JP2002529414A5 - - Google Patents
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- 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
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- -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
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- 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
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- 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
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- 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
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 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
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| PCT/US1999/026565 WO2000027395A1 (en) | 1998-11-10 | 1999-11-10 | Reversing advanced glycosylation cross-links using heterocyclic-substituted thiazolium salts |
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Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
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| FI119756B (fi) | 1995-01-18 | 2009-03-13 | Alteon Inc | Tiatsoliumyhdisteiden käyttö pitkälle edenneen glykosylaation lopputuotteiden muodostumisen estossa ja suunnan muutoksessa |
| 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 |
| CA2400694A1 (en) * | 2000-02-23 | 2001-08-30 | Alteon, Inc. | Thiazolium compounds and treatments of disorders associated with protein aging |
| US20020068729A1 (en) * | 2000-07-13 | 2002-06-06 | Alteon, Inc. | Method for treating fibrotic diseases or other indications IC |
| US6982278B2 (en) * | 2000-08-23 | 2006-01-03 | Eli Lilly And Company | Oxazolyl-aryloxyacetic acid derivatives and their use as ppar agonists |
| EP1353676A4 (en) * | 2000-12-29 | 2006-05-31 | Alteon Inc | METHOD FOR THE TREATMENT OF FIBROUS OR OTHER INDICATIONS |
| MXPA03005922A (es) * | 2000-12-29 | 2004-05-04 | Alteon Inc | Metodo para tratar glaucoma ib. |
| WO2002053101A2 (en) * | 2000-12-29 | 2002-07-11 | Alteon, Inc. | Method for treating fibrotic diseases or other indications |
| JP2004525904A (ja) * | 2000-12-29 | 2004-08-26 | 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ｉｉｉｃの治療方法 |
| 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 |
| CA2448294A1 (en) * | 2001-05-30 | 2002-12-05 | Alteon Inc. | Method for treating fibrotic diseases or other indications vi |
| 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 |
| KR20070004730A (ko) * | 2004-02-17 | 2007-01-09 | 다이나미스 테라퓨틱스, 인코포레이티드 | 프룩토스아민 3 키나아제 및 콜라겐 및 엘라스틴의 형성 |
| 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 |
| 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 |
| 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 |
| MX338062B (es) * | 2006-01-23 | 2016-04-01 | Milliken & Co | Composiciones de cuidado de lavanderia con tinte de tiazolio. |
| 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 |
| US9221765B2 (en) | 2009-06-10 | 2015-12-29 | 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 |
| CA1273011A (en) * | 1984-07-02 | 1990-08-21 | Susan M. Schmitt | Carbapenems having an externally alkylated mono- or bicyclic 2-quaternary heteroarylalkylthio substituent |
| CA1273012A (en) * | 1984-07-02 | 1990-08-21 | Burton G. Christensen | 1-methylcarbapenems having an externally alkylated mono- of bicyclic 2-quarternary heteroarylalkylthio substituent |
| US4683312A (en) * | 1984-11-13 | 1987-07-28 | Eli Lilly And Company | Imidazolium hypoglycemic agents |
| US4609670A (en) * | 1984-11-13 | 1986-09-02 | Eli Lilly And Company | Imidazolium hypoglycemic agents |
| ZA86171B (en) | 1985-01-16 | 1986-08-27 | Hoffmann La Roche | Polycyclic salts |
| 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 |
| US5219852A (en) * | 1986-03-13 | 1993-06-15 | Dr. Karl Thomae Gmbh | Substituted thiazoles and oxazoles and pharmaceutical compositions and methods thereof |
| 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 |
| US5225425A (en) * | 1990-05-04 | 1993-07-06 | American Cyanamid Company | Bis-aryl amide antagonists of platelet activating factor |
| US5128351A (en) * | 1990-05-04 | 1992-07-07 | American Cyanamid Company | Bis-aryl amide and urea 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 |
| ATE144249T1 (de) * | 1992-07-30 | 1996-11-15 | Drug Delivery System Inst Ltd | Im intracerebralen bereich verweisende verbindungen und deren anwendung |
| TW268952B (cg-RX-API-DMAC7.html) * | 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 |
| MX9705449A (es) * | 1995-01-18 | 1998-02-28 | Alteon Inc | Uso de compuestos de tiazolio para evitar y revertir la formacion de productos finales de glicosilacion avanzada. |
| 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 MX MXPA01004721A patent/MXPA01004721A/es unknown
- 1999-11-10 AT AT99971712T patent/ATE388704T1/de not_active IP Right Cessation
- 1999-11-10 KR KR1020017005846A patent/KR20010080969A/ko not_active Ceased
- 1999-11-10 NZ NZ511569A patent/NZ511569A/xx unknown
- 1999-11-10 AU AU14748/00A patent/AU767889B2/en not_active Ceased
- 1999-11-10 DE DE69938357T patent/DE69938357D1/de not_active Expired - Lifetime
- 1999-11-10 CA CA002350211A patent/CA2350211A1/en not_active Abandoned
- 1999-11-10 JP JP2000580624A patent/JP2002529414A/ja active Pending
- 1999-11-10 WO PCT/US1999/026565 patent/WO2000027395A1/en not_active Ceased
- 1999-11-10 EP EP99971712A patent/EP1128830B1/en not_active Expired - Lifetime
-
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
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