SI20159A - Nov postopek za odstranitev sililoksi zaščitne skupine iz 4-sililoksi tetrahidro-piran-2-on-ov - Google Patents

Nov postopek za odstranitev sililoksi zaščitne skupine iz 4-sililoksi tetrahidro-piran-2-on-ov Download PDF

Info

Publication number: SI20159A
Authority: SI; Slovenia
Prior art keywords: atoms; alkyl; hydrogen; formula; independently hydrogen
Prior art date: 1999-02-04

Application number

SI9900025A

Other languages

English (en)

Slovenian (sl)

Inventor

Rudolf Ru�man

Marko �li�ar

Original Assignee

LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-02-04

Filing date

1999-02-04

Publication date

2000-08-31

1999-02-04 Application filed by LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d. filed Critical LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d.

1999-02-04 Priority to SI9900025A priority Critical patent/SI20159A/sl

2000-02-02 Priority to DE60010659T priority patent/DE60010659T2/de

2000-02-02 Priority to JP2000597287A priority patent/JP2002536372A/ja

2000-02-02 Priority to EP00901283A priority patent/EP1149086B1/de

2000-02-02 Priority to US09/869,372 priority patent/US6509479B1/en

2000-02-02 Priority to AT00901283T priority patent/ATE266653T1/de

2000-02-02 Priority to AU21241/00A priority patent/AU2124100A/en

2000-02-02 Priority to PCT/IB2000/000105 priority patent/WO2000046217A1/en

2000-02-02 Priority to ES00901283T priority patent/ES2216853T3/es

2000-08-31 Publication of SI20159A publication Critical patent/SI20159A/sl

Links

238000000034 method Methods 0.000 title claims abstract description 32
125000006239 protecting group Chemical group 0.000 title claims description 4
125000004469 siloxy group Chemical group [SiH3]O* 0.000 title claims description 4
RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims abstract description 15
229960002855 simvastatin Drugs 0.000 claims abstract description 15
RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims abstract description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
238000010511 deprotection reaction Methods 0.000 claims description 12
239000002904 solvent Substances 0.000 claims description 10
DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 claims description 9
-1 trimethylsilyloxy, triethylsilyloxy, isopropyldimethylsilyloxy Chemical group 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 8
KVBCYCWRDBDGBG-UHFFFAOYSA-N azane;dihydrofluoride Chemical compound [NH4+].F.[F-] KVBCYCWRDBDGBG-UHFFFAOYSA-N 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
239000003960 organic solvent Substances 0.000 claims description 5
150000007524 organic acids Chemical group 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
238000003786 synthesis reaction Methods 0.000 abstract description 8
238000000855 fermentation Methods 0.000 abstract description 4
230000004151 fermentation Effects 0.000 abstract description 4
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 abstract description 3
XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 abstract description 3
229960005370 atorvastatin Drugs 0.000 abstract description 3
244000005700 microbiome Species 0.000 abstract description 3
FJLGEFLZQAZZCD-MCBHFWOFSA-N (3R,5S)-fluvastatin Chemical compound C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 FJLGEFLZQAZZCD-MCBHFWOFSA-N 0.000 abstract description 2
241000187643 Amycolatopsis Species 0.000 abstract description 2
229940121710 HMGCoA reductase inhibitor Drugs 0.000 abstract description 2
PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 abstract description 2
241000228347 Monascus <ascomycete fungus> Species 0.000 abstract description 2
241000235395 Mucor Species 0.000 abstract description 2
241000187654 Nocardia Species 0.000 abstract description 2
241000228143 Penicillium Species 0.000 abstract description 2
TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 abstract description 2
AJLFOPYRIVGYMJ-UHFFFAOYSA-N SJ000287055 Natural products C12C(OC(=O)C(C)CC)CCC=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 AJLFOPYRIVGYMJ-UHFFFAOYSA-N 0.000 abstract description 2
230000000326 anti-hypercholesterolaemic effect Effects 0.000 abstract description 2
SEERZIQQUAZTOL-ANMDKAQQSA-N cerivastatin Chemical compound COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)=C1C1=CC=C(F)C=C1 SEERZIQQUAZTOL-ANMDKAQQSA-N 0.000 abstract description 2
229960003765 fluvastatin Drugs 0.000 abstract description 2
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 abstract description 2
229960004844 lovastatin Drugs 0.000 abstract description 2
PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 abstract description 2
QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 abstract description 2
229950009116 mevastatin Drugs 0.000 abstract description 2
AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 abstract description 2
BOZILQFLQYBIIY-UHFFFAOYSA-N mevastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CCC=C21 BOZILQFLQYBIIY-UHFFFAOYSA-N 0.000 abstract description 2
229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 abstract description 2
229960002965 pravastatin Drugs 0.000 abstract description 2
TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 abstract description 2
229960005110 cerivastatin Drugs 0.000 abstract 1
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 10
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
239000012071 phase Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000006227 byproduct Substances 0.000 description 4
239000012467 final product Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
150000001335 aliphatic alkanes Chemical class 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
229910000040 hydrogen fluoride Inorganic materials 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
230000008929 regeneration Effects 0.000 description 2
238000011069 regeneration method Methods 0.000 description 2
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
PARWIGJQSWCJKP-UHFFFAOYSA-N 4-silyloxyoxan-2-one Chemical class [SiH3]OC1CCOC(=O)C1 PARWIGJQSWCJKP-UHFFFAOYSA-N 0.000 description 1
241000228212 Aspergillus Species 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
LDDQLRUQCUTJBB-UHFFFAOYSA-O azanium;hydrofluoride Chemical compound [NH4+].F LDDQLRUQCUTJBB-UHFFFAOYSA-O 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
OZJPLYNZGCXSJM-UHFFFAOYSA-N delta-Valerolactone Natural products O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 1
239000012351 deprotecting agent Substances 0.000 description 1
238000002086 displacement chromatography Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
238000011141 high resolution liquid chromatography Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000009413 insulation Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002596 lactones Chemical group 0.000 description 1
238000007273 lactonization reaction Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000012262 resinous product Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007790 scraping Methods 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
239000002699 waste material Substances 0.000 description 1

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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyrane Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SI9900025A 1999-02-04 1999-02-04 Nov postopek za odstranitev sililoksi zaščitne skupine iz 4-sililoksi tetrahidro-piran-2-on-ov SI20159A (sl)

Priority Applications (9)

Application Number	Priority Date	Filing Date	Title
SI9900025A SI20159A (sl)	1999-02-04	1999-02-04	Nov postopek za odstranitev sililoksi zaščitne skupine iz 4-sililoksi tetrahidro-piran-2-on-ov
DE60010659T DE60010659T2 (de)	1999-02-04	2000-02-02	Verfahren zur entfernung einer silyloxy-schutzgruppe von 4-silyloxy-tetrahydropyran-2-onen
JP2000597287A JP2002536372A (ja)	1999-02-04	2000-02-02	４−シリロキシ−テトラヒドロ−ピラン−２−オン類からシリロキシ保護基を取り除く新規な方法
EP00901283A EP1149086B1 (de)	1999-02-04	2000-02-02	Verfahren zur entfernung einer silyloxy-schutzgruppe von 4-silyloxy-tetrahydropyran-2-onen
US09/869,372 US6509479B1 (en)	1999-02-04	2000-02-02	Process for the removal of a silyloxy protecting group from 4-silyloxy-tetrahydro-pyran-2-ones
AT00901283T ATE266653T1 (de)	1999-02-04	2000-02-02	Verfahren zur entfernung einer silyloxy- schutzgruppe von 4-silyloxy-tetrahydropyran-2- onen
AU21241/00A AU2124100A (en)	1999-02-04	2000-02-02	Novel process for the removal of a silyloxy protecting group from 4-silyloxy-tetrahydro-pyran-2-ones
PCT/IB2000/000105 WO2000046217A1 (en)	1999-02-04	2000-02-02	Novel process for the removal of a silyloxy protecting group from 4-silyloxy-tetrahydro-pyran-2-ones
ES00901283T ES2216853T3 (es)	1999-02-04	2000-02-02	Nuevo procedimiento para la eliminacion de un grupo sililoxi protector de 4-sililoxi-tetrahidro-piran-2-onas.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
SI9900025A SI20159A (sl)	1999-02-04	1999-02-04	Nov postopek za odstranitev sililoksi zaščitne skupine iz 4-sililoksi tetrahidro-piran-2-on-ov

Publications (1)

Publication Number	Publication Date
SI20159A true SI20159A (sl)	2000-08-31

Family

ID=20432398

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SI9900025A SI20159A (sl)	1999-02-04	1999-02-04	Nov postopek za odstranitev sililoksi zaščitne skupine iz 4-sililoksi tetrahidro-piran-2-on-ov

Country Status (9)

Country	Link
US (1)	US6509479B1 (de)
EP (1)	EP1149086B1 (de)
JP (1)	JP2002536372A (de)
AT (1)	ATE266653T1 (de)
AU (1)	AU2124100A (de)
DE (1)	DE60010659T2 (de)
ES (1)	ES2216853T3 (de)
SI (1)	SI20159A (de)
WO (1)	WO2000046217A1 (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100417841B1 (ko) *	2001-02-13	2004-02-05	주식회사종근당	심바스타틴의 개선된 제조방법
EP1363516B1 (de) *	2001-02-27	2005-08-31	Chong Kun Dang Pharmaceutical Corp.	Verbessertes verfahren zur herstellung von simvastatin
SI21187A (sl) *	2002-03-26	2003-10-31	Krka, Tovarna Zdravil D.D., Novo Mesto	Postopek za pripravo 4-oksitetrahidropiran-2-onov
WO2005058861A1 (en) *	2003-12-16	2005-06-30	Uk Chemipharm Co., Ltd.	Process for preparing simvastatin.

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4444784A (en)	1980-08-05	1984-04-24	Merck & Co., Inc.	Antihypercholesterolemic compounds
US5021453A (en) *	1988-03-02	1991-06-04	Merck & Co., Inc.	3-keto HMG-CoA reductase inhibitors
FI893004L (fi)	1988-06-29	1989-12-30	Merck & Co Inc	5-oxygenerade hmg-coa-reduktas -inhibitorer.
US5041562A (en) *	1989-06-09	1991-08-20	Merck & Co., Inc.	3-keto HMG-CoA reductase inhibitors

1999
- 1999-02-04 SI SI9900025A patent/SI20159A/sl not_active IP Right Cessation
2000
- 2000-02-02 WO PCT/IB2000/000105 patent/WO2000046217A1/en not_active Ceased
- 2000-02-02 US US09/869,372 patent/US6509479B1/en not_active Expired - Fee Related
- 2000-02-02 AT AT00901283T patent/ATE266653T1/de not_active IP Right Cessation
- 2000-02-02 DE DE60010659T patent/DE60010659T2/de not_active Expired - Fee Related
- 2000-02-02 JP JP2000597287A patent/JP2002536372A/ja not_active Withdrawn
- 2000-02-02 ES ES00901283T patent/ES2216853T3/es not_active Expired - Lifetime
- 2000-02-02 AU AU21241/00A patent/AU2124100A/en not_active Abandoned
- 2000-02-02 EP EP00901283A patent/EP1149086B1/de not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ES2216853T3 (es)	2004-11-01
EP1149086A1 (de)	2001-10-31
DE60010659D1 (de)	2004-06-17
ATE266653T1 (de)	2004-05-15
AU2124100A (en)	2000-08-25
WO2000046217A1 (en)	2000-08-10
EP1149086B1 (de)	2004-05-12
JP2002536372A (ja)	2002-10-29
US6509479B1 (en)	2003-01-21
DE60010659T2 (de)	2005-05-19

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Date	Code	Title	Description
2005-01-10	IF	Valid on the event date
2007-02-28	KO00	Lapse of patent	Effective date: 20061023

Publication	Publication Date	Title
CA2173830C (en)	1998-04-07	Process for producing simvastatin and analogs thereof
FI88719B (fi)	1993-03-15	Foerfarande foer -c-alkylering av 8-acylgruppen i mevinolin och dess analoger
EP0864569B1 (de)	2001-08-16	Verfahren zur Herstellung Simvastatin von Lovastatin oder Mevinolinsäure
HUP0103021A2 (hu)	2001-12-28	Eljárás szimvasztatinszármazékok előállítására
EP1135380B1 (de)	2003-07-09	Verfahren zur herstellung von simvastatin und deren analogen
SI20159A (sl)	2000-08-31	Nov postopek za odstranitev sililoksi zaščitne skupine iz 4-sililoksi tetrahidro-piran-2-on-ov
EP1056737A1 (de)	2000-12-06	Verfahren zur herstellung von simvastatin und ihren derivaten
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US6573392B1 (en)	2003-06-03	Process for manufacturing simvastatin and the novel intermediates
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