FI76557C - Foerfarande foer framstaellning av farmakologiskt aktiva n-(aryltioalkyl)-n'-(aminoalkyl)-ureafoereningar. - Google Patents
Foerfarande foer framstaellning av farmakologiskt aktiva n-(aryltioalkyl)-n'-(aminoalkyl)-ureafoereningar. Download PDFInfo
- Publication number
- FI76557C FI76557C FI821776A FI821776A FI76557C FI 76557 C FI76557 C FI 76557C FI 821776 A FI821776 A FI 821776A FI 821776 A FI821776 A FI 821776A FI 76557 C FI76557 C FI 76557C
- Authority
- FI
- Finland
- Prior art keywords
- ethyl
- compound
- urea
- methylethyl
- process according
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 139
- 238000000034 method Methods 0.000 claims description 82
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 71
- 238000002360 preparation method Methods 0.000 claims description 66
- 239000002904 solvent Substances 0.000 claims description 55
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 41
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 40
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 37
- -1 allyl diamine Chemical class 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 31
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 30
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 20
- 239000004202 carbamide Substances 0.000 claims description 19
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 18
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 18
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 14
- 239000000460 chlorine Substances 0.000 claims description 14
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 14
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 13
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 9
- 230000003288 anthiarrhythmic effect Effects 0.000 claims description 7
- 150000003975 aryl alkyl amines Chemical class 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims description 6
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- GJFNRSDCSTVPCJ-UHFFFAOYSA-N 1,8-bis(dimethylamino)naphthalene Chemical compound C1=CC(N(C)C)=C2C(N(C)C)=CC=CC2=C1 GJFNRSDCSTVPCJ-UHFFFAOYSA-N 0.000 claims description 4
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 150000004677 hydrates Chemical class 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 229940095064 tartrate Drugs 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- 150000003585 thioureas Chemical class 0.000 claims description 4
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- OSTGVQSWUXGHKL-UHFFFAOYSA-N 1-[2-(benzenesulfonyl)ethyl]-3-[2-(diethylamino)ethyl]-1-propan-2-ylurea Chemical compound CCN(CC)CCNC(=O)N(C(C)C)CCS(=O)(=O)C1=CC=CC=C1 OSTGVQSWUXGHKL-UHFFFAOYSA-N 0.000 claims description 2
- XLEAOZTZHMDLLD-UHFFFAOYSA-N 1-[2-(benzenesulfonyl)ethyl]-3-[2-(dimethylamino)ethyl]-1-propan-2-ylurea Chemical compound CN(C)CCNC(=O)N(C(C)C)CCS(=O)(=O)C1=CC=CC=C1 XLEAOZTZHMDLLD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 101150009274 nhr-1 gene Proteins 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 2
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims 2
- JOLWDJLIVSXFFI-UHFFFAOYSA-N 1-[2-(benzenesulfonyl)ethyl]-3-[3-(diethylamino)propyl]-1-propan-2-ylurea Chemical compound CCN(CC)CCCNC(=O)N(C(C)C)CCS(=O)(=O)C1=CC=CC=C1 JOLWDJLIVSXFFI-UHFFFAOYSA-N 0.000 claims 1
- WXVUWTMDBLIMIA-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-1-propan-2-ylurea Chemical compound CN(CCN(C(=O)N)C(C)C)C WXVUWTMDBLIMIA-UHFFFAOYSA-N 0.000 claims 1
- BDYZUNGZVADADC-UHFFFAOYSA-N 1-[3-(benzenesulfonyl)propyl]-3-[2-(diethylamino)ethyl]-1-propan-2-ylurea Chemical compound CCN(CC)CCNC(=O)N(C(C)C)CCCS(=O)(=O)C1=CC=CC=C1 BDYZUNGZVADADC-UHFFFAOYSA-N 0.000 claims 1
- QGEVTHVVPPEWMD-UHFFFAOYSA-N 1-[3-(benzenesulfonyl)propyl]-3-[3-(diethylamino)propyl]-1-propan-2-ylurea Chemical compound CCN(CC)CCCNC(=O)N(C(C)C)CCCS(=O)(=O)C1=CC=CC=C1 QGEVTHVVPPEWMD-UHFFFAOYSA-N 0.000 claims 1
- HEQRCRDWYIWJFU-UHFFFAOYSA-N 3-[2-(diethylamino)ethyl]-1-[2-(4-methylphenyl)sulfinylethyl]-1-propan-2-ylurea Chemical compound CCN(CC)CCNC(=O)N(C(C)C)CCS(=O)C1=CC=C(C)C=C1 HEQRCRDWYIWJFU-UHFFFAOYSA-N 0.000 claims 1
- DQFILEDQWQKIMM-UHFFFAOYSA-N 3-[2-(diethylamino)ethyl]-1-[2-(4-methylphenyl)sulfonylethyl]-1-propan-2-ylurea Chemical compound CCN(CC)CCNC(=O)N(C(C)C)CCS(=O)(=O)C1=CC=C(C)C=C1 DQFILEDQWQKIMM-UHFFFAOYSA-N 0.000 claims 1
- OXZPYJSEGQSLJG-UHFFFAOYSA-N 3-[2-(dimethylamino)ethyl]-1-(2-naphthalen-1-ylsulfanylethyl)-1-propan-2-ylurea Chemical compound C1=CC=C2C(SCCN(C(C)C)C(=O)NCCN(C)C)=CC=CC2=C1 OXZPYJSEGQSLJG-UHFFFAOYSA-N 0.000 claims 1
- GJSXJZQMEUGRST-UHFFFAOYSA-N CC1=CC=C(C=C1)S(=O)(=O)CCN(C(C)C)C(=O)N Chemical compound CC1=CC=C(C=C1)S(=O)(=O)CCN(C(C)C)C(=O)N GJSXJZQMEUGRST-UHFFFAOYSA-N 0.000 claims 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 177
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 172
- 239000000243 solution Substances 0.000 description 161
- 239000003921 oil Substances 0.000 description 128
- 235000019198 oils Nutrition 0.000 description 128
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 105
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 78
- 238000004458 analytical method Methods 0.000 description 61
- 239000010410 layer Substances 0.000 description 59
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 51
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 50
- 239000000203 mixture Substances 0.000 description 49
- 239000012458 free base Substances 0.000 description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 39
- 239000007787 solid Substances 0.000 description 37
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- 238000010992 reflux Methods 0.000 description 26
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 25
- 239000000047 product Substances 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- 238000001704 evaporation Methods 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 230000008020 evaporation Effects 0.000 description 21
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 17
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 206010003119 arrhythmia Diseases 0.000 description 15
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 13
- 239000004480 active ingredient Substances 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
- 239000011976 maleic acid Substances 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 8
- 230000006793 arrhythmia Effects 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 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 7
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- 239000000706 filtrate Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
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- 239000000463 material Substances 0.000 description 6
- VPPLBSVKOFEITE-UHFFFAOYSA-N n-[2-(benzenesulfonyl)ethyl]propan-2-amine Chemical compound CC(C)NCCS(=O)(=O)C1=CC=CC=C1 VPPLBSVKOFEITE-UHFFFAOYSA-N 0.000 description 6
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
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- 230000000747 cardiac effect Effects 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 5
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- 229960001922 sodium perborate Drugs 0.000 description 5
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- DPHNJPUOMLRELT-UHFFFAOYSA-N 2,3-dihydro-1h-inden-4-ol Chemical compound OC1=CC=CC2=C1CCC2 DPHNJPUOMLRELT-UHFFFAOYSA-N 0.000 description 4
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- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
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- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 4
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 4
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
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- 210000003191 femoral vein Anatomy 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 229960004194 lidocaine Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- RHMQNXNXUZLEIY-UHFFFAOYSA-N methanol;2-propan-2-yloxypropane Chemical compound OC.CC(C)OC(C)C RHMQNXNXUZLEIY-UHFFFAOYSA-N 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- CURJNMSGPBXOGK-UHFFFAOYSA-N n',n'-di(propan-2-yl)ethane-1,2-diamine Chemical compound CC(C)N(C(C)C)CCN CURJNMSGPBXOGK-UHFFFAOYSA-N 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- LIUGRXFEJOSPIA-UHFFFAOYSA-N n'-benzyl-n'-methylethane-1,2-diamine Chemical compound NCCN(C)CC1=CC=CC=C1 LIUGRXFEJOSPIA-UHFFFAOYSA-N 0.000 description 1
- PHWISQNXPLXQRU-UHFFFAOYSA-N n,n-dimethylcarbamothioyl chloride Chemical compound CN(C)C(Cl)=S PHWISQNXPLXQRU-UHFFFAOYSA-N 0.000 description 1
- PKIHBVBGNNVQLX-UHFFFAOYSA-N n-(2-naphthalen-2-ylsulfanylethyl)propan-2-amine;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(SCCNC(C)C)=CC=C21 PKIHBVBGNNVQLX-UHFFFAOYSA-N 0.000 description 1
- XZHDRPHEFLNCNA-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)sulfanylethyl]propan-2-amine;hydrochloride Chemical compound Cl.CC(C)NCCSC1=CC=C(Cl)C(Cl)=C1 XZHDRPHEFLNCNA-UHFFFAOYSA-N 0.000 description 1
- KZKWGXQAMKHKGK-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)sulfonylethyl]propan-2-amine Chemical compound CC(C)NCCS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 KZKWGXQAMKHKGK-UHFFFAOYSA-N 0.000 description 1
- VEOXTCXOHHMWQD-UHFFFAOYSA-N n-[2-(4-chlorophenyl)sulfonylethyl]propan-2-amine Chemical compound CC(C)NCCS(=O)(=O)C1=CC=C(Cl)C=C1 VEOXTCXOHHMWQD-UHFFFAOYSA-N 0.000 description 1
- ZODNMAISYLFSAN-UHFFFAOYSA-N n-[2-(4-fluorophenyl)sulfanylethyl]propan-2-amine;hydrochloride Chemical compound Cl.CC(C)NCCSC1=CC=C(F)C=C1 ZODNMAISYLFSAN-UHFFFAOYSA-N 0.000 description 1
- JCMGQXFXAVGUBR-UHFFFAOYSA-N n-[2-(4-methoxyphenyl)sulfonylethyl]propan-2-amine Chemical compound COC1=CC=C(S(=O)(=O)CCNC(C)C)C=C1 JCMGQXFXAVGUBR-UHFFFAOYSA-N 0.000 description 1
- ABCMQEWNGOVMCX-UHFFFAOYSA-N n-[2-(4-methoxyphenyl)sulfonylethyl]propan-2-amine;hydrochloride Chemical compound Cl.COC1=CC=C(S(=O)(=O)CCNC(C)C)C=C1 ABCMQEWNGOVMCX-UHFFFAOYSA-N 0.000 description 1
- ZGHDQSWEJBOANY-UHFFFAOYSA-N n-[2-(4-tert-butylphenyl)sulfonylethyl]propan-2-amine Chemical compound CC(C)NCCS(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 ZGHDQSWEJBOANY-UHFFFAOYSA-N 0.000 description 1
- FZEBVEKQWAUQIT-UHFFFAOYSA-N n-[2-(benzenesulfonyl)ethyl]propan-2-amine;hydrochloride Chemical compound Cl.CC(C)NCCS(=O)(=O)C1=CC=CC=C1 FZEBVEKQWAUQIT-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- JZRHVCORTRGUJJ-UHFFFAOYSA-N n-pentan-2-ylbenzenesulfonamide Chemical compound CCCC(C)NS(=O)(=O)C1=CC=CC=C1 JZRHVCORTRGUJJ-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SEXOVMIIVBKGGM-UHFFFAOYSA-N naphthalene-1-thiol Chemical compound C1=CC=C2C(S)=CC=CC2=C1 SEXOVMIIVBKGGM-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 150000002926 oxygen Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- KZQOANVNISGCOE-UHFFFAOYSA-N phenyl n-[2-(3,4-dichlorophenyl)sulfanylethyl]-n-propan-2-ylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)N(C(C)C)CCSC1=CC=C(Cl)C(Cl)=C1 KZQOANVNISGCOE-UHFFFAOYSA-N 0.000 description 1
- RSVOAEOUUDEBLP-UHFFFAOYSA-N phenyl n-[2-(4-chlorophenyl)sulfanylethyl]-n-propan-2-ylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)N(C(C)C)CCSC1=CC=C(Cl)C=C1 RSVOAEOUUDEBLP-UHFFFAOYSA-N 0.000 description 1
- VLKQYRUSJQZCRX-UHFFFAOYSA-N phenyl n-[2-(4-chlorophenyl)sulfonylethyl]-n-propan-2-ylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)N(C(C)C)CCS(=O)(=O)C1=CC=C(Cl)C=C1 VLKQYRUSJQZCRX-UHFFFAOYSA-N 0.000 description 1
- KHFGNBZOAOLKTM-UHFFFAOYSA-N phenyl n-[2-(4-fluorophenyl)sulfanylethyl]-n-propan-2-ylcarbamate Chemical compound C=1C=CC=CC=1OC(=O)N(C(C)C)CCSC1=CC=C(F)C=C1 KHFGNBZOAOLKTM-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- ZRHANBBTXQZFSP-UHFFFAOYSA-M potassium;4-amino-3,5,6-trichloropyridine-2-carboxylate Chemical compound [K+].NC1=C(Cl)C(Cl)=NC(C([O-])=O)=C1Cl ZRHANBBTXQZFSP-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- LZMATGARSSLFMQ-UHFFFAOYSA-N propan-2-ylurea Chemical compound CC(C)NC(N)=O LZMATGARSSLFMQ-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 150000004685 tetrahydrates Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- 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
- 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
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/43—Y being a hetero atom
- C07C323/44—X or Y being nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
- C07C335/08—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26527881A | 1981-05-20 | 1981-05-20 | |
| US26527881 | 1981-05-20 | ||
| US34545282A | 1982-02-03 | 1982-02-03 | |
| US34545282 | 1982-02-03 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI821776A0 FI821776A0 (fi) | 1982-05-19 |
| FI76557B FI76557B (fi) | 1988-07-29 |
| FI76557C true FI76557C (fi) | 1988-11-10 |
Family
ID=26951096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI821776A FI76557C (fi) | 1981-05-20 | 1982-05-19 | Foerfarande foer framstaellning av farmakologiskt aktiva n-(aryltioalkyl)-n'-(aminoalkyl)-ureafoereningar. |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0066415B1 (OSRAM) |
| KR (1) | KR890001811B1 (OSRAM) |
| AU (1) | AU544976B2 (OSRAM) |
| CA (1) | CA1180013A (OSRAM) |
| DE (1) | DE3266645D1 (OSRAM) |
| DK (1) | DK228482A (OSRAM) |
| ES (3) | ES512329A0 (OSRAM) |
| FI (1) | FI76557C (OSRAM) |
| GR (1) | GR76412B (OSRAM) |
| HK (1) | HK96986A (OSRAM) |
| IE (1) | IE53342B1 (OSRAM) |
| IL (1) | IL65567A (OSRAM) |
| IN (1) | IN155992B (OSRAM) |
| NO (1) | NO153848C (OSRAM) |
| NZ (1) | NZ200669A (OSRAM) |
| PH (1) | PH23473A (OSRAM) |
| PT (1) | PT74930B (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL74140A (en) * | 1984-04-10 | 1988-05-31 | Robins Co Inc A H | Substituted n-((amino)alkyl)-1-pyrrolidine,-1-piperidine and-1-homopiperidine-carboxamides and pharmaceutical compositions containing them |
| US4895840A (en) * | 1987-06-10 | 1990-01-23 | A. H. Robins Company, Incorporated | N-(aryl-,aryloxy-,arylthio-arylsulfinyl-and arylsulfonyl-)alkyl-N,N'-(or n'n')alkylaminoalkyl ureas and cyanoguanidines |
| FR2664269B1 (fr) * | 1990-07-05 | 1992-10-02 | Roussel Uclaf | Nouveaux derives n-substitues d'alpha-mercapto alkylamines, leur procede de preparation, leur application a titre de medicaments et les compositions les renfermant. |
| WO2001023350A1 (en) * | 1999-09-28 | 2001-04-05 | Nihon Nohyaku Co., Ltd. | Thioalkylamine derivatives and process for the preparation thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2832756A (en) * | 1955-04-15 | 1958-04-29 | Rohm & Haas | Monomeric polymerizable ureido and thioureido compounds, methods for producing them and polymers thereof |
| FR2296406A1 (fr) * | 1974-12-31 | 1976-07-30 | Oreal | Nouvelles compositions cosmetiques a base de derives sulfoxydes de la cysteamine |
| GB1604674A (en) * | 1977-05-17 | 1981-12-16 | Allen & Hanburys Ltd | Aminoalkyl-benzene derivatives |
-
1982
- 1982-04-21 IL IL65567A patent/IL65567A/xx unknown
- 1982-05-12 PH PH27278A patent/PH23473A/en unknown
- 1982-05-13 GR GR68143A patent/GR76412B/el unknown
- 1982-05-18 IE IE1191/82A patent/IE53342B1/en unknown
- 1982-05-18 IN IN557/CAL/82A patent/IN155992B/en unknown
- 1982-05-19 ES ES512329A patent/ES512329A0/es active Granted
- 1982-05-19 CA CA000403325A patent/CA1180013A/en not_active Expired
- 1982-05-19 DK DK228482A patent/DK228482A/da not_active Application Discontinuation
- 1982-05-19 ES ES512328A patent/ES8303303A1/es not_active Expired
- 1982-05-19 NZ NZ200669A patent/NZ200669A/en unknown
- 1982-05-19 FI FI821776A patent/FI76557C/fi not_active IP Right Cessation
- 1982-05-19 PT PT74930A patent/PT74930B/pt unknown
- 1982-05-19 EP EP82302557A patent/EP0066415B1/en not_active Expired
- 1982-05-19 DE DE8282302557T patent/DE3266645D1/de not_active Expired
- 1982-05-19 ES ES512330A patent/ES512330A0/es active Granted
- 1982-05-19 NO NO821668A patent/NO153848C/no unknown
- 1982-05-20 KR KR8202205A patent/KR890001811B1/ko not_active Expired
- 1982-05-20 AU AU83881/82A patent/AU544976B2/en not_active Ceased
-
1986
- 1986-12-11 HK HK969/86A patent/HK96986A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0066415A2 (en) | 1982-12-08 |
| KR890001811B1 (ko) | 1989-05-23 |
| PH23473A (en) | 1989-08-07 |
| ES512328A0 (es) | 1983-02-01 |
| IE53342B1 (en) | 1988-10-26 |
| AU544976B2 (en) | 1985-06-27 |
| NZ200669A (en) | 1985-12-13 |
| NO153848B (no) | 1986-02-24 |
| ES8303305A1 (es) | 1983-02-01 |
| ES512330A0 (es) | 1983-02-01 |
| IN155992B (OSRAM) | 1985-04-20 |
| AU8388182A (en) | 1982-11-25 |
| IL65567A (en) | 1985-11-29 |
| NO821668L (no) | 1982-11-22 |
| EP0066415A3 (en) | 1983-09-14 |
| DE3266645D1 (de) | 1985-11-07 |
| DK228482A (da) | 1982-11-21 |
| KR830010057A (ko) | 1983-12-24 |
| NO153848C (no) | 1986-06-04 |
| EP0066415B1 (en) | 1985-10-02 |
| IE821191L (en) | 1982-11-20 |
| IL65567A0 (en) | 1982-07-30 |
| PT74930A (en) | 1982-06-01 |
| FI76557B (fi) | 1988-07-29 |
| CA1180013A (en) | 1984-12-27 |
| FI821776A0 (fi) | 1982-05-19 |
| ES8303304A1 (es) | 1983-02-01 |
| ES8303303A1 (es) | 1983-02-01 |
| GR76412B (OSRAM) | 1984-08-10 |
| ES512329A0 (es) | 1983-02-01 |
| HK96986A (en) | 1986-12-19 |
| PT74930B (en) | 1983-12-07 |
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