IE31982L - Morpholine derivatives - Google Patents
Morpholine derivativesInfo
- Publication number
- IE31982L IE31982L IE28868A IE28868A IE31982L IE 31982 L IE31982 L IE 31982L IE 28868 A IE28868 A IE 28868A IE 28868 A IE28868 A IE 28868A IE 31982 L IE31982 L IE 31982L
- Authority
- IE
- Ireland
- Prior art keywords
- morpholine
- benzyl
- methylenedioxyphenyl
- methylenedioxy
- cis
- Prior art date
Links
- 150000002780 morpholines Chemical class 0.000 title abstract 4
- -1 polymethyleneimino group Polymers 0.000 abstract 8
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- GZGXWSZGKAWATN-UHFFFAOYSA-N 2-(2,2-diethoxyethyl)oxirane Chemical compound CCOC(OCC)CC1CO1 GZGXWSZGKAWATN-UHFFFAOYSA-N 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 150000001241 acetals Chemical class 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 238000004809 thin layer chromatography Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,184,396. Morpholine derivatives. J. R. GEIGY A.G. 12 March, 1968 [13 March, 1967; 14 Sept., 1967], No. 11923/68. Heading C2C. Novel morpholine derivatives of the formula wherein X is H, OH or NH 2 and Am is NH 2 , C 1-4 alkylamine, di C 1-4 alkylamino, polymethyleneimino group having 5-8 ring members and optionally substituted by one or more alkyl groups having 1 to 4 carbon atoms, or morpholino and their addition salts with inorganic and organic acids are prepared by reacting the corresponding ester in which Am is replaced by -OR, where R is a C 1-6 alkyl group with ammonia or an amine of the formula AmH. The diastereoisomeric ethyl esters of d,l-cis (diequat.) - 6 - C3,4 - methylenedioxyphenyl)- 2- morpholine lactic acid are obtained by the hydrogenolysis of the corresponding isomers of d,l - cis (equat.) - 4 - benzyl - 6 - (3.4 - methylenedioxyphenyl) - 2 - morpholine lactic acid ethyl esters, separated from each other by thin layer chromatography,and prepared by the hydrolysis and esterification of d,l - cis (diequat.) - 4- benzyl - 6 - (3,4 - methylenedioxyphenyl) - 2- morpholine acetaldehyde cyanohydrin, which is in turn obtained by reacting KCN with the corresponding aldehyde derivative resulting from the hydrolysis of its diethyl acetal compound, said acetal being prepared by the cyclization of 4-[N- benzyl - N - (3,4 - methylenedioxy - # - hydroxyphenylethyl) - amino] - 3 - hydroxybutyraldehyde diethyl acetal, obtained by refluxing an ethanol solution of 1,1-diethoxy-3,4-epoxy-butane and 3,4 - methylenedioxy - α - (benzylaminomethyl) benzyl alcohol the latter compound resulting from the reduction with sodium borohydride of 3,4 - methylenedioxy - α - (benzylideneaminomethyl-benzyl alcohol formed by the elimination of water between α-aminomethyl-3,4-methylenedioxybenzyl alcohol and benzaldehyde. Pharmaceutical compositions, having hypotensive activity and suitable for oral, parenteral or rectal administration, contain the above novel morpholine compounds or acid addition salts thereof as the active ingredient.
[GB1184396A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH370767A CH480360A (en) | 1967-03-13 | 1967-03-13 | Process for the preparation of new morpholine derivatives |
| CH1286867 | 1967-09-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE31982L true IE31982L (en) | 1968-09-13 |
| IE31982B1 IE31982B1 (en) | 1973-03-07 |
Family
ID=25693667
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE28868A IE31982B1 (en) | 1967-03-13 | 1968-03-12 | New morpholine derivatives,process for their production and compositions containing them |
Country Status (10)
| Country | Link |
|---|---|
| AT (1) | AT274828B (en) |
| BE (1) | BE712057A (en) |
| CH (1) | CH480360A (en) |
| DE (1) | DE1695127A1 (en) |
| ES (1) | ES351511A1 (en) |
| FR (1) | FR1555439A (en) |
| GB (1) | GB1184396A (en) |
| IE (1) | IE31982B1 (en) |
| NL (1) | NL6803508A (en) |
| SE (1) | SE342046B (en) |
-
1967
- 1967-03-13 CH CH370767A patent/CH480360A/en not_active IP Right Cessation
-
1968
- 1968-03-12 AT AT242768A patent/AT274828B/en active
- 1968-03-12 IE IE28868A patent/IE31982B1/en unknown
- 1968-03-12 SE SE324768A patent/SE342046B/xx unknown
- 1968-03-12 BE BE712057D patent/BE712057A/xx unknown
- 1968-03-12 DE DE19681695127 patent/DE1695127A1/en active Pending
- 1968-03-12 FR FR1555439D patent/FR1555439A/fr not_active Expired
- 1968-03-12 NL NL6803508A patent/NL6803508A/xx unknown
- 1968-03-12 GB GB1192368A patent/GB1184396A/en not_active Expired
- 1968-03-12 ES ES351511A patent/ES351511A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT274828B (en) | 1969-10-10 |
| ES351511A1 (en) | 1969-06-01 |
| CH480360A (en) | 1969-10-31 |
| SE342046B (en) | 1972-01-24 |
| DE1695127A1 (en) | 1971-04-08 |
| GB1184396A (en) | 1970-03-18 |
| IE31982B1 (en) | 1973-03-07 |
| BE712057A (en) | 1968-09-12 |
| FR1555439A (en) | 1969-01-24 |
| NL6803508A (en) | 1968-09-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IE37316L (en) | Optically active esters of ó-amino acids | |
| IE36797L (en) | 1,5-benzodiazepin-2-one derivatives. | |
| GB1466724A (en) | Thiaprostaglandins process for their manufacture and pharmaceu tical preparations containing them | |
| GB1367598A (en) | Derivatives of delta 1-pyrroline their method of preparation and their applications | |
| IE36116B1 (en) | Furylmethyl morphinane derivatives and pharmaceutical compositions containing them | |
| IE31982L (en) | Morpholine derivatives | |
| US3203962A (en) | Alpha-phenyl-beta pyrrolidino-propiophenones | |
| GB1496491A (en) | Dihydroergopeptine derivatives | |
| DE3483881D1 (en) | 1,3-DIOXANE-4-YLALKEN ACID. | |
| GB1361863A (en) | Piperazine derivatives their preparation and pharmaceutical compositions containing them | |
| IE32928L (en) | Amino bicyclo carboxylic acids | |
| GB1173212A (en) | Hydantoins and processes for the preparation thereof | |
| GB1476053A (en) | Glycyrrhetinic acid derivatives | |
| GB1129955A (en) | Unsaturated nitriles and esters and derivatives thereof | |
| GB1348258A (en) | 9-oxo-6.9-dihydro-4h-dioxino-4,5-g-quinolyl-8-carboxylic acids and their isomers, 10-oxo-7,10-dihydro-1h-dioxino-5,4-f-quinolyl- 9-carboxylic acids | |
| GB1185987A (en) | Morpholine Derivatives and Process for their Production | |
| GB1179900A (en) | Tropic acid derivatives | |
| IE35323B1 (en) | Tropane-3-ol derivatives and processes for their preparation | |
| GB1126860A (en) | Novel 4-substituted-7- and 8-chloroquinolines and a process for the preparation thereof | |
| GB1449222A (en) | N-hereroarylmethyl-desoxy-normorphines and-norcodeines | |
| GB1451043A (en) | Biologicylly acitve compounds and compositions | |
| IL40597A (en) | Anti-hypertensively active pharmaceutical preparations containing an anti-hypertensively active amino acid and a beta-hydroxylase inhibitor | |
| GB1164496A (en) | 0-Oxaphenanthridine Derivatives and Method for the Preparation | |
| ES348973A1 (en) | Improvements in or relating to New But-2-Yne Derivative and Process for Preparing same | |
| GB1187733A (en) | 0,3,10-Berbine Derivatives, their Acid Addition Salts, and Process for the Preparation Thereof |