WO2003042150A1 - Nouveaux derives de benzophenone ou sels de ceux-ci - Google Patents

Nouveaux derives de benzophenone ou sels de ceux-ci Download PDF

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Publication number
WO2003042150A1
WO2003042150A1 PCT/JP2002/011846 JP0211846W WO03042150A1 WO 2003042150 A1 WO2003042150 A1 WO 2003042150A1 JP 0211846 W JP0211846 W JP 0211846W WO 03042150 A1 WO03042150 A1 WO 03042150A1
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WO
WIPO (PCT)
Prior art keywords
salts
optionally
remedies
arthritis
useful
Prior art date
Application number
PCT/JP2002/011846
Other languages
English (en)
French (fr)
Inventor
Hisaaki Chaki
Hironori Kotsubo
Tadashi Tanaka
Yukihiko Aikawa
Shuichi Hirono
Shunichi Shiozawa
Original Assignee
Toyama Chemical Co., Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to IL16173602A priority Critical patent/IL161736A0/xx
Priority to HU0402025A priority patent/HUP0402025A3/hu
Application filed by Toyama Chemical Co., Ltd. filed Critical Toyama Chemical Co., Ltd.
Priority to JP2003543987A priority patent/JP4554926B2/ja
Priority to AU2002349777A priority patent/AU2002349777B2/en
Priority to US10/493,223 priority patent/US7772285B2/en
Priority to MXPA04004654A priority patent/MXPA04004654A/es
Priority to EP02781763A priority patent/EP1445249B1/en
Priority to BR0214177-9A priority patent/BR0214177A/pt
Priority to ROA200400442A priority patent/RO123430B1/ro
Priority to DK02781763.4T priority patent/DK1445249T3/da
Priority to CN028248120A priority patent/CN1602291B/zh
Priority to ES02781763T priority patent/ES2394963T3/es
Priority to NZ532810A priority patent/NZ532810A/en
Priority to CA2467261A priority patent/CA2467261C/en
Publication of WO2003042150A1 publication Critical patent/WO2003042150A1/ja
Priority to IL161736A priority patent/IL161736A/en
Priority to ZA2004/03373A priority patent/ZA200403373B/en
Priority to NO20042495A priority patent/NO329094B1/no

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
    • C07C205/34—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms of the carbon skeleton
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/76—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
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    • C07C271/62—Compounds containing any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylcarbamates
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    • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
    • C07C65/34—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups polycyclic
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    • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
    • C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
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    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/734—Ethers
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    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
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    • C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
    • C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
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    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/94—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of polycyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of six-membered aromatic rings
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PCT/JP2002/011846 2001-11-16 2002-11-13 Nouveaux derives de benzophenone ou sels de ceux-ci WO2003042150A1 (fr)

Priority Applications (17)

Application Number Priority Date Filing Date Title
NZ532810A NZ532810A (en) 2001-11-16 2002-11-13 Novel bensophenone derivatives or salts thereof
BR0214177-9A BR0214177A (pt) 2001-11-16 2002-11-13 Derivado de benzofenona, agente preventivo ou terapêutico para uma doença em que está envolvida expressão excessiva de ap-1, e, inibidor de ap-1
JP2003543987A JP4554926B2 (ja) 2001-11-16 2002-11-13 新規なベンゾフェノン誘導体またはその塩
AU2002349777A AU2002349777B2 (en) 2001-11-16 2002-11-13 Novel benzophenone derivatives or salts thereof
US10/493,223 US7772285B2 (en) 2001-11-16 2002-11-13 Benzophenone derivatives or salts thereof
MXPA04004654A MXPA04004654A (es) 2001-11-16 2002-11-13 Novedosos derivados de benzofenona o sus sales.
EP02781763A EP1445249B1 (en) 2001-11-16 2002-11-13 Novel bensophenone derivatives or salts thereof
IL16173602A IL161736A0 (en) 2001-11-16 2002-11-13 Novel benzophenone derivatives or salts thereof
ROA200400442A RO123430B1 (ro) 2001-11-16 2002-11-13 Derivaţi noi de benzofenonă sau sărurile acestora
CN028248120A CN1602291B (zh) 2001-11-16 2002-11-13 新二苯甲酮衍生物或其盐
DK02781763.4T DK1445249T3 (da) 2001-11-16 2002-11-13 Nye bensophenon-derivater eller salte deraf
ES02781763T ES2394963T3 (es) 2001-11-16 2002-11-13 Nuevos derivados de benzofenona o sales de los mismos
HU0402025A HUP0402025A3 (en) 2001-11-16 2002-11-13 Novel bensophenone derivatives or salts thereof and their use
CA2467261A CA2467261C (en) 2001-11-16 2002-11-13 Novel benzophenone derivatives or salts thereof
IL161736A IL161736A (en) 2001-11-16 2004-05-03 Benzophenone derivatives or salts thereof
ZA2004/03373A ZA200403373B (en) 2001-11-16 2004-05-04 Novel benzophenone derivatives or salts thereof
NO20042495A NO329094B1 (no) 2001-11-16 2004-06-15 Bensofenonderivater eller salter derav samt forebyggende eller terapeutisk middel inneholdende slike

Applications Claiming Priority (4)

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JP2001-351217 2001-11-16
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WO2007097279A1 (ja) * 2006-02-21 2007-08-30 Toyama Chemical Co., Ltd. ３－｛５－［４－（シクロペンチルオキシ）－２－ヒドロキシベンゾイル］－２－［（３－オキソ－２－置換－２，３－ジヒドロ－１，２－ベンズイソオキサゾール－６－イル）メトキシ］フェニル｝プロピオン酸エステルの製造法およびその中間体
WO2007138996A1 (ja) 2006-05-26 2007-12-06 Toyama Chemical Co., Ltd. ３－｛５－［４－（シクロペンチルオキシ）－２－ヒドロキシベンゾイル］－２－［（３－ヒドロキシ－１，２－ベンズイソオキサゾール－６－イル）メトキシ］フェニル｝プロピオン酸の新規な結晶
WO2007138997A1 (ja) 2006-05-26 2007-12-06 Toyama Chemical Co., Ltd. ３－｛５－［４－（シクロペンチルオキシ）－２－ヒドロキシベンゾイル］－２－［（３－ヒドロキシ－１，２－ベンズイソオキサゾール－６－イル）メトキシ］フェニル｝プロピオン酸またはその塩を含有する経口用組成物
WO2009040952A1 (ja) * 2007-09-28 2009-04-02 Toyama Chemical Co., Ltd. ベンゾフェノン誘導体またはその塩を含有する薬剤
WO2009069643A1 (ja) * 2007-11-27 2009-06-04 Toyama Chemical Co., Ltd. ３－｛５－［４－（シクロペンチルオキシ）－２－ヒドロキシベンゾイル］－２－［（３－ヒドロキシ－１，２－ベンズイソオキサゾール－６－イル）メトキシ］フェニル｝プロピオン酸またはその塩を含有する固体分散体またはその組成物
WO2009119652A1 (ja) 2008-03-27 2009-10-01 富山化学工業株式会社 ベンゾフェノン誘導体またはその塩およびＴＮＦα阻害剤を組み合わせて使用する方法ならびにこれらを含有する医薬組成物
WO2009131098A1 (ja) 2008-04-22 2009-10-29 富山化学工業株式会社 ベンゾフェノン誘導体またはその塩および免疫抑制剤を組み合わせて使用する方法ならびにこれらを含有する医薬組成物
EP2468743A1 (en) 2005-06-24 2012-06-27 Toyama Chemical Co., Ltd. Nitrogen-containing bicyclic compounds useful as antibacterial agents
AU2012200254B2 (en) * 2006-02-21 2012-08-30 Toyama Chemical Co., Ltd. Process for the production of 3-[5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-oxo-2-substituted-2,3-dihydro- 1,2-benzisoxazol-6-yl)methoxy]phenyl]propionate ester and intermediate for the process
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WO2014157623A1 (ja) * 2013-03-29 2014-10-02 富山化学工業株式会社 ベンゾフェノン誘導体またはその塩を含有する肺高血圧症治療薬

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CN103183647B (zh) * 2011-12-28 2017-06-09 天津市国际生物医药联合研究院有限公司 3‑{[2‑[3‑氧‑(1,2‑苯并异噻唑‑6‑基)甲氧基‑5‑(2‑羟基‑4‑环戊氧基苯甲酰基)]苯基}丙酸的制备方法
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JP2006008675A (ja) * 2004-05-27 2006-01-12 Nippon Nohyaku Co Ltd 置換ピラジンカルボン酸アニリド誘導体又はその塩類、その中間体及び農園芸用薬剤並びにその使用方法
WO2005115994A1 (ja) * 2004-05-27 2005-12-08 Nihon Nohyaku Co., Ltd. 置換ピラジンカルボン酸アニリド誘導体又はその塩類、その中間体及び農園芸用薬剤並びにその使用方法
EP2468743A1 (en) 2005-06-24 2012-06-27 Toyama Chemical Co., Ltd. Nitrogen-containing bicyclic compounds useful as antibacterial agents
CN102285931A (zh) * 2006-02-21 2011-12-21 富山化学工业株式会社 3-[5-[4-（环戊氧基）-2-羟基苯甲酰基]-2-[（3-氧代-2-取代的-2,3-二氢-1,2-苯并异噁唑-6-基）甲氧基]苯基]丙酸酯的制备方法和用于该方法的中间体
WO2007097279A1 (ja) * 2006-02-21 2007-08-30 Toyama Chemical Co., Ltd. ３－｛５－［４－（シクロペンチルオキシ）－２－ヒドロキシベンゾイル］－２－［（３－オキソ－２－置換－２，３－ジヒドロ－１，２－ベンズイソオキサゾール－６－イル）メトキシ］フェニル｝プロピオン酸エステルの製造法およびその中間体
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JP5236456B2 (ja) * 2006-02-21 2013-07-17 富山化学工業株式会社 ３−｛５−［４−（シクロペンチルオキシ）−２−ヒドロキシベンゾイル］−２−［（３−オキソ−２−置換−２，３−ジヒドロ−１，２−ベンズイソオキサゾール−６−イル）メトキシ］フェニル｝プロピオン酸エステルの製造法およびその中間体
EP2562170A1 (en) 2006-02-21 2013-02-27 Toyama Chemical Co., Ltd. Process for production of 3-[5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-oxo-2-substituted-2,3-dihydro-1,2-benzisoxazol-6-yl)methoxy]phenyl]propionate ester and intermediate for the process
AU2012200254B2 (en) * 2006-02-21 2012-08-30 Toyama Chemical Co., Ltd. Process for the production of 3-[5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-oxo-2-substituted-2,3-dihydro- 1,2-benzisoxazol-6-yl)methoxy]phenyl]propionate ester and intermediate for the process
US8153816B2 (en) 2006-02-21 2012-04-10 Toyama Chemical Co., Ltd. Process for production of 3-[5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-OXO-2-substituted-2,3-dihydro-1,2-benzisoxazol-6-yl)methoxy]phenyl]propionate ester and intermediate for the process
US8017789B2 (en) 2006-02-21 2011-09-13 Toyama Chemical Co., Ltd. Process for production of 3-[5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-OXO-2-substituted-2,3-dihydro-1,2-benzisoxazol-6-yl]methoxy]phenyl]proprionate ester and intermediate for the process
KR101389038B1 (ko) * 2006-05-26 2014-04-28 토야마 케미칼 컴퍼니 리미티드 3-｛5-[4-(시클로펜틸옥시)-2-하이드록시벤조일]-2-[(3-하이드록시-1,2-벤즈이소옥사졸-6-일)메톡시]페닐｝프로피온산의 신규의 결정
WO2007138997A1 (ja) 2006-05-26 2007-12-06 Toyama Chemical Co., Ltd. ３－｛５－［４－（シクロペンチルオキシ）－２－ヒドロキシベンゾイル］－２－［（３－ヒドロキシ－１，２－ベンズイソオキサゾール－６－イル）メトキシ］フェニル｝プロピオン酸またはその塩を含有する経口用組成物
US7977492B2 (en) 2006-05-26 2011-07-12 Toyama Chemical Co., Ltd. Crystal of 3-[5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-hydroxy-1,2-benzisoxazol-6-yl)methoxy]phenyl]propionic acid
WO2007138996A1 (ja) 2006-05-26 2007-12-06 Toyama Chemical Co., Ltd. ３－｛５－［４－（シクロペンチルオキシ）－２－ヒドロキシベンゾイル］－２－［（３－ヒドロキシ－１，２－ベンズイソオキサゾール－６－イル）メトキシ］フェニル｝プロピオン酸の新規な結晶
JP5117381B2 (ja) * 2006-05-26 2013-01-16 富山化学工業株式会社 ３−｛５−［４−（シクロペンチルオキシ）−２−ヒドロキシベンゾイル］−２−［（３−ヒドロキシ−１，２−ベンズイソオキサゾール−６−イル）メトキシ］フェニル｝プロピオン酸の新規な結晶
US8093289B2 (en) 2006-05-26 2012-01-10 Toyama Chemical Co., Ltd. Oral composition comprising 3-[5-[4-(cyclopentyloxy)-2-hydroxybenzoyl]-2-[(3-hydroxy-1,2-benzisoxazol-6-yl)methoxy]phenyl]propionic acid or salt thereof
JP5161077B2 (ja) * 2006-05-26 2013-03-13 富山化学工業株式会社 ３−｛５−［４−（シクロペンチルオキシ）−２−ヒドロキシベンゾイル］−２−［（３−ヒドロキシ−１，２−ベンズイソオキサゾール−６−イル）メトキシ］フェニル｝プロピオン酸またはその塩を含有する経口用組成物
US9012482B2 (en) 2007-09-28 2015-04-21 Toyama Chemical Co., Ltd. Drug containing benzophenone derivative or its salt
WO2009040952A1 (ja) * 2007-09-28 2009-04-02 Toyama Chemical Co., Ltd. ベンゾフェノン誘導体またはその塩を含有する薬剤
WO2009069643A1 (ja) * 2007-11-27 2009-06-04 Toyama Chemical Co., Ltd. ３－｛５－［４－（シクロペンチルオキシ）－２－ヒドロキシベンゾイル］－２－［（３－ヒドロキシ－１，２－ベンズイソオキサゾール－６－イル）メトキシ］フェニル｝プロピオン酸またはその塩を含有する固体分散体またはその組成物
JP5615554B2 (ja) * 2007-11-27 2014-10-29 富山化学工業株式会社 ３−｛５−［４−（シクロペンチルオキシ）−２−ヒドロキシベンゾイル］−２−［（３−ヒドロキシ−１，２−ベンズイソオキサゾール−６−イル）メトキシ］フェニル｝プロピオン酸またはその塩を含有する固体分散体の組成物
WO2009119652A1 (ja) 2008-03-27 2009-10-01 富山化学工業株式会社 ベンゾフェノン誘導体またはその塩およびＴＮＦα阻害剤を組み合わせて使用する方法ならびにこれらを含有する医薬組成物
JP5512510B2 (ja) * 2008-03-27 2014-06-04 富山化学工業株式会社 ベンゾフェノン誘導体またはその塩およびＴＮＦα阻害剤を組み合わせて使用する方法ならびにこれらを含有する医薬組成物
RU2522272C2 (ru) * 2008-03-27 2014-07-10 Тояма Кемикал Ко., Лтд. ПРИМЕНЕНИЕ БЕНЗОФЕНОНОВОГО ПРОИЗВОДНОГО ИЛИ ЕГО СОЛИ И ИНГИБИТОРА TNF-α В КОМБИНАЦИИ, И ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, СОДЕРЖАЩАЯ ДАННОЕ ПРОИЗВОДНОЕ ИЛИ ЕГО СОЛЬ И ИНГИБИТОР
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US9066977B2 (en) 2008-04-22 2015-06-30 Toyama Chemical Co., Ltd. Method of utilization of combination of benzophenone derivative or salt thereof and immunosuppressing agent, and pharmaceutical composition comprising these components
JP5512511B2 (ja) * 2008-04-22 2014-06-04 富山化学工業株式会社 ベンゾフェノン誘導体またはその塩および免疫抑制剤を組み合わせて使用する方法ならびにこれらを含有する医薬組成物
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JP2014166984A (ja) * 2008-04-22 2014-09-11 Toyama Chem Co Ltd ベンゾフェノン誘導体またはその塩および免疫抑制剤を組み合わせて使用する方法ならびにこれらを含有する医薬組成物
US8772293B2 (en) 2010-07-09 2014-07-08 Pfizer Limited Chemical compounds
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US8685977B2 (en) 2010-07-12 2014-04-01 Pfizer Limited Chemical compounds
WO2014157623A1 (ja) * 2013-03-29 2014-10-02 富山化学工業株式会社 ベンゾフェノン誘導体またはその塩を含有する肺高血圧症治療薬
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CN1602291A (zh) 2005-03-30
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AU2002349777B2 (en) 2007-12-20
EP1445249B1 (en) 2012-11-07
PT1445249E (pt) 2013-01-16
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HUP0402025A2 (hu) 2005-02-28
US7772285B2 (en) 2010-08-10
ZA200403373B (en) 2006-01-25
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PL206100B1 (pl) 2010-06-30
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PL370224A1 (en) 2005-05-16
CY1113657T1 (el) 2016-06-22
KR100947253B1 (ko) 2010-03-11
EP1445249A1 (en) 2004-08-11
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