JPS6032633B2 - 新規イソキノリン誘導体及びこの誘導体を含有する心臓機能不全治療剤 - Google Patents

新規イソキノリン誘導体及びこの誘導体を含有する心臓機能不全治療剤

Info

Publication number: JPS6032633B2
Authority: JP; Japan
Prior art keywords: isoquinoline; tetrahydro; hydroxy; propoxy; novel
Prior art date: 1975-04-30
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

JP51000401A

Other languages

English (en)

Japanese (ja)

Other versions

JPS51131882A (en

Inventor

アルバート・ヴエスターマン

フランク・ツインメルマン

デイルウ・ヴツペルマン

ルートヴイヒ・フリートリツハ

マンフレート・ラシヤツク

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.)

Abbott GmbH and Co KG

Original Assignee

Knoll GmbH

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.)

1975-04-30

Filing date

1976-01-01

Publication date

1985-07-29

1976-01-01 Application filed by Knoll GmbH filed Critical Knoll GmbH

1976-11-16 Publication of JPS51131882A publication Critical patent/JPS51131882A/ja

1985-07-29 Publication of JPS6032633B2 publication Critical patent/JPS6032633B2/ja

Status Expired legal-status Critical Current

Links

230000000747 cardiac effect Effects 0.000 title description 6
239000003814 drug Substances 0.000 title description 4
230000004064 dysfunction Effects 0.000 title description 4
229940124597 therapeutic agent Drugs 0.000 title description 2
125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title 1
-1 methoxy-2-propionyl-isoquinoline Chemical compound 0.000 claims description 20
239000002253 acid Substances 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 7
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
150000002537 isoquinolines Chemical class 0.000 claims 25
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 77
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
230000008018 melting Effects 0.000 description 51
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VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
231100000682 maximum tolerated dose Toxicity 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
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229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
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239000000454 talc Substances 0.000 description 2
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230000002349 favourable effect Effects 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000003292 glue Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
230000005986 heart dysfunction Effects 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000019713 millet Nutrition 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
230000002028 premature Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002994 raw material Substances 0.000 description 1
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
239000012465 retentate Substances 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000036262 stenosis Effects 0.000 description 1
208000037804 stenosis Diseases 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
231100000816 toxic dose Toxicity 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000820 toxicity test Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
210000000689 upper leg Anatomy 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

JP51000401A 1975-04-30 1976-01-01 新規イソキノリン誘導体及びこの誘導体を含有する心臓機能不全治療剤 Expired JPS6032633B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE2519163A DE2519163C2 (de)	1975-04-30	1975-04-30	2-Formyl-1,2,3,4-tetrahydro-5-(2-hydroxy-3-tert.butyl-aminopropoxy)-isochinolin, dessen Salze, Verfahren zu deren Herstellung und ihre Verwendung
DE2519163.3		1975-04-30

Publications (2)

Publication Number	Publication Date
JPS51131882A JPS51131882A (en)	1976-11-16
JPS6032633B2 true JPS6032633B2 (ja)	1985-07-29

Family

ID=5945358

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP51000401A Expired JPS6032633B2 (ja)	1975-04-30	1976-01-01	新規イソキノリン誘導体及びこの誘導体を含有する心臓機能不全治療剤

Country Status (3)

Country	Link
JP (1)	JPS6032633B2 (fr)
CA (1)	CA1050986A (fr)
DE (1)	DE2519163C2 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5280667A (en) *	1975-12-26	1977-07-06	Kazuo Tsumura	High frequency heating type deodorizing apparatus

1975
- 1975-04-30 DE DE2519163A patent/DE2519163C2/de not_active Expired
- 1975-12-10 CA CA241,417A patent/CA1050986A/fr not_active Expired
1976
- 1976-01-01 JP JP51000401A patent/JPS6032633B2/ja not_active Expired

Also Published As

Publication number	Publication date
DE2519163A1 (de)	1976-11-11
DE2519163C2 (de)	1983-12-01
JPS51131882A (en)	1976-11-16
CA1050986A (fr)	1979-03-20

Publication	Publication Date	Title
FR2554719A1 (fr)	1985-05-17	Medicaments a base de nouveaux derives de la vinyl-6 furo-(3,4-c)-pyridine
JPS5919539B2 (ja)	1984-05-07	３，４−ジヒドロカルボスチリル誘導体
JPS6229566A (ja)	1987-02-07	新規グアニジノメチル安息香酸誘導体
US4375479A (en)	1983-03-01	Indanyl derivatives and use
JPS5921850B2 (ja)	1984-05-22	新ナフタレン誘導体の製法
US3483221A (en)	1969-12-09	1 - (isopropylamino)-2-hydroxy-3-(alkenyloxyphenoxy) - propanes and the salts thereof
US4596806A (en)	1986-06-24	7-piperidino-1,2,3,5-tetrahydroimidazo[2,1-b]-quinazolin-2-one having platelet aggregation inhibitory activity
FI79524B (fi)	1989-09-29	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 4-fenyl-4-oxo-2-ensmoersyraderivat.
US4173577A (en)	1979-11-06	Phenylacetohydroxamic acids
US4092430A (en)	1978-05-30	Antiphlogistic phenylacetohydroxamic acid compositions
JPS6032633B2 (ja)	1985-07-29	新規イソキノリン誘導体及びこの誘導体を含有する心臓機能不全治療剤
CA1146953A (fr)	1983-05-24	Acides (3-alkylamino-2-hydroxypropoxy)- furane-2-carboxyliques anilides, leurs sels d'addition d'acide toleres par l'organisme, les methodes pour les preparer et les medicaments les renfermant
EP0011747B1 (fr)	1982-05-19	Dérivés aminopropanols de 6-hydroxy-2,3,4,5-tétrahydro-1H-1-benzazépin-2-ones, procédé pour leur préparation, et compositions pharmaceutiques les contenant
CH449652A (fr)	1968-01-15	Procédé de préparation de nouvelles hydroxydiamines
JPS6026785B2 (ja)	1985-06-25	新規イリキノリン誘導体の製法
US3840539A (en)	1974-10-08	Phthalazine derivatives
US4143143A (en)	1979-03-06	Substituted imidazo[5,1-a]isoquinolines
US4067873A (en)	1978-01-10	Certain 1-amino-3-(1-isoquinolinyl)oxy-2-propanol derivatives
JP2800830B2 (ja)	1998-09-21	１，２，３，４−テトラヒドロイソキノリン抗不整脈薬
US3583994A (en)	1971-06-08	5-benzoyloxy-2-lower alkyl decahydroisoquinolines
US3810986A (en)	1974-05-14	Novel method and composition
US2246529A (en)	1941-06-24	Xylyl methyl carbinamine
JPH0124146B2 (fr)	1989-05-10
US3711505A (en)	1973-01-16	2-(2-imidazolin-2-ylthio)-acetanilides
US3971798A (en)	1976-07-27	Pyridine derivative, processes of preparation and pharmaceutical compositions