ZA200501297B - Novel indoline compound and medicinal use thereof - Google Patents
Novel indoline compound and medicinal use thereof Download PDFInfo
- Publication number
- ZA200501297B ZA200501297B ZA200501297A ZA200501297A ZA200501297B ZA 200501297 B ZA200501297 B ZA 200501297B ZA 200501297 A ZA200501297 A ZA 200501297A ZA 200501297 A ZA200501297 A ZA 200501297A ZA 200501297 B ZA200501297 B ZA 200501297B
- Authority
- ZA
- South Africa
- Prior art keywords
- dimethylpropanamide
- alkyl group
- pharmaceutically acceptable
- acceptable salt
- compound
- Prior art date
Links
- -1 indoline compound Chemical class 0.000 title claims abstract description 68
- 150000003839 salts Chemical class 0.000 claims abstract description 66
- 150000001875 compounds Chemical class 0.000 claims abstract description 34
- 239000003112 inhibitor Substances 0.000 claims abstract description 12
- 230000002248 lipoperoxidative effect Effects 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 88
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- XIPFMBOWZXULIA-UHFFFAOYSA-N pivalamide Chemical compound CC(C)(C)C(N)=O XIPFMBOWZXULIA-UHFFFAOYSA-N 0.000 claims description 4
- 229940123324 Acyltransferase inhibitor Drugs 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 102100030817 Liver carboxylesterase 1 Human genes 0.000 claims description 3
- 101710181187 Liver carboxylesterase 1 Proteins 0.000 claims description 3
- 239000002404 acyltransferase inhibitor Substances 0.000 claims description 3
- XUNQZFVPKMXPIZ-UHFFFAOYSA-N methyl n-[[7-(2,2-dimethylpropanoylamino)-4,6-dimethyl-1-octyl-2,3-dihydroindol-5-yl]sulfamoyl]carbamate Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(=O)(=O)NC(=O)OC)=C(C)C2=C1N(CCCCCCCC)CC2 XUNQZFVPKMXPIZ-UHFFFAOYSA-N 0.000 claims description 2
- JWAYGSIVSWDBCG-UHFFFAOYSA-N n-(4,6-dimethyl-5-nitro-1-octyl-2,3-dihydroindol-7-yl)-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C([N+]([O-])=O)=C(C)C2=C1N(CCCCCCCC)CC2 JWAYGSIVSWDBCG-UHFFFAOYSA-N 0.000 claims description 2
- PXCNVWWWTVXCME-UHFFFAOYSA-N n-[1-(2-ethoxyethyl)-4,6-dimethyl-5-(sulfamoylamino)-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(N)(=O)=O)=C(C)C2=C1N(CCOCC)CC2 PXCNVWWWTVXCME-UHFFFAOYSA-N 0.000 claims description 2
- KJJNCFKHNDJFJP-UHFFFAOYSA-N n-[1-(2-methoxyethyl)-2,4,6-trimethyl-5-(sulfamoylamino)-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(N)(=O)=O)=C(C)C2=C1N(CCOC)C(C)C2 KJJNCFKHNDJFJP-UHFFFAOYSA-N 0.000 claims description 2
- JTOFAJKSDOSNHT-UHFFFAOYSA-N n-[1-(cyclopropylmethyl)-5-(methanesulfonamido)-4,6-dimethyl-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound C12=C(NC(=O)C(C)(C)C)C(C)=C(NS(C)(=O)=O)C(C)=C2CCN1CC1CC1 JTOFAJKSDOSNHT-UHFFFAOYSA-N 0.000 claims description 2
- VUWPQSKZGDOIAI-UHFFFAOYSA-N n-[1-ethyl-5-(methanesulfonamido)-4,6-dimethyl-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(C)(=O)=O)=C(C)C2=C1N(CC)CC2 VUWPQSKZGDOIAI-UHFFFAOYSA-N 0.000 claims description 2
- BUKOQMILSXIEOU-UHFFFAOYSA-N n-[4,6-dimethyl-1-pentyl-5-(sulfamoylamino)-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(N)(=O)=O)=C(C)C2=C1N(CCCCC)CC2 BUKOQMILSXIEOU-UHFFFAOYSA-N 0.000 claims description 2
- CPHBNOIPZQORBL-UHFFFAOYSA-N n-[4,6-dimethyl-1-propyl-5-(sulfamoylamino)-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(N)(=O)=O)=C(C)C2=C1N(CCC)CC2 CPHBNOIPZQORBL-UHFFFAOYSA-N 0.000 claims description 2
- XSYOJEBRSRVCJK-UHFFFAOYSA-N n-[4,6-dimethyl-2-(methylsulfanylmethyl)-1-propyl-5-(sulfamoylamino)-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(N)(=O)=O)=C(C)C2=C1N(CCC)C(CSC)C2 XSYOJEBRSRVCJK-UHFFFAOYSA-N 0.000 claims description 2
- SPKCBUDGUXFYNU-UHFFFAOYSA-N n-[4,6-dimethyl-7-(sulfamoylamino)-2,3-dihydro-1h-indol-5-yl]-2,2-dimethylundecanamide Chemical compound NS(=O)(=O)NC1=C(C)C(NC(=O)C(C)(C)CCCCCCCCC)=C(C)C2=C1NCC2 SPKCBUDGUXFYNU-UHFFFAOYSA-N 0.000 claims description 2
- GGQVOQWCJWFEFU-UHFFFAOYSA-N n-[5-(methanesulfonamido)-4,6-dimethyl-1-(3-methylbutyl)-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(C)(=O)=O)=C(C)C2=C1N(CCC(C)C)CC2 GGQVOQWCJWFEFU-UHFFFAOYSA-N 0.000 claims description 2
- RBKNPTJINPQTRO-UHFFFAOYSA-N n-[5-(methanesulfonamido)-4,6-dimethyl-1-pentyl-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(C)(=O)=O)=C(C)C2=C1N(CCCCC)CC2 RBKNPTJINPQTRO-UHFFFAOYSA-N 0.000 claims description 2
- JWHOUIDVSOIXTL-UHFFFAOYSA-N n-[5-(methanesulfonamidomethyl)-4,6-dimethyl-1-octyl-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(CNS(C)(=O)=O)=C(C)C2=C1N(CCCCCCCC)CC2 JWHOUIDVSOIXTL-UHFFFAOYSA-N 0.000 claims description 2
- FITYLPBGJXBNCW-UHFFFAOYSA-N 2,2-dimethyloctanamide Chemical compound CCCCCCC(C)(C)C(N)=O FITYLPBGJXBNCW-UHFFFAOYSA-N 0.000 claims 1
- RACODSRWKOEMAV-UHFFFAOYSA-N 2,2-dimethylundecanamide Chemical compound CCCCCCCCCC(C)(C)C(N)=O RACODSRWKOEMAV-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- SMWYQJHNQZBCPG-UHFFFAOYSA-N n-[1-(2,2-dimethylpropyl)-5-(methanesulfonamido)-4,6-dimethyl-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC1=C(NS(C)(=O)=O)C(C)=C2CCN(CC(C)(C)C)C2=C1NC(=O)C(C)(C)C SMWYQJHNQZBCPG-UHFFFAOYSA-N 0.000 claims 1
- LJHDMKYZBGPNFB-UHFFFAOYSA-N n-[1-(2-ethoxyethyl)-2,4,6-trimethyl-5-(sulfamoylamino)-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(N)(=O)=O)=C(C)C2=C1N(CCOCC)C(C)C2 LJHDMKYZBGPNFB-UHFFFAOYSA-N 0.000 claims 1
- KNEHLMHPIRXMHL-UHFFFAOYSA-N n-[1-(2-ethoxyethyl)-5-(methanesulfonamido)-4,6-dimethyl-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(C)(=O)=O)=C(C)C2=C1N(CCOCC)CC2 KNEHLMHPIRXMHL-UHFFFAOYSA-N 0.000 claims 1
- QZMPWNOZKQARGD-UHFFFAOYSA-N n-[1-(2-ethylsulfanylethyl)-4,6-dimethyl-5-(sulfamoylamino)-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide;hydrochloride Chemical compound Cl.CC(C)(C)C(=O)NC1=C(C)C(NS(N)(=O)=O)=C(C)C2=C1N(CCSCC)CC2 QZMPWNOZKQARGD-UHFFFAOYSA-N 0.000 claims 1
- PCIFQGCUSPXADK-UHFFFAOYSA-N n-[1-cyclopentyl-4,6-dimethyl-5-(sulfamoylamino)-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound C12=C(NC(=O)C(C)(C)C)C(C)=C(NS(N)(=O)=O)C(C)=C2CCN1C1CCCC1 PCIFQGCUSPXADK-UHFFFAOYSA-N 0.000 claims 1
- GBAZFSZYDJBYPD-UHFFFAOYSA-N n-[1-cyclopentyl-5-(methanesulfonamido)-4,6-dimethyl-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound C12=C(NC(=O)C(C)(C)C)C(C)=C(NS(C)(=O)=O)C(C)=C2CCN1C1CCCC1 GBAZFSZYDJBYPD-UHFFFAOYSA-N 0.000 claims 1
- LRBAKVDDHNPCCC-UHFFFAOYSA-N n-[4,6-dimethyl-1-(2-methylpropyl)-5-(sulfamoylamino)-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(N)(=O)=O)=C(C)C2=C1N(CC(C)C)CC2 LRBAKVDDHNPCCC-UHFFFAOYSA-N 0.000 claims 1
- CQUOFRSQDGIQFR-UHFFFAOYSA-N n-[4,6-dimethyl-1-octyl-5-(sulfamoylamino)-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(N)(=O)=O)=C(C)C2=C1N(CCCCCCCC)CC2 CQUOFRSQDGIQFR-UHFFFAOYSA-N 0.000 claims 1
- GGXSHQIVFLJCKB-UHFFFAOYSA-N n-[4,6-dimethyl-7-(propan-2-ylsulfonylamino)-2,3-dihydro-1h-indol-5-yl]-2,2-dimethylundecanamide Chemical compound CC(C)S(=O)(=O)NC1=C(C)C(NC(=O)C(C)(C)CCCCCCCCC)=C(C)C2=C1NCC2 GGXSHQIVFLJCKB-UHFFFAOYSA-N 0.000 claims 1
- CSUFHLNECBNNEF-UHFFFAOYSA-N n-[5-(methanesulfonamido)-1,4,6-trimethyl-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(C)(=O)=O)=C(C)C2=C1N(C)CC2 CSUFHLNECBNNEF-UHFFFAOYSA-N 0.000 claims 1
- CMFVHXWONLKWQY-UHFFFAOYSA-N n-[5-(methanesulfonamido)-1-(2-methoxyethyl)-4,6-dimethyl-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(C)(=O)=O)=C(C)C2=C1N(CCOC)CC2 CMFVHXWONLKWQY-UHFFFAOYSA-N 0.000 claims 1
- BYQLAIWMFUGUJH-UHFFFAOYSA-N n-[5-(methanesulfonamido)-4,6-dimethyl-1-(2-methylpropyl)-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(C)(=O)=O)=C(C)C2=C1N(CC(C)C)CC2 BYQLAIWMFUGUJH-UHFFFAOYSA-N 0.000 claims 1
- IGDFPFBDPLCYJY-UHFFFAOYSA-N n-[5-(methanesulfonamido)-4,6-dimethyl-1-octyl-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(C)(=O)=O)=C(C)C2=C1N(CCCCCCCC)CC2 IGDFPFBDPLCYJY-UHFFFAOYSA-N 0.000 claims 1
- NELINRKCEJHCEZ-UHFFFAOYSA-N n-[5-(methanesulfonamido)-4,6-dimethyl-1-propan-2-yl-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(C)(=O)=O)=C(C)C2=C1N(C(C)C)CC2 NELINRKCEJHCEZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 abstract description 11
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol 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)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 30
- 235000012000 cholesterol Nutrition 0.000 description 12
- 206010003210 Arteriosclerosis Diseases 0.000 description 9
- 208000011775 arteriosclerosis disease Diseases 0.000 description 9
- 239000008280 blood Substances 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 150000001840 cholesterol esters Chemical class 0.000 description 7
- 238000009825 accumulation Methods 0.000 description 6
- 239000008177 pharmaceutical agent Substances 0.000 description 6
- 230000001629 suppression Effects 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 210000000813 small intestine Anatomy 0.000 description 4
- 230000007423 decrease Effects 0.000 description 3
- 108010007622 LDL Lipoproteins Proteins 0.000 description 2
- 102000007330 LDL Lipoproteins Human genes 0.000 description 2
- 108010062497 VLDL Lipoproteins Proteins 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 210000004400 mucous membrane Anatomy 0.000 description 2
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 description 1
- 229940123239 Cholesterol synthesis inhibitor Drugs 0.000 description 1
- 108010004103 Chylomicrons Proteins 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 102000001494 Sterol O-Acyltransferase Human genes 0.000 description 1
- 108010054082 Sterol O-acyltransferase Proteins 0.000 description 1
- 230000001919 adrenal effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 230000007012 clinical effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 201000005577 familial hyperlipidemia Diseases 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 208000023589 ischemic disease Diseases 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- CYFHBFULKLKGEA-UHFFFAOYSA-N n-[1-butyl-4,6-dimethyl-5-(sulfamoylamino)-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(N)(=O)=O)=C(C)C2=C1N(CCCC)CC2 CYFHBFULKLKGEA-UHFFFAOYSA-N 0.000 description 1
- FGJWURYDKWXTGD-UHFFFAOYSA-N n-[2-(ethylsulfanylmethyl)-4,6-dimethyl-1-propyl-5-(sulfamoylamino)-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(N)(=O)=O)=C(C)C2=C1N(CCC)C(CSCC)C2 FGJWURYDKWXTGD-UHFFFAOYSA-N 0.000 description 1
- PJJUSNJQEQRCGV-UHFFFAOYSA-N n-[2-(methoxymethyl)-4,6-dimethyl-1-propyl-5-(sulfamoylamino)-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(N)(=O)=O)=C(C)C2=C1N(CCC)C(COC)C2 PJJUSNJQEQRCGV-UHFFFAOYSA-N 0.000 description 1
- UUAFCVIQFWPWJR-UHFFFAOYSA-N n-[4,6-dimethyl-1-(3-methylbutyl)-5-(sulfamoylamino)-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(N)(=O)=O)=C(C)C2=C1N(CCC(C)C)CC2 UUAFCVIQFWPWJR-UHFFFAOYSA-N 0.000 description 1
- XUDTVJUTBDIXCG-UHFFFAOYSA-N n-[5-(acetylsulfamoylamino)-4,6-dimethyl-1-octyl-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NS(=O)(=O)NC(C)=O)=C(C)C2=C1N(CCCCCCCC)CC2 XUDTVJUTBDIXCG-UHFFFAOYSA-N 0.000 description 1
- NGUYGKGSPHDXAM-UHFFFAOYSA-N n-[5-(carbamoylamino)-4,6-dimethyl-1-octyl-2,3-dihydroindol-7-yl]-2,2-dimethylpropanamide Chemical compound CC(C)(C)C(=O)NC1=C(C)C(NC(N)=O)=C(C)C2=C1N(CCCCCCCC)CC2 NGUYGKGSPHDXAM-UHFFFAOYSA-N 0.000 description 1
- PLVDBOIGHDMEIZ-UHFFFAOYSA-N n-[7-(carbamoylamino)-4,6-dimethyl-2,3-dihydro-1h-indol-5-yl]-2,2-dimethylundecanamide Chemical compound NC(=O)NC1=C(C)C(NC(=O)C(C)(C)CCCCCCCCC)=C(C)C2=C1NCC2 PLVDBOIGHDMEIZ-UHFFFAOYSA-N 0.000 description 1
- PPNPLVCBSPHXQV-UHFFFAOYSA-N n-[7-(methanesulfonamido)-4,6-dimethyl-2,3-dihydro-1h-indol-5-yl]-2,2-dimethylundecanamide Chemical compound CS(=O)(=O)NC1=C(C)C(NC(=O)C(C)(C)CCCCCCCCC)=C(C)C2=C1NCC2 PPNPLVCBSPHXQV-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000000329 smooth muscle myocyte Anatomy 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—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
- 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
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002208878 | 2002-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200501297B true ZA200501297B (en) | 2006-10-25 |
Family
ID=30112861
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200501297A ZA200501297B (en) | 2002-07-17 | 2003-07-16 | Novel indoline compound and medicinal use thereof |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US7429612B2 (ja) |
| EP (1) | EP1541553B1 (ja) |
| JP (1) | JP4485357B2 (ja) |
| CN (1) | CN100349868C (ja) |
| AT (1) | ATE469884T1 (ja) |
| AU (1) | AU2003252638B8 (ja) |
| BR (1) | BR0312734A (ja) |
| CA (1) | CA2492669A1 (ja) |
| CO (1) | CO5690574A2 (ja) |
| DE (1) | DE60332851D1 (ja) |
| DK (1) | DK1541553T3 (ja) |
| HK (1) | HK1083839A1 (ja) |
| IL (1) | IL166313A0 (ja) |
| MX (1) | MXPA05000749A (ja) |
| NO (1) | NO20050834L (ja) |
| NZ (1) | NZ538226A (ja) |
| PL (1) | PL374919A1 (ja) |
| RS (1) | RS20050127A (ja) |
| RU (1) | RU2318808C2 (ja) |
| TW (1) | TWI285196B (ja) |
| WO (1) | WO2004007450A1 (ja) |
| ZA (1) | ZA200501297B (ja) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102011076931A1 (de) | 2011-06-03 | 2012-12-06 | Basf Se | Wässrige Lösung, enthaltend Acrylsäure und deren konjugierte Base |
| JP2018052818A (ja) * | 2015-01-28 | 2018-04-05 | 武田薬品工業株式会社 | スルホンアミド化合物 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4013404A (en) * | 1970-12-06 | 1977-03-22 | American Cyanamid Company | Method of dyeing hair with indolines, indoles and indazoles |
| CH644116A5 (de) * | 1980-08-21 | 1984-07-13 | Hoffmann La Roche | Imidazolderivate. |
| US4803218A (en) * | 1982-09-29 | 1989-02-07 | Mcneilab, Inc. | 3-aminoalkyl-1H-indole-5-urea and amide derivatives |
| US4956372A (en) * | 1987-10-02 | 1990-09-11 | Kyorin Pharmaceutical Co., Ltd. | Cyclic anthranilic acid derivatives and process for their preparation |
| US5166429A (en) * | 1988-01-20 | 1992-11-24 | Yamanouchi Pharmaceutical Co., Ltd. | Diurea derivatives useful as medicaments and processes for the preparation thereof |
| US5227492A (en) | 1988-01-20 | 1993-07-13 | Yamanouchi Pharmaceutical Co., Ltd. | Diurea derivatives useful as medicaments and processes for the preparation thereof |
| CN1021819C (zh) * | 1988-01-20 | 1993-08-18 | 山之内制药株式会社 | 作为药物有用的双脲衍生物的制备方法 |
| JPH02117651A (ja) | 1988-01-20 | 1990-05-02 | Yamanouchi Pharmaceut Co Ltd | ジウレア誘導体及びその製造法 |
| IE892088L (en) * | 1988-07-12 | 1990-01-12 | William Henry Deryk Morris | Quinoline derivatives, their production and use |
| JPH0753714B2 (ja) | 1988-07-12 | 1995-06-07 | 武田薬品工業株式会社 | Ａｃａｔ阻害剤、キノリン誘導体及びその製造法 |
| US5153226A (en) | 1989-08-31 | 1992-10-06 | Warner-Lambert Company | Acat inhibitors for treating hypocholesterolemia |
| ATE115558T1 (de) | 1990-03-12 | 1994-12-15 | Yamanouchi Pharma Co Ltd | Harnstoffderivate, deren herstellung sowie diese enthaltende pharmazeutische zusammensetzungen. |
| US5258405A (en) * | 1990-03-12 | 1993-11-02 | Yamanouchi Pharmaceutical Co., Ltd. | Urea derivatives and salts thereof in method for inhibiting the ACAT enzyme |
| JPH0466568A (ja) | 1990-06-29 | 1992-03-02 | Takeda Chem Ind Ltd | 中枢性抗酸化剤化合物 |
| JP3086295B2 (ja) | 1990-08-17 | 2000-09-11 | 武田薬品工業株式会社 | チエノピリジン誘導体、その製造法およびａｃａｔ阻害剤 |
| US5256782A (en) * | 1990-08-17 | 1993-10-26 | Takeda Chemical Industries, Ltd. | Thienopyridine derivatives which are intermediates |
| US5143919A (en) * | 1990-08-17 | 1992-09-01 | Takeda Chemical Industries, Ltd. | Thienopyridine derivatives and their pharmaceutical use |
| FR2673625B1 (fr) * | 1991-03-08 | 1993-05-07 | Adir | Nouveaux derives d'acylaminophenol, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2674522B1 (fr) * | 1991-03-26 | 1993-07-16 | Lipha | Nouveaux derives de l'indole, procedes de preparation et medicaments les contenant. |
| IL101785A0 (en) | 1991-05-10 | 1992-12-30 | Fujisawa Pharmaceutical Co | Urea derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same |
| CA2121391A1 (en) | 1993-04-28 | 1994-10-29 | Atsuyuki Kojima | Indoloylguanidine derivatives |
| US6169107B1 (en) * | 1993-04-28 | 2001-01-02 | Sumitomo Pharmaceutical Co., Ltd. | Indoloylguanidine derivatives |
| JP3720395B2 (ja) | 1994-09-20 | 2005-11-24 | 京都薬品工業株式会社 | 新規ヘテロ環誘導体、その製造方法およびその医薬用途 |
| CA2160600A1 (en) | 1994-10-18 | 1996-04-19 | Masahumi Kitano | Indoloylguanidine derivatives |
| JPH08208602A (ja) | 1994-10-18 | 1996-08-13 | Sumitomo Pharmaceut Co Ltd | インドロイルグアニジン誘導体 |
| US5767129A (en) * | 1995-08-24 | 1998-06-16 | Warner-Lambert Company | Substituted quinolines and isoquinolines as calcium channel blockers, their preparation and the use thereof |
| US6063806A (en) * | 1995-10-05 | 2000-05-16 | Kyoto Pharmaceutical Industries, Ltd. | Indolyl or indolinyl derivatives and medicinal use thereof as ACAT or lipid peroxidation inhibitors |
| EP0793140B1 (en) | 1996-03-04 | 2000-08-09 | Fuji Photo Film Co., Ltd. | Processing composition for silver halide photographic light-sensitive material, developer and processing method using the same |
| JP2002047269A (ja) | 2000-08-01 | 2002-02-12 | Kyoto Pharmaceutical Industries Ltd | ヘテロ環化合物の製造方法およびその中間体 |
| JP2002302481A (ja) | 2001-02-02 | 2002-10-18 | Sankyo Co Ltd | インドリン誘導体と製造法 |
| MXPA05010174A (es) * | 2003-04-25 | 2005-11-08 | Lundbeck & Co As H | Derivados de indol e indolina sustituidos. |
-
2003
- 2003-07-16 MX MXPA05000749A patent/MXPA05000749A/es active IP Right Grant
- 2003-07-16 DK DK03764206.3T patent/DK1541553T3/da active
- 2003-07-16 IL IL16631303A patent/IL166313A0/xx unknown
- 2003-07-16 EP EP03764206A patent/EP1541553B1/en not_active Expired - Lifetime
- 2003-07-16 ZA ZA200501297A patent/ZA200501297B/en unknown
- 2003-07-16 BR BR0312734-6A patent/BR0312734A/pt not_active IP Right Cessation
- 2003-07-16 NZ NZ538226A patent/NZ538226A/en unknown
- 2003-07-16 CN CNB038220881A patent/CN100349868C/zh not_active Expired - Fee Related
- 2003-07-16 RU RU2005104238/04A patent/RU2318808C2/ru not_active IP Right Cessation
- 2003-07-16 WO PCT/JP2003/009012 patent/WO2004007450A1/ja active Application Filing
- 2003-07-16 CA CA002492669A patent/CA2492669A1/en not_active Abandoned
- 2003-07-16 JP JP2004521216A patent/JP4485357B2/ja not_active Expired - Fee Related
- 2003-07-16 AT AT03764206T patent/ATE469884T1/de not_active IP Right Cessation
- 2003-07-16 DE DE60332851T patent/DE60332851D1/de not_active Expired - Fee Related
- 2003-07-16 RS YUP-2005/0127A patent/RS20050127A/sr unknown
- 2003-07-16 AU AU2003252638A patent/AU2003252638B8/en not_active Ceased
- 2003-07-16 PL PL03374919A patent/PL374919A1/xx not_active Application Discontinuation
- 2003-07-16 US US10/521,175 patent/US7429612B2/en not_active Expired - Fee Related
- 2003-07-17 TW TW092119477A patent/TWI285196B/zh not_active IP Right Cessation
-
2005
- 2005-02-16 NO NO20050834A patent/NO20050834L/no not_active Application Discontinuation
- 2005-02-16 CO CO05013959A patent/CO5690574A2/es not_active Application Discontinuation
-
2006
- 2006-03-30 HK HK06103972A patent/HK1083839A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| RS20050127A (en) | 2007-06-04 |
| AU2003252638B8 (en) | 2009-03-05 |
| AU2003252638A1 (en) | 2004-02-02 |
| BR0312734A (pt) | 2005-04-26 |
| CN1681781A (zh) | 2005-10-12 |
| TWI285196B (en) | 2007-08-11 |
| EP1541553B1 (en) | 2010-06-02 |
| HK1083839A1 (en) | 2006-07-14 |
| IL166313A0 (en) | 2006-01-15 |
| NZ538226A (en) | 2006-08-31 |
| RU2318808C2 (ru) | 2008-03-10 |
| WO2004007450A1 (ja) | 2004-01-22 |
| EP1541553A1 (en) | 2005-06-15 |
| CN100349868C (zh) | 2007-11-21 |
| US20060128787A1 (en) | 2006-06-15 |
| AU2003252638B2 (en) | 2009-02-05 |
| DE60332851D1 (de) | 2010-07-15 |
| TW200407304A (en) | 2004-05-16 |
| CA2492669A1 (en) | 2004-01-22 |
| JPWO2004007450A1 (ja) | 2005-11-10 |
| PL374919A1 (en) | 2005-11-14 |
| ATE469884T1 (de) | 2010-06-15 |
| JP4485357B2 (ja) | 2010-06-23 |
| NO20050834L (no) | 2005-04-15 |
| US7429612B2 (en) | 2008-09-30 |
| MXPA05000749A (es) | 2005-04-28 |
| EP1541553A4 (en) | 2007-04-11 |
| DK1541553T3 (da) | 2010-09-20 |
| RU2005104238A (ru) | 2005-08-27 |
| CO5690574A2 (es) | 2006-10-31 |
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