FR2497199A1 - Procede, composition et concentre pour la preparation de derives d'uree substitues - Google Patents
Procede, composition et concentre pour la preparation de derives d'uree substitues Download PDFInfo
- Publication number
- FR2497199A1 FR2497199A1 FR8124411A FR8124411A FR2497199A1 FR 2497199 A1 FR2497199 A1 FR 2497199A1 FR 8124411 A FR8124411 A FR 8124411A FR 8124411 A FR8124411 A FR 8124411A FR 2497199 A1 FR2497199 A1 FR 2497199A1
- Authority
- FR
- France
- Prior art keywords
- solvent
- water
- weight
- acetone
- organic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims description 42
- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 7
- 239000012141 concentrate Substances 0.000 title claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title abstract description 8
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 94
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- 239000002904 solvent Substances 0.000 claims description 23
- 150000001412 amines Chemical class 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 150000003672 ureas Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 7
- 239000003960 organic solvent Substances 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
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- VREVKZLUMZQJRI-UHFFFAOYSA-N [SH2]=N Chemical compound [SH2]=N VREVKZLUMZQJRI-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 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
- 229940086542 triethylamine Drugs 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- -1 [2- (2-methoxy-5-chlorobenzamido) ethyl] -benzenesulfonyl- Chemical group 0.000 description 14
- 239000000155 melt Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 9
- 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 7
- 238000001816 cooling Methods 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- 239000004202 carbamide Substances 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000012948 isocyanate Substances 0.000 description 5
- 150000002513 isocyanates Chemical class 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- CYMRPDYINXWJFU-UHFFFAOYSA-N 2-carbamoylbenzoic acid Chemical compound NC(=O)C1=CC=CC=C1C(O)=O CYMRPDYINXWJFU-UHFFFAOYSA-N 0.000 description 4
- 230000006181 N-acylation Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 150000003456 sulfonamides Chemical class 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 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
- DSUPUOGOCIFZBG-UHFFFAOYSA-N 2-(phenylcarbamoyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)NC1=CC=CC=C1 DSUPUOGOCIFZBG-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 238000007259 addition reaction Methods 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- YZKMURMKJCXVIE-UHFFFAOYSA-N 1-(2-aminoethyl)-3-phenylurea Chemical compound NCCNC(=O)NC1=CC=CC=C1 YZKMURMKJCXVIE-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
- 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
- OBGFMRSXJROQDT-UHFFFAOYSA-N 1-methoxy-1-methylurea Chemical compound CON(C)C(N)=O OBGFMRSXJROQDT-UHFFFAOYSA-N 0.000 description 1
- HCRZGHMVMHLMNF-UHFFFAOYSA-N 1-methyl-3-(oxomethylidene)urea Chemical compound CNC(=O)N=C=O HCRZGHMVMHLMNF-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
- KEBUEWXZQBMCNB-UHFFFAOYSA-N 1h-benzimidazol-2-yl carbamate Chemical compound C1=CC=C2NC(OC(=O)N)=NC2=C1 KEBUEWXZQBMCNB-UHFFFAOYSA-N 0.000 description 1
- HZFOJDJUDSUXSX-UHFFFAOYSA-N 2-(butylcarbamoyl)benzoic acid Chemical compound CCCCNC(=O)C1=CC=CC=C1C(O)=O HZFOJDJUDSUXSX-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 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
- 241001465754 Metazoa Species 0.000 description 1
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
- GPLUYPFUSVDDII-UHFFFAOYSA-N N=[S+]C1=CC=CC=C1 Chemical compound N=[S+]C1=CC=CC=C1 GPLUYPFUSVDDII-UHFFFAOYSA-N 0.000 description 1
- YVOFKSGFOGNJHF-UHFFFAOYSA-N [SH2]=N.C(C1=CC=CC=C1)(=O)O Chemical compound [SH2]=N.C(C1=CC=CC=C1)(=O)O YVOFKSGFOGNJHF-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
- 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
- 239000004480 active ingredient Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000001217 buttock Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 125000006333 difluoro benzoyl group Chemical group 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 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
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- DZIRZHBFUPWNFK-UHFFFAOYSA-N n-alkylphthalic monoamide Chemical compound CNC(=O)C1=CC=CC=C1C(O)=O DZIRZHBFUPWNFK-UHFFFAOYSA-N 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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000001953 recrystallisation 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
- 230000009291 secondary effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 239000002341 toxic gas Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Pyridine Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
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 (2)
| Publication Number | Publication Date |
|---|---|
| FR2497199A1 true FR2497199A1 (fr) | 1982-07-02 |
| FR2497199B1 FR2497199B1 (en, 2012) | 1984-06-29 |
Family
ID=10962729
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8124411A Granted FR2497199A1 (fr) | 1980-12-29 | 1981-12-29 | Procede, composition et concentre pour la preparation de derives d'uree substitues |
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
Non-Patent Citations (1)
| Title |
|---|
| Néant * |
Also Published As
| Publication number | Publication date |
|---|---|
| PL234489A1 (en, 2012) | 1982-08-16 |
| HU185294B (en) | 1984-12-28 |
| 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 |
| 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 |
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| ST | Notification of lapse |