JP2011525538A - カリウムチャネルモジュレーターとして有用なベンジルオキシアニリド誘導体 - Google Patents
カリウムチャネルモジュレーターとして有用なベンジルオキシアニリド誘導体 Download PDFInfo
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- JP2011525538A JP2011525538A JP2011516617A JP2011516617A JP2011525538A JP 2011525538 A JP2011525538 A JP 2011525538A JP 2011516617 A JP2011516617 A JP 2011516617A JP 2011516617 A JP2011516617 A JP 2011516617A JP 2011525538 A JP2011525538 A JP 2011525538A
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- -1 cycloalkyl compound Chemical class 0.000 claims description 48
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- WWMQXBPCROZJKE-UHFFFAOYSA-N n-[4-[(2,4-difluorophenyl)methoxy]-2,6-dimethylphenyl]-3,3-dimethylbutanamide Chemical compound CC1=C(NC(=O)CC(C)(C)C)C(C)=CC(OCC=2C(=CC(F)=CC=2)F)=C1 WWMQXBPCROZJKE-UHFFFAOYSA-N 0.000 description 1
- KAWULRQIBQZKKV-UHFFFAOYSA-N n-[4-[(3,4-difluorophenyl)methoxy]-2,6-dimethylphenyl]-3,3-dimethylbutanamide Chemical compound CC1=C(NC(=O)CC(C)(C)C)C(C)=CC(OCC=2C=C(F)C(F)=CC=2)=C1 KAWULRQIBQZKKV-UHFFFAOYSA-N 0.000 description 1
- IWYXKNSUXCXZIW-UHFFFAOYSA-N n-[4-[(4-bromophenyl)methoxy]-2,6-dimethylphenyl]-3,3-dimethylbutanamide Chemical compound CC1=C(NC(=O)CC(C)(C)C)C(C)=CC(OCC=2C=CC(Br)=CC=2)=C1 IWYXKNSUXCXZIW-UHFFFAOYSA-N 0.000 description 1
- MYDDTOMAZFZWNO-UHFFFAOYSA-N n-[4-[(4-chlorophenyl)methoxy]-2,6-dimethylphenyl]-3,3-dimethylbutanamide Chemical compound CC1=C(NC(=O)CC(C)(C)C)C(C)=CC(OCC=2C=CC(Cl)=CC=2)=C1 MYDDTOMAZFZWNO-UHFFFAOYSA-N 0.000 description 1
- YASUEAJKINEMNB-UHFFFAOYSA-N n-[4-[(4-fluorophenyl)methoxy]-2,6-dimethylphenyl]-3,3-dimethylbutanamide Chemical compound CC1=C(NC(=O)CC(C)(C)C)C(C)=CC(OCC=2C=CC(F)=CC=2)=C1 YASUEAJKINEMNB-UHFFFAOYSA-N 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 238000002732 pharmacokinetic assay Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 229940069328 povidone Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012910 preclinical development Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 230000036390 resting membrane potential Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000008137 solubility enhancer Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- GKCBAIGFKIBETG-UHFFFAOYSA-N tetracaine Chemical compound CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 GKCBAIGFKIBETG-UHFFFAOYSA-N 0.000 description 1
- 229960002372 tetracaine Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/24—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/26—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a saturated carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7530708P | 2008-06-24 | 2008-06-24 | |
| US61/075,307 | 2008-06-24 | ||
| PCT/US2009/048504 WO2010008894A1 (en) | 2008-06-24 | 2009-06-24 | Benzyloxy anilide derivatives useful as potassium channel modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011525538A true JP2011525538A (ja) | 2011-09-22 |
| JP2011525538A5 JP2011525538A5 (https=) | 2013-03-21 |
Family
ID=41448228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011516617A Pending JP2011525538A (ja) | 2008-06-24 | 2009-06-24 | カリウムチャネルモジュレーターとして有用なベンジルオキシアニリド誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US8188314B2 (https=) |
| EP (1) | EP2310369A4 (https=) |
| JP (1) | JP2011525538A (https=) |
| AU (1) | AU2009271302A1 (https=) |
| CA (1) | CA2728915A1 (https=) |
| MX (1) | MX2010014461A (https=) |
| WO (1) | WO2010008894A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20150053257A (ko) | 2012-04-30 | 2015-05-15 | 사이플루어 라이프 사이언시즈, 엘엘씨 | 플루오르화 2-아미노-4-(벤질아미노)페닐카르바메이트 유도체 |
| CN103508943B (zh) * | 2012-06-29 | 2017-06-09 | 江苏先声药业有限公司 | 作为钾通道调节剂的化合物 |
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| JPS49426A (https=) * | 1972-04-15 | 1974-01-05 | ||
| JPS5257196A (en) * | 1975-10-30 | 1977-05-11 | Miles Lab | 22substituted hydroxyanilinoo hexahydroo2hhbenzo *alpha* quinolidine derivative |
| JPS5323962A (en) * | 1976-07-23 | 1978-03-06 | Takeda Chem Ind Ltd | Tetrahydroisophthalimide derivatives and their preparation |
| JPS6072787A (ja) * | 1983-09-30 | 1985-04-24 | Hodogaya Chem Co Ltd | 感熱記録材料 |
| JPH05112542A (ja) * | 1991-04-16 | 1993-05-07 | Delalande Sa | ３−アリールオキサゾリジノン誘導体、その製造方法およびその治療的使用 |
| JPH09505275A (ja) * | 1993-09-22 | 1997-05-27 | グラクソ、グループ、リミテッド | ３‐（５‐テトラゾリル‐ベンジル）アミノ‐ピペリジン誘導体およびタチキニンのアンタゴニスト |
| JP2002501502A (ja) * | 1997-04-25 | 2002-01-15 | スミスクライン・ビーチャム・コーポレイション | プロテアーゼ阻害物質 |
| JP2003026683A (ja) * | 2001-07-10 | 2003-01-29 | Sankyo Co Ltd | 新規ガランタミン類縁体 |
| JP2006503829A (ja) * | 2002-09-13 | 2006-02-02 | アストラゼネカ・アクチエボラーグ | スルホンアミド誘導体およびそのｔａｃｅインヒビターとしての使用 |
| JP2006523196A (ja) * | 2003-03-11 | 2006-10-12 | ニューロサーチ、アクティーゼルスカブ | 新規ｋｃｎｑチャネルを調節する化合物及びその医薬用途 |
| JP2007512255A (ja) * | 2003-11-13 | 2007-05-17 | アンビット バイオサイエンシス コーポレーション | キナーゼ調節因子としての尿素誘導体 |
| JP2007525482A (ja) * | 2003-10-07 | 2007-09-06 | レノビス， インコーポレイテッド | イオンチャネルリガンドとしてのアミド化合物およびその使用 |
| WO2008020607A1 (en) * | 2006-08-17 | 2008-02-21 | Dainippon Sumitomo Pharma Co., Ltd. | Phthalide derivative and salt thereof |
| JP2008512402A (ja) * | 2004-09-13 | 2008-04-24 | ハー・ルンドベック・アクチエゼルスカベット | 置換されたアニリン誘導体 |
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| US4180509A (en) * | 1977-07-01 | 1979-12-25 | Merrell Toraude Et Compagnie | α-Ethynyl tryptophanes |
| EP0927164A1 (en) * | 1996-09-10 | 1999-07-07 | PHARMACIA & UPJOHN COMPANY | 8-hydroxy-7-substituted quinolines as anti-viral agents |
| EA009372B1 (ru) * | 2002-05-29 | 2007-12-28 | Ф. Хоффманн-Ля Рош Аг | N-ациламинобензольные производные в качестве селективных ингибиторов моноаминооксидазы в |
| US7718692B2 (en) * | 2004-02-13 | 2010-05-18 | Carson John R | Hetero-substituted acetanilide derivatives as analgesic agents |
| AR043507A1 (es) * | 2003-03-14 | 2005-08-03 | Lundbeck & Co As H | Derivados de anilina sustituidos y composiciones farmaceuticas |
| WO2006022442A1 (ja) * | 2004-08-24 | 2006-03-02 | Santen Pharmaceutical Co., Ltd. | ジヒドロオロテートデヒドロゲナーゼ阻害活性を有する新規複素環アミド誘導体 |
| BRPI0716715B1 (pt) * | 2006-08-23 | 2021-07-06 | Xenon Pharmaceuticals, Inc | Derivados de 4-(n-azacicloalquil) anilidas como moduladores de canal de potássio, seus usos, produto, composição, comprimido e cápsula |
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2009
- 2009-06-24 AU AU2009271302A patent/AU2009271302A1/en not_active Abandoned
- 2009-06-24 JP JP2011516617A patent/JP2011525538A/ja active Pending
- 2009-06-24 US US12/491,055 patent/US8188314B2/en not_active Expired - Fee Related
- 2009-06-24 CA CA2728915A patent/CA2728915A1/en not_active Abandoned
- 2009-06-24 EP EP09798525.3A patent/EP2310369A4/en not_active Withdrawn
- 2009-06-24 WO PCT/US2009/048504 patent/WO2010008894A1/en not_active Ceased
- 2009-06-24 MX MX2010014461A patent/MX2010014461A/es not_active Application Discontinuation
-
2012
- 2012-05-29 US US13/483,018 patent/US8492588B2/en not_active Expired - Fee Related
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| JPS49426A (https=) * | 1972-04-15 | 1974-01-05 | ||
| JPS5257196A (en) * | 1975-10-30 | 1977-05-11 | Miles Lab | 22substituted hydroxyanilinoo hexahydroo2hhbenzo *alpha* quinolidine derivative |
| JPS5323962A (en) * | 1976-07-23 | 1978-03-06 | Takeda Chem Ind Ltd | Tetrahydroisophthalimide derivatives and their preparation |
| JPS6072787A (ja) * | 1983-09-30 | 1985-04-24 | Hodogaya Chem Co Ltd | 感熱記録材料 |
| JPH05112542A (ja) * | 1991-04-16 | 1993-05-07 | Delalande Sa | ３−アリールオキサゾリジノン誘導体、その製造方法およびその治療的使用 |
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| JP2002501502A (ja) * | 1997-04-25 | 2002-01-15 | スミスクライン・ビーチャム・コーポレイション | プロテアーゼ阻害物質 |
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Also Published As
| Publication number | Publication date |
|---|---|
| WO2010008894A1 (en) | 2010-01-21 |
| US20120329869A1 (en) | 2012-12-27 |
| AU2009271302A1 (en) | 2010-01-21 |
| EP2310369A1 (en) | 2011-04-20 |
| EP2310369A4 (en) | 2014-02-19 |
| US20090326059A1 (en) | 2009-12-31 |
| US8492588B2 (en) | 2013-07-23 |
| MX2010014461A (es) | 2011-04-28 |
| US8188314B2 (en) | 2012-05-29 |
| CA2728915A1 (en) | 2010-01-21 |
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