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
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 150000002475 indoles Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 10
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 239000002253 acid Substances 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 7
- 125000003545 alkoxy group Chemical group 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 150000007513 acids Chemical class 0.000 abstract 4
- 125000002252 acyl group Chemical group 0.000 abstract 3
- -1 hydroxy, benzyloxy Chemical group 0.000 abstract 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000006277 halobenzyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 125000005059 halophenyl group Chemical group 0.000 abstract 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 abstract 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 238000006722 reduction reaction Methods 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- 238000006856 Wolf-Kishner-Huang Minlon reduction reaction Methods 0.000 abstract 1
- 239000002250 absorbent Substances 0.000 abstract 1
- 230000002745 absorbent Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000003841 chloride salts Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 239000006210 lotion Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 230000000475 sunscreen effect Effects 0.000 abstract 1
- 239000000516 sunscreening agent Substances 0.000 abstract 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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 FR FR906094A patent/FR1505309A/en not_active Expired
- 1962-08-03 BE BE621047A patent/BE621047A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1007583A (en) | 1965-10-13 |
| BE621047A (en) | 1963-02-04 |
| FR1505309A (en) | 1967-12-15 |
| DE1470380A1 (en) | 1969-12-11 |
| CH437289A (en) | 1967-06-15 |
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