FI69833C - Foerfarande foer framstaellning av terapeutiskt anvaendbara sustituerade heterocykliska bensamider - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara sustituerade heterocykliska bensamider Download PDFInfo
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- FI69833C FI69833C FI790181A FI790181A FI69833C FI 69833 C FI69833 C FI 69833C FI 790181 A FI790181 A FI 790181A FI 790181 A FI790181 A FI 790181A FI 69833 C FI69833 C FI 69833C
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- 238000010438 heat treatment Methods 0.000 title description 5
- -1 heterocyclic benzamides Chemical class 0.000 claims abstract description 39
- 229940054066 benzamide antipsychotics Drugs 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 41
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- QTWZISKLRIHFNO-UHFFFAOYSA-N n-(2,5-dichloropentyl)-2-methoxy-5-sulfamoylbenzamide Chemical group COC1=CC=C(S(N)(=O)=O)C=C1C(=O)NCC(Cl)CCCCl QTWZISKLRIHFNO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000000543 intermediate Substances 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 150000003936 benzamides Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 2
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 238000005342 ion exchange Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 abstract description 2
- 238000012986 modification Methods 0.000 abstract 1
- 230000004048 modification Effects 0.000 abstract 1
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- 239000000243 solution Substances 0.000 description 121
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 85
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 85
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 80
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- 239000002244 precipitate Substances 0.000 description 63
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- 239000013078 crystal Substances 0.000 description 48
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
- 238000002844 melting Methods 0.000 description 41
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- 229910021529 ammonia Inorganic materials 0.000 description 34
- 229960000583 acetic acid Drugs 0.000 description 27
- 235000011054 acetic acid Nutrition 0.000 description 26
- 238000010992 reflux Methods 0.000 description 26
- 239000000725 suspension Substances 0.000 description 26
- 239000000706 filtrate Substances 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 239000003610 charcoal Substances 0.000 description 20
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 20
- 238000009835 boiling Methods 0.000 description 19
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 238000003756 stirring Methods 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 15
- 239000003708 ampul Substances 0.000 description 15
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- 239000012074 organic phase Substances 0.000 description 13
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000006229 carbon black Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 10
- OJVNCXHGGYYOPH-UHFFFAOYSA-N 4-amino-5-ethylsulfonyl-2-methoxybenzoic acid Chemical compound CCS(=O)(=O)C1=CC(C(O)=O)=C(OC)C=C1N OJVNCXHGGYYOPH-UHFFFAOYSA-N 0.000 description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 235000011181 potassium carbonates Nutrition 0.000 description 8
- FWZCSDNSXJJNLH-UHFFFAOYSA-N (1-cyclohexylpyrrolidin-2-yl)methanamine Chemical compound NCC1CCCN1C1CCCCC1 FWZCSDNSXJJNLH-UHFFFAOYSA-N 0.000 description 7
- 230000003474 anti-emetic effect Effects 0.000 description 7
- 238000004090 dissolution Methods 0.000 description 7
- QFIYFROFRTUSPW-UHFFFAOYSA-N [1-(cyclopropylmethyl)pyrrolidin-2-yl]methanamine Chemical compound NCC1CCCN1CC1CC1 QFIYFROFRTUSPW-UHFFFAOYSA-N 0.000 description 6
- 230000002903 catalepsic effect Effects 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- YEVQOPOKMKTXMD-UHFFFAOYSA-N 2,3-dimethoxy-5-sulfamoylbenzoic acid Chemical compound COC1=CC(S(N)(=O)=O)=CC(C(O)=O)=C1OC YEVQOPOKMKTXMD-UHFFFAOYSA-N 0.000 description 5
- XFZMCFJADJFEBB-UHFFFAOYSA-N 2-methoxy-5-sulfamoylbenzoyl chloride Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(Cl)=O XFZMCFJADJFEBB-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- SBSSXCKDVHHANA-UHFFFAOYSA-N 1-(cyclohexylmethyl)pyrrolidin-3-amine Chemical compound C1C(N)CCN1CC1CCCCC1 SBSSXCKDVHHANA-UHFFFAOYSA-N 0.000 description 4
- WWZAQUJXWBZQLQ-UHFFFAOYSA-N 1-(cyclopropylmethyl)pyrrolidin-3-amine Chemical compound C1C(N)CCN1CC1CC1 WWZAQUJXWBZQLQ-UHFFFAOYSA-N 0.000 description 4
- XXXLNTRZWHZOCN-UHFFFAOYSA-N 2,3-dimethoxy-5-(methylsulfamoyl)benzoic acid Chemical compound CNS(=O)(=O)C1=CC(OC)=C(OC)C(C(O)=O)=C1 XXXLNTRZWHZOCN-UHFFFAOYSA-N 0.000 description 4
- ATGSLQBVSZNJMT-UHFFFAOYSA-N 2,5-dichloropentan-1-amine;hydrochloride Chemical compound Cl.NCC(Cl)CCCCl ATGSLQBVSZNJMT-UHFFFAOYSA-N 0.000 description 4
- ISAWQVIALQROTK-UHFFFAOYSA-N 5-ethylsulfonyl-2,3-dimethoxybenzoic acid Chemical compound CCS(=O)(=O)C1=CC(OC)=C(OC)C(C(O)=O)=C1 ISAWQVIALQROTK-UHFFFAOYSA-N 0.000 description 4
- FBHYCUIQJPFIGD-UHFFFAOYSA-N 5-ethylsulfonyl-2,3-dimethoxybenzoyl chloride Chemical compound CCS(=O)(=O)C1=CC(OC)=C(OC)C(C(Cl)=O)=C1 FBHYCUIQJPFIGD-UHFFFAOYSA-N 0.000 description 4
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- YARZWCAMQSVZLU-UHFFFAOYSA-N (1-cyclopentylpyrrolidin-2-yl)methanamine Chemical compound NCC1CCCN1C1CCCC1 YARZWCAMQSVZLU-UHFFFAOYSA-N 0.000 description 3
- MFEGMDSNERQIEI-UHFFFAOYSA-N 4-amino-N-[[1-(cyclopropylmethyl)pyrrolidin-2-yl]methyl]-2-methoxy-5-(methylsulfamoyl)benzamide Chemical compound C1(CC1)CN1C(CCC1)CNC(C1=C(C=C(C(=C1)S(NC)(=O)=O)N)OC)=O MFEGMDSNERQIEI-UHFFFAOYSA-N 0.000 description 3
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- PVMQHXAMKMMDNP-UHFFFAOYSA-N 4-amino-n-[(1-cyclohexylpyrrolidin-2-yl)methyl]-5-ethylsulfonyl-2-methoxybenzamide Chemical compound C1=C(N)C(S(=O)(=O)CC)=CC(C(=O)NCC2N(CCC2)C2CCCCC2)=C1OC PVMQHXAMKMMDNP-UHFFFAOYSA-N 0.000 description 3
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- 238000002329 infrared spectrum Methods 0.000 description 3
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- LLAREYWYSUDGCP-UHFFFAOYSA-N n-[(1-cyclohexylpyrrolidin-2-yl)methyl]-2,3-dimethoxy-5-(methylsulfamoyl)benzamide Chemical compound CNS(=O)(=O)C1=CC(OC)=C(OC)C(C(=O)NCC2N(CCC2)C2CCCCC2)=C1 LLAREYWYSUDGCP-UHFFFAOYSA-N 0.000 description 3
- PTTMZJCWHXWNMI-UHFFFAOYSA-N n-[(1-cyclohexylpyrrolidin-2-yl)methyl]-2-methoxy-5-(methylsulfamoyl)benzamide Chemical compound CNS(=O)(=O)C1=CC=C(OC)C(C(=O)NCC2N(CCC2)C2CCCCC2)=C1 PTTMZJCWHXWNMI-UHFFFAOYSA-N 0.000 description 3
- JUMQGYPYUCYLKT-UHFFFAOYSA-N n-[(1-cyclohexylpyrrolidin-2-yl)methyl]-2-methoxy-5-sulfamoylbenzamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(=O)NCC1N(C2CCCCC2)CCC1 JUMQGYPYUCYLKT-UHFFFAOYSA-N 0.000 description 3
- MHAJIJIZSZAWAS-UHFFFAOYSA-N n-[1-(cyclohexylmethyl)pyrrolidin-3-yl]-2-methoxy-5-methylsulfonylbenzamide Chemical compound COC1=CC=C(S(C)(=O)=O)C=C1C(=O)NC1CN(CC2CCCCC2)CC1 MHAJIJIZSZAWAS-UHFFFAOYSA-N 0.000 description 3
- ZRUKCMQRXVKXQN-UHFFFAOYSA-N n-[1-(cyclopropylmethyl)pyrrolidin-3-yl]-2-methoxy-5-sulfamoylbenzamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(=O)NC1CN(CC2CC2)CC1 ZRUKCMQRXVKXQN-UHFFFAOYSA-N 0.000 description 3
- DXDVIHWHNZVPOK-UHFFFAOYSA-N (1-cyclopropylpyrrolidin-2-yl)methanamine Chemical compound NCC1CCCN1C1CC1 DXDVIHWHNZVPOK-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
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- LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
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- SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
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- DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical compound OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 description 1
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- IRGMWPMUTWZIIJ-UHFFFAOYSA-N methyl 4-amino-2-methoxy-5-thiocyanatobenzoate Chemical compound COC(=O)C1=CC(SC#N)=C(N)C=C1OC IRGMWPMUTWZIIJ-UHFFFAOYSA-N 0.000 description 1
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- WFERTIUAFYPSKZ-UHFFFAOYSA-N n-[[1-(cyclohexylmethyl)pyrrolidin-2-yl]methyl]-2,3-dimethoxy-5-sulfamoylbenzamide Chemical compound COC1=CC(S(N)(=O)=O)=CC(C(=O)NCC2N(CCC2)CC2CCCCC2)=C1OC WFERTIUAFYPSKZ-UHFFFAOYSA-N 0.000 description 1
- URRSYDOURLSJKC-UHFFFAOYSA-N n-[[1-(cyclopropylmethyl)pyrrolidin-2-yl]methyl]-2,3-dimethoxy-5-sulfamoylbenzamide Chemical compound COC1=CC(S(N)(=O)=O)=CC(C(=O)NCC2N(CCC2)CC2CC2)=C1OC URRSYDOURLSJKC-UHFFFAOYSA-N 0.000 description 1
- PAHNDJYHGKMAFM-UHFFFAOYSA-N n-[[1-(cyclopropylmethyl)pyrrolidin-3-yl]methyl]-2,3-dimethoxy-5-sulfamoylbenzamide Chemical compound COC1=CC(S(N)(=O)=O)=CC(C(=O)NCC2CN(CC3CC3)CC2)=C1OC PAHNDJYHGKMAFM-UHFFFAOYSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
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- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000005049 silicon tetrachloride Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
- C07C65/28—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7801633 | 1978-01-20 | ||
FR7801633A FR2424909A1 (fr) | 1978-01-20 | 1978-01-20 | Nouveaux derives d'ortho-anisamides utiles comme medicaments modificateurs du comportement, et leurs procedes de preparation |
FR7831458A FR2440946A2 (fr) | 1978-01-20 | 1978-11-07 | Nouveaux benzamides heterocycliques substitues, leurs procedes de preparation et leur application comme modificateurs du comportement |
FR7831458 | 1978-11-07 |
Publications (3)
Publication Number | Publication Date |
---|---|
FI790181A FI790181A (fi) | 1979-07-21 |
FI69833B FI69833B (fi) | 1985-12-31 |
FI69833C true FI69833C (fi) | 1986-05-26 |
Family
ID=26220412
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI790181A FI69833C (fi) | 1978-01-20 | 1979-01-19 | Foerfarande foer framstaellning av terapeutiskt anvaendbara sustituerade heterocykliska bensamider |
Country Status (39)
Country | Link |
---|---|
US (2) | US4673686A (nl) |
JP (1) | JPS54138553A (nl) |
AR (2) | AR221355A1 (nl) |
AT (2) | AT377254B (nl) |
AU (1) | AU520746B2 (nl) |
BE (1) | BE873522A (nl) |
BG (2) | BG48335A3 (nl) |
CA (1) | CA1133477A (nl) |
CH (2) | CH639369A5 (nl) |
CS (2) | CS241016B2 (nl) |
CY (1) | CY1202A (nl) |
DD (1) | DD141521A5 (nl) |
DE (1) | DE2901170A1 (nl) |
DK (1) | DK157008C (nl) |
EG (1) | EG13764A (nl) |
ES (2) | ES476757A1 (nl) |
FI (1) | FI69833C (nl) |
FR (1) | FR2440946A2 (nl) |
GB (2) | GB2013662B (nl) |
GR (1) | GR64398B (nl) |
HK (1) | HK12284A (nl) |
HU (1) | HU177902B (nl) |
IE (2) | IE48209B1 (nl) |
IL (2) | IL56413A (nl) |
IN (1) | IN150618B (nl) |
IT (1) | IT1164821B (nl) |
LU (1) | LU80793A1 (nl) |
MC (1) | MC1231A1 (nl) |
MX (2) | MX6192E (nl) |
NL (1) | NL7900455A (nl) |
NO (1) | NO153530C (nl) |
NZ (2) | NZ189381A (nl) |
OA (1) | OA06153A (nl) |
PL (1) | PL117195B1 (nl) |
PT (1) | PT69069A (nl) |
RO (2) | RO76554A (nl) |
SE (2) | SE449862B (nl) |
SU (1) | SU1158040A3 (nl) |
YU (2) | YU41608B (nl) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE8101536L (sv) * | 1981-03-11 | 1982-09-12 | Astra Laekemedel Ab | Bensamid-derivat |
SE8205135D0 (sv) * | 1982-09-09 | 1982-09-09 | Astra Laekemedel Ab | Benzamido-derivatives |
CH656126A5 (de) * | 1983-08-18 | 1986-06-13 | Ciba Geigy Ag | Durch 2-propynyloxygruppen substituierte phthalsaeureanhydride. |
SE8400478D0 (sv) * | 1984-01-31 | 1984-01-31 | Astra Laekemedel Ab | Oxysalicylamido derivatives |
US5240957A (en) * | 1984-01-31 | 1993-08-31 | Astra Lakemedel Akteibolag | Oxysalicylamido derivatives |
FR2574795B1 (fr) * | 1984-12-18 | 1987-11-20 | Ile De France | Nouveau procede industriel de synthese du n-((1'-allyl 2'-pyrrolidinyl) methyl) 2-methoxy 4,5-azimido benzamide |
FR2586018B1 (fr) * | 1985-08-12 | 1988-03-25 | Ile De France | Nouveau benzodioxepanne, son procede de synthese et ses applications en therapeutique |
US4772459A (en) * | 1986-09-09 | 1988-09-20 | Erbamont, Inc. | Method for controlling emesis caused by chemotherapeutic agents and antiemetic agents useful therein |
US5154913A (en) * | 1987-11-19 | 1992-10-13 | Vanderbilt University | Radioiodinated benzamines method of their use as radioimaging agents |
EP0320630A1 (en) * | 1987-11-19 | 1989-06-21 | The Vanderbilt University | Enantiometric iodobenzamides |
CN1054980A (zh) * | 1990-02-19 | 1991-10-02 | 杏林制药株式会社 | 具有旋光活性的8-甲氧基喹诺酮羧酸衍生物,它们的制备方法以及它们的中间体 |
FR2678266A1 (fr) * | 1991-06-28 | 1992-12-31 | Delagrange Laboratoires | Nouveaux derives de 2-hydroxy 4-amino 5-ethylsulfonyl benzamide utiles comme anxiolytiques. |
US6517811B2 (en) | 1993-05-06 | 2003-02-11 | Research Corporation Technologies, Inc. | Compounds for cancer imaging and therapy |
WO1994026314A1 (en) * | 1993-05-06 | 1994-11-24 | John Christy S | Compounds for cancer imaging and therapy |
US5993777A (en) * | 1993-05-06 | 1999-11-30 | Research Corporation Technologies, Inc. | Benzamide compounds for cancer imaging and therapy |
US5911970A (en) * | 1993-05-06 | 1999-06-15 | Research Corporation Technologies, Inc. | Methods for cancer imaging and therapy using benzamine compounds |
CN103450058B (zh) * | 2013-09-18 | 2015-10-14 | 广安凯特医药化工有限公司 | 一种氨磺必利酸的制备方法 |
CN105503666A (zh) * | 2015-12-30 | 2016-04-20 | 苏州诚和医药化学有限公司 | 一种便捷合成2-甲氧基-5-氨磺酰基苯甲酸甲酯的方法 |
Family Cites Families (27)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3342826A (en) * | 1964-01-13 | 1967-09-19 | Ile De France | Heterocyclic aminoalkyl benzamides |
FR6787M (nl) * | 1967-08-17 | 1969-03-17 | ||
US3891671A (en) * | 1968-08-01 | 1975-06-24 | Ile De France | N-(2-pyrrolidyl or piperidyl alkyl)-4-hydroxy benzamides |
US3959477A (en) * | 1968-08-01 | 1976-05-25 | Societe D'etudes Scientifiques Et Industrielles De L'ile-De-France | Methods of protection against emesis in mammals by administration of a heterocyclic benzamide |
US3577440A (en) * | 1968-12-23 | 1971-05-04 | Robins Co Inc A H | 1-substituted-3-amido-pyrrolidines |
GB1364231A (en) * | 1968-12-23 | 1974-08-21 | Robins Co Inc A H | N-/1-substituted-3-pyrrolidinyl/benzamides and thiobenzamides |
FR2097031A1 (en) * | 1970-07-29 | 1972-03-03 | Berri Balzac | 2-aminoethoxyethyl-6,6-dimethyl nor pinane derivs - local anaesthetics spasmolytics and anticholinergics |
GB1392194A (en) * | 1971-09-23 | 1975-04-30 | Wyeth John & Brother Ltd | Pyrrolidine derivatives |
US3966957A (en) * | 1972-04-03 | 1976-06-29 | A. H. Robins Company, Incorporated | Method for controlling emesis with N-(1-substituted-3-pyrrolidinyl)benzamides and thiobenzamides |
US4279822A (en) * | 1972-04-03 | 1981-07-21 | A. H. Robins Company, Inc. | N-(1-Substituted-3-pyrrolidinyl)benzamides |
US3862139A (en) * | 1972-06-23 | 1975-01-21 | Delmar Chem | Heterocyclic benzamide compounds |
US4048321A (en) * | 1973-12-14 | 1977-09-13 | Science Union Et Cie | Disubstituted azabicycloalkanes |
CH605793A5 (nl) * | 1974-03-05 | 1978-10-13 | Ile De France | |
DE2556457C3 (de) * | 1974-12-18 | 1981-02-12 | Synthelabo S.A., Paris | N-(Pyrrolidin-2-yl-methyl)-2-methoxybenzamide, deren Salze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
US4172143A (en) * | 1974-12-18 | 1979-10-23 | Synthelabo | 2-Methoxy-benzamide derivatives |
US4158060A (en) * | 1974-12-18 | 1979-06-12 | Synthelabo | 2-Methoxy-benzamide derivatives |
US4039672A (en) * | 1975-01-11 | 1977-08-02 | Societe D'etudes Scientifiques Et Industrielles De L'ile-De-France | N-(1'-allypyrrolidinyl 2'-methyl) 2-methoxy 4,5-azimido benzamide and its pharmaceutically acceptable salts |
GB1520584A (en) * | 1975-04-02 | 1978-08-09 | Yamanouchi Pharma Co Ltd | 2 - alkoxy - 5 substituted benzamide derivatives and their use in pharmaceutical compositions |
US4197243A (en) * | 1975-04-02 | 1980-04-08 | Yamanouchi Pharmaceutical Co., Ltd. | N-1-Benzyl-3-pyrrolidinyl-4-dimethylamino benzamide derivatives |
CH614709A5 (nl) * | 1975-09-25 | 1979-12-14 | Ciba Geigy Ag | |
JPS5248661A (en) * | 1975-10-14 | 1977-04-18 | Synthelabo | 22methoxyybenzamide derivatives |
NZ186175A (en) * | 1977-01-27 | 1980-03-05 | Shionogi & Co | Meta-sulphonamidobenzamide derivatives |
FR2415099A1 (fr) * | 1978-01-20 | 1979-08-17 | Ile De France | Nouveaux derives de 4-amino-5-alkylsulfonyl ortho-anisamides, leurs procedes de preparation et leur application comme psychotropes |
IL61642A0 (en) * | 1979-12-20 | 1981-01-30 | Beecham Group Ltd | Aniline derivatives,their preparation and pharmalceutical compositions containing them |
IL61972A0 (en) * | 1980-01-30 | 1981-02-27 | Beecham Group Ltd | Azabicyclic compounds,their preparation and pharmaceutical compositions containing them |
US4352802A (en) * | 1980-06-10 | 1982-10-05 | Beecham Group Limited | Bicyclo[3.3.1]nonyl-benzamide |
FR2493848B2 (fr) * | 1980-11-07 | 1986-05-16 | Delalande Sa | Nouveaux derives des nor-tropane et granatane, leur procede de preparation et leur application en therapeutique |
-
1978
- 1978-11-07 FR FR7831458A patent/FR2440946A2/fr active Granted
-
1979
- 1979-01-11 ES ES476757A patent/ES476757A1/es not_active Expired
- 1979-01-11 IL IL56413A patent/IL56413A/xx unknown
- 1979-01-11 AR AR275135A patent/AR221355A1/es active
- 1979-01-11 MC MC791354A patent/MC1231A1/xx unknown
- 1979-01-12 PT PT69069A patent/PT69069A/pt unknown
- 1979-01-13 DE DE19792901170 patent/DE2901170A1/de active Granted
- 1979-01-15 BG BG042076A patent/BG48335A3/xx unknown
- 1979-01-15 AU AU43374/79A patent/AU520746B2/en not_active Ceased
- 1979-01-15 GR GR58091A patent/GR64398B/el unknown
- 1979-01-15 BG BG043504A patent/BG48336A3/xx unknown
- 1979-01-15 NZ NZ189381A patent/NZ189381A/en unknown
- 1979-01-16 LU LU80793A patent/LU80793A1/xx unknown
- 1979-01-17 BE BE1/9242A patent/BE873522A/xx not_active IP Right Cessation
- 1979-01-17 IN IN46/CAL/79A patent/IN150618B/en unknown
- 1979-01-17 CY CY1202A patent/CY1202A/xx unknown
- 1979-01-17 YU YU105/79A patent/YU41608B/xx unknown
- 1979-01-17 GB GB7901688A patent/GB2013662B/en not_active Expired
- 1979-01-17 EG EG28/79A patent/EG13764A/xx active
- 1979-01-17 GB GB8119940A patent/GB2083459B/en not_active Expired
- 1979-01-17 SE SE7900419A patent/SE449862B/sv not_active IP Right Cessation
- 1979-01-18 RO RO7996327A patent/RO76554A/ro unknown
- 1979-01-18 RO RO79103351A patent/RO80716A/ro unknown
- 1979-01-18 IT IT47707/79A patent/IT1164821B/it active
- 1979-01-18 DK DK021079A patent/DK157008C/da not_active IP Right Cessation
- 1979-01-18 CH CH50979A patent/CH639369A5/fr not_active IP Right Cessation
- 1979-01-18 NO NO790179A patent/NO153530C/no unknown
- 1979-01-19 DD DD79210558A patent/DD141521A5/de unknown
- 1979-01-19 MX MX797670U patent/MX6192E/es unknown
- 1979-01-19 NL NL7900455A patent/NL7900455A/nl not_active Application Discontinuation
- 1979-01-19 OA OA56713A patent/OA06153A/xx unknown
- 1979-01-19 AT AT0039779A patent/AT377254B/de not_active IP Right Cessation
- 1979-01-19 PL PL1979212898A patent/PL117195B1/pl unknown
- 1979-01-19 JP JP548479A patent/JPS54138553A/ja active Granted
- 1979-01-19 CS CS79444A patent/CS241016B2/cs unknown
- 1979-01-19 CS CS8380A patent/CS241039B2/cs unknown
- 1979-01-19 CA CA319,968A patent/CA1133477A/en not_active Expired
- 1979-01-19 FI FI790181A patent/FI69833C/fi not_active IP Right Cessation
- 1979-01-19 HU HU79SO1242A patent/HU177902B/hu not_active IP Right Cessation
- 1979-01-19 SU SU792712702A patent/SU1158040A3/ru active
- 1979-01-19 MX MX7911207U patent/MX7622E/es unknown
- 1979-01-30 IE IE2021/81A patent/IE48209B1/en not_active IP Right Cessation
- 1979-01-30 IE IE91/79A patent/IE48208B1/en not_active IP Right Cessation
- 1979-02-16 ES ES477783A patent/ES477783A1/es not_active Expired
-
1980
- 1980-07-10 AR AR281712A patent/AR221428A1/es active
-
1981
- 1981-03-04 NZ NZ196409A patent/NZ196409A/xx unknown
-
1982
- 1982-02-03 IL IL64928A patent/IL64928A0/xx not_active IP Right Cessation
- 1982-12-03 YU YU2685/82A patent/YU43809B/xx unknown
-
1983
- 1983-05-26 CH CH289083A patent/CH641154A5/fr not_active IP Right Cessation
- 1983-08-24 AT AT0301483A patent/AT377979B/de not_active IP Right Cessation
-
1984
- 1984-02-16 HK HK122/84A patent/HK12284A/xx unknown
-
1985
- 1985-08-26 US US06/769,796 patent/US4673686A/en not_active Expired - Fee Related
-
1986
- 1986-04-30 US US06/858,906 patent/US4816471A/en not_active Expired - Fee Related
- 1986-10-16 SE SE8604394A patent/SE463972B/sv not_active IP Right Cessation
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