GB970949A - New 6-aminoquinoline derivatives - Google Patents
New 6-aminoquinoline derivativesInfo
- Publication number
- GB970949A GB970949A GB5353/62A GB535362A GB970949A GB 970949 A GB970949 A GB 970949A GB 5353/62 A GB5353/62 A GB 5353/62A GB 535362 A GB535362 A GB 535362A GB 970949 A GB970949 A GB 970949A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- quinoline
- group
- prepared
- specifications
- 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
- 150000005016 6-aminoquinolines Chemical class 0.000 title 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract 5
- RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- WNGDNTBKRFOEFC-UHFFFAOYSA-N 5,8-dimethoxyquinolin-6-ol Chemical compound OC=1C(=C2C=CC=NC2=C(C=1)OC)OC WNGDNTBKRFOEFC-UHFFFAOYSA-N 0.000 abstract 1
- 150000004325 8-hydroxyquinolines Chemical class 0.000 abstract 1
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 abstract 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- -1 amino alkylamine Chemical class 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000005013 aryl ether group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000001728 carbonyl compounds Chemical class 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 150000002828 nitro derivatives Chemical class 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 230000001737 promoting effect Effects 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000003786 synthesis reaction Methods 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
-
- 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
- C07D215/36—Sulfur 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
- C07D215/42—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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises 6-(aminoalkylamino)-quinoline derivatives which are substituted in the 5- and 8-positions by alkoxy, alkenyloxy, aralkyl or aryl ether groups, with or without a further alkyl group in a position other than the 5- or 8-position, and their pharmaceutically acceptable non-toxic neutral salts thereof with inorganic and organic acids. The compounds may be prepared by (a) reacting an appropriate 6-amino quinoline with a reactive ester of an aminoalcohol or condensing the aminoalcohol themselves with the 6-aminoquinoline; (b) by exchanging a group in the 6-position of an appropriate quinoline for an amino alkylamino radical by reaction of the group (e.g. hydroxyl) with an amino alkylamine; (c) by reacting 8-hydroxyquinoline compounds and their derivatives which also carry an exchangeable substituent in the 6-position, and which also carry in the 5-position a substituent promoting the exchangeability of the adjacent 6-position with an aminoalkylamine and converting the substituents in the 5- and 8-positions to ether groups as defined above; (d) introducing a 5-hydroxyl group or its ether into the 5-position of an 8-hydroxy -6- aminoalkylamino quinoline by preparing the 5-azo-or-5-nitrocompound reducing this to the 5-amino derivative and converting the amino group to an etherified hydroxyl group, (e) forming a Schiffs base between a 6-aminoquinoline and a basic carbonyl compound and reducing the base so formed; (f) by a ring closure, quinoline, synthesis, or (g) by a stepioise procedure to build up the amino alkyl chain in the 6-aminoalkylamino residue. 6-Amino-5, 8-dimethoxy-, -5, 8-diethoxy-, -5- phenoxy -8- methoxy-, and -5, 8-dimethoxy -2- methyl-quinolines are prepared by reduction of the corresponding nitro compounds. 6-Hydroxy-5, 8-dimethoxy-quinoline is prepared from the 6-amino compound by diazotistation. Specifications 267,169 and 433,625 and German Specifications 602,049 and 642,378 are referred to.ALSO:A red dyestuff, 6-(5-diethylamino-pentyl-2-amino) - 5 - phenylazo - 8 - methoxyquinoline, is prepared from diazotized aniline and 6-(5-diethylaminopentyl - 2 - amino) - 8 - methoxyquinoline. Specifications 267,169 and 433,625 and German Specifications 602,049 and 642,378 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DESCH29286A DE1186861B (en) | 1961-02-24 | 1961-02-24 | Process for the preparation of 6- (5'-diaethylaminopentyl-2'-amino) -5,8-dimethoxyquinolines or quinaldines useful as malaria remedies |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB970949A true GB970949A (en) | 1964-09-23 |
Family
ID=7431378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5353/62A Expired GB970949A (en) | 1961-02-24 | 1962-02-12 | New 6-aminoquinoline derivatives |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE614245A (en) |
| CH (1) | CH422788A (en) |
| DE (1) | DE1186861B (en) |
| GB (1) | GB970949A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3614756A1 (en) * | 1986-04-30 | 1987-11-05 | Ruetgerswerke Ag | METHOD FOR THE PRODUCTION OF 5-ALKYLCHINOLIN ACIDS AND AGENT FOR IMPLEMENTING THE METHOD |
-
1961
- 1961-02-24 DE DESCH29286A patent/DE1186861B/en active Pending
-
1962
- 1962-02-02 CH CH129162A patent/CH422788A/en unknown
- 1962-02-12 GB GB5353/62A patent/GB970949A/en not_active Expired
- 1962-02-22 BE BE614245A patent/BE614245A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE614245A (en) | 1962-08-22 |
| DE1186861B (en) | 1965-02-11 |
| CH422788A (en) | 1966-10-31 |
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