GB1285711A - New benzoxazine derivatives - Google Patents
New benzoxazine derivativesInfo
- Publication number
- GB1285711A GB1285711A GB5316868A GB5316868A GB1285711A GB 1285711 A GB1285711 A GB 1285711A GB 5316868 A GB5316868 A GB 5316868A GB 5316868 A GB5316868 A GB 5316868A GB 1285711 A GB1285711 A GB 1285711A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- hydrogen atom
- atom
- alkyl
- dihydro
- 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
- 150000005130 benzoxazines Chemical class 0.000 title 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 11
- 229910052783 alkali metal Inorganic materials 0.000 abstract 5
- -1 alkali metal salt Chemical class 0.000 abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 abstract 3
- JAUGKWITCJRISD-UHFFFAOYSA-N 3-oxo-4h-1,4-benzoxazine-2-carboxamide Chemical class C1=CC=C2NC(=O)C(C(=O)N)OC2=C1 JAUGKWITCJRISD-UHFFFAOYSA-N 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- QRAOZQGIUIDZQZ-UHFFFAOYSA-N 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazine Chemical compound C=1C=C2N(C)CCOC2=CC=1B1OC(C)(C)C(C)(C)O1 QRAOZQGIUIDZQZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 241001620634 Roger Species 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000001773 anti-convulsant effect Effects 0.000 abstract 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract 1
- 229960003965 antiepileptics Drugs 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000000147 hypnotic effect Effects 0.000 abstract 1
- WRIRWRKPLXCTFD-UHFFFAOYSA-N malonamide Chemical compound NC(=O)CC(N)=O WRIRWRKPLXCTFD-UHFFFAOYSA-N 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/36—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
1285711 2 - Carbamoyl - 3 - oxo - 2,3 - dihydro - 1,4 - benzoxazines LABORATOIRE ROGER BELLON 10 Nov 1969 [8 Nov 1968] 53168/68 Heading C2C Novel 2 - carbamoyl - 3 - oxo - 2,3 - dihydro- 1,4-benzoxazines of the general formula wherein R 1 and R 2 are each a hydrogen atom or a C 1-6 alkyl, cycloalkyl or optionally substituted aryl group, or R 1 and R 2 , together with the nitrogen atom to which they are attached form a heterocyclic radical wherein the heterocyclic ring contains 5 or 6 ring members, which ring may include a hetero atom in addition to the nitrogen atom; R 3 is a hydrogen atom or a C 1-6 alkyl or -CH 2 CONR 6 R 7 group, in which R 6 and R 7 are each a hydrogen atom or C 1-6 alkyl group or NR 6 R 7 is a morpholino or piperidino group; and R 4 and R 5 are each a hydrogen or halogen atom or a C 1-6 alkyl or C 1-6 alkoxy group, are prepared (i) when R 3 is a hydrogen atom, by (a) condensing an alkali metal salt of an o-nitrophenol of the general formula wherein M is an alkali metal, with a C 1-6 alkyl halomalonate of the general formula XCH(COOR<SP>11</SP>) 2 , wherein X is a halogen atom and R 2 is a C 1-6 alkyl group, (b) reductively cyclizing the resulting alkyl o-nitrophenoxymalonate of the general formula and (c) reacting the resulting 2-carbalkoxy-3- oxo - 2,3 - dihydro - 1,4 - benzorazine of the general formula with ammonia or an amine of the general formula R 1 R 2 NH; (ii) when R 3 is a hydrogen atom and R 1 and R 2 are not hydrogen atoms, by (a) condensing an alkali metal salt of an o-nitrophenol of the second general formula above with a halomalondiamide of the general formula CXH(CONR 1 R 2 ) 2 , (b) reducing the resulting oitnrophenoxymalondiamide of the general formula and (c) cyclizing the resulting o-aminophenoxymalondiamide of the general formula by heating in an acid medium; (iii) when R 3 is a hydrogen atom and R 1 and R 2 are not hydrogen atoms, by (a) condensing an alkali metal salt of an o-nitrophenol of the second general formula above with a halomalonic ester-amide of the general formula XCH(COOC 2 H 5 ) (CONR 1 R 2 ) and (b) reductively cyclizing the resulting 0-nitrophenoxymalonic ester-amide of the general formula and (iv) when R 3 is other than a hydrogen atom, by reaction of an alkali metal salt of the corresponding 2 - carbamoyl - 3 - oxo - 2,3 - dihydro- 1,4-benzoxazine of the first general formula above wherein R 3 is a hydrogen atom with a compound of the general formula R 3 X, wherein R 3 is other than a hydrogen atom. Bromomalondiamides of the seventh general formula above (X is a bromine atom) are prepared by reaction of a malondiamide of the general formula CH 2 (CONR 1 R 2 ) 2 with bromine in carbon tetrachloride. Bromomalonic esteramides of the tenth general formula above (X is a bromine atom) are prepared analogously. Pharmaceutical compositions having analgesic, anticonvulsant and hypnotic activity comprise, as active ingredient, a 2-carbamoyl-3- oxo-2,3-dihydro- 1 4-benzoxazine of the first general formula above, in association with a pharmaceutical carrier.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5316868A GB1285711A (en) | 1968-11-08 | 1968-11-08 | New benzoxazine derivatives |
| FR6936403A FR2024816B1 (en) | 1968-11-08 | 1969-10-23 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5316868A GB1285711A (en) | 1968-11-08 | 1968-11-08 | New benzoxazine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1285711A true GB1285711A (en) | 1972-08-16 |
Family
ID=10466865
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5316868A Expired GB1285711A (en) | 1968-11-08 | 1968-11-08 | New benzoxazine derivatives |
Country Status (2)
| Country | Link |
|---|---|
| FR (1) | FR2024816B1 (en) |
| GB (1) | GB1285711A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9101634B2 (en) | 2010-05-20 | 2015-08-11 | Shandong University | Application of 2, 3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine in preparation of drugs inducing embryonic stem cells to differentiate to vascular endothelial cells |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2565976B1 (en) * | 1984-06-18 | 1987-05-15 | Roussel Uclaf | NOVEL 3-OXOBENZOXAZINE DERIVATIVES, SALTS THEREOF, PROCESS FOR THEIR PREPARATION, APPLICATION AS MEDICAMENTS, AND COMPOSITIONS CONTAINING THEM |
| AU638154B2 (en) * | 1990-10-04 | 1993-06-17 | Suntory Limited | Benzoxazine derivative and herbicide containing same as an active ingredient |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1173942A (en) * | 1967-06-06 | 1969-12-10 | Bellon Labor Sa Roger | New 2,3-Dihydro-1,4-Benzoxazines |
-
1968
- 1968-11-08 GB GB5316868A patent/GB1285711A/en not_active Expired
-
1969
- 1969-10-23 FR FR6936403A patent/FR2024816B1/fr not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9101634B2 (en) | 2010-05-20 | 2015-08-11 | Shandong University | Application of 2, 3-dihydro-3-hydroxymethyl-6-amino-[1,4]-benzoxazine in preparation of drugs inducing embryonic stem cells to differentiate to vascular endothelial cells |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2024816A1 (en) | 1970-09-04 |
| FR2024816B1 (en) | 1974-03-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |