ZA200306370B - Heterocyclic compounds for aging-related and diabetic vascular complications. - Google Patents
Heterocyclic compounds for aging-related and diabetic vascular complications. Download PDFInfo
- Publication number
- ZA200306370B ZA200306370B ZA200306370A ZA200306370A ZA200306370B ZA 200306370 B ZA200306370 B ZA 200306370B ZA 200306370 A ZA200306370 A ZA 200306370A ZA 200306370 A ZA200306370 A ZA 200306370A ZA 200306370 B ZA200306370 B ZA 200306370B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyrazol
- oxoethyl
- acceptable salt
- pharmaceutically acceptable
- methyl
- Prior art date
Links
- 201000009101 diabetic angiopathy Diseases 0.000 title description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 230000002431 foraging effect Effects 0.000 title 1
- -1 nitro, cyano, amino Chemical group 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 43
- 206010012601 diabetes mellitus Diseases 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 230000032683 aging Effects 0.000 claims description 20
- 238000009825 accumulation Methods 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- 238000000502 dialysis Methods 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 230000002159 abnormal effect Effects 0.000 claims description 8
- 208000017169 kidney disease Diseases 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000002845 discoloration Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000036542 oxidative stress Effects 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 201000001881 impotence Diseases 0.000 claims description 4
- 230000004768 organ dysfunction Effects 0.000 claims description 4
- 208000037803 restenosis Diseases 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 3
- 208000017442 Retinal disease Diseases 0.000 claims description 3
- 239000000385 dialysis solution Substances 0.000 claims description 3
- 206010062198 microangiopathy Diseases 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 230000002792 vascular Effects 0.000 claims description 3
- 206010048554 Endothelial dysfunction Diseases 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- 208000028389 Nerve injury Diseases 0.000 claims description 2
- 206010038923 Retinopathy Diseases 0.000 claims description 2
- 230000008694 endothelial dysfunction Effects 0.000 claims description 2
- 230000001900 immune effect Effects 0.000 claims description 2
- 230000008764 nerve damage Effects 0.000 claims description 2
- 208000017376 neurovascular disease Diseases 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims 128
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims 90
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims 63
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 claims 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 11
- 125000001424 substituent group Chemical group 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 7
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 7
- 125000005842 heteroatom Chemical group 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 6
- 150000001602 bicycloalkyls Chemical group 0.000 claims 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 150000002923 oximes Chemical class 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims 5
- 239000011593 sulfur Substances 0.000 claims 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 4
- 125000004171 alkoxy aryl group Chemical group 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 239000002904 solvent Substances 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- HBAVKOOREUXHAA-UHFFFAOYSA-N 3-[5-[(3,5-dimethylpyrazol-1-yl)methyl]-1h-pyrazol-3-yl]pyridine Chemical compound N1=C(C)C=C(C)N1CC1=NNC(C=2C=NC=CC=2)=C1 HBAVKOOREUXHAA-UHFFFAOYSA-N 0.000 claims 3
- RVRWNKUZSSNZRA-UHFFFAOYSA-M 5-pyridin-1-ium-1-yl-1,3-oxazole bromide Chemical compound [Br-].O1C=NC=C1[N+]1=CC=CC=C1 RVRWNKUZSSNZRA-UHFFFAOYSA-M 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- 125000005000 thioaryl group Chemical group 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910019142 PO4 Inorganic materials 0.000 claims 2
- UIYSONPKAAGPDJ-UHFFFAOYSA-M [Cl-].Br[N+]1=CC=CC=C1 Chemical compound [Cl-].Br[N+]1=CC=CC=C1 UIYSONPKAAGPDJ-UHFFFAOYSA-M 0.000 claims 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 2
- 230000003178 anti-diabetic effect Effects 0.000 claims 2
- 239000003472 antidiabetic agent Substances 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 claims 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 2
- 235000021317 phosphate Nutrition 0.000 claims 2
- 229940085991 phosphate ion Drugs 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims 1
- 125000006709 (C5-C7) cycloalkenyl group Chemical group 0.000 claims 1
- CFAGXGJRSVJIDE-UHFFFAOYSA-M 1-(1H-pyrazol-5-yl)pyridin-1-ium chloride Chemical compound [Cl-].c1cc([nH]n1)-[n+]1ccccc1 CFAGXGJRSVJIDE-UHFFFAOYSA-M 0.000 claims 1
- BLTFWPJNHGSYLM-UHFFFAOYSA-M 1-(5-methyl-1H-pyrazol-3-yl)pyridin-1-ium bromide Chemical compound [Br-].CC1=NNC(=C1)[N+]1=CC=CC=C1 BLTFWPJNHGSYLM-UHFFFAOYSA-M 0.000 claims 1
- BHDGTFLYMFNTDK-UHFFFAOYSA-M 1-(5-methylthiophen-2-yl)-2-[3-[5-(2-phenylethyl)-1h-pyrazol-3-yl]pyridin-1-ium-1-yl]ethanone;chloride Chemical compound [Cl-].S1C(C)=CC=C1C(=O)C[N+]1=CC=CC(C=2NN=C(CCC=3C=CC=CC=3)C=2)=C1 BHDGTFLYMFNTDK-UHFFFAOYSA-M 0.000 claims 1
- CNBJYYXRLNMBTE-UHFFFAOYSA-M 1-(5-methylthiophen-2-yl)-2-[3-[5-(thiophen-3-ylmethyl)-1h-pyrazol-3-yl]pyridin-1-ium-1-yl]ethanone;chloride Chemical compound [Cl-].S1C(C)=CC=C1C(=O)C[N+]1=CC=CC(C=2NN=C(CC3=CSC=C3)C=2)=C1 CNBJYYXRLNMBTE-UHFFFAOYSA-M 0.000 claims 1
- QPTXCMKRSUPTPK-UHFFFAOYSA-M 1-(5-phenyl-1H-pyrazol-3-yl)quinolin-1-ium chloride Chemical compound [Cl-].C1(=CC=CC=C1)C1=NNC(=C1)[N+]1=CC=CC2=CC=CC=C12 QPTXCMKRSUPTPK-UHFFFAOYSA-M 0.000 claims 1
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical class CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 claims 1
- UPHOPMSGKZNELG-UHFFFAOYSA-N 2-hydroxynaphthalene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)=C(O)C=CC2=C1 UPHOPMSGKZNELG-UHFFFAOYSA-N 0.000 claims 1
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical class OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 claims 1
- LPQQFLSAMKBWKV-UHFFFAOYSA-N 3-[5-(2-cyclohexylethyl)-1h-pyrazol-3-yl]pyridine Chemical compound C1CCCCC1CCC(=NN1)C=C1C1=CC=CN=C1 LPQQFLSAMKBWKV-UHFFFAOYSA-N 0.000 claims 1
- FNAOAOSRHLCODW-UHFFFAOYSA-N 3-[5-[(3,5-dimethylpyrazol-1-yl)methyl]-1H-pyrazol-3-yl]pyridin-1-ium bromide Chemical compound [Br-].CC1=NN(C(=C1)C)CC1=NNC(=C1)C=1C=[NH+]C=CC=1 FNAOAOSRHLCODW-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- 239000004475 Arginine Substances 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 150000000994 L-ascorbates Chemical class 0.000 claims 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 229920002472 Starch Polymers 0.000 claims 1
- 150000001242 acetic acid derivatives Chemical class 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
- 159000000013 aluminium salts Chemical class 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- 150000007860 aryl ester derivatives Chemical class 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000005841 biaryl group Chemical group 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 150000001642 boronic acid derivatives Chemical class 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 1
- 229960001231 choline Drugs 0.000 claims 1
- 150000001860 citric acid derivatives Chemical class 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 150000002315 glycerophosphates Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 claims 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 239000000644 isotonic solution Substances 0.000 claims 1
- 239000008101 lactose Substances 0.000 claims 1
- 239000006210 lotion Substances 0.000 claims 1
- 235000019359 magnesium stearate Nutrition 0.000 claims 1
- 150000002688 maleic acid derivatives Chemical class 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims 1
- 229940051866 mouthwash Drugs 0.000 claims 1
- GRMOAAZJHLRPIL-UHFFFAOYSA-N n-cyclopropyl-2-[3-[5-[(3,5-dimethylpyrazol-1-yl)methyl]-1h-pyrazol-3-yl]pyridin-1-ium-1-yl]acetamide;bromide Chemical compound [Br-].N1=C(C)C=C(C)N1CC1=NNC(C=2C=[N+](CC(=O)NC3CC3)C=CC=2)=C1 GRMOAAZJHLRPIL-UHFFFAOYSA-N 0.000 claims 1
- 150000002823 nitrates Chemical class 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 claims 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 1
- WJKIGWPCVFLGAT-UHFFFAOYSA-N pyridine;dihydrobromide Chemical class [Br-].[Br-].C1=CC=[NH+]C=C1.C1=CC=[NH+]C=C1 WJKIGWPCVFLGAT-UHFFFAOYSA-N 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 150000003873 salicylate salts Chemical class 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000008107 starch Substances 0.000 claims 1
- 235000019698 starch Nutrition 0.000 claims 1
- 150000003890 succinate salts Chemical class 0.000 claims 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 1
- 239000000454 talc Substances 0.000 claims 1
- 229910052623 talc Inorganic materials 0.000 claims 1
- 150000003892 tartrate salts Chemical class 0.000 claims 1
- 125000004001 thioalkyl group Chemical group 0.000 claims 1
- 229940034610 toothpaste Drugs 0.000 claims 1
- 239000000606 toothpaste Substances 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 108010005094 Advanced Glycation End Products Proteins 0.000 description 92
- 230000015572 biosynthetic process Effects 0.000 description 30
- 210000003491 skin Anatomy 0.000 description 28
- 108090000623 proteins and genes Proteins 0.000 description 25
- 102000004169 proteins and genes Human genes 0.000 description 24
- 210000001519 tissue Anatomy 0.000 description 18
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 102000008186 Collagen Human genes 0.000 description 10
- 108010035532 Collagen Proteins 0.000 description 10
- 229920001436 collagen Polymers 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 9
- 230000036252 glycation Effects 0.000 description 8
- 230000001965 increasing effect Effects 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 7
- 230000002255 enzymatic effect Effects 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 102000016942 Elastin Human genes 0.000 description 6
- 108010014258 Elastin Proteins 0.000 description 6
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 208000035475 disorder Diseases 0.000 description 6
- 229920002549 elastin Polymers 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 206010040954 Skin wrinkling Diseases 0.000 description 5
- 239000002537 cosmetic Substances 0.000 description 5
- 210000004207 dermis Anatomy 0.000 description 5
- 230000003511 endothelial effect Effects 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 230000007246 mechanism Effects 0.000 description 5
- 210000001616 monocyte Anatomy 0.000 description 5
- 210000000214 mouth Anatomy 0.000 description 5
- 230000002441 reversible effect Effects 0.000 description 5
- 208000024827 Alzheimer disease Diseases 0.000 description 4
- 206010012689 Diabetic retinopathy Diseases 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 210000000056 organ Anatomy 0.000 description 4
- 208000007342 Diabetic Nephropathies Diseases 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 230000001413 cellular effect Effects 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 230000006735 deficit Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 208000033679 diabetic kidney disease Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000013595 glycosylation Effects 0.000 description 3
- 238000006206 glycosylation reaction Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 235000000346 sugar Nutrition 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 230000037303 wrinkles Effects 0.000 description 3
- 206010003694 Atrophy Diseases 0.000 description 2
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 2
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 2
- 208000002249 Diabetes Complications Diseases 0.000 description 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 2
- 206010012655 Diabetic complications Diseases 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 102000005622 Receptor for Advanced Glycation End Products Human genes 0.000 description 2
- 108010045108 Receptor for Advanced Glycation End Products Proteins 0.000 description 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 2
- 101710172711 Structural protein Proteins 0.000 description 2
- 210000001789 adipocyte Anatomy 0.000 description 2
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 2
- 230000000890 antigenic effect Effects 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 230000037444 atrophy Effects 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000001736 capillary Anatomy 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229960003260 chlorhexidine Drugs 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 210000003038 endothelium Anatomy 0.000 description 2
- 210000002615 epidermis Anatomy 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000007760 free radical scavenging Effects 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 238000001631 haemodialysis Methods 0.000 description 2
- 230000000322 hemodialysis Effects 0.000 description 2
- 208000026278 immune system disease Diseases 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 230000002427 irreversible effect Effects 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 230000005012 migration Effects 0.000 description 2
- 238000013508 migration Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000007823 neuropathy Effects 0.000 description 2
- 206010033675 panniculitis Diseases 0.000 description 2
- 230000000750 progressive effect Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 210000004304 subcutaneous tissue Anatomy 0.000 description 2
- 230000000451 tissue damage Effects 0.000 description 2
- 231100000827 tissue damage Toxicity 0.000 description 2
- UJOUHMMIDLYDDD-UHFFFAOYSA-N 1-phenyl-2-(1,3-thiazol-3-ium-2-yl)ethanone;bromide Chemical compound [Br-].C=1C=CC=CC=1C(=O)CC1=[NH+]C=CS1 UJOUHMMIDLYDDD-UHFFFAOYSA-N 0.000 description 1
- 206010001580 Albuminuria Diseases 0.000 description 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 description 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 241000283014 Dama Species 0.000 description 1
- 206010063547 Diabetic macroangiopathy Diseases 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 102000003974 Fibroblast growth factor 2 Human genes 0.000 description 1
- 108090000379 Fibroblast growth factor 2 Proteins 0.000 description 1
- 229940123457 Free radical scavenger Drugs 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 238000012404 In vitro experiment Methods 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- 206010054805 Macroangiopathy Diseases 0.000 description 1
- 108010057466 NF-kappa B Proteins 0.000 description 1
- 102000003945 NF-kappa B Human genes 0.000 description 1
- 206010029113 Neovascularisation Diseases 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 206010053159 Organ failure Diseases 0.000 description 1
- 108010038512 Platelet-Derived Growth Factor Proteins 0.000 description 1
- 102000010780 Platelet-Derived Growth Factor Human genes 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 102000016611 Proteoglycans Human genes 0.000 description 1
- 108010067787 Proteoglycans Proteins 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 description 1
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 description 1
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 206010048222 Xerosis Diseases 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- MKOMESMZHZNBIZ-UHFFFAOYSA-M alagebrium Chemical compound [Cl-].CC1=C(C)SC=[N+]1CC(=O)C1=CC=CC=C1 MKOMESMZHZNBIZ-UHFFFAOYSA-M 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000033115 angiogenesis Effects 0.000 description 1
- 230000002882 anti-plaque Effects 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 210000002469 basement membrane Anatomy 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- QQFYLZXBFWWJHR-UHFFFAOYSA-M benzyl(triethyl)phosphanium;bromide Chemical compound [Br-].CC[P+](CC)(CC)CC1=CC=CC=C1 QQFYLZXBFWWJHR-UHFFFAOYSA-M 0.000 description 1
- 230000008238 biochemical pathway Effects 0.000 description 1
- 230000003851 biochemical process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000004155 blood-retinal barrier Anatomy 0.000 description 1
- 230000004378 blood-retinal barrier Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 239000001058 brown pigment Substances 0.000 description 1
- 230000009084 cardiovascular function Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000005779 cell damage Effects 0.000 description 1
- 230000008809 cell oxidative stress Effects 0.000 description 1
- 230000006041 cell recruitment Effects 0.000 description 1
- 230000003399 chemotactic effect Effects 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 230000006999 cognitive decline Effects 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 230000002596 correlated effect Effects 0.000 description 1
- 230000009260 cross reactivity Effects 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- VEVRNHHLCPGNDU-MUGJNUQGSA-O desmosine Chemical compound OC(=O)[C@@H](N)CCCC[N+]1=CC(CC[C@H](N)C(O)=O)=C(CCC[C@H](N)C(O)=O)C(CC[C@H](N)C(O)=O)=C1 VEVRNHHLCPGNDU-MUGJNUQGSA-O 0.000 description 1
- JNSGIVNNHKGGRU-JYRVWZFOSA-N diethoxyphosphinothioyl (2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetate Chemical compound CCOP(=S)(OCC)OC(=O)C(=N/OC)\C1=CSC(N)=N1 JNSGIVNNHKGGRU-JYRVWZFOSA-N 0.000 description 1
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 1
- 230000003828 downregulation Effects 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 210000004709 eyebrow Anatomy 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 230000008921 facial expression Effects 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 210000004907 gland Anatomy 0.000 description 1
- 210000000585 glomerular basement membrane Anatomy 0.000 description 1
- 230000009229 glucose formation Effects 0.000 description 1
- 102000035122 glycosylated proteins Human genes 0.000 description 1
- 108091005608 glycosylated proteins Proteins 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000003102 growth factor Substances 0.000 description 1
- 230000002650 habitual effect Effects 0.000 description 1
- 210000003780 hair follicle Anatomy 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229960002591 hydroxyproline Drugs 0.000 description 1
- 230000008105 immune reaction Effects 0.000 description 1
- 230000037189 immune system physiology Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 210000001821 langerhans cell Anatomy 0.000 description 1
- 239000002960 lipid emulsion Substances 0.000 description 1
- 210000001165 lymph node Anatomy 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 210000002752 melanocyte Anatomy 0.000 description 1
- 230000004118 muscle contraction Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 231100000189 neurotoxic Toxicity 0.000 description 1
- 230000002887 neurotoxic effect Effects 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 230000021368 organ growth Effects 0.000 description 1
- 239000002357 osmotic agent Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000004796 pathophysiological change Effects 0.000 description 1
- 230000004963 pathophysiological condition Effects 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 210000004303 peritoneum Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000008832 photodamage Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 201000003004 ptosis Diseases 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000007348 radical reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 230000008085 renal dysfunction Effects 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 210000001732 sebaceous gland Anatomy 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 210000000106 sweat gland Anatomy 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 230000036344 tooth staining Effects 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 230000003827 upregulation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- 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
-
- 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
- A61P17/10—Anti-acne agents
-
- 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
- A61P17/16—Emollients or protectives, e.g. against radiation
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P27/12—Ophthalmic agents for cataracts
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US28138001P | 2001-04-05 | 2001-04-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200306370B true ZA200306370B (en) | 2004-06-07 |
Family
ID=23077044
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200306370A ZA200306370B (en) | 2001-04-05 | 2003-08-15 | Heterocyclic compounds for aging-related and diabetic vascular complications. |
Country Status (22)
Country | Link |
---|---|
US (2) | US7223777B2 (hu) |
EP (1) | EP1373263B1 (hu) |
JP (2) | JP4485744B2 (hu) |
KR (1) | KR100785109B1 (hu) |
CN (1) | CN1259316C (hu) |
AT (1) | ATE280766T1 (hu) |
AU (1) | AU2002253432B2 (hu) |
BR (1) | BR0208561A (hu) |
CA (1) | CA2439593C (hu) |
CZ (1) | CZ20032013A3 (hu) |
DE (1) | DE60201740T2 (hu) |
DK (1) | DK1373263T3 (hu) |
ES (1) | ES2231685T3 (hu) |
HK (1) | HK1061234A1 (hu) |
HU (1) | HUP0400823A3 (hu) |
MX (1) | MXPA03008089A (hu) |
PL (1) | PL365441A1 (hu) |
PT (1) | PT1373263E (hu) |
RU (1) | RU2291154C2 (hu) |
SI (1) | SI1373263T1 (hu) |
WO (1) | WO2002085897A1 (hu) |
ZA (1) | ZA200306370B (hu) |
Families Citing this family (54)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1355645A4 (en) * | 2000-12-29 | 2005-02-23 | Alteon Inc | METHOD FOR THE TREATMENT OF FIBROUS OR OTHER IIIC INDICATIONS |
HUP0400823A3 (en) * | 2001-04-05 | 2010-06-28 | Torrent Pharmaceuticals Ltd | Heterocyclic compounds for treating aging-related and diabetic vascular complications, their preparation and pharmaceutical compositions containing them |
CN100436445C (zh) * | 2003-02-07 | 2008-11-26 | 第一制药株式会社 | 吡唑衍生物 |
PL377848A1 (pl) | 2003-02-07 | 2006-02-20 | Daiichi Pharmaceutical Co., Ltd. | Pochodne pirazoli |
EP1669348A4 (en) | 2003-09-30 | 2009-03-11 | Eisai R&D Man Co Ltd | NEW ANTIPILIC AGENT CONTAINING A HETEROCYCLIC COMPOUND |
US7354938B2 (en) * | 2004-03-23 | 2008-04-08 | Amgen Inc. | Pyrazole compounds and uses related thereto |
US20050241110A1 (en) * | 2004-04-09 | 2005-11-03 | Bruce Baker | Ergonomic handles, especially for garden tools |
WO2006002983A1 (en) * | 2004-07-06 | 2006-01-12 | Novartis Ag | Combination of organic compounds |
US20090227799A1 (en) * | 2004-08-09 | 2009-09-10 | Kazutaka Nakamoto | Novel Antimalarial Agent Containing Heterocyclic Compound |
WO2006033943A2 (en) | 2004-09-17 | 2006-03-30 | Exelixis, Inc | Pyrazole kinase modulators and methods of use |
WO2006069063A1 (en) | 2004-12-20 | 2006-06-29 | Genentech, Inc. | Pyrrolidine inhibitors of iap |
WO2006091761A1 (en) * | 2005-02-24 | 2006-08-31 | University Of Washington | Methods for treatment of retinal degenerative disease |
EP1864980A4 (en) | 2005-03-30 | 2010-08-18 | Eisai R&D Man Co Ltd | A PYRIDINE DERIVATIVE ANTIPILIC AGENT |
KR101003569B1 (ko) | 2005-10-31 | 2010-12-22 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 헤테로환 치환 피리딘 유도체 및 이들을 함유하는 항진균제 |
CN101300250B (zh) * | 2005-10-31 | 2012-09-05 | 卫材R&D管理有限公司 | 杂环取代吡啶衍生物及含有该衍生物的抗真菌剂 |
TWI385169B (zh) | 2005-10-31 | 2013-02-11 | Eisai R&D Man Co Ltd | 經雜環取代之吡啶衍生物及含有彼之抗真菌劑 |
SA07280004B1 (ar) | 2006-02-02 | 2011-10-29 | استرازينيكا ايه بي | ملح سترات من مركب 2- هيدروكسي –3- [5- (مورفولين –4- يل ميثيل) بيريدين –2- يل] 1h- إندول –5- كربونيتريل سترات |
AU2007270814B2 (en) | 2006-07-05 | 2011-07-14 | Pfizer Products Inc. | Pyrazole derivatives as cytochrome P450 inhibitors |
WO2008035726A1 (fr) | 2006-09-21 | 2008-03-27 | Eisai R & D Management Co., Ltd. | Dérivé de pyridine substitué par un cycle hétéroaryle, et agent antifongique le comprenant |
ES2421326T3 (es) | 2006-11-29 | 2013-08-30 | Abbvie Inc. | Inhibidores de la enzima diacilglicerol O-aciltransferasa de tipo 1 |
US20090197819A1 (en) * | 2007-03-20 | 2009-08-06 | Clarence Albert Johnson | Compositions for improving and repairing skin |
US20080312169A1 (en) * | 2007-03-20 | 2008-12-18 | Clarence Albert Johnson | Cosmetic use of D-ribose |
CN102702185A (zh) | 2007-04-27 | 2012-10-03 | 卫材R&D管理有限公司 | 杂环取代吡啶衍生物的盐的结晶 |
TW200841879A (en) | 2007-04-27 | 2008-11-01 | Eisai R&D Man Co Ltd | Pyridine derivatives substituted by heterocyclic ring and phosphonoamino group, and anti-fungal agent containing same |
KR20100024923A (ko) | 2007-04-30 | 2010-03-08 | 제넨테크, 인크. | Iap의 억제제 |
FR2918570B1 (fr) * | 2007-07-09 | 2012-10-05 | Engelhard Lyon | DIGLYCATION DES AGEs. |
WO2009042542A1 (en) * | 2007-09-26 | 2009-04-02 | Indiana University Research And Technology Corporation | Benzoquinone derivative e3330 in combination with chemotherapeutic agents for the treatment of cancer and angiogenesis |
US8410277B2 (en) | 2007-12-26 | 2013-04-02 | Eisai R&D Managment Co., Ltd. | Method for manufacturing heterocycle substituted pyridine derivatives |
US8513287B2 (en) | 2007-12-27 | 2013-08-20 | Eisai R&D Management Co., Ltd. | Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same |
KR100989093B1 (ko) | 2008-01-18 | 2010-10-25 | 한화제약주식회사 | 생강나무 가지의 추출물을 포함하는 심혈관계 질환의 예방 및 치료용 조성물 |
RU2010135524A (ru) * | 2008-01-25 | 2012-02-27 | Торрент Фармасьютикалз Лтд. (In) | Фармацевтические комбинации |
US20090232750A1 (en) * | 2008-03-13 | 2009-09-17 | St Cyr John A | Compositions for indoor tanning |
EP2318395A4 (en) | 2008-08-02 | 2011-10-26 | Genentech Inc | IPA INHIBITORS |
EP2345328A4 (en) * | 2008-09-19 | 2014-06-25 | Sumitomo Chemical Co | COMPOSITION FOR USE IN AGRICULTURE |
CN102186477B (zh) * | 2008-10-16 | 2013-07-17 | 奥梅-杨森制药有限公司 | 作为代谢型谷氨酸受体调节剂的吲哚和苯并吗啉衍生物 |
US8188119B2 (en) | 2008-10-24 | 2012-05-29 | Eisai R&D Management Co., Ltd | Pyridine derivatives substituted with heterocyclic ring and γ-glutamylamino group, and antifungal agents containing same |
EP2427432A2 (en) | 2009-05-07 | 2012-03-14 | Torrent Pharmaceuticals Limited | Novel heterocyclic compounds |
KR101040162B1 (ko) * | 2009-05-12 | 2011-06-09 | 주식회사 카모스 | 감시카메라의 브라켓 |
WO2011051198A2 (de) | 2009-10-30 | 2011-05-05 | Bayer Cropscience Ag | Pyridin-derivate als pflanzenschutzmittel |
KR101018881B1 (ko) * | 2009-11-03 | 2011-03-04 | 주식회사 엑스트론아이앤티 | 감시카메라용 브라켓 |
CN102858748B (zh) * | 2010-04-28 | 2015-06-17 | 东丽株式会社 | 阿尔茨海默病的治疗剂或预防剂 |
WO2012020738A1 (ja) * | 2010-08-09 | 2012-02-16 | 武田薬品工業株式会社 | 複素環化合物およびその用途 |
SI2968249T1 (sl) | 2013-02-22 | 2019-04-30 | Samumed, Llc | Gama-diketoni kot aktivatorji signalne poti Wnt/beta-katenin |
US9226890B1 (en) | 2013-12-10 | 2016-01-05 | Englewood Lab, Llc | Polysilicone base for scar treatment |
EP3145923B1 (en) * | 2014-05-22 | 2019-01-30 | F. Hoffmann-La Roche AG | Indolin-2-one and 1,3-dihydro-pyrrolo[3,2-c]pyridin-2-one derivatives |
CN107106549B (zh) | 2014-08-20 | 2020-06-16 | 萨穆梅德有限公司 | 用于治疗和预防老化皮肤和皱纹的γ–二酮 |
FR3026947B1 (fr) * | 2014-10-10 | 2017-12-08 | Basf Beauty Care Solutions France Sas | Activite deglycation d'une combinaison d'un extrait de salvia miltiorrhiza et de niacine et/ou de niacinamide |
MX2017012943A (es) | 2015-04-08 | 2018-01-30 | Torrent Pharmaceuticals Ltd | Nuevos compuestos de piridinio. |
CN106806886B (zh) * | 2015-12-01 | 2021-07-16 | 华中科技大学 | 一种快速消除口臭的口气清新剂及其医药用途 |
CN111698989B (zh) | 2017-12-07 | 2023-08-01 | 安普利克斯制药公司 | 杂环取代的吡啶衍生物抗真菌剂 |
CN108157405B (zh) * | 2018-02-06 | 2020-10-02 | 上海应用技术大学 | 一种灭蟑螂饵剂及其制备方法和应用 |
WO2020005860A1 (en) * | 2018-06-25 | 2020-01-02 | Amplyx Pharmaceuticals, Inc. | Pyridine derivatives substituted by heterocyclic ring and amino group |
EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | PYRROLE AND PYRAZOLE COMPOUNDS AND METHODS OF USE THERE |
DE202022104072U1 (de) | 2022-07-19 | 2022-07-29 | Siva Subramanian Narayanasamy | Heterozyklisch substituierte pyridinderivate antimykotische Mittel |
Family Cites Families (24)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3501484A (en) * | 1968-01-15 | 1970-03-17 | Miles Lab | Certain substituted 3 - (2-indolyl)-1,2,5,6-tetrahydropyridines and derivatives thereof |
US3501312A (en) * | 1968-07-22 | 1970-03-17 | Eastman Kodak Co | Direct positive silver halide emulsions containing trimethine cyanine dyes |
US3957805A (en) * | 1974-07-24 | 1976-05-18 | American Cyanamid Company | Substituted pyridines and diazines and methods of preparing the same |
US5514676A (en) | 1984-03-19 | 1996-05-07 | The Rockefeller University | Amino-benzoic acids and derivatives, and methods of use |
US5272176A (en) * | 1984-03-19 | 1993-12-21 | The Rockefeller University | Advanced glycation inhibitors containing amino-benzoic acids and derivatives, and methods of use |
US4758583A (en) | 1984-03-19 | 1988-07-19 | The Rockefeller University | Method and agents for inhibiting protein aging |
US5137916A (en) | 1985-11-14 | 1992-08-11 | The Rockefeller University | Advanced glycation inhibitors containing amino-benzoic acids and derivatives, and methods of use |
GB8714789D0 (en) * | 1987-06-24 | 1987-07-29 | Lundbeck & Co As H | Heterocyclic compounds |
EP0339496A3 (en) | 1988-04-26 | 1991-05-08 | Ono Pharmaceutical Co., Ltd. | Aminoguanidine derivatives |
US5330994A (en) * | 1992-03-24 | 1994-07-19 | Warner-Lambert Company | Tetrahydropyridine isoxazoline derivatives |
DE4210502A1 (de) * | 1992-03-31 | 1993-10-07 | Bayer Ag | Verwendung von 3-aminosubstituierten Isoxazolderivaten zur Bekämpfung von Endoparasiten, neue 3-aminosubstituierte Isoxazolderivate und Verfahren zu ihrer Herstellung |
US5656261A (en) | 1995-01-18 | 1997-08-12 | The Picower Institute For Medical Research | Preventing and reversing advanced glycosylation endproducts |
DE69629176T2 (de) | 1995-01-18 | 2004-06-03 | Alteon Inc. | Verwendung von thiazoliumverbindungen zum verhindern und umkehren der bildung von endprodukten der fortgeschrittenen glykosylierung |
US6228858B1 (en) * | 1995-09-12 | 2001-05-08 | University Of Kansas Medical Center | Advanced glycation end-product intermediaries and post-amadori inhibition |
JPH09291082A (ja) * | 1996-02-27 | 1997-11-11 | Sankyo Co Ltd | イソキサゾール誘導体 |
AU7553198A (en) * | 1997-06-12 | 1998-12-30 | Sumitomo Pharmaceuticals Company, Limited | Pyrazole derivatives |
AU3512400A (en) * | 1999-03-05 | 2000-09-21 | Kansas University Medical Center | Novel post-amadori inhibitors of advanced glycation reactions |
US20010044445A1 (en) * | 1999-04-08 | 2001-11-22 | Bamaung Nwe Y. | Azole inhibitors of cytokine production |
WO2000066101A2 (en) * | 1999-04-30 | 2000-11-09 | City Of Hope | Method of inhibiting glycation product formation |
FR2796278B1 (fr) | 1999-07-16 | 2002-05-03 | Oreal | Utilisation d'au moins un hydroxystilbene comme agent anti-glycation |
HU227523B1 (en) * | 1999-10-06 | 2011-07-28 | Torrent Pharmaceuticals Ltd | Pyridinium derivatives for the management of aging-related and diabetic vascular complications, process for their preparation and therapeutic uses thereof |
CA2351075A1 (en) * | 1999-10-06 | 2001-04-12 | Torrent Pharmaceuticals Ltd. | Pyridinium derivatives for the treatment of diabetic and aging-related vascular complications |
FR2802420B1 (fr) | 1999-12-21 | 2002-02-22 | Oreal | Utilisation du 3,3', 5,5'-tetrahydroxystilbene comme agent anti-glycation |
HUP0400823A3 (en) * | 2001-04-05 | 2010-06-28 | Torrent Pharmaceuticals Ltd | Heterocyclic compounds for treating aging-related and diabetic vascular complications, their preparation and pharmaceutical compositions containing them |
-
2002
- 2002-04-02 HU HU0400823A patent/HUP0400823A3/hu unknown
- 2002-04-02 JP JP2002583424A patent/JP4485744B2/ja not_active Expired - Fee Related
- 2002-04-02 CZ CZ20032013A patent/CZ20032013A3/cs unknown
- 2002-04-02 MX MXPA03008089A patent/MXPA03008089A/es active IP Right Grant
- 2002-04-02 CA CA2439593A patent/CA2439593C/en not_active Expired - Fee Related
- 2002-04-02 DE DE60201740T patent/DE60201740T2/de not_active Expired - Lifetime
- 2002-04-02 EP EP02722547A patent/EP1373263B1/en not_active Expired - Lifetime
- 2002-04-02 BR BR0208561-5A patent/BR0208561A/pt not_active IP Right Cessation
- 2002-04-02 PT PT02722547T patent/PT1373263E/pt unknown
- 2002-04-02 SI SI200230069T patent/SI1373263T1/xx unknown
- 2002-04-02 DK DK02722547T patent/DK1373263T3/da active
- 2002-04-02 ES ES02722547T patent/ES2231685T3/es not_active Expired - Lifetime
- 2002-04-02 AT AT02722547T patent/ATE280766T1/de not_active IP Right Cessation
- 2002-04-02 KR KR1020037012877A patent/KR100785109B1/ko not_active IP Right Cessation
- 2002-04-02 RU RU2003128076/04A patent/RU2291154C2/ru not_active IP Right Cessation
- 2002-04-02 PL PL02365441A patent/PL365441A1/xx not_active Application Discontinuation
- 2002-04-02 WO PCT/IB2002/001137 patent/WO2002085897A1/en active IP Right Grant
- 2002-04-02 CN CNB028069803A patent/CN1259316C/zh not_active Expired - Fee Related
- 2002-04-02 AU AU2002253432A patent/AU2002253432B2/en not_active Ceased
- 2002-04-05 US US10/116,135 patent/US7223777B2/en not_active Expired - Fee Related
-
2003
- 2003-08-15 ZA ZA200306370A patent/ZA200306370B/en unknown
-
2004
- 2004-06-11 HK HK04104243A patent/HK1061234A1/xx not_active IP Right Cessation
-
2007
- 2007-03-29 US US11/727,909 patent/US20070167493A1/en not_active Abandoned
-
2009
- 2009-12-25 JP JP2009295336A patent/JP2010100640A/ja active Pending
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ZA200306370B (en) | Heterocyclic compounds for aging-related and diabetic vascular complications. | |
AU2002253432A1 (en) | Heterocyclic compounds for aging-related and diabetic vascular complications | |
KR20080055874A (ko) | 당뇨병 치료용 디펩티딜 펩티다아제 억제제 | |
WO2005044192A2 (en) | Triazole compounds and uses related thereto | |
JP2002535256A (ja) | 化合物および方法 | |
JP4068843B2 (ja) | 老化関連及び糖尿病性血管合併症の管理のためのピリジニウム誘導体、それらの製造方法並びにそれらの治療的使用 | |
EP1304101A1 (en) | Composition and method for use of pyridinium derivatives in cosmetic and therapeutic applications | |
JPH07500811A (ja) | アミノ置換ピリミジン、その誘導体及びその使用方法 | |
MXPA02003496A (es) | Derivados de piridinio para el tratamiento de complicaciones vasculares diabeticas y relacionadas con la edad. | |
US6608094B2 (en) | Compounds for the management of aging-related and diabetic vascular complications, process for their preparation and therapeutic uses thereof | |
US20020103228A1 (en) | Composition and method for use of pyridinium derivatives in cosmetic and therapeutic applications | |
JP4471141B2 (ja) | 老化関連及び糖尿病脈管合併症の管理のための新規化合物、その製造方法及び治療的使用 | |
US20010018524A1 (en) | Novel compounds for the management of aging-related and diabetic vascular complications, process for their preparation and therapeutic uses thereof | |
JP2002515033A (ja) | 置換イミダゾリウム塩、及びタンパク質老化を阻止するためのそれらの使用 | |
WO2015003625A1 (zh) | 噻唑内盐类化合物、其制备方法及用途 | |
JP2014070051A (ja) | ニペコチン酸誘導体及びその医薬用途 | |
AU8936901A (en) | Composition and method for use of pyridinium derivatives in cosmetic and therapeutic applications | |
MXPA06004674A (en) | Triazole compounds and uses related thereto |