CA1049038A - Amidinoureas - Google Patents
AmidinoureasInfo
- Publication number
- CA1049038A CA1049038A CA74204780A CA204780A CA1049038A CA 1049038 A CA1049038 A CA 1049038A CA 74204780 A CA74204780 A CA 74204780A CA 204780 A CA204780 A CA 204780A CA 1049038 A CA1049038 A CA 1049038A
- Authority
- CA
- Canada
- Prior art keywords
- amidino
- urea
- chloro
- biguanide
- methyl
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- -1 2-iodo-4-ethylphenylisocyanate Chemical compound 0.000 claims description 149
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229940123208 Biguanide Drugs 0.000 claims description 24
- XNCOSPRUTUOJCJ-UHFFFAOYSA-N Biguanide Chemical compound NC(N)=NC(N)=N XNCOSPRUTUOJCJ-UHFFFAOYSA-N 0.000 claims description 21
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 14
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 8
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 8
- QCDIKKQNJMTXFA-UHFFFAOYSA-N 1-(2-chloro-4-methylphenyl)-3-(diaminomethylidene)urea Chemical compound CC1=CC=C(NC(=O)NC(N)=N)C(Cl)=C1 QCDIKKQNJMTXFA-UHFFFAOYSA-N 0.000 claims description 6
- ADYCAQMNDOBKKP-UHFFFAOYSA-N 1-(diaminomethylidene)-3-(2,6-difluorophenyl)urea Chemical compound NC(=N)NC(=O)NC1=C(F)C=CC=C1F ADYCAQMNDOBKKP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- MLMWUUSXMWYJDP-UHFFFAOYSA-N 1-(2-bromo-4-methylphenyl)-3-(diaminomethylidene)urea Chemical compound CC1=CC=C(NC(=O)NC(N)=N)C(Br)=C1 MLMWUUSXMWYJDP-UHFFFAOYSA-N 0.000 claims description 5
- OXFPIUXTFWKNRQ-UHFFFAOYSA-N 1-(2-chloro-6-fluorophenyl)-3-(diaminomethylidene)urea Chemical compound NC(N)=NC(=O)NC1=C(F)C=CC=C1Cl OXFPIUXTFWKNRQ-UHFFFAOYSA-N 0.000 claims description 5
- FFAWNQBQSBZLKM-UHFFFAOYSA-N 1-(4-bromo-2,6-dichlorophenyl)-3-(diaminomethylidene)urea Chemical compound NC(=N)NC(=O)NC1=C(Cl)C=C(Br)C=C1Cl FFAWNQBQSBZLKM-UHFFFAOYSA-N 0.000 claims description 5
- LPNQZYHDCRCPRR-UHFFFAOYSA-N 1-(diaminomethylidene)-3-(2,6-dichloro-4-methylphenyl)urea Chemical compound CC1=CC(Cl)=C(NC(=O)NC(N)=N)C(Cl)=C1 LPNQZYHDCRCPRR-UHFFFAOYSA-N 0.000 claims description 5
- KBZVAHQLKHWPST-UHFFFAOYSA-N 1-(diaminomethylidene)-3-(2,6-dichlorophenyl)urea Chemical compound NC(N)=NC(=O)NC1=C(Cl)C=CC=C1Cl KBZVAHQLKHWPST-UHFFFAOYSA-N 0.000 claims description 5
- OYWRJJBDWXNKRO-UHFFFAOYSA-N 1-(4-bromo-2-chloro-6-methylphenyl)-3-(diaminomethylidene)urea Chemical compound CC1=CC(Br)=CC(Cl)=C1NC(=O)NC(N)=N OYWRJJBDWXNKRO-UHFFFAOYSA-N 0.000 claims description 4
- OWDCRKNKUCSXKJ-UHFFFAOYSA-N 1-(diaminomethylidene)-3-(2,4-dichlorophenyl)urea Chemical compound NC(=N)NC(=O)NC1=CC=C(Cl)C=C1Cl OWDCRKNKUCSXKJ-UHFFFAOYSA-N 0.000 claims description 4
- PZXIBLJRRIQYKP-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2,6-dichlorophenyl)guanidine Chemical compound NC(N)=NC(N)=NC1=C(Cl)C=CC=C1Cl PZXIBLJRRIQYKP-UHFFFAOYSA-N 0.000 claims description 3
- 150000004283 biguanides Chemical class 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical class O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims 13
- 239000000126 substance Substances 0.000 claims 13
- 125000001475 halogen functional group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- BMFSTWONJUKKBH-UHFFFAOYSA-N 1,3-dichloro-2-isocyanato-5-methylbenzene Chemical compound CC1=CC(Cl)=C(N=C=O)C(Cl)=C1 BMFSTWONJUKKBH-UHFFFAOYSA-N 0.000 claims 1
- HMVKMAMIRAVXAN-UHFFFAOYSA-N 1,3-dichloro-2-isocyanatobenzene Chemical compound ClC1=CC=CC(Cl)=C1N=C=O HMVKMAMIRAVXAN-UHFFFAOYSA-N 0.000 claims 1
- YXHDLKWTPVMIOH-UHFFFAOYSA-N 1,3-difluoro-2-isocyanatobenzene Chemical compound FC1=CC=CC(F)=C1N=C=O YXHDLKWTPVMIOH-UHFFFAOYSA-N 0.000 claims 1
- YUOBDYAVSVCCNI-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2,4-dichlorophenyl)guanidine Chemical compound NC(N)=NC(N)=NC1=CC=C(Cl)C=C1Cl YUOBDYAVSVCCNI-UHFFFAOYSA-N 0.000 claims 1
- XQFLNNBZLXBUMI-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2,6-dichloro-4-methylphenyl)guanidine Chemical compound CC1=CC(Cl)=C(NC(=N)NC(N)=N)C(Cl)=C1 XQFLNNBZLXBUMI-UHFFFAOYSA-N 0.000 claims 1
- ZVASOCGASDVJTH-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2,6-difluorophenyl)guanidine Chemical compound NC(N)=NC(N)=NC1=C(F)C=CC=C1F ZVASOCGASDVJTH-UHFFFAOYSA-N 0.000 claims 1
- HXCQXVWVRJDQEA-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(4-ethyl-2-iodophenyl)guanidine Chemical compound CCC1=CC=C(NC(=N)NC(N)=N)C(I)=C1 HXCQXVWVRJDQEA-UHFFFAOYSA-N 0.000 claims 1
- OLBJNSPBWLCTOT-UHFFFAOYSA-N 2,4-dichloro-1-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C(Cl)=C1 OLBJNSPBWLCTOT-UHFFFAOYSA-N 0.000 claims 1
- SBUVFTSXGVZGPA-UHFFFAOYSA-N 2-(2-bromo-4-methylphenyl)-1-(diaminomethylidene)guanidine Chemical compound CC1=CC=C(NC(=N)NC(N)=N)C(Br)=C1 SBUVFTSXGVZGPA-UHFFFAOYSA-N 0.000 claims 1
- UVVFIFNNQGSNMX-UHFFFAOYSA-N 2-(2-chloro-4-methylphenyl)-1-(diaminomethylidene)guanidine Chemical compound CC1=CC=C(NC(=N)NC(N)=N)C(Cl)=C1 UVVFIFNNQGSNMX-UHFFFAOYSA-N 0.000 claims 1
- SCRXCIYIDHGLQA-UHFFFAOYSA-N 2-(2-chloro-6-fluorophenyl)-1-(diaminomethylidene)guanidine Chemical compound NC(=N)NC(=N)NC1=C(F)C=CC=C1Cl SCRXCIYIDHGLQA-UHFFFAOYSA-N 0.000 claims 1
- NLSUINOVFLSKCP-UHFFFAOYSA-N 2-(4-bromo-2,6-dichlorophenyl)-1-(diaminomethylidene)guanidine Chemical compound ClC1=C(C(=CC(=C1)Br)Cl)NC(=N)NC(=N)N NLSUINOVFLSKCP-UHFFFAOYSA-N 0.000 claims 1
- HDTUBLAAFISJRQ-UHFFFAOYSA-N 2-(4-bromo-2-chloro-6-methylphenyl)-1-(diaminomethylidene)guanidine Chemical compound CC1=CC(Br)=CC(Cl)=C1NC(=N)NC(N)=N HDTUBLAAFISJRQ-UHFFFAOYSA-N 0.000 claims 1
- HUSGEXYNVCQXKA-UHFFFAOYSA-N 2-bromo-1-isocyanato-4-methylbenzene Chemical compound CC1=CC=C(N=C=O)C(Br)=C1 HUSGEXYNVCQXKA-UHFFFAOYSA-N 0.000 claims 1
- QVCZOTVTRWNPAF-UHFFFAOYSA-N 2-chloro-1-isocyanato-4-methylbenzene Chemical compound CC1=CC=C(N=C=O)C(Cl)=C1 QVCZOTVTRWNPAF-UHFFFAOYSA-N 0.000 claims 1
- ABZXFFSLKUIGHE-UHFFFAOYSA-N 2-chloro-4-fluoro-1-isocyanatobenzene Chemical compound FC1=CC=C(N=C=O)C(Cl)=C1 ABZXFFSLKUIGHE-UHFFFAOYSA-N 0.000 claims 1
- ORUUIJNIVAHYOR-UHFFFAOYSA-N 2-chloro-4-iodo-1-isocyanatobenzene Chemical compound ClC1=CC(I)=CC=C1N=C=O ORUUIJNIVAHYOR-UHFFFAOYSA-N 0.000 claims 1
- MMRGGBUYPQQMBY-UHFFFAOYSA-N 5-bromo-1,3-dichloro-2-isocyanatobenzene Chemical compound ClC1=CC(Br)=CC(Cl)=C1N=C=O MMRGGBUYPQQMBY-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000002496 gastric effect Effects 0.000 abstract description 4
- 206010020601 Hyperchlorhydria Diseases 0.000 abstract description 2
- 206010020772 Hypertension Diseases 0.000 abstract description 2
- 208000005392 Spasm Diseases 0.000 abstract description 2
- 208000025865 Ulcer Diseases 0.000 abstract description 2
- 230000036269 ulceration Effects 0.000 abstract description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 17
- 239000004202 carbamide Substances 0.000 description 16
- 239000000460 chlorine Substances 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000001246 bromo group Chemical group Br* 0.000 description 8
- 125000001309 chloro group Chemical group Cl* 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- VCICDODDLJVAMV-UHFFFAOYSA-N 3-(diaminomethylidene)-1-(2,6-dichlorophenyl)-1-methylurea Chemical compound NC(=N)NC(=O)N(C)C1=C(Cl)C=CC=C1Cl VCICDODDLJVAMV-UHFFFAOYSA-N 0.000 description 5
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 5
- 231100000252 nontoxic Toxicity 0.000 description 5
- 230000003000 nontoxic effect Effects 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 4
- 235000011167 hydrochloric acid Nutrition 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- UAIFOYXPOOWRRD-UHFFFAOYSA-N 1-(2-bromo-4-chlorophenyl)-3-(diaminomethylidene)urea Chemical compound NC(=N)NC(=O)NC1=CC=C(Cl)C=C1Br UAIFOYXPOOWRRD-UHFFFAOYSA-N 0.000 description 3
- KJOSTYAYEPMARI-UHFFFAOYSA-N 1-(2-bromo-6-chlorophenyl)-3-(diaminomethylidene)urea Chemical compound NC(=N)NC(=O)NC1=C(Cl)C=CC=C1Br KJOSTYAYEPMARI-UHFFFAOYSA-N 0.000 description 3
- PHNZBLPHKJSKRK-UHFFFAOYSA-N 1-(2-chloro-4-fluorophenyl)-3-(diaminomethylidene)urea Chemical compound NC(=N)NC(=O)NC1=CC=C(F)C=C1Cl PHNZBLPHKJSKRK-UHFFFAOYSA-N 0.000 description 3
- XWPPIJPOMBRJMB-UHFFFAOYSA-N 1-(4-bromo-2-chlorophenyl)-3-(diaminomethylidene)urea Chemical compound NC(=N)NC(=O)NC1=CC=C(Br)C=C1Cl XWPPIJPOMBRJMB-UHFFFAOYSA-N 0.000 description 3
- AKBMRPWYKSGYFF-UHFFFAOYSA-N 1-(diaminomethylidene)-3-(2,4-dichloro-6-fluorophenyl)urea Chemical compound NC(=N)NC(=O)NC1=C(F)C=C(Cl)C=C1Cl AKBMRPWYKSGYFF-UHFFFAOYSA-N 0.000 description 3
- PSHONDXYBGKITH-UHFFFAOYSA-N 1-(diaminomethylidene)-3-(2,6-dibromophenyl)urea Chemical compound NC(N)=NC(=O)NC1=C(Br)C=CC=C1Br PSHONDXYBGKITH-UHFFFAOYSA-N 0.000 description 3
- DRCAIESCJLDBPS-UHFFFAOYSA-N 1-(diaminomethylidene)-3-(2,6-dichloro-4-ethylphenyl)urea Chemical compound CCC1=CC(Cl)=C(NC(=O)NC(N)=N)C(Cl)=C1 DRCAIESCJLDBPS-UHFFFAOYSA-N 0.000 description 3
- MVWKDWUETXWSJT-UHFFFAOYSA-N 1-(diaminomethylidene)-3-(4-ethyl-2-fluorophenyl)urea Chemical compound CCC1=CC=C(NC(=O)NC(N)=N)C(F)=C1 MVWKDWUETXWSJT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229910002651 NO3 Inorganic materials 0.000 description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001448 anilines Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- SSYNNVXRKBFPBJ-UHFFFAOYSA-N 1-(2-bromo-4,6-dichlorophenyl)-3-(diaminomethylidene)urea Chemical compound NC(=N)NC(=O)NC1=C(Cl)C=C(Cl)C=C1Br SSYNNVXRKBFPBJ-UHFFFAOYSA-N 0.000 description 2
- QCENRHQRHPNZPS-UHFFFAOYSA-N 1-(2-bromo-4,6-difluorophenyl)-3-(diaminomethylidene)urea Chemical compound NC(=N)NC(=O)NC1=C(F)C=C(F)C=C1Br QCENRHQRHPNZPS-UHFFFAOYSA-N 0.000 description 2
- KZAABNDHGRBMCA-UHFFFAOYSA-N 1-(2-bromo-4,6-dimethylphenyl)-3-(diaminomethylidene)urea Chemical compound CC1=CC(C)=C(NC(=O)NC(N)=N)C(Br)=C1 KZAABNDHGRBMCA-UHFFFAOYSA-N 0.000 description 2
- WLCYQOGCXOGDSC-UHFFFAOYSA-N 1-(2-bromo-4-chlorophenyl)-3-(diaminomethylidene)-1-methylurea Chemical compound NC(=N)NC(=O)N(C)C1=CC=C(Cl)C=C1Br WLCYQOGCXOGDSC-UHFFFAOYSA-N 0.000 description 2
- NEGBKHDERGIXCG-UHFFFAOYSA-N 1-(2-bromo-4-fluorophenyl)-3-(diaminomethylidene)urea Chemical compound NC(=N)NC(=O)NC1=CC=C(F)C=C1Br NEGBKHDERGIXCG-UHFFFAOYSA-N 0.000 description 2
- GMMPILRUZZTIPN-UHFFFAOYSA-N 1-(2-bromo-6-fluorophenyl)-3-(diaminomethylidene)urea Chemical compound NC(=N)NC(=O)NC1=C(F)C=CC=C1Br GMMPILRUZZTIPN-UHFFFAOYSA-N 0.000 description 2
- JDDVWQQDGXIWSA-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(diaminomethylidene)urea Chemical compound NC(=N)NC(=O)NC1=CC=CC=C1Br JDDVWQQDGXIWSA-UHFFFAOYSA-N 0.000 description 2
- GPOSSFVIFBFHRS-UHFFFAOYSA-N 1-(2-chloro-4,6-difluorophenyl)-3-(diaminomethylidene)urea Chemical compound NC(=N)NC(=O)NC1=C(F)C=C(F)C=C1Cl GPOSSFVIFBFHRS-UHFFFAOYSA-N 0.000 description 2
- GWEFRLKGYDCARZ-UHFFFAOYSA-N 1-(2-chloro-4-ethylphenyl)-3-(diaminomethylidene)urea Chemical compound CCC1=CC=C(NC(=O)NC(N)=N)C(Cl)=C1 GWEFRLKGYDCARZ-UHFFFAOYSA-N 0.000 description 2
- NYCGNCBWROOKFA-UHFFFAOYSA-N 1-(2-chloro-4-propylphenyl)-3-(diaminomethylidene)-1-methylurea Chemical compound CCCC1=CC=C(N(C)C(=O)NC(N)=N)C(Cl)=C1 NYCGNCBWROOKFA-UHFFFAOYSA-N 0.000 description 2
- BLHRSMBQBWAYHK-UHFFFAOYSA-N 1-(2-chloro-4-propylphenyl)-3-(diaminomethylidene)urea Chemical compound CCCC1=CC=C(NC(=O)NC(N)=N)C(Cl)=C1 BLHRSMBQBWAYHK-UHFFFAOYSA-N 0.000 description 2
- SELMTSRRPHOXHD-UHFFFAOYSA-N 1-(2-chloro-6-fluorophenyl)-3-(diaminomethylidene)-1-methylurea Chemical compound NC(=N)NC(=O)N(C)C1=C(F)C=CC=C1Cl SELMTSRRPHOXHD-UHFFFAOYSA-N 0.000 description 2
- WMFPEWHOKIVRRT-UHFFFAOYSA-N 1-(2-chloro-6-methoxyphenyl)-3-(diaminomethylidene)urea Chemical compound COC1=CC=CC(Cl)=C1NC(=O)NC(N)=N WMFPEWHOKIVRRT-UHFFFAOYSA-N 0.000 description 2
- LQIJFASMGMALLJ-UHFFFAOYSA-N 1-(2-chloro-6-nitrophenyl)-3-(diaminomethylidene)urea Chemical compound NC(=N)NC(=O)NC1=C(Cl)C=CC=C1[N+]([O-])=O LQIJFASMGMALLJ-UHFFFAOYSA-N 0.000 description 2
- DOTWUEJTERLXKJ-UHFFFAOYSA-N 1-(4-bromo-2-chloro-6-fluorophenyl)-3-(diaminomethylidene)urea Chemical compound NC(=N)NC(=O)NC1=C(F)C=C(Br)C=C1Cl DOTWUEJTERLXKJ-UHFFFAOYSA-N 0.000 description 2
- RYHUNQXWDVFAAW-UHFFFAOYSA-N 1-(4-chloro-2,6-difluorophenyl)-3-(diaminomethylidene)urea Chemical compound NC(=N)NC(=O)NC1=C(F)C=C(Cl)C=C1F RYHUNQXWDVFAAW-UHFFFAOYSA-N 0.000 description 2
- YVTUOFHTTUSJQA-UHFFFAOYSA-N 1-(4-chloro-2-fluorophenyl)-3-(diaminomethylidene)urea Chemical compound NC(=N)NC(=O)NC1=CC=C(Cl)C=C1F YVTUOFHTTUSJQA-UHFFFAOYSA-N 0.000 description 2
- XRGLAPWSRYQNHZ-UHFFFAOYSA-N 1-(diaminomethylidene)-3-(2,4,6-trichlorophenyl)urea Chemical compound NC(=N)NC(=O)NC1=C(Cl)C=C(Cl)C=C1Cl XRGLAPWSRYQNHZ-UHFFFAOYSA-N 0.000 description 2
- APORUJARFXUBNI-UHFFFAOYSA-N 1-(diaminomethylidene)-3-(2,4-diethyl-6-fluorophenyl)urea Chemical compound CCC1=CC(F)=C(NC(=O)NC(N)=N)C(CC)=C1 APORUJARFXUBNI-UHFFFAOYSA-N 0.000 description 2
- TUEFFVPVDPYSAQ-UHFFFAOYSA-N 1-(diaminomethylidene)-3-(2,4-difluorophenyl)urea Chemical compound NC(=N)NC(=O)NC1=CC=C(F)C=C1F TUEFFVPVDPYSAQ-UHFFFAOYSA-N 0.000 description 2
- IPUUVIORKWBVLW-UHFFFAOYSA-N 1-(diaminomethylidene)-3-(2,6-dichloro-4-fluorophenyl)urea Chemical compound NC(=N)NC(=O)NC1=C(Cl)C=C(F)C=C1Cl IPUUVIORKWBVLW-UHFFFAOYSA-N 0.000 description 2
- XUUVCCFAUMBOSO-UHFFFAOYSA-N 1-(diaminomethylidene)-3-(2-fluoro-4-methylphenyl)urea Chemical compound CC1=CC=C(NC(=O)NC(N)=N)C(F)=C1 XUUVCCFAUMBOSO-UHFFFAOYSA-N 0.000 description 2
- STRDOISCXCQAKH-UHFFFAOYSA-N 1-(diaminomethylidene)-3-(2-fluorophenyl)urea Chemical compound NC(=N)NC(=O)NC1=CC=CC=C1F STRDOISCXCQAKH-UHFFFAOYSA-N 0.000 description 2
- FRJFKKCYRHRKRP-UHFFFAOYSA-N 2,6-dichloro-n-methylaniline Chemical compound CNC1=C(Cl)C=CC=C1Cl FRJFKKCYRHRKRP-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
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- OLOOMVFGFOMGAR-UHFFFAOYSA-N 3-(diaminomethylidene)-1-(2,4-dichlorophenyl)-1-methylurea Chemical compound NC(=N)NC(=O)N(C)C1=CC=C(Cl)C=C1Cl OLOOMVFGFOMGAR-UHFFFAOYSA-N 0.000 description 2
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- DCLPFHMMMGAEPS-UHFFFAOYSA-N 3-(diaminomethylidene)-1-(2,4-difluorophenyl)-1-propylguanidine Chemical compound NC(N)=NC(=N)N(CCC)C1=CC=C(F)C=C1F DCLPFHMMMGAEPS-UHFFFAOYSA-N 0.000 description 1
- DMTMGFOQOAZQNF-UHFFFAOYSA-N 3-(diaminomethylidene)-1-(2,4-difluorophenyl)-1-propylurea Chemical compound NC(=N)NC(=O)N(CCC)C1=CC=C(F)C=C1F DMTMGFOQOAZQNF-UHFFFAOYSA-N 0.000 description 1
- CAAFGOJAXLNBLK-UHFFFAOYSA-N 3-(diaminomethylidene)-1-(2,6-dibromophenyl)-1-methylurea Chemical compound NC(=N)NC(=O)N(C)C1=C(Br)C=CC=C1Br CAAFGOJAXLNBLK-UHFFFAOYSA-N 0.000 description 1
- NTSTUEVIIBTFAN-UHFFFAOYSA-N 3-(diaminomethylidene)-1-(2,6-dichloro-4-ethylphenyl)-1-methylurea Chemical compound CCC1=CC(Cl)=C(N(C)C(=O)NC(N)=N)C(Cl)=C1 NTSTUEVIIBTFAN-UHFFFAOYSA-N 0.000 description 1
- GCTXVMFPBQIVOZ-UHFFFAOYSA-N 3-(diaminomethylidene)-1-(2,6-dichloro-4-propylphenyl)-1-methylurea Chemical compound CCCC1=CC(Cl)=C(N(C)C(=O)NC(N)=N)C(Cl)=C1 GCTXVMFPBQIVOZ-UHFFFAOYSA-N 0.000 description 1
- UGBZZEKLNOFIIP-UHFFFAOYSA-N 3-(diaminomethylidene)-1-(2,6-dichlorophenyl)-1-propylguanidine Chemical compound NC(=N)NC(=N)N(CCC)C1=C(Cl)C=CC=C1Cl UGBZZEKLNOFIIP-UHFFFAOYSA-N 0.000 description 1
- QBXSDJFBIDTYPW-UHFFFAOYSA-N 3-(diaminomethylidene)-1-(2,6-difluorophenyl)-1-methylurea Chemical compound NC(=N)NC(=O)N(C)C1=C(F)C=CC=C1F QBXSDJFBIDTYPW-UHFFFAOYSA-N 0.000 description 1
- WQMUWWAUIZOYBG-UHFFFAOYSA-N 3-(diaminomethylidene)-1-(2,6-difluorophenyl)-1-propylurea Chemical compound NC(=N)NC(=O)N(CCC)C1=C(F)C=CC=C1F WQMUWWAUIZOYBG-UHFFFAOYSA-N 0.000 description 1
- UJAVVFYIFBYBSA-UHFFFAOYSA-N 3-(diaminomethylidene)-1-(2-fluoro-4,6-dimethylphenyl)-1-methylguanidine Chemical compound NC(=N)NC(=N)N(C)C1=C(C)C=C(C)C=C1F UJAVVFYIFBYBSA-UHFFFAOYSA-N 0.000 description 1
- SUQZBBSNSKAWTI-UHFFFAOYSA-N 3-(diaminomethylidene)-1-(2-fluoro-4-methylphenyl)-1-methylurea Chemical compound NC(=N)NC(=O)N(C)C1=CC=C(C)C=C1F SUQZBBSNSKAWTI-UHFFFAOYSA-N 0.000 description 1
- BZIPATMAACBJOW-UHFFFAOYSA-N 3-(diaminomethylidene)-1-(2-fluoro-6-methoxyphenyl)-1-methylurea Chemical compound COC1=CC=CC(F)=C1N(C)C(=O)NC(N)=N BZIPATMAACBJOW-UHFFFAOYSA-N 0.000 description 1
- WMBYZNRCUUIKHG-UHFFFAOYSA-N 3-(diaminomethylidene)-1-(2-fluoro-6-nitrophenyl)-1-methylurea Chemical compound NC(=N)NC(=O)N(C)C1=C(F)C=CC=C1[N+]([O-])=O WMBYZNRCUUIKHG-UHFFFAOYSA-N 0.000 description 1
- AMDNUQLZVMXCQX-UHFFFAOYSA-N 3-(diaminomethylidene)-1-(4-ethyl-2-fluorophenyl)-1-methylurea Chemical compound CCC1=CC=C(N(C)C(=O)NC(N)=N)C(F)=C1 AMDNUQLZVMXCQX-UHFFFAOYSA-N 0.000 description 1
- FFTFCGKIWUFFDP-UHFFFAOYSA-N 3-(diaminomethylidene)-1-[2,4-dichloro-6-(trifluoromethyl)phenyl]-1-methylurea Chemical compound NC(=N)NC(=O)N(C)C1=C(Cl)C=C(Cl)C=C1C(F)(F)F FFTFCGKIWUFFDP-UHFFFAOYSA-N 0.000 description 1
- XSLYYTFDJDAMPI-UHFFFAOYSA-N 3-(diaminomethylidene)-1-[2,4-difluoro-6-(trifluoromethyl)phenyl]-1-methylurea Chemical compound NC(=N)NC(=O)N(C)C1=C(F)C=C(F)C=C1C(F)(F)F XSLYYTFDJDAMPI-UHFFFAOYSA-N 0.000 description 1
- KMYNFFSDFIWXTA-UHFFFAOYSA-N 3-(diaminomethylidene)-1-ethyl-1-(2-fluoro-4,6-dimethylphenyl)guanidine Chemical compound NC(=N)NC(=N)N(CC)C1=C(C)C=C(C)C=C1F KMYNFFSDFIWXTA-UHFFFAOYSA-N 0.000 description 1
- SBNIZOMSKMHWLY-UHFFFAOYSA-N 3-(diaminomethylidene)-1-ethyl-1-(2-fluoro-4-methylphenyl)urea Chemical compound NC(=N)NC(=O)N(CC)C1=CC=C(C)C=C1F SBNIZOMSKMHWLY-UHFFFAOYSA-N 0.000 description 1
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- HGNONAHZRMPHON-UHFFFAOYSA-N 4-bromo-2-fluoro-n-methylaniline Chemical compound CNC1=CC=C(Br)C=C1F HGNONAHZRMPHON-UHFFFAOYSA-N 0.000 description 1
- WRSZHBJQAAQAKJ-UHFFFAOYSA-N 4-chloro-2-fluoro-n-propylaniline Chemical compound CCCNC1=CC=C(Cl)C=C1F WRSZHBJQAAQAKJ-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- QGEPSZBLSOLJFH-UHFFFAOYSA-N C(CC)NC1=C(C=CC=C1Cl)Cl.C(CC)NC1=C(C=C(C=C1)CC)F Chemical compound C(CC)NC1=C(C=CC=C1Cl)Cl.C(CC)NC1=C(C=C(C=C1)CC)F QGEPSZBLSOLJFH-UHFFFAOYSA-N 0.000 description 1
- DILMQANQZBXWRZ-UHFFFAOYSA-N C(CCC)NC1=C(C=C(C=C1)C)F.C(CCC)NC1=C(C=C(C=C1)C)Cl Chemical compound C(CCC)NC1=C(C=C(C=C1)C)F.C(CCC)NC1=C(C=C(C=C1)C)Cl DILMQANQZBXWRZ-UHFFFAOYSA-N 0.000 description 1
- DZHPAFYXMXJYBW-UHFFFAOYSA-N C(N)(=N)NC(=O)N(C)C1=C(C=C(C=C1Br)C)C.C(N)(=N)NC(=O)N(C)C1=C(C=C(C=C1Cl)C)C Chemical compound C(N)(=N)NC(=O)N(C)C1=C(C=C(C=C1Br)C)C.C(N)(=N)NC(=O)N(C)C1=C(C=C(C=C1Cl)C)C DZHPAFYXMXJYBW-UHFFFAOYSA-N 0.000 description 1
- NNTSQMYFTSBNOW-UHFFFAOYSA-N C(N)(=N)NC(=O)N(C)C1=C(C=C(C=C1Cl)F)F.C(N)(=N)NC(=O)N(C)C1=C(C=C(C=C1Cl)Br)Br Chemical compound C(N)(=N)NC(=O)N(C)C1=C(C=C(C=C1Cl)F)F.C(N)(=N)NC(=O)N(C)C1=C(C=C(C=C1Cl)Br)Br NNTSQMYFTSBNOW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- XGVXNTVBGYLJIR-UHFFFAOYSA-N fluoroiodomethane Chemical compound FCI XGVXNTVBGYLJIR-UHFFFAOYSA-N 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XNEFVTBPCXGIRX-UHFFFAOYSA-M methanesulfinate Chemical compound CS([O-])=O XNEFVTBPCXGIRX-UHFFFAOYSA-M 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- KBJLUBYSRLTYID-UHFFFAOYSA-N n-butyl-2,4-dichloroaniline Chemical compound CCCCNC1=CC=C(Cl)C=C1Cl KBJLUBYSRLTYID-UHFFFAOYSA-N 0.000 description 1
- XIQDLTHOELVUDR-UHFFFAOYSA-N n-butyl-2,4-difluoroaniline Chemical compound CCCCNC1=CC=C(F)C=C1F XIQDLTHOELVUDR-UHFFFAOYSA-N 0.000 description 1
- SXXLALYAVYIVGB-UHFFFAOYSA-N n-ethyl-2,4-difluoroaniline Chemical compound CCNC1=CC=C(F)C=C1F SXXLALYAVYIVGB-UHFFFAOYSA-N 0.000 description 1
- PYJRYGGMMNMYNW-UHFFFAOYSA-N n-ethyl-2-fluoro-4-methylaniline Chemical compound CCNC1=CC=C(C)C=C1F PYJRYGGMMNMYNW-UHFFFAOYSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000004672 propanoic acids Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37977373A | 1973-07-16 | 1973-07-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1049038A true CA1049038A (en) | 1979-02-20 |
Family
ID=23498624
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA74204780A Expired CA1049038A (en) | 1973-07-16 | 1974-07-15 | Amidinoureas |
Country Status (4)
| Country | Link |
|---|---|
| JP (2) | JPS5714668B2 (en, 2012) |
| CA (1) | CA1049038A (en, 2012) |
| DE (1) | DE2433993C3 (en, 2012) |
| SE (1) | SE409112B (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6293402U (en, 2012) * | 1985-12-02 | 1987-06-15 |
-
1974
- 1974-07-15 SE SE7409227A patent/SE409112B/xx not_active IP Right Cessation
- 1974-07-15 DE DE2433993A patent/DE2433993C3/de not_active Expired
- 1974-07-15 CA CA74204780A patent/CA1049038A/en not_active Expired
- 1974-07-16 JP JP8162474A patent/JPS5714668B2/ja not_active Expired
-
1980
- 1980-10-27 JP JP15058880A patent/JPS5695160A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE2433993C3 (de) | 1982-05-27 |
| DE2433993B2 (de) | 1981-10-15 |
| SE7409227L (sv) | 1975-01-17 |
| DE2433993A1 (de) | 1975-02-06 |
| JPS5695160A (en) | 1981-08-01 |
| SE409112B (sv) | 1979-07-30 |
| JPS5716097B2 (en, 2012) | 1982-04-02 |
| AU7121774A (en) | 1976-01-15 |
| JPS5040545A (en, 2012) | 1975-04-14 |
| JPS5714668B2 (en, 2012) | 1982-03-25 |
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