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
Links
- 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
- CTJFHHYKXSRZLX-UHFFFAOYSA-N 5-amino-3-anilino-n-(4-bromo-2-methylphenyl)-1,2,4-triazole-1-carboxamide Chemical compound CC1=CC(Br)=CC=C1NC(=O)N1C(N)=NC(NC=2C=CC=CC=2)=N1 CTJFHHYKXSRZLX-UHFFFAOYSA-N 0.000 claims description 2
- SNSCDIOVRMCIOW-UHFFFAOYSA-N 5-amino-3-anilino-n-(4-phenoxyphenyl)-1,2,4-triazole-1-carboxamide Chemical compound N=1N(C(=O)NC=2C=CC(OC=3C=CC=CC=3)=CC=2)C(N)=NC=1NC1=CC=CC=C1 SNSCDIOVRMCIOW-UHFFFAOYSA-N 0.000 claims description 2
- DOBHLKAMPAQXKC-UHFFFAOYSA-N 5-amino-3-anilino-n-naphthalen-1-yl-1,2,4-triazole-1-carboxamide Chemical compound N=1N(C(=O)NC=2C3=CC=CC=C3C=CC=2)C(N)=NC=1NC1=CC=CC=C1 DOBHLKAMPAQXKC-UHFFFAOYSA-N 0.000 claims description 2
- CWVPBBILDVOUCB-UHFFFAOYSA-N 5-amino-n-(4-chlorophenyl)-3-(4-methoxyanilino)-1,2,4-triazole-1-carboxamide Chemical compound C1=CC(OC)=CC=C1NC1=NN(C(=O)NC=2C=CC(Cl)=CC=2)C(N)=N1 CWVPBBILDVOUCB-UHFFFAOYSA-N 0.000 claims description 2
- SCUSPKIJTTXPKV-UHFFFAOYSA-N [3-(5-amino-3-anilino-1,2,4-triazole-1-carbonyl)phenyl]-phenylmethanone Chemical compound N=1N(C(=O)C=2C=C(C=CC=2)C(=O)C=2C=CC=CC=2)C(N)=NC=1NC1=CC=CC=C1 SCUSPKIJTTXPKV-UHFFFAOYSA-N 0.000 claims description 2
- QXDIWEGFHBDDPV-UHFFFAOYSA-N [4-amino-2-(3,4-dichloroanilino)-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=C(Cl)C(Cl)=C1 QXDIWEGFHBDDPV-UHFFFAOYSA-N 0.000 claims description 2
- LKBMCCDTJAZVIE-UHFFFAOYSA-N [4-amino-2-(4-chloroanilino)-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=C(Cl)C=C1 LKBMCCDTJAZVIE-UHFFFAOYSA-N 0.000 claims description 2
- DOPTXFSKHKVWMK-UHFFFAOYSA-N [4-amino-2-(ethylamino)-1,3-thiazol-5-yl]-phenylmethanone Chemical compound S1C(NCC)=NC(N)=C1C(=O)C1=CC=CC=C1 DOPTXFSKHKVWMK-UHFFFAOYSA-N 0.000 claims description 2
- RGFSWTNITOFXBJ-UHFFFAOYSA-N [4-amino-2-(propylamino)-1,3-thiazol-5-yl]-pyridin-3-ylmethanone Chemical compound S1C(NCCC)=NC(N)=C1C(=O)C1=CC=CN=C1 RGFSWTNITOFXBJ-UHFFFAOYSA-N 0.000 claims description 2
- GUDBDNYMUVSMPF-UHFFFAOYSA-N [4-amino-2-(pyridin-3-ylamino)-1,3-thiazol-5-yl]-phenylmethanone Chemical compound S1C(C(=O)C=2C=CC=CC=2)=C(N)N=C1NC1=CC=CN=C1 GUDBDNYMUVSMPF-UHFFFAOYSA-N 0.000 claims description 2
- GOABPJHGEWRGSL-UHFFFAOYSA-N [5-amino-3-(3-chloroanilino)-1,2,4-triazol-1-yl]-phenylmethanone Chemical compound N=1N(C(=O)C=2C=CC=CC=2)C(N)=NC=1NC1=CC=CC(Cl)=C1 GOABPJHGEWRGSL-UHFFFAOYSA-N 0.000 claims description 2
- IWTRHJOLQTUTJU-UHFFFAOYSA-N [5-amino-3-(5-chloro-2-methylanilino)-1,2,4-triazol-1-yl]-phenylmethanone Chemical compound CC1=CC=C(Cl)C=C1NC1=NN(C(=O)C=2C=CC=CC=2)C(N)=N1 IWTRHJOLQTUTJU-UHFFFAOYSA-N 0.000 claims description 2
- WCCYEJYTLNWYCC-UHFFFAOYSA-N chembl337300 Chemical compound N1C2=CC=CC=C2C(N=O)=C1C1=C(O)NC2=CC=C(I)C=C21 WCCYEJYTLNWYCC-UHFFFAOYSA-N 0.000 claims description 2
- 239000007943 implant Substances 0.000 claims description 2
- HBDSHCUSXQATPO-BGBJRWHRSA-N indirubin-3'-monoxime Chemical compound O=C/1NC2=CC=CC=C2C\1=C\1/C(=N/O)/C2=CC=CC=C2N/1 HBDSHCUSXQATPO-BGBJRWHRSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229940122049 Glycogen synthase inhibitor Drugs 0.000 claims 1
- JRSHCTNXHJJDLH-UHFFFAOYSA-N [4-amino-2-(3-methoxypropylamino)-1,3-thiazol-5-yl]-pyridin-3-ylmethanone Chemical compound S1C(NCCCOC)=NC(N)=C1C(=O)C1=CC=CN=C1 JRSHCTNXHJJDLH-UHFFFAOYSA-N 0.000 claims 1
- JMYVMOUINOAAPA-UHFFFAOYSA-N cyclopropanecarbaldehyde Chemical compound O=CC1CC1 JMYVMOUINOAAPA-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 6
- 230000000694 effects Effects 0.000 abstract description 3
- 208000003098 Ganglion Cysts Diseases 0.000 abstract description 2
- 208000005400 Synovial Cyst Diseases 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 210000001525 retina Anatomy 0.000 abstract description 2
- 230000007721 medicinal effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 108090000623 proteins and genes Proteins 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 235000018102 proteins Nutrition 0.000 description 10
- 102000004169 proteins and genes Human genes 0.000 description 10
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 9
- 108050003627 Wnt Proteins 0.000 description 9
- 102000013814 Wnt Human genes 0.000 description 9
- 230000007423 decrease Effects 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 102000015735 Beta-catenin Human genes 0.000 description 7
- 108060000903 Beta-catenin Proteins 0.000 description 7
- 230000026731 phosphorylation Effects 0.000 description 7
- 238000006366 phosphorylation reaction Methods 0.000 description 7
- 206010012601 diabetes mellitus Diseases 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 230000037361 pathway Effects 0.000 description 6
- 102100030058 Secreted frizzled-related protein 1 Human genes 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 208000024827 Alzheimer disease Diseases 0.000 description 4
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 4
- 229960000686 benzalkonium chloride Drugs 0.000 description 4
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 4
- 229940061607 dibasic sodium phosphate Drugs 0.000 description 4
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 4
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 208000015122 neurodegenerative disease Diseases 0.000 description 4
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 4
- 229940068968 polysorbate 80 Drugs 0.000 description 4
- 229920000053 polysorbate 80 Polymers 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- 230000004382 visual function Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 208000020925 Bipolar disease Diseases 0.000 description 3
- 206010012289 Dementia Diseases 0.000 description 3
- 108010057784 Fusion Regulatory Protein-1 Proteins 0.000 description 3
- 210000001742 aqueous humor Anatomy 0.000 description 3
- 208000028683 bipolar I disease Diseases 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 230000004406 elevated intraocular pressure Effects 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 229940054534 ophthalmic solution Drugs 0.000 description 3
- 239000002997 ophthalmic solution Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 201000004569 Blindness Diseases 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 description 2
- 102100038104 Glycogen synthase kinase-3 beta Human genes 0.000 description 2
- 239000004166 Lanolin Substances 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000033228 biological regulation Effects 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 210000004240 ciliary body Anatomy 0.000 description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 2
- 235000018417 cysteine Nutrition 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
- 229940039717 lanolin Drugs 0.000 description 2
- 235000019388 lanolin Nutrition 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000000626 neurodegenerative effect Effects 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 210000001328 optic nerve Anatomy 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 230000010412 perfusion Effects 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 210000003994 retinal ganglion cell Anatomy 0.000 description 2
- 230000008054 signal transmission Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- LPPMDPRPEQCOPW-UHFFFAOYSA-N 5-amino-3-anilino-n-cyclohexyl-1,2,4-triazole-1-carboxamide Chemical compound N=1N(C(=O)NC2CCCCC2)C(N)=NC=1NC1=CC=CC=C1 LPPMDPRPEQCOPW-UHFFFAOYSA-N 0.000 description 1
- KNUBLBZSYZLDJB-UHFFFAOYSA-N 5-amino-3-anilino-n-phenyl-1,2,4-triazole-1-carboxamide Chemical compound N=1N(C(=O)NC=2C=CC=CC=2)C(N)=NC=1NC1=CC=CC=C1 KNUBLBZSYZLDJB-UHFFFAOYSA-N 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 108091007914 CDKs Proteins 0.000 description 1
- 102000008122 Casein Kinase I Human genes 0.000 description 1
- 108010049812 Casein Kinase I Proteins 0.000 description 1
- 102000003903 Cyclin-dependent kinases Human genes 0.000 description 1
- 108090000266 Cyclin-dependent kinases Proteins 0.000 description 1
- 229920002148 Gellan gum Polymers 0.000 description 1
- 108010001483 Glycogen Synthase Proteins 0.000 description 1
- 229920002907 Guar gum Polymers 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 239000007993 MOPS buffer Substances 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical class O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000019022 Mood disease Diseases 0.000 description 1
- 206010061323 Optic neuropathy Diseases 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 229940123924 Protein kinase C inhibitor Drugs 0.000 description 1
- 201000007737 Retinal degeneration Diseases 0.000 description 1
- 208000017442 Retinal disease Diseases 0.000 description 1
- 206010057430 Retinal injury Diseases 0.000 description 1
- 208000007014 Retinitis pigmentosa Diseases 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- 108010090804 Streptavidin Proteins 0.000 description 1
- 230000004156 Wnt signaling pathway Effects 0.000 description 1
- PCLAGPUDXPMUBV-UHFFFAOYSA-N [4-amino-2-(4-bromoanilino)-1,3-thiazol-5-yl]-cyclopropylmethanone Chemical compound S1C(C(=O)C2CC2)=C(N)N=C1NC1=CC=C(Br)C=C1 PCLAGPUDXPMUBV-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229940006133 antiglaucoma drug and miotics carbonic anhydrase inhibitors Drugs 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000003489 carbonate dehydratase inhibitor Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000001086 cytosolic effect Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- ZVTIPQFMCWWBPZ-UHFFFAOYSA-N ethyl 3-[[4-amino-5-(pyridine-3-carbonyl)-1,3-thiazol-2-yl]amino]butanoate Chemical compound S1C(NC(C)CC(=O)OCC)=NC(N)=C1C(=O)C1=CC=CN=C1 ZVTIPQFMCWWBPZ-UHFFFAOYSA-N 0.000 description 1
- 230000004438 eyesight Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000010492 gellan gum Nutrition 0.000 description 1
- 239000000216 gellan gum Substances 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000003572 glycogen synthase kinase 3 inhibitor Substances 0.000 description 1
- 239000000665 guar gum Substances 0.000 description 1
- 235000010417 guar gum Nutrition 0.000 description 1
- 229960002154 guar gum Drugs 0.000 description 1
- 208000024963 hair loss Diseases 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 230000037041 intracellular level Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
- 239000011654 magnesium acetate Substances 0.000 description 1
- 229940069446 magnesium acetate Drugs 0.000 description 1
- 235000011285 magnesium acetate Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000009223 neuronal apoptosis Effects 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940100654 ophthalmic suspension Drugs 0.000 description 1
- 208000020911 optic nerve disease Diseases 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 150000003905 phosphatidylinositols Chemical class 0.000 description 1
- 210000000608 photoreceptor cell Anatomy 0.000 description 1
- 108091008695 photoreceptors Proteins 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 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
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 150000003180 prostaglandins Chemical class 0.000 description 1
- 239000003881 protein kinase C inhibitor Substances 0.000 description 1
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004258 retinal degeneration Effects 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 201000000980 schizophrenia Diseases 0.000 description 1
- 125000003607 serino group Chemical class [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 102000035160 transmembrane proteins Human genes 0.000 description 1
- 108091005703 transmembrane proteins Proteins 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000004393 visual impairment Effects 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0048—Eye, e.g. artificial tears
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
-
- 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
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Hematology (AREA)
- Rheumatology (AREA)
- Dermatology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32539001P | 2001-09-27 | 2001-09-27 | |
| US60/325,390 | 2001-09-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2004112766A RU2004112766A (ru) | 2005-03-27 |
| RU2297243C2 true RU2297243C2 (ru) | 2007-04-20 |
Family
ID=23267686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2004112766/14A RU2297243C2 (ru) | 2001-09-27 | 2002-09-23 | Ингибиторы киназы-3 гликогенсинтазы (gsk-3) для лечения глаукомы |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US7598288B2 (enExample) |
| EP (2) | EP1430120A4 (enExample) |
| JP (2) | JP2005504101A (enExample) |
| KR (1) | KR20040047824A (enExample) |
| CN (2) | CN1561393A (enExample) |
| AR (1) | AR036684A1 (enExample) |
| AU (1) | AU2002334635B2 (enExample) |
| BR (1) | BR0212924A (enExample) |
| CA (1) | CA2460000C (enExample) |
| MX (1) | MXPA04002137A (enExample) |
| PL (1) | PL207022B1 (enExample) |
| RU (1) | RU2297243C2 (enExample) |
| TW (2) | TW201041580A (enExample) |
| WO (1) | WO2003027275A1 (enExample) |
| ZA (1) | ZA200401846B (enExample) |
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 |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2400543C (en) * | 2001-08-31 | 2011-11-01 | Centre For Addiction And Mental Health | The involvement of the bdnf gene in mood disorders |
| US7351407B2 (en) * | 2002-04-30 | 2008-04-01 | Alcon, Inc. | Agents which regulate, inhibit, or modulate the activity and/or expression of connective tissue growth factor (CTGF) as a unique means to both lower intraocular pressure and treat glaucomatous retinopathies/optic neuropathies |
| EP1925306A3 (en) * | 2002-04-30 | 2008-09-17 | Alcon, Inc. | Agents which Regulate, Inhibit, or Modulate the Activity and/or Expression of Connective Tissue Growth Factor (CTGF) to Lower Intraocular Pressure |
| US7385055B2 (en) | 2003-05-19 | 2008-06-10 | Board Of Trustees Of Michigan State University | Preparation of hymenialdisine derivatives and use thereof |
| CA2548146A1 (en) * | 2003-12-22 | 2005-07-14 | Alcon, Inc. | Agents for treatment of diabetic retinopathy and drusen formation in macular degeneration |
| MXPA06006980A (es) * | 2003-12-22 | 2006-12-14 | Alcon Inc | Agentes para tratamiento de retinopatia glaucomatosa y neuropatia optica. |
| TW200526224A (en) * | 2003-12-22 | 2005-08-16 | Alcon Inc | Short form c-Maf transcription factor antagonists for treatment of glaucoma |
| JP2007516989A (ja) * | 2003-12-24 | 2007-06-28 | バイエル クロップサイエンス ゲーエムベーハー | 植物成長調節 |
| US20080096238A1 (en) * | 2004-03-30 | 2008-04-24 | Alcon, Inc. | High throughput assay for human rho kinase activity with enhanced signal-to-noise ratio |
| US20050222127A1 (en) * | 2004-03-30 | 2005-10-06 | Alcon, Inc. | Use of Rho kinase inhibitors in the treatment of hearing loss, tinnitus and improving body balance |
| US20100152044A1 (en) * | 2004-05-12 | 2010-06-17 | 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 |
| WO2006099353A1 (en) * | 2005-03-11 | 2006-09-21 | 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 |
| US7884119B2 (en) | 2005-09-07 | 2011-02-08 | Rigel Pharmaceuticals, Inc. | Triazole derivatives useful as Axl inhibitors |
| JP2009541219A (ja) * | 2006-06-12 | 2009-11-26 | メルク エンド カムパニー インコーポレーテッド | 高眼圧治療のための眼科組成物 |
| EP2078010B1 (en) | 2006-12-29 | 2014-01-29 | Rigel Pharmaceuticals, Inc. | Polycyclic heteroaryl substituted triazoles useful as axl inhibitors |
| WO2008083353A1 (en) | 2006-12-29 | 2008-07-10 | Rigel Pharmaceuticals, Inc. | Bicyclic aryl and bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| CA2710046C (en) | 2006-12-29 | 2016-02-09 | Rigel Pharmaceuticals, Inc. | N3-heteroaryl substituted triazoles and n5-heteroaryl substituted triazoles useful as axl inhibitors |
| JP2010514810A (ja) | 2006-12-29 | 2010-05-06 | 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置換トリアゾール |
| US8012965B2 (en) | 2006-12-29 | 2011-09-06 | Rigel Pharmaceuticals, Inc. | Bridged bicyclic aryl and bridged bicyclic heteroaryl substituted triazoles useful as axl inhibitors |
| EP2205592B1 (en) | 2007-10-26 | 2013-05-08 | Rigel Pharmaceuticals, Inc. | Polycyclic aryl substituted triazoles and polycyclic heteroaryl substituted triazoles useful as axl inhibitors |
| ES2537480T3 (es) | 2008-07-09 | 2015-06-08 | Rigel Pharmaceuticals, Inc. | Triazoles sustituidos con heteroarilo policíclicos útiles como inhibidores de Axl |
| JP5613156B2 (ja) | 2008-07-09 | 2014-10-22 | 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架橋二環ヘテロアリール置換トリアゾール |
| PL2387395T3 (pl) | 2009-01-16 | 2015-03-31 | Rigel Pharmaceuticals Inc | Inhibitory Axl do zastosowania w terapii skojarzonej do zapobiegania, leczenia lub postępowania z nowotworem przerzutowym |
| UA103918C2 (en) * | 2009-03-02 | 2013-12-10 | Айерем Элелси | N-(hetero)aryl, 2-(hetero)aryl-substituted acetamides for use as wnt signaling modulators |
| CA2903306A1 (en) | 2013-03-15 | 2014-09-18 | Fundacio Institut De Recerca Biomedica (Irb Barcelona) | Method for the diagnosis, prognosis and treatment of metastatic cancer |
| WO2015103480A1 (en) * | 2014-01-02 | 2015-07-09 | Massachusetts Eye & Ear Infirmary | Treating ocular neovascularization |
| CA2945263A1 (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 |
| US11338059B2 (en) | 2014-05-12 | 2022-05-24 | Gholam A. Peyman | Method of corneal and scleral inlay crosslinking and preservation |
| 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 |
| US11565023B2 (en) | 2014-05-12 | 2023-01-31 | Gholam A. Peyman | Method of corneal transplantation or corneal inlay implantation with cross-linking |
| US10925889B2 (en) | 2014-05-12 | 2021-02-23 | Gholam A. Peyman | Method of treating, reducing, or alleviating a medical condition in a patient |
| US12396889B2 (en) | 2014-05-12 | 2025-08-26 | Gholam A. Peyman | Lamellar corneal autologous or homologous graft in refractive surgery |
| 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 |
| 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 |
| 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 |
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 |
| 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 |
| RU2002100646A (ru) * | 1999-06-16 | 2003-08-20 | РЕКИК Элиес Бен Мохамед Рауф | Офтальмологические нейро- и ретинопротекторные лекарственные средства |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ227850A (en) | 1988-02-10 | 1991-11-26 | Hoffmann La Roche | Indole substituted pyrrole derivatives; preparatory process and medicaments for use against inflammatory immunological, bronchopulmonary or vascular disorders |
| MC2096A1 (fr) | 1989-02-23 | 1991-02-15 | Hoffmann La Roche | Pyrroles substitues |
| DE3914764A1 (de) | 1989-05-05 | 1990-11-08 | Goedecke Ag | Maleinimid-derivate und deren verwendung als arzneimittel |
| CA2015996C (en) | 1989-05-05 | 2001-08-28 | Hartmut Osswald | Bis-(1h-indol-3-yl)-maleinimide derivatives and their use as pharmaceuticals |
| DE4005970A1 (de) | 1990-02-26 | 1991-08-29 | Boehringer Mannheim Gmbh | Neue trisubstituierte maleinimide, verfahren zu ihrer herstellung sowie arzneimittel, die diese verbindungen enthalten |
| DE4005969A1 (de) | 1990-02-26 | 1991-08-29 | Boehringer Mannheim Gmbh | Neue trisubstituierte pyrrole, verfahren zu ihrer herstellung sowie arzneimittel, die diese verbindungen enthalten |
| CA2046801C (en) | 1990-08-07 | 2002-02-26 | Peter D. Davis | Substituted pyrroles |
| CA2108146A1 (en) | 1991-04-11 | 1992-10-12 | Stuart W. Mccombie | Anti-tumor and anti-psoriatic agents |
| GB9123396D0 (en) | 1991-11-04 | 1991-12-18 | Hoffmann La Roche | A process for the manufacture of substituted maleimides |
| AU3761393A (en) | 1992-03-20 | 1993-10-21 | Wellcome Foundation Limited, The | Indole derivatives with antiviral activity |
| US5547976A (en) | 1992-03-20 | 1996-08-20 | Burroughs Wellcome Co. | Further indole derivatives with antiviral activity |
| DE4217964A1 (de) | 1992-05-30 | 1993-12-02 | Goedecke Ag | Indolocarbazol-Imide und deren Verwendung |
| DE4243321A1 (de) | 1992-12-21 | 1994-06-23 | Goedecke Ag | Aminosäurederivate von Heterocyclen als PKC-Inhibitoren |
| GB9319297D0 (en) | 1993-09-17 | 1993-11-03 | Wellcome Found | Indole derivatives |
| GB9416467D0 (en) | 1994-08-13 | 1994-10-05 | Wellcome Found | Compounds for use in medicine |
| US5681854A (en) * | 1995-11-22 | 1997-10-28 | Alcon Laboratories, Inc. | Use of aliphatic carboxylic acid derivatives in ophthalmic disorders |
| US6057117A (en) | 1996-04-04 | 2000-05-02 | Chiron Corporation | Identification and use of selective inhibitors of glycogen synthase kinase 3 |
| WO1997041854A1 (en) * | 1996-05-07 | 1997-11-13 | The Trustees Of The University Of Pennsylvania | Inhibitors of glycogen synthase kinase-3 and methods for identifying and using the same |
| PE91498A1 (es) * | 1996-07-29 | 1998-12-22 | Hoffmann La Roche | Pirroles sustituidos |
| PE91698A1 (es) | 1996-07-29 | 1998-12-24 | Hoffmann La Roche | Pirroles sustituidos |
| PE91598A1 (es) | 1996-07-29 | 1998-12-24 | Hoffmann La Roche | Pirroles sustituidos |
| SE9603285D0 (sv) | 1996-09-10 | 1996-09-10 | Astra Ab | New compounds |
| SE9603283D0 (sv) | 1996-09-10 | 1996-09-10 | Astra Ab | New compounds |
| US6255485B1 (en) * | 1997-08-07 | 2001-07-03 | The Regents Of The University Of California | Purine inhibitors of protein kinases, G proteins and polymerases |
| AU2548699A (en) | 1998-02-23 | 1999-09-06 | Rei Asakai | Cell death inhibitors |
| AU6111699A (en) | 1998-10-08 | 2000-05-01 | Smithkline Beecham Plc | Novel method and compounds |
| GB9828640D0 (en) | 1998-12-23 | 1999-02-17 | Smithkline Beecham Plc | Novel method and compounds |
| GB9918180D0 (en) | 1999-08-02 | 1999-10-06 | Smithkline Beecham Plc | Novel compositions |
| WO2001013916A1 (en) * | 1999-08-20 | 2001-03-01 | Sagami Chemical Research Center | Drugs inhibiting cell death |
| ES2213996T3 (es) | 1999-12-08 | 2004-09-01 | Centre National De La Recherche Scientifique (Cnrs) | Uso de himenialdisina o sus derivados en la fabricacion de medicamentos. |
| AU2337601A (en) | 1999-12-23 | 2001-07-09 | Ontario Cancer Institute, The | Inhibition of gsk-3beta |
| WO2001049709A1 (en) | 2000-01-03 | 2001-07-12 | Ramot University Authority For Applied Research & Industrial Development Ltd. | Glycogen synthase kinase-3 inhibitors |
| AU2001230026A1 (en) | 2000-02-04 | 2001-08-14 | Novo-Nordisk A/S | 2,4-diaminothiazole derivatives |
| WO2001064949A2 (en) * | 2000-02-29 | 2001-09-07 | Alcon Laboratories, Inc. | Diagnostics and therapeutics for glaucoma |
| WO2001070727A1 (en) * | 2000-03-23 | 2001-09-27 | Sanofi-Synthelabo | 2-(arylalkylamino)pyrimidone derivatives and 2-(heteroarylalkylamino)pyrimidone derivatives |
| EP1136482A1 (en) * | 2000-03-23 | 2001-09-26 | Sanofi-Synthelabo | 2-Amino-3-(alkyl)-pyrimidone derivatives as GSK3beta inhibitors |
| EP1136099A1 (en) * | 2000-03-23 | 2001-09-26 | Sanofi-Synthelabo | 2-(Indolylalkylamino)pyrimidone derivatives as GSK3beta inhibitors |
| CA2457965C (en) | 2001-09-21 | 2010-06-01 | Sanofi-Synthelabo | Substituted 2-pyridinyl-6,7,8,9-tetrahydropyrimido[1,2-a]pyrimidin-4-one and 7-pyridinyl-2,3-dihydroimidazo[1,2-a]pyrimidin-5(1h)one derivatives |
-
2002
- 2002-09-10 TW TW099127943A patent/TW201041580A/zh unknown
- 2002-09-10 TW TW091120600A patent/TWI335221B/zh not_active IP Right Cessation
- 2002-09-23 BR BR0212924-8A patent/BR0212924A/pt not_active IP Right Cessation
- 2002-09-23 EP EP02799603A patent/EP1430120A4/en not_active Withdrawn
- 2002-09-23 MX MXPA04002137A patent/MXPA04002137A/es active IP Right Grant
- 2002-09-23 CA CA2460000A patent/CA2460000C/en not_active Expired - Fee Related
- 2002-09-23 PL PL369130A patent/PL207022B1/pl not_active IP Right Cessation
- 2002-09-23 KR KR10-2004-7003638A patent/KR20040047824A/ko not_active Ceased
- 2002-09-23 RU RU2004112766/14A patent/RU2297243C2/ru not_active IP Right Cessation
- 2002-09-23 EP EP10181455A patent/EP2281560A1/en not_active Withdrawn
- 2002-09-23 CN CNA028190106A patent/CN1561393A/zh active Pending
- 2002-09-23 US US10/488,496 patent/US7598288B2/en not_active Expired - Fee Related
- 2002-09-23 CN CNA2008100990379A patent/CN101380319A/zh active Pending
- 2002-09-23 WO PCT/US2002/030059 patent/WO2003027275A1/en not_active Ceased
- 2002-09-23 JP JP2003530847A patent/JP2005504101A/ja active Pending
- 2002-09-23 AU AU2002334635A patent/AU2002334635B2/en not_active Ceased
- 2002-09-26 AR ARP020103638A patent/AR036684A1/es unknown
-
2004
- 2004-03-05 ZA ZA200401846A patent/ZA200401846B/en unknown
-
2005
- 2005-07-21 JP JP2005211956A patent/JP2005320350A/ja active Pending
-
2009
- 2009-08-21 US US12/545,611 patent/US20090312390A1/en not_active Abandoned
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 |
Non-Patent Citations (2)
| Title |
|---|
| 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 |
|---|---|
| TWI335221B (en) | 2011-01-01 |
| JP2005504101A (ja) | 2005-02-10 |
| JP2005320350A (ja) | 2005-11-17 |
| TW201041580A (en) | 2010-12-01 |
| CN101380319A (zh) | 2009-03-11 |
| PL369130A1 (en) | 2005-04-18 |
| EP1430120A1 (en) | 2004-06-23 |
| EP1430120A4 (en) | 2007-06-20 |
| CA2460000C (en) | 2013-01-29 |
| KR20040047824A (ko) | 2004-06-05 |
| US20040186159A1 (en) | 2004-09-23 |
| PL207022B1 (pl) | 2010-10-29 |
| ZA200401846B (en) | 2005-03-07 |
| US7598288B2 (en) | 2009-10-06 |
| AU2002334635B2 (en) | 2007-06-21 |
| US20090312390A1 (en) | 2009-12-17 |
| BR0212924A (pt) | 2005-01-04 |
| MXPA04002137A (es) | 2004-06-29 |
| AR036684A1 (es) | 2004-09-29 |
| CA2460000A1 (en) | 2003-04-03 |
| EP2281560A1 (en) | 2011-02-09 |
| WO2003027275A1 (en) | 2003-04-03 |
| RU2004112766A (ru) | 2005-03-27 |
| CN1561393A (zh) | 2005-01-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2297243C2 (ru) | Ингибиторы киназы-3 гликогенсинтазы (gsk-3) для лечения глаукомы | |
| AU2002334635A1 (en) | Inhibitors of glycogen synthase kinase-3 (GSK-3) for treating glaucoma | |
| JP4934653B2 (ja) | Ｒｈｏキナーゼ阻害剤とβ遮断薬からなる緑内障治療剤 | |
| JP5174777B2 (ja) | Ｒｈｏキナーゼ阻害剤とプロスタグランジン類からなる緑内障治療剤 | |
| JP4482726B2 (ja) | Ｒｈｏキナーゼ阻害剤とプロスタグランジン類からなる緑内障治療剤 | |
| EP4338751B1 (en) | Combination of sepetaprost and netarsudil for use in the prophylaxis or treatment of glaucoma or ocular hypertension | |
| KR100499903B1 (ko) | 안압 제어 및 녹내장 치료용 5ｈｔ2 효능제 | |
| EP1859795A1 (en) | Therapeutic agent for ophthalmic disease | |
| HK1153935A (en) | Inhibitors of glycogen synthase kinase-3 (gsk-3) for treating glaucomatous optic neuropathy | |
| US20060211700A1 (en) | (R)-8,9-dichloro-2,3,4,4a-tetrahydro-1H,6H-pyrazino[1,2-a]quinoxalin-5-one for controlling IOP and treating glaucoma | |
| HK40102807B (en) | Combination of sepetaprost and netarsudil for use in the prophylaxis or treatment of glaucoma or ocular hypertension | |
| HK40102807A (en) | Combination of sepetaprost and netarsudil for use in the prophylaxis or treatment of glaucoma or ocular hypertension | |
| KR20080074128A (ko) | 각결막 장애 치료제 | |
| KR20070053283A (ko) | 각결막장해 치료제 | |
| HK40029829A (en) | Combination of sepetaprost and ripasudil for use in the prophylaxis or treatment of glaucoma or ocular hypertension | |
| CA2434691A1 (en) | Use of propentofylline to control intraocular pressure | |
| HK40029829B (en) | Combination of sepetaprost and ripasudil for use in the prophylaxis or treatment of glaucoma or ocular hypertension | |
| WO2014143591A1 (en) | Inhibition of neovascularization by simultaneous inhibition of prostanoid ip and ep4 receptors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20130924 |