JP2009102423A5 - - Google Patents
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- Publication number
- JP2009102423A5 JP2009102423A5 JP2009024338A JP2009024338A JP2009102423A5 JP 2009102423 A5 JP2009102423 A5 JP 2009102423A5 JP 2009024338 A JP2009024338 A JP 2009024338A JP 2009024338 A JP2009024338 A JP 2009024338A JP 2009102423 A5 JP2009102423 A5 JP 2009102423A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- ethoxy
- pharmacologically acceptable
- esters
- acceptable salts
- 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.)
- Pending
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- 150000003839 salts Chemical class 0.000 claims 87
- 150000002148 esters Chemical class 0.000 claims 79
- 150000001875 compounds Chemical class 0.000 claims 29
- 239000008194 pharmaceutical composition Substances 0.000 claims 18
- 239000012453 solvate Substances 0.000 claims 10
- 238000000034 method Methods 0.000 claims 9
- -1 cyano, phenyl Chemical group 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 4
- 239000002775 capsule Substances 0.000 claims 4
- 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 4
- 239000002245 particle Substances 0.000 claims 4
- 239000000843 powder Substances 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- 239000000725 suspension Substances 0.000 claims 4
- 239000006188 syrup Substances 0.000 claims 4
- 235000020357 syrup Nutrition 0.000 claims 4
- 239000003826 tablet Substances 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 3
- SNTURKBPGZDIEI-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(2-ethyl-5-methylpyrrol-1-yl)ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(CC)=CC=C1C SNTURKBPGZDIEI-UHFFFAOYSA-N 0.000 claims 3
- JSXBSXFWASSZDJ-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(2-ethylpyrrol-1-yl)ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(CC)=CC=C1 JSXBSXFWASSZDJ-UHFFFAOYSA-N 0.000 claims 3
- QPWMIWSKNIKXSC-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(2-formylpyrrol-1-yl)ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=O)=CC=C1 QPWMIWSKNIKXSC-UHFFFAOYSA-N 0.000 claims 3
- LWZCFGKRNSKBAB-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(2-methyl-4-phenylpyrrol-1-yl)ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C)=CC(C=2C=CC=CC=2)=C1 LWZCFGKRNSKBAB-UHFFFAOYSA-N 0.000 claims 3
- ULCZHKYPCCVHPW-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(2-methyl-5-propylpyrrol-1-yl)ethoxy]phenyl]propanoic acid Chemical compound CCCC1=CC=C(C)N1CCOC1=CC=C(CC(OCC)C(O)=O)C=C1 ULCZHKYPCCVHPW-UHFFFAOYSA-N 0.000 claims 3
- SCHAPNBXIYKTGU-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(2-methylsulfanylpyrrol-1-yl)ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(SC)=CC=C1 SCHAPNBXIYKTGU-UHFFFAOYSA-N 0.000 claims 3
- HGONGSWUWHPWJD-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(2-phenylpyrrol-1-yl)ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC=CC=2)=CC=C1 HGONGSWUWHPWJD-UHFFFAOYSA-N 0.000 claims 3
- YNEOMLJPTDWWKY-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[2-(4-ethoxyphenyl)-5-methylpyrrol-1-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC(OCC)=CC=2)=CC=C1C YNEOMLJPTDWWKY-UHFFFAOYSA-N 0.000 claims 3
- XPXLGXIKOZQXMC-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[2-(4-fluorophenyl)-5-methylpyrrol-1-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC(F)=CC=2)=CC=C1C XPXLGXIKOZQXMC-UHFFFAOYSA-N 0.000 claims 3
- ZWXKNHFMILUPGS-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[2-methyl-5-[1-(4-methylphenyl)sulfonylpyrrol-2-yl]pyrrol-1-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2N(C=CC=2)S(=O)(=O)C=2C=CC(C)=CC=2)=CC=C1C ZWXKNHFMILUPGS-UHFFFAOYSA-N 0.000 claims 3
- MGUVOXOKEQWNKP-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[5-(4-fluorophenyl)-3-(phenylcarbamoyl)-2-propan-2-ylpyrrol-1-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C(C)C)=C(C(=O)NC=2C=CC=CC=2)C=C1C1=CC=C(F)C=C1 MGUVOXOKEQWNKP-UHFFFAOYSA-N 0.000 claims 3
- RNHNFCIPDVFAPN-UHFFFAOYSA-N 3-[4-[2-(2,5-diethylpyrrol-1-yl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(CC)=CC=C1CC RNHNFCIPDVFAPN-UHFFFAOYSA-N 0.000 claims 3
- GLTSPDYBFGMGHK-UHFFFAOYSA-N 3-[4-[2-(2-acetylpyrrol-1-yl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C(C)=O)=CC=C1 GLTSPDYBFGMGHK-UHFFFAOYSA-N 0.000 claims 3
- WFSKOWBBXJNUNZ-UHFFFAOYSA-N 3-[4-[2-(2-benzoylpyrrol-1-yl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C(=O)C=2C=CC=CC=2)=CC=C1 WFSKOWBBXJNUNZ-UHFFFAOYSA-N 0.000 claims 3
- AMPHKMYZXIKJTF-UHFFFAOYSA-N 3-[4-[2-(2-butyl-5-methylpyrrol-1-yl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound CCCCC1=CC=C(C)N1CCOC1=CC=C(CC(OCC)C(O)=O)C=C1 AMPHKMYZXIKJTF-UHFFFAOYSA-N 0.000 claims 3
- XCTXGVNJAJPLSU-UHFFFAOYSA-N 3-[4-[2-[2,5-di(propan-2-yl)pyrrol-1-yl]ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C(C)C)=CC=C1C(C)C XCTXGVNJAJPLSU-UHFFFAOYSA-N 0.000 claims 3
- JGSPMYQWTAMHSN-UHFFFAOYSA-N 3-[4-[2-[2-(3,4-dimethoxyphenyl)-5-methylpyrrol-1-yl]ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=C(OC)C(OC)=CC=2)=CC=C1C JGSPMYQWTAMHSN-UHFFFAOYSA-N 0.000 claims 3
- QWRXTXRIAGSFFT-UHFFFAOYSA-N 3-[4-[2-[2-(4-acetamidophenyl)-5-methylpyrrol-1-yl]ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC(NC(C)=O)=CC=2)=CC=C1C QWRXTXRIAGSFFT-UHFFFAOYSA-N 0.000 claims 3
- ZKSSIMHFZBOILK-UHFFFAOYSA-N 3-[4-[2-[2-(4-bromophenyl)-5-methylpyrrol-1-yl]ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC(Br)=CC=2)=CC=C1C ZKSSIMHFZBOILK-UHFFFAOYSA-N 0.000 claims 3
- VMDZYIINZMKAJE-UHFFFAOYSA-N 3-[4-[2-[2-(4-chlorophenyl)-5-methylpyrrol-1-yl]ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC(Cl)=CC=2)=CC=C1C VMDZYIINZMKAJE-UHFFFAOYSA-N 0.000 claims 3
- MHPGBVAIMXTBEC-UHFFFAOYSA-N 3-[4-[2-[2-(4-ethenoxyphenyl)-5-methylpyrrol-1-yl]ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC(OC=C)=CC=2)=CC=C1C MHPGBVAIMXTBEC-UHFFFAOYSA-N 0.000 claims 3
- BCICZBGKZJPHQB-UHFFFAOYSA-N CCOC(C)CC(C=C1)=CC=C1OCCN1C(C(C=C2)=CC=C2OCCN2CCCCC2)=CC=C1C Chemical class CCOC(C)CC(C=C1)=CC=C1OCCN1C(C(C=C2)=CC=C2OCCN2CCCCC2)=CC=C1C BCICZBGKZJPHQB-UHFFFAOYSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- XORAGNZHECJGBV-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[2-(3-methoxyphenyl)-5-methylpyrrol-1-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=C(OC)C=CC=2)=CC=C1C XORAGNZHECJGBV-UHFFFAOYSA-N 0.000 claims 2
- MBZKHQGDPOGQGZ-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[2-(4-methoxyphenyl)-5-methylpyrrol-1-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC(OC)=CC=2)=CC=C1C MBZKHQGDPOGQGZ-UHFFFAOYSA-N 0.000 claims 2
- FETPSQWCURZEKW-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-[2-methyl-5-(4-propan-2-yloxyphenyl)pyrrol-1-yl]ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC(OC(C)C)=CC=2)=CC=C1C FETPSQWCURZEKW-UHFFFAOYSA-N 0.000 claims 2
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 2
- 239000004475 Arginine Substances 0.000 claims 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims 2
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims 2
- 229940123208 Biguanide Drugs 0.000 claims 2
- 229920001268 Cholestyramine Polymers 0.000 claims 2
- 229920002911 Colestipol Polymers 0.000 claims 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 102000004877 Insulin Human genes 0.000 claims 2
- 108090001061 Insulin Proteins 0.000 claims 2
- 229940122199 Insulin secretagogue Drugs 0.000 claims 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 2
- 239000004472 Lysine Substances 0.000 claims 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 2
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 2
- 229940100389 Sulfonylurea Drugs 0.000 claims 2
- 229960001138 acetylsalicylic acid Drugs 0.000 claims 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims 2
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 2
- 229940076810 beta sitosterol Drugs 0.000 claims 2
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 claims 2
- NJKOMDUNNDKEAI-UHFFFAOYSA-N beta-sitosterol Natural products CCC(CCC(C)C1CCC2(C)C3CC=C4CC(O)CCC4C3CCC12C)C(C)C NJKOMDUNNDKEAI-UHFFFAOYSA-N 0.000 claims 2
- 239000011575 calcium Substances 0.000 claims 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 2
- 229960001231 choline Drugs 0.000 claims 2
- GMRWGQCZJGVHKL-UHFFFAOYSA-N colestipol Chemical compound ClCC1CO1.NCCNCCNCCNCCN GMRWGQCZJGVHKL-UHFFFAOYSA-N 0.000 claims 2
- 229960002604 colestipol Drugs 0.000 claims 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 2
- 229940125753 fibrate Drugs 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- 229940125396 insulin Drugs 0.000 claims 2
- 239000011777 magnesium Substances 0.000 claims 2
- 229960003512 nicotinic acid Drugs 0.000 claims 2
- 235000001968 nicotinic acid Nutrition 0.000 claims 2
- 239000011664 nicotinic acid Substances 0.000 claims 2
- FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 claims 2
- 229960003912 probucol Drugs 0.000 claims 2
- KZJWDPNRJALLNS-VJSFXXLFSA-N sitosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CC[C@@H](CC)C(C)C)[C@@]1(C)CC2 KZJWDPNRJALLNS-VJSFXXLFSA-N 0.000 claims 2
- 229950005143 sitosterol Drugs 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 2
- 230000002195 synergetic effect Effects 0.000 claims 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 2
- 229960000281 trometamol Drugs 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- UEOJCDJJSRLGFA-HAVVHWLPSA-N (E)-2-ethoxy-3-[4-[2-(2-methyl-5-phenylpyrrol-1-yl)ethoxy]phenyl]prop-2-enoic acid Chemical compound C1=CC(/C=C(/OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC=CC=2)=CC=C1C UEOJCDJJSRLGFA-HAVVHWLPSA-N 0.000 claims 1
- UEOJCDJJSRLGFA-QJOMJCCJSA-N (z)-2-ethoxy-3-[4-[2-(2-methyl-5-phenylpyrrol-1-yl)ethoxy]phenyl]prop-2-enoic acid Chemical compound C1=CC(\C=C(/OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC=CC=2)=CC=C1C UEOJCDJJSRLGFA-QJOMJCCJSA-N 0.000 claims 1
- UEOJCDJJSRLGFA-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(2-methyl-5-phenylpyrrol-1-yl)ethoxy]phenyl]prop-2-enoic acid Chemical compound C1=CC(C=C(OCC)C(O)=O)=CC=C1OCCN1C(C=2C=CC=CC=2)=CC=C1C UEOJCDJJSRLGFA-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000004492 methyl ester group Chemical group 0.000 claims 1
- 230000000269 nucleophilic effect Effects 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000005000 thioaryl group Chemical group 0.000 claims 1
- 0 C*[n]1c(*)c(*)c(*)c1* Chemical compound C*[n]1c(*)c(*)c(*)c1* 0.000 description 2
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN711MU2001 | 2001-07-26 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003515234A Division JP4313194B2 (ja) | 2001-07-26 | 2002-07-25 | 脂質とコレステロールを低下させる活性を有する新規なピロール、そのピロールの調製方法、そのピロールを含む医薬組成物、医療におけるそのピロールの利用法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009102423A JP2009102423A (ja) | 2009-05-14 |
| JP2009102423A5 true JP2009102423A5 (enExample) | 2009-10-08 |
Family
ID=11097270
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003515234A Expired - Fee Related JP4313194B2 (ja) | 2001-07-26 | 2002-07-25 | 脂質とコレステロールを低下させる活性を有する新規なピロール、そのピロールの調製方法、そのピロールを含む医薬組成物、医療におけるそのピロールの利用法 |
| JP2009024338A Pending JP2009102423A (ja) | 2001-07-26 | 2009-02-04 | 脂質とコレステロールを低下させる活性を有する新規なピロール、そのピロールの調製方法、そのピロールを含む医薬組成物、医療におけるそのピロールの利用法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003515234A Expired - Fee Related JP4313194B2 (ja) | 2001-07-26 | 2002-07-25 | 脂質とコレステロールを低下させる活性を有する新規なピロール、そのピロールの調製方法、そのピロールを含む医薬組成物、医療におけるそのピロールの利用法 |
Country Status (31)
| Country | Link |
|---|---|
| US (6) | US6987123B2 (enExample) |
| EP (1) | EP1414439B1 (enExample) |
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Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6987123B2 (en) * | 2001-07-26 | 2006-01-17 | Cadila Healthcare Limited | Heterocyclic compounds, their preparation, pharmaceutical compositions containing them and their use in medicine |
| WO2003105864A1 (en) * | 2002-06-13 | 2003-12-24 | Board Of Regents, The University Of Texas System | Methods and compositions involving aldose reductase inhibitors |
| US20050288373A1 (en) * | 2002-10-24 | 2005-12-29 | Ron Eyal S | Methods of treating various conditions by administration of sustained release L-arginine |
| US20040248972A1 (en) * | 2003-05-16 | 2004-12-09 | Ambit Biosciences Corporation | Compounds and uses thereof |
| US20050182125A1 (en) * | 2003-05-16 | 2005-08-18 | Ambit Biosciences Corporation | Pyrrole compounds and uses thereof |
| US20040248957A1 (en) * | 2003-05-16 | 2004-12-09 | Ambit Biosciences Corporation | Heterocyclic compounds and uses thereof |
| US9518899B2 (en) * | 2003-08-11 | 2016-12-13 | Sakura Finetek U.S.A., Inc. | Automated reagent dispensing system and method of operation |
| US7744817B2 (en) * | 2003-08-11 | 2010-06-29 | Sakura Finetek U.S.A., Inc. | Manifold assembly |
| US7767152B2 (en) * | 2003-08-11 | 2010-08-03 | Sakura Finetek U.S.A., Inc. | Reagent container and slide reaction retaining tray, and method of operation |
| PT1773768T (pt) | 2004-07-30 | 2018-11-30 | Exelixis Inc | Derivados de pirrol como agentes farmacêuticos |
| US20110092566A1 (en) * | 2004-11-19 | 2011-04-21 | Srivastava Satish K | Treatment of cancer with aldose reductase inhibitors |
| US8735595B2 (en) | 2006-02-15 | 2014-05-27 | Abbvie Inc. | Acetyl-CoA carboxylase (ACC) inhibitors and their use in diabetes, obesity and metabolic syndrome |
| US8748627B2 (en) | 2006-02-15 | 2014-06-10 | Abbvie Inc. | Acetyl-CoA carboxylase (ACC) inhibitors and their use in diabetes, obesity and metabolic syndrome |
| US8459509B2 (en) | 2006-05-25 | 2013-06-11 | Sakura Finetek U.S.A., Inc. | Fluid dispensing apparatus |
| CA2685202C (en) | 2007-03-23 | 2017-11-28 | The Board Of Regents Of The University Of Texas System | Methods for treating allergic asthma |
| US20090270490A1 (en) * | 2008-04-24 | 2009-10-29 | The Board Of Regents Of The University Of Texas System | Methods involving aldose reductase inhibition |
| AU2015258299B2 (en) * | 2010-08-18 | 2017-10-19 | Samumed, Llc | Diketones and hydroxyketones as catenin signaling pathway activators |
| EP3915367A1 (en) * | 2010-08-18 | 2021-12-01 | BioSplice Therapeutics, Inc. | Diketones and hydroxyketones as catenin signaling pathway activators |
| AU2015268725B2 (en) * | 2011-01-31 | 2016-10-20 | Zydus Lifesciences Limited | Treatment for lipodystrophy |
| EP3009136A1 (en) * | 2011-01-31 | 2016-04-20 | Cadila Healthcare Limited | Treatment for lipodystrophy |
| US8752732B2 (en) | 2011-02-01 | 2014-06-17 | Sakura Finetek U.S.A., Inc. | Fluid dispensing system |
| JP5971657B2 (ja) * | 2011-04-20 | 2016-08-17 | 塩野義製薬株式会社 | Ｔｒｐｖ４阻害活性を有する芳香族複素環誘導体 |
| US8580568B2 (en) | 2011-09-21 | 2013-11-12 | Sakura Finetek U.S.A., Inc. | Traceability for automated staining system |
| US8932543B2 (en) | 2011-09-21 | 2015-01-13 | Sakura Finetek U.S.A., Inc. | Automated staining system and reaction chamber |
| US8754084B2 (en) | 2012-03-27 | 2014-06-17 | The Board Of Trustees Of The University Of Illinois | Therapeutic methods and agents for treating myotonic dystrophy |
| PE20151721A1 (es) | 2013-02-22 | 2015-12-07 | Samumed Llc | Y-dicetonas como activadores de la ruta de senalizacion de wnt/b-catenina |
| UA114360C2 (uk) | 2013-04-22 | 2017-05-25 | Каділа Хелткере Лімітед | Спосіб лікування та/або зменшення інтенсивності неалкогольної жирової хвороби печінки (нжхп) |
| US20160107989A1 (en) | 2013-05-30 | 2016-04-21 | Cadila Healthcare Limited | A process for preparation of pyrroles having hypolipidemic hypocholesteremic activities |
| TW201513857A (zh) | 2013-07-05 | 2015-04-16 | Cadila Healthcare Ltd | 協同性組成物 |
| IN2013MU02470A (enExample) | 2013-07-25 | 2015-06-26 | Cadila Healthcare Ltd | |
| US9951009B2 (en) * | 2013-08-29 | 2018-04-24 | Cadila Healthcare Limited | Polymorphic form of pyrrole derivative and intermediate thereof |
| IN2013MU02905A (enExample) | 2013-09-06 | 2015-07-03 | Cadila Healthcare Ltd | |
| CA2956464C (en) | 2014-08-08 | 2023-05-09 | The Board Of Trustees Of The University Of Illinois | Bisamidinium-based inhibitors for the treatment of myotonic dystrophy |
| DK3206686T3 (da) | 2014-08-20 | 2019-12-16 | Samumed Llc | Gamma-diketoner til behandling og forebyggelse af ældning af huden og rynker |
| WO2017064635A2 (en) | 2015-10-14 | 2017-04-20 | Cadila Healthcare Limited | Pyrrole compound, compositions and process for preparation thereof |
| WO2017089979A1 (en) | 2015-11-26 | 2017-06-01 | Cadila Healthcare Limited | Dual ppar modulators for the treatment of diabetic nephropathy and related diseases |
| WO2017089980A1 (en) | 2015-11-26 | 2017-06-01 | Cadila Healthcare Limited | Dual ppar modulators for the treatment of diabetic retinopathy and diabetic eye diseases |
| EP3551180B1 (en) | 2016-12-09 | 2021-09-29 | Cadila Healthcare Limited | Treatment for primary biliary cholangitis |
| US11242326B2 (en) | 2017-08-25 | 2022-02-08 | The Board Of Trustees Of The University Of Illinois | Multivalent ligand for myotonic dystrophy |
| EP4775207A2 (en) | 2018-12-05 | 2026-07-15 | Viking Therapeutics, Inc. | Compositions for the treatment of fibrosis |
| US12201609B2 (en) | 2018-12-18 | 2025-01-21 | Zydus Lifesciences Limited | Saroglitazar for the treatment of hepatocellular carcinoma |
| CN110372677B (zh) * | 2019-07-25 | 2021-01-05 | 浙江海森药业股份有限公司 | 一种无溶剂法制备阿托伐他汀关键中间体l1的方法 |
| WO2021220236A1 (en) * | 2020-05-01 | 2021-11-04 | Cadila Healthcare Limited | Pharmaceutical compositions for combination therapy |
| US12201611B2 (en) | 2020-07-24 | 2025-01-21 | Zydus Lifesciences Limited | Composition comprising high purity pyrrole derivative and method for preparation thereof |
| JP7765474B2 (ja) * | 2020-12-03 | 2025-11-06 | デルタ ４ ゲーエムベーハー | 巣状分節性糸球体硬化症（ｆｓｇｓ）の治療における使用のためのサログリタザールおよびミリスチン酸 |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5089514A (en) * | 1990-06-14 | 1992-02-18 | Pfizer Inc. | 3-coxazolyl [phenyl, chromanyl or benzofuranyl]-2-hydroxypropionic acid derivatives and analogs as hypoglycemic agents |
| SK695A3 (en) | 1992-07-03 | 1995-07-11 | Smithkline Beecham Plc | Heterocyclic compounds method of their production and using |
| GB9225386D0 (en) | 1992-12-04 | 1993-01-27 | Smithkline Beecham Plc | Novel compounds |
| GB9311644D0 (en) | 1993-06-05 | 1993-07-21 | Smithkline Beecham Plc | Novel compounds |
| US5387613A (en) | 1993-07-23 | 1995-02-07 | Ribogene, Inc. | Treatment of tachyarrhythmias of supraventricular origin |
| GB9326171D0 (en) | 1993-12-22 | 1994-02-23 | Smithkline Beecham Plc | Novel compounds |
| WO1996004261A1 (en) | 1994-07-29 | 1996-02-15 | Smithkline Beecham Plc | Benzoxazoles and pryridine derivatives useful in the treatment of the type ii diabetes |
| US6075140A (en) | 1995-04-28 | 2000-06-13 | Daiichi Pharmaceutical Co., Ltd. | Pentacyclic compound |
| NZ286920A (en) | 1995-07-03 | 1997-06-24 | Sankyo Co | Use of combination of hmg-coa reductase inhibitors and of insulin sensitizers for the prevention/treatment of arteriosclerosis or xanthoma |
| JP3220373B2 (ja) | 1995-11-28 | 2001-10-22 | バイエル薬品株式会社 | 持続性ニフエジピン製剤 |
| GB9600464D0 (en) * | 1996-01-09 | 1996-03-13 | Smithkline Beecham Plc | Novel method |
| DE19607953A1 (de) | 1996-03-01 | 1997-09-04 | Kalle Nalo Gmbh | Nach dem Aminoxidverfahren hergestellte Nahrungsmittelhüllen auf Cellulosebasis |
| GB9606805D0 (en) | 1996-03-30 | 1996-06-05 | Glaxo Wellcome Inc | Medicaments |
| ZA973850B (en) | 1996-05-06 | 1997-12-02 | Reddy Research Foundation | Novel antidiabetic compounds having hypolipidaemic, anti-hypertensive properties, process for their preparation and pharmaceutical compositions containing them. |
| ZA973848B (en) | 1996-05-06 | 1997-12-02 | Reddy Research Foundation | Novel heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them. |
| AU744518B2 (en) * | 1996-07-01 | 2002-02-28 | Dr. Reddy's Laboratories Limited | Novel heterocyclic compounds process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases |
| US5885997A (en) | 1996-07-01 | 1999-03-23 | Dr. Reddy's Research Foundation | Heterocyclic compounds, process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases |
| AU3552697A (en) | 1996-07-12 | 1998-02-09 | Smithkline Beecham Plc | Novel treatment of leptine resistance |
| US6039033A (en) | 1996-12-24 | 2000-03-21 | Daewoo Motor Co., Ltd. | Apparatus of exhaust gas recirculation valve for an internal combustion engine |
| US6313113B1 (en) | 1997-04-15 | 2001-11-06 | Reddy-Cheminor, Inc. | Heterocyclic compounds having antidiabetic, hypolipidemic and antihypertensive properties, process for their preparation and pharmaceutical compositions containing them |
| US6011031A (en) | 1997-05-30 | 2000-01-04 | Dr. Reddy's Research Foundation | Azolidinediones useful for the treatment of diabetes, dyslipidemia and hypertension: process for their preparation and pharmaceutical compositions containing them |
| CZ284734B6 (cs) | 1997-09-02 | 1999-02-17 | Rieter Elitex A.S. | Spřádací ústrojí rotorového dopřádacího stroje |
| DK1015441T3 (da) * | 1997-09-11 | 2004-07-26 | Upjohn Co | Fremgangsmåde til fremstilling af 4-hydroxy-2-oxo-pyranderivater, der er nyttige som proteaseinhibitorer |
| ES2200248T3 (es) | 1997-09-19 | 2004-03-01 | Ssp Co., Ltd. | Derivados de acudi fenilpropionico sustituido en alfa y medicamento que los contienen. |
| EP1124807A1 (en) | 1997-10-27 | 2001-08-22 | Dr. Reddy's Research Foundation | Novel heterocyclic compounds and their use in medicine, process for their preparation and pharmaceutical compositions containing them |
| US6369067B1 (en) | 1997-10-27 | 2002-04-09 | Dr. Reddy's Research Foundation | Monocyclic compounds and their use in medicine: process for their preparation and pharmaceutical compositions containing them |
| BR9812772A (pt) * | 1997-10-27 | 2000-10-10 | Reddy Research Foundation | "compostos tricìclicos inéditos e o seu emprego na medicina;processo para a sua preparação e composições farmacêuticas contendo os mesmos" |
| US6265401B1 (en) | 1997-10-27 | 2001-07-24 | Reddy-Cheminor, Inc. | Bicyclic compounds and their use in medicine, process for their preparation and pharmaceutical compositions containing them |
| US6444816B1 (en) | 1997-10-27 | 2002-09-03 | Dr. Reddy's Research Foundation | Fused 7-oxo-pyrimidinyl compounds, preparation, composition and use thereof |
| US6440961B1 (en) | 1997-10-27 | 2002-08-27 | Dr. Reddy's Research Foundation | Tricyclic compounds and their use in medicine: process for their preparation and pharmaceutical compositions containing them |
| WO1999019313A1 (en) | 1997-10-27 | 1999-04-22 | Dr. Reddy's Research Foundation | Novel tricyclic compounds and their use in medicine; process for their preparation and pharmaceutical compositions containing them |
| WO1999038850A1 (en) | 1998-01-29 | 1999-08-05 | Dr. Reddy's Research Foundation | Novel alkanoic acids and their use in medicine, process for their preparation and pharmaceutical compositions containing them |
| CN1208326C (zh) | 1998-04-23 | 2005-06-29 | 雷迪实验室有限公司 | 杂环化合物及其在医药方面的应用、其制备方法及含有它们的药物组合物 |
| DE69902657T2 (de) | 1998-05-05 | 2003-04-30 | Sepracor Inc., Marlborough | Hydroxyomeprazol-enthaltende zubereitungen und verwendungen |
| JP2002507543A (ja) | 1998-05-27 | 2002-03-12 | ドクター・レディーズ・リサーチ・ファウンデーション | 二環系化合物、その製造方法およびそれらを含有する薬学的組成物 |
| SE9801990D0 (sv) | 1998-06-04 | 1998-06-04 | Astra Ab | New 3-aryl propionic acid derivatives and analogs |
| US6589969B1 (en) | 1998-10-16 | 2003-07-08 | Ono Pharmaceutical Co., Ltd. | Carboxylic acid derivatives and drugs containing the same as the active ingredient |
| EP1123269A1 (en) | 1998-10-21 | 2001-08-16 | Novo Nordisk A/S | New compounds, their preparation and use |
| US6248781B1 (en) | 1998-10-21 | 2001-06-19 | Novo Nordisk A/S | Compounds useful in the treatment of conditions mediated by peroxisome proliferator-activated receptors (PPAR) |
| WO2000023445A1 (en) | 1998-10-21 | 2000-04-27 | Novo Nordisk A/S | New compounds, their preparation and use |
| EP1123297A1 (en) | 1998-10-21 | 2001-08-16 | Novo Nordisk A/S | New compounds, their preparation and use |
| CA2374995C (en) | 1999-07-20 | 2010-12-07 | Dow Agrosciences Llc | Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation |
| US6312113B1 (en) * | 1999-10-29 | 2001-11-06 | Marconi Data Systems Inc. | Ink circulation system |
| ES2449194T3 (es) | 2000-01-19 | 2014-03-18 | Cadila Healthcare Limited | Compuestos que tienen actividades hipolipidémica e hipocolesterolémica, procedimiento para su preparación y composiciones farmacéuticas que los contienen |
| US6569901B2 (en) | 2000-01-28 | 2003-05-27 | Novo Nordisk A/S | Alkynyl-substituted propionic acid derivatives, their preparation and use |
| CA2415742A1 (en) | 2000-07-25 | 2002-01-31 | Merck & Co., Inc. | N-substituted indoles useful in the treatment of diabetes |
| US6987123B2 (en) | 2001-07-26 | 2006-01-17 | Cadila Healthcare Limited | Heterocyclic compounds, their preparation, pharmaceutical compositions containing them and their use in medicine |
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2001
- 2001-08-10 US US09/928,242 patent/US6987123B2/en not_active Expired - Lifetime
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2002
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- 2002-07-25 NZ NZ550375A patent/NZ550375A/en not_active IP Right Cessation
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- 2002-07-25 CO CO02064455A patent/CO5390079A1/es active IP Right Grant
- 2002-07-25 WO PCT/IN2002/000155 patent/WO2003009841A1/en not_active Ceased
- 2002-07-25 HR HRP20040138AA patent/HRP20040138B1/hr not_active IP Right Cessation
- 2002-07-25 JP JP2003515234A patent/JP4313194B2/ja not_active Expired - Fee Related
- 2002-07-25 OA OA1200400020A patent/OA12702A/en unknown
- 2002-07-25 DK DK02751609.5T patent/DK1414439T3/da active
- 2002-07-25 CA CA2454863A patent/CA2454863C/en not_active Expired - Fee Related
- 2002-07-25 DE DE60239939T patent/DE60239939D1/de not_active Expired - Lifetime
- 2002-07-25 ES ES02751609T patent/ES2366279T3/es not_active Expired - Lifetime
- 2002-07-25 NZ NZ545896A patent/NZ545896A/en not_active IP Right Cessation
- 2002-07-25 EA EA200400226A patent/EA006858B1/ru not_active IP Right Cessation
- 2002-07-25 SI SI200230947T patent/SI1414439T1/sl unknown
- 2002-07-25 KR KR1020067015951A patent/KR20060094545A/ko not_active Withdrawn
- 2002-07-25 EP EP02751609A patent/EP1414439B1/en not_active Expired - Lifetime
- 2002-07-25 IL IL160042A patent/IL160042A/en not_active IP Right Cessation
- 2002-07-25 MY MYPI20022774A patent/MY140057A/en unknown
- 2002-07-25 KR KR1020047001174A patent/KR100667710B1/ko not_active Expired - Fee Related
- 2002-07-25 PL PL368289A patent/PL224397B1/pl unknown
- 2002-07-25 BR BRPI0211665A patent/BRPI0211665B8/pt not_active IP Right Cessation
- 2002-07-25 UA UA2004021090A patent/UA76992C2/uk unknown
- 2002-07-25 AU AU2002355205A patent/AU2002355205B2/en not_active Ceased
- 2002-07-25 CN CNB028189833A patent/CN100450477C/zh not_active Expired - Fee Related
- 2002-07-25 AT AT02751609T patent/ATE507828T1/de active
- 2002-07-25 RS YU17404A patent/RS51837B/sr unknown
- 2002-07-25 PT PT02751609T patent/PT1414439E/pt unknown
- 2002-07-25 AP APAP/P/2004/002973A patent/AP1808A/en active
- 2002-07-25 MX MXPA04000758A patent/MXPA04000758A/es active IP Right Grant
- 2002-07-26 AR ARP020102839A patent/AR036347A1/es active IP Right Grant
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2004
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- 2004-01-26 ZA ZA200400563A patent/ZA200400563B/en unknown
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