DE69631423T2 - Chinolone und deren therapeutische verwendung - Google Patents
Chinolone und deren therapeutische verwendung Download PDFInfo
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- DE69631423T2 DE69631423T2 DE69631423T DE69631423T DE69631423T2 DE 69631423 T2 DE69631423 T2 DE 69631423T2 DE 69631423 T DE69631423 T DE 69631423T DE 69631423 T DE69631423 T DE 69631423T DE 69631423 T2 DE69631423 T2 DE 69631423T2
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- ethyl
- use according
- dihydro
- carboxamide
- pyrido
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Classifications
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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9515812.7A GB9515812D0 (en) | 1995-08-02 | 1995-08-02 | Novel compounds |
| GB9515812 | 1995-08-02 | ||
| GBGB9523679.0A GB9523679D0 (en) | 1995-11-20 | 1995-11-20 | Novel compounds |
| GB9523679 | 1995-11-20 | ||
| GB9605865 | 1996-03-20 | ||
| GBGB9605865.6A GB9605865D0 (en) | 1996-03-20 | 1996-03-20 | Novel compounds |
| GB9611898 | 1996-06-07 | ||
| GBGB9611898.9A GB9611898D0 (en) | 1996-06-07 | 1996-06-07 | Quinolones and their therapeutic use |
| PCT/GB1996/001866 WO1997004775A1 (en) | 1995-08-02 | 1996-07-31 | Quinolones and their therapeutic use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69631423D1 DE69631423D1 (de) | 2004-03-04 |
| DE69631423T2 true DE69631423T2 (de) | 2004-12-02 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69631423T Expired - Fee Related DE69631423T2 (de) | 1995-08-02 | 1996-07-31 | Chinolone und deren therapeutische verwendung |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5753666A (enExample) |
| EP (1) | EP0841927B1 (enExample) |
| JP (1) | JPH11510156A (enExample) |
| AT (1) | ATE258437T1 (enExample) |
| AU (1) | AU695132B2 (enExample) |
| CA (1) | CA2225555A1 (enExample) |
| DE (1) | DE69631423T2 (enExample) |
| ES (1) | ES2211965T3 (enExample) |
| MX (1) | MX9800921A (enExample) |
| WO (1) | WO1997004775A1 (enExample) |
Families Citing this family (51)
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| GB9605437D0 (en) * | 1996-03-15 | 1996-05-15 | Iaf Biochem Int | Cytomegalovirus inhibiting compounds |
| CA2268190A1 (en) * | 1997-08-06 | 1999-02-18 | Suntory Limited | 1-aryl-1,8-naphthylidin-4-one derivative as type iv phosphodiesterase inhibitor |
| US6331548B1 (en) | 1998-01-29 | 2001-12-18 | Suntory Limited | 1-cycloalkyl-1,8-naphthyridin-4-one derivative as type IV phosphodiesterase inhibitor |
| AU4849199A (en) * | 1998-07-01 | 2000-01-24 | Celgro | Fungal growth inhibitors |
| US6248739B1 (en) * | 1999-01-08 | 2001-06-19 | Pharmacia & Upjohn Company | Quinolinecarboxamides as antiviral agents |
| AU2001243240A1 (en) | 2000-03-21 | 2001-10-15 | Pharmacia And Upjohn Company Llc | 4-oxo-1,4-dihydro(1,8)naphthyridine-3-carboxamides as antiviral agents |
| CN1398258A (zh) | 2000-03-21 | 2003-02-19 | 法玛西雅厄普约翰美国公司 | 用作抗病毒剂的4－羟基噌啉－3－甲酰胺化合物 |
| HK1054037A1 (zh) | 2000-03-21 | 2003-11-14 | 法玛西雅厄普约翰美国公司 | 作为抗病毒剂的4-羟基-1，8-二氮杂萘-3-羧酰胺 |
| SI1265873T1 (en) | 2000-03-21 | 2004-02-29 | Pharmacia & Upjohn Company | 4-oxo-1,4-dihydro-3-cinnolinecarboxamides as antiviral agents |
| PE20011349A1 (es) * | 2000-06-16 | 2002-01-19 | Upjohn Co | 1-aril-4-oxo-1,4-dihidro-3-quinolincarboxamidas como agentes antivirales |
| US6559145B2 (en) | 2000-07-12 | 2003-05-06 | Pharmacia & Upjohn Company | Heterocycle carboxamides as antiviral agents |
| US6730682B2 (en) * | 2000-07-12 | 2004-05-04 | Pharmacia & Upjohn Company | Heterocycle carboxamides as antiviral agents |
| US6562822B2 (en) | 2000-07-12 | 2003-05-13 | Pharmacia & Upjohn Company | Heterocyle carboxamides as antiviral agents |
| IL155089A0 (en) * | 2000-10-12 | 2003-10-31 | Merck & Co Inc | Aza and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors |
| CA2425625A1 (en) * | 2000-10-12 | 2002-07-18 | Merck & Co., Inc. | Aza-and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors |
| EP1326611B1 (en) * | 2000-10-12 | 2007-06-13 | Merck & Co., Inc. | Aza- and polyaza-naphthalenyl-carboxamides useful as hiv integrase inhibitors |
| CZ20031910A3 (cs) | 2000-12-11 | 2003-12-17 | Tularik Inc. | Sloučenina s antagonistickými účinky na CXCR3 a farmaceutický postředek |
| PE20020856A1 (es) * | 2001-02-13 | 2002-11-11 | Aventis Pharma Gmbh | 1,2,3,4-tetrahidronaftil aminas aciladas |
| TWI243164B (en) | 2001-02-13 | 2005-11-11 | Aventis Pharma Gmbh | Acylated indanyl amines and their use as pharmaceuticals |
| AU2002257459B2 (en) * | 2001-05-24 | 2006-12-14 | Merck Frosst Canada Ltd | 1-biaryl-1,8-napthyridin-4-one phosphodiesterase-4 inhibitors |
| US6794379B2 (en) | 2001-06-06 | 2004-09-21 | Tularik Inc. | CXCR3 antagonists |
| WO2003077850A2 (en) * | 2002-03-15 | 2003-09-25 | Merck & Co., Inc. | N-(substituted benzyl)-8-hydroxy-1,6-naphthyridine-7- carboxamides useful as hiv integrase inhibitors |
| IS7839A (is) * | 2002-11-22 | 2004-05-23 | Merck Frosst Canada Ltd. | 4-oxó-1-(3-setið fenýl-1,4-díhýdró-1,8-naftýridín-3-karboxamíð fosfódíesterasa-4 hindrar |
| KR20060041254A (ko) * | 2003-07-24 | 2006-05-11 | 아스텔라스세이야쿠 가부시키가이샤 | 퀴놀론 유도체 또는 그의 염 |
| US8354427B2 (en) | 2004-06-24 | 2013-01-15 | Vertex Pharmaceutical Incorporated | Modulators of ATP-binding cassette transporters |
| PT1773816E (pt) * | 2004-06-24 | 2015-04-29 | Vertex Pharma | Moduladores de transportadores de cassete de ligação de atp |
| DE102004035203A1 (de) | 2004-07-21 | 2006-02-16 | Bayer Healthcare Ag | Substituierte Chinolone |
| DE102005030524A1 (de) | 2005-06-30 | 2007-01-18 | Aicuris Gmbh & Co. Kg | Substituierte Chinolone II |
| TW200800983A (en) * | 2005-09-14 | 2008-01-01 | Janssen Pharmaceutica Nv | 5-oxo-5,8-dihydro-pyrido-pyrimidines as inhibitors of C-FMS kinase |
| JP5175207B2 (ja) * | 2005-11-10 | 2013-04-03 | ケモセントリックス インコーポレーティッド | 置換キノロンおよび使用法 |
| EP1979367A2 (en) * | 2005-12-24 | 2008-10-15 | Vertex Pharmaceuticals Incorporated | Quinolin-4-one derivatives as modulators of abc transporters |
| RS55940B1 (sr) | 2005-12-28 | 2017-09-29 | Vertex Pharma | Čvrsti oblici n-[2,4-bis(1,1-dimetiletil)-5-hidroksifenil]-1,4-dihidro-4-oksohinolin-3-karboksamida |
| DE102006005861A1 (de) | 2006-02-09 | 2007-08-23 | Aicuris Gmbh & Co. Kg | Substituierte Chinolone III |
| FR2917412B1 (fr) * | 2007-06-13 | 2009-08-21 | Sanofi Aventis Sa | Derives de 7-alkynyl, 1,8-naphthyridones, leur preparation et leur application en therapeutique |
| FR2917413B1 (fr) | 2007-06-13 | 2009-08-21 | Sanofi Aventis Sa | Derives de 7-alkynyl-1,8-naphthyridones, leur preparation et leur application en therapeutique |
| NZ583878A (en) | 2007-09-14 | 2012-10-26 | Vertex Pharma | Modulators of ABC transporter and cystic fibrosis transmembrane conductance regulator (CFTR) |
| US20100074949A1 (en) | 2008-08-13 | 2010-03-25 | William Rowe | Pharmaceutical composition and administration thereof |
| US12458635B2 (en) | 2008-08-13 | 2025-11-04 | Vertex Pharmaceuticals Incorporated | Pharmaceutical composition and administrations thereof |
| EP2196465A1 (en) | 2008-12-15 | 2010-06-16 | Almirall, S.A. | (3-oxo)pyridazin-4-ylurea derivatives as PDE4 inhibitors |
| US8415333B2 (en) | 2009-02-24 | 2013-04-09 | Respiratorious Ab | Bronchodilating diazaheteroaryls |
| EP2226323A1 (en) | 2009-02-27 | 2010-09-08 | Almirall, S.A. | New tetrahydropyrazolo[3,4-c]isoquinolin-5-amine derivatives |
| EP2821400B1 (en) | 2009-03-20 | 2017-09-27 | Vertex Pharmaceuticals Incorporated | Process for making modulators of cystic fibrosis transmembrane conductance regulator |
| EP2380890A1 (en) | 2010-04-23 | 2011-10-26 | Almirall, S.A. | New 7,8-dihydro-1,6-naphthyridin-5(6h)-one-derivatives as PDE4 inhibitors |
| EP2394998A1 (en) | 2010-05-31 | 2011-12-14 | Almirall, S.A. | 3-(5-Amino-6-oxo-1,6-dihydropyridazin-3-yl)-biphenyl derivatives as PDE4 inhibitors |
| US8802700B2 (en) | 2010-12-10 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
| CN102643268B (zh) * | 2011-12-30 | 2014-05-21 | 沈阳药科大学 | 喹啉类及噌啉类化合物及其应用 |
| EP2800568A4 (en) * | 2012-01-06 | 2015-06-10 | Univ South Florida | COMPOSITIONS, USE METHOD AND TREATMENT METHOD THEREFOR |
| MX2014010253A (es) | 2012-02-27 | 2014-11-12 | Vertex Pharma | Composicion farmaceutica y administraciones de la misma. |
| RU2749213C2 (ru) | 2014-10-07 | 2021-06-07 | Вертекс Фармасьютикалз Инкорпорейтед | Сокристаллы модуляторов регулятора трансмембранной проводимости при кистозном фиброзе |
| CN107998131B (zh) * | 2017-12-27 | 2019-09-24 | 湖北工业大学 | 芳香酯类化合物用于制备抗adv-7病毒药物 |
| CN111646941A (zh) * | 2020-07-17 | 2020-09-11 | 天津科技大学 | 一种磺酰胺类衍生物及其制备方法和应用 |
Family Cites Families (4)
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|---|---|---|---|---|
| US3524858A (en) * | 1967-05-18 | 1970-08-18 | Warner Lambert Pharmaceutical | 1,4 - dihydro-1-substituted alkyl-6,7-methylenedioxy - 4 - oxoquinoline-3-carboxylic acid |
| FR2564832B1 (fr) * | 1984-05-23 | 1987-05-15 | Panmedica Sa | Nouveaux n-acyl derives d'amino-acides et leurs esters, leur procede de preparation et medicaments les contenant |
| US4786644A (en) * | 1987-11-27 | 1988-11-22 | Hoechst-Roussel Pharmaceuticals Inc. | 1-aryl-3-quinolinecarboxamide |
| JPH02124871A (ja) * | 1988-07-27 | 1990-05-14 | Dainippon Pharmaceut Co Ltd | １位が置換された複素環式カルボン酸アミド誘導体 |
-
1996
- 1996-07-31 CA CA002225555A patent/CA2225555A1/en not_active Abandoned
- 1996-07-31 JP JP9507375A patent/JPH11510156A/ja not_active Ceased
- 1996-07-31 ES ES96925909T patent/ES2211965T3/es not_active Expired - Lifetime
- 1996-07-31 DE DE69631423T patent/DE69631423T2/de not_active Expired - Fee Related
- 1996-07-31 WO PCT/GB1996/001866 patent/WO1997004775A1/en not_active Ceased
- 1996-07-31 AT AT96925909T patent/ATE258437T1/de not_active IP Right Cessation
- 1996-07-31 AU AU66266/96A patent/AU695132B2/en not_active Ceased
- 1996-07-31 EP EP96925909A patent/EP0841927B1/en not_active Expired - Lifetime
- 1996-07-31 MX MX9800921A patent/MX9800921A/es not_active IP Right Cessation
- 1996-08-02 US US08/691,339 patent/US5753666A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2225555A1 (en) | 1997-02-13 |
| ATE258437T1 (de) | 2004-02-15 |
| ES2211965T3 (es) | 2004-07-16 |
| EP0841927A1 (en) | 1998-05-20 |
| MX9800921A (es) | 1998-05-31 |
| WO1997004775A1 (en) | 1997-02-13 |
| EP0841927B1 (en) | 2004-01-28 |
| US5753666A (en) | 1998-05-19 |
| AU6626696A (en) | 1997-02-26 |
| DE69631423D1 (de) | 2004-03-04 |
| JPH11510156A (ja) | 1999-09-07 |
| AU695132B2 (en) | 1998-08-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |