PL71391B1 - 3-alkoxy-thia naphthene-2-carboxamides [us3745175a] - Google Patents
3-alkoxy-thia naphthene-2-carboxamides [us3745175a] Download PDFInfo
- Publication number
- PL71391B1 PL71391B1 PL1969135088A PL13508869A PL71391B1 PL 71391 B1 PL71391 B1 PL 71391B1 PL 1969135088 A PL1969135088 A PL 1969135088A PL 13508869 A PL13508869 A PL 13508869A PL 71391 B1 PL71391 B1 PL 71391B1
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- PL
- Poland
- Prior art keywords
- acid
- carboxylic acid
- amide
- ethyl
- methoxy
- Prior art date
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- -1 alkyl 2-carbomethoxymethylthiobenzoate Chemical compound 0.000 claims abstract description 50
- 239000002253 acid Substances 0.000 claims abstract description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 3
- 150000001412 amines Chemical class 0.000 claims abstract description 3
- 125000003277 amino group Chemical group 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims description 14
- 150000001408 amides Chemical class 0.000 claims description 13
- 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 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 150000003254 radicals Chemical class 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 claims 2
- BLCLUNNBJQETOU-UHFFFAOYSA-N 2-(2-methoxy-2-oxoethyl)benzenecarbothioic S-acid Chemical compound COC(CC1=C(C(=S)O)C=CC=C1)=O BLCLUNNBJQETOU-UHFFFAOYSA-N 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 28
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- LMFXURFVDJYQJY-UHFFFAOYSA-N 2-(2-sulfanylcarbonylphenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1C(O)=S LMFXURFVDJYQJY-UHFFFAOYSA-N 0.000 abstract description 5
- PYMSTJLTQHAJIG-UHFFFAOYSA-N 2-(carboxymethylsulfanyl)-4,5-dimethoxybenzoic acid Chemical compound COC1=CC(SCC(O)=O)=C(C(O)=O)C=C1OC PYMSTJLTQHAJIG-UHFFFAOYSA-N 0.000 abstract description 4
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract description 4
- 230000003474 anti-emetic effect Effects 0.000 abstract description 4
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 abstract description 4
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract description 3
- 229940106681 chloroacetic acid Drugs 0.000 abstract description 3
- QQFHCCQSCQBKBG-UHFFFAOYSA-N methyl 2-amino-4,5-dimethoxybenzoate Chemical compound COC(=O)C1=CC(OC)=C(OC)C=C1N QQFHCCQSCQBKBG-UHFFFAOYSA-N 0.000 abstract description 3
- 150000002828 nitro derivatives Chemical class 0.000 abstract description 3
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 abstract description 3
- QUEKGYQTRJVEQC-UHFFFAOYSA-N 2516-96-3 Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC=C1Cl QUEKGYQTRJVEQC-UHFFFAOYSA-N 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000443 aerosol Substances 0.000 abstract description 2
- 239000002111 antiemetic agent Substances 0.000 abstract description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 239000001301 oxygen Chemical group 0.000 abstract description 2
- 230000000506 psychotropic effect Effects 0.000 abstract description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- 230000002152 alkylating effect Effects 0.000 abstract 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 2
- 241000497851 Anaphes Species 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000005336 allyloxy group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000011065 in-situ storage Methods 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 96
- 239000000243 solution Substances 0.000 description 72
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 68
- 239000000047 product Substances 0.000 description 59
- 239000000203 mixture Substances 0.000 description 56
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
- 238000010438 heat treatment Methods 0.000 description 47
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 description 42
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 238000010992 reflux Methods 0.000 description 33
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 32
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 238000002844 melting Methods 0.000 description 26
- 230000008018 melting Effects 0.000 description 26
- 238000007792 addition Methods 0.000 description 25
- 235000019441 ethanol Nutrition 0.000 description 25
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 24
- 230000000694 effects Effects 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000002244 precipitate Substances 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 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 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000007868 Raney catalyst Substances 0.000 description 7
- 229910000564 Raney nickel Inorganic materials 0.000 description 7
- 229910052759 nickel Inorganic materials 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000012458 free base Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
- 239000006229 carbon black Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 3
- 229960004046 apomorphine Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- PJPCSHBTNKBEBS-UHFFFAOYSA-N methyl 2-(2-methoxy-2-oxoethyl)sulfanyl-5-nitrobenzoate Chemical compound COC(=O)CSC1=CC=C([N+]([O-])=O)C=C1C(=O)OC PJPCSHBTNKBEBS-UHFFFAOYSA-N 0.000 description 3
- WVCXTJCZOZYWMX-UHFFFAOYSA-N methyl 2-(2-methoxycarbothioylphenyl)acetate Chemical compound COC(=O)CC1=CC=CC=C1C(=S)OC WVCXTJCZOZYWMX-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ZMURVXNAGCJFEK-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine;hydrochloride Chemical compound Cl.CCN1CCCC1CN ZMURVXNAGCJFEK-UHFFFAOYSA-N 0.000 description 2
- KTHAOBTZABTOCS-UHFFFAOYSA-N 1-ethylpyrrolidin-2-amine Chemical compound CCN1CCCC1N KTHAOBTZABTOCS-UHFFFAOYSA-N 0.000 description 2
- OHUNNGBOLPPURJ-UHFFFAOYSA-N 2-(carboxymethylsulfanyl)-5-nitrobenzoic acid Chemical compound OC(=O)CSC1=CC=C([N+]([O-])=O)C=C1C(O)=O OHUNNGBOLPPURJ-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 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
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- RCVLCUFQNYXLMC-UHFFFAOYSA-N methyl 4,5-dimethoxy-2-(2-methoxy-2-oxoethyl)sulfanylbenzoate Chemical compound COC(=O)CSC1=CC(OC)=C(OC)C=C1C(=O)OC RCVLCUFQNYXLMC-UHFFFAOYSA-N 0.000 description 2
- SYYKLKHBZGFKOC-UHFFFAOYSA-N methyl 4,5-dimethoxy-2-nitrobenzoate Chemical compound COC(=O)C1=CC(OC)=C(OC)C=C1[N+]([O-])=O SYYKLKHBZGFKOC-UHFFFAOYSA-N 0.000 description 2
- 229940102396 methyl bromide Drugs 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- LEKNBLYGRWKNSE-UHFFFAOYSA-N (1-ethylpiperidin-2-yl)methanamine Chemical compound CCN1CCCCC1CN LEKNBLYGRWKNSE-UHFFFAOYSA-N 0.000 description 1
- IFZHGQSUNAKKSN-UHFFFAOYSA-N 1,1-diethylhydrazine Chemical compound CCN(N)CC IFZHGQSUNAKKSN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MQWGOZLHMBMYJL-UHFFFAOYSA-N 1-pyrrolidin-2-ylpropan-1-amine Chemical compound CCC(N)C1CCCN1 MQWGOZLHMBMYJL-UHFFFAOYSA-N 0.000 description 1
- RIZUCYSQUWMQLX-UHFFFAOYSA-N 2,3-dimethylbenzoic acid Chemical compound CC1=CC=CC(C(O)=O)=C1C RIZUCYSQUWMQLX-UHFFFAOYSA-N 0.000 description 1
- STPWPICGADJXAM-UHFFFAOYSA-N 2-(carboxymethylsulfonyl)benzoic acid Chemical compound OC(=O)CS(=O)(=O)C1=CC=CC=C1C(O)=O STPWPICGADJXAM-UHFFFAOYSA-N 0.000 description 1
- OKSWTTKPZQFGEH-UHFFFAOYSA-N 2-(diethylamino)ethylazanium;chloride Chemical compound Cl.CCN(CC)CCN OKSWTTKPZQFGEH-UHFFFAOYSA-N 0.000 description 1
- KTHTXLUIEAIGCD-UHFFFAOYSA-N 2-amino-3,5-dichlorobenzoic acid Chemical compound NC1=C(Cl)C=C(Cl)C=C1C(O)=O KTHTXLUIEAIGCD-UHFFFAOYSA-N 0.000 description 1
- GNMFPYJORUCLEY-UHFFFAOYSA-N 2-aminobenzoic acid;hydrochloride Chemical compound Cl.NC1=CC=CC=C1C(O)=O GNMFPYJORUCLEY-UHFFFAOYSA-N 0.000 description 1
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 241001062472 Stokellia anisodon Species 0.000 description 1
- 208000010513 Stupor Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 229940064734 aminobenzoate Drugs 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 230000002903 catalepsic effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000002895 emetic Substances 0.000 description 1
- UHIWBULTEZXYLI-UHFFFAOYSA-N ethanamine;pyrrolidine Chemical compound CCN.C1CCNC1 UHIWBULTEZXYLI-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- JPPSLDGKNMDURB-UHFFFAOYSA-N methyl 2,3-dimethoxy-6-nitrobenzoate Chemical compound COC(C1=C(C=CC(=C1OC)OC)[N+](=O)[O-])=O JPPSLDGKNMDURB-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000000051 modifying effect Effects 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
- GFMUAWWLXMJVRV-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine;hydrochloride Chemical compound [Cl-].C[NH+](C)CCN GFMUAWWLXMJVRV-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004622 sleep time Effects 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000012712 vegetable carbon Nutrition 0.000 description 1
- 239000004108 vegetable carbon Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000012991 xanthate Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- 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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR161060A FR7627M (enExample) | 1968-07-29 | 1968-07-29 | |
| FR171684 | 1968-10-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL71391B1 true PL71391B1 (en) | 1974-06-29 |
Family
ID=26182149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1969135088A PL71391B1 (en) | 1968-07-29 | 1969-07-28 | 3-alkoxy-thia naphthene-2-carboxamides [us3745175a] |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3745175A (enExample) |
| JP (1) | JPS4832109B1 (enExample) |
| BE (1) | BE736561A (enExample) |
| CH (2) | CH526571A (enExample) |
| DE (1) | DE1937514C3 (enExample) |
| DK (1) | DK122133B (enExample) |
| ES (1) | ES369934A1 (enExample) |
| FI (1) | FI49977C (enExample) |
| GB (1) | GB1234699A (enExample) |
| IE (1) | IE33497B1 (enExample) |
| IL (1) | IL32713A (enExample) |
| LU (1) | LU59171A1 (enExample) |
| MC (1) | MC807A1 (enExample) |
| NL (1) | NL6911587A (enExample) |
| NO (1) | NO126019B (enExample) |
| OA (1) | OA03890A (enExample) |
| PH (1) | PH10146A (enExample) |
| PL (1) | PL71391B1 (enExample) |
| RO (1) | RO56165A (enExample) |
| SE (1) | SE359838B (enExample) |
| YU (2) | YU36516B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3862320A (en) * | 1968-07-29 | 1975-01-21 | Ile De France | Methods of protection against emesis in mammals by administration of a 3-alkoxy-thianaphthene-2-carboxamide |
| US3976780A (en) * | 1968-07-29 | 1976-08-24 | Societe D'etudes Scientifiques Et Industrielles L'ile-De-France | Methods of protection against emesis in mammals by administration of a 3-alkoxy-thianaphthene-2-carboxamide |
| US4056526A (en) * | 1972-05-26 | 1977-11-01 | Warner-Lambert Company | Benzo(b)thiophene derivatives |
| JPS53124764A (en) * | 1977-04-06 | 1978-10-31 | Katsura Seiki Mfg | Magnetic force type control device |
| JPS59186969A (ja) * | 1983-04-08 | 1984-10-23 | Yoshitomi Pharmaceut Ind Ltd | ベンゾフラン−およびベンゾピランカルボキサミド誘導体 |
| US5175173A (en) * | 1983-12-22 | 1992-12-29 | Sun Jung Hui | Carboxamides useful as antiemetic or antipsychotic agents |
| US4888353A (en) * | 1986-02-28 | 1989-12-19 | Erbamont, Inc. | Carboxamides useful as antiemetic or antipsychotic agents |
| DE3445377A1 (de) * | 1983-12-23 | 1985-07-04 | Sandoz-Patent-GmbH, 7850 Lörrach | Carbocylische und heterocyclische carbonsaeureester und -amide von ueberbrueckten und nicht ueberbrueckten cyclischen stickstoffhaltigen aminen oder alkoholen |
| US5068248A (en) * | 1984-04-02 | 1991-11-26 | Merck & Co., Inc. | N-alkenyl-3-hydroxybenzo[b]thiophene-2-carboxamide derivatives as dual cyclooxygenase and lipoxygenase inhibitors |
| IL74694A0 (en) * | 1984-04-02 | 1985-06-30 | Merck & Co Inc | N-alkenyl-3-hydroxybenzo(b)thiophene-2-carboxamide derivatives,their preparation and pharmaceutical compositions containing them |
| US4800211A (en) * | 1986-08-18 | 1989-01-24 | Merck & Co., Inc. | 5-methylthio-3-hydroxybenzo [b]thiophene-2-carboxamide derivatives as cyclooxygenase and lipoxygenase inhibitors |
| US4772459A (en) * | 1986-09-09 | 1988-09-20 | Erbamont, Inc. | Method for controlling emesis caused by chemotherapeutic agents and antiemetic agents useful therein |
| ES2087463T3 (es) * | 1991-11-18 | 1996-07-16 | Lilly Industries Ltd | Benzo(b)tiofen-2-carboxamidas para el tratamiento de trastornos del sistema nervioso central. |
| GB9218113D0 (en) * | 1992-08-26 | 1992-10-14 | Lilly Industries Ltd | Pharmaceutical compounds |
| US7674822B2 (en) | 2004-11-24 | 2010-03-09 | Wyeth | PTP1b inhibitors |
| US12605353B2 (en) * | 2019-12-02 | 2026-04-21 | Academia Sinica | PDIA4 inhibitors and use thereof for inhibiting β-cell pathogenesis and treating diabetes |
-
1960
- 1960-07-25 MC MC835A patent/MC807A1/fr unknown
-
1969
- 1969-07-23 OA OA53682A patent/OA03890A/xx unknown
- 1969-07-23 DE DE1937514A patent/DE1937514C3/de not_active Expired
- 1969-07-24 IE IE1026/69A patent/IE33497B1/xx unknown
- 1969-07-25 SE SE10506/69A patent/SE359838B/xx unknown
- 1969-07-25 BE BE736561D patent/BE736561A/xx not_active IP Right Cessation
- 1969-07-25 LU LU59171D patent/LU59171A1/xx unknown
- 1969-07-26 ES ES369934A patent/ES369934A1/es not_active Expired
- 1969-07-26 JP JP44059282A patent/JPS4832109B1/ja active Pending
- 1969-07-27 IL IL32713A patent/IL32713A/en unknown
- 1969-07-28 GB GB37796/69A patent/GB1234699A/en not_active Expired
- 1969-07-28 PL PL1969135088A patent/PL71391B1/pl unknown
- 1969-07-28 DK DK407169AA patent/DK122133B/da not_active IP Right Cessation
- 1969-07-28 NO NO3098/69A patent/NO126019B/no unknown
- 1969-07-29 FI FI692246A patent/FI49977C/fi active
- 1969-07-29 CH CH1154369A patent/CH526571A/fr not_active IP Right Cessation
- 1969-07-29 NL NL6911587A patent/NL6911587A/xx unknown
- 1969-07-29 RO RO60666A patent/RO56165A/ro unknown
- 1969-07-29 CH CH253171A patent/CH526572A/fr not_active IP Right Cessation
- 1969-07-29 YU YU01964/69A patent/YU36516B/xx unknown
-
1971
- 1971-05-05 US US00140605A patent/US3745175A/en not_active Expired - Lifetime
-
1973
- 1973-08-10 PH PH14901A patent/PH10146A/en unknown
-
1977
- 1977-09-20 YU YU2336/77A patent/YU37162B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU36516B (en) | 1984-02-29 |
| BE736561A (enExample) | 1970-01-26 |
| IL32713A0 (en) | 1969-09-25 |
| IL32713A (en) | 1973-08-29 |
| YU196469A (en) | 1982-02-25 |
| NL6911587A (enExample) | 1970-02-02 |
| IE33497B1 (en) | 1974-07-24 |
| DK122133B (da) | 1972-01-24 |
| GB1234699A (en) | 1971-06-09 |
| DE1937514C3 (de) | 1975-03-13 |
| CH526571A (fr) | 1972-08-15 |
| NO126019B (enExample) | 1972-12-11 |
| YU37162B (en) | 1984-08-31 |
| DE1937514B2 (de) | 1974-07-11 |
| US3745175A (en) | 1973-07-10 |
| SE359838B (enExample) | 1973-09-10 |
| FI49977C (fi) | 1975-11-10 |
| FI49977B (enExample) | 1975-07-31 |
| CH526572A (fr) | 1972-08-15 |
| DE1937514A1 (de) | 1970-02-19 |
| IE33497L (en) | 1970-01-29 |
| PH10146A (en) | 1976-09-06 |
| OA03890A (fr) | 1975-08-14 |
| LU59171A1 (enExample) | 1970-01-26 |
| YU233677A (en) | 1983-04-27 |
| ES369934A1 (es) | 1971-12-01 |
| JPS4832109B1 (enExample) | 1973-10-04 |
| RO56165A (enExample) | 1974-04-29 |
| MC807A1 (fr) | 1970-07-30 |
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