DE1695091A1 - 2-,3-,5-substituierte 5-Nitrotetrahydro-1,3-oxazinderivate und Verfahren zu ihrer Herstellung - Google Patents
2-,3-,5-substituierte 5-Nitrotetrahydro-1,3-oxazinderivate und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1695091A1 DE1695091A1 DE19661695091 DE1695091A DE1695091A1 DE 1695091 A1 DE1695091 A1 DE 1695091A1 DE 19661695091 DE19661695091 DE 19661695091 DE 1695091 A DE1695091 A DE 1695091A DE 1695091 A1 DE1695091 A1 DE 1695091A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- cyclohexyl
- preparation
- substituted
- nitrotetrahydro
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 5-substituted 5-nitrotetrahydro-1,3-oxazine Chemical class 0.000 title description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims description 4
- 125000005504 styryl group Chemical group 0.000 claims description 4
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 229940117916 cinnamic aldehyde Drugs 0.000 claims description 3
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XIFHEJPWOZEGLV-UHFFFAOYSA-N 5-nitro-1,3-oxazinane Chemical group [O-][N+](=O)C1CNCOC1 XIFHEJPWOZEGLV-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- VIROVYVQCGLCII-UHFFFAOYSA-N amobarbital Chemical compound CC(C)CCC1(CC)C(=O)NC(=O)NC1=O VIROVYVQCGLCII-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000003840 hydrochlorides Chemical class 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 206010003445 Ascites Diseases 0.000 description 1
- ZJLBLPKQNCPIAX-UHFFFAOYSA-N CCCC(C1)(COC(C)N1C1CCCCC1)[N+]([O-])=O Chemical compound CCCC(C1)(COC(C)N1C1CCCCC1)[N+]([O-])=O ZJLBLPKQNCPIAX-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- AXMVYSVVTMKQSL-UHFFFAOYSA-N UNPD142122 Natural products OC1=CC=C(C=CC=O)C=C1O AXMVYSVVTMKQSL-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229940098184 amytal Drugs 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003217 anti-cancerogenic effect Effects 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 230000005907 cancer growth Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000000247 oncostatic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 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
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
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 |
|---|---|---|---|
| PL106889A PL54007B1 (enExample) | 1965-01-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1695091A1 true DE1695091A1 (de) | 1972-03-16 |
Family
ID=19944368
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661695091 Pending DE1695091A1 (de) | 1965-01-07 | 1966-01-07 | 2-,3-,5-substituierte 5-Nitrotetrahydro-1,3-oxazinderivate und Verfahren zu ihrer Herstellung |
| DE19661695051 Pending DE1695051A1 (de) | 1965-01-07 | 1966-01-07 | 2-,3-,5-substituierte 5-Nitrotetrahydro-1,3-oxazinderivate,Verfahren zu ihrer Herstellung und Verwendung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661695051 Pending DE1695051A1 (de) | 1965-01-07 | 1966-01-07 | 2-,3-,5-substituierte 5-Nitrotetrahydro-1,3-oxazinderivate,Verfahren zu ihrer Herstellung und Verwendung |
Country Status (4)
| Country | Link |
|---|---|
| DE (2) | DE1695091A1 (enExample) |
| FR (1) | FR1501718A (enExample) |
| GB (1) | GB1120793A (enExample) |
| NL (1) | NL6600207A (enExample) |
-
1966
- 1966-01-07 DE DE19661695091 patent/DE1695091A1/de active Pending
- 1966-01-07 FR FR45156A patent/FR1501718A/fr not_active Expired
- 1966-01-07 DE DE19661695051 patent/DE1695051A1/de active Pending
- 1966-01-07 NL NL6600207A patent/NL6600207A/xx unknown
- 1966-01-07 GB GB89866A patent/GB1120793A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1501718A (fr) | 1967-11-18 |
| GB1120793A (en) | 1968-07-24 |
| DE1695051A1 (de) | 1972-03-02 |
| NL6600207A (enExample) | 1966-07-08 |
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