IL46783A - Aromatic dicarboximides their manufacture and pharmaceutical preparations containing them - Google Patents
Aromatic dicarboximides their manufacture and pharmaceutical preparations containing themInfo
- Publication number
- IL46783A IL46783A IL46783A IL4678375A IL46783A IL 46783 A IL46783 A IL 46783A IL 46783 A IL46783 A IL 46783A IL 4678375 A IL4678375 A IL 4678375A IL 46783 A IL46783 A IL 46783A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- amino
- tolyl
- lower alkyl
- mono
- Prior art date
Links
- -1 Aromatic dicarboximides Chemical class 0.000 title claims description 91
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
- 125000001153 fluoro group Chemical group F* 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
- 125000001246 bromo group Chemical group Br* 0.000 claims description 12
- 125000005551 pyridylene group Chemical group 0.000 claims description 12
- 125000005556 thienylene group Chemical group 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 7
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 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 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 4
- 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 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 3
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 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
- UWPCAWVMZUJSOR-UHFFFAOYSA-N 2-(5-amino-2-methylphenyl)-4-methylisoindole-1,3-dione Chemical compound O=C1C=2C(C)=CC=CC=2C(=O)N1C1=CC(N)=CC=C1C UWPCAWVMZUJSOR-UHFFFAOYSA-N 0.000 claims description 2
- GLMPYMOLUCLFIH-UHFFFAOYSA-N 2-(5-amino-2-methylphenyl)-5-(trifluoromethyl)isoindole-1,3-dione Chemical compound CC1=CC=C(N)C=C1N1C(=O)C2=CC(C(F)(F)F)=CC=C2C1=O GLMPYMOLUCLFIH-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
- DNORDOQIBZEGKB-UHFFFAOYSA-N 2-(5-amino-2-methylphenyl)-5-methoxyisoindole-1,3-dione Chemical compound O=C1C2=CC(OC)=CC=C2C(=O)N1C1=CC(N)=CC=C1C DNORDOQIBZEGKB-UHFFFAOYSA-N 0.000 claims description 2
- ZNUVSTISSXCIQL-UHFFFAOYSA-N 2-(5-amino-2-methylphenyl)-5-methylsulfonylisoindole-1,3-dione Chemical compound CC1=CC=C(N)C=C1N1C(=O)C2=CC(S(C)(=O)=O)=CC=C2C1=O ZNUVSTISSXCIQL-UHFFFAOYSA-N 0.000 claims description 2
- FJMKECYGAMETLJ-UHFFFAOYSA-N 2-[4-amino-2-(hydroxymethyl)phenyl]-5-chloroisoindole-1,3-dione Chemical compound OCC1=CC(N)=CC=C1N1C(=O)C2=CC(Cl)=CC=C2C1=O FJMKECYGAMETLJ-UHFFFAOYSA-N 0.000 claims description 2
- AUWRAAUOPMIGEE-UHFFFAOYSA-N 2-[4-amino-2-(methylsulfanylmethyl)phenyl]-5-chloroisoindole-1,3-dione Chemical compound CSCC1=CC(N)=CC=C1N1C(=O)C2=CC(Cl)=CC=C2C1=O AUWRAAUOPMIGEE-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- GGADWALRTAARHP-UHFFFAOYSA-N 2-(5-amino-2-methylphenyl)-5-bromoisoindole-1,3-dione Chemical compound CC1=CC=C(N)C=C1N1C(=O)C2=CC(Br)=CC=C2C1=O GGADWALRTAARHP-UHFFFAOYSA-N 0.000 claims 1
- 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
- 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 1
- IJSUCKBFRBOYOZ-UHFFFAOYSA-N 5-(5-amino-2-methylphenyl)thieno[2,3-c]pyrrole-4,6-dione Chemical compound CC1=CC=C(N)C=C1N1C(=O)C(SC=C2)=C2C1=O IJSUCKBFRBOYOZ-UHFFFAOYSA-N 0.000 claims 1
- YZISCJMABKVLMM-UHFFFAOYSA-N 6-(5-amino-2-methylphenyl)pyrrolo[3,4-b]pyridine-5,7-dione Chemical compound CC1=CC=C(N)C=C1N1C(=O)C2=NC=CC=C2C1=O YZISCJMABKVLMM-UHFFFAOYSA-N 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract description 3
- 229940125681 anticonvulsant agent Drugs 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
- 238000002844 melting Methods 0.000 description 54
- 230000008018 melting Effects 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- 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
- 229940093499 ethyl acetate Drugs 0.000 description 34
- 235000019439 ethyl acetate Nutrition 0.000 description 34
- 239000000243 solution Substances 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- 239000007858 starting material Substances 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 239000000706 filtrate Substances 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- 239000001257 hydrogen Substances 0.000 description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
- XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 16
- 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000000725 suspension Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 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
- 229910052757 nitrogen Inorganic materials 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 5
- 206010010904 Convulsion Diseases 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 5
- 150000003949 imides Chemical class 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 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 4
- RSLFVGGLNAVTNI-UHFFFAOYSA-N 5-chloro-2-[2-(methylsulfanylmethyl)-4-nitrophenyl]isoindole-1,3-dione Chemical compound CSCC1=CC([N+]([O-])=O)=CC=C1N1C(=O)C2=CC(Cl)=CC=C2C1=O RSLFVGGLNAVTNI-UHFFFAOYSA-N 0.000 description 4
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 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 3
- 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 3
- DVIPPHSQIBKWSA-UHFFFAOYSA-N 4-chlorophthalic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1C(O)=O DVIPPHSQIBKWSA-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- ONBDMPZNIMUOFB-UHFFFAOYSA-N 2-(2-methyl-5-nitrophenyl)-5-(trifluoromethyl)isoindole-1,3-dione Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N1C(=O)C2=CC(C(F)(F)F)=CC=C2C1=O ONBDMPZNIMUOFB-UHFFFAOYSA-N 0.000 description 2
- GXWCKSQMZBQZAB-UHFFFAOYSA-N 2-(2-methyl-5-nitrophenyl)pyrrolo[3,4-c]pyridine-1,3-dione Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N1C(=O)C2=CN=CC=C2C1=O GXWCKSQMZBQZAB-UHFFFAOYSA-N 0.000 description 2
- HCRSXTSGSLECNB-UHFFFAOYSA-N 2-(methylsulfanylmethyl)-4-nitroaniline Chemical compound CSCC1=CC([N+]([O-])=O)=CC=C1N HCRSXTSGSLECNB-UHFFFAOYSA-N 0.000 description 2
- LLLFDOWKSSVDOT-UHFFFAOYSA-N 2-[4-chloro-2-[(2-methyl-5-nitrophenyl)carbamoyl]phenyl]acetic acid Chemical compound CC1=CC=C([N+]([O-])=O)C=C1NC(=O)C1=CC(Cl)=CC=C1CC(O)=O LLLFDOWKSSVDOT-UHFFFAOYSA-N 0.000 description 2
- NHHKPBFJBQZOGL-UHFFFAOYSA-N 4-chloro-2-(2-methyl-5-nitrophenyl)isoindole-1,3-dione Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N1C(=O)C2=C(Cl)C=CC=C2C1=O NHHKPBFJBQZOGL-UHFFFAOYSA-N 0.000 description 2
- OYRBBSKHKUSUBI-UHFFFAOYSA-N 4-chloro-2-ethylbenzoic acid Chemical compound CCC1=CC(Cl)=CC=C1C(O)=O OYRBBSKHKUSUBI-UHFFFAOYSA-N 0.000 description 2
- GUGFNRBSYQUGCB-UHFFFAOYSA-N 4-methyl-2-(2-methyl-5-nitrophenyl)isoindole-1,3-dione Chemical compound O=C1C=2C(C)=CC=CC=2C(=O)N1C1=CC([N+]([O-])=O)=CC=C1C GUGFNRBSYQUGCB-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
- TYHXNAQWBHYGBB-UHFFFAOYSA-N 5-chloro-2-[2-(iodomethyl)-4-nitrophenyl]isoindole-1,3-dione Chemical compound ICC1=CC([N+](=O)[O-])=CC=C1N1C(=O)C2=CC(Cl)=CC=C2C1=O TYHXNAQWBHYGBB-UHFFFAOYSA-N 0.000 description 2
- NUYSHFWPXCGHTC-UHFFFAOYSA-N 5-methoxy-2-(2-methyl-5-nitrophenyl)isoindole-1,3-dione Chemical compound O=C1C2=CC(OC)=CC=C2C(=O)N1C1=CC([N+]([O-])=O)=CC=C1C NUYSHFWPXCGHTC-UHFFFAOYSA-N 0.000 description 2
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- KZZFTKWLYNNBGP-UHFFFAOYSA-N 6-chloro-2-(2-methyl-5-nitrophenyl)-4H-isoquinoline-1,3-dione Chemical compound CC1=CC=C([N+]([O-])=O)C=C1N1C(=O)C2=CC=C(Cl)C=C2CC1=O KZZFTKWLYNNBGP-UHFFFAOYSA-N 0.000 description 2
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- 125000006351 ethylthiomethyl group Chemical group [H]C([H])([H])C([H])([H])SC([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000004508 fractional distillation Methods 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
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N hydroxymaleic acid group Chemical group O/C(/C(=O)O)=C/C(=O)O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions 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
- 239000000644 isotonic solution Substances 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000155 melt 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 group 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- AYDYFHOKCIHJOM-UHFFFAOYSA-N methyl 2-(2-methyl-5-nitrophenyl)-1,3-dioxoisoindole-5-carboxylate Chemical compound O=C1C2=CC(C(=O)OC)=CC=C2C(=O)N1C1=CC([N+]([O-])=O)=CC=C1C AYDYFHOKCIHJOM-UHFFFAOYSA-N 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
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 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
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 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
- 229960005235 piperonyl butoxide Drugs 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
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 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
- 238000000746 purification Methods 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
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000000926 separation method Methods 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
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 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
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000001148 spastic effect Effects 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 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
- 101150068774 thyX gene Proteins 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 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
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent 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)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (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 (2)
| Publication Number | Publication Date |
|---|---|
| IL46783A0 IL46783A0 (en) | 1975-05-22 |
| IL46783A true IL46783A (en) | 1977-11-30 |
Family
ID=23785818
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL46783A IL46783A (en) | 1974-03-11 | 1975-03-10 | Aromatic dicarboximides their manufacture and pharmaceutical preparations containing them |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3941883A (cs) |
| JP (1) | JPS50121263A (cs) |
| AT (1) | AT345273B (cs) |
| BE (1) | BE826464A (cs) |
| CS (2) | CS188941B2 (cs) |
| DE (1) | DE2509922A1 (cs) |
| DK (1) | DK97175A (cs) |
| ES (1) | ES435491A1 (cs) |
| FR (1) | FR2263766A1 (cs) |
| GB (1) | GB1480181A (cs) |
| HU (1) | HU172625B (cs) |
| IE (1) | IE40768B1 (cs) |
| IL (1) | IL46783A (cs) |
| NL (1) | NL7502878A (cs) |
| SE (1) | SE7502028L (cs) |
| ZA (2) | ZA75575B (cs) |
Families Citing this family (12)
| 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 |
| DE3402026A1 (de) * | 1984-01-21 | 1985-07-25 | Basf Ag, 6700 Ludwigshafen | Neue 2-aminothiophenderivate |
| 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 |
| DE4023048A1 (de) * | 1990-07-20 | 1992-01-23 | Basf Ag | Dicarbonsaeureimide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| 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 DE DE19752509922 patent/DE2509922A1/de active Pending
- 1975-03-07 FR FR7507176A patent/FR2263766A1/fr not_active Withdrawn
- 1975-03-10 ZA ZA00751432A patent/ZA751432B/xx unknown
- 1975-03-10 AT AT182475A patent/AT345273B/de active
- 1975-03-10 IL IL46783A patent/IL46783A/en unknown
- 1975-03-10 IE IE510/75A patent/IE40768B1/xx unknown
- 1975-03-10 DK DK97175*#A patent/DK97175A/da unknown
- 1975-03-10 BE BE154155A patent/BE826464A/xx unknown
- 1975-03-10 HU HU75CI00001554A patent/HU172625B/hu unknown
- 1975-03-11 NL NL7502878A patent/NL7502878A/xx not_active Application Discontinuation
- 1975-03-11 ES ES435491A patent/ES435491A1/es not_active Expired
- 1975-03-11 JP JP50028730A patent/JPS50121263A/ja active Pending
- 1975-03-11 CS CS751631A patent/CS188941B2/cs unknown
- 1975-03-11 CS CS765801A patent/CS188950B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK97175A (cs) | 1975-09-12 |
| FR2263766A1 (cs) | 1975-10-10 |
| US3941883A (en) | 1976-03-02 |
| AU7894675A (en) | 1976-09-16 |
| ATA182475A (de) | 1978-01-15 |
| ZA751432B (en) | 1976-02-25 |
| IE40768B1 (en) | 1979-08-15 |
| ES435491A1 (es) | 1977-01-01 |
| ZA75575B (en) | 1976-01-28 |
| SE7502028L (cs) | 1975-09-12 |
| HU172625B (hu) | 1978-11-28 |
| JPS50121263A (cs) | 1975-09-23 |
| GB1480181A (en) | 1977-07-20 |
| CS188941B2 (en) | 1979-03-30 |
| BE826464A (fr) | 1975-09-10 |
| IL46783A0 (en) | 1975-05-22 |
| AT345273B (de) | 1978-09-11 |
| DE2509922A1 (de) | 1975-09-25 |
| IE40768L (en) | 1975-09-11 |
| CS188950B2 (en) | 1979-03-30 |
| NL7502878A (nl) | 1975-09-15 |
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