GB585363A - New heterocyclic compounds - Google Patents
New heterocyclic compoundsInfo
- Publication number
- GB585363A GB585363A GB1044144A GB1044144A GB585363A GB 585363 A GB585363 A GB 585363A GB 1044144 A GB1044144 A GB 1044144A GB 1044144 A GB1044144 A GB 1044144A GB 585363 A GB585363 A GB 585363A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- chloro
- chloroanilino
- quinazoline
- chloroquinoline
- 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
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
-
- 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
- C07D215/42—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)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Quinoline and quinazoline derivatives, carrying in 2- or 4-position an arylamino group free from acidic substituents and in the 4- or 2-position a basic group of the general formula -NR11-A-NRR1, wherein R11 represents H, alkyl or substituted alkyl, A represents an aliphatic, alicyclic or aliphatic-carbocyclic linking group, free from acidic substituents, and -NRR1 is a strongly basic amino or substituted amino group, are obtained by interaction of a diamine of the general formula NHR11-A-NRR1 with an appropriate 2- or 4-arylamino-quinoline or quinazoline, free from acidic substituents and carrying in the 4- or 2-position a labile atom or group, e.g. halogen or an alkoxy, aryloxy or alkylmercapto group. Alternatively, the 4- or 2-substituent may be introduced in stages by interaction of the appropriate arylamino-quinoline or quinazoline with a compound of the general formula NHR11-A1-B, wherein A1 represents the whole or part of the linking group and B represents a reactive group and reacting the product with ammonia or a primary or secondary amine to form the group -NRR1 or a group -A11-NRR1 such that A1 and A11 together constitute the group A. Another alternative when both R and R1 represent hydrogen is to react the labile group in the 2-or 4-position of the arylamino-quinoline or quinazoline compound with an acylated diamine NH.R11-A-NH.Ac, the acyl group being subsequently hydrolysed off. The free amino group so generated may be modified as by alkylation, conversion to a heterocyclic group such as piperidino or by reaction with a halogeno-substituted amine Hal-A11-NRR1 so as to extend the linking group A to A-NH-A111. Examples relate to the interaction of (1) 4-chloro-2-p-chloroanilinoquinazoline with b - diethylaminoethylamino, (2) 4 - chloro - 2 - p - chloroanilinoquinazoline with g - diethylaminopropylamine, (3) to (8), 4-chloro-2-p-methoxyanilino-quinazoline with g - diethylaminopropylamine, (4) b - dimethylaminoethylamine, (5) g - dimethylaminopropylamine, (6) g - piperidinopropylamine, (7) g - butylaminopropylamine, (8) d - diethylaminobutyamine, (9) 4 - chloro - 2 - p - chloronilinoquinazoline with b -acetylaminoethylamine, with subsequent hydrolysis of the acetyl group, (10) 2 - p - chloroanil - 4 - ethoxyquinazoline with b -diethylaminoethylamine, (11) to (17), 2 - p - chloroanilino-4-ethoxyquinazoline with (11) g - dibutylaminopropylamine, (12) d - dibutylaminobutylamine, (13) d - dimethylaminobutylamine, (14) 5 - dimethylamino amylamine, (15) 6 - dimethylaminohexylamine, (16) b - piperidinopropylamine, (17) g - (N - methyl - N - isopropylamino) - propylamine; (18) 2 - chloro - 4 - p - chloroanilinoquinazoline with g -diethylaminopropylamine; (19) to (26) 2 - p - chloroanilino - 4 - ethoxyquinazoline with (19) 5-diethylamino-2-aminopentane, (20) b - piperidinoethylamine, (21) b - pyrrolidinoethylamine, (22) b - piperidino - a - methylethylamine, (23) ö - butylaminopropylamine, (24) ethylene diamine-hydrate, (25) hexamethylene diamine, (26) g -(N-methyl-N-b -diethylaminoethylamino) - propylamine; (27) 2 - p - chloroanilino-4-phenoxyquinazoline with b -diethylaminoethylamine, (28) 2-p-chloroanilino-4-methylthioquinazoline with b -diethylaminoethylamine, (29) 2 - p - chloroanilino - 4 - ethoxyquinazoline with N : N1-dimethyltrimethylene diamine; (30) and (31) 2-chloro-4 p-chloroanilinoquinoline with (30) b -diethylaminoethylamine, (31) g -di-n-butylaminopropylamine; (32) to (37) 2-p-chloroanilino-4 chloroquinoline with (32) b -diethylaminoethylamine, (33) g -diethylaminopropylamine, (34) g -piperidinopropylamine, (35) g -dimethylaminopropylamine, (36) d - diethylaminobutylamine, (37) d - diethylamino - a - methyl - butylamine; (38) to (40) b -diethylaminoethylamine with (38) 2 - p - methoxyanilino - 4 - chloroquinoline, (39) 2 - p - methylanilino - 4 - chloroquinoline, (40) 2 - b - naphthylamino - 4 - chloroquinoline; (41) to (44) g -diethylaminopropylamine with (41) 2 - p - chloroanilino - 4 - chloro - 7 : 8 - benzquinoline, (42) 2-(61-bromo-21-naphthylamino)-4-chloroquinoline, (43) 2-p-nitroanilino-4-chloroquinoline, (44) 2-p-chloroaniline-3-methyl-4-chloroquinoline. Specification 585,362 is referred to. Specification 579,502 also is referred to in the second Provisional Specification. 4 - Chloro - 2 - p - chloroanilinoquinazoline is obtained by treating with phosphorus oxychloride the product of reaction of 2-chloro-4-hydroxy-quinazoline with p-chloroaniline. 2 - p - Chloroanilino - 4 - ethoxyquinazoline, 2 - chloro - 4 - p - chloroanilino-quinazoline, 2 - p - chloroanilino - 4 - phenoxy - quinazoline and 2 - p - chloroanilino - 4 - methylthioquinazoline are obtained by the reaction of p-chloroaniline with 2-chloro-4-ethoxyquinazoline, 2 : 4-dichloroquinazoline, 2-chloro-4-phenoxyquinazoline and 2 - chloro - 4 - methylthioquinazoline respectively.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1044144A GB585363A (en) | 1944-08-31 | 1944-08-31 | New heterocyclic compounds |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1044144A GB585363A (en) | 1944-08-31 | 1944-08-31 | New heterocyclic compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
GB585363A true GB585363A (en) | 1947-02-05 |
Family
ID=9967923
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1044144A Expired GB585363A (en) | 1944-08-31 | 1944-08-31 | New heterocyclic compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB585363A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003509501A (en) * | 1999-09-23 | 2003-03-11 | アストラゼネカ・アクチエボラーグ | Therapeutic quinazoline compounds |
-
1944
- 1944-08-31 GB GB1044144A patent/GB585363A/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2003509501A (en) * | 1999-09-23 | 2003-03-11 | アストラゼネカ・アクチエボラーグ | Therapeutic quinazoline compounds |
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