JP2003507328A5 - - Google Patents
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- Publication number
- JP2003507328A5 JP2003507328A5 JP2001516534A JP2001516534A JP2003507328A5 JP 2003507328 A5 JP2003507328 A5 JP 2003507328A5 JP 2001516534 A JP2001516534 A JP 2001516534A JP 2001516534 A JP2001516534 A JP 2001516534A JP 2003507328 A5 JP2003507328 A5 JP 2003507328A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- cyclopropyl
- urea
- amino
- phenethyl
- 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.)
- Withdrawn
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- -1 carboxy, amino Chemical group 0.000 description 34
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 21
- 239000004202 carbamide Substances 0.000 description 21
- 238000000034 method Methods 0.000 description 20
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 15
- 125000000623 heterocyclic group Chemical group 0.000 description 14
- XAEGRAIWWBXIRR-UHFFFAOYSA-N 1h-pyrazol-5-ylurea Chemical class NC(=O)NC=1C=CNN=1 XAEGRAIWWBXIRR-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 13
- 125000000753 cycloalkyl group Chemical group 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 6
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 6
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 description 6
- 125000003282 alkyl amino group Chemical group 0.000 description 6
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 6
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 6
- 125000004414 alkyl thio group Chemical group 0.000 description 6
- 125000005336 allyloxy group Chemical group 0.000 description 6
- 125000004103 aminoalkyl group Chemical group 0.000 description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 125000004663 dialkyl amino group Chemical group 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 125000004043 oxo group Chemical group O=* 0.000 description 6
- 206010028980 Neoplasm Diseases 0.000 description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
- RRGJIRNODFCZTR-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(1h-indol-6-yl)urea Chemical compound C=1C=C2C=CNC2=CC=1NC(=O)NC(NN=1)=CC=1C1CC1 RRGJIRNODFCZTR-UHFFFAOYSA-N 0.000 description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 2
- KBWOXTUACGNTJX-UHFFFAOYSA-N 1-(1,3-benzothiazol-5-yl)-3-(5-cyclopropyl-1h-pyrazol-3-yl)urea Chemical compound C=1C=C2SC=NC2=CC=1NC(=O)NC(NN=1)=CC=1C1CC1 KBWOXTUACGNTJX-UHFFFAOYSA-N 0.000 description 2
- FUUVDMXWFLVEAL-UHFFFAOYSA-N 1-(1-benzylpiperidin-4-yl)-3-(5-cyclopentyl-1h-pyrazol-3-yl)urea Chemical compound C=1C(C2CCCC2)=NNC=1NC(=O)NC(CC1)CCN1CC1=CC=CC=C1 FUUVDMXWFLVEAL-UHFFFAOYSA-N 0.000 description 2
- HLYWVPZUDNCLTA-UHFFFAOYSA-N 1-(2-chlorophenyl)-3-(5-cyclopropyl-1h-pyrazol-3-yl)urea Chemical compound ClC1=CC=CC=C1NC(=O)NC1=CC(C2CC2)=NN1 HLYWVPZUDNCLTA-UHFFFAOYSA-N 0.000 description 2
- JNERJKKRDPVUEX-UHFFFAOYSA-N 1-(2-phenylethyl)-3-[5-(2-phenylethyl)-1h-pyrazol-3-yl]urea Chemical compound C=1C(CCC=2C=CC=CC=2)=NNC=1NC(=O)NCCC1=CC=CC=C1 JNERJKKRDPVUEX-UHFFFAOYSA-N 0.000 description 2
- LJWNEBAMSQLONR-UHFFFAOYSA-N 1-(3-acetylphenyl)-3-(5-cyclopropyl-1h-pyrazol-3-yl)urea Chemical compound CC(=O)C1=CC=CC(NC(=O)NC=2NN=C(C=2)C2CC2)=C1 LJWNEBAMSQLONR-UHFFFAOYSA-N 0.000 description 2
- LMAUENNWIDTDEI-UHFFFAOYSA-N 1-(3-aminophenyl)-3-(5-cyclopropyl-1h-pyrazol-3-yl)urea Chemical compound NC1=CC=CC(NC(=O)NC=2NN=C(C=2)C2CC2)=C1 LMAUENNWIDTDEI-UHFFFAOYSA-N 0.000 description 2
- AIEYGYPQUCKGQD-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-3-(5-cyclopropyl-1h-pyrazol-3-yl)urea Chemical compound C=1C=C2N=CNC2=CC=1NC(=O)NC(NN=1)=CC=1C1CC1 AIEYGYPQUCKGQD-UHFFFAOYSA-N 0.000 description 2
- DBJNONLXERNMRY-UHFFFAOYSA-N 1-(4-aminophenyl)-3-(5-cyclopropyl-1h-pyrazol-3-yl)urea Chemical compound C1=CC(N)=CC=C1NC(=O)NC1=CC(C2CC2)=NN1 DBJNONLXERNMRY-UHFFFAOYSA-N 0.000 description 2
- UVBKTBFRVPPOKN-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-(5-cyclopropyl-1h-pyrazol-3-yl)urea Chemical compound C=1C=C(C#N)C=CC=1NC(=O)NC(NN=1)=CC=1C1CC1 UVBKTBFRVPPOKN-UHFFFAOYSA-N 0.000 description 2
- LPAQWHHDOXAKNP-UHFFFAOYSA-N 1-(5-cyclopentyl-1h-pyrazol-3-yl)-3-(2-phenylethyl)urea Chemical compound C=1C(C2CCCC2)=NNC=1NC(=O)NCCC1=CC=CC=C1 LPAQWHHDOXAKNP-UHFFFAOYSA-N 0.000 description 2
- XHHMORVGUBZUCC-UHFFFAOYSA-N 1-(5-cyclopentyl-1h-pyrazol-3-yl)-3-[2-(3,4-dimethoxyphenyl)ethyl]urea Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)NC1=CC(C2CCCC2)=NN1 XHHMORVGUBZUCC-UHFFFAOYSA-N 0.000 description 2
- UVOYJUDGAPNFLO-UHFFFAOYSA-N 1-(5-cyclopentyl-1h-pyrazol-3-yl)-3-[2-(4-hydroxyphenyl)ethyl]urea Chemical compound C1=CC(O)=CC=C1CCNC(=O)NC1=CC(C2CCCC2)=NN1 UVOYJUDGAPNFLO-UHFFFAOYSA-N 0.000 description 2
- FPXSIHNCQOGEIE-UHFFFAOYSA-N 1-(5-cyclopentyl-1h-pyrazol-3-yl)-3-propylurea Chemical compound N1C(NC(=O)NCCC)=CC(C2CCCC2)=N1 FPXSIHNCQOGEIE-UHFFFAOYSA-N 0.000 description 2
- TUWACJYUEHXZQM-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(1h-indol-5-yl)urea Chemical compound C=1C=C2NC=CC2=CC=1NC(=O)NC(NN=1)=CC=1C1CC1 TUWACJYUEHXZQM-UHFFFAOYSA-N 0.000 description 2
- CQAUMHHMFNEAEF-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(2,3-dimethylphenyl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2NN=C(C=2)C2CC2)=C1C CQAUMHHMFNEAEF-UHFFFAOYSA-N 0.000 description 2
- KSTNBJOADDSFJM-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(2,4-dimethylphenyl)urea Chemical compound CC1=CC(C)=CC=C1NC(=O)NC1=CC(C2CC2)=NN1 KSTNBJOADDSFJM-UHFFFAOYSA-N 0.000 description 2
- RPOPBLOLIWMNIR-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(2,5-dimethylpyrazol-3-yl)urea Chemical compound CN1N=C(C)C=C1NC(=O)NC1=CC(C2CC2)=NN1 RPOPBLOLIWMNIR-UHFFFAOYSA-N 0.000 description 2
- YHSVZCPQAZCNPZ-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(2,6-dimethylphenyl)urea Chemical compound CC1=CC=CC(C)=C1NC(=O)NC1=CC(C2CC2)=NN1 YHSVZCPQAZCNPZ-UHFFFAOYSA-N 0.000 description 2
- NIYXUXSXSVROSP-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(2-hydroxyphenyl)urea Chemical compound OC1=CC=CC=C1NC(=O)NC1=CC(C2CC2)=NN1 NIYXUXSXSVROSP-UHFFFAOYSA-N 0.000 description 2
- FBGOFSYQLFPPIH-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC(C2CC2)=NN1 FBGOFSYQLFPPIH-UHFFFAOYSA-N 0.000 description 2
- OJRWHECJGITDRU-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(2-piperidin-1-ylethyl)urea Chemical compound C=1C(C2CC2)=NNC=1NC(=O)NCCN1CCCCC1 OJRWHECJGITDRU-UHFFFAOYSA-N 0.000 description 2
- WTENIFDFISCSNB-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(2-pyridin-2-ylethyl)urea Chemical compound C=1C(C2CC2)=NNC=1NC(=O)NCCC1=CC=CC=N1 WTENIFDFISCSNB-UHFFFAOYSA-N 0.000 description 2
- YWIJHJCJXNMHLF-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(2-pyrrolidin-1-ylethyl)urea Chemical compound C=1C(C2CC2)=NNC=1NC(=O)NCCN1CCCC1 YWIJHJCJXNMHLF-UHFFFAOYSA-N 0.000 description 2
- SBZFKIXGUOMWGU-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(3,4-dimethoxyphenyl)urea Chemical compound C1=C(OC)C(OC)=CC=C1NC(=O)NC1=CC(C2CC2)=NN1 SBZFKIXGUOMWGU-UHFFFAOYSA-N 0.000 description 2
- IRDDJYLPWTWDKU-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(3,5-dimethylphenyl)urea Chemical compound CC1=CC(C)=CC(NC(=O)NC=2NN=C(C=2)C2CC2)=C1 IRDDJYLPWTWDKU-UHFFFAOYSA-N 0.000 description 2
- APNVWKOKVDQKME-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(3-ethynylphenyl)urea Chemical compound C=1C=CC(C#C)=CC=1NC(=O)NC(NN=1)=CC=1C1CC1 APNVWKOKVDQKME-UHFFFAOYSA-N 0.000 description 2
- MCQYWOOGZUCFGA-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(3-hydroxy-4-methylphenyl)urea Chemical compound C1=C(O)C(C)=CC=C1NC(=O)NC1=CC(C2CC2)=NN1 MCQYWOOGZUCFGA-UHFFFAOYSA-N 0.000 description 2
- OWXBILRETZOPMU-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(3-hydroxyphenyl)urea Chemical compound OC1=CC=CC(NC(=O)NC=2NN=C(C=2)C2CC2)=C1 OWXBILRETZOPMU-UHFFFAOYSA-N 0.000 description 2
- DGUDRQUMTLNZRN-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(3-methoxyphenyl)urea Chemical compound COC1=CC=CC(NC(=O)NC=2NN=C(C=2)C2CC2)=C1 DGUDRQUMTLNZRN-UHFFFAOYSA-N 0.000 description 2
- DDYCCVXHBHBNEN-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(4-hydroxyphenyl)urea Chemical compound C1=CC(O)=CC=C1NC(=O)NC1=CC(C2CC2)=NN1 DDYCCVXHBHBNEN-UHFFFAOYSA-N 0.000 description 2
- RCYWFLFHXSNCBO-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(furan-2-ylmethyl)urea Chemical compound C=1C(C2CC2)=NNC=1NC(=O)NCC1=CC=CO1 RCYWFLFHXSNCBO-UHFFFAOYSA-N 0.000 description 2
- XLEUVNGBAINYTR-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(piperidin-4-ylmethyl)urea Chemical compound C=1C(C2CC2)=NNC=1NC(=O)NCC1CCNCC1 XLEUVNGBAINYTR-UHFFFAOYSA-N 0.000 description 2
- ZEQRTZUKZJYXFY-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-(pyridin-4-ylmethyl)urea Chemical compound C=1C(C2CC2)=NNC=1NC(=O)NCC1=CC=NC=C1 ZEQRTZUKZJYXFY-UHFFFAOYSA-N 0.000 description 2
- VIEMSIQIDUUAPS-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[(1-ethylpyrrolidin-2-yl)methyl]urea Chemical compound CCN1CCCC1CNC(=O)NC1=CC(C2CC2)=NN1 VIEMSIQIDUUAPS-UHFFFAOYSA-N 0.000 description 2
- LQJRZXJBGXLONK-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[(2,3-dimethoxyphenyl)methyl]urea Chemical compound COC1=CC=CC(CNC(=O)NC=2NN=C(C=2)C2CC2)=C1OC LQJRZXJBGXLONK-UHFFFAOYSA-N 0.000 description 2
- VVKLIMBQAJSOGP-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[(2,4-dichlorophenyl)methyl]urea Chemical compound ClC1=CC(Cl)=CC=C1CNC(=O)NC1=CC(C2CC2)=NN1 VVKLIMBQAJSOGP-UHFFFAOYSA-N 0.000 description 2
- DNZMSQNUCPUAEN-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[(2-ethoxyphenyl)methyl]urea Chemical compound CCOC1=CC=CC=C1CNC(=O)NC1=CC(C2CC2)=NN1 DNZMSQNUCPUAEN-UHFFFAOYSA-N 0.000 description 2
- MLJRGKUBYURCTM-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[(3,4-dichlorophenyl)methyl]urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CNC(=O)NC1=CC(C2CC2)=NN1 MLJRGKUBYURCTM-UHFFFAOYSA-N 0.000 description 2
- OUNHSJDDZBBHHP-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[(3,4-dimethoxyphenyl)methyl]urea Chemical compound C1=C(OC)C(OC)=CC=C1CNC(=O)NC1=CC(C2CC2)=NN1 OUNHSJDDZBBHHP-UHFFFAOYSA-N 0.000 description 2
- BUQIQPBZYXASIC-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[(3,4-dimethylphenyl)methyl]urea Chemical compound C1=C(C)C(C)=CC=C1CNC(=O)NC1=CC(C2CC2)=NN1 BUQIQPBZYXASIC-UHFFFAOYSA-N 0.000 description 2
- DHWDDTUFDWHZBO-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[(3-fluorophenyl)methyl]urea Chemical compound FC1=CC=CC(CNC(=O)NC=2NN=C(C=2)C2CC2)=C1 DHWDDTUFDWHZBO-UHFFFAOYSA-N 0.000 description 2
- JBNQPPUHAZQJRM-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[(3-methoxyphenyl)methyl]urea Chemical compound COC1=CC=CC(CNC(=O)NC=2NN=C(C=2)C2CC2)=C1 JBNQPPUHAZQJRM-UHFFFAOYSA-N 0.000 description 2
- RQGKFXBYCVIDLR-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[(4-fluorophenyl)methyl]urea Chemical compound C1=CC(F)=CC=C1CNC(=O)NC1=CC(C2CC2)=NN1 RQGKFXBYCVIDLR-UHFFFAOYSA-N 0.000 description 2
- NFYOPSBJJNREDE-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[(4-hydroxy-3-methoxyphenyl)methyl]urea Chemical compound C1=C(O)C(OC)=CC(CNC(=O)NC=2NN=C(C=2)C2CC2)=C1 NFYOPSBJJNREDE-UHFFFAOYSA-N 0.000 description 2
- ALKIPBUKIYZEEG-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[(4-methylphenyl)methyl]urea Chemical compound C1=CC(C)=CC=C1CNC(=O)NC1=CC(C2CC2)=NN1 ALKIPBUKIYZEEG-UHFFFAOYSA-N 0.000 description 2
- SSSIXPWCPBDBDK-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[2-(2h-imidazol-4-yl)ethyl]urea Chemical compound C=1C(C2CC2)=NNC=1NC(=O)NCCC1=NCN=C1 SSSIXPWCPBDBDK-UHFFFAOYSA-N 0.000 description 2
- RYSPROVYFMKASI-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[2-(5-methoxy-1h-indol-3-yl)ethyl]urea Chemical compound C12=CC(OC)=CC=C2NC=C1CCNC(=O)NC(NN=1)=CC=1C1CC1 RYSPROVYFMKASI-UHFFFAOYSA-N 0.000 description 2
- SXVKCJMRCYDIMZ-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[3-(3-hydroxybut-1-ynyl)phenyl]urea Chemical compound CC(O)C#CC1=CC=CC(NC(=O)NC2=NNC(=C2)C2CC2)=C1 SXVKCJMRCYDIMZ-UHFFFAOYSA-N 0.000 description 2
- DEAQNJSXFUFWEV-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[3-(methanesulfonamido)phenyl]urea Chemical compound CS(=O)(=O)NC1=CC=CC(NC(=O)NC=2NN=C(C=2)C2CC2)=C1 DEAQNJSXFUFWEV-UHFFFAOYSA-N 0.000 description 2
- NZBKQUHEKXICTI-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[3-[3-(dimethylamino)prop-1-ynyl]phenyl]urea Chemical compound CN(C)CC#CC1=CC=CC(NC(=O)NC=2NN=C(C=2)C2CC2)=C1 NZBKQUHEKXICTI-UHFFFAOYSA-N 0.000 description 2
- CAHHXBJGROIOFC-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-[[3-(trifluoromethyl)phenyl]methyl]urea Chemical compound FC(F)(F)C1=CC=CC(CNC(=O)NC=2NN=C(C=2)C2CC2)=C1 CAHHXBJGROIOFC-UHFFFAOYSA-N 0.000 description 2
- OUAPTOAHWNWJFF-UHFFFAOYSA-N 1-(5-cyclopropyl-1h-pyrazol-3-yl)-3-phenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC(NN=1)=CC=1C1CC1 OUAPTOAHWNWJFF-UHFFFAOYSA-N 0.000 description 2
- GLKUJDRNEWGWED-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-3-(5-cyclopropyl-1h-pyrazol-3-yl)urea Chemical compound ClC1=CC=CC=C1CNC(=O)NC1=CC(C2CC2)=NN1 GLKUJDRNEWGWED-UHFFFAOYSA-N 0.000 description 2
- AMFRZCFUWOMRSB-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-3-(5-cyclopropyl-1h-pyrazol-3-yl)urea Chemical compound C1=CC(Cl)=CC=C1CNC(=O)NC1=CC(C2CC2)=NN1 AMFRZCFUWOMRSB-UHFFFAOYSA-N 0.000 description 2
- RKVLCPXRRPHEHB-UHFFFAOYSA-N 1-[2-(3,4-dimethoxyphenyl)ethyl]-3-[5-(2-phenylethyl)-1h-pyrazol-3-yl]urea Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)NC1=CC(CCC=2C=CC=CC=2)=NN1 RKVLCPXRRPHEHB-UHFFFAOYSA-N 0.000 description 2
- MEFQJYDWUSDIGD-UHFFFAOYSA-N 1-[2-(4-hydroxyphenyl)ethyl]-3-[5-(2-phenylethyl)-1h-pyrazol-3-yl]urea Chemical compound C1=CC(O)=CC=C1CCNC(=O)NC1=CC(CCC=2C=CC=CC=2)=NN1 MEFQJYDWUSDIGD-UHFFFAOYSA-N 0.000 description 2
- UJOBEPBAPVBUAM-UHFFFAOYSA-N 1-[2-[[cyclohexyl(methyl)amino]methyl]phenyl]-3-(5-cyclopropyl-1h-pyrazol-3-yl)urea Chemical compound C1CCCCC1N(C)CC1=CC=CC=C1NC(=O)NC(NN=1)=CC=1C1CC1 UJOBEPBAPVBUAM-UHFFFAOYSA-N 0.000 description 2
- SSGTWBRHHUEXQF-UHFFFAOYSA-N 1-[5-(2-phenylethyl)-1h-pyrazol-3-yl]-3-propylurea Chemical compound N1C(NC(=O)NCCC)=CC(CCC=2C=CC=CC=2)=N1 SSGTWBRHHUEXQF-UHFFFAOYSA-N 0.000 description 2
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| US3754887A (en) * | 1969-05-05 | 1973-08-28 | Du Pont | Ureidopyrazoles defoliants |
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| DE69720051T2 (de) * | 1996-12-03 | 2003-09-04 | Banyu Pharmaceutical Co., Ltd. | Harnstoffderivate |
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-
1999
- 1999-08-12 US US09/372,833 patent/US6387900B1/en not_active Expired - Fee Related
-
2000
- 2000-08-03 PE PE2000000771A patent/PE20010482A1/es not_active Application Discontinuation
- 2000-08-10 CO CO00059913A patent/CO5200848A1/es not_active Application Discontinuation
- 2000-08-10 AR ARP000104118A patent/AR035557A1/es unknown
- 2000-08-11 DE DE60034683T patent/DE60034683T2/de not_active Expired - Fee Related
- 2000-08-11 AU AU67470/00A patent/AU6747000A/en not_active Abandoned
- 2000-08-11 EA EA200200249A patent/EA200200249A1/ru unknown
- 2000-08-11 HU HU0301857A patent/HUP0301857A2/hu unknown
- 2000-08-11 AT AT00955241T patent/ATE361070T1/de not_active IP Right Cessation
- 2000-08-11 NZ NZ517238A patent/NZ517238A/en unknown
- 2000-08-11 CN CN00812736A patent/CN1379668A/zh active Pending
- 2000-08-11 SK SK208-2002A patent/SK2082002A3/sk unknown
- 2000-08-11 KR KR1020027001815A patent/KR20020060158A/ko not_active Application Discontinuation
- 2000-08-11 PL PL00354058A patent/PL354058A1/xx not_active Application Discontinuation
- 2000-08-11 BR BR0013277-2A patent/BR0013277A/pt not_active Application Discontinuation
- 2000-08-11 ES ES00955241T patent/ES2284518T3/es not_active Expired - Lifetime
- 2000-08-11 JP JP2001516534A patent/JP2003507328A/ja not_active Withdrawn
- 2000-08-11 MX MXPA02001497A patent/MXPA02001497A/es active IP Right Grant
- 2000-08-11 CA CA002380786A patent/CA2380786A1/en not_active Abandoned
- 2000-08-11 WO PCT/US2000/017878 patent/WO2001012188A1/en active IP Right Grant
- 2000-08-11 EP EP00955241A patent/EP1202734B1/en not_active Expired - Lifetime
- 2000-08-11 IL IL14792500A patent/IL147925A0/xx unknown
-
2002
- 2002-02-08 ZA ZA200201118A patent/ZA200201118B/en unknown
- 2002-02-11 NO NO20020687A patent/NO20020687L/no not_active Application Discontinuation
-
2003
- 2003-03-14 HK HK03101874.6A patent/HK1049790A1/zh unknown
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