DE2221669A1 - Neue substituierte Tetrahydrochinoline - Google Patents
Neue substituierte TetrahydrochinolineInfo
- Publication number
- DE2221669A1 DE2221669A1 DE19722221669 DE2221669A DE2221669A1 DE 2221669 A1 DE2221669 A1 DE 2221669A1 DE 19722221669 DE19722221669 DE 19722221669 DE 2221669 A DE2221669 A DE 2221669A DE 2221669 A1 DE2221669 A1 DE 2221669A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- group
- compound
- turning
- hydrogen
- 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.)
- Ceased
Links
- 150000003530 tetrahydroquinolines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 28
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 5
- 125000005042 acyloxymethyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 244000005700 microbiome Species 0.000 claims 2
- -1 Alkoxynvethyl Chemical group 0.000 claims 1
- 241000228212 Aspergillus Species 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- 239000012458 free base Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 6
- 238000003306 harvesting Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 150000008054 sulfonate salts Chemical class 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000000347 anti-schistosomal effect Effects 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical class CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- LAOOXBLMIJHMFO-UHFFFAOYSA-N 1-[2-(diethylamino)ethylamino]-4-methylthioxanthen-9-one;hydron;chloride Chemical class Cl.S1C2=CC=CC=C2C(=O)C2=C1C(C)=CC=C2NCCN(CC)CC LAOOXBLMIJHMFO-UHFFFAOYSA-N 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- AFLUJRQPQFHJIF-UHFFFAOYSA-M C12(C(=O)CC(CC1)C2(C)C)CS(=O)(=O)[O-].[Br+] Chemical compound C12(C(=O)CC(CC1)C2(C)C)CS(=O)(=O)[O-].[Br+] AFLUJRQPQFHJIF-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000862448 Chlorocebus Species 0.000 description 1
- 240000001414 Eucalyptus viminalis Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000845082 Panama Species 0.000 description 1
- 241000242678 Schistosoma Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004849 alkoxymethyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002550 fecal effect Effects 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000003975 mesenteric artery Anatomy 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001843 schistosomicidal effect Effects 0.000 description 1
- 239000003198 schistosomicide agent Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
Classifications
-
- 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
- C07D215/18—Halogen atoms or nitro radicals
-
- 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1345171A GB1366683A (en) | 1971-05-06 | 1971-05-06 | Substituted tetrahydroquinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2221669A1 true DE2221669A1 (de) | 1972-12-28 |
Family
ID=10023227
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722221669 Ceased DE2221669A1 (de) | 1971-05-06 | 1972-05-03 | Neue substituierte Tetrahydrochinoline |
Country Status (8)
| Country | Link |
|---|---|
| AR (1) | AR205874A1 (enExample) |
| AU (1) | AU4164572A (enExample) |
| BE (1) | BE782924A (enExample) |
| CH (1) | CH575396A5 (enExample) |
| DE (1) | DE2221669A1 (enExample) |
| ES (1) | ES402483A1 (enExample) |
| FR (1) | FR2135348B1 (enExample) |
| GB (1) | GB1366683A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0808835A1 (en) * | 1996-05-21 | 1997-11-26 | CHINOIN Gyògyszer és Vegyészeti Termékek Gyára RT. | Process for the preparation of optically active compounds |
| EP0819677A1 (en) * | 1996-05-21 | 1998-01-21 | CHINOIN Gyògyszer és Vegyészeti Termékek Gyára RT. | Process for the preparation of optically active compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1278273A (en) * | 1970-01-29 | 1972-06-21 | Pfizer Ltd | Substituted tetrahydroquinolines |
-
1971
- 1971-05-06 GB GB1345171A patent/GB1366683A/en not_active Expired
-
1972
- 1972-01-01 AR AR24180572A patent/AR205874A1/es active
- 1972-04-27 AU AU41645/72A patent/AU4164572A/en not_active Expired
- 1972-05-02 BE BE782924A patent/BE782924A/xx not_active IP Right Cessation
- 1972-05-03 DE DE19722221669 patent/DE2221669A1/de not_active Ceased
- 1972-05-04 CH CH665172A patent/CH575396A5/xx not_active IP Right Cessation
- 1972-05-05 FR FR7216235A patent/FR2135348B1/fr not_active Expired
- 1972-05-06 ES ES402483A patent/ES402483A1/es not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0808835A1 (en) * | 1996-05-21 | 1997-11-26 | CHINOIN Gyògyszer és Vegyészeti Termékek Gyára RT. | Process for the preparation of optically active compounds |
| EP0819677A1 (en) * | 1996-05-21 | 1998-01-21 | CHINOIN Gyògyszer és Vegyészeti Termékek Gyára RT. | Process for the preparation of optically active compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2135348B1 (enExample) | 1976-04-16 |
| BE782924A (fr) | 1972-11-03 |
| AR205874A1 (es) | 1976-06-15 |
| ES402483A1 (es) | 1975-03-16 |
| CH575396A5 (enExample) | 1976-05-14 |
| AU4164572A (en) | 1973-11-01 |
| GB1366683A (en) | 1974-09-11 |
| FR2135348A1 (enExample) | 1972-12-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2921072A1 (de) | Phenoxyalkylcarbonsaeure-derivate und diese verbindungen enthaltende arzneimittel | |
| DE1300575B (de) | Benzo[b]thiophene | |
| DE2719211A1 (de) | Arylalkylpiperidine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
| DE2702537A1 (de) | Neue piperazinderivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel | |
| DE2724478C2 (de) | 5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-on-derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2221669A1 (de) | Neue substituierte Tetrahydrochinoline | |
| DE2103550C3 (de) | 2-Benzoylalkyl-6,7-benzomorphane, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate | |
| DD153550A5 (de) | Verfahren zur herstellung von neuer 1,2,4-oxadiazolin-5-on-derivaten | |
| DE1695855B2 (de) | 4-(5-Isobutyl-2-pyrimidinyl)-sulfonamidophenylessigsäure-(2-methoxy-5-Chloranilid) und dessen Salze mit physiologisch verträglichen Basen | |
| DE1620007B2 (de) | Decahydroisochinoline | |
| DE2624918A1 (de) | Arzneimittel mit antiarrhythmischer wirkung | |
| DE2412388A1 (de) | Dibenzothiophenderivate, verfahren zu deren herstellung und sie enthaltende arzneimittel | |
| DE1543744C3 (de) | 3-Alkylflavanone und Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel | |
| DE3104387A1 (de) | Neue indanderivate, verfahren zu ihrer herstellung und ihre verwendung | |
| DE2436721A1 (de) | 2,2-disubstituierte benzodioxol- aether | |
| DE2423725A1 (de) | 5-phenyl-4-oxo-delta hoch 2,alphathiazolidinessigsaeureester | |
| DE2327659C2 (de) | Phenoxycarbonsäurederivate und sie enthaltende Arzneimittel | |
| DE1568858C (de) | Dialkalisalze des 4,4 Disulfoxy di phenyl (2 pyridyl) methans und Verfahren zu ihrer Herstellung | |
| DE1913701C3 (de) | Aminsubstituierte tri cyclische Verbindungen und ihre Salze, Verfahren zu ihrer Herstellung sowie diese enthaltende pharmazeutische Zusammensetzungen | |
| DE1418540C (de) | Verfahren zur Herstellung von 1,3,2 Dioxaborolanen oder 1,3,2 Dioxabonnanen | |
| DE2458374A1 (de) | Neuartige 1,3-benzodioxol-abkoemmlinge | |
| DE2428680A1 (de) | Neue substituierte 1-(2',4',6'/rihydroxyphenyl)-propandion-(1,2)- verbindungen und arzneimittel | |
| DE2335665C3 (de) | Terpennitrolamlne, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Zubereitungen | |
| CH643833A5 (de) | Aminoisochinolinderivate, verfahren zur herstellung derselben und solche verbindungen enthaltende arzneimittel. | |
| DE2159679C3 (de) | Isonipecotinsäurederivate |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8131 | Rejection |