IL41664A - 2,6-diamino-dihydropyridines,their production and pharmaceutical compositions containing them - Google Patents
2,6-diamino-dihydropyridines,their production and pharmaceutical compositions containing themInfo
- Publication number
- IL41664A IL41664A IL7341664A IL4166473A IL41664A IL 41664 A IL41664 A IL 41664A IL 7341664 A IL7341664 A IL 7341664A IL 4166473 A IL4166473 A IL 4166473A IL 41664 A IL41664 A IL 41664A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- radical
- alkyl
- radicals
- alkoxy
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4418—Non condensed pyridines; Hydrogenated derivatives thereof having a carbocyclic group directly attached to the heterocyclic ring, e.g. cyproheptadine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
1379005 Dihydropyridines BAYER AG 6 March 1973 [6 March 1972 12 Sept 1972] 10759/73 Heading C2C The invention comprises novel compounds of the tautomeric formulae in which R is a saturated or unsaturated, straight-chain, branched or cyclic hydrocarbon radical, or an aryl radical optionally carrying 1, 2 or 3 identical or different substitutents selected from aryl, alkyl, alkoxy, azido, halogen, nitro, cyano, trifluoromethyl, carbalkoxy and -SO n -Alkyl (in which n = 0, 1 or 2) radicals, or a naphthyl, quinolyl, isoquinolyl, pyridyl, pyrimidyl, thenyl, furyl or pyrryl radical optionally carrying at least one substituent selected from alkyl, alkoxy and halogen radicals; and R<SP>1</SP> and R<SP>2</SP> which can be the same or different, are each a radical -OR<SP>1</SP> in which R<SP>1</SP> is a straight-chain, branched or cyclic, saturated or unsaturated aliphatic hydrocarbon radical the carbon chain of which may be interrupted by 1 or 2 oxygen atoms, or an amino, alkylamino, or dialkylamino group. They are made by reacting an amidine of formula with RCHO or with an ylidene cyanoacetic acid derivative of formula R<SP>1</SP>OC-C(.CN)(:CHR). Pharmaceutical preparations especially useful as coronary and anti-hypertensive agents contain the novel compounds as active ingredients; standard administration forms are described.
[GB1379005A]
Claims (1)
1. ! 41664/2 „ ί CLAIMS ! 1. 2,6-Diamino-dihydropyridines of the tautomeric general formula:- . ■ ' ' c in which R is lower alkyl,. phenyl optionally substituted by- one or two identical or different substituents selected from phenyl, alkyl, alkoxy, azido, halogen, nitro, cyano, trifluoromethyl, lower carbalkoxy, and lower" aikylthio, or is a naphtyl, quinolyl, pyr/idyl furyl,or pyrimidyl radical optionally carrying at least one substituent selected from lower alkyl , ..■.·"' lower alkoxy and halogen, and 1 2 R and R which can be the same or different are each lower alkoxy or lower alkynyloxy. * 2. Compounds according to Claim 1 in which R is a k straight-chai or branched alkyl radical with up to f carbon j 41664/2 i ' atoms, or a phenyl radical carrying 1 or 2 identical or different substituents selected from alk l radicals with up to 4 carbon atoms, (alkoxy radicals with up to 4 carbon 'atoms, chlorine, bromine, nitro, cyjano and trifluoromethyl radicals,- carbalkoxy radicals with 'up to 4 carbon atoms in the alkoxy group, alkylthio in which the alkyl contains up to 4 carbon at'oms, or is a naphthyl, quinolyl, pyridyl, pyrimidyl, or furyl radical, optionally carrying at least one substituent selectee! from alkyl radicals with up to 4 carbon atoms, alkoxy radicals with up to 4 carbon atoms, chlorine and bromine atoms. 3. Compounds according to claim 1 or 2 in which 2 and R are each a radical -OR' in which R1 is a straight- chain or branched alkyl radical with up to 6 carbon atoms tho oarbon ohain of whioh may bo intorruptod by ono oxygon an alkyfiyl radical. 4. The compound of the formula:- T e oompound. of the formula ; L A 1 225 -29- 6. The compound of the formula: - 7. The compound of the formula: 8. The compound of the formul :- 9. Compounds according to claim 1 that are hereinbefore specifically mentioned other than those claimed in claims 4 to 8 and those specifically mentioned in Examples 22, 23 and 24. 10. Compounds according to claim 1 which are hereinbefore specifically mentioned in Examples 22, 23 and 24. 11. A process for the production of a compound according to any of claims 1 to 9 in which either: - (a) an aldehyde of the general formula:- RCHO (II) is reacted with two moles of an amidine of the general formula:- in an inert organic solvent; or (b) an ylidene cyanoacetic acid derivative of the general formula:- R1 OC-C=CHR f (IV) CN is reacted with an amidine of the general formula:- in the presence of an alkali metal alcoholate and an inert organic solvent; 1 2 (in which general formulae II to IV, R, R and R are as defined in any of claims 1 to 3). 12. A process according to claim 11 in which the solvent is an alcohol, an ether, pyridine, dimethylformamide, dimethyl-sulphoxide or acetonitrile. 13. process according to claim 11 or 12 in which the reaction is carried out at 20 to 200°G. 1 . A process for the production of a compound according to claim 1 substantially as hereinbefore described in any of Examples 1 to 21. 15. A process for the production of a compound according to claim 1 substantially as hereinbefore described in Example 22, 23 or 24. 16. Compounds according to claim 1 whenever produced by a process according to any of claims 11 t'o 14. 17. Compounds according to claim 1 whenever produced by a Le A 14 225 -31- process according to claim 15. 18. A pharmaceutical composition containing as an active ingredient a compound according to any of claims 1 to 9 and 16 in admixture with a solid or liquefied gaseous diluent or in admixture with a liquid diluent other than a solvent of a molecular weight less than 200 except in the presence of a surface-active agent. 19. A pharmaceutical composition containing as an active ingredient a compound according to any of claims 1 to 9 and 16 in the form of a sterile or isotonic aqueous solution. 20. A composition according to claim 18 or 19 containing 0.1 to 90 of active ingredient by weight. 21. A pharmaceutical composition according to claim 18 or 1 in which the said compound is a compound according to claim 10 or 17. 22. A pharmaceutical composition according to claim 18 or 1 substantially as hereinbefore described. 23. A medicament in dosage unit form comprising a compound according to an of claims 1 to 9 and 16 either alone or in admixture with a diluent. 24. A medicament in the form of tablets, pills, dragees, capsules, ampoules or suppositories comprising a compound according to any of claims 1 to 9 and 16 either alone or in admixture with a diluent. 25. A medicament according to any of claims 22 to 24 in which the said compound is a compound according to claim 10 or 17. 26. A medicament according to claim 23 or 24 substantiall as hereinbefore described. 27. A method of combatting circulatory disturbances in human and non-human animals which comprises administering to Le A 1 225 the animal an active compound according to any of claims 1 to 9 and 16 either alone or in admixture with a diluent or in the form of a medicament according to claim 23 or 24. 28. A method according to claim 27 in which the active compound is administered intravenously. 29. A method according to claim 28 in which the active compound is administered in an amount of 0.05 to 10 mg/kg body weight/day. 30. A method according to claim 27 in which the active compound is administered perorally. 31. A method according to claim 30 in which the active compound is administered in an amount of 1 to 20 mg/kg body weight/day. 32. A method according to any of claims 27 to 31 in which the active compound is a compound according to claim 10 or 17 according to claim 27 33· A method /of combatting circulatory disturbances, substantially as hereinbefore described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2210687A DE2210687C3 (en) | 1972-03-06 | 1972-03-06 | 2,6-diamino-3,5-diethoxycarbonyldihydropyridines, process for their preparation and pharmaceuticals containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41664A0 IL41664A0 (en) | 1973-05-31 |
| IL41664A true IL41664A (en) | 1976-01-30 |
Family
ID=5838037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL7341664A IL41664A (en) | 1972-03-06 | 1973-03-02 | 2,6-diamino-dihydropyridines,their production and pharmaceutical compositions containing them |
Country Status (24)
| Country | Link |
|---|---|
| JP (2) | JPS5626659B2 (en) |
| KR (1) | KR780000119B1 (en) |
| AT (3) | AT327904B (en) |
| BE (1) | BE796279A (en) |
| BG (2) | BG22815A3 (en) |
| CA (1) | CA988524A (en) |
| CH (2) | CH577473A5 (en) |
| CS (2) | CS182781B2 (en) |
| DD (1) | DD106833A5 (en) |
| DE (1) | DE2210687C3 (en) |
| DK (1) | DK136061C (en) |
| ES (1) | ES412323A1 (en) |
| FI (1) | FI55996C (en) |
| FR (1) | FR2181789B1 (en) |
| GB (1) | GB1379005A (en) |
| HU (1) | HU167089B (en) |
| IE (1) | IE37370B1 (en) |
| IL (1) | IL41664A (en) |
| LU (1) | LU67147A1 (en) |
| NL (1) | NL7303137A (en) |
| PL (2) | PL89256B1 (en) |
| RO (2) | RO63068A (en) |
| SE (1) | SE384208B (en) |
| ZA (1) | ZA731501B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2210687C3 (en) * | 1972-03-06 | 1981-09-24 | Bayer Ag, 5090 Leverkusen | 2,6-diamino-3,5-diethoxycarbonyldihydropyridines, process for their preparation and pharmaceuticals containing them |
| DE2406198C2 (en) * | 1974-02-09 | 1983-12-15 | Bayer Ag, 5090 Leverkusen | Process for the preparation of new 2-amino-6-dialkylamino-dihydropyridines |
| JPS5922593U (en) * | 1982-08-03 | 1984-02-10 | 日本マランツ株式会社 | Horn mounting structure for headphone |
| JPS5922594U (en) * | 1982-08-03 | 1984-02-10 | 日本マランツ株式会社 | earplug type headphone |
| JPS6282898A (en) * | 1985-10-08 | 1987-04-16 | Matsushita Electric Ind Co Ltd | Headphone |
| JPS6293060U (en) * | 1985-11-28 | 1987-06-13 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3855231A (en) * | 1972-03-06 | 1974-12-17 | Bayer Ag | 2,6-diamino-1,4-dihydropyridine derivatives |
| DE2210687C3 (en) * | 1972-03-06 | 1981-09-24 | Bayer Ag, 5090 Leverkusen | 2,6-diamino-3,5-diethoxycarbonyldihydropyridines, process for their preparation and pharmaceuticals containing them |
| DE2406198C2 (en) * | 1974-02-09 | 1983-12-15 | Bayer Ag, 5090 Leverkusen | Process for the preparation of new 2-amino-6-dialkylamino-dihydropyridines |
-
1972
- 1972-03-06 DE DE2210687A patent/DE2210687C3/en not_active Expired
-
1973
- 1973-02-13 RO RO7300082647A patent/RO63068A/ro unknown
- 1973-02-13 RO RO73832A patent/RO61192A/ro unknown
- 1973-02-26 DD DD169048A patent/DD106833A5/xx unknown
- 1973-02-28 BG BG022858A patent/BG22815A3/en unknown
- 1973-02-28 BG BG024472A patent/BG20583A3/en unknown
- 1973-03-02 IL IL7341664A patent/IL41664A/en unknown
- 1973-03-02 JP JP2445273A patent/JPS5626659B2/ja not_active Expired
- 1973-03-02 CH CH220176A patent/CH577473A5/xx not_active IP Right Cessation
- 1973-03-02 FI FI657/73A patent/FI55996C/en active
- 1973-03-02 LU LU67147A patent/LU67147A1/xx unknown
- 1973-03-02 CH CH313273A patent/CH580589A5/xx not_active IP Right Cessation
- 1973-03-03 PL PL1973161010A patent/PL89256B1/pl unknown
- 1973-03-03 PL PL1973182270A patent/PL92078B1/pl unknown
- 1973-03-05 DK DK118073A patent/DK136061C/en active
- 1973-03-05 ZA ZA731501A patent/ZA731501B/en unknown
- 1973-03-05 BE BE128374A patent/BE796279A/en not_active IP Right Cessation
- 1973-03-05 IE IE346/73A patent/IE37370B1/en unknown
- 1973-03-05 KR KR7300356A patent/KR780000119B1/en active
- 1973-03-05 ES ES412323A patent/ES412323A1/en not_active Expired
- 1973-03-05 CA CA165,209A patent/CA988524A/en not_active Expired
- 1973-03-05 SE SE7303021A patent/SE384208B/en unknown
- 1973-03-06 AT AT925774*7A patent/AT327904B/en not_active IP Right Cessation
- 1973-03-06 HU HUBA2892A patent/HU167089B/hu unknown
- 1973-03-06 FR FR7307923A patent/FR2181789B1/fr not_active Expired
- 1973-03-06 CS CS7300001593A patent/CS182781B2/en unknown
- 1973-03-06 AT AT925774A patent/ATA925774A/en unknown
- 1973-03-06 NL NL7303137A patent/NL7303137A/xx not_active Application Discontinuation
- 1973-03-06 CS CS7500003602A patent/CS182792B2/en unknown
- 1973-03-06 GB GB1075973A patent/GB1379005A/en not_active Expired
- 1973-03-06 AT AT197373A patent/AT324338B/en not_active IP Right Cessation
-
1980
- 1980-12-27 JP JP55185147A patent/JPS5911584B2/en not_active Expired
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