CH420149A - Verfahren zur Herstellung von Chinolinderivaten - Google Patents
Verfahren zur Herstellung von ChinolinderivatenInfo
- Publication number
- CH420149A CH420149A CH7081359A CH7081359A CH420149A CH 420149 A CH420149 A CH 420149A CH 7081359 A CH7081359 A CH 7081359A CH 7081359 A CH7081359 A CH 7081359A CH 420149 A CH420149 A CH 420149A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- quinoline
- piperazine
- formula
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 2
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- -1 6-methoxy-8- (piperazino-n-hexylamino) - quinoline Chemical compound 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 241000222722 Leishmania <genus> Species 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 3
- WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- 210000000952 spleen Anatomy 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 229960004756 ethanol Drugs 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- DHCXOJNSYQZFBE-UHFFFAOYSA-N 6-ethoxyquinolin-8-amine Chemical compound N1=CC=CC2=CC(OCC)=CC(N)=C21 DHCXOJNSYQZFBE-UHFFFAOYSA-N 0.000 description 2
- 241000699800 Cricetinae Species 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VXDQCNRBICUPEY-UHFFFAOYSA-N n-(3-chloropropyl)-6-methoxyquinolin-8-amine Chemical compound N1=CC=CC2=CC(OC)=CC(NCCCCl)=C21 VXDQCNRBICUPEY-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- INDBQLZJXZLFIT-UHFFFAOYSA-N primaquine Chemical compound N1=CC=CC2=CC(OC)=CC(NC(C)CCCN)=C21 INDBQLZJXZLFIT-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- LWEOFVINMVZGAS-UHFFFAOYSA-N 3-piperazin-1-ylpropan-1-ol Chemical compound OCCCN1CCNCC1 LWEOFVINMVZGAS-UHFFFAOYSA-N 0.000 description 1
- RDFZQTDLGKFDNB-UHFFFAOYSA-N 5,6-dimethoxyquinolin-8-amine Chemical compound N1=CC=CC2=C(OC)C(OC)=CC(N)=C21 RDFZQTDLGKFDNB-UHFFFAOYSA-N 0.000 description 1
- OCJXADFZUXMLLE-UHFFFAOYSA-N 6-methoxy-n-(3-piperazin-1-ylpropyl)quinolin-8-amine Chemical compound C=12N=CC=CC2=CC(OC)=CC=1NCCCN1CCNCC1 OCJXADFZUXMLLE-UHFFFAOYSA-N 0.000 description 1
- YGGTVPCTAKYCSQ-UHFFFAOYSA-N 6-methoxyquinolin-8-amine Chemical compound N1=CC=CC2=CC(OC)=CC(N)=C21 YGGTVPCTAKYCSQ-UHFFFAOYSA-N 0.000 description 1
- 241000222727 Leishmania donovani Species 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- C07D215/40—Nitrogen atoms attached in position 8
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB854758A GB878461A (en) | 1958-03-17 | 1958-03-17 | Quinoline derivatives and the manufacture thereof |
| GB1019458 | 1958-03-31 | ||
| GB2392458 | 1958-07-24 | ||
| GB2392558 | 1958-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH420149A true CH420149A (de) | 1966-09-15 |
Family
ID=27447662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7081359A CH420149A (de) | 1958-03-17 | 1959-03-16 | Verfahren zur Herstellung von Chinolinderivaten |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH420149A (da) |
| DK (2) | DK104572C (da) |
| ES (1) | ES247953A1 (da) |
| SE (1) | SE308109B (da) |
-
1959
- 1959-03-14 SE SE2497/59A patent/SE308109B/xx unknown
- 1959-03-16 DK DK441063AA patent/DK104572C/da active
- 1959-03-16 CH CH7081359A patent/CH420149A/de unknown
- 1959-03-16 ES ES0247953A patent/ES247953A1/es not_active Expired
- 1959-03-16 DK DK93859AA patent/DK104516C/da active
Also Published As
| Publication number | Publication date |
|---|---|
| SE308109B (da) | 1969-02-03 |
| DK104572C (da) | 1966-06-06 |
| ES247953A1 (es) | 1959-07-01 |
| DK104516C (da) | 1966-05-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH615152A5 (en) | Process for the preparation of carboxylic acid amides and the carboxylic acid amides thus prepared | |
| DE3441975C2 (da) | ||
| DE2065636A1 (de) | Neue tricyclische verbindungen | |
| CH638799A5 (de) | 2h-benzofuran-3-on-derivate sowie ein verfahren zu deren herstellung und solche verbindungen enthaltende pharmazeutische praeparate. | |
| DE2428486A1 (de) | Azapurinone | |
| AT371460B (de) | Verfahren zur herstellung neuer benzopyranderivate und ihrer salze | |
| DE69014930T2 (de) | Aralkylamin-Verbindungen. | |
| EP0064255A1 (de) | Benzopyranylether, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel und Zwischenprodukte | |
| CH631973A5 (de) | Verfahren zur herstellung von benzimidazolderivaten. | |
| DE3642497A1 (de) | Substituierte aminopropionsaeureamide, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung sowie die bei der herstellung anfallenden neuen zwischenprodukte | |
| DE2253914A1 (de) | Neue chromonderivate und verfahren zu ihrer herstellung | |
| CH420149A (de) | Verfahren zur Herstellung von Chinolinderivaten | |
| DE1795653A1 (de) | Verfahren zur herstellung von 2alkoxy-4.5-azimidobenzamiden | |
| DE2819215C2 (da) | ||
| DE1097996B (de) | Verfahren zur Herstellung von Phenthiazinderivaten | |
| CH356121A (de) | Verfahren zur Herstellung von N-monosubstituierten Amiden vona-Aminoalkyl-a-phenyl-essigsäuren | |
| CH369759A (de) | Verfahren zur Herstellung von N-Alkylpiperidin-a-carbonsäureaniliden | |
| DE2827932A1 (de) | Biphenylsulfonyliminoverbindungen | |
| DE2423725A1 (de) | 5-phenyl-4-oxo-delta hoch 2,alphathiazolidinessigsaeureester | |
| DE932127C (de) | Verfahren zur Herstellung von neuen Derivaten des Pyrimidins | |
| DE1695382A1 (de) | Neue 2-substituierte 2,3-Diaminopyridine und Verfahren zu ihrer Herstellung | |
| AT205040B (de) | Verfahren zur Herstellung von neuen N-Methyldiaminen | |
| AT234680B (de) | Verfahren zur Herstellung von neuen Aminosäuren | |
| AT226723B (de) | Verfahren zur Umwandlung von Thiaxanthenen | |
| AT202147B (de) | Verfahren zur Herstellung von neuen Piperazinderivaten und von deren Salzen |