NO123348B - - Google Patents

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Info

Publication number: NO123348B
Authority: NO; Norway
Prior art keywords: alkyl group; lower alkyl; ammonia; dihydropyridine; ester
Prior art date: 1967-03-20

Application number

NO1058/68A

Other languages

English (en)

Norwegian (no)

Inventor

F Bossert

W Vater

Original Assignee

Bayer Ag

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.)

1967-03-20

Filing date

1968-03-19

Publication date

1971-11-01

1968-03-19 Application filed by Bayer Ag filed Critical Bayer Ag

1971-11-01 Publication of NO123348B publication Critical patent/NO123348B/no

Links

QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 10
229910021529 ammonia Inorganic materials 0.000 claims description 10
-1 pyrimidine aldehydes Chemical class 0.000 claims description 7
YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical class C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
235000014113 dietary fatty acids Nutrition 0.000 claims description 2
229930195729 fatty acid Natural products 0.000 claims description 2
239000000194 fatty acid Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
238000009835 boiling Methods 0.000 description 9
150000001875 compounds Chemical class 0.000 description 8
239000013078 crystal Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
206010002383 Angina Pectoris Diseases 0.000 description 4
230000000694 effects Effects 0.000 description 4
WQGFZQFGVYDFOP-UHFFFAOYSA-N 4,6-dimethoxypyrimidine-5-carbaldehyde Chemical compound COC1=NC=NC(OC)=C1C=O WQGFZQFGVYDFOP-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000008298 dragée Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000829 suppository Substances 0.000 description 3
238000011282 treatment Methods 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
201000010099 disease Diseases 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
FREJAOSUHFGDBW-UHFFFAOYSA-N pyrimidine-5-carbaldehyde Chemical compound O=CC1=CN=CN=C1 FREJAOSUHFGDBW-UHFFFAOYSA-N 0.000 description 2
XBYXYDVSCMMJDT-UHFFFAOYSA-N 2-(dimethylamino)pyrimidine-5-carbaldehyde Chemical compound CN(C)C1=NC=C(C=O)C=N1 XBYXYDVSCMMJDT-UHFFFAOYSA-N 0.000 description 1
BDCLDNALSPBWPQ-UHFFFAOYSA-N 3-oxohexanoic acid Chemical compound CCCC(=O)CC(O)=O BDCLDNALSPBWPQ-UHFFFAOYSA-N 0.000 description 1
GTPSZGHZFDNCPQ-UHFFFAOYSA-N 4,6-dimethoxy-2-(methylamino)pyrimidine-5-carbaldehyde Chemical compound CNC1=NC(=C(C(=N1)OC)C=O)OC GTPSZGHZFDNCPQ-UHFFFAOYSA-N 0.000 description 1
LGKQVMSGOUJVCB-UHFFFAOYSA-N 5-methyl-3-oxohexanoic acid Chemical compound CC(C)CC(=O)CC(O)=O LGKQVMSGOUJVCB-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
206010052895 Coronary artery insufficiency Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000010339 dilation Effects 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
229940079593 drug Drugs 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
239000000155 melt Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
GVIIRWAJDFKJMJ-UHFFFAOYSA-N propan-2-yl 3-oxobutanoate Chemical compound CC(C)OC(=O)CC(C)=O GVIIRWAJDFKJMJ-UHFFFAOYSA-N 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
OKULHRWWYCFJAB-UHFFFAOYSA-N pyrimidine-4-carbaldehyde Chemical compound O=CC1=CC=NC=N1 OKULHRWWYCFJAB-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Liquid Crystal Substances (AREA)
Hydrogenated Pyridines (AREA)

NO1058/68A 1967-03-20 1968-03-19 NO123348B (fi)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0051880		1967-03-20

Publications (1)

Publication Number	Publication Date
NO123348B true NO123348B (fi)	1971-11-01

Family

ID=7104983

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO1058/68A NO123348B (fi)	1967-03-20	1968-03-19

Country Status (13)

Country	Link
US (1)	US3511837A (fi)
BE (1)	BE712346A (fi)
DE (1)	DE1670826A1 (fi)
DK (1)	DK119559B (fi)
ES (1)	ES351796A1 (fi)
FI (1)	FI50420C (fi)
FR (2)	FR1557376A (fi)
GB (1)	GB1173105A (fi)
IL (1)	IL29568A (fi)
NL (1)	NL6803565A (fi)
NO (1)	NO123348B (fi)
SE (1)	SE347263B (fi)
YU (1)	YU32464B (fi)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3950336A (en) *	1972-03-06	1976-04-13	Bayer Aktiengesellschaft	2,6-diamino-1,4-dihydropyridine derivatives
US3988458A (en) *	1972-03-06	1976-10-26	Bayer Aktiengesellschaft	Bicyclic derivatives of 1,4-dihydropyridine 3,5-carboxylic acid esters
DE3022030A1 (de) *	1980-06-12	1981-12-17	Bayer Ag, 5090 Leverkusen	4-thiazol- bzw. 4-imidazol-substituierte, 1,4-dihydropyridine, verfahren zu deren herstellung sowie diese enthaltende arzneimittel
US4833150A (en) *	1985-03-14	1989-05-23	Nelson Research & Development Co.	1,4-dihydropyridines
US4849436A (en) *	1986-03-11	1989-07-18	Nelson Research & Development Co.	1,4-dihydropyridines

1967
- 1967-03-20 DE DE19671670826 patent/DE1670826A1/de active Pending
1968
- 1968-02-02 FI FI680267A patent/FI50420C/fi active
- 1968-03-04 IL IL6829568A patent/IL29568A/xx unknown
- 1968-03-13 NL NL6803565A patent/NL6803565A/xx unknown
- 1968-03-14 US US712911A patent/US3511837A/en not_active Expired - Lifetime
- 1968-03-15 YU YU0596/68A patent/YU32464B/xx unknown
- 1968-03-18 BE BE712346D patent/BE712346A/xx unknown
- 1968-03-19 NO NO1058/68A patent/NO123348B/no unknown
- 1968-03-19 SE SE03602/68A patent/SE347263B/xx unknown
- 1968-03-19 DK DK118368AA patent/DK119559B/da unknown
- 1968-03-20 GB GB03480/68A patent/GB1173105A/en not_active Expired
- 1968-03-20 ES ES351796A patent/ES351796A1/es not_active Expired
- 1968-03-20 FR FR1557376D patent/FR1557376A/fr not_active Expired
- 1968-06-19 FR FR155573A patent/FR7774M/fr not_active Expired

Also Published As

Publication number	Publication date
NL6803565A (fi)	1968-09-23
YU32464B (en)	1974-12-31
DE1670826A1 (de)	1971-03-11
YU59668A (en)	1974-06-30
BE712346A (fi)	1968-09-18
DK119559B (da)	1971-01-25
US3511837A (en)	1970-05-12
FI50420C (fi)	1976-03-10
FR1557376A (fi)	1969-02-14
GB1173105A (en)	1969-12-03
SE347263B (fi)	1972-07-31
ES351796A1 (es)	1969-06-16
FR7774M (fi)	1970-03-23
IL29568A (en)	1971-12-29
FI50420B (fi)	1975-12-01

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NO123804B (fi)	1972-01-17
US3485847A (en)	1969-12-23	4-aryl-1,4-dihydropyridines
US3178348A (en)	1965-04-13	Hypotensive quinolines
US2835669A (en)	1958-05-20	Process for the production of substi-
NO123348B (fi)	1971-11-01
CH647519A5 (de)	1985-01-31	Bluthochdruck senkende amine.
US2922744A (en)	1960-01-26	Therapeutic processes employing aminobenzodioxane medicaments
JPH0411547B2 (fi)	1992-02-28
US3001992A (en)	1961-09-26	S-niteo-z-fubftjewdene
Lesesne et al.	1942	Utilization of Alkoxy Ketones in the Synthesis of Quinolines by the Pfitzinger Reaction. II1
NO173990B (no)	1993-11-22	Analogifremgangsmaate for fremstilling av terapeutisk aktive 9-amino-1,4-etan-1,2,3,4-tetrahydroakridiner
US2941002A (en)	1960-06-14	Beta-hydroxy carboxylic acid amides substituted at the nitrogen atom
DE3721222A1 (de)	1988-01-14	Glycinderivate
US2954381A (en)	1960-09-27	Heteroaryloxazolidinediones
US2820738A (en)	1958-01-21	Xjhitc
US2882273A (en)	1959-04-14	Therapeutic agents
US3325515A (en)	1967-06-13	Coumarin derivatives and their preparation
US2928835A (en)	1960-03-15	New esters
US2891063A (en)	1959-06-16	Piperazine derivatives and process of
EP0005091B1 (fr)	1981-11-25	Nouvelles pipérazines monosubstituées, leurs procédés de préparation et les compositions pharmaceutiques les renfermant
DE2313338B2 (de)	1980-06-26	N-Hexamethylenimino-derivate, deren Salze, Verfahren zu deren Herstellung sowie diese enthaltende pharmazeutische Zubereitung
FR2864535A1 (fr)	2005-07-01	Derives acides de quinoline et leurs applications en therapeutique
DE2734270C2 (fi)	1990-06-21
DE2624918A1 (de)	1977-12-15	Arzneimittel mit antiarrhythmischer wirkung
CS225823B2 (en)	1984-02-13	The production of the pyridine derivates