GB1057969A - Aryloxyamines and process for preparation - Google Patents
Aryloxyamines and process for preparationInfo
- Publication number
- GB1057969A GB1057969A GB5370865A GB5370865A GB1057969A GB 1057969 A GB1057969 A GB 1057969A GB 5370865 A GB5370865 A GB 5370865A GB 5370865 A GB5370865 A GB 5370865A GB 1057969 A GB1057969 A GB 1057969A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- benzyl
- substituted
- pharmaceutically acceptable
- starting compounds
- Prior art date
- 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.)
- Expired
Links
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- -1 methylenedioxy group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000000954 anitussive effect Effects 0.000 abstract 1
- 230000002082 anti-convulsion Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 230000002921 anti-spasmodic effect Effects 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 229940124584 antitussives Drugs 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 239000000812 cholinergic antagonist Substances 0.000 abstract 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- PWRKXLBZLTYQGN-UHFFFAOYSA-N hydroxysulfanylmethylbenzene Chemical compound OSCC1=CC=CC=C1 PWRKXLBZLTYQGN-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 abstract 1
Classifications
-
- 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
- C07D295/08—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 bound oxygen or sulfur atoms
- C07D295/084—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Novel o-substituted aryloxyamines of the formula <FORM:1057969/C2/1> wherein R1 and R2 are either the same or different lower alkyl groups, or when taken with the amino nitrogen atom form a closed chain heterocyclic group, R3, R4 and R5 may be the same or different hydrogen or halogen atoms or lower alkyl or lower alkoxy groups or together form a methylenedioxy group; Z is oxygen or sulphur and n is 2 or 3, and the pharmaceutically acceptable acid addition salts thereof are obtained in a process which comprises reacting an aryloxyamine of the formula <FORM:1057969/C2/2> with a benzyl halide of the formula <FORM:1057969/C2/3> wherein Y is halogen, and, if desired, forming the pharmaceutically acceptable salts. The starting compounds may be obtained by reacting o-hydroxybenzaldehyde with the hydrochloride salt of a substituted aminochloroalkane to form o-(substituted amino lower alkoxy)benzaldehyde which is reduced to form the corresponding benzyl alcohol. The benzyl chloride and benzyl thio-alcohol starting compounds are obtained therefrom by treatment with thionyl chloride and sodium hydrosulphide successively. Pharmaceutical compositions having anti-spasmodic, anti-inflammatory, anti-tussive, sedative, anti-pyretic and anti-convulsive activity are administered orally or parenterally.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43291764A | 1964-12-23 | 1964-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1057969A true GB1057969A (en) | 1967-02-08 |
Family
ID=23718097
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5370865A Expired GB1057969A (en) | 1964-12-23 | 1965-12-17 | Aryloxyamines and process for preparation |
Country Status (3)
| Country | Link |
|---|---|
| DK (1) | DK115336B (en) |
| FR (1) | FR5215M (en) |
| GB (1) | GB1057969A (en) |
-
1965
- 1965-12-17 GB GB5370865A patent/GB1057969A/en not_active Expired
- 1965-12-22 FR FR43375A patent/FR5215M/fr not_active Expired
- 1965-12-23 DK DK659865A patent/DK115336B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK115336B (en) | 1969-09-29 |
| DE1518453A1 (en) | 1972-04-20 |
| DE1518453B2 (en) | 1976-01-29 |
| FR5215M (en) | 1967-07-03 |
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