CN101274926A - β淀粉样蛋白生成抑制剂含氟和三氟烷基杂环磺酰胺及其衍生物 - Google Patents
β淀粉样蛋白生成抑制剂含氟和三氟烷基杂环磺酰胺及其衍生物 Download PDFInfo
- Publication number
- CN101274926A CN101274926A CNA2008100013400A CN200810001340A CN101274926A CN 101274926 A CN101274926 A CN 101274926A CN A2008100013400 A CNA2008100013400 A CN A2008100013400A CN 200810001340 A CN200810001340 A CN 200810001340A CN 101274926 A CN101274926 A CN 101274926A
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- Prior art keywords
- fluoro
- thiophene
- sulphonamide
- chloro
- methylol
- 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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- 108010090849 Amyloid beta-Peptides Proteins 0.000 title claims abstract description 30
- 102000013455 Amyloid beta-Peptides Human genes 0.000 title claims abstract description 30
- -1 heterocyclic sulfonamide Chemical class 0.000 title claims description 242
- 229940124530 sulfonamide Drugs 0.000 title claims description 72
- 125000004950 trifluoroalkyl group Chemical group 0.000 title description 13
- 239000003112 inhibitor Substances 0.000 title description 10
- 125000003709 fluoroalkyl group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 177
- 238000000034 method Methods 0.000 claims abstract description 108
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 54
- 239000001257 hydrogen Substances 0.000 claims abstract description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 36
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 30
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 26
- 150000002367 halogens Chemical group 0.000 claims abstract description 24
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 24
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 22
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 19
- 150000001993 dienes Chemical group 0.000 claims abstract description 15
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 14
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 125000005017 substituted alkenyl group Chemical group 0.000 claims abstract description 7
- 125000004426 substituted alkynyl group Chemical group 0.000 claims abstract description 6
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- 238000002360 preparation method Methods 0.000 claims description 43
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 42
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 16
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- BWJZHYWAXLWLTB-UHFFFAOYSA-N thiophene-3-sulfonamide Chemical compound NS(=O)(=O)C=1C=CSC=1 BWJZHYWAXLWLTB-UHFFFAOYSA-N 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 9
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- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 claims description 9
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 claims description 8
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- 210000004556 brain Anatomy 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
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- 208000010877 cognitive disease Diseases 0.000 claims description 4
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
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- 239000011777 magnesium Substances 0.000 claims description 3
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 3
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
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- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- UZMQSZBTFGHLAH-UHFFFAOYSA-N 1-benzothiophene-2-sulfonamide Chemical compound C1=CC=C2SC(S(=O)(=O)N)=CC2=C1 UZMQSZBTFGHLAH-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 239000001273 butane Substances 0.000 claims 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 193
- 238000003756 stirring Methods 0.000 description 108
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 96
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- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
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- 125000003373 pyrazinyl group Chemical group 0.000 description 1
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- 210000000582 semen Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate 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
- 235000009518 sodium iodide Nutrition 0.000 description 1
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- 229960001479 tosylchloramide sodium Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- 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
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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
-
- 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)
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| US45922803P | 2003-03-31 | 2003-03-31 | |
| US60/459228 | 2003-03-31 |
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| SG (1) | SG167669A1 (https=) |
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| HUP0303857A3 (en) * | 2000-12-13 | 2007-07-30 | Wyeth Corp | Heterocyclic sulifonamide inhibitors of beta amyloid production |
| CN1289469C (zh) * | 2001-12-20 | 2006-12-13 | 布里斯托尔-迈尔斯斯奎布公司 | α－(N－磺酰氨基)乙酰胺衍生物作为β－淀粉样蛋白抑制剂 |
| 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 |
| BRPI0408962A (pt) * | 2003-03-31 | 2006-04-04 | Wyeth Corp | inibidores sulfonamidas heterocìclicos contendo flúor- e trifluoroalquila da produção de beta amilóide e seus derivados |
| ES2330451T3 (es) * | 2004-01-16 | 2009-12-10 | Wyeth | Inhibidores a base de sulfonamidas heterociclicas de la produccion de beta-amiloides que contienen un azol. |
| 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 |
| 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 |
| JP2009534385A (ja) * | 2006-04-21 | 2009-09-24 | ワイス | キラル的に純粋なアミノアルコール中間体、それらの誘導体の製造、及びそれらの使用 |
| CA2667802A1 (en) * | 2006-11-03 | 2008-05-29 | Northwestern University | Multiple sclerosis therapy |
| EP2193117A1 (en) * | 2007-07-16 | 2010-06-09 | Wyeth a Corporation of the State of Delaware | Inhibitors of beta amyloid production |
| WO2009012203A1 (en) * | 2007-07-16 | 2009-01-22 | Wyeth | Processes and intermediates for the preparation of heterocyclic sulfonamide compounds |
| PA8789601A1 (es) * | 2007-07-16 | 2009-02-09 | Wyeth Corp | Proceso para la preparación de trifluoralquil-fenil sulfonamidas y de sulfonamidas heterocíclicas |
| 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 |
| 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 |
| CL2009000019A1 (es) * | 2008-01-11 | 2009-05-22 | Wyeth Corp | Compuestos derivados de aril sulfonamida que contienen o-sulfato u o-fosfato; procedimiento de preparacion; composicion farmaceutica que los comprende; y uso como profarmacos para incrementar la semivida de circulacion de compuestos inhibidores de la produccion de beta-amiloide, utiles en el tratamiento del alzheimer y cancer. |
| CN102088855A (zh) * | 2008-05-08 | 2011-06-08 | 百时美施贵宝公司 | 2-芳基甘氨酰胺衍生物 |
| US8992783B2 (en) | 2008-09-05 | 2015-03-31 | Max-Planck-Gessellschaft 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 |
| WO2011112858A1 (en) * | 2010-03-10 | 2011-09-15 | North Carolina Central University | Phenoxy thiophene sulfonamides and their use as inhibitors of glucuronidase |
| CA2884309A1 (en) | 2012-09-07 | 2014-03-13 | Massachusetts Eye And Ear Infirmary | Methods and compositions for regenerating hair cells and/or supporting cells from differentiated cochlear cells or differentiated utricular cells by modulation of notch and cmyc activity |
| 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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| US5571821A (en) * | 1993-05-20 | 1996-11-05 | Texas Biotechnology Corporation | Sulfonamides and derivatives thereof that modulate the activity of endothelin |
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| EP0939629A4 (en) | 1996-07-22 | 2002-07-17 | Monsanto Co | THIOL SULFONAMIDE METALLOPROTEASE INHIBITORS |
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| DE19650196A1 (de) * | 1996-12-04 | 1998-06-10 | Bayer Ag | Thienylsulfonylamino(thio)carbonylverbindungen |
| JPH11343279A (ja) | 1998-03-16 | 1999-12-14 | Shionogi & Co Ltd | スルホンアミド誘導体およびそれらを含有するＴＮＦ―α産生抑制剤 |
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2004
- 2004-03-26 BR BRPI0408962-6A patent/BRPI0408962A/pt not_active IP Right Cessation
- 2004-03-26 NZ NZ542468A patent/NZ542468A/en not_active IP Right Cessation
- 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 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
- 2004-03-26 CN CN2004800087813A patent/CN1780829B/zh not_active Expired - Fee Related
- 2004-03-26 TW TW093108219A patent/TWI336698B/zh not_active IP Right Cessation
- 2004-03-26 CA CA002517155A patent/CA2517155A1/en not_active Abandoned
- 2004-03-26 UA UAA200510177A patent/UA82093C2/uk unknown
- 2004-03-26 AU AU2004230844A patent/AU2004230844B2/en not_active Expired - Fee Related
- 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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- 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
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Also Published As
| Publication number | Publication date |
|---|---|
| UA82093C2 (uk) | 2008-03-11 |
| 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 |
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