FI58131C - Foerfarande foer framstaellning av terapeutiskt vaerdefulla ampicillinderivat - Google Patents
Foerfarande foer framstaellning av terapeutiskt vaerdefulla ampicillinderivat Download PDFInfo
- Publication number
- FI58131C FI58131C FI1458/73A FI145873A FI58131C FI 58131 C FI58131 C FI 58131C FI 1458/73 A FI1458/73 A FI 1458/73A FI 145873 A FI145873 A FI 145873A FI 58131 C FI58131 C FI 58131C
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- FI
- Finland
- Prior art keywords
- solution
- group
- mixture
- dichloromethane
- added
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- 238000000034 method Methods 0.000 title claims description 9
- 230000001225 therapeutic effect Effects 0.000 title 1
- -1 methoxy, ethoxy, methylthio Chemical group 0.000 claims description 102
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical class C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 41
- 229960000723 ampicillin Drugs 0.000 claims description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000006239 protecting group Chemical group 0.000 claims description 10
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004043 oxo group Chemical group 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
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 322
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 165
- 239000000243 solution Substances 0.000 description 163
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 144
- 239000000203 mixture Substances 0.000 description 121
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 68
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 60
- 239000013078 crystal Substances 0.000 description 55
- 239000002244 precipitate Substances 0.000 description 51
- 238000003756 stirring Methods 0.000 description 49
- 238000001914 filtration Methods 0.000 description 43
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 40
- 238000002844 melting Methods 0.000 description 38
- 230000008018 melting Effects 0.000 description 38
- 150000001408 amides Chemical class 0.000 description 37
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- 238000002329 infrared spectrum Methods 0.000 description 34
- 229940056360 penicillin g Drugs 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 150000007942 carboxylates Chemical class 0.000 description 32
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 32
- 239000000725 suspension Substances 0.000 description 31
- 229960003311 ampicillin trihydrate Drugs 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000007795 chemical reaction product Substances 0.000 description 26
- 150000002576 ketones Chemical class 0.000 description 23
- 150000001875 compounds Chemical class 0.000 description 22
- 239000005457 ice water Substances 0.000 description 22
- 150000003952 β-lactams Chemical class 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000001816 cooling Methods 0.000 description 21
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 19
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 19
- 235000019341 magnesium sulphate Nutrition 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 18
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 17
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 16
- 239000000706 filtrate Substances 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 14
- 235000019371 penicillin G benzathine Nutrition 0.000 description 13
- 239000012071 phase Substances 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 8
- 239000011780 sodium chloride Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 241000894006 Bacteria Species 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 5
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000001226 reprecipitation Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
- ORASOOKDQIQMDZ-UHFFFAOYSA-N 4-hydroxy-6-oxo-1h-pyridine-3-carboxamide Chemical compound NC(=O)C1=CN=C(O)C=C1O ORASOOKDQIQMDZ-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 229930182555 Penicillin Natural products 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229940049954 penicillin Drugs 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- BNQAGSFYJKPXBR-GFCCVEGCSA-N (2R)-2-[(4-hydroxy-6-oxo-1H-pyridine-3-carbonyl)amino]-2-phenylacetic acid Chemical compound N([C@@H](C(=O)O)C=1C=CC=CC=1)C(=O)C1=CN=C(O)C=C1O BNQAGSFYJKPXBR-GFCCVEGCSA-N 0.000 description 2
- AVKUERGKIZMTKX-YXLKDIQASA-N (2s,5r)-6-[(2-amino-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound C1([C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)NC(=O)C(N)C1=CC=CC=C1 AVKUERGKIZMTKX-YXLKDIQASA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 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
- WCYWWSXYAZERCV-UHFFFAOYSA-N 4-chloro-5-methoxypyridine-2-carbonyl chloride;hydrochloride Chemical compound Cl.COC1=CN=C(C(Cl)=O)C=C1Cl WCYWWSXYAZERCV-UHFFFAOYSA-N 0.000 description 2
- CGRRUFNHHQCLDZ-UHFFFAOYSA-N 5-hydroxypyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(O)C=N1 CGRRUFNHHQCLDZ-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 241000589516 Pseudomonas Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 238000010306 acid treatment Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 230000020477 pH reduction Effects 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 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
- 239000000376 reactant Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZSEJADLCFCHIGX-UHFFFAOYSA-N 1-ethyl-4-oxoquinoline-3-carboxylic acid Chemical compound C1=CC=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 ZSEJADLCFCHIGX-UHFFFAOYSA-N 0.000 description 1
- FGFJOULNUAEAAQ-UHFFFAOYSA-N 1-ethyl-7-methyl-1,8-naphthyridin-4-one Chemical compound C1=C(C)N=C2N(CC)C=CC(=O)C2=C1 FGFJOULNUAEAAQ-UHFFFAOYSA-N 0.000 description 1
- ZGLHYUCKHXCQKM-UHFFFAOYSA-N 2-(dimethylamino)-4-oxo-3H-quinoline-3-carbonyl chloride Chemical compound CN(C)C1=NC2=CC=CC=C2C(C1C(=O)Cl)=O ZGLHYUCKHXCQKM-UHFFFAOYSA-N 0.000 description 1
- UEYQJQVBUVAELZ-UHFFFAOYSA-N 2-Hydroxynicotinic acid Chemical compound OC(=O)C1=CC=CN=C1O UEYQJQVBUVAELZ-UHFFFAOYSA-N 0.000 description 1
- ZJLWYBVHSLSSCN-UHFFFAOYSA-N 2-[(4-oxo-1h-pyridine-3-carbonyl)amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NC(=O)C1=CNC=CC1=O ZJLWYBVHSLSSCN-UHFFFAOYSA-N 0.000 description 1
- BXHCJLRTXPHUGH-UHFFFAOYSA-N 2-oxo-1h-pyridine-4-carboxylic acid Chemical compound OC(=O)C=1C=CNC(=O)C=1 BXHCJLRTXPHUGH-UHFFFAOYSA-N 0.000 description 1
- SIHMMTANWQXEHE-UHFFFAOYSA-N 2-oxo-5-phenyl-1h-pyridine-3-carboxylic acid Chemical compound N1C(=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1 SIHMMTANWQXEHE-UHFFFAOYSA-N 0.000 description 1
- HJQLQTVZSPAUGT-UHFFFAOYSA-N 4-chloropyridine-2-carbonyl chloride;hydrochloride Chemical compound Cl.ClC(=O)C1=CC(Cl)=CC=N1 HJQLQTVZSPAUGT-UHFFFAOYSA-N 0.000 description 1
- KYBAJHSBLMJOTJ-UHFFFAOYSA-N 4-chloropyridine-3-carbonyl chloride;hydrochloride Chemical compound Cl.ClC(=O)C1=CN=CC=C1Cl KYBAJHSBLMJOTJ-UHFFFAOYSA-N 0.000 description 1
- SCCSALTVILWDAC-UHFFFAOYSA-N 4-hydroxy-6-oxo-1h-pyridine-3-carbonyl azide Chemical compound OC1=CC(=O)C(C(=O)N=[N+]=[N-])=CN1 SCCSALTVILWDAC-UHFFFAOYSA-N 0.000 description 1
- QJLHSJRQOWSNMD-UHFFFAOYSA-N 4-hydroxy-6-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CNC(O)=CC1=O QJLHSJRQOWSNMD-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- MXXLHBCSVDDTIX-UHFFFAOYSA-N 4-oxo-1h-pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC(O)=CC=N1 MXXLHBCSVDDTIX-UHFFFAOYSA-N 0.000 description 1
- HXDFIFKXAVCLJS-UHFFFAOYSA-N 4-oxo-1h-pyridine-3-carbonyl chloride Chemical compound OC1=CC=NC=C1C(Cl)=O HXDFIFKXAVCLJS-UHFFFAOYSA-N 0.000 description 1
- CHCUBGPSZDGABM-UHFFFAOYSA-N 4-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CNC=CC1=O CHCUBGPSZDGABM-UHFFFAOYSA-N 0.000 description 1
- ILNJBIQQAIIMEY-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=C(O)C(C(=O)O)=CN=C21 ILNJBIQQAIIMEY-UHFFFAOYSA-N 0.000 description 1
- ASXFTGFWMQJKMS-UHFFFAOYSA-N 5-methoxy-4-oxo-1h-pyridine-2-carboxylic acid Chemical compound COC1=CNC(C(O)=O)=CC1=O ASXFTGFWMQJKMS-UHFFFAOYSA-N 0.000 description 1
- VRCWSYYXUCKEED-UHFFFAOYSA-N 6-Hydroxypicolinic acid Chemical compound OC(=O)C1=CC=CC(=O)N1 VRCWSYYXUCKEED-UHFFFAOYSA-N 0.000 description 1
- DFGKGUXTPFWHIX-UHFFFAOYSA-N 6-[2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]acetyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)C1=CC2=C(NC(O2)=O)C=C1 DFGKGUXTPFWHIX-UHFFFAOYSA-N 0.000 description 1
- AZPRIZBZQGJFGG-UHFFFAOYSA-N 6-ethoxy-4-oxo-3h-quinoline-3-carboxylic acid Chemical compound N1=CC(C(O)=O)C(=O)C2=CC(OCC)=CC=C21 AZPRIZBZQGJFGG-UHFFFAOYSA-N 0.000 description 1
- BLHCMGRVFXRYRN-UHFFFAOYSA-N 6-hydroxynicotinic acid Chemical compound OC(=O)C1=CC=C(O)N=C1 BLHCMGRVFXRYRN-UHFFFAOYSA-N 0.000 description 1
- GDMSROKTSLKQPM-UHFFFAOYSA-N 6-methyl-9-oxo-[1,3]thiazolo[5,4-f]quinoline-8-carboxylic acid Chemical compound C1=C2N(C)C=C(C(O)=O)C(=O)C2=C2SC=NC2=C1 GDMSROKTSLKQPM-UHFFFAOYSA-N 0.000 description 1
- QZUCTUIUIAGUSQ-UHFFFAOYSA-N 7-chloro-1-ethyl-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(Cl)C=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 QZUCTUIUIAGUSQ-UHFFFAOYSA-N 0.000 description 1
- UEZCMDFHCHWUFM-UHFFFAOYSA-N 7-chloro-1-methyl-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(Cl)C=C2N(C)C=C(C(O)=O)C(=O)C2=C1 UEZCMDFHCHWUFM-UHFFFAOYSA-N 0.000 description 1
- 208000031295 Animal disease Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- CSGQJHQYWJLPKY-UHFFFAOYSA-N CITRAZINIC ACID Chemical compound OC(=O)C=1C=C(O)NC(=O)C=1 CSGQJHQYWJLPKY-UHFFFAOYSA-N 0.000 description 1
- 101100173790 Caulobacter vibrioides (strain ATCC 19089 / CB15) flbD gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 101150000419 GPC gene Proteins 0.000 description 1
- 241000828585 Gari Species 0.000 description 1
- 101000899806 Homo sapiens Retinal guanylyl cyclase 1 Proteins 0.000 description 1
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 101000831256 Oryza sativa subsp. japonica Cysteine proteinase inhibitor 1 Proteins 0.000 description 1
- 101001077374 Oryza sativa subsp. japonica UMP-CMP kinase 3 Proteins 0.000 description 1
- 101001009851 Rattus norvegicus Guanylate cyclase 2G Proteins 0.000 description 1
- 102100022663 Retinal guanylyl cyclase 1 Human genes 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 1
- NVVMIVJVAAXSCG-UHFFFAOYSA-N [Na].C(C)N Chemical compound [Na].C(C)N NVVMIVJVAAXSCG-UHFFFAOYSA-N 0.000 description 1
- KMNWCNNLFBCDJR-UHFFFAOYSA-N [Si].[K] Chemical compound [Si].[K] KMNWCNNLFBCDJR-UHFFFAOYSA-N 0.000 description 1
- UWMLSXCBFHQUTH-UHFFFAOYSA-M [chloro(dimethylamino)methylidene]-dimethylazanium;chloride Chemical compound [Cl-].CN(C)C(Cl)=[N+](C)C UWMLSXCBFHQUTH-UHFFFAOYSA-M 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 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
- 235000014121 butter Nutrition 0.000 description 1
- FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 description 1
- 229960003669 carbenicillin Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- ZSOGBNYKSJURBJ-UHFFFAOYSA-N carbonochloridoyl ethyl carbonate Chemical compound CCOC(=O)OC(Cl)=O ZSOGBNYKSJURBJ-UHFFFAOYSA-N 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- PMPYSSMGWFNAAQ-UHFFFAOYSA-N dichloromethane;n,n-diethylethanamine Chemical compound ClCCl.CCN(CC)CC PMPYSSMGWFNAAQ-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- XCPXPFNKTCFWTA-UHFFFAOYSA-N ethyl carbonobromidate Chemical compound CCOC(Br)=O XCPXPFNKTCFWTA-UHFFFAOYSA-N 0.000 description 1
- LKHYFCSSVZVVNF-UHFFFAOYSA-N ethyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OCC LKHYFCSSVZVVNF-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 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
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- LFKYBJLFJOOKAE-UHFFFAOYSA-N imidazol-2-ylidenemethanone Chemical compound O=C=C1N=CC=N1 LFKYBJLFJOOKAE-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical compound C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 150000005331 phenylglycines Chemical class 0.000 description 1
- SFZTYTSYMOZBIY-UHFFFAOYSA-M potassium;butan-1-ol;2-ethylhexanoate Chemical compound [K+].CCCCO.CCCCC(CC)C([O-])=O SFZTYTSYMOZBIY-UHFFFAOYSA-M 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
- C07D499/68—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms with aromatic rings as additional substituents on the carbon chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4511872 | 1972-05-08 | ||
| JP4511872A JPS5547036B2 (de) | 1972-05-08 | 1972-05-08 | |
| JP8342472A JPS4941396A (de) | 1972-08-21 | 1972-08-21 | |
| JP8342472 | 1972-08-21 | ||
| JP8510372A JPS4942693A (de) | 1972-08-25 | 1972-08-25 | |
| JP8510372 | 1972-08-25 | ||
| JP8510272 | 1972-08-25 | ||
| JP8510272A JPS4942692A (de) | 1972-08-25 | 1972-08-25 | |
| JP12595272A JPS4981388A (de) | 1972-12-15 | 1972-12-15 | |
| JP12595272 | 1972-12-15 | ||
| JP1991773 | 1973-02-18 | ||
| JP1991773A JPS49108092A (de) | 1973-02-18 | 1973-02-18 | |
| JP3813273A JPS49125386A (de) | 1973-04-04 | 1973-04-04 | |
| JP3813273 | 1973-04-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI58131B FI58131B (fi) | 1980-08-29 |
| FI58131C true FI58131C (fi) | 1980-12-10 |
Family
ID=27563884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI1458/73A FI58131C (fi) | 1972-05-08 | 1973-05-07 | Foerfarande foer framstaellning av terapeutiskt vaerdefulla ampicillinderivat |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3953428A (de) |
| AR (2) | AR204813A1 (de) |
| AT (1) | AT331970B (de) |
| BE (1) | BE799202A (de) |
| CA (1) | CA1050971A (de) |
| DE (1) | DE2322750A1 (de) |
| DK (1) | DK139754B (de) |
| FI (1) | FI58131C (de) |
| FR (1) | FR2183895B1 (de) |
| GB (1) | GB1407566A (de) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4202900A (en) * | 1972-09-27 | 1980-05-13 | Ciba-Geigy Corporation | Derivatives of penam-3-carboxylic acid and a pharmaceutical composition containing the same |
| JPS5751837B2 (de) * | 1973-04-05 | 1982-11-04 | ||
| US3994874A (en) * | 1973-11-07 | 1976-11-30 | Richardson-Merrell Inc. | 6-[(2-Oxo-1-pyridinyl)acylamino]penicillin derivatives |
| US3954734A (en) * | 1974-01-21 | 1976-05-04 | Parke, Davis & Company | Novel antibacterial amide compounds and process means for producing the same |
| IL47168A (en) * | 1974-05-09 | 1979-07-25 | Toyama Chemical Co Ltd | Mono or dioxo piperazino(thio)carbonylamino derivatives ofpenicillins and cephalosporins and process for producing the same |
| US3989687A (en) * | 1974-09-27 | 1976-11-02 | Richardson-Merrell Inc. | 4-Oxo-1-pyridinyl penicillin derivatives |
| GB1568962A (en) * | 1975-10-31 | 1980-06-11 | Beecham Group Ltd | Reparation and compositions containing them (heterocyclic-carbonylamino)pencillins methods for their p |
| NZ184434A (en) * | 1976-06-30 | 1979-03-28 | Dainippon Pharmaceutical Co | Penicillins with a substituted p-hydroxy-benzyl side-chain, and injectable pharmaceutical compositions |
| GB1579362A (en) * | 1977-03-16 | 1980-11-19 | Beecham Group Ltd | 6-(a-heterocyclylcarbonyl amino-acetamido)-penicillins and compositions containing them |
| EP0001041A3 (de) * | 1977-07-27 | 1979-06-27 | Sandoz Ag | Alpha(Pyridonecarboxylamino)Alpha-acetamid-substituierte Penicilline und Cephalosporine, Verfahren zu ihrer Herstellung, ihre Verwendung als Arzneimittel; Pyridone für ihre Herstellung |
| GB2010250B (en) * | 1977-12-06 | 1982-07-14 | Nippon Chemiphar Co | Penicillin and cephalosporin derivatives and a process for producing the same |
| US4231928A (en) * | 1979-04-24 | 1980-11-04 | Bristol-Myers Company | Antibacterial agents |
| JPS5651488A (en) * | 1979-10-02 | 1981-05-09 | Meiji Seika Kaisha Ltd | Penicillin derivative and its preparation |
| US5281612A (en) * | 1982-09-09 | 1994-01-25 | Warner-Lambert Company | Naphthyridine antibacterial agents |
| IE55898B1 (en) * | 1982-09-09 | 1991-02-14 | Warner Lambert Co | Antibacterial agents |
| IT1215277B (it) * | 1985-05-27 | 1990-01-31 | Pomezia Roma A | Derivato chinolin-lattaminico ad attivita' antibatterica ed inibitrice delle b-lattamasi. |
| US5273973A (en) * | 1988-10-24 | 1993-12-28 | Norwich Eaton Pharmaceuticals, Inc. | Antimicrobial quinolonyl esters |
| US5328908A (en) * | 1988-10-24 | 1994-07-12 | Procter & Gamble Pharmaceuticals, Inc. | Antimicrobial quinolone thioureas |
| CA2001203C (en) * | 1988-10-24 | 2001-02-13 | Thomas P. Demuth, Jr. | Novel antimicrobial dithiocarbamoyl quinolones |
| EP0997466A1 (de) * | 1988-10-24 | 2000-05-03 | PROCTER & GAMBLE PHARMACEUTICALS, INC. | Antimikrobielle Laktamchinolone |
| US5491139A (en) * | 1988-10-24 | 1996-02-13 | The Procter & Gamble Company | Antimicrobial quinolonyl lactams |
| US5180719A (en) * | 1988-10-24 | 1993-01-19 | Norwich Eaton Pharmaceuticals, Inc. | Antimicrobial quinolonyl lactam esters |
| ES2147721T3 (es) * | 1990-04-18 | 2000-10-01 | Procter & Gamble Pharma | Quinolonil lactamas antimicrobianas. |
| FR2713637B1 (fr) * | 1993-12-15 | 1996-01-05 | Cird Galderma | Nouveaux composés bi-aromatiques dérivés d'amide, compositions pharmaceutiques et cosmétiques les contenant et utilisations. |
| US6143760A (en) | 1997-08-25 | 2000-11-07 | Neurogen Corporation | Substituted 4-oxo-napthyridine-3-carboxamides: GABA brain receptor ligands |
| PL338783A1 (en) * | 1997-08-25 | 2000-11-20 | Neurogen Corp | Substituted 4-oxo-naphtyridin-3-carboxamides as ligands of cerebral gaba receptors |
| US7939558B2 (en) * | 2004-06-04 | 2011-05-10 | The Regents Of The University Of California | Compounds having activity in increasing ion transport by mutant-CFTR and uses thereof |
| US8669370B2 (en) | 2011-01-26 | 2014-03-11 | Sanofi | Substituted 3-heteroaroylamino-propionic acid derivatives and their use as pharmaceuticals |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1180745A (en) * | 1966-10-04 | 1970-02-11 | Beecham Group Ltd | Penicillins |
| US3668198A (en) * | 1970-06-01 | 1972-06-06 | Squibb & Sons Inc | {60 -ureido-2,4,6-cycloheptatrienylmethylpenicillins |
| US3711471A (en) * | 1971-02-03 | 1973-01-16 | Bristol Myers Co | Purification of 6-{8 d-{60 -(3-guanyl-1-ureido)phenylacetamido{9 {0 penicillanic acid |
-
1973
- 1973-01-01 AR ARJA247904A patent/AR204813A1/es active
- 1973-01-01 AR AR251189A patent/AR204162A1/es active
- 1973-04-30 CA CA169,846A patent/CA1050971A/en not_active Expired
- 1973-05-01 US US05/356,120 patent/US3953428A/en not_active Expired - Lifetime
- 1973-05-05 DE DE2322750A patent/DE2322750A1/de not_active Withdrawn
- 1973-05-07 AT AT399573A patent/AT331970B/de not_active IP Right Cessation
- 1973-05-07 BE BE130836A patent/BE799202A/xx unknown
- 1973-05-07 DK DK248973AA patent/DK139754B/da not_active IP Right Cessation
- 1973-05-07 FI FI1458/73A patent/FI58131C/fi active
- 1973-05-08 GB GB2195173A patent/GB1407566A/en not_active Expired
- 1973-05-08 FR FR7316416A patent/FR2183895B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA1050971A (en) | 1979-03-20 |
| ATA399573A (de) | 1975-12-15 |
| DE2322750A1 (de) | 1973-11-29 |
| AT331970B (de) | 1975-12-15 |
| FI58131B (fi) | 1980-08-29 |
| GB1407566A (en) | 1975-09-24 |
| AU5504573A (en) | 1974-11-07 |
| AR204162A1 (es) | 1975-11-28 |
| DK139754C (de) | 1979-09-24 |
| US3953428A (en) | 1976-04-27 |
| AR204813A1 (es) | 1976-03-05 |
| DK139754B (da) | 1979-04-09 |
| FR2183895B1 (de) | 1976-07-02 |
| BE799202A (fr) | 1973-08-31 |
| FR2183895A1 (de) | 1973-12-21 |
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