LT3264B - Therapeutic heterocyclic compounds - Google Patents
Therapeutic heterocyclic compounds Download PDFInfo
- Publication number
- LT3264B LT3264B LTIP419A LTIP419A LT3264B LT 3264 B LT3264 B LT 3264B LT IP419 A LTIP419 A LT IP419A LT IP419 A LTIP419 A LT IP419A LT 3264 B LT3264 B LT 3264B
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- LT
- Lithuania
- Prior art keywords
- formula
- compound
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- 230000001225 therapeutic effect Effects 0.000 title description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 188
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- 150000003839 salts Chemical class 0.000 claims abstract description 40
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229940124597 therapeutic agent Drugs 0.000 claims abstract description 4
- -1 N, N-dimethyl-2- [5- (2-oxo-1,3-oxazolin-4-ylmethyl) -1H-indol-3-yl] ethylamine Chemical compound 0.000 claims description 40
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- YJBKVPRVZAQTPY-UHFFFAOYSA-J tetrachlorostannane;dihydrate Chemical compound O.O.Cl[Sn](Cl)(Cl)Cl YJBKVPRVZAQTPY-UHFFFAOYSA-J 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- C07D401/14—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 three or more hetero rings
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D413/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909012672A GB9012672D0 (en) | 1990-06-07 | 1990-06-07 | Therapeutic heterocyclic compounds |
| GB919102182A GB9102182D0 (en) | 1991-02-01 | 1991-02-01 | Therapeutic heterocyclic compounds |
| PCT/GB1991/000908 WO1991018897A1 (en) | 1990-06-07 | 1991-06-06 | Therapeutic heterocyclic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP419A LTIP419A (en) | 1994-11-25 |
| LT3264B true LT3264B (en) | 1995-05-25 |
Family
ID=26297174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP419A LT3264B (en) | 1990-06-07 | 1993-03-15 | Therapeutic heterocyclic compounds |
Country Status (37)
| Country | Link |
|---|---|
| US (3) | US5399574A (de) |
| EP (2) | EP0636623B1 (de) |
| JP (1) | JP2738461B2 (de) |
| KR (1) | KR100215627B1 (de) |
| AT (2) | ATE156823T1 (de) |
| AU (1) | AU646871B2 (de) |
| CA (2) | CA2064815C (de) |
| CZ (1) | CZ288351B6 (de) |
| DE (3) | DE69132691T2 (de) |
| DK (1) | DK0486666T3 (de) |
| EG (1) | EG19650A (de) |
| ES (1) | ES2104708T3 (de) |
| FI (3) | FI105686B (de) |
| GR (1) | GR3024828T3 (de) |
| HK (1) | HK1000534A1 (de) |
| HR (1) | HRP940524B1 (de) |
| HU (2) | HU219974B (de) |
| IE (1) | IE911931A1 (de) |
| IL (3) | IL114690A (de) |
| LT (1) | LT3264B (de) |
| LU (1) | LU90205I2 (de) |
| LV (1) | LV10274B (de) |
| MC (1) | MC2210A1 (de) |
| MX (1) | MX9203421A (de) |
| MY (1) | MY110226A (de) |
| NL (1) | NL980001I2 (de) |
| NO (2) | NO300634B1 (de) |
| NZ (1) | NZ238424A (de) |
| PL (1) | PL166214B1 (de) |
| PT (1) | PT97888B (de) |
| RU (1) | RU2160736C2 (de) |
| SA (1) | SA05260104B1 (de) |
| SI (2) | SI21560B (de) |
| SK (1) | SK281621B6 (de) |
| UA (1) | UA37178C2 (de) |
| WO (1) | WO1991018897A1 (de) |
| YU (1) | YU48855B (de) |
Families Citing this family (128)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ283018B6 (cs) * | 1991-02-01 | 1997-12-17 | Merck Sharp And Dohme Limited | Deriváty imidazolu, triazolu a tetrazolu a farmaceutické přípravky na jejich bázi |
| TW263508B (de) * | 1991-02-12 | 1995-11-21 | Pfizer | |
| JP2840448B2 (ja) * | 1991-11-25 | 1998-12-24 | フアイザー・インコーポレイテツド | インドール誘導体 |
| GB9201038D0 (en) * | 1992-01-16 | 1992-03-11 | Glaxo Group Ltd | Chemical compounds |
| TW288010B (de) * | 1992-03-05 | 1996-10-11 | Pfizer | |
| AU669160B2 (en) * | 1992-03-13 | 1996-05-30 | Merck Sharp & Dohme Limited | Imidazole, triazole and tetrazole derivatives |
| GB9207396D0 (en) * | 1992-04-03 | 1992-05-13 | Merck Sharp & Dohme | Therapeutic agents |
| US6380233B1 (en) | 1992-04-07 | 2002-04-30 | Pfizer Inc | Indole derivatives as 5-HT1 agonists |
| RU2101283C1 (ru) | 1992-04-07 | 1998-01-10 | Пфайзер Инк. | Производные индола или их фармацевтически приемлемые соли |
| DE69307875T2 (de) * | 1992-04-10 | 1997-05-22 | Pfizer | Acylaminoindolderivate als 5-ht1 agonisten |
| GB9207930D0 (en) * | 1992-04-10 | 1992-05-27 | Pfizer Ltd | Indoles |
| GB9208161D0 (en) * | 1992-04-14 | 1992-05-27 | Pfizer Ltd | Indoles |
| GB9208463D0 (en) * | 1992-04-16 | 1992-06-03 | Merck Sharp & Dohme | Therapeutic agents |
| GB9209882D0 (en) * | 1992-05-07 | 1992-06-24 | Glaxo Lab Sa | Compositions |
| GB9211277D0 (en) | 1992-05-28 | 1992-07-15 | Glaxo Group Inc | Pharmaceutical compositions |
| WO1994002477A1 (en) * | 1992-07-24 | 1994-02-03 | Merck Sharp & Dohme Limited | Imidazole, triazole and tetrazole derivatives |
| GB9216009D0 (en) * | 1992-07-28 | 1992-09-09 | Almirall Lab | New indol derivatives |
| IL106445A (en) * | 1992-07-30 | 1998-01-04 | Merck Sharp & Dohme | History of 1,2,4-Trans-Triazole 4-Transform, Preparation and Pharmaceutical Preparations Containing Them |
| ES2056025B1 (es) * | 1992-10-08 | 1995-05-01 | Almirall Lab | Nuevos derivados de indol. |
| TW251284B (de) * | 1992-11-02 | 1995-07-11 | Pfizer | |
| GB9226532D0 (en) * | 1992-12-21 | 1993-02-17 | Smithkline Beecham Plc | Compounds |
| FR2701026B1 (fr) * | 1993-02-02 | 1995-03-31 | Adir | Nouveaux dérivés de l'indole, de l'indazole et du benzisoxazole, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent. |
| ES2070087B1 (es) * | 1993-08-13 | 1996-02-16 | Pfizer | Derivados de indol |
| AU686654B2 (en) * | 1993-08-31 | 1998-02-12 | Pfizer Inc. | 5-arylindole derivatives |
| US5468768A (en) * | 1994-01-06 | 1995-11-21 | Bristol-Myers Squibb Company | Antimigraine derivatives of indolylcycloalkanylamines |
| US6423731B2 (en) * | 1994-01-06 | 2002-07-23 | Zeneca Limited | Indole derivatives as prodrugs of 5-HT1-like receptor agonists |
| GB9401436D0 (en) * | 1994-01-26 | 1994-03-23 | Wellcome Found | Therapeutic heterocyclic compounds |
| JPH10501212A (ja) * | 1994-05-19 | 1998-02-03 | メルク シヤープ エンド ドーム リミテツド | ５−ｈｔ▲下１ｄ▼−アルファ作働薬としてのインドール−３−イルアルキルのピペラジン、ピペリジンおよびテトラヒドロピリジン誘導体 |
| DK0765322T3 (da) * | 1994-06-01 | 2001-10-22 | Astrazeneca Ab | Indolderivater som pro-drugs for 5-HT1-lignende receptoragonister |
| CA2194984C (en) * | 1994-07-26 | 2002-07-02 | John Eugene Macor | 4-indole derivatives as serotonin agonists and antagonists |
| US5521196A (en) * | 1994-10-05 | 1996-05-28 | Eli Lilly And Company | 5-HT1F agonists for the treatment of migraine |
| GB9423682D0 (en) * | 1994-11-23 | 1995-01-11 | Merck Sharp & Dohme | Therapeutic agents |
| US5521197A (en) * | 1994-12-01 | 1996-05-28 | Eli Lilly And Company | 3-<1-alkylenearyl>-4-<1,2,3,6-tetrahydropyridinyl>-and 3-<1-alkylenearyl>-4-piperidinyl-1h-indoles: new 5-HT1F agonists |
| JPH10509721A (ja) * | 1994-12-06 | 1998-09-22 | メルク シヤープ エンド ドーム リミテツド | ５ｈｔ１レセプターアゴニストとしてのアゼチジン、ピロリジン及びピペリジン誘導体 |
| DE4443892A1 (de) * | 1994-12-09 | 1996-06-13 | Bayer Ag | 4-(Chinolin-2-yl-methoxy)-phenyl-essigsäurederivate |
| GB9501865D0 (en) * | 1995-01-31 | 1995-03-22 | Merck Sharp & Dohme | Therapeutic agents |
| TR199700993T1 (xx) * | 1995-03-20 | 1998-03-21 | Eli Lilly And Company | 5-ikameli-3-(1,2,3,6-tetrahidropridin-4-il)- ve 3-(piperidin-4-il)-1H-indoller: yeni 5-HT1F agonistler. |
| GB9515060D0 (en) * | 1995-07-22 | 1995-09-20 | Wellcome Found | Therapeutic heterocyclic compounds |
| GB9515305D0 (en) * | 1995-07-26 | 1995-09-20 | Wellcome Found | Therapeutic heterocyclic compounds |
| GB9516145D0 (en) * | 1995-08-07 | 1995-10-04 | Wellcome Found | Improved chemical synthesis |
| GB9516143D0 (en) * | 1995-08-07 | 1995-10-04 | Wellcome Found | Improved chemical synthesis |
| US6909005B1 (en) * | 1995-08-07 | 2005-06-21 | Astrazeneca Uk Limited | One post synthesis of 2-oxazolidinone derivatives |
| JPH11513666A (ja) * | 1995-10-10 | 1999-11-24 | イーライ・リリー・アンド・カンパニー | Ｎ−［２−置換−３−（２−アミノエチル）−１ｈ−インドール−５−イル］−アミド：新規５−ｈｔ▲下１ｆ▼作動剤 |
| AU7319096A (en) * | 1995-11-02 | 1997-05-22 | Merck Sharp & Dohme Limited | Bicyclic heteroaryl-alkylene-(homo)piperazinones and thione analogues thereof, their preparation and their use as selective agonists of 5-ht1-like receptors |
| GB9609374D0 (en) * | 1996-05-03 | 1996-07-10 | Merck Sharp & Dohme | Therapeutic agents |
| US5891885A (en) * | 1996-10-09 | 1999-04-06 | Algos Pharmaceutical Corporation | Method for treating migraine |
| GB9706089D0 (en) * | 1997-03-24 | 1997-05-14 | Scherer Ltd R P | Pharmaceutical composition |
| US6066092A (en) * | 1997-11-06 | 2000-05-23 | Cady; Roger K. | Preemptive prophylaxis of migraine device and method |
| US7189753B1 (en) | 1997-11-06 | 2007-03-13 | Cady Roger K | Preemptive prophylaxis of migraine |
| AR017200A1 (es) | 1997-12-23 | 2001-08-22 | Astrazeneca Ab | Compuestos inhibidores de la proteina cinasa c, sales farmaceuticamente aceptables de los mismos, formulaciones farmaceuitcas que los comprenden, usode las mismas y proceso para la sintesis de dichos compuestos |
| SE9800835D0 (sv) | 1998-03-13 | 1998-03-13 | Astra Ab | New Compounds |
| AU4961499A (en) * | 1998-06-26 | 2000-01-17 | Eli Lilly And Company | 5-HT1f agonists |
| US6492406B1 (en) | 1999-05-21 | 2002-12-10 | Astrazeneca Ab | Pharmaceutically active compounds |
| US6346625B1 (en) * | 1999-06-23 | 2002-02-12 | Astrazeneca Ab | Protein kinase inhibitors |
| GB9928578D0 (en) * | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Pharmaceutical formulations |
| ATE374192T1 (de) * | 2000-11-29 | 2007-10-15 | Lilly Co Eli | 1-(2-m-methansulfonamidophenylethyl)-4-(m- trifluoromethylphenyl)piperazine und ihre akzeptablen pharmazeutischen salze und solvate und ihre verwendung zur behandlung von inkontinenz |
| US7645442B2 (en) | 2001-05-24 | 2010-01-12 | Alexza Pharmaceuticals, Inc. | Rapid-heating drug delivery article and method of use |
| US7090830B2 (en) * | 2001-05-24 | 2006-08-15 | Alexza Pharmaceuticals, Inc. | Drug condensation aerosols and kits |
| US7585493B2 (en) | 2001-05-24 | 2009-09-08 | Alexza Pharmaceuticals, Inc. | Thin-film drug delivery article and method of use |
| US20070122353A1 (en) * | 2001-05-24 | 2007-05-31 | Hale Ron L | Drug condensation aerosols and kits |
| US7458374B2 (en) | 2002-05-13 | 2008-12-02 | Alexza Pharmaceuticals, Inc. | Method and apparatus for vaporizing a compound |
| US20030051728A1 (en) * | 2001-06-05 | 2003-03-20 | Lloyd Peter M. | Method and device for delivering a physiologically active compound |
| US8329734B2 (en) | 2009-07-27 | 2012-12-11 | Afgin Pharma Llc | Topical therapy for migraine |
| EP1435945B1 (de) * | 2001-06-05 | 2008-08-13 | Aung-din, Ronald | Topische migränetherapie |
| US20030017175A1 (en) * | 2001-07-05 | 2003-01-23 | R.T. Alamo Ventures I, Inc. | Sublingual administration of dihydroergotamine for the treatment of migraine |
| US6685951B2 (en) | 2001-07-05 | 2004-02-03 | R. T. Alamo Ventures I, Inc. | Administration of dihydroergotamine as a sublingual spray or aerosol for the treatment of migraine |
| US20030198669A1 (en) * | 2001-07-05 | 2003-10-23 | R.T. Alamo Ventures I, Llc | Compositions and methods for rapid dissolving formulations of dihydroergotamine and caffeine for the treatment of migraine |
| AU2003217676B2 (en) | 2002-02-22 | 2009-06-11 | Takeda Pharmaceutical Company Limited | Active agent delivery systems and methods for protecting and administering active agents |
| CA2490115C (en) | 2002-06-21 | 2009-09-01 | Suven Life Sciences Limited | Arylalkyl indoles having serotonin receptor affinity useful as therapeutic agents, process for their preparation and pharmaceutical compositions containing them |
| WO2004000849A2 (en) | 2002-06-21 | 2003-12-31 | Suven Life Sciences Limited | Tetracyclic arylsulfonyl indoles having serotonin receptor affinity |
| ES2204302B2 (es) | 2002-08-07 | 2005-03-01 | Laboratorios Vita, S.A. | Procedimiento para la obtencion de un compuesto farmaceuticamente activo. |
| DE10237722A1 (de) * | 2002-08-17 | 2004-08-19 | Aventis Pharma Deutschland Gmbh | Indol- oder Benzimidazolderivate zur Modulation der IKappaB-Kinase |
| US20040105818A1 (en) * | 2002-11-26 | 2004-06-03 | Alexza Molecular Delivery Corporation | Diuretic aerosols and methods of making and using them |
| US7913688B2 (en) * | 2002-11-27 | 2011-03-29 | Alexza Pharmaceuticals, Inc. | Inhalation device for producing a drug aerosol |
| EP1567492B1 (de) | 2002-11-28 | 2013-05-22 | Suven Life Sciences Limited | N-arylsulfonyl-3-aminoalkoxyindole |
| KR100818508B1 (ko) | 2002-11-28 | 2008-03-31 | 수벤 라이프 사이언시스 리미티드 | 세로토닌 수용체 친화력을 가지는 엔-아릴술포닐-3-치환인돌, 그 제조방법 및 그를 포함하는 약제학적 조성물 |
| KR100739987B1 (ko) | 2002-12-18 | 2007-07-16 | 수벤 라이프 사이언시스 리미티드 | 세로토닌 수용체 친화력을 가지는 테트라사이클릭 3-치환인돌 |
| AU2003299227A1 (en) * | 2002-12-20 | 2004-07-14 | Ciba Specialty Chemicals Holding Inc. | Synthesis of amines and intermediates for the synthesis thereof |
| WO2004063175A1 (en) * | 2003-01-13 | 2004-07-29 | Natco Pharma Limited | A novel and an improved process for the preparation of (s)-4-(4-aminobenzyl)-2- oxazolidinone |
| GB0302094D0 (en) | 2003-01-29 | 2003-02-26 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| US20040192958A1 (en) * | 2003-03-25 | 2004-09-30 | Hyatt John Anthony | Process for preparing derivatives of 4-halobutyraldehyde |
| JP2007516149A (ja) | 2003-05-21 | 2007-06-21 | アレックザ ファーマシューティカルズ， インコーポレイテッド | 基板温度の均一性を制御する方法、および、内蔵式加熱ユニットおよびそれを使用する薬剤供給ユニット |
| AR044688A1 (es) | 2003-06-12 | 2005-09-21 | Euro Celtique Sa | Agentes terapeuticos utiles para el tratamiento del dolor |
| US20070065463A1 (en) * | 2003-06-20 | 2007-03-22 | Ronald Aung-Din | Topical therapy for the treatment of migranes, muscle sprains, muscle spasms, spasticity and related conditions |
| ATE430741T1 (de) * | 2003-07-24 | 2009-05-15 | Euro Celtique Sa | Piperidinverbindungen und pharmazeutische zusammensetzungen, die diese enthalten |
| GB0324269D0 (en) | 2003-10-16 | 2003-11-19 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| US20070173536A1 (en) * | 2004-02-06 | 2007-07-26 | Ciba Specialty Chemicals Holding Inc. | Crystalline forms of zolmitriptan |
| US7540286B2 (en) * | 2004-06-03 | 2009-06-02 | Alexza Pharmaceuticals, Inc. | Multiple dose condensation aerosol devices and methods of forming condensation aerosols |
| CA2576961A1 (en) * | 2004-08-12 | 2006-03-02 | Alexza Pharmaceuticals, Inc. | Aerosol drug delivery device incorporating percussively activated heat packages |
| US20060211751A1 (en) * | 2004-11-19 | 2006-09-21 | Reuven Izsak | Zolmitriptan crystal forms |
| BRPI0607517A2 (pt) | 2005-04-13 | 2009-09-08 | Neuraxon Inc | compostos de indol substituìdo, composição farmacêutica compreendendo o mesmo, método para tratar e uso do mesmo |
| WO2007083320A2 (en) | 2006-01-19 | 2007-07-26 | Matrix Laboratories Ltd | Conversion of aromatic diazonium salt to aryl hydrazine |
| US7989447B2 (en) | 2006-04-13 | 2011-08-02 | Neuraxon, Inc. | 1,5 and 3,6-substituted indole compounds having NOS inhibitory activity |
| WO2008018090A2 (en) * | 2006-08-09 | 2008-02-14 | Matrix Laboratories Ltd | An improved process for the preparation of zolmitriptan |
| AU2007310949A1 (en) * | 2006-10-19 | 2008-04-24 | Auspex Pharmaceuticals, Inc. | Substituted indoles |
| PT2425820E (pt) | 2007-02-11 | 2015-08-04 | Map Pharmaceuticals Inc | Método de administração terapêutica de dhe para permitir o rápido alívio das enxaquecas ao mesmo tempo que minimiza o perfil de efeitos secundários |
| CZ2007158A3 (cs) * | 2007-02-26 | 2008-10-22 | Zentiva, A. S. | Zpusob prípravy zolmitriptanu |
| EP2121088B1 (de) | 2007-03-09 | 2016-07-13 | Alexza Pharmaceuticals, Inc. | Erhitzungseinheit zur verwendung in einer arzneimittelabgabevorrichtung |
| CN101932570B (zh) | 2007-04-27 | 2014-11-26 | 普渡制药公司 | Trpv1拮抗剂以及其用途 |
| EP2479173A1 (de) * | 2007-04-27 | 2012-07-25 | Purdue Pharma LP | Zur Behandlung von Schmerzen geeignete therapeutische Mittel |
| EP2201003A1 (de) * | 2007-10-03 | 2010-06-30 | Generics Ýuk¨Limited | Verfahren zur herstellung von zolmitriptan, salzen und solvaten davon |
| WO2009062318A1 (en) * | 2007-11-16 | 2009-05-22 | Neuraxon, Inc. | 3,5-substituted indole compounds having nos and norepinephrine reuptake inhibitory activity |
| EP2219449A4 (de) * | 2007-11-16 | 2010-10-27 | Univ Arizona State | Verfahren zum behandeln von darmschmerzen |
| MX356032B (es) * | 2007-11-16 | 2018-04-11 | Neuraxon Inc | Compuestos indola y métodos para tratar el dolor visceral. |
| CN101181267B (zh) * | 2007-11-30 | 2010-09-08 | 重庆医科大学医药研究所 | 佐米曲普坦舌下片 |
| KR101517415B1 (ko) | 2008-05-14 | 2015-05-07 | 에스케이바이오팜 주식회사 | 난용성 항경련제를 함유하는 경비 항경련성 약학 조성물 |
| US8592424B2 (en) | 2008-06-30 | 2013-11-26 | Afgin Pharma Llc | Topical regional neuro-affective therapy |
| US20100217013A1 (en) * | 2008-12-15 | 2010-08-26 | Wenge Li | Enantioselective process for the preparation of zolmitriptan |
| US20110171141A1 (en) * | 2009-06-26 | 2011-07-14 | Kellerman Donald J | Administration of dihydroergotamine mesylate particles using a metered dose inhaler |
| US20110038928A1 (en) * | 2009-08-12 | 2011-02-17 | Glenmark Generics Ltd | Orally disintegrating tablets of zolmitriptan |
| CA2813648C (en) | 2010-10-15 | 2019-06-25 | Concit Pharma Aps | Combinations of serotonin receptor agonists for treatment of movement disorders |
| EP3173411B1 (de) | 2011-06-22 | 2018-05-09 | Purdue Pharma L.P. | Trpv1-antagonisten mit dihydroxy-substituent und ihre verwendung |
| EP2734634B1 (de) | 2011-07-22 | 2019-08-21 | The University of Chicago | Igf-1 zur behandlung von migräne |
| US9006453B2 (en) | 2011-09-02 | 2015-04-14 | Emcure Pharmaceuticals Limited | Process for preparation of zolmitriptan |
| MX361372B (es) | 2012-04-18 | 2018-12-05 | Contera Pharma Aps | Formulacion farmaceutica disponible por via oral adecuada para manejo mejorado de trastornos del movimiento. |
| US9394314B2 (en) | 2012-12-21 | 2016-07-19 | Map Pharmaceuticals, Inc. | 8′-hydroxy-dihydroergotamine compounds and compositions |
| CA2978605A1 (en) | 2015-03-02 | 2016-09-09 | Afgin Pharma, Llc | Topical regional neuro-affective therapy with cannabinoids |
| US10383816B2 (en) | 2015-03-02 | 2019-08-20 | Afgin Pharma, Llc | Topical regional neuro-affective therapy with cannabinoid combination products |
| WO2017122161A1 (en) | 2016-01-15 | 2017-07-20 | Cadila Healthcare Limited | An intranasal composition comprising 5ht1b/1d receptor agonists |
| JP7126260B2 (ja) | 2016-01-27 | 2022-08-26 | インスター テクノロジーズ アクチオヴァ スプルチュノスト | 治療処置用の口腔粘膜ナノファイバ担体 |
| CA3030089C (en) | 2016-07-11 | 2024-04-23 | Contera Pharma Aps | Pulsatile drug delivery system for treating morning akinesia |
| US20180049994A1 (en) | 2016-08-16 | 2018-02-22 | Afgin Pharma, Llc | Topical regional neuro-affective therapy with caryophyllene |
| US12214118B2 (en) | 2018-02-02 | 2025-02-04 | Alexza Pharmaceuticals, Inc. | Electrical condensation aerosol device |
| JP7667097B2 (ja) | 2019-06-14 | 2025-04-22 | ヤンセン ファーマシューティカ エヌ．ベー． | 置換ピラゾロ－ピリジンアミド及びｇｌｕｎ２ｂ受容体調節因子としてのその使用 |
| JP2022536773A (ja) | 2019-06-14 | 2022-08-18 | ヤンセン ファーマシューティカ エヌ．ベー． | 置換ピラゾロピラジン及びｇｌｕｎ２ｂ受容体調節因子としてのそれらの使用 |
| EP3766483A1 (de) | 2019-07-19 | 2021-01-20 | BioPharma Synergies, S. L. | Orodispergierbare pulverzusammensetzung mit einem triptan |
| US20210322343A1 (en) | 2020-04-15 | 2021-10-21 | Farzana Shaheen | Nasally administered pharmaceutical composition for the treatment of epilepsy and related disorders |
| CN114394962A (zh) * | 2021-12-22 | 2022-04-26 | 深圳市祥根生物医药有限公司 | 一种n-去甲基佐米曲普坦的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0313397A1 (de) | 1987-10-23 | 1989-04-26 | The Wellcome Foundation Limited | Heterocyclische Verbindungen mit therapeutischer Wirkung |
Family Cites Families (70)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB148879A (en) * | 1919-02-14 | 1921-11-10 | Emil Vincance Noser | Locks for shift levers of automobiles |
| US3320282A (en) * | 1962-10-29 | 1967-05-16 | Pfizer & Co C | Process for preparing esters of 2-hydroxy-3-(3-indolyl) alkanoic acids |
| US3879410A (en) * | 1971-02-08 | 1975-04-22 | Messrs Lab Guidotti & C S P A | 4-Aryl-4-oxazolin-2-ones exhibiting myotonic and myorelaxing activity |
| BE795457A (fr) * | 1972-02-16 | 1973-08-16 | Clin Midy | Amines indoliques, leur preparation et leur application en therapeutiques |
| FR2179582B1 (de) * | 1972-04-13 | 1975-10-10 | Synthelabo | |
| US3873559A (en) * | 1973-03-30 | 1975-03-25 | Squibb & Sons Inc | Heterocyclic carboxamido thiazolinyl indoles |
| IT995110B (it) * | 1973-08-01 | 1975-11-10 | Snam Progetti | Procedimento per la produzione di composti eterociclici e prodotti ottenuti |
| US4042595A (en) * | 1973-08-01 | 1977-08-16 | Snam Progetti S.P.A. | Processes for the production of heterocyclic compounds |
| US3931229A (en) * | 1973-08-23 | 1976-01-06 | Warner-Lambert Company | 3-Thiomethyl-2[2-(dialkylamino)ethyl]indoles |
| US4049816A (en) * | 1975-03-24 | 1977-09-20 | Beecham Group Limited | Antiviral 2-amino-5-[1-(indol-3-yl)alkyl]-2-thiazolin-4-ones |
| FR2315925A1 (fr) * | 1975-07-04 | 1977-01-28 | Nippon Chemiphar Co | Nouveaux derives de 5-benzyle-2-oxazolidone, leur procede de preparation et leur application en therapeutique |
| GB1482879A (en) * | 1975-07-24 | 1977-08-17 | Nippon Chemiphar Co | 5-benzyl-2-oxazolidone derivatives and a process for producing the same |
| GB1469200A (en) * | 1975-11-28 | 1977-03-30 | Warner Lambert Co | 3-thiomethyl-2-2-dialkylamino-ethyl-indoles |
| DE2557341A1 (de) * | 1975-12-19 | 1977-06-30 | Hoechst Ag | Basisch substituierte indolderivate und verfahren zu ihrer herstellung |
| IT1109002B (it) * | 1977-09-22 | 1985-12-16 | Menarini Sas | Derivati del 2 oxazolidone e loro metodi di preparazione |
| US4198501A (en) * | 1977-12-20 | 1980-04-15 | Hoffmann-La Roche Inc. | Synthesis of tryptophans |
| US4137404A (en) * | 1977-12-20 | 1979-01-30 | Hoffmann-La Roche Inc. | Synthesis of tryptophans |
| JPS6014032B2 (ja) * | 1978-01-20 | 1985-04-11 | 日本ケミフア株式会社東京 | ５‐フエネチル‐２‐オキサゾリドン誘導体およびその製法 |
| US4348393A (en) * | 1978-06-09 | 1982-09-07 | Delalande S.A. | N-Aryl oxazolidinones, oxazolidinethiones, pyrrolidinones, pyrrolidines and thiazolidinones |
| DE2933636A1 (de) * | 1978-08-30 | 1980-03-20 | Sandoz Ag | Neue n-phenylindolinderivate, ihre herstellung und pharmazeutische praeparate, welche diese verbindungen enthalten |
| ZA795239B (en) * | 1978-10-12 | 1980-11-26 | Glaxo Group Ltd | Heterocyclic compounds |
| DK151884C (da) * | 1979-03-07 | 1988-06-13 | Pfizer | Analogifremgangsmaade til fremstilling af 3-(1-imidazolylalkyl)indolderivater eller farmaceutisk acceptable syreadditionssalte deraf |
| US4255432A (en) * | 1979-09-06 | 1981-03-10 | Syntex (U.S.A.) Inc. | 8-[2-3-Indolyl)ethyl]-1-oxa-3-,8-diazaspiro[4.5]decan-2-ones, pharmaceutical compositions thereof and methods of use thereof |
| US4272555A (en) * | 1979-09-21 | 1981-06-09 | Monsanto Company | Conversion of carbon-containing materials to carbon monoxide |
| DE3164982D1 (de) * | 1980-04-10 | 1984-08-30 | Sandoz Ag | Isoxazolyl indolamines |
| JPS574986A (en) * | 1980-06-13 | 1982-01-11 | Paamakemu Asia:Kk | Preparation of oxazolidine derivative |
| US4753956A (en) * | 1981-01-02 | 1988-06-28 | Pfizer Inc. | Hypoglycemic 5-substituted oxazolidine-2,4-diones |
| US4367234A (en) * | 1980-07-28 | 1983-01-04 | Pfizer Inc. | Hypoglycemic 5-substituted oxazolidine-2,4-diones |
| BE889931A (fr) * | 1980-08-12 | 1982-02-11 | Glaxo Group Ltd | Derives indoliques, leur preparation et leurs applications en tant que medicaments |
| ZW19381A1 (en) * | 1980-08-12 | 1983-03-09 | Glaxo Group Ltd | Heterocyclic compounds |
| DK157920C (da) * | 1980-08-12 | 1990-08-06 | Glaxo Group Ltd | Analogifremgangsmaade til fremstilling af indolderivater |
| US4407811A (en) * | 1981-01-02 | 1983-10-04 | Pfizer Inc. | Hypoglycemic 5-substituted oxazolidine-2,4-diones |
| US4448971A (en) * | 1981-01-02 | 1984-05-15 | Pfizer Inc. | Hypoglycemic 5-phenyl-substituted oxazolidine-2,4-diones |
| US4399296A (en) * | 1981-01-02 | 1983-08-16 | Pfizer Inc. | Hypoglycemic 5-substituted oxazolidine-2,4-diones |
| JPS57169458A (en) * | 1981-04-13 | 1982-10-19 | Paamakemu Asia:Kk | Preparation of indole derivative |
| CH656124A5 (de) * | 1982-04-13 | 1986-06-13 | Sandoz Ag | 2-substituierte-3-indolamine, verfahren zu deren herstellung sowie deren verwendung. |
| GR79215B (de) * | 1982-06-07 | 1984-10-22 | Glaxo Group Ltd | |
| US4803218A (en) * | 1982-09-29 | 1989-02-07 | Mcneilab, Inc. | 3-aminoalkyl-1H-indole-5-urea and amide derivatives |
| US4500717A (en) * | 1983-03-28 | 1985-02-19 | The Dow Chemical Company | Process for preparation of 2-oxazolidinones |
| US4831153A (en) * | 1983-06-27 | 1989-05-16 | The Dow Chemical Company | Preparation of N-vinyl-2-oxazolidinone |
| GB8321813D0 (en) * | 1983-08-12 | 1983-09-14 | Vickers Plc | Radiation sensitive compounds |
| DE3333450A1 (de) * | 1983-09-16 | 1985-04-11 | Hoechst Ag, 6230 Frankfurt | Trihalogenmethylgruppen enthaltende carbonylmethylenheterocyclen, verfahren zu ihrer herstellung und lichtempfindliches gemisch, das diese verbindungen enthaelt |
| HU196752B (en) * | 1983-12-06 | 1989-01-30 | Glaxo Group Ltd | Process for production of medical compositions containing indole-derivatives and these compounds |
| DE3430284A1 (de) * | 1984-08-17 | 1986-02-27 | Troponwerke GmbH & Co KG, 5000 Köln | Neue tryptamin-derivate, ein verfahren zu ihrer herstellung und ihre verwendung |
| SE8505715L (sv) * | 1984-12-04 | 1986-06-05 | Glaxo Group Ltd | Indolderivat |
| GB8431426D0 (en) * | 1984-12-13 | 1985-01-23 | Glaxo Group Ltd | Chemical compounds |
| DE3514696A1 (de) * | 1985-04-24 | 1986-11-06 | Bayer Ag, 5090 Leverkusen | N-indolylethyl-sulfonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung |
| DE3531658A1 (de) * | 1985-09-05 | 1987-03-12 | Boehringer Mannheim Gmbh | Heterocyclisch substituierte indole, zwischenprodukte, verfahren zu ihrer herstellung und arzneimittel |
| US4833153A (en) * | 1985-11-08 | 1989-05-23 | Glaxo Group Limited | Indole derivatives |
| GB8531612D0 (en) * | 1985-12-23 | 1986-02-05 | Beecham Wuelfing Gmbh & Co Kg | Compounds |
| SE451840B (sv) * | 1986-01-03 | 1987-11-02 | Astra Laekemedel Ab | Optiskt rent monohydrat av s-(-)-1-propyl-2',6'-pipekoloxylididhydroklorid, sett att framstella denna och farmaceutiska beredningar for lokalbedovning |
| GB8600397D0 (en) * | 1986-01-08 | 1986-02-12 | Glaxo Group Ltd | Chemical compounds |
| GB8600398D0 (en) * | 1986-01-08 | 1986-02-12 | Glaxo Group Ltd | Chemical compounds |
| GB8607824D0 (en) * | 1986-03-27 | 1986-04-30 | Glaxo Group Ltd | Chemical compounds |
| DE3643957A1 (de) * | 1986-12-22 | 1988-06-30 | Bayer Ag | Substituierte n-methylisoxazolidine |
| GB8719167D0 (en) * | 1987-08-13 | 1987-09-23 | Glaxo Group Ltd | Chemical compounds |
| ATE92057T1 (de) * | 1987-08-13 | 1993-08-15 | Glaxo Group Ltd | Indol-derivate. |
| DE3730777A1 (de) * | 1987-09-12 | 1989-03-23 | Basf Ag | Verfahren zur herstellung von imidazolidinonen und oxazolidinonen |
| US4965268A (en) * | 1987-10-09 | 1990-10-23 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US4921869A (en) * | 1987-10-09 | 1990-05-01 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| US4801600A (en) * | 1987-10-09 | 1989-01-31 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
| DE3823299A1 (de) * | 1988-07-07 | 1990-01-11 | Schering Ag | Substituierte phenyl-pyrrolidin-2-one, -oxazolidin-2-one und -imidazolidin-2-one, ihre herstellung sowie verwendung in arzneimitteln |
| GB8819024D0 (en) * | 1988-08-10 | 1988-09-14 | Glaxo Group Ltd | Chemical compounds |
| AU617871B2 (en) * | 1988-09-15 | 1991-12-05 | Pharmacia & Upjohn Company | In position 3 substituted-5-beta-amidomethyl-oxazolidin-2- ones |
| US5164510A (en) * | 1988-09-15 | 1992-11-17 | The Upjohn Company | 5'Indolinyl-5β-amidomethyloxazolidin-2-ones |
| DE3939238A1 (de) * | 1989-11-28 | 1991-05-29 | Bayer Ag | Heterocyclisch substituierte acrylsaeureester |
| DE4013907A1 (de) * | 1990-04-26 | 1991-10-31 | Schering Ag | Verfahren zur herstellung von gramin-derivaten |
| CZ283018B6 (cs) * | 1991-02-01 | 1997-12-17 | Merck Sharp And Dohme Limited | Deriváty imidazolu, triazolu a tetrazolu a farmaceutické přípravky na jejich bázi |
| GB9104136D0 (en) * | 1991-02-27 | 1991-04-17 | Merck Sharp & Dohme | Therapeutic agents |
| US5409941A (en) * | 1992-02-03 | 1995-04-25 | Pfizer Inc. | 5-heteroyl indole derivatives |
-
1991
- 1991-06-06 DE DE69132691T patent/DE69132691T2/de not_active Expired - Lifetime
- 1991-06-06 UA UA93002089A patent/UA37178C2/uk unknown
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- 1991-06-06 JP JP3510103A patent/JP2738461B2/ja not_active Expired - Lifetime
- 1991-06-06 CZ CS19911727A patent/CZ288351B6/cs not_active IP Right Cessation
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- 1991-06-06 DE DE1991627260 patent/DE19775091I2/de active Active
- 1991-06-06 WO PCT/GB1991/000908 patent/WO1991018897A1/en not_active Ceased
- 1991-06-06 SI SI9119001A patent/SI21560B/sl active Search and Examination
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- 1991-06-06 AT AT91911486T patent/ATE156823T1/de active
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- 1991-06-06 EP EP91911486A patent/EP0486666B1/de not_active Expired - Lifetime
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- 1991-06-06 KR KR1019920700284A patent/KR100215627B1/ko not_active Expired - Lifetime
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1992
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1993
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1994
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1995
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1996
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1997
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1998
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0313397A1 (de) | 1987-10-23 | 1989-04-26 | The Wellcome Foundation Limited | Heterocyclische Verbindungen mit therapeutischer Wirkung |
Non-Patent Citations (1)
| Title |
|---|
| P.B. BRADLEY, G. ENGEL, W. FENIUK, J.R. FOZAR: "Proposals for the classification and nomenclature of functional receptors for 5-hydroxytryptamine", NEUROPHARMACOLOGY |
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