IL28962A - 3,1-benzoxazine derivatives and process for their manufacture - Google Patents
3,1-benzoxazine derivatives and process for their manufactureInfo
- Publication number
- IL28962A IL28962A IL28962A IL2896267A IL28962A IL 28962 A IL28962 A IL 28962A IL 28962 A IL28962 A IL 28962A IL 2896267 A IL2896267 A IL 2896267A IL 28962 A IL28962 A IL 28962A
- Authority
- IL
- Israel
- Prior art keywords
- benzoxazine
- chloro
- methyl
- compound
- phenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 230000008569 process Effects 0.000 title claims description 13
- GTYZDORKFFSTLS-UHFFFAOYSA-N 2h-3,1-benzoxazine Chemical class C1=CC=CC2=NCOC=C21 GTYZDORKFFSTLS-UHFFFAOYSA-N 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- -1 oyoloalkenyl Chemical group 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 7
- 150000002513 isocyanates Chemical class 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 150000003585 thioureas Chemical class 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 150000003672 ureas Chemical class 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000005864 Sulphur Chemical group 0.000 claims description 4
- 238000010306 acid treatment Methods 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000007514 bases Chemical class 0.000 claims description 4
- 235000013877 carbamide Nutrition 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 229910052987 metal hydride Inorganic materials 0.000 claims description 3
- 150000004681 metal hydrides Chemical class 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- PSFXVKGWHCTLKA-UHFFFAOYSA-N 6-chloro-N,4-diethyl-4-phenyl-1H-3,1-benzoxazin-2-imine Chemical compound C(C)NC1=NC2=C(C(O1)(C1=CC=CC=C1)CC)C=C(C=C2)Cl PSFXVKGWHCTLKA-UHFFFAOYSA-N 0.000 claims description 2
- KRZZKXYTSCQNNE-UHFFFAOYSA-N 6-chloro-n,4-dimethyl-4-phenyl-3,1-benzoxazin-2-amine Chemical compound O1C(NC)=NC2=CC=C(Cl)C=C2C1(C)C1=CC=CC=C1 KRZZKXYTSCQNNE-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000005265 dialkylamine group Chemical group 0.000 claims description 2
- 230000000506 psychotropic effect Effects 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- SEGVYZVDFPUJCK-UHFFFAOYSA-N 6-chloro-N-ethyl-4-phenyl-4-propyl-1H-3,1-benzoxazin-2-imine Chemical compound C(C)NC1=NC2=C(C(O1)(C1=CC=CC=C1)CCC)C=C(C=C2)Cl SEGVYZVDFPUJCK-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
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- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000003236 psychic effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 91
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 48
- 238000002844 melting Methods 0.000 description 46
- 230000008018 melting Effects 0.000 description 45
- 239000013078 crystal Substances 0.000 description 27
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- 239000000243 solution Substances 0.000 description 16
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- 239000002904 solvent Substances 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- 229910000474 mercury oxide Inorganic materials 0.000 description 14
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- 239000000047 product Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
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- 238000001953 recrystallisation Methods 0.000 description 10
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- 239000000126 substance Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
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- 235000019445 benzyl alcohol Nutrition 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
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- 238000002425 crystallisation Methods 0.000 description 4
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- 229940073584 methylene chloride Drugs 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 150000003938 benzyl alcohols Chemical class 0.000 description 3
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- 229940093915 gynecological organic acid Drugs 0.000 description 3
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- 239000012280 lithium aluminium hydride Substances 0.000 description 3
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- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 230000002048 spasmolytic effect Effects 0.000 description 3
- ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 108010010803 Gelatin Proteins 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 1
- 150000007945 N-acyl ureas Chemical class 0.000 description 1
- UEWBCTYKGQYRDI-UHFFFAOYSA-N N-ethyl-4,4-dimethyl-1H-3,1-benzoxazin-2-imine Chemical compound C(C)NC1=NC2=C(C(O1)(C)C)C=CC=C2 UEWBCTYKGQYRDI-UHFFFAOYSA-N 0.000 description 1
- 206010029333 Neurosis Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 208000032140 Sleepiness Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- GOLCXWYRSKYTSP-UHFFFAOYSA-N arsenic trioxide Inorganic materials O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 1
- GSEZYWGNEACOIW-UHFFFAOYSA-N bis(2-aminophenyl)methanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1N GSEZYWGNEACOIW-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001912 cyanamides Chemical class 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 208000037765 diseases and disorders Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229910003439 heavy metal oxide Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- UGVPKMAWLOMPRS-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].CC[CH2-] UGVPKMAWLOMPRS-UHFFFAOYSA-M 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004899 motility Effects 0.000 description 1
- LASJRIHCUCYPGY-UHFFFAOYSA-N n,n-diethyl-2-isothiocyanatoethanamine Chemical compound CCN(CC)CCN=C=S LASJRIHCUCYPGY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- VYFOAVADNIHPTR-UHFFFAOYSA-N o-aminobenzyl alcohol Natural products NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil 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
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Load-Bearing And Curtain Walls (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1670772A DE1670772C3 (de) | 1966-11-24 | 1966-11-24 | 4H-3,1-Benzoxazin-Derivate, deren Salze und pharmazeutische Präparate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL28962A true IL28962A (en) | 1972-05-30 |
Family
ID=7104042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL28962A IL28962A (en) | 1966-11-24 | 1967-11-17 | 3,1-benzoxazine derivatives and process for their manufacture |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3725404A (cs) |
| AT (4) | AT278024B (cs) |
| BE (1) | BE707013A (cs) |
| CH (2) | CH522671A (cs) |
| CS (5) | CS154239B2 (cs) |
| DE (1) | DE1670772C3 (cs) |
| DK (1) | DK131905C (cs) |
| ES (2) | ES347430A1 (cs) |
| FI (1) | FI48595C (cs) |
| FR (2) | FR1571287A (cs) |
| GB (1) | GB1197479A (cs) |
| IL (1) | IL28962A (cs) |
| NL (1) | NL156402B (cs) |
| NO (1) | NO119743B (cs) |
| SE (1) | SE329620B (cs) |
| YU (1) | YU32857B (cs) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1670772C3 (de) * | 1966-11-24 | 1978-04-20 | Hoechst Ag, 6000 Frankfurt | 4H-3,1-Benzoxazin-Derivate, deren Salze und pharmazeutische Präparate |
| US4596801A (en) * | 1983-03-24 | 1986-06-24 | Chugai Seiyaku Kabushiki Kaisha | 4H-3,1-benzoxazine derivatives, process for producing the same and agricultural or horticultural fungicide containing the same |
| FR2888749B1 (fr) | 2005-07-19 | 2007-10-12 | Biocodex | Composition pharmaceutique destinee a la prevention ou au traitement des oedemes cerebraux |
| FR2888748B1 (fr) | 2005-07-19 | 2007-10-12 | Biocodex | Composes neuroprotecteurs et compositions pharmaceutiques les comprenant |
| EP2007741A1 (en) | 2006-03-20 | 2008-12-31 | Xytis Inc. | Enantiomerically pure s-etifoxine, pharmaceutical compositions thereof and methods of their use |
| US20080039453A1 (en) * | 2006-03-20 | 2008-02-14 | David Putman | Enantiomerically pure R-etifoxine, pharmaceutical compositions thereof and methods of their use |
| FR2930891B1 (fr) | 2008-05-06 | 2010-09-24 | Biocodex | Composes anti-amnesiants et compositions pharmaceutiques les comprenant |
| FR2937552B1 (fr) | 2008-10-27 | 2011-05-06 | Biocodex | Composition pharmaceutique destinee a la prevention ou au traitement du syndrome de sevrage alcoolique |
| US20120071471A1 (en) * | 2009-03-13 | 2012-03-22 | Neurosearch A/S | Novel benzoxazinone derivatives useful for the treatment of cns disorders |
| FR2972192A1 (fr) | 2011-03-04 | 2012-09-07 | Biocodex | Composition pharmaceutique destinee a la prevention ou au traitement des cancers |
| FR3016881B1 (fr) | 2014-01-29 | 2016-03-04 | Biocodex | Traitement des degenerescences et des lesions photo-induites de la retine |
| JP6762507B2 (ja) | 2015-03-20 | 2020-09-30 | ギャバ セラピューティクス、インコーポレイテッド | エチホキシンの重水素化類似体、それらの誘導体、およびそれらの使用 |
| CN108884025A (zh) * | 2016-03-31 | 2018-11-23 | 陶氏环球技术有限责任公司 | 双碳二亚胺和聚碳二亚胺及其制备方法 |
| FR3051114B1 (fr) | 2016-05-11 | 2019-09-27 | Biocodex | Composes pour le traitement de la maladie d'alzheimer |
| US10420773B2 (en) | 2017-09-26 | 2019-09-24 | Ovid Therapeutics Inc. | Methods of treating developmental disorders and/or seizure disorders with etifoxine |
| CN117586198B (zh) * | 2023-11-24 | 2024-10-25 | 南开大学 | 溴苯并恶嗪类化合物的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1545820A1 (de) * | 1965-06-03 | 1969-12-11 | Hoechst Ag | Verfahren zur Herstellung von 3,1-Benzothiazin-Derivaten |
| DE1670772C3 (de) * | 1966-11-24 | 1978-04-20 | Hoechst Ag, 6000 Frankfurt | 4H-3,1-Benzoxazin-Derivate, deren Salze und pharmazeutische Präparate |
-
1966
- 1966-11-24 DE DE1670772A patent/DE1670772C3/de not_active Expired
-
1967
- 1967-11-17 IL IL28962A patent/IL28962A/en unknown
- 1967-11-17 NL NL6715652.A patent/NL156402B/xx not_active IP Right Cessation
- 1967-11-20 CS CS556272*1A patent/CS154239B2/cs unknown
- 1967-11-20 CS CS556372*1A patent/CS154240B2/cs unknown
- 1967-11-20 CS CS821567A patent/CS154238B2/cs unknown
- 1967-11-20 CS CS556472*1A patent/CS154241B2/cs unknown
- 1967-11-20 GB GB52643/67A patent/GB1197479A/en not_active Expired
- 1967-11-20 CS CS793372*1A patent/CS154242B2/cs unknown
- 1967-11-21 YU YU2271/67A patent/YU32857B/xx unknown
- 1967-11-21 ES ES347430A patent/ES347430A1/es not_active Expired
- 1967-11-22 AT AT1136668A patent/AT278024B/de not_active IP Right Cessation
- 1967-11-22 AT AT1055167A patent/AT276412B/de active
- 1967-11-22 AT AT1136868A patent/AT278026B/de not_active IP Right Cessation
- 1967-11-22 CH CH1635167A patent/CH522671A/de not_active IP Right Cessation
- 1967-11-22 CH CH1083571A patent/CH534174A/de not_active IP Right Cessation
- 1967-11-22 AT AT1136768A patent/AT278025B/de not_active IP Right Cessation
- 1967-11-22 SE SE16017/67A patent/SE329620B/xx unknown
- 1967-11-23 NO NO170669A patent/NO119743B/no unknown
- 1967-11-23 DK DK587767A patent/DK131905C/da not_active IP Right Cessation
- 1967-11-24 FR FR1571287D patent/FR1571287A/fr not_active Expired
- 1967-11-24 FI FI673169A patent/FI48595C/fi active
- 1967-11-24 BE BE707013D patent/BE707013A/xx not_active IP Right Cessation
-
1968
- 1968-02-23 FR FR141043A patent/FR7358M/fr not_active Expired
-
1969
- 1969-05-05 ES ES366801A patent/ES366801A1/es not_active Expired
-
1971
- 1971-06-09 US US00151599A patent/US3725404A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| NO119743B (cs) | 1970-06-29 |
| DE1670772C3 (de) | 1978-04-20 |
| CS154239B2 (cs) | 1974-03-29 |
| CS154242B2 (cs) | 1974-03-29 |
| DE1670772B2 (de) | 1977-08-25 |
| BE707013A (cs) | 1968-05-24 |
| CS154238B2 (cs) | 1974-03-29 |
| AT278024B (de) | 1970-01-26 |
| NL156402B (nl) | 1978-04-17 |
| AT278026B (de) | 1970-01-26 |
| YU227167A (en) | 1974-10-31 |
| AT278025B (de) | 1970-01-26 |
| ES347430A1 (es) | 1969-11-01 |
| FI48595B (cs) | 1974-07-31 |
| DK131905B (da) | 1975-09-22 |
| GB1197479A (en) | 1970-07-08 |
| DE1670772A1 (de) | 1970-07-16 |
| US3725404A (en) | 1973-04-03 |
| FI48595C (fi) | 1974-11-11 |
| NL6715652A (cs) | 1968-05-27 |
| SE329620B (cs) | 1970-10-19 |
| AT276412B (de) | 1969-11-25 |
| FR7358M (cs) | 1969-10-20 |
| FR1571287A (cs) | 1969-06-20 |
| DK131905C (da) | 1976-02-23 |
| ES366801A1 (es) | 1971-07-16 |
| CS154241B2 (cs) | 1974-03-29 |
| CH522671A (de) | 1972-06-30 |
| YU32857B (en) | 1975-10-31 |
| CH534174A (de) | 1973-02-28 |
| CS154240B2 (cs) | 1974-03-29 |
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