UA82093C2 - Фтор- та трифторалкіловмісні гетероциклічні сульфонамідні інгібітори утворення бета-амілоїду та їх похідні - Google Patents
Фтор- та трифторалкіловмісні гетероциклічні сульфонамідні інгібітори утворення бета-амілоїду та їх похідні Download PDFInfo
- Publication number
- UA82093C2 UA82093C2 UAA200510177A UAA200510177A UA82093C2 UA 82093 C2 UA82093 C2 UA 82093C2 UA A200510177 A UAA200510177 A UA A200510177A UA A200510177 A UAA200510177 A UA A200510177A UA 82093 C2 UA82093 C2 UA 82093C2
- Authority
- UA
- Ukraine
- Prior art keywords
- trifluoro
- sulfonamide
- hydroxymethyl
- chloro
- solution
- Prior art date
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- 108010090849 Amyloid beta-Peptides Proteins 0.000 title claims abstract description 29
- 102000013455 Amyloid beta-Peptides Human genes 0.000 title claims abstract description 29
- 229940124530 sulfonamide Drugs 0.000 title claims description 109
- -1 heterocyclic sulfonamide Chemical class 0.000 title claims description 70
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 239000003112 inhibitor Substances 0.000 title description 9
- 125000004950 trifluoroalkyl group Chemical group 0.000 title description 9
- 125000003709 fluoroalkyl group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 165
- 238000000034 method Methods 0.000 claims abstract description 71
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 56
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- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 13
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- 125000001010 sulfinic acid amide group Chemical group 0.000 claims description 9
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- 239000003054 catalyst Substances 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 7
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- UMQSLMSNBMTPJY-UHFFFAOYSA-N 2,5-dichlorothiophene-3-sulfonic acid Chemical compound OS(=O)(=O)C=1C=C(Cl)SC=1Cl UMQSLMSNBMTPJY-UHFFFAOYSA-N 0.000 claims description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
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- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
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- PSRZMXNNQTWAGB-UHFFFAOYSA-N ethyl 4,4,4-trifluorobutanoate Chemical compound CCOC(=O)CCC(F)(F)F PSRZMXNNQTWAGB-UHFFFAOYSA-N 0.000 description 1
- DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
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- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
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- QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical compound CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
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- JEGUKCSWCFPDGT-UHFFFAOYSA-M hydroxide;hydrate Chemical compound O.[OH-] JEGUKCSWCFPDGT-UHFFFAOYSA-M 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
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- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 210000001589 microsome Anatomy 0.000 description 1
- 208000027061 mild cognitive impairment Diseases 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- SBOJXQVPLKSXOG-UHFFFAOYSA-N o-amino-hydroxylamine Chemical compound NON SBOJXQVPLKSXOG-UHFFFAOYSA-N 0.000 description 1
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- 238000012261 overproduction Methods 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- 231100000915 pathological change Toxicity 0.000 description 1
- 230000036285 pathological change Effects 0.000 description 1
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- 239000000312 peanut oil Substances 0.000 description 1
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- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
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- 239000013612 plasmid Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
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- 125000006239 protecting group Chemical group 0.000 description 1
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- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
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- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229960000999 sodium citrate dihydrate Drugs 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
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- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- 238000011830 transgenic mouse model Methods 0.000 description 1
- 238000003146 transient transfection Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- OILVALOYRFDGPW-UHFFFAOYSA-M triphenyl(3,3,3-trifluoropropyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC(F)(F)F)C1=CC=CC=C1 OILVALOYRFDGPW-UHFFFAOYSA-M 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- ICBQNKQWOYQWLF-UHFFFAOYSA-N triphenylphosphane;hydrate Chemical compound O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 ICBQNKQWOYQWLF-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
- C07D231/18—One oxygen or sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45922803P | 2003-03-31 | 2003-03-31 | |
| PCT/US2004/009268 WO2004092155A1 (en) | 2003-03-31 | 2004-03-26 | Fluoro-and trifluoroalkyl-containing heterocyclic sulfonamide inhibitors of beta amyloid production and derivatives thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA82093C2 true UA82093C2 (uk) | 2008-03-11 |
Family
ID=33299665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA200510177A UA82093C2 (uk) | 2003-03-31 | 2004-03-26 | Фтор- та трифторалкіловмісні гетероциклічні сульфонамідні інгібітори утворення бета-амілоїду та їх похідні |
Country Status (22)
| Country | Link |
|---|---|
| US (3) | US7300951B2 (https=) |
| EP (1) | EP1608638A1 (https=) |
| JP (1) | JP2006522126A (https=) |
| KR (1) | KR20060002908A (https=) |
| CN (2) | CN101274926A (https=) |
| AR (1) | AR043940A1 (https=) |
| AU (1) | AU2004230844B2 (https=) |
| BR (1) | BRPI0408962A (https=) |
| CA (1) | CA2517155A1 (https=) |
| CL (1) | CL2004000647A1 (https=) |
| CO (1) | CO5640049A2 (https=) |
| CR (1) | CR7951A (https=) |
| EC (1) | ECSP056128A (https=) |
| MX (1) | MXPA05010368A (https=) |
| NO (1) | NO20054263L (https=) |
| NZ (1) | NZ542468A (https=) |
| RU (1) | RU2342374C2 (https=) |
| SG (1) | SG167669A1 (https=) |
| TW (1) | TWI336698B (https=) |
| UA (1) | UA82093C2 (https=) |
| WO (1) | WO2004092155A1 (https=) |
| ZA (1) | ZA200507896B (https=) |
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| JP4530849B2 (ja) * | 2002-06-11 | 2010-08-25 | ワイス・エルエルシー | βアミロイド産生の置換フェニルスルホンアミド阻害剤 |
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| US7838550B2 (en) * | 2006-02-17 | 2010-11-23 | Wyeth Llc | Selective N-sulfonylation of 2-amino fluoro- and trifluoroalkyl substituted alcohols |
| PE20080169A1 (es) * | 2006-02-17 | 2008-04-11 | Wyeth Corp | Metodo para preparar alcoholes sustituidos con sulfonamidas y sus compuestos intermedios |
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| CA2883896C (en) | 2012-09-07 | 2023-03-07 | Massachusetts Eye & Ear Infirmary | Treating hearing loss |
| JP6319912B2 (ja) | 2013-04-19 | 2018-05-09 | 国立大学法人 岡山大学 | アミロイドβ蛋白質により誘発される認知障害の治療剤およびアルツハイマー病治療薬、ならびにこれらに関連する治療方法および病態解析方法 |
| EP3212773B1 (en) | 2014-10-29 | 2021-09-15 | Massachusetts Eye and Ear Infirmary | Efficient delivery of therapeutic molecules to cells of the inner ear |
| JP6840774B2 (ja) | 2016-05-16 | 2021-03-10 | ザ ジェネラル ホスピタル コーポレイション | 肺上皮エンジニアリングにおけるヒト気道幹細胞 |
| WO2019148067A1 (en) | 2018-01-26 | 2019-08-01 | Massachusetts Eye And Ear Infirmary | Treatment of hearing loss |
| EP4299062A1 (en) | 2022-06-30 | 2024-01-03 | Vilnius University | Inhibition of protein amyloid aggregation using fluorinated benzenesulfonamides |
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2004
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- 2004-03-26 CL CL200400647A patent/CL2004000647A1/es unknown
- 2004-03-26 SG SG200708961-8A patent/SG167669A1/en unknown
- 2004-03-26 AR ARP040101022A patent/AR043940A1/es unknown
- 2004-03-26 JP JP2006509331A patent/JP2006522126A/ja active Pending
- 2004-03-26 WO PCT/US2004/009268 patent/WO2004092155A1/en not_active Ceased
- 2004-03-26 CN CNA2008100013400A patent/CN101274926A/zh active Pending
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- 2004-03-26 TW TW093108219A patent/TWI336698B/zh not_active IP Right Cessation
- 2004-03-26 CA CA002517155A patent/CA2517155A1/en not_active Abandoned
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- 2004-03-26 RU RU2005133434/04A patent/RU2342374C2/ru not_active IP Right Cessation
- 2004-03-26 EP EP04758978A patent/EP1608638A1/en not_active Withdrawn
- 2004-03-26 KR KR1020057018637A patent/KR20060002908A/ko not_active Ceased
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| US20090227667A1 (en) | 2009-09-10 |
| CA2517155A1 (en) | 2004-10-28 |
| EP1608638A1 (en) | 2005-12-28 |
| RU2342374C2 (ru) | 2008-12-27 |
| AU2004230844A1 (en) | 2004-10-28 |
| WO2004092155A1 (en) | 2004-10-28 |
| RU2005133434A (ru) | 2006-07-10 |
| NO20054263L (no) | 2005-12-14 |
| CN1780829B (zh) | 2010-12-29 |
| KR20060002908A (ko) | 2006-01-09 |
| CL2004000647A1 (es) | 2005-02-04 |
| US7858658B2 (en) | 2010-12-28 |
| AU2004230844B2 (en) | 2010-12-09 |
| US7300951B2 (en) | 2007-11-27 |
| US20070254929A1 (en) | 2007-11-01 |
| TW200504047A (en) | 2005-02-01 |
| US20040198778A1 (en) | 2004-10-07 |
| NO20054263D0 (no) | 2005-09-15 |
| CR7951A (es) | 2008-10-29 |
| ECSP056128A (es) | 2006-03-01 |
| CO5640049A2 (es) | 2006-05-31 |
| CN1780829A (zh) | 2006-05-31 |
| BRPI0408962A (pt) | 2006-04-04 |
| ZA200507896B (en) | 2007-03-28 |
| AR043940A1 (es) | 2005-08-17 |
| SG167669A1 (en) | 2011-01-28 |
| NZ542468A (en) | 2009-01-31 |
| TWI336698B (en) | 2011-02-01 |
| US7547725B2 (en) | 2009-06-16 |
| JP2006522126A (ja) | 2006-09-28 |
| MXPA05010368A (es) | 2005-11-17 |
| CN101274926A (zh) | 2008-10-01 |
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