TWI291957B - Beta-lactam compounds, process for repoducing the same and serum cholesterol-lowering agents containing the same - Google Patents
Beta-lactam compounds, process for repoducing the same and serum cholesterol-lowering agents containing the same Download PDFInfo
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- TWI291957B TWI291957B TW091102310A TW91102310A TWI291957B TW I291957 B TWI291957 B TW I291957B TW 091102310 A TW091102310 A TW 091102310A TW 91102310 A TW91102310 A TW 91102310A TW I291957 B TWI291957 B TW I291957B
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- -1 Beta-lactam compounds Chemical class 0.000 title description 2
- 238000000034 method Methods 0.000 title description 2
- 210000002966 serum Anatomy 0.000 title description 2
- 239000003529 anticholesteremic agent Substances 0.000 title 1
- 229940127226 anticholesterol agent Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 19
- 150000003839 salts Chemical class 0.000 abstract description 8
- 125000005843 halogen group Chemical group 0.000 abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000005243 carbonyl alkyl group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ZGNPLWZYVAFUNZ-UHFFFAOYSA-N tert-butylphosphane Chemical compound CC(C)(C)P ZGNPLWZYVAFUNZ-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 description 1
- MXVMRHIWTSFDPU-UHFFFAOYSA-N 2-chlorobenzenecarboximidamide Chemical compound NC(=N)C1=CC=CC=C1Cl MXVMRHIWTSFDPU-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- UKZCGMDMXDLAGZ-UHFFFAOYSA-M magnesium;2-methylpropane;bromide Chemical compound [Mg+2].[Br-].C[C-](C)C UKZCGMDMXDLAGZ-UHFFFAOYSA-M 0.000 description 1
- LWLPYZUDBNFNAH-UHFFFAOYSA-M magnesium;butane;bromide Chemical compound [Mg+2].[Br-].CCC[CH2-] LWLPYZUDBNFNAH-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 125000001010 sulfinic acid amide group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Description
蔻0808
(R3)p 、申請專利範圍 n、P、q及r爲0、1或2之整數〕〇 2. 種以通式（Ϊ )所表不之化合物或其藥學上能容 許之鹽類之製造方法，其特徵爲，係使得以通式（π ): (H) 〔式中，A丨、A?、I及p與上述相同、X爲鹵素等之 脫離基或旋光性的磺內醯胺衍生物〕所表示之化合物，與 以通式（羾）： 、 (m) (請先閲讀背面之注意事項再填寫本頁) 、τ ·· 線 (式中A3、A4、R3及η、q、r與上述相同）所表示 之化合物’於鹼存在下加熱回流來進行史陶丁格 (Stuadinger)反應或曼尼希(Mannich)反應。 3. —種以通式（I )所表示之化合物或其藥學上能容 許之鹽類之製造方法，其特徵爲，係使得以通式（IV):
本紙張尺度適用中國國家標準(CNS)A4規格(210 X 297公釐) A8B8C8D8
X 申請專利範圍 之化合物，與以通式（V): ·Α2、 (V) (式中，Α】、Α2、ρ、X及R3與上述相同）所表示之 化合物於鹼存在下反應。 4. 一種以通式（I )所表示之化合物或其藥學上能容 許之鹽類之製造方法，其特徵爲，係使得以通式（VI): (R3)q (VI) (請先閲讀背面之注意事項再填寫本頁)
(R3), •1T: 〔式中，η、p、q、r、Ai、A2、A3、A4 及 R3 與上述 相同’ Y爲旋光性的磺內醯胺衍生物〕所表示之化合物在 氫氧化鋰等鹼存在下反應來去除旋光性的磺內醯胺衍生物 成爲以通式(VI-1):
A 必 A2r^(R3)q 0¾¾ …… ^ A4 (R3)r 〔式中，η、p、q、r、Αι、A2 ' A3 ' A4 以及 R3 與上述 相同〕所表示之化合物，之後， a)於無溶劑或二氯甲烷、二氯乙烷等之溶劑中、鹵化 本紙張尺度適用中國國家標準(CNS)A4規格(210 X 297公爱) A8BSC8D8 申請專利範圍 劑存在下反應； b) 於縮合劑與二氯甲烷、DMF (N，N—二甲基甲醯胺） 等之溶劑中，鹼存在下反應； c) 於BihP(第三丁基膦）、Ph3P(三苯基膦)之存在下’使 光延試劑反應； d) 於BiuP(第三丁基膦）、PbP(三苯基膦)之存在下’使 (PyS) 2反應；或是， e) 於2,6—二氯化苯甲醯氯、2,4,6—三氯化苯甲醯氯等 反應在NaH存在下反應，然後以氫氧化鈉水溶液處理； 來進行通式(VI-1)所表示之化合物之環化反應。 5. —種以通式（I )所表示之化合物或其藥學上能容 許之鹽類之製造方法，其特徵爲，係使得以通式（VI): •CR3)« (請先閲讀背面之注意事項再填寫本頁) (VI)
,^γ·α4 (R3)r 線 〔式中，η、p、q、r、Αι、A2、A3、八4、R3 以及 γ 與 上述相同〕所表示之化合物在氫氧化鋰等鹼存在下反應$ 去除旋光性的磺內醯胺衍生物成爲以通式(VI-1): 本紙張尺度適用中國國家標準(CNS)A4規格(210 X 297公釐) A8 B8 C8 D8 六、申請專利範圍
〔式中，n、p、q、r、Αι、Ας、A3、At 以及 Rj 與上述 相同〕所表示之化合物之後’進行酯化成爲以通式(VI-2):
〔式中，η、p、q、r、Αι ' A2、A3、A4 以及 R3 與上述 相同，R7係甲基或乙基〕所表示之化合物，之後， a) 與LDA (二異丙醯胺鋰）或是LiHMDS〔雙（三甲 基甲矽烷基）醯胺鋰〕等鹼在溶劑中反應；或是 b) 與EtMgBr(溴化乙基鎂）、t-BuMgBr(溴化正丁基鎂) 等之格利雅試劑反應， 來進行通式(VI-2)所表示之化合物之環化反應。 6. —種以通式（VII)所表示之化合物或其藥學上能容 許之鹽類的製造方法， (請先閲讀背面之注意事項再塡寫本頁) 線 本纸張夂度適用中國國家標準(CNS)A4規格(210 X 297公楚·) 申請專利範圍 A8 B8 C8 D8
式中，A]、A〗、八4、R_3、η、p、q及r與上述相同；R? 爲單鍵(一）、_CH=HC—或一 OCH2 ; k'爲0或1〜9的整數 〕所表示之化合物或其藥學上能容許之鹽類；其特徵在於 ，係使得以通式（VEI) 7
A
(vm) 〔式中，Αι、A2、A4、R3、η、p、q及R3與上述相同 ;Z爲鹵素原子或三氟甲磺酸基等之脫離基，k'爲0或1〜 10的整數〕所表示之化合物，與以通式（IX ): R3y^R3 1^6-(012卜0人112 (式中，112及R3與上述相同，R6爲鹵素原子、一 CH CH2或-CH2〇H)所表示之化合物，在醋酸鈀以及2_ ( 三級丁基膦基）聯苯存在下進行偶合反應。 (IX) (請先閲讀背面之注意事項再塡寫本頁) 線 本紙張尺度適用中國國家標準(CNS)A4規格(210 X 297公釐) A8B8C8D8 六、申請專利範圍 7. —種降血清膽固醇組成物，係含有以通式（I )所 表示之化合物或其藥學上能容許之鹽類。 8. 如申請專利範圍第7項之降血清膽固醇組成物，係 進一步倂用/5 -內酿胺酶抑制劑。 (請先閲讀背面之注意事項再填寫本頁)
-P 、\έ 線 本紙張尺度適用中國國家標準(CNS)A4規格(210 X 297公釐)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001048202 | 2001-02-23 | ||
| JP2001128031 | 2001-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI291957B true TWI291957B (en) | 2008-01-01 |
Family
ID=26609978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091102310A TWI291957B (en) | 2001-02-23 | 2002-02-08 | Beta-lactam compounds, process for repoducing the same and serum cholesterol-lowering agents containing the same |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7045515B2 (zh) |
| EP (1) | EP1362855B1 (zh) |
| JP (1) | JP4229701B2 (zh) |
| KR (1) | KR100721639B1 (zh) |
| CN (1) | CN1273467C (zh) |
| AT (1) | ATE374769T1 (zh) |
| AU (1) | AU2002237522B2 (zh) |
| BR (1) | BRPI0206193B1 (zh) |
| CA (1) | CA2438961C (zh) |
| DE (1) | DE60222742T2 (zh) |
| DK (1) | DK1362855T3 (zh) |
| ES (1) | ES2294101T3 (zh) |
| MX (1) | MXPA03005073A (zh) |
| PT (1) | PT1362855E (zh) |
| RU (1) | RU2301799C2 (zh) |
| TW (1) | TWI291957B (zh) |
| WO (1) | WO2002066464A1 (zh) |
Families Citing this family (59)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RS50386B (sr) | 2001-03-28 | 2009-12-31 | Schering Corporation, | Enantioselektivna sinteza intermedijarnih jedinjenja azetidinona |
| GB0215579D0 (en) * | 2002-07-05 | 2002-08-14 | Astrazeneca Ab | Chemical compounds |
| 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 |
| CN1870988A (zh) * | 2003-10-30 | 2006-11-29 | 默克公司 | 作为抗高胆固醇血症药的2－氮杂环丁烷酮 |
| EP1918000A2 (en) | 2003-11-05 | 2008-05-07 | Schering Corporation | Combinations of lipid modulating agents and substituted azetidinones and treatments for vascular conditions |
| DE602004008100T2 (de) * | 2003-11-10 | 2008-04-30 | Microbia Inc., Cambridge | 4-biarylyl-1-phenylazetidin-2-one |
| SI1682499T1 (sl) * | 2003-11-10 | 2008-02-29 | Microbia Inc | 4-biarilil-1-fenilazetidin-2-oni |
| WO2005061452A1 (en) | 2003-12-23 | 2005-07-07 | Astrazeneca Ab | Diphenylazetidinone derivates possessing cholesterol absorption inhibitory activity |
| CN100471835C (zh) | 2003-12-23 | 2009-03-25 | 默克公司 | 抗高胆固醇血症化合物 |
| BRPI0510150A (pt) | 2004-05-21 | 2007-10-02 | Sanofi Aventis Deutschland | processo para preparação de derivados de 1,4-difenilacetidinonas |
| CA2581596A1 (en) * | 2004-09-29 | 2006-04-13 | Schering Corporation | Combinations of substituted azetidonones and cb1 antagonists |
| CA2589483C (en) | 2004-12-03 | 2013-10-29 | Schering Corporation | Substituted piperazines as cb1 antagonists |
| TW200726746A (en) * | 2005-05-06 | 2007-07-16 | Microbia Inc | Processes for production of 4-biphenylylazetidin-2-ones |
| MX2007014172A (es) * | 2005-05-11 | 2008-04-02 | Microbia Inc | Procedimiento para la produccion de 4-bifenililacetidina-2-onas fenolicos. |
| US7737155B2 (en) | 2005-05-17 | 2010-06-15 | Schering Corporation | Nitrogen-containing heterocyclic compounds and methods of use thereof |
| BRPI0611415A2 (pt) * | 2005-05-25 | 2010-09-08 | Microbia Inc | ácidos fosfÈnicos de 4-(bifenilil)azetidin-2-ona e processo para a produção dos mesmos |
| CN101198338A (zh) * | 2005-06-15 | 2008-06-11 | 默克公司 | 抗高胆固醇血化合物 |
| EP1902046B1 (en) | 2005-06-20 | 2009-12-02 | Schering Corporation | Piperidine derivatives useful as histamine h3 antagonists |
| UY29607A1 (es) | 2005-06-20 | 2007-01-31 | Astrazeneca Ab | Compuestos quimicos |
| AR057072A1 (es) | 2005-06-22 | 2007-11-14 | Astrazeneca Ab | Compuestos quimicos derivados de 2-azetidinona, formulacion farmaceutica y un proceso de preparacion del compuesto |
| 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 |
| RU2008112198A (ru) | 2005-09-29 | 2009-10-10 | Санофи-Авентис (Fr) | Производные фенил-1,2,4-оксадиазолона, способы их получения и их применение в качестве фармацевтических средств |
| TW200806623A (en) * | 2005-10-05 | 2008-02-01 | Merck & Co Inc | Anti-hypercholesterolemic compounds |
| NZ569814A (en) * | 2006-01-18 | 2011-10-28 | Schering Corp | Cannibinoid receptor modulators |
| JP4880348B2 (ja) * | 2006-04-25 | 2012-02-22 | 壽製薬株式会社 | アズレン誘導体及びそれを有効成分とする血清コレステロール低下剤 |
| AR060623A1 (es) | 2006-04-27 | 2008-07-02 | Astrazeneca Ab | Compuestos derivados de 2-azetidinona y un metodo de preparacion |
| JP2010500300A (ja) | 2006-08-08 | 2010-01-07 | サノフィ−アベンティス | アリールアミノアリール−アルキル−置換イミダゾリジン−２，４−ジオン、それらの製造法、それらの化合物を含有する薬剤、およびそれらの使用 |
| WO2008033464A2 (en) * | 2006-09-15 | 2008-03-20 | Schering Corporation | Azetidinone derivatives for the treatment of disorders of the lipid metabolism |
| AU2007294771A1 (en) | 2006-09-15 | 2008-03-20 | Schering Corporation | Azetidine and azetidone derivatives useful in treating pain and disorders of lipid metabolism |
| CN101541795A (zh) | 2006-09-15 | 2009-09-23 | 先灵公司 | 用于治疗疼痛、糖尿病和脂类代谢紊乱的螺-稠合氮杂环丁烷衍生物 |
| MX2009002924A (es) * | 2006-09-15 | 2009-05-28 | Schering Corp | Derivados de azetidinona espirociclica para el tratamiento de trastornos del metabolismo de los lipidos, el dolor, la diabetes y otros trastornos. |
| US20100035857A1 (en) * | 2006-12-20 | 2010-02-11 | Devita Robert J | Anti-hypercholesterolemic compounds |
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| WO2011157827A1 (de) | 2010-06-18 | 2011-12-22 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
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| JPS5857360A (ja) | 1981-10-01 | 1983-04-05 | Ajinomoto Co Inc | アゼチジノン誘導体 |
| DE69222532T2 (de) * | 1991-07-23 | 1998-02-26 | Schering Corp | Substituierte beta-lactam-verbindungen als hypocholesterolemische mittel und verfahren zu deren herstellung |
| SK282164B6 (sk) * | 1992-09-18 | 2001-11-06 | Merck & Co., Inc. | Spôsob výroby beta-metylkarbapenémových medziproduktov, medziprodukty na vykonávanie tohto postupu a spôsob výroby medziproduktov |
| US5412092A (en) * | 1993-04-23 | 1995-05-02 | Bristol-Myers Squibb Company | N-substituted 2-azetidinones |
| US5631365A (en) | 1993-09-21 | 1997-05-20 | Schering Corporation | Hydroxy-substituted azetidinone compounds useful as hypocholesterolemic agents |
| ATE219495T1 (de) * | 1995-10-31 | 2002-07-15 | Schering Corp | Zuckersubstituierte 2-azetidinone, verwendbar als hypocholesterdenische arzneimittel |
| WO1997016424A1 (en) * | 1995-11-02 | 1997-05-09 | Schering Corporation | Process for preparing 1-(4-fluorophenyl)-3(r)-(3(s)-hydroxy-3-([phenyl or 4-fluorophenyl])-propyl)-4(s)-(4-hydroxyphenyl)-2-azetidinone |
| IL156548A0 (en) * | 2000-12-21 | 2004-01-04 | Aventis Pharma Gmbh | Diphenyl azetidinone derivatives, method for the production thereof, medicaments containing these compounds, and their use |
-
2002
- 2002-02-08 TW TW091102310A patent/TWI291957B/zh not_active IP Right Cessation
- 2002-02-20 EP EP02703861A patent/EP1362855B1/en not_active Expired - Lifetime
- 2002-02-20 CA CA2438961A patent/CA2438961C/en not_active Expired - Fee Related
- 2002-02-20 RU RU2003128424/04A patent/RU2301799C2/ru not_active IP Right Cessation
- 2002-02-20 ES ES02703861T patent/ES2294101T3/es not_active Expired - Lifetime
- 2002-02-20 MX MXPA03005073A patent/MXPA03005073A/es active IP Right Grant
- 2002-02-20 CN CNB028052013A patent/CN1273467C/zh not_active Expired - Fee Related
- 2002-02-20 KR KR1020037010927A patent/KR100721639B1/ko not_active Expired - Fee Related
- 2002-02-20 PT PT02703861T patent/PT1362855E/pt unknown
- 2002-02-20 DK DK02703861T patent/DK1362855T3/da active
- 2002-02-20 WO PCT/JP2002/001481 patent/WO2002066464A1/ja not_active Ceased
- 2002-02-20 JP JP2002565979A patent/JP4229701B2/ja not_active Expired - Lifetime
- 2002-02-20 BR BRPI0206193A patent/BRPI0206193B1/pt not_active IP Right Cessation
- 2002-02-20 AU AU2002237522A patent/AU2002237522B2/en not_active Ceased
- 2002-02-20 US US10/450,171 patent/US7045515B2/en not_active Expired - Lifetime
- 2002-02-20 DE DE60222742T patent/DE60222742T2/de not_active Expired - Lifetime
- 2002-02-20 AT AT02703861T patent/ATE374769T1/de active
Also Published As
| Publication number | Publication date |
|---|---|
| PT1362855E (pt) | 2007-12-04 |
| DE60222742T2 (de) | 2008-07-17 |
| BRPI0206193B1 (pt) | 2016-05-24 |
| CA2438961C (en) | 2010-02-16 |
| US20040063929A1 (en) | 2004-04-01 |
| JP4229701B2 (ja) | 2009-02-25 |
| KR20030076690A (ko) | 2003-09-26 |
| DK1362855T3 (da) | 2008-01-28 |
| EP1362855A4 (en) | 2005-02-23 |
| MXPA03005073A (es) | 2003-09-05 |
| ATE374769T1 (de) | 2007-10-15 |
| WO2002066464A1 (fr) | 2002-08-29 |
| EP1362855A1 (en) | 2003-11-19 |
| CN1492865A (zh) | 2004-04-28 |
| AU2002237522B2 (en) | 2007-08-02 |
| EP1362855B1 (en) | 2007-10-03 |
| CN1273467C (zh) | 2006-09-06 |
| HK1060357A1 (zh) | 2004-08-06 |
| US7045515B2 (en) | 2006-05-16 |
| JPWO2002066464A1 (ja) | 2004-06-17 |
| RU2003128424A (ru) | 2005-01-27 |
| KR100721639B1 (ko) | 2007-05-23 |
| DE60222742D1 (de) | 2007-11-15 |
| BR0206193A (pt) | 2004-02-03 |
| RU2301799C2 (ru) | 2007-06-27 |
| CA2438961A1 (en) | 2002-08-29 |
| ES2294101T3 (es) | 2008-04-01 |
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