SE410857B - Forfarande for framstellning av nya derivat av naftyridin - Google Patents
Forfarande for framstellning av nya derivat av naftyridinInfo
- Publication number
- SE410857B SE410857B SE7406452A SE7406452A SE410857B SE 410857 B SE410857 B SE 410857B SE 7406452 A SE7406452 A SE 7406452A SE 7406452 A SE7406452 A SE 7406452A SE 410857 B SE410857 B SE 410857B
- Authority
- SE
- Sweden
- Prior art keywords
- naphthyridin
- chloro
- carbon atoms
- prepared
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000005054 naphthyridines Chemical class 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- AKGSNUOZGBDODP-UHFFFAOYSA-N piperazine-1-carbonyl chloride Chemical compound ClC(=O)N1CCNCC1 AKGSNUOZGBDODP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 63
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- -1 alkali metal salt Chemical class 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 150000001875 compounds Chemical class 0.000 description 30
- 238000002844 melting Methods 0.000 description 23
- 230000008018 melting Effects 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 238000001914 filtration Methods 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- NULPJOMEXMOGEJ-UHFFFAOYSA-N O=C(OC1=CC=CC=C1)OC(C=C1CN2C3=NC4=NC(Cl)=CC=C4C=C3)=CC=C1C2=O Chemical compound O=C(OC1=CC=CC=C1)OC(C=C1CN2C3=NC4=NC(Cl)=CC=C4C=C3)=CC=C1C2=O NULPJOMEXMOGEJ-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- FBAIGEMWTOSCRU-UHFFFAOYSA-N 4-methylpiperazine-1-carbonyl chloride Chemical compound CN1CCN(C(Cl)=O)CC1 FBAIGEMWTOSCRU-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- CRADWWWVIYEAFR-UHFFFAOYSA-N 1,8-naphthyridin-2-amine Chemical compound C1=CC=NC2=NC(N)=CC=C21 CRADWWWVIYEAFR-UHFFFAOYSA-N 0.000 description 4
- NSPQTGOJGZXAJM-UHFFFAOYSA-N 7-amino-1h-1,8-naphthyridin-2-one Chemical compound C1=CC(=O)NC2=NC(N)=CC=C21 NSPQTGOJGZXAJM-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 4
- 229910000397 disodium phosphate Inorganic materials 0.000 description 4
- 235000019800 disodium phosphate Nutrition 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000001488 sodium phosphate Substances 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
- JUQWFONZRDXAAB-UHFFFAOYSA-N 1-methyl-1-oxidopiperazin-1-ium Chemical compound C[N+]1([O-])CCNCC1 JUQWFONZRDXAAB-UHFFFAOYSA-N 0.000 description 3
- UWERZJBLURGYFF-UHFFFAOYSA-N 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-3h-isoindol-1-one Chemical compound C1=CC(Cl)=NC2=NC(N3C(C4=CC=CC=C4C3=O)O)=CC=C21 UWERZJBLURGYFF-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- DBJNMMAUXLACNG-UHFFFAOYSA-N [6-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] phenyl carbonate Chemical compound C12=CC(Cl)=CC=C2C(=O)N(C=2N=C3N=C(Cl)C=CC3=CC=2)C1OC(=O)OC1=CC=CC=C1 DBJNMMAUXLACNG-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 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 description 3
- QBGUEJRWLZECIL-UHFFFAOYSA-N tert-butyl 4-methyl-4-oxidopiperazin-4-ium-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[N+](C)([O-])CC1 QBGUEJRWLZECIL-UHFFFAOYSA-N 0.000 description 3
- CJDYFMIDIQXELO-UHFFFAOYSA-N tert-butyl 4-methylpiperazine-1-carboxylate Chemical compound CN1CCN(C(=O)OC(C)(C)C)CC1 CJDYFMIDIQXELO-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- PVMNSAIKFPWDQG-UHFFFAOYSA-N 1-tert-butylpiperazine Chemical compound CC(C)(C)N1CCNCC1 PVMNSAIKFPWDQG-UHFFFAOYSA-N 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- HIYHXPYINQXNHU-UHFFFAOYSA-N 3-hydroxy-2-(1,8-naphthyridin-2-yl)-3h-isoindol-1-one Chemical compound C1=CC=NC2=NC(N3C(C4=CC=CC=C4C3=O)O)=CC=C21 HIYHXPYINQXNHU-UHFFFAOYSA-N 0.000 description 2
- RBRXXRAIVAAGGH-UHFFFAOYSA-N 3-hydroxy-2-(7-methyl-1,8-naphthyridin-2-yl)-3h-isoindol-1-one Chemical compound OC1C2=CC=CC=C2C(=O)N1C1=NC2=NC(C)=CC=C2C=C1 RBRXXRAIVAAGGH-UHFFFAOYSA-N 0.000 description 2
- BTTRMCQEPDPCPA-UHFFFAOYSA-N 4-chlorophthalic anhydride Chemical compound ClC1=CC=C2C(=O)OC(=O)C2=C1 BTTRMCQEPDPCPA-UHFFFAOYSA-N 0.000 description 2
- ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 4-nitrobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=C([N+]([O-])=O)C=C1 ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 0.000 description 2
- LDCOFKXSMUTNAB-UHFFFAOYSA-N 5-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-3h-isoindol-1-one Chemical compound C1=CC(Cl)=NC2=NC(N3C(C4=CC(Cl)=CC=C4C3=O)O)=CC=C21 LDCOFKXSMUTNAB-UHFFFAOYSA-N 0.000 description 2
- SWCFXQOKDPKZQD-UHFFFAOYSA-N 5-chloro-7a-(7-chloro-1,8-naphthyridin-2-yl)-3ah-isoindole-1,3-dione Chemical compound C1=CC(Cl)=NC2=NC(C34C(=O)NC(=O)C3C=C(C=C4)Cl)=CC=C21 SWCFXQOKDPKZQD-UHFFFAOYSA-N 0.000 description 2
- NIITWRNWQGFEPV-UHFFFAOYSA-N 5-chloro-7a-(7-oxo-8h-1,8-naphthyridin-2-yl)-3ah-isoindole-1,3-dione Chemical compound C1=CC(=O)NC2=NC(C34C(=O)NC(=O)C3C=C(C=C4)Cl)=CC=C21 NIITWRNWQGFEPV-UHFFFAOYSA-N 0.000 description 2
- NWVXRRVAIYVQLB-UHFFFAOYSA-N 7-(1,3-dioxo-7ah-isoindol-3a-yl)-1,8-naphthyridine-2-carbonitrile Chemical compound C1=CC(C#N)=NC2=NC(C34C(=O)NC(C3C=CC=C4)=O)=CC=C21 NWVXRRVAIYVQLB-UHFFFAOYSA-N 0.000 description 2
- XXRLVPWHPZUGAQ-UHFFFAOYSA-N 7-(1-hydroxy-3-oxo-1h-isoindol-2-yl)-1,8-naphthyridine-2-carbonitrile Chemical compound C1=CC(C#N)=NC2=NC(N3C(C4=CC=CC=C4C3=O)O)=CC=C21 XXRLVPWHPZUGAQ-UHFFFAOYSA-N 0.000 description 2
- WLEQWVIWIDRMKX-UHFFFAOYSA-N 7-methoxy-1,8-naphthyridin-2-amine Chemical compound C1=CC(N)=NC2=NC(OC)=CC=C21 WLEQWVIWIDRMKX-UHFFFAOYSA-N 0.000 description 2
- ZIFGWWCUONMOLI-UHFFFAOYSA-N 7-methyl-1,8-naphthyridin-2-amine Chemical compound C1=CC(N)=NC2=NC(C)=CC=C21 ZIFGWWCUONMOLI-UHFFFAOYSA-N 0.000 description 2
- IGRKVXUMVLAWJS-UHFFFAOYSA-N 7a-(7-bromo-1,8-naphthyridin-2-yl)-3ah-isoindole-1,3-dione Chemical compound C1=CC=CC2C(=O)NC(=O)C21C1=NC2=NC(Br)=CC=C2C=C1 IGRKVXUMVLAWJS-UHFFFAOYSA-N 0.000 description 2
- RJLATJCUBXLWQV-UHFFFAOYSA-N 7a-(7-chloro-1,8-naphthyridin-2-yl)-3ah-isoindole-1,3-dione Chemical compound C1=CC=CC2C(=O)NC(=O)C21C1=NC2=NC(Cl)=CC=C2C=C1 RJLATJCUBXLWQV-UHFFFAOYSA-N 0.000 description 2
- HTRFNCJOXVMBSF-UHFFFAOYSA-N 7a-(7-methoxy-1,8-naphthyridin-2-yl)-3ah-isoindole-1,3-dione Chemical compound C1=CC=CC2C(=O)NC(=O)C21C1=NC2=NC(OC)=CC=C2C=C1 HTRFNCJOXVMBSF-UHFFFAOYSA-N 0.000 description 2
- TXOYUYXQCCSRCM-UHFFFAOYSA-N 7a-(7-methyl-1,8-naphthyridin-2-yl)-3ah-isoindole-1,3-dione Chemical compound C1=CC=CC2C(=O)NC(=O)C21C1=NC2=NC(C)=CC=C2C=C1 TXOYUYXQCCSRCM-UHFFFAOYSA-N 0.000 description 2
- RMPKHFJYALJCOR-UHFFFAOYSA-N 7a-(7-oxo-8h-1,8-naphthyridin-2-yl)-3ah-isoindole-1,3-dione Chemical compound C1=CC(=O)NC2=NC(C34C(=O)NC(C3C=CC=C4)=O)=CC=C21 RMPKHFJYALJCOR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- ZLBJGPDQZPOCRP-UHFFFAOYSA-N [2-(1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] phenyl carbonate Chemical compound C=1C=C2C=CC=NC2=NC=1N1C(=O)C2=CC=CC=C2C1OC(=O)OC1=CC=CC=C1 ZLBJGPDQZPOCRP-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229950005228 bromoform Drugs 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 150000003949 imides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VIIPRKFEGDDHCU-UHFFFAOYSA-N n-(7-chloro-1,8-naphthyridin-2-yl)acetamide Chemical compound C1=CC(Cl)=NC2=NC(NC(=O)C)=CC=C21 VIIPRKFEGDDHCU-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- YKSVXVKIYYQWBB-UHFFFAOYSA-N 1-butylpiperazine Chemical compound CCCCN1CCNCC1 YKSVXVKIYYQWBB-UHFFFAOYSA-N 0.000 description 1
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
- ZWAQJGHGPPDZSF-UHFFFAOYSA-N 1-prop-2-enylpiperazine Chemical compound C=CCN1CCNCC1 ZWAQJGHGPPDZSF-UHFFFAOYSA-N 0.000 description 1
- GWCSATTUAOHJDK-UHFFFAOYSA-N 1-prop-2-ynylpiperazine Chemical compound C#CCN1CCNCC1 GWCSATTUAOHJDK-UHFFFAOYSA-N 0.000 description 1
- WHKWMTXTYKVFLK-UHFFFAOYSA-N 1-propan-2-ylpiperazine Chemical compound CC(C)N1CCNCC1 WHKWMTXTYKVFLK-UHFFFAOYSA-N 0.000 description 1
- NLNNRNIJRFYGFB-UHFFFAOYSA-N 5-hydroxy-2,3-dihydroisoindol-1-one Chemical compound OC1=CC=C2C(=O)NCC2=C1 NLNNRNIJRFYGFB-UHFFFAOYSA-N 0.000 description 1
- PFQITXIZEKDKRG-UHFFFAOYSA-N 6-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-3h-isoindol-1-one Chemical compound C1=CC(Cl)=NC2=NC(N3C(C4=CC=C(Cl)C=C4C3=O)O)=CC=C21 PFQITXIZEKDKRG-UHFFFAOYSA-N 0.000 description 1
- ZAAFDJAJRDALSO-UHFFFAOYSA-N 7a-(1,8-naphthyridin-2-yl)-3ah-isoindole-1,3-dione Chemical compound C1=CC=NC2=NC(C34C(=O)NC(C3C=CC=C4)=O)=CC=C21 ZAAFDJAJRDALSO-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Natural products O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- BYBHKYZZGFSRQE-UHFFFAOYSA-N [2-(1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] 4-methylpiperazine-1-carboxylate Chemical compound C1CN(C)CCN1C(=O)OC1C2=CC=CC=C2C(=O)N1C1=CC=C(C=CC=N2)C2=N1 BYBHKYZZGFSRQE-UHFFFAOYSA-N 0.000 description 1
- QETYPTHHDUOZTA-UHFFFAOYSA-N [2-(7-bromo-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] 4-methylpiperazine-1-carboxylate Chemical compound C1CN(C)CCN1C(=O)OC1C2=CC=CC=C2C(=O)N1C1=CC=C(C=CC(Br)=N2)C2=N1 QETYPTHHDUOZTA-UHFFFAOYSA-N 0.000 description 1
- UNSOABGSINKNCQ-UHFFFAOYSA-N [2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] 4-methylpiperazine-1-carboxylate Chemical compound C1CN(C)CCN1C(=O)OC1C2=CC=CC=C2C(=O)N1C1=CC=C(C=CC(Cl)=N2)C2=N1 UNSOABGSINKNCQ-UHFFFAOYSA-N 0.000 description 1
- ZESSRQSTYNMBBB-UHFFFAOYSA-N [2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] phenyl carbonate Chemical compound N=1C2=NC(Cl)=CC=C2C=CC=1N(C(C1=CC=CC=C11)=O)C1OC(=O)OC1=CC=CC=C1 ZESSRQSTYNMBBB-UHFFFAOYSA-N 0.000 description 1
- KDLRYXPXUQSJRY-UHFFFAOYSA-N [2-(7-cyano-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] 4-methylpiperazine-1-carboxylate Chemical compound C1CN(C)CCN1C(=O)OC1C2=CC=CC=C2C(=O)N1C1=CC=C(C=CC(=N2)C#N)C2=N1 KDLRYXPXUQSJRY-UHFFFAOYSA-N 0.000 description 1
- YRSCICITCAUSPR-UHFFFAOYSA-N [2-(7-fluoro-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] 4-methylpiperazine-1-carboxylate Chemical compound C1CN(C)CCN1C(=O)OC1C2=CC=CC=C2C(=O)N1C1=CC=C(C=CC(F)=N2)C2=N1 YRSCICITCAUSPR-UHFFFAOYSA-N 0.000 description 1
- AUJOVSASBXBMMJ-UHFFFAOYSA-N [2-(7-methyl-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] 4-methylpiperazine-1-carboxylate Chemical compound C1CN(C)CCN1C(=O)OC1C2=CC=CC=C2C(=O)N1C1=CC=C(C=CC(C)=N2)C2=N1 AUJOVSASBXBMMJ-UHFFFAOYSA-N 0.000 description 1
- ACABQFVNSCWRLW-UHFFFAOYSA-N [2-(7-methyl-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] phenyl carbonate Chemical compound N=1C2=NC(C)=CC=C2C=CC=1N(C(C1=CC=CC=C11)=O)C1OC(=O)OC1=CC=CC=C1 ACABQFVNSCWRLW-UHFFFAOYSA-N 0.000 description 1
- MMSOBSHGLQAIOD-UHFFFAOYSA-N [6-chloro-2-(7-chloro-1,8-naphthyridin-2-yl)-3-oxo-1h-isoindol-1-yl] 4-methylpiperazine-1-carboxylate Chemical compound C1CN(C)CCN1C(=O)OC1C2=CC(Cl)=CC=C2C(=O)N1C1=CC=C(C=CC(Cl)=N2)C2=N1 MMSOBSHGLQAIOD-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000002152 aqueous-organic solution Substances 0.000 description 1
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- DNGSHNXJZOYVGI-UHFFFAOYSA-N butyl-bis(2-chloroethyl)azanium;chloride Chemical compound Cl.CCCCN(CCCl)CCCl DNGSHNXJZOYVGI-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 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
- 238000011065 in-situ storage Methods 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000006742 locomotor activity Effects 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- SXPGFJZLDDFUHA-UHFFFAOYSA-N n,n-bis(2-chloroethyl)butan-1-amine Chemical compound CCCCN(CCCl)CCCl SXPGFJZLDDFUHA-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 238000011197 physicochemical method Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7317516A FR2229400A1 (en) | 1973-05-15 | 1973-05-15 | 2-(Naphthyridin-2-yl)-isoindolin-1-one derivs - contg. 3-(piperazin-1-yl-carbonyloxy) gp., used as tranquillisers and antidepressants |
| FR7408728A FR2286642A2 (fr) | 1974-03-14 | 1974-03-14 | Nouveaux derives de l'isoindoline, leur preparation et les compositions qui les contiennent |
| FR7408730A FR2263752A1 (en) | 1974-03-14 | 1974-03-14 | 1,8-Naphthyridine derivs - tranquillizers and anti-convulsants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE410857B true SE410857B (sv) | 1979-11-12 |
Family
ID=27250114
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7406452A SE410857B (sv) | 1973-05-15 | 1974-05-14 | Forfarande for framstellning av nya derivat av naftyridin |
Country Status (23)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS537455B1 (enrdf_load_stackoverflow) * | 1971-02-01 | 1978-03-17 | ||
| FR2324305A2 (fr) * | 1975-09-22 | 1977-04-15 | Rhone Poulenc Ind | Nouveaux derives de l'isoindoline, leur preparation et les compositions qui les contiennent |
| AR208414A1 (es) * | 1974-11-07 | 1976-12-27 | Rhone Poulenc Ind | Procedimiento para obtener nuevos derivados de la((acil-4piperazinil-1)carboniloxi-5 pirrolinona-2) |
| FR2322600A1 (fr) * | 1975-09-04 | 1977-04-01 | Rhone Poulenc Ind | Nouveaux derives de la pyrrolo (3,4-b) pyrazine, leur preparation et les compositions qui les contiennent |
| OA05287A (fr) * | 1975-04-07 | 1981-02-28 | Rhone Poulenc Ind | Nouveaux composés hétérocycliques et leur préparation. |
| JPS5546257A (en) * | 1978-09-27 | 1980-03-31 | Hitachi Cable | Flame retardant cable |
| JPS5546256A (en) * | 1978-09-27 | 1980-03-31 | Hitachi Cable | Flame retardant insulated wire |
| JPS63191981U (enrdf_load_stackoverflow) * | 1987-05-30 | 1988-12-09 | ||
| RO115159B1 (ro) * | 1995-01-11 | 1999-11-30 | Samjin Pharmaceutical Co., Ltd | Derivaţi de piperazină şi compoziţii farmaceutice care îi conţin |
| PL325341A1 (en) * | 1996-06-29 | 1998-07-20 | Samjin Pharmaceutical Co | Derivatives od piperazine and method of obtaining them |
-
1974
- 1974-04-29 OA OA55189A patent/OA04700A/xx unknown
- 1974-04-30 PH PH15794A patent/PH11400A/en unknown
- 1974-05-08 NL NL7406194A patent/NL7406194A/xx not_active Application Discontinuation
- 1974-05-13 GB GB2108174A patent/GB1417935A/en not_active Expired
- 1974-05-13 IE IE1012/74A patent/IE39263B1/xx unknown
- 1974-05-13 IL IL44815A patent/IL44815A/en unknown
- 1974-05-13 HU HURO780A patent/HU169609B/hu unknown
- 1974-05-13 JP JP49052378A patent/JPS5758345B2/ja not_active Expired
- 1974-05-14 SE SE7406452A patent/SE410857B/sv not_active IP Right Cessation
- 1974-05-14 SU SU7402026597A patent/SU583757A3/ru active
- 1974-05-14 LU LU70071A patent/LU70071A1/xx unknown
- 1974-05-14 ES ES426336A patent/ES426336A1/es not_active Expired
- 1974-05-14 DD DD178499A patent/DD111078A5/xx unknown
- 1974-05-14 CH CH659574A patent/CH592662A5/xx not_active IP Right Cessation
- 1974-05-14 NO NO741744A patent/NO140012C/no unknown
- 1974-05-14 DK DK263374AA patent/DK136819B/da not_active IP Right Cessation
- 1974-05-14 CH CH53477A patent/CH592663A5/xx not_active IP Right Cessation
- 1974-05-14 ES ES426335A patent/ES426335A1/es not_active Expired
- 1974-05-15 YU YU01336/74A patent/YU133674A/xx unknown
- 1974-05-15 AT AT400874A patent/AT336030B/de not_active IP Right Cessation
- 1974-05-15 CS CS743472A patent/CS191881B2/cs unknown
- 1974-05-15 DE DE2423650A patent/DE2423650A1/de not_active Withdrawn
- 1974-05-15 FI FI1498/74A patent/FI55659C/fi active
- 1974-05-15 PL PL1974171103A patent/PL90061B1/pl unknown
- 1974-05-15 AR AR253755A patent/AR209421A1/es active
-
1975
- 1975-01-29 AR AR257458A patent/AR210851A1/es active
- 1975-03-18 SU SU752112823A patent/SU589916A3/ru active
-
1981
- 1981-12-08 YU YU02877/81A patent/YU287781A/xx unknown
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| JPS6160832B2 (enrdf_load_stackoverflow) |
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