CN103415290B - 用于治疗aids的化合物 - Google Patents
用于治疗aids的化合物 Download PDFInfo
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- CN103415290B CN103415290B CN201180060026.XA CN201180060026A CN103415290B CN 103415290 B CN103415290 B CN 103415290B CN 201180060026 A CN201180060026 A CN 201180060026A CN 103415290 B CN103415290 B CN 103415290B
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- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- 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
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- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/12—Ophthalmic agents for cataracts
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
- C07D401/02—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
- C07D401/12—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 chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- AIDS & HIV (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
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- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Dermatology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10306417A EP2465502A1 (en) | 2010-12-15 | 2010-12-15 | Compounds useful for treating AIDS |
| EP10306417.6 | 2010-12-15 | ||
| PCT/IB2011/055643 WO2012080953A1 (en) | 2010-12-15 | 2011-12-13 | Compounds useful for treating aids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103415290A CN103415290A (zh) | 2013-11-27 |
| CN103415290B true CN103415290B (zh) | 2016-09-14 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201180060026.XA Active CN103415290B (zh) | 2010-12-15 | 2011-12-13 | 用于治疗aids的化合物 |
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| EP (2) | EP2465502A1 (enExample) |
| JP (1) | JP6049630B2 (enExample) |
| KR (1) | KR101749232B1 (enExample) |
| CN (1) | CN103415290B (enExample) |
| AR (1) | AR084277A1 (enExample) |
| AU (1) | AU2011342826B2 (enExample) |
| BR (1) | BR112013014943B1 (enExample) |
| CA (1) | CA2819317C (enExample) |
| CU (1) | CU20130080A7 (enExample) |
| DK (1) | DK2651416T3 (enExample) |
| ES (1) | ES2681539T3 (enExample) |
| HR (1) | HRP20181190T1 (enExample) |
| MX (1) | MX337258B (enExample) |
| PL (1) | PL2651416T3 (enExample) |
| PT (1) | PT2651416T (enExample) |
| RU (1) | RU2598845C2 (enExample) |
| WO (1) | WO2012080953A1 (enExample) |
| ZA (1) | ZA201303922B (enExample) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10253020B2 (en) | 2009-06-12 | 2019-04-09 | Abivax | Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging |
| KR102016889B1 (ko) | 2009-06-12 | 2019-08-30 | 아비박스 | 조기 노화, 구체적으로 조로증을 치료하는데 유용한 화합물 |
| EP2757161A1 (en) | 2013-01-17 | 2014-07-23 | Splicos | miRNA-124 as a biomarker of viral infection |
| JP6895251B2 (ja) * | 2013-07-05 | 2021-06-30 | アビバックス | レトロウイルスにより引き起こされる疾患を処理する為に有用な化合物 |
| EP2975034A1 (en) * | 2014-07-17 | 2016-01-20 | Abivax | A quinoline derivative for the treatment of inflammatory diseases and AIDS |
| EP2974729A1 (en) * | 2014-07-17 | 2016-01-20 | Abivax | Quinoline derivatives for use in the treatment of inflammatory diseases |
| EP3059591A1 (en) * | 2015-02-23 | 2016-08-24 | Abivax | Methods for screening compounds for treating or preventing a viral infection or a virus-related condition |
| EP3059236A1 (en) | 2015-02-23 | 2016-08-24 | Abivax | A new quinoline derivative for use in the treatment and prevention of viral infections |
| EP3058940A1 (en) * | 2015-02-23 | 2016-08-24 | Abivax | Quinoline derivatives for use in the treatment or prevention of viral infection |
| US11130736B2 (en) * | 2015-08-21 | 2021-09-28 | University Of Kansas | Human TLR8-selective agonists |
| WO2017158201A1 (en) * | 2016-03-18 | 2017-09-21 | Ratiopharm Gmbh | Process for preparing quinolin-2-yl-phenylamine derivatives and their salts |
| KR101966351B1 (ko) * | 2016-06-08 | 2019-04-08 | 한국과학기술연구원 | 히스톤 메틸전달효소 저해용 퀴놀린 유도체 및 이의 용도 |
| WO2019002228A1 (en) | 2017-06-26 | 2019-01-03 | Institut Pasteur | TREATMENTS TO REMOVE HIV RESERVOIRS AND REDUCE VIRAL LOAD |
| WO2019186277A1 (en) | 2018-03-28 | 2019-10-03 | Institut Pasteur | Ultrasensitive hiv-1 p24 detection assay |
| EP3594206A1 (en) * | 2018-07-09 | 2020-01-15 | Abivax | Phenyl-n-quinoline derivatives for treating a rna virus infection |
| EP3594205A1 (en) | 2018-07-09 | 2020-01-15 | Abivax | Phenyl-n-aryl derivatives for treating a rna virus infection |
| EP3669874A1 (en) * | 2018-12-20 | 2020-06-24 | Abivax | Quinoline derivatives for use in the treatment or prevention of cancer |
| EP3669873A1 (en) | 2018-12-20 | 2020-06-24 | Abivax | Quinoline derivatives for use ine the traeatment of inflammation diseases |
| WO2020128033A1 (en) | 2018-12-20 | 2020-06-25 | Institut Pasteur | Cellular metabolism of hiv-1 reservoir seeding in cd4+ t cells |
| CN109776498B (zh) * | 2019-03-13 | 2020-04-07 | 浙江永宁药业股份有限公司 | 一种西洛他唑的制备方法 |
| EP4063351A1 (en) * | 2021-03-26 | 2022-09-28 | Abivax | Preparation method of quinoline derivative compounds |
| EP4212156A1 (en) | 2022-01-13 | 2023-07-19 | Abivax | Combination of 8-chloro-n-(4-(trifluoromethoxy)phenyl)quinolin-2-amine and its derivatives with a s1p receptor modulator |
| EP4215196A1 (en) | 2022-01-24 | 2023-07-26 | Abivax | Combination of 8-chloro-n-(4-(trifluoromethoxy)phenyl)quinolin-2-amine and its derivatives with a jak inhibitor |
| WO2024109936A1 (zh) * | 2022-11-25 | 2024-05-30 | 江苏恒瑞医药股份有限公司 | 一种喹啉胺类化合物晶型及其制备方法 |
| WO2025027388A1 (en) | 2023-08-01 | 2025-02-06 | Abivax | Obefazimod for treatment of ulcerative colitis |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004078731A1 (en) * | 2003-03-06 | 2004-09-16 | 'chemical Diversity Research Institute', Ltd. | Quinoline-carboxylic acids and the derivatives thereof, a focused library |
| US20080161353A1 (en) * | 2002-07-16 | 2008-07-03 | Kevin Jeffrey Barnham | 8-Hydroxy quinoline derivatives |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2419199A (en) * | 1945-02-09 | 1947-04-22 | Parke Davis & Co | Quinoline compounds and process of making same |
| FR2387229A1 (fr) | 1977-04-13 | 1978-11-10 | Anvar | Dipyrido (4,3-b) (3,4-f) indoles, procede d'obtention, application therapeutique et compositions pharmaceutiques les contenant |
| FR2436786A1 (fr) | 1978-09-21 | 1980-04-18 | Anvar | Nouveaux derives des pyrido (4,3-b) carbazoles (ellipticines), substitues en position 1 par une chaine polyaminee, leur obtention et leur application a titre de medicaments |
| JPS59501318A (ja) * | 1982-07-26 | 1984-07-26 | アメリカン ホスピタル サプライ コ−ポレ−シヨン | ヘテロアリ−ル置換アミノメチルベンゼン誘導体 |
| US4466965A (en) * | 1982-07-26 | 1984-08-21 | American Hospital Supply Corporation | Phthalazine compounds, compositions and use |
| FR2627493B1 (fr) | 1988-02-23 | 1991-10-31 | Sanofi Sa | Procede de preparation de derives d'isoquinoleine |
| FR2645861A1 (fr) | 1989-04-17 | 1990-10-19 | Inst Nat Sante Rech Med | Utilisation de dipyrido (4,3-b) (3,4-f) indoles pour la preparation de medicaments utiles pour le traitement du sida |
| ATE260099T1 (de) | 1999-04-05 | 2004-03-15 | Hope City | Neue hemmern von fortgeschrittenen glykosilierung-endprodukten |
| UA75055C2 (uk) * | 1999-11-30 | 2006-03-15 | Пфайзер Продактс Інк. | Похідні бензоімідазолу, що використовуються як антипроліферативний засіб, фармацевтична композиція на їх основі |
| ATE493987T1 (de) | 2002-05-22 | 2011-01-15 | Amgen Inc | Aminopyrimidin-derivate zur verwendung als vanilloid-rezeptor-liganden zur behandlung von schmerzen |
| WO2004009552A1 (en) | 2002-07-19 | 2004-01-29 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors, including n-substituted aniline and diphenylamine analogs |
| WO2006081444A2 (en) | 2005-01-28 | 2006-08-03 | The Government Of The Usa As Represented By The Secretary Of The Dept. Of Health And Human Services | Farnesyltransferase inhibitors for treatment of laminopathies, cellular aging and atherosclerosis |
| FR2849474B3 (fr) | 2002-12-27 | 2004-12-03 | Olivier Jean Noel Juin | Installation de transformation de l'energie cinetique d'un fluide en energie electrique |
| FR2859474B1 (fr) | 2003-09-04 | 2006-01-13 | Centre Nat Rech Scient | Utilisation de composes derives d'indole pour la preparation d'un medicament utile pour le traitement de maladies genetiques resultant de l'alteration des processus d'epissage |
| FR2859475A1 (fr) | 2003-09-04 | 2005-03-11 | Centre Nat Rech Scient | Utilisation de composes derives d'ellipticine et d'aza-ellipticine pour la preparation d'un medicament utile pour le traitement de maladies genetiques resultant de l'alteration des processus d'epissage |
| FR2903312B1 (fr) | 2006-07-05 | 2008-09-26 | Univ Aix Marseille Ii | Utilisation d'inhibiteurs d'hmg-coa reductase et de farnesyl-pyrophosphate synthase dans la preparation d'un medicament |
| US8030487B2 (en) | 2006-07-07 | 2011-10-04 | Targegen, Inc. | 2-amino—5-substituted pyrimidine inhibitors |
| FR2912745A1 (fr) | 2007-02-19 | 2008-08-22 | Centre Nat Rech Scient | Nouveaux composes derives d'indole et compositions pharmaceutiques les contenant |
| CA2681481A1 (en) | 2007-03-16 | 2008-09-25 | Mount Sinai School Of Medicine | Induction and/or maintenance of tumor dormancy by disruption of urokinase plasminogen activator receptor-integrin interaction |
| JP5603233B2 (ja) | 2007-05-17 | 2014-10-08 | エルジー・ケム・リミテッド | 新規なアントラセン誘導体およびそれを用いた有機電子素子 |
| CN101801194A (zh) | 2007-08-15 | 2010-08-11 | 记忆医药公司 | 具有5-ht6受体亲和力的3’取代的化合物 |
| FR2926297B1 (fr) | 2008-01-10 | 2013-03-08 | Centre Nat Rech Scient | Molecules chimiques inhibitrices du mecanisme d'epissage pour traiter des maladies resultant d'anomalies d'epissage. |
| KR102016889B1 (ko) | 2009-06-12 | 2019-08-30 | 아비박스 | 조기 노화, 구체적으로 조로증을 치료하는데 유용한 화합물 |
-
2010
- 2010-12-15 EP EP10306417A patent/EP2465502A1/en not_active Withdrawn
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2011
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- 2011-12-13 DK DK11805230.7T patent/DK2651416T3/en active
- 2011-12-13 ES ES11805230.7T patent/ES2681539T3/es active Active
- 2011-12-13 RU RU2013126947/04A patent/RU2598845C2/ru active
- 2011-12-13 AU AU2011342826A patent/AU2011342826B2/en active Active
- 2011-12-13 BR BR112013014943-4A patent/BR112013014943B1/pt active IP Right Grant
- 2011-12-13 HR HRP20181190TT patent/HRP20181190T1/hr unknown
- 2011-12-13 MX MX2013006322A patent/MX337258B/es active IP Right Grant
- 2011-12-13 PL PL11805230T patent/PL2651416T3/pl unknown
- 2011-12-13 US US13/993,990 patent/US9061999B2/en active Active
- 2011-12-13 KR KR1020137018457A patent/KR101749232B1/ko active Active
- 2011-12-13 PT PT118052307T patent/PT2651416T/pt unknown
- 2011-12-13 WO PCT/IB2011/055643 patent/WO2012080953A1/en not_active Ceased
- 2011-12-13 JP JP2013543948A patent/JP6049630B2/ja active Active
- 2011-12-13 CN CN201180060026.XA patent/CN103415290B/zh active Active
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- 2011-12-14 AR ARP110104670A patent/AR084277A1/es active IP Right Grant
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2013
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- 2013-06-13 CU CUP2013000080A patent/CU20130080A7/es unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080161353A1 (en) * | 2002-07-16 | 2008-07-03 | Kevin Jeffrey Barnham | 8-Hydroxy quinoline derivatives |
| WO2004078731A1 (en) * | 2003-03-06 | 2004-09-16 | 'chemical Diversity Research Institute', Ltd. | Quinoline-carboxylic acids and the derivatives thereof, a focused library |
Also Published As
| Publication number | Publication date |
|---|---|
| BR112013014943A8 (pt) | 2018-06-12 |
| HRP20181190T1 (hr) | 2019-03-08 |
| DK2651416T3 (en) | 2018-08-06 |
| AU2011342826A1 (en) | 2013-07-04 |
| US20130267703A1 (en) | 2013-10-10 |
| CA2819317A1 (en) | 2012-06-21 |
| PL2651416T3 (pl) | 2018-09-28 |
| MX337258B (es) | 2016-02-22 |
| US9061999B2 (en) | 2015-06-23 |
| JP6049630B2 (ja) | 2016-12-21 |
| ZA201303922B (en) | 2014-07-30 |
| WO2012080953A1 (en) | 2012-06-21 |
| CN103415290A (zh) | 2013-11-27 |
| JP2013545798A (ja) | 2013-12-26 |
| CA2819317C (en) | 2017-02-28 |
| ES2681539T3 (es) | 2018-09-13 |
| BR112013014943A2 (pt) | 2016-09-13 |
| KR20140041402A (ko) | 2014-04-04 |
| RU2598845C2 (ru) | 2016-09-27 |
| AU2011342826B2 (en) | 2016-02-11 |
| AR084277A1 (es) | 2013-05-02 |
| RU2013126947A (ru) | 2015-01-20 |
| EP2465502A1 (en) | 2012-06-20 |
| KR101749232B1 (ko) | 2017-07-03 |
| PT2651416T (pt) | 2018-07-30 |
| BR112013014943B1 (pt) | 2022-05-03 |
| EP2651416B1 (en) | 2018-05-09 |
| CU20130080A7 (es) | 2013-08-29 |
| EP2651416A1 (en) | 2013-10-23 |
| MX2013006322A (es) | 2013-10-25 |
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Owner name: ABIVAX S. A. Free format text: FORMER OWNER: SPLICOS SAS Effective date: 20150108 |
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| C41 | Transfer of patent application or patent right or utility model | ||
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Effective date of registration: 20150108 Address after: France Applicant after: ABIVAX company Applicant after: National Research Center Applicant after: Institut Curie Applicant after: Univ. Montpellier II Address before: Montpelier, France Applicant before: Splicos Applicant before: National Research Center Applicant before: Institut Curie Applicant before: Univ. Montpellier II |
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Effective date of registration: 20170302 Address after: France Patentee after: ABIVAX company Patentee after: National Research Center Patentee after: Institut Curie Patentee after: Universite De Montpellier Address before: France Patentee before: ABIVAX company Patentee before: National Research Center Patentee before: Institut Curie Patentee before: Univ. Montpellier II |