ZA200600059B - New benzamides as prary modulators - Google Patents
New benzamides as prary modulators Download PDFInfo
- Publication number
- ZA200600059B ZA200600059B ZA200600059A ZA200600059A ZA200600059B ZA 200600059 B ZA200600059 B ZA 200600059B ZA 200600059 A ZA200600059 A ZA 200600059A ZA 200600059 A ZA200600059 A ZA 200600059A ZA 200600059 B ZA200600059 B ZA 200600059B
- Authority
- ZA
- South Africa
- Prior art keywords
- several
- optionally substituted
- alkyl
- benzyloxyphenyl
- alkanoyl
- Prior art date
Links
- 229940054066 benzamide antipsychotics Drugs 0.000 title description 4
- 150000003936 benzamides Chemical class 0.000 title description 4
- -1 amine radical Chemical class 0.000 claims abstract description 57
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 7
- 201000010099 disease Diseases 0.000 claims abstract description 6
- 238000009109 curative therapy Methods 0.000 claims abstract 7
- 230000000069 prophylactic effect Effects 0.000 claims abstract 7
- 238000011321 prophylaxis Methods 0.000 claims abstract 6
- 230000001404 mediated effect Effects 0.000 claims abstract 4
- 150000003254 radicals Chemical class 0.000 claims description 69
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 30
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
- 125000004423 acyloxy group Chemical group 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 16
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 16
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- 125000000623 heterocyclic group Chemical class 0.000 claims description 13
- 125000002619 bicyclic group Chemical group 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 8
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 8
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 8
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
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- 125000003118 aryl group Chemical class 0.000 claims description 3
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- 239000002253 acid Substances 0.000 claims 11
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 10
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims 7
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 4
- 230000004054 inflammatory process Effects 0.000 claims 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- KLMHSLXWYOPIFW-UHFFFAOYSA-N 2-[[4-[(4-bromophenyl)methoxy]benzoyl]amino]-3-phenylpropanoic acid Chemical compound C=1C=C(OCC=2C=CC(Br)=CC=2)C=CC=1C(=O)NC(C(=O)O)CC1=CC=CC=C1 KLMHSLXWYOPIFW-UHFFFAOYSA-N 0.000 claims 1
- ULYHRMQCQLRBFW-UHFFFAOYSA-N 2-[[4-[(4-butylphenyl)methoxy]benzoyl]-[(3-phenylmethoxyphenyl)methyl]amino]acetic acid Chemical compound C1=CC(CCCC)=CC=C1COC1=CC=C(C(=O)N(CC(O)=O)CC=2C=C(OCC=3C=CC=CC=3)C=CC=2)C=C1 ULYHRMQCQLRBFW-UHFFFAOYSA-N 0.000 claims 1
- CUVVUWFSSFVJLM-UHFFFAOYSA-N 2-[[4-[(4-butylphenyl)methoxy]benzoyl]amino]-3-cyclohexylpropanoic acid Chemical compound C1=CC(CCCC)=CC=C1COC1=CC=C(C(=O)NC(CC2CCCCC2)C(O)=O)C=C1 CUVVUWFSSFVJLM-UHFFFAOYSA-N 0.000 claims 1
- OAWGSPHGVKUKNQ-UHFFFAOYSA-N 2-[[4-[(4-methoxyphenyl)methoxy]benzoyl]amino]-3-phenylpropanoic acid Chemical compound C1=CC(OC)=CC=C1COC1=CC=C(C(=O)NC(CC=2C=CC=CC=2)C(O)=O)C=C1 OAWGSPHGVKUKNQ-UHFFFAOYSA-N 0.000 claims 1
- LZQDIFZVPHBPCY-UHFFFAOYSA-N 3-(4-phenylmethoxyphenyl)-2-[[4-[(4-phenylmethoxyphenyl)methoxy]benzoyl]amino]propanoic acid Chemical compound C=1C=C(OCC=2C=CC(OCC=3C=CC=CC=3)=CC=2)C=CC=1C(=O)NC(C(=O)O)CC(C=C1)=CC=C1OCC1=CC=CC=C1 LZQDIFZVPHBPCY-UHFFFAOYSA-N 0.000 claims 1
- IMGKVHBGPVMNFM-UHFFFAOYSA-N 3-[[4-[(3-phenylmethoxyphenyl)methoxy]benzoyl]-[(3-phenylmethoxyphenyl)methyl]amino]propanoic acid Chemical compound C=1C=C(OCC=2C=C(OCC=3C=CC=CC=3)C=CC=2)C=CC=1C(=O)N(CCC(=O)O)CC(C=1)=CC=CC=1OCC1=CC=CC=C1 IMGKVHBGPVMNFM-UHFFFAOYSA-N 0.000 claims 1
- ULTZZNFRQVAHGS-UHFFFAOYSA-N 3-phenyl-2-[(4-phenylmethoxybenzoyl)amino]propanoic acid Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1C(=O)NC(C(=O)O)CC1=CC=CC=C1 ULTZZNFRQVAHGS-UHFFFAOYSA-N 0.000 claims 1
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- 230000000968 intestinal effect Effects 0.000 claims 1
- VXQMFZZSNAJQKE-YTTGMZPUSA-N methyl (2s)-2-[[4-[2-(3-methylquinoxalin-2-yl)oxyethoxy]benzoyl]amino]-3-(4-phenylmethoxyphenyl)propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)C=1C=CC(OCCOC=2C(=NC3=CC=CC=C3N=2)C)=CC=1)C(C=C1)=CC=C1OCC1=CC=CC=C1 VXQMFZZSNAJQKE-YTTGMZPUSA-N 0.000 claims 1
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- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C235/52—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
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- C07D215/20—Oxygen atoms
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- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
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- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
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- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
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- C—CHEMISTRY; METALLURGY
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- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
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- Chemical & Material Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
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- Endocrinology (AREA)
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- Emergency Medicine (AREA)
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- Dermatology (AREA)
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- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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EP (1) | EP1644321B1 (ru) |
JP (1) | JP2006527233A (ru) |
KR (1) | KR20060061300A (ru) |
CN (1) | CN1835914A (ru) |
AT (1) | ATE497945T1 (ru) |
AU (1) | AU2004247389C1 (ru) |
BR (1) | BRPI0411412A (ru) |
CA (1) | CA2528231A1 (ru) |
CR (1) | CR8173A (ru) |
DE (1) | DE602004031339D1 (ru) |
EA (1) | EA008798B1 (ru) |
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UA (1) | UA84429C2 (ru) |
WO (1) | WO2004110983A2 (ru) |
ZA (1) | ZA200600059B (ru) |
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DE102005004885B4 (de) * | 2005-02-03 | 2010-09-30 | Bruker Daltonik Gmbh | Transport von Ionen ins Vakuum |
NZ565141A (en) * | 2005-07-19 | 2010-12-24 | Daiichi Sankyo Co Ltd | Substituted propanamide derivative and pharmaceutical composition containing the same |
EP1911744B1 (en) | 2005-07-20 | 2013-09-04 | Masanori Somei | Tryptophan derivative and use thereof |
WO2008094860A2 (en) | 2007-01-30 | 2008-08-07 | Allergan, Inc. | Treating ocular diseases using peroxisome proliferator-activated receptor delta antagonists |
AU2008338963A1 (en) * | 2007-12-13 | 2009-06-25 | Sri International | PPAR-delta ligands and methods of their use |
US8372885B2 (en) * | 2008-09-17 | 2013-02-12 | Novartis Ag | Organic compounds and their uses |
MX340488B (es) | 2010-11-05 | 2016-07-08 | Senomyx Inc | Compuestos utiles como moduladores de trpm8. |
US9278910B2 (en) | 2011-05-31 | 2016-03-08 | Receptos, Inc. | GLP-1 receptor stabilizers and modulators |
BR112015031040A8 (pt) | 2013-06-11 | 2018-01-02 | Receptos Inc | Novos moduladores do receptor de glp-1 |
JP2017538711A (ja) | 2014-12-10 | 2017-12-28 | セルジーン インターナショナル ツー エスエーアールエル | Glp−1レセプターモジュレーター |
CN108473484B (zh) | 2015-10-01 | 2021-06-29 | 弗门尼舍公司 | 可用作trpm8调节剂的化合物 |
CN107176914B (zh) * | 2016-03-09 | 2022-06-28 | 浙江旭晨医药科技有限公司 | 新型gvs系列化合物及其用途 |
WO2018011230A1 (en) * | 2016-07-13 | 2018-01-18 | Universite D'aix-Marseille | Peroxisome proliferator-activated receptor gamma agonists, method of preparation and uses thereof |
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AU6709596A (en) * | 1995-08-22 | 1997-03-19 | Japan Tobacco Inc. | Amide compounds and use of the same |
JPH09124571A (ja) * | 1995-11-01 | 1997-05-13 | Japan Tobacco Inc | アミド化合物及びその用途 |
AU712607B2 (en) * | 1996-02-02 | 1999-11-11 | Merck & Co., Inc. | Method of treating diabetes and related disease states |
EP1161412A1 (en) * | 1999-03-16 | 2001-12-12 | Glaxo Group Limited | Nuclear receptor arylating compounds |
TWI302149B (en) * | 1999-09-22 | 2008-10-21 | Bristol Myers Squibb Co | Substituted acid derivatives useful as antiodiabetic and antiobesity agents and method |
AU2003265398A1 (en) * | 2002-08-09 | 2004-02-25 | Transtech Pharma, Inc. | Aryl and heteroaryl compounds and methods to modulate coagulation |
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2006
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IL172385A0 (en) | 2006-04-10 |
EA008798B1 (ru) | 2007-08-31 |
GEP20084477B (en) | 2008-09-10 |
AU2004247389A1 (en) | 2004-12-23 |
WO2004110983A2 (en) | 2004-12-23 |
WO2004110983A3 (en) | 2005-02-10 |
EP1644321A2 (en) | 2006-04-12 |
UA84429C2 (ru) | 2008-10-27 |
BRPI0411412A (pt) | 2006-07-25 |
CA2528231A1 (en) | 2004-12-23 |
ECSP056260A (es) | 2006-04-19 |
EP1644321B1 (en) | 2011-02-09 |
KR20060061300A (ko) | 2006-06-07 |
WO2004110983A8 (en) | 2005-05-26 |
EA200600023A1 (ru) | 2006-08-25 |
AU2004247389B2 (en) | 2009-12-10 |
ATE497945T1 (de) | 2011-02-15 |
CR8173A (es) | 2006-05-31 |
MXPA05013653A (es) | 2006-02-24 |
CN1835914A (zh) | 2006-09-20 |
DE602004031339D1 (de) | 2011-03-24 |
JP2006527233A (ja) | 2006-11-30 |
US20060160894A1 (en) | 2006-07-20 |
NZ544468A (en) | 2009-09-25 |
AU2004247389C1 (en) | 2010-05-27 |
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