GB1007584A - Improvements in or relating to benz[c,d]indole derivatives and the manufacture thereof - Google Patents
Improvements in or relating to benz[c,d]indole derivatives and the manufacture thereofInfo
- Publication number
- GB1007584A GB1007584A GB3941464A GB3941464A GB1007584A GB 1007584 A GB1007584 A GB 1007584A GB 3941464 A GB3941464 A GB 3941464A GB 3941464 A GB3941464 A GB 3941464A GB 1007584 A GB1007584 A GB 1007584A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- carbon atoms
- compounds
- alkoxy
- hydrogen
- 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
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
- A61K8/492—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid having condensed rings, e.g. indol
-
- 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
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
Abstract
The invention comprises compounds of the general formula <FORM:1007584/C2/1> wherein R is hydrogen or C1 to C8 alkyl, R1\t is hydrogen, C1 to C4 alkyl, phenyl, hydroxyphenyl, alkoxyphenyl wherein alkoxy is of 1 to 4 carbon atoms, or halophenyl, R2 is hydrogen, alkanoyl of from 1 to 4 carbon atoms, benzyl or halobenzyl which can be substituted with alkyl or alkoxy of 1 to 4 carbon atoms, or alkyl of from 1 to 4 carbon atoms, R3 is hydroxy, benzyloxy, halogen, or alkyl or alkoxy of from 1 to 4 carbon atoms, and n is zero, 1 or 2. The compounds may be prepared by subjecting the 5-oxo group of a compound of the general formula <FORM:1007584/C2/2> wherein R, R1, R2, R3 and n are as defined above, to a Huang-Minlon reduction and, in the case where R2 in the starting material represents an alkanoyl group, optionally N-acylating the acid so produced. The acids may be esterified by conventional procedures, for example, via the acid chlorides, and the resultant esters may be purified and then hydrolysed to the acids, resulting in upgrading of the acids. The compounds of the invention, wherein R is H, may be decarboxylated by heating to give compounds of the general formula. <FORM:1007584/C2/3> wherein R1, R2, R3 and n are as defined above. The compounds of the invention, wherein R is H, may also be esterified in accordance with U.S.A. Specification 2,220,521, to form betathiocyanoethyl esters. The Huang-Minulon reduction is performed by conversion of the acid or the ester to the corresponding salt, followed by reduction with hydrazine hydrate. Many suitably values of R, R1, R2 and R3 are specified. Examples are given, including examples of the hydrogenolysis of acids containing a 6- or 8-benzyloxy substituent to give the corresponding free hydroxy compounds.ALSO:Sun-screen lotions may incorporate, as ultraviolet absorbents, compounds of the general formula <FORM:1007584/A5-A6/1> wherein R is hydrogen or C1 C8 alkyl, R, is hydrogen, C1 to C4 alkyl, phenyl, hydroxyphenyl, alkoxyphenyl wherein alkoxy is of 1 to 4 carbon atoms, or halophenyl, R2 is hydrogen, alkanoyl of from 1 to 4 carbon atoms, benzyl or halobenzyl which can be substituted with alkyl or alkoxy of 1 to 4 carbon atoms, or alkyl of from 1 to 4 carbon atoms, R3 is hydroxy, benzyloxy, halogen, or alkyl or alkoxy of from 1 to 4 carbon atoms, and n is zero, 1 or 2 (see Division C2).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12922161A | 1961-08-04 | 1961-08-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1007584A true GB1007584A (en) | 1965-10-13 |
Family
ID=22438953
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3941464A Expired GB1007584A (en) | 1961-08-04 | 1962-07-09 | Improvements in or relating to benz[c,d]indole derivatives and the manufacture thereof |
| GB2628962A Expired GB1007583A (en) | 1961-08-04 | 1962-07-09 | Improvements in or relating to benz[e,d]indole derivatives and the manufacture thereof |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2628962A Expired GB1007583A (en) | 1961-08-04 | 1962-07-09 | Improvements in or relating to benz[e,d]indole derivatives and the manufacture thereof |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE621047A (en) |
| CH (1) | CH437289A (en) |
| DE (1) | DE1470380A1 (en) |
| FR (1) | FR1505309A (en) |
| GB (2) | GB1007584A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4543360A (en) * | 1981-09-10 | 1985-09-24 | Degussa Aktiengesellschaft | 2-(Hydroxy-phenyl)-indoles and process for their production |
-
1962
- 1962-07-09 GB GB3941464A patent/GB1007584A/en not_active Expired
- 1962-07-09 GB GB2628962A patent/GB1007583A/en not_active Expired
- 1962-07-17 CH CH858762A patent/CH437289A/en unknown
- 1962-07-28 DE DE19621470380 patent/DE1470380A1/en active Pending
- 1962-08-03 BE BE621047A patent/BE621047A/en unknown
- 1962-08-03 FR FR906094A patent/FR1505309A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1505309A (en) | 1967-12-15 |
| CH437289A (en) | 1967-06-15 |
| GB1007583A (en) | 1965-10-13 |
| BE621047A (en) | 1963-02-04 |
| DE1470380A1 (en) | 1969-12-11 |
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