ZA200503553B - 4(Pheny-piperazinyl-methyl) benzamide derivatives and their use for the treatment of pain or gastrointestinal disorders - Google Patents
4(Pheny-piperazinyl-methyl) benzamide derivatives and their use for the treatment of pain or gastrointestinal disorders Download PDFInfo
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- ZA200503553B ZA200503553B ZA200503553A ZA200503553A ZA200503553B ZA 200503553 B ZA200503553 B ZA 200503553B ZA 200503553 A ZA200503553 A ZA 200503553A ZA 200503553 A ZA200503553 A ZA 200503553A ZA 200503553 B ZA200503553 B ZA 200503553B
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- A61P25/34—Tobacco-abuse
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- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
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- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- 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
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- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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SE0203300A SE0203300D0 (sv) | 2002-11-07 | 2002-11-07 | Novel Compounds |
Publications (1)
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ZA200503553B true ZA200503553B (en) | 2006-09-27 |
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ZA200503553A ZA200503553B (en) | 2002-11-07 | 2005-05-04 | 4(Pheny-piperazinyl-methyl) benzamide derivatives and their use for the treatment of pain or gastrointestinal disorders |
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US (1) | US7396834B2 (sv) |
EP (1) | EP1562922A1 (sv) |
JP (1) | JP2006507296A (sv) |
KR (1) | KR20050072794A (sv) |
CN (1) | CN100471844C (sv) |
AR (1) | AR041898A1 (sv) |
AU (1) | AU2003274884B2 (sv) |
BR (1) | BR0315998A (sv) |
CA (1) | CA2502733A1 (sv) |
IS (1) | IS7864A (sv) |
MX (1) | MXPA05004709A (sv) |
NO (1) | NO20052699D0 (sv) |
NZ (1) | NZ539483A (sv) |
PL (1) | PL376895A1 (sv) |
RU (1) | RU2326875C2 (sv) |
SE (1) | SE0203300D0 (sv) |
TW (1) | TW200418823A (sv) |
UA (1) | UA79824C2 (sv) |
WO (1) | WO2004041800A1 (sv) |
ZA (1) | ZA200503553B (sv) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL158631A0 (en) * | 2001-05-18 | 2004-05-12 | Astrazeneca Ab | 4-(phenyl-piperazinyl-methyl) benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders |
SE0203302D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
SE0203300D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
SE0203303D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
NZ546834A (en) | 2003-10-01 | 2010-03-26 | Adolor Corp | Spirocyclic heterocyclic derivatives and methods of their use |
MX2007001240A (es) | 2004-08-02 | 2007-03-23 | Astrazeneca Ab | Derivados de diarilmetil-piperazina, preparaciones y usos de las mismas. |
SE0401968D0 (sv) * | 2004-08-02 | 2004-08-02 | Astrazeneca Ab | Diarylmethyl piperazine derivatives, preparations thereof and uses thereof |
CN101128447A (zh) * | 2005-02-28 | 2008-02-20 | 阿斯利康(瑞典)有限公司 | 二芳基甲基哌嗪衍生物,其制备及其用途 |
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 |
ES2283220B1 (es) * | 2006-04-12 | 2008-11-01 | Consejo Superior Investig. Cientificas | Uso de agonistas del receptor opioide delta en la elaboracion de composiciones farmaceuticas, composiciones farmaceuticas que las contienen y sus aplicaciones en el tratamiento de tumores. |
MX2010012325A (es) * | 2008-05-20 | 2010-12-02 | Astrazeneca Ab | Metodo para tratar trastorno ansioso depresivo mayor. |
RU2505536C1 (ru) * | 2012-12-29 | 2014-01-27 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Ярославский государственный технический университет" | 4-(1-гидрокси-1-метил-2-морфолиноэтил)бензойная и 4-(1-гидрокси-2-морфолиноциклогексил)бензойная кислоты, их фармацевтически приемлемые соли, сложные эфиры, обладающие анксиолитической активностью, и способ их получения |
Family Cites Families (43)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH585209A5 (sv) | 1973-06-29 | 1977-02-28 | Cermol Sa | |
DE2900810A1 (de) | 1979-01-11 | 1980-07-24 | Cassella Ag | Substituierte n-benzhydryl-n'-p- hydroxybenzyl-piperazine und verfahren zu ihrer herstellung |
IT1140978B (it) | 1980-05-23 | 1986-10-10 | Selvi & C Spa | 1-(4-clorobenzidril)-4-(2,3-diidros sipropil)-piperazina, metodi per la sua preparazione e relative composizione farmaceutiche |
GB8320701D0 (en) | 1983-08-01 | 1983-09-01 | Wellcome Found | Chemotherapeutic agent |
IT1196150B (it) | 1984-06-19 | 1988-11-10 | Poli Ind Chimica Spa | Derivati di 1-(bis-(4-fluorofenil)metil)-4-(3-fenil-2-propenil)-esaidro-1h-1,4-diazepina ad attivita' calcio antagonista,sua preparazione e composizioni che lo contengono |
SE8500573D0 (sv) | 1985-02-08 | 1985-02-08 | Ferrosan Ab | Novel piperazinecarboxamides having a phenoxyalkyl or thiophenoxyalkyl side chain |
US5028610A (en) | 1987-03-18 | 1991-07-02 | Sankyo Company Limited | N-benzhydryl-substituted heterocyclic derivatives, their preparation and their use |
US4829065A (en) | 1987-04-24 | 1989-05-09 | Syntex Pharmaceuticals, Ltd. | Substituted imidazolyl-alkyl-piperazine and -diazepine derivatives |
US4826844A (en) | 1987-09-30 | 1989-05-02 | American Home Products Corporation | Substituted 1-(aralkyl-piperazinoalkyl) cycloalkanols |
DK0577171T3 (da) | 1989-11-22 | 2002-06-03 | Janssen Pharmaceutica Nv | Anvendelse af piperazinacetamidderivater mod reperfusionsskader |
US5840896A (en) | 1989-11-22 | 1998-11-24 | Janssen Pharmaceutica, N.V. | Method of preventing or limiting reperfusion damage |
CA2087004C (en) | 1990-08-29 | 1998-04-21 | Noriie Itoh | Tropolone derivatives and pharmaceutical composition thereof for preventing and treating ischemic diseases |
CZ280532B6 (cs) | 1990-10-10 | 1996-02-14 | Schering Corporation | Pyridinové a pyridin-N-oxidové deriváty diaryl-methyl-piperidinů nebo piperazinů, jejich použití a způsob jejich přípravy, farmaceutický prostředek je obsahující |
US5807858A (en) | 1996-06-05 | 1998-09-15 | Delta Pharmaceutical, Inc. | Compositions and methods for reducing respiratory depression |
GB9202238D0 (en) | 1992-02-03 | 1992-03-18 | Wellcome Found | Compounds |
US5574159A (en) | 1992-02-03 | 1996-11-12 | Delta Pharmaceuticals, Inc. | Opioid compounds and methods for making therefor |
US5681830A (en) | 1992-02-03 | 1997-10-28 | Delta Pharmaceuticals, Inc. | Opioid compounds |
FR2696744B1 (fr) | 1992-10-12 | 1994-12-30 | Logeais Labor Jacques | Dérivés de 2-pyrrolidone, leur procédé de préparation et leurs applications en thérapeutique. |
RU2124511C1 (ru) | 1993-05-14 | 1999-01-10 | Фармасьютикал Ко., Лтд | Производные пиперазина |
CN1054850C (zh) | 1993-07-30 | 2000-07-26 | 德尔塔药物公司 | 用于治疗的哌嗪化合物 |
JP3352184B2 (ja) | 1993-11-12 | 2002-12-03 | 株式会社アズウェル | ピペラジン不飽和脂肪酸誘導体 |
IL117149A0 (en) | 1995-02-23 | 1996-06-18 | Schering Corp | Muscarinic antagonists |
SE9504661D0 (sv) | 1995-12-22 | 1995-12-22 | Astra Pharma Inc | New compounds |
TW548271B (en) | 1996-12-20 | 2003-08-21 | Astra Pharma Inc | Novel piperidine derivatives having an exocyclic double bond with analgesic effects |
SE9604786D0 (sv) | 1996-12-20 | 1996-12-20 | Astra Pharma Inc | New compounds |
ZA9811842B (en) | 1997-12-24 | 2000-06-23 | Ortho Mcneil Pharm Inc | 4-[aryl(piperidin-4-yl)]aminobenzamides. |
SE9904673D0 (sv) | 1999-12-20 | 1999-12-20 | Astra Pharma Inc | Novel compounds |
SE9904675D0 (sv) | 1999-12-20 | 1999-12-20 | Astra Pharma Inc | Novel compounds |
SE9904674D0 (sv) | 1999-12-20 | 1999-12-20 | Astra Pharma Inc | Novel compounds |
SE0001209D0 (sv) | 2000-04-04 | 2000-04-04 | Astrazeneca Canada Inc | Novel compounds |
IL158631A0 (en) | 2001-05-18 | 2004-05-12 | Astrazeneca Ab | 4-(phenyl-piperazinyl-methyl) benzamide derivatives and their use for the treatment of pain, anxiety or gastrointestinal disorders |
SE0101765D0 (sv) | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
SE0101766D0 (sv) | 2001-05-18 | 2001-05-18 | Astrazeneca Ab | Novel compounds |
SE0103313D0 (sv) | 2001-10-03 | 2001-10-03 | Astrazeneca Ab | Novel compounds |
RU2314809C2 (ru) | 2001-10-29 | 2008-01-20 | Маунт Кук Байосайенсиз, Инк. | Способ лечения депрессии соединениями-агонистами дельта-рецепторов |
US8476280B2 (en) | 2002-05-09 | 2013-07-02 | Versi Group, Llc | Compositions and methods for combating lower urinary tract dysfunctions with delta opioid receptor agonists |
SE0203302D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
SE0203300D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
SE0203303D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
SE0300105D0 (sv) | 2003-01-16 | 2003-01-16 | Astrazeneca Ab | Diarylmethylidene piperdine derivatives, preparations thereof and uses thereof |
SE0400027D0 (sv) | 2004-01-09 | 2004-01-09 | Astrazeneca Ab | Diarylmethyl piperazine derivatives, preparations thereof and uses thereof |
SE0401968D0 (sv) | 2004-08-02 | 2004-08-02 | Astrazeneca Ab | Diarylmethyl piperazine derivatives, preparations thereof and uses thereof |
CN101128447A (zh) | 2005-02-28 | 2008-02-20 | 阿斯利康(瑞典)有限公司 | 二芳基甲基哌嗪衍生物,其制备及其用途 |
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2002
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2003
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2005
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- 2005-06-06 NO NO20052699A patent/NO20052699D0/no not_active Application Discontinuation
Also Published As
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BR0315998A (pt) | 2005-09-20 |
CN100471844C (zh) | 2009-03-25 |
KR20050072794A (ko) | 2005-07-12 |
WO2004041800A1 (en) | 2004-05-21 |
NO20052699L (no) | 2005-06-06 |
JP2006507296A (ja) | 2006-03-02 |
IS7864A (is) | 2005-05-25 |
PL376895A1 (pl) | 2006-01-09 |
AR041898A1 (es) | 2005-06-01 |
US20060167004A1 (en) | 2006-07-27 |
TW200418823A (en) | 2004-10-01 |
NO20052699D0 (no) | 2005-06-06 |
US7396834B2 (en) | 2008-07-08 |
MXPA05004709A (es) | 2005-08-03 |
AU2003274884A1 (en) | 2004-06-07 |
RU2326875C2 (ru) | 2008-06-20 |
AU2003274884B2 (en) | 2007-11-15 |
EP1562922A1 (en) | 2005-08-17 |
CA2502733A1 (en) | 2004-05-21 |
UA79824C2 (en) | 2007-07-25 |
SE0203300D0 (sv) | 2002-11-07 |
RU2005111983A (ru) | 2006-01-20 |
NZ539483A (en) | 2007-12-21 |
CN1711251A (zh) | 2005-12-21 |
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