GB1280941A - New basically substituted 1,2,3-benzotriazine-4(3h)-one derivatives and processes for the production thereof - Google Patents
New basically substituted 1,2,3-benzotriazine-4(3h)-one derivatives and processes for the production thereofInfo
- Publication number
- GB1280941A GB1280941A GB2467970A GB2467970A GB1280941A GB 1280941 A GB1280941 A GB 1280941A GB 2467970 A GB2467970 A GB 2467970A GB 2467970 A GB2467970 A GB 2467970A GB 1280941 A GB1280941 A GB 1280941A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- trimethoxy
- propyl
- amino
- benzotriazin
- 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
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/08—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 condensed with carbocyclic rings or ring systems
Abstract
1280941 3 - (y - Amino - # - hydroxy - propyl)- 1,2,3 - benzotriazin - 4(3H) - ones CASSELLA FARBWERKE MAINKUR AG 21 May 1970 [22 May 1969] 24679/70 Heading C2C Novel 3 - (y - amino - # - hydroxy - propyl)- 1,2,3 - benzotriazin - 4(3H) - ones of the general formula wherein R is a secondary aliphatic, cycloaliphatic or araliphatic amine radical having 2-10 carbon atoms or the radical of a 5, 6 or 7-ring membered heterocyclic optionally containing a further N, O or S heteroatom, R<SP>1</SP> is a C 1-4 alkoxy group and n is 2 or 3, the alkoxy groups being in the 6 and 7 or 6, 7 and 8 positions, are prepared (a) by condensation of a 3 - (γ - halo - # - hydroxypropyl) - 1,2,3 - benzotriazin-4(3H)-one of the general formula wherein Hal is a chlorine or bromine atom, or the corresponding 3-(2<SP>1</SP>,3<SP>1</SP>-epoxypropyl) compound of the general formula with a secondary amine of the general formula RH; (b) by reaction of a 1,2,3-benzotriazin- 4(3H)-one of the general formula with a y-halo-#-hydroxy-propylamine of the general formula Hal-CH 2 -CH-(OH)-CH 2 R; and (c) by diazotization of a 2-amino-N-(γ- amino-#-hydroxy-propyl)-benzamide of the general formula 3 - (γ - Chloro - # - hydroxypropyl) - 6,7,8- trimethoxy - 1,2,3 - benzotriazin - 4(3H) - one is prepared by reaction of 3-chloro-1-aminopropanol-(2) hydrochloride with 2-nitro-3,4,5- trimethoxybenzoyl chloride, catalytic hydrogenation of the resulting 2-nitro-3,4,5-trimethoxy - N - (γ - chloro - # - hydroxy - propyl)- benzamide and diazotization of the resulting 2- amino - 3,4,5 - trimethoxy - N - (y - chloro - #- hydroxy - propyl) - benzamide hydrochloride. 3 - (2<SP>1</SP>,3<SP>1 </SP>- Epoxy - propyl) - 6,7,8 - trimethoxy- 1,2,3 - benzotriazin - 4(3H) - one is prepared by diazotization of 3,4,5-trimethoxyanthranilamide and reaction of the resulting 6,7,8-trimethoxy- 1,2,3 - benzotriazin - 4(3H) - one with epichlorohydrin. 2 - Amino - 3,4,5 - trimethoxy - N- (γ - morpholino - # - hydroxy - propyl) - benzamide dihydrochloride is prepared (a) by reaction of 2 - nitro - 3,4,5 - trimethoxy - N - (γ - chloro- B - hydroxy - propyl) - benzamide with morpholine and catalytic hydrogenation of the resulting 2 - nitro - 3,4,5 - trimethoxy - N - (γ- morpholino - # - hydroxy - propyl) - benzamide, (b) by reaction of 2-nitro-3,4,5-trimethoxybenzoyl chloride with N-(γ-amino-#-hydroxypropyl)-morpholine, followed by catalytic hydrogenation as in (a) and (c) by reaction of phosgene with 3,4,5-trimethoxy-2-amino-benzoic acid hydrochloride and reaction of the resulting 3,4,5 - trimethoxyisatoic anhydride with y-morpholino-#-hydroxy-propylamine.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19691926076 DE1926076B2 (en) | 1969-05-22 | 1969-05-22 | 3- (3-Amino-2-hydroxy-propyl) -6.7> 8trimethoxy-SH-M ^ -benzotriazin ^ -one derivatives and their preparation |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1280941A true GB1280941A (en) | 1972-07-12 |
Family
ID=5734860
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2467970A Expired GB1280941A (en) | 1969-05-22 | 1970-05-21 | New basically substituted 1,2,3-benzotriazine-4(3h)-one derivatives and processes for the production thereof |
Country Status (10)
Country | Link |
---|---|
AT (3) | AT297723B (en) |
BE (1) | BE750842A (en) |
BR (1) | BR6915397D0 (en) |
CA (1) | CA956945A (en) |
CH (3) | CH547295A (en) |
DE (1) | DE1926076B2 (en) |
FR (1) | FR2048612A5 (en) |
GB (1) | GB1280941A (en) |
IT (1) | IT1031004B (en) |
NL (1) | NL7006792A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4552878A (en) * | 1982-09-22 | 1985-11-12 | Lipha, Lyonnaise Industrielle Pharmaceutique | Benzo- and thieno-triazine-1,2,3 ones-4 |
WO2006117760A1 (en) * | 2005-05-03 | 2006-11-09 | Ranbaxy Laboratories Limited | Adrenergic receptor antagonists |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2551753B2 (en) * | 1982-09-22 | 1986-02-28 | Lipha | BENZOTRIAZINE-1,2,3-ONES-4, PROCESS FOR THE PREPARATION AND MEDICAMENTS CONTAINING THEM |
CN108276352B (en) * | 2018-03-13 | 2022-09-20 | 华东理工大学 | Nitrogen-containing heterocyclic compound with nematicidal activity and preparation method and application thereof |
-
1969
- 1969-05-22 DE DE19691926076 patent/DE1926076B2/en not_active Withdrawn
- 1969-12-19 BR BR21539769A patent/BR6915397D0/en unknown
-
1970
- 1970-05-11 NL NL7006792A patent/NL7006792A/xx unknown
- 1970-05-20 IT IT2489870A patent/IT1031004B/en active
- 1970-05-21 AT AT454470A patent/AT297723B/en not_active IP Right Cessation
- 1970-05-21 FR FR7018463A patent/FR2048612A5/fr not_active Expired
- 1970-05-21 GB GB2467970A patent/GB1280941A/en not_active Expired
- 1970-05-21 CA CA083,278A patent/CA956945A/en not_active Expired
- 1970-05-21 AT AT454570A patent/AT297724B/en not_active IP Right Cessation
- 1970-05-21 AT AT454370A patent/AT297722B/en not_active IP Right Cessation
- 1970-05-22 BE BE750842D patent/BE750842A/en unknown
- 1970-05-22 CH CH764170A patent/CH547295A/en not_active IP Right Cessation
- 1970-05-22 CH CH762970A patent/CH547294A/en not_active IP Right Cessation
- 1970-05-22 CH CH763170A patent/CH527830A/en not_active IP Right Cessation
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4552878A (en) * | 1982-09-22 | 1985-11-12 | Lipha, Lyonnaise Industrielle Pharmaceutique | Benzo- and thieno-triazine-1,2,3 ones-4 |
WO2006117760A1 (en) * | 2005-05-03 | 2006-11-09 | Ranbaxy Laboratories Limited | Adrenergic receptor antagonists |
Also Published As
Publication number | Publication date |
---|---|
CH527830A (en) | 1972-09-15 |
AT297724B (en) | 1972-04-10 |
CH547295A (en) | 1974-03-29 |
BE750842A (en) | 1970-11-23 |
BR6915397D0 (en) | 1973-01-04 |
FR2048612A5 (en) | 1971-03-19 |
IT1031004B (en) | 1979-04-30 |
CA956945A (en) | 1974-10-29 |
AT297723B (en) | 1972-04-10 |
CH547294A (en) | 1974-03-29 |
NL7006792A (en) | 1970-11-24 |
DE1926076A1 (en) | 1970-12-03 |
AT297722B (en) | 1972-04-10 |
DE1926076B2 (en) | 1979-12-20 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |