SK16992000A3 - Benzotiofény, benzofurány, indoly, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents

Benzotiofény, benzofurány, indoly, farmaceutický prostriedok s ich obsahom a ich použitie Download PDF

Info

Publication number: SK16992000A3
Authority: SK; Slovakia
Prior art keywords: carbon atoms; naphtho; thiophen; bromo; dimethyl
Prior art date: 1998-05-12

Application number

SK1699-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Jay Edward Wrobel

Arlene Joan Dietrich

Madelene Miyoko Antane

Original Assignee

American Home Products Corporation

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.)

1998-05-12

Filing date

1999-05-10

Publication date

2001-04-09

1999-05-10 Application filed by American Home Products Corporation filed Critical American Home Products Corporation

2001-04-09 Publication of SK16992000A3 publication Critical patent/SK16992000A3/sk

Links

208000001072 type 2 diabetes mellitus Diseases 0.000 title claims abstract description 27
206010022489 Insulin Resistance Diseases 0.000 title claims abstract description 19
201000001421 hyperglycemia Diseases 0.000 title claims abstract description 10
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title claims description 7
150000001907 coumarones Chemical class 0.000 title claims description 5
150000002475 indoles Chemical class 0.000 title claims description 5
150000001875 compounds Chemical class 0.000 claims abstract description 248
150000003839 salts Chemical class 0.000 claims abstract description 51
208000030159 metabolic disease Diseases 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 428
125000000217 alkyl group Chemical group 0.000 claims description 297
-1 nitro, amino Chemical group 0.000 claims description 260
229910052739 hydrogen Inorganic materials 0.000 claims description 228
125000003118 aryl group Chemical group 0.000 claims description 195
229910052736 halogen Inorganic materials 0.000 claims description 164
150000002367 halogens Chemical class 0.000 claims description 164
229910052760 oxygen Chemical group 0.000 claims description 164
229910052717 sulfur Inorganic materials 0.000 claims description 163
125000003710 aryl alkyl group Chemical group 0.000 claims description 154
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 120
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 118
125000005010 perfluoroalkyl group Chemical group 0.000 claims description 95
229910052799 carbon Inorganic materials 0.000 claims description 90
125000005163 aryl sulfanyl group Chemical group 0.000 claims description 87
239000001257 hydrogen Substances 0.000 claims description 83
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 82
125000003545 alkoxy group Chemical group 0.000 claims description 81
125000004414 alkyl thio group Chemical group 0.000 claims description 65
239000002253 acid Substances 0.000 claims description 35
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
239000008103 glucose Substances 0.000 claims description 18
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 16
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 16
125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 13
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 10
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
DTOSLKDCIXNWRZ-UHFFFAOYSA-N 2,6-dibromo-4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)phenol Chemical compound C=12C(C)=C(C)SC2=C(Br)C2=CC=CC=C2C=1C1=CC(Br)=C(O)C(Br)=C1 DTOSLKDCIXNWRZ-UHFFFAOYSA-N 0.000 claims description 8
125000004104 aryloxy group Chemical group 0.000 claims description 8
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 7
GBQTYLAQGXLQOV-UHFFFAOYSA-N 2,6-dibromo-4-(2,3-dimethyl-9-phenylsulfanylbenzo[f][1]benzothiol-4-yl)phenol Chemical compound C12=CC=CC=C2C(C=2C=C(Br)C(O)=C(Br)C=2)=C2C(C)=C(C)SC2=C1SC1=CC=CC=C1 GBQTYLAQGXLQOV-UHFFFAOYSA-N 0.000 claims description 6
DADVNWPKORBKAA-UHFFFAOYSA-N 6-bromo-4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-6-nitrocyclohexa-2,4-dien-1-ol Chemical compound C=12C(C)=C(C)SC2=C(Br)C2=CC=CC=C2C=1C1=CC(Br)([N+]([O-])=O)C(O)C=C1 DADVNWPKORBKAA-UHFFFAOYSA-N 0.000 claims description 6
125000002897 diene group Chemical group 0.000 claims description 6
YJSKKYXMKLNJHQ-UHFFFAOYSA-N 2,6-dibromo-4-[9-bromo-2-(diethylaminomethyl)-3-methylbenzo[f][1]benzothiol-4-yl]phenol Chemical compound C=12C(C)=C(CN(CC)CC)SC2=C(Br)C2=CC=CC=C2C=1C1=CC(Br)=C(O)C(Br)=C1 YJSKKYXMKLNJHQ-UHFFFAOYSA-N 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
PGLMYLRQHITYKV-AREMUKBSSA-N (2r)-2-[2-bromo-4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-6-propan-2-ylphenoxy]-3-phenylpropanoic acid Chemical compound C([C@@H](OC1=C(Br)C=C(C=C1C(C)C)C=1C2=CC=CC=C2C(Br)=C2SC(C)=C(C)C2=1)C(O)=O)C1=CC=CC=C1 PGLMYLRQHITYKV-AREMUKBSSA-N 0.000 claims description 4
YFTHHCRTKXURKH-UHFFFAOYSA-N 2-[4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-2,6-di(propan-2-yl)phenoxy]acetic acid Chemical compound CC(C)C1=C(OCC(O)=O)C(C(C)C)=CC(C=2C3=CC=CC=C3C(Br)=C3SC(C)=C(C)C3=2)=C1 YFTHHCRTKXURKH-UHFFFAOYSA-N 0.000 claims description 4
KMOBQTBRQNRVQL-UHFFFAOYSA-N 2-bromo-4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-6-propan-2-ylphenol Chemical compound BrC1=C(O)C(C(C)C)=CC(C=2C3=CC=CC=C3C(Br)=C3SC(C)=C(C)C3=2)=C1 KMOBQTBRQNRVQL-UHFFFAOYSA-N 0.000 claims description 4
OYHZWLRDRACBCR-UHFFFAOYSA-N 4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-2-nitrophenol Chemical compound C=12C(C)=C(C)SC2=C(Br)C2=CC=CC=C2C=1C1=CC=C(O)C([N+]([O-])=O)=C1 OYHZWLRDRACBCR-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
MCJCMPYIPPYNQQ-UHFFFAOYSA-N [4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C1=C(C(C)=C(C)S2)C2=C(Br)C2=CC=CC=C12 MCJCMPYIPPYNQQ-UHFFFAOYSA-N 0.000 claims description 4
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000001301 oxygen Chemical group 0.000 claims description 4
229950009215 phenylbutanoic acid Drugs 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
JGIRDKSSVIOQPU-SSEXGKCCSA-N (2r)-2-[4-(2,3-dimethylbenzo[f][1]benzothiol-4-yl)-2,6-di(propan-2-yl)phenoxy]-3-phenylpropanoic acid Chemical compound C([C@@H](OC1=C(C(C)C)C=C(C=C1C(C)C)C=1C2=CC=CC=C2C=C2SC(C)=C(C)C2=1)C(O)=O)C1=CC=CC=C1 JGIRDKSSVIOQPU-SSEXGKCCSA-N 0.000 claims description 3
PWGGPFARYFWXFE-AREMUKBSSA-N (2r)-2-[4-(2,3-dimethylbenzo[f][1]benzothiol-4-yl)-2,6-dimethylphenoxy]-3-phenylpropanoic acid Chemical compound C([C@@H](OC1=C(C)C=C(C=C1C)C=1C2=CC=CC=C2C=C2SC(=C(C2=1)C)C)C(O)=O)C1=CC=CC=C1 PWGGPFARYFWXFE-AREMUKBSSA-N 0.000 claims description 3
DEDAJYFSMOZFMF-MUUNZHRXSA-N (2r)-2-[4-(2,3-dimethylbenzo[f][1]benzothiol-4-yl)-2-propan-2-ylphenoxy]-3-phenylpropanoic acid Chemical compound C([C@@H](OC1=CC=C(C=C1C(C)C)C=1C2=CC=CC=C2C=C2SC(C)=C(C)C2=1)C(O)=O)C1=CC=CC=C1 DEDAJYFSMOZFMF-MUUNZHRXSA-N 0.000 claims description 3
VWTGUCRWZOQMEO-QOHVGFNKSA-N (2r)-2-[6-bromo-4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-6-cyclopentylcyclohexa-2,4-dien-1-yl]oxy-3-phenylpropanoic acid Chemical compound C=12C(C)=C(C)SC2=C(Br)C2=CC=CC=C2C=1C(C=CC1O[C@H](CC=2C=CC=CC=2)C(O)=O)=CC1(Br)C1CCCC1 VWTGUCRWZOQMEO-QOHVGFNKSA-N 0.000 claims description 3
YMRIDJQAEZFTSC-UHFFFAOYSA-N 2,3-dihydro-1h-tetrazole Chemical compound N1NC=NN1 YMRIDJQAEZFTSC-UHFFFAOYSA-N 0.000 claims description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
ZQDKWFBAFUXBST-UHFFFAOYSA-N 4-(2,3-dimethyl-9-phenylsulfanylbenzo[f][1]benzothiol-4-yl)phenol Chemical compound C12=CC=CC=C2C(C=2C=CC(O)=CC=2)=C2C(C)=C(C)SC2=C1SC1=CC=CC=C1 ZQDKWFBAFUXBST-UHFFFAOYSA-N 0.000 claims description 3
XQDKOANVSQEFEK-UHFFFAOYSA-N 4-(2,3-dimethylbenzo[f][1]benzothiol-4-yl)phenol Chemical compound C=12C(C)=C(C)SC2=CC2=CC=CC=C2C=1C1=CC=C(O)C=C1 XQDKOANVSQEFEK-UHFFFAOYSA-N 0.000 claims description 3
CURDELKOPHWSTA-UHFFFAOYSA-N 4-[9-bromo-2-(diethylaminomethyl)-3-methylbenzo[f][1]benzothiol-4-yl]phenol Chemical compound C=12C(C)=C(CN(CC)CC)SC2=C(Br)C2=CC=CC=C2C=1C1=CC=C(O)C=C1 CURDELKOPHWSTA-UHFFFAOYSA-N 0.000 claims description 3
LLRBBFWBVOVYGA-UHFFFAOYSA-N [4-(2,3-dimethylbenzo[f][1]benzothiol-4-yl)phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C1=C(C(C)=C(C)S2)C2=CC2=CC=CC=C12 LLRBBFWBVOVYGA-UHFFFAOYSA-N 0.000 claims description 3
KHRNWPFHHRZBJP-UHFFFAOYSA-N [4-(2,3-dimethylbenzo[f][1]benzothiol-4-yl)phenyl] methanesulfonate Chemical compound C=12C(C)=C(C)SC2=CC2=CC=CC=C2C=1C1=CC=C(OS(C)(=O)=O)C=C1 KHRNWPFHHRZBJP-UHFFFAOYSA-N 0.000 claims description 3
YBGOWILNHUTXCX-UHFFFAOYSA-N [4-(9-iodo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)phenyl] methanesulfonate Chemical compound C=12C(C)=C(C)SC2=C(I)C2=CC=CC=C2C=1C1=CC=C(OS(C)(=O)=O)C=C1 YBGOWILNHUTXCX-UHFFFAOYSA-N 0.000 claims description 3
RBPZRTFWTYBMRQ-UHFFFAOYSA-N [4-[9-bromo-2-(chloromethyl)-3-methylbenzo[f][1]benzothiol-4-yl]phenyl] acetate Chemical compound C1=CC(OC(=O)C)=CC=C1C1=C(C(C)=C(CCl)S2)C2=C(Br)C2=CC=CC=C12 RBPZRTFWTYBMRQ-UHFFFAOYSA-N 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
SFNBAPJDUBXJPL-RUZDIDTESA-N (2r)-2-[2-bromo-4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-6-ethylphenoxy]-3-phenylpropanoic acid Chemical compound C([C@@H](OC1=C(Br)C=C(C=C1CC)C=1C2=CC=CC=C2C(Br)=C2SC(C)=C(C)C2=1)C(O)=O)C1=CC=CC=C1 SFNBAPJDUBXJPL-RUZDIDTESA-N 0.000 claims description 2
VOHWEAVTNNNDAV-SSEXGKCCSA-N (2r)-2-[2-cyclopentyl-4-(2,3-dimethylbenzo[f][1]benzothiol-4-yl)phenoxy]-3-phenylpropanoic acid Chemical compound C([C@@H](OC1=CC=C(C=C1C1CCCC1)C=1C2=CC=CC=C2C=C2SC(=C(C2=1)C)C)C(O)=O)C1=CC=CC=C1 VOHWEAVTNNNDAV-SSEXGKCCSA-N 0.000 claims description 2
IWVDPVRBDLFFKF-UHFFFAOYSA-N 2-[2,6-dibromo-4-[9-bromo-3-methyl-2-(morpholin-4-ylmethyl)benzo[f][1]benzothiol-4-yl]phenoxy]propanoic acid Chemical compound C1=C(Br)C(OC(C)C(O)=O)=C(Br)C=C1C1=C(C(C)=C(CN2CCOCC2)S2)C2=C(Br)C2=CC=CC=C12 IWVDPVRBDLFFKF-UHFFFAOYSA-N 0.000 claims description 2
PFBBZEQYIVORNG-UHFFFAOYSA-N 2-[6-bromo-4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-6-nitrocyclohexa-2,4-dien-1-yl]oxyacetic acid Chemical compound C=12C(C)=C(C)SC2=C(Br)C2=CC=CC=C2C=1C1=CC(Br)([N+]([O-])=O)C(OCC(O)=O)C=C1 PFBBZEQYIVORNG-UHFFFAOYSA-N 0.000 claims description 2
IFSFZIDCRMWDQW-UHFFFAOYSA-N 2-amino-4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)phenol Chemical compound C=12C(C)=C(C)SC2=C(Br)C2=CC=CC=C2C=1C1=CC=C(O)C(N)=C1 IFSFZIDCRMWDQW-UHFFFAOYSA-N 0.000 claims description 2
JYLCIXQRFYGEAE-UHFFFAOYSA-N 2-amino-6-bromo-4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)phenol Chemical compound C=12C(C)=C(C)SC2=C(Br)C2=CC=CC=C2C=1C1=CC(N)=C(O)C(Br)=C1 JYLCIXQRFYGEAE-UHFFFAOYSA-N 0.000 claims description 2
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
FYDTTWDGNADGFK-UHFFFAOYSA-N 4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)phenol Chemical compound C=12C(C)=C(C)SC2=C(Br)C2=CC=CC=C2C=1C1=CC=C(O)C=C1 FYDTTWDGNADGFK-UHFFFAOYSA-N 0.000 claims description 2
DFLUHPCOXUZOKK-LLVKDONJSA-N C1=C(Br)C(O[C@H](C)C(O)=O)=C(Br)C=C1C1=C(C(C)=C(C)S2)C2=C(Br)C2=CC=CC=C12 Chemical compound C1=C(Br)C(O[C@H](C)C(O)=O)=C(Br)C=C1C1=C(C(C)=C(C)S2)C2=C(Br)C2=CC=CC=C12 DFLUHPCOXUZOKK-LLVKDONJSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 2
241000124008 Mammalia Species 0.000 claims 3
KFKYBCSQCXMALN-AREMUKBSSA-N (2r)-2-[4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-2-ethylphenoxy]-3-phenylpropanoic acid Chemical compound C([C@@H](OC1=CC=C(C=C1CC)C=1C2=CC=CC=C2C(Br)=C2SC(C)=C(C)C2=1)C(O)=O)C1=CC=CC=C1 KFKYBCSQCXMALN-AREMUKBSSA-N 0.000 claims 2
IZUGNNXXWNTRFV-MKAWVKDUSA-N (2r)-2-[2-bromo-4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-6-butan-2-ylphenoxy]-3-phenylpropanoic acid Chemical compound C([C@@H](OC1=C(Br)C=C(C=C1C(C)CC)C=1C2=CC=CC=C2C(Br)=C2SC(C)=C(C)C2=1)C(O)=O)C1=CC=CC=C1 IZUGNNXXWNTRFV-MKAWVKDUSA-N 0.000 claims 1
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LOWURJWSVHYTAV-JWPKJQAESA-N (2r)-2-[4-(9-bromo-2,3-dimethyl-1-oxobenzo[f][1]benzothiol-4-yl)-2,6-dimethylphenoxy]-3-phenylpropanoic acid Chemical compound C([C@@H](OC1=C(C)C=C(C=C1C)C=1C2=CC=CC=C2C(Br)=C2S(=O)C(C)=C(C=12)C)C(O)=O)C1=CC=CC=C1 LOWURJWSVHYTAV-JWPKJQAESA-N 0.000 claims 1
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CMEPHZRVXYDTSO-UHFFFAOYSA-N 2-[4-[9-bromo-2-(diethylaminomethyl)-3-methylbenzo[f][1]benzothiol-4-yl]-2,6-dimethylphenoxy]-3-phenylpropanoic acid Chemical compound C=12C(C)=C(CN(CC)CC)SC2=C(Br)C2=CC=CC=C2C=1C(C=C1C)=CC(C)=C1OC(C(O)=O)CC1=CC=CC=C1 CMEPHZRVXYDTSO-UHFFFAOYSA-N 0.000 claims 1
LLFOKYWCITZTHK-UHFFFAOYSA-N 2-bromo-4-(2,3-dimethylbenzo[f][1]benzofuran-4-yl)-6-ethylphenol Chemical compound BrC1=C(O)C(CC)=CC(C=2C3=CC=CC=C3C=C3OC(C)=C(C)C3=2)=C1 LLFOKYWCITZTHK-UHFFFAOYSA-N 0.000 claims 1
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IDVHXQYUFVMOMB-UHFFFAOYSA-N 3-(2,3-dimethylbenzo[f][1]benzofuran-4-yl)-2-ethylphenol Chemical compound CC1=C(C2=C(O1)C=C1C=CC=CC1=C2C=1C(=C(C=CC=1)O)CC)C IDVHXQYUFVMOMB-UHFFFAOYSA-N 0.000 claims 1
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HDNVQNGQIMQDFS-UHFFFAOYSA-N [2-cyclopentyl-4-(2,3-dimethylbenzo[f][1]benzofuran-4-yl)phenyl] acetate Chemical compound CC(=O)OC1=CC=C(C=2C3=CC=CC=C3C=C3OC(C)=C(C)C3=2)C=C1C1CCCC1 HDNVQNGQIMQDFS-UHFFFAOYSA-N 0.000 claims 1
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125000001041 indolyl group Chemical group 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
ZPNFWUPYTFPOJU-LPYSRVMUSA-N iniprol Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC=4C=CC=CC=4)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC2=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]2N(CCC2)C(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N2[C@@H](CCC2)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N2[C@@H](CCC2)C(=O)N3)C(=O)NCC(=O)NCC(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](C(=O)N1)C(C)C)[C@@H](C)O)[C@@H](C)CC)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 ZPNFWUPYTFPOJU-LPYSRVMUSA-N 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
230000003914 insulin secretion Effects 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000012336 iodinating agent Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
NWMAFUPEQLTLPX-UHFFFAOYSA-N iodo(iodomethoxy)methane Chemical class ICOCI NWMAFUPEQLTLPX-UHFFFAOYSA-N 0.000 description 1
210000004153 islets of langerhan Anatomy 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
GDBQQVLCIARPGH-ULQDDVLXSA-N leupeptin Chemical compound CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCN=C(N)N GDBQQVLCIARPGH-ULQDDVLXSA-N 0.000 description 1
108010052968 leupeptin Proteins 0.000 description 1
150000002641 lithium Chemical class 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
HMRCZKQIOFZACX-UHFFFAOYSA-N lithium;trimethylsilylazanide Chemical compound [Li+].C[Si](C)(C)[NH-] HMRCZKQIOFZACX-UHFFFAOYSA-N 0.000 description 1
210000001853 liver microsome Anatomy 0.000 description 1
238000011068 loading method Methods 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 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
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
210000004379 membrane Anatomy 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
UCOSFDFCEQMRFM-WJOKGBTCSA-N methyl (2r)-2-[2-cyclopentyl-4-(2,3-dimethylbenzo[f][1]benzothiol-4-yl)phenoxy]-3-phenylpropanoate Chemical compound C([C@H](C(=O)OC)OC=1C(=CC(=CC=1)C=1C2=CC=CC=C2C=C2SC(C)=C(C)C2=1)C1CCCC1)C1=CC=CC=C1 UCOSFDFCEQMRFM-WJOKGBTCSA-N 0.000 description 1
XQNWHSQJQDPKBG-GDLZYMKVSA-N methyl (2r)-2-[4-(2,3-dimethylbenzo[f][1]benzothiol-4-yl)-2-propan-2-ylphenoxy]-3-phenylpropanoate Chemical compound C([C@H](C(=O)OC)OC=1C(=CC(=CC=1)C=1C2=CC=CC=C2C=C2SC(C)=C(C)C2=1)C(C)C)C1=CC=CC=C1 XQNWHSQJQDPKBG-GDLZYMKVSA-N 0.000 description 1
VRLKBMWMAQFZHP-AREMUKBSSA-N methyl (2r)-2-[4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-2,6-dimethylphenoxy]-3-phenylpropanoate Chemical compound C([C@H](C(=O)OC)OC=1C(=CC(=CC=1C)C=1C2=CC=CC=C2C(Br)=C2SC(C)=C(C)C2=1)C)C1=CC=CC=C1 VRLKBMWMAQFZHP-AREMUKBSSA-N 0.000 description 1
UCGZTBKHBYBLPZ-SSEXGKCCSA-N methyl (2r)-2-[4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-2-cyclopentylphenoxy]-3-phenylpropanoate Chemical compound C([C@H](C(=O)OC)OC=1C(=CC(=CC=1)C=1C2=CC=CC=C2C(Br)=C2SC(C)=C(C)C2=1)C1CCCC1)C1=CC=CC=C1 UCGZTBKHBYBLPZ-SSEXGKCCSA-N 0.000 description 1
PEGZOXFHIDEKBO-RUZDIDTESA-N methyl (2r)-2-[4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-2-fluorophenoxy]-3-phenylpropanoate Chemical compound C([C@H](C(=O)OC)OC=1C(=CC(=CC=1)C=1C2=CC=CC=C2C(Br)=C2SC(C)=C(C)C2=1)F)C1=CC=CC=C1 PEGZOXFHIDEKBO-RUZDIDTESA-N 0.000 description 1
ANVPOIVRQSOYPI-UHFFFAOYSA-N methyl 2-[4-(9-bromo-2,3-dimethylbenzo[f][1]benzothiol-4-yl)-2,6-di(propan-2-yl)phenoxy]acetate Chemical compound C1=C(C(C)C)C(OCC(=O)OC)=C(C(C)C)C=C1C1=C(C(C)=C(C)S2)C2=C(Br)C2=CC=CC=C12 ANVPOIVRQSOYPI-UHFFFAOYSA-N 0.000 description 1
RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 description 1
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235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000002763 monocarboxylic acids Chemical class 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
238000010172 mouse model Methods 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
YFCUZWYIPBUQBD-ZOWNYOTGSA-N n-[(3s)-7-amino-1-chloro-2-oxoheptan-3-yl]-4-methylbenzenesulfonamide;hydron;chloride Chemical compound Cl.CC1=CC=C(S(=O)(=O)N[C@@H](CCCCN)C(=O)CCl)C=C1 YFCUZWYIPBUQBD-ZOWNYOTGSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
238000007410 oral glucose tolerance test Methods 0.000 description 1
239000008203 oral pharmaceutical composition Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001979 organolithium group Chemical group 0.000 description 1
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 1
239000008188 pellet Substances 0.000 description 1
108010091212 pepstatin Proteins 0.000 description 1
FAXGPCHRFPCXOO-LXTPJMTPSA-N pepstatin A Chemical compound OC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)C[C@H](O)[C@H](CC(C)C)NC(=O)[C@H](C(C)C)NC(=O)[C@H](C(C)C)NC(=O)CC(C)C FAXGPCHRFPCXOO-LXTPJMTPSA-N 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229940049953 phenylacetate Drugs 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
150000003009 phosphonic acids Chemical class 0.000 description 1
230000026731 phosphorylation Effects 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
108091008695 photoreceptors Proteins 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000013641 positive control Substances 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
229920003124 powdered cellulose Polymers 0.000 description 1
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239000002244 precipitate Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
150000003858 primary carboxamides Chemical group 0.000 description 1
238000012545 processing Methods 0.000 description 1
OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 1
238000002731 protein assay Methods 0.000 description 1
230000009822 protein phosphorylation Effects 0.000 description 1
QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000000523 sample Substances 0.000 description 1
238000012216 screening Methods 0.000 description 1
230000019491 signal transduction Effects 0.000 description 1
230000011664 signaling Effects 0.000 description 1
102000035025 signaling receptors Human genes 0.000 description 1
108091005475 signaling receptors Proteins 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
VLHOVNZJTJUSQU-UHFFFAOYSA-M sodium;carbonofluoridate Chemical compound [Na+].[O-]C(F)=O VLHOVNZJTJUSQU-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
210000002820 sympathetic nervous system Anatomy 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000007916 tablet composition Substances 0.000 description 1
239000007885 tablet disintegrant Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 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
238000012956 testing procedure Methods 0.000 description 1
230000035924 thermogenesis Effects 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
150000003577 thiophenes Chemical class 0.000 description 1
238000004448 titration Methods 0.000 description 1
238000000844 transformation Methods 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
230000002792 vascular Effects 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1
239000000230 xanthan gum Substances 0.000 description 1
235000010493 xanthan gum Nutrition 0.000 description 1
229920001285 xanthan gum Polymers 0.000 description 1
229940082509 xanthan gum Drugs 0.000 description 1

Classifications

- 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
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
- 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
- A61P3/08—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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/60—Naphtho [b] pyrroles; Hydrogenated naphtho [b] pyrroles
- 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
- C07D333/74—Naphthothiophenes

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Diabetes (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (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)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Endocrinology (AREA)
Hematology (AREA)
Obesity (AREA)
Emergency Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Furan Compounds (AREA)

SK1699-2000A 1998-05-12 1999-05-10 Benzotiofény, benzofurány, indoly, farmaceutický prostriedok s ich obsahom a ich použitie SK16992000A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US7671298A	1998-05-12	1998-05-12
PCT/US1999/010209 WO1999061435A1 (en)	1998-05-12	1999-05-10	Benzothiophenes, benzofurans, and indoles useful in the treatment of insulin resistance and hyperglycemia

Publications (1)

Publication Number	Publication Date
SK16992000A3 true SK16992000A3 (sk)	2001-04-09

Family

ID=22133746

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1699-2000A SK16992000A3 (sk)	1998-05-12	1999-05-10	Benzotiofény, benzofurány, indoly, farmaceutický prostriedok s ich obsahom a ich použitie

Country Status (22)

Country	Link
EP (1)	EP1077969A1 (bg)
JP (1)	JP2002516321A (bg)
KR (1)	KR20010043539A (bg)
CN (1)	CN1308626A (bg)
AR (1)	AR015294A1 (bg)
AU (1)	AU756337B2 (bg)
BG (1)	BG104918A (bg)
BR (1)	BR9911779A (bg)
CA (1)	CA2330620A1 (bg)
EA (1)	EA200001175A1 (bg)
EE (1)	EE200000653A (bg)
HR (1)	HRP20000767A2 (bg)
HU (1)	HUP0101792A3 (bg)
ID (1)	ID26244A (bg)
IL (1)	IL139132A0 (bg)
NO (1)	NO20005677L (bg)
PL (1)	PL344081A1 (bg)
SK (1)	SK16992000A3 (bg)
TR (1)	TR200003333T2 (bg)
TW (1)	TW510900B (bg)
WO (1)	WO1999061435A1 (bg)
ZA (1)	ZA200005961B (bg)

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- 1999-05-10 JP JP2000550841A patent/JP2002516321A/ja active Pending
- 1999-05-10 EE EEP200000653A patent/EE200000653A/xx unknown
- 1999-05-10 SK SK1699-2000A patent/SK16992000A3/sk unknown
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- 1999-05-10 WO PCT/US1999/010209 patent/WO1999061435A1/en not_active Application Discontinuation
- 1999-05-10 AU AU38939/99A patent/AU756337B2/en not_active Ceased
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- 1999-05-10 ID IDW20002311A patent/ID26244A/id unknown
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- 1999-05-10 CA CA002330620A patent/CA2330620A1/en not_active Abandoned
- 1999-05-10 KR KR1020007012649A patent/KR20010043539A/ko not_active Application Discontinuation
- 1999-05-10 EP EP99921829A patent/EP1077969A1/en not_active Withdrawn
- 1999-05-12 AR ARP990102229A patent/AR015294A1/es unknown
2000
- 2000-10-24 ZA ZA200005961A patent/ZA200005961B/xx unknown
- 2000-11-07 BG BG104918A patent/BG104918A/bg unknown
- 2000-11-10 NO NO20005677A patent/NO20005677L/no not_active Application Discontinuation
- 2000-11-10 HR HR20000767A patent/HRP20000767A2/hr not_active Application Discontinuation

Also Published As

Publication number	Publication date
WO1999061435A1 (en)	1999-12-02
JP2002516321A (ja)	2002-06-04
TW510900B (en)	2002-11-21
BR9911779A (pt)	2001-02-06
HUP0101792A3 (en)	2003-01-28
KR20010043539A (ko)	2001-05-25
AR015294A1 (es)	2001-04-18
EE200000653A (et)	2002-04-15
ID26244A (id)	2000-12-07
AU756337B2 (en)	2003-01-09
NO20005677L (no)	2000-12-05
AU3893999A (en)	1999-12-13
NO20005677D0 (no)	2000-11-10
CN1308626A (zh)	2001-08-15
HRP20000767A2 (en)	2001-10-31
ZA200005961B (en)	2001-10-24
BG104918A (bg)	2001-08-31
TR200003333T2 (tr)	2001-02-21
IL139132A0 (en)	2001-11-25
HUP0101792A2 (hu)	2002-01-28
EA200001175A1 (ru)	2001-06-25
CA2330620A1 (en)	1999-12-02
EP1077969A1 (en)	2001-02-28
PL344081A1 (en)	2001-09-24

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