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
- 239000008194 pharmaceutical composition Substances 0.000 title claims 5
- 150000001875 compounds Chemical class 0.000 claims abstract 30
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract 6
- 125000001424 substituent group Chemical group 0.000 claims abstract 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000004480 active ingredient Substances 0.000 claims abstract 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract 4
- 150000001409 amidines Chemical class 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 3
- 125000005493 quinolyl group Chemical group 0.000 claims abstract 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002541 furyl group Chemical group 0.000 claims abstract 2
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 14
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 239000003085 diluting agent Substances 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 230000037396 body weight Effects 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- XNJATKPGORTUCP-UHFFFAOYSA-N 1,2-dihydropyridine-2,6-diamine Chemical class NC1NC(N)=CC=C1 XNJATKPGORTUCP-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 1
- 241001465754 Metazoa Species 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims 1
- 239000008298 dragée Substances 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000829 suppository Substances 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 claims 1
- -1 cyclic hydrocarbon radical Chemical class 0.000 abstract 4
- 150000003254 radicals Chemical class 0.000 abstract 3
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 239000002220 antihypertensive agent Substances 0.000 abstract 1
- 229940030600 antihypertensive agent Drugs 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 abstract 1
- 125000005956 isoquinolyl group Chemical group 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
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)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Vascular Medicine (AREA)
- Pulmonology (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) | AT324338B (en) |
| BE (1) | BE796279A (en) |
| BG (2) | BG20583A3 (en) |
| CA (1) | CA988524A (en) |
| CH (2) | CH580589A5 (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) | PL92078B1 (en) |
| RO (2) | RO63068A (en) |
| SE (1) | SE384208B (en) |
| ZA (1) | ZA731501B (en) |
Families Citing this family (7)
| 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 | ||
| US20230416203A1 (en) * | 2020-11-30 | 2023-12-28 | Nanyang Technological University | Potent and selective inhibitors of the calcium-activated potassium channel, kca3.1, for use as platform therapeutics |
Family Cites Families (3)
| 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 |
| US3855231A (en) * | 1972-03-06 | 1974-12-17 | Bayer Ag | 2,6-diamino-1,4-dihydropyridine derivatives |
| 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 BG024472A patent/BG20583A3/en unknown
- 1973-02-28 BG BG022858A patent/BG22815A3/en unknown
- 1973-03-02 CH CH313273A patent/CH580589A5/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 CH220176A patent/CH577473A5/xx not_active IP Right Cessation
- 1973-03-02 JP JP2445273A patent/JPS5626659B2/ja not_active Expired
- 1973-03-02 IL IL7341664A patent/IL41664A/en unknown
- 1973-03-03 PL PL1973182270A patent/PL92078B1/pl unknown
- 1973-03-03 PL PL1973161010A patent/PL89256B1/pl unknown
- 1973-03-05 CA CA165,209A patent/CA988524A/en not_active Expired
- 1973-03-05 KR KR7300356A patent/KR780000119B1/en not_active Expired
- 1973-03-05 ES ES412323A patent/ES412323A1/en not_active Expired
- 1973-03-05 SE SE7303021A patent/SE384208B/en unknown
- 1973-03-05 IE IE346/73A patent/IE37370B1/en unknown
- 1973-03-05 BE BE128374A patent/BE796279A/en not_active IP Right Cessation
- 1973-03-05 ZA ZA731501A patent/ZA731501B/en unknown
- 1973-03-05 DK DK118073A patent/DK136061C/en active
- 1973-03-06 HU HUBA2892A patent/HU167089B/hu unknown
- 1973-03-06 AT AT197373A patent/AT324338B/en not_active IP Right Cessation
- 1973-03-06 AT AT925774A patent/ATA925774A/en unknown
- 1973-03-06 AT AT925774*7A patent/AT327904B/en not_active IP Right Cessation
- 1973-03-06 GB GB1075973A patent/GB1379005A/en not_active Expired
- 1973-03-06 CS CS7300001593A patent/CS182781B2/en unknown
- 1973-03-06 FR FR7307923A patent/FR2181789B1/fr not_active Expired
- 1973-03-06 NL NL7303137A patent/NL7303137A/xx not_active Application Discontinuation
- 1973-03-06 CS CS7500003602A patent/CS182792B2/en unknown
-
1980
- 1980-12-27 JP JP55185147A patent/JPS5911584B2/en not_active Expired
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