ES2883295T3 - Forma cristalina de 1-(1-metil-1h-pirazol-4-il)-n-((1r,5s,7s)-9-metil-3-oxa-9-azabiciclo[3.3.1]nonan-7-il)-1h-indol-3-carboxamida - Google Patents
Forma cristalina de 1-(1-metil-1h-pirazol-4-il)-n-((1r,5s,7s)-9-metil-3-oxa-9-azabiciclo[3.3.1]nonan-7-il)-1h-indol-3-carboxamida Download PDFInfo
- Publication number
- ES2883295T3 ES2883295T3 ES15778162T ES15778162T ES2883295T3 ES 2883295 T3 ES2883295 T3 ES 2883295T3 ES 15778162 T ES15778162 T ES 15778162T ES 15778162 T ES15778162 T ES 15778162T ES 2883295 T3 ES2883295 T3 ES 2883295T3
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- Prior art keywords
- methyl
- nonan
- oxa
- indole
- carboxamide
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- IBAUKGNDWVSETP-UHFFFAOYSA-N suproclone Chemical compound C1CN(C(=O)CC)CCN1C(=O)OC1C(SCCS2)=C2C(=O)N1C1=CC=C(C=CC(Cl)=N2)C2=N1 IBAUKGNDWVSETP-UHFFFAOYSA-N 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 210000005222 synovial tissue Anatomy 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229960005333 tetrabenazine Drugs 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000008646 thermal stress Effects 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- NZFNXWQNBYZDAQ-UHFFFAOYSA-N thioridazine hydrochloride Chemical compound Cl.C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C NZFNXWQNBYZDAQ-UHFFFAOYSA-N 0.000 description 1
- 229960004098 thioridazine hydrochloride Drugs 0.000 description 1
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- 150000005075 thioxanthenes Chemical class 0.000 description 1
- 229950002859 tracazolate Drugs 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229960003741 tranylcypromine Drugs 0.000 description 1
- 229950002464 trepipam Drugs 0.000 description 1
- 229960003386 triazolam Drugs 0.000 description 1
- JOFWLTCLBGQGBO-UHFFFAOYSA-N triazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1Cl JOFWLTCLBGQGBO-UHFFFAOYSA-N 0.000 description 1
- BXDAOUXDMHXPDI-UHFFFAOYSA-N trifluoperazine hydrochloride Chemical compound [H+].[H+].[Cl-].[Cl-].C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 BXDAOUXDMHXPDI-UHFFFAOYSA-N 0.000 description 1
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- QDWJJTJNXAKQKD-UHFFFAOYSA-N trihexyphenidyl hydrochloride Chemical compound Cl.C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 QDWJJTJNXAKQKD-UHFFFAOYSA-N 0.000 description 1
- 229960004479 trihexyphenidyl hydrochloride Drugs 0.000 description 1
- 229950004526 uldazepam Drugs 0.000 description 1
- DTMPGSXFUXZBDK-UHFFFAOYSA-N uldazepam Chemical compound C12=CC(Cl)=CC=C2N=C(NOCC=C)CN=C1C1=CC=CC=C1Cl DTMPGSXFUXZBDK-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
- 229960000604 valproic acid Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229960001255 viloxazine Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- HUNXMJYCHXQEGX-UHFFFAOYSA-N zaleplon Chemical compound CCN(C(C)=O)C1=CC=CC(C=2N3N=CC(=C3N=CC=2)C#N)=C1 HUNXMJYCHXQEGX-UHFFFAOYSA-N 0.000 description 1
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- ZAFYATHCZYHLPB-UHFFFAOYSA-N zolpidem Chemical compound N1=C2C=CC(C)=CN2C(CC(=O)N(C)C)=C1C1=CC=C(C)C=C1 ZAFYATHCZYHLPB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
-
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/22—Anxiolytics
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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
- A61P25/24—Antidepressants
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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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Nutrition Science (AREA)
- Addiction (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Otolaryngology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462056982P | 2014-09-29 | 2014-09-29 | |
| PCT/US2015/052806 WO2016053947A1 (en) | 2014-09-29 | 2015-09-29 | Crystalline form of 1-(1-methyl-1h-pyrazol-4-yl)-n-((1r,5s,7s)-9-methyl-3-oxa-9-azabicyclo[3.3.1]nonan-7-yl)-1h-indole-3-carboxamide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2883295T3 true ES2883295T3 (es) | 2021-12-07 |
Family
ID=54289137
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES15778162T Active ES2883295T3 (es) | 2014-09-29 | 2015-09-29 | Forma cristalina de 1-(1-metil-1h-pirazol-4-il)-n-((1r,5s,7s)-9-metil-3-oxa-9-azabiciclo[3.3.1]nonan-7-il)-1h-indol-3-carboxamida |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US10329306B2 (enExample) |
| EP (1) | EP3201203B1 (enExample) |
| JP (2) | JP7055017B2 (enExample) |
| CN (1) | CN106795172B (enExample) |
| CA (1) | CA2962429C (enExample) |
| DK (1) | DK3201203T3 (enExample) |
| ES (1) | ES2883295T3 (enExample) |
| HU (1) | HUE055175T2 (enExample) |
| MA (1) | MA40771B1 (enExample) |
| PL (1) | PL3201203T3 (enExample) |
| PT (1) | PT3201203T (enExample) |
| WO (1) | WO2016053947A1 (enExample) |
Family Cites Families (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4107288A (en) | 1974-09-18 | 1978-08-15 | Pharmaceutical Society Of Victoria | Injectable compositions, nanoparticles useful therein, and process of manufacturing same |
| FR2531083B1 (fr) | 1982-06-29 | 1986-11-28 | Sandoz Sa | Nouveaux derives de la piperidine, leur preparation et leur utilisation comme medicaments |
| JPS5936675A (ja) | 1982-07-13 | 1984-02-28 | サンド・アクチエンゲゼルシヤフト | 二環性複素環式カルボン酸アザビシクロアルキルエステルまたはアミド |
| GB8510752D0 (en) | 1985-04-27 | 1985-06-05 | Beecham Group Plc | Compounds |
| DE3687080T2 (de) | 1985-04-27 | 1993-03-25 | Beecham Group Plc | Azabicyclononyl-indazol-carboxamid mit 5-ht-antagonistischer wirkung. |
| US4910193A (en) | 1985-12-16 | 1990-03-20 | Sandoz Ltd. | Treatment of gastrointestinal disorders |
| DE3722069A1 (de) | 1986-08-21 | 1988-02-25 | Toyoda Gosei Kk | Signalhornschaltvorrichtung fuer ein steuerrad |
| EP0279114B2 (en) | 1986-11-21 | 1995-08-23 | Glaxo Group Limited | Medicaments for the treatment or prevention of the withdrawal syndrome |
| IT1226389B (it) * | 1988-07-12 | 1991-01-15 | Angeli Inst Spa | Nuovi derivati ammidinici e guanidinici |
| GB8829079D0 (en) | 1988-12-13 | 1989-01-25 | Beecham Group Plc | Novel compounds |
| JPH0421681A (ja) | 1990-05-14 | 1992-01-24 | Fujisawa Pharmaceut Co Ltd | ピロロピリジン誘導体 |
| JP3251954B2 (ja) | 1990-07-31 | 2002-01-28 | 日清ファルマ株式会社 | アザビシクロ誘導体 |
| US5187166A (en) | 1990-07-31 | 1993-02-16 | Nisshin Flour Milling Co., Ltd. | Azabicyclo derivatives and their use as antiemetics |
| HU211081B (en) | 1990-12-18 | 1995-10-30 | Sandoz Ag | Process for producing indole derivatives as serotonin antagonists and pharmaceutical compositions containing the same |
| US5145684A (en) | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
| US5149962A (en) | 1991-06-03 | 1992-09-22 | Simmonds Precision Products, Inc. | Proximity detector using faraday effect and bidirectional transmission |
| US5344831A (en) | 1992-01-31 | 1994-09-06 | Nisshin Flour Milling Co., Ltd. | Diazabicyclo derivatives |
| GB9216154D0 (en) | 1992-07-30 | 1992-09-09 | Glaxo Group Ltd | Chemical compounds |
| GB9406857D0 (en) | 1994-04-07 | 1994-06-01 | Sandoz Ltd | Improvements in or relating to organic compounds |
| JP3904254B2 (ja) | 1994-10-20 | 2007-04-11 | 株式会社日清製粉グループ本社 | ５−ｈｔ４受容体作動薬 |
| CA2160420A1 (en) | 1994-10-20 | 1996-04-21 | Haruhiko Kikuchi | 5-ht4 receptor agonists |
| WO1996012722A1 (en) | 1994-10-20 | 1996-05-02 | Nisshin Flour Milling Co., Ltd. | 5-ht4 receptor agonist |
| AU2319100A (en) | 1999-01-28 | 2000-08-18 | Nippon Shinyaku Co. Ltd. | Amide derivatives and drug compositions |
| AU1887401A (en) | 1999-12-14 | 2001-06-25 | Nippon Shinyaku Co. Ltd. | Medicinal composition |
| US20030109550A1 (en) | 2001-09-19 | 2003-06-12 | Michael Clare | Substituted indazole compounds for the treatment of inflammation |
| US20040038958A1 (en) | 2002-07-11 | 2004-02-26 | Chris Rundfeldt | Topical treatment of skin diseases |
| CA2499128C (en) | 2002-09-25 | 2012-07-31 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, and benzoisothiazoles, and preparation and uses thereof |
| KR20050111318A (ko) * | 2003-01-13 | 2005-11-24 | 다이노젠 파마세우티컬스, 인코포레이티드 | 기능성 장 질환을 치료하는 방법 |
| DE602004027171D1 (de) | 2003-04-11 | 2010-06-24 | High Point Pharmaceuticals Llc | Verbindungen mit Aktivität an der 11Beta-Hydroxasteroiddehydrogenase |
| WO2005092890A2 (en) | 2004-03-25 | 2005-10-06 | Memory Pharmaceuticals Corporation | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
| UA93348C2 (ru) | 2004-03-25 | 2011-02-10 | Меморі Фармас'Ютікалз Корпорейшн | Индазолы, бензотиазолы, бензоизотиазолы, их получение и применение |
| JP2008527028A (ja) | 2005-01-19 | 2008-07-24 | バイオリポックス エービー | 炎症の治療に有用なインドール類 |
| CN101312968A (zh) | 2005-09-23 | 2008-11-26 | 记忆药物公司 | 吲唑、苯并噻唑、苯并异噻唑、苯并异噁唑、吡唑并吡啶、异噻唑并吡啶及其制备和用途 |
| CN101460458A (zh) | 2006-02-15 | 2009-06-17 | 阿勒根公司 | 具有1－磷酸－鞘氨醇(s1p)受体拮抗剂生物活性的带芳基或者杂芳基基团的吲哚－3－羧酸的酰胺、酯、硫代酰胺和硫羟酸酯化合物 |
| AU2007214434B2 (en) | 2006-02-15 | 2012-06-14 | Allergan, Inc. | Indole-3-carboxylic acid amide, ester, thioamide and thiol ester compounds bearing aryl or heteroaryl groups having sphingosine-1-phosphate (S1P) receptor antagonist biological activity |
| SG172685A1 (en) | 2006-06-28 | 2011-07-28 | Amgen Inc | Glycine transporter-1 inhibitors |
| US7960569B2 (en) | 2006-10-17 | 2011-06-14 | Bristol-Myers Squibb Company | Indole antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| WO2008097930A1 (en) | 2007-02-05 | 2008-08-14 | Amira Pharmaceuticals, Inc. | Reverse indoles as 5-lipoxygenase-activating protein (flap) inhibitors |
| EP2134683A2 (en) | 2007-02-12 | 2009-12-23 | Intermune, Inc. | Novel inhibitors hepatitis c virus replication |
| EP2185560A4 (en) | 2007-08-10 | 2011-10-05 | Lundbeck & Co As H | HETEROARYLAMIDE ANALOGS |
| WO2009108551A2 (en) | 2008-02-25 | 2009-09-03 | H. Lundbeck A/S | Heteroaryl amide analogues |
| KR101653707B1 (ko) | 2008-05-29 | 2016-09-02 | 알바니 몰레큘라 리써치, 인크. | 5-ｈｔ3 수용체 조절제, 이의 제조 방법, 및 그의 용도 |
| TWI429628B (zh) | 2010-03-29 | 2014-03-11 | Univ Taipei Medical | 吲哚基或吲哚啉基羥肟酸化合物 |
| WO2011153553A2 (en) | 2010-06-04 | 2011-12-08 | The Regents Of The University Of California | Methods and compositions for kinase inhibition |
| JOP20130213B1 (ar) | 2012-07-17 | 2021-08-17 | Takeda Pharmaceuticals Co | معارضات لمستقبلht3-5 |
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- 2015-09-29 US US15/515,263 patent/US10329306B2/en active Active
- 2015-09-29 PL PL15778162T patent/PL3201203T3/pl unknown
- 2015-09-29 ES ES15778162T patent/ES2883295T3/es active Active
- 2015-09-29 HU HUE15778162A patent/HUE055175T2/hu unknown
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- 2015-09-29 MA MA40771A patent/MA40771B1/fr unknown
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- 2015-09-29 EP EP15778162.6A patent/EP3201203B1/en active Active
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2021
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Also Published As
| Publication number | Publication date |
|---|---|
| DK3201203T3 (da) | 2021-08-23 |
| WO2016053947A1 (en) | 2016-04-07 |
| MA40771B1 (fr) | 2021-09-30 |
| PT3201203T (pt) | 2021-08-09 |
| CN106795172A (zh) | 2017-05-31 |
| US20170233406A1 (en) | 2017-08-17 |
| US10329306B2 (en) | 2019-06-25 |
| EP3201203B1 (en) | 2021-05-19 |
| JP2022036978A (ja) | 2022-03-08 |
| JP2017529379A (ja) | 2017-10-05 |
| EP3201203A1 (en) | 2017-08-09 |
| PL3201203T3 (pl) | 2021-11-22 |
| JP7055017B2 (ja) | 2022-04-15 |
| HUE055175T2 (hu) | 2021-11-29 |
| CA2962429A1 (en) | 2016-04-07 |
| CN106795172B (zh) | 2020-07-28 |
| CA2962429C (en) | 2023-01-03 |
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