RU2297243C2 - Ингибиторы киназы-3 гликогенсинтазы (gsk-3) для лечения глаукомы - Google Patents
Ингибиторы киназы-3 гликогенсинтазы (gsk-3) для лечения глаукомы Download PDFInfo
- Publication number
- RU2297243C2 RU2297243C2 RU2004112766/14A RU2004112766A RU2297243C2 RU 2297243 C2 RU2297243 C2 RU 2297243C2 RU 2004112766/14 A RU2004112766/14 A RU 2004112766/14A RU 2004112766 A RU2004112766 A RU 2004112766A RU 2297243 C2 RU2297243 C2 RU 2297243C2
- Authority
- RU
- Russia
- Prior art keywords
- amino
- triazole
- anilino
- phenylaminothiazol
- methanone
- Prior art date
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- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 title claims abstract description 39
- 239000003112 inhibitor Substances 0.000 title claims abstract description 26
- 208000010412 Glaucoma Diseases 0.000 title claims description 25
- 102000001267 GSK3 Human genes 0.000 title abstract 2
- 101150090422 gsk-3 gene Proteins 0.000 title 1
- 230000004410 intraocular pressure Effects 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 33
- CRDNMYFJWFXOCH-YPKPFQOOSA-N (3z)-3-(3-oxo-1h-indol-2-ylidene)-1h-indol-2-one Chemical class N/1C2=CC=CC=C2C(=O)C\1=C1/C2=CC=CC=C2NC1=O CRDNMYFJWFXOCH-YPKPFQOOSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 10
- CRDNMYFJWFXOCH-BUHFOSPRSA-N Couroupitine B Natural products N\1C2=CC=CC=C2C(=O)C/1=C1/C2=CC=CC=C2NC1=O CRDNMYFJWFXOCH-BUHFOSPRSA-N 0.000 claims description 8
- -1 indirubin sulfonamide Chemical class 0.000 claims description 8
- CRDNMYFJWFXOCH-UHFFFAOYSA-N isoindigotin Natural products N1C2=CC=CC=C2C(=O)C1=C1C2=CC=CC=C2NC1=O CRDNMYFJWFXOCH-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- ATBAETXFFCOZOY-UHFFFAOYSA-N hymenialdisine Natural products N1C(N)=NC(=O)C1=C1C(C=C(Br)N2)=C2C(=O)NCC1 ATBAETXFFCOZOY-UHFFFAOYSA-N 0.000 claims description 7
- QPCBNXNDVYOBIP-WHFBIAKZSA-N hymenialdisine Chemical compound NC1=NC(=O)C([C@@H]2[C@@H]3C=C(Br)N=C3C(=O)NCC2)=N1 QPCBNXNDVYOBIP-WHFBIAKZSA-N 0.000 claims description 6
- WKXCZMFWXZRMEZ-UHFFFAOYSA-N 1,3-thiazole-2,4-diamine Chemical class NC1=CSC(N)=N1 WKXCZMFWXZRMEZ-UHFFFAOYSA-N 0.000 claims description 5
- LJVQHXICFCZRJN-UHFFFAOYSA-N 1h-1,2,4-triazole-5-carboxylic acid Chemical compound OC(=O)C1=NC=NN1 LJVQHXICFCZRJN-UHFFFAOYSA-N 0.000 claims description 5
- AQNWXPHYWRBUPD-UHFFFAOYSA-N (5-amino-3-anilino-1,2,4-triazol-1-yl)-(3-bromophenyl)methanone Chemical compound N=1N(C(=O)C=2C=C(Br)C=CC=2)C(N)=NC=1NC1=CC=CC=C1 AQNWXPHYWRBUPD-UHFFFAOYSA-N 0.000 claims description 4
- CUYIXXWIOGQFRF-ONEGZZNKSA-N (E)-3-(furan-2-yl)-1-(1H-1,2,4-triazol-5-yl)prop-2-en-1-one Chemical compound N1=CNN=C1C(=O)\C=C\C1=CC=CO1 CUYIXXWIOGQFRF-ONEGZZNKSA-N 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 230000000699 topical effect Effects 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 230000004493 normal intraocular pressure Effects 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- UDNXQZJGGDMKKM-UHFFFAOYSA-N (3,5-diamino-1,2,4-triazol-1-yl)-phenylmethanone Chemical compound N1=C(N)N=C(N)N1C(=O)C1=CC=CC=C1 UDNXQZJGGDMKKM-UHFFFAOYSA-N 0.000 claims description 2
- BVNBNSCPHAHTIE-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-(2,6-dichlorophenyl)methanone Chemical compound S1C(C(=O)C=2C(=CC=CC=2Cl)Cl)=C(N)N=C1NC1=CC=CC=C1 BVNBNSCPHAHTIE-UHFFFAOYSA-N 0.000 claims description 2
- XFLAXJFZEBKLQS-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-(2,6-difluorophenyl)methanone Chemical compound S1C(C(=O)C=2C(=CC=CC=2F)F)=C(N)N=C1NC1=CC=CC=C1 XFLAXJFZEBKLQS-UHFFFAOYSA-N 0.000 claims description 2
- CBRJQALCGJQKIP-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-(2-methoxyphenyl)methanone Chemical compound COC1=CC=CC=C1C(=O)C1=C(N)N=C(NC=2C=CC=CC=2)S1 CBRJQALCGJQKIP-UHFFFAOYSA-N 0.000 claims description 2
- GEDMTOFKGPETRL-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-(3,4-dichlorophenyl)methanone Chemical compound S1C(C(=O)C=2C=C(Cl)C(Cl)=CC=2)=C(N)N=C1NC1=CC=CC=C1 GEDMTOFKGPETRL-UHFFFAOYSA-N 0.000 claims description 2
- AWVVZVCWYAVHMC-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-(3,4-difluorophenyl)methanone Chemical compound S1C(C(=O)C=2C=C(F)C(F)=CC=2)=C(N)N=C1NC1=CC=CC=C1 AWVVZVCWYAVHMC-UHFFFAOYSA-N 0.000 claims description 2
- FKVUXPCXYYHCAR-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-(3-fluorophenyl)methanone Chemical compound S1C(C(=O)C=2C=C(F)C=CC=2)=C(N)N=C1NC1=CC=CC=C1 FKVUXPCXYYHCAR-UHFFFAOYSA-N 0.000 claims description 2
- LXKAYWZVBXYTGU-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC=CC=3)S2)N)=C1 LXKAYWZVBXYTGU-UHFFFAOYSA-N 0.000 claims description 2
- PHDVIZKEBAVUCZ-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-(3-methyl-1-benzothiophen-2-yl)methanone Chemical compound S1C2=CC=CC=C2C(C)=C1C(=O)C(=C(N=1)N)SC=1NC1=CC=CC=C1 PHDVIZKEBAVUCZ-UHFFFAOYSA-N 0.000 claims description 2
- XENRODQOGJOOHA-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-(3-phenylmethoxyphenyl)methanone Chemical compound S1C(C(=O)C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=C(N)N=C1NC1=CC=CC=C1 XENRODQOGJOOHA-UHFFFAOYSA-N 0.000 claims description 2
- OUEOKGGLZBYZLG-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-(4-chloro-3-methylphenyl)methanone Chemical compound C1=C(Cl)C(C)=CC(C(=O)C2=C(N=C(NC=3C=CC=CC=3)S2)N)=C1 OUEOKGGLZBYZLG-UHFFFAOYSA-N 0.000 claims description 2
- MBWDTZNLSGZQED-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-(4-fluorophenyl)methanone Chemical compound S1C(C(=O)C=2C=CC(F)=CC=2)=C(N)N=C1NC1=CC=CC=C1 MBWDTZNLSGZQED-UHFFFAOYSA-N 0.000 claims description 2
- MWRZPNGRLYXGKP-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(N)N=C(NC=2C=CC=CC=2)S1 MWRZPNGRLYXGKP-UHFFFAOYSA-N 0.000 claims description 2
- SJYNBJHBIDSODI-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-(4-phenylphenyl)methanone Chemical compound S1C(C(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)=C(N)N=C1NC1=CC=CC=C1 SJYNBJHBIDSODI-UHFFFAOYSA-N 0.000 claims description 2
- YLSSZUIMVBZWMK-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-cyclopropylmethanone Chemical compound S1C(C(=O)C2CC2)=C(N)N=C1NC1=CC=CC=C1 YLSSZUIMVBZWMK-UHFFFAOYSA-N 0.000 claims description 2
- RKBALHPGBQMZOG-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-naphthalen-2-ylmethanone Chemical compound S1C(C(=O)C=2C=C3C=CC=CC3=CC=2)=C(N)N=C1NC1=CC=CC=C1 RKBALHPGBQMZOG-UHFFFAOYSA-N 0.000 claims description 2
- YOZXSIIEHFGLLO-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-phenylmethanone Chemical compound S1C(C(=O)C=2C=CC=CC=2)=C(N)N=C1NC1=CC=CC=C1 YOZXSIIEHFGLLO-UHFFFAOYSA-N 0.000 claims description 2
- BWPYRRUOUILTPU-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-pyridin-2-ylmethanone Chemical compound S1C(C(=O)C=2N=CC=CC=2)=C(N)N=C1NC1=CC=CC=C1 BWPYRRUOUILTPU-UHFFFAOYSA-N 0.000 claims description 2
- LERGLIZTDGVNRO-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-pyridin-3-ylmethanone Chemical compound S1C(C(=O)C=2C=NC=CC=2)=C(N)N=C1NC1=CC=CC=C1 LERGLIZTDGVNRO-UHFFFAOYSA-N 0.000 claims description 2
- WRGGJHVBIVHHSU-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-pyridin-4-ylmethanone Chemical compound S1C(C(=O)C=2C=CN=CC=2)=C(N)N=C1NC1=CC=CC=C1 WRGGJHVBIVHHSU-UHFFFAOYSA-N 0.000 claims description 2
- XPKVIZDAFGYGOY-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-thiophen-2-ylmethanone Chemical compound S1C(C(=O)C=2SC=CC=2)=C(N)N=C1NC1=CC=CC=C1 XPKVIZDAFGYGOY-UHFFFAOYSA-N 0.000 claims description 2
- IFTIYGIGGFHYGS-UHFFFAOYSA-N (4-amino-2-anilino-1,3-thiazol-5-yl)-thiophen-3-ylmethanone Chemical compound S1C(C(=O)C2=CSC=C2)=C(N)N=C1NC1=CC=CC=C1 IFTIYGIGGFHYGS-UHFFFAOYSA-N 0.000 claims description 2
- XSDKWAUOJXYJGA-UHFFFAOYSA-N (5-amino-3-anilino-1,2,4-triazol-1-yl)-(1,3-benzodioxol-5-yl)methanone Chemical compound N=1N(C(=O)C=2C=C3OCOC3=CC=2)C(N)=NC=1NC1=CC=CC=C1 XSDKWAUOJXYJGA-UHFFFAOYSA-N 0.000 claims description 2
- JWHANWDZXLKUDX-UHFFFAOYSA-N (5-amino-3-anilino-1,2,4-triazol-1-yl)-(2-phenoxyphenyl)methanone Chemical compound N=1N(C(=O)C=2C(=CC=CC=2)OC=2C=CC=CC=2)C(N)=NC=1NC1=CC=CC=C1 JWHANWDZXLKUDX-UHFFFAOYSA-N 0.000 claims description 2
- UJNJSOKQSPNASJ-UHFFFAOYSA-N (5-amino-3-anilino-1,2,4-triazol-1-yl)-(3,5-dichlorophenyl)methanone Chemical compound N=1N(C(=O)C=2C=C(Cl)C=C(Cl)C=2)C(N)=NC=1NC1=CC=CC=C1 UJNJSOKQSPNASJ-UHFFFAOYSA-N 0.000 claims description 2
- BMVYDSFWVQQGFZ-UHFFFAOYSA-N (5-amino-3-anilino-1,2,4-triazol-1-yl)-(4-chlorophenyl)methanone Chemical compound N=1N(C(=O)C=2C=CC(Cl)=CC=2)C(N)=NC=1NC1=CC=CC=C1 BMVYDSFWVQQGFZ-UHFFFAOYSA-N 0.000 claims description 2
- HXUFQNJENCXTHZ-UHFFFAOYSA-N (5-amino-3-anilino-1,2,4-triazol-1-yl)-(4-phenylphenyl)methanone Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C(N)=NC=1NC1=CC=CC=C1 HXUFQNJENCXTHZ-UHFFFAOYSA-N 0.000 claims description 2
- WNAZAYNAVGRRAW-UHFFFAOYSA-N (5-amino-3-anilino-1,2,4-triazol-1-yl)-[4-(trifluoromethyl)phenyl]methanone Chemical compound N=1N(C(=O)C=2C=CC(=CC=2)C(F)(F)F)C(N)=NC=1NC1=CC=CC=C1 WNAZAYNAVGRRAW-UHFFFAOYSA-N 0.000 claims description 2
- RBHFKINQTKFFAH-UHFFFAOYSA-N (5-amino-3-anilino-1,2,4-triazol-1-yl)-cyclohexylmethanone Chemical compound N=1N(C(=O)C2CCCCC2)C(N)=NC=1NC1=CC=CC=C1 RBHFKINQTKFFAH-UHFFFAOYSA-N 0.000 claims description 2
- GPWONEKAEXFDIJ-UHFFFAOYSA-N (5-amino-3-anilino-1,2,4-triazol-1-yl)-naphthalen-2-ylmethanone Chemical compound N=1N(C(=O)C=2C=C3C=CC=CC3=CC=2)C(N)=NC=1NC1=CC=CC=C1 GPWONEKAEXFDIJ-UHFFFAOYSA-N 0.000 claims description 2
- MDYVPKCEHAOTPR-UHFFFAOYSA-N (5-amino-3-anilino-1,2,4-triazol-1-yl)-phenylmethanone Chemical compound N=1N(C(=O)C=2C=CC=CC=2)C(N)=NC=1NC1=CC=CC=C1 MDYVPKCEHAOTPR-UHFFFAOYSA-N 0.000 claims description 2
- ZIPTVBLEXXRQIA-UHFFFAOYSA-N 1-(3-amino-5-anilino-1,2,4-triazol-1-yl)-2-cyclopent-2-en-1-ylethanone Chemical compound C1CC=CC1CC(=O)N1N=C(N)N=C1NC1=CC=CC=C1 ZIPTVBLEXXRQIA-UHFFFAOYSA-N 0.000 claims description 2
- COIULFCMHXNEAK-UHFFFAOYSA-N 1-(3-amino-5-anilino-1,2,4-triazol-1-yl)-2-phenylethanone Chemical compound C=1C=CC=CC=1CC(=O)N1N=C(N)N=C1NC1=CC=CC=C1 COIULFCMHXNEAK-UHFFFAOYSA-N 0.000 claims description 2
- ZYCCMMGEMIRHJZ-UHFFFAOYSA-N 1-(4-amino-2-anilino-1,3-thiazol-5-yl)ethanone Chemical compound NC1=C(C(=O)C)SC(NC=2C=CC=CC=2)=N1 ZYCCMMGEMIRHJZ-UHFFFAOYSA-N 0.000 claims description 2
- SZYPURHXPKGDPG-UHFFFAOYSA-N 1-(4-amino-2-anilino-1,3-thiazol-5-yl)propan-1-one Chemical compound NC1=C(C(=O)CC)SC(NC=2C=CC=CC=2)=N1 SZYPURHXPKGDPG-UHFFFAOYSA-N 0.000 claims description 2
- MIJJYKPHIIBMBN-UHFFFAOYSA-N 1-(5-amino-3-anilino-1,2,4-triazol-1-yl)-2-(1h-indol-3-yl)ethanone Chemical compound N=1N(C(=O)CC=2C3=CC=CC=C3NC=2)C(N)=NC=1NC1=CC=CC=C1 MIJJYKPHIIBMBN-UHFFFAOYSA-N 0.000 claims description 2
- JQADZCNSJILHIF-UHFFFAOYSA-N 1-(5-amino-3-anilino-1,2,4-triazol-1-yl)-2-(4-fluorophenyl)ethanone Chemical compound N=1N(C(=O)CC=2C=CC(F)=CC=2)C(N)=NC=1NC1=CC=CC=C1 JQADZCNSJILHIF-UHFFFAOYSA-N 0.000 claims description 2
- JNTYRUUIWJEEJL-UHFFFAOYSA-N 1-(5-amino-3-anilino-1,2,4-triazol-1-yl)-2-(4-phenylphenyl)ethanone Chemical compound N=1N(C(=O)CC=2C=CC(=CC=2)C=2C=CC=CC=2)C(N)=NC=1NC1=CC=CC=C1 JNTYRUUIWJEEJL-UHFFFAOYSA-N 0.000 claims description 2
- YWOWQBAGQKJVRB-UHFFFAOYSA-N 1-(5-amino-3-anilino-1,2,4-triazol-1-yl)-2-thiophen-2-ylethanone Chemical compound N=1N(C(=O)CC=2SC=CC=2)C(N)=NC=1NC1=CC=CC=C1 YWOWQBAGQKJVRB-UHFFFAOYSA-N 0.000 claims description 2
- SSSBHYRKQGGOQM-UHFFFAOYSA-N 1-[3-amino-5-(3-chloroanilino)-1,2,4-triazol-1-yl]-2-phenylethanethione Chemical compound C=1C=CC=CC=1CC(=S)N1N=C(N)N=C1NC1=CC=CC(Cl)=C1 SSSBHYRKQGGOQM-UHFFFAOYSA-N 0.000 claims description 2
- GDSXGXCSFWNMDA-UHFFFAOYSA-N 1-[4-(5-amino-3-anilino-1,2,4-triazole-1-carbonyl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C(=O)N1C(N)=NC(NC=2C=CC=CC=2)=N1 GDSXGXCSFWNMDA-UHFFFAOYSA-N 0.000 claims description 2
- FRBNYENXXIMVOJ-UHFFFAOYSA-N 1-[5-amino-3-(3-chloroanilino)-1,2,4-triazol-1-yl]-2-naphthalen-2-ylethanone Chemical compound N=1N(C(=O)CC=2C=C3C=CC=CC3=CC=2)C(N)=NC=1NC1=CC=CC(Cl)=C1 FRBNYENXXIMVOJ-UHFFFAOYSA-N 0.000 claims description 2
- CLIBZBQUNLIVTN-UHFFFAOYSA-N 1-[5-amino-3-(3-chloroanilino)-1,2,4-triazol-1-yl]-3,3-diphenylpropan-1-one Chemical compound N=1N(C(=O)CC(C=2C=CC=CC=2)C=2C=CC=CC=2)C(N)=NC=1NC1=CC=CC(Cl)=C1 CLIBZBQUNLIVTN-UHFFFAOYSA-N 0.000 claims description 2
- NJAIVALYSJBHKD-UHFFFAOYSA-N 1-[5-amino-3-(3-chloroanilino)-1,2,4-triazol-1-yl]-4-phenylbutane-1,4-dione Chemical compound N=1N(C(=O)CCC(=O)C=2C=CC=CC=2)C(N)=NC=1NC1=CC=CC(Cl)=C1 NJAIVALYSJBHKD-UHFFFAOYSA-N 0.000 claims description 2
- BLGJHQMNSBYLEZ-UHFFFAOYSA-N 2-hydroxyethanesulfonamide Chemical compound NS(=O)(=O)CCO BLGJHQMNSBYLEZ-UHFFFAOYSA-N 0.000 claims description 2
- ZVVZSDXDMZJUDE-UHFFFAOYSA-N 3-(2-chlorophenyl)-4-[1-(3-hydroxypropyl)indol-3-yl]pyrrole-2,5-dione Chemical compound C12=CC=CC=C2N(CCCO)C=C1C(C(NC1=O)=O)=C1C1=CC=CC=C1Cl ZVVZSDXDMZJUDE-UHFFFAOYSA-N 0.000 claims description 2
- FDDYLQMUXCLOSY-UHFFFAOYSA-N 3-[1-(3-aminopropyl)indol-3-yl]-4-(2-chlorophenyl)pyrrole-2,5-dione Chemical group C12=CC=CC=C2N(CCCN)C=C1C(C(NC1=O)=O)=C1C1=CC=CC=C1Cl FDDYLQMUXCLOSY-UHFFFAOYSA-N 0.000 claims description 2
- QDPJAKLUVOFGBT-UHFFFAOYSA-N 3-amino-5-anilino-n-cyclohexyl-1,2,4-triazole-1-carboxamide Chemical compound C1CCCCC1NC(=O)N1N=C(N)N=C1NC1=CC=CC=C1 QDPJAKLUVOFGBT-UHFFFAOYSA-N 0.000 claims description 2
- JYRJOQGKGMHTOO-UHFFFAOYSA-N 4-(2-amino-4-oxo-1h-imidazol-5-ylidene)-1,5,6,7-tetrahydropyrrolo[2,3-c]azepin-8-one Chemical compound N1C(N)=NC(=O)C1=C1C(C=CN2)=C2C(=O)NCC1 JYRJOQGKGMHTOO-UHFFFAOYSA-N 0.000 claims description 2
- BRUXPEXNSDOYTJ-UHFFFAOYSA-N 4-[5-amino-3-(3-chloroanilino)-1,2,4-triazol-1-yl]-2-methyl-1-phenylbutane-1,4-dione Chemical compound C=1C=CC=CC=1C(=O)C(C)CC(=O)N(C(=N1)N)N=C1NC1=CC=CC(Cl)=C1 BRUXPEXNSDOYTJ-UHFFFAOYSA-N 0.000 claims description 2
- IBYHCQCKHCBPNP-UHFFFAOYSA-N 4-amino-2-(pyridin-3-ylamino)-1,3-thiazole-5-carbaldehyde Chemical compound S1C(C=O)=C(N)N=C1NC1=CC=CN=C1 IBYHCQCKHCBPNP-UHFFFAOYSA-N 0.000 claims description 2
- IEPJSURKNFXCPB-UHFFFAOYSA-N 5-amino-3-anilino-1,2,4-triazole-1-carboxylic acid;4-phenylbenzamide Chemical compound C1=CC(C(=O)N)=CC=C1C1=CC=CC=C1.OC(=O)N1C(N)=NC(NC=2C=CC=CC=2)=N1 IEPJSURKNFXCPB-UHFFFAOYSA-N 0.000 claims description 2
- FOXRJMAZHSGDLO-UHFFFAOYSA-N 5-amino-3-anilino-n-(3-methoxyphenyl)-1,2,4-triazole-1-carboxamide Chemical compound COC1=CC=CC(NC(=O)N2C(=NC(NC=3C=CC=CC=3)=N2)N)=C1 FOXRJMAZHSGDLO-UHFFFAOYSA-N 0.000 claims description 2
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Cited By (1)
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| RU2456266C1 (ru) * | 2011-04-06 | 2012-07-20 | Максим Эдуардович Запольский | Производные 4,4'-бифениламидов, обладающие фармакологической активностью, и лекарственные средства на их основе |
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| RU2332213C2 (ru) * | 2002-04-30 | 2008-08-27 | Алькон, Инк. | Агенты, которые регулируют, ингибируют или модулируют активность и/или экспрессию факторов роста соединительной ткани (фрст), в качестве уникальных средств для снижения внутриглазного давления и лечения глаукоматозных ретинопатий/оптических невропатий |
| EP1616568A3 (en) * | 2002-04-30 | 2006-06-21 | Alcon, Inc | GSK-3 inhibitors and CDK inhibitors as anti-glaucoma agents |
| WO2004103958A2 (en) | 2003-05-19 | 2004-12-02 | Michigan State University | Preparation of hymenialdisine derivatives and use thereof |
| CN1897972A (zh) * | 2003-12-22 | 2007-01-17 | 爱尔康公司 | 用于治疗青光眼性视网膜病和视神经病的活性剂 |
| TW200526224A (en) * | 2003-12-22 | 2005-08-16 | Alcon Inc | Short form c-Maf transcription factor antagonists for treatment of glaucoma |
| US20050137147A1 (en) * | 2003-12-22 | 2005-06-23 | Alcon, Inc. | Agents for treatment of diabetic retinopathy and drusen formation in macular degeneration |
| CA2550891A1 (en) * | 2003-12-24 | 2005-07-14 | Bayer Cropscience Gmbh | Plant growth regulation |
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| US20080096238A1 (en) * | 2004-03-30 | 2008-04-24 | Alcon, Inc. | High throughput assay for human rho kinase activity with enhanced signal-to-noise ratio |
| CA2566392A1 (en) * | 2004-05-12 | 2005-11-17 | Bayer Cropscience Gmbh | Plant growth regulation |
| WO2006089874A1 (en) * | 2005-02-22 | 2006-08-31 | Gpc Biotech Ag | Benzo[2,3]azepino[4,5-b]indol-6-ones |
| EP1856259A1 (en) * | 2005-03-11 | 2007-11-21 | Alcon Inc. | Rnai-mediated inhibition of frizzled related protein-1 for treatment of glaucoma |
| RU2284192C1 (ru) * | 2005-04-01 | 2006-09-27 | Государственное учреждение Межотраслевой научно-технический комплекс "Микрохирургия глаза" им. акад. С.Н. Федорова Министерства здравоохранения РФ | Способ лечения глаукомной оптической нейропатии |
| US20080207594A1 (en) | 2005-05-04 | 2008-08-28 | Davelogen Aktiengesellschaft | Use of Gsk-3 Inhibitors for Preventing and Treating Pancreatic Autoimmune Disorders |
| EP1757607A1 (en) | 2005-08-24 | 2007-02-28 | Molisa GmbH | N5-substituted benzo¬2,3|azepino¬4,5-b|indol-6-ones for treating tropical diseases |
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| WO2007146136A2 (en) * | 2006-06-12 | 2007-12-21 | Merck & Co., Inc. | Ophthalmic compositions for treating ocular hypertension |
| CA2710230C (en) | 2006-12-29 | 2016-02-23 | Rigel Pharmaceuticals, Inc. | Bridged bicyclic aryl and bridged bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| EP2079736B1 (en) | 2006-12-29 | 2017-10-18 | Rigel Pharmaceuticals, Inc. | Substituted triazoles useful as axl inhibitors |
| JP5567837B2 (ja) | 2006-12-29 | 2014-08-06 | ライジェル ファーマシューティカルズ， インコーポレイテッド | Ａｘｌインヒビターとして有用なＮ３−ヘテロアリール置換トリアゾールおよびＮ５−ヘテロアリール置換トリアゾール |
| CA2710043C (en) | 2006-12-29 | 2016-02-09 | Rigel Pharmaceuticals, Inc. | Bicyclic aryl and bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| WO2008083367A2 (en) | 2006-12-29 | 2008-07-10 | Rigel Pharmaceuticals, Inc. | Polycyclic heteroaryl substituted triazoles useful as axl inhibitors |
| WO2009054864A1 (en) | 2007-10-26 | 2009-04-30 | Rigel Pharmaceuticals, Inc. | Polycyclic aryl substituted triazoles and polycyclic heteroaryl substituted triazoles useful as axl inhibitors |
| JP5592884B2 (ja) | 2008-07-09 | 2014-09-17 | ライジェル ファーマシューティカルズ， インコーポレイテッド | Ａｘｌ阻害剤として有用な多環式ヘテロアリール置換トリアゾール |
| WO2010005879A1 (en) | 2008-07-09 | 2010-01-14 | Rigel Pharmaceuticals, Inc. | Bridged bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| CN102281875B (zh) | 2009-01-16 | 2017-09-22 | 里格尔药品股份有限公司 | 预防、治疗或应对转移癌的使用axl抑制剂的组合疗法 |
| UA103918C2 (en) * | 2009-03-02 | 2013-12-10 | Айерем Элелси | N-(hetero)aryl, 2-(hetero)aryl-substituted acetamides for use as wnt signaling modulators |
| EP3272880B1 (en) | 2013-03-15 | 2020-11-25 | Fundació Institut de Recerca Biomèdica (IRB Barcelona) | Method for the diagnosis, prognosis and treatment of metastatic cancer |
| EP3089748A4 (en) * | 2014-01-02 | 2017-09-27 | Massachusetts Eye & Ear Infirmary | Treating ocular neovascularization |
| WO2015155738A2 (en) | 2014-04-09 | 2015-10-15 | Christopher Rudd | Use of gsk-3 inhibitors or activators which modulate pd-1 or t-bet expression to modulate t cell immunity |
| US12396889B2 (en) | 2014-05-12 | 2025-08-26 | Gholam A. Peyman | Lamellar corneal autologous or homologous graft in refractive surgery |
| US11565023B2 (en) | 2014-05-12 | 2023-01-31 | Gholam A. Peyman | Method of corneal transplantation or corneal inlay implantation with cross-linking |
| US10583221B2 (en) | 2014-05-12 | 2020-03-10 | Gholam A. Peyman | Method of corneal transplantation or corneal inlay implantation with cross-linking |
| US11045352B2 (en) | 2014-05-12 | 2021-06-29 | Gholam A. Peyman | Methods for treatment of dry eye and other acute or chronic inflammatory processes |
| US11338059B2 (en) | 2014-05-12 | 2022-05-24 | Gholam A. Peyman | Method of corneal and scleral inlay crosslinking and preservation |
| US10881503B2 (en) | 2014-05-12 | 2021-01-05 | Gholam A. Peyman | Method of corneal transplantation or corneal inlay implantation with cross-linking |
| US11648261B2 (en) | 2014-05-12 | 2023-05-16 | Gholam A. Peyman | Method of treating, reducing, or alleviating a medical condition in a patient |
| US10925889B2 (en) | 2014-05-12 | 2021-02-23 | Gholam A. Peyman | Method of treating, reducing, or alleviating a medical condition in a patient |
| US11666777B2 (en) | 2014-05-12 | 2023-06-06 | Gholam A. Peyman | Photodynamic therapy technique for preventing damage to the fovea of the eye or another body portion of a patient |
| TWI677489B (zh) | 2014-06-20 | 2019-11-21 | 美商基利科學股份有限公司 | 多環型胺甲醯基吡啶酮化合物之合成 |
| WO2019221959A1 (en) * | 2018-05-16 | 2019-11-21 | Peyman Gholam A | Method of treating, reducing, or alleviating a medical condition in a patient |
| US11707518B2 (en) | 2019-04-28 | 2023-07-25 | Gholam A. Peyman | Method of treating, reducing, or alleviating a medical condition in a patient |
| US12226478B2 (en) | 2019-04-28 | 2025-02-18 | Gholam A. Peyman | Method of treating, reducing, or alleviating a medical condition in a patient |
| US12110278B2 (en) * | 2020-10-13 | 2024-10-08 | Yale University | Selective JAK2 pseudokinase ligands and methods of use |
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| GB9319297D0 (en) | 1993-09-17 | 1993-11-03 | Wellcome Found | Indole derivatives |
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| PE91498A1 (es) | 1996-07-29 | 1998-12-22 | Hoffmann La Roche | Pirroles sustituidos |
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- 2002-09-23 PL PL369130A patent/PL207022B1/pl not_active IP Right Cessation
- 2002-09-23 US US10/488,496 patent/US7598288B2/en not_active Expired - Fee Related
- 2002-09-23 EP EP10181455A patent/EP2281560A1/en not_active Withdrawn
- 2002-09-23 JP JP2003530847A patent/JP2005504101A/ja active Pending
- 2002-09-23 KR KR10-2004-7003638A patent/KR20040047824A/ko not_active Ceased
- 2002-09-23 BR BR0212924-8A patent/BR0212924A/pt not_active IP Right Cessation
- 2002-09-23 RU RU2004112766/14A patent/RU2297243C2/ru not_active IP Right Cessation
- 2002-09-26 AR ARP020103638A patent/AR036684A1/es unknown
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999062503A2 (en) * | 1998-05-29 | 1999-12-09 | Cnrs (Centre National De Recherche Scientifique) France Innovation Scientifique Et Transfert | Use of indigoid bisindole derivatives for the manufacture of a medicament to inhibit cyclin dependent kinases |
| RU2002100646A (ru) * | 1999-06-16 | 2003-08-20 | РЕКИК Элиес Бен Мохамед Рауф | Офтальмологические нейро- и ретинопротекторные лекарственные средства |
| WO2001037819A2 (fr) * | 1999-11-23 | 2001-05-31 | Centre National De La Recherche Scientifique (C.N.R.S.) | Utilisation de derives d'indirubine pour la fabrication de medicaments |
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| Title |
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| реферат. * |
| реферат. Нестеров А.П. Глаукома. - М.: Медицина, 1995, с.11. Shmyreva V.F. et al. "Determination of individually endurable intraocular pressure (pressure of target) in primary glaucoma" // Vestn Oftalmol. 2003 Nov-Dec; 119(6): 3-5. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2456266C1 (ru) * | 2011-04-06 | 2012-07-20 | Максим Эдуардович Запольский | Производные 4,4'-бифениламидов, обладающие фармакологической активностью, и лекарственные средства на их основе |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005320350A (ja) | 2005-11-17 |
| US20040186159A1 (en) | 2004-09-23 |
| EP1430120A1 (en) | 2004-06-23 |
| US7598288B2 (en) | 2009-10-06 |
| AR036684A1 (es) | 2004-09-29 |
| MXPA04002137A (es) | 2004-06-29 |
| CN101380319A (zh) | 2009-03-11 |
| TWI335221B (en) | 2011-01-01 |
| ZA200401846B (en) | 2005-03-07 |
| PL369130A1 (en) | 2005-04-18 |
| AU2002334635B2 (en) | 2007-06-21 |
| CA2460000A1 (en) | 2003-04-03 |
| BR0212924A (pt) | 2005-01-04 |
| PL207022B1 (pl) | 2010-10-29 |
| RU2004112766A (ru) | 2005-03-27 |
| WO2003027275A1 (en) | 2003-04-03 |
| TW201041580A (en) | 2010-12-01 |
| JP2005504101A (ja) | 2005-02-10 |
| US20090312390A1 (en) | 2009-12-17 |
| EP1430120A4 (en) | 2007-06-20 |
| CA2460000C (en) | 2013-01-29 |
| KR20040047824A (ko) | 2004-06-05 |
| EP2281560A1 (en) | 2011-02-09 |
| CN1561393A (zh) | 2005-01-05 |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20130924 |