DK172811B1 - Naphthalenderivat og fremgangsmåde til fremstilling deraf - Google Patents

Naphthalenderivat og fremgangsmåde til fremstilling deraf Download PDF

Info

Publication number: DK172811B1
Authority: DK; Denmark
Prior art keywords: alkyl; carbon atoms; osi; process according; methyl
Prior art date: 1987-07-10

Application number

DK198803807A

Other languages

Danish (da)

English (en)

Other versions

DK380788A (da

DK380788D0 (da

Inventor

David Askin

Thomas R Verhoeven

Original Assignee

Merck & Co Inc

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.)

1987-07-10

Filing date

1988-07-08

Publication date

1999-07-26

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=22105351&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=DK172811(B1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1988-07-08 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1988-07-08 Publication of DK380788D0 publication Critical patent/DK380788D0/da

1989-02-15 Publication of DK380788A publication Critical patent/DK380788A/da

1999-07-26 Application granted granted Critical

1999-07-26 Publication of DK172811B1 publication Critical patent/DK172811B1/da

Links

238000000034 method Methods 0.000 title claims abstract description 28
150000002790 naphthalenes Chemical class 0.000 title claims description 5
238000002360 preparation method Methods 0.000 title description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
-1 alkali metal amide Chemical class 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
229910052783 alkali metal Inorganic materials 0.000 claims description 6
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical group CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 4
229910052744 lithium Inorganic materials 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
150000003973 alkyl amines Chemical class 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
239000012298 atmosphere Substances 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
FJDQVJUXXNIHNB-UHFFFAOYSA-N lithium;pyrrolidin-1-ide Chemical group [Li+].C1CC[N-]C1 FJDQVJUXXNIHNB-UHFFFAOYSA-N 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
125000000623 heterocyclic group Chemical group 0.000 claims 1
239000011630 iodine Chemical group 0.000 claims 1
229910052740 iodine Chemical group 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
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 10
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 9
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 9
150000001350 alkyl halides Chemical class 0.000 abstract description 5
230000002152 alkylating effect Effects 0.000 abstract description 2
239000000203 mixture Substances 0.000 description 13
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
239000007858 starting material Substances 0.000 description 8
239000000047 product Substances 0.000 description 7
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
238000005804 alkylation reaction Methods 0.000 description 6
239000002585 base Substances 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical group CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 description 3
WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical group CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
102000004286 Hydroxymethylglutaryl CoA Reductases Human genes 0.000 description 3
108090000895 Hydroxymethylglutaryl CoA Reductases Proteins 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
238000000855 fermentation Methods 0.000 description 3
230000004151 fermentation Effects 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
VGMFHMLQOYWYHN-UHFFFAOYSA-N Compactin Natural products OCC1OC(OC2C(O)C(O)C(CO)OC2Oc3cc(O)c4C(=O)C(=COc4c3)c5ccc(O)c(O)c5)C(O)C(O)C1O VGMFHMLQOYWYHN-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 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 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
150000002148 esters Chemical group 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
150000002596 lactones Chemical class 0.000 description 2
229960004844 lovastatin Drugs 0.000 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 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 description 2
239000012074 organic phase Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
FHSAZOGISLHXPK-UHFFFAOYSA-N 3-hydroxyoxan-2-one Chemical compound OC1CCCOC1=O FHSAZOGISLHXPK-UHFFFAOYSA-N 0.000 description 1
125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
UUIQMZJEGPQKFD-UHFFFAOYSA-N Methyl butyrate Chemical group CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
238000010961 commercial manufacture process Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
229940102396 methyl bromide Drugs 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
230000037361 pathway Effects 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000006884 silylation reaction Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Steroid Compounds (AREA)
Cephalosporin Compounds (AREA)
Peptides Or Proteins (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DK198803807A 1987-07-10 1988-07-08 Naphthalenderivat og fremgangsmåde til fremstilling deraf DK172811B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US07/072,066 US4820850A (en)	1987-07-10	1987-07-10	Process for α-C-alkylation of the 8-acyl group on mevinolin and analogs thereof
US7206687		1987-07-10

Publications (3)

Publication Number	Publication Date
DK380788D0 DK380788D0 (da)	1988-07-08
DK380788A DK380788A (da)	1989-02-15
DK172811B1 true DK172811B1 (da)	1999-07-26

Family

ID=22105351

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK198803807A DK172811B1 (da)	1987-07-10	1988-07-08	Naphthalenderivat og fremgangsmåde til fremstilling deraf

Country Status (22)

Country	Link
US (1)	US4820850A (de)
EP (1)	EP0299656B1 (de)
JP (2)	JPH0717663B2 (de)
KR (1)	KR950009314B1 (de)
CN (1)	CN1019395B (de)
AT (1)	ATE59036T1 (de)
AU (1)	AU604937B2 (de)
CA (1)	CA1287063C (de)
CY (1)	CY1613A (de)
DE (1)	DE3861270D1 (de)
DK (1)	DK172811B1 (de)
ES (1)	ES2018710B3 (de)
FI (1)	FI88719C (de)
GR (1)	GR3001351T3 (de)
HK (1)	HK98991A (de)
IE (1)	IE61025B1 (de)
IL (1)	IL86968A (de)
NO (1)	NO172239C (de)
NZ (1)	NZ225306A (de)
PT (1)	PT87909B (de)
SG (1)	SG84691G (de)
ZA (1)	ZA884924B (de)

Families Citing this family (116)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5159104A (en) *	1991-05-01	1992-10-27	Merck & Co., Inc.	Process to simvastatin ester
GB9123933D0 (en) *	1991-11-11	1992-01-02	British Bio Technology	Compounds
US5393893A (en) *	1993-11-08	1995-02-28	Apotex, Inc.	Process for producing simvastatin and analogs thereof
US5763653A (en) *	1997-03-13	1998-06-09	Ranbaxy Laboratories, Ltd.	Key intermediates in the manufacture of simvastatin
CA2185961A1 (en) *	1996-09-19	1998-03-20	K.S. Keshava Murthy	Process for producing simvastatin
US5763646A (en) *	1997-03-13	1998-06-09	Ranbaxy Laboratories, Ltd.	Process for manufacturing simvastatin from lovastatin or mevinolinic acid
ES2266671T3 (es)	1997-01-28	2007-03-01	Plus Chemicals B.V.	Proceso para la produccion de estatinas semisinteticas a traves de nuevos intermediarios.
IN186879B (de) *	1997-10-28	2001-12-01	Ranbaxy Lab Ltd
IN186880B (de) *	1997-10-28	2001-12-01	Ranbaxy Lab Ltd
SI9800057A (sl) *	1998-02-26	1999-08-31	Krka, Tovarna Zdravil, D.D.	Postopek za pripravo simvastatina in njegovih derivatov
EP0940395A1 (de) *	1998-03-05	1999-09-08	Synthon B.V.	Verfahren zur Erzeugung von Simvatarin in und/oder deren Derivate
NO991045L (no) *	1998-03-05	1999-09-06	Synthon Bv	FremgangsmÕte ved fremstilling av simvastatin og/eller dets derivater
ZA9810764B (en) *	1998-04-22	1999-08-13	Ranbaxy Lab Ltd	An improved process of lactonization in the preparation of statins.
CA2240983A1 (en) *	1998-06-18	1999-12-18	Yong Tao	Process to manufacture simvastatin and intermediates
SI20116A (sl)	1998-12-02	2000-06-30	LEK, tovarna farmacevtskih in kemi�nih izdelkov, d.d.	Nov postopek za pripravo simvastatina in njegovih analogov
CO5140104A1 (es)	1999-02-16	2002-03-22	Novartis Ag	Derivados de mevinolina y preparacion farmaceuticas que los contienen
US6569461B1 (en) *	1999-03-08	2003-05-27	Merck & Co., Inc.	Dihydroxy open-acid and salts of HMG-CoA reductase inhibitors
WO2001030773A2 (en)	1999-10-27	2001-05-03	Merck & Co., Inc.	Lactonization process
AU2127500A (en)	1999-11-11	2001-06-06	Biocon India Limited	Process for manufacturing simvastatin and the novel intermediates
US6573385B1 (en)	1999-11-11	2003-06-03	Biocon India Limited	Process for manufacturing simvastatin and novel intermediates thereof
CA2402061A1 (en)	2000-03-03	2001-09-13	Vilmos Keri	A process for purifying lovastatin and simvastatin with reduced levels of dimeric impurities
CZ2003554A3 (cs)	2000-07-27	2003-08-13	Plus Chemicals, B. V.	Vysoce přečištěný simvastatin
WO2002024675A1 (en) *	2000-09-13	2002-03-28	Biocon India Limited	Process for manufacturing simvastatin and the novel intermediates
NL1017548C2 (nl)	2001-03-09	2002-09-10	Synthon Bv	Een lactonisatie proces.
EP1294706A1 (de) *	2001-05-18	2003-03-26	Aurobindo Pharma Limited	Prozess zur herstellung von simvastatin durch lactonisierung
US6797831B2 (en) *	2001-05-18	2004-09-28	Aurobindo Pharma Limited	Process for lactonization to produce simvastatin
KR100407758B1 (ko) *	2001-08-27	2003-12-01	씨제이 주식회사	스타틴의 제조에 있어서 락톤화 방법
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1987
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1988
- 1988-07-01 DE DE8888306050T patent/DE3861270D1/de not_active Expired - Lifetime
- 1988-07-01 AT AT88306050T patent/ATE59036T1/de not_active IP Right Cessation
- 1988-07-01 ES ES88306050T patent/ES2018710B3/es not_active Expired - Lifetime
- 1988-07-01 EP EP88306050A patent/EP0299656B1/de not_active Expired - Lifetime
- 1988-07-04 PT PT87909A patent/PT87909B/pt not_active IP Right Cessation
- 1988-07-04 FI FI883184A patent/FI88719C/fi not_active IP Right Cessation
- 1988-07-04 IL IL86968A patent/IL86968A/xx not_active IP Right Cessation
- 1988-07-06 NZ NZ225306A patent/NZ225306A/xx unknown
- 1988-07-08 NO NO883062A patent/NO172239C/no not_active IP Right Cessation
- 1988-07-08 ZA ZA884924A patent/ZA884924B/xx unknown
- 1988-07-08 CA CA000571603A patent/CA1287063C/en not_active Expired - Lifetime
- 1988-07-08 AU AU18850/88A patent/AU604937B2/en not_active Expired
- 1988-07-08 IE IE210688A patent/IE61025B1/en not_active IP Right Cessation
- 1988-07-08 DK DK198803807A patent/DK172811B1/da not_active IP Right Cessation
- 1988-07-09 JP JP63170054A patent/JPH0717663B2/ja not_active Expired - Fee Related
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1991
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1992
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1994
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Publication number	Publication date
JPH07196641A (ja)	1995-08-01
NZ225306A (en)	1990-06-26
FI88719B (fi)	1993-03-15
KR890002199A (ko)	1989-04-08
IE882106L (en)	1989-01-10
NO172239C (no)	1993-06-23
ATE59036T1 (de)	1990-12-15
AU1885088A (en)	1989-01-12
CN1019395B (zh)	1992-12-09
US4820850A (en)	1989-04-11
IL86968A0 (en)	1988-12-30
JPH0717663B2 (ja)	1995-03-01
NO883062L (no)	1989-01-11
CN1031086A (zh)	1989-02-15
GR3001351T3 (en)	1992-09-11
IE61025B1 (en)	1994-09-07
ES2018710B3 (es)	1991-05-01
FI88719C (fi)	1993-06-28
EP0299656B1 (de)	1990-12-12
FI883184A7 (fi)	1989-01-11
JP2527535B2 (ja)	1996-08-28
PT87909A (pt)	1989-06-30
CY1613A (en)	1992-07-10
HK98991A (en)	1991-12-13
ZA884924B (en)	1989-01-17
AU604937B2 (en)	1991-01-03
JPS6470481A (en)	1989-03-15
CA1287063C (en)	1991-07-30
EP0299656A1 (de)	1989-01-18
DK380788A (da)	1989-02-15
IL86968A (en)	1992-12-01
DK380788D0 (da)	1988-07-08
PT87909B (pt)	1995-03-01
KR950009314B1 (ko)	1995-08-19
SG84691G (en)	1991-11-22
FI883184A0 (fi)	1988-07-04
NO172239B (no)	1993-03-15
DE3861270D1 (de)	1991-01-24
NO883062D0 (no)	1988-07-08

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1999-07-26	B1	Patent granted (law 1993)
2008-07-28	PUP	Patent expired

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