CH527172A - Verfahren zur Herstellung von Sulfonylharnstoffen oder -semicarbaziden - Google Patents
Verfahren zur Herstellung von Sulfonylharnstoffen oder -semicarbazidenInfo
- Publication number
- CH527172A CH527172A CH488568A CH488568A CH527172A CH 527172 A CH527172 A CH 527172A CH 488568 A CH488568 A CH 488568A CH 488568 A CH488568 A CH 488568A CH 527172 A CH527172 A CH 527172A
- Authority
- CH
- Switzerland
- Prior art keywords
- lower alkyl
- opt
- substituted
- radical
- carbon atoms
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims abstract description 11
- 125000003884 phenylalkyl group Chemical group 0.000 title abstract 4
- 125000001931 aliphatic group Chemical group 0.000 title abstract 2
- -1 hexamethylenimino Chemical group 0.000 claims abstract description 58
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- MZPZAIVRISPTJQ-UHFFFAOYSA-N 2,3,3a,4,5,6-hexahydro-1h-isoindole Chemical compound C1CCC2CNCC2=C1 MZPZAIVRISPTJQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- PDELQDSYLBLPQO-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-indole Chemical compound C1CCCC2NCCC21 PDELQDSYLBLPQO-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
- 235000013877 carbamide Nutrition 0.000 claims description 21
- 150000003349 semicarbazides Chemical class 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 150000003672 ureas Chemical class 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 5
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 4
- 239000003849 aromatic solvent Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 230000007717 exclusion Effects 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 125000006413 ring segment Chemical group 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 93
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
- 239000000203 mixture Substances 0.000 description 22
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 19
- 229910000104 sodium hydride Inorganic materials 0.000 description 19
- 239000012312 sodium hydride Substances 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 16
- 239000004202 carbamide Substances 0.000 description 14
- 229940100389 Sulfonylurea Drugs 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 10
- 229910021529 ammonia Inorganic materials 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000155 melt Substances 0.000 description 9
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CNWSQCLBDWYLAN-UHFFFAOYSA-N butylurea Chemical compound CCCCNC(N)=O CNWSQCLBDWYLAN-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000020477 pH reduction Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- ZQZJKHIIQFPZCS-UHFFFAOYSA-N propylurea Chemical compound CCCNC(N)=O ZQZJKHIIQFPZCS-UHFFFAOYSA-N 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- ASRMWYDEZPXXBA-UHFFFAOYSA-N (sulfonylamino)urea Chemical class NC(=O)NN=S(=O)=O ASRMWYDEZPXXBA-UHFFFAOYSA-N 0.000 description 2
- MFSBMDDDBZVNEO-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)sulfonyl-3-propylurea Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C(Cl)=C1 MFSBMDDDBZVNEO-UHFFFAOYSA-N 0.000 description 2
- TYZHJGCYLYXPSB-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-3-cyclohexylurea Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 TYZHJGCYLYXPSB-UHFFFAOYSA-N 0.000 description 2
- KJEOOPXZTLEKJY-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-3-piperidin-1-ylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCC1 KJEOOPXZTLEKJY-UHFFFAOYSA-N 0.000 description 2
- DNIIWANRGRGVRG-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-cyclohexylurea Chemical compound C=1C=CC=CC=1S(=O)(=O)NC(=O)NC1CCCCC1 DNIIWANRGRGVRG-UHFFFAOYSA-N 0.000 description 2
- ZMTSMVZAFDWQRM-UHFFFAOYSA-N 2-phenylethylurea Chemical compound NC(=O)NCCC1=CC=CC=C1 ZMTSMVZAFDWQRM-UHFFFAOYSA-N 0.000 description 2
- NYIBPWGZGSXURD-UHFFFAOYSA-N 3,4-dichlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1Cl NYIBPWGZGSXURD-UHFFFAOYSA-N 0.000 description 2
- DTJVECUKADWGMO-UHFFFAOYSA-N 4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1 DTJVECUKADWGMO-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- RIGBPMDIGYBTBJ-UHFFFAOYSA-N glycyclamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 RIGBPMDIGYBTBJ-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- AFOGBLYPWJJVAL-UHFFFAOYSA-N phenbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=CC=C1 AFOGBLYPWJJVAL-UHFFFAOYSA-N 0.000 description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 150000003461 sulfonyl halides Chemical class 0.000 description 2
- OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- OBSWMRYVEFRSHI-UHFFFAOYSA-N 1-(benzenesulfonyl)-3-piperidin-1-ylurea Chemical compound C1(=CC=CC=C1)S(=O)(=O)NC(=O)NN1CCCCC1 OBSWMRYVEFRSHI-UHFFFAOYSA-N 0.000 description 1
- IRMBSCHMQJLMEG-UHFFFAOYSA-N 1-butyl-3-(4-methoxyphenyl)sulfonylurea Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(OC)C=C1 IRMBSCHMQJLMEG-UHFFFAOYSA-N 0.000 description 1
- XTOBSLUVJNOXGB-UHFFFAOYSA-N 1-cyclooctyl-3-(4-methylphenyl)sulfonylurea Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCCCC1 XTOBSLUVJNOXGB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LACFLXDRFOQEFZ-UHFFFAOYSA-N 4-ethylbenzenesulfonyl chloride Chemical compound CCC1=CC=C(S(Cl)(=O)=O)C=C1 LACFLXDRFOQEFZ-UHFFFAOYSA-N 0.000 description 1
- NTSFJZORNYYLFW-UHFFFAOYSA-N 4-methylbenzenesulfonyl bromide Chemical compound CC1=CC=C(S(Br)(=O)=O)C=C1 NTSFJZORNYYLFW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241001101720 Murgantia histrionica Species 0.000 description 1
- DQNHNVJSWPPXFY-UHFFFAOYSA-N N-cyclooctylurea Chemical compound NC(=O)NC1CCCCCCC1 DQNHNVJSWPPXFY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- LSNDGFYQJRXEAR-UHFFFAOYSA-N benzenesulfonamidourea Chemical class NC(=O)NNS(=O)(=O)C1=CC=CC=C1 LSNDGFYQJRXEAR-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- JESCPVSKEGXYSC-UHFFFAOYSA-N chlorobenzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.ClC1=CC=CC=C1 JESCPVSKEGXYSC-UHFFFAOYSA-N 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- SKJJGBRWKOFYAD-UHFFFAOYSA-N piperidin-1-ylurea Chemical compound NC(=O)NN1CCCCC1 SKJJGBRWKOFYAD-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000007127 saponification reaction 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
- 238000005245 sintering Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- AWLUSOLTCFEHNE-UHFFFAOYSA-N sodium;urea Chemical compound [Na].NC(N)=O AWLUSOLTCFEHNE-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- WZHRJGWXUCLILI-UHFFFAOYSA-N sulfonylcarbamic acid Chemical class OC(=O)N=S(=O)=O WZHRJGWXUCLILI-UHFFFAOYSA-N 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
Classifications
-
- 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
- C07D295/22—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 with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
- C07D295/32—Nitrogen atoms acylated with carboxylic or carbonic acids, or their nitrogen or sulfur analogues
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0052032 | 1967-04-05 | ||
| DEF0053634 | 1967-09-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH527172A true CH527172A (de) | 1972-08-31 |
Family
ID=25977603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH488568A CH527172A (de) | 1967-04-05 | 1968-04-03 | Verfahren zur Herstellung von Sulfonylharnstoffen oder -semicarbaziden |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT281053B (enrdf_load_stackoverflow) |
| CH (1) | CH527172A (enrdf_load_stackoverflow) |
| DE (2) | DE1618399A1 (enrdf_load_stackoverflow) |
| DK (1) | DK119975B (enrdf_load_stackoverflow) |
| ES (1) | ES352338A1 (enrdf_load_stackoverflow) |
| FR (1) | FR1558886A (enrdf_load_stackoverflow) |
| NL (1) | NL6804107A (enrdf_load_stackoverflow) |
| SE (1) | SE343298B (enrdf_load_stackoverflow) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1329812A (en) * | 1971-02-15 | 1973-09-12 | Science Union & Cie | Benzenesulphonyl semicarbazides and a process for their preparation |
| DE2413514C3 (de) | 1974-03-21 | 1982-03-04 | Hoechst Ag, 6000 Frankfurt | N-Acylaminoathylbenzolsulfonyl-N'-methylharnstoffe, Verfahren zu ihrer Herstellung und deren Verwendung |
| US5705585A (en) | 1993-06-30 | 1998-01-06 | Arqule, Inc. | Aminimide-containing molecules and materials as molecular recognition agents |
| JPH08500339A (ja) * | 1992-06-30 | 1996-01-16 | レゴマー パートナーズ，エル．ピー． | アミンイミド含有分子および分子認識剤としての物質 |
| CA2179983A1 (en) * | 1993-12-28 | 1995-07-06 | Joseph C. Hogan, Jr. | Modular design and synthesis of aminimide containing molecules |
| US5734082A (en) | 1994-10-20 | 1998-03-31 | Arqule Inc. | Hydroxyethyl aminimides |
| US5712171A (en) | 1995-01-20 | 1998-01-27 | Arqule, Inc. | Method of generating a plurality of chemical compounds in a spatially arranged array |
-
1967
- 1967-04-05 DE DE19671618399 patent/DE1618399A1/de active Pending
- 1967-09-30 DE DE19671670933 patent/DE1670933A1/de active Pending
-
1968
- 1968-03-22 NL NL6804107A patent/NL6804107A/xx not_active Application Discontinuation
- 1968-04-03 CH CH488568A patent/CH527172A/de not_active IP Right Cessation
- 1968-04-03 AT AT323568A patent/AT281053B/de not_active IP Right Cessation
- 1968-04-03 ES ES352338A patent/ES352338A1/es not_active Expired
- 1968-04-04 DK DK148768A patent/DK119975B/da unknown
- 1968-04-05 SE SE458668A patent/SE343298B/xx unknown
- 1968-04-15 FR FR1558886D patent/FR1558886A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK119975B (da) | 1971-03-22 |
| NL6804107A (enrdf_load_stackoverflow) | 1968-10-07 |
| FR1558886A (enrdf_load_stackoverflow) | 1969-02-28 |
| DE1618399A1 (de) | 1970-11-05 |
| DE1670933A1 (de) | 1971-04-08 |
| SE343298B (sv) | 1972-03-06 |
| ES352338A1 (es) | 1970-01-01 |
| AT281053B (de) | 1970-05-11 |
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