FI58126C - Foerfarande foer framstaellning av kardiotona och blodtryckssaenkande 2-fenyl-1h-imidatso(4,5-b)pyridiner - Google Patents
Foerfarande foer framstaellning av kardiotona och blodtryckssaenkande 2-fenyl-1h-imidatso(4,5-b)pyridiner Download PDFInfo
- Publication number
- FI58126C FI58126C FI3989/73A FI398973A FI58126C FI 58126 C FI58126 C FI 58126C FI 3989/73 A FI3989/73 A FI 3989/73A FI 398973 A FI398973 A FI 398973A FI 58126 C FI58126 C FI 58126C
- Authority
- FI
- Finland
- Prior art keywords
- phenyl
- imidazo
- methoxy
- pyridine
- group
- Prior art date
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- -1 methylamino, dimethylamino, morpholino Chemical group 0.000 claims description 143
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 98
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000005336 allyloxy group Chemical group 0.000 claims description 3
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 230000003177 cardiotonic effect Effects 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003222 pyridines Chemical class 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
- 239000006188 syrup Substances 0.000 claims 1
- 235000020357 syrup Nutrition 0.000 claims 1
- 238000002844 melting Methods 0.000 description 201
- 230000008018 melting Effects 0.000 description 201
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 118
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 109
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 99
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 70
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 62
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 32
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 30
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
- GPVDHNVGGIAOQT-UHFFFAOYSA-N 2,4-dimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OC)=C1 GPVDHNVGGIAOQT-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 238000010992 reflux Methods 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- ZAFBRSZVPHJXGB-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-1h-imidazo[4,5-b]pyridine;hydrochloride Chemical compound Cl.COC1=CC(OC)=CC=C1C1=NC2=NC=CC=C2N1 ZAFBRSZVPHJXGB-UHFFFAOYSA-N 0.000 description 16
- 229910021529 ammonia Inorganic materials 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 15
- 238000001816 cooling Methods 0.000 description 15
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 14
- 239000012362 glacial acetic acid Substances 0.000 description 14
- 229960004592 isopropanol Drugs 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 239000012071 phase Substances 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 11
- 230000008020 evaporation Effects 0.000 description 11
- ILUJQPXNXACGAN-UHFFFAOYSA-N O-methylsalicylic acid Chemical compound COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- DRTZAIDVOGUYSP-UHFFFAOYSA-N pyridin-1-ium;chloride;hydrochloride Chemical compound Cl.Cl.C1=CC=NC=C1 DRTZAIDVOGUYSP-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 6
- MEQBJJUWDCYIAB-UHFFFAOYSA-N 2-chloropyridin-3-amine Chemical compound NC1=CC=CN=C1Cl MEQBJJUWDCYIAB-UHFFFAOYSA-N 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
- YKILTKQGVVJNPD-UHFFFAOYSA-N 2-[4-(3-chloropropoxy)-2-methoxyphenyl]-1h-imidazo[4,5-b]pyridine;hydrochloride Chemical compound Cl.COC1=CC(OCCCCl)=CC=C1C1=NC2=NC=CC=C2N1 YKILTKQGVVJNPD-UHFFFAOYSA-N 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QLAJNZSPVITUCQ-UHFFFAOYSA-N 1,3,2-dioxathietane 2,2-dioxide Chemical compound O=S1(=O)OCO1 QLAJNZSPVITUCQ-UHFFFAOYSA-N 0.000 description 4
- UMXBATVGSBGWII-UHFFFAOYSA-N 2-methylsulfanyl-1,3-dithiolane Chemical compound CSC1SCCS1 UMXBATVGSBGWII-UHFFFAOYSA-N 0.000 description 4
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000009090 positive inotropic effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- XQRDAEMFUZSXOO-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC(OC)=CC=C1C1=NC2=NC=CC=C2N1 XQRDAEMFUZSXOO-UHFFFAOYSA-N 0.000 description 3
- LXMALGKMQWWXOS-UHFFFAOYSA-N 2-[2-(2-chloroethoxy)-4-methoxyphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound ClCCOC1=CC(OC)=CC=C1C1=NC2=NC=CC=C2N1 LXMALGKMQWWXOS-UHFFFAOYSA-N 0.000 description 3
- GTUZKGFHWANOGV-UHFFFAOYSA-N 2-[2-(3-chloropropoxy)-4-methoxyphenyl]-1h-imidazo[4,5-b]pyridine Chemical compound ClCCCOC1=CC(OC)=CC=C1C1=NC2=NC=CC=C2N1 GTUZKGFHWANOGV-UHFFFAOYSA-N 0.000 description 3
- FIBUUFSNPAKRQH-UHFFFAOYSA-N 2-[2-(3-chloropropoxy)-4-methoxyphenyl]-1h-imidazo[4,5-b]pyridine;hydrochloride Chemical compound Cl.ClCCCOC1=CC(OC)=CC=C1C1=NC2=NC=CC=C2N1 FIBUUFSNPAKRQH-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
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000009835 boiling Methods 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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- WLYUBJCCNATTIS-UHFFFAOYSA-N n-(4-chlorophenyl)-2,4-dimethoxybenzamide Chemical compound COC1=CC(OC)=CC=C1C(=O)NC1=CC=C(Cl)C=C1 WLYUBJCCNATTIS-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- XQZNKJRFTGYVDR-UHFFFAOYSA-N (2,4-dimethoxyphenyl)-morpholin-4-ylmethanone Chemical compound COC1=CC(OC)=CC=C1C(=O)N1CCOCC1 XQZNKJRFTGYVDR-UHFFFAOYSA-N 0.000 description 2
- ADHQUNYXOLRGJQ-UHFFFAOYSA-N (2,5-dimethoxyphenyl)-morpholin-4-ylmethanethione Chemical compound COC1=CC=C(OC)C(C(=S)N2CCOCC2)=C1 ADHQUNYXOLRGJQ-UHFFFAOYSA-N 0.000 description 2
- OECXXBUSZDYBMV-UHFFFAOYSA-N (2-hydroxy-4-methoxyphenyl)-morpholin-4-ylmethanone Chemical compound OC1=CC(OC)=CC=C1C(=O)N1CCOCC1 OECXXBUSZDYBMV-UHFFFAOYSA-N 0.000 description 2
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
- FRZIFMKSYWAOSE-UHFFFAOYSA-N 1h-imidazo[4,5-b]pyridine;hydrochloride Chemical compound Cl.C1=CC=C2NC=NC2=N1 FRZIFMKSYWAOSE-UHFFFAOYSA-N 0.000 description 2
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 2
- MBIZFBDREVRUHY-UHFFFAOYSA-N 2,6-Dimethoxybenzoic acid Chemical compound COC1=CC=CC(OC)=C1C(O)=O MBIZFBDREVRUHY-UHFFFAOYSA-N 0.000 description 2
- XLYKYZQEKDEJKG-UHFFFAOYSA-N 2-(2,4,5-trimethoxyphenyl)-1,3-dithiolan-1-ium iodide Chemical compound [I-].COC1=C(C=C(C(=C1)OC)OC)C1[SH+]CCS1 XLYKYZQEKDEJKG-UHFFFAOYSA-N 0.000 description 2
- IAVIKOCDVQVIOF-UHFFFAOYSA-N 2-(2,4,5-trimethoxyphenyl)-1H-imidazo[4,5-b]pyridine hydrochloride Chemical compound Cl.COC1=C(C=C(C(=C1)OC)OC)C=1NC=2C(=NC=CC2)N1 IAVIKOCDVQVIOF-UHFFFAOYSA-N 0.000 description 2
- KJLBOVOZDLZTPV-UHFFFAOYSA-N 2-(2,4,6-trimethoxyphenyl)-1H-imidazo[4,5-b]pyridine hydrochloride Chemical compound Cl.COC1=C(C(=CC(=C1)OC)OC)C=1NC=2C(=NC=CC2)N1 KJLBOVOZDLZTPV-UHFFFAOYSA-N 0.000 description 2
- WTLSGGNAGIQOPF-UHFFFAOYSA-N 2-(2,5-dimethoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound COC1=CC=C(OC)C(C=2NC3=NC=CC=C3N=2)=C1 WTLSGGNAGIQOPF-UHFFFAOYSA-N 0.000 description 2
- AUVVMEHKSWBYCT-UHFFFAOYSA-N 2-(2-fluoro-5-methylsulfanylphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound CSC1=CC=C(F)C(C=2NC3=CC=CN=C3N=2)=C1 AUVVMEHKSWBYCT-UHFFFAOYSA-N 0.000 description 2
- GHNMQHAPKQYWCU-UHFFFAOYSA-N 2-(3,4,5-trimethoxyphenyl)-1h-imidazo[4,5-b]pyridine Chemical compound COC1=C(OC)C(OC)=CC(C=2NC3=CC=CN=C3N=2)=C1 GHNMQHAPKQYWCU-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- CIGPWXUOWOGBDU-UHFFFAOYSA-N 2-[2-(2-chloroethoxy)-4-methoxyphenyl]-1h-imidazo[4,5-b]pyridine;hydrochloride Chemical compound Cl.ClCCOC1=CC(OC)=CC=C1C1=NC2=NC=CC=C2N1 CIGPWXUOWOGBDU-UHFFFAOYSA-N 0.000 description 2
- IWCMLFNLLPSVLQ-UHFFFAOYSA-N 2-[2-(3-ethylsulfanylpropoxy)-4-methoxyphenyl]-1h-imidazo[4,5-b]pyridine;hydrochloride Chemical compound Cl.CCSCCCOC1=CC(OC)=CC=C1C1=NC2=NC=CC=C2N1 IWCMLFNLLPSVLQ-UHFFFAOYSA-N 0.000 description 2
- NVVWLGVECJYTDY-UHFFFAOYSA-N 2-[4-(2-ethylsulfanylethoxy)-2-methoxyphenyl]-1h-imidazo[4,5-b]pyridine;hydrochloride Chemical compound Cl.COC1=CC(OCCSCC)=CC=C1C1=NC2=NC=CC=C2N1 NVVWLGVECJYTDY-UHFFFAOYSA-N 0.000 description 2
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- 239000012024 dehydrating agents Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- UNIWZWQHMHLZSG-UHFFFAOYSA-N hydron;2-(2-methoxy-4-methylsulfanylphenyl)-1h-imidazo[4,5-b]pyridine;chloride Chemical compound Cl.COC1=CC(SC)=CC=C1C1=NC2=NC=CC=C2N1 UNIWZWQHMHLZSG-UHFFFAOYSA-N 0.000 description 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 239000007937 lozenge 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
- WREDNSAXDZCLCP-UHFFFAOYSA-N methanedithioic acid Chemical compound SC=S WREDNSAXDZCLCP-UHFFFAOYSA-N 0.000 description 1
- IHIJFZWLGPEYPJ-UHFFFAOYSA-N methyl 2,4-dimethoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C=C1OC IHIJFZWLGPEYPJ-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- 229960002275 pentobarbital sodium Drugs 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- IXHWPHKAIWPAKX-UHFFFAOYSA-N pyridine;trihydrochloride Chemical compound Cl.Cl.Cl.C1=CC=NC=C1 IXHWPHKAIWPAKX-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000001391 thioamide group Chemical group 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- WKOLLVMJNQIZCI-UHFFFAOYSA-N vanillic acid Chemical compound COC1=CC(C(O)=O)=CC=C1O WKOLLVMJNQIZCI-UHFFFAOYSA-N 0.000 description 1
- TUUBOHWZSQXCSW-UHFFFAOYSA-N vanillic acid Natural products COC1=CC(O)=CC(C(O)=O)=C1 TUUBOHWZSQXCSW-UHFFFAOYSA-N 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- 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
- C07D295/18—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 carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
-
- 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
- C07D295/18—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 carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/194—Radicals derived from thio- or thiono carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2305339A DE2305339C3 (de) | 1973-02-03 | 1973-02-03 | Imidazo [4,5-b] pyridine, ihre Herstellung und ihre Verwendung als Cardiötonica |
| DE2305339 | 1973-02-03 | ||
| DE2361757 | 1973-12-12 | ||
| DE2361757A DE2361757A1 (de) | 1973-12-12 | 1973-12-12 | Neue imidazo eckige klammer auf 4,5-b eckige klammer zu pyridine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI58126B FI58126B (fi) | 1980-08-29 |
| FI58126C true FI58126C (fi) | 1980-12-10 |
Family
ID=25764640
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI3989/73A FI58126C (fi) | 1973-02-03 | 1973-12-27 | Foerfarande foer framstaellning av kardiotona och blodtryckssaenkande 2-fenyl-1h-imidatso(4,5-b)pyridiner |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS5748556B2 (ro) |
| AT (1) | AT332873B (ro) |
| BG (1) | BG23902A3 (ro) |
| CA (1) | CA1041502A (ro) |
| CH (1) | CH605939A5 (ro) |
| CS (1) | CS200169B2 (ro) |
| DD (1) | DD108989A5 (ro) |
| DK (1) | DK140760B (ro) |
| ES (1) | ES422450A1 (ro) |
| FI (1) | FI58126C (ro) |
| FR (1) | FR2215968B1 (ro) |
| GB (1) | GB1445824A (ro) |
| HK (1) | HK4080A (ro) |
| HU (1) | HU170909B (ro) |
| IE (1) | IE39066B1 (ro) |
| IL (1) | IL44127A (ro) |
| NL (1) | NL173645C (ro) |
| NO (1) | NO139386C (ro) |
| PH (1) | PH14988A (ro) |
| PL (1) | PL93127B1 (ro) |
| RO (2) | RO84276B (ro) |
| SE (1) | SE411451B (ro) |
| SU (2) | SU563917A3 (ro) |
| YU (2) | YU36955B (ro) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49109394A (ro) * | 1973-02-27 | 1974-10-17 | ||
| DE3132754A1 (de) * | 1981-08-19 | 1983-03-03 | Merck Patent Gmbh, 6100 Darmstadt | "2-aryl-imidazo(4,5-b)pyridine, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung" |
| ES8401486A1 (es) * | 1981-11-10 | 1983-12-01 | Wellcome Found | Un procedimiento para la preparacion de nuevos derivados de imidazo (4,5-c)piridina. |
| ZA832938B (en) * | 1982-05-03 | 1984-12-24 | Lilly Co Eli | 2-phenylimidazo(4,5-c)pyridines |
| US4772600A (en) * | 1986-06-09 | 1988-09-20 | A. H. Robins Company, Inc. | Fused imidazoheterocyclic compounds and pharmaceutical compositions |
| JPH01190663A (ja) * | 1988-01-22 | 1989-07-31 | Terumo Corp | システアミン誘導体及びこれを含有する抗リウマチ剤 |
| US6653309B1 (en) | 1999-04-26 | 2003-11-25 | Vertex Pharmaceuticals Incorporated | Inhibitors of IMPDH enzyme technical field of the invention |
| US9273027B2 (en) | 2010-02-24 | 2016-03-01 | Research Triangle Institute | Arylpiperazine opioid receptor antagonists |
| BR122019003178B1 (pt) * | 2010-12-24 | 2020-04-28 | Sumitomo Chemical Co | método de controle de pestes |
| WO2013191189A1 (ja) * | 2012-06-21 | 2013-12-27 | 住友化学株式会社 | 縮合複素環化合物 |
| CN104395300A (zh) | 2012-06-22 | 2015-03-04 | 住友化学株式会社 | 稠合杂环化合物 |
-
1973
- 1973-12-27 FI FI3989/73A patent/FI58126C/fi active
-
1974
- 1974-01-10 AT AT16474*#A patent/AT332873B/de not_active IP Right Cessation
- 1974-01-19 ES ES422450A patent/ES422450A1/es not_active Expired
- 1974-01-23 CS CS74443A patent/CS200169B2/cs unknown
- 1974-01-23 BG BG025577A patent/BG23902A3/xx unknown
- 1974-01-24 YU YU0176/74A patent/YU36955B/xx unknown
- 1974-01-29 SU SU7401990335A patent/SU563917A3/ru active
- 1974-01-30 NL NLAANVRAGE7401254,A patent/NL173645C/xx not_active IP Right Cessation
- 1974-01-31 CH CH136374A patent/CH605939A5/xx not_active IP Right Cessation
- 1974-01-31 RO RO106042A patent/RO84276B/ro unknown
- 1974-01-31 RO RO7477478A patent/RO79057A/ro unknown
- 1974-02-01 DD DD176324A patent/DD108989A5/xx unknown
- 1974-02-01 DK DK56374AA patent/DK140760B/da not_active IP Right Cessation
- 1974-02-01 IL IL44127A patent/IL44127A/en unknown
- 1974-02-01 IE IE195/74A patent/IE39066B1/en unknown
- 1974-02-01 SE SE7401393A patent/SE411451B/xx unknown
- 1974-02-01 FR FR7403491A patent/FR2215968B1/fr not_active Expired
- 1974-02-01 JP JP49013568A patent/JPS5748556B2/ja not_active Expired
- 1974-02-01 GB GB480874A patent/GB1445824A/en not_active Expired
- 1974-02-01 NO NO740327A patent/NO139386C/no unknown
- 1974-02-01 HU HU74TO00000951A patent/HU170909B/hu unknown
- 1974-02-01 CA CA191,585A patent/CA1041502A/en not_active Expired
- 1974-02-02 PL PL1974168533A patent/PL93127B1/pl unknown
-
1975
- 1975-08-27 SU SU752170503A patent/SU634673A3/ru active
-
1976
- 1976-05-25 PH PH18455A patent/PH14988A/en unknown
-
1980
- 1980-01-31 HK HK40/80A patent/HK4080A/xx unknown
- 1980-04-22 YU YU1104/80A patent/YU36956B/xx unknown
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