Showing content from https://patents.google.com/patent/GB1109502A/en below:
GB1109502A - Substituted n-benzyl-ethylenediamines - Google Patents
GB1109502A - Substituted n-benzyl-ethylenediamines - Google PatentsSubstituted n-benzyl-ethylenediamines Info
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Publication number
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GB1109502A
GB1109502A GB1618164A GB1618164A GB1109502A GB 1109502 A GB1109502 A GB 1109502A GB 1618164 A GB1618164 A GB 1618164A GB 1618164 A GB1618164 A GB 1618164A GB 1109502 A GB1109502 A GB 1109502A
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Authority
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GB
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United Kingdom
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Prior art keywords
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general formula
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group
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reacting
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quaternary ammonium
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heterocyclic ring
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Prior art date
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1964-04-18
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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.)
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Expired
Application number
GB1618164A
Inventor
Gwynn Pennant Ellis
Colin Fitzmaurice
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.)
Fisons Pharmaceuticals Ltd
Original Assignee
Fisons Pharmaceuticals Ltd
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.)
1964-04-18
Filing date
1964-04-18
Publication date
1968-04-10
1964-04-18 Application filed by Fisons Pharmaceuticals Ltd filed Critical Fisons Pharmaceuticals Ltd
1964-04-18 Priority to GB1618164A priority Critical patent/GB1109502A/en
1968-04-10 Publication of GB1109502A publication Critical patent/GB1109502A/en
Status Expired legal-status Critical Current
Links
- 150000001875 compounds Chemical class 0.000 abstract 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- -1 aminoethyl halide Chemical class 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910006124 SOCl2 Inorganic materials 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 230000001387 anti-histamine Effects 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 150000002917 oxazolidines Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Novel compounds of the general formula <FORM:1109502/C2/1> (wherein R1 represents H or a group of the formula <FORM:1109502/C2/2> R2 represents OH or a lower alkoxy group or, when R1 is other than H, a hydrogen or halogen atom, R3 represents H or an alkyl or aralkyl group, and -NR4R5 represents a five-membered heterocyclic ring, or a six-membered heterocyclic ring containing at least two N atoms, both of which rings are optionally substituted by a 2-hydroxyalkyl group, and n is 1 or 2), and their acid addition salts and quaternary ammonium salts, are prepared by reacting an aminoethyl halide of the general formula <FORM:1109502/C2/3> with a cyclic base R4.NH.R5, and, if desired, converting the product into an acid addition or quaternary ammonium salt. Aminoethyl halides used as starting materials are prepared by reacting an aldehyde or ketone of the general formula <FORM:1109502/C2/4> with ethanolamine to form a substituted oxazolidine of the general formula <FORM:1109502/C2/5> catalytically hydrogenating this to a compound of the general formula <FORM:1109502/C2/6> and treating this with a halogenating agent, e.g. SOCl2, with or without first alkylating or aralkylating it on the N atom. Pharmaceutical compositions, having anti-histaminic activity, comprise the novel compounds of the invention in association with pharmaceutical carriers or diluents.
GB1618164A 1964-04-18 1964-04-18 Substituted n-benzyl-ethylenediamines Expired GB1109502A (en) Priority Applications (1) Application Number Priority Date Filing Date Title GB1618164A GB1109502A (en) 1964-04-18 1964-04-18 Substituted n-benzyl-ethylenediamines Applications Claiming Priority (1) Application Number Priority Date Filing Date Title GB1618164A GB1109502A (en) 1964-04-18 1964-04-18 Substituted n-benzyl-ethylenediamines Publications (1) Publication Number Publication Date GB1109502A true GB1109502A (en) 1968-04-10 Family ID=10072629 Family Applications (1) Application Number Title Priority Date Filing Date GB1618164A Expired GB1109502A (en) 1964-04-18 1964-04-18 Substituted n-benzyl-ethylenediamines Country Status (1) Cited By (4) * Cited by examiner, â Cited by third party Publication number Priority date Publication date Assignee Title DE2639357A1 (en) * 1975-09-02 1977-03-10 Merck & Co Inc POLYAMINES EP0094562A1 (en) * 1982-05-15 1983-11-23 BASF Aktiengesellschaft Diamine derivatives, process for their production and their use as fungicides US4448776A (en) * 1981-02-12 1984-05-15 Karl Bucher Method of using certain substituted aliphatic secondary amines or their salts for easing breathing US4599335A (en) * 1983-05-06 1986-07-08 Basf Aktiengesellschaft Diamine derivatives, compositions and use
Cited By (4) * Cited by examiner, â Cited by third party Publication number Priority date Publication date Assignee Title DE2639357A1 (en) * 1975-09-02 1977-03-10 Merck & Co Inc POLYAMINES US4448776A (en) * 1981-02-12 1984-05-15 Karl Bucher Method of using certain substituted aliphatic secondary amines or their salts for easing breathing EP0094562A1 (en) * 1982-05-15 1983-11-23 BASF Aktiengesellschaft Diamine derivatives, process for their production and their use as fungicides US4599335A (en) * 1983-05-06 1986-07-08 Basf Aktiengesellschaft Diamine derivatives, compositions and use Similar Documents Publication Publication Date Title GB1047935A (en) 1966-11-09 Substituted piperazines and preparation thereof NL177403C (en) 1985-09-16 PROCESS FOR MANUFACTURING A PHARMACEUTICAL PREPARATION WITH ANTIMICROBIC ACTION BASED ON A 14-DESOXY-14-ACETOXYMUTILINE DERIVATIVE AND METHOD FOR PREPARING A COMPOUND SUITABLE FOR THE SAID PROCESS. SE7714184L (en) 1978-06-15 PIPERAZINE DERIVATIVES GB1120463A (en) 1968-07-17 Derivatives of 1,3-diazafluoranthene-1-oxide SE7602144L (en) 1976-09-13 QUATER IMIDAZOLIUM ASSOCIATIONS GB1105522A (en) 1968-03-06 N-phenylpiperazine compounds GB961037A (en) 1964-06-17 Pyrazolones and processes for their preparation GB1041536A (en) 1966-09-07 Quaternary ammonium derivatives of dibenzo[a,d]-cycloheptadiene derivatives GB1109502A (en) 1968-04-10 Substituted n-benzyl-ethylenediamines GB1111338A (en) 1968-04-24 Aralkyl substituted resorcinols ES400963A1 (en) 1975-02-01 3-benzylpyridines GB1452448A (en) 1976-10-13 Derivatives of 2-amino-1,3-thiazine GB1029228A (en) 1966-05-11 A method of preparing new quaternary ammonium salts with disinfectant activity GB1096301A (en) 1967-12-29 1,4-benzodioxane derivatives GB1024643A (en) 1966-03-30 Optically active naphthalene derivatives GB901455A (en) 1962-07-18 C-substituted piperazinones and the manufacture thereof ES394907A1 (en) 1974-01-16 1,2-dihydro-8-carbamoyloxyquinolines GB1429045A (en) 1976-03-24 Hiazole cardiovascular agents GB980251A (en) 1965-01-13 New piperazine derivatives GB1269776A (en) 1972-04-06 Epoxides and halohydrins and conversion thereof to alkanolamine derivatives GB1094982A (en) 1967-12-13 1,4-benzodioxanes GB951026A (en) 1964-03-04 The manufacture of sulphonamides GB1081542A (en) 1967-08-31 Peri-naphthazole cyanine dyestuffs GB1343090A (en) 1974-01-10 Coumarine derivatives their preparation and use as brighteners GB1017450A (en) 1966-01-19 2-amino-4-alkoxy-úÃ-triazines
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