HU185294B - Process for producing substituted urea derivatives - Google Patents
Process for producing substituted urea derivatives Download PDFInfo
- Publication number
- HU185294B HU185294B HU803135A HU313580A HU185294B HU 185294 B HU185294 B HU 185294B HU 803135 A HU803135 A HU 803135A HU 313580 A HU313580 A HU 313580A HU 185294 B HU185294 B HU 185294B
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- acetone
- water
- phenyl
- urea derivatives
- Prior art date
Links
- 150000003672 ureas Chemical class 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims abstract description 13
- 150000001412 amines Chemical class 0.000 claims abstract description 15
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 143
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 150000007530 organic bases Chemical class 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002576 ketones Chemical group 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000003884 phenylalkyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 abstract description 2
- 230000004071 biological effect Effects 0.000 abstract description 2
- 230000002363 herbicidal effect Effects 0.000 abstract description 2
- 230000000749 insecticidal effect Effects 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 101100242909 Streptococcus pneumoniae (strain ATCC BAA-255 / R6) pbpA gene Proteins 0.000 abstract 2
- 101100269618 Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) aliA gene Proteins 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000005429 oxyalkyl group Chemical group 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 16
- 238000003756 stirring Methods 0.000 description 16
- 239000000725 suspension Substances 0.000 description 13
- -1 2-methoxy-5-chloro-benzamido Chemical group 0.000 description 11
- XNXURANYMGXTNI-UHFFFAOYSA-N [SH2]=N.OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC=C1 Chemical compound [SH2]=N.OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC=C1 XNXURANYMGXTNI-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 230000006181 N-acylation Effects 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- VHKREQQTTZHFAC-UHFFFAOYSA-N [SH2]=N.CCCCNC(=O)C1=CC=CC=C1C(O)=O Chemical compound [SH2]=N.CCCCNC(=O)C1=CC=CC=C1C(O)=O VHKREQQTTZHFAC-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- ZWOULFZCQXICLZ-UHFFFAOYSA-N 1,3-dimethyl-1-phenylurea Chemical compound CNC(=O)N(C)C1=CC=CC=C1 ZWOULFZCQXICLZ-UHFFFAOYSA-N 0.000 description 1
- RLFMTSNQZYKQLE-UHFFFAOYSA-N 1-(2-hydroxyethyl)-3-phenylurea Chemical compound OCCNC(=O)NC1=CC=CC=C1 RLFMTSNQZYKQLE-UHFFFAOYSA-N 0.000 description 1
- NXVUMPGGLOJSOO-UHFFFAOYSA-N 1-(4-chloro-2-nitrophenyl)-3-cyclohexylurea Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1NC(=O)NC1CCCCC1 NXVUMPGGLOJSOO-UHFFFAOYSA-N 0.000 description 1
- NTRVJFMCRHBODE-UHFFFAOYSA-N 1-(4-methoxyphenyl)-3-phenylurea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=CC=C1 NTRVJFMCRHBODE-UHFFFAOYSA-N 0.000 description 1
- LPAFKALFDTZCSC-UHFFFAOYSA-N 1-benzyl-3-(4-chlorophenyl)urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NCC1=CC=CC=C1 LPAFKALFDTZCSC-UHFFFAOYSA-N 0.000 description 1
- XXFBRXQVPJVXFB-UHFFFAOYSA-N 1-benzyl-3-phenylurea Chemical compound C=1C=CC=CC=1NC(=O)NCC1=CC=CC=C1 XXFBRXQVPJVXFB-UHFFFAOYSA-N 0.000 description 1
- JFYNDZSUPRRXEA-UHFFFAOYSA-N 1-butyl-3-(4-methylphenyl)urea Chemical compound CCCCNC(=O)NC1=CC=C(C)C=C1 JFYNDZSUPRRXEA-UHFFFAOYSA-N 0.000 description 1
- WPLYTRWMCWBZEN-UHFFFAOYSA-N 1-cyclohexyl-3-phenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1CCCCC1 WPLYTRWMCWBZEN-UHFFFAOYSA-N 0.000 description 1
- XUFXDODGXLVPNJ-UHFFFAOYSA-N 1-ethyl-3-phenylurea Chemical compound CCNC(=O)NC1=CC=CC=C1 XUFXDODGXLVPNJ-UHFFFAOYSA-N 0.000 description 1
- CDTIOGUIESQOJT-UHFFFAOYSA-N 1-phenyl-3-[2-(phenylcarbamoylamino)ethyl]urea Chemical compound C=1C=CC=CC=1NC(=O)NCCNC(=O)NC1=CC=CC=C1 CDTIOGUIESQOJT-UHFFFAOYSA-N 0.000 description 1
- CIBUQXSYGPGEGX-UHFFFAOYSA-N 1-phenyl-3-propan-2-ylurea Chemical compound CC(C)NC(=O)NC1=CC=CC=C1 CIBUQXSYGPGEGX-UHFFFAOYSA-N 0.000 description 1
- FDMIXRXCYIIUDY-UHFFFAOYSA-N 1-phenyl-3-pyridin-2-ylurea Chemical compound C=1C=CC=NC=1NC(=O)NC1=CC=CC=C1 FDMIXRXCYIIUDY-UHFFFAOYSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- DTCJYIIKPVRVDD-UHFFFAOYSA-N Benzthiazuron Chemical compound C1=CC=C2SC(NC(=O)NC)=NC2=C1 DTCJYIIKPVRVDD-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- NLYNUTMZTCLNOO-UHFFFAOYSA-N Chlorbromuron Chemical compound CON(C)C(=O)NC1=CC=C(Br)C(Cl)=C1 NLYNUTMZTCLNOO-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- KXZIXJSKGAELEC-UHFFFAOYSA-N [SH2]=N.CCNC(=O)C1=CC=CC=C1C(O)=O Chemical compound [SH2]=N.CCNC(=O)C1=CC=CC=C1C(O)=O KXZIXJSKGAELEC-UHFFFAOYSA-N 0.000 description 1
- OLDRZWKGXUGNOW-UHFFFAOYSA-N [SH2]=N.CNC(=O)C1=CC=CC=C1C(O)=O Chemical compound [SH2]=N.CNC(=O)C1=CC=CC=C1C(O)=O OLDRZWKGXUGNOW-UHFFFAOYSA-N 0.000 description 1
- BEXNGNKZKUBBQC-UHFFFAOYSA-N [SH2]=N.OC(=O)C1=CC=CC=C1C(=O)NC1CCCCC1 Chemical compound [SH2]=N.OC(=O)C1=CC=CC=C1C(=O)NC1CCCCC1 BEXNGNKZKUBBQC-UHFFFAOYSA-N 0.000 description 1
- KCEGBVVSJJFOPO-UHFFFAOYSA-N [SH2]=N.OC(=O)C1=CC=CC=C1C(=O)NCC1=CC=CC=C1 Chemical compound [SH2]=N.OC(=O)C1=CC=CC=C1C(=O)NCC1=CC=CC=C1 KCEGBVVSJJFOPO-UHFFFAOYSA-N 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 241000411851 herbal medicine Species 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- RMZWDJQFNRZMOQ-UHFFFAOYSA-N n-phenyl-3,4-dihydro-1h-isoquinoline-2-carboxamide Chemical compound C1CC2=CC=CC=C2CN1C(=O)NC1=CC=CC=C1 RMZWDJQFNRZMOQ-UHFFFAOYSA-N 0.000 description 1
- MNKRJSJKVHUXIG-UHFFFAOYSA-N n-phenylmorpholine-4-carboxamide Chemical compound C1COCCN1C(=O)NC1=CC=CC=C1 MNKRJSJKVHUXIG-UHFFFAOYSA-N 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU803135A HU185294B (en) | 1980-12-29 | 1980-12-29 | Process for producing substituted urea derivatives |
| GB8138962A GB2091257B (en) | 1980-12-29 | 1981-12-24 | Process composition and concentrate for preparing substituted urea derivatives |
| YU03080/81A YU308081A (en) | 1980-12-29 | 1981-12-25 | Process for obtaining carbamide derivatives |
| SU813377199A SU1176834A3 (ru) | 1980-12-29 | 1981-12-28 | Способ получени производных мочевины |
| US06/334,470 US4435567A (en) | 1980-12-29 | 1981-12-28 | Process for preparing substituted urea derivatives |
| BR8108416A BR8108416A (pt) | 1980-12-29 | 1981-12-28 | Processo para a preparacao de derivados de ureia;composicao n-acilante;concentrado n-acilante |
| JP56210117A JPS57171957A (en) | 1980-12-29 | 1981-12-28 | Substituted urea derivative manufacture, composition and condensate |
| DE19813151685 DE3151685A1 (de) | 1980-12-29 | 1981-12-28 | Verfahren und komposition zur herstellung von substituierten harnstoffderivaten |
| PL1981234489A PL128520B1 (en) | 1980-12-29 | 1981-12-29 | Method of obtaining urea derivatives |
| DD81236378A DD202538A5 (de) | 1980-12-29 | 1981-12-29 | Verfahren zur herstellung von substituierten harnstoffderivaten |
| FR8124411A FR2497199A1 (fr) | 1980-12-29 | 1981-12-29 | Procede, composition et concentre pour la preparation de derives d'uree substitues |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU803135A HU185294B (en) | 1980-12-29 | 1980-12-29 | Process for producing substituted urea derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU185294B true HU185294B (en) | 1984-12-28 |
Family
ID=10962729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU803135A HU185294B (en) | 1980-12-29 | 1980-12-29 | Process for producing substituted urea derivatives |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4435567A (en, 2012) |
| JP (1) | JPS57171957A (en, 2012) |
| BR (1) | BR8108416A (en, 2012) |
| DD (1) | DD202538A5 (en, 2012) |
| DE (1) | DE3151685A1 (en, 2012) |
| FR (1) | FR2497199A1 (en, 2012) |
| GB (1) | GB2091257B (en, 2012) |
| HU (1) | HU185294B (en, 2012) |
| PL (1) | PL128520B1 (en, 2012) |
| SU (1) | SU1176834A3 (en, 2012) |
| YU (1) | YU308081A (en, 2012) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU185294B (en) | 1980-12-29 | 1984-12-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing substituted urea derivatives |
| US4670041A (en) * | 1981-12-16 | 1987-06-02 | E. I. Du Pont De Nemours And Company | Oxabicycloalkane herbicides |
| US4818271A (en) * | 1985-10-31 | 1989-04-04 | Fmc Corporation | Pyridinylurea compounds and agricultural uses |
| US4837348A (en) * | 1986-04-30 | 1989-06-06 | Varian Associates, Inc. | Bonded phase chromatographic supports |
| EP0427963B1 (de) * | 1989-11-10 | 1994-03-30 | Agrolinz Agrarchemikalien Gesellschaft M.B.H. | Verfahren zur Herstellung reiner, unsymmetrisch disubstituierter Harnstoffe |
| DE3940261A1 (de) * | 1989-12-06 | 1991-06-13 | Agrolinz Agrarchemikalien Muen | Verfahren zur herstellung reiner, unsymmetrisch disubstituierter harnstoffe |
| EP1473292A1 (en) * | 1997-11-03 | 2004-11-03 | Boehringer Ingelheim Pharmaceuticals, Inc. | Aromatic heterocyclic compounds as anti-inflammatory agents |
| WO1999023091A1 (en) | 1997-11-03 | 1999-05-14 | Boehringer Ingelheim Pharmaceuticals, Inc. | Aromatic heterocyclic compounds as anti-inflammatory agents |
| UA73492C2 (en) | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| JP2002537397A (ja) | 1999-02-22 | 2002-11-05 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | 抗炎症剤としての多環ヘテロ環式誘導体 |
| JP2002539206A (ja) | 1999-03-12 | 2002-11-19 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | 抗炎症剤としての芳香族複素環化合物 |
| US6358945B1 (en) * | 1999-03-12 | 2002-03-19 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as anti-inflammatory agents |
| CA2374737C (en) | 1999-07-09 | 2008-02-12 | Boehringer Ingelheim Pharmaceuticals, Inc. | Novel process for synthesis of heteroaryl-substituted urea compounds |
| MXPA02002578A (es) * | 1999-09-08 | 2002-10-23 | Guilford Pharm Inc | Compuestos de union a ciclofilina no peptidicos, y su uso. |
| MXPA02004879A (es) | 1999-11-16 | 2002-08-30 | Boehringer Ingelheim Pharma | Derivados de urea como agentes antiinflamatorios. |
| US6525046B1 (en) | 2000-01-18 | 2003-02-25 | Boehringer Ingelheim Pharmaceuticals, Inc. | Aromatic heterocyclic compounds as antiinflammatory agents |
| US6608052B2 (en) | 2000-02-16 | 2003-08-19 | Boehringer Ingelheim Pharmaceuticals, Inc. | Compounds useful as anti-inflammatory agents |
| WO2002059080A2 (en) | 2001-01-25 | 2002-08-01 | Guilford Pharmaceuticals Inc. | Trisubstituted carbocyclic cyclophilin binding compounds and their use |
| EP1392661A1 (en) | 2001-05-16 | 2004-03-03 | Boehringer Ingelheim Pharmaceuticals Inc. | Diarylurea derivatives useful as anti-inflammatory agents |
| CA2448626A1 (en) | 2001-05-25 | 2002-12-05 | Boehringer Ingelheim Pharmaceuticals, Inc. | Carbamate and oxamide compounds as inhibitors of cytokine production |
| US20030118575A1 (en) * | 2001-12-11 | 2003-06-26 | Boehringer Ingelheim Pharmaceuticals, Inc. | Method for administering BIRB 796 BS |
| JP4629978B2 (ja) * | 2002-02-25 | 2011-02-09 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | サイトカイン媒介疾患の治療に有用な１，４−二置換ベンゾ縮合シクロアルキル尿素化合物 |
| MX2013005479A (es) * | 2010-11-15 | 2013-06-12 | Abbvie Inc | Inhibidores de nampt. |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU184063B (en) * | 1979-11-08 | 1984-06-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing carbamoic-acid-phenyl-ester derivatives |
| HU185294B (en) | 1980-12-29 | 1984-12-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing substituted urea derivatives |
-
1980
- 1980-12-29 HU HU803135A patent/HU185294B/hu unknown
-
1981
- 1981-12-24 GB GB8138962A patent/GB2091257B/en not_active Expired
- 1981-12-25 YU YU03080/81A patent/YU308081A/xx unknown
- 1981-12-28 SU SU813377199A patent/SU1176834A3/ru active
- 1981-12-28 JP JP56210117A patent/JPS57171957A/ja active Pending
- 1981-12-28 DE DE19813151685 patent/DE3151685A1/de active Granted
- 1981-12-28 BR BR8108416A patent/BR8108416A/pt unknown
- 1981-12-28 US US06/334,470 patent/US4435567A/en not_active Expired - Fee Related
- 1981-12-29 FR FR8124411A patent/FR2497199A1/fr active Granted
- 1981-12-29 PL PL1981234489A patent/PL128520B1/pl unknown
- 1981-12-29 DD DD81236378A patent/DD202538A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| PL234489A1 (en, 2012) | 1982-08-16 |
| YU308081A (en) | 1983-10-31 |
| DE3151685C2 (en, 2012) | 1987-08-13 |
| FR2497199B1 (en, 2012) | 1984-06-29 |
| DE3151685A1 (de) | 1982-08-12 |
| GB2091257A (en) | 1982-07-28 |
| BR8108416A (pt) | 1982-10-13 |
| PL128520B1 (en) | 1984-02-29 |
| US4435567A (en) | 1984-03-06 |
| JPS57171957A (en) | 1982-10-22 |
| FR2497199A1 (fr) | 1982-07-02 |
| SU1176834A3 (ru) | 1985-08-30 |
| GB2091257B (en) | 1984-08-22 |
| DD202538A5 (de) | 1983-09-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |