JPS645570B2 - - Google Patents

Info

Publication number: JPS645570B2
Authority: JP; Japan
Prior art keywords: carboxylic acid; monacolin; clathrate; gel; salt
Prior art date: 1981-09-25
Legal status (The legal status 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 status listed.): Expired

Application number

JP15161981A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5855415A (ja

Inventor

Akira Endo

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sankyo Co Ltd

Original Assignee

Sankyo Co Ltd

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

1981-09-25

Publication date

1989-01-31

1981-09-25 Application filed by Sankyo Co Ltd filed Critical Sankyo Co Ltd

1981-09-25 Priority to JP15161981A priority Critical patent/JPS5855415A/ja

1983-04-01 Publication of JPS5855415A publication Critical patent/JPS5855415A/ja

1989-01-31 Publication of JPS645570B2 publication Critical patent/JPS645570B2/ja

Status Granted legal-status Critical Current

Links

-1 monacolin K carboxylic acid Chemical class 0.000 claims description 65
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 claims description 36
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 claims description 21
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 claims description 18
239000003814 drug Substances 0.000 claims description 7
229910052751 metal Inorganic materials 0.000 claims description 7
239000002184 metal Substances 0.000 claims description 7
208000031226 Hyperlipidaemia Diseases 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 5
229940124597 therapeutic agent Drugs 0.000 claims description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
229920000936 Agarose Polymers 0.000 claims description 2
229920002307 Dextran Polymers 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
150000003863 ammonium salts Chemical class 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
229920002401 polyacrylamide Polymers 0.000 claims description 2
229920002554 vinyl polymer Polymers 0.000 claims description 2
229920000642 polymer Polymers 0.000 claims 4
150000002148 esters Chemical class 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
238000003756 stirring Methods 0.000 description 13
239000000243 solution Substances 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
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 8
230000000694 effects Effects 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
235000001014 amino acid Nutrition 0.000 description 5
150000001413 amino acids Chemical class 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000008280 blood Substances 0.000 description 3
238000004108 freeze drying Methods 0.000 description 3
210000003000 inclusion body Anatomy 0.000 description 3
238000000034 method Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
230000003472 neutralizing effect Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
OGNSCSPNOLGXSM-UHFFFAOYSA-N 2,4-diaminobutyric acid Chemical compound NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000700159 Rattus Species 0.000 description 2
229920005654 Sephadex Polymers 0.000 description 2
239000012507 Sephadex™ Substances 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
239000007853 buffer solution Substances 0.000 description 2
150000004676 glycans Chemical class 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
150000002596 lactones Chemical class 0.000 description 2
229920001282 polysaccharide Polymers 0.000 description 2
239000005017 polysaccharide Substances 0.000 description 2
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 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
125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 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
125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 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
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])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
DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229920002271 DEAE-Sepharose Polymers 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
206010015719 Exsanguination Diseases 0.000 description 1
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 description 1
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 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
HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
229920002684 Sepharose Polymers 0.000 description 1
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 1
238000002835 absorbance Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000003529 anticholesteremic agent Substances 0.000 description 1
229940127226 anticholesterol agent Drugs 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000006278 bromobenzyl group Chemical group 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
150000001868 cobalt Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
159000000014 iron salts Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000007774 longterm Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
235000018977 lysine Nutrition 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002815 nickel Chemical class 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
239000003826 tablet Substances 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
MDYZKJNTKZIUSK-UHFFFAOYSA-N tyloxapol Chemical compound O=C.C1CO1.CC(C)(C)CC(C)(C)C1=CC=C(O)C=C1 MDYZKJNTKZIUSK-UHFFFAOYSA-N 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Landscapes

Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

JP15161981A 1981-09-25 1981-09-25 高脂血症治療剤 Granted JPS5855415A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP15161981A JPS5855415A (ja)	1981-09-25	1981-09-25	高脂血症治療剤

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP15161981A JPS5855415A (ja)	1981-09-25	1981-09-25	高脂血症治療剤

Publications (2)

Publication Number	Publication Date
JPS5855415A JPS5855415A (ja)	1983-04-01
JPS645570B2 true JPS645570B2 (fr)	1989-01-31

Family

ID=15522492

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP15161981A Granted JPS5855415A (ja)	1981-09-25	1981-09-25	高脂血症治療剤

Country Status (1)

Country	Link
JP (1)	JPS5855415A (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH02235482A (ja) *	1989-03-09	1990-09-18	Tookado:Kk	ビデオカメラ及びビデオライト用の給電装置
JPH06105199A (ja) *	1993-04-02	1994-04-15	Tookado:Kk	ビデオカメラ及びビデオライト用の給電装置

1981
- 1981-09-25 JP JP15161981A patent/JPS5855415A/ja active Granted

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH02235482A (ja) *	1989-03-09	1990-09-18	Tookado:Kk	ビデオカメラ及びビデオライト用の給電装置
JPH06105199A (ja) *	1993-04-02	1994-04-15	Tookado:Kk	ビデオカメラ及びビデオライト用の給電装置

Also Published As

Publication number	Publication date
JPS5855415A (ja)	1983-04-01

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CH527218A (fr)	1972-08-31	Procédé pour préparer des complexes de coordination de l'aluminium
Katchalski et al.	1946	Synthesis of lysine anhydride
JPH0655722B2 (ja)	1994-07-27	医薬用組成物
JPH0323081B2 (fr)	1991-03-28
WO1991016338A1 (fr)	1991-10-31	Derive de glutathion a substitution-s-(acide gras inferieur)
US4163058A (en)	1979-07-31	Derivatives of 5,5-diphenylhydantoin exhibiting enhanced solubility and the therapeutic use thereof
JPH05148274A (ja)	1993-06-15	ガリウム化合物
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JPS6058209B2 (ja)	1985-12-19	β，γ−ジヒドロポリプレニルアルコ−ルおよびそれからなる血圧降下剤
US4985466A (en)	1991-01-15	Method for treating tumors susceptible to treatment with reduced wool alcohol
NL7908988A (nl)	1980-06-17	Paracetamolderivaat, de bereiding en toepassing daar- van.
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JPS60155197A (ja)	1985-08-15	アルギニン　バソプレツシンきつ抗薬の新規誘導体
US4762850A (en)	1988-08-09	Dopamine-beta-hydroxylase inhibitors
JP3898850B2 (ja)	2007-03-28	金属配位能を有する糖誘導体から成るゲル化剤
US4241055A (en)	1980-12-23	Derivatives of aspirin
JPS62294616A (ja)	1987-12-22	抗真菌用薬剤
JPH07500087A (ja)	1995-01-05	代謝可能な血漿代用品
Zutshi et al.	1990	Kinetic fate of potassium embelate, a non-narcotic centrally acting analgesic after oral and intravenous administration
JPS5855415A (ja)	1983-04-01	高脂血症治療剤
JPS6126526B2 (fr)	1986-06-20
Rauws	1969	Comparison of bromisoval and carbromal in the rat
US3262847A (en)	1966-07-26	Calcium salt of dextran for treating cattle delivery paresis

JPS645570B2 - - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=15522492

Family Applications (1)

Country Status (1)

Cited By (2)

Cited By (2)

Also Published As

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