GB1021422A - Asymmetrical disubstituted hydrazines - Google Patents
Asymmetrical disubstituted hydrazinesInfo
- Publication number
- GB1021422A GB1021422A GB673461A GB673461A GB1021422A GB 1021422 A GB1021422 A GB 1021422A GB 673461 A GB673461 A GB 673461A GB 673461 A GB673461 A GB 673461A GB 1021422 A GB1021422 A GB 1021422A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzyl
- amine
- prepared
- alkyl
- methyl
- 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
- 150000002429 hydrazines Chemical class 0.000 title abstract 2
- 150000001412 amines Chemical class 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 3
- RPSOLZRELOLSFM-UHFFFAOYSA-N 2-(1-benzyl-5-methoxy-2-methylindol-3-yl)ethanamine Chemical compound CC1=C(CCN)C2=CC(OC)=CC=C2N1CC1=CC=CC=C1 RPSOLZRELOLSFM-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 150000005840 aryl radicals Chemical group 0.000 abstract 2
- 238000009472 formulation Methods 0.000 abstract 2
- 150000002832 nitroso derivatives Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- GELRGGMHFAHZKK-UHFFFAOYSA-N 1-benzyl-1-(4-methoxyphenyl)hydrazine Chemical compound C1=CC(OC)=CC=C1N(N)CC1=CC=CC=C1 GELRGGMHFAHZKK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 1
- XVRIEWDDMODMGA-UHFFFAOYSA-N 5-chloropentan-2-one Chemical compound CC(=O)CCCCl XVRIEWDDMODMGA-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- -1 alkylene radical Chemical class 0.000 abstract 1
- 230000000172 allergic effect Effects 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 208000010668 atopic eczema Diseases 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000009935 nitrosation Effects 0.000 abstract 1
- 238000007034 nitrosation reaction Methods 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 208000017520 skin disease Diseases 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/10—Hydrazines
- C07C243/22—Hydrazines having nitrogen atoms of hydrazine groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C241/02—Preparation of hydrazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention comprises hydrazines of the general formula R.R1N(NH2)R11 and their acid addition salts, wherein R is an aryl radical, R1 an alkylene radical and R11 an aryl radical optionally substituted by an alkyl or alkoxy group with the proviso that R.R1 is not benzyl when R11 is p-methoxyphenyl, and the preparation of compounds R.R1N(NH2)R11, where R, R1 and R11 are olefined as above but R.R1 and R11 are not subject to the foregoing proviso, by reduction of the nitroso compound R.R1N(NO)R11 The process of the invention may be combined with one wherein the nitroso compound is prepared by nitrosation of the amine R.R1NHR11, the amine in turn being optionally prepared by reduction of the corresponding Schiff's base prepared by the condensation of an amine R11NH2, with an appropriate aldehyde. 1 - Benzyl - 2 - methyl - 5 - methoxytryptamine and its N-alkyl, N-aralkyl- and N,N-dialkyl homologues and their acid addition salts may be prepared by reacting N-benzyl-N-p-methoxy-phenylhydrazine with 5-chloro-pentan-2-one to form 1 - benzyl - 2 - methyl - 3 - (b - chloroethyl) -5-methoxyindole and reacting this with ammonia or an amine.ALSO:Compositions for topical application comprise 1-benzyl-2-methyl-5-methoxytryptamine or an N-alkyl, N-aralkyl or N, N-dialkyl derivative thereof with a pharmaceutical carrier. An example of a cream formulation containing the N, N-diethyl derivative is given. The formulations are of use in the treatment of allergic skin diseases.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB673461A GB1021422A (en) | 1961-02-23 | 1961-02-23 | Asymmetrical disubstituted hydrazines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB673461A GB1021422A (en) | 1961-02-23 | 1961-02-23 | Asymmetrical disubstituted hydrazines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1021422A true GB1021422A (en) | 1966-03-02 |
Family
ID=9819799
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB673461A Expired GB1021422A (en) | 1961-02-23 | 1961-02-23 | Asymmetrical disubstituted hydrazines |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1021422A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011060976A1 (en) * | 2009-11-20 | 2011-05-26 | Universite De Liege | Tryptamine-derived compounds as antibacterial agents |
-
1961
- 1961-02-23 GB GB673461A patent/GB1021422A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011060976A1 (en) * | 2009-11-20 | 2011-05-26 | Universite De Liege | Tryptamine-derived compounds as antibacterial agents |
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