NO832056L - Fremgangsmaate for fremstilling av aminobenzamidderivater - Google Patents
Fremgangsmaate for fremstilling av aminobenzamidderivaterInfo
- Publication number
- NO832056L NO832056L NO832056A NO832056A NO832056L NO 832056 L NO832056 L NO 832056L NO 832056 A NO832056 A NO 832056A NO 832056 A NO832056 A NO 832056A NO 832056 L NO832056 L NO 832056L
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- pyridinylamino
- alkyl
- carbon atoms
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title claims description 7
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 67
- -1 2-furanylmethylamino, 2-thienylmethylamino Chemical group 0.000 claims description 29
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 24
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000004820 halides Chemical class 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 239000012458 free base Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- 229910021529 ammonia Inorganic materials 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- YMODINPJYNHPTM-UHFFFAOYSA-N piperidin-1-yl-[2-(pyridin-4-ylamino)phenyl]methanone Chemical compound C=1C=CC=C(NC=2C=CN=CC=2)C=1C(=O)N1CCCCC1 YMODINPJYNHPTM-UHFFFAOYSA-N 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 3
- 150000005751 4-halopyridines Chemical class 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005322 morpholin-1-yl group Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000000376 reactant Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 150000002823 nitrates Chemical class 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- 238000002844 melting Methods 0.000 description 47
- 230000008018 melting Effects 0.000 description 47
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
- 239000000843 powder Substances 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 15
- YXTROGRGRSPWKL-UHFFFAOYSA-N 1-benzoylpiperidine Chemical compound C=1C=CC=CC=1C(=O)N1CCCCC1 YXTROGRGRSPWKL-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 206010020772 Hypertension Diseases 0.000 description 13
- 229960000583 acetic acid Drugs 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000001631 hypertensive effect Effects 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 241000282472 Canis lupus familiaris Species 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 230000037396 body weight Effects 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 230000036772 blood pressure Effects 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- MJHIUTGYCYFAQM-UHFFFAOYSA-N 2-(pyridin-4-ylamino)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1NC1=CC=NC=C1 MJHIUTGYCYFAQM-UHFFFAOYSA-N 0.000 description 6
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 6
- PVMNPAUTCMBOMO-UHFFFAOYSA-N 4-chloropyridine Chemical compound ClC1=CC=NC=C1 PVMNPAUTCMBOMO-UHFFFAOYSA-N 0.000 description 6
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 229960002003 hydrochlorothiazide Drugs 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- YJTQPHOSNYIGPC-UHFFFAOYSA-N (2-aminophenyl)-piperidin-1-ylmethanone Chemical compound NC1=CC=CC=C1C(=O)N1CCCCC1 YJTQPHOSNYIGPC-UHFFFAOYSA-N 0.000 description 5
- 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 5
- XGAFCCUNHIMIRV-UHFFFAOYSA-N 4-chloropyridine;hydron;chloride Chemical compound Cl.ClC1=CC=NC=C1 XGAFCCUNHIMIRV-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000003276 anti-hypertensive effect Effects 0.000 description 5
- 229940030600 antihypertensive agent Drugs 0.000 description 5
- 239000002220 antihypertensive agent Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 230000035488 systolic blood pressure Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229960004050 aminobenzoic acid Drugs 0.000 description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 4
- 229940011051 isopropyl acetate Drugs 0.000 description 4
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- GWFRXASQNMRZDR-UHFFFAOYSA-N 2-(pyridin-4-ylamino)benzamide Chemical compound NC(=O)C1=CC=CC=C1NC1=CC=NC=C1 GWFRXASQNMRZDR-UHFFFAOYSA-N 0.000 description 3
- XZGYYDNYYBXBMG-UHFFFAOYSA-N 3-(pyridin-4-ylamino)benzoic acid Chemical compound OC(=O)C1=CC=CC(NC=2C=CN=CC=2)=C1 XZGYYDNYYBXBMG-UHFFFAOYSA-N 0.000 description 3
- OEWZQATXQINCCC-UHFFFAOYSA-N 4-(pyridin-4-ylamino)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=CC=NC=C1 OEWZQATXQINCCC-UHFFFAOYSA-N 0.000 description 3
- FWRWRJKSLHIUSB-UHFFFAOYSA-N 5-chloro-2-(pyridin-4-ylamino)benzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1NC1=CC=NC=C1 FWRWRJKSLHIUSB-UHFFFAOYSA-N 0.000 description 3
- HUXLJYVIDYDFAM-UHFFFAOYSA-N 5-methoxy-2-(pyridin-4-ylamino)benzoic acid Chemical compound OC(=O)C1=CC(OC)=CC=C1NC1=CC=NC=C1 HUXLJYVIDYDFAM-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 3
- JXLPJCAIPGVFAA-UHFFFAOYSA-N azanium;acetonitrile;hydroxide Chemical compound [NH4+].[OH-].CC#N JXLPJCAIPGVFAA-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000035487 diastolic blood pressure Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 2
- KABOMADKZMEQDW-UHFFFAOYSA-N 4-(pyridin-4-ylamino)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1NC1=CC=NC=C1 KABOMADKZMEQDW-UHFFFAOYSA-N 0.000 description 2
- CMHGAONVNWWTNW-UHFFFAOYSA-N 5-bromo-2-(pyridin-4-ylamino)benzamide Chemical compound NC(=O)C1=CC(Br)=CC=C1NC1=CC=NC=C1 CMHGAONVNWWTNW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- UUWCBYCDJVXAJY-UHFFFAOYSA-N [2-(methylamino)phenyl]-piperidin-1-ylmethanone Chemical compound CNC1=CC=CC=C1C(=O)N1CCCCC1 UUWCBYCDJVXAJY-UHFFFAOYSA-N 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- DQQBKLSTSBKMNE-UHFFFAOYSA-N (2-ethylpiperidin-1-yl)-[2-(pyridin-4-ylamino)phenyl]methanone Chemical compound CCC1CCCCN1C(=O)C1=CC=CC=C1NC1=CC=NC=C1 DQQBKLSTSBKMNE-UHFFFAOYSA-N 0.000 description 1
- SVCGCPMEYICOTD-UHFFFAOYSA-N (2-methylpiperidin-1-yl)-[2-(pyridin-4-ylamino)phenyl]methanone Chemical compound CC1CCCCN1C(=O)C1=CC=CC=C1NC1=CC=NC=C1 SVCGCPMEYICOTD-UHFFFAOYSA-N 0.000 description 1
- RRYBWBQTLYFEEE-UHFFFAOYSA-N (3-methylpiperidin-1-yl)-[2-(pyridin-4-ylamino)phenyl]methanone Chemical compound C1C(C)CCCN1C(=O)C1=CC=CC=C1NC1=CC=NC=C1 RRYBWBQTLYFEEE-UHFFFAOYSA-N 0.000 description 1
- OQHUDIOWOXLSHI-UHFFFAOYSA-N (4-methylpiperidin-1-yl)-[2-(pyridin-4-ylamino)phenyl]methanone Chemical compound C1CC(C)CCN1C(=O)C1=CC=CC=C1NC1=CC=NC=C1 OQHUDIOWOXLSHI-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- ALACKQVKUUIRKO-UHFFFAOYSA-N 2-(2-pyridin-2-ylethylamino)benzamide Chemical class NC(=O)C1=CC=CC=C1NCCC1=CC=CC=N1 ALACKQVKUUIRKO-UHFFFAOYSA-N 0.000 description 1
- 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 1
- BDKLKNJTMLIAFE-UHFFFAOYSA-N 2-(3-fluorophenyl)-1,3-oxazole-4-carbaldehyde Chemical compound FC1=CC=CC(C=2OC=C(C=O)N=2)=C1 BDKLKNJTMLIAFE-UHFFFAOYSA-N 0.000 description 1
- RFQGAFQKNITSIA-UHFFFAOYSA-N 2-(carboxyamino)benzoic acid Chemical compound OC(=O)NC1=CC=CC=C1C(O)=O RFQGAFQKNITSIA-UHFFFAOYSA-N 0.000 description 1
- UMKSAURFQFUULT-UHFFFAOYSA-N 2-Amino-5-methoxybenzoic acid Chemical compound COC1=CC=C(N)C(C(O)=O)=C1 UMKSAURFQFUULT-UHFFFAOYSA-N 0.000 description 1
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- 241000416162 Astragalus gummifer Species 0.000 description 1
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
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- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
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- DGYOLFSCUVSVDJ-UHFFFAOYSA-N [5-methoxy-2-(pyridin-4-ylamino)phenyl]-piperidin-1-ylmethanone Chemical compound C1CCCCN1C(=O)C1=CC(OC)=CC=C1NC1=CC=NC=C1 DGYOLFSCUVSVDJ-UHFFFAOYSA-N 0.000 description 1
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- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- QVDYYQXUNAQSNI-UHFFFAOYSA-N ethyl acetate;pentane Chemical compound CCCCC.CCOC(C)=O QVDYYQXUNAQSNI-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
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- 150000003840 hydrochlorides Chemical class 0.000 description 1
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- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000009399 inbreeding Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
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- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate 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
- 238000005259 measurement Methods 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- JDXSPAHEAWMBIV-UHFFFAOYSA-N morpholin-4-yl-[2-(pyridin-4-ylamino)phenyl]methanone Chemical compound C=1C=CC=C(NC=2C=CN=CC=2)C=1C(=O)N1CCOCC1 JDXSPAHEAWMBIV-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- VLMDRHXZTGHJNR-UHFFFAOYSA-N n,n-diethyl-2-(pyridin-4-ylamino)benzamide Chemical compound CCN(CC)C(=O)C1=CC=CC=C1NC1=CC=NC=C1 VLMDRHXZTGHJNR-UHFFFAOYSA-N 0.000 description 1
- HCARMQVSFQVDIX-UHFFFAOYSA-N n,n-dimethyl-2-(pyridin-4-ylamino)benzamide Chemical compound CN(C)C(=O)C1=CC=CC=C1NC1=CC=NC=C1 HCARMQVSFQVDIX-UHFFFAOYSA-N 0.000 description 1
- XOZLUEHQSJYXKM-UHFFFAOYSA-N n,n-dimethyl-3-(piperidine-1-carbonyl)-4-(pyridin-4-ylamino)benzenesulfonamide Chemical compound C1CCCCN1C(=O)C1=CC(S(=O)(=O)N(C)C)=CC=C1NC1=CC=NC=C1 XOZLUEHQSJYXKM-UHFFFAOYSA-N 0.000 description 1
- GWKMAWSLVIKHLV-UHFFFAOYSA-N n-(furan-2-ylmethyl)-2-(pyridin-4-ylamino)benzamide Chemical compound C=1C=CC=C(NC=2C=CN=CC=2)C=1C(=O)NCC1=CC=CO1 GWKMAWSLVIKHLV-UHFFFAOYSA-N 0.000 description 1
- WDQRAFWYGTUVFK-UHFFFAOYSA-N n-ethyl-n-methyl-2-(pyridin-4-ylamino)benzamide Chemical compound CCN(C)C(=O)C1=CC=CC=C1NC1=CC=NC=C1 WDQRAFWYGTUVFK-UHFFFAOYSA-N 0.000 description 1
- FNNYMKDEIPYYSZ-UHFFFAOYSA-N n-heptyl-2-(pyridin-4-ylamino)benzamide Chemical compound CCCCCCCNC(=O)C1=CC=CC=C1NC1=CC=NC=C1 FNNYMKDEIPYYSZ-UHFFFAOYSA-N 0.000 description 1
- AVYSTTQCZBGVGZ-UHFFFAOYSA-N n-hexyl-2-(pyridin-4-ylamino)benzamide Chemical compound CCCCCCNC(=O)C1=CC=CC=C1NC1=CC=NC=C1 AVYSTTQCZBGVGZ-UHFFFAOYSA-N 0.000 description 1
- GZXIOJLHXDLNNV-UHFFFAOYSA-N n-methyl-2-(pyridin-4-ylamino)benzamide Chemical compound CNC(=O)C1=CC=CC=C1NC1=CC=NC=C1 GZXIOJLHXDLNNV-UHFFFAOYSA-N 0.000 description 1
- JLKCTIPJVMSEQQ-UHFFFAOYSA-N n-methyl-3-(piperidine-1-carbonyl)-4-(pyridin-4-ylamino)benzenesulfonamide Chemical compound C1CCCCN1C(=O)C1=CC(S(=O)(=O)NC)=CC=C1NC1=CC=NC=C1 JLKCTIPJVMSEQQ-UHFFFAOYSA-N 0.000 description 1
- VZTWMUNVPXMUOB-UHFFFAOYSA-N n-pentyl-2-(pyridin-4-ylamino)benzamide Chemical compound CCCCCNC(=O)C1=CC=CC=C1NC1=CC=NC=C1 VZTWMUNVPXMUOB-UHFFFAOYSA-N 0.000 description 1
- RRPLBNGHWIOQJC-UHFFFAOYSA-N n-propan-2-yl-2-(pyridin-4-ylamino)benzamide Chemical compound CC(C)NC(=O)C1=CC=CC=C1NC1=CC=NC=C1 RRPLBNGHWIOQJC-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FMPYNHKBCMPLAY-UHFFFAOYSA-N n-propyl-2-(pyridin-4-ylamino)benzamide Chemical compound CCCNC(=O)C1=CC=CC=C1NC1=CC=NC=C1 FMPYNHKBCMPLAY-UHFFFAOYSA-N 0.000 description 1
- QTVHHZDBEDDGSN-UHFFFAOYSA-N n-tert-butyl-2-(2-pyridin-4-ylethyl)benzamide Chemical compound CC(C)(C)NC(=O)C1=CC=CC=C1CCC1=CC=NC=C1 QTVHHZDBEDDGSN-UHFFFAOYSA-N 0.000 description 1
- 239000013642 negative control Substances 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- VUNXBQRNMNVUMV-UHFFFAOYSA-N phenyl(piperazin-1-yl)methanone Chemical compound C=1C=CC=CC=1C(=O)N1CCNCC1 VUNXBQRNMNVUMV-UHFFFAOYSA-N 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
Classifications
-
- 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
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38808082A | 1982-06-14 | 1982-06-14 | |
| US48592383A | 1983-04-18 | 1983-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO832056L true NO832056L (no) | 1983-12-15 |
Family
ID=27012132
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO832056A NO832056L (no) | 1982-06-14 | 1983-06-07 | Fremgangsmaate for fremstilling av aminobenzamidderivater |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0098951A3 (de) |
| AU (1) | AU1500583A (de) |
| DK (1) | DK263583A (de) |
| ES (1) | ES523198A0 (de) |
| FI (1) | FI832069L (de) |
| GR (1) | GR79293B (de) |
| IL (1) | IL68772A0 (de) |
| NO (1) | NO832056L (de) |
| PT (1) | PT76828B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991018891A1 (en) * | 1990-06-04 | 1991-12-12 | Pfizer Inc. | Aromatic pyrrolidine and thiazolidine amides |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3226394A (en) * | 1964-06-16 | 1965-12-28 | Shulton Inc | Pyridylethylated anthranilamides and derivatives thereof |
| BE754586A (fr) * | 1969-08-08 | 1971-02-08 | Upjohn Co | Preparations pharmaceutiques a base de p-(4-quinolylamino) benzamide etleur utilisation |
| JPS5572167A (en) * | 1978-11-27 | 1980-05-30 | Dainippon Pharmaceut Co Ltd | Pyridylaminophenylacetic acid derivative and its preparation |
-
1983
- 1983-05-24 IL IL68772A patent/IL68772A0/xx unknown
- 1983-05-26 AU AU15005/83A patent/AU1500583A/en not_active Abandoned
- 1983-05-26 EP EP83105245A patent/EP0098951A3/de not_active Withdrawn
- 1983-06-02 GR GR71553A patent/GR79293B/el unknown
- 1983-06-07 PT PT76828A patent/PT76828B/pt unknown
- 1983-06-07 NO NO832056A patent/NO832056L/no unknown
- 1983-06-08 FI FI832069A patent/FI832069L/fi not_active Application Discontinuation
- 1983-06-09 DK DK263583A patent/DK263583A/da not_active Application Discontinuation
- 1983-06-13 ES ES523198A patent/ES523198A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FI832069L (fi) | 1983-12-15 |
| PT76828A (en) | 1983-07-01 |
| EP0098951A3 (de) | 1985-01-23 |
| AU1500583A (en) | 1983-12-22 |
| GR79293B (de) | 1984-10-22 |
| ES8503659A1 (es) | 1985-03-16 |
| DK263583A (da) | 1983-12-15 |
| FI832069A0 (fi) | 1983-06-08 |
| ES523198A0 (es) | 1985-03-16 |
| PT76828B (en) | 1986-01-15 |
| DK263583D0 (da) | 1983-06-09 |
| EP0098951A2 (de) | 1984-01-25 |
| IL68772A0 (en) | 1983-09-30 |
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