GB999237A - Quinoline derivatives - Google Patents
Quinoline derivativesInfo
- Publication number
- GB999237A GB999237A GB2488763A GB2488763A GB999237A GB 999237 A GB999237 A GB 999237A GB 2488763 A GB2488763 A GB 2488763A GB 2488763 A GB2488763 A GB 2488763A GB 999237 A GB999237 A GB 999237A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- formula
- compounds
- compound
- ethyl
- 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
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title 1
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 11
- QNGUPQRODVPRDC-UHFFFAOYSA-N 7-chloroquinoline Chemical compound C1=CC=NC2=CC(Cl)=CC=C21 QNGUPQRODVPRDC-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 238000009833 condensation Methods 0.000 abstract 2
- 230000005494 condensation Effects 0.000 abstract 2
- 125000003916 ethylene diamine group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- OVVDHASRRHVOPG-UHFFFAOYSA-N 2-[2-[2-(1,3-dioxoisoindol-2-yl)ethyl-ethylamino]ethyl]isoindole-1,3-dione Chemical compound C(C)N(CCN1C(C=2C(C1=O)=CC=CC=2)=O)CCN1C(C=2C(C1=O)=CC=CC=2)=O OVVDHASRRHVOPG-UHFFFAOYSA-N 0.000 abstract 1
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 abstract 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000000507 anthelmentic effect Effects 0.000 abstract 1
- 230000000078 anti-malarial effect Effects 0.000 abstract 1
- 239000003430 antimalarial agent Substances 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- LQAWSZYJRFRCHK-UHFFFAOYSA-N n'-(2-aminoethyl)-n'-ethylethane-1,2-diamine Chemical compound NCCN(CC)CCN LQAWSZYJRFRCHK-UHFFFAOYSA-N 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the formulae <FORM:0999237/C2/1> wherein A represents a divalent straight or branched chain aliphatic hydrocarbon group containing 2 to 6 carbon atoms, R and R1 represent, the same or different, a hydrogen atom or an alkyl group containing up to 4 carbon atoms and B represents a single bond or a group -A1-NH-, in which A1 has the same significance as A and is attached to the nitrogen atom of the ethylenediamine group, and non-toxic acid addition salts thereof and the preparation thereof by reacting a 7-chloroquinoline of the formula <FORM:0999237/C2/2> with a compound of the formula <FORM:0999237/C2/3> where (a) Y represent a halogen atom or phenoxy group, one of V and W represents a group -ANH-, the group A being attached to a nitrogen atom of the ethylenediamine group, and the other represents the symbol B in the formula I; (b) Y represents the group <FORM:0999237/C2/4> , wherein X represents the acid residue of a reactive ester, Z represents a hydrogen atom, an alkanoyl group of up to 4 carbon atoms or a benzoyl group, V represents a single bond and W represents B1, i e a single bond or the group -A1-NZ-; and, if necessary, removing from the resultant product the group Z The compounds are also prepared by reacting two molecules of a 7-chloroquinoline of the formula II wherein Y represents a halogen atom or phenoxy group with one molecule of a compound of the formula <FORM:0999237/C2/5> and where B represents a group identical with that represented by -HN-A-, by reacting two molecules of a 7-chloroquinoline of the formula <FORM:0999237/C2/6> with one molecule of a compound of the formula <FORM:0999237/C2/7> Compounds of the formula III may be made by condensing equimolecular proportions of a compound of the formula II and a compound of the formula IV <FORM:0999237/C2/8> wherein Y, V and W have the significance set out under the heading (a) above. Where V represents a single bond and W represents the group -A-NZ-, compounds of the formula III may be made by condensing equimolecular proportions of compounds of the formulae V and VI. 1,10 - Diamino - 4,7 - diazadecane is prepared by catalytic reduction of 1,8-dicyano-3,6-diazooctane which is made by condensation of acrylonitrile with ethylene diamine. N - Ethyl - N,N - bis(2 - aminoethyl)amine is made by dephthalimidation of N-ethyl-N,N-bis (2-phthalimido-ethyl)amine which is made by the condensation of N-ethyl-N,N-bis(2-chloroethyl) amine with potassium phthalimide. Pharmaceutical compositions for oral, rectal and parenteral administration, which have antimalarial, amoebicidic and anthelmintic properties and which may take the form of tablets, pills, dispersible powders, granules, emulsions, solutions, suspensions, syrups and elixirs comprise compounds of the general formula I and addition salts thereof.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR901653 | 1962-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB999237A true GB999237A (en) | 1965-07-21 |
Family
ID=8781651
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2488763A Expired GB999237A (en) | 1962-06-22 | 1963-06-21 | Quinoline derivatives |
Country Status (7)
| Country | Link |
|---|---|
| AT (1) | AT240364B (en) |
| CH (1) | CH424781A (en) |
| DE (1) | DE1296635B (en) |
| DK (2) | DK107807C (en) |
| ES (1) | ES289291A1 (en) |
| GB (1) | GB999237A (en) |
| LU (1) | LU43783A1 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001044198A1 (en) * | 1999-12-17 | 2001-06-21 | G.O.T. Gesellschaft Für Therapieoptimierung Und Targeting Entwicklungs Mbh | Amphiphilic quinolylpolyamines as transfer agents for biologically active macromolecules |
| WO2007097450A1 (en) * | 2006-02-27 | 2007-08-30 | Nagoya City University | Compound with antimalarial activity and antimalarial drug containing the same as active ingredient |
| JP2014513101A (en) * | 2011-04-29 | 2014-05-29 | ザ・トラステイーズ・オブ・ザ・ユニバーシテイ・オブ・ペンシルベニア | Novel bisaminoquinoline compounds, pharmaceutical compositions prepared therefrom, and uses thereof |
| US10221140B2 (en) | 2014-08-08 | 2019-03-05 | The Trustees Of The University Of Pennsylvania | Asymmetric bisaminoquinolines and bisaminoquinolines with varied linkers as autophagy inhibitors for cancer and other therapy |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1052356A (en) * | 1952-03-12 | 1954-01-25 | Rhone Poulenc Sa | New quinoline derivatives and their preparation process |
-
1963
- 1963-05-21 LU LU43783D patent/LU43783A1/xx unknown
- 1963-06-14 CH CH742463A patent/CH424781A/en unknown
- 1963-06-18 DE DE1963R0035446 patent/DE1296635B/en active Pending
- 1963-06-21 AT AT500663A patent/AT240364B/en active
- 1963-06-21 GB GB2488763A patent/GB999237A/en not_active Expired
- 1963-06-22 DK DK288564A patent/DK107807C/en active
- 1963-06-22 ES ES289291A patent/ES289291A1/en not_active Expired
- 1963-06-22 DK DK297463A patent/DK104735C/en active
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001044198A1 (en) * | 1999-12-17 | 2001-06-21 | G.O.T. Gesellschaft Für Therapieoptimierung Und Targeting Entwicklungs Mbh | Amphiphilic quinolylpolyamines as transfer agents for biologically active macromolecules |
| WO2007097450A1 (en) * | 2006-02-27 | 2007-08-30 | Nagoya City University | Compound with antimalarial activity and antimalarial drug containing the same as active ingredient |
| JP2014513101A (en) * | 2011-04-29 | 2014-05-29 | ザ・トラステイーズ・オブ・ザ・ユニバーシテイ・オブ・ペンシルベニア | Novel bisaminoquinoline compounds, pharmaceutical compositions prepared therefrom, and uses thereof |
| AU2012249646B2 (en) * | 2011-04-29 | 2017-06-08 | The Trustees Of The University Of Pennsylvania | Novel bisaminoquinoline compounds, pharmaceutical compositions prepared therefrom and their use |
| US10047052B2 (en) | 2011-04-29 | 2018-08-14 | The Trustees Of The University Of Pennsylvania | Bisaminoquinoline compounds, pharmaceutical compositions prepared therefrom and their use |
| US11591298B2 (en) | 2011-04-29 | 2023-02-28 | The Trustees Of The University Of Pennsylvania | Bisaminoquinoline compounds, pharmaceutical compositions prepared therefrom and their use |
| US10221140B2 (en) | 2014-08-08 | 2019-03-05 | The Trustees Of The University Of Pennsylvania | Asymmetric bisaminoquinolines and bisaminoquinolines with varied linkers as autophagy inhibitors for cancer and other therapy |
| US11001558B2 (en) | 2014-08-08 | 2021-05-11 | The Trustees Of The University Of Pennsylvania | Asymmetric bisaminoquinolines and bisaminoquinolines with varied linkers as autophagy inhibitors for cancer and other therapy |
| US11639335B2 (en) | 2014-08-08 | 2023-05-02 | The Trustees Of The University Of Pennsylvania | Asymmetric bisaminoquinolines and bisaminoquinolines with varied linkers as autophagy inhibitors for cancer and other therapy |
Also Published As
| Publication number | Publication date |
|---|---|
| DK107807C (en) | 1967-07-10 |
| CH424781A (en) | 1966-11-30 |
| DE1296635B (en) | 1969-09-18 |
| ES289291A1 (en) | 1963-12-16 |
| LU43783A1 (en) | 1963-07-22 |
| AT240364B (en) | 1965-05-25 |
| DK104735C (en) | 1966-06-27 |
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