NO329178B1 - Esterforbindelser og farmasoytiske midler og sammensetninger omfattende forbindelsene, MTP inhibitor samt bfenylforbindelse - Google Patents
Esterforbindelser og farmasoytiske midler og sammensetninger omfattende forbindelsene, MTP inhibitor samt bfenylforbindelse Download PDFInfo
- Publication number
- NO329178B1 NO329178B1 NO20041872A NO20041872A NO329178B1 NO 329178 B1 NO329178 B1 NO 329178B1 NO 20041872 A NO20041872 A NO 20041872A NO 20041872 A NO20041872 A NO 20041872A NO 329178 B1 NO329178 B1 NO 329178B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- amino
- acetoxymethyl
- carbonyl
- acid diethyl
- Prior art date
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- -1 Ester Compounds Chemical class 0.000 title claims description 262
- 239000003814 drug Substances 0.000 title claims description 50
- 239000003112 inhibitor Substances 0.000 title claims description 16
- 150000001875 compounds Chemical class 0.000 title description 379
- 239000000203 mixture Substances 0.000 title description 70
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 111
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 93
- 150000003839 salts Chemical class 0.000 claims description 90
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 86
- 102100031545 Microsomal triglyceride transfer protein large subunit Human genes 0.000 claims description 84
- 108010038232 microsomal triglyceride transfer protein Proteins 0.000 claims description 84
- 239000001257 hydrogen Substances 0.000 claims description 76
- 229910052739 hydrogen Inorganic materials 0.000 claims description 76
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 74
- 229910052736 halogen Inorganic materials 0.000 claims description 65
- 150000002367 halogens Chemical class 0.000 claims description 65
- 239000003795 chemical substances by application Substances 0.000 claims description 62
- 238000011282 treatment Methods 0.000 claims description 60
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 57
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 56
- 238000011321 prophylaxis Methods 0.000 claims description 53
- 229940079593 drug Drugs 0.000 claims description 48
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims description 47
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 47
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 47
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 38
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 38
- 125000001424 substituent group Chemical group 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 36
- 125000006823 (C1-C6) acyl group Chemical group 0.000 claims description 35
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 32
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000004423 acyloxy group Chemical group 0.000 claims description 31
- 125000003368 amide group Chemical group 0.000 claims description 31
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 31
- 150000002148 esters Chemical class 0.000 claims description 30
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 29
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 27
- 230000003111 delayed effect Effects 0.000 claims description 27
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 239000004305 biphenyl Substances 0.000 claims description 25
- 235000010290 biphenyl Nutrition 0.000 claims description 25
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 25
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 23
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 23
- 125000001624 naphthyl group Chemical group 0.000 claims description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
- 239000004480 active ingredient Substances 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 206010020772 Hypertension Diseases 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 206010012601 diabetes mellitus Diseases 0.000 claims description 15
- 208000008589 Obesity Diseases 0.000 claims description 14
- 235000020824 obesity Nutrition 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 12
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 12
- 208000029078 coronary artery disease Diseases 0.000 claims description 12
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 12
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- 239000000194 fatty acid Substances 0.000 claims description 11
- 229930195729 fatty acid Natural products 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 claims description 8
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- 239000003472 antidiabetic agent Substances 0.000 claims description 7
- 239000002220 antihypertensive agent Substances 0.000 claims description 7
- 229940127088 antihypertensive drug Drugs 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 239000007963 capsule composition Substances 0.000 claims description 7
- MEAPRSDUXBHXGD-UHFFFAOYSA-N 3-chloro-n-(4-propan-2-ylphenyl)propanamide Chemical compound CC(C)C1=CC=C(NC(=O)CCCl)C=C1 MEAPRSDUXBHXGD-UHFFFAOYSA-N 0.000 claims description 6
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- FPUQGCOBYOXAED-UHFFFAOYSA-N diethyl 2-[[2-[3-(dimethylcarbamoyl)-4-[[2-[4-(trifluoromethyl)phenyl]benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1C(=O)N(C)C)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C(F)(F)F)C=C1 FPUQGCOBYOXAED-UHFFFAOYSA-N 0.000 claims description 6
- 229940125396 insulin Drugs 0.000 claims description 6
- 229960002508 pindolol Drugs 0.000 claims description 6
- PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 claims description 6
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol hydrochloride Natural products C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 claims description 6
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- 125000005914 C6-C14 aryloxy group Chemical group 0.000 claims description 5
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims description 5
- 230000001315 anti-hyperlipaemic effect Effects 0.000 claims description 5
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- AIKVCUNQWYTVTO-UHFFFAOYSA-N nicardipine hydrochloride Chemical compound Cl.COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 AIKVCUNQWYTVTO-UHFFFAOYSA-N 0.000 claims description 4
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- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims description 3
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 claims description 3
- BOVGTQGAOIONJV-BETUJISGSA-N 1-[(3ar,6as)-3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1C[C@H]2CCC[C@H]2C1 BOVGTQGAOIONJV-BETUJISGSA-N 0.000 claims description 3
- PPWLAQVKIFDULF-UHFFFAOYSA-N 2-phenyl-1h-pyrrolo[2,3-b]pyridine Chemical compound N1C2=NC=CC=C2C=C1C1=CC=CC=C1 PPWLAQVKIFDULF-UHFFFAOYSA-N 0.000 claims description 3
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- BGLKZLSYHVCCKG-UHFFFAOYSA-N diethyl 2-[[2-[4-[[2-(4-methylphenyl)benzoyl]amino]phenyl]acetyl]oxymethyl]-2-phenylpropanedioate Chemical compound C=1C=CC=CC=1C(C(=O)OCC)(C(=O)OCC)COC(=O)CC(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C1=CC=C(C)C=C1 BGLKZLSYHVCCKG-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 18
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- NSVFSAJIGAJDMR-UHFFFAOYSA-N 2-[benzyl(phenyl)amino]ethyl 5-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylate Chemical compound CC=1NC(C)=C(C(=O)OCCN(CC=2C=CC=CC=2)C=2C=CC=CC=2)C(C=2C=C(C=CC=2)[N+]([O-])=O)C=1P1(=O)OCC(C)(C)CO1 NSVFSAJIGAJDMR-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07—ORGANIC CHEMISTRY
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
- C07D207/40—2,5-Pyrrolidine-diones
- C07D207/404—2,5-Pyrrolidine-diones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. succinimide
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- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
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- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D295/04—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
- C07D295/12—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
- 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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- C07D295/16—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 acylated on ring nitrogen atoms
- C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
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- 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
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- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
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JP2002053876 | 2002-02-28 | ||
PCT/JP2003/002398 WO2003072532A1 (fr) | 2002-02-28 | 2003-02-28 | Compose d'esters et ses utilisation en medecine |
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US (2) | US7625948B2 (fr) |
EP (1) | EP1479666A4 (fr) |
JP (1) | JP2010043098A (fr) |
KR (2) | KR100717098B1 (fr) |
CN (3) | CN1943786A (fr) |
AU (1) | AU2003211617C1 (fr) |
BR (1) | BR0306292A (fr) |
CA (1) | CA2460682C (fr) |
CO (1) | CO5570695A2 (fr) |
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NO (1) | NO329178B1 (fr) |
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SG (1) | SG165154A1 (fr) |
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Families Citing this family (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2002307839B2 (en) | 2001-06-28 | 2006-03-16 | Zoetis P Llc | Triamide-substituted indoles, benzofuranes and benzothiophenes as inhibitors of microsomal triglyceride transfer protein (MTP) and/or apolipoprotein B (Apo B) secretion |
KR100717098B1 (ko) | 2002-02-28 | 2007-05-10 | 니뽄 다바코 산교 가부시키가이샤 | 에스테르 화합물 및 그 의약 용도 |
MX2007000397A (es) * | 2003-02-28 | 2007-03-30 | Japan Tobacco Inc | Agente para el tratamiento o prevencion de diabetes, obesidad o arteriosclerosis. |
EP1669345A4 (fr) * | 2003-08-29 | 2008-02-20 | Japan Tobacco Inc | Derive d'ester et utilisation medicale de celui-ci |
WO2005063678A1 (fr) * | 2003-12-26 | 2005-07-14 | Daiichi Pharmaceutical Co., Ltd | Procede de production d'un derive de l'acide phenylacetique |
KR100799802B1 (ko) | 2004-02-04 | 2008-01-31 | 화이자 프로덕츠 인크. | 치환된 퀴놀린 화합물 |
WO2005087234A1 (fr) | 2004-03-05 | 2005-09-22 | The Trustees Of The University Of Pennsylvania | Traitement a faibles effets secondaires contre des affections liees a l'hyperlipidemie et l'hypercholesterolemie |
AU2012200214B2 (en) * | 2004-05-14 | 2013-10-24 | Emisphere Technologies, Inc. | Compounds and compositions for delivering active agents |
US20060030623A1 (en) * | 2004-07-16 | 2006-02-09 | Noboru Furukawa | Agent for the treatment or prevention of diabetes, obesity or arteriosclerosis |
EP1772149A1 (fr) * | 2004-07-27 | 2007-04-11 | Kowa Company. Ltd. | Médicament pour la prévention ou le traitement du diabète |
JP5060133B2 (ja) * | 2004-10-18 | 2012-10-31 | 日本たばこ産業株式会社 | エステル誘導体及びその医薬用途 |
RU2431480C2 (ru) * | 2004-10-18 | 2011-10-20 | Джапан Тобакко Инк. | Сложноэфирные производные и их медицинское применение |
KR20070085263A (ko) * | 2004-10-18 | 2007-08-27 | 니뽄 다바코 산교 가부시키가이샤 | 에스테르 유도체 및 그의 약학적 용도 |
US8101774B2 (en) | 2004-10-18 | 2012-01-24 | Japan Tobacco Inc. | Ester derivatives and medicinal use thereof |
MX2007004973A (es) * | 2004-10-25 | 2007-06-14 | Japan Tobacco Inc | Formulacion solida con solubilidad y estabilidad mejoradas y metodo para producir la formulacion. |
ZA200704246B (en) * | 2004-10-25 | 2009-09-30 | Japan Tobacco Inc | Solid medicinal preparation improved in solubility and stability and process for producing the same |
WO2007047880A2 (fr) * | 2005-10-18 | 2007-04-26 | Aegerion Pharmaceuticals | Methodes de traitement de troubles associees l'hyperlipidemie chez un mammifere |
PT2081921E (pt) | 2006-07-10 | 2010-12-10 | Paion Uk Ltd | Sais de benzodiazepina de acção curta e suas formas polimórficas |
US20080033019A1 (en) | 2006-08-07 | 2008-02-07 | Duke University | Cholesterol lowering drug combination |
EP2120927A1 (fr) * | 2006-12-21 | 2009-11-25 | Aegerion Pharmaceuticals, Inc. | Procédés de traitement de l'obésité à l'aide d'une combinaison comprenant un inhibiteur de mtp et un inhibiteur de l'absorption du cholestérol |
BRPI0813176A2 (pt) * | 2007-06-15 | 2014-12-30 | Mission Pharma Co | Moléculas e composições par ainibir fator edema e adenilil ciclase |
CA2741125A1 (fr) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Nouveaux derives de benzimidazole cycliques utiles comme agents anti-diabetiques |
WO2010051206A1 (fr) | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Nouveaux agents antidiabétiques utiles avec des dérivés de benzimidazole cycliques |
WO2010148179A1 (fr) * | 2009-06-18 | 2010-12-23 | Japan Tobacco Inc. | Procédé de traitement d'un trouble associé à mtp |
US8895596B2 (en) | 2010-02-25 | 2014-11-25 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
WO2012049566A1 (fr) | 2010-10-14 | 2012-04-19 | Japan Tobacco Inc. | Polythérapie pour l'utilisation dans le traitement du diabète |
EP2450039A1 (fr) | 2010-11-08 | 2012-05-09 | PAION UK Ltd. | Régime de dosage permettant la sédation avec CNS 7056 (Remimazolam) |
EP2677869B1 (fr) | 2011-02-25 | 2017-11-08 | Merck Sharp & Dohme Corp. | Nouveaux dérivés d'azabenzimidazole cyclique utiles en tant qu'agents antidiabétiques |
EP2744782A1 (fr) * | 2011-08-18 | 2014-06-25 | Basf Se | Carbamoylméthoxy- et carbamoylméthylthio- et carbamoylméthylamino-benzamides pour lutter contre des organismes nuisibles invertébrés |
AU2013296470B2 (en) | 2012-08-02 | 2016-03-17 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
AU2014219020A1 (en) | 2013-02-22 | 2015-07-23 | Merck Sharp & Dohme Corp. | Antidiabetic bicyclic compounds |
AR094963A1 (es) | 2013-03-04 | 2015-09-09 | Ono Pharmaceutical Co | Reacción de oxidación excelente en el índice de conversión |
WO2014139388A1 (fr) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Nouveaux dérivés d'indole utiles en tant qu'agents antidiabétiques |
WO2015051496A1 (fr) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Composés tricycliques antidiabétiques |
EP3551176A4 (fr) | 2016-12-06 | 2020-06-24 | Merck Sharp & Dohme Corp. | Composés hétérocycliques antidiabétiques |
EP3558298A4 (fr) | 2016-12-20 | 2020-08-05 | Merck Sharp & Dohme Corp. | Composés de spirochromane antidiabétiques |
SG11202000230VA (en) | 2017-07-11 | 2020-02-27 | Vertex Pharma | Carboxamides as modulators of sodium channels |
CN109810001B (zh) * | 2019-01-22 | 2022-04-01 | 深圳市第二人民医院 | 盐酸罗匹尼罗中间体2-甲基-3-硝基苯乙酸的合成方法 |
CN112336719A (zh) * | 2020-10-19 | 2021-02-09 | 济南大学 | 一种噻唑衍生物作为α-葡萄糖苷酶抑制剂及其应用 |
CN116940582A (zh) * | 2020-11-11 | 2023-10-24 | 渤健马萨诸塞州股份有限公司 | 寡核苷酸、试剂及其制备 |
WO2022202566A1 (fr) * | 2021-03-26 | 2022-09-29 | 日清オイリオグループ株式会社 | Procédé d'augmentation de la concentration en acide décanoïque du sang, agent augmentant la concentration en acide décanoïque du sang, composition pharmaceutique et composition alimentaire |
Family Cites Families (71)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5110382Y2 (fr) | 1971-04-12 | 1976-03-19 | ||
DE2517229A1 (de) * | 1975-04-18 | 1976-10-28 | Boehringer Mannheim Gmbh | Phenylalkylcarbonsaeure-derivate und verfahren zu ihrer herstellung |
EP0023569B1 (fr) * | 1979-07-13 | 1983-06-22 | Dr. Karl Thomae GmbH | Dérivés d'acides carboxyliques, leur préparation et médicaments les contenant |
JPS57206612A (en) | 1982-04-16 | 1982-12-18 | Bayer Ag | Collapsible absorptive compressed mold article of hard soluble medicine |
GB8925833D0 (en) * | 1989-11-15 | 1990-01-04 | Robertet Sa | Derivatives of aromatic benzoates as inhibitors of esterase-producing micro-organisms |
JPH0597672A (ja) | 1991-10-08 | 1993-04-20 | Terumo Corp | アミド誘導体含有固形製剤およびその製造方法 |
GB9307527D0 (en) | 1993-04-13 | 1993-06-02 | Fujisawa Pharmaceutical Co | New venzamide derivatives,processes for the preparation thereof and pharmaceutical composition comprising the same |
GB9408185D0 (en) | 1994-04-25 | 1994-06-15 | Fujisawa Pharmaceutical Co | New benzamide derivatives, processes for the preparation thereof and pharmaceutical composition comprising the same |
DE4435477A1 (de) | 1994-10-04 | 1996-04-11 | Bayer Ag | Cycloalkano-indol- und -azaindol-derivate |
JPH08179504A (ja) | 1994-12-21 | 1996-07-12 | Mitsubishi Chem Corp | 光重合性組成物 |
JPH08208476A (ja) | 1995-02-01 | 1996-08-13 | Kanebo Ltd | ニフェジピン含有持続性製剤 |
WO1996040640A1 (fr) | 1995-06-07 | 1996-12-19 | Pfizer Inc. | DERIVES DE BIPHENYL-2-ACIDE CARBOXYLIQUE-TETRAHYDRO-ISOQUINOLEINE-6-YL AMIDES, PREPARATION DE CES AMIDES ET UTILISATION EN TANT QU'INHIBITEURS DE LA PROTEINE DE TRANSFERT DE TRIGLYCERIDE MICROSOMAL ET/OU DE LA SECRETION D'APOLIPOPROTEINES B (Apo B) |
JPH0959159A (ja) | 1995-08-24 | 1997-03-04 | Eisai Co Ltd | 吸収改善された薬剤組成物 |
EP0904262B1 (fr) | 1996-01-16 | 2004-04-21 | Bristol-Myers Squibb Company | Composes aromatiques a conformation restreinte servant d'inhibiteurs de la proteine de transfert de triglyceride microsomique et procede associe |
WO1997034610A1 (fr) | 1996-03-18 | 1997-09-25 | Nissan Chemical Industries, Ltd. | Procede de production de preparations d'hydrochlorure d'efonidipine |
JP4074966B2 (ja) | 1996-03-18 | 2008-04-16 | 日産化学工業株式会社 | 塩酸エホニジピン製剤の製造法 |
US5962440A (en) | 1996-05-09 | 1999-10-05 | Bristol-Myers Squibb Company | Cyclic phosphonate ester inhibitors of microsomal triglyceride transfer protein and method |
US6057339A (en) | 1996-05-09 | 2000-05-02 | Bristol-Myers Squibb Company | Method of inhibiting or treating phytosterolemia with an MTP inhibitor |
US5827875A (en) | 1996-05-10 | 1998-10-27 | Bristol-Myers Squibb Company | Inhibitors of microsomal triglyceride transfer protein and method |
CA2240161C (fr) | 1996-05-20 | 2005-05-24 | Janssen Pharmaceutica N.V. | Compositions antifongiques avec biodisponibilite amelioree |
YU23499A (sh) | 1996-11-27 | 2001-07-10 | Pfizer Inc. | Inhibitorski amidi apo-b-sekrecije/mtp-a |
TR199902579T2 (xx) | 1997-04-18 | 2000-01-21 | Pfizer Inc. | 4'-Triflorometil-Bifenil-2-Karboksilik asit (1,2,3,4-Tetrahidro-Izokinolin-6-�l)-Amid' in haz�rlanmas� i�in y�ntem ve ara�lar |
US5919970A (en) * | 1997-04-24 | 1999-07-06 | Allergan Sales, Inc. | Substituted diaryl or diheteroaryl methanes, ethers and amines having retinoid agonist, antagonist or inverse agonist type biological activity |
JPH1135555A (ja) | 1997-07-23 | 1999-02-09 | Wakunaga Pharmaceut Co Ltd | アミノメチル環状アミン化合物及びこれを含有する医薬 |
JP2959765B2 (ja) | 1997-12-12 | 1999-10-06 | 日本たばこ産業株式会社 | 3−ピペリジル−4−オキソキナゾリン誘導体及びそれを含有してなる医薬組成物 |
JPH11246404A (ja) | 1998-03-04 | 1999-09-14 | Taiho Yakuhin Kogyo Kk | 吸収を改善した医薬組成物 |
KR19990075252A (ko) | 1998-03-18 | 1999-10-15 | 성재갑 | 비가역성 hiv프로테아제 억제제를 포함하는 경구투여용 약학적 조성물 |
AU4543899A (en) | 1998-06-08 | 1999-12-30 | Advanced Medicine, Inc. | Multibinding inhibitors of microsomal triglyceride transferase protein |
CO5090829A1 (es) | 1998-07-21 | 2001-10-30 | Novartis Ag | Compuestos organicos de la formula i, utiles como inhibido res de la proteina de transferencia de triglicerido microso mal y de la secrecion de la apolipoproteina b. |
JP4261639B2 (ja) * | 1998-08-05 | 2009-04-30 | 日本曹達株式会社 | フェニルイミダゾール系抗高脂血症薬 |
GB9826412D0 (en) | 1998-12-03 | 1999-01-27 | Glaxo Group Ltd | Chemical compounds |
IL133201A0 (en) | 1998-12-04 | 2001-03-19 | Pfizer Prod Inc | Lowering blood levels of lipoproten (a) |
JP2002533318A (ja) | 1998-12-22 | 2002-10-08 | ニューロサーチ、アクティーゼルスカブ | イオンチャネル調節剤 |
ATE307808T1 (de) | 1999-03-24 | 2005-11-15 | Scherer Technologies Inc R P | Pharmazeutische formulierungen mit verbesserter löslichkeit in wasser |
JP2000281561A (ja) | 1999-03-26 | 2000-10-10 | Ajinomoto Co Inc | 新規溶媒法固体分散体製剤 |
DE19929065A1 (de) | 1999-06-25 | 2000-12-28 | Bayer Ag | Kombination von MTP-Inhibitoren und HMG-CoA-Reduktase-Inhibitoren und ihre Verwendung in Arzneimitteln |
DE19929031A1 (de) | 1999-06-25 | 2000-12-28 | Bayer Ag | Kombination von MTP-Inhibitoren und Lipidsenkern und ihre Verwendung in Arzneimitteln |
DE19929012A1 (de) | 1999-06-25 | 2000-12-28 | Bayer Ag | Kombination von MTP-Inhibitoren und stoffwechselbeeinflussenden Wirkstoffen und ihre Verwendung in Arzneimitteln |
DE19933926A1 (de) | 1999-07-20 | 2001-01-25 | Boehringer Ingelheim Pharma | Biphenylderivate, ihre Herstellung und ihre Verwendung als Arzneimittel |
JP2003104971A (ja) * | 1999-08-12 | 2003-04-09 | Wakunaga Pharmaceut Co Ltd | 新規アニリド誘導体又はその塩及びこれを含有する医薬 |
DE19945594A1 (de) | 1999-09-23 | 2001-03-29 | Boehringer Ingelheim Pharma | Substituierte Piperazinderivate, ihre Herstellung und ihre Verwendung als Arzneimittel |
CA2324800A1 (fr) | 1999-11-10 | 2001-05-10 | Mary Anne Hickman | Utilisation d'inhibiteurs de secretion d'apo b et/ou de mtp |
CA2325358C (fr) | 1999-11-10 | 2005-08-02 | Pfizer Products Inc. | Amides de l'acide 7-¬(4'-trifluoromethylbiphenyl-2-carbonyl)amino|-quinoleine-3-carboxylique et methodes pour inhiber la secretion d'apolipoproteine b |
DE19963235A1 (de) | 1999-12-27 | 2001-07-05 | Boehringer Ingelheim Pharma | Substituierte Piperazinderivate, ihre Herstellung und ihre Verwendung als Arzneimittel |
DE19963234A1 (de) | 1999-12-27 | 2002-01-24 | Boehringer Ingelheim Pharma | Substituierte Piperazinderivate, ihre Herstellung und ihre Verwendung als Arzneimittel |
WO2001053260A1 (fr) | 2000-01-18 | 2001-07-26 | Novartis Ag | Carboxamides utilises comme inhibiteurs de proteine de transfert triglyceridique microsomique et de la secretion d'apolipoproteine b |
DE10008159B4 (de) | 2000-02-15 | 2005-08-18 | Rudy Dr. Susilo | Verwendung von 2-Methyl-thiazolidin-2,4-dicarbonsäure und/oder ihrer physiologisch verträglichen Salze als Antikrebsmittel |
WO2001077077A1 (fr) | 2000-04-10 | 2001-10-18 | Novartis Ag | Derives d'(hetero)aryl-carboxamide en tant qu'inhibiteurs de la proteine microsomale de transfert des triglycerides (mtp) et de la secretion d'apolipoproteine b (apo b) |
GB0013378D0 (en) | 2000-06-01 | 2000-07-26 | Glaxo Group Ltd | Use of therapeutic benzamide derivatives |
DE10033337A1 (de) * | 2000-07-08 | 2002-01-17 | Boehringer Ingelheim Pharma | Biphenylcarbonsäureamide, ihre Herstellung und ihre Verwendung als Arzneimittel |
US20020032238A1 (en) | 2000-07-08 | 2002-03-14 | Henning Priepke | Biphenylcarboxylic acid amides, the preparation thereof and the use thereof as medicaments |
JO2654B1 (en) | 2000-09-04 | 2012-06-17 | شركة جانسين فارماسوتيكا ان. في | Multiple aryl caroxa amides are useful as lipid - lowering agents |
EP1326835A1 (fr) | 2000-10-05 | 2003-07-16 | Fujisawa Pharmaceutical Co., Ltd. | Derives de benzamides utiles comme inhibiteurs de la secretion d'apo-b |
JO2409B1 (en) | 2000-11-21 | 2007-06-17 | شركة جانسين فارماسوتيكا ان. في | Second-phenyl carboxy amides are useful as lipid-lowering agents |
FR2816940A1 (fr) | 2000-11-23 | 2002-05-24 | Lipha | Derives de 4-(biphenylcarbonylamino)-piperidine, compositions les contenant et leur utilisation |
EP1350792A1 (fr) | 2000-12-11 | 2003-10-08 | Takeda Chemical Industries, Ltd. | Composition medicinale dont la solubilite dans l'eau est amelioree |
IT1320176B1 (it) | 2000-12-22 | 2003-11-26 | Nicox Sa | Dispersioni solide di principi attivi nitrati. |
JP2002220345A (ja) | 2001-01-24 | 2002-08-09 | Sumitomo Pharmaceut Co Ltd | 脂肪肝改善剤 |
JO2390B1 (en) | 2001-04-06 | 2007-06-17 | شركة جانسين فارماسوتيكا ان. في | Diphenylcarboxamides act as lipid-lowering agents |
US20050153913A1 (en) * | 2001-04-10 | 2005-07-14 | Kosak Kenneth M. | Nucleic acid carrier compositions and methods for their synthesis |
WO2002098839A1 (fr) | 2001-06-01 | 2002-12-12 | Tanabe Seiyaku Co., Ltd. | Biphenylcarboxamides et procede de preparation de ceux-ci |
JP4644397B2 (ja) | 2001-09-05 | 2011-03-02 | 信越化学工業株式会社 | 難溶性薬物を含む医薬用固形製剤の製造方法 |
KR100717098B1 (ko) | 2002-02-28 | 2007-05-10 | 니뽄 다바코 산교 가부시키가이샤 | 에스테르 화합물 및 그 의약 용도 |
JP3662566B2 (ja) | 2002-02-28 | 2005-06-22 | 日本たばこ産業株式会社 | エステル化合物及びその医薬用途 |
JP2004010575A (ja) | 2002-06-10 | 2004-01-15 | Kyowa Yakuhin Kogyo Kk | 溶解性を改善した医薬組成物 |
MX2007000397A (es) | 2003-02-28 | 2007-03-30 | Japan Tobacco Inc | Agente para el tratamiento o prevencion de diabetes, obesidad o arteriosclerosis. |
EP1669345A4 (fr) | 2003-08-29 | 2008-02-20 | Japan Tobacco Inc | Derive d'ester et utilisation medicale de celui-ci |
US20060030623A1 (en) | 2004-07-16 | 2006-02-09 | Noboru Furukawa | Agent for the treatment or prevention of diabetes, obesity or arteriosclerosis |
US8101774B2 (en) | 2004-10-18 | 2012-01-24 | Japan Tobacco Inc. | Ester derivatives and medicinal use thereof |
KR20070085263A (ko) | 2004-10-18 | 2007-08-27 | 니뽄 다바코 산교 가부시키가이샤 | 에스테르 유도체 및 그의 약학적 용도 |
MX2007004973A (es) | 2004-10-25 | 2007-06-14 | Japan Tobacco Inc | Formulacion solida con solubilidad y estabilidad mejoradas y metodo para producir la formulacion. |
-
2003
- 2003-02-28 KR KR1020047007905A patent/KR100717098B1/ko not_active IP Right Cessation
- 2003-02-28 KR KR1020067007778A patent/KR20060053023A/ko not_active Application Discontinuation
- 2003-02-28 WO PCT/JP2003/002398 patent/WO2003072532A1/fr active Application Filing
- 2003-02-28 ZA ZA200502495A patent/ZA200502495B/xx unknown
- 2003-02-28 IL IL16113403A patent/IL161134A0/xx unknown
- 2003-02-28 CN CNA2006100997097A patent/CN1943786A/zh active Pending
- 2003-02-28 US US10/492,831 patent/US7625948B2/en not_active Expired - Fee Related
- 2003-02-28 CN CN038047349A patent/CN1630629B/zh not_active Expired - Fee Related
- 2003-02-28 ZA ZA200502496A patent/ZA200502496B/xx unknown
- 2003-02-28 RU RU2004124370/04A patent/RU2293721C2/ru not_active IP Right Cessation
- 2003-02-28 NZ NZ531890A patent/NZ531890A/en not_active IP Right Cessation
- 2003-02-28 SG SG200605879-6A patent/SG165154A1/en unknown
- 2003-02-28 CN CN201010156863A patent/CN101838218A/zh active Pending
- 2003-02-28 MX MXPA04002602A patent/MXPA04002602A/es active IP Right Grant
- 2003-02-28 EP EP03743078A patent/EP1479666A4/fr not_active Withdrawn
- 2003-02-28 BR BR0306292-9A patent/BR0306292A/pt not_active IP Right Cessation
- 2003-02-28 CA CA2460682A patent/CA2460682C/fr not_active Expired - Fee Related
- 2003-02-28 AU AU2003211617A patent/AU2003211617C1/en not_active Ceased
-
2004
- 2004-03-23 ZA ZA200402275A patent/ZA200402275B/en unknown
- 2004-04-23 CO CO04037601A patent/CO5570695A2/es not_active Application Discontinuation
- 2004-05-06 NO NO20041872A patent/NO329178B1/no not_active IP Right Cessation
-
2006
- 2006-03-01 RU RU2006106451/04A patent/RU2006106451A/ru not_active Application Discontinuation
-
2009
- 2009-09-23 IL IL201111A patent/IL201111A0/en unknown
- 2009-09-28 JP JP2009221747A patent/JP2010043098A/ja not_active Withdrawn
-
2010
- 2010-02-12 US US12/627,535 patent/US20100158996A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
RU2004124370A (ru) | 2006-01-20 |
US7625948B2 (en) | 2009-12-01 |
CO5570695A2 (es) | 2005-10-31 |
CN1943786A (zh) | 2007-04-11 |
CA2460682C (fr) | 2010-11-30 |
CA2460682A1 (fr) | 2003-09-04 |
NZ531890A (en) | 2006-02-24 |
ZA200502495B (en) | 2005-09-20 |
RU2006106451A (ru) | 2007-09-27 |
KR20060053023A (ko) | 2006-05-19 |
CN1630629B (zh) | 2010-05-05 |
MXPA04002602A (es) | 2004-08-11 |
CN1630629A (zh) | 2005-06-22 |
NO20041872L (no) | 2004-05-06 |
EP1479666A1 (fr) | 2004-11-24 |
KR20040077852A (ko) | 2004-09-07 |
BR0306292A (pt) | 2004-08-24 |
AU2003211617C1 (en) | 2008-03-06 |
CN101838218A (zh) | 2010-09-22 |
WO2003072532A1 (fr) | 2003-09-04 |
ZA200502496B (en) | 2005-10-12 |
RU2293721C2 (ru) | 2007-02-20 |
IL201111A0 (en) | 2010-05-17 |
IL161134A0 (en) | 2004-08-31 |
ZA200402275B (en) | 2005-04-23 |
AU2003211617A1 (en) | 2003-09-09 |
US20050075367A1 (en) | 2005-04-07 |
EP1479666A4 (fr) | 2010-10-13 |
JP2010043098A (ja) | 2010-02-25 |
AU2003211617B2 (en) | 2006-02-02 |
SG165154A1 (en) | 2010-10-28 |
US20100158996A1 (en) | 2010-06-24 |
KR100717098B1 (ko) | 2007-05-10 |
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