HRP20010785A2 - Substituted bicyclic heterocycles, process for their preparation and their use as antiobesity and hypocholesterolemic agents - Google Patents
Substituted bicyclic heterocycles, process for their preparation and their use as antiobesity and hypocholesterolemic agents Download PDFInfo
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- HRP20010785A2 HRP20010785A2 HR20010785A HRP20010785A HRP20010785A2 HR P20010785 A2 HRP20010785 A2 HR P20010785A2 HR 20010785 A HR20010785 A HR 20010785A HR P20010785 A HRP20010785 A HR P20010785A HR P20010785 A2 HRP20010785 A2 HR P20010785A2
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- phenyl
- dihydro
- ethoxy
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- 238000000034 method Methods 0.000 title claims 13
- 230000008569 process Effects 0.000 title claims 6
- 230000003579 anti-obesity Effects 0.000 title 1
- 239000000883 anti-obesity agent Substances 0.000 title 1
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- 125000002618 bicyclic heterocycle group Chemical group 0.000 title 1
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- FJDMCJKQTKAEJG-UHFFFAOYSA-N 3-[2-(2,3-dihydro-1,4-benzoxazin-4-ylmethyl)-1-benzofuran-5-yl]-2-ethoxypropanoic acid Chemical compound C1COC2=CC=CC=C2N1CC1=CC2=CC(CC(OCC)C(O)=O)=CC=C2O1 FJDMCJKQTKAEJG-UHFFFAOYSA-N 0.000 claims 6
- GKBWKSJWXJMEEQ-UHFFFAOYSA-N 3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C2=CC=CC=C2SCC1 GKBWKSJWXJMEEQ-UHFFFAOYSA-N 0.000 claims 6
- XSSLBZJZTWIQPZ-UHFFFAOYSA-N 3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-hydroxypropanoic acid Chemical compound C1=CC(CC(O)C(O)=O)=CC=C1OCCN1C2=CC=CC=C2SCC1 XSSLBZJZTWIQPZ-UHFFFAOYSA-N 0.000 claims 6
- YPCXMZHWVUITBA-UHFFFAOYSA-N 3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound C=1C=C(OCCN2C3=CC=CC=C3SCC2)C=CC=1CC(C(=O)O)OC1=CC=CC=C1 YPCXMZHWVUITBA-UHFFFAOYSA-N 0.000 claims 6
- NPIGSANZDQELNH-UHFFFAOYSA-N 3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-ethoxy-2-methylpropanoic acid Chemical compound C1=CC(CC(C)(OCC)C(O)=O)=CC=C1OCCN1C2=CC=CC=C2OCC1 NPIGSANZDQELNH-UHFFFAOYSA-N 0.000 claims 6
- BFLZHLOGOOYEAN-UHFFFAOYSA-N 3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-hexoxypropanoic acid Chemical compound C1=CC(CC(OCCCCCC)C(O)=O)=CC=C1OCCN1C2=CC=CC=C2OCC1 BFLZHLOGOOYEAN-UHFFFAOYSA-N 0.000 claims 6
- KRNNZPFAPLHPNP-UHFFFAOYSA-N 3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-phenoxypropanoic acid Chemical compound C=1C=C(OCCN2C3=CC=CC=C3OCC2)C=CC=1CC(C(=O)O)OC1=CC=CC=C1 KRNNZPFAPLHPNP-UHFFFAOYSA-N 0.000 claims 6
- LVGVAOOYUUFWNS-UHFFFAOYSA-N 3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-phenylmethoxypropanoic acid Chemical compound C=1C=C(OCCN2C3=CC=CC=C3OCC2)C=CC=1CC(C(=O)O)OCC1=CC=CC=C1 LVGVAOOYUUFWNS-UHFFFAOYSA-N 0.000 claims 6
- WQBNZXVSFXLTGV-UHFFFAOYSA-N 3-[6-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]naphthalen-1-yl]-2-ethoxypropanoic acid Chemical compound C1COC2=CC=CC=C2N1CCOC1=CC=C2C(CC(OCC)C(O)=O)=CC=CC2=C1 WQBNZXVSFXLTGV-UHFFFAOYSA-N 0.000 claims 6
- HBDHWQKZINLCPK-UHFFFAOYSA-N 2-ethoxy-3-[4-[2-(3-oxo-1,4-benzothiazin-4-yl)ethoxy]phenyl]propanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C2=CC=CC=C2SCC1=O HBDHWQKZINLCPK-UHFFFAOYSA-N 0.000 claims 5
- GGAOXTIHFIYDPC-UHFFFAOYSA-N 3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCCN1C2=CC=CC=C2OCC1 GGAOXTIHFIYDPC-UHFFFAOYSA-N 0.000 claims 5
- KCOTUBYAAREJGC-UHFFFAOYSA-N 3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-methyl-2-phenoxypropanoic acid Chemical compound C=1C=C(OCCN2C3=CC=CC=C3OCC2)C=CC=1CC(C)(C(O)=O)OC1=CC=CC=C1 KCOTUBYAAREJGC-UHFFFAOYSA-N 0.000 claims 5
- BAOZZIMJVLTJIQ-UHFFFAOYSA-N 3-[6-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]naphthalen-1-yl]-2-ethoxypropanoic acid Chemical compound C1CSC2=CC=CC=C2N1CCOC1=CC=C2C(CC(OCC)C(O)=O)=CC=CC2=C1 BAOZZIMJVLTJIQ-UHFFFAOYSA-N 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 5
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 5
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 5
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- MHMMGRGOOBJCSR-UHFFFAOYSA-N 2-[[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]methyl]-2-ethoxy-3-(2-fluorophenyl)propanoic acid Chemical compound C=1C=C(OCCN2C3=CC=CC=C3OCC2)C=CC=1CC(OCC)(C(O)=O)CC1=CC=CC=C1F MHMMGRGOOBJCSR-UHFFFAOYSA-N 0.000 claims 3
- ROHGIKOWUPXUPJ-UHFFFAOYSA-N 3-[4-[(4-benzyl-2,3-dihydro-1,4-benzoxazin-2-yl)methoxy]phenyl]-2-ethoxy-2-(4-nitrophenyl)propanoic acid Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C(OCC)(C(O)=O)CC(C=C1)=CC=C1OCC(OC1=CC=CC=C11)CN1CC1=CC=CC=C1 ROHGIKOWUPXUPJ-UHFFFAOYSA-N 0.000 claims 3
- XTADJISLWFZGIO-UHFFFAOYSA-N 3-[4-[(4-benzyl-2,3-dihydro-1,4-benzoxazin-2-yl)methoxy]phenyl]-2-ethoxypropanoic acid Chemical compound C1=CC(CC(OCC)C(O)=O)=CC=C1OCC1OC2=CC=CC=C2N(CC=2C=CC=CC=2)C1 XTADJISLWFZGIO-UHFFFAOYSA-N 0.000 claims 3
- BTNSRAJLQDPUHB-UHFFFAOYSA-N 3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-ethoxy-n-methylpropanamide Chemical compound C1=CC(CC(OCC)C(=O)NC)=CC=C1OCCN1C2=CC=CC=C2SCC1 BTNSRAJLQDPUHB-UHFFFAOYSA-N 0.000 claims 3
- DQDCKBWSBKGOQH-UHFFFAOYSA-N 3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-ethoxypropanamide Chemical compound C1=CC(CC(OCC)C(N)=O)=CC=C1OCCN1C2=CC=CC=C2SCC1 DQDCKBWSBKGOQH-UHFFFAOYSA-N 0.000 claims 3
- ODYZDBJNDOGJKT-UHFFFAOYSA-N 3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-methyl-2-phenoxypropanoic acid Chemical compound C=1C=C(OCCN2C3=CC=CC=C3SCC2)C=CC=1CC(C)(C(O)=O)OC1=CC=CC=C1 ODYZDBJNDOGJKT-UHFFFAOYSA-N 0.000 claims 3
- BSDNCIHDROVWCO-UHFFFAOYSA-N 3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-ethoxy-n-methylpropanamide Chemical compound C1=CC(CC(OCC)C(=O)NC)=CC=C1OCCN1C2=CC=CC=C2OCC1 BSDNCIHDROVWCO-UHFFFAOYSA-N 0.000 claims 3
- BDCDPHXWHMTYJB-UHFFFAOYSA-N 3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-ethoxypropanamide Chemical compound C1=CC(CC(OCC)C(N)=O)=CC=C1OCCN1C2=CC=CC=C2OCC1 BDCDPHXWHMTYJB-UHFFFAOYSA-N 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- CKYQFZCHIWADPF-UHFFFAOYSA-N ethyl 2-butoxy-3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCCCC)C(=O)OCC)=CC=C1OCCN1C2=CC=CC=C2OCC1 CKYQFZCHIWADPF-UHFFFAOYSA-N 0.000 claims 3
- FJVZJKKVARYFMD-UHFFFAOYSA-N ethyl 3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-phenylmethoxypropanoate Chemical compound C=1C=C(OCCN2C3=CC=CC=C3OCC2)C=CC=1CC(C(=O)OCC)OCC1=CC=CC=C1 FJVZJKKVARYFMD-UHFFFAOYSA-N 0.000 claims 3
- MNQXEPWTCARIMG-UHFFFAOYSA-N methyl 2-[[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]methyl]-2-ethoxy-3-(2-fluorophenyl)propanoate Chemical compound C=1C=C(OCCN2C3=CC=CC=C3OCC2)C=CC=1CC(OCC)(C(=O)OC)CC1=CC=CC=C1F MNQXEPWTCARIMG-UHFFFAOYSA-N 0.000 claims 3
- XKJXOGKPOAQHGP-UHFFFAOYSA-N methyl 3-[2-(2,3-dihydro-1,4-benzoxazin-4-ylmethyl)-1-benzofuran-5-yl]-2-ethoxypropanoate Chemical compound C1COC2=CC=CC=C2N1CC1=CC2=CC(CC(OCC)C(=O)OC)=CC=C2O1 XKJXOGKPOAQHGP-UHFFFAOYSA-N 0.000 claims 3
- XFECTTWJODDBNV-UHFFFAOYSA-N methyl 3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OC)=CC=C1OCCN1C2=CC=CC=C2OCC1 XFECTTWJODDBNV-UHFFFAOYSA-N 0.000 claims 3
- UNILYMLSNCMOMF-UHFFFAOYSA-N methyl 3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-phenoxypropanoate Chemical compound C=1C=C(OCCN2C3=CC=CC=C3OCC2)C=CC=1CC(C(=O)OC)OC1=CC=CC=C1 UNILYMLSNCMOMF-UHFFFAOYSA-N 0.000 claims 3
- PBZSAMQPGQTMLD-UHFFFAOYSA-N methyl 3-[6-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]naphthalen-1-yl]-2-ethoxypropanoate Chemical compound C1CSC2=CC=CC=C2N1CCOC1=CC=C2C(CC(OCC)C(=O)OC)=CC=CC2=C1 PBZSAMQPGQTMLD-UHFFFAOYSA-N 0.000 claims 3
- GGPUBHNWQRASQZ-UHFFFAOYSA-N n-benzyl-3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-ethoxypropanamide Chemical compound C=1C=C(OCCN2C3=CC=CC=C3SCC2)C=CC=1CC(OCC)C(=O)NCC1=CC=CC=C1 GGPUBHNWQRASQZ-UHFFFAOYSA-N 0.000 claims 3
- ITTKNPXOMGJVDP-UHFFFAOYSA-N n-benzyl-3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-ethoxypropanamide Chemical compound C=1C=C(OCCN2C3=CC=CC=C3OCC2)C=CC=1CC(OCC)C(=O)NCC1=CC=CC=C1 ITTKNPXOMGJVDP-UHFFFAOYSA-N 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 150000003458 sulfonic acid derivatives Chemical class 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- IKCYLYMMVOWCGZ-UHFFFAOYSA-N ethyl 3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-hydroxypropanoate Chemical compound C1=CC(CC(O)C(=O)OCC)=CC=C1OCCN1C2=CC=CC=C2SCC1 IKCYLYMMVOWCGZ-UHFFFAOYSA-N 0.000 claims 2
- PQXCSWWRPIMVIP-UHFFFAOYSA-N ethyl 3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-hexoxypropanoate Chemical compound C1=CC(CC(OCCCCCC)C(=O)OCC)=CC=C1OCCN1C2=CC=CC=C2OCC1 PQXCSWWRPIMVIP-UHFFFAOYSA-N 0.000 claims 2
- PEBWFGOQVARCHJ-UHFFFAOYSA-N ethyl 3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-hydroxypropanoate Chemical compound C1=CC(CC(O)C(=O)OCC)=CC=C1OCCN1C2=CC=CC=C2OCC1 PEBWFGOQVARCHJ-UHFFFAOYSA-N 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 239000013067 intermediate product Substances 0.000 claims 2
- ZOVHBEKKCBZCRQ-UHFFFAOYSA-N methyl 2-ethoxy-3-[4-[(4-methyl-2,3-dihydro-1,4-benzoxazin-2-yl)methoxy]phenyl]propanoate Chemical compound C1=CC(CC(OCC)C(=O)OC)=CC=C1OCC1OC2=CC=CC=C2N(C)C1 ZOVHBEKKCBZCRQ-UHFFFAOYSA-N 0.000 claims 2
- FHJUQGWOIOSEHW-UHFFFAOYSA-N methyl 3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-ethoxypropanoate Chemical compound C1=CC(CC(OCC)C(=O)OC)=CC=C1OCCN1C2=CC=CC=C2SCC1 FHJUQGWOIOSEHW-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 150000003460 sulfonic acids Chemical class 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 claims 1
- 235000011613 Pinus brutia Nutrition 0.000 claims 1
- 241000018646 Pinus brutia Species 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 150000008064 anhydrides Chemical group 0.000 claims 1
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 claims 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- FOGZPJPPKVOAEG-LKUDQCMESA-N c1cc(OCCN2CCSc3ccccc32)ccc1\C=C(C(=O)OCC)\Oc1ccccc1 Chemical compound c1cc(OCCN2CCSc3ccccc32)ccc1\C=C(C(=O)OCC)\Oc1ccccc1 FOGZPJPPKVOAEG-LKUDQCMESA-N 0.000 claims 1
- TUVOUXLADZJVBL-RCCKNPSSSA-N c1cc(\C=C(\OCC)C(=O)OCC)ccc1OCCN1C(=O)COc2ccccc12 Chemical compound c1cc(\C=C(\OCC)C(=O)OCC)ccc1OCCN1C(=O)COc2ccccc12 TUVOUXLADZJVBL-RCCKNPSSSA-N 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 125000004598 dihydrobenzofuryl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004586 dihydrobenzopyranyl group Chemical group O1C(CCC2=C1C=CC=C2)* 0.000 claims 1
- 238000005906 dihydroxylation reaction Methods 0.000 claims 1
- PONXTPCRRASWKW-KBPBESRZSA-N diphenylethylenediamine Chemical compound C1([C@H](N)[C@@H](N)C=2C=CC=CC=2)=CC=CC=C1 PONXTPCRRASWKW-KBPBESRZSA-N 0.000 claims 1
- CINHGPHCEQNNKA-HEHNFIMWSA-N ethyl (E)-3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-ethoxyprop-2-enoate Chemical compound C1=CC(\C=C(\OCC)C(=O)OCC)=CC=C1OCCN1C2=CC=CC=C2SCC1 CINHGPHCEQNNKA-HEHNFIMWSA-N 0.000 claims 1
- FDBUMAZMKYPOHP-LHLOQNFPSA-N ethyl (E)-3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-phenoxyprop-2-enoate Chemical compound C=1C=C(OCCN2C3=CC=CC=C3OCC2)C=CC=1\C=C(C(=O)OCC)\OC1=CC=CC=C1 FDBUMAZMKYPOHP-LHLOQNFPSA-N 0.000 claims 1
- ATTHDPUAOALIJO-PLRJNAJWSA-N ethyl (Z)-3-[6-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]naphthalen-1-yl]-2-ethoxyprop-2-enoate Chemical compound C1CSC2=CC=CC=C2N1CCOC1=CC=C2C(/C=C(\OCC)C(=O)OCC)=CC=CC2=C1 ATTHDPUAOALIJO-PLRJNAJWSA-N 0.000 claims 1
- CBJLDOAEMVGSDO-OEAKJJBVSA-N ethyl (e)-3-[2-(2,3-dihydro-1,4-benzoxazin-4-ylmethyl)-1-benzofuran-5-yl]-2-ethoxyprop-2-enoate Chemical compound C1COC2=CC=CC=C2N1CC1=CC2=CC(\C=C(\OCC)C(=O)OCC)=CC=C2O1 CBJLDOAEMVGSDO-OEAKJJBVSA-N 0.000 claims 1
- OPYWHBQNRJKQBY-OQKWZONESA-N ethyl (e)-3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-ethoxyprop-2-enoate Chemical compound C1=CC(\C=C(\OCC)C(=O)OCC)=CC=C1OCCN1C2=CC=CC=C2OCC1 OPYWHBQNRJKQBY-OQKWZONESA-N 0.000 claims 1
- TUVOUXLADZJVBL-QNGOZBTKSA-N ethyl (z)-2-ethoxy-3-[4-[2-(3-oxo-1,4-benzoxazin-4-yl)ethoxy]phenyl]prop-2-enoate Chemical compound C1=CC(/C=C(\OCC)C(=O)OCC)=CC=C1OCCN1C2=CC=CC=C2OCC1=O TUVOUXLADZJVBL-QNGOZBTKSA-N 0.000 claims 1
- CBJLDOAEMVGSDO-UCQKPKSFSA-N ethyl (z)-3-[2-(2,3-dihydro-1,4-benzoxazin-4-ylmethyl)-1-benzofuran-5-yl]-2-ethoxyprop-2-enoate Chemical compound C1COC2=CC=CC=C2N1CC1=CC2=CC(/C=C(\OCC)C(=O)OCC)=CC=C2O1 CBJLDOAEMVGSDO-UCQKPKSFSA-N 0.000 claims 1
- CINHGPHCEQNNKA-FXBPSFAMSA-N ethyl (z)-3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-ethoxyprop-2-enoate Chemical compound C1=CC(/C=C(\OCC)C(=O)OCC)=CC=C1OCCN1C2=CC=CC=C2SCC1 CINHGPHCEQNNKA-FXBPSFAMSA-N 0.000 claims 1
- FOGZPJPPKVOAEG-QQTULTPQSA-N ethyl (z)-3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-phenoxyprop-2-enoate Chemical compound C=1C=C(OCCN2C3=CC=CC=C3SCC2)C=CC=1/C=C(C(=O)OCC)\OC1=CC=CC=C1 FOGZPJPPKVOAEG-QQTULTPQSA-N 0.000 claims 1
- OPYWHBQNRJKQBY-XLNRJJMWSA-N ethyl (z)-3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-ethoxyprop-2-enoate Chemical compound C1=CC(/C=C(\OCC)C(=O)OCC)=CC=C1OCCN1C2=CC=CC=C2OCC1 OPYWHBQNRJKQBY-XLNRJJMWSA-N 0.000 claims 1
- FDBUMAZMKYPOHP-QOMWVZHYSA-N ethyl (z)-3-[4-[2-(2,3-dihydro-1,4-benzoxazin-4-yl)ethoxy]phenyl]-2-phenoxyprop-2-enoate Chemical compound C=1C=C(OCCN2C3=CC=CC=C3OCC2)C=CC=1/C=C(C(=O)OCC)\OC1=CC=CC=C1 FDBUMAZMKYPOHP-QOMWVZHYSA-N 0.000 claims 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 1
- 125000001041 indolyl group Chemical group 0.000 claims 1
- RQVFFEZMPZAZTE-UHFFFAOYSA-N methyl 3-[4-[2-(2,3-dihydro-1,4-benzothiazin-4-yl)ethoxy]phenyl]-2-phenoxypropanoate Chemical compound C=1C=C(OCCN2C3=CC=CC=C3SCC2)C=CC=1CC(C(=O)OC)OC1=CC=CC=C1 RQVFFEZMPZAZTE-UHFFFAOYSA-N 0.000 claims 1
- ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 claims 1
- HMSINBTULZNZRC-UHFFFAOYSA-N n-acetyl-n-(2-aminoethyl)acetamide Chemical compound CC(=O)N(C(C)=O)CCN HMSINBTULZNZRC-UHFFFAOYSA-N 0.000 claims 1
- 125000004957 naphthylene group Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 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
- 230000009467 reduction Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 125000004149 thio group Chemical group *S* 0.000 claims 1
- 125000004001 thioalkyl group Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
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- C07D279/16—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Physical Education & Sports Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Reproductive Health (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Vascular Medicine (AREA)
- Dermatology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Ophthalmology & Optometry (AREA)
- Emergency Medicine (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Child & Adolescent Psychology (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN484MA1999 | 1999-04-28 | ||
| PCT/IB2000/000501 WO2000066572A1 (en) | 1999-04-28 | 2000-04-25 | Substituted bicyclic heterocycles, process for their preparation and their use as antiobesity and hypocholesterolemic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20010785A2 true HRP20010785A2 (en) | 2003-02-28 |
Family
ID=11095336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20010785A HRP20010785A2 (en) | 1999-04-28 | 2001-10-24 | Substituted bicyclic heterocycles, process for their preparation and their use as antiobesity and hypocholesterolemic agents |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7348426B1 (no) |
| EP (1) | EP1175412A1 (no) |
| JP (1) | JP2002543194A (no) |
| KR (1) | KR100610578B1 (no) |
| CN (1) | CN1353699A (no) |
| AU (1) | AU781079B2 (no) |
| BG (1) | BG106146A (no) |
| BR (1) | BR0010139A (no) |
| CA (1) | CA2371757A1 (no) |
| CZ (1) | CZ20013832A3 (no) |
| EE (1) | EE200100540A (no) |
| HR (1) | HRP20010785A2 (no) |
| HU (1) | HUP0600105A3 (no) |
| IL (1) | IL146104A0 (no) |
| MX (1) | MXPA01010916A (no) |
| NO (1) | NO320805B1 (no) |
| NZ (1) | NZ515284A (no) |
| PL (1) | PL351987A1 (no) |
| RU (1) | RU2278114C2 (no) |
| SK (1) | SK15092001A3 (no) |
| TR (1) | TR200103848T2 (no) |
| UA (1) | UA73501C2 (no) |
| WO (1) | WO2000066572A1 (no) |
| YU (1) | YU75101A (no) |
| ZA (1) | ZA200108733B (no) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2002212672A1 (en) * | 2000-10-12 | 2002-04-22 | Dr. Reddy's Research Foundation | Salts of benzothiazine and benzoxazine derivatives and pharmaceutical compositions containing them |
| DE60210784T2 (de) * | 2001-08-29 | 2006-11-02 | Warner-Lambert Co. Llc | Orale antidiabetische wirkstoffe |
| WO2003024944A1 (en) * | 2001-09-20 | 2003-03-27 | Dr. Reddy's Laboratories Ltd. | An improved process for the preparation of bicyclic antidiabetic compounds |
| WO2003027084A1 (en) * | 2001-09-25 | 2003-04-03 | Dr. Reddy's Laboratories Ltd. | Improved process for the preparation of optically active phenoxazine derivatives as antidiabetic agents |
| WO2003033456A1 (en) | 2001-10-16 | 2003-04-24 | Dr. Reddy's Laboratories Ltd. | NOVEL β-PHENYL-α-OXYSUBSTITUTED PROPIONIC DERIVATIVES: PROCESS FOR ITS PREPARATION AND THEIR USE IN THE PREPARATION OF PHARMACEUTICALLY IMPORTANT COMPOUNDS |
| AU2003244514A1 (en) * | 2002-02-07 | 2003-09-02 | Dr. Reddy's Laboratories Limited | Novel polymorphic forms of bicyclic antidiabetic agents: process for their preparation and pharmaceutical compositions containing them |
| US6716842B2 (en) | 2002-04-05 | 2004-04-06 | Warner-Lambert Company, Llc | Antidiabetic agents |
| ATE384699T1 (de) * | 2002-04-30 | 2008-02-15 | Ucb Pharma Sa | 2,6-chinolinyl- und 2,6-naphthylderivate und deren verwendungen zur behandlung von vla-4 bezogenen krankheiten |
| WO2003099800A1 (en) * | 2002-05-23 | 2003-12-04 | Dr. Reddy's Laboratories Limited | An improved process for the preparation of bicyclic antidiabetic agents |
| MXPA05004743A (es) | 2002-11-08 | 2005-08-03 | Hoffmann La Roche | Derivados 4-alcoxioxazol sustituidos como agonistas ppar. |
| US7262303B2 (en) | 2003-09-29 | 2007-08-28 | Hoffman-La Roche Inc. | Process for the production of chiral propionic acid derivatives |
| DE202004002953U1 (de) * | 2004-02-26 | 2004-04-29 | Winkler, Wilhelm | Verbindungseinheit |
| US7572807B2 (en) | 2005-06-09 | 2009-08-11 | Bristol-Myers Squibb Company | Heteroaryl 11-beta-hydroxysteroid dehydrogenase type I inhibitors |
| US7579360B2 (en) | 2005-06-09 | 2009-08-25 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| KR20080021085A (ko) | 2005-06-09 | 2008-03-06 | 유씨비 파마, 에스.에이. | 2，6 퀴놀리닐 유도체, 이들을 제조하는 방법 및 이들의약제로서의 용도 |
| US8119658B2 (en) | 2007-10-01 | 2012-02-21 | Bristol-Myers Squibb Company | Triazolopyridine 11-beta hydroxysteroid dehydrogenase type I inhibitors |
| RU2684779C2 (ru) * | 2016-02-05 | 2019-04-15 | АО "Институт химических наук им. А.Б. Бектурова" | Применение производного бета-морфолинопропиоамидоксима в качестве противодиабетического средства |
| CN110092774B (zh) * | 2018-01-29 | 2022-04-08 | 中国科学院上海药物研究所 | 芳香丙酸类衍生物、及其制备方法和用途 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DK173350B1 (da) | 1985-02-26 | 2000-08-07 | Sankyo Co | Thiazolidinderivater, deres fremstilling og farmaceutisk paæparat indeholdende dem |
| GB9027023D0 (en) | 1990-12-12 | 1991-01-30 | Wellcome Found | Anti-atherosclerotic aryl compounds |
| GB9225386D0 (en) | 1992-12-04 | 1993-01-27 | Smithkline Beecham Plc | Novel compounds |
| BR9508468A (pt) * | 1994-07-29 | 1997-11-25 | Smithkline Beecham Plc | Composto processo para a preparação do mesmo composição farmacéutica processos para o tratamento e/ou profilaxia de hiperglicemia em um mamifero humano ou não humano e para o tratamento de hiperlípidemia hipertensão doença cardiovascular alguns distúrbios de alimentação o tratamento e/ou profilaxia de doença renal a prevenção revers o estabilização ou retardo da progressão de microalbuminuria em um mamifero humano ou não humano uso do composto e composto intermediário |
| JPH0912575A (ja) * | 1995-06-28 | 1997-01-14 | Sankyo Co Ltd | ベンゾオキサジンおよびベンゾチアジン誘導体 |
| GB9600464D0 (en) * | 1996-01-09 | 1996-03-13 | Smithkline Beecham Plc | Novel method |
| AU1856997A (en) | 1996-02-02 | 1997-08-22 | Merck & Co., Inc. | Method for raising hdl cholesterol levels |
| GB9604242D0 (en) | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
| GB9606805D0 (en) * | 1996-03-30 | 1996-06-05 | Glaxo Wellcome Inc | Medicaments |
| WO1998002159A1 (en) | 1996-07-12 | 1998-01-22 | Smithkline Beecham Plc | Novel treatment of leptine resistance |
| WO1999020614A1 (en) | 1998-05-27 | 1999-04-29 | Dr. Reddy's Research Foundation | Bicyclic compounds, process for their preparation and pharmaceutical compositions containing them |
| RU2247722C2 (ru) * | 1997-10-27 | 2005-03-10 | Др. Редди`З Лабораториз Лимитед | Производные арилкарбоновых кислот, способы их получения, фармацевтическая композиция на их основе, способы лечения и предупреждения различных заболеваний, промежуточные соединения и способы их получения |
| 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 |
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2000
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- 2000-04-25 EP EP00919081A patent/EP1175412A1/en not_active Withdrawn
- 2000-04-25 NZ NZ515284A patent/NZ515284A/xx unknown
- 2000-04-25 YU YU75101A patent/YU75101A/sh unknown
- 2000-04-25 TR TR2001/03848T patent/TR200103848T2/xx unknown
- 2000-04-25 KR KR1020017013604A patent/KR100610578B1/ko not_active IP Right Cessation
- 2000-04-25 WO PCT/IB2000/000501 patent/WO2000066572A1/en not_active Application Discontinuation
- 2000-04-25 AU AU39831/00A patent/AU781079B2/en not_active Ceased
- 2000-04-25 HU HU0600105A patent/HUP0600105A3/hu unknown
- 2000-04-25 CZ CZ20013832A patent/CZ20013832A3/cs unknown
- 2000-04-25 RU RU2001132085/04A patent/RU2278114C2/ru not_active IP Right Cessation
- 2000-04-25 SK SK1509-2001A patent/SK15092001A3/sk unknown
- 2000-04-25 IL IL14610400A patent/IL146104A0/xx unknown
- 2000-04-25 PL PL00351987A patent/PL351987A1/xx not_active Application Discontinuation
- 2000-04-25 MX MXPA01010916A patent/MXPA01010916A/es active IP Right Grant
- 2000-04-25 CA CA002371757A patent/CA2371757A1/en not_active Abandoned
- 2000-04-25 US US09/959,093 patent/US7348426B1/en not_active Expired - Fee Related
- 2000-04-25 EE EEP200100540A patent/EE200100540A/xx unknown
- 2000-04-25 CN CN00808424A patent/CN1353699A/zh active Pending
- 2000-04-25 UA UA2001118039A patent/UA73501C2/uk unknown
- 2000-04-25 BR BR0010139-7A patent/BR0010139A/pt not_active IP Right Cessation
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2001
- 2001-10-23 ZA ZA200108733A patent/ZA200108733B/en unknown
- 2001-10-24 HR HR20010785A patent/HRP20010785A2/hr not_active Application Discontinuation
- 2001-10-26 NO NO20015259A patent/NO320805B1/no unknown
- 2001-11-26 BG BG106146A patent/BG106146A/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1175412A1 (en) | 2002-01-30 |
| KR100610578B1 (ko) | 2006-08-09 |
| NO20015259L (no) | 2001-11-15 |
| TR200103848T2 (tr) | 2002-04-22 |
| ZA200108733B (en) | 2003-01-23 |
| CZ20013832A3 (cs) | 2002-04-17 |
| NO20015259D0 (no) | 2001-10-26 |
| AU3983100A (en) | 2000-11-17 |
| CA2371757A1 (en) | 2000-11-09 |
| BG106146A (bg) | 2002-05-31 |
| RU2278114C2 (ru) | 2006-06-20 |
| HUP0600105A3 (en) | 2006-11-28 |
| JP2002543194A (ja) | 2002-12-17 |
| HUP0600105A2 (en) | 2006-05-29 |
| IL146104A0 (en) | 2002-07-25 |
| KR20010113891A (ko) | 2001-12-28 |
| US7348426B1 (en) | 2008-03-25 |
| MXPA01010916A (es) | 2002-06-21 |
| AU781079B2 (en) | 2005-05-05 |
| UA73501C2 (en) | 2005-08-15 |
| EE200100540A (et) | 2002-12-16 |
| NZ515284A (en) | 2004-12-24 |
| PL351987A1 (en) | 2003-07-14 |
| YU75101A (sh) | 2005-07-19 |
| SK15092001A3 (sk) | 2002-05-09 |
| NO320805B1 (no) | 2006-01-30 |
| CN1353699A (zh) | 2002-06-12 |
| BR0010139A (pt) | 2004-03-02 |
| WO2000066572A1 (en) | 2000-11-09 |
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