DE2509922A1 - Neue aromatische dicarbonsaeureimide - Google Patents
Neue aromatische dicarbonsaeureimideInfo
- Publication number
- DE2509922A1 DE2509922A1 DE19752509922 DE2509922A DE2509922A1 DE 2509922 A1 DE2509922 A1 DE 2509922A1 DE 19752509922 DE19752509922 DE 19752509922 DE 2509922 A DE2509922 A DE 2509922A DE 2509922 A1 DE2509922 A1 DE 2509922A1
- Authority
- DE
- Germany
- Prior art keywords
- lower alkyl
- amino
- group
- tolyl
- carbamoyl
- 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
- -1 DICARBONIC ACID IMIDES Chemical class 0.000 title claims description 144
- 239000000203 mixture Substances 0.000 claims description 80
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- 150000001875 compounds Chemical class 0.000 claims description 69
- 238000000034 method Methods 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 47
- 239000007858 starting material Substances 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 239000011737 fluorine Substances 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 19
- 150000002367 halogens Chemical class 0.000 claims description 19
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 13
- 125000005556 thienylene group Chemical group 0.000 claims description 13
- 125000005551 pyridylene group Chemical group 0.000 claims description 12
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 11
- 230000007062 hydrolysis Effects 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- 125000004442 acylamino group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 8
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 8
- LIVAQMJLPOCEMO-UHFFFAOYSA-N 2-(4-amino-2-methylphenyl)-5-chloroisoindole-1,3-dione Chemical compound CC1=CC(N)=CC=C1N1C(=O)C2=CC(Cl)=CC=C2C1=O LIVAQMJLPOCEMO-UHFFFAOYSA-N 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 6
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 239000000047 product Substances 0.000 claims description 6
- KLYCPFXDDDMZNQ-UHFFFAOYSA-N Benzyne Chemical group C1=CC#CC=C1 KLYCPFXDDDMZNQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 4
- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- YERSZEGWYFWZIQ-UHFFFAOYSA-N 2-(4-amino-2-chlorophenyl)-5-chloroisoindole-1,3-dione Chemical compound ClC1=CC(N)=CC=C1N1C(=O)C2=CC(Cl)=CC=C2C1=O YERSZEGWYFWZIQ-UHFFFAOYSA-N 0.000 claims description 2
- XDXDWTYQHIEUOG-UHFFFAOYSA-N 2-(5-amino-2-methylphenyl)-1,3-dioxoisoindole-5-carbonitrile Chemical compound CC1=CC=C(N)C=C1N1C(=O)C2=CC(C#N)=CC=C2C1=O XDXDWTYQHIEUOG-UHFFFAOYSA-N 0.000 claims description 2
- LXIBNUOUQMCEBC-UHFFFAOYSA-N 2-(5-amino-2-methylphenyl)-1,3-dioxoisoindole-5-carboxamide Chemical compound CC1=CC=C(N)C=C1N1C(=O)C2=CC(C(N)=O)=CC=C2C1=O LXIBNUOUQMCEBC-UHFFFAOYSA-N 0.000 claims description 2
- RHPVVHLQCVXXEB-UHFFFAOYSA-N 2-(5-amino-2-methylphenyl)-1,3-dioxoisoindole-5-carboxylic acid Chemical compound CC1=CC=C(N)C=C1N1C(=O)C2=CC(C(O)=O)=CC=C2C1=O RHPVVHLQCVXXEB-UHFFFAOYSA-N 0.000 claims description 2
- BXAAQVVGUZEPEQ-UHFFFAOYSA-N 2-(5-amino-2-methylphenyl)-4-chloroisoindole-1,3-dione Chemical compound CC1=CC=C(N)C=C1N1C(=O)C2=C(Cl)C=CC=C2C1=O BXAAQVVGUZEPEQ-UHFFFAOYSA-N 0.000 claims description 2
- MAXHQZMZUYWJTK-UHFFFAOYSA-N 2-(5-amino-2-methylphenyl)-5-fluoroisoindole-1,3-dione Chemical compound CC1=CC=C(N)C=C1N1C(=O)C2=CC(F)=CC=C2C1=O MAXHQZMZUYWJTK-UHFFFAOYSA-N 0.000 claims description 2
- SZOABRZVQFUPCK-UHFFFAOYSA-N 2-(5-amino-2-methylphenyl)-6-chloro-4H-isoquinoline-1,3-dione Chemical compound CC1=CC=C(N)C=C1N1C(=O)C2=CC=C(Cl)C=C2CC1=O SZOABRZVQFUPCK-UHFFFAOYSA-N 0.000 claims description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims description 2
- FXRXRNKZCCOPBG-UHFFFAOYSA-N methyl 2-(5-amino-2-methylphenyl)-1,3-dioxoisoindole-5-carboxylate Chemical compound O=C1C2=CC(C(=O)OC)=CC=C2C(=O)N1C1=CC(N)=CC=C1C FXRXRNKZCCOPBG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims 2
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 2
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims 2
- SJSNHCAZZZUXPK-UHFFFAOYSA-N 2-(5-amino-2-methylphenyl)-5-methylisoindole-1,3-dione Chemical compound O=C1C2=CC(C)=CC=C2C(=O)N1C1=CC(N)=CC=C1C SJSNHCAZZZUXPK-UHFFFAOYSA-N 0.000 claims 1
- YJZMBMRBTKUHPQ-UHFFFAOYSA-N 2-[4-amino-2-(methylsulfonylmethyl)phenyl]-5-chloroisoindole-1,3-dione Chemical compound CS(=O)(=O)CC1=CC(N)=CC=C1N1C(=O)C2=CC(Cl)=CC=C2C1=O YJZMBMRBTKUHPQ-UHFFFAOYSA-N 0.000 claims 1
- WJLSSUNOKGJYMR-UHFFFAOYSA-N 5-methylsulfonylisoindole-1,3-dione Chemical compound CS(=O)(=O)C=1C=C2C(C(=O)NC2=O)=CC1 WJLSSUNOKGJYMR-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000012024 dehydrating agents Substances 0.000 claims 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- GPTFURBXHJWNHR-UHFFFAOYSA-N protopine Chemical compound C1=C2C(=O)CC3=CC=C4OCOC4=C3CN(C)CCC2=CC2=C1OCO2 GPTFURBXHJWNHR-UHFFFAOYSA-N 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 108
- 239000000155 melt Substances 0.000 description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
- 239000000243 solution Substances 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- 239000011541 reaction mixture Substances 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 239000000706 filtrate Substances 0.000 description 24
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 239000001257 hydrogen Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000007868 Raney catalyst Substances 0.000 description 15
- 229910000564 Raney nickel Inorganic materials 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- BTTRMCQEPDPCPA-UHFFFAOYSA-N 4-chlorophthalic anhydride Chemical compound ClC1=CC=C2C(=O)OC(=O)C2=C1 BTTRMCQEPDPCPA-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
- 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 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- HLABBEPDPGRESK-UHFFFAOYSA-N 5-chloro-2-(2-methyl-5-nitrophenyl)isoindole-1,3-dione Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N1C(=O)C2=CC(Cl)=CC=C2C1=O HLABBEPDPGRESK-UHFFFAOYSA-N 0.000 description 3
- MHXLKLZJYJZEDU-UHFFFAOYSA-N 5-chloro-2-(5-isocyanato-2-methylphenyl)isoindole-1,3-dione Chemical compound CC1=CC=C(N=C=O)C=C1N1C(=O)C2=CC(Cl)=CC=C2C1=O MHXLKLZJYJZEDU-UHFFFAOYSA-N 0.000 description 3
- BGJNRQSGJHVURK-UHFFFAOYSA-N 5-chloroisoindole-1,3-dione Chemical compound ClC1=CC=C2C(=O)NC(=O)C2=C1 BGJNRQSGJHVURK-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- 241000699670 Mus sp. Species 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
- 229910003446 platinum oxide Inorganic materials 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OEFAGVKLMZRDTB-UHFFFAOYSA-N 2-(2-methyl-5-nitrophenyl)-1,3-dioxoisoindole-5-carboxamide Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N1C(=O)C2=CC(C(N)=O)=CC=C2C1=O OEFAGVKLMZRDTB-UHFFFAOYSA-N 0.000 description 2
- PKJAHSJIWCHJMH-UHFFFAOYSA-N 2-(2-methyl-5-nitrophenyl)-1,3-dioxoisoindole-5-carboxylic acid Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N1C(=O)C2=CC(C(O)=O)=CC=C2C1=O PKJAHSJIWCHJMH-UHFFFAOYSA-N 0.000 description 2
- MJWKQOKCUJXBHA-UHFFFAOYSA-N 3-(5-chloro-1,3-dioxoisoindol-2-yl)-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1N1C(=O)C2=CC(Cl)=CC=C2C1=O MJWKQOKCUJXBHA-UHFFFAOYSA-N 0.000 description 2
- DVIPPHSQIBKWSA-UHFFFAOYSA-N 4-chlorophthalic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1C(O)=O DVIPPHSQIBKWSA-UHFFFAOYSA-N 0.000 description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
- DJZCKUIPFPEPQO-UHFFFAOYSA-N 5-chloro-2-(2-chloro-4-nitrophenyl)isoindole-1,3-dione Chemical compound ClC1=CC([N+](=O)[O-])=CC=C1N1C(=O)C2=CC(Cl)=CC=C2C1=O DJZCKUIPFPEPQO-UHFFFAOYSA-N 0.000 description 2
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- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
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- IGOQWCINLZXOHL-UHFFFAOYSA-N diethyl 4-chlorobenzene-1,2-dicarboxylate Chemical compound CCOC(=O)C1=CC=C(Cl)C=C1C(=O)OCC IGOQWCINLZXOHL-UHFFFAOYSA-N 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
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- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- JWJSFBKJNPGUGM-UHFFFAOYSA-N ethyl 2-ethoxycarbothioyl-5-methylbenzoate Chemical compound CC=1C=C(C(C(=S)OCC)=CC1)C(=O)OCC JWJSFBKJNPGUGM-UHFFFAOYSA-N 0.000 description 1
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- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- MCQOWYALZVKMAR-UHFFFAOYSA-N furo[3,4-b]pyridine-5,7-dione Chemical compound C1=CC=C2C(=O)OC(=O)C2=N1 MCQOWYALZVKMAR-UHFFFAOYSA-N 0.000 description 1
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- 150000004820 halides Chemical class 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000003949 imides Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- UKEKSQXYJALFKZ-UHFFFAOYSA-N methylsulfanylmethane;potassium Chemical compound [K].CSC UKEKSQXYJALFKZ-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- QFCSRGLEMDRBMN-UHFFFAOYSA-N n-(2-methylphenyl)nitramide Chemical compound CC1=CC=CC=C1N[N+]([O-])=O QFCSRGLEMDRBMN-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003472 neutralizing 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
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
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- 239000011368 organic material Substances 0.000 description 1
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- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- VJKUPQSHOVKBCO-AHMKVGDJSA-N picrotoxin Chemical compound O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(=C)C)[C@@H]1C(=O)O2.O=C([C@@]12O[C@@H]1C[C@]1(O)[C@@]32C)O[C@@H]3[C@H]2[C@@H](C(C)(O)C)[C@@H]1C(=O)O2 VJKUPQSHOVKBCO-AHMKVGDJSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
- 229910001958 silver carbonate Inorganic materials 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- PAYGMRRPBHYIMA-UHFFFAOYSA-N sodium;trihydrate Chemical compound O.O.O.[Na] PAYGMRRPBHYIMA-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 230000001148 spastic effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- QTEXGRHCLJVILH-UHFFFAOYSA-N tert-butyl n-[3-(5-chloro-1,3-dioxoisoindol-2-yl)-4-methylphenyl]carbamate Chemical compound CC1=CC=C(NC(=O)OC(C)(C)C)C=C1N1C(=O)C2=CC(Cl)=CC=C2C1=O QTEXGRHCLJVILH-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- FIDKFEIEZJGDBE-UHFFFAOYSA-N thieno[2,3-c]furan-4,6-dione Chemical compound S1C=CC2=C1C(=O)OC2=O FIDKFEIEZJGDBE-UHFFFAOYSA-N 0.000 description 1
- OFBPGACXRPVDQW-UHFFFAOYSA-N thiirane 1,1-dioxide Chemical compound O=S1(=O)CC1 OFBPGACXRPVDQW-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- NJMOHBDCGXJLNJ-UHFFFAOYSA-N trimellitic anhydride chloride Chemical compound ClC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 NJMOHBDCGXJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/76—Benzo[c]pyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/449,872 US3941883A (en) | 1974-03-11 | 1974-03-11 | Aromatic dicarboxamides as anticonvulsants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2509922A1 true DE2509922A1 (de) | 1975-09-25 |
Family
ID=23785818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752509922 Pending DE2509922A1 (de) | 1974-03-11 | 1975-03-07 | Neue aromatische dicarbonsaeureimide |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3941883A (Direct) |
| JP (1) | JPS50121263A (Direct) |
| AT (1) | AT345273B (Direct) |
| BE (1) | BE826464A (Direct) |
| CS (2) | CS188950B2 (Direct) |
| DE (1) | DE2509922A1 (Direct) |
| DK (1) | DK97175A (Direct) |
| ES (1) | ES435491A1 (Direct) |
| FR (1) | FR2263766A1 (Direct) |
| GB (1) | GB1480181A (Direct) |
| HU (1) | HU172625B (Direct) |
| IE (1) | IE40768B1 (Direct) |
| IL (1) | IL46783A (Direct) |
| NL (1) | NL7502878A (Direct) |
| SE (1) | SE7502028L (Direct) |
| ZA (2) | ZA75575B (Direct) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0150034A3 (en) * | 1984-01-21 | 1985-10-30 | Basf Aktiengesellschaft | Derivatives of 2-aminothiophene |
| US5276009A (en) * | 1990-07-20 | 1994-01-04 | Basf Aktiengesellschaft | Dicarboximides and their use as herbicides |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4025505A (en) * | 1975-02-04 | 1977-05-24 | Ciba-Geigy Corporation | Aromatic dicarboxamides |
| US4124593A (en) * | 1975-11-13 | 1978-11-07 | Ciba-Geigy Corporation | Aromatic dicarboximides |
| CH644362A5 (de) * | 1980-05-06 | 1984-07-31 | Ciba Geigy Ag | 3,5-disubstituierte phthalsaeureimide. |
| US4467100A (en) * | 1981-05-26 | 1984-08-21 | Lord Corporation | Epoxy resin compositions cured with imide-amine at ambient temperatures to afford products having useful properties at high temperatures |
| US5227461A (en) * | 1983-06-17 | 1993-07-13 | The Boeing Company | Extended difunctional end-cap monomers |
| US5610317A (en) * | 1985-09-05 | 1997-03-11 | The Boeing Company | Multiple chemically functional end cap monomers |
| US4935523A (en) * | 1985-09-30 | 1990-06-19 | The Boeing Company | Crosslinking imidophenylamines |
| US4985568A (en) * | 1985-09-30 | 1991-01-15 | The Boeing Company | Method of making crosslinking imidophenylamines |
| US5144000A (en) * | 1987-02-20 | 1992-09-01 | The Boeing Company | Method for forming crosslinking polyetherimide oligomers |
| US6881815B2 (en) * | 2002-09-25 | 2005-04-19 | General Electric Company | Method for the preparation poly(etherimide)s |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3767805A (en) * | 1968-03-27 | 1973-10-23 | Ciba Geigy Corp | Tertiary aminoacids in antiinflammatory compositions |
-
1974
- 1974-03-11 US US05/449,872 patent/US3941883A/en not_active Expired - Lifetime
-
1975
- 1975-01-28 ZA ZA00750575A patent/ZA75575B/xx unknown
- 1975-02-24 SE SE7502028A patent/SE7502028L/xx unknown
- 1975-03-07 GB GB9582/75A patent/GB1480181A/en not_active Expired
- 1975-03-07 FR FR7507176A patent/FR2263766A1/fr not_active Withdrawn
- 1975-03-07 DE DE19752509922 patent/DE2509922A1/de active Pending
- 1975-03-10 DK DK97175*#A patent/DK97175A/da unknown
- 1975-03-10 IE IE510/75A patent/IE40768B1/xx unknown
- 1975-03-10 HU HU75CI00001554A patent/HU172625B/hu unknown
- 1975-03-10 AT AT182475A patent/AT345273B/de active
- 1975-03-10 ZA ZA00751432A patent/ZA751432B/xx unknown
- 1975-03-10 IL IL46783A patent/IL46783A/en unknown
- 1975-03-10 BE BE154155A patent/BE826464A/xx unknown
- 1975-03-11 NL NL7502878A patent/NL7502878A/xx not_active Application Discontinuation
- 1975-03-11 CS CS765801A patent/CS188950B2/cs unknown
- 1975-03-11 CS CS751631A patent/CS188941B2/cs unknown
- 1975-03-11 ES ES435491A patent/ES435491A1/es not_active Expired
- 1975-03-11 JP JP50028730A patent/JPS50121263A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0150034A3 (en) * | 1984-01-21 | 1985-10-30 | Basf Aktiengesellschaft | Derivatives of 2-aminothiophene |
| US5276009A (en) * | 1990-07-20 | 1994-01-04 | Basf Aktiengesellschaft | Dicarboximides and their use as herbicides |
Also Published As
| Publication number | Publication date |
|---|---|
| CS188941B2 (en) | 1979-03-30 |
| BE826464A (fr) | 1975-09-10 |
| IE40768B1 (en) | 1979-08-15 |
| CS188950B2 (en) | 1979-03-30 |
| JPS50121263A (Direct) | 1975-09-23 |
| ES435491A1 (es) | 1977-01-01 |
| IL46783A0 (en) | 1975-05-22 |
| ZA75575B (en) | 1976-01-28 |
| AT345273B (de) | 1978-09-11 |
| NL7502878A (nl) | 1975-09-15 |
| AU7894675A (en) | 1976-09-16 |
| HU172625B (hu) | 1978-11-28 |
| IL46783A (en) | 1977-11-30 |
| SE7502028L (Direct) | 1975-09-12 |
| ATA182475A (de) | 1978-01-15 |
| FR2263766A1 (Direct) | 1975-10-10 |
| GB1480181A (en) | 1977-07-20 |
| IE40768L (en) | 1975-09-11 |
| DK97175A (Direct) | 1975-09-12 |
| ZA751432B (en) | 1976-02-25 |
| US3941883A (en) | 1976-03-02 |
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Legal Events
| Date | Code | Title | Description |
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| OHN | Withdrawal |