DE60317632T2 - 2-oxazolamine und ihre verwendung als 5-ht2b-rezeptor-antagonisten - Google Patents
2-oxazolamine und ihre verwendung als 5-ht2b-rezeptor-antagonisten Download PDFInfo
- Publication number
- DE60317632T2 DE60317632T2 DE60317632T DE60317632T DE60317632T2 DE 60317632 T2 DE60317632 T2 DE 60317632T2 DE 60317632 T DE60317632 T DE 60317632T DE 60317632 T DE60317632 T DE 60317632T DE 60317632 T2 DE60317632 T2 DE 60317632T2
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- Prior art keywords
- alkyl
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- optionally substituted
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- Prior art date
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- Expired - Lifetime
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- 239000002464 receptor antagonist Substances 0.000 title description 4
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- 108010072584 5-HT2B Serotonin Receptor Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 110
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 104
- -1 cyano, amino Chemical group 0.000 claims description 98
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- 238000000034 method Methods 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 62
- 125000001072 heteroaryl group Chemical group 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000005488 carboaryl group Chemical group 0.000 claims description 22
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 125000003368 amide group Chemical group 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 239000012453 solvate Substances 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 7
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- JGFDZZLUDWMUQH-UHFFFAOYSA-N Didecyldimethylammonium Chemical compound CCCCCCCCCC[N+](C)(C)CCCCCCCCCC JGFDZZLUDWMUQH-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
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- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- ACTKAGSPIFDCMF-UHFFFAOYSA-N 1,3-oxazol-2-amine Chemical compound NC1=NC=CO1 ACTKAGSPIFDCMF-UHFFFAOYSA-N 0.000 description 15
- CFKWTZWWRBCTIQ-UHFFFAOYSA-N 4-naphthalen-1-yl-1,3-oxazol-2-amine Chemical compound O1C(N)=NC(C=2C3=CC=CC=C3C=CC=2)=C1 CFKWTZWWRBCTIQ-UHFFFAOYSA-N 0.000 description 15
- 125000003277 amino group Chemical group 0.000 description 15
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- AWMZQHKHKGWNFG-UHFFFAOYSA-N 4-methyl-5-naphthalen-1-yl-1,3-oxazol-2-amine Chemical compound N1=C(N)OC(C=2C3=CC=CC=C3C=CC=2)=C1C AWMZQHKHKGWNFG-UHFFFAOYSA-N 0.000 description 13
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- 238000006243 chemical reaction Methods 0.000 description 13
- 125000000524 functional group Chemical group 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- CDKJLANLZOZBNT-UHFFFAOYSA-N 4-(7-bromonaphthalen-1-yl)-1,3-oxazol-2-amine Chemical compound O1C(N)=NC(C=2C3=CC(Br)=CC=C3C=CC=2)=C1 CDKJLANLZOZBNT-UHFFFAOYSA-N 0.000 description 12
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/421—1,3-Oxazoles, e.g. pemoline, trimethadione
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/422—Oxazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/48—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0203412.2A GB0203412D0 (en) | 2002-02-13 | 2002-02-13 | 5-HT 2B receptor antagonists |
| GB0203412 | 2002-02-13 | ||
| PCT/GB2003/000552 WO2003068226A1 (en) | 2002-02-13 | 2003-02-11 | 2-oxazolamines and their use as 5-ht2b receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60317632D1 DE60317632D1 (de) | 2008-01-03 |
| DE60317632T2 true DE60317632T2 (de) | 2008-10-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60317632T Expired - Lifetime DE60317632T2 (de) | 2002-02-13 | 2003-02-11 | 2-oxazolamine und ihre verwendung als 5-ht2b-rezeptor-antagonisten |
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| Country | Link |
|---|---|
| US (1) | US7429607B2 (enExample) |
| EP (1) | EP1474140B1 (enExample) |
| JP (1) | JP4439266B2 (enExample) |
| KR (1) | KR20040084905A (enExample) |
| CN (1) | CN1633291A (enExample) |
| AU (1) | AU2003207297B2 (enExample) |
| CA (1) | CA2472762A1 (enExample) |
| DE (1) | DE60317632T2 (enExample) |
| EA (1) | EA200401077A1 (enExample) |
| GB (1) | GB0203412D0 (enExample) |
| IL (1) | IL163110A (enExample) |
| MX (1) | MXPA04007738A (enExample) |
| NO (1) | NO327465B1 (enExample) |
| NZ (1) | NZ534539A (enExample) |
| PL (1) | PL370221A1 (enExample) |
| WO (1) | WO2003068226A1 (enExample) |
| ZA (1) | ZA200406010B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1299948B1 (it) | 1998-04-02 | 2000-04-04 | Azionaria Costruzioni Acma Spa | Metodo e dispositivo per la formazione di gruppi di articoli appiattiti. |
| US20050176791A1 (en) * | 2002-02-13 | 2005-08-11 | Oxford Alexander W. | 5-HT2B receptor antagonists |
| JP2006528617A (ja) * | 2003-07-24 | 2006-12-21 | ファーマジーン ラボラトリーズ リミテッド | ５−ｈｔ２ｂ受容体アンタゴニスト |
| WO2005079845A1 (ja) | 2004-02-20 | 2005-09-01 | Astellas Pharma Inc. | 片頭痛予防薬 |
| SE0400850D0 (sv) * | 2004-03-30 | 2004-03-31 | Astrazeneca Ab | Novel Compounds |
| WO2005097113A2 (en) * | 2004-04-08 | 2005-10-20 | Pharmagene Laboratories Limited | 5-ht2b receptor antagonists |
| PL1797038T3 (pl) | 2004-09-29 | 2012-11-30 | Bayer Healthcare Llc | Termodynamicznie trwała postać tosylanu bay 43-9006 |
| WO2014085413A1 (en) * | 2012-11-28 | 2014-06-05 | Temple University - Of The Commonwealth System Of Higher Education | Disubstituted oxazolidin-2-ones 5-hydroxytryptamine receptor 2b activity modulators |
| KR101592068B1 (ko) | 2013-11-08 | 2016-02-05 | 순천향대학교 산학협력단 | 플라즈마 아포리포프로테인 h를 포함하는 아스피린 과민성 호흡계 질환 및 아스피린 내성 천식 구별 진단용 마커 및 구별 진단용 키트 |
| CN116789549A (zh) * | 2023-06-16 | 2023-09-22 | 山东科源化工有限公司 | 一种羟基乙酸乙烯酯的制备工艺 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0658559A1 (de) * | 1993-12-14 | 1995-06-21 | Chemisch Pharmazeutische Forschungsgesellschaft m.b.H. | Thienothiazinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als 5-dipoxygenase und Cyclooxygenaseinhibitoren |
| WO1995024200A1 (en) | 1994-03-11 | 1995-09-14 | Eli Lilly And Company | Method for treating 5ht2b receptor related conditions |
| US5663178A (en) | 1995-02-06 | 1997-09-02 | Eli Lilly And Company | Tetrahydro-beta carbolines |
| ATE227710T1 (de) * | 1996-04-03 | 2002-11-15 | Takeda Chemical Industries Ltd | Oxazole derivate,ihre herstellung und verwendung |
| US5958934A (en) | 1996-05-23 | 1999-09-28 | Syntex (U.S.A.) Inc. | Aryl pyrimidine derivatives and uses thereof |
| US5952331A (en) | 1996-05-23 | 1999-09-14 | Syntex (Usa) Inc. | Aryl pyrimidine derivatives |
| TW440563B (en) * | 1996-05-23 | 2001-06-16 | Hoffmann La Roche | Aryl pyrimidine derivatives and a pharmaceutical composition thereof |
| WO2000023444A1 (en) * | 1998-10-21 | 2000-04-27 | Abbott Laboratories | 5,7-disubstituted-4-aminopyrido[2,3-d]pyrimidine compounds |
| EP1200093B1 (en) | 1999-07-30 | 2003-09-24 | Pharmagene Laboratories Ltd | Use of 2-amino-4-(4-fluoronaphth-1-yl)-6-isopropylpyrimidine in the treatment of gi disorders |
| AR035016A1 (es) * | 1999-08-25 | 2004-04-14 | Takeda Chemical Industries Ltd | Composicion de azol promotor de produccion/secrecion de neurotrofina, compuesto prodroga del mismo, composicion farmaceutica que lo comprende y uso del mismo para preparar esta ultima. |
-
2002
- 2002-02-13 GB GBGB0203412.2A patent/GB0203412D0/en not_active Ceased
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2003
- 2003-02-11 DE DE60317632T patent/DE60317632T2/de not_active Expired - Lifetime
- 2003-02-11 WO PCT/GB2003/000552 patent/WO2003068226A1/en not_active Ceased
- 2003-02-11 NZ NZ534539A patent/NZ534539A/en not_active IP Right Cessation
- 2003-02-11 KR KR10-2004-7012479A patent/KR20040084905A/ko not_active Ceased
- 2003-02-11 CN CNA038039532A patent/CN1633291A/zh active Pending
- 2003-02-11 AU AU2003207297A patent/AU2003207297B2/en not_active Ceased
- 2003-02-11 PL PL03370221A patent/PL370221A1/xx not_active IP Right Cessation
- 2003-02-11 EP EP03704768A patent/EP1474140B1/en not_active Expired - Lifetime
- 2003-02-11 JP JP2003567408A patent/JP4439266B2/ja not_active Expired - Fee Related
- 2003-02-11 EA EA200401077A patent/EA200401077A1/ru unknown
- 2003-02-11 MX MXPA04007738A patent/MXPA04007738A/es active IP Right Grant
- 2003-02-11 CA CA002472762A patent/CA2472762A1/en not_active Abandoned
- 2003-02-12 US US10/364,672 patent/US7429607B2/en not_active Expired - Fee Related
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2004
- 2004-07-20 IL IL163110A patent/IL163110A/en not_active IP Right Cessation
- 2004-07-28 ZA ZA200406010A patent/ZA200406010B/en unknown
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| Publication number | Publication date |
|---|---|
| ZA200406010B (en) | 2005-06-08 |
| DE60317632D1 (de) | 2008-01-03 |
| JP2005528341A (ja) | 2005-09-22 |
| EP1474140A1 (en) | 2004-11-10 |
| US20040010022A1 (en) | 2004-01-15 |
| MXPA04007738A (es) | 2004-10-15 |
| NZ534539A (en) | 2006-02-24 |
| US7429607B2 (en) | 2008-09-30 |
| NO327465B1 (no) | 2009-07-06 |
| EA200401077A1 (ru) | 2005-06-30 |
| KR20040084905A (ko) | 2004-10-06 |
| GB0203412D0 (en) | 2002-04-03 |
| WO2003068226A1 (en) | 2003-08-21 |
| CN1633291A (zh) | 2005-06-29 |
| EP1474140B1 (en) | 2007-11-21 |
| CA2472762A1 (en) | 2003-08-21 |
| IL163110A (en) | 2010-12-30 |
| AU2003207297A2 (en) | 2003-09-04 |
| JP4439266B2 (ja) | 2010-03-24 |
| NO20043799L (no) | 2004-09-10 |
| AU2003207297A1 (en) | 2003-09-04 |
| AU2003207297B2 (en) | 2008-11-06 |
| PL370221A1 (en) | 2005-05-16 |
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