CH496713A - Verfahren zur Herstellung von Pyrazinamiden - Google Patents
Verfahren zur Herstellung von PyrazinamidenInfo
- Publication number
- CH496713A CH496713A CH803767A CH803767A CH496713A CH 496713 A CH496713 A CH 496713A CH 803767 A CH803767 A CH 803767A CH 803767 A CH803767 A CH 803767A CH 496713 A CH496713 A CH 496713A
- Authority
- CH
- Switzerland
- Prior art keywords
- lower alkyl
- alkyl
- amino
- methyl
- phenyl
- Prior art date
Links
- 239000002934 diuretic Substances 0.000 title abstract description 4
- SFSMATGDLFHTHE-UHFFFAOYSA-N 3-aminopyrazine-2-carboxamide Chemical class NC(=O)C1=NC=CN=C1N SFSMATGDLFHTHE-UHFFFAOYSA-N 0.000 title abstract description 3
- 230000001882 diuretic effect Effects 0.000 title abstract description 3
- -1 piperidino, pyrrolidino Chemical group 0.000 claims abstract description 117
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 64
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 6
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000005059 halophenyl group Chemical group 0.000 claims abstract description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 239000000460 chlorine Chemical group 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 229960005206 pyrazinamide Drugs 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
- 125000004799 bromophenyl group Chemical group 0.000 claims description 2
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 230000001419 dependent effect Effects 0.000 claims 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 4
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 125000005122 aminoalkylamino group Chemical group 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- JGAJCAJHSHUPGH-UHFFFAOYSA-N methyl 3-amino-6-chloropyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=CN=C1N JGAJCAJHSHUPGH-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000000155 melt Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000001953 recrystallisation Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- NJAYXNFNZKQGNE-UHFFFAOYSA-N methyl 3-bromo-6-chloropyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=CN=C1Br NJAYXNFNZKQGNE-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- ZXCBLBWKVUMUBW-UHFFFAOYSA-N 3-amino-5-(trifluoromethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC=C(N1)C(F)(F)F)C(=O)N ZXCBLBWKVUMUBW-UHFFFAOYSA-N 0.000 description 3
- MHBZGKFJMRITHV-UHFFFAOYSA-N 3-amino-6-(trifluoromethyl)pyrazine-2-carboxamide Chemical compound NC=1C(=NC(=CN1)C(F)(F)F)C(=O)N MHBZGKFJMRITHV-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- RRKJFUSUDZZRGJ-UHFFFAOYSA-N ethyl 3-amino-6-(trifluoromethyl)pyrazine-2-carboxylate Chemical compound NC=1C(=NC(=CN1)C(F)(F)F)C(=O)OCC RRKJFUSUDZZRGJ-UHFFFAOYSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- KOOBYHRLTYIPTH-UHFFFAOYSA-N methyl 3,5-diamino-6-chloropyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=C(N)N=C1N KOOBYHRLTYIPTH-UHFFFAOYSA-N 0.000 description 3
- ZRRKFICDIUCPIE-UHFFFAOYSA-N methyl 3-(benzylamino)-6-chloropyrazine-2-carboxylate Chemical compound C(C1=CC=CC=C1)NC=1C(=NC(=CN1)Cl)C(=O)OC ZRRKFICDIUCPIE-UHFFFAOYSA-N 0.000 description 3
- ZARHJADZMQHHQM-UHFFFAOYSA-N methyl 3-amino-5-(trifluoromethyl)pyrazine-2-carboxylate Chemical compound COC(=O)C1=NC=C(C(F)(F)F)N=C1N ZARHJADZMQHHQM-UHFFFAOYSA-N 0.000 description 3
- JFUCSIYDDKQAAT-UHFFFAOYSA-N methyl 3-bromo-6-chloro-5-(ethylamino)pyrazine-2-carboxylate Chemical compound CCNC1=NC(Br)=C(C(=O)OC)N=C1Cl JFUCSIYDDKQAAT-UHFFFAOYSA-N 0.000 description 3
- BYRBCXRBGPGOFL-UHFFFAOYSA-N methyl 6-chloro-3-[(4-chlorophenyl)methylamino]pyrazine-2-carboxylate Chemical compound ClC1=CC=C(CNC=2C(=NC(=CN2)Cl)C(=O)OC)C=C1 BYRBCXRBGPGOFL-UHFFFAOYSA-N 0.000 description 3
- NSMCAYXUTZQFCS-UHFFFAOYSA-N methyl 6-chloro-3-[(4-methoxyphenyl)methylamino]pyrazine-2-carboxylate Chemical compound COC1=CC=C(CNC=2C(=NC(=CN2)Cl)C(=O)OC)C=C1 NSMCAYXUTZQFCS-UHFFFAOYSA-N 0.000 description 3
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical class NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 description 3
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 description 2
- TZBHPYXJOJGKDT-UHFFFAOYSA-N 1,3-oxazin-4-one Chemical compound O=C1C=COC=N1 TZBHPYXJOJGKDT-UHFFFAOYSA-N 0.000 description 2
- GOLVGZOPWLLUSF-UHFFFAOYSA-N 1-ethylpyrrolidin-3-amine Chemical compound CCN1CCC(N)C1 GOLVGZOPWLLUSF-UHFFFAOYSA-N 0.000 description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- OZMUCSYTBBYNTK-UHFFFAOYSA-N 3-amino-5-(trifluoromethyl)pyrazine-2-carboxylic acid Chemical compound NC1=NC(C(F)(F)F)=CN=C1C(O)=O OZMUCSYTBBYNTK-UHFFFAOYSA-N 0.000 description 2
- NFSLHYFMCJZNRI-UHFFFAOYSA-N 3-amino-6-bromo-n-(2-morpholin-4-ylethyl)pyrazine-2-carboxamide Chemical compound NC1=NC=C(Br)N=C1C(=O)NCCN1CCOCC1 NFSLHYFMCJZNRI-UHFFFAOYSA-N 0.000 description 2
- GPIMZXJMWKALDA-UHFFFAOYSA-N 6-chloro-2-methylpyrazino[2,3-d][1,3]oxazin-4-one Chemical compound C1=C(Cl)N=C2C(=O)OC(C)=NC2=N1 GPIMZXJMWKALDA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- OKNXJFRSNAYEJQ-UHFFFAOYSA-N methyl 6-chloro-5-(ethylamino)-3-(2-methoxyethylamino)pyrazine-2-carboxylate Chemical compound COCCNC=1C(=NC(=C(N1)NCC)Cl)C(=O)OC OKNXJFRSNAYEJQ-UHFFFAOYSA-N 0.000 description 2
- IVKNUIVDQMARCO-UHFFFAOYSA-N oxazin-4-one Chemical compound O=C1C=CON=C1 IVKNUIVDQMARCO-UHFFFAOYSA-N 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JUFKJRCMBLLXNH-UHFFFAOYSA-N (1-methylpyrrolidin-2-yl)methanamine Chemical compound CN1CCCC1CN JUFKJRCMBLLXNH-UHFFFAOYSA-N 0.000 description 1
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 1
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 description 1
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
- KTHAOBTZABTOCS-UHFFFAOYSA-N 1-ethylpyrrolidin-2-amine Chemical compound CCN1CCCC1N KTHAOBTZABTOCS-UHFFFAOYSA-N 0.000 description 1
- IDBNECMSCRAUNU-UHFFFAOYSA-N 1-ethylpyrrolidin-3-ol Chemical compound CCN1CCC(O)C1 IDBNECMSCRAUNU-UHFFFAOYSA-N 0.000 description 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 1
- HEPPAPZASXFWTB-UHFFFAOYSA-N 3,3-dibromo-1,1,1-trifluoropropan-2-one Chemical compound FC(F)(F)C(=O)C(Br)Br HEPPAPZASXFWTB-UHFFFAOYSA-N 0.000 description 1
- RGUABPVONIGVAT-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propan-1-amine Chemical compound CN1CCN(CCCN)CC1 RGUABPVONIGVAT-UHFFFAOYSA-N 0.000 description 1
- VHJTYBBMITYNSU-UHFFFAOYSA-N 3-acetamidopyrazine-2-carboxamide Chemical class CC(=O)NC1=NC=CN=C1C(N)=O VHJTYBBMITYNSU-UHFFFAOYSA-N 0.000 description 1
- HQYQZNRBJGOWFW-UHFFFAOYSA-N 3-amino-6-benzylsulfanylpyrazine-2-carboxylic acid Chemical compound NC=1C(=NC(=CN1)SCC1=CC=CC=C1)C(=O)O HQYQZNRBJGOWFW-UHFFFAOYSA-N 0.000 description 1
- WDBPDIQNBCWYOY-UHFFFAOYSA-N 3-chloro-1-ethylpyrrolidine Chemical compound CCN1CCC(Cl)C1 WDBPDIQNBCWYOY-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- QORCUZKFFLYPSH-UHFFFAOYSA-N 4H-pyrazino[2,3-e]oxazin-3-one Chemical class C1=CN=C2ONC(=O)CC2=N1 QORCUZKFFLYPSH-UHFFFAOYSA-N 0.000 description 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 206010041277 Sodium retention Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XGISSQPLCGFZQW-UHFFFAOYSA-N methyl 2-amino-5-chloro-6-oxo-1h-pyrazine-3-carboxylate Chemical compound COC(=O)C=1N=C(Cl)C(=O)NC=1N XGISSQPLCGFZQW-UHFFFAOYSA-N 0.000 description 1
- QQALIOHMNFPVQU-UHFFFAOYSA-N methyl 3-amino-5-(azepan-1-yl)-6-chloropyrazine-2-carboxylate Chemical compound N1=C(N)C(C(=O)OC)=NC(Cl)=C1N1CCCCCC1 QQALIOHMNFPVQU-UHFFFAOYSA-N 0.000 description 1
- FLCZFLPPQOXHDF-UHFFFAOYSA-N methyl 3-amino-5-(benzylamino)-6-chloropyrazine-2-carboxylate Chemical compound N1=C(N)C(C(=O)OC)=NC(Cl)=C1NCC1=CC=CC=C1 FLCZFLPPQOXHDF-UHFFFAOYSA-N 0.000 description 1
- OVZBAPDKNOBBLW-UHFFFAOYSA-N methyl 3-amino-5-[amino(methyl)amino]-6-chloropyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(=C(N=C1N)N(N)C)Cl OVZBAPDKNOBBLW-UHFFFAOYSA-N 0.000 description 1
- QJGXKXOVHBBAQW-UHFFFAOYSA-N methyl 3-amino-5-anilino-6-chloropyrazine-2-carboxylate Chemical compound NC=1C(=NC(=C(N1)NC1=CC=CC=C1)Cl)C(=O)OC QJGXKXOVHBBAQW-UHFFFAOYSA-N 0.000 description 1
- DTBYHFIAYGJCQR-UHFFFAOYSA-N methyl 3-amino-5-cyclohexylpyrazine-2-carboxylate Chemical compound NC=1C(=NC=C(N1)C1CCCCC1)C(=O)OC DTBYHFIAYGJCQR-UHFFFAOYSA-N 0.000 description 1
- FIJWEFVSBHLUCL-UHFFFAOYSA-N methyl 3-amino-5-methylpyrazine-2-carboxylate Chemical compound COC(=O)C1=NC=C(C)N=C1N FIJWEFVSBHLUCL-UHFFFAOYSA-N 0.000 description 1
- GWSYTJJRDBPAKI-UHFFFAOYSA-N methyl 3-amino-5-phenylpyrazine-2-carboxylate Chemical compound N1=C(N)C(C(=O)OC)=NC=C1C1=CC=CC=C1 GWSYTJJRDBPAKI-UHFFFAOYSA-N 0.000 description 1
- CNXSIRHOIFRMOB-UHFFFAOYSA-N methyl 3-amino-6-bromopyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Br)=CN=C1N CNXSIRHOIFRMOB-UHFFFAOYSA-N 0.000 description 1
- UXJIDHYQEAVMTO-UHFFFAOYSA-N methyl 3-amino-6-chloro-5-(2,2,2-trifluoroethylamino)pyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=C(NCC(F)(F)F)N=C1N UXJIDHYQEAVMTO-UHFFFAOYSA-N 0.000 description 1
- ALPRBSDJHBOCNQ-UHFFFAOYSA-N methyl 3-amino-6-chloro-5-(4-methylpiperazin-1-yl)pyrazine-2-carboxylate Chemical compound N1=C(N)C(C(=O)OC)=NC(Cl)=C1N1CCN(C)CC1 ALPRBSDJHBOCNQ-UHFFFAOYSA-N 0.000 description 1
- ISXUSIRUFLPZRM-UHFFFAOYSA-N methyl 3-amino-6-chloro-5-(cyclopropylamino)pyrazine-2-carboxylate Chemical compound NC=1C(=NC(=C(N=1)NC1CC1)Cl)C(=O)OC ISXUSIRUFLPZRM-UHFFFAOYSA-N 0.000 description 1
- CIJAOZNANCPBRB-UHFFFAOYSA-N methyl 3-amino-6-chloro-5-(dimethylamino)pyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=C(N(C)C)N=C1N CIJAOZNANCPBRB-UHFFFAOYSA-N 0.000 description 1
- KRBPFWZEXJXVNU-UHFFFAOYSA-N methyl 3-amino-6-chloro-5-(ethylamino)pyrazine-2-carboxylate Chemical compound NC=1C(=NC(=C(N1)NCC)Cl)C(=O)OC KRBPFWZEXJXVNU-UHFFFAOYSA-N 0.000 description 1
- HQBNNWNATXSQHR-UHFFFAOYSA-N methyl 3-amino-6-chloro-5-(methylamino)pyrazine-2-carboxylate Chemical compound CNC1=NC(N)=C(C(=O)OC)N=C1Cl HQBNNWNATXSQHR-UHFFFAOYSA-N 0.000 description 1
- URPDFRRWOZWYHS-UHFFFAOYSA-N methyl 3-amino-6-chloro-5-(prop-2-ynylamino)pyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=C(NCC#C)N=C1N URPDFRRWOZWYHS-UHFFFAOYSA-N 0.000 description 1
- FQXZYTMQNZJAEN-UHFFFAOYSA-N methyl 3-amino-6-chloro-5-methylsulfanylpyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Cl)=C(SC)N=C1N FQXZYTMQNZJAEN-UHFFFAOYSA-N 0.000 description 1
- XWFBDHHUSDNXNJ-UHFFFAOYSA-N methyl 3-amino-6-chloro-5-pyrrolidin-1-ylpyrazine-2-carboxylate Chemical compound N1=C(N)C(C(=O)OC)=NC(Cl)=C1N1CCCC1 XWFBDHHUSDNXNJ-UHFFFAOYSA-N 0.000 description 1
- CUNYHDGUCFIXGF-UHFFFAOYSA-N methyl 3-amino-6-cyclohexylpyrazine-2-carboxylate Chemical compound NC=1C(=NC(=CN1)C1CCCCC1)C(=O)OC CUNYHDGUCFIXGF-UHFFFAOYSA-N 0.000 description 1
- FDLARAKNPMCCKJ-UHFFFAOYSA-N methyl 3-amino-6-iodopyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(I)=CN=C1N FDLARAKNPMCCKJ-UHFFFAOYSA-N 0.000 description 1
- VFKIJMHDBGWTIH-UHFFFAOYSA-N methyl 3-amino-6-methylpyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(C)=CN=C1N VFKIJMHDBGWTIH-UHFFFAOYSA-N 0.000 description 1
- RVVQRVZLKXYWAR-UHFFFAOYSA-N methyl 3-amino-6-phenylpyrazine-2-carboxylate Chemical compound N1=C(N)C(C(=O)OC)=NC(C=2C=CC=CC=2)=C1 RVVQRVZLKXYWAR-UHFFFAOYSA-N 0.000 description 1
- LUDBFTINYRPZDE-UHFFFAOYSA-N methyl 6-bromo-3-(dimethylamino)pyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(Br)=CN=C1N(C)C LUDBFTINYRPZDE-UHFFFAOYSA-N 0.000 description 1
- UKVSTTVEIRVEMS-UHFFFAOYSA-N methyl 6-bromo-3-(methylamino)pyrazine-2-carboxylate Chemical compound CNC1=NC=C(Br)N=C1C(=O)OC UKVSTTVEIRVEMS-UHFFFAOYSA-N 0.000 description 1
- XGMKPVLGFQAAOJ-UHFFFAOYSA-N methyl 6-bromo-3-piperidin-1-ylpyrazine-2-carboxylate Chemical compound N1(CCCCC1)C=1C(=NC(=CN1)Br)C(=O)OC XGMKPVLGFQAAOJ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- TXQWFIVRZNOPCK-UHFFFAOYSA-N pyridin-4-ylmethanamine Chemical compound NCC1=CC=NC=C1 TXQWFIVRZNOPCK-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000000894 saliuretic effect Effects 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000003396 thiol group Chemical class [H]S* 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US57344766A | 1966-08-17 | 1966-08-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH496713A true CH496713A (de) | 1970-09-30 |
Family
ID=24292032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH803767A CH496713A (de) | 1966-08-17 | 1967-06-07 | Verfahren zur Herstellung von Pyrazinamiden |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE699431A (enrdf_load_stackoverflow) |
| CH (1) | CH496713A (enrdf_load_stackoverflow) |
| DK (1) | DK116662B (enrdf_load_stackoverflow) |
| ES (1) | ES341317A1 (enrdf_load_stackoverflow) |
| FR (1) | FR6796M (enrdf_load_stackoverflow) |
| GB (1) | GB1181288A (enrdf_load_stackoverflow) |
| NL (1) | NL6707566A (enrdf_load_stackoverflow) |
| SE (1) | SE324367B (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1261335A (en) * | 1984-08-29 | 1989-09-26 | Hoffmann-La Roche Limited/Hoffmann-La Roche Limitee | Ethylenediamine monoamide derivatives |
| GB8810934D0 (en) * | 1987-05-26 | 1988-06-15 | Ici America Inc | Amides |
| GB8810933D0 (en) * | 1987-05-26 | 1988-06-15 | Ici America Inc | Heterocyclic compounds |
| GB8812342D0 (en) * | 1988-05-25 | 1988-06-29 | Ici America Inc | Bicyclic compounds |
| KR20180040699A (ko) * | 2015-08-20 | 2018-04-20 | 베링거 인겔하임 인터내셔날 게엠베하 | 신규한 어닐링된 벤즈아미드 |
-
1967
- 1967-05-31 NL NL6707566A patent/NL6707566A/xx unknown
- 1967-06-01 DK DK286667A patent/DK116662B/da unknown
- 1967-06-02 ES ES341317A patent/ES341317A1/es not_active Expired
- 1967-06-02 BE BE699431D patent/BE699431A/xx unknown
- 1967-06-07 GB GB2621067A patent/GB1181288A/en not_active Expired
- 1967-06-07 CH CH803767A patent/CH496713A/de not_active IP Right Cessation
- 1967-06-09 SE SE812567A patent/SE324367B/xx unknown
- 1967-09-04 FR FR119888A patent/FR6796M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6707566A (enrdf_load_stackoverflow) | 1968-02-19 |
| SE324367B (enrdf_load_stackoverflow) | 1970-06-01 |
| DK116662B (da) | 1970-02-02 |
| BE699431A (enrdf_load_stackoverflow) | 1967-12-04 |
| FR6796M (enrdf_load_stackoverflow) | 1969-03-17 |
| ES341317A1 (es) | 1968-10-01 |
| GB1181288A (en) | 1970-02-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |