ZA200605022B - Benzofurans and benzothiophenes - Google Patents

Benzofurans and benzothiophenes Download PDF

Info

Publication number: ZA200605022B
Authority: ZA; South Africa
Prior art keywords: alk; benzo; yloxy; formula; chosen
Prior art date: 2003-11-20

Application number

ZA200605022A

Other languages

English (en)

Inventor

Moinet Gurard

Kergoat Micheline

Leriche Caroline

Original Assignee

Merck Patent Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-11-20

Filing date

2006-06-19

Publication date

2007-10-31

2006-06-19 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2007-10-31 Publication of ZA200605022B publication Critical patent/ZA200605022B/en

Links

150000001907 coumarones Chemical class 0.000 title description 3
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title description 2
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 77
125000005605 benzo group Chemical group 0.000 claims description 72
150000001875 compounds Chemical class 0.000 claims description 69
150000003839 salts Chemical class 0.000 claims description 41
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 31
-1 alkyl radical Chemical group 0.000 claims description 30
238000000034 method Methods 0.000 claims description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
230000008569 process Effects 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 8
239000002798 polar solvent Substances 0.000 claims description 8
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 7
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
206010012601 diabetes mellitus Diseases 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
201000001421 hyperglycemia Diseases 0.000 claims description 5
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
ALJWLHQGTSSBHL-UHFFFAOYSA-N (3-hydroxy-1-benzothiophen-2-yl)-phenylmethanone Chemical compound S1C2=CC=CC=C2C(O)=C1C(=O)C1=CC=CC=C1 ALJWLHQGTSSBHL-UHFFFAOYSA-N 0.000 claims description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
PKICAZMQMYKBKV-UHFFFAOYSA-N 1-(1-adamantyl)-2-[(2-benzoyl-1-benzofuran-3-yl)oxy]ethanone Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)COC(C1=CC=CC=C1O1)=C1C(=O)C1=CC=CC=C1 PKICAZMQMYKBKV-UHFFFAOYSA-N 0.000 claims description 2
ZSCBRURAYGWTDT-UHFFFAOYSA-N 2-[(2-benzoyl-1-benzofuran-3-yl)oxy]-1-(2,4-dimethoxyphenyl)ethanone Chemical compound COC1=CC(OC)=CC=C1C(=O)COC1=C(C(=O)C=2C=CC=CC=2)OC2=CC=CC=C12 ZSCBRURAYGWTDT-UHFFFAOYSA-N 0.000 claims description 2
GMBJDGNPVIPFPL-UHFFFAOYSA-N 2-[(2-benzoyl-1-benzofuran-3-yl)oxy]-1-(2-phenylmethoxyphenyl)ethanone Chemical compound C=1C=CC=C(OCC=2C=CC=CC=2)C=1C(=O)COC(C1=CC=CC=C1O1)=C1C(=O)C1=CC=CC=C1 GMBJDGNPVIPFPL-UHFFFAOYSA-N 0.000 claims description 2
NPBDHUQYKIFSAS-UHFFFAOYSA-N 2-[(2-benzoyl-1-benzofuran-3-yl)oxy]-1-(4-chlorophenyl)ethanone Chemical compound C1=CC(Cl)=CC=C1C(=O)COC1=C(C(=O)C=2C=CC=CC=2)OC2=CC=CC=C12 NPBDHUQYKIFSAS-UHFFFAOYSA-N 0.000 claims description 2
HDPFJYHUCFPFRB-UHFFFAOYSA-N 2-[(2-benzoyl-1-benzofuran-3-yl)oxy]-1-(4-methylphenyl)ethanone Chemical compound C1=CC(C)=CC=C1C(=O)COC1=C(C(=O)C=2C=CC=CC=2)OC2=CC=CC=C12 HDPFJYHUCFPFRB-UHFFFAOYSA-N 0.000 claims description 2
HQKKCAWOXRSYFN-UHFFFAOYSA-N 2-[(2-benzoyl-1-benzofuran-3-yl)oxy]-1-(4-phenylmethoxyphenyl)ethanone Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1C(=O)COC(C1=CC=CC=C1O1)=C1C(=O)C1=CC=CC=C1 HQKKCAWOXRSYFN-UHFFFAOYSA-N 0.000 claims description 2
UYKFMNLJHBVPLF-UHFFFAOYSA-N 2-[(2-benzoyl-1-benzofuran-3-yl)oxy]-1-(4-phenylphenyl)ethanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)COC(C1=CC=CC=C1O1)=C1C(=O)C1=CC=CC=C1 UYKFMNLJHBVPLF-UHFFFAOYSA-N 0.000 claims description 2
NSARJWHYFYWBJY-UHFFFAOYSA-N 2-[(2-benzoyl-1-benzofuran-3-yl)oxy]-1-naphthalen-2-ylethanone Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)COC(C1=CC=CC=C1O1)=C1C(=O)C1=CC=CC=C1 NSARJWHYFYWBJY-UHFFFAOYSA-N 0.000 claims description 2
201000001320 Atherosclerosis Diseases 0.000 claims description 2
208000032928 Dyslipidaemia Diseases 0.000 claims description 2
206010054805 Macroangiopathy Diseases 0.000 claims description 2
208000008589 Obesity Diseases 0.000 claims description 2
208000017442 Retinal disease Diseases 0.000 claims description 2
206010038923 Retinopathy Diseases 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
208000037849 arterial hypertension Diseases 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
230000004054 inflammatory process Effects 0.000 claims description 2
206010062198 microangiopathy Diseases 0.000 claims description 2
201000001119 neuropathy Diseases 0.000 claims description 2
230000007823 neuropathy Effects 0.000 claims description 2
235000020824 obesity Nutrition 0.000 claims description 2
208000033808 peripheral neuropathy Diseases 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims description 2
239000003814 drug Substances 0.000 claims 5
LFMABXGWBMPFNQ-UHFFFAOYSA-N (3-hydroxy-1-benzofuran-2-yl)-phenylmethanone Chemical compound O1C2=CC=CC=C2C(O)=C1C(=O)C1=CC=CC=C1 LFMABXGWBMPFNQ-UHFFFAOYSA-N 0.000 claims 1
AYKYTNDOJJTYQO-UHFFFAOYSA-N 2-[(2-benzoyl-1-benzofuran-3-yl)oxy]-1-(2-methoxyphenyl)ethanone Chemical compound COC1=CC=CC=C1C(=O)COC1=C(C(=O)C=2C=CC=CC=2)OC2=CC=CC=C12 AYKYTNDOJJTYQO-UHFFFAOYSA-N 0.000 claims 1
IGGDJOASAMLGEW-UHFFFAOYSA-N 2-[(2-benzoyl-1-benzofuran-3-yl)oxy]-1-(3,4-dimethoxyphenyl)ethanone Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)COC1=C(C(=O)C=2C=CC=CC=2)OC2=CC=CC=C12 IGGDJOASAMLGEW-UHFFFAOYSA-N 0.000 claims 1
XXKMXLCPBBSHFD-UHFFFAOYSA-N 2-[(2-benzoyl-1-benzofuran-3-yl)oxy]-1-(4-fluorophenyl)ethanone Chemical compound C1=CC(F)=CC=C1C(=O)COC1=C(C(=O)C=2C=CC=CC=2)OC2=CC=CC=C12 XXKMXLCPBBSHFD-UHFFFAOYSA-N 0.000 claims 1
ADUAOIAPQARAJA-UHFFFAOYSA-N 2-[(2-benzoyl-1-benzofuran-3-yl)oxy]-1-(4-methoxyphenyl)ethanone Chemical compound C1=CC(OC)=CC=C1C(=O)COC1=C(C(=O)C=2C=CC=CC=2)OC2=CC=CC=C12 ADUAOIAPQARAJA-UHFFFAOYSA-N 0.000 claims 1
LJGDUXHNLQKBOO-UHFFFAOYSA-N 2-[(2-benzoyl-1-benzothiophen-3-yl)oxy]-1-(4-chlorophenyl)ethanone Chemical compound C1=CC(Cl)=CC=C1C(=O)COC1=C(C(=O)C=2C=CC=CC=2)SC2=CC=CC=C12 LJGDUXHNLQKBOO-UHFFFAOYSA-N 0.000 claims 1
VWBZKUVQIVWLPC-UHFFFAOYSA-N 2-[(2-benzoyl-1-benzothiophen-3-yl)oxy]-1-(4-methoxyphenyl)ethanone Chemical compound C1=CC(OC)=CC=C1C(=O)COC1=C(C(=O)C=2C=CC=CC=2)SC2=CC=CC=C12 VWBZKUVQIVWLPC-UHFFFAOYSA-N 0.000 claims 1
YSCNBEFFOMKVTE-UHFFFAOYSA-N 2-[(2-benzoyl-1-benzothiophen-3-yl)oxy]-1-(4-methylphenyl)ethanone Chemical compound C1=CC(C)=CC=C1C(=O)COC1=C(C(=O)C=2C=CC=CC=2)SC2=CC=CC=C12 YSCNBEFFOMKVTE-UHFFFAOYSA-N 0.000 claims 1
RKUBBXQHZYRJQM-UHFFFAOYSA-N 3-[[2-(4-cyanobenzoyl)-1-benzothiophen-3-yl]oxymethyl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C(=O)C=1SC2=CC=CC=C2C=1OCC1=CC=CC(C#N)=C1 RKUBBXQHZYRJQM-UHFFFAOYSA-N 0.000 claims 1
ONHFZTWBAKXWME-UHFFFAOYSA-N 4-(3-phenacyloxy-1-benzothiophene-2-carbonyl)benzonitrile Chemical compound C=1C=CC=CC=1C(=O)COC(C1=CC=CC=C1S1)=C1C(=O)C1=CC=C(C#N)C=C1 ONHFZTWBAKXWME-UHFFFAOYSA-N 0.000 claims 1
JXHZONYXNKLCMD-UHFFFAOYSA-N 4-[3-(2-naphthalen-2-yl-2-oxoethoxy)-1-benzothiophene-2-carbonyl]benzonitrile Chemical compound C=1C=C2C=CC=CC2=CC=1C(=O)COC(C1=CC=CC=C1S1)=C1C(=O)C1=CC=C(C#N)C=C1 JXHZONYXNKLCMD-UHFFFAOYSA-N 0.000 claims 1
CNNIOXAWNMIOMR-UHFFFAOYSA-N 4-[3-[(2-chloro-4-fluorophenyl)methoxy]-1-benzothiophene-2-carbonyl]benzonitrile Chemical compound ClC1=CC(F)=CC=C1COC1=C(C(=O)C=2C=CC(=CC=2)C#N)SC2=CC=CC=C12 CNNIOXAWNMIOMR-UHFFFAOYSA-N 0.000 claims 1
VUCBTALHYFJNPG-UHFFFAOYSA-N 4-[3-[2-(3-methoxy-4-phenylmethoxyphenyl)-2-oxoethoxy]-1-benzothiophene-2-carbonyl]benzonitrile Chemical compound COC1=CC(C(=O)COC=2C3=CC=CC=C3SC=2C(=O)C=2C=CC(=CC=2)C#N)=CC=C1OCC1=CC=CC=C1 VUCBTALHYFJNPG-UHFFFAOYSA-N 0.000 claims 1
SHFIUZMXUVEWKT-UHFFFAOYSA-N 4-[3-[2-(4-methoxyphenyl)-2-oxoethoxy]-1-benzothiophene-2-carbonyl]benzonitrile Chemical compound C1=CC(OC)=CC=C1C(=O)COC1=C(C(=O)C=2C=CC(=CC=2)C#N)SC2=CC=CC=C12 SHFIUZMXUVEWKT-UHFFFAOYSA-N 0.000 claims 1
CEIWVGZBFADNGQ-UHFFFAOYSA-N 4-[3-[2-(5-fluoro-2-phenylmethoxyphenyl)-2-oxoethoxy]-1-benzothiophene-2-carbonyl]benzonitrile Chemical compound C=1C=C(C#N)C=CC=1C(=O)C=1SC2=CC=CC=C2C=1OCC(=O)C1=CC(F)=CC=C1OCC1=CC=CC=C1 CEIWVGZBFADNGQ-UHFFFAOYSA-N 0.000 claims 1
RBYPPBLGVAEGBR-UHFFFAOYSA-N 4-[3-[2-oxo-2-(2-phenylmethoxyphenyl)ethoxy]-1-benzothiophene-2-carbonyl]benzonitrile Chemical compound C=1C=CC=C(OCC=2C=CC=CC=2)C=1C(=O)COC(C1=CC=CC=C1S1)=C1C(=O)C1=CC=C(C#N)C=C1 RBYPPBLGVAEGBR-UHFFFAOYSA-N 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 1
CSARTJUJYSOABI-UHFFFAOYSA-N [3-[2-(4-fluorophenoxy)ethoxy]-1-benzothiophen-2-yl]-phenylmethanone Chemical compound C1=CC(F)=CC=C1OCCOC1=C(C(=O)C=2C=CC=CC=2)SC2=CC=CC=C12 CSARTJUJYSOABI-UHFFFAOYSA-N 0.000 claims 1
125000004093 cyano group Chemical group *C#N 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
JLCGWFXPNGYTLN-UHFFFAOYSA-N methyl 2-[(2-benzoyl-1-benzofuran-3-yl)oxy]-3-methoxypropanoate Chemical compound O1C2=CC=CC=C2C(OC(COC)C(=O)OC)=C1C(=O)C1=CC=CC=C1 JLCGWFXPNGYTLN-UHFFFAOYSA-N 0.000 claims 1
WIIYBLVINGKVGP-UHFFFAOYSA-N methyl 2-[(2-benzoyl-1-benzothiophen-3-yl)oxy]-3-methoxypropanoate Chemical compound S1C2=CC=CC=C2C(OC(COC)C(=O)OC)=C1C(=O)C1=CC=CC=C1 WIIYBLVINGKVGP-UHFFFAOYSA-N 0.000 claims 1
XTQAKTPVYQKXJK-UHFFFAOYSA-N methyl 3-[4-[2-[(2-benzoyl-1-benzothiophen-3-yl)oxy]ethoxy]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OC)=CC=C1OCCOC1=C(C(=O)C=2C=CC=CC=2)SC2=CC=CC=C12 XTQAKTPVYQKXJK-UHFFFAOYSA-N 0.000 claims 1
ASYSMEXEEHKQCA-UHFFFAOYSA-N phenyl-(3-phenylmethoxy-1-benzothiophen-2-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)C=1SC2=CC=CC=C2C=1OCC1=CC=CC=C1 ASYSMEXEEHKQCA-UHFFFAOYSA-N 0.000 claims 1
ASMBJUGWBZXRGU-UHFFFAOYSA-M sodium;2-(4-cyanobenzoyl)-1-benzothiophen-3-olate Chemical compound [Na+].S1C2=CC=CC=C2C([O-])=C1C(=O)C1=CC=C(C#N)C=C1 ASMBJUGWBZXRGU-UHFFFAOYSA-M 0.000 claims 1
239000002253 acid Substances 0.000 description 10
230000006978 adaptation Effects 0.000 description 7
239000000243 solution Substances 0.000 description 7
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229910052500 inorganic mineral Inorganic materials 0.000 description 6
235000010755 mineral Nutrition 0.000 description 6
239000011707 mineral Substances 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
239000002585 base Substances 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000000047 product Substances 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
239000002904 solvent Substances 0.000 description 5
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000012458 free base Substances 0.000 description 4
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 4
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125000002098 pyridazinyl group Chemical group 0.000 description 3
125000004076 pyridyl group Chemical group 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
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GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
229960002023 chloroprocaine Drugs 0.000 description 1
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
JWOSTXBESVWMJW-UHFFFAOYSA-N cyclohexyl sulfamate Chemical class NS(=O)(=O)OC1CCCCC1 JWOSTXBESVWMJW-UHFFFAOYSA-N 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007547 defect Effects 0.000 description 1
230000006735 deficit Effects 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
125000003838 furazanyl group Chemical group 0.000 description 1
229960005219 gentisic acid Drugs 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
125000005945 imidazopyridyl group Chemical group 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
229940001447 lactate Drugs 0.000 description 1
229940099584 lactobionate Drugs 0.000 description 1
JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000004137 magnesium phosphate Substances 0.000 description 1
GVALZJMUIHGIMD-UHFFFAOYSA-H magnesium phosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O GVALZJMUIHGIMD-UHFFFAOYSA-H 0.000 description 1
229960002261 magnesium phosphate Drugs 0.000 description 1
229910000157 magnesium phosphate Inorganic materials 0.000 description 1
235000010994 magnesium phosphates Nutrition 0.000 description 1
229940049920 malate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
150000002690 malonic acid derivatives Chemical class 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
229940057952 methanol Drugs 0.000 description 1
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 1
DERGNIMCQQTSFB-UHFFFAOYSA-N methyl 4-[(2-benzoyl-1-benzothiophen-3-yl)oxymethyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1COC1=C(C(=O)C=2C=CC=CC=2)SC2=CC=CC=C12 DERGNIMCQQTSFB-UHFFFAOYSA-N 0.000 description 1
235000019426 modified starch Nutrition 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
125000005487 naphthalate group Chemical group 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003791 organic solvent mixture Substances 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
229940039748 oxalate Drugs 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
229940075930 picrate Drugs 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
239000006187 pill Substances 0.000 description 1
229950010765 pivalate Drugs 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
ANBFRLKBEIFNQU-UHFFFAOYSA-M potassium;octadecanoate Chemical class [K+].CCCCCCCCCCCCCCCCCC([O-])=O ANBFRLKBEIFNQU-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
125000006085 pyrrolopyridyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
150000003873 salicylate salts Chemical class 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229930195734 saturated hydrocarbon Natural products 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
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012453 solvate Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 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
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 description 1
229940103494 thiosalicylic acid Drugs 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
230000002792 vascular Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/64—Oxygen atoms
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- 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
- 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
- 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
- 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
- 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
- A61P9/12—Antihypertensives
- 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
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Diabetes (AREA)
Obesity (AREA)
Hematology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Endocrinology (AREA)
Emergency Medicine (AREA)
Child & Adolescent Psychology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Ophthalmology & Optometry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Furan Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Peptides Or Proteins (AREA)

ZA200605022A 2003-11-20 2006-06-19 Benzofurans and benzothiophenes ZA200605022B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR0313615A FR2862646B1 (fr)	2003-11-20	2003-11-20	Nouveaux composes antidiabetiques contenant des derives benzofuranes, benzothiophenes

Publications (1)

Publication Number	Publication Date
ZA200605022B true ZA200605022B (en)	2007-10-31

Family

ID=34531152

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200605022A ZA200605022B (en)	2003-11-20	2006-06-19	Benzofurans and benzothiophenes

Country Status (16)

Country	Link
US (1)	US7371774B2 (de)
EP (1)	EP1685122B1 (de)
JP (1)	JP4819692B2 (de)
KR (1)	KR20060101492A (de)
CN (1)	CN1882562A (de)
AR (1)	AR046645A1 (de)
AT (1)	ATE400566T1 (de)
AU (1)	AU2004295036B9 (de)
BR (1)	BRPI0416790A (de)
CA (1)	CA2546651C (de)
DE (1)	DE602004014966D1 (de)
ES (1)	ES2308270T3 (de)
FR (1)	FR2862646B1 (de)
MX (1)	MXPA06005591A (de)
WO (1)	WO2005054226A1 (de)
ZA (1)	ZA200605022B (de)

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FR2862645B1 (fr) *	2003-11-20	2007-06-22	Merck Sante Sas	Composes antidiabetiques contenant des derives benzofuranes, benzothiophenes
GB0506133D0 (en) *	2005-03-24	2005-05-04	Sterix Ltd	Compound
CN101830872A (zh) *	2010-04-14	2010-09-15	南方医科大学	一种3-羟基苯并呋喃类衍生物的合成方法
ES2935125T3 (es) *	2015-12-09	2023-03-01	Univ Illinois	Reguladores a la baja selectivos de los receptores de estrógenos con base en benzotiofeno
WO2018081168A2 (en)	2016-10-24	2018-05-03	The Board Of Trustees Of The University Of Illinois	Benzothiophene-based selective mixed estrogen receptor downregulators
AR110728A1 (es)	2017-01-06	2019-04-24	G1 Therapeutics Inc	Terapia combinada para el tratamiento del cáncer
TW201835064A (zh)	2017-02-10	2018-10-01	美商G1治療公司	苯并噻吩雌激素受體調節劑

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GB1084290A (de) *	1963-12-02	1900-01-01
SE351639B (de) *	1964-11-11	1972-12-04	Haessle Ab
JPH10175970A (ja) *	1996-12-19	1998-06-30	Mitsui Chem Inc	ベンゾチオフェン誘導体およびそれを有効成分として含有する医薬品
CN1308621A (zh) *	1998-05-12	2001-08-15	美国家用产品公司	用于治疗胰岛素抗性和高血糖的苯基氧代－乙酸
ATE298323T1 (de) *	2000-09-19	2005-07-15	Warner Lambert Co	Hemmer der verzweigtenaminosäure-abhängigen aminotransferase und deren verwendung in der behandlung von neurodegenerativen erkrankungen
JP2006526608A (ja) *	2003-06-05	2006-11-24	ワーナー−ランバートカンパニーリミティドライアビリティーカンパニー	Ｐｉ３ｋ活性を有する治療薬としてのテトラゾールベンゾフランカルボキシアミド
FR2862645B1 (fr) *	2003-11-20	2007-06-22	Merck Sante Sas	Composes antidiabetiques contenant des derives benzofuranes, benzothiophenes

2003
- 2003-11-20 FR FR0313615A patent/FR2862646B1/fr not_active Expired - Fee Related
2004
- 2004-11-08 US US10/579,996 patent/US7371774B2/en not_active Expired - Fee Related
- 2004-11-08 AT AT04797711T patent/ATE400566T1/de not_active IP Right Cessation
- 2004-11-08 BR BRPI0416790-2A patent/BRPI0416790A/pt not_active Application Discontinuation
- 2004-11-08 AU AU2004295036A patent/AU2004295036B9/en not_active Ceased
- 2004-11-08 JP JP2006540238A patent/JP4819692B2/ja not_active Expired - Fee Related
- 2004-11-08 WO PCT/EP2004/012620 patent/WO2005054226A1/en not_active Ceased
- 2004-11-08 DE DE602004014966T patent/DE602004014966D1/de not_active Expired - Lifetime
- 2004-11-08 KR KR1020067009680A patent/KR20060101492A/ko not_active Withdrawn
- 2004-11-08 EP EP04797711A patent/EP1685122B1/de not_active Expired - Lifetime
- 2004-11-08 MX MXPA06005591A patent/MXPA06005591A/es unknown
- 2004-11-08 ES ES04797711T patent/ES2308270T3/es not_active Expired - Lifetime
- 2004-11-08 CA CA2546651A patent/CA2546651C/en not_active Expired - Fee Related
- 2004-11-08 CN CNA2004800341918A patent/CN1882562A/zh active Pending
- 2004-11-19 AR ARP040104274A patent/AR046645A1/es unknown
2006
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Also Published As

Publication number	Publication date
CA2546651A1 (en)	2005-06-16
AR046645A1 (es)	2005-12-14
AU2004295036B2 (en)	2010-12-23
DE602004014966D1 (de)	2008-08-21
US7371774B2 (en)	2008-05-13
AU2004295036B9 (en)	2011-02-03
ATE400566T1 (de)	2008-07-15
JP2007511556A (ja)	2007-05-10
BRPI0416790A (pt)	2007-03-06
FR2862646B1 (fr)	2006-02-24
EP1685122A1 (de)	2006-08-02
CN1882562A (zh)	2006-12-20
KR20060101492A (ko)	2006-09-25
WO2005054226A1 (en)	2005-06-16
JP4819692B2 (ja)	2011-11-24
AU2004295036A1 (en)	2005-06-16
MXPA06005591A (es)	2006-08-11
US20070066680A1 (en)	2007-03-22
EP1685122B1 (de)	2008-07-09
FR2862646A1 (fr)	2005-05-27
CA2546651C (en)	2012-12-18
ES2308270T3 (es)	2008-12-01

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MXPA99011996A (en)	2000-06-01	Bis-indole derivatives having antimetastatic activity, a process for their preparation and pharmaceutical compositions containing them