JP4879991B2 - 抗高コレステロール血症化合物 - Google Patents
抗高コレステロール血症化合物 Download PDFInfo
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- JP4879991B2 JP4879991B2 JP2008534613A JP2008534613A JP4879991B2 JP 4879991 B2 JP4879991 B2 JP 4879991B2 JP 2008534613 A JP2008534613 A JP 2008534613A JP 2008534613 A JP2008534613 A JP 2008534613A JP 4879991 B2 JP4879991 B2 JP 4879991B2
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- JP
- Japan
- Prior art keywords
- mmol
- phenyl
- formula
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- compounds
- 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
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- GGOQYHOZFCWTNM-UHFFFAOYSA-N CC(NCC#C)=O Chemical compound CC(NCC#C)=O GGOQYHOZFCWTNM-UHFFFAOYSA-N 0.000 description 1
- NABKXCLVIQJWTD-UHFFFAOYSA-N CN(C)C(NCC#C)=O Chemical compound CN(C)C(NCC#C)=O NABKXCLVIQJWTD-UHFFFAOYSA-N 0.000 description 1
- ARSQCIRDYSOFEN-UHFFFAOYSA-N CS(NCC#C)(=O)=O Chemical compound CS(NCC#C)(=O)=O ARSQCIRDYSOFEN-UHFFFAOYSA-N 0.000 description 1
- WBPMZUSZPMAOEN-CBOMQKSFSA-N CS(NCCCc(cc1)ccc1N([C@@H](C1CC[C@@H](c(cc2)ccc2F)O)c(ccc(CCC(CO)(CO)O)c2)c2O)C1=O)(=O)=O Chemical compound CS(NCCCc(cc1)ccc1N([C@@H](C1CC[C@@H](c(cc2)ccc2F)O)c(ccc(CCC(CO)(CO)O)c2)c2O)C1=O)(=O)=O WBPMZUSZPMAOEN-CBOMQKSFSA-N 0.000 description 1
- TUFWMKGAULHQRU-BRWRJTIESA-M O[C@@H](CCC([C@@H](c(cc1)ccc1O[C@@H]([C@@H]([C@H]([C@@H]1O)O)O)O[C@@H]1C(O)=O)N1[AlH2])C1=O)I Chemical compound O[C@@H](CCC([C@@H](c(cc1)ccc1O[C@@H]([C@@H]([C@H]([C@@H]1O)O)O)O[C@@H]1C(O)=O)N1[AlH2])C1=O)I TUFWMKGAULHQRU-BRWRJTIESA-M 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P9/10—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
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Description
本発明の1つの目的は、式I
本発明の新規なコレステロール吸収阻害剤は、式I
Ar1は、アリール及びR4−置換アリールからなる群から選択され;
X、Y及びZは、独立して、−CH2−、−CH(C1−6アルキル)−及び−C(C1−6アルキル)2−からなる群から選択され;
Rは、−OR6、−O(CO)R6、−O(CO)OR8、−O(CO)NR6R7、糖残基、二糖残基、三糖残基及び四糖残基からなる群から選択され;
R1は、−H、−C1−6アルキル及びアリールからなる群から選択されるか、又はR及びR1が一緒になってオキソとなり;
R2は、−OR6、−O(CO)R6、−O(CO)OR8及び−O(CO)NR6R7からなる群から選択され;
R3は、−H、−C1−6アルキル及びアリールからなる群から選択されるか、又はR2及びR3が一緒になってオキソとなり;
q及びrは、それぞれ独立して0及び1から選択される整数であり、但し、q及びrの少なくとも1つが1であり;
m、n及びpは、それぞれ独立して0、1、2、3及び4から選択される整数であり;但し、m、n、p、q及びrの合計は1、2、3、4、5又は6であり;
tは0、1及び2から選択される整数であり;
R4は、各存在ごとに独立して、−OR5、−O(CO)R5、−O(CO)OR8、−O−C1−5アルキル−OR5、−O(CO)NR5R6、−NR5R6、−NR5(CO)R6、−NR5(CO)OR8、−NR5(CO)NR6R7、−NR5SO2R8、−COOR5、−CONR5R6、−COR5、−SO2NR5R6、−S(O)tR8、−O−C1−10アルキル−COOR5、−O−C1−10アルキル−CONR5R6及びフルオロからなる群から選択される1〜5個の置換基であり;
R5、R6及びR7は、各存在ごとに独立して、−H、−C1−6アルキル、アリール及びアリール置換−C1−6アルキルからなる群から選択され;
R8は、−C1−6アルキル、アリール及びアリール置換−C1−6アルキルからなる群から選択され;
R9は、−C≡C−(CH2)y−NR10R11、−C=C−(CH2)y−NR10R11及び−(CH2)w−NR10R11からなる群から選択され;
wは1、2、3、4、5、6、7及び8から選択される整数であり;
yは1、2、3、4、5及び6から選択される整数であり、
R10は、−H及び−C1−3アルキルからなる群から選択され;
R11は、−H、−C1−3アルキル、−C(O)−C1−3アルキル、−C(O)−NR10R10、−SO2−C1−3アルキル及び−SO2−フェニルからなる群から選択され;
R12は、−OHでモノ−又はポリ置換された−C1−15アルキル、−OHでモノ−又はポリ−置換された−CH=CH−C1−13アルキル、−OHでモノ−又はポリ−置換された−C≡C−C1−13アルキル、及び
からなる群から選択され;
R13は、−H及び−OHからなる群から選択される。)で表される化合物、その薬学的に許容される塩及びエステルである。
本発明の別の実施態様は、構造式Ia
10〜14週齢のC57BL/6のオスマウス(n=6/グループ)に、試験化合物あり又はなし、又はエゼチミベ(0.12〜10mg/kg)を、0.25%メチルセルロース溶液2mLを用いて経口的に投与した。30分後、全てのマウスに、マウスあたり2μCi[3H]コレステロールを含むINTRALIPID(商標)0.2mLを経口的に投与した。5時間後、動物を安楽死させ、肝臓及び血液を集めた。肝臓及び血漿中のコレステロール値を定量し、コレステロール吸収阻害の割合を計算した。
工程A:4−[(2S,3R)−3−[(3S)−3−(アセチルオキシ)−3−(4−フルオロフェニル)プロピル]−1−(4−{3−[(メチルスルホニル)アミノ]プロパ−1−イン−1−イル}フェニル)−4−オキソアゼチジン−2−イル]フェニルアセテート(R 10 が−Hであるi−9)の製造
工程A:4−[(2S,3R)−3−[(3S)−3−(アセチルオキシ)−3−(4−フルオロフェニル)プロピル]−1−(4−{3−[メチル(メチルスルホニル)アミノ]プロパ−1−イン−1−イル}フェニル)−4−オキソアゼチジン−2−イル]フェニルアセテート(R 10 が−CH 3 であるi−9)の製造
工程A:(1S)−3−[(2S,3R)−2−[2,4−ビス(ベンジルオキシ)フェニル]−1−(4−{3−[(メチルスルホニル)アミノ]プロパ−1−イン−1−イル}フェニル)−4−オキソアゼチジン−3−イル]−1−(4−フルオロフェニル)プロピルアセテートの製造
Claims (4)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US72378105P | 2005-10-05 | 2005-10-05 | |
US60/723,781 | 2005-10-05 | ||
PCT/US2006/038551 WO2007044318A2 (en) | 2005-10-05 | 2006-09-29 | Anti-hypercholesterolemic compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2009511475A JP2009511475A (ja) | 2009-03-19 |
JP4879991B2 true JP4879991B2 (ja) | 2012-02-22 |
Family
ID=37845278
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2008534613A Expired - Fee Related JP4879991B2 (ja) | 2005-10-05 | 2006-09-29 | 抗高コレステロール血症化合物 |
Country Status (25)
Country | Link |
---|---|
US (2) | US20090137546A1 (ja) |
EP (1) | EP1934175B1 (ja) |
JP (1) | JP4879991B2 (ja) |
KR (1) | KR20080050610A (ja) |
CN (1) | CN101277930A (ja) |
AR (1) | AR058068A1 (ja) |
AT (1) | ATE488495T1 (ja) |
AU (1) | AU2006302584B2 (ja) |
BR (1) | BRPI0616834A2 (ja) |
CA (1) | CA2624481C (ja) |
CR (1) | CR9903A (ja) |
DE (1) | DE602006018341D1 (ja) |
DO (1) | DOP2006000211A (ja) |
EA (1) | EA200801008A1 (ja) |
ES (1) | ES2354460T3 (ja) |
GT (1) | GT200600444A (ja) |
IL (1) | IL190434A0 (ja) |
MA (1) | MA30006B1 (ja) |
NO (1) | NO20082075L (ja) |
PE (1) | PE20070493A1 (ja) |
SV (1) | SV2009002863A (ja) |
TN (1) | TNSN08153A1 (ja) |
TW (1) | TW200806623A (ja) |
WO (1) | WO2007044318A2 (ja) |
ZA (1) | ZA200802587B (ja) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7176193B2 (en) * | 2002-06-19 | 2007-02-13 | Sanofi-Aventis Deutschland Gmbh | Acid-group-substituted diphenylazetidinones, process for their preparation, medicaments comprising these compounds, and their use |
GB0215579D0 (en) * | 2002-07-05 | 2002-08-14 | Astrazeneca Ab | Chemical compounds |
GB0329778D0 (en) * | 2003-12-23 | 2004-01-28 | Astrazeneca Ab | Chemical compounds |
US7871998B2 (en) * | 2003-12-23 | 2011-01-18 | Astrazeneca Ab | Diphenylazetidinone derivatives possessing cholesterol absorption inhibitory activity |
WO2005062824A2 (en) * | 2003-12-23 | 2005-07-14 | Merck & Co., Inc. | Anti-hypercholesterolemic compounds |
UY29607A1 (es) * | 2005-06-20 | 2007-01-31 | Astrazeneca Ab | Compuestos quimicos |
AR057380A1 (es) * | 2005-06-22 | 2007-11-28 | Astrazeneca Ab | Compuestos quimicos derivados de 2-azetidinona y uso terapeutico de los mismos |
SA06270191B1 (ar) * | 2005-06-22 | 2010-03-29 | استرازينيكا ايه بي | مشتقات من 2- أزيتيدينون جديدة باعتبارها مثبطات لامتصاص الكوليسترول لعلاج حالات فرط نسبة الدهون في الدم |
AR054482A1 (es) * | 2005-06-22 | 2007-06-27 | Astrazeneca Ab | Derivados de azetidinona para el tratamiento de hiperlipidemias |
AR057383A1 (es) * | 2005-06-22 | 2007-12-05 | Astrazeneca Ab | Compuestos quimicos derivados de 2-azetidinona, formulacion farmaceutica y un proceso de preparacion del compuesto |
MY148538A (en) * | 2005-06-22 | 2013-04-30 | Astrazeneca Ab | Novel 2-azetidinone derivatives as cholesterol absorption inhibitors for the treatment of hyperlipidaemic conditions |
TW200806623A (en) * | 2005-10-05 | 2008-02-01 | Merck & Co Inc | Anti-hypercholesterolemic compounds |
DE102005055726A1 (de) * | 2005-11-23 | 2007-08-30 | Sanofi-Aventis Deutschland Gmbh | Hydroxy-substituierte Diphenylazetidinone, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
TW200811098A (en) * | 2006-04-27 | 2008-03-01 | Astrazeneca Ab | Chemical compounds |
JP2010513485A (ja) * | 2006-12-20 | 2010-04-30 | メルク・シャープ・エンド・ドーム・コーポレイション | 抗高コレステロール血症化合物 |
DE102009023046B4 (de) | 2008-05-30 | 2016-10-13 | Hyundai Motor Company | Automatisch schaltbares Getriebe eines Kraftfahrzeuges |
WO2010056788A1 (en) * | 2008-11-17 | 2010-05-20 | Merck Sharp & Dohme Corp. | Anti-hypercholesterolemic compounds |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW223059B (ja) * | 1991-07-23 | 1994-05-01 | Schering Corp | |
US5631365A (en) * | 1993-09-21 | 1997-05-20 | Schering Corporation | Hydroxy-substituted azetidinone compounds useful as hypocholesterolemic agents |
AU2943095A (en) * | 1994-06-20 | 1996-01-15 | Schering Corporation | Substituted azetidinone compounds useful as hypocholesterolemic agents |
US5624920A (en) * | 1994-11-18 | 1997-04-29 | Schering Corporation | Sulfur-substituted azetidinone compounds useful as hypocholesterolemic agents |
RS50864B (sr) * | 2000-12-21 | 2010-08-31 | Sanofi-Aventis Deutschland Gmbh. | Novi 1,2-difenil-azetidinoni, postupak za njihovu proizvodnju, lekovi koji sadrže ova jedinjenja i njihova primena za lečenje poremećaja u metabolizmu lipida |
TWI291957B (en) * | 2001-02-23 | 2008-01-01 | Kotobuki Pharmaceutical Co Ltd | Beta-lactam compounds, process for repoducing the same and serum cholesterol-lowering agents containing the same |
US7176194B2 (en) * | 2002-06-19 | 2007-02-13 | Sanofi-Aventis Deutschland Gmbh | Ring-substituted diphenylazetidinones, process for their preparation, medicaments comprising these compounds, and their use |
US7176193B2 (en) * | 2002-06-19 | 2007-02-13 | Sanofi-Aventis Deutschland Gmbh | Acid-group-substituted diphenylazetidinones, process for their preparation, medicaments comprising these compounds, and their use |
DE602004016123D1 (de) * | 2003-03-07 | 2008-10-09 | Schering Corp | Substituierte azetidinon-derivate, deren pharmazeutische formulierungen und deren verwendung zur behandlung von hypercholesterolemia |
JP2005015434A (ja) * | 2003-06-27 | 2005-01-20 | Kotobuki Seiyaku Kk | 血清コレステロール低下剤或はアテローム性硬化症の予防又は治療剤 |
WO2005062824A2 (en) * | 2003-12-23 | 2005-07-14 | Merck & Co., Inc. | Anti-hypercholesterolemic compounds |
EP1851197A2 (en) * | 2005-02-09 | 2007-11-07 | Microbia, Inc. | Phenylazetidinone derivatives |
WO2006138163A2 (en) * | 2005-06-15 | 2006-12-28 | Merck & Co., Inc. | Anti-hypercholesterolemic compounds |
TW200806623A (en) * | 2005-10-05 | 2008-02-01 | Merck & Co Inc | Anti-hypercholesterolemic compounds |
DE102005055726A1 (de) * | 2005-11-23 | 2007-08-30 | Sanofi-Aventis Deutschland Gmbh | Hydroxy-substituierte Diphenylazetidinone, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung |
WO2008052658A1 (de) * | 2006-11-02 | 2008-05-08 | Sanofi-Aventis Deutschland Gmbh | Neues mit piperazin-1-sulfonsäure substituiertes diphenylazetidinon mit verbesserten pharmakologischen eigenschaften |
-
2006
- 2006-09-26 TW TW095135631A patent/TW200806623A/zh unknown
- 2006-09-27 AR ARP060104231A patent/AR058068A1/es unknown
- 2006-09-29 KR KR1020087008305A patent/KR20080050610A/ko not_active Application Discontinuation
- 2006-09-29 WO PCT/US2006/038551 patent/WO2007044318A2/en active Application Filing
- 2006-09-29 JP JP2008534613A patent/JP4879991B2/ja not_active Expired - Fee Related
- 2006-09-29 EP EP06816084A patent/EP1934175B1/en active Active
- 2006-09-29 CA CA2624481A patent/CA2624481C/en not_active Expired - Fee Related
- 2006-09-29 EA EA200801008A patent/EA200801008A1/ru unknown
- 2006-09-29 AU AU2006302584A patent/AU2006302584B2/en not_active Ceased
- 2006-09-29 CN CNA2006800369359A patent/CN101277930A/zh active Pending
- 2006-09-29 ES ES06816084T patent/ES2354460T3/es active Active
- 2006-09-29 DE DE602006018341T patent/DE602006018341D1/de active Active
- 2006-09-29 BR BRPI0616834A patent/BRPI0616834A2/pt not_active IP Right Cessation
- 2006-09-29 US US11/992,990 patent/US20090137546A1/en not_active Abandoned
- 2006-09-29 AT AT06816084T patent/ATE488495T1/de not_active IP Right Cessation
- 2006-10-03 PE PE2006001201A patent/PE20070493A1/es not_active Application Discontinuation
- 2006-10-03 GT GT200600444A patent/GT200600444A/es unknown
- 2006-10-04 US US11/542,966 patent/US7704988B2/en not_active Expired - Fee Related
- 2006-10-05 DO DO2006000211A patent/DOP2006000211A/es unknown
-
2008
- 2008-03-20 ZA ZA200802587A patent/ZA200802587B/xx unknown
- 2008-03-25 IL IL190434A patent/IL190434A0/en unknown
- 2008-04-04 SV SV2008002863A patent/SV2009002863A/es not_active Application Discontinuation
- 2008-04-04 TN TNP2008000153A patent/TNSN08153A1/en unknown
- 2008-04-18 CR CR9903A patent/CR9903A/es not_active Application Discontinuation
- 2008-05-02 MA MA30894A patent/MA30006B1/fr unknown
- 2008-05-02 NO NO20082075A patent/NO20082075L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
GT200600444A (es) | 2007-05-04 |
CA2624481C (en) | 2012-04-03 |
JP2009511475A (ja) | 2009-03-19 |
AR058068A1 (es) | 2008-01-23 |
SV2009002863A (es) | 2009-02-19 |
DE602006018341D1 (de) | 2010-12-30 |
PE20070493A1 (es) | 2007-06-13 |
TNSN08153A1 (en) | 2009-10-30 |
WO2007044318A3 (en) | 2007-07-12 |
CN101277930A (zh) | 2008-10-01 |
EP1934175B1 (en) | 2010-11-17 |
DOP2006000211A (es) | 2007-05-31 |
AU2006302584B2 (en) | 2011-10-13 |
CR9903A (es) | 2008-07-29 |
EA200801008A1 (ru) | 2009-02-27 |
ES2354460T3 (es) | 2011-03-15 |
US20090137546A1 (en) | 2009-05-28 |
ATE488495T1 (de) | 2010-12-15 |
US7704988B2 (en) | 2010-04-27 |
US20070078098A1 (en) | 2007-04-05 |
IL190434A0 (en) | 2008-11-03 |
EP1934175A2 (en) | 2008-06-25 |
MA30006B1 (fr) | 2008-12-01 |
TW200806623A (en) | 2008-02-01 |
KR20080050610A (ko) | 2008-06-09 |
AU2006302584A1 (en) | 2007-04-19 |
NO20082075L (no) | 2008-07-04 |
WO2007044318A2 (en) | 2007-04-19 |
ZA200802587B (en) | 2009-06-24 |
BRPI0616834A2 (pt) | 2016-08-23 |
CA2624481A1 (en) | 2007-04-19 |
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