CA2614585A1 - Compounds for treatment of lipase-mediated diseases - Google Patents
Compounds for treatment of lipase-mediated diseases Download PDFInfo
- Publication number
- CA2614585A1 CA2614585A1 CA002614585A CA2614585A CA2614585A1 CA 2614585 A1 CA2614585 A1 CA 2614585A1 CA 002614585 A CA002614585 A CA 002614585A CA 2614585 A CA2614585 A CA 2614585A CA 2614585 A1 CA2614585 A1 CA 2614585A1
- Authority
- CA
- Canada
- Prior art keywords
- benzoquinone
- undecyl
- bis
- compound
- prodrug
- 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.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 169
- 108090001060 Lipase Proteins 0.000 title claims abstract description 84
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 37
- 201000010099 disease Diseases 0.000 title claims abstract description 29
- 238000011282 treatment Methods 0.000 title claims abstract description 29
- 230000001404 mediated effect Effects 0.000 title claims abstract description 17
- 102000004882 Lipase Human genes 0.000 title claims description 45
- 239000004367 Lipase Substances 0.000 title claims description 37
- 235000019421 lipase Nutrition 0.000 title claims description 37
- 238000000034 method Methods 0.000 claims abstract description 52
- 239000000651 prodrug Substances 0.000 claims abstract description 47
- 229940002612 prodrug Drugs 0.000 claims abstract description 47
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 32
- 230000001603 reducing effect Effects 0.000 claims abstract description 29
- 230000003287 optical effect Effects 0.000 claims abstract description 28
- 150000002148 esters Chemical class 0.000 claims abstract description 19
- 150000002170 ethers Chemical class 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 17
- 150000004657 carbamic acid derivatives Chemical class 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 13
- 208000008589 Obesity Diseases 0.000 claims abstract description 13
- 235000020824 obesity Nutrition 0.000 claims abstract description 13
- 150000002923 oximes Chemical class 0.000 claims abstract description 13
- 230000002265 prevention Effects 0.000 claims abstract description 13
- 208000030159 metabolic disease Diseases 0.000 claims abstract description 12
- 208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 11
- 206010033307 Overweight Diseases 0.000 claims abstract description 11
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 10
- 208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 10
- 208000001145 Metabolic Syndrome Diseases 0.000 claims abstract description 10
- 206010033645 Pancreatitis Diseases 0.000 claims abstract description 9
- 239000002537 cosmetic Substances 0.000 claims abstract description 9
- 208000006575 hypertriglyceridemia Diseases 0.000 claims abstract description 9
- 230000008569 process Effects 0.000 claims abstract description 4
- -1 nitro, amino Chemical group 0.000 claims description 117
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- 108090000790 Enzymes Proteins 0.000 claims description 52
- IRSFLDGTOHBADP-UHFFFAOYSA-N embelin Chemical compound CCCCCCCCCCCC1=C(O)C(=O)C=C(O)C1=O IRSFLDGTOHBADP-UHFFFAOYSA-N 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 35
- 239000012453 solvate Substances 0.000 claims description 24
- 150000004677 hydrates Chemical class 0.000 claims description 23
- 238000010521 absorption reaction Methods 0.000 claims description 21
- 229940005561 1,4-benzoquinone Drugs 0.000 claims description 20
- 238000009825 accumulation Methods 0.000 claims description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 19
- 230000004060 metabolic process Effects 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 239000003085 diluting agent Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 230000001413 cellular effect Effects 0.000 claims description 14
- 241000124008 Mammalia Species 0.000 claims description 13
- 210000001124 body fluid Anatomy 0.000 claims description 13
- 239000010839 body fluid Substances 0.000 claims description 13
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 11
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
- 150000003973 alkyl amines Chemical class 0.000 claims description 9
- 150000004982 aromatic amines Chemical class 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
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- 125000001475 halogen functional group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 201000001421 hyperglycemia Diseases 0.000 claims description 7
- XBZUMPSWLOLGDK-UHFFFAOYSA-N (4-benzoyloxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl) benzoate Chemical compound O=C1C=C(OC(=O)C=2C=CC=CC=2)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=CC=C1 XBZUMPSWLOLGDK-UHFFFAOYSA-N 0.000 claims description 6
- OYWIJKKXWNBXFR-UHFFFAOYSA-N [4-(2-bromobenzoyl)oxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl] 2-bromobenzoate Chemical compound O=C1C=C(OC(=O)C=2C(=CC=CC=2)Br)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=CC=C1Br OYWIJKKXWNBXFR-UHFFFAOYSA-N 0.000 claims description 6
- LDDRTLOTTQBRIA-UHFFFAOYSA-N [4-(2-chlorobenzoyl)oxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl] 2-chlorobenzoate Chemical compound O=C1C=C(OC(=O)C=2C(=CC=CC=2)Cl)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=CC=C1Cl LDDRTLOTTQBRIA-UHFFFAOYSA-N 0.000 claims description 6
- IYUYGFCCNHQVLX-UHFFFAOYSA-N [4-(2-fluorobenzoyl)oxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl] 2-fluorobenzoate Chemical compound O=C1C=C(OC(=O)C=2C(=CC=CC=2)F)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=CC=C1F IYUYGFCCNHQVLX-UHFFFAOYSA-N 0.000 claims description 6
- QGFOKQPWPSSDJD-UHFFFAOYSA-N [4-(2-iodobenzoyl)oxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl] 2-iodobenzoate Chemical compound O=C1C=C(OC(=O)C=2C(=CC=CC=2)I)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=CC=C1I QGFOKQPWPSSDJD-UHFFFAOYSA-N 0.000 claims description 6
- XMXCRWMTZJYJBG-UHFFFAOYSA-N [4-(3-chlorobenzoyl)oxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl] 3-chlorobenzoate Chemical compound O=C1C=C(OC(=O)C=2C=C(Cl)C=CC=2)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=CC(Cl)=C1 XMXCRWMTZJYJBG-UHFFFAOYSA-N 0.000 claims description 6
- BOFLDBHBFSECDO-UHFFFAOYSA-N [4-(3-fluorobenzoyl)oxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl] 3-fluorobenzoate Chemical compound O=C1C=C(OC(=O)C=2C=C(F)C=CC=2)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=CC(F)=C1 BOFLDBHBFSECDO-UHFFFAOYSA-N 0.000 claims description 6
- XEKUTURRTQPHGD-UHFFFAOYSA-N [4-(3-methoxybenzoyl)oxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl] 3-methoxybenzoate Chemical compound O=C1C=C(OC(=O)C=2C=C(OC)C=CC=2)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=CC(OC)=C1 XEKUTURRTQPHGD-UHFFFAOYSA-N 0.000 claims description 6
- SFAJJAGJWFWPKF-UHFFFAOYSA-N [4-(3-methylbenzoyl)oxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl] 3-methylbenzoate Chemical compound O=C1C=C(OC(=O)C=2C=C(C)C=CC=2)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=CC(C)=C1 SFAJJAGJWFWPKF-UHFFFAOYSA-N 0.000 claims description 6
- OMXJGXWYPAEFSH-UHFFFAOYSA-N [4-(3-nitrobenzoyl)oxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl] 3-nitrobenzoate Chemical compound O=C1C=C(OC(=O)C=2C=C(C=CC=2)[N+]([O-])=O)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=CC([N+]([O-])=O)=C1 OMXJGXWYPAEFSH-UHFFFAOYSA-N 0.000 claims description 6
- GUFYMXWSHTWBCB-UHFFFAOYSA-N [4-(4-bromobenzoyl)oxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl] 4-bromobenzoate Chemical compound O=C1C=C(OC(=O)C=2C=CC(Br)=CC=2)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=C(Br)C=C1 GUFYMXWSHTWBCB-UHFFFAOYSA-N 0.000 claims description 6
- PNBWFNBVRCHKIS-UHFFFAOYSA-N [4-(4-chlorobenzoyl)oxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl] 4-chlorobenzoate Chemical compound O=C1C=C(OC(=O)C=2C=CC(Cl)=CC=2)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=C(Cl)C=C1 PNBWFNBVRCHKIS-UHFFFAOYSA-N 0.000 claims description 6
- YDERXQNYGGLMCO-UHFFFAOYSA-N [4-(4-fluorobenzoyl)oxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl] 4-fluorobenzoate Chemical compound O=C1C=C(OC(=O)C=2C=CC(F)=CC=2)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=C(F)C=C1 YDERXQNYGGLMCO-UHFFFAOYSA-N 0.000 claims description 6
- UNZGSPJCHFRGDA-UHFFFAOYSA-N [4-(4-methoxybenzoyl)oxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl] 4-methoxybenzoate Chemical compound O=C1C=C(OC(=O)C=2C=CC(OC)=CC=2)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=C(OC)C=C1 UNZGSPJCHFRGDA-UHFFFAOYSA-N 0.000 claims description 6
- CLJABOGYVPHYTK-UHFFFAOYSA-N [4-(4-methylbenzoyl)oxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl] 4-methylbenzoate Chemical compound O=C1C=C(OC(=O)C=2C=CC(C)=CC=2)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=C(C)C=C1 CLJABOGYVPHYTK-UHFFFAOYSA-N 0.000 claims description 6
- CUWSMSXZJPPCKM-UHFFFAOYSA-N [4-(4-tert-butylbenzoyl)oxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl] 4-tert-butylbenzoate Chemical compound O=C1C=C(OC(=O)C=2C=CC(=CC=2)C(C)(C)C)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=C(C(C)(C)C)C=C1 CUWSMSXZJPPCKM-UHFFFAOYSA-N 0.000 claims description 6
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- DPVIXVNAMBUWEF-UHFFFAOYSA-N [4-(2-nitrobenzoyl)oxy-3,6-dioxo-5-undecylcyclohexa-1,4-dien-1-yl] 2-nitrobenzoate Chemical compound O=C1C=C(OC(=O)C=2C(=CC=CC=2)[N+]([O-])=O)C(=O)C(CCCCCCCCCCC)=C1OC(=O)C1=CC=CC=C1[N+]([O-])=O DPVIXVNAMBUWEF-UHFFFAOYSA-N 0.000 claims description 5
- 238000001990 intravenous administration Methods 0.000 claims description 5
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/02—Quinones with monocyclic quinoid structure
- C07C50/04—Benzoquinones, i.e. C6H4O2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Communicable Diseases (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Oncology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN864/MUM/2005 | 2005-07-21 | ||
| IN864MU2005 | 2005-07-21 | ||
| PCT/IN2005/000318 WO2007010546A1 (en) | 2005-07-21 | 2005-09-19 | Compounds for treatment of lipase-mediated diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2614585A1 true CA2614585A1 (en) | 2007-01-25 |
Family
ID=36121552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002614585A Abandoned CA2614585A1 (en) | 2005-07-21 | 2005-09-19 | Compounds for treatment of lipase-mediated diseases |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1937622A1 (xx) |
| JP (1) | JP2009505953A (xx) |
| KR (1) | KR100928954B1 (xx) |
| CN (1) | CN101228108A (xx) |
| AU (1) | AU2005334672A1 (xx) |
| BR (1) | BRPI0520515A2 (xx) |
| CA (1) | CA2614585A1 (xx) |
| IL (1) | IL188894A0 (xx) |
| NZ (1) | NZ565878A (xx) |
| RU (1) | RU2420513C2 (xx) |
| WO (1) | WO2007010546A1 (xx) |
| ZA (1) | ZA200800567B (xx) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9623021B2 (en) * | 2007-01-22 | 2017-04-18 | Gtx, Inc. | Nuclear receptor binding agents |
| AU2014230640B2 (en) * | 2013-03-14 | 2018-08-16 | Shionogi & Co., Ltd. | Monoclonal antibody inhibiting enzymatic activity of endothelial lipase |
| JP2016534049A (ja) * | 2013-10-08 | 2016-11-04 | テンプル・ユニバーシティ−オブ・ザ・コモンウェルス・システム・オブ・ハイアー・エデュケイションＴｅｍｐｌｅ Ｕｎｉｖｅｒｓｉｔｙ−Ｏｆ Ｔｈｅ Ｃｏｍｍｏｎｗｅａｌｔｈ Ｓｙｓｔｅｍ Ｏｆ Ｈｉｇｈｅｒ Ｅｄｕｃａｔｉｏｎ | 内皮リパーゼ阻害を示す官能基化フラン−２−スルホンアミド |
| US10259804B2 (en) | 2014-09-26 | 2019-04-16 | Shifa Biomedical Corporation | Anti-endothelial lipase compounds and methods of using the same in the treatment and/or prevention of cardiovascular diseases |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7510536A (en) * | 1975-09-05 | 1977-03-08 | Council Scient Ind Res | Salts of embelin with primary amines |
| DE2540282A1 (de) * | 1975-09-10 | 1977-03-24 | Council Scient Ind Res | Kondensationsprodukt von embelin mit einem primaeren amin und verfahren zu seiner herstellung |
| US20010047032A1 (en) * | 1999-12-30 | 2001-11-29 | Castillo Gerardo M. | Polyhydroxylated aromatic compounds for the treatment of amyloidosis and alpha-synuclein fibril diseases |
-
2005
- 2005-09-19 WO PCT/IN2005/000318 patent/WO2007010546A1/en active Application Filing
- 2005-09-19 BR BRPI0520515-8A patent/BRPI0520515A2/pt not_active IP Right Cessation
- 2005-09-19 AU AU2005334672A patent/AU2005334672A1/en not_active Abandoned
- 2005-09-19 EP EP05823794A patent/EP1937622A1/en not_active Withdrawn
- 2005-09-19 CN CNA2005800511311A patent/CN101228108A/zh active Pending
- 2005-09-19 RU RU2008106628/04A patent/RU2420513C2/ru not_active IP Right Cessation
- 2005-09-19 CA CA002614585A patent/CA2614585A1/en not_active Abandoned
- 2005-09-19 KR KR1020087001911A patent/KR100928954B1/ko not_active IP Right Cessation
- 2005-09-19 NZ NZ565878A patent/NZ565878A/en not_active IP Right Cessation
- 2005-09-19 JP JP2008522176A patent/JP2009505953A/ja active Pending
-
2008
- 2008-01-18 ZA ZA200800567A patent/ZA200800567B/xx unknown
- 2008-01-20 IL IL188894A patent/IL188894A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ565878A (en) | 2010-04-30 |
| JP2009505953A (ja) | 2009-02-12 |
| RU2420513C2 (ru) | 2011-06-10 |
| CN101228108A (zh) | 2008-07-23 |
| RU2008106628A (ru) | 2009-08-27 |
| ZA200800567B (en) | 2008-11-26 |
| KR20080030044A (ko) | 2008-04-03 |
| BRPI0520515A2 (pt) | 2009-05-12 |
| AU2005334672A1 (en) | 2007-01-25 |
| KR100928954B1 (ko) | 2009-11-30 |
| EP1937622A1 (en) | 2008-07-02 |
| WO2007010546A1 (en) | 2007-01-25 |
| IL188894A0 (en) | 2008-04-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20130919 |