GB1093912A - Pseudo-indole derivatives - Google Patents
Pseudo-indole derivativesInfo
- Publication number
- GB1093912A GB1093912A GB23980/65A GB2398065A GB1093912A GB 1093912 A GB1093912 A GB 1093912A GB 23980/65 A GB23980/65 A GB 23980/65A GB 2398065 A GB2398065 A GB 2398065A GB 1093912 A GB1093912 A GB 1093912A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- alkyl
- hydrazine
- phenyl
- prepared
- 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([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
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 150000002429 hydrazines Chemical class 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 abstract 1
- 229940067157 phenylhydrazine Drugs 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Novel compounds of formula <FORM:1093912/C2/1> and acid addition salts thereof wherein R1 is methyl or phenyl, R1 is H, halogen, methyl or methoxy, R3 is C1- 4 alkyl or phenyl optionally substituted by halogen atoms or C1- 4 alkyl or alkoxy groups, A is a divalent C2- 4 straight or branched chain aliphatic hydrocarbon group, R4 is C1- 4 alkyl and R5 is C1- 4 optionally substituted by alkenyl, cycloalkyl or aralkyl or NR4R5 is a saturated heterocyclic ring which may contain a further hetero atom, are prepared by cyclization by a condensation agent capable of eliminating ammonia of a hydrazine of formula <FORM:1093912/C2/2> optionally followed by salt formation. Hydrazine derivatives of the last general formula above are prepared by reaction of the appropriate phenyl hydrazine and ketone. Amino ketones of formula R1.CO.CH(R3).A.N.R4.R5 are prepared according to W. Wilson, J. Chem. Soc. 1952, p.9. Pharmaceutical compositions comprise an above novel compound and a carrier therefor and are in conventional forms for oral, rectal or parenteral administration.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET0026315 | 1964-06-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1093912A true GB1093912A (en) | 1967-12-06 |
Family
ID=7552694
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23980/65A Expired GB1093912A (en) | 1964-06-05 | 1965-06-04 | Pseudo-indole derivatives |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH457433A (en) |
| DE (1) | DE1470370C3 (en) |
| FR (1) | FR4423M (en) |
| GB (1) | GB1093912A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2825192A1 (en) * | 1978-06-08 | 1979-12-20 | Thomae Gmbh Dr K | 2,3-DIHYDRO-2-METHYL-3 SQUARE CLAMP ON 2- (DIMETHYLAMINO) -PROPYL SQUARE CLAMP TO -3-PHENYL-1H-INDOL-1-CARBOXALDEHYDE, METHOD FOR THE PRODUCTION THEREOF AND THEIR CONTAINERS |
-
1964
- 1964-06-05 DE DE1470370A patent/DE1470370C3/en not_active Expired
-
1965
- 1965-06-04 CH CH785065A patent/CH457433A/en unknown
- 1965-06-04 GB GB23980/65A patent/GB1093912A/en not_active Expired
- 1965-06-04 FR FR19655A patent/FR4423M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1470370B2 (en) | 1974-02-28 |
| CH457433A (en) | 1968-06-15 |
| FR4423M (en) | 1966-09-12 |
| DE1470370C3 (en) | 1974-10-10 |
| DE1470370A1 (en) | 1970-01-02 |
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