KR20090007413A - 4,5-디페닐-피리미디닐-옥시 또는 -머캅토 치환된 카복실산, 이의 제조방법 및 약물로서의 이의 용도 - Google Patents
4,5-디페닐-피리미디닐-옥시 또는 -머캅토 치환된 카복실산, 이의 제조방법 및 약물로서의 이의 용도 Download PDFInfo
- Publication number
- KR20090007413A KR20090007413A KR1020087027547A KR20087027547A KR20090007413A KR 20090007413 A KR20090007413 A KR 20090007413A KR 1020087027547 A KR1020087027547 A KR 1020087027547A KR 20087027547 A KR20087027547 A KR 20087027547A KR 20090007413 A KR20090007413 A KR 20090007413A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- inhibitors
- formula
- compound
- agonists
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 229910052731 fluorine Inorganic materials 0.000 claims description 30
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 28
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- RADKZDMFGJYCBB-UHFFFAOYSA-N pyridoxal hydrochloride Natural products CC1=NC=C(CO)C(C=O)=C1O RADKZDMFGJYCBB-UHFFFAOYSA-N 0.000 description 1
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- 238000010561 standard procedure Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
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- ZAOPBCHLHBOUPR-UHFFFAOYSA-N tert-butyl 1-[2-[di(propan-2-yl)amino]ethylcarbamoyl]-6-phenylmethoxy-3,4-dihydro-1h-isoquinoline-2-carboxylate Chemical compound C=1C=C2C(C(=O)NCCN(C(C)C)C(C)C)N(C(=O)OC(C)(C)C)CCC2=CC=1OCC1=CC=CC=C1 ZAOPBCHLHBOUPR-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
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- CMSGWTNRGKRWGS-NQIIRXRSSA-N torcetrapib Chemical compound COC(=O)N([C@H]1C[C@@H](CC)N(C2=CC=C(C=C21)C(F)(F)F)C(=O)OCC)CC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 CMSGWTNRGKRWGS-NQIIRXRSSA-N 0.000 description 1
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
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- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
-
- 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
- A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
-
- 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
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Endocrinology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006021872A DE102006021872B4 (de) | 2006-05-11 | 2006-05-11 | 4,5-Diphenyl-pyrimidinyl-oxy oder -mercapto substituierte Carbonsäuren, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE102006021872.8 | 2006-05-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20090007413A true KR20090007413A (ko) | 2009-01-16 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020087027547A Abandoned KR20090007413A (ko) | 2006-05-11 | 2007-04-30 | 4,5-디페닐-피리미디닐-옥시 또는 -머캅토 치환된 카복실산, 이의 제조방법 및 약물로서의 이의 용도 |
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|---|---|
| US (1) | US7709494B2 (enExample) |
| EP (1) | EP2024339B1 (enExample) |
| JP (1) | JP2009536626A (enExample) |
| KR (1) | KR20090007413A (enExample) |
| CN (1) | CN101421249A (enExample) |
| AR (1) | AR060993A1 (enExample) |
| AU (1) | AU2007250210B2 (enExample) |
| BR (1) | BRPI0711399A2 (enExample) |
| CA (1) | CA2651466A1 (enExample) |
| DE (1) | DE102006021872B4 (enExample) |
| IL (1) | IL195178A0 (enExample) |
| MX (1) | MX2008014208A (enExample) |
| MY (1) | MY148483A (enExample) |
| NO (1) | NO20085064L (enExample) |
| TW (1) | TW200815367A (enExample) |
| WO (1) | WO2007131619A1 (enExample) |
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| US7465804B2 (en) | 2005-05-20 | 2008-12-16 | Amgen Inc. | Compounds, pharmaceutical compositions and methods for their use in treating metabolic disorders |
| EP1924546A1 (en) | 2005-09-14 | 2008-05-28 | Amgen, Inc | Conformationally constrained 3- (4-hydroxy-phenyl) - substituted-propanoic acids useful for treating metabolic disorders |
| EP2061760A1 (en) | 2006-09-07 | 2009-05-27 | Amgen, Inc | Benzo-fused compounds for use in treating metabolic disorders |
| WO2008030520A1 (en) | 2006-09-07 | 2008-03-13 | Amgen Inc. | Heterocyclic gpr40 modulators |
| JP2010524932A (ja) | 2007-04-16 | 2010-07-22 | アムジエン・インコーポレーテツド | 置換ビフェニルフェノキシ−、チオフェニル−及びアミノフェニルプロパン酸ｇｐｒ４０調節物質 |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| KR20100090249A (ko) | 2007-10-10 | 2010-08-13 | 암젠 인크 | 치환된 비페닐 ｇｒｐ４０ 조절제 |
| US8450522B2 (en) | 2008-03-06 | 2013-05-28 | Amgen Inc. | Conformationally constrained carboxylic acid derivatives useful for treating metabolic disorders |
| ES2450567T3 (es) | 2008-10-15 | 2014-03-25 | Amgen, Inc | Moduladores de GPR40 espirocíclicos |
| EP3777839A1 (en) | 2009-05-19 | 2021-02-17 | Neuroderm Ltd | Compositions for continuous administration of dopa decarboxylase inhibitors |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP3159331A1 (en) | 2010-05-05 | 2017-04-26 | Infinity Pharmaceuticals, Inc. | Tetrazolones as inhibitors of fatty acid synthase |
| US8450350B2 (en) | 2010-05-05 | 2013-05-28 | Infinity Pharmaceuticals, Inc. | Triazoles as inhibitors of fatty acid synthase |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| WO2012030165A2 (ko) | 2010-08-31 | 2012-03-08 | 서울대학교산학협력단 | P P A R δ 활성물질의 태자재프로그래밍용도 |
| NZ610911A (en) * | 2010-11-15 | 2015-02-27 | Neuroderm Ltd | Continuous administration of l-dopa, dopa decarboxylase inhibitors, catechol-o-methyl transferase inhibitors and compositions for same |
| US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683705B1 (de) | 2011-03-08 | 2015-04-22 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2854764B1 (en) | 2012-06-05 | 2018-12-12 | Neuroderm Ltd | Compositions comprising apomorphine and organic acids and uses thereof |
| CN105142621A (zh) | 2012-10-24 | 2015-12-09 | 国家健康科学研究所 | 用于预防或治疗糖尿病和促进β-细胞存活的TPL2激酶抑制剂 |
| US9957219B2 (en) | 2013-12-04 | 2018-05-01 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
| US10059667B2 (en) | 2014-02-06 | 2018-08-28 | Merck Sharp & Dohme Corp. | Antidiabetic compounds |
| US10258585B2 (en) | 2014-03-13 | 2019-04-16 | Neuroderm, Ltd. | DOPA decarboxylase inhibitor compositions |
| EP3777833B1 (en) | 2014-03-13 | 2023-10-18 | Neuroderm Ltd. | Dopa decarboxylase inhibitor compositions |
| CN104193731B (zh) * | 2014-08-27 | 2017-03-15 | 广东东阳光药业有限公司 | 一种脲取代联苯类化合物及其组合物及用途 |
| WO2016151018A1 (en) | 2015-03-24 | 2016-09-29 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Method and pharmaceutical composition for use in the treatment of diabetes |
| CN111712494A (zh) | 2018-02-13 | 2020-09-25 | 吉利德科学公司 | Pd-1/pd-l1抑制剂 |
| EP4600247A3 (en) | 2018-04-19 | 2025-11-19 | Gilead Sciences, Inc. | Pd-1/pd-l1 inhibitors |
| KR20230159715A (ko) | 2018-07-13 | 2023-11-21 | 길리애드 사이언시즈, 인코포레이티드 | Pd-1/pd-l1 억제제 |
| AU2019366355B2 (en) | 2018-10-24 | 2022-10-13 | Gilead Sciences, Inc. | PD-1/PD-L1 inhibitors |
| US11213502B1 (en) | 2020-11-17 | 2022-01-04 | Neuroderm, Ltd. | Method for treatment of parkinson's disease |
| US11331293B1 (en) | 2020-11-17 | 2022-05-17 | Neuroderm, Ltd. | Method for treatment of Parkinson's disease |
| US11844754B2 (en) | 2020-11-17 | 2023-12-19 | Neuroderm, Ltd. | Methods for treatment of Parkinson's disease |
| US12161612B2 (en) | 2023-04-14 | 2024-12-10 | Neuroderm, Ltd. | Methods and compositions for reducing symptoms of Parkinson's disease |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2665159B1 (fr) * | 1990-07-24 | 1992-11-13 | Rhone Poulenc Sante | Nouveaux derives de la pyridine et de la quinoleine, leur preparation et les compositions pharmaceutiques qui les contiennent. |
| JP2006510597A (ja) * | 2002-09-27 | 2006-03-30 | メルク エンド カムパニー インコーポレーテッド | 置換ピリミジン類 |
| US20040259887A1 (en) * | 2003-06-18 | 2004-12-23 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
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- 2007-04-30 CA CA002651466A patent/CA2651466A1/en not_active Abandoned
- 2007-04-30 BR BRPI0711399-4A patent/BRPI0711399A2/pt not_active IP Right Cessation
- 2007-04-30 AU AU2007250210A patent/AU2007250210B2/en not_active Ceased
- 2007-04-30 MY MYPI20084471A patent/MY148483A/en unknown
- 2007-04-30 EP EP07724730.2A patent/EP2024339B1/de not_active Not-in-force
- 2007-04-30 MX MX2008014208A patent/MX2008014208A/es active IP Right Grant
- 2007-04-30 CN CNA2007800133694A patent/CN101421249A/zh active Pending
- 2007-04-30 WO PCT/EP2007/003803 patent/WO2007131619A1/de not_active Ceased
- 2007-05-09 TW TW096116360A patent/TW200815367A/zh unknown
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- 2008-11-10 US US12/267,925 patent/US7709494B2/en not_active Expired - Fee Related
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| CN101421249A (zh) | 2009-04-29 |
| EP2024339B1 (de) | 2013-04-10 |
| IL195178A0 (en) | 2009-08-03 |
| AU2007250210A1 (en) | 2007-11-22 |
| BRPI0711399A2 (pt) | 2011-11-01 |
| MX2008014208A (es) | 2008-11-14 |
| AR060993A1 (es) | 2008-07-30 |
| US7709494B2 (en) | 2010-05-04 |
| AU2007250210B2 (en) | 2011-11-10 |
| WO2007131619A1 (de) | 2007-11-22 |
| EP2024339A1 (de) | 2009-02-18 |
| DE102006021872B4 (de) | 2008-04-17 |
| CA2651466A1 (en) | 2007-11-22 |
| DE102006021872A1 (de) | 2007-12-27 |
| TW200815367A (en) | 2008-04-01 |
| JP2009536626A (ja) | 2009-10-15 |
| US20090149486A1 (en) | 2009-06-11 |
| MY148483A (en) | 2013-04-30 |
| NO20085064L (no) | 2009-02-06 |
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