JP2006522126A5 - - Google Patents
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- Publication number
- JP2006522126A5 JP2006522126A5 JP2006509331A JP2006509331A JP2006522126A5 JP 2006522126 A5 JP2006522126 A5 JP 2006522126A5 JP 2006509331 A JP2006509331 A JP 2006509331A JP 2006509331 A JP2006509331 A JP 2006509331A JP 2006522126 A5 JP2006522126 A5 JP 2006522126A5
- Authority
- JP
- Japan
- Prior art keywords
- sulfonamide
- trifluoro
- thiophene
- compound
- hydroxymethyl
- 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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- 150000001875 compounds Chemical class 0.000 claims 40
- 125000000217 alkyl group Chemical group 0.000 claims 21
- 239000011780 sodium chloride Substances 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 14
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims 11
- -1 CF 3 Chemical group 0.000 claims 11
- 229960001663 sulfanilamide Drugs 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 239000000651 prodrug Substances 0.000 claims 8
- 229940002612 prodrugs Drugs 0.000 claims 8
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims 6
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 239000012024 dehydrating agents Substances 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 125000001010 sulfinic acid amide group Chemical group 0.000 claims 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N (E)-but-2-enedioate;hydron Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- 206010002023 Amyloidosis Diseases 0.000 claims 2
- 206010002022 Amyloidosis Diseases 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 2
- IBVWKWXNEQMZMK-UHFFFAOYSA-N [ethyl(propan-2-yloxy)alumanyl]formonitrile Chemical group CC[Al](C#N)OC(C)C IBVWKWXNEQMZMK-UHFFFAOYSA-N 0.000 claims 2
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims 2
- 235000008206 alpha-amino acids Nutrition 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 2
- 150000001993 dienes Chemical class 0.000 claims 2
- XGZNHFPFJRZBBT-UHFFFAOYSA-N ethanol;titanium Chemical group [Ti].CCO.CCO.CCO.CCO XGZNHFPFJRZBBT-UHFFFAOYSA-N 0.000 claims 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- NRIVLCBZUZOJKF-UHFFFAOYSA-N 2,5-dichloro-N-[4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butan-2-yl]thiophene-3-sulfonamide Chemical compound FC(F)(F)C(C(F)(F)F)C(CO)NS(=O)(=O)C=1C=C(Cl)SC=1Cl NRIVLCBZUZOJKF-UHFFFAOYSA-N 0.000 claims 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 1
- HGHZXRLQQGFESX-UHFFFAOYSA-N 4,5-dichloro-N-[4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butan-2-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C(C(F)(F)F)C(CO)NS(=O)(=O)C1=CC(Cl)=C(Cl)S1 HGHZXRLQQGFESX-UHFFFAOYSA-N 0.000 claims 1
- UXPMWBRBKHZFJJ-UHFFFAOYSA-N 5-chloro-3-(4,4,4-trifluoro-1-hydroxybutan-2-yl)thiophene-2-sulfonamide Chemical compound NS(=O)(=O)C=1SC(Cl)=CC=1C(CO)CC(F)(F)F UXPMWBRBKHZFJJ-UHFFFAOYSA-N 0.000 claims 1
- UJIHZLJAUMPTFR-RNFRBKRXSA-N 5-chloro-N-[(2S,3R)-5,5,5-trifluoro-1-hydroxy-3-methylpentan-2-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C[C@@H](C)[C@@H](CO)NS(=O)(=O)C1=CC=C(Cl)S1 UJIHZLJAUMPTFR-RNFRBKRXSA-N 0.000 claims 1
- FKECWLIGCZXHBY-LDWIPMOCSA-N 5-chloro-N-[(3S,4R)-6,6,6-trifluoro-4-methyl-2-oxohexan-3-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C[C@@H](C)[C@@H](C(C)=O)NS(=O)(=O)C1=CC=C(Cl)S1 FKECWLIGCZXHBY-LDWIPMOCSA-N 0.000 claims 1
- HHRPDEFXZGZRDB-UHFFFAOYSA-N 5-chloro-N-[1-(4,4-difluorocyclohexyl)-2-hydroxyethyl]thiophene-2-sulfonamide Chemical compound C1CC(F)(F)CCC1C(CO)NS(=O)(=O)C1=CC=C(Cl)S1 HHRPDEFXZGZRDB-UHFFFAOYSA-N 0.000 claims 1
- 206010001897 Alzheimer's disease Diseases 0.000 claims 1
- 208000006141 Amyloid angiopathy Diseases 0.000 claims 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 claims 1
- 108010090849 Amyloid beta-Peptides Proteins 0.000 claims 1
- 102100000129 CHURC1 Human genes 0.000 claims 1
- 101710014631 CHURC1 Proteins 0.000 claims 1
- 208000005145 Cerebral Amyloid Angiopathy Diseases 0.000 claims 1
- 206010057668 Cognitive disease Diseases 0.000 claims 1
- 201000010374 Down syndrome Diseases 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N Malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N Mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 claims 1
- JRZREWWYEJRTFF-RXMQYKEDSA-N N-[(2S)-4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butan-2-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C(C(F)(F)F)[C@@H](CO)NS(=O)(=O)C1=CC=CS1 JRZREWWYEJRTFF-RXMQYKEDSA-N 0.000 claims 1
- QGNNYWYWUIHAIR-ZCFIWIBFSA-N N-[(2S)-4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butan-2-yl]thiophene-3-sulfonamide Chemical compound FC(F)(F)C(C(F)(F)F)[C@@H](CO)NS(=O)(=O)C=1C=CSC=1 QGNNYWYWUIHAIR-ZCFIWIBFSA-N 0.000 claims 1
- NFRHMCWDOSGFLS-UHFFFAOYSA-N N-[4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butan-2-yl]-1-benzothiophene-2-sulfonamide Chemical compound C1=CC=C2SC(S(=O)(=O)NC(CO)C(C(F)(F)F)C(F)(F)F)=CC2=C1 NFRHMCWDOSGFLS-UHFFFAOYSA-N 0.000 claims 1
- JRZREWWYEJRTFF-UHFFFAOYSA-N N-[4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butan-2-yl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C(C(F)(F)F)C(CO)NS(=O)(=O)C1=CC=CS1 JRZREWWYEJRTFF-UHFFFAOYSA-N 0.000 claims 1
- QGNNYWYWUIHAIR-UHFFFAOYSA-N N-[4,4,4-trifluoro-1-hydroxy-3-(trifluoromethyl)butan-2-yl]thiophene-3-sulfonamide Chemical compound FC(F)(F)C(C(F)(F)F)C(CO)NS(=O)(=O)C=1C=CSC=1 QGNNYWYWUIHAIR-UHFFFAOYSA-N 0.000 claims 1
- 229910005965 SO 2 Inorganic materials 0.000 claims 1
- CESUXLKAADQNTB-UHFFFAOYSA-N Tert-Butanesulfinamide Chemical compound CC(C)(C)S(N)=O CESUXLKAADQNTB-UHFFFAOYSA-N 0.000 claims 1
- 206010044688 Trisomy 21 Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 201000001084 cerebrovascular disease Diseases 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000005712 crystallization Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 239000008079 hexane Substances 0.000 claims 1
- 229960000443 hydrochloric acid Drugs 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing Effects 0.000 claims 1
- 201000008319 inclusion body myositis Diseases 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-L lithium;dihydroxide Chemical compound [Li+].[OH-].[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-L 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 239000001630 malic acid Substances 0.000 claims 1
- 229940099690 malic acid Drugs 0.000 claims 1
- 235000011090 malic acid Nutrition 0.000 claims 1
- 229960002510 mandelic acid Drugs 0.000 claims 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000002808 molecular sieve Substances 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 239000001384 succinic acid Substances 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 229960001367 tartaric acid Drugs 0.000 claims 1
- GUJWNCDSIDXKBJ-UHFFFAOYSA-N CCOC(C(C(C)C(F)(F)F)NC(C)c1ccccc1)=O Chemical compound CCOC(C(C(C)C(F)(F)F)NC(C)c1ccccc1)=O GUJWNCDSIDXKBJ-UHFFFAOYSA-N 0.000 description 1
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 (2)
| Publication Number | Publication Date |
|---|---|
| JP2006522126A JP2006522126A (ja) | 2006-09-28 |
| JP2006522126A5 true JP2006522126A5 (US07858658-20101228-C00033.png) | 2009-06-04 |
Family
ID=33299665
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006509331A Pending JP2006522126A (ja) | 2003-03-31 | 2004-03-26 | βアミロイド生産のフルオロ含有およびトリフルオロアルキル含有複素環スルホンアミド阻害物質およびその誘導体 |
Country Status (22)
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE330950T1 (de) * | 2000-12-13 | 2006-07-15 | Wyeth Corp | Heterocyclische sulfonamide als inhibitoren der beta-amyloid-produktion |
| RS51155B (sr) * | 2001-12-20 | 2010-10-31 | Bristol-Myers Squibb Company | DERIVATI α -(N-SULFONAMIDO)ACETAMIDA KAO INHIBITORI β -AMILOIDA |
| AU2003237518B8 (en) * | 2002-06-11 | 2009-03-12 | Arqule, Inc. | Substituted phenylsulfonamide inhibitors of beta amyloid production |
| KR20060002908A (ko) * | 2003-03-31 | 2006-01-09 | 와이어쓰 | 베타 아밀로이드 생산 억제제인 플루오로- 및트리플루오로알킬-함유 헤테로사이클릭 설폰아미드 및 이의유도체 |
| ATE443701T1 (de) * | 2004-01-16 | 2009-10-15 | Wyeth Corp | Heterocyclische, ein azol enthaltende sulfonamidinhibitoren der beta-amyloid-produktion |
| CA2637615A1 (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 |
| US7476762B2 (en) | 2006-04-21 | 2009-01-13 | Wyeth | Methods for preparing sulfonamide compounds |
| US7550629B2 (en) | 2006-04-21 | 2009-06-23 | Wyeth | Trifluoromethyl-containing phenylsulfonamide beta amyloid inhibitors |
| CN101472877A (zh) | 2006-04-21 | 2009-07-01 | 惠氏公司 | 制备手性纯氨基醇中间体、其衍生物及其用途 |
| JP2010509235A (ja) * | 2006-11-03 | 2010-03-25 | ノースウェスタン ユニバーシティ | 多発性硬化症の治療 |
| PA8789701A1 (es) * | 2007-07-16 | 2009-04-23 | Wyeth Corp | Inhibidores de producción de beta amiloide |
| PA8789601A1 (es) * | 2007-07-16 | 2009-02-09 | Wyeth Corp | Proceso para la preparación de trifluoralquil-fenil sulfonamidas y de sulfonamidas heterocíclicas |
| PE20090810A1 (es) * | 2007-07-16 | 2009-07-20 | Wyeth Corp | Procesos e intermediarios para la preparacion de compuestos de sulfonamida heterociclica |
| US8093276B2 (en) * | 2007-10-31 | 2012-01-10 | Bristol-Myers Squibb Company | Alpha-(N-sulfonamido)acetamide compound as an inhibitor of beta amyloid peptide production |
| US8084477B2 (en) | 2007-10-31 | 2011-12-27 | Bristol-Myers Squibb Company | Alpha-(N-sulfonamido)acetamide compound as an inhibitor of beta amyloid peptide production |
| WO2009089237A1 (en) * | 2008-01-11 | 2009-07-16 | Wyeth | Compositions containing o-sulfate and o-phosphate containing aryl sulfonamide derivatives useful as beta-amyloid inhibitors |
| US20110059940A1 (en) * | 2008-05-08 | 2011-03-10 | Bristol- Myers Squibb Company | 2-Aryl Glycinamide Derivatives |
| WO2010025968A2 (en) * | 2008-09-05 | 2010-03-11 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e. V. | Process for enantioseparation of chiral systems with compound formation using two subsequent crystallization steps |
| US8044077B2 (en) * | 2009-03-19 | 2011-10-25 | Bristol-Myers Squibb Company | Alpha-(N-sulfonamido)acetamide compounds incorporating deuterium as inhibitors of beta amyloid peptide production |
| US20110071199A1 (en) * | 2009-03-20 | 2011-03-24 | Bristol-Myers Squibb Company | Thiophenyl Sulfonamides for the Treatment of Alzheimer's Disease |
| US7977362B2 (en) * | 2009-03-20 | 2011-07-12 | Bristol-Myers Squibb Company | Alpha-(N-benzenesulfonamido)cycloalkyl derivatives |
| TW201043269A (en) * | 2009-04-14 | 2010-12-16 | Bristol Myers Squibb Co | Bioavailable compositions of amorphous alpha-(N-sulfonamido)acetamide compound |
| US8252821B2 (en) * | 2009-04-14 | 2012-08-28 | Bristol-Myers Squibb Company | Bioavailable capsule compositions of amorphous alpha-(N-sulfonamido)acetamide compound |
| WO2010126002A1 (ja) * | 2009-04-28 | 2010-11-04 | 塩野義製薬株式会社 | ヘテロ環スルホンアミド化合物を含有する医薬 |
| WO2011084503A1 (en) * | 2009-12-16 | 2011-07-14 | North Carolina Central University | Phenoxy thiophene sulfonamides and their use in the treatment of neurodegenerative diseases |
| US9223209B2 (en) * | 2010-02-19 | 2015-12-29 | International Business Machines Corporation | Sulfonamide-containing photoresist compositions and methods of use |
| US9223217B2 (en) * | 2010-02-19 | 2015-12-29 | International Business Machines Corporation | Sulfonamide-containing topcoat and photoresist additive compositions and methods of use |
| US9617239B2 (en) | 2010-03-10 | 2017-04-11 | North Carolina Central University | Phenoxy thiophene sulfonamides and their use as inhibitors of glucuronidase |
| US20150209367A1 (en) | 2012-09-07 | 2015-07-30 | Massachusetts Eye & Ear Infirmary | Treating Hearing Loss |
| US20160067306A1 (en) | 2013-04-19 | 2016-03-10 | National University Corporation Hokkaido University | Treatment agent for cognitive impairment induced by amyloid beta-protein, therapeutic agent for alzheimer's disease, and treatment method and pathological analysis method related to these |
| EP3212773B1 (en) | 2014-10-29 | 2021-09-15 | Massachusetts Eye and Ear Infirmary | Efficient delivery of therapeutic molecules to cells of the inner ear |
| EP3458076A4 (en) | 2016-05-16 | 2020-01-22 | The General Hospital Corporation | HUMAN RESPIRATORY STEM CELLS IN BREEDING LUNG EPITHEL |
| EP3743057A4 (en) | 2018-01-26 | 2021-11-17 | Massachusetts Eye & Ear Infirmary | TREATMENT OF HEARING LOSS |
| EP4299062A1 (en) | 2022-06-30 | 2024-01-03 | Vilnius University | Inhibition of protein amyloid aggregation using fluorinated benzenesulfonamides |
Family Cites Families (43)
| Publication number | Priority date | Publication date | Assignee | Title |
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2004
- 2004-03-26 KR KR1020057018637A patent/KR20060002908A/ko not_active Application Discontinuation
- 2004-03-26 RU RU2005133434/04A patent/RU2342374C2/ru not_active IP Right Cessation
- 2004-03-26 WO PCT/US2004/009268 patent/WO2004092155A1/en active Application Filing
- 2004-03-26 BR BRPI0408962-6A patent/BRPI0408962A/pt not_active IP Right Cessation
- 2004-03-26 JP JP2006509331A patent/JP2006522126A/ja active Pending
- 2004-03-26 AU AU2004230844A patent/AU2004230844B2/en not_active Expired - Fee Related
- 2004-03-26 EP EP04758978A patent/EP1608638A1/en not_active Withdrawn
- 2004-03-26 UA UAA200510177A patent/UA82093C2/uk unknown
- 2004-03-26 CN CNA2008100013400A patent/CN101274926A/zh active Pending
- 2004-03-26 NZ NZ542468A patent/NZ542468A/en not_active IP Right Cessation
- 2004-03-26 SG SG200708961-8A patent/SG167669A1/en unknown
- 2004-03-26 CN CN2004800087813A patent/CN1780829B/zh not_active Expired - Fee Related
- 2004-03-26 AR ARP040101022A patent/AR043940A1/es unknown
- 2004-03-26 US US10/810,517 patent/US7300951B2/en not_active Expired - Fee Related
- 2004-03-26 MX MXPA05010368A patent/MXPA05010368A/es active IP Right Grant
- 2004-03-26 CL CL200400647A patent/CL2004000647A1/es unknown
- 2004-03-26 CA CA002517155A patent/CA2517155A1/en not_active Abandoned
- 2004-03-26 TW TW093108219A patent/TWI336698B/zh not_active IP Right Cessation
-
2005
- 2005-08-19 CR CR7951A patent/CR7951A/es unknown
- 2005-09-15 NO NO20054263A patent/NO20054263L/no not_active Application Discontinuation
- 2005-09-29 ZA ZA200507896A patent/ZA200507896B/en unknown
- 2005-10-26 CO CO05109226A patent/CO5640049A2/es not_active Application Discontinuation
- 2005-10-28 EC EC2005006128A patent/ECSP056128A/es unknown
-
2007
- 2007-06-15 US US11/818,630 patent/US7547725B2/en not_active Expired - Fee Related
-
2009
- 2009-05-05 US US12/435,442 patent/US7858658B2/en not_active Expired - Fee Related
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