JP2002529414A - 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 - Google Patents
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Info
- Publication number
- JP2002529414A JP2002529414A JP2000580624A JP2000580624A JP2002529414A JP 2002529414 A JP2002529414 A JP 2002529414A JP 2000580624 A JP2000580624 A JP 2000580624A JP 2000580624 A JP2000580624 A JP 2000580624A JP 2002529414 A JP2002529414 A JP 2002529414A
- Authority
- JP
- Japan
- Prior art keywords
- oxoethyl
- dimethylthiazolium
- group
- piperidinyl
- piperazinyl
- 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
- 125000000623 heterocyclic group Chemical group 0.000 title claims description 51
- 150000003839 salts Chemical class 0.000 title claims description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 74
- 238000000034 method Methods 0.000 claims abstract description 47
- 239000000203 mixture Substances 0.000 claims abstract description 37
- -1 azosinyl Chemical group 0.000 claims description 144
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 37
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 18
- 239000011593 sulfur Substances 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 239000001301 oxygen Substances 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 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 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 6
- 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 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 241001465754 Metazoa Species 0.000 claims description 5
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
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- 125000002947 alkylene group Chemical group 0.000 claims 8
- 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 claims 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 claims 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 claims 4
- 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 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 claims 4
- 125000002785 azepinyl group Chemical group 0.000 claims 4
- 150000002500 ions Chemical class 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000001806 thionaphthenyl group Chemical group 0.000 claims 4
- 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 compound CCOC(=O)CC1=CSC(NC(=O)C[N+]=2C(=C(C)SC=2)C)=N1 UDUZHEYUSZGXTJ-UHFFFAOYSA-O 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 125000004931 azocinyl group Chemical group N1=C(C=CC=CC=C1)* 0.000 claims 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 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000037394 skin elasticity Effects 0.000 claims 1
- 230000003966 vascular damage Effects 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 abstract description 30
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- 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
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
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- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5355—Non-condensed oxazines and containing further heterocyclic rings
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- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/541—Non-condensed thiazines containing further heterocyclic rings
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- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catalysts (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
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 true JP2002529414A (ja) | 2002-09-10 |
| JP2002529414A5 JP2002529414A5 (enExample) | 2007-01-25 |
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| 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 |
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| 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) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010533143A (ja) * | 2007-07-09 | 2010-10-21 | ビーエーエスエフ ビューティ ケア ソリューションズ フランス エスエーエス | Ａｇｅの脱糖化 |
Families Citing this family (27)
| 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 |
| AU780205B2 (en) * | 2000-02-23 | 2005-03-10 | Alteon Inc. | Thiazolium compounds and treatments of disorders associated with protein aging |
| JP2004504389A (ja) * | 2000-07-13 | 2004-02-12 | アルテオン インコーポレーテッド | シアノメチル置換化チアゾリウム及びイミダゾリウム、並びにタンパク質老化と関連する疾患の治療 |
| US6982278B2 (en) * | 2000-08-23 | 2006-01-03 | Eli Lilly And Company | Oxazolyl-aryloxyacetic acid derivatives and their use as ppar agonists |
| WO2002053101A2 (en) * | 2000-12-29 | 2002-07-11 | Alteon, Inc. | Method for treating fibrotic diseases or other indications |
| EP1353676A4 (en) * | 2000-12-29 | 2006-05-31 | Alteon Inc | METHOD FOR THE TREATMENT OF FIBROUS OR OTHER INDICATIONS |
| MXPA03005954A (es) * | 2000-12-29 | 2004-05-24 | Alteon Inc | Metodo para tratar enfermedades fibroticas u otras indicaciones iiic. |
| DE60130030T2 (de) * | 2000-12-29 | 2008-04-30 | Alteon Inc. | Verfahren zur behandlung von glaukom |
| 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 |
| EP1404339A4 (en) * | 2001-05-30 | 2004-08-25 | 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 |
| MXPA06009363A (es) * | 2004-02-17 | 2007-01-26 | Dynamis Therapeutics Inc | Fructosaamina 3 cinasa y la formacion de colageno y elastina. |
| 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 |
| CN101370925B (zh) * | 2006-01-23 | 2014-03-26 | 美利肯公司 | 含噻唑鎓染料的洗熨护理组合物 |
| 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 |
| US9005643B2 (en) * | 2008-04-04 | 2015-04-14 | 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 |
| US12274809B2 (en) | 2015-05-01 | 2025-04-15 | 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 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996022095A2 (en) * | 1995-01-18 | 1996-07-25 | Alteon Inc. | Use of thiazolium compounds for preventing and reversing the formation of advanced glycosylation endproducts |
| WO1997009981A1 (en) * | 1995-09-12 | 1997-03-20 | University Of Kansas Medical Center | Advanced glycation end-product intermediaries and post-amadori inhibition |
Family Cites Families (29)
| 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 |
| US4886814A (en) * | 1986-03-13 | 1989-12-12 | Dr. Karl Thomas Gmbh | Substituted thiazoles and oxazoles and 2-hydroxy-morpholines |
| 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 |
| 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 |
| CA2120248A1 (en) * | 1992-07-30 | 1994-02-17 | Toyoaki Ishikura | Compounds which can be retained in brain |
| 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 |
| 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 |
-
1998
- 1998-11-10 US US09/189,200 patent/US6121300A/en not_active Expired - Fee Related
-
1999
- 1999-11-10 WO PCT/US1999/026565 patent/WO2000027395A1/en not_active Ceased
- 1999-11-10 NZ NZ511569A patent/NZ511569A/xx unknown
- 1999-11-10 KR KR1020017005846A patent/KR20010080969A/ko not_active Ceased
- 1999-11-10 MX MXPA01004721A patent/MXPA01004721A/es unknown
- 1999-11-10 JP JP2000580624A patent/JP2002529414A/ja active Pending
- 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
- 1999-11-10 EP EP99971712A patent/EP1128830B1/en not_active Expired - Lifetime
- 1999-11-10 AU AU14748/00A patent/AU767889B2/en not_active Ceased
- 1999-11-10 CA CA002350211A patent/CA2350211A1/en not_active Abandoned
-
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
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996022095A2 (en) * | 1995-01-18 | 1996-07-25 | Alteon Inc. | Use of thiazolium compounds for preventing and reversing the formation of advanced glycosylation endproducts |
| WO1997009981A1 (en) * | 1995-09-12 | 1997-03-20 | University Of Kansas Medical Center | Advanced glycation end-product intermediaries and post-amadori inhibition |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010533143A (ja) * | 2007-07-09 | 2010-10-21 | ビーエーエスエフ ビューティ ケア ソリューションズ フランス エスエーエス | Ａｇｅの脱糖化 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2350211A1 (en) | 2000-05-18 |
| US6319934B1 (en) | 2001-11-20 |
| WO2000027395A1 (en) | 2000-05-18 |
| MXPA01004721A (es) | 2002-09-18 |
| EP1128830B1 (en) | 2008-03-12 |
| US6790859B2 (en) | 2004-09-14 |
| KR20010080969A (ko) | 2001-08-25 |
| US20030176417A1 (en) | 2003-09-18 |
| AU767889B2 (en) | 2003-11-27 |
| EP1128830A4 (en) | 2004-03-31 |
| AU1474800A (en) | 2000-05-29 |
| NZ511569A (en) | 2003-06-30 |
| US6121300A (en) | 2000-09-19 |
| DE69938357D1 (de) | 2008-04-24 |
| ATE388704T1 (de) | 2008-03-15 |
| US20020160992A1 (en) | 2002-10-31 |
| EP1128830A1 (en) | 2001-09-05 |
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