JP2003503487A5 - - Google Patents
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- Publication number
- JP2003503487A5 JP2003503487A5 JP2001507818A JP2001507818A JP2003503487A5 JP 2003503487 A5 JP2003503487 A5 JP 2003503487A5 JP 2001507818 A JP2001507818 A JP 2001507818A JP 2001507818 A JP2001507818 A JP 2001507818A JP 2003503487 A5 JP2003503487 A5 JP 2003503487A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituted
- compound
- hydrogen
- atom
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 description 27
- -1 bicyclo [3.2.1] octanyl Chemical group 0.000 description 13
- 229910052801 chlorine Inorganic materials 0.000 description 11
- 239000001257 hydrogen Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 229910052731 fluorine Chemical group 0.000 description 6
- 150000004677 hydrates Chemical class 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000012453 solvate Substances 0.000 description 6
- 150000001412 amines Chemical group 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 2
- 150000001638 boron Chemical class 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000000460 chlorine Chemical group 0.000 description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 201000000980 schizophrenia Diseases 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004342 dicyclopropylmethyl group Chemical group [H]C1([H])C([H])([H])C1([H])C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9908532A FR2795724B1 (fr) | 1999-07-02 | 1999-07-02 | Nouveaux derives du benzene, un procede pour leur preparation et les compositions pharmaceutiques les contenant |
| FR99/08532 | 1999-07-02 | ||
| PCT/FR2000/001790 WO2001002380A1 (fr) | 1999-07-02 | 2000-06-27 | N-aralkyl amines cycliques antipsychotiques |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003503487A JP2003503487A (ja) | 2003-01-28 |
| JP2003503487A5 true JP2003503487A5 (enExample) | 2007-06-14 |
| JP4931309B2 JP4931309B2 (ja) | 2012-05-16 |
Family
ID=9547628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001507818A Expired - Fee Related JP4931309B2 (ja) | 1999-07-02 | 2000-06-27 | 抗精神病薬の環式ｎ−アラルキルアミン |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6908914B1 (enExample) |
| EP (1) | EP1196403B1 (enExample) |
| JP (1) | JP4931309B2 (enExample) |
| KR (1) | KR100760446B1 (enExample) |
| CN (1) | CN1156462C (enExample) |
| AR (1) | AR029374A1 (enExample) |
| AT (1) | ATE309231T1 (enExample) |
| AU (1) | AU778299B2 (enExample) |
| BG (1) | BG65209B1 (enExample) |
| BR (1) | BR0012463B1 (enExample) |
| CA (1) | CA2376691C (enExample) |
| CO (1) | CO5021196A1 (enExample) |
| CZ (1) | CZ300936B6 (enExample) |
| DE (1) | DE60023898T2 (enExample) |
| DK (1) | DK1196403T3 (enExample) |
| EA (1) | EA004048B1 (enExample) |
| ES (1) | ES2250160T3 (enExample) |
| FR (1) | FR2795724B1 (enExample) |
| HK (1) | HK1043122A1 (enExample) |
| HR (1) | HRP20010949B1 (enExample) |
| HU (1) | HU228983B1 (enExample) |
| IL (2) | IL147069A0 (enExample) |
| ME (1) | MEP25508A (enExample) |
| MX (1) | MXPA01013207A (enExample) |
| NO (1) | NO322230B1 (enExample) |
| NZ (1) | NZ516342A (enExample) |
| RS (1) | RS50266B (enExample) |
| TW (1) | TWI285640B (enExample) |
| UA (1) | UA71009C2 (enExample) |
| WO (1) | WO2001002380A1 (enExample) |
| ZA (1) | ZA200200018B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE50207026D1 (de) * | 2001-08-23 | 2006-07-06 | Bayer Cropscience Sa | Substituierte propargylamine |
| WO2007047978A2 (en) | 2005-10-21 | 2007-04-26 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| JP2009513672A (ja) | 2005-10-31 | 2009-04-02 | ブレインセルス，インコーポレイティド | 神経発生のｇａｂａ受容体媒介調節 |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| MX2008014320A (es) | 2006-05-09 | 2009-03-25 | Braincells Inc | Neurogenesis mediada por el receptor de 5-hidroxitriptamina. |
| EP2377531A2 (en) | 2006-05-09 | 2011-10-19 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE790971A (fr) * | 1971-11-09 | 1973-05-07 | Janssen Pharmaceutica Nv | Metode ter voorkoming van patologische reakties die de funktie van het komplement vereisen |
| JPS504086A (enExample) * | 1973-01-18 | 1975-01-16 | ||
| GB1475314A (en) * | 1973-11-02 | 1977-06-01 | Cm Ind | Phenyl-propylamine derivatives |
| US4104383A (en) * | 1973-11-02 | 1978-08-01 | C M Industries | Derivatives of phenylpropenylamine |
| US4912222A (en) * | 1988-06-17 | 1990-03-27 | Fisons Corporation | Antihistamines related to cyproheptadine |
| US4855462A (en) * | 1988-06-17 | 1989-08-08 | Pennwalt Corporation | Antihistamines |
| EP0347123A3 (en) * | 1988-06-17 | 1991-07-03 | Fisons Corporation | Dibenzo-cycloheptenyl, -cycloheptyl and -oxepinyl amines having antihistaminic properties |
| FR2663328B1 (fr) | 1990-06-14 | 1994-08-05 | Sanofi Sa | Derives d'hexahydroazepines, un procede pour leur preparation et compositions pharmaceutiques les contenant. |
| JPH06509069A (ja) * | 1991-06-27 | 1994-10-13 | バージニア・コモンウェルス・ユニバーシティ | シグマレセプターリガンドおよびその用途 |
| JP3199405B2 (ja) * | 1991-08-30 | 2001-08-20 | 生化学工業株式会社 | 肝細胞球状集塊化剤及び球状集塊化肝細胞の製造方法 |
| US5486517A (en) * | 1994-05-10 | 1996-01-23 | Warner-Lambert Company | Benzimidazoles and imidazopyridines as central nervous system agents |
| FR2751645B1 (fr) * | 1996-07-29 | 1998-12-24 | Sanofi Sa | Amines pour la fabrication de medicaments destines a empecher la proliferation de cellules tumorales |
| TR199902283T2 (xx) * | 1997-03-18 | 1999-12-21 | Smithkline Beecham P.L.C. | �kame edilmi� izokuinolin t�revleri ve bunlar�n antikonvulsant olarak kullan�m�. |
-
1999
- 1999-07-02 FR FR9908532A patent/FR2795724B1/fr not_active Expired - Fee Related
-
2000
- 2000-06-27 JP JP2001507818A patent/JP4931309B2/ja not_active Expired - Fee Related
- 2000-06-27 CN CNB008111413A patent/CN1156462C/zh not_active Expired - Fee Related
- 2000-06-27 NZ NZ516342A patent/NZ516342A/en not_active IP Right Cessation
- 2000-06-27 UA UA2001128823A patent/UA71009C2/uk unknown
- 2000-06-27 MX MXPA01013207A patent/MXPA01013207A/es active IP Right Grant
- 2000-06-27 AT AT00946022T patent/ATE309231T1/de active
- 2000-06-27 RS YU91101A patent/RS50266B/sr unknown
- 2000-06-27 HK HK02104681.4A patent/HK1043122A1/zh unknown
- 2000-06-27 HU HU0202200A patent/HU228983B1/hu not_active IP Right Cessation
- 2000-06-27 WO PCT/FR2000/001790 patent/WO2001002380A1/fr not_active Ceased
- 2000-06-27 CA CA002376691A patent/CA2376691C/en not_active Expired - Fee Related
- 2000-06-27 ME MEP-255/08A patent/MEP25508A/xx unknown
- 2000-06-27 ES ES00946022T patent/ES2250160T3/es not_active Expired - Lifetime
- 2000-06-27 EA EA200101209A patent/EA004048B1/ru not_active IP Right Cessation
- 2000-06-27 EP EP00946022A patent/EP1196403B1/fr not_active Expired - Lifetime
- 2000-06-27 DE DE60023898T patent/DE60023898T2/de not_active Expired - Lifetime
- 2000-06-27 IL IL14706900A patent/IL147069A0/xx active IP Right Grant
- 2000-06-27 BR BRPI0012463-0A patent/BR0012463B1/pt not_active IP Right Cessation
- 2000-06-27 CZ CZ20014697A patent/CZ300936B6/cs not_active IP Right Cessation
- 2000-06-27 US US10/019,205 patent/US6908914B1/en not_active Expired - Lifetime
- 2000-06-27 KR KR1020017016966A patent/KR100760446B1/ko not_active Expired - Fee Related
- 2000-06-27 HR HR20010949A patent/HRP20010949B1/xx not_active IP Right Cessation
- 2000-06-27 AU AU59924/00A patent/AU778299B2/en not_active Ceased
- 2000-06-27 DK DK00946022T patent/DK1196403T3/da active
- 2000-06-27 TW TW089112618A patent/TWI285640B/zh not_active IP Right Cessation
- 2000-06-28 CO CO00048530A patent/CO5021196A1/es unknown
- 2000-06-30 AR ARP000103334A patent/AR029374A1/es active IP Right Grant
-
2001
- 2001-12-12 IL IL147069A patent/IL147069A/en not_active IP Right Cessation
- 2001-12-20 BG BG106255A patent/BG65209B1/bg unknown
- 2001-12-27 NO NO20016392A patent/NO322230B1/no not_active IP Right Cessation
-
2002
- 2002-01-02 ZA ZA200200018A patent/ZA200200018B/en unknown
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