GB1111489A - Pseudo-indole derivatives - Google Patents
Pseudo-indole derivativesInfo
- Publication number
- GB1111489A GB1111489A GB3629966A GB3629966A GB1111489A GB 1111489 A GB1111489 A GB 1111489A GB 3629966 A GB3629966 A GB 3629966A GB 3629966 A GB3629966 A GB 3629966A GB 1111489 A GB1111489 A GB 1111489A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- alkyl
- formula
- halogen
- substituted
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000007857 hydrazones Chemical class 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000000954 anitussive effect Effects 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 230000001741 anti-phlogistic effect Effects 0.000 abstract 1
- 229940124584 antitussives Drugs 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- -1 compound halogen Chemical class 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
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 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
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 230000002048 spasmolytic effect Effects 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (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)
Abstract
Novel compounds of formula <FORM:1111489/C2/1> and acid addition salts thereof where R1 is CH3 or phenyl, R2 is H, halogen, CH3 or methoxy R3 is C1- 4 alkyl or phenyl optionally substituted by halogen atoms or C1- 4 alkyl or alkoxy groups, R4 is C2- 4 alkenyl and R5 is an alkyl group substituted by a C3- 8 cycloalkyl group, aralkyl or alkenyl or R4 and R5 together with the nitrogen atom to which they are attached form a saturated or partly saturated heterocyclic ring which may contain an additional oxygen or nitrogen atom and is substituted by phenyl which may itself be substituted by halogen, hydroxy, C1- 4 alkoxy or C1- 4 alkyl and A is a straight or branched chain C2- 4 hydrocarbon group are prepared by cyclisation of a hydrazone of formula <FORM:1111489/C2/2> optionally followed by salt formation. Hydrazones of the last formula above are prepared by reacting the appropriate phenyl hydrazine with a ketone of formula <FORM:1111489/C2/3> which has been prepared for example by reaction of a phenyl acetone and a compound halogen -A-NR4.R5. Pharmaceutical compositions in conventional forms for oral, rectal and parenteral administration and having analgesic, antiphlogistic, antitussive and spasmolytic activity comprise an above novel compound and a carrier or excipient.
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL133995D NL133995C (en) | 1965-08-21 | ||
| DE19661620565 DE1620565A1 (en) | 1965-08-21 | 1966-09-20 | Process for the production of new basic substituted pseudoindoles |
| FR292D FR292F (en) | 1965-08-21 | 1967-01-31 | |
| BE693450D BE693450A (en) | 1965-08-21 | 1967-01-31 | |
| NL6710605A NL6710605A (en) | 1965-08-21 | 1967-08-01 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DET0029248 | 1965-08-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1111489A true GB1111489A (en) | 1968-04-24 |
Family
ID=7554736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3629966A Expired GB1111489A (en) | 1965-08-19 | 1966-08-12 | Pseudo-indole derivatives |
Country Status (3)
| Country | Link |
|---|---|
| DE (1) | DE1620511A1 (en) |
| FR (1) | FR212F (en) |
| GB (1) | GB1111489A (en) |
-
0
- FR FR212D patent/FR212F/fr active Active
-
1965
- 1965-08-19 DE DE19651620511 patent/DE1620511A1/en active Pending
-
1966
- 1966-08-12 GB GB3629966A patent/GB1111489A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR212F (en) | |
| DE1620511A1 (en) | 1970-04-30 |
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