GB1441519A - Cinchonidine and cinchonidine derivatives - Google Patents
Cinchonidine and cinchonidine derivativesInfo
- Publication number
- GB1441519A GB1441519A GB5284374A GB5284374A GB1441519A GB 1441519 A GB1441519 A GB 1441519A GB 5284374 A GB5284374 A GB 5284374A GB 5284374 A GB5284374 A GB 5284374A GB 1441519 A GB1441519 A GB 1441519A
- Authority
- GB
- United Kingdom
- Prior art keywords
- trifluoromethyl
- ethyl
- bis
- compound
- piperidyl
- 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
- KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 title abstract 4
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 9
- 229940111121 antirheumatic drug quinolines Drugs 0.000 abstract 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 4
- -1 1 -substituted - 2 - trifluoromethyl - 4 - quinolinol Chemical class 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 239000000543 intermediate Substances 0.000 abstract 3
- 150000002642 lithium compounds Chemical class 0.000 abstract 3
- HWXMQNMPJULKCQ-UHFFFAOYSA-N 4-methyl-2,8-bis(trifluoromethyl)quinoline Chemical compound C1=CC=C2C(C)=CC(C(F)(F)F)=NC2=C1C(F)(F)F HWXMQNMPJULKCQ-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 238000011065 in-situ storage Methods 0.000 abstract 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 2
- SHXHPUAKLCCLDV-UHFFFAOYSA-N 1,1,1-trifluoropentane-2,4-dione Chemical compound CC(=O)CC(=O)C(F)(F)F SHXHPUAKLCCLDV-UHFFFAOYSA-N 0.000 abstract 1
- SJNVVYLZZUSUDI-HKUYNNGSSA-N 1-[(3R,4S)-1-benzoyl-3-ethylpiperidin-4-yl]-3-[2,8-bis(trifluoromethyl)quinolin-4-yl]propan-2-one Chemical compound FC(C1=NC2=C(C=CC=C2C(=C1)CC(C[C@H]1[C@H](CN(CC1)C(C1=CC=CC=C1)=O)CC)=O)C(F)(F)F)(F)F SJNVVYLZZUSUDI-HKUYNNGSSA-N 0.000 abstract 1
- NPMAASFLXZLSHY-STQMWFEESA-N 1-[2,8-bis(trifluoromethyl)quinolin-4-yl]-3-[(3R,4S)-3-ethylpiperidin-4-yl]propan-2-one Chemical compound FC(C1=NC2=C(C=CC=C2C(=C1)CC(C[C@H]1[C@H](CNCC1)CC)=O)C(F)(F)F)(F)F NPMAASFLXZLSHY-STQMWFEESA-N 0.000 abstract 1
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 abstract 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- CTUYBUXNBUTGOW-UHFFFAOYSA-N C1=CC=C2C([Li])=CC(C(F)(F)F)=NC2=C1C(F)(F)F Chemical compound C1=CC=C2C([Li])=CC(C(F)(F)F)=NC2=C1C(F)(F)F CTUYBUXNBUTGOW-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 230000000078 anti-malarial effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 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 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 230000000640 hydroxylating effect Effects 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 150000003248 quinolines Chemical class 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 229910001961 silver nitrate Inorganic materials 0.000 abstract 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
-
- 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
- C07D215/12—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 substituted hydrocarbon radicals attached to ring carbon atoms
-
- 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
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42264573A | 1973-12-07 | 1973-12-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1441519A true GB1441519A (en) | 1976-07-07 |
Family
ID=23675777
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5284374A Expired GB1441519A (en) | 1973-12-07 | 1974-12-06 | Cinchonidine and cinchonidine derivatives |
Country Status (17)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2381044A1 (fr) * | 1977-02-17 | 1978-09-15 | Hoffmann La Roche | Procede pour la preparation de mefloquine |
| HU191508B (en) * | 1982-12-02 | 1987-02-27 | Alkaloida Vegyeszeti Gyar,Hu | Process for preparing new chloromethyl-quinoline derivatives |
| WO1999012532A2 (en) * | 1997-09-08 | 1999-03-18 | F.Hoffmann-La Roche Ag | Piperidine derivatives against malaria |
| JP2002360830A (ja) * | 2001-06-04 | 2002-12-17 | Heiwa Corp | 球貯蔵入賞装置 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1217427A (en) * | 1967-12-21 | 1970-12-31 | America Home Products Corp | Cinchona alkaloid derivatives |
| CH590275A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1970-03-16 | 1977-07-29 | Hoffmann La Roche | |
| CH565792A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-01-07 | 1975-08-29 | Hoffmann La Roche |
-
1974
- 1974-11-30 CH CH1586274A patent/CH605916A5/xx not_active IP Right Cessation
- 1974-12-02 PH PH16586A patent/PH10837A/en unknown
- 1974-12-02 ZA ZA00747664A patent/ZA747664B/xx unknown
- 1974-12-03 SE SE7415160A patent/SE415100B/xx unknown
- 1974-12-04 IL IL46181A patent/IL46181A/xx unknown
- 1974-12-05 FR FR7439824A patent/FR2292476A1/fr active Granted
- 1974-12-05 CA CA215,292A patent/CA1039283A/en not_active Expired
- 1974-12-06 NL NL7415931A patent/NL7415931A/xx not_active Application Discontinuation
- 1974-12-06 BR BR10249/74A patent/BR7410249A/pt unknown
- 1974-12-06 DK DK637674AA patent/DK141700B/da unknown
- 1974-12-06 GB GB5284374A patent/GB1441519A/en not_active Expired
- 1974-12-06 BE BE151217A patent/BE823023A/xx unknown
- 1974-12-06 AT AT977974A patent/AT339310B/de not_active IP Right Cessation
- 1974-12-06 JP JP49140423A patent/JPS5088076A/ja active Pending
- 1974-12-09 DE DE19742458146 patent/DE2458146A1/de not_active Withdrawn
-
1977
- 1977-01-18 AT AT24577A patent/AT353792B/de not_active IP Right Cessation
- 1977-03-30 KE KE2718A patent/KE2718A/xx unknown
- 1977-12-30 MY MY239/77A patent/MY7700239A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5088076A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-15 |
| IL46181A (en) | 1978-03-10 |
| DK637674A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-07-28 |
| DK141700C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-12-08 |
| BR7410249A (pt) | 1976-06-29 |
| DK141700B (da) | 1980-05-27 |
| AT353792B (de) | 1979-12-10 |
| NL7415931A (nl) | 1975-06-10 |
| FR2292476A1 (fr) | 1976-06-25 |
| ZA747664B (en) | 1976-01-28 |
| SE415100B (sv) | 1980-09-08 |
| SE7415160L (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-06-09 |
| ATA24577A (de) | 1979-05-15 |
| FR2292476B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1979-05-18 |
| BE823023A (fr) | 1975-06-06 |
| CA1039283A (en) | 1978-09-26 |
| ATA977974A (de) | 1977-02-15 |
| CH605916A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-10-13 |
| PH10837A (en) | 1977-09-09 |
| AU7559274A (en) | 1976-05-27 |
| AT339310B (de) | 1977-10-10 |
| DE2458146A1 (de) | 1975-06-12 |
| MY7700239A (en) | 1977-12-31 |
| IL46181A0 (en) | 1975-03-13 |
| KE2718A (en) | 1977-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |