GB1113804A - Improvements in or relating to substituted quinolines and the manufacture thereof - Google Patents
Improvements in or relating to substituted quinolines and the manufacture thereofInfo
- Publication number
- GB1113804A GB1113804A GB5237867A GB5237867A GB1113804A GB 1113804 A GB1113804 A GB 1113804A GB 5237867 A GB5237867 A GB 5237867A GB 5237867 A GB5237867 A GB 5237867A GB 1113804 A GB1113804 A GB 1113804A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- chloro
- quinoline
- amino
- formula
- 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
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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen 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
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
-
- 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
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Novel 7 - chloro - 4 - (1 - methyl - 2 - piperidinylmethylamino) - quinoline, 7 - chloro - 4 - (1 - methyl - 3 - piperidinylmethylamino)-quinoline, 7 - chloro - 4 - (4 - amino - 4 - methylpentylamino) - quinoline, 4 - substituted - 7 - chloroquinolines of the formula <FORM:1113804/C2/1> wherein R1 and R2 are lower alkyl radicals containing from 1 to 4 carbon atoms or R1 and R2, taken together with the N atom to which they are attached, form a pyrrolidino, piperidino or morpholino ring, and pharmaceutically acceptable acid addition salts thereof are prepared by condensation of 2-aminomethyl-1-methylpiperidine, 3 - amino - methyl - 1 - methylpiperidine, 1 - amino - 4 - methyl - 4 - nitropentane or a 1 - amino - 4 - methyl - 4 - aminopentane derivative of the formula <FORM:1113804/C2/2> respectively, with 7-chloro-4-phenoxyquinoline hydrochloride; followed by hydrogenation, in the case of 7-chloro-4-(4-amino-4-methylpentylamino)-quinoline, of the resulting 7-chloro-4-(4-methyl-4-nitropentylamino)-quinoline; followed by optional conversion to a pharmaceutically acceptable acid addition salt of the product. Pharmaceutical compositions, having anti-inflammatory and anti-amebic activity and being useful in the treatment of malarial infections, comprise as active ingredient 7-chloro-4 - (1 - methyl - 2 - piperidinylmethylamino)-quinoline, 7 - chloro - 4 - (1 - methyl - 3 - piperidinylmethylamino) - quinoline, 7 - chloro - 4 - (4-amino - 4 - methylpentylamino) - quinoline, a 4 - substituted - 7 - chloro - quinoline of the first formula above, or a pharmaceutically acceptable acid addition salt thereof, together with a pharmaceutically acceptable carrier. 2 - Aminomethyl - 1 - methylpiperidine is prepared by treating 2-(acetamidomethyl)-pyridine with iodomethane, converting the resulting 2-(acetamidomethyl) - 1 - methylpyridinium iodide to the corresponding chloride with silver chloride, reducing the chloride to give 2-(acetamidomethyl) - 1 - methylpiperidine and finally hydrolysing. 1 - Amino - 4 - methyl - 4 - nitropentane is prepared by reacting 1-bromo-4-methyl - 4 - nitropentane with potassium phthalimide and treating the resulting 4-methyl-4 - nitro - 1 - phthalimidopentane with hydrazine hydrate. 1 - Amino - 4 - methyl - 4 - aminopentane derivatives of the second formula above are prepared by reacting 2,5-dibromo-2-methylpentane with potassium phthalimide, reacting the 4 - bromo - 4 - methyl - 1 - phthalimidopentane so obtained with a secondary amine of the formula R1R2NH and then treating the resulting phthalimide of the formula <FORM:1113804/C2/3> with hydrazine hydrate.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US37181164A | 1964-06-01 | 1964-06-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1113804A true GB1113804A (en) | 1968-05-15 |
Family
ID=23465490
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB5237767A Expired GB1113803A (en) | 1964-06-01 | 1965-05-21 | Improvements in or relating to substituted quinolines and the manufacture thereof |
GB2165565A Expired GB1113802A (en) | 1964-06-01 | 1965-05-21 | Improvements in or relating to substituted quinolines and the manufacture thereof |
GB5237867A Expired GB1113804A (en) | 1964-06-01 | 1965-05-21 | Improvements in or relating to substituted quinolines and the manufacture thereof |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB5237767A Expired GB1113803A (en) | 1964-06-01 | 1965-05-21 | Improvements in or relating to substituted quinolines and the manufacture thereof |
GB2165565A Expired GB1113802A (en) | 1964-06-01 | 1965-05-21 | Improvements in or relating to substituted quinolines and the manufacture thereof |
Country Status (4)
Country | Link |
---|---|
DE (2) | DE1620228A1 (en) |
GB (3) | GB1113803A (en) |
IL (1) | IL23555A (en) |
NL (1) | NL6506950A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1179599A3 (en) * | 2000-07-13 | 2003-07-09 | Ajinomoto Co., Inc. | Method for producing lysine derivative |
EP1613322A2 (en) * | 2003-04-11 | 2006-01-11 | Taigen Biotechnology | Aminoquinoline compounds |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102010048476A1 (en) * | 2010-10-14 | 2012-08-23 | Julius-Maximilians-Universität Würzburg | Hybrid compounds of 4- and 8-aminoquinolines for the prophylactic and therapeutic treatment of malaria and other parasitic diseases |
-
1965
- 1965-05-17 IL IL2355565A patent/IL23555A/en unknown
- 1965-05-21 GB GB5237767A patent/GB1113803A/en not_active Expired
- 1965-05-21 GB GB2165565A patent/GB1113802A/en not_active Expired
- 1965-05-21 GB GB5237867A patent/GB1113804A/en not_active Expired
- 1965-05-31 DE DE19651620228 patent/DE1620228A1/en active Pending
- 1965-05-31 DE DE19651620229 patent/DE1620229A1/en active Pending
- 1965-06-01 NL NL6506950A patent/NL6506950A/xx unknown
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1179599A3 (en) * | 2000-07-13 | 2003-07-09 | Ajinomoto Co., Inc. | Method for producing lysine derivative |
US6664412B2 (en) | 2000-07-13 | 2003-12-16 | Ajinomoto Co., Inc. | Method for producing lysine derivative |
EP1613322A2 (en) * | 2003-04-11 | 2006-01-11 | Taigen Biotechnology | Aminoquinoline compounds |
EP1613322A4 (en) * | 2003-04-11 | 2008-08-13 | Taigen Biotechnology Co Ltd | Aminoquinoline compounds |
Also Published As
Publication number | Publication date |
---|---|
IL23555A (en) | 1969-05-28 |
NL6506950A (en) | 1965-12-02 |
DE1620229A1 (en) | 1970-06-04 |
GB1113803A (en) | 1968-05-15 |
GB1113802A (en) | 1968-05-15 |
DE1620228A1 (en) | 1970-06-04 |
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