JP4974463B2 - インダン酢酸誘導体ならびに製薬学的薬剤としてのそれらの使用、中間体及び製造方法 - Google Patents
インダン酢酸誘導体ならびに製薬学的薬剤としてのそれらの使用、中間体及び製造方法 Download PDFInfo
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- JP4974463B2 JP4974463B2 JP2004563903A JP2004563903A JP4974463B2 JP 4974463 B2 JP4974463 B2 JP 4974463B2 JP 2004563903 A JP2004563903 A JP 2004563903A JP 2004563903 A JP2004563903 A JP 2004563903A JP 4974463 B2 JP4974463 B2 JP 4974463B2
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- Prior art keywords
- propoxy
- acetic acid
- indanyl
- alkyl
- mmol
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- 238000002360 preparation method Methods 0.000 title description 146
- 238000000034 method Methods 0.000 title description 93
- RJVZEPWRJJBXLH-UHFFFAOYSA-N 2-(2,3-dihydro-1h-inden-1-yl)acetic acid Chemical class C1=CC=C2C(CC(=O)O)CCC2=C1 RJVZEPWRJJBXLH-UHFFFAOYSA-N 0.000 title description 3
- 239000008177 pharmaceutical agent Substances 0.000 title 1
- 239000012450 pharmaceutical intermediate Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 269
- -1 C 1 -C 6 alkoxy Chemical group 0.000 claims description 157
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 113
- 150000003839 salts Chemical class 0.000 claims description 47
- 229920006395 saturated elastomer Polymers 0.000 claims description 39
- 125000005843 halogen group Chemical group 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 229910052760 oxygen Inorganic materials 0.000 claims description 36
- 229910052717 sulfur Inorganic materials 0.000 claims description 33
- 150000002148 esters Chemical class 0.000 claims description 29
- 125000005842 heteroatom Chemical group 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000002837 carbocyclic group Chemical group 0.000 claims description 20
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 19
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 18
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 15
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 125000002619 bicyclic group Chemical group 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000002950 monocyclic group Chemical group 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- INSJDULTKROYCO-SFHVURJKSA-N 2-[(1s)-5-[3-[5-(4,5-dimethyl-1,3-thiazol-2-yl)pyridin-2-yl]oxypropoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound S1C(C)=C(C)N=C1C(C=N1)=CC=C1OCCCOC1=CC=C([C@H](CC(O)=O)CC2)C2=C1 INSJDULTKROYCO-SFHVURJKSA-N 0.000 claims description 2
- 238000010276 construction Methods 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims 6
- 125000004001 thioalkyl group Chemical group 0.000 claims 6
- NRMLKMKBUYOILR-QFIPXVFZSA-N 2-[(1s)-5-[3-[[2-(4-ethoxyphenyl)-5-methylpyrimidin-4-yl]methylamino]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=CC(OCC)=CC=C1C1=NC=C(C)C(CNCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)=N1 NRMLKMKBUYOILR-QFIPXVFZSA-N 0.000 claims 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
- JIBRBEPRUAKTNJ-AHWVRZQESA-N (2s)-2-[(1s)-5-[2-[6-(4-ethylphenyl)pyridin-2-yl]ethoxy]-2,3-dihydro-1h-inden-1-yl]butanoic acid Chemical compound C([C@H](C1=CC=2)[C@H](CC)C(O)=O)CC1=CC=2OCCC(N=1)=CC=CC=1C1=CC=C(CC)C=C1 JIBRBEPRUAKTNJ-AHWVRZQESA-N 0.000 claims 1
- TTXZAMXYYZRBGI-CUXXENAFSA-N 2-[(1r)-5-[3-[2-propyl-4-(3,5,6,7-tetrahydro-2h-pyrano[2,3-d][1,3]thiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C(S1)NC2=C1CCCO2 TTXZAMXYYZRBGI-CUXXENAFSA-N 0.000 claims 1
- WYZVWTYQKOZQQS-NRFANRHFSA-N 2-[(1s)-5-[2-[6-(4-acetylphenyl)pyridin-2-yl]ethoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=CC(C(=O)C)=CC=C1C1=CC=CC(CCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)=N1 WYZVWTYQKOZQQS-NRFANRHFSA-N 0.000 claims 1
- IAOGDTFZZMHYHP-QFIPXVFZSA-N 2-[(1s)-5-[3-(4-phenoxy-2-propylphenoxy)propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1OC1=CC=CC=C1 IAOGDTFZZMHYHP-QFIPXVFZSA-N 0.000 claims 1
- GYLMBHYEEPSETC-KRWDZBQOSA-N 2-[(1s)-5-[3-[(3,7-dimethyl-1,2-benzoxazol-6-yl)oxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=C2[C@H](CC(O)=O)CCC2=CC(OCCCOC=2C(C)=C3ON=C(C3=CC=2)C)=C1 GYLMBHYEEPSETC-KRWDZBQOSA-N 0.000 claims 1
- NUTUSSDZMGFKKF-SFHVURJKSA-N 2-[(1s)-5-[3-[(3-methyl-7-propyl-1,2-benzoxazol-6-yl)oxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=C2[C@H](CC(O)=O)CCC2=CC(OCCCOC2=C(C=3ON=C(C)C=3C=C2)CCC)=C1 NUTUSSDZMGFKKF-SFHVURJKSA-N 0.000 claims 1
- KHWSFWPKNKLKPX-FQEVSTJZSA-N 2-[(1s)-5-[3-[2-ethoxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1CCCC(S2)=C1N=C2C1=CC=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(OCC)=C1 KHWSFWPKNKLKPX-FQEVSTJZSA-N 0.000 claims 1
- HGRRXAJCQVQKSP-HSYKDVHTSA-N 2-[(1s)-5-[3-[2-methoxy-4-(3,5,6,7-tetrahydro-2h-pyrano[2,3-d][1,3]thiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(OC)=CC=1C(S1)NC2=C1CCCO2 HGRRXAJCQVQKSP-HSYKDVHTSA-N 0.000 claims 1
- NPZMDWHUIIGJNS-IBGZPJMESA-N 2-[(1s)-5-[3-[2-methoxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1CCCC(S2)=C1N=C2C1=CC=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(OC)=C1 NPZMDWHUIIGJNS-IBGZPJMESA-N 0.000 claims 1
- BLJVVKCIOACNOQ-IBGZPJMESA-N 2-[(1s)-5-[3-[2-methoxy-4-(4,5,6,7-tetrahydro-1,3-benzoxazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1CCCC(O2)=C1N=C2C1=CC=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(OC)=C1 BLJVVKCIOACNOQ-IBGZPJMESA-N 0.000 claims 1
- YUWKOSPDHRFEEF-KRWDZBQOSA-N 2-[(1s)-5-[3-[2-methoxy-4-(4-methoxy-1,3-thiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound COC1=CSC(C=2C=C(OC)C(OCCCOC=3C=C4CC[C@@H](CC(O)=O)C4=CC=3)=CC=2)=N1 YUWKOSPDHRFEEF-KRWDZBQOSA-N 0.000 claims 1
- BRUFULPAONKCPM-INIZCTEOSA-N 2-[(1s)-5-[3-[2-methyl-4-[3-(trifluoromethyl)-1,2,4-thiadiazol-5-yl]phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(C)=CC=1C1=NC(C(F)(F)F)=NS1 BRUFULPAONKCPM-INIZCTEOSA-N 0.000 claims 1
- SLUNRBMNJCMKOE-NRFANRHFSA-N 2-[(1s)-5-[3-[2-propoxy-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1CCCC(S2)=C1N=C2C1=CC=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(OCCC)=C1 SLUNRBMNJCMKOE-NRFANRHFSA-N 0.000 claims 1
- VCBBROSSYZDABH-IBGZPJMESA-N 2-[(1s)-5-[3-[2-propyl-4-(1,3-thiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC=CS1 VCBBROSSYZDABH-IBGZPJMESA-N 0.000 claims 1
- TTXZAMXYYZRBGI-OORIHMLWSA-N 2-[(1s)-5-[3-[2-propyl-4-(3,5,6,7-tetrahydro-2h-pyrano[2,3-d][1,3]thiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C(S1)NC2=C1CCCO2 TTXZAMXYYZRBGI-OORIHMLWSA-N 0.000 claims 1
- IAFVOFFJCUHEHP-NRFANRHFSA-N 2-[(1s)-5-[3-[2-propyl-4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1CCCC(S2)=C1N=C2C1=CC=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=C1 IAFVOFFJCUHEHP-NRFANRHFSA-N 0.000 claims 1
- DPXRRYRDBWDWRM-NRFANRHFSA-N 2-[(1s)-5-[3-[2-propyl-4-(4,5,6,7-tetrahydro-1,3-benzoxazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1CCCC(O2)=C1N=C2C1=CC=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=C1 DPXRRYRDBWDWRM-NRFANRHFSA-N 0.000 claims 1
- UJRNVHVWFAPHHZ-KRWDZBQOSA-N 2-[(1s)-5-[3-[2-propyl-4-(trifluoromethyl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound CCCC1=CC(C(F)(F)F)=CC=C1OCCCOC1=CC=C([C@H](CC(O)=O)CC2)C2=C1 UJRNVHVWFAPHHZ-KRWDZBQOSA-N 0.000 claims 1
- HEGJINSQHTYDEX-SFHVURJKSA-N 2-[(1s)-5-[3-[2-propyl-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(C(F)(F)F)=CS1 HEGJINSQHTYDEX-SFHVURJKSA-N 0.000 claims 1
- UBZORZBZKNRJFC-IBGZPJMESA-N 2-[(1s)-5-[3-[4-(1,3-benzothiazol-2-yl)-2-methoxyphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=CC=C2SC(C=3C=C(C(=CC=3)OCCCOC=3C=C4CC[C@@H](CC(O)=O)C4=CC=3)OC)=NC2=C1 UBZORZBZKNRJFC-IBGZPJMESA-N 0.000 claims 1
- NTVBAWSNQRKVKF-FQEVSTJZSA-N 2-[(1s)-5-[3-[4-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1CCCC(S2)=C1N=C2C(C=C1)=CC=C1OCCCOC1=CC=C2[C@H](CC(=O)O)CCC2=C1 NTVBAWSNQRKVKF-FQEVSTJZSA-N 0.000 claims 1
- ZZKJSMBFWZMRRS-FQEVSTJZSA-N 2-[(1s)-5-[3-[4-(4,5,6,7-tetrahydro-1,3-benzoxazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1CCCC(O2)=C1N=C2C(C=C1)=CC=C1OCCCOC1=CC=C2[C@H](CC(=O)O)CCC2=C1 ZZKJSMBFWZMRRS-FQEVSTJZSA-N 0.000 claims 1
- ZBFIQWUEGZKBFS-IBGZPJMESA-N 2-[(1s)-5-[3-[4-(4,5-dimethyl-1,3-thiazol-2-yl)-2-methoxyphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(OC)=CC=1C1=NC(C)=C(C)S1 ZBFIQWUEGZKBFS-IBGZPJMESA-N 0.000 claims 1
- KZAIHPRSXFXXNU-FQEVSTJZSA-N 2-[(1s)-5-[3-[4-(4,5-dimethyl-1,3-thiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound S1C(C)=C(C)N=C1C(C=C1)=CC=C1OCCCOC1=CC=C([C@H](CC(O)=O)CC2)C2=C1 KZAIHPRSXFXXNU-FQEVSTJZSA-N 0.000 claims 1
- WMOAALINFRTEGC-SFHVURJKSA-N 2-[(1s)-5-[3-[4-(4-ethoxy-1,3-thiazol-2-yl)-2-methoxyphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound CCOC1=CSC(C=2C=C(OC)C(OCCCOC=3C=C4CC[C@@H](CC(O)=O)C4=CC=3)=CC=2)=N1 WMOAALINFRTEGC-SFHVURJKSA-N 0.000 claims 1
- DTSZUNRPQWYGHX-FQEVSTJZSA-N 2-[(1s)-5-[3-[4-(4-ethoxy-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(OCC)=CS1 DTSZUNRPQWYGHX-FQEVSTJZSA-N 0.000 claims 1
- UQFZTBWTJZBMDL-IBGZPJMESA-N 2-[(1s)-5-[3-[4-(4-ethoxy-5-methyl-1,3-thiazol-2-yl)-2-methoxyphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound S1C(C)=C(OCC)N=C1C(C=C1OC)=CC=C1OCCCOC1=CC=C([C@H](CC(O)=O)CC2)C2=C1 UQFZTBWTJZBMDL-IBGZPJMESA-N 0.000 claims 1
- XFEBTJLTAZGGPY-NRFANRHFSA-N 2-[(1s)-5-[3-[4-(4-ethoxy-5-methyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(OCC)=C(C)S1 XFEBTJLTAZGGPY-NRFANRHFSA-N 0.000 claims 1
- WLFRWUYWTYPAOJ-SFHVURJKSA-N 2-[(1s)-5-[3-[4-(4-ethyl-1,3-oxazol-2-yl)-2-methoxyphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound CCC1=COC(C=2C=C(OC)C(OCCCOC=3C=C4CC[C@@H](CC(O)=O)C4=CC=3)=CC=2)=N1 WLFRWUYWTYPAOJ-SFHVURJKSA-N 0.000 claims 1
- KKELJTWGLRARIG-FQEVSTJZSA-N 2-[(1s)-5-[3-[4-(4-ethyl-1,3-oxazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(CC)=CO1 KKELJTWGLRARIG-FQEVSTJZSA-N 0.000 claims 1
- YVTAAESLMBHKDQ-SFHVURJKSA-N 2-[(1s)-5-[3-[4-(4-ethyl-1,3-thiazol-2-yl)-2-methoxyphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound CCC1=CSC(C=2C=C(OC)C(OCCCOC=3C=C4CC[C@@H](CC(O)=O)C4=CC=3)=CC=2)=N1 YVTAAESLMBHKDQ-SFHVURJKSA-N 0.000 claims 1
- WCDXSIMIKBDXKI-FQEVSTJZSA-N 2-[(1s)-5-[3-[4-(4-ethyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(CC)=CS1 WCDXSIMIKBDXKI-FQEVSTJZSA-N 0.000 claims 1
- HBKNDUAKMHVGNM-SFHVURJKSA-N 2-[(1s)-5-[3-[4-(4-methoxy-1,3-thiazol-2-yl)phenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound COC1=CSC(C=2C=CC(OCCCOC=3C=C4CC[C@@H](CC(O)=O)C4=CC=3)=CC=2)=N1 HBKNDUAKMHVGNM-SFHVURJKSA-N 0.000 claims 1
- DABDLIFECGXQNC-NRFANRHFSA-N 2-[(1s)-5-[3-[4-(4-propan-2-yloxy-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(OC(C)C)=CS1 DABDLIFECGXQNC-NRFANRHFSA-N 0.000 claims 1
- ZTQUDSFSSMPWPD-NRFANRHFSA-N 2-[(1s)-5-[3-[4-(4-tert-butyl-1,3-thiazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C=1C=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=CC=1C1=NC(C(C)(C)C)=CS1 ZTQUDSFSSMPWPD-NRFANRHFSA-N 0.000 claims 1
- QJKOTSRVMJGHRK-NRFANRHFSA-N 2-[(1s)-5-[3-[4-(5,5-dimethyl-7-oxo-4,6-dihydro-1,3-benzothiazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1C(C)(C)CC(=O)C(S2)=C1N=C2C1=CC=C(OCCCOC=2C=C3CC[C@@H](CC(O)=O)C3=CC=2)C(CCC)=C1 QJKOTSRVMJGHRK-NRFANRHFSA-N 0.000 claims 1
- IELCDGLGXNKKIF-SFHVURJKSA-N 2-[(1s)-5-[3-[4-(5,6-dihydro-4h-cyclopenta[d][1,3]thiazol-2-yl)-2-methoxyphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=C2[C@H](CC(O)=O)CCC2=CC(OCCCOC2=CC=C(C=C2OC)C=2SC=3CCCC=3N=2)=C1 IELCDGLGXNKKIF-SFHVURJKSA-N 0.000 claims 1
- FQTHEIJACHCXRP-FQEVSTJZSA-N 2-[(1s)-5-[3-[4-(5,6-dihydro-4h-cyclopenta[d][1,3]thiazol-2-yl)-2-propylphenoxy]propoxy]-2,3-dihydro-1h-inden-1-yl]acetic acid Chemical compound C1=C2[C@H](CC(O)=O)CCC2=CC(OCCCOC2=CC=C(C=C2CCC)C=2SC=3CCCC=3N=2)=C1 FQTHEIJACHCXRP-FQEVSTJZSA-N 0.000 claims 1
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- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
- 229960004425 sibutramine Drugs 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 229940083542 sodium Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 229960003885 sodium benzoate Drugs 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 239000007886 soft shell capsule Substances 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000010009 steroidogenesis Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- JQZFTTNXRQSVDT-UHFFFAOYSA-N tert-butyl 2-amino-4-bromobutanoate Chemical compound CC(C)(C)OC(=O)C(N)CCBr JQZFTTNXRQSVDT-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UTYRQCFTOYUATF-UHFFFAOYSA-N tert-butyl(chloro)silane Chemical compound CC(C)(C)[SiH2]Cl UTYRQCFTOYUATF-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000035922 thirst Effects 0.000 description 1
- 239000005495 thyroid hormone Substances 0.000 description 1
- 229940036555 thyroid hormone Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
- 230000003966 vascular damage Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229960001729 voglibose Drugs 0.000 description 1
- 229940002552 xenical Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- 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
- A61P3/04—Anorexiants; Antiobesity agents
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/45—Monoamines
- C07C211/48—N-alkylated amines
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
- C07C217/14—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring
- C07C217/24—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system containing rings other than six-membered aromatic rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/48—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to carbon atoms of six-membered aromatic rings
-
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
- C07C333/04—Monothiocarbamic acids; Derivatives thereof having nitrogen atoms of thiocarbamic groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/734—Ethers
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- 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
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/83—Thioacids; Thioesters; Thioamides; Thioimides
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
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- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
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- C07D513/04—Ortho-condensed systems
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- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
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- Organic Chemistry (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Quinoline Compounds (AREA)
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- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| PT1599468E (pt) | 2003-01-14 | 2008-01-14 | Arena Pharm Inc | Derivados de arilo e heteroarilo 1,2,3.-trissubstituídos comomoduladores do metabolismo, e profilaxia e tratamento dedesordens relacionadas tais como diabetes e hiperglicemia |
| JP2006523698A (ja) * | 2003-04-17 | 2006-10-19 | カリプシス・インコーポレーテッド | Ppar変調薬としての(3−{3−(2,4−ビス−トリフルオロメチル−ベンジル)−(5−エチル−ピリミジン−2−イル)−アミノ−プロポキシ}−フェニル)−酢酸および関連化合物、ならびに代謝性障害の処置方法 |
| WO2004106276A1 (ja) * | 2003-05-30 | 2004-12-09 | Takeda Pharmaceutical Company Limited | 縮合環化合物 |
| JP4805552B2 (ja) * | 2003-05-30 | 2011-11-02 | 武田薬品工業株式会社 | 縮合環化合物 |
| EP2287165A3 (en) | 2003-07-14 | 2011-06-22 | Arena Pharmaceuticals, Inc. | Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto |
| AU2004285530A1 (en) * | 2003-10-31 | 2005-05-12 | Janssen Pharmaceutica N.V. | Phenoxyacetic acids derivatives useful as peroxisome proliferator-activated receptor (PPAR) dual agonists |
| EP1687274A1 (en) * | 2003-11-20 | 2006-08-09 | Warner-Lambert Company LLC | Androgen receptor modulators |
| US7622491B2 (en) * | 2004-08-13 | 2009-11-24 | Metabolex Inc. | Modulators of PPAR and methods of their preparation |
| MY148521A (en) | 2005-01-10 | 2013-04-30 | Arena Pharm Inc | Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto |
| US20100130737A1 (en) * | 2005-02-18 | 2010-05-27 | Takeda Pharmaceutical Company Limited | Regulating Agent of GPR34 Receptor Function |
| EP1866293A1 (en) * | 2005-03-31 | 2007-12-19 | UCB Pharma, S.A. | Compounds comprising an oxazole or thiazole moiety, processes for making them, and their uses |
| US7816536B2 (en) | 2005-06-10 | 2010-10-19 | The Research Foundation Of State University Of New York | 4-substituted and 7-substituted indoles, benzofurans, benzothiophenes, benzimidazoles, benzoxazoles, and benzothiazoles and methods for making same |
| US8653115B2 (en) | 2006-06-13 | 2014-02-18 | Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences | Heterocyclic non-nucleoside compounds, their preparation, pharmaceutical composition and their use as antiviral agents |
| TW200936130A (en) * | 2008-02-26 | 2009-09-01 | Lundbeck & Co As H | Uses of indane compounds |
| EP2389368B1 (en) | 2009-01-23 | 2015-06-17 | Merck Sharp & Dohme Corp. | Bridged and fused antidiabetic compounds |
| AU2010206786A1 (en) * | 2009-01-23 | 2011-07-28 | Merck Sharp & Dohme Corp. | Bridged and fused heterocyclic antidiabetic compounds |
| TW201040186A (en) | 2009-02-05 | 2010-11-16 | Schering Corp | Phthalazine-containing antidiabetic compounds |
| WO2010141696A1 (en) * | 2009-06-04 | 2010-12-09 | Dara Biosciences, Inc. | Methods of treating or preventing psoriasis, and/or alzheimer's disease using indane acetic acid derivatives |
| JP2012188352A (ja) * | 2009-07-13 | 2012-10-04 | Dainippon Sumitomo Pharma Co Ltd | 3−(4−置換アルキル−フェニル)−2−フランカルボン酸誘導体およびその薬学的に許容される塩 |
| JP5941916B2 (ja) | 2010-09-22 | 2016-06-29 | アリーナ ファーマシューティカルズ, インコーポレイテッド | Gpr119レセプターのモジュレーターおよびそれに関連する障害の処置 |
| WO2012074980A2 (en) * | 2010-12-01 | 2012-06-07 | Dara Biosciences, Inc. | Methods of treating or preventing autoimmune disorders and liver disorders using indane acetic acid derivatives |
| PL3242666T3 (pl) | 2015-01-06 | 2025-02-17 | Arena Pharmaceuticals, Inc. | Związek do zastosowania w leczeniu dolegliwości związanych z receptorem s1p1 |
| DK3310760T3 (da) | 2015-06-22 | 2022-10-24 | Arena Pharm Inc | Krystallinsk L-argininsalt af (R)-2-(7-(4-cyclopentyl-3-(trifluormethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3- yl)eddikesyre til anvendelse ved S1P1-receptor-associerede lidelser |
| CN110520124A (zh) | 2017-02-16 | 2019-11-29 | 艾尼纳制药公司 | 用于治疗原发性胆汁性胆管炎的化合物和方法 |
| BR112020024762A2 (pt) | 2018-06-06 | 2021-03-23 | Arena Pharmaceuticals, Inc. | métodos de tratamento de condições relacionadas ao receptor s1p1 |
| BR112021013807A2 (pt) * | 2019-01-18 | 2021-11-30 | Astrazeneca Ab | Inibidores de pcsk9 e seus métodos de uso |
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| JPS6197241A (ja) * | 1984-10-16 | 1986-05-15 | Yamanouchi Pharmaceut Co Ltd | 新規カルボン酸誘導体 |
| CA1314224C (en) * | 1987-07-07 | 1993-03-09 | Shinichiro Ashida | Antidiabetic agent |
| AR036237A1 (es) * | 2001-07-27 | 2004-08-25 | Bayer Corp | Derivados del acido indan acetico, intermediarios, y metodo para su preparacion, composicion farmaceutica y el uso de dichos derivados para la manufactura de un medicamento |
| UA79755C2 (en) | 2002-04-16 | 2007-07-25 | Bayer Pharmaceuticals Corp | Indane acetic acid derivatives and their use as pharmaceutical agents, intermediates, and method of preparation |
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| US7714004B2 (en) | 2010-05-11 |
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| Publication | Publication Date | Title |
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