DK171877B1 - Analogifremgangsmåde til fremstilling af octahydronaphthalenderivater, de frie hydroxycarboxylsyrer,estere eller salte deraf - Google Patents

Analogifremgangsmåde til fremstilling af octahydronaphthalenderivater, de frie hydroxycarboxylsyrer,estere eller salte deraf Download PDF

Info

Publication number: DK171877B1
Authority: DK; Denmark
Prior art keywords: dihydro; formula; compound; oxo; carboxylate
Prior art date: 1981-09-25

Application number

DK426682A

Other languages

Danish (da)

English (en)

Other versions

DK426682A (da

Inventor

Junya Ide

Shigeki Muramatsu

Yoshio Tsujita

Masao Kuroda

Original Assignee

Sankyo Co

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.)

1981-09-25

Filing date

1982-09-24

Publication date

1997-07-28

1982-09-24 Application filed by Sankyo Co filed Critical Sankyo Co

1983-03-26 Publication of DK426682A publication Critical patent/DK426682A/da

1997-07-28 Application granted granted Critical

1997-07-28 Publication of DK171877B1 publication Critical patent/DK171877B1/da

Links

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XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
150000007517 lewis acids Chemical class 0.000 description 2
230000002503 metabolic effect Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
LXZBFUBRYYVRQJ-AXHZAXLDSA-M sodium;(3r,5r)-7-[(1s,2s,6r,8s,8ar)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate Chemical compound [Na+].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](C)C=C21 LXZBFUBRYYVRQJ-AXHZAXLDSA-M 0.000 description 2
241000894007 species Species 0.000 description 2
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 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
YETDVLVHYIHONL-UHFFFAOYSA-N (chloroamino)oxymethane Chemical compound CONCl YETDVLVHYIHONL-UHFFFAOYSA-N 0.000 description 1
POPHMOPNVVKGRW-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7-octahydronaphthalene Chemical class C1CCC2CCCCC2=C1 POPHMOPNVVKGRW-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
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WGTASENVNYJZBK-UHFFFAOYSA-N 3,4,5-trimethoxyamphetamine Chemical compound COC1=CC(CC(C)N)=CC(OC)=C1OC WGTASENVNYJZBK-UHFFFAOYSA-N 0.000 description 1
125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 description 1
125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
102100029077 3-hydroxy-3-methylglutaryl-coenzyme A reductase Human genes 0.000 description 1
101710158485 3-hydroxy-3-methylglutaryl-coenzyme A reductase Proteins 0.000 description 1
125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 1
125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
229910015900 BF3 Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
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 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
235000002233 Penicillium roqueforti Nutrition 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000005599 alkyl carboxylate group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000010171 animal model Methods 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000326 anti-hypercholesterolaemic effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
150000003974 aralkylamines Chemical class 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
229910001863 barium hydroxide Inorganic materials 0.000 description 1
239000002585 base Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
150000001734 carboxylic acid salts Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
210000004748 cultured cell Anatomy 0.000 description 1
VXVVUHQULXCUPF-UHFFFAOYSA-N cycloheptanamine Chemical compound NC1CCCCCC1 VXVVUHQULXCUPF-UHFFFAOYSA-N 0.000 description 1
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
HERPVHLYIHBEFW-ZETCQYMHSA-N diethyl (2s)-2-aminopentanedioate Chemical compound CCOC(=O)CC[C@H](N)C(=O)OCC HERPVHLYIHBEFW-ZETCQYMHSA-N 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
MLSGRWDEDYJNER-UHFFFAOYSA-N ethyl 2-anilinoacetate Chemical compound CCOC(=O)CNC1=CC=CC=C1 MLSGRWDEDYJNER-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
229960002442 glucosamine Drugs 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
XKIOBYHZFPTKCZ-SECBINFHSA-N methyl (3r)-3-amino-3-phenylpropanoate Chemical compound COC(=O)C[C@@H](N)C1=CC=CC=C1 XKIOBYHZFPTKCZ-SECBINFHSA-N 0.000 description 1
QVDXUKJJGUSGLS-LURJTMIESA-N methyl L-leucinate Chemical compound COC(=O)[C@@H](N)CC(C)C QVDXUKJJGUSGLS-LURJTMIESA-N 0.000 description 1
125000006178 methyl benzyl group Chemical group 0.000 description 1
244000005700 microbiome Species 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 description 1
ZEFLPHRHPMEVPM-UHFFFAOYSA-N n,n-dimethylcyclopentanamine Chemical compound CN(C)C1CCCC1 ZEFLPHRHPMEVPM-UHFFFAOYSA-N 0.000 description 1
ZWRDBWDXRLPESY-UHFFFAOYSA-N n-benzyl-n-ethylethanamine Chemical compound CCN(CC)CC1=CC=CC=C1 ZWRDBWDXRLPESY-UHFFFAOYSA-N 0.000 description 1
ABRGFZIXRKAUJS-UHFFFAOYSA-N n-benzyl-n-methylethanamine Chemical compound CCN(C)CC1=CC=CC=C1 ABRGFZIXRKAUJS-UHFFFAOYSA-N 0.000 description 1
VFPQRGMSTSEZFW-UHFFFAOYSA-N n-ethylcycloheptanamine Chemical compound CCNC1CCCCCC1 VFPQRGMSTSEZFW-UHFFFAOYSA-N 0.000 description 1
AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
KKTBUCVHSCATGB-UHFFFAOYSA-N n-methylcyclopentanamine Chemical compound CNC1CCCC1 KKTBUCVHSCATGB-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000000039 preparative column chromatography Methods 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
LNSVFWNJSKUQAL-LLVKDONJSA-N propyl (3r)-3-amino-3-phenylpropanoate Chemical compound CCCOC(=O)C[C@@H](N)C1=CC=CC=C1 LNSVFWNJSKUQAL-LLVKDONJSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
- 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
- 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
- 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

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Organic Chemistry (AREA)
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Animal Behavior & Ethology (AREA)
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Obesity (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Hematology (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrane Compounds (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Artificial Filaments (AREA)
Compositions Of Macromolecular Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Indole Compounds (AREA)

DK426682A 1981-09-25 1982-09-24 Analogifremgangsmåde til fremstilling af octahydronaphthalenderivater, de frie hydroxycarboxylsyrer,estere eller salte deraf DK171877B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP56151871A JPS5855443A (ja)	1981-09-25	1981-09-25	オクタヒドロナフタリン誘導体およびその製造法
JP15187181		1981-09-25

Publications (2)

Publication Number	Publication Date
DK426682A DK426682A (da)	1983-03-26
DK171877B1 true DK171877B1 (da)	1997-07-28

Family

ID=15528032

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK426682A DK171877B1 (da)	1981-09-25	1982-09-24	Analogifremgangsmåde til fremstilling af octahydronaphthalenderivater, de frie hydroxycarboxylsyrer,estere eller salte deraf

Country Status (12)

Country	Link
US (2)	US4604472A (fi)
EP (1)	EP0076601B1 (fi)
JP (1)	JPS5855443A (fi)
KR (1)	KR890000364B1 (fi)
AT (1)	ATE19074T1 (fi)
AU (1)	AU555242B2 (fi)
CA (1)	CA1298845C (fi)
DE (1)	DE3270445D1 (fi)
DK (1)	DK171877B1 (fi)
ES (1)	ES8308556A1 (fi)
FI (1)	FI79706C (fi)
IE (1)	IE53910B1 (fi)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5855443A (ja) *	1981-09-25	1983-04-01	Sankyo Co Ltd	オクタヒドロナフタリン誘導体およびその製造法
US4472426A (en) *	1982-12-22	1984-09-18	Merck & Co., Inc.	Antihypercholesterolemic compounds
US4719229A (en) *	1987-05-13	1988-01-12	Merck & Co., Inc.	Antihypercholesterolemic agents
US4997848A (en) *	1987-10-27	1991-03-05	Sankyo Company, Limited	Octahydronaphthalene oxime derivatives for cholesterol synthesis inhibition
JP2542429B2 (ja) *	1987-10-27	1996-10-09	三共株式会社	オクタヒドロナフタリン置換オキシム誘導体
US4841074A (en) *	1987-12-11	1989-06-20	Merck & Co., Inc.	Intermediates and processes for 6-carboxy HMG-CoA reductase inhibitors
US5021453A (en) *	1988-03-02	1991-06-04	Merck & Co., Inc.	3-keto HMG-CoA reductase inhibitors
US4857522A (en) *	1988-03-21	1989-08-15	E. R. Squibb & Sons, Inc.	Derivatives of pravastatin for inhibiting cholesterol biosynthesis
US4963538A (en) *	1988-06-29	1990-10-16	Merck & Co., Inc.	5-oxygenated HMG-CoA reductase inhibitors
US4921974A (en) *	1988-09-29	1990-05-01	Merck & Co., Inc.	Intermediates and processes in the preparation of 5-oxygenated HMG-COA reductase inhibitors
JPH0233347U (fi) *	1988-08-27	1990-03-02
US5166364A (en) *	1989-02-27	1992-11-24	E. R. Squibb & Sons, Inc.	Mevinic acid derivatives useful as antihypercholesterolemic agents and method for preparing same
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1981
- 1981-09-25 JP JP56151871A patent/JPS5855443A/ja active Granted
1982
- 1982-09-21 CA CA000411825A patent/CA1298845C/en not_active Expired - Fee Related
- 1982-09-23 EP EP82305015A patent/EP0076601B1/en not_active Expired
- 1982-09-23 DE DE8282305015T patent/DE3270445D1/de not_active Expired
- 1982-09-23 AT AT82305015T patent/ATE19074T1/de not_active IP Right Cessation
- 1982-09-24 FI FI823282A patent/FI79706C/fi not_active IP Right Cessation
- 1982-09-24 ES ES515954A patent/ES8308556A1/es not_active Expired
- 1982-09-24 DK DK426682A patent/DK171877B1/da active
- 1982-09-24 IE IE2319/82A patent/IE53910B1/en not_active IP Right Cessation
- 1982-09-24 AU AU88666/82A patent/AU555242B2/en not_active Expired
1985
- 1985-07-09 US US06/753,254 patent/US4604472A/en not_active Expired - Lifetime
1986
- 1986-05-06 US US06/860,185 patent/US4733003A/en not_active Expired - Lifetime
1988
- 1988-09-22 KR KR1019880012273A patent/KR890000364B1/ko not_active IP Right Cessation

Also Published As

Publication number	Publication date
JPS5855443A (ja)	1983-04-01
KR890000364B1 (ko)	1989-03-15
FI79706C (fi)	1990-02-12
FI823282A0 (fi)	1982-09-24
US4733003A (en)	1988-03-22
FI823282L (fi)	1983-03-26
EP0076601B1 (en)	1986-04-09
DE3270445D1 (en)	1986-05-15
ES515954A0 (es)	1983-09-16
ES8308556A1 (es)	1983-09-16
JPH0153662B2 (fi)	1989-11-15
FI79706B (fi)	1989-10-31
IE53910B1 (en)	1989-04-12
AU8866682A (en)	1983-03-31
EP0076601A1 (en)	1983-04-13
ATE19074T1 (de)	1986-04-15
DK426682A (da)	1983-03-26
AU555242B2 (en)	1986-09-18
CA1298845C (en)	1992-04-14
US4604472A (en)	1986-08-05
IE822319L (en)	1983-03-25

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EP0216785B1 (en)	1991-01-30	Indene analogs of mevalonolactone and derivatives thereof
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NO762107L (fi)	1976-12-28
CA2027765C (en)	2001-04-17	Mevinic acid derivatives
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KR880002462B1 (ko)	1988-11-14	옥타히드로나프탈렌 유도체의 제조방법
FR2515642A1 (fr)	1983-05-06	Nouvelles (11r)-11-deoxy-11-alkyl-6-oxo-prostaglandines et compositions pharmaceutiques les contenant
CA1307263C (en)	1992-09-08	Hmg-coa reductase inhibitors
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FI92061C (fi)	1994-09-26	1,3-substituoitu-(14-/7-metyyli-4,6-diokso-heksa-hydro-naft-8-yyli/etyyli)-16-suojattu hydroksi-14,15,17-tetrahydro-18H-pyran-18-onit ja niiden valmistus
US5149835A (en)	1992-09-22	Substituted mevalonolactones, and methods for stereoselective preparation thereof and desmethyl homologues thereof
Bagli et al.	1975	Prostaglandin VIII—Synthesis of some 9-oxoprostynoic acids
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GB2072672A (en)	1981-10-07	Process for the preparation of 2- substituted-4-hydroxy-2-cyclopenten- 1-ones