DE2806909C2 - - Google Patents
Info
- Publication number
- DE2806909C2 DE2806909C2 DE2806909A DE2806909A DE2806909C2 DE 2806909 C2 DE2806909 C2 DE 2806909C2 DE 2806909 A DE2806909 A DE 2806909A DE 2806909 A DE2806909 A DE 2806909A DE 2806909 C2 DE2806909 C2 DE 2806909C2
- Authority
- DE
- Germany
- Prior art keywords
- bis
- trifluoromethyl
- quinoline
- methanol
- solution
- 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
- BUDRHPWUUSCWLP-UHFFFAOYSA-N [2-(trifluoromethyl)quinolin-4-yl]methanol Chemical compound C1=CC=C2C(CO)=CC(C(F)(F)F)=NC2=C1 BUDRHPWUUSCWLP-UHFFFAOYSA-N 0.000 claims description 12
- DXALAFAFIXJDOS-UHFFFAOYSA-N 4-bromo-2,8-bis(trifluoromethyl)quinoline Chemical compound C1=CC=C(C(F)(F)F)C2=NC(C(F)(F)F)=CC(Br)=C21 DXALAFAFIXJDOS-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- 241000223960 Plasmodium falciparum Species 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- XEEQGYMUWCZPDN-DOMZBBRYSA-N (-)-(11S,2'R)-erythro-mefloquine Chemical compound C([C@@H]1[C@@H](O)C=2C3=CC=CC(=C3N=C(C=2)C(F)(F)F)C(F)(F)F)CCCN1 XEEQGYMUWCZPDN-DOMZBBRYSA-N 0.000 description 1
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
- JIWHKBAFGFPZKM-UHFFFAOYSA-N 2,8-bis(trifluoromethyl)-1h-quinolin-4-one Chemical compound C1=CC=C2C(O)=CC(C(F)(F)F)=NC2=C1C(F)(F)F JIWHKBAFGFPZKM-UHFFFAOYSA-N 0.000 description 1
- SUNAMHNJYSQUPL-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-quinolin-4-one Chemical compound C1=CC=C2NC(C(F)(F)F)=CC(=O)C2=C1 SUNAMHNJYSQUPL-UHFFFAOYSA-N 0.000 description 1
- 241000282708 Aotus <primate> Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000224017 Plasmodium berghei Species 0.000 description 1
- 240000002380 Rosa carolina Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- LUDFDSXDVJABBT-UHFFFAOYSA-N [2,8-bis(trifluoromethyl)quinolin-4-yl]-pyridin-2-ylmethanol Chemical compound C=1C(C(F)(F)F)=NC2=C(C(F)(F)F)C=CC=C2C=1C(O)C1=CC=CC=N1 LUDFDSXDVJABBT-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960003677 chloroquine Drugs 0.000 description 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- OCJKUQIPRNZDTK-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)(F)F OCJKUQIPRNZDTK-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- -1 hexane Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 229960001962 mefloquine Drugs 0.000 description 1
- HOSVRPJWWKEZBN-UHFFFAOYSA-N methanol;quinoline Chemical class OC.N1=CC=CC2=CC=CC=C21 HOSVRPJWWKEZBN-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76981677A | 1977-02-17 | 1977-02-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2806909A1 DE2806909A1 (de) | 1978-08-24 |
| DE2806909C2 true DE2806909C2 (en:Method) | 1988-04-07 |
Family
ID=25086585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782806909 Granted DE2806909A1 (de) | 1977-02-17 | 1978-02-17 | Verfahren zur herstellung von mefloquin |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS53103478A (en:Method) |
| AT (1) | AT358044B (en:Method) |
| BE (1) | BE864002A (en:Method) |
| CH (2) | CH640530A5 (en:Method) |
| DE (1) | DE2806909A1 (en:Method) |
| FR (1) | FR2381044A1 (en:Method) |
| GB (1) | GB1594282A (en:Method) |
| IT (1) | IT1158450B (en:Method) |
| NL (1) | NL7801787A (en:Method) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2940443A1 (de) * | 1979-10-05 | 1981-04-16 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von erythro-(alpha)-2-piperidyl-2,8-bis-(trifluormethyl)-4-chinolin-methanol |
| FR2485014A1 (fr) * | 1980-06-20 | 1981-12-24 | Pharmindustrie | Nouveaux derives de (quinolyl-2, -3 ou -4)-1 (piperidyl ou pyrrolidinyl-2 ou -3)-2 ou -3 ethanone ou propanone, procedes pour leur preparation, et leur utilisation comme medicaments |
| DE3038504A1 (de) | 1980-10-11 | 1982-06-03 | Basf Ag, 6700 Ludwigshafen | Neue 4-chinolinmethanderivate, ihre herstellung und verwendung zur darstellung von substanzen mit arzneimittelwirkung |
| US4507482A (en) * | 1982-04-14 | 1985-03-26 | Hoffmann-La Roche Inc. | Purification of mefloquin hydrochloride |
| DK160499C (da) * | 1982-09-10 | 1991-08-26 | Hoffmann La Roche | Fremgangsmaade til fremstilling af mefloquin og mellemprodukt til anvendelse herved |
| JPH0234129U (en:Method) * | 1989-05-25 | 1990-03-05 | ||
| HUT54363A (en) * | 1989-07-25 | 1991-02-28 | Alkaloida Vegyeszeti Gyar | Process for producing pyridyl-methyl-quinolin derivatives |
| GB9819382D0 (en) * | 1998-09-04 | 1998-10-28 | Cerebrus Ltd | Chemical compounds I |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH590274A5 (en:Method) * | 1970-03-16 | 1977-07-29 | Hoffmann La Roche | |
| CH605916A5 (en:Method) * | 1973-12-07 | 1978-10-13 | Hoffmann La Roche |
-
1978
- 1978-02-15 FR FR7804271A patent/FR2381044A1/fr active Granted
- 1978-02-16 NL NL7801787A patent/NL7801787A/xx not_active Application Discontinuation
- 1978-02-16 GB GB6207/78A patent/GB1594282A/en not_active Expired
- 1978-02-16 JP JP1601378A patent/JPS53103478A/ja active Granted
- 1978-02-16 AT AT113378A patent/AT358044B/de not_active IP Right Cessation
- 1978-02-16 BE BE185206A patent/BE864002A/xx not_active IP Right Cessation
- 1978-02-16 IT IT20331/78A patent/IT1158450B/it active
- 1978-02-16 CH CH169578A patent/CH640530A5/de not_active IP Right Cessation
- 1978-02-17 DE DE19782806909 patent/DE2806909A1/de active Granted
-
1982
- 1982-05-14 CH CH301282A patent/CH640531A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7801787A (nl) | 1978-08-21 |
| BE864002A (fr) | 1978-08-16 |
| JPS53103478A (en) | 1978-09-08 |
| DE2806909A1 (de) | 1978-08-24 |
| CH640530A5 (en) | 1984-01-13 |
| IT7820331A0 (it) | 1978-02-16 |
| GB1594282A (en) | 1981-07-30 |
| IT1158450B (it) | 1987-02-18 |
| ATA113378A (de) | 1980-01-15 |
| JPS6257631B2 (en:Method) | 1987-12-02 |
| FR2381044B1 (en:Method) | 1983-06-10 |
| FR2381044A1 (fr) | 1978-09-15 |
| AT358044B (de) | 1980-08-11 |
| CH640531A5 (en) | 1984-01-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OB | Request for examination as to novelty | ||
| OC | Search report available | ||
| 8110 | Request for examination paragraph 44 | ||
| 8181 | Inventor (new situation) |
Free format text: GRETHE, GUENTHER, NORTH CALDWELL, N.J., US MITT, TOOMAS, BLOOMFIELD, N.J., US |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8327 | Change in the person/name/address of the patent owner |
Owner name: F. HOFFMANN-LA ROCHE AG, BASEL, CH |
|
| 8328 | Change in the person/name/address of the agent |
Free format text: LEDERER, F., DIPL.-CHEM. DR., 8000 MUENCHEN RIEDERER FRHR. VON PAAR ZU SCHOENAU, A., DIPL.-ING., PAT.-ANWAELTE, 8300 LANDSHUT |
|
| 8339 | Ceased/non-payment of the annual fee |