JP2009102423A5 - - Google Patents

Download PDF

Info

Publication number: JP2009102423A5
Authority: JP; Japan
Prior art keywords: phenyl; ethoxy; pharmacologically acceptable; esters; acceptable salts
Prior art date: 2009-02-04
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

Application number

JP2009024338A

Other languages

English (en)

Japanese (ja)

Other versions

JP2009102423A (ja

Filing date

2009-02-04

Publication date

2009-10-08

2009-02-04 Application filed filed Critical

2009-05-14 Publication of JP2009102423A publication Critical patent/JP2009102423A/ja

2009-10-08 Publication of JP2009102423A5 publication Critical patent/JP2009102423A5/ja

Status Pending legal-status Critical Current

Links

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

JP2009024338A 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 Pending JP2009102423A (ja)

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 (2)	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 (2)
EP (1)	EP1414439B1 (2)
JP (2)	JP4313194B2 (2)
KR (2)	KR20060094545A (2)
CN (1)	CN100450477C (2)
AP (1)	AP1808A (2)
AR (1)	AR036347A1 (2)
AT (1)	ATE507828T1 (2)
AU (1)	AU2002355205B2 (2)
BR (1)	BRPI0211665B8 (2)
CA (1)	CA2454863C (2)
CO (1)	CO5390079A1 (2)
CY (1)	CY1111876T1 (2)
DE (1)	DE60239939D1 (2)
DK (1)	DK1414439T3 (2)
EA (1)	EA006858B1 (2)
ES (1)	ES2366279T3 (2)
HR (1)	HRP20040138B1 (2)
IL (1)	IL160042A (2)
MX (1)	MXPA04000758A (2)
MY (1)	MY140057A (2)
NO (1)	NO326698B1 (2)
NZ (2)	NZ550375A (2)
OA (1)	OA12702A (2)
PL (1)	PL224397B1 (2)
PT (1)	PT1414439E (2)
RS (1)	RS51837B (2)
SI (1)	SI1414439T1 (2)
UA (1)	UA76992C2 (2)
WO (1)	WO2003009841A1 (2)
ZA (1)	ZA200400563B (2)

Families Citing this family (44)

* Cited by examiner, † Cited by third party
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
US20050182125A1 (en) *	2003-05-16	2005-08-18	Ambit Biosciences Corporation	Pyrrole compounds and uses thereof
WO2004103960A2 (en) *	2003-05-16	2004-12-02	Ambit Biosciences Corporation	Compounds and uses thereof
US20040248972A1 (en) *	2003-05-16	2004-12-09	Ambit Biosciences Corporation	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
CA2573426C (en)	2004-07-30	2015-11-17	Exelixis, Inc.	Pyrrole derivatives as pharmaceutical agents
US20110092566A1 (en) *	2004-11-19	2011-04-21	Srivastava Satish K	Treatment of cancer with aldose reductase inhibitors
CN101484433A (zh)	2006-02-15	2009-07-15	艾博特公司	新的乙酰辅酶a羧化酶(acc)抑制剂及其在糖尿病、肥胖症和代谢综合征中的应用
JP2009526868A (ja)	2006-02-15	2009-07-23	アボット・ラボラトリーズ	新規なアセチル−ＣｏＡカルボキシラーゼ（ＡＣＣ）阻害薬およびこれらの糖尿病、肥満および代謝症候群における使用
US8459509B2 (en) *	2006-05-25	2013-06-11	Sakura Finetek U.S.A., Inc.	Fluid dispensing apparatus
EP2848252A3 (en)	2007-03-23	2015-06-17	The Board of Regents of the University of Texas System	Aldose reductase inhibitors for use in treating uveitis
US20090270490A1 (en) *	2008-04-24	2009-10-29	The Board Of Regents Of The University Of Texas System	Methods involving aldose reductase inhibition
RU2592694C2 (ru)	2010-08-18	2016-07-27	СЭМЬЮМЕД, ЭлЭлСи	Дикетоны и гидроксикетоны в качестве активатора сигнального пути катенина
AU2015258299B2 (en) *	2010-08-18	2017-10-19	Samumed, Llc	Diketones and hydroxyketones as catenin signaling pathway activators
KR101633720B1 (ko) *	2011-01-31	2016-06-27	카딜라 핼쓰캐어 리미티드	지방이상증의 치료
AU2015268725B2 (en) *	2011-01-31	2016-10-20	Zydus Lifesciences Limited	Treatment for lipodystrophy
US8752732B2 (en)	2011-02-01	2014-06-17	Sakura Finetek U.S.A., Inc.	Fluid dispensing system
WO2012144661A1 (en)	2011-04-20	2012-10-26	Shionogi & Co., Ltd.	Aromatic heterocyclic derivative having trpv4-inhibiting activity
US8932543B2 (en)	2011-09-21	2015-01-13	Sakura Finetek U.S.A., Inc.	Automated staining system and reaction chamber
US8580568B2 (en)	2011-09-21	2013-11-12	Sakura Finetek U.S.A., Inc.	Traceability for automated staining system
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
DK2968249T3 (en)	2013-02-22	2019-03-04	Samumed Llc	GAMMA DIKETONS AS WNT / BETA-CATENIN SIGNAL ROAD ACTIVATORS
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 (2)	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 (2)	2013-09-06	2015-07-03	Cadila Healthcare Ltd
US9376421B2 (en)	2014-08-08	2016-06-28	The Board Of Trustees Of The University Of Illinois	Compounds and methods for myotonic dystrophy therapy
MA40454B1 (fr)	2014-08-20	2020-01-31	Samumed Llc	Gamma-dicétones pour le traitement et la prévention des rides et du vieillissement de la peau
US10385017B2 (en)	2015-10-14	2019-08-20	Cadila Healthcare Limited	Pyrrole compound, compositions and process for preparation thereof
WO2017089980A1 (en)	2015-11-26	2017-06-01	Cadila Healthcare Limited	Dual ppar modulators for the treatment of diabetic retinopathy and diabetic eye diseases
WO2017089979A1 (en)	2015-11-26	2017-06-01	Cadila Healthcare Limited	Dual ppar modulators for the treatment of diabetic nephropathy and related diseases
MX382765B (es)	2016-12-09	2025-03-13	Zydus Lifesciences Ltd	Tratamiento para la colangitis biliar primaria.
US11242326B2 (en)	2017-08-25	2022-02-08	The Board Of Trustees Of The University Of Illinois	Multivalent ligand for myotonic dystrophy
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
US20240041825A1 (en) *	2020-12-03	2024-02-08	Delta 4 Gmbh	Saroglitazar and myristic acid for use in the treatment of focal segmental glomerulosclerosis (fsgs)

Family Cites Families (47)

* Cited by examiner, † Cited by third party
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
CZ1095A3 (en) *	1992-07-03	1995-10-18	Smithkline Beecham Plc	Heterocyclic compounds, process of their preparation, their use for the preparation of a pharmaceutical preparation and the pharmaceutical composition containing thereof
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
BR9608040B1 (pt)	1995-04-28	2010-02-23		composto taxàide pentacÍclico.
IL118778A (en)	1995-07-03	1999-07-14	Sankyo Co	Pharmaceutical compositions for the treatment of arteriosclerosis and xanthoma containing an hmg-coa reductase inhibitor
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
US5889025A (en)	1996-05-06	1999-03-30	Reddy's Research Foundation	Antidiabetic compounds having hypolipidaemic, antihypertensive 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.
CA2258949C (en) *	1996-07-01	2008-05-06	Reddy-Cheminor, Inc.	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
CA2260044A1 (en)	1996-07-12	1998-01-22	Stephen Alistair Smith	Novel treatment of leptine resistance
JPH11505006A (ja)	1996-12-24	1999-05-11	デウー・モーター・シーオー・エルティーディー	内燃機関の排気ガス再循環弁装置
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
CZ298847B6 (cs) *	1997-09-11	2008-02-27	Pharmacia & Upjohn Company	Zpusob výroby proteázového inhibitoru
ES2200248T3 (es)	1997-09-19	2004-03-01	Ssp Co., Ltd.	Derivados de acudi fenilpropionico sustituido en alfa y medicamento que los contienen.
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
MXPA00004036A (es) *	1997-10-27	2006-05-24	Reddys Lab Ltd Dr	Compuestos triciclicos novedosos y su uso en medicina; proceso para su preparacion y composiciones farmaceuticas que los contienen..
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
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
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
CN1280574A (zh) *	1997-10-27	2001-01-17	雷迪研究基金会	新的杂环化合物及其在医药中的应用、它们的制备方法和含有它们的药物组合物
EP1051403A1 (en)	1998-01-29	2000-11-15	Dr. Reddy's Research Foundation	Novel alkanoic acids and their use in medicine, process for their preparation and pharmaceutical compositions containing them
EP1073643B1 (en)	1998-04-23	2004-12-29	Dr. Reddy's Laboratories Ltd.	New heterocyclic compounds and their use in medicine, process for their preparation and pharmaceutical compositions containing them
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
EP1123292A1 (en)	1998-10-21	2001-08-16	Novo Nordisk A/S	New compounds, their preparation and use
WO2000023451A1 (en)	1998-10-21	2000-04-27	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)
EP1123269A1 (en)	1998-10-21	2001-08-16	Novo Nordisk A/S	New compounds, their preparation and use
ES2546386T3 (es)	1999-07-20	2015-09-23	Dow Agrosciences, Llc	Amidas aromáticas heterocíclicas fungicidas y sus composiciones, métodos de uso y preparación
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
AU7705601A (en)	2000-07-25	2002-02-05	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

2001
- 2001-08-10 US US09/928,242 patent/US6987123B2/en not_active Expired - Lifetime
2002
- 2002-07-19 US US10/200,107 patent/US7041837B2/en not_active Expired - Lifetime
- 2002-07-25 BR BRPI0211665A patent/BRPI0211665B8/pt not_active IP Right Cessation
- 2002-07-25 PL PL368289A patent/PL224397B1/pl unknown
- 2002-07-25 HR HRP20040138AA patent/HRP20040138B1/hr not_active IP Right Cessation
- 2002-07-25 KR KR1020067015951A patent/KR20060094545A/ko not_active Withdrawn
- 2002-07-25 UA UA2004021090A patent/UA76992C2/uk unknown
- 2002-07-25 EA EA200400226A patent/EA006858B1/ru not_active IP Right Cessation
- 2002-07-25 MX MXPA04000758A patent/MXPA04000758A/es active IP Right Grant
- 2002-07-25 DE DE60239939T patent/DE60239939D1/de not_active Expired - Lifetime
- 2002-07-25 KR KR1020047001174A patent/KR100667710B1/ko not_active Expired - Fee Related
- 2002-07-25 IL IL160042A patent/IL160042A/en not_active IP Right Cessation
- 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 US US10/592,880 patent/US8212057B2/en not_active Expired - Fee Related
- 2002-07-25 EP EP02751609A patent/EP1414439B1/en not_active Expired - Lifetime
- 2002-07-25 AU AU2002355205A patent/AU2002355205B2/en not_active Ceased
- 2002-07-25 PT PT02751609T patent/PT1414439E/pt unknown
- 2002-07-25 OA OA1200400020A patent/OA12702A/en unknown
- 2002-07-25 RS YU17404A patent/RS51837B/sr unknown
- 2002-07-25 AT AT02751609T patent/ATE507828T1/de active
- 2002-07-25 CN CNB028189833A patent/CN100450477C/zh not_active Expired - Fee Related
- 2002-07-25 NZ NZ550375A patent/NZ550375A/en not_active IP Right Cessation
- 2002-07-25 SI SI200230947T patent/SI1414439T1/sl 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 NZ NZ545896A patent/NZ545896A/en not_active IP Right Cessation
- 2002-07-25 MY MYPI20022774A patent/MY140057A/en unknown
- 2002-07-25 ES ES02751609T patent/ES2366279T3/es not_active Expired - Lifetime
- 2002-07-25 AP APAP/P/2004/002973A patent/AP1808A/en active
- 2002-07-25 JP JP2003515234A patent/JP4313194B2/ja not_active Expired - Fee Related
- 2002-07-26 AR ARP020102839A patent/AR036347A1/es active IP Right Grant
2004
- 2004-01-23 NO NO20040301A patent/NO326698B1/no not_active IP Right Cessation
- 2004-01-26 ZA ZA200400563A patent/ZA200400563B/en unknown
- 2004-03-01 US US10/790,647 patent/US7323491B2/en not_active Expired - Lifetime
2008
- 2008-01-23 US US12/018,555 patent/US8110598B2/en not_active Expired - Fee Related
2009
- 2009-02-04 JP JP2009024338A patent/JP2009102423A/ja active Pending
2011
- 2011-04-25 US US13/066,807 patent/US8558009B2/en not_active Expired - Fee Related
- 2011-07-20 CY CY20111100708T patent/CY1111876T1/el unknown

Publication	Publication Date	Title
JP2009102423A5 (2)	2009-10-08
CA2454863A1 (en)	2003-02-06	Novel pyrroles having hypolipidemic hypocholesteremic activities, process for their preparation and pharmaceutical compositions containing them and their use in medicine
CA1165689A (en)	1984-04-17	Method of increasing oral absorption of polar bioactive agents
US20180133199A1 (en)	2018-05-17	Single-dose, ready-to-use injectable formulations
US20110118292A1 (en)	2011-05-19	Method of treating atherosclerosis, dyslipidemias and related conditions
US20080139604A1 (en)	2008-06-12	Method of Treating Atherosclerosis, Dyslipidemias and Related Conditions
MX2013005124A (es)	2013-10-30	Estimuladores de la gcs.
US20230059381A1 (en)	2023-02-23	Prophylactic or therapeutic agent for neuropathic pain associated with guillain-barre syndrome
JP2018502101A5 (2)	2019-01-31
JP2005526696A5 (2)	2006-01-05
US9592233B2 (en)	2017-03-14	Pharmaceutical combination drug
JP2015505550A5 (2)	2016-03-24
JP2022533958A (ja)	2022-07-27	痛風または高尿酸血症を処置するための化合物
JP2012517441A5 (2)	2013-03-28
RU2009148507A (ru)	2011-07-10	Производное тетрагидроизохинолин-1-она или его соль
RU2012146874A (ru)	2014-05-27	Производные пиразолопиридина
JP2024542248A5 (2)	2025-12-03
JP2005501091A5 (2)	2006-01-12
JP2012520279A (ja)	2012-09-06	ロスバスタチンおよびアトルバスタチン誘導体
US20120108604A1 (en)	2012-05-03	Processes for preparing amine salts of sildenafil-analogues and use thereof
EP2395837A1 (en)	2011-12-21	Secretory phospholipase a2 (spla2) inhibitor and niacin drug compositions and methods for treating cardiovascular disease and dyslipidemia
JP2008115166A5 (2)	2010-07-22
WO2006097809B1 (en)	2007-06-07	Novel tyrosine derivatives
US20130116291A1 (en)	2013-05-09	Association of xanthine oxidase inhibitors and statins and use thereof
US20050085489A1 (en)	2005-04-21	Pharmaceutical composition comprising a glitazone and a 4-oxobutanoic acid, and the use thereof for treating diabetes