NO128572B - - Google Patents
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- Publication number
- NO128572B NO128572B NO03766/68A NO376668A NO128572B NO 128572 B NO128572 B NO 128572B NO 03766/68 A NO03766/68 A NO 03766/68A NO 376668 A NO376668 A NO 376668A NO 128572 B NO128572 B NO 128572B
- Authority
- NO
- Norway
- Prior art keywords
- benzoxazine
- formula
- lower alkyl
- chloro
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 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 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- BZQYQHBLAIWZAC-UHFFFAOYSA-N 1h-2,3-benzoxazine Chemical class C1=CC=C2CON=CC2=C1 BZQYQHBLAIWZAC-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 4
- -1 hydrazone compounds Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 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 3
- 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 claims description 3
- KJDQNEMYJJCGMR-UHFFFAOYSA-N 4-chloro-1h-2,3-benzoxazine Chemical compound C1=CC=C2C(Cl)=NOCC2=C1 KJDQNEMYJJCGMR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000007306 turnover Effects 0.000 claims 1
- 239000002023 wood Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 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
- 239000002904 solvent Substances 0.000 description 6
- 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 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 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 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- JKOGLZJKPQGMRA-UHFFFAOYSA-N 6-chloro-n-(ethylideneamino)-n-methyl-1h-2,3-benzoxazin-4-amine Chemical compound C1=C(Cl)C=C2C(N(C)N=CC)=NOCC2=C1 JKOGLZJKPQGMRA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 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
- 230000001143 conditioned effect Effects 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- ODKARNMCYIQDOK-UHFFFAOYSA-N 6-chloro-n-methyl-n-(propylideneamino)-1h-2,3-benzoxazin-4-amine Chemical compound C1=C(Cl)C=C2C(N(C)N=CCC)=NOCC2=C1 ODKARNMCYIQDOK-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000009194 climbing Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 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
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 239000005554 hypnotics and sedatives Substances 0.000 description 1
- 229940005535 hypnotics and sedatives Drugs 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
- 238000011835 investigation Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 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
- 229940124641 pain reliever Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 230000008925 spontaneous activity Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 231100000048 toxicity data Toxicity 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 (1)
| Publication Number | Publication Date |
|---|---|
| NO128572B true NO128572B (sv) | 1973-12-10 |
Family
ID=10429582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO03766/68A NO128572B (sv) | 1967-09-25 | 1968-09-24 |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS4946630B1 (sv) |
| AT (1) | AT278841B (sv) |
| BE (1) | BE721356A (sv) |
| CA (1) | CA929522A (sv) |
| CH (1) | CH481934A (sv) |
| DE (1) | DE1795384C3 (sv) |
| DK (2) | DK124205B (sv) |
| ES (1) | ES358442A1 (sv) |
| FI (1) | FI48842C (sv) |
| FR (2) | FR7757M (sv) |
| GB (1) | GB1225612A (sv) |
| IL (1) | IL30757A (sv) |
| LU (1) | LU56962A1 (sv) |
| NL (1) | NL6813657A (sv) |
| NO (1) | NO128572B (sv) |
| SE (2) | SE332988B (sv) |
| YU (1) | YU31966B (sv) |
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/sv active
- 1968-09-22 IL IL30757A patent/IL30757A/xx unknown
- 1968-09-23 DK DK456268AA patent/DK124205B/da 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 ES ES358442A patent/ES358442A1/es not_active Expired
- 1968-09-24 NO NO03766/68A patent/NO128572B/no unknown
- 1968-09-24 NL NL6813657A patent/NL6813657A/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 BE BE721356D patent/BE721356A/xx unknown
- 1968-09-25 YU YU2244/68A patent/YU31966B/xx unknown
- 1968-09-25 FR FR167488A patent/FR7757M/fr not_active Expired
- 1968-09-25 CA CA030877A patent/CA929522A/en not_active Expired
- 1968-09-25 FR FR1598168D patent/FR1598168A/fr 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 |
|---|---|
| AT278841B (de) | 1970-02-10 |
| DE1795384A1 (de) | 1972-03-09 |
| LU56962A1 (sv) | 1969-02-05 |
| YU224468A (en) | 1973-08-31 |
| DK124205B (da) | 1972-09-25 |
| DK124889B (da) | 1972-12-04 |
| DE1795384B2 (de) | 1974-10-03 |
| FI48842B (sv) | 1974-09-30 |
| NL6813657A (sv) | 1969-03-27 |
| JPS4946630B1 (sv) | 1974-12-11 |
| ES358442A1 (es) | 1970-06-16 |
| DE1795384C3 (de) | 1975-07-17 |
| SE351218B (sv) | 1972-11-20 |
| SE332988B (sv) | 1971-03-01 |
| YU31966B (en) | 1974-02-28 |
| CH481934A (fr) | 1969-11-30 |
| FR1598168A (sv) | 1970-07-06 |
| GB1225612A (sv) | 1971-03-17 |
| CA929522A (en) | 1973-07-03 |
| IL30757A0 (en) | 1970-03-22 |
| FR7757M (sv) | 1970-03-16 |
| FI48842C (sv) | 1975-01-10 |
| IL30757A (en) | 1973-05-31 |
| BE721356A (sv) | 1969-03-03 |
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