JP2002529414A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2002529414A5 JP2002529414A5 JP2000580624A JP2000580624A JP2002529414A5 JP 2002529414 A5 JP2002529414 A5 JP 2002529414A5 JP 2000580624 A JP2000580624 A JP 2000580624A JP 2000580624 A JP2000580624 A JP 2000580624A JP 2002529414 A5 JP2002529414 A5 JP 2002529414A5
- Authority
- JP
- Japan
- Prior art keywords
- oxoethyl
- dimethylthiazolium
- group
- bromide
- piperidinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 azosinyl Chemical group 0.000 description 136
- 150000001875 compounds Chemical class 0.000 description 68
- 125000000623 heterocyclic group Chemical group 0.000 description 48
- 239000000203 mixture Substances 0.000 description 42
- 125000000217 alkyl group Chemical group 0.000 description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 38
- 238000000034 method Methods 0.000 description 27
- 102000004169 proteins and genes Human genes 0.000 description 26
- 108090000623 proteins and genes Proteins 0.000 description 26
- 125000003545 alkoxy group Chemical group 0.000 description 24
- 206010012601 diabetes mellitus Diseases 0.000 description 24
- 125000001544 thienyl group Chemical group 0.000 description 23
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 230000032683 aging Effects 0.000 description 21
- 125000001424 substituent group Chemical group 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 229910052717 sulfur Inorganic materials 0.000 description 19
- 108010005094 Advanced Glycation End Products Proteins 0.000 description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 18
- 125000005842 heteroatom Chemical group 0.000 description 18
- 239000011593 sulfur Substances 0.000 description 18
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 16
- 229910052760 oxygen Inorganic materials 0.000 description 16
- 239000001301 oxygen Substances 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 13
- 230000002441 reversible effect Effects 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 238000000354 decomposition reaction Methods 0.000 description 12
- 210000003743 erythrocyte Anatomy 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000006206 glycosylation reaction Methods 0.000 description 11
- 239000003814 drug Substances 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 230000013595 glycosylation Effects 0.000 description 10
- 238000001727 in vivo Methods 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 9
- 102000008186 Collagen Human genes 0.000 description 9
- 108010035532 Collagen Proteins 0.000 description 9
- 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 9
- 125000003710 aryl alkyl group Chemical group 0.000 description 9
- 229920001436 collagen Polymers 0.000 description 9
- 238000004132 cross linking Methods 0.000 description 9
- 239000008103 glucose Substances 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 125000004043 oxo group Chemical group O=* 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- 108010055267 advanced glycation end products-bovine serum albumin Proteins 0.000 description 7
- 235000013305 food Nutrition 0.000 description 7
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 7
- 229920000136 polysorbate Polymers 0.000 description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 7
- JTRLSFYRCWFESV-UHFFFAOYSA-M 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-(furan-2-yl)ethanone;bromide Chemical compound [Br-].CC1=C(C)SC=[N+]1CC(=O)C1=CC=CO1 JTRLSFYRCWFESV-UHFFFAOYSA-M 0.000 description 6
- WYJOVVXUZNRJQY-UHFFFAOYSA-N 2-Acetylthiophene Chemical compound CC(=O)C1=CC=CS1 WYJOVVXUZNRJQY-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 6
- 125000000842 isoxazolyl group Chemical group 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 125000002769 thiazolinyl group Chemical group 0.000 description 6
- 125000000335 thiazolyl group Chemical group 0.000 description 6
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 229940027941 immunoglobulin g Drugs 0.000 description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 4
- LLFTXXTVSJOFFL-UHFFFAOYSA-N 1-(2,6-dimethylmorpholin-4-yl)-2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)ethanone Chemical compound C1C(C)OC(C)CN1C(=O)C[N+]1=CSC(C)=C1C LLFTXXTVSJOFFL-UHFFFAOYSA-N 0.000 description 4
- DONDNTYCSHDZSU-UHFFFAOYSA-N 1-(2,6-dimethylpiperidin-1-yl)-2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)ethanone Chemical compound CC1CCCC(C)N1C(=O)C[N+]1=CSC(C)=C1C DONDNTYCSHDZSU-UHFFFAOYSA-N 0.000 description 4
- JEHZYOQJTSWSSN-UHFFFAOYSA-N 1-(3-phenyl-1,2-oxazol-5-yl)-2-(1,3-thiazol-3-ium-3-yl)ethanone Chemical compound C=1C(C=2C=CC=CC=2)=NOC=1C(=O)C[N+]=1C=CSC=1 JEHZYOQJTSWSSN-UHFFFAOYSA-N 0.000 description 4
- TZXYREZVXALUJX-UHFFFAOYSA-M 1-(3-phenyl-1,2-oxazol-5-yl)-2-(1,3-thiazol-3-ium-3-yl)ethanone;bromide Chemical compound [Br-].C=1C(C=2C=CC=CC=2)=NOC=1C(=O)C[N+]=1C=CSC=1 TZXYREZVXALUJX-UHFFFAOYSA-M 0.000 description 4
- JZZFUZSEDNWQNM-UHFFFAOYSA-N 1-(azocan-1-yl)-2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)ethanone Chemical compound CC1=C(C)SC=[N+]1CC(=O)N1CCCCCCC1 JZZFUZSEDNWQNM-UHFFFAOYSA-N 0.000 description 4
- WMPUJZZUHKBSSK-UHFFFAOYSA-N 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-(2-methylpiperidin-1-yl)ethanone Chemical compound CC1CCCCN1C(=O)C[N+]1=CSC(C)=C1C WMPUJZZUHKBSSK-UHFFFAOYSA-N 0.000 description 4
- GJMFMWXBNPLVEK-UHFFFAOYSA-N 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-(3-phenyl-1,2-oxazol-5-yl)ethanone Chemical compound CC1=C(C)SC=[N+]1CC(=O)C1=CC(C=2C=CC=CC=2)=NO1 GJMFMWXBNPLVEK-UHFFFAOYSA-N 0.000 description 4
- CYGNBGKNQOUSCK-UHFFFAOYSA-N 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-(4-phenylpiperazin-1-yl)ethanone Chemical compound CC1=C(C)SC=[N+]1CC(=O)N1CCN(C=2C=CC=CC=2)CC1 CYGNBGKNQOUSCK-UHFFFAOYSA-N 0.000 description 4
- CDTRVOSWWYAVKH-UHFFFAOYSA-N 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-[4-(2-methoxyphenyl)piperazin-1-yl]ethanone Chemical compound COC1=CC=CC=C1N1CCN(C(=O)C[N+]=2C(=C(C)SC=2)C)CC1 CDTRVOSWWYAVKH-UHFFFAOYSA-N 0.000 description 4
- KXXSZJFQJBDQIM-UHFFFAOYSA-N 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-morpholin-4-ylethanone Chemical compound CC1=C(C)SC=[N+]1CC(=O)N1CCOCC1 KXXSZJFQJBDQIM-UHFFFAOYSA-N 0.000 description 4
- ZJWFKIGDSAYRSB-UHFFFAOYSA-N 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-piperidin-1-ylethanone Chemical compound CC1=C(C)SC=[N+]1CC(=O)N1CCCCC1 ZJWFKIGDSAYRSB-UHFFFAOYSA-N 0.000 description 4
- SCXNWXMCNPKVAL-UHFFFAOYSA-N 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-pyridin-2-ylethanone Chemical compound CC1=C(C)SC=[N+]1CC(=O)C1=CC=CC=N1 SCXNWXMCNPKVAL-UHFFFAOYSA-N 0.000 description 4
- VOUPWJIDKUXSDA-UHFFFAOYSA-N 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-pyrrolidin-1-ylethanone Chemical compound CC1=C(C)SC=[N+]1CC(=O)N1CCCC1 VOUPWJIDKUXSDA-UHFFFAOYSA-N 0.000 description 4
- DYAXUGSBIQQKBH-UHFFFAOYSA-N 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-thiomorpholin-4-ylethanone Chemical compound CC1=C(C)SC=[N+]1CC(=O)N1CCSCC1 DYAXUGSBIQQKBH-UHFFFAOYSA-N 0.000 description 4
- DDTLCHVGIIPVPH-UHFFFAOYSA-N 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-thiophen-2-ylethanone Chemical compound CC1=C(C)SC=[N+]1CC(=O)C1=CC=CS1 DDTLCHVGIIPVPH-UHFFFAOYSA-N 0.000 description 4
- KWCRMLXZLWVARI-UHFFFAOYSA-M 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-thiophen-2-ylethanone;bromide Chemical compound [Br-].CC1=C(C)SC=[N+]1CC(=O)C1=CC=CS1 KWCRMLXZLWVARI-UHFFFAOYSA-M 0.000 description 4
- FLBDNKMVHLLUFD-UHFFFAOYSA-N 2-[5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium-3-yl]-1-(3-phenyl-1,2-oxazol-5-yl)ethanone Chemical compound CC1=C(CCO)SC=[N+]1CC(=O)C1=CC(C=2C=CC=CC=2)=NO1 FLBDNKMVHLLUFD-UHFFFAOYSA-N 0.000 description 4
- CJTRNNWDXJDOMI-UHFFFAOYSA-N 2-[5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium-3-yl]-1-thiophen-2-ylethanone Chemical compound CC1=C(CCO)SC=[N+]1CC(=O)C1=CC=CS1 CJTRNNWDXJDOMI-UHFFFAOYSA-N 0.000 description 4
- UHWNENCHFSDZQP-UHFFFAOYSA-N 2-bromo-1-thiophen-2-ylethanone Chemical compound BrCC(=O)C1=CC=CS1 UHWNENCHFSDZQP-UHFFFAOYSA-N 0.000 description 4
- UWSONZCNXUSTKW-UHFFFAOYSA-N 4,5-Dimethylthiazole Chemical compound CC=1N=CSC=1C UWSONZCNXUSTKW-UHFFFAOYSA-N 0.000 description 4
- KUBZVKFPEKCOCA-UHFFFAOYSA-O 6-[2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)acetyl]-3,4-dihydro-1h-quinolin-2-one Chemical compound CC1=C(C)SC=[N+]1CC(=O)C1=CC=C(NC(=O)CC2)C2=C1 KUBZVKFPEKCOCA-UHFFFAOYSA-O 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 125000002785 azepinyl group Chemical group 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 125000002757 morpholinyl group Chemical group 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 125000004193 piperazinyl group Chemical group 0.000 description 4
- 125000003386 piperidinyl group Chemical group 0.000 description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000007017 scission Effects 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- 150000008163 sugars Chemical class 0.000 description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- LCVRJZFIUGHMBL-UHFFFAOYSA-M 1-(2,6-dimethylmorpholin-4-yl)-2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)ethanone;bromide Chemical compound [Br-].C1C(C)OC(C)CN1C(=O)C[N+]1=CSC(C)=C1C LCVRJZFIUGHMBL-UHFFFAOYSA-M 0.000 description 3
- WXUOLERBCYPQQQ-UHFFFAOYSA-M 1-(2,6-dimethylpiperidin-1-yl)-2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)ethanone;chloride Chemical compound [Cl-].CC1CCCC(C)N1C(=O)C[N+]1=CSC(C)=C1C WXUOLERBCYPQQQ-UHFFFAOYSA-M 0.000 description 3
- FFSPIRQPLYRQJH-UHFFFAOYSA-N 1-(4-benzylpiperazin-1-yl)-2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)ethanone Chemical compound CC1=C(C)SC=[N+]1CC(=O)N1CCN(CC=2C=CC=CC=2)CC1 FFSPIRQPLYRQJH-UHFFFAOYSA-N 0.000 description 3
- SPYGDICNRQMZMX-UHFFFAOYSA-M 1-(4-benzylpiperazin-1-yl)-2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)ethanone;chloride Chemical compound [Cl-].CC1=C(C)SC=[N+]1CC(=O)N1CCN(CC=2C=CC=CC=2)CC1 SPYGDICNRQMZMX-UHFFFAOYSA-M 0.000 description 3
- QDGTZBZUCUCILP-UHFFFAOYSA-M 1-(4-benzylpiperidin-1-yl)-2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)ethanone;chloride Chemical compound [Cl-].CC1=C(C)SC=[N+]1CC(=O)N1CCC(CC=2C=CC=CC=2)CC1 QDGTZBZUCUCILP-UHFFFAOYSA-M 0.000 description 3
- GWHYXUQIRILHEJ-UHFFFAOYSA-M 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-(2-methylpiperidin-1-yl)ethanone;chloride Chemical compound [Cl-].CC1CCCCN1C(=O)C[N+]1=CSC(C)=C1C GWHYXUQIRILHEJ-UHFFFAOYSA-M 0.000 description 3
- IWQKISJSDFXZAT-UHFFFAOYSA-M 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-(3-phenyl-1,2-oxazol-5-yl)ethanone;bromide Chemical compound [Br-].CC1=C(C)SC=[N+]1CC(=O)C1=CC(C=2C=CC=CC=2)=NO1 IWQKISJSDFXZAT-UHFFFAOYSA-M 0.000 description 3
- MGJAIGKTZLCDLL-UHFFFAOYSA-M 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-(4-phenylpiperazin-1-yl)ethanone;bromide Chemical compound [Br-].CC1=C(C)SC=[N+]1CC(=O)N1CCN(C=2C=CC=CC=2)CC1 MGJAIGKTZLCDLL-UHFFFAOYSA-M 0.000 description 3
- MFIFQGQIIUNDEY-UHFFFAOYSA-M 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-[4-(2-methoxyphenyl)piperazin-1-yl]ethanone;chloride Chemical compound [Cl-].COC1=CC=CC=C1N1CCN(C(=O)C[N+]=2C(=C(C)SC=2)C)CC1 MFIFQGQIIUNDEY-UHFFFAOYSA-M 0.000 description 3
- BSEUFZMCJGIXAV-UHFFFAOYSA-M 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-morpholin-4-ylethanone;bromide Chemical compound [Br-].CC1=C(C)SC=[N+]1CC(=O)N1CCOCC1 BSEUFZMCJGIXAV-UHFFFAOYSA-M 0.000 description 3
- OHFBSVCCNJIHCO-UHFFFAOYSA-M 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-piperidin-1-ylethanone;bromide Chemical compound [Br-].CC1=C(C)SC=[N+]1CC(=O)N1CCCCC1 OHFBSVCCNJIHCO-UHFFFAOYSA-M 0.000 description 3
- ZQGZYARQBGFRNE-UHFFFAOYSA-M 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-pyridin-2-ylethanone;bromide Chemical compound [Br-].CC1=C(C)SC=[N+]1CC(=O)C1=CC=CC=N1 ZQGZYARQBGFRNE-UHFFFAOYSA-M 0.000 description 3
- QHQQHTYVQOPPPR-UHFFFAOYSA-M 2-[5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium-3-yl]-1-(3-phenyl-1,2-oxazol-5-yl)ethanone;bromide Chemical compound [Br-].CC1=C(CCO)SC=[N+]1CC(=O)C1=CC(C=2C=CC=CC=2)=NO1 QHQQHTYVQOPPPR-UHFFFAOYSA-M 0.000 description 3
- WLVMFPIVEOQCCF-UHFFFAOYSA-M 2-[5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium-3-yl]-1-thiophen-2-ylethanone;bromide Chemical compound [Br-].CC1=C(CCO)SC=[N+]1CC(=O)C1=CC=CS1 WLVMFPIVEOQCCF-UHFFFAOYSA-M 0.000 description 3
- AAOSLLBWWRKJIR-UHFFFAOYSA-N 2-chloro-1-pyrrolidin-1-ylethanone Chemical compound ClCC(=O)N1CCCC1 AAOSLLBWWRKJIR-UHFFFAOYSA-N 0.000 description 3
- KIZIQPFGFKRKGB-UHFFFAOYSA-N 6-[2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)acetyl]-3,4-dihydro-1h-quinolin-2-one;bromide Chemical compound [Br-].CC1=C(C)SC=[N+]1CC(=O)C1=CC=C(NC(=O)CC2)C2=C1 KIZIQPFGFKRKGB-UHFFFAOYSA-N 0.000 description 3
- 201000001320 Atherosclerosis Diseases 0.000 description 3
- 108010017384 Blood Proteins Proteins 0.000 description 3
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 206010040954 Skin wrinkling Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 101710172711 Structural protein Proteins 0.000 description 3
- WTPAMUNPUPPCMC-UHFFFAOYSA-M [Cl-].CCOC(=O)Cc1csc(n1)C(=O)C(N)[n+]1csc(C)c1C Chemical compound [Cl-].CCOC(=O)Cc1csc(n1)C(=O)C(N)[n+]1csc(C)c1C WTPAMUNPUPPCMC-UHFFFAOYSA-M 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004204 blood vessel Anatomy 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000002526 effect on cardiovascular system Effects 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 230000036252 glycation Effects 0.000 description 3
- 230000000670 limiting effect Effects 0.000 description 3
- 210000004379 membrane Anatomy 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000008092 positive effect Effects 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 230000037303 wrinkles Effects 0.000 description 3
- KNAYMWOVMIIFRR-UHFFFAOYSA-M 1-(azocan-1-yl)-2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)ethanone;bromide Chemical compound [Br-].CC1=C(C)SC=[N+]1CC(=O)N1CCCCCCC1 KNAYMWOVMIIFRR-UHFFFAOYSA-M 0.000 description 2
- RIOICWPXWNSBNN-UHFFFAOYSA-M 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-pyrrolidin-1-ylethanone;bromide Chemical compound [Br-].CC1=C(C)SC=[N+]1CC(=O)N1CCCC1 RIOICWPXWNSBNN-UHFFFAOYSA-M 0.000 description 2
- HALVBIFIRDXSQN-UHFFFAOYSA-M 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-thiomorpholin-4-ylethanone;bromide Chemical compound [Br-].CC1=C(C)SC=[N+]1CC(=O)N1CCSCC1 HALVBIFIRDXSQN-UHFFFAOYSA-M 0.000 description 2
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical compound BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 2
- 102000002260 Alkaline Phosphatase Human genes 0.000 description 2
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 2
- 102000004506 Blood Proteins Human genes 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 102000016942 Elastin Human genes 0.000 description 2
- 108010014258 Elastin Proteins 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 101000941893 Felis catus Leucine-rich repeat and calponin homology domain-containing protein 1 Proteins 0.000 description 2
- 208000002740 Muscle Rigidity Diseases 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 230000001746 atrial effect Effects 0.000 description 2
- OHDRQQURAXLVGJ-HLVWOLMTSA-N azane;(2e)-3-ethyl-2-[(e)-(3-ethyl-6-sulfo-1,3-benzothiazol-2-ylidene)hydrazinylidene]-1,3-benzothiazole-6-sulfonic acid Chemical compound [NH4+].[NH4+].S/1C2=CC(S([O-])(=O)=O)=CC=C2N(CC)C\1=N/N=C1/SC2=CC(S([O-])(=O)=O)=CC=C2N1CC OHDRQQURAXLVGJ-HLVWOLMTSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 239000001058 brown pigment Substances 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 210000001715 carotid artery Anatomy 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- 238000007405 data analysis Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 229920002549 elastin Polymers 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- UDUZHEYUSZGXTJ-UHFFFAOYSA-O ethyl 2-[2-[[2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)acetyl]amino]-1,3-thiazol-4-yl]acetate Chemical class CCOC(=O)CC1=CSC(NC(=O)C[N+]=2C(=C(C)SC=2)C)=N1 UDUZHEYUSZGXTJ-UHFFFAOYSA-O 0.000 description 2
- 210000000585 glomerular basement membrane Anatomy 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 201000001421 hyperglycemia Diseases 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000006384 methylpyridyl group Chemical group 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 201000008482 osteoarthritis Diseases 0.000 description 2
- 230000007170 pathology Effects 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- 230000036513 peripheral conductance Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- 125000005490 tosylate group Chemical class 0.000 description 2
- 0 *c1c(*)[n]c*1* Chemical compound *c1c(*)[n]c*1* 0.000 description 1
- LQZPFKLFIHYYMP-UHFFFAOYSA-M 1-(2,6-dimethylpiperidin-1-yl)-2-(4-methyl-1,3-thiazol-3-ium-3-yl)ethanone;chloride Chemical compound [Cl-].CC1CCCC(C)N1C(=O)C[N+]1=CSC=C1C LQZPFKLFIHYYMP-UHFFFAOYSA-M 0.000 description 1
- WPCNEFZMIKLWQH-UHFFFAOYSA-N 1-(4-benzylpiperidin-1-yl)-2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)ethanone Chemical compound CC1=C(C)SC=[N+]1CC(=O)N1CCC(CC=2C=CC=CC=2)CC1 WPCNEFZMIKLWQH-UHFFFAOYSA-N 0.000 description 1
- NBLLPEOFDQJKRF-UHFFFAOYSA-M 1-(4-benzylpiperidin-1-yl)-2-(5-methyl-1,3-thiazol-3-ium-3-yl)ethanone;chloride Chemical compound [Cl-].S1C(C)=C[N+](CC(=O)N2CCC(CC=3C=CC=CC=3)CC2)=C1 NBLLPEOFDQJKRF-UHFFFAOYSA-M 0.000 description 1
- ALBRQHHDIDCOEP-UHFFFAOYSA-M 1-(4-phenylpiperazin-1-yl)-2-(1,3-thiazol-3-ium-3-yl)ethanone;bromide Chemical compound [Br-].C1CN(C=2C=CC=CC=2)CCN1C(=O)C[N+]=1C=CSC=1 ALBRQHHDIDCOEP-UHFFFAOYSA-M 0.000 description 1
- IAECUCJVDGWKFF-UHFFFAOYSA-M 1-(furan-2-yl)-2-[4-(2-hydroxypentyl)-1,3-thiazol-3-ium-3-yl]ethanone;bromide Chemical compound [Br-].CCCC(O)CC1=CSC=[N+]1CC(=O)C1=CC=CO1 IAECUCJVDGWKFF-UHFFFAOYSA-M 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- LXFQSRIDYRFTJW-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonic acid Chemical class CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-N 0.000 description 1
- OBSLLHNATPQFMJ-UHFFFAOYSA-N 2,4-Dimethylthiazole Chemical compound CC1=CSC(C)=N1 OBSLLHNATPQFMJ-UHFFFAOYSA-N 0.000 description 1
- HJNHOBQOPVGZQM-UHFFFAOYSA-M 2-(1,3-thiazol-3-ium-3-yl)-1-thiomorpholin-4-ylethanone;bromide Chemical compound [Br-].C1CSCCN1C(=O)C[N+]=1C=CSC=1 HJNHOBQOPVGZQM-UHFFFAOYSA-M 0.000 description 1
- HTKJZDXVZXNXFC-UHFFFAOYSA-M 2-(1,3-thiazol-3-ium-3-yl)-1-thiophen-2-ylethanone;bromide Chemical compound [Br-].C=1C=CSC=1C(=O)C[N+]=1C=CSC=1 HTKJZDXVZXNXFC-UHFFFAOYSA-M 0.000 description 1
- HGCDHPJFPHNPOH-UHFFFAOYSA-M 2-(4,5-didodecyl-1,3-thiazol-3-ium-3-yl)-1-piperidin-1-ylethanone;bromide Chemical compound [Br-].CCCCCCCCCCCCC1=C(CCCCCCCCCCCC)SC=[N+]1CC(=O)N1CCCCC1 HGCDHPJFPHNPOH-UHFFFAOYSA-M 0.000 description 1
- UIGUQXDPXAUWPF-UHFFFAOYSA-M 2-(4,5-diethyl-1,3-thiazol-3-ium-3-yl)-1-pyrrolidin-1-ylethanone;bromide Chemical compound [Br-].CCC1=C(CC)SC=[N+]1CC(=O)N1CCCC1 UIGUQXDPXAUWPF-UHFFFAOYSA-M 0.000 description 1
- IRJRKLXWHOBCTB-UHFFFAOYSA-M 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-pyrrolidin-1-ylethanone;chloride Chemical compound [Cl-].CC1=C(C)SC=[N+]1CC(=O)N1CCCC1 IRJRKLXWHOBCTB-UHFFFAOYSA-M 0.000 description 1
- XMQJKZAWDAZTLY-UHFFFAOYSA-L 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-pyrrolidin-1-ylethanone;dichloride Chemical compound [Cl-].[Cl-].CC1=C(C)SC=[N+]1CC(=O)N1CCCC1.CC1=C(C)SC=[N+]1CC(=O)N1CCCC1 XMQJKZAWDAZTLY-UHFFFAOYSA-L 0.000 description 1
- PZIBNOZRVWNTOJ-UHFFFAOYSA-M 2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)-1-thiomorpholin-4-ylethanone;chloride Chemical compound [Cl-].CC1=C(C)SC=[N+]1CC(=O)N1CCSCC1 PZIBNOZRVWNTOJ-UHFFFAOYSA-M 0.000 description 1
- RGHHWDRTIMXOKK-UHFFFAOYSA-M 2-(4,5-dioctadecyl-1,3-thiazol-3-ium-3-yl)-1-morpholin-4-ylethanone;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCCC1=C(CCCCCCCCCCCCCCCCCC)SC=[N+]1CC(=O)N1CCOCC1 RGHHWDRTIMXOKK-UHFFFAOYSA-M 0.000 description 1
- PEYJOSALINQWNW-UHFFFAOYSA-M 2-(4,5-dioctyl-1,3-thiazol-3-ium-3-yl)-1-pyridin-2-ylethanone;bromide Chemical compound [Br-].CCCCCCCCC1=C(CCCCCCCC)SC=[N+]1CC(=O)C1=CC=CC=N1 PEYJOSALINQWNW-UHFFFAOYSA-M 0.000 description 1
- NTCHMNLAIQXLDX-UHFFFAOYSA-M 2-(4,5-dipropyl-1,3-thiazol-3-ium-3-yl)-1-(2-methylpiperidin-1-yl)ethanone;chloride Chemical compound [Cl-].CCCC1=C(CCC)SC=[N+]1CC(=O)N1C(C)CCCC1 NTCHMNLAIQXLDX-UHFFFAOYSA-M 0.000 description 1
- PCFZDIKQKKSBHH-UHFFFAOYSA-M 2-(4-octyl-1,3-thiazol-3-ium-3-yl)-1-(3-phenyl-1,2-oxazol-5-yl)ethanone;bromide Chemical compound [Br-].CCCCCCCCC1=CSC=[N+]1CC(=O)C1=CC(C=2C=CC=CC=2)=NO1 PCFZDIKQKKSBHH-UHFFFAOYSA-M 0.000 description 1
- CFTMHXOTUFMVDG-UHFFFAOYSA-M 2-(5-decyl-1,3-thiazol-3-ium-3-yl)-1-(furan-2-yl)ethanone;bromide Chemical compound [Br-].S1C(CCCCCCCCCC)=C[N+](CC(=O)C=2OC=CC=2)=C1 CFTMHXOTUFMVDG-UHFFFAOYSA-M 0.000 description 1
- BXGLPLWKBGTBTI-UHFFFAOYSA-M 2-[5-(6-hydroxyhexyl)-4-methyl-1,3-thiazol-3-ium-3-yl]-1-(3-phenyl-1,2-oxazol-5-yl)ethanone;bromide Chemical compound [Br-].CC1=C(CCCCCCO)SC=[N+]1CC(=O)C1=CC(C=2C=CC=CC=2)=NO1 BXGLPLWKBGTBTI-UHFFFAOYSA-M 0.000 description 1
- MPSMNABALLGJBN-UHFFFAOYSA-M 2-[5-(6-hydroxyhexyl)-4-methyl-1,3-thiazol-3-ium-3-yl]-1-thiophen-2-ylethanone;bromide Chemical compound [Br-].CC1=C(CCCCCCO)SC=[N+]1CC(=O)C1=CC=CS1 MPSMNABALLGJBN-UHFFFAOYSA-M 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- XZKIHKMTEMTJQX-UHFFFAOYSA-N 4-Nitrophenyl Phosphate Chemical compound OP(O)(=O)OC1=CC=C([N+]([O-])=O)C=C1 XZKIHKMTEMTJQX-UHFFFAOYSA-N 0.000 description 1
- UUBHUCBNFXCFES-UHFFFAOYSA-N 6-[2-(4,5-dioctyl-1,3-thiazol-3-ium-3-yl)acetyl]-3,4-dihydro-1h-quinolin-2-one;bromide Chemical compound [Br-].CCCCCCCCC1=C(CCCCCCCC)SC=[N+]1CC(=O)C1=CC=C(NC(=O)CC2)C2=C1 UUBHUCBNFXCFES-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DHVFYTVYZRHGCO-UHFFFAOYSA-M CC1=C(C)SC=[N+]1CC([S+]1C=CC=C1)=O.[Br-] Chemical compound CC1=C(C)SC=[N+]1CC([S+]1C=CC=C1)=O.[Br-] DHVFYTVYZRHGCO-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000002177 Cataract Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000014824 Crystallins Human genes 0.000 description 1
- 108010064003 Crystallins Proteins 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 238000002965 ELISA Methods 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 108060003393 Granulin Proteins 0.000 description 1
- 108010001336 Horseradish Peroxidase Proteins 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 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 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 208000018262 Peripheral vascular disease Diseases 0.000 description 1
- 208000017442 Retinal disease Diseases 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010040799 Skin atrophy Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- ICEOIBIVBSHHLB-UHFFFAOYSA-M [Br-].CC1CN(CC(O1)C)C(C[N+]1=CSC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O Chemical compound [Br-].CC1CN(CC(O1)C)C(C[N+]1=CSC(=C1C1=CC=CC=C1)C1=CC=CC=C1)=O ICEOIBIVBSHHLB-UHFFFAOYSA-M 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005243 carbonyl alkyl group Chemical group 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 210000002808 connective tissue Anatomy 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 208000033679 diabetic kidney disease Diseases 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 230000003511 endothelial effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007515 enzymatic degradation Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IYJRZOSANXSHFR-UHFFFAOYSA-N ethyl 2-[2-[[2-(4,5-dimethyl-1,3-thiazol-3-ium-3-yl)acetyl]amino]-1,3-thiazol-4-yl]acetate;chloride Chemical compound [Cl-].CCOC(=O)CC1=CSC(NC(=O)C[N+]=2C(=C(C)SC=2)C)=N1 IYJRZOSANXSHFR-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 206010061989 glomerulosclerosis Diseases 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 238000010874 in vitro model Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 238000012332 laboratory investigation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 210000000653 nervous system Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 231100000255 pathogenic effect Toxicity 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 229920001184 polypeptide Chemical group 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 108090000765 processed proteins & peptides Chemical group 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 230000037394 skin elasticity Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012064 sodium phosphate buffer Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 230000003966 vascular damage Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/189,200 US6121300A (en) | 1998-11-10 | 1998-11-10 | Reversing advanced glycosylation cross-links using heterocyclic-substituted thiazolium salts |
| US09/189,200 | 1998-11-10 | ||
| PCT/US1999/026565 WO2000027395A1 (en) | 1998-11-10 | 1999-11-10 | Reversing advanced glycosylation cross-links using heterocyclic-substituted thiazolium salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002529414A JP2002529414A (ja) | 2002-09-10 |
| JP2002529414A5 true JP2002529414A5 (enExample) | 2007-01-25 |
Family
ID=22696355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000580624A Pending JP2002529414A (ja) | 1998-11-10 | 1999-11-10 | 複素環置換チアゾリウム塩を使用する進行したグリコシル化架橋物の逆転 |
Country Status (11)
| Country | Link |
|---|---|
| US (4) | US6121300A (enExample) |
| EP (1) | EP1128830B1 (enExample) |
| JP (1) | JP2002529414A (enExample) |
| KR (1) | KR20010080969A (enExample) |
| AT (1) | ATE388704T1 (enExample) |
| AU (1) | AU767889B2 (enExample) |
| CA (1) | CA2350211A1 (enExample) |
| DE (1) | DE69938357D1 (enExample) |
| MX (1) | MXPA01004721A (enExample) |
| NZ (1) | NZ511569A (enExample) |
| WO (1) | WO2000027395A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO315930B1 (no) | 1995-01-18 | 2003-11-17 | Picower Inst For Medical Res T | Anvendelse av tiazoliumforbindelser ved fremstilling av farmasöytiske preparater, preparater som inneholder forbindelsene, samt nyetiazoliumforbindelser |
| US5656261A (en) | 1995-01-18 | 1997-08-12 | The Picower Institute For Medical Research | Preventing and reversing advanced glycosylation endproducts |
| US6121300A (en) * | 1998-11-10 | 2000-09-19 | Wagle; Dilip R. | Reversing advanced glycosylation cross-links using heterocyclic-substituted thiazolium salts |
| US6458819B1 (en) * | 2000-02-23 | 2002-10-01 | Alteon, Inc. | Thiazolium compounds and treatments of disorders associated with protein aging |
| MXPA03000386A (es) * | 2000-07-13 | 2004-02-26 | Alteon Inc | Imidazolios y tiazolios substituidos con cianometilo y tratamientos de desordenes asociados con la maduracion de la proteina. |
| EP1313715B1 (en) * | 2000-08-23 | 2007-08-01 | Eli Lilly And Company | Oxazolyl-aryloxyacetic acid derivatives and their use as ppar agonists |
| WO2002053161A1 (en) * | 2000-12-29 | 2002-07-11 | Alteon, Inc. | Method for treating fibrotic diseases or other indications |
| WO2002053101A2 (en) * | 2000-12-29 | 2002-07-11 | Alteon, Inc. | Method for treating fibrotic diseases or other indications |
| MXPA03005954A (es) * | 2000-12-29 | 2004-05-24 | Alteon Inc | Metodo para tratar enfermedades fibroticas u otras indicaciones iiic. |
| CA2433346A1 (en) * | 2000-12-29 | 2002-07-11 | John J. Egan | Method for treating glaucoma ib |
| WO2002056836A2 (en) * | 2001-01-22 | 2002-07-25 | Farrington Pharmaceuticals, Llc | Method and composition for rejuvenating hair, nails, tissues, cells and organs by ex-vivo or immersive treatment |
| US7022721B1 (en) * | 2001-02-07 | 2006-04-04 | Peter C Ulrich | Method and composition for rejuvenating cells, tissues, organs, hair and nails |
| JP2004532862A (ja) * | 2001-05-30 | 2004-10-28 | アルテオン インコーポレイテッド | 線維性疾患又は他の適応症の治療方法 |
| CN1324019C (zh) * | 2003-04-02 | 2007-07-04 | 深圳市东阳光实业发展有限公司 | 氮杂双环盐类化合物及其治疗蛋白老化疾病的用途 |
| US20050014747A1 (en) * | 2003-04-18 | 2005-01-20 | Emily Reinhard | Dihydrothiazine prodrugs of thiazolium agents |
| US20040265238A1 (en) | 2003-06-27 | 2004-12-30 | Imtiaz Chaudry | Inhalable formulations for treating pulmonary hypertension and methods of using same |
| EP1753861A4 (en) * | 2004-02-17 | 2010-03-10 | Dynamis Therapeutics Inc | FRUCTOSAMINE-3-KINASE AND THE FORMATION OF COLLAGEN AND ELASTIN |
| CN100560589C (zh) * | 2004-04-21 | 2009-11-18 | 北京摩力克科技有限公司 | 咪唑并硒唑类化合物及其预防和/或者治疗与蛋白老化相关疾病的用途 |
| CN1690057B (zh) * | 2004-04-21 | 2010-05-26 | 北京摩力克科技有限公司 | 硒吩类衍生物及其预防和/或者治疗蛋白老化相关疾病的用途 |
| WO2006032165A1 (en) * | 2004-09-23 | 2006-03-30 | Beijing Molecule Science And Technology Co., Ltd | Novel substituted 5-membered-n-heterocyclic compounds and the use of them in treatment of the diseases associated with the aging of proteins |
| BRPI0707211A2 (pt) * | 2006-01-23 | 2011-04-26 | Procter & Gamble | composições para tratamento na lavagem de roupas com corante de tiazólio |
| CN101007789B (zh) | 2006-01-27 | 2014-08-20 | 北京摩力克科技有限公司 | 取代五元氮杂环盐类化合物及其治疗蛋白老化相关疾病的用途 |
| FR2918570B1 (fr) * | 2007-07-09 | 2012-10-05 | Engelhard Lyon | DIGLYCATION DES AGEs. |
| WO2009123753A1 (en) | 2008-04-04 | 2009-10-08 | North Carolina State University | Inhibition of bacterial biofilms with imidazole-phenyl derivatives |
| WO2010144686A1 (en) | 2009-06-10 | 2010-12-16 | North Carolina State University | Inhibition and dispersion of bacterial biofilms with benzimidazole derivatives |
| US9796952B2 (en) | 2012-09-25 | 2017-10-24 | The Procter & Gamble Company | Laundry care compositions with thiazolium dye |
| WO2016179089A1 (en) | 2015-05-01 | 2016-11-10 | Rensselaer Polytechnic Institute | Biomimetic nano-composite scaffold for enhanced bone healing and fracture repair |
| CN109431850A (zh) * | 2018-03-16 | 2019-03-08 | 广东众尔健生物科技有限公司 | 一种鼠尾胶原在化妆品领域的应用 |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5857116A (ja) * | 1981-09-30 | 1983-04-05 | Konishiroku Photo Ind Co Ltd | マイクロプロセツサを塔載したカメラ |
| GB8300728D0 (en) * | 1983-01-12 | 1983-02-16 | Erba Farmitalia | Substituted carboxy-thiazolo / 3 2 - a / pyrimidine derivatives |
| JPS60184038A (ja) * | 1984-03-01 | 1985-09-19 | Nippon Kasei Kk | １−ヒドロキシ−２−オン類の製造方法 |
| CA1273012A (en) * | 1984-07-02 | 1990-08-21 | Burton G. Christensen | 1-methylcarbapenems having an externally alkylated mono- of bicyclic 2-quarternary heteroarylalkylthio substituent |
| CA1273011A (en) * | 1984-07-02 | 1990-08-21 | Susan M. Schmitt | Carbapenems having an externally alkylated mono- or bicyclic 2-quaternary heteroarylalkylthio substituent |
| US4609670A (en) * | 1984-11-13 | 1986-09-02 | Eli Lilly And Company | Imidazolium hypoglycemic agents |
| US4683312A (en) * | 1984-11-13 | 1987-07-28 | Eli Lilly And Company | Imidazolium hypoglycemic agents |
| ZA86171B (en) | 1985-01-16 | 1986-08-27 | Hoffmann La Roche | Polycyclic salts |
| US5219852A (en) * | 1986-03-13 | 1993-06-15 | Dr. Karl Thomae Gmbh | Substituted thiazoles and oxazoles and pharmaceutical compositions and methods thereof |
| DE3621775A1 (de) * | 1986-03-13 | 1988-01-07 | Thomae Gmbh Dr K | Neue substituierte thiazole und oxazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| US4886814A (en) * | 1986-03-13 | 1989-12-12 | Dr. Karl Thomas Gmbh | Substituted thiazoles and oxazoles and 2-hydroxy-morpholines |
| US5185334A (en) * | 1989-07-31 | 1993-02-09 | Schering Corporation | 2,2-disubstituted glycerol and glycerol-like compounds, compositions and methods of use |
| JP2817219B2 (ja) * | 1988-09-08 | 1998-10-30 | 武田薬品工業株式会社 | カルバジン酸誘導体、その製造法及び製剤 |
| DE3839758A1 (de) * | 1988-10-24 | 1990-04-26 | Bayer Ag | Substituierte 2-aminothiazole |
| US5302608A (en) * | 1988-11-18 | 1994-04-12 | Takeda Chemical Industries, Ltd. | Age formation inhibitors |
| US5128351A (en) * | 1990-05-04 | 1992-07-07 | American Cyanamid Company | Bis-aryl amide and urea antagonists of platelet activating factor |
| US5225425A (en) * | 1990-05-04 | 1993-07-06 | American Cyanamid Company | Bis-aryl amide antagonists of platelet activating factor |
| DE4124587A1 (de) * | 1991-07-24 | 1993-01-28 | Luitpold Werk Chem Pharm | Dimethylacetessigsaeureamide, verfahren zu ihrer herstellung und arzneimittel |
| US5230998A (en) * | 1991-07-25 | 1993-07-27 | Neurath Alexander R | Method for the prescreening of drugs targeted to the V3 hypervariable loop of the HIV-1 envelope glycoprotein gp 120 |
| DE4129742A1 (de) * | 1991-09-06 | 1993-03-11 | Bayer Ag | Heterocyclisch substituierte chinolylmethoxy-phenylacetamide |
| DE4218159C2 (de) * | 1992-06-02 | 1997-07-31 | Luitpold Pharma Gmbh | 4,4,4-Trifluoracetessigsäureamide, Verfahren zu ihrer Herstellung und Arzneimittel |
| DE4222980A1 (de) * | 1992-07-13 | 1994-01-20 | Cassella Ag | Verwendung von 2-(N-(2-Aminoethyl)amino)-essigsäure-derivaten |
| ES2096933T3 (es) * | 1992-07-30 | 1997-03-16 | Drug Delivery System Inst Ltd | Compuesto capaz de permanecer en la region intracerebral y utilizacion del mismo. |
| TW268952B (enExample) * | 1993-02-26 | 1996-01-21 | Takeda Pharm Industry Co Ltd | |
| JP3126541B2 (ja) * | 1993-03-26 | 2001-01-22 | 千寿製薬株式会社 | ベンゾチアゾール誘導体、その製法及びその用途 |
| DE4341526A1 (de) * | 1993-12-06 | 1995-06-08 | Basf Ag | 2,4-Diaminothiazole und ihre Herstellung |
| US5700819A (en) * | 1994-11-29 | 1997-12-23 | Grelan Pharmaceutical Co., Ltd. | 2-substituted benzothiazole derivatives and prophylactic and therapeutic agents for the treatment of diabetic complications |
| EP1327887A3 (en) * | 1995-01-18 | 2008-12-10 | Synvista Therapeutics, Inc. | Use of thiazolium compounds for preventing and reversing the formation of advanced glycosylation end products |
| US5656261A (en) * | 1995-01-18 | 1997-08-12 | The Picower Institute For Medical Research | Preventing and reversing advanced glycosylation endproducts |
| US5744451A (en) * | 1995-09-12 | 1998-04-28 | Warner-Lambert Company | N-substituted glutamic acid derivatives with interleukin-1 β converting enzyme inhibitory activity |
| US6121300A (en) * | 1998-11-10 | 2000-09-19 | Wagle; Dilip R. | Reversing advanced glycosylation cross-links using heterocyclic-substituted thiazolium salts |
-
1998
- 1998-11-10 US US09/189,200 patent/US6121300A/en not_active Expired - Fee Related
-
1999
- 1999-11-10 KR KR1020017005846A patent/KR20010080969A/ko not_active Ceased
- 1999-11-10 NZ NZ511569A patent/NZ511569A/xx unknown
- 1999-11-10 EP EP99971712A patent/EP1128830B1/en not_active Expired - Lifetime
- 1999-11-10 JP JP2000580624A patent/JP2002529414A/ja active Pending
- 1999-11-10 AU AU14748/00A patent/AU767889B2/en not_active Ceased
- 1999-11-10 MX MXPA01004721A patent/MXPA01004721A/es unknown
- 1999-11-10 CA CA002350211A patent/CA2350211A1/en not_active Abandoned
- 1999-11-10 WO PCT/US1999/026565 patent/WO2000027395A1/en not_active Ceased
- 1999-11-10 DE DE69938357T patent/DE69938357D1/de not_active Expired - Lifetime
- 1999-11-10 AT AT99971712T patent/ATE388704T1/de not_active IP Right Cessation
-
2000
- 2000-08-23 US US09/644,024 patent/US6319934B1/en not_active Expired - Fee Related
-
2001
- 2001-10-23 US US10/003,514 patent/US20020160992A1/en not_active Abandoned
-
2003
- 2003-01-21 US US10/348,378 patent/US6790859B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2002529414A5 (enExample) | ||
| US6319934B1 (en) | Reversing advanced glycosylation cross-links using heterocyclic-substituted thiazolium compounds | |
| EP1303501B1 (en) | Cyanomethyl substituted thiazoliums and imidazoliums and treatments of disorders associated with protein aging | |
| US6596744B2 (en) | Method for treating fibrotic diseases or other indications IIC | |
| AU782500B2 (en) | Thiazole, imidazole and oxazole compounds and treatments of disorders associated with protein aging | |
| US20060281749A1 (en) | Method for treating glaucoma IV B | |
| AU2001280546A1 (en) | Cyanomethyl substituted thiazoliums and imidazoliums and treatments of disorders associated with protein aging | |
| JP2010248205A (ja) | 強皮症の治療のためのベンザゾール誘導体 | |
| US6458819B1 (en) | Thiazolium compounds and treatments of disorders associated with protein aging | |
| DE60130030T2 (de) | Verfahren zur behandlung von glaukom | |
| WO1996040622A1 (en) | Bis-(2-aryl)hydrazones as inhibitors of the formation of advanced glycosylation endproducts | |
| WO2002053156A1 (en) | Method for treating glaucoma ii b | |
| JP3968388B2 (ja) | 膵炎治療剤 | |
| JP2006504627A (ja) | 化合物および方法 | |
| JPH11511138A (ja) | 酸化窒素シンターゼ（ｎｏｓ）阻害剤 | |
| JP2002515870A (ja) | タンパク質グリコシル化阻害のための１，２，４―トリアジン誘導体 |