JPS6411617B2 - - Google Patents

Info

Publication number: JPS6411617B2
Authority: JP; Japan
Prior art keywords: monacolin; ester; formula; salts; carboxylic acid
Prior art date: 1980-02-19
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

JP1938680A

Other languages

English (en)

Japanese (ja)

Other versions

JPS56115717A (en

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.)

Individual

Original Assignee

Individual

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.)

1980-02-19

Filing date

1980-02-19

Publication date

1989-02-27

1980-02-19 Application filed by Individual filed Critical Individual

1980-02-19 Priority to JP1938680A priority Critical patent/JPS56115717A/ja

1981-09-11 Publication of JPS56115717A publication Critical patent/JPS56115717A/ja

1989-02-27 Publication of JPS6411617B2 publication Critical patent/JPS6411617B2/ja

Status Granted legal-status Critical Current

Links

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 17
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 10
206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 8
208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 8
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 8
239000003814 drug Substances 0.000 claims description 7
229940124597 therapeutic agent Drugs 0.000 claims description 6
230000000069 prophylactic effect Effects 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 3
-1 amino acid salts Chemical class 0.000 description 46
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Chemical class 0.000 description 8
241000282472 Canis lupus familiaris Species 0.000 description 7
150000003839 salts Chemical class 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
125000000217 alkyl group Chemical group 0.000 description 3
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
230000027939 micturition Effects 0.000 description 3
201000004240 prostatic hypertrophy Diseases 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
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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 2
241000699670 Mus sp. Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
150000001413 amino acids Chemical class 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
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
150000001733 carboxylic acid esters Chemical class 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
238000002559 palpation Methods 0.000 description 2
210000002307 prostate Anatomy 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 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
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
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
239000004475 Arginine Substances 0.000 description 1
229910015900 BF3 Inorganic materials 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000031003 Monascus ruber Species 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
241000228143 Penicillium Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
206010051482 Prostatomegaly Diseases 0.000 description 1
241000981595 Zoysia japonica Species 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
230000002378 acidificating effect Effects 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic 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
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
125000006278 bromobenzyl group Chemical group 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000001868 cobalt Chemical class 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
229940079593 drug Drugs 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 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
231100000053 low toxicity Toxicity 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
238000000034 method Methods 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 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
230000003472 neutralizing effect Effects 0.000 description 1
150000002815 nickel Chemical class 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1

Landscapes

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

JP1938680A 1980-02-19 1980-02-19 Preventive and remedy for prostatomegaly Granted JPS56115717A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP1938680A JPS56115717A (en)	1980-02-19	1980-02-19	Preventive and remedy for prostatomegaly

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP1938680A JPS56115717A (en)	1980-02-19	1980-02-19	Preventive and remedy for prostatomegaly

Publications (2)

Publication Number	Publication Date
JPS56115717A JPS56115717A (en)	1981-09-11
JPS6411617B2 true JPS6411617B2 (fr)	1989-02-27

Family

ID=11997848

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP1938680A Granted JPS56115717A (en)	1980-02-19	1980-02-19	Preventive and remedy for prostatomegaly

Country Status (1)

Country	Link
JP (1)	JPS56115717A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT642341E (pt) *	1992-05-13	2001-01-31	Us Health	Utilizacao de inibidores de redutase de 3-hidroxi-3-metilglutaril coenzima a no tratamento de cancro

1980
- 1980-02-19 JP JP1938680A patent/JPS56115717A/ja active Granted

Also Published As

Publication number	Publication date
JPS56115717A (en)	1981-09-11

Publication	Publication Date	Title
US4137322A (en)	1979-01-30	ML-236B carboxylic acid derivatives and their use as antihyperlipemic agents
SU1052507A1 (ru)	1983-11-07	Смесь 1,3- и 1,2-бис-/ди-н-пропилацетат/глицерина,обладающа противосудорожной активностью
IE41724B1 (en)	1980-03-12	Diphenylsulphoxide derivatives
US20180344752A1 (en)	2018-12-06	Thyroid hormone receptor agonist and use thereof
US3934034A (en)	1976-01-20	Hydroxy substituted diphenylalkyls for treatment of lipidemia
JPS6229423B2 (fr)	1987-06-25
US4654363A (en)	1987-03-31	Synthetic analogs of mevinolin
LU80016A1 (fr)	1980-02-14	Procede de preparation de nouvelles 4-pyrones substituees en positions 2,3 et 6 et medicament les contenant
DD210027B3 (de)	1990-07-18	Verfahren zur herstellung von carbacyclinderivaten
US4791133A (en)	1988-12-13	Phenylene, furyl, and thienyl leukotriene B4 analogues
US5149697A (en)	1992-09-22	Cobalt porphyrin pharmaceutical compositions
US4292319A (en)	1981-09-29	Antiphlogistic pharmaceutical compositions and method of use
JPS6341474A (ja)	1988-02-22	抗炎症剤
JPH0234951B2 (fr)	1990-08-07
JPS6412246B2 (fr)	1989-02-28
JPH0365338B2 (fr)	1991-10-11
JP3357378B2 (ja)	2002-12-16	糖尿病処置用のオキシランカルボン酸
MX2024002146A (es)	2024-03-08	Compuestos para el tratamiento de afecciones relacionadas con la actividad de pcsk9.
JPH037670B2 (fr)	1991-02-04
US3558626A (en)	1971-01-26	2-(4 - (diphenyl-2-pyrimidinyl)phenoxy) lower aliphatic monocarbocyclic acids and esters
LU81285A1 (fr)	1980-12-16	Derive de tetrahydro-isoquinoleine
US4440691A (en)	1984-04-03	Indancarboxylic acid zinc salts
JPS645570B2 (fr)	1989-01-31
JPS5883694A (ja)	1983-05-19	８−ベンゾイルアミノアルキルピロリチジン誘導体
EP0067008B1 (fr)	1985-08-21	Ester d'acide carboxylique