GB991838A - Quinoline derivatives - Google Patents
Quinoline derivativesInfo
- Publication number
- GB991838A GB991838A GB23888/63A GB2388863A GB991838A GB 991838 A GB991838 A GB 991838A GB 23888/63 A GB23888/63 A GB 23888/63A GB 2388863 A GB2388863 A GB 2388863A GB 991838 A GB991838 A GB 991838A
- Authority
- GB
- United Kingdom
- Prior art keywords
- piperazinyl
- prepared
- bis
- quinolyl
- chloro
- 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
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
-
- 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
- C07D401/14—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 three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of general formula <FORM:0991838/C2/1> wherein A is any C1-C12 hydrocarbon group, R and R1 are halogen or alkoxy (C1-C4) in the 6- or 7-position of the quinoline nucleus, and the piperazine rings may be substituted with one or more alkyl (C1-C4) groups, and non-toxic acid addition salts thereof, and the preparation of the above compounds by one of the following methods: (a) by reacting a compound of formula <FORM:0991838/C2/2> with a compound of formula <FORM:0991838/C2/3> wherein Y represents the acid residue of a reactive ester such as a halogen atom or a sulphuric or sulphonic ester residue, and other symbols have the above meaning; (b) by reacting 2 mols. of a compound of the third formula above with 1 mol. of a diester Y-A-Y, symbols being defined as above; (method (a) or (b) may optionally be carried out in an inert solvent in the presence of an alkali metal derivative or tertiary amine as condensing agent); (c) by reacting a quinoline derivative of formula <FORM:0991838/C2/4> with a compound of formula <FORM:0991838/C2/5> wherein X represents a halogen atom a methoxy or phenoxy group and other sumbols are as defined above; (d) by reacting 2 mols. of a quinoline derivative as in (c) with a compound of general formula <FORM:0991838/C2/6> the symbols being as defined above; (method (c) or (d) may be carried out in an inert organic solvent with a high boiling-point, for example, between 110 DEG and 200 DEG C.); (e) by reducing the carbonyl group or groups of a compound of formula <FORM:0991838/C2/7> wherein either or both B1 and B are carbonyl groups at least one being carbonyl, A1 is a hydrocarbon group of not more than 10 carbon atoms and other symbols are as defined above, to a methylene group or groups preferably with lithium aluminium hydride in an inert solvent between 20 DEG and 50 DEG C.; (f) in the case where A is a saturated hydrocarbon group by hydrogenating the corresponding compounds in which A contains an ethynylene or vinylene grouping, preferably in the presence of a Raney nickel or Adam's platinum catalyst (in the case where the reactant contains an ethynylene group, the hydrogenation may be stopped at the stage where a vinylene group is formed). 1,5 - Bis - 1 - piperazinyl - pentane is prepared by debenzylating 1,5 - bis - (1 - benzyl-4 - piperazinyl - pentane using hydrogen in the presence of palladium on charcoal, the latter compound is obtained by condensing glutaryl chloride with 1-benzylpiperazine and reducing with lithium aluminium hydride, the resulting 1,5 - bis - (1 - benzyl - 4 - piperazinyl) - 1,5-dioxo-pentane. By a similar method there are prepared 1,5 - bis - 11 - piperazinyl - 3,3-dimethylpentane is prepared the intermediates are 1,5 - bis - (4 - benzyl - 1 - piperazinyl) -3,3-dimethylpentane, and 1,5 - bis - (4 - benzyl - 1 -piperazinyl) -1,5-dioxo-3,3-dimethylpentane) and 1,4 - bis - 11-piperazinylbutane (the intermediates are 1,4-bis-(4-benzyl - 1 - piperazinyl)-butane, and 1,4 - bis - (4 - benzyl - 1 - piperazinyl)-1,4-dioxo-butane). 1,9 - Bis - 11 - piperazinyl - nonane is prepared by reducing 1,9-bis-11-piperazinyl-1,9-dioxo-nonane with lithium aluminium hydride and the latter compound is prepared by reacting benzylpiperazine and azeloyl chloride and debenzylating the resulting 1,9-bis-(4-benzyl-1-piperazinyl)-1,9-dioxo-nonane. 1,4 - Bis - 11 - piperazinylmethyl - benzene is prepared by reacting p-xylylene chloride and piperazine. 7 - Chloro - 4 - 11 - piperazinyl - quinoline is prepared by condensing 4,7-dichloroquinoline and piperazine. By a similar method 1-(7-methoxy - 4 - quinolyl) - piperazine is prepared from 7 - methoxy - 4 - chloro - quinoline and 1 - (6 - chloro - 4 - quinolyl) - piperazine is obtained from 4,6-dichloroquinoline. 1 - (1 - 71 - Chloro - 41 - quinolyl - 4 -piperazinyl)-2-chloroethane is prepared by condensing 1 - 21 - hydroxyethyl - piperazine with 4,7-dichloro-quinoline and treating the resulting 2 - (1 - 71 - chloro - 41 - quinolyl - 4 -piperazinyl)-ethanol with thionyl chloride. 1,4 - Dichlorobut - 2 - yne is prepared by chlorinating but-2-yne-1,4-diol in pyridine. 1,4 - Bis - (1 - 71 - chloro - 41 - quinolyl - 4 -piperazinyl) - 1 - oxo - butane is prepared by reacting 1 - 71 - chloro - 41 - quinolyl - piperazine with 4-chlorobutyryl chloride, and reacting the resulting 1-(1-71-chloro-41-quinolyl-4-piperazinyl - 1 - oxo - 4 - chlorobutane (the picrate thereof is also prepared) with 1-71-chloro-41-quinolylpiperazine. 1 - (7 - Chloro - 4 - quinolyl) - trans - 2,5-dimethyl - piperazin is prepared by reacting 4,7 - dichloroquinoline with trans - 2,5 - dimethylpiperazine and phenol. 1 - (1 - 71 - Chloro - 41 - quinolyl - 4 - piperazinyl) - 3 - chloropropane is prepared by condensing 4,7 - dichloroquinoline and 1 - (3-hydroxypropyl) - piperazine and 4,7 - dichloroquinoline and treating the resulting 3-(1-71-chloro - 41 - quinolyl - 4 - piperazinyl) - propanol with thionyl chloride. By a similar method 1 - (1 - 71 - methoxy - 41 - quinolyl - 4 -piperazinyl) - 3 - chloropropane and the intermediate 3 - (1 - 71 - methoxy - 41 - quinolyl - 4 -piperazinyl) - propanol are prepared. Substituted quinolines of the third general formula above may be obtained from compounds of general formula <FORM:0991838/C2/8> wherein R1 and A have the above meaning by methods known per se, for example, chlorination with thionyl chloride. Substituted piperazines of general formula <FORM:0991838/C2/9> wherein the symbols have the above meaning, may be prepared by condensation of an alpha, omega, dihaloalkane with a 1-ethoxycarbonyl-piperazine, followed by hydrolysis of the ethoxycarbonyl groups in the resulting alpha, omega - bis - (1 - ethoxycarbonyl) - 4 - piperazinyl(-alkane. Substituted quinolines of the formula <FORM:0991838/C2/100> wherein the symbols have the above meaning, may be obtained by reacting compounds of the general formula <FORM:0991838/C2/111> wherein the symbols have the above meaning with compounds of the formula <FORM:0991838/C2/122> respectively, wherein the symbols have the above meaning, or by reacting two mols. of a compound of the general formula <FORM:0991838/C2/133> wherein the symbols have the above meaning, with one mol of Cl-CO-A1-CO-Cl, or by reacting a compound of one of the general formulae <FORM:0991838/C2/144> with a compound of the general formula <FORM:0991838/C2/155> The invention also provides pharmaceutical compositions useful as antimalarials, anthelmintics and amoebicides which comprise a compound of the first general formula above, or a non-toxic acid addition salt thereof, and a pharmaceutical carrier such as an inert solid or liquid, the compositions being for oral, rectal or parenteral administration.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR900747A FR1392458A (en) | 1962-06-14 | 1962-06-14 | New quinoline derivatives and their preparation |
FR908215A FR84902E (en) | 1962-08-30 | 1962-08-30 | New quinoline derivatives and their preparation |
Publications (1)
Publication Number | Publication Date |
---|---|
GB991838A true GB991838A (en) | 1965-05-12 |
Family
ID=26196161
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB23888/63A Expired GB991838A (en) | 1962-06-14 | 1963-06-14 | Quinoline derivatives |
Country Status (6)
Country | Link |
---|---|
CH (1) | CH416628A (en) |
DK (4) | DK105410C (en) |
ES (1) | ES289028A1 (en) |
GB (1) | GB991838A (en) |
LU (1) | LU43730A1 (en) |
OA (1) | OA01392A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002094789A1 (en) * | 2001-05-21 | 2002-11-28 | F. Hoffmann-La Roche Ag | Quinoline derivatives as ligands for the neuropeptide y receptor |
JP2019167331A (en) * | 2018-03-22 | 2019-10-03 | 株式会社東芝 | Amine compound, work medium and water treatment system |
-
1963
- 1963-05-13 LU LU43730D patent/LU43730A1/xx unknown
- 1963-05-31 CH CH683563A patent/CH416628A/en unknown
- 1963-06-14 DK DK418064AA patent/DK105410C/en active
- 1963-06-14 DK DK281863AA patent/DK105340C/en active
- 1963-06-14 DK DK417864AA patent/DK105341C/en active
- 1963-06-14 DK DK417964AA patent/DK105409C/en active
- 1963-06-14 ES ES289028A patent/ES289028A1/en not_active Expired
- 1963-06-14 GB GB23888/63A patent/GB991838A/en not_active Expired
-
1964
- 1964-12-31 OA OA51853A patent/OA01392A/en unknown
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2002094789A1 (en) * | 2001-05-21 | 2002-11-28 | F. Hoffmann-La Roche Ag | Quinoline derivatives as ligands for the neuropeptide y receptor |
US6818767B2 (en) | 2001-05-21 | 2004-11-16 | Hoffmann-La Roche Inc. | Quinoline derivatives |
CN100376557C (en) * | 2001-05-21 | 2008-03-26 | 霍夫曼-拉罗奇有限公司 | Quinoline derivatives as ligands for the neuropeptide y receptor |
JP2019167331A (en) * | 2018-03-22 | 2019-10-03 | 株式会社東芝 | Amine compound, work medium and water treatment system |
Also Published As
Publication number | Publication date |
---|---|
LU43730A1 (en) | 1963-07-13 |
OA01392A (en) | 1969-07-04 |
DK105410C (en) | 1966-09-26 |
CH416628A (en) | 1966-07-15 |
DK105409C (en) | 1966-09-26 |
DK105340C (en) | 1966-09-19 |
DK105341C (en) | 1966-09-19 |
ES289028A1 (en) | 1963-11-16 |
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