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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- 125000002757 morpholinyl group Chemical group 0.000 description 1
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- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
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- 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
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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
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 |
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| UAA200510177A UA82093C2 (uk) | 2003-03-31 | 2004-03-26 | Фтор- та трифторалкіловмісні гетероциклічні сульфонамідні інгібітори утворення бета-амілоїду та їх похідні |
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| CN1263750C (zh) * | 2000-12-13 | 2006-07-12 | 惠氏 | β淀粉样蛋白产生的杂环磺酰胺类抑制剂 |
| AU2002357333B2 (en) * | 2001-12-20 | 2008-02-28 | Bristol-Myers Squibb Company | Alpha-(N-sulphonamido)acetamide derivatives as Beta-amyloid inhibitors |
| BR0311767A (pt) * | 2002-06-11 | 2005-03-08 | Wyeth Corp | Compostos inibidores de sulfonamida substituìda da produção de beta amilóide, suas composições e usos |
| KR20060002908A (ko) * | 2003-03-31 | 2006-01-09 | 와이어쓰 | 베타 아밀로이드 생산 억제제인 플루오로- 및트리플루오로알킬-함유 헤테로사이클릭 설폰아미드 및 이의유도체 |
| CN1910158A (zh) * | 2004-01-16 | 2007-02-07 | 惠氏公司 | 含有氮杂环的β淀粉样蛋白生成的杂环磺酰胺抑制剂 |
| AU2007217966A1 (en) * | 2006-02-17 | 2007-08-30 | Wyeth | Selective N-sulfonylation of 2-amino trifluoroalkyl substituted alcohols |
| CA2641013A1 (en) * | 2006-02-17 | 2007-08-30 | Wyeth | Methods for preparing sulfonamide substituted alcohols and intermediates thereof |
| MX2008013539A (es) * | 2006-04-21 | 2008-10-29 | Wyeth Corp | Produccion de intermediarios de amino alcohol quiralmente puros, derivados de los mismos, y usos de los mismos. |
| US7550629B2 (en) * | 2006-04-21 | 2009-06-23 | Wyeth | Trifluoromethyl-containing phenylsulfonamide beta amyloid inhibitors |
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- 2004-03-26 CN CN2004800087813A patent/CN1780829B/zh not_active Expired - Fee Related
- 2004-03-26 CL CL200400647A patent/CL2004000647A1/es unknown
- 2004-03-26 MX MXPA05010368A patent/MXPA05010368A/es active IP Right Grant
- 2004-03-26 JP JP2006509331A patent/JP2006522126A/ja active Pending
- 2004-03-26 UA UAA200510177A patent/UA82093C2/uk unknown
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| NZ542468A (en) | 2009-01-31 |
| BRPI0408962A (pt) | 2006-04-04 |
| JP2006522126A (ja) | 2006-09-28 |
| CR7951A (es) | 2008-10-29 |
| CL2004000647A1 (es) | 2005-02-04 |
| ZA200507896B (en) | 2007-03-28 |
| RU2005133434A (ru) | 2006-07-10 |
| CN1780829B (zh) | 2010-12-29 |
| AU2004230844B2 (en) | 2010-12-09 |
| CN1780829A (zh) | 2006-05-31 |
| US7300951B2 (en) | 2007-11-27 |
| NO20054263L (no) | 2005-12-14 |
| US7858658B2 (en) | 2010-12-28 |
| US20090227667A1 (en) | 2009-09-10 |
| EP1608638A1 (en) | 2005-12-28 |
| MXPA05010368A (es) | 2005-11-17 |
| RU2342374C2 (ru) | 2008-12-27 |
| CO5640049A2 (es) | 2006-05-31 |
| US7547725B2 (en) | 2009-06-16 |
| TW200504047A (en) | 2005-02-01 |
| ECSP056128A (es) | 2006-03-01 |
| NO20054263D0 (no) | 2005-09-15 |
| CN101274926A (zh) | 2008-10-01 |
| SG167669A1 (en) | 2011-01-28 |
| US20070254929A1 (en) | 2007-11-01 |
| WO2004092155A1 (en) | 2004-10-28 |
| CA2517155A1 (en) | 2004-10-28 |
| TWI336698B (en) | 2011-02-01 |
| AR043940A1 (es) | 2005-08-17 |
| US20040198778A1 (en) | 2004-10-07 |
| AU2004230844A1 (en) | 2004-10-28 |
| KR20060002908A (ko) | 2006-01-09 |
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