RU2003131968A - Производные 4-(фенил-пиперидин-4-илиден-метил)-бензамида и их применение для лечения боли, тревоги или желудочно-кишечных расстройств - Google Patents
Производные 4-(фенил-пиперидин-4-илиден-метил)-бензамида и их применение для лечения боли, тревоги или желудочно-кишечных расстройств Download PDFInfo
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- RU2003131968A RU2003131968A RU2003131968/04A RU2003131968A RU2003131968A RU 2003131968 A RU2003131968 A RU 2003131968A RU 2003131968/04 A RU2003131968/04 A RU 2003131968/04A RU 2003131968 A RU2003131968 A RU 2003131968A RU 2003131968 A RU2003131968 A RU 2003131968A
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- phenyl
- methyl
- ylidene
- compound
- piperidin
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- 0 CC(C)C(C(C)C)=CC(c(cc1)ccc1C(c1cccc(O)c1)=C1CCN(*)CC1)=O Chemical compound CC(C)C(C(C)C)=CC(c(cc1)ccc1C(c1cccc(O)c1)=C1CCN(*)CC1)=O 0.000 description 2
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D405/06—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 carbon chain containing only aliphatic carbon atoms
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- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Addiction (AREA)
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- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
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- Heart & Thoracic Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
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- Orthopedic Medicine & Surgery (AREA)
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- Hydrogenated Pyridines (AREA)
Claims (15)
1. Соединение формулы I
где R1 выбран из любого из
(1) фенила
(2) пиридинила
(3) тиенила
(4) фуранила
(5) имидазолила
(6) триазолила
(7) пирролила
(8) тиазолила
(9) пиридил-N-оксида
где каждое фенильное кольцо R1 и гетероароматическое кольцо R1 может быть независимо дополнительно замещено 1, 2 или 3 заместителями, независимо выбранными из прямого и разветвленного C1-С6алкила, NO2, CF3, C1-С6алкокси, хлоро, фторо, бромо и йодо; а также его соли.
2. Соединение по п.1, где каждое фенильное кольцо R1 и гетероароматическое кольцо R1 может быть независимо дополнительно замещено 1, 2 или 3 заместителями, независимо выбранными из метила, CF3, хлоро, фторо, бромо и йодо.
3. Соединение по п.1, где каждое фенильное кольцо R1 и гетероароматическое кольцо R1 может быть независимо дополнительно замещено метильной группой.
4. Соединение по п.1, где R1 представляет собой фенил, пирролил, пиридинил, тиенил или фуранил.
5. Соединение по п.1, выбранное из любого из:
4-[1-(1-бензил-пиперидин-4-илиден)-1-(3-гидрокси-фенил)-метил]-N,N-диизопропил-бензамида;
4-[1-(3-гидрокси-фенил)-1-(1-тиофен-2-илметил-пиперидин-4-илиден)-метил]-N,N-диизопропил-бензамида;
4-[1-(3-гидрокси-фенил)-1-(1-тиофен-3-илметил-пиперидин-4-илиден)-метил]-N,N-диизопропил-бензамида;
4-[1-(3-гидрокси-фенил)-1-(1-пиридин-4-илметил-пиперидин-4-илиден)-метил]-N,N-диизопропил-бензамида;
4-[1-(3-гидрокси-фенил)-1-(1-пиридин-2-илметил-пиперидин-4-илиден)-метил]-N,N-диизопропил-бензамида;
4-[1-(1-фуран-2-илметил-пиперидин-4-илиден)-1-(3-гидрокси-фенил)-метил]-N,N-диизопропил-бензамида;
4-[1-(3-гидрокси-фенил)-1-(1-тиазол-2-илметил-пиперидин-4-илиден)-метил]-N,N-диизопропил-бензамида;
4-{1-(3-гидрокси-фенил)-1-[1-(1Н-имидазол-2-илметил)-пиперидин-4-илиден]-метил}-N,N-диизопропил-бензамида;
4-[1-[1-(4-бром-бензил)-пиперидин-4-илиден]-1-(3-гидрокси-фенил)-метил]-N,N-диизопропил-бензамида;
4-[1-(1-пиррол-2-илметил-пиперидин-4-илиден)-1-(3-гидрокси-фенил)-метил]-N,N-диизопропил-бензамида;
4-[1-[1-(4-метокси-бензил)-пиперидин-4-илиден]-1-(3-гидрокси-фенил)-метил]-N,N-диизопропил-бензамида и
4-[1-(1-фуран-3-илметил-пиперидин-4-илиден)-1-(3-гидрокси-фенил)-метил]-N,N-диизопропил-бензамида.
6. Соединение по любому из пп.1-5 в форме его солей гидрохлорида, дигидрохлорида, сульфата, тартрата, дитрифторацетата или цитрата.
7. Способ получения соединения формулы I, при котором осуществляют реакцию А), в которой соединение общей формулы II
где PG представляет собой защитную группу уретана, такую как Boc или CBZ, либо бензильную или замещенную бензильную защитную группу, такую как 2,4-диметоксибензил, подвергают взаимодействию с 3-гидроксифенилбороновой кислотой, используя палладиевый катализатор, например Pd(PPh3)4, в присутствии основания, например Na2СО3, с получением соединений общей формулы III
после чего с указанных соединений удаляют защиту в стандартных условиях и подвергают алкилированию в восстановительных условиях соединением общей формулы R1-CHO с получением соединений общей формулы I.
8. Соединение по п.1 для применения в терапии.
9. Соединение по п.8, где терапия представляет собой устранение боли.
10. Фармацевтическая композиция, содержащая в качестве активного ингредиента соединение формулы I по п.1 вместе с фармацевтически приемлемым носителем.
11. Способ лечения боли, при котором субъекту, нуждающемуся в устранении боли, вводят эффективное количество соединения формулы I по п.1.
12. Способ лечения функциональных желудочно-кишечных расстройств, при котором субъекту, страдающему указанным функциональным желудочно-кишечным расстройством, вводят эффективное количество соединения формулы I по п.1.
13. Способ лечения тревоги, при котором субъекту, страдающему указанной тревогой, вводят эффективное количество соединения формулы I по п.1.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE0101767-2 | 2001-05-18 | ||
SE0101767A SE0101767D0 (sv) | 2001-05-18 | 2001-05-18 | Novel compounds |
Publications (1)
Publication Number | Publication Date |
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RU2003131968A true RU2003131968A (ru) | 2005-05-10 |
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ID=20284170
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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RU2003131968/04A RU2003131968A (ru) | 2001-05-18 | 2002-05-16 | Производные 4-(фенил-пиперидин-4-илиден-метил)-бензамида и их применение для лечения боли, тревоги или желудочно-кишечных расстройств |
Country Status (25)
Country | Link |
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US (1) | US20040138259A1 (ru) |
EP (1) | EP1395574B1 (ru) |
JP (1) | JP2005507372A (ru) |
KR (1) | KR20030094423A (ru) |
CN (1) | CN1547579A (ru) |
AR (1) | AR033756A1 (ru) |
AT (1) | ATE287400T1 (ru) |
BG (1) | BG108328A (ru) |
BR (1) | BR0209667A (ru) |
CA (1) | CA2446331A1 (ru) |
CO (1) | CO5540304A2 (ru) |
CZ (1) | CZ20033087A3 (ru) |
DE (1) | DE60202679T2 (ru) |
EE (1) | EE200300543A (ru) |
HU (1) | HUP0401285A2 (ru) |
IL (1) | IL158695A0 (ru) |
IS (1) | IS7024A (ru) |
MX (1) | MXPA03010438A (ru) |
NO (1) | NO20035118D0 (ru) |
PL (1) | PL366389A1 (ru) |
RU (1) | RU2003131968A (ru) |
SE (1) | SE0101767D0 (ru) |
SK (1) | SK13932003A3 (ru) |
WO (1) | WO2002094810A1 (ru) |
ZA (1) | ZA200308635B (ru) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CL2004000754A1 (es) * | 2003-04-11 | 2005-02-25 | Janssen Pharmaceutica Nv | Uso de compuestos derivados de 4-fenil-4-(1h-imidazol-2-il)piperidina, como agonistas delta-opioides no peptidicos, para preparar un medicamento util en prevenir o tratar trastornos del sistema nervioso central. |
SE0301443D0 (sv) * | 2003-05-16 | 2003-05-16 | Astrazeneca Ab | Diarylmethylidene piperidine derivatives, preparations thereof and uses thereof |
JP2007503457A (ja) * | 2003-05-16 | 2007-02-22 | アストラゼネカ・アクチエボラーグ | ジアリールメチリデンピペリジン誘導体、その製造およびその使用 |
WO2005005478A2 (en) * | 2003-07-02 | 2005-01-20 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with g protein-coupled opioid receptor; delta 1 (oprd1) |
NZ546834A (en) | 2003-10-01 | 2010-03-26 | Adolor Corp | Spirocyclic heterocyclic derivatives and methods of their use |
US7598261B2 (en) | 2005-03-31 | 2009-10-06 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
US7576207B2 (en) | 2006-04-06 | 2009-08-18 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
JP2010503669A (ja) | 2006-09-12 | 2010-02-04 | アドラー コーポレーション | 認知機能の強化のためのn含有スピロ化合物の使用 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2898339A (en) * | 1957-07-29 | 1959-08-04 | Wm S Merrell Co | N-substituted benzhydrol, benzhydryl, and benzhydrylidene piperidine |
US4581171A (en) * | 1983-07-27 | 1986-04-08 | Janssen Pharmaceutica, N.V. | [[Bis(aryl)methylene]-1-piperidinyl]alkyl-pyrimidinones useful for treating psychotropic disorders |
US4816586A (en) * | 1987-07-29 | 1989-03-28 | Regents Of The University Of Minnesota | Delta opioid receptor antagonists |
US5140029A (en) * | 1989-01-09 | 1992-08-18 | Janssen Pharmaceutica N.V. | 2-aminopyrimidinone derivatives |
US4939137A (en) * | 1989-06-28 | 1990-07-03 | Ortho Pharmaceutical Corporation | Ring-fused thienopyrimidinedione derivatives |
US5683998A (en) * | 1991-04-23 | 1997-11-04 | Toray Industries, Inc. | Tricyclic triazolo derivatives, processes for producing the same and the uses of the same |
US5574159A (en) * | 1992-02-03 | 1996-11-12 | Delta Pharmaceuticals, Inc. | Opioid compounds and methods for making therefor |
TW548271B (en) * | 1996-12-20 | 2003-08-21 | Astra Pharma Inc | Novel piperidine derivatives having an exocyclic double bond with analgesic effects |
US6436959B1 (en) * | 1998-12-23 | 2002-08-20 | Ortho-Mcneil Pharmaceutical, Inc. | 4-[aryl(piperidin-4-yl)]aminobenzamides |
SE0001207D0 (sv) * | 2000-04-04 | 2000-04-04 | Astrazeneca Canada Inc | Novel compounds |
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- 2001-05-18 SE SE0101767A patent/SE0101767D0/xx unknown
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- 2002-05-16 JP JP2002591483A patent/JP2005507372A/ja active Pending
- 2002-05-16 HU HU0401285A patent/HUP0401285A2/hu unknown
- 2002-05-16 KR KR10-2003-7014944A patent/KR20030094423A/ko not_active Application Discontinuation
- 2002-05-16 DE DE60202679T patent/DE60202679T2/de not_active Expired - Fee Related
- 2002-05-16 AT AT02733703T patent/ATE287400T1/de not_active IP Right Cessation
- 2002-05-16 CZ CZ20033087A patent/CZ20033087A3/cs unknown
- 2002-05-16 CA CA002446331A patent/CA2446331A1/en not_active Abandoned
- 2002-05-16 EE EEP200300543A patent/EE200300543A/xx unknown
- 2002-05-16 BR BR0209667-6A patent/BR0209667A/pt not_active Application Discontinuation
- 2002-05-16 PL PL02366389A patent/PL366389A1/xx not_active Application Discontinuation
- 2002-05-16 EP EP02733703A patent/EP1395574B1/en not_active Expired - Lifetime
- 2002-05-16 AR ARP020101812A patent/AR033756A1/es not_active Application Discontinuation
- 2002-05-16 IL IL15869502A patent/IL158695A0/xx unknown
- 2002-05-16 RU RU2003131968/04A patent/RU2003131968A/ru not_active Application Discontinuation
- 2002-05-16 SK SK1393-2003A patent/SK13932003A3/sk unknown
- 2002-05-16 US US10/477,854 patent/US20040138259A1/en not_active Abandoned
- 2002-05-16 WO PCT/SE2002/000946 patent/WO2002094810A1/en not_active Application Discontinuation
- 2002-05-16 CN CNA02810191XA patent/CN1547579A/zh active Pending
- 2002-05-16 MX MXPA03010438A patent/MXPA03010438A/es unknown
-
2003
- 2003-11-05 ZA ZA200308635A patent/ZA200308635B/en unknown
- 2003-11-07 BG BG108328A patent/BG108328A/bg unknown
- 2003-11-11 IS IS7024A patent/IS7024A/is unknown
- 2003-11-12 CO CO03100160A patent/CO5540304A2/es not_active Application Discontinuation
- 2003-11-17 NO NO20035118A patent/NO20035118D0/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
PL366389A1 (en) | 2005-01-24 |
BR0209667A (pt) | 2004-04-20 |
CA2446331A1 (en) | 2002-11-28 |
MXPA03010438A (es) | 2004-03-09 |
IS7024A (is) | 2003-11-11 |
HUP0401285A2 (hu) | 2004-12-28 |
CN1547579A (zh) | 2004-11-17 |
SE0101767D0 (sv) | 2001-05-18 |
ATE287400T1 (de) | 2005-02-15 |
JP2005507372A (ja) | 2005-03-17 |
US20040138259A1 (en) | 2004-07-15 |
DE60202679D1 (de) | 2005-02-24 |
EE200300543A (et) | 2004-02-16 |
NO20035118D0 (no) | 2003-11-17 |
CZ20033087A3 (cs) | 2004-05-12 |
IL158695A0 (en) | 2004-05-12 |
ZA200308635B (en) | 2005-02-07 |
CO5540304A2 (es) | 2005-07-29 |
BG108328A (bg) | 2004-12-30 |
DE60202679T2 (de) | 2006-03-30 |
WO2002094810A1 (en) | 2002-11-28 |
EP1395574B1 (en) | 2005-01-19 |
AR033756A1 (es) | 2004-01-07 |
SK13932003A3 (sk) | 2004-05-04 |
EP1395574A1 (en) | 2004-03-10 |
KR20030094423A (ko) | 2003-12-11 |
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