FI78082B - Foerfarande foer framstaellning av terapeutiskt aktiva 6(r)-/2-(8-acyloxi-2,6-dimetylpolyhydronaftyl-1)- etyl/-4(r)-hydroxi-3,4,5,6-tetrahydro-2h-pyranoner och 7-/8-acyloxi- 2,6-dimetylpolyhydronaftyl-1/-3(r),5(r)-dihydroxiheptansyror. - Google Patents
Foerfarande foer framstaellning av terapeutiskt aktiva 6(r)-/2-(8-acyloxi-2,6-dimetylpolyhydronaftyl-1)- etyl/-4(r)-hydroxi-3,4,5,6-tetrahydro-2h-pyranoner och 7-/8-acyloxi- 2,6-dimetylpolyhydronaftyl-1/-3(r),5(r)-dihydroxiheptansyror. Download PDFInfo
- Publication number
- FI78082B FI78082B FI810287A FI810287A FI78082B FI 78082 B FI78082 B FI 78082B FI 810287 A FI810287 A FI 810287A FI 810287 A FI810287 A FI 810287A FI 78082 B FI78082 B FI 78082B
- Authority
- FI
- Finland
- Prior art keywords
- hydroxy
- formula
- pyran
- tetrahydro
- solution
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen 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
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen 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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Steroid Compounds (AREA)
Claims (4)
1. Förfarande för framställning av terapeutiskt ak-tiva 6 (R) -D-- (8-acyloxi-2,6-dimetylpolyhydronaftyl-l) -etyi7-5 4(R)-hydroxi-3,4,5,6-tetrahydro-2H-pyran-2-oner med formeln H0 ίο I o = H 5 R-C-0 ^ ch3 15 »Ws. "h? Cfi3 väri R är oförgrenad eller förgrenad C3_<j-alkyl förutom 2-(S)-butyl, cyklopropyl, adamantyl, C4_g-alkenyl, CF3~ 20 substituerad propyl, p-fluorfenyl eller bensyl, och streckade linjerna X och Z betecknar eventuella dubbelbind-ningar, varvid nämnda dubbelbindningar, ifall närvarande, befinner sig antingen vid X och Z eller vid X allena; och motsvarande 7-/l3-acyloxi-2,6-dimetylpolyhydronaftyl-l7- 25 3(R),5(R)-dihydroxiheptansyror med formeln II, HO k/0H .30 = o 1
1. CHo 3 n 35 43 7 8 0 8 2 väri R, X och Z betecknar samma som i formeln I, och lägre alkylestrar eller 2,3-dihydroxipropylestrar av föreningar med formeln II, kännetecknat därav, att man 1. uppvärmer 6(R)-£2-(8-(2-metylbutyryloxi)-2,6-di-5 metylpolyhydronaftyl-1)-etylJ-4(R)-hydroxi-3,4,5,6-tetra- hydro-2H-pyran-2-on med formeln III 10 .3Γ O β * I H I III
15 JL xX Zj med en alkalimetallhydroxid i ett protiskt lösningsmedel och surgör reaktionsblandningen och laktoniserar produkten 20 för erhällande av 6(R)-£1-(8-hydroxi-2,6-dimetylpolyhydro-naftyl-1)-ety!7-4(R)-hydroxi-3,4,5,6-tetrahydro-2H-pyran-2-on med formeln IV 25 H0 TV CHV3 2. omsätter den erhällna föreningen med formeln IV 35 med tert.-butyldimetylklorsilan under en inert skyddsgas vid rumstemperatur i närvaro av en syraacceptor för erhäl- 44 78082 lande av en motsvarande skyddad förening med formeIn V CH, CHo 1 1 CHo-C-Si-0w< k L3 \J HO S' V ?* JcV”3 3. acylerar den erhillna 4-tert.-butyldimetylsilyl-oxiföreningen genom 15 a) omrörande av densamma i en lösning med en syra- klorid RCOC1, i pyridinlösning i en inert skyddsgas i när-varo av en acyleringskatalysator, eller b) omrörande av densamma i en lösning vid rumstempe-ratur med en syra RCOOH och Ν,Ν-dicyklohexylkarbodiimid i 2. närvaro av en acyleringskatalysator, och 4. avlägsnar silylgruppen frän den erhcillna f öreningen med formeln VI CH-3 CH-, 1 3 1.
25 CH3-c-Sx-o^s^yo ch3 ch3 R-CO-O S = H VI s m ^ rvt 3. y\l/\>H 3 CHf genom omröring av silylföreningen vid rumstemperatur i tet-35 rahydrofuran med 3 ekvivalenter av tetrabutylammoniumfluo-rid och 4 ekvivalenter av ättiksyra per en ekvivalent av
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11805180A | 1980-02-04 | 1980-02-04 | |
| US11804980A | 1980-02-04 | 1980-02-04 | |
| US11805180 | 1980-02-04 | ||
| US11804980 | 1980-02-04 | ||
| US17546080A | 1980-08-05 | 1980-08-05 | |
| US17523280 | 1980-08-05 | ||
| US17546080 | 1980-08-05 | ||
| US06/175,232 US4293496A (en) | 1980-02-04 | 1980-08-05 | 6(R)-[2-(8-Hydroxy-2,6-dimethylpolyhydronaphthyl-1)-ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-ones |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI810287L FI810287L (fi) | 1981-08-05 |
| FI78082B true FI78082B (fi) | 1989-02-28 |
| FI78082C FI78082C (sv) | 1989-06-12 |
Family
ID=27494171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI810287A FI78082C (sv) | 1980-02-04 | 1981-02-02 | Förfarande för framställning av terapeutiskt aktiva 6(R)-/2-(8-acyloxi -2,6-dimetylpolyhydronaftyl-1)-etyl/-4(R)-hydroxi-3,4,5,6-tetrahydro-2 H-pyranoner och 7-/8-acyloxi-2,6-dimetylpolyhydronaftyl-1/-3(R),5(R)-d ihydroxiheptansyror |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0033538B1 (sv) |
| AU (1) | AU548996B2 (sv) |
| CA (1) | CA1199322A (sv) |
| CY (1) | CY1404A (sv) |
| DD (1) | DD155989A5 (sv) |
| DE (1) | DE3173042D1 (sv) |
| DK (1) | DK157292C (sv) |
| ES (1) | ES499079A0 (sv) |
| FI (1) | FI78082C (sv) |
| GR (1) | GR74798B (sv) |
| HK (1) | HK16488A (sv) |
| IE (1) | IE51478B1 (sv) |
| IL (1) | IL62044A (sv) |
| MA (1) | MA19054A1 (sv) |
| MY (1) | MY8700745A (sv) |
| NL (1) | NL930009I2 (sv) |
| NO (2) | NO154229C (sv) |
| NZ (1) | NZ196172A (sv) |
| PT (1) | PT72441B (sv) |
| RO (1) | RO82367B (sv) |
| SG (1) | SG61087G (sv) |
| YU (1) | YU28181A (sv) |
Families Citing this family (54)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0692381B2 (ja) * | 1980-03-31 | 1994-11-16 | 三共株式会社 | Ｍｂ−５３０ａ誘導体 |
| US4343814A (en) * | 1980-11-17 | 1982-08-10 | Merck & Co., Inc. | Hypocholesterolemic fermentation products |
| US4432996A (en) * | 1980-11-17 | 1984-02-21 | Merck & Co., Inc. | Hypocholesterolemic fermentation products and process of preparation |
| EP0094443A1 (en) * | 1982-05-17 | 1983-11-23 | Merck & Co. Inc. | 6(R)-(2-(8(S) (2,2-dimethylbutyryloxy)-2(S),6(S)-dimethyl-1,2,3,4,4a(S),5,6,7,8,8a(S)-decahydronaphthyl-1(S))ethyl)-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one, process for preparing and pharmaceutical composition containing the same |
| US4503072A (en) * | 1982-12-22 | 1985-03-05 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| DE3461180D1 (en) * | 1983-01-24 | 1986-12-11 | Sandoz Ag | Analogs of mevalonolactone and derivatives thereof, processes for their production, pharmaceutical compositions containing them and their use as pharmaceuticals |
| EP0137444B1 (en) * | 1983-10-11 | 1990-01-31 | Merck & Co. Inc. | Processes for preparing 6(R)-[2-[8(S)(2,2-dimethylbutyryloxy)-2(S),6(S)-dimethyl-1,2,3,4,4a(S),5,6,7,8,8a(S)-Decahydronaphthyl-1(S)]ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one |
| DE3480923D1 (de) * | 1983-10-11 | 1990-02-08 | Merck & Co Inc | Verfahren zur c-methylierung von 2-methylbutyraten. |
| US4668699A (en) * | 1985-08-05 | 1987-05-26 | Merck & Co., Inc. | Novel HMG-CoA reductase inhibitors |
| US4833258A (en) * | 1987-02-17 | 1989-05-23 | Merck & Co., Inc. | Intermediates useful in the preparation of HMG-COA reductase inhibitors |
| US4997848A (en) | 1987-10-27 | 1991-03-05 | Sankyo Company, Limited | Octahydronaphthalene oxime derivatives for cholesterol synthesis inhibition |
| US5021451A (en) * | 1988-11-14 | 1991-06-04 | Hoffman-La Roche Inc. | Method for inhibiting hyperproliferative diseases |
| GB8915280D0 (en) * | 1989-07-04 | 1989-08-23 | British Bio Technology | Compounds |
| US5110825A (en) * | 1989-12-28 | 1992-05-05 | Shionogi & Co., Ltd. | Benzofuran derivative |
| GB9100174D0 (en) * | 1991-01-04 | 1991-02-20 | British Bio Technology | Compounds |
| NZ250609A (en) * | 1992-12-28 | 1995-07-26 | Sankyo Co | Hexahydronaphthalene esters and ring closed lactones; preparation and medicaments |
| US6268392B1 (en) | 1994-09-13 | 2001-07-31 | G. D. Searle & Co. | Combination therapy employing ileal bile acid transport inhibiting benzothiepines and HMG Co-A reductase inhibitors |
| US6642268B2 (en) | 1994-09-13 | 2003-11-04 | G.D. Searle & Co. | Combination therapy employing ileal bile acid transport inhibiting benzothipines and HMG Co-A reductase inhibitors |
| HUP9601808A3 (en) * | 1995-07-03 | 2000-06-28 | Sankyo Co | Treatment of arteriosclerosis and xanthoma |
| DE877742T1 (de) * | 1995-12-06 | 1999-07-22 | Antibiotic Co., Razgrad | Verfahren zur herstellung von lovastatin |
| CA2185961A1 (en) | 1996-09-19 | 1998-03-20 | K.S. Keshava Murthy | Process for producing simvastatin |
| US6083497A (en) | 1997-11-05 | 2000-07-04 | Geltex Pharmaceuticals, Inc. | Method for treating hypercholesterolemia with unsubstituted polydiallylamine polymers |
| SI9800057A (sl) * | 1998-02-26 | 1999-08-31 | Krka, Tovarna Zdravil, D.D. | Postopek za pripravo simvastatina in njegovih derivatov |
| CA2240983A1 (en) | 1998-06-18 | 1999-12-18 | Yong Tao | Process to manufacture simvastatin and intermediates |
| KR20010108046A (ko) | 1998-12-23 | 2001-12-07 | 윌리암스 로저 에이 | 심장혈관의 징후에 대한 회장 담즙산 수송 저해제 및콜레스테릴 에스테르 운반 단백질 저해제의 조합물 |
| PT1140184E (pt) | 1998-12-23 | 2003-10-31 | Searle Llc | Combinacoes de inibidores de proteina de transferencia de ester de colesterilo com derivados de acido nicotinico para indicacoes cardiovasculares |
| PT1140186E (pt) | 1998-12-23 | 2003-10-31 | Searle Llc | Combinacoes de inibidores de proteina de transferencia de ester de colesterilo com derivados de acido fibrico para indicacoes cardiovasculares |
| ATE242008T1 (de) | 1998-12-23 | 2003-06-15 | Searle Llc | Kombnationen von cholesteryl ester transfer protein inhibitoren und gallensäure sequestriermitteln für kardiovaskuläre indikationen |
| DK1140189T3 (da) | 1998-12-23 | 2003-09-15 | Searle Llc | Kombinationer af ileal galdesyre-transportinhibitorer og fibrinsyrederivater til cardiovaskulære indikationer |
| AU2157400A (en) | 1998-12-23 | 2000-07-31 | G.D. Searle & Co. | Combinations of cholesteryl ester transfer protein inhibitors and hmg coa reductase inhibitors for cardiovascular indications |
| PL348609A1 (en) | 1998-12-23 | 2002-06-03 | Searle Llc | Combinations of ileal bile acid transport inhibitors and bile acid sequestring agents for cardiovascular indications |
| EP1286984A2 (en) | 2000-03-10 | 2003-03-05 | Pharmacia Corporation | Method for the preparation of tetrahydrobenzothiepines |
| SI1323701T1 (sl) * | 2000-09-07 | 2009-12-31 | Kaneka Corp | Postopki za kristalizacijo hidroksikarboksilnih kislin |
| EP1448546A4 (en) | 2001-11-02 | 2005-02-02 | Searle Llc | MONO- AND DI-FLUORINATED BENZOTHIEPINE COMPOUNDS AS INHIBITORS OF TRANSPORT OF ACIDICALLY DEPENDENT SODIUM ACILIC (ASBT) BILIARY ACIDS AND TAUROCHOLATE RECOVERY |
| JP2005521653A (ja) | 2002-01-17 | 2005-07-21 | ファルマシア コーポレイション | 先端ナトリウム同時依存性胆汁酸輸送（ａｓｂｔ）およびタウロコール酸塩取込みの阻害剤としての新規アルキル／アリールヒドロキシまたはケトチエピン化合物 |
| SI21187A (sl) | 2002-03-26 | 2003-10-31 | Krka, Tovarna Zdravil D.D., Novo Mesto | Postopek za pripravo 4-oksitetrahidropiran-2-onov |
| KR20040092790A (ko) * | 2003-04-29 | 2004-11-04 | 씨제이 주식회사 | 심바스타틴 중간체 제조방법 |
| EP1741427A1 (en) | 2005-07-06 | 2007-01-10 | KRKA, D.D., Novo Mesto | Pharmaceutical composition comprising simvastatin and ezetimibe |
| NZ594369A (en) | 2006-07-05 | 2013-10-25 | Takeda Gmbh | Combination of HMG-CoA reductase inhibitors with phosphodiesterase 4 inhibitors for the treatment of inflammatory pulmonary diseases |
| WO2009013764A2 (en) * | 2007-07-24 | 2009-01-29 | Jubilant Organosys Limited | Process for producing 6(r)-[2-(8'(s)-2 ',2 '-dimethylbutyryloxy-2'(s),6'(r)-dimethyl-1,2,6,7', 8',8a'(r)- hexahydronaphthyl-l'(s))ethyl]-4(r)-hydroxy-3,4,5,6- tetrahydro-2h-pyran-2-one |
| JOP20080381B1 (ar) | 2007-08-23 | 2023-03-28 | Amgen Inc | بروتينات مرتبطة بمولدات مضادات تتفاعل مع بروبروتين كونفيرتاز سيتيليزين ككسين من النوع 9 (pcsk9) |
| ES2330184B1 (es) | 2008-06-03 | 2010-07-05 | Neuron Biopharma, S.A. | Uso de estatinas como anticonvulsivantes, antiepilepticos y neuroprotectores. |
| ES2343049B1 (es) | 2008-10-15 | 2011-06-10 | Neuron Biopharma, S.A. | Biosintesis de derivados de monacolina j. |
| EP2204170A1 (en) | 2008-12-01 | 2010-07-07 | LEK Pharmaceuticals D.D. | Pharmaceutical composition comprising ezetimibe and simvastatin |
| EP2373609B1 (en) | 2008-12-19 | 2013-10-16 | KRKA, D.D., Novo Mesto | Use of amphiphilic compounds for controlled crystallization of statins and statin intermediates |
| EP2327682A1 (en) | 2009-10-29 | 2011-06-01 | KRKA, D.D., Novo Mesto | Use of amphiphilic compounds for controlled crystallization of statins and statin intermediates |
| EP2216016A1 (en) | 2009-02-06 | 2010-08-11 | LEK Pharmaceuticals d.d. | Process for the preparation of a pharmaceutical composition comprising ezetimibe |
| EP2241561A1 (en) * | 2009-04-16 | 2010-10-20 | Neuron Biopharma, S.A. | Neuroprotective, hypocholesterolemic and antiepileptic compound |
| WO2011002424A2 (en) | 2009-07-02 | 2011-01-06 | Bilgic Mahmut | Solubility and stability enchancing pharmaceutical formulation |
| AR079336A1 (es) | 2009-12-11 | 2012-01-18 | Irm Llc | Antagonistas de la pro-proteina convertasa-subtilisina/quexina tipo 9 (pcsk9) |
| EP2368543A1 (en) | 2010-03-25 | 2011-09-28 | KRKA, tovarna zdravil, d.d., Novo mesto | Method of preparing a granulated pharmaceutical composition comprising simvastatin and/or ezetimibe |
| ES2380473B1 (es) * | 2010-10-13 | 2013-02-19 | Neuron Biopharma, S.A. | Compuesto neuroprotector, hipocolesterolémico, antiinflamatorio y antiepiléptico. |
| EP2797641B1 (en) | 2011-12-29 | 2019-07-10 | Trustees Of Tufts College | Functionalization of biomaterials to control regeneration and inflammation responses |
| TW201410706A (zh) | 2012-06-15 | 2014-03-16 | Genentech Inc | 抗－ｐｃｓｋ９抗體、調配物、劑量及使用方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5612114B2 (sv) * | 1974-06-07 | 1981-03-18 | ||
| US4049495A (en) * | 1974-06-07 | 1977-09-20 | Sankyo Company Limited | Physiologically active substances and fermentative process for producing the same |
| US4137322A (en) | 1976-11-02 | 1979-01-30 | Sankyo Company Limited | ML-236B carboxylic acid derivatives and their use as antihyperlipemic agents |
| JPS6026094B2 (ja) | 1978-07-04 | 1985-06-21 | 三共株式会社 | テトラヒドロｍｌ↓−２３６ｂおよびその誘導体並びにそれを有効成分とする高脂血症治療剤 |
| JPS5925599B2 (ja) * | 1979-02-20 | 1984-06-19 | 三共株式会社 | 新生理活性物質モナコリンｋおよびその製造法 |
| US4231938A (en) * | 1979-06-15 | 1980-11-04 | Merck & Co., Inc. | Hypocholesteremic fermentation products and process of preparation |
| AU535944B2 (en) * | 1979-06-15 | 1984-04-12 | Merck & Co., Inc. | Hypocholestermic fermentation products from aspergillus |
| PT72394B (en) | 1980-02-04 | 1982-09-06 | Merck & Co Inc | Process for preparing dihydro and tetrahydromevinoline hypocholesterolimics |
-
1981
- 1981-01-23 AU AU66573/81A patent/AU548996B2/en not_active Expired
- 1981-01-29 MA MA19255A patent/MA19054A1/fr unknown
- 1981-02-02 EP EP81100729A patent/EP0033538B1/en not_active Expired
- 1981-02-02 FI FI810287A patent/FI78082C/sv not_active IP Right Cessation
- 1981-02-02 GR GR64028A patent/GR74798B/el unknown
- 1981-02-02 CY CY140481A patent/CY1404A/xx unknown
- 1981-02-02 IL IL62044A patent/IL62044A/xx not_active IP Right Cessation
- 1981-02-02 DE DE8181100729T patent/DE3173042D1/de not_active Expired
- 1981-02-03 CA CA000369992A patent/CA1199322A/en not_active Expired
- 1981-02-03 PT PT72441A patent/PT72441B/pt unknown
- 1981-02-03 DK DK046181A patent/DK157292C/da active
- 1981-02-03 IE IE204/81A patent/IE51478B1/en not_active IP Right Cessation
- 1981-02-03 ES ES499079A patent/ES499079A0/es active Granted
- 1981-02-03 YU YU00281/81A patent/YU28181A/xx unknown
- 1981-02-03 DD DD81227405A patent/DD155989A5/de unknown
- 1981-02-03 NO NO810358A patent/NO154229C/no unknown
- 1981-02-03 NZ NZ196172A patent/NZ196172A/en unknown
- 1981-02-04 RO RO103303A patent/RO82367B/ro unknown
-
1987
- 1987-07-27 SG SG610/87A patent/SG61087G/en unknown
- 1987-12-30 MY MY745/87A patent/MY8700745A/xx unknown
-
1988
- 1988-03-03 HK HK164/88A patent/HK16488A/xx not_active IP Right Cessation
-
1993
- 1993-02-09 NL NL930009C patent/NL930009I2/nl unknown
-
1994
- 1994-07-01 NO NO1994001C patent/NO1994001I1/no unknown
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| ND | Supplementary protection certificate (spc) granted | ||
| SPCG | Supplementary protection certificate granted |
Spc suppl protection certif: L14 Extension date: 20030406 |
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| MA | Patent expired |
Owner name: MERCK & CO., INC. |