ES336999A1 - Imidazo-(1,5-a)-quinoline Derivatives - Google Patents
Imidazo-(1,5-a)-quinoline DerivativesInfo
- Publication number
- ES336999A1 ES336999A1 ES336999A ES336999A ES336999A1 ES 336999 A1 ES336999 A1 ES 336999A1 ES 336999 A ES336999 A ES 336999A ES 336999 A ES336999 A ES 336999A ES 336999 A1 ES336999 A1 ES 336999A1
- Authority
- ES
- Spain
- Prior art keywords
- lower alkyl
- piperazinyl
- pyrrolidinyl
- compound
- formula
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Novel compounds of Formula I or a pharmaceutically acceptable acid addition salt thereof wherein R and R 1 are hydrogen, halogen, lower alkyl, lower alkoxy or trifluoromethyl R 2 is hydrogen, lower alkyl or halogen, Y is oxygen or sulphur n is an integer from 1 to 4 and R 3 and R 4 are hydrogen, lower alkyl, lower alkenyl, cycloalkyl, aralkyl, or lower (cycloalkyl) methyl, or -NR 3 R 4 , when taken together, is 1-pyrrolidinyl, lower alkyl-1-pyrrolidinyl, piperidino, lower alkylpiperidino, morpholino, lower alkylmorpholino, hexamethyleneimino, 1-piperazinyl, 1 -(lower alkyl) -4-piperazinyl, 1 -(hydroxy lower alkyl)-4-piperazinyl, 1 - (lower alkanoyloxyalkyl) - 4 - piperazinyl- 1 - phenyl - 4 - piperazinyl, 1 - (lower alkoxyphenyl) - 4 - piperazinyl, 1 - trifluoromethyl, phenyl - 4 - piperazinyl, 1 - (lower alkylphenyl)- 4 - piperazinyl, 1 - halophenyl - 4 - piperazinyl, 4 - phenyl - 1,2,4,5 - tetrahydro - 1 - pyridinyl, 4 - alkylphenyl - 1,2,5,6 - tetrahydro - 1- pyridinyl, 4 - halophenyl - 1,2,5,6 - tetrahydro- 1 - pyridinyl, 4 - lower alkoxyphenyl - 1,2,5,6- tetrahydro - 1 - pyridinyl, 4 - trifluoromethylphenyl - 1,2,5,6 - tetrahydro - 1 - pyridinyl or azabicyclo - [3.2.2] - nonan - 3 - yl or -C n H 2n - NR 3 R 4 , when taken together, is (2-pyrrolidinyl)- lower alkyl, (3-pyrrolidinyl) lower alkyl, (1- lower alkylpyrrolidinyl) lower alkyl, (1-benzylpyrrolidinyl) - lower alkyl, [1 - (halobenzyl)- pyrrolidinyl - lower alkyl, (1 - lower alkylpyrrolidinyl) - lower alkyl, (1 - benzylpyrrolidinyl) - lower alkyl, [1 - (halobenzyl) - pyrrolidinyl] - lower alkyl, [1 - (lower alkoxybenzyl)- pyrrolidinyl] - lower alkyl, [1 - (lower alkylbenzyl) - pyrrolidinyl] - lower alkyl, piperidinyl lower alkyl, (1-lower alkyl piperdinyl)- lower alkyl, (1 -benzylpiperidinyl)-lower alkyl, [1 - (halobenzyl) - piperidinyl] - lower alkyl, [1 - (lower alkoxybenzyl) - piperidinyl] - lower alkyl, or [1 - (lower alkylbenzyl) - piperidinyl]- lower alkyl and radicals qualified by the term " lower " contain up to 4 carbon atoms are prepared either (a) by heating a compound of Formula II wherein Z is H or -C n H 2n X wher X is halogen, (C 1 -C 4 ) alkylsulphonyloxy or arylsulphonyloxy, (1) when Z is H, with a compound of formula X-C n H 2n NR 3 R 4 or (2) when Z is C n H 2n X 1 with a compound of formula H-NR 3 - R 4 , in both eases optionally followed by reacting the product with P 2 S 5 and/or salt formation and/or removal of a group R 3 is benzyl by hydrogenolysis or (b) reacting a compound of formula with a cyclizing agent providing a carbonyl or thioketone group such as phosgene, thiophosgene, ethyl chloroformate or N,N1-carbonyl diimidazole or (c) where n is 1 by reaction of a compound of Formula II above with formaldehyde/formic acid and a compound of formula HNR 3 R 4 . 2 - (3 - Bromopropyl) - 3,3a,4,5 - tetrahydroimidazo - [1,5-a] - quinolin - 1 - (2H) - one is prepared by reaction of 1,3-dibromopropane and the 2-unsubstituted compound. Pharmaceutical compositions in conventional forms for oral administration and having tranquilizing activity comprise an above novel compound or salt and a carrier therefor.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US52835466A | 1966-02-18 | 1966-02-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
ES336999A1 true ES336999A1 (en) | 1968-06-01 |
Family
ID=24105342
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES336999A Expired ES336999A1 (en) | 1966-02-18 | 1967-02-18 | Imidazo-(1,5-a)-quinoline Derivatives |
Country Status (9)
Country | Link |
---|---|
BE (1) | BE694205A (en) |
CH (1) | CH521366A (en) |
DE (1) | DE1645955A1 (en) |
ES (1) | ES336999A1 (en) |
FR (2) | FR6101M (en) |
GB (1) | GB1172426A (en) |
IL (1) | IL27396A (en) |
NL (1) | NL6702347A (en) |
SE (1) | SE335345B (en) |
-
1967
- 1967-02-06 IL IL2739667A patent/IL27396A/en unknown
- 1967-02-08 GB GB613067A patent/GB1172426A/en not_active Expired
- 1967-02-15 DE DE19671645955 patent/DE1645955A1/en active Pending
- 1967-02-16 CH CH222167A patent/CH521366A/en not_active IP Right Cessation
- 1967-02-16 NL NL6702347A patent/NL6702347A/xx unknown
- 1967-02-17 FR FR95484A patent/FR6101M/fr not_active Expired
- 1967-02-17 FR FR95485A patent/FR1511914A/en not_active Expired
- 1967-02-17 BE BE694205D patent/BE694205A/xx unknown
- 1967-02-17 SE SE223867A patent/SE335345B/xx unknown
- 1967-02-18 ES ES336999A patent/ES336999A1/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
NL6702347A (en) | 1967-08-21 |
DE1645955A1 (en) | 1970-07-16 |
SE335345B (en) | 1971-05-24 |
IL27396A (en) | 1971-03-24 |
GB1172426A (en) | 1969-11-26 |
BE694205A (en) | 1967-08-17 |
FR6101M (en) | 1968-06-10 |
FR1511914A (en) | 1968-02-02 |
CH521366A (en) | 1972-04-15 |
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