JP4966659B2 - 異なる細胞に機能的に影響を及ぼし、免疫性疾患、炎症性疾患、神経疾患、およびその他の疾患を治療するための二重のアラニルアミノペプチダーゼおよびジペプチジルペプチダーゼivの阻害剤 - Google Patents
異なる細胞に機能的に影響を及ぼし、免疫性疾患、炎症性疾患、神経疾患、およびその他の疾患を治療するための二重のアラニルアミノペプチダーゼおよびジペプチジルペプチダーゼivの阻害剤 Download PDFInfo
- Publication number
- JP4966659B2 JP4966659B2 JP2006534707A JP2006534707A JP4966659B2 JP 4966659 B2 JP4966659 B2 JP 4966659B2 JP 2006534707 A JP2006534707 A JP 2006534707A JP 2006534707 A JP2006534707 A JP 2006534707A JP 4966659 B2 JP4966659 B2 JP 4966659B2
- Authority
- JP
- Japan
- Prior art keywords
- unsubstituted
- substituted
- diseases
- disease
- compound
- 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.)
- Expired - Fee Related
Links
- NSMUCVGGQFSZFU-UHFFFAOYSA-N Cc1c(C(c2ccc[s]2)N2CCCCC2)c2ccccc2[nH]1 Chemical compound Cc1c(C(c2ccc[s]2)N2CCCCC2)c2ccccc2[nH]1 NSMUCVGGQFSZFU-UHFFFAOYSA-N 0.000 description 2
- LALOBMVQHNZYAW-HEHNFIMWSA-N C/C(/N)=C(\C(c(cc1)ccc1OC)N1CCCC1)/c1ccccc1C Chemical compound C/C(/N)=C(\C(c(cc1)ccc1OC)N1CCCC1)/c1ccccc1C LALOBMVQHNZYAW-HEHNFIMWSA-N 0.000 description 1
- ZRDDBXWEPWIZHF-UHFFFAOYSA-N CC(C1)C(OC)=CC=C1C(c1c(C)[nH]c2ccccc12)N1CCCC1 Chemical compound CC(C1)C(OC)=CC=C1C(c1c(C)[nH]c2ccccc12)N1CCCC1 ZRDDBXWEPWIZHF-UHFFFAOYSA-N 0.000 description 1
- RGCOGHQLHYSEEJ-UHFFFAOYSA-N Cc1c(C(C2=NC=CCC2)N2CCCC2)c2ccccc2[nH]1 Chemical compound Cc1c(C(C2=NC=CCC2)N2CCCC2)c2ccccc2[nH]1 RGCOGHQLHYSEEJ-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C327/00—Thiocarboxylic acids
- C07C327/38—Amides of thiocarboxylic acids
- C07C327/48—Amides of thiocarboxylic acids having carbon atoms of thiocarboxamide groups bound to carbon atoms of six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/02—Antidotes
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/83—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Description
ジペプチジルペプチダーゼIVおよびアラニルアミノペプチダーゼの新規な二重阻害剤の阻害特性
実験的自己免疫性脳脊髄炎(EAE)マウス(多発性硬化症の動物モデル)に対するアラニルアミノペプチダーゼおよび類似の効果を有する酵素、ならびにジペプチジルペプチダーゼIVおよび類似の効果を有する酵素の阻害を組み合わせた治療効果
デキストラン硫酸塩誘発大腸炎マウス(慢性炎症性腸疾患の動物モデル)に対する、アラニルアミノペプチダーゼおよび類似の効果を有する酵素の阻害、ならびにジペプチジルペプチダーゼIVおよび類似の効果を有する酵素の阻害の組み合わせによる治療効果
オボアルブミン誘発気管支喘息マウス(ヒトの気管支喘息の動物モデル)におけるアラニルアミノペプチダーゼおよび類似の効果を有する酵素、ならびにジペプチジルペプチダーゼIVおよび類似の効果を有する酵素の阻害を組み合わせた治療効果。図3は、肺機能の尺度としての平均呼気流速(EF50)の減少についてのペプチダーゼ阻害を組み合わせた影響(図3A)、および気管支喘息による肺の炎症の特徴としての好酸球増加についてのペプチダーゼ阻害を組み合わせた影響(図3B)を示す。
Claims (18)
- アラニルアミノペプチダーゼおよびジペプチジルペプチダーゼIVの活性を阻害するための、一般式(C4)の少なくとも1つの化合物を含む医薬品または化粧料組成物:
Y1、Y2、およびY3は同一または異なり得、置換されたまたは非置換の炭素原子ユニットまたは環原子N、O、P、またはSを有するヘテロ原子ユニットを表し;
R1およびR2は各部分環の置換パターンを表し、該R1は1〜4個の同一または異なる置換基を表し、該R2は1〜6個の同一または異なる置換基を表し、該置換基およびR3は水素、非置換または置換された直鎖または分岐のC1−C12アルキル、C2−C12アルケニルおよびC2−C12アルキニル、ヒドロキシ、チオール、C1−C12アルコキシ、C1−C12アルキルチオ、N、O、PおよびSからなる群より選択される1個または数個のヘテロ原子を含んでいてもよい非置換または置換された非縮合または縮合アリールおよびシクロアルキル、非置換または置換されたアミノ、非置換または置換されたカルボニル、非置換または置換されたチオカルボニル、および非置換または置換されたイミノからなる群より選択され;そして
該複素芳香環残基または複素環残基が、該一般式(C4)の基本構造にC原子またはヘテロ原子を介して結合されている)
であって、該化合物が、以下の式:
- 一般式(C4)の少なくとも1つの化合物の使用であって、アラニルアミノペプチダーゼおよびジペプチジルペプチダーゼIVの活性を阻害するための医薬品または化粧料の製造における使用:
Y1、Y2、およびY3は同一または異なり得、置換されたまたは非置換の炭素原子ユニットまたは環原子N、O、P、またはSを有するヘテロ原子ユニットを表し;
R1およびR2は各部分環の置換パターンを表し、該R1は1〜4個の同一または異なる置換基を表し、該R2は1〜6個の同一または異なる置換基を表し、該置換基およびR3は水素、非置換または置換された直鎖または分岐のC1−C12アルキル、C2−C12アルケニルおよびC2−C12アルキニル、ヒドロキシ、チオール、C1−C12アルコキシ、C1−C12アルキルチオ、N、O、PおよびSからなる群より選択される1個または数個のヘテロ原子を含んでいてもよい非置換または置換された非縮合または縮合アリールおよびシクロアルキル、非置換または置換されたアミノ、非置換または置換されたカルボニル、非置換または置換されたチオカルボニル、および非置換または置換されたイミノからなる群より選択され;そして
該複素芳香環残基または複素環残基が、該一般式(C4)の基本構造にC原子またはヘテロ原子を介して結合されている)
であって、該化合物が、以下の式:
- アラニルアミノペプチダーゼおよびジペプチジルペプチダーゼIVの活性を局所的に阻害するための請求項2に記載の使用。
- 多発性硬化症、クローン病、潰瘍性大腸炎、関節リウマチ、I型糖尿病、自己免疫性甲状腺疾患、ウェゲナー病、内臓の全身エリテマトーデス、またはその他の自己免疫性疾患、ならびに炎症性疾患を予防または治療するための請求項2に記載の使用。
- アレルギー性気管支喘息、アレルギー性鼻炎、食品アレルギー、アトピー性湿疹、接触性皮膚炎、じんま疹、血管浮腫、またはその他のアレルギー性疾患を予防または治療するための請求項2に記載の使用。
- 腎臓、心臓、肝臓、膵臓、皮膚、または幹細胞移植片のような同種または異種の移植された器官、組織、または細胞の拒絶反応、ならびに移植片対宿主疾患を予防または治療するための請求項2に記載の使用。
- 皮膚病および粘膜症、乾癬、ざ瘡、ならびに線維芽細胞の異常増殖または変異した分化状態に関連する皮膚病を予防または治療するための請求項2に記載の使用。
- 急性神経疾患、虚血性または出血性脳卒中後の虚血に起因する脳障害、頭部外傷、心停止、心筋梗塞、または心臓手術後の心筋梗塞を予防または治療するための請求項2に記載の使用。
- 慢性神経疾患、アルツハイマー病、ピック病、進行性核上性麻痺、大脳皮質基底核変性症、前頭側頭型痴呆、パーキンソン病、ハンチントン病、プリオンによって引き起こされる疾患、または筋萎縮性側索硬化症を予防または治療するための請求項2に記載の使用。
- アテローム性動脈硬化症、動脈の炎症、再潅流症候群、またはステント再狭窄を予防または治療するための請求項2に記載の使用。
- 植え込まれた医療デバイスにおける炎症反応、または植え込まれた医療デバイスに起因する炎症反応を予防または治療するための請求項2に記載の使用。
- 請求項11に記載の使用であって、デバイス上におけるコーティングまたは層の形態、または少なくとも1つの化合物または組成物の材料混合物のデバイス材料への付与の形態で;あるいは局所投与または全身投与の形態での使用。
- 慢性閉塞性肺疾患を予防または治療するための請求項2に記載の使用。
- 前立腺ガンまたはその他の腫瘍ならびに転移を予防または治療するための請求項2に記載の使用。
- 重症急性呼吸器症候群を予防または治療するための請求項2に記載の使用。
- 敗血症または敗血症様の状態を予防または治療するための請求項2に記載の使用。
- ペプチダーゼの活性を阻害するための阻害剤であって、該阻害剤が少なくとも1つの化合物を含み、該化合物が一般式(C4):
Y1、Y2、およびY3は同一または異なり得、置換されたまたは非置換の炭素原子ユニットまたは環原子N、O、P、またはSを有するヘテロ原子ユニットを表し;
R1およびR2は各部分環の置換パターンを表し、該R1は1〜4個の同一または異なる置換基を表し、該R2は1〜6個の同一または異なる置換基を表し、該置換基およびR3は水素、非置換または置換された直鎖または分岐のC1−C12アルキル、C2−C12アルケニルおよびC2−C12アルキニル、ヒドロキシ、チオール、C1−C12アルコキシ、C1−C12アルキルチオ、N、O、PおよびSからなる群より選択される1個または数個のヘテロ原子を含んでいてもよい非置換または置換された非縮合または縮合アリールおよびシクロアルキル、非置換または置換されたアミノ、非置換または置換されたカルボニル、非置換または置換されたチオカルボニル、および非置換または置換されたイミノからなる群より選択され;そして
該複素芳香環残基または複素環残基が、該一般式(C4)の基本構造にC原子またはヘテロ原子を介して結合されている)
を有し、該化合物が、以下の式:
- アラニルアミノペプチダーゼおよびジペプチジルペプチダーゼIVの活性を阻害するための、請求項17に記載の阻害剤。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10348044A DE10348044A1 (de) | 2003-10-15 | 2003-10-15 | Duale Alanyl-Aminopeptidase- und Dipeptidylpeptidase IV-Inhibitoren zur funktionellen Beeinflussung unterschiedlicher Zellen und zur Behandlung immunologischer, entzündlicher, neuronaler und anderer Erkrankungen |
DE10348044.7 | 2003-10-15 | ||
PCT/EP2004/011644 WO2005034940A2 (de) | 2003-10-15 | 2004-10-15 | Duale alanyl-aminopeptidase- und dipeptidylpeptidase iv-inhibitoren zur funktionellen beeinflussung unterschiedlicher zellen und zur behandlung immunologischer, entzündlicher, neuronaler und anderer erkrankungen |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007508350A JP2007508350A (ja) | 2007-04-05 |
JP4966659B2 true JP4966659B2 (ja) | 2012-07-04 |
Family
ID=34428431
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006534707A Expired - Fee Related JP4966659B2 (ja) | 2003-10-15 | 2004-10-15 | 異なる細胞に機能的に影響を及ぼし、免疫性疾患、炎症性疾患、神経疾患、およびその他の疾患を治療するための二重のアラニルアミノペプチダーゼおよびジペプチジルペプチダーゼivの阻害剤 |
Country Status (8)
Country | Link |
---|---|
US (1) | US8263636B2 (ja) |
EP (2) | EP1673082A2 (ja) |
JP (1) | JP4966659B2 (ja) |
CN (1) | CN1882332A (ja) |
AU (1) | AU2004280090B2 (ja) |
CA (1) | CA2542592A1 (ja) |
DE (1) | DE10348044A1 (ja) |
WO (1) | WO2005034940A2 (ja) |
Families Citing this family (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2004094409A1 (en) * | 2003-03-27 | 2004-11-04 | Lankenau Institute For Medical Research | Novel ido inhibitors and methods of use |
DE10348022A1 (de) * | 2003-10-15 | 2005-05-25 | Imtm Gmbh | Neue Dipeptidylpeptidase IV-Inhibitoren zur funktionellen Beeinflussung unterschiedlicher Zellen und zur Behandlung immunologischer, entzündlicher, neuronaler und anderer Erkrankungen |
DOP2006000008A (es) | 2005-01-10 | 2006-08-31 | Arena Pharm Inc | Terapia combinada para el tratamiento de la diabetes y afecciones relacionadas y para el tratamiento de afecciones que mejoran mediante un incremento de la concentración sanguínea de glp-1 |
DE102005054700B4 (de) * | 2005-11-16 | 2009-01-08 | Imtm Gmbh | Neue duale Peptidase-Inhibitoren als Prodrugs zur Therapie von entzündlichen und anderen Erkrankungen |
PE20071221A1 (es) | 2006-04-11 | 2007-12-14 | Arena Pharm Inc | Agonistas del receptor gpr119 en metodos para aumentar la masa osea y para tratar la osteoporosis y otras afecciones caracterizadas por masa osea baja, y la terapia combinada relacionada a estos agonistas |
US8962677B2 (en) | 2007-07-12 | 2015-02-24 | Acumen Pharmaceuticals, Inc. | Methods of restoring cognitive ability using non-peptidic compounds |
WO2009009768A2 (en) * | 2007-07-12 | 2009-01-15 | Acumen Pharmaceuticals, Inc. | METHODS OF INHIBITING THE FORMATION OF AMYLOID-β DIFFUSABLE LIGANDS USING A ACYLHYDRAZIDE COMPOUDS |
US9006283B2 (en) | 2007-07-12 | 2015-04-14 | Acumen Pharmaceuticals, Inc. | Methods of modifying amyloid β oligomers using non-peptidic compounds |
DE102007039429A1 (de) * | 2007-08-21 | 2009-02-26 | Imtm Gmbh | Verfahren zur Aktivierung regulatorischer T-Zellen |
CA2707309A1 (en) | 2007-12-18 | 2009-06-25 | Acumen Pharmaceuticals, Inc. | Novel addl receptor polypeptides, polynucleotides and host cells for recombinant production |
KR20100118991A (ko) * | 2008-02-04 | 2010-11-08 | 아이데닉스 파마슈티칼스, 인코포레이티드 | 매크로시클릭 세린 프로테아제 억제제 |
EP2108960A1 (en) | 2008-04-07 | 2009-10-14 | Arena Pharmaceuticals, Inc. | Methods of using A G protein-coupled receptor to identify peptide YY (PYY) secretagogues and compounds useful in the treatment of conditons modulated by PYY |
US8377962B2 (en) | 2009-04-08 | 2013-02-19 | Idenix Pharmaceuticals, Inc. | Macrocyclic serine protease inhibitors |
AR077642A1 (es) | 2009-07-09 | 2011-09-14 | Arena Pharm Inc | Moduladores del metabolismo y el tratamiento de trastornos relacionados con el mismo |
TW201117812A (en) | 2009-08-05 | 2011-06-01 | Idenix Pharmaceuticals Inc | Macrocyclic serine protease inhibitors |
WO2011127192A2 (en) * | 2010-04-06 | 2011-10-13 | Brigham Young University | Antimetastatic compounds |
BR112012025592A2 (pt) | 2010-04-06 | 2019-09-24 | Arena Pharm Inc | moduladores do receptor de gpr119 e o tratamento de distúrbios relacionados com os mesmos |
EP2418196A1 (en) * | 2010-07-29 | 2012-02-15 | IMTM GmbH | Dual alanyl-aminopeptidase and dipeptidyl-peptidase IV inhibitors |
PE20131371A1 (es) | 2010-09-22 | 2013-11-25 | Arena Pharm Inc | Moduladores del receptor gpr119 y el tratamiento de trastornos relacionados con este |
US9353100B2 (en) | 2011-02-10 | 2016-05-31 | Idenix Pharmaceuticals Llc | Macrocyclic serine protease inhibitors, pharmaceutical compositions thereof, and their use for treating HCV infections |
WO2012135570A1 (en) | 2011-04-01 | 2012-10-04 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
WO2012145361A1 (en) | 2011-04-19 | 2012-10-26 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
WO2012145603A1 (en) | 2011-04-22 | 2012-10-26 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
WO2012145604A1 (en) | 2011-04-22 | 2012-10-26 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
WO2012170702A1 (en) | 2011-06-08 | 2012-12-13 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
WO2013055910A1 (en) | 2011-10-12 | 2013-04-18 | Arena Pharmaceuticals, Inc. | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
MX356509B (es) | 2011-12-22 | 2018-05-30 | Alios Biopharma Inc | Nucleósidos sustituidos, nucleótidos y análogos de los mismos. |
USRE48171E1 (en) | 2012-03-21 | 2020-08-25 | Janssen Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
US9441007B2 (en) | 2012-03-21 | 2016-09-13 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
WO2014074668A1 (en) | 2012-11-08 | 2014-05-15 | Arena Pharmaceuticals, Inc. | Modulators of gpr119 and the treatment of disorders related thereto |
CN103864653A (zh) * | 2012-12-10 | 2014-06-18 | 韩冰 | 一类降低眼压的化合物及其用途 |
CN103864797A (zh) * | 2012-12-10 | 2014-06-18 | 韩冰 | 一类具有神经保护作用的化合物及其用途 |
RU2644769C2 (ru) | 2013-01-23 | 2018-02-14 | Астразенека Аб | Химические соединения |
US8906951B1 (en) | 2013-06-24 | 2014-12-09 | Tigercat Pharma, Inc. | Use of NK-1 receptor antagonists in pruritus |
US9198898B2 (en) | 2013-06-24 | 2015-12-01 | Tigercat Pharma, Inc. | Use of NK-1 receptor antagonists in pruritus |
WO2016144862A1 (en) | 2015-03-09 | 2016-09-15 | Intekrin Therapeutics, Inc. | Methods for the treatment of nonalcoholic fatty liver disease and/or lipodystrophy |
EP3804706B1 (en) * | 2015-05-29 | 2023-08-23 | Emory University | 2-amino-n'-benzylideneacetohydrazides and derivatives for the management of cftr protein mediated diseases |
WO2016196303A1 (en) | 2015-05-29 | 2016-12-08 | Emory University | 3-(phenyl)-n-(4-phenoxybenzyl)-1,2,4-oxadiazole-5-carboxamide compounds for the management of cftr protein mediated diseases |
AU2016288230A1 (en) | 2015-07-02 | 2018-01-25 | Horizon Orphan Llc | ADO-resistant cysteamine analogs and uses thereof |
EP3606527A1 (en) | 2017-04-03 | 2020-02-12 | Coherus Biosciences, Inc. | Ppar-gamma agonist for treatment of progressive supranuclear palsy |
GB201706162D0 (en) * | 2017-04-19 | 2017-05-31 | Nat Univ Singapore | Compounds |
Family Cites Families (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD296075A5 (de) | 1989-08-07 | 1991-11-21 | Martin-Luther-Universitaet Halle-Wittenberg,De | Verfahren zur herstellung neuer inhibitoren der dipeptidyl peptidase iv |
US6090250A (en) * | 1993-09-20 | 2000-07-18 | Waters Investments Limited | Chiral surfactants and methods for their use in chiral separations |
US5484940A (en) * | 1994-11-28 | 1996-01-16 | Grant; Francine S. | Substituted 3-indolyl-5-pyrazolone compounds |
US6429212B1 (en) * | 1996-08-16 | 2002-08-06 | Ishihara Sangyo Kaisha Ltd. | Medicinal composition |
US6410584B1 (en) * | 1998-01-14 | 2002-06-25 | Cell Pathways, Inc. | Method for inhibiting neoplastic cells with indole derivatives |
DE10025464A1 (de) | 2000-05-23 | 2001-12-06 | Inst Medizintechnologie Magdeb | Kombinierte Verwendung von Enzyminhibitoren zur Therapie von Autoimmunerkrankungen, bei Transplantationen und Tumorerkrankungen sowie Kombinationen von Enzyminhibitoren umfassende pharmazeutische Zubereitungen |
US7229969B2 (en) | 2001-01-02 | 2007-06-12 | Imtm Gmbh | Combinations of enzyme inhibitors and the use thereof |
DE10155093A1 (de) | 2001-11-09 | 2003-06-12 | Inst Medizintechnologie Magdeb | Kombinierte Verwendung der Inhibitoren von Enzymen mit Aktivitäten der Aminopeptidase N und der Dipeptidylpeptidase IV und pharmazeutischen Zubereitungen daraus zur Therapie und Prävention dermatologischer Erkrankungen mit follikulären und epidermalen Hyperkeratosen und einer verstärkten Keratinozytenproliferation |
DE10100053A1 (de) | 2001-01-02 | 2002-08-22 | Keyneurotek Ag I G | Verwendung von Enzyminhibitoren der Dipeptidylpeptidase IV sowie der Aminopeptidase N und pharmazeutischen Zubereitungen daraus zur Prävention und/oder Therapie Ischämie-bedingter akuter und chronischer neurodegenerativer Prozesse und Erkrankungen |
KR100883277B1 (ko) | 2001-02-24 | 2009-02-12 | 베링거 잉겔하임 파르마 게엠베하 운트 코 카게 | 크산틴 유도체 및 이의 제조방법 |
US7253172B2 (en) * | 2001-06-20 | 2007-08-07 | Merck & Co., Inc. | Dipeptidyl peptidase inhibitors for the treatment of diabetes |
WO2003024899A2 (en) * | 2001-09-17 | 2003-03-27 | Bristol-Myers Squibb Company | CYCLIC HYDROXAMIC ACIDS AS INHIBITORS OF MATRIX METALLOPROTEINASES AND/OR TNF-α CONVERTING ENZYME (TACE) |
GB0125446D0 (en) | 2001-10-23 | 2001-12-12 | Ferring Bv | Novel anti-diabetic agents |
EP2316470A3 (en) | 2001-11-26 | 2011-08-24 | Trustees Of Tufts College | Peptidomimetic inhibitors of post-proline cleaving enzymes |
DE10211555A1 (de) | 2002-03-15 | 2003-10-02 | Imtm Inst Fuer Medizintechnolo | Verwendung der Inhibitoren von Enzymen mit Aktivitäten der Aminopeptidase N und/oder der Dipeptidylpeptidase IV und pharmazeutischen Zubereitungen daraus zur Therapie und Prävention dermatologischer Erkrankungen mit sebozytärer Hyperproliferation und veränderten Differenzierungszuständen |
DE10230381A1 (de) | 2002-07-05 | 2004-01-22 | Institut für Medizintechnologie Magdeburg GmbH, IMTM | Verwendung von Inhibitoren der Alanyl-Aminopeptidasen und diese umfassende pharmazeutischen Zubereitungen |
DE10251927A1 (de) | 2002-11-08 | 2004-05-19 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Xanthinderivate, deren Herstellung und deren Verwendung als Arzneimittel |
US7482337B2 (en) | 2002-11-08 | 2009-01-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Xanthine derivatives, the preparation thereof and their use as pharmaceutical compositions |
US6830706B2 (en) * | 2002-11-21 | 2004-12-14 | Matsushita Electric Industrial Co., Ltd. | Stable blue phosphor for plasma display panel applications |
WO2004094409A1 (en) | 2003-03-27 | 2004-11-04 | Lankenau Institute For Medical Research | Novel ido inhibitors and methods of use |
DE10330842A1 (de) | 2003-07-08 | 2005-02-10 | Institut für Medizintechnologie Magdeburg GmbH, IMTM | Verwendung der Inhibitoren von Enzymen mit Aktivitäten der Aminopeptidase N und/oder der Dipeptidylpeptidase IV und pharmazeutischen Zubereitungen daraus zur Therapie und Prävention dermatologischer Erkrankungen mit Hyperproliferation und veränderten Differenzierungszuständen von Fibroblasten |
DE10337074A1 (de) | 2003-08-12 | 2005-03-17 | Keyneurotek Ag | Verwendung der Inhibitoren von Enzymen mit Aktivitäten der Aminopeptidase N und/oder der Dipeptidylpeptidase IV und pharmazeutischen Zubereitungen daraus zur Therapie und Prävention von chronischen neurodegenerativen Erkrankungen |
-
2003
- 2003-10-15 DE DE10348044A patent/DE10348044A1/de not_active Withdrawn
-
2004
- 2004-10-15 JP JP2006534707A patent/JP4966659B2/ja not_active Expired - Fee Related
- 2004-10-15 CN CNA2004800339000A patent/CN1882332A/zh active Pending
- 2004-10-15 EP EP04790486A patent/EP1673082A2/de not_active Withdrawn
- 2004-10-15 WO PCT/EP2004/011644 patent/WO2005034940A2/de active Application Filing
- 2004-10-15 US US10/575,878 patent/US8263636B2/en not_active Expired - Fee Related
- 2004-10-15 AU AU2004280090A patent/AU2004280090B2/en not_active Ceased
- 2004-10-15 EP EP09160132A patent/EP2105441A1/de not_active Withdrawn
- 2004-10-15 CA CA002542592A patent/CA2542592A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
CN1882332A (zh) | 2006-12-20 |
DE10348044A1 (de) | 2005-05-19 |
US20070078130A1 (en) | 2007-04-05 |
AU2004280090A1 (en) | 2005-04-21 |
WO2005034940A3 (de) | 2005-12-08 |
CA2542592A1 (en) | 2005-04-21 |
AU2004280090B2 (en) | 2009-08-13 |
EP2105441A1 (de) | 2009-09-30 |
WO2005034940A8 (de) | 2006-06-01 |
WO2005034940A2 (de) | 2005-04-21 |
US8263636B2 (en) | 2012-09-11 |
EP1673082A2 (de) | 2006-06-28 |
JP2007508350A (ja) | 2007-04-05 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP4966659B2 (ja) | 異なる細胞に機能的に影響を及ぼし、免疫性疾患、炎症性疾患、神経疾患、およびその他の疾患を治療するための二重のアラニルアミノペプチダーゼおよびジペプチジルペプチダーゼivの阻害剤 | |
JP2008500270A (ja) | 異なるタイプの細胞に機能的に影響を及ぼし、免疫性疾患、炎症性疾患、神経疾患、およびその他の疾患を治療するための新規なジペプチジルペプチダーゼiv阻害剤 | |
JP2007508349A (ja) | 異なるタイプの細胞に機能的に影響を及ぼし、免疫性疾患、炎症性疾患、神経疾患、およびその他の疾患を治療するための新規なアラニルアミノペプチダーゼ阻害剤 | |
AU751963B2 (en) | Alpha-ketoamide multicatalytic protease inhibitors | |
JPH08508027A (ja) | 金属タンパク加水分解酵素阻害剤である天然アミノ酸誘導体 | |
PL211429B1 (pl) | Zastosowanie medyczne omega-aminoalkiloamidów kwasów R-2-arylo-propionowych oraz nowa klasa omega -R-2-aminoalkiloamidów kwasów R-2-arylo-propionowych i sposób ich wytwarzania | |
AU2008290827B2 (en) | Method for activating regulatory t-cells | |
US8470855B2 (en) | Dual-use peptidase inhibitors as prodrugs for a therapy of inflammatory and other diseases | |
EP2543660A1 (en) | Prophylactic or therapeutic agent for diabetes or obesity | |
CN1306526A (zh) | 具有半胱氨酸蛋白酶抑制作用的新的杂环取代酰胺 | |
CN1303372A (zh) | 新的杂环取代酰胺、其制备以及应用 | |
US20120028995A1 (en) | Novel compounds for medical use as peptidase effectors | |
TW200407310A (en) | Compounds | |
US20120258960A1 (en) | Novel multifunctional peptidase inhibitors, especially for medical use | |
JPS63310820A (ja) | 5−リポキシゲナーゼ阻害剤としてのフエノール チオアルキルアミド化合物 | |
EP3708563A1 (en) | Selenopsammaplin a and derivative thereof, preparation method therefor, and composition for preventing and treating cancer, containing same as active ingredients | |
Li et al. | Novel potent 2, 5-pyrrolidinedione peptidomimetics as aminopeptidase N inhibitors. Design, synthesis and activity evaluation | |
EP0372409B1 (en) | Acylaminoalkylpyridineamides as inhibitors of tumor metastasis | |
EP0372410A2 (en) | Use of heterocyclic amides to inhibit tumor metastasis | |
KR100520096B1 (ko) | 항산화 활성을 갖는 페닐아미딘 유도체 및 이를 포함하는약학적 조성물 | |
JP2005516062A (ja) | Xa因子活性を阻害する新規化合物 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20091117 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20100216 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20100223 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100309 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20100615 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20100914 |
|
RD02 | Notification of acceptance of power of attorney |
Free format text: JAPANESE INTERMEDIATE CODE: A7422 Effective date: 20100914 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20100916 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20101014 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20101102 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20101104 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20101130 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20110823 |
|
A521 | Written amendment |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20111221 |
|
A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20120110 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20120207 |
|
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20120307 |
|
A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20120314 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20120402 |
|
R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150406 Year of fee payment: 3 |
|
FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20150406 Year of fee payment: 3 |
|
R154 | Certificate of patent or utility model (reissue) |
Free format text: JAPANESE INTERMEDIATE CODE: R154 |
|
LAPS | Cancellation because of no payment of annual fees |