JP2007505083A5 - - Google Patents
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- Publication number
- JP2007505083A5 JP2007505083A5 JP2006525827A JP2006525827A JP2007505083A5 JP 2007505083 A5 JP2007505083 A5 JP 2007505083A5 JP 2006525827 A JP2006525827 A JP 2006525827A JP 2006525827 A JP2006525827 A JP 2006525827A JP 2007505083 A5 JP2007505083 A5 JP 2007505083A5
- Authority
- JP
- Japan
- Prior art keywords
- benzothiazol
- acetonitrile
- pyrimidin
- amino
- ethyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 67
- -1 C 1 -C 6 - alkoxy Chemical group 0.000 claims 33
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- 125000003118 aryl group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 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 claims 6
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 102000004877 Insulin Human genes 0.000 claims 3
- 108090001061 Insulin Proteins 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 229940125396 insulin Drugs 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- SEAQTHCVAGBRFY-INWYIAFRSA-N (2r,4s)-6-fluoro-2-methylspiro[2,3-dihydrochromene-4,5'-imidazolidine]-2',4'-dione Chemical compound C([C@H](OC1=CC=C(F)C=C11)C)[C@@]21NC(=O)NC2=O SEAQTHCVAGBRFY-INWYIAFRSA-N 0.000 claims 2
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 2
- 206010022489 Insulin Resistance Diseases 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical class C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 108010026951 Short-Acting Insulin Proteins 0.000 claims 2
- 229940123958 Short-acting insulin Drugs 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- CHNUOJQWGUIOLD-NFZZJPOKSA-N epalrestat Chemical compound C=1C=CC=CC=1\C=C(/C)\C=C1/SC(=S)N(CC(O)=O)C1=O CHNUOJQWGUIOLD-NFZZJPOKSA-N 0.000 claims 2
- 229950010170 epalrestat Drugs 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- 229960003069 tolrestat Drugs 0.000 claims 2
- LUBHDINQXIHVLS-UHFFFAOYSA-N tolrestat Chemical compound OC(=O)CN(C)C(=S)C1=CC=CC2=C(C(F)(F)F)C(OC)=CC=C21 LUBHDINQXIHVLS-UHFFFAOYSA-N 0.000 claims 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims 1
- WAAPEIZFCHNLKK-UFBFGSQYSA-N (2s,4s)-6-fluoro-2',5'-dioxospiro[2,3-dihydrochromene-4,4'-imidazolidine]-2-carboxamide Chemical compound C([C@H](OC1=CC=C(F)C=C11)C(=O)N)[C@@]21NC(=O)NC2=O WAAPEIZFCHNLKK-UFBFGSQYSA-N 0.000 claims 1
- BMHZAHGTGIZZCT-LJQANCHMSA-N (4r)-2-[(4-bromo-2-fluorophenyl)methyl]-6-fluorospiro[isoquinoline-4,3'-pyrrolidine]-1,2',3,5'-tetrone Chemical compound C1([C@]2(C(NC(=O)C2)=O)C2=O)=CC(F)=CC=C1C(=O)N2CC1=CC=C(Br)C=C1F BMHZAHGTGIZZCT-LJQANCHMSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- ZJSUDHQFSBHLDV-UHFFFAOYSA-N 1-[(3-bromo-1-benzofuran-2-yl)sulfonyl]imidazolidine-2,4-dione Chemical compound O1C2=CC=CC=C2C(Br)=C1S(=O)(=O)N1CC(=O)NC1=O ZJSUDHQFSBHLDV-UHFFFAOYSA-N 0.000 claims 1
- QCCHBHSAIQIQGO-UHFFFAOYSA-N 2,7-difluorospiro[fluorene-9,5'-imidazolidine]-2',4'-dione Chemical compound C12=CC(F)=CC=C2C2=CC=C(F)C=C2C21NC(=O)NC2=O QCCHBHSAIQIQGO-UHFFFAOYSA-N 0.000 claims 1
- PKNYJVSQHRVGTB-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2-(2-methoxypyrimidin-4-yl)acetonitrile Chemical compound COC1=NC=CC(C(C#N)C=2SC3=CC=CC=C3N=2)=N1 PKNYJVSQHRVGTB-UHFFFAOYSA-N 0.000 claims 1
- YUVRNNOCMJJUCI-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2-(2-phenylmethoxypyrimidin-4-yl)acetonitrile 2-(1,3-benzothiazol-2-yl)-2-[2-(2H-tetrazol-5-ylmethylamino)pyrimidin-4-yl]acetonitrile Chemical compound N=1C2=CC=CC=C2SC=1C(C#N)C(N=1)=CC=NC=1NCC1=NN=NN1.N=1C2=CC=CC=C2SC=1C(C#N)C(N=1)=CC=NC=1OCC1=CC=CC=C1 YUVRNNOCMJJUCI-UHFFFAOYSA-N 0.000 claims 1
- ZZIAFWOQBREWEQ-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2-[2-(2-phenylethylamino)pyrimidin-4-yl]acetonitrile 2-(1,3-benzothiazol-2-yl)-2-(2-pyrrolidin-1-ylpyrimidin-4-yl)acetonitrile Chemical compound N=1C2=CC=CC=C2SC=1C(C#N)C(N=1)=CC=NC=1N1CCCC1.N=1C2=CC=CC=C2SC=1C(C#N)C(N=1)=CC=NC=1NCCC1=CC=CC=C1 ZZIAFWOQBREWEQ-UHFFFAOYSA-N 0.000 claims 1
- LVNXDCHGOBMXPF-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2-[2-(4-methylpiperazin-1-yl)pyrimidin-4-yl]acetonitrile 2-(1,3-benzothiazol-2-yl)-2-(2-morpholin-4-ylpyrimidin-4-yl)acetonitrile Chemical compound N=1C2=CC=CC=C2SC=1C(C#N)C(N=1)=CC=NC=1N1CCOCC1.C1CN(C)CCN1C1=NC=CC(C(C#N)C=2SC3=CC=CC=C3N=2)=N1 LVNXDCHGOBMXPF-UHFFFAOYSA-N 0.000 claims 1
- ALFIAYHEMBNSLM-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2-[2-(methylamino)pyrimidin-4-yl]acetonitrile 2-(1,3-benzothiazol-2-yl)-2-[2-[4-(2-morpholin-4-ylethyl)piperazin-1-yl]pyrimidin-4-yl]acetonitrile Chemical compound CNC1=NC=CC(C(C#N)C=2SC3=CC=CC=C3N=2)=N1.N=1C2=CC=CC=C2SC=1C(C#N)C(N=1)=CC=NC=1N(CC1)CCN1CCN1CCOCC1 ALFIAYHEMBNSLM-UHFFFAOYSA-N 0.000 claims 1
- IRUYJPYDSSPSLG-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2-[2-(pyridin-4-ylmethoxy)pyrimidin-4-yl]acetonitrile 2-(1,3-benzothiazol-2-yl)-2-[2-[(4-pyridin-3-ylphenyl)methoxy]pyrimidin-4-yl]acetonitrile Chemical compound N=1C2=CC=CC=C2SC=1C(C#N)C(N=1)=CC=NC=1OCC1=CC=NC=C1.N=1C2=CC=CC=C2SC=1C(C#N)C(N=1)=CC=NC=1OCC(C=C1)=CC=C1C1=CC=CN=C1 IRUYJPYDSSPSLG-UHFFFAOYSA-N 0.000 claims 1
- BIDRVSQGIUDCOE-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2-[2-[2-(4-hydroxyphenyl)ethylamino]pyrimidin-4-yl]acetonitrile Chemical compound C1=CC(O)=CC=C1CCNC1=NC=CC(C(C#N)C=2SC3=CC=CC=C3N=2)=N1 BIDRVSQGIUDCOE-UHFFFAOYSA-N 0.000 claims 1
- GRMMETGASZZNCC-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2-[2-[3-(dimethylamino)propylamino]pyrimidin-4-yl]acetonitrile Chemical compound CN(C)CCCNC1=NC=CC(C(C#N)C=2SC3=CC=CC=C3N=2)=N1 GRMMETGASZZNCC-UHFFFAOYSA-N 0.000 claims 1
- OCPKDAUTBFRFJR-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2-[2-[4-[3-(trifluoromethylsulfonyl)anilino]piperidin-1-yl]pyrimidin-4-yl]acetonitrile Chemical compound FC(F)(F)S(=O)(=O)C1=CC=CC(NC2CCN(CC2)C=2N=C(C=CN=2)C(C#N)C=2SC3=CC=CC=C3N=2)=C1 OCPKDAUTBFRFJR-UHFFFAOYSA-N 0.000 claims 1
- XJPGQODRLCGCEX-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2-[2-[[4-(piperazin-1-ylmethyl)phenyl]methoxy]pyrimidin-4-yl]acetonitrile Chemical compound N=1C2=CC=CC=C2SC=1C(C#N)C(N=1)=CC=NC=1OCC(C=C1)=CC=C1CN1CCNCC1 XJPGQODRLCGCEX-UHFFFAOYSA-N 0.000 claims 1
- BEECSAAPHNLHIJ-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2-[2-[[4-[(4-formylpiperazin-1-yl)methyl]phenyl]methoxy]pyrimidin-4-yl]acetonitrile Chemical compound C1CN(C=O)CCN1CC(C=C1)=CC=C1COC1=NC=CC(C(C#N)C=2SC3=CC=CC=C3N=2)=N1 BEECSAAPHNLHIJ-UHFFFAOYSA-N 0.000 claims 1
- ZSSFFXPVIKQLKX-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)-2-[5-bromo-2-[2-(dimethylamino)ethylamino]pyrimidin-4-yl]acetonitrile 2-(1,3-benzothiazol-2-yl)-2-[2-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]acetonitrile Chemical compound CN(C)CCNC1=NC=C(Br)C(C(C#N)C=2SC3=CC=CC=C3N=2)=N1.N=1C2=CC=CC=C2SC=1C(C#N)C(N=1)=CC=NC=1NCCN1CCOCC1 ZSSFFXPVIKQLKX-UHFFFAOYSA-N 0.000 claims 1
- ZMZSYUSDGRJZNT-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-yl)acetonitrile Chemical compound C1=CC=C2SC(CC#N)=NC2=C1 ZMZSYUSDGRJZNT-UHFFFAOYSA-N 0.000 claims 1
- PGSHIGZRDRODHI-UHFFFAOYSA-N 2-(3h-1,3-benzothiazol-2-ylidene)-2-[2-[[4-[(4-ethylpiperazin-1-yl)methyl]phenyl]methoxy]pyrimidin-4-yl]acetonitrile Chemical compound C1CN(CC)CCN1CC(C=C1)=CC=C1COC1=NC=CC(C(C#N)=C2SC3=CC=CC=C3N2)=N1 PGSHIGZRDRODHI-UHFFFAOYSA-N 0.000 claims 1
- VGKVFERUIRFOKX-UHFFFAOYSA-N 2-(3h-1,3-benzothiazol-2-ylidene)-2-[2-[[4-[[4-(2-hydroxyethyl)piperazin-1-yl]methyl]phenyl]methoxy]pyrimidin-4-yl]acetonitrile Chemical compound C1CN(CCO)CCN1CC(C=C1)=CC=C1COC1=NC=CC(C(C#N)=C2SC3=CC=CC=C3N2)=N1 VGKVFERUIRFOKX-UHFFFAOYSA-N 0.000 claims 1
- FNCDTXZTVYLDJK-UHFFFAOYSA-N 2-(3h-1,3-benzothiazol-2-ylidene)-2-[2-[[4-[[4-(2-methoxyethyl)piperazin-1-yl]methyl]phenyl]methoxy]pyrimidin-4-yl]acetonitrile Chemical compound C1CN(CCOC)CCN1CC(C=C1)=CC=C1COC1=NC=CC(C(C#N)=C2SC3=CC=CC=C3N2)=N1 FNCDTXZTVYLDJK-UHFFFAOYSA-N 0.000 claims 1
- KYWRNCCCDDBXBJ-UHFFFAOYSA-N 2-[2-[[4-[(4-acetylpiperazin-1-yl)methyl]phenyl]methoxy]pyrimidin-4-yl]-2-(1,3-benzothiazol-2-yl)acetonitrile Chemical compound C1CN(C(=O)C)CCN1CC(C=C1)=CC=C1COC1=NC=CC(C(C#N)C=2SC3=CC=CC=C3N=2)=N1 KYWRNCCCDDBXBJ-UHFFFAOYSA-N 0.000 claims 1
- AECJEFDDXQMHSC-UHFFFAOYSA-N 2-[2-[[4-[[4-(2-aminoacetyl)piperazin-1-yl]methyl]phenyl]methoxy]pyrimidin-4-yl]-2-(3h-1,3-benzothiazol-2-ylidene)acetonitrile Chemical compound C1CN(C(=O)CN)CCN1CC(C=C1)=CC=C1COC1=NC=CC(C(C#N)=C2SC3=CC=CC=C3N2)=N1 AECJEFDDXQMHSC-UHFFFAOYSA-N 0.000 claims 1
- YREIRIKJAMPPHC-UHFFFAOYSA-N 2-[3-[(3-nitrophenyl)methyl]-2,4,5-trioxoimidazolidin-1-yl]acetic acid Chemical compound O=C1C(=O)N(CC(=O)O)C(=O)N1CC1=CC=CC([N+]([O-])=O)=C1 YREIRIKJAMPPHC-UHFFFAOYSA-N 0.000 claims 1
- LKBFFDOJUKLQNY-UHFFFAOYSA-N 2-[3-[(4-bromo-2-fluorophenyl)methyl]-4-oxo-1-phthalazinyl]acetic acid Chemical compound O=C1C2=CC=CC=C2C(CC(=O)O)=NN1CC1=CC=C(Br)C=C1F LKBFFDOJUKLQNY-UHFFFAOYSA-N 0.000 claims 1
- BEGJKQPWVJRBPU-UHFFFAOYSA-N 2-[3-methyl-5-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]phenyl]acetic acid Chemical compound CC1=CC(CC(O)=O)=CC(CC=2SC3=C(F)C=C(F)C(F)=C3N=2)=C1 BEGJKQPWVJRBPU-UHFFFAOYSA-N 0.000 claims 1
- BUYWFAJWTSIACV-UHFFFAOYSA-N 2-[3-oxo-4-[(4,5,7-trifluoro-1,3-benzothiazol-2-yl)methyl]-1,4-benzothiazin-2-yl]acetic acid Chemical compound FC1=CC(F)=C2SC(CN3C4=CC=CC=C4SC(C3=O)CC(=O)O)=NC2=C1F BUYWFAJWTSIACV-UHFFFAOYSA-N 0.000 claims 1
- YVVTYSYWNBMCMH-UHFFFAOYSA-N 2-[4-[[4-[[4-[3h-1,3-benzothiazol-2-ylidene(cyano)methyl]pyrimidin-2-yl]oxymethyl]phenyl]methyl]piperazin-1-yl]acetamide Chemical compound C1CN(CC(=O)N)CCN1CC(C=C1)=CC=C1COC1=NC=CC(C(C#N)=C2SC3=CC=CC=C3N2)=N1 YVVTYSYWNBMCMH-UHFFFAOYSA-N 0.000 claims 1
- BCSVCWVQNOXFGL-UHFFFAOYSA-N 3,4-dihydro-4-oxo-3-((5-trifluoromethyl-2-benzothiazolyl)methyl)-1-phthalazine acetic acid Chemical compound O=C1C2=CC=CC=C2C(CC(=O)O)=NN1CC1=NC2=CC(C(F)(F)F)=CC=C2S1 BCSVCWVQNOXFGL-UHFFFAOYSA-N 0.000 claims 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- KLUBTNKBAIYKRM-UHFFFAOYSA-N 4-[[4-[[4-[3h-1,3-benzothiazol-2-ylidene(cyano)methyl]pyrimidin-2-yl]oxymethyl]phenyl]methyl]-n,n-dimethylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1CC(C=C1)=CC=C1COC1=NC=CC(C(C#N)=C2SC3=CC=CC=C3N2)=N1 KLUBTNKBAIYKRM-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- WSYVVXHNGMBHFS-UHFFFAOYSA-N 7-[3-[(4-boronophenoxy)methyl]-1,5-dimethylpyrazolidin-4-yl]-3-(3-naphthalen-1-yloxypropyl)-2,3-dihydro-1H-indole-2-carboxylic acid Chemical compound CC1C(C(COc2ccc(cc2)B(O)O)NN1C)c1cccc2C(CCCOc3cccc4ccccc34)C(Nc12)C(O)=O WSYVVXHNGMBHFS-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 claims 1
- 229940123208 Biguanide Drugs 0.000 claims 1
- VIVXQUJHDKZCRT-UHFFFAOYSA-N C(C)(=O)N1CCN(CC1)C1=CC=C(OC2=NC=CC(=N2)C(C#N)C=2SC3=C(N2)C=CC=C3)C=C1.S1C(=NC3=C1C=CC=C3)C(C#N)C3=NC(=NC=C3)OC3=CC=C(C=C3)OCCCC Chemical compound C(C)(=O)N1CCN(CC1)C1=CC=C(OC2=NC=CC(=N2)C(C#N)C=2SC3=C(N2)C=CC=C3)C=C1.S1C(=NC3=C1C=CC=C3)C(C#N)C3=NC(=NC=C3)OC3=CC=C(C=C3)OCCCC VIVXQUJHDKZCRT-UHFFFAOYSA-N 0.000 claims 1
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| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| EP2382975A3 (en) | 2006-05-09 | 2012-02-29 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| EA016853B1 (ru) | 2006-08-24 | 2012-08-30 | Юниверсити Оф Теннесси Рисерч Фаундейшн | Замещенные ациланилиды и их применение |
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| US10987334B2 (en) | 2012-07-13 | 2021-04-27 | University Of Tennessee Research Foundation | Method of treating ER mutant expressing breast cancers with selective androgen receptor modulators (SARMs) |
| US10314807B2 (en) | 2012-07-13 | 2019-06-11 | Gtx, Inc. | Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS) |
| US9622992B2 (en) | 2012-07-13 | 2017-04-18 | Gtx, Inc. | Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMs) |
| WO2014011220A2 (en) | 2012-07-13 | 2014-01-16 | Gtx, Inc. | A method of treating androgen receptor (ar)-positive breast cancers with selective androgen receptor modulator (sarms) |
| US10258596B2 (en) | 2012-07-13 | 2019-04-16 | Gtx, Inc. | Method of treating HER2-positive breast cancers with selective androgen receptor modulators (SARMS) |
| US9744149B2 (en) | 2012-07-13 | 2017-08-29 | Gtx, Inc. | Method of treating androgen receptor (AR)-positive breast cancers with selective androgen receptor modulator (SARMs) |
| US9969683B2 (en) | 2012-07-13 | 2018-05-15 | Gtx, Inc. | Method of treating estrogen receptor (ER)-positive breast cancers with selective androgen receptor modulator (SARMS) |
| CN104903331A (zh) * | 2013-01-24 | 2015-09-09 | 山东亨利医药科技有限责任公司 | Jnk抑制剂 |
| WO2017025980A2 (en) * | 2015-08-12 | 2017-02-16 | Shoolineuniversity Of Biotechnology And Management Sciences | Novel benzothiazole derivatives with enhanced biological activity |
| CN115887434B (zh) * | 2022-11-23 | 2024-12-24 | 四川大学 | 具有抗氧化作用的药物用于制备治疗多囊卵巢综合征药物的用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1176269A (en) * | 1981-03-02 | 1984-10-16 | Kazimir Sestanj | N-naphthoylglycine derivatives |
| US4927831A (en) * | 1988-10-20 | 1990-05-22 | American Home Products | Spiro-isoquinoline-pyrrolidine tetrones and analogs thereof useful as aldose reductase inhibitors |
| US6559188B1 (en) * | 1999-09-17 | 2003-05-06 | Novartis Ag | Method of treating metabolic disorders especially diabetes, or a disease or condition associated with diabetes |
| EP1110957A1 (en) * | 1999-12-24 | 2001-06-27 | Applied Research Systems ARS Holding N.V. | Benzazole derivatives and their use as JNK modulators |
| DE60215042T2 (de) * | 2001-12-07 | 2007-10-04 | Applied Research Systems Ars Holding N.V. | Benzazole derivate zur behandlung von scleroderma |
| IL164796A0 (en) * | 2002-04-25 | 2005-12-18 | Applied Res | Piperazine benzothiazole derivatives, their preparation, pharmaceutical compositions containing themand their use |
-
2004
- 2004-09-08 DE DE602004010178T patent/DE602004010178T2/de not_active Expired - Lifetime
- 2004-09-08 ES ES04787110T patent/ES2297494T3/es not_active Expired - Lifetime
- 2004-09-08 JP JP2006525827A patent/JP5021307B2/ja not_active Expired - Fee Related
- 2004-09-08 HR HR20070527T patent/HRP20070527T3/xx unknown
- 2004-09-08 PL PL04787110T patent/PL1696909T3/pl unknown
- 2004-09-08 SI SI200430550T patent/SI1696909T1/sl unknown
- 2004-09-08 CA CA2534314A patent/CA2534314C/en not_active Expired - Fee Related
- 2004-09-08 EP EP04787110A patent/EP1696909B1/en not_active Expired - Lifetime
- 2004-09-08 WO PCT/EP2004/052090 patent/WO2005025567A1/en not_active Ceased
- 2004-09-08 DK DK04787110T patent/DK1696909T3/da active
- 2004-09-08 US US10/571,291 patent/US20070088017A1/en not_active Abandoned
- 2004-09-08 PT PT04787110T patent/PT1696909E/pt unknown
- 2004-09-08 AU AU2004271740A patent/AU2004271740B2/en not_active Ceased
- 2004-09-08 AT AT04787110T patent/ATE378047T1/de active
-
2006
- 2006-03-12 IL IL174250A patent/IL174250A/en not_active IP Right Cessation
- 2006-04-07 NO NO20061600A patent/NO20061600L/no not_active Application Discontinuation
-
2007
- 2007-12-04 CY CY20071101543T patent/CY1107820T1/el unknown
-
2013
- 2013-10-08 US US14/048,690 patent/US20140107116A1/en not_active Abandoned
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