHCY-UHFFFAOYSA-N 0.000 description 5
- 230000009471 action Effects 0.000 description 5
- 239000000556 agonist Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- 229960001534 risperidone Drugs 0.000 description 5
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- KBNNCAROXLDQEL-UHFFFAOYSA-N tert-butyl-[[2-(chloromethyl)-1-benzofuran-7-yl]oxy]-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1OC(CCl)=C2 KBNNCAROXLDQEL-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 241000282414 Homo sapiens Species 0.000 description 4
- 229910010082 LiAlH Inorganic materials 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- ZOKDKWMOOALWLH-UHFFFAOYSA-N [3-(cyclopenten-1-yl)phenyl]methanol Chemical compound OCC1=CC=CC(C=2CCCC=2)=C1 ZOKDKWMOOALWLH-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- GLGIFCYFLAOYDG-UHFFFAOYSA-N tert-butyl-dimethyl-[(2-methylidene-3h-1-benzofuran-7-yl)oxy]silane Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=CC2=C1OC(=C)C2 GLGIFCYFLAOYDG-UHFFFAOYSA-N 0.000 description 4
- QRZUMYVBZFGJBI-UHFFFAOYSA-N 1-(5-bromopyridin-3-yl)cyclopentan-1-ol Chemical compound C=1N=CC(Br)=CC=1C1(O)CCCC1 QRZUMYVBZFGJBI-UHFFFAOYSA-N 0.000 description 3
- UXACNZAQSBHVJT-UHFFFAOYSA-N 3-(2-fluorocyclopenten-1-yl)benzaldehyde Chemical compound C1CCC(F)=C1C1=CC=CC(C=O)=C1 UXACNZAQSBHVJT-UHFFFAOYSA-N 0.000 description 3
- MFNYHRBARJXEIW-UHFFFAOYSA-N 5-(cyclopenten-1-yl)pyridine-3-carbaldehyde Chemical compound O=CC1=CN=CC(C=2CCCC=2)=C1 MFNYHRBARJXEIW-UHFFFAOYSA-N 0.000 description 3
- 230000001090 anti-dopaminergic effect Effects 0.000 description 3
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- XJUROKFTAHXDMI-UHFFFAOYSA-N n-[[5-(cyclopenten-1-yl)pyridin-3-yl]methyl]-2-[(2,2-dimethyl-3h-1-benzofuran-7-yl)oxy]ethanamine Chemical compound C=12OC(C)(C)CC2=CC=CC=1OCCNCC(C=1)=CN=CC=1C1=CCCC1 XJUROKFTAHXDMI-UHFFFAOYSA-N 0.000 description 3
- 150000003138 primary alcohols Chemical group 0.000 description 3
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- 239000003723 serotonin 1A agonist Substances 0.000 description 3
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- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- XIGAHNVCEFUYOV-BTJKTKAUSA-N (z)-but-2-enedioic acid;n-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-n-pyridin-2-ylcyclohexanecarboxamide Chemical compound OC(=O)\C=C/C(O)=O.COC1=CC=CC=C1N1CCN(CCN(C(=O)C2CCCCC2)C=2N=CC=CC=2)CC1 XIGAHNVCEFUYOV-BTJKTKAUSA-N 0.000 description 2
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 2
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
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- 238000002474 experimental method Methods 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- XUKRJAQJZUVBSQ-UHFFFAOYSA-N n-[[3-(cyclopenten-1-yl)phenyl]methyl]-2-(2,3-dihydro-1-benzofuran-7-yloxy)ethanamine Chemical compound C=1C=CC=2CCOC=2C=1OCCNCC(C=1)=CC=CC=1C1=CCCC1 XUKRJAQJZUVBSQ-UHFFFAOYSA-N 0.000 description 2
- YMSPIDTUTRJXKM-UHFFFAOYSA-N n-[[3-(cyclopenten-1-yl)phenyl]methyl]-2-[(2-methyl-1-benzofuran-7-yl)oxy]ethanamine Chemical compound C=12OC(C)=CC2=CC=CC=1OCCNCC(C=1)=CC=CC=1C1=CCCC1 YMSPIDTUTRJXKM-UHFFFAOYSA-N 0.000 description 2
- 230000000926 neurological effect Effects 0.000 description 2
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
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- KMNZBBQMIDTINA-UHFFFAOYSA-N ethyl 3-cyclopentylbenzoate Chemical compound CCOC(=O)C1=CC=CC(C2CCCC2)=C1 KMNZBBQMIDTINA-UHFFFAOYSA-N 0.000 description 1
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- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- 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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/548—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings having unsaturation outside the six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/55—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/48—Aldehydo radicals
-
- 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
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/86—Benzo [b] furans; Hydrogenated benzo [b] furans with an oxygen atom directly attached in position 7
-
- 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
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0212854 | 2002-10-16 | ||
| FR0212854A FR2845992B1 (fr) | 2002-10-16 | 2002-10-16 | Derives de 3-(cyclopenten-1yl)-benzyl-ou3-(cyclopenten-1yl)- heteroarylmethyl-amines et leur utilisation a titre de medicaments pour le traitement de la schizophrenie |
| PCT/FR2003/003053 WO2004035561A1 (fr) | 2002-10-16 | 2003-10-16 | Derives de 3-(cyclopenten-1-yl)-benzyl- ou 3-(cyclopenten-1-yl)-heteroarylmethyl-amines et leur utilisation a titre de medicaments pour le traitement de la schizophrenie |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60305339D1 DE60305339D1 (de) | 2006-06-22 |
| DE60305339T2 true DE60305339T2 (de) | 2007-02-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60305339T Expired - Lifetime DE60305339T2 (de) | 2002-10-16 | 2003-10-16 | 3-(cyclopenten-1-yl)-benzyl- oder 3-(cyclopenten-1-yl)heteroarylmethylaminderivate und deren verwendung als arzneimittel zur behandlung von schizophrenie |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7163957B2 (https=) |
| EP (1) | EP1551821B1 (https=) |
| JP (1) | JP4566749B2 (https=) |
| CN (1) | CN1319962C (https=) |
| AT (1) | ATE326456T1 (https=) |
| AU (1) | AU2003301277B2 (https=) |
| BR (1) | BR0315365A (https=) |
| CA (1) | CA2502528C (https=) |
| DE (1) | DE60305339T2 (https=) |
| ES (1) | ES2264780T3 (https=) |
| FR (1) | FR2845992B1 (https=) |
| MX (1) | MXPA05004114A (https=) |
| PT (1) | PT1551821E (https=) |
| WO (1) | WO2004035561A1 (https=) |
| ZA (1) | ZA200503822B (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2898601A1 (fr) * | 2006-03-14 | 2007-09-21 | Pierre Fabre Medicament Sa | Procede de preparation de derives (2-(2,3-dihydro-benzofuran ou benzofuran-7-yloxy)-ethyl)-(3-cyclopenten-1-yl-benzyl) amines et intermediaire de synthese |
| US20090288701A1 (en) * | 2008-05-23 | 2009-11-26 | E.I.Du Pont De Nemours And Company | Solar cell laminates having colored multi-layer encapsulant sheets |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05125024A (ja) * | 1991-11-05 | 1993-05-21 | Yamanouchi Pharmaceut Co Ltd | 新規なアリールオキシアルキルアミン誘導体又はその塩 |
| JPH05255302A (ja) * | 1992-03-09 | 1993-10-05 | Yamanouchi Pharmaceut Co Ltd | 新規なクロマニルオキシアルキルアミン誘導体 |
| US5955495A (en) * | 1996-05-03 | 1999-09-21 | Hoffmann-La Roche Inc. | Method of treating diseases of the CNS |
| AU4088897A (en) * | 1996-08-27 | 1998-03-19 | American Home Products Corporation | 4-aminoethoxy indolone derivatives |
| AU3386199A (en) * | 1998-04-08 | 1999-10-25 | American Home Products Corporation | N-aryloxyethyl-indoly-alkylamines for the treatment of depression (5-ht1a receptor active agents) |
| CA2332275A1 (en) * | 1998-05-14 | 1999-11-18 | Zoltan Tamas Nagy | Benzofuran derivatives, pharmaceutical composition containing the same, and a process for the preparation of the active ingredient |
| FR2791676B1 (fr) * | 1999-03-29 | 2001-06-22 | Pf Medicament | Nouveaux derives de [(2-substitue-5-[thienyl])-benzyl]- [2-([isopropoxy-5-fluoro]-phenoxy) ethyl]-amine, leur procede de preparation et leur utilisation a titre de medicaments |
-
2002
- 2002-10-16 FR FR0212854A patent/FR2845992B1/fr not_active Expired - Fee Related
-
2003
- 2003-10-16 CA CA2502528A patent/CA2502528C/fr not_active Expired - Fee Related
- 2003-10-16 BR BR0315365-7A patent/BR0315365A/pt not_active IP Right Cessation
- 2003-10-16 AT AT03808761T patent/ATE326456T1/de not_active IP Right Cessation
- 2003-10-16 AU AU2003301277A patent/AU2003301277B2/en not_active Ceased
- 2003-10-16 DE DE60305339T patent/DE60305339T2/de not_active Expired - Lifetime
- 2003-10-16 EP EP03808761A patent/EP1551821B1/fr not_active Expired - Lifetime
- 2003-10-16 WO PCT/FR2003/003053 patent/WO2004035561A1/fr not_active Ceased
- 2003-10-16 JP JP2004544396A patent/JP4566749B2/ja not_active Expired - Fee Related
- 2003-10-16 PT PT03808761T patent/PT1551821E/pt unknown
- 2003-10-16 ES ES03808761T patent/ES2264780T3/es not_active Expired - Lifetime
- 2003-10-16 US US10/531,587 patent/US7163957B2/en not_active Expired - Fee Related
- 2003-10-16 MX MXPA05004114A patent/MXPA05004114A/es active IP Right Grant
- 2003-10-16 CN CNB200380101676XA patent/CN1319962C/zh not_active Expired - Fee Related
-
2005
- 2005-05-12 ZA ZA200503822A patent/ZA200503822B/en unknown
-
2006
- 2006-07-28 US US11/494,697 patent/US7235568B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003301277B2 (en) | 2009-06-18 |
| EP1551821A1 (fr) | 2005-07-13 |
| US20060014827A1 (en) | 2006-01-19 |
| CN1319962C (zh) | 2007-06-06 |
| CA2502528C (fr) | 2011-12-13 |
| US20060264471A1 (en) | 2006-11-23 |
| FR2845992B1 (fr) | 2005-02-04 |
| AU2003301277A1 (en) | 2004-05-04 |
| JP4566749B2 (ja) | 2010-10-20 |
| ATE326456T1 (de) | 2006-06-15 |
| CA2502528A1 (fr) | 2004-04-29 |
| MXPA05004114A (es) | 2005-06-22 |
| BR0315365A (pt) | 2005-08-23 |
| US7163957B2 (en) | 2007-01-16 |
| US7235568B2 (en) | 2007-06-26 |
| FR2845992A1 (fr) | 2004-04-23 |
| JP2006508080A (ja) | 2006-03-09 |
| CN1705653A (zh) | 2005-12-07 |
| ES2264780T3 (es) | 2007-01-16 |
| ZA200503822B (en) | 2006-03-29 |
| HK1073112A1 (en) | 2005-09-23 |
| WO2004035561A1 (fr) | 2004-04-29 |
| DE60305339D1 (de) | 2006-06-22 |
| EP1551821B1 (fr) | 2006-05-17 |
| PT1551821E (pt) | 2006-09-29 |
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