DE1795384C3 - 1 H-2,3-Benzoxazine, Verfahren zu deren Herstellung sowie Arzneimittel - Google Patents
1 H-2,3-Benzoxazine, Verfahren zu deren Herstellung sowie ArzneimittelInfo
- Publication number
- DE1795384C3 DE1795384C3 DE1795384A DE1795384A DE1795384C3 DE 1795384 C3 DE1795384 C3 DE 1795384C3 DE 1795384 A DE1795384 A DE 1795384A DE 1795384 A DE1795384 A DE 1795384A DE 1795384 C3 DE1795384 C3 DE 1795384C3
- Authority
- DE
- Germany
- Prior art keywords
- benzoxazine
- chloro
- general formula
- benzoxazines
- isopropylidene
- 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
- 238000000034 method Methods 0.000 title claims description 5
- 239000003814 drug Substances 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- ZCKSETHMUBXEOS-UHFFFAOYSA-N 1-(6-chloro-1h-2,3-benzoxazin-4-yl)-1-methylhydrazine Chemical compound C1=C(Cl)C=C2C(N(N)C)=NOCC2=C1 ZCKSETHMUBXEOS-UHFFFAOYSA-N 0.000 claims description 2
- XBQCPGQMXAXYME-UHFFFAOYSA-N 6-chloro-n-(propan-2-ylideneamino)-1h-2,3-benzoxazin-4-amine Chemical compound C1=C(Cl)C=C2C(NN=C(C)C)=NOCC2=C1 XBQCPGQMXAXYME-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- -1 isopropylidene amino group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000011514 reflex Effects 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 229960004815 meprobamate Drugs 0.000 description 3
- 230000002936 tranquilizing effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HJEALFMKMBRWQO-UHFFFAOYSA-N (6-chloro-1h-2,3-benzoxazin-4-yl)hydrazine Chemical compound C1=C(Cl)C=C2C(NN)=NOCC2=C1 HJEALFMKMBRWQO-UHFFFAOYSA-N 0.000 description 2
- SWDJXULAVXHWBD-UHFFFAOYSA-N 4,6-dichloro-1h-2,3-benzoxazine Chemical compound C1=C(Cl)C=C2C(Cl)=NOCC2=C1 SWDJXULAVXHWBD-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000000049 anti-anxiety effect Effects 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- BZQYQHBLAIWZAC-UHFFFAOYSA-N 1h-2,3-benzoxazine Chemical compound C1=CC=C2CON=CC2=C1 BZQYQHBLAIWZAC-UHFFFAOYSA-N 0.000 description 1
- IZXHRPUCSXCXSO-UHFFFAOYSA-N 6-chloro-n,n-dimethyl-1h-2,3-benzoxazin-4-amine Chemical compound C1=C(Cl)C=C2C(N(C)C)=NOCC2=C1 IZXHRPUCSXCXSO-UHFFFAOYSA-N 0.000 description 1
- GUXQXIRGDSFDLP-UHFFFAOYSA-N 6-chloro-n-methyl-1h-2,3-benzoxazin-4-amine Chemical compound C1=C(Cl)C=C2C(NC)=NOCC2=C1 GUXQXIRGDSFDLP-UHFFFAOYSA-N 0.000 description 1
- MFHUOYADTVLXMD-UHFFFAOYSA-N 6-chloro-n-methyl-n-(propan-2-ylideneamino)-1h-2,3-benzoxazin-4-amine Chemical compound C1=C(Cl)C=C2C(N(N=C(C)C)C)=NOCC2=C1 MFHUOYADTVLXMD-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000030360 Peromyscus truei Species 0.000 description 1
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000037007 arousal Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 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
- C07D265/02—1,2-Oxazines; Hydrogenated 1,2-oxazines
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4362167 | 1967-09-25 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1795384A1 DE1795384A1 (de) | 1972-03-09 |
| DE1795384B2 DE1795384B2 (de) | 1974-10-03 |
| DE1795384C3 true DE1795384C3 (de) | 1975-07-17 |
Family
ID=10429582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1795384A Expired DE1795384C3 (de) | 1967-09-25 | 1968-09-24 | 1 H-2,3-Benzoxazine, Verfahren zu deren Herstellung sowie Arzneimittel |
Country Status (17)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4005082A (en) * | 1967-09-25 | 1977-01-25 | Gruppo Lepetit S.P.A. | 1H-2,3-Benzoxazines |
| FR2068436A6 (en) * | 1969-11-18 | 1971-08-27 | Lepetit Spa | 1h-2,3-benzoxazine derivs, nerve drugs and - anti-inflammatory agents |
| ZA738362B (en) * | 1972-12-22 | 1974-09-25 | Lepetit Spa | New 3,5-disubstituted triazole active on the c.n.s. |
-
1967
- 1967-09-25 GB GB4362167A patent/GB1225612A/en not_active Expired
-
1968
- 1968-09-18 AT AT910868A patent/AT278841B/de not_active IP Right Cessation
- 1968-09-18 FI FI682624A patent/FI48842C/fi active
- 1968-09-22 IL IL30757A patent/IL30757A/xx unknown
- 1968-09-23 DK DK456268AA patent/DK124205B/da unknown
- 1968-09-24 ES ES358442A patent/ES358442A1/es not_active Expired
- 1968-09-24 NO NO03766/68A patent/NO128572B/no unknown
- 1968-09-24 DE DE1795384A patent/DE1795384C3/de not_active Expired
- 1968-09-24 SE SE12868/68A patent/SE332988B/xx unknown
- 1968-09-24 NL NL6813657A patent/NL6813657A/xx unknown
- 1968-09-25 FR FR167488A patent/FR7757M/fr not_active Expired
- 1968-09-25 BE BE721356D patent/BE721356A/xx unknown
- 1968-09-25 YU YU2244/68A patent/YU31966B/xx unknown
- 1968-09-25 LU LU56962D patent/LU56962A1/xx unknown
- 1968-09-25 CH CH1430868A patent/CH481934A/fr not_active IP Right Cessation
- 1968-09-25 FR FR1598168D patent/FR1598168A/fr not_active Expired
- 1968-09-25 CA CA030877A patent/CA929522A/en not_active Expired
-
1970
- 1970-09-03 DK DK453470AA patent/DK124889B/da unknown
- 1970-10-29 SE SE14604/70A patent/SE351218B/xx unknown
-
1971
- 1971-02-10 JP JP46005918A patent/JPS4946630B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4946630B1 (enrdf_load_stackoverflow) | 1974-12-11 |
| FR1598168A (enrdf_load_stackoverflow) | 1970-07-06 |
| NL6813657A (enrdf_load_stackoverflow) | 1969-03-27 |
| BE721356A (enrdf_load_stackoverflow) | 1969-03-03 |
| DK124889B (da) | 1972-12-04 |
| FR7757M (enrdf_load_stackoverflow) | 1970-03-16 |
| CH481934A (fr) | 1969-11-30 |
| ES358442A1 (es) | 1970-06-16 |
| DK124205B (da) | 1972-09-25 |
| GB1225612A (enrdf_load_stackoverflow) | 1971-03-17 |
| DE1795384A1 (de) | 1972-03-09 |
| NO128572B (enrdf_load_stackoverflow) | 1973-12-10 |
| IL30757A (en) | 1973-05-31 |
| YU31966B (en) | 1974-02-28 |
| DE1795384B2 (de) | 1974-10-03 |
| FI48842C (fi) | 1975-01-10 |
| CA929522A (en) | 1973-07-03 |
| IL30757A0 (en) | 1970-03-22 |
| SE332988B (enrdf_load_stackoverflow) | 1971-03-01 |
| YU224468A (en) | 1973-08-31 |
| FI48842B (enrdf_load_stackoverflow) | 1974-09-30 |
| SE351218B (enrdf_load_stackoverflow) | 1972-11-20 |
| AT278841B (de) | 1970-02-10 |
| LU56962A1 (enrdf_load_stackoverflow) | 1969-02-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |