JP2003507328A5 - - Google Patents
Download PDFInfo
- 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- Withdrawn
Links
- -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
- URQFBYJGBGJFJB-UHFFFAOYSA-N 1-benzyl-3-(5-cyclopentyl-1h-pyrazol-3-yl)urea Chemical compound C=1C(C2CCCC2)=NNC=1NC(=O)NCC1=CC=CC=C1 URQFBYJGBGJFJB-UHFFFAOYSA-N 0.000 description 2
- CJEXSISEQQOIDM-UHFFFAOYSA-N 1-benzyl-3-(5-cyclopropyl-1h-pyrazol-3-yl)urea Chemical compound C=1C(C2CC2)=NNC=1NC(=O)NCC1=CC=CC=C1 CJEXSISEQQOIDM-UHFFFAOYSA-N 0.000 description 2
- TZYSGZKYMGIRSE-UHFFFAOYSA-N 1-benzyl-3-[5-(2-phenylethyl)-1h-pyrazol-3-yl]urea Chemical compound C=1C(CCC=2C=CC=CC=2)=NNC=1NC(=O)NCC1=CC=CC=C1 TZYSGZKYMGIRSE-UHFFFAOYSA-N 0.000 description 2
- NTMDAPLYMTYWFT-UHFFFAOYSA-N 1-butyl-3-(5-cyclopropyl-1h-pyrazol-3-yl)urea Chemical compound N1C(NC(=O)NCCCC)=CC(C2CC2)=N1 NTMDAPLYMTYWFT-UHFFFAOYSA-N 0.000 description 2
- DPJODIHOOVIXPY-UHFFFAOYSA-N 2-chloro-5-[(5-cyclopropyl-1h-pyrazol-3-yl)carbamoylamino]benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(NC(=O)NC=2NN=C(C=2)C2CC2)=C1 DPJODIHOOVIXPY-UHFFFAOYSA-N 0.000 description 2
- HYRCDJCRHWAAJR-UHFFFAOYSA-N 3-[(5-cyclopropyl-1h-pyrazol-3-yl)carbamoylamino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)NC=2NN=C(C=2)C2CC2)=C1 HYRCDJCRHWAAJR-UHFFFAOYSA-N 0.000 description 2
- MDLSRYFYCFBVLY-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-ylmethyl)-N-(5-cyclopropyl-1H-pyrazol-3-yl)piperazine-1-carboxamide Chemical compound C1(CC1)C1=NNC(=C1)NC(=O)N1CCN(CC1)CC1=CC2=C(OCO2)C=C1 MDLSRYFYCFBVLY-UHFFFAOYSA-N 0.000 description 2
- XDIRCIUYUWHOIO-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-ylmethyl)-n-[5-(2-phenylethyl)-1h-pyrazol-3-yl]piperazine-1-carboxamide Chemical compound C1CN(CC=2C=C3OCOC3=CC=2)CCN1C(=O)NC(NN=1)=CC=1CCC1=CC=CC=C1 XDIRCIUYUWHOIO-UHFFFAOYSA-N 0.000 description 2
- NXJOUUPOIKRHKE-UHFFFAOYSA-N 4-(aminomethyl)-n-(5-cyclopentyl-1h-pyrazol-3-yl)piperidine-1-carboxamide Chemical compound C1CC(CN)CCN1C(=O)NC1=CC(C2CCCC2)=NN1 NXJOUUPOIKRHKE-UHFFFAOYSA-N 0.000 description 2
- YLUKNHHMAPJELC-UHFFFAOYSA-N 4-(aminomethyl)-n-[5-(2-phenylethyl)-1h-pyrazol-3-yl]piperidine-1-carboxamide Chemical compound C1CC(CN)CCN1C(=O)NC1=CC(CCC=2C=CC=CC=2)=NN1 YLUKNHHMAPJELC-UHFFFAOYSA-N 0.000 description 2
- HPEUFTOMXSOAMP-UHFFFAOYSA-N 4-[2-nitro-4-(trifluoromethyl)phenyl]-n-[5-(2-phenylethyl)-1h-pyrazol-3-yl]piperazine-1-carboxamide Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1N1CCN(C(=O)NC=2NN=C(CCC=3C=CC=CC=3)C=2)CC1 HPEUFTOMXSOAMP-UHFFFAOYSA-N 0.000 description 2
- UFPLCCLBXJKWPZ-UHFFFAOYSA-N 4-benzyl-n-(5-cyclopentyl-1h-pyrazol-3-yl)piperazine-1-carboxamide Chemical compound C1CN(CC=2C=CC=CC=2)CCN1C(=O)NC(NN=1)=CC=1C1CCCC1 UFPLCCLBXJKWPZ-UHFFFAOYSA-N 0.000 description 2
- DTZHLGKCUSWJAU-UHFFFAOYSA-N 4-benzyl-n-[5-(2-phenylethyl)-1h-pyrazol-3-yl]piperazine-1-carboxamide Chemical compound C1CN(CC=2C=CC=CC=2)CCN1C(=O)NC(NN=1)=CC=1CCC1=CC=CC=C1 DTZHLGKCUSWJAU-UHFFFAOYSA-N 0.000 description 2
- CCKDCFIPKHSBLP-UHFFFAOYSA-N 4-methyl-n-[5-(2-phenylethyl)-1h-pyrazol-3-yl]piperazine-1-carboxamide Chemical compound C1CN(C)CCN1C(=O)NC1=CC(CCC=2C=CC=CC=2)=NN1 CCKDCFIPKHSBLP-UHFFFAOYSA-N 0.000 description 2
- NUHPXWLXOFUHMG-UHFFFAOYSA-N 4-phenyl-n-[5-(2-phenylethyl)-1h-pyrazol-3-yl]piperazine-1-carboxamide Chemical compound C1CN(C=2C=CC=CC=2)CCN1C(=O)NC(NN=1)=CC=1CCC1=CC=CC=C1 NUHPXWLXOFUHMG-UHFFFAOYSA-N 0.000 description 2
- MQFRYRWYXRXZIG-UHFFFAOYSA-N 5-[(5-cyclopropyl-1h-pyrazol-3-yl)carbamoylamino]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(NC(=O)NC2=NNC(=C2)C2CC2)=C1 MQFRYRWYXRXZIG-UHFFFAOYSA-N 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 125000004415 heterocyclylalkyl group Chemical group 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- ZWUDNZGGEODYHA-UHFFFAOYSA-N n-(5-cyclopentyl-1h-pyrazol-3-yl)-4-[2-nitro-4-(trifluoromethyl)phenyl]piperazine-1-carboxamide Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1N1CCN(C(=O)NC=2NN=C(C=2)C2CCCC2)CC1 ZWUDNZGGEODYHA-UHFFFAOYSA-N 0.000 description 2
- AHFFUFRQYKJGJO-UHFFFAOYSA-N n-(5-cyclopentyl-1h-pyrazol-3-yl)-4-methylpiperazine-1-carboxamide Chemical compound C1CN(C)CCN1C(=O)NC1=CC(C2CCCC2)=NN1 AHFFUFRQYKJGJO-UHFFFAOYSA-N 0.000 description 2
- ZAOJKSRSJWRKMB-UHFFFAOYSA-N n-(5-cyclopentyl-1h-pyrazol-3-yl)-4-phenylpiperazine-1-carboxamide Chemical compound C1CN(C=2C=CC=CC=2)CCN1C(=O)NC(NN=1)=CC=1C1CCCC1 ZAOJKSRSJWRKMB-UHFFFAOYSA-N 0.000 description 2
- QTOIYFFZKXQIAT-UHFFFAOYSA-N n-(5-cyclopentyl-1h-pyrazol-3-yl)morpholine-4-carboxamide Chemical compound C1COCCN1C(=O)NC(NN=1)=CC=1C1CCCC1 QTOIYFFZKXQIAT-UHFFFAOYSA-N 0.000 description 2
- LUHBNVCYMYNIDQ-UHFFFAOYSA-N n-(5-cyclopentyl-1h-pyrazol-3-yl)piperazine-1-carboxamide Chemical compound C1CNCCN1C(=O)NC(NN=1)=CC=1C1CCCC1 LUHBNVCYMYNIDQ-UHFFFAOYSA-N 0.000 description 2
- BPBJODNQCKQQKF-UHFFFAOYSA-N n-(5-cyclopentyl-1h-pyrazol-3-yl)piperidine-1-carboxamide Chemical compound C1CCCCN1C(=O)NC(NN=1)=CC=1C1CCCC1 BPBJODNQCKQQKF-UHFFFAOYSA-N 0.000 description 2
- UBIIGQCTNRNDGP-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-3,4-dihydro-1h-isoquinoline-2-carboxamide Chemical compound C1CC2=CC=CC=C2CN1C(=O)NC(NN=1)=CC=1C1CC1 UBIIGQCTNRNDGP-UHFFFAOYSA-N 0.000 description 2
- SKFBJASZPXIBBR-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)-3-oxo-2,4-dihydroquinoxaline-1-carboxamide Chemical compound C1C(=O)NC2=CC=CC=C2N1C(=O)NC(NN=1)=CC=1C1CC1 SKFBJASZPXIBBR-UHFFFAOYSA-N 0.000 description 2
- LQGSEEMUDCINIB-UHFFFAOYSA-N n-(5-cyclopropyl-1h-pyrazol-3-yl)morpholine-4-carboxamide Chemical compound C1COCCN1C(=O)NC(NN=1)=CC=1C1CC1 LQGSEEMUDCINIB-UHFFFAOYSA-N 0.000 description 2
- UZHSOWAHRQEJTG-UHFFFAOYSA-N n-[3-[(5-cyclopropyl-1h-pyrazol-3-yl)carbamoylamino]-4-methoxyphenyl]acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1NC(=O)NC1=CC(C2CC2)=NN1 UZHSOWAHRQEJTG-UHFFFAOYSA-N 0.000 description 2
- DBCGSQWGSHLWLE-UHFFFAOYSA-N n-[4-[(5-cyclopropyl-1h-pyrazol-3-yl)carbamoylamino]phenyl]-n-methylacetamide Chemical compound C1=CC(N(C(C)=O)C)=CC=C1NC(=O)NC1=CC(C2CC2)=NN1 DBCGSQWGSHLWLE-UHFFFAOYSA-N 0.000 description 2
- UINIGLCEPAMPBD-UHFFFAOYSA-N n-[5-(2-phenylethyl)-1h-pyrazol-3-yl]morpholine-4-carboxamide Chemical compound C1COCCN1C(=O)NC(NN=1)=CC=1CCC1=CC=CC=C1 UINIGLCEPAMPBD-UHFFFAOYSA-N 0.000 description 2
- ZRXIDGLJJYNNPC-UHFFFAOYSA-N n-[5-(2-phenylethyl)-1h-pyrazol-3-yl]piperazine-1-carboxamide Chemical compound C1CNCCN1C(=O)NC(NN=1)=CC=1CCC1=CC=CC=C1 ZRXIDGLJJYNNPC-UHFFFAOYSA-N 0.000 description 2
- AMQRDSWZYLWQFB-UHFFFAOYSA-N n-[5-(2-phenylethyl)-1h-pyrazol-3-yl]piperidine-1-carboxamide Chemical compound C1CCCCN1C(=O)NC(NN=1)=CC=1CCC1=CC=CC=C1 AMQRDSWZYLWQFB-UHFFFAOYSA-N 0.000 description 2
- SMJLZWKZTCCUDX-UHFFFAOYSA-N n-[5-(2-phenylethyl)-1h-pyrazol-3-yl]pyrrolidine-1-carboxamide Chemical compound C1CCCN1C(=O)NC(NN=1)=CC=1CCC1=CC=CC=C1 SMJLZWKZTCCUDX-UHFFFAOYSA-N 0.000 description 2
- DFDXQZWRNFBGCA-UHFFFAOYSA-N n-[5-[(5-cyclopropyl-1h-pyrazol-3-yl)carbamoylamino]-2-methoxyphenyl]acetamide Chemical compound C1=C(NC(C)=O)C(OC)=CC=C1NC(=O)NC1=CC(C2CC2)=NN1 DFDXQZWRNFBGCA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 125000003884 phenylalkyl group Chemical group 0.000 description 2
- 230000002062 proliferating effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 0 *c1cc(N)n[n]1 Chemical compound *c1cc(N)n[n]1 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 description 1
- GUJITMGNBDAQQU-UHFFFAOYSA-N C1CCC(C1)C2=CC(=NN2)NC(=O)NC3CC3 Chemical compound C1CCC(C1)C2=CC(=NN2)NC(=O)NC3CC3 GUJITMGNBDAQQU-UHFFFAOYSA-N 0.000 description 1
- 102000016736 Cyclin Human genes 0.000 description 1
- 108050006400 Cyclin Proteins 0.000 description 1
- 201000006107 Familial adenomatous polyposis Diseases 0.000 description 1
- 208000004463 Follicular Adenocarcinoma Diseases 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 208000007766 Kaposi sarcoma Diseases 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 208000009905 Neurofibromatoses Diseases 0.000 description 1
- 208000031481 Pathologic Constriction Diseases 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- 208000004403 Prostatic Hyperplasia Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 201000010208 Seminoma Diseases 0.000 description 1
- 206010043276 Teratoma Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 210000001185 bone marrow Anatomy 0.000 description 1
- 208000035269 cancer or benign tumor Diseases 0.000 description 1
- 230000022131 cell cycle Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 208000029664 classic familial adenomatous polyposis Diseases 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 230000001085 cytostatic effect Effects 0.000 description 1
- 239000002254 cytotoxic agent Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 231100000599 cytotoxic agent Toxicity 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 208000019691 hematopoietic and lymphoid cell neoplasm Diseases 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 210000004324 lymphatic system Anatomy 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- JAJDVVVDCVBRJD-UHFFFAOYSA-N n-(5-cyclopentyl-1h-pyrazol-3-yl)pyrrolidine-1-carboxamide Chemical compound C1CCCN1C(=O)NC(NN=1)=CC=1C1CCCC1 JAJDVVVDCVBRJD-UHFFFAOYSA-N 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 201000004931 neurofibromatosis Diseases 0.000 description 1
- 201000008968 osteosarcoma Diseases 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 206010041823 squamous cell carcinoma Diseases 0.000 description 1
- 208000037804 stenosis Diseases 0.000 description 1
- 230000036262 stenosis Effects 0.000 description 1
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 description 1
- 230000005747 tumor angiogenesis Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/372,833 | 1999-08-12 | ||
| US09/372,833 US6387900B1 (en) | 1999-08-12 | 1999-08-12 | 3(5)-ureido-pyrazole derivatives process for their preparation and their use as antitumor agents |
| PCT/US2000/017878 WO2001012188A1 (en) | 1999-08-12 | 2000-08-11 | 3(5)-ureido-pyrazole derivatives, process for their preparation and their use as antitumor agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003507328A JP2003507328A (ja) | 2003-02-25 |
| JP2003507328A5 true JP2003507328A5 (US20050059668A1-20050317-C00061.png) | 2007-05-24 |
Family
ID=23469810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001516534A Withdrawn JP2003507328A (ja) | 1999-08-12 | 2000-08-11 | ３（５）−ウレイド−ピラゾール誘導体、その調製方法および抗腫瘍剤としての使用 |
Country Status (25)
Families Citing this family (75)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070244120A1 (en) * | 2000-08-18 | 2007-10-18 | Jacques Dumas | Inhibition of raf kinase using substituted heterocyclic ureas |
| US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| EP1158985B1 (en) | 1999-01-13 | 2011-12-28 | Bayer HealthCare LLC | OMEGA-CARBOXY ARYL SUBSTITUTED DIPHENYL UREAS AS p38 KINASE INHIBITORS |
| EA005212B1 (ru) | 1999-12-24 | 2004-12-30 | Авентис Фарма Лимитед | Азаиндолы |
| CA2399274A1 (en) * | 2000-02-07 | 2001-08-09 | Mark E. Salvati | 3-aminopyrazole inhibitors of cyclin dependent kinases |
| ES2236217T3 (es) | 2000-04-25 | 2005-07-16 | Bristol-Myers Squibb Company | Uso de 5.tio.,sulfinil- y sulfonilpirazolo 3,4-b)-piridinas como inhibidores de la quinasa dependiente de la ciclina. |
| YU14703A (sh) * | 2000-08-31 | 2006-05-25 | Pfizer Products Inc. | Derivati pirazola i njihova upotreba kao inhibitora protein kinaze |
| AU2002215053A1 (en) * | 2000-11-27 | 2002-06-24 | Pharmacia Italia S.P.A. | Phenylacetamido- pyrazole derivatives and their use as antitumor agents |
| GB0115109D0 (en) | 2001-06-21 | 2001-08-15 | Aventis Pharma Ltd | Chemical compounds |
| DK2305255T3 (da) * | 2001-12-03 | 2012-12-10 | Bayer Healthcare Llc | Arylurinstofforbindelser i kombination med andre cytostatiske eller cytotoksiske midler til behandling af humane cancere |
| US20050113283A1 (en) * | 2002-01-18 | 2005-05-26 | David Solow-Cordero | Methods of treating conditions associated with an EDG-4 receptor |
| SI1478358T1 (sl) | 2002-02-11 | 2013-09-30 | Bayer Healthcare Llc | Sorafenib tozilat za zdravljenje bolezni, značilnih po abnormalni angiogenezi |
| KR20030071029A (ko) * | 2002-02-27 | 2003-09-03 | 주식회사 팜제니아 | 항암제 및 방사선 치료 증진제로서 유용한 조성물 |
| US20030225089A1 (en) * | 2002-04-10 | 2003-12-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pharmaceutical compositions based on anticholinergics and p38 kinase inhibitors |
| DE10221052A1 (de) * | 2002-05-10 | 2003-12-04 | Transmit Technologietransfer | Wirkstoffe zu Therapie, Diagnostik und Prophylaxe von Erkrankungen, bei denen abnorme Proteinstrukturen auftreten |
| AU2003227741A1 (en) * | 2002-05-17 | 2003-12-02 | Pharmacia Italia S.P.A. | Aminoindazole derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| CA2493458A1 (en) | 2002-07-24 | 2004-01-29 | Ptc Therapeutics, Inc. | Ureido substituted benzoic acid compounds, their use for nonsense suppression and the treatment of diseases caused by such mutations |
| ATE435199T1 (de) * | 2002-09-05 | 2009-07-15 | Neurosearch As | Diarylharnstoffderivate und deren verwendung als chloridkanalblocker |
| CA2501799C (en) | 2002-10-09 | 2008-06-17 | Pfizer Products Inc. | Pyrazole compounds for treatment of neurodegenerative disorders |
| UA81790C2 (uk) | 2002-12-19 | 2008-02-11 | Фармация Италия С.П.А. | Заміщені піролопіразольні похідні як інгібітори кінази |
| UY28213A1 (es) | 2003-02-28 | 2004-09-30 | Bayer Pharmaceuticals Corp | Nuevos derivados de cianopiridina útiles en el tratamiento de cáncer y otros trastornos. |
| GB0305426D0 (en) * | 2003-03-08 | 2003-04-16 | Glaxo Group Ltd | Novel compounds |
| DK1636585T3 (da) | 2003-05-20 | 2008-05-26 | Bayer Pharmaceuticals Corp | Diarylurinstoffer med kinasehæmmende aktivitet |
| CA2526578C (en) | 2003-05-22 | 2012-01-24 | Pharmacia Italia S.P.A. | Pyrazolo-quinazoline derivatives, process for their preparation and their use as kinase inhibitors |
| US7141568B2 (en) | 2003-07-09 | 2006-11-28 | Pfizer Italia S.R.L. | Pyrrolo[3,4-c]pyrazole derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| CL2004001834A1 (es) | 2003-07-23 | 2005-06-03 | Bayer Pharmaceuticals Corp | Compuesto 4-{4-[3-(4-cloro-3-trifluorometilfenil)-ureido]-3-fluorofenoxi}-piridin-2-metilamida, inhibidor de la raf, vegfr, p38 y pdgfr quinasas, sus sales; composiicon farmaceutica; combinacion farmaceutica; y su uso para tratar trastornos hiperprol |
| TW200526204A (en) | 2004-02-03 | 2005-08-16 | Pharmacia Italia Spa | 1h-thieno[2,3-c]pyrazole derivatives useful as kinase inhibitors |
| US7244757B2 (en) * | 2004-04-01 | 2007-07-17 | Pfizer Inc | Pyrazole-amine compounds for the treatment of neurodegenerative disorders |
| EP1609789A1 (en) * | 2004-06-23 | 2005-12-28 | Eli Lilly And Company | Ureido-pyrazole derivatives and their use as kinase inhibitors |
| CA2576297C (en) * | 2004-08-12 | 2011-01-25 | Pfizer Inc. | Triazolopyridinylsulfanyl derivatives as p38 map kinase inhibitors |
| WO2006074025A1 (en) | 2004-12-30 | 2006-07-13 | Janssen Pharmaceutica N.V. | Piperazinyl and piperidinyl ureas as modulators of fatty acid amide hydrolase |
| US20060183758A1 (en) * | 2005-02-17 | 2006-08-17 | Cb Research And Development, Inc. | Method for synthesis of AZA-annelated pyrroles, thiophenes, and furans |
| US7429800B2 (en) * | 2005-06-30 | 2008-09-30 | Sabic Innovative Plastics Ip B.V. | Molding composition and method, and molded article |
| WO2007009898A1 (en) | 2005-07-19 | 2007-01-25 | Nerviano Medical Sciences S.R.L. | 1h-thieno[2,3-c]pyrazole compounds useful as kinase inhibitors |
| AR059826A1 (es) | 2006-03-13 | 2008-04-30 | Univ California | Inhibidores de urea conformacionalmente restringidos de epoxido hidrolasa soluble |
| EP2016068A1 (en) * | 2006-05-03 | 2009-01-21 | AstraZeneca AB | Pyrazole derivatives and their use as pi3k inhibitors |
| JP5406030B2 (ja) | 2006-10-21 | 2014-02-05 | アボット ゲーエムベーハー ウント カンパニー カーゲー | 複素環化合物およびそれらのグリコーゲンシンターゼキナーゼ３阻害薬としての使用 |
| CL2008000119A1 (es) | 2007-01-16 | 2008-05-16 | Wyeth Corp | Compuestos derivados de pirazol, antagonistas del receptor nicotinico de acetilcolina; composicion farmaceutica; y uso en el tratamiento de enfermedades tales como demencia senil, alzheimer y esquizofrenia. |
| US9512082B2 (en) | 2007-04-18 | 2016-12-06 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| EP2164493A2 (en) * | 2007-05-25 | 2010-03-24 | Janssen Pharmaceutica, N.V. | Heteroaryl-substituted urea modulators of fatty acid amide hydrolase |
| EP2163541A1 (en) * | 2008-09-12 | 2010-03-17 | Bayer Schering Pharma Aktiengesellschaft | Piperazine derivatives for binding and imaging amyloid plaques and their use |
| AU2009310352A1 (en) * | 2008-10-01 | 2010-05-06 | The University Of North Carolina At Chapel Hill | Hematopoietic protection against ionizing radiation using selective cyclin-dependent kinase 4/6 inhibitors |
| WO2010068453A1 (en) | 2008-11-25 | 2010-06-17 | Janssen Pharmaceutica Nv | Heteroaryl-substituted urea modulators of fatty acid amide hydrolase |
| US8598356B2 (en) * | 2008-11-25 | 2013-12-03 | Janssen Pharmaceutica Nv | Heteroaryl-substituted urea modulators of fatty acid amide hydrolase |
| EP3406260B1 (en) | 2009-05-13 | 2020-09-23 | The University of North Carolina at Chapel Hill | Cyclin dependent kinase inhibitors and methods of use |
| US8901111B2 (en) | 2009-06-05 | 2014-12-02 | Janssen Pharmaceutica Nv | Aryl-substituted heterocyclic urea modulators of fatty acid amide hydrolase |
| WO2010141817A1 (en) | 2009-06-05 | 2010-12-09 | Janssen Pharmaceutica Nv | Heteroaryl-substituted spirocyclic diamine urea modulators of fatty acid amide hydrolase |
| WO2012054093A2 (en) | 2010-01-29 | 2012-04-26 | The Regents Of The University Of California | Acyl piperidine inhibitors of soluble epoxide hydrolase |
| UA108233C2 (uk) | 2010-05-03 | 2015-04-10 | Модулятори активності гідролази амідів жирних кислот | |
| AU2011274369A1 (en) * | 2010-07-02 | 2012-12-06 | Ventana Medical Systems, Inc. | Hapten conjugates for target detection |
| CA2806634A1 (en) * | 2010-08-20 | 2012-02-23 | Gruenenthal Gmbh | Substituted cyclic carboxamide and urea derivatives as ligands of the vanilloid receptor |
| EP2621914B1 (en) | 2010-09-27 | 2016-12-28 | Abbott GmbH & Co. KG | Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors |
| CN103501789A (zh) | 2010-11-17 | 2014-01-08 | 北卡罗来纳大学查珀尔希尔分校 | 通过抑制增殖性激酶cdk4和cdk6保护肾组织免于局部缺血 |
| BR112013008527A2 (pt) | 2010-12-17 | 2016-07-12 | Nerviano Medical Sciences Srl | derivados de pirazolo-quinazolina substituídos como inibidores de cinase |
| US9090592B2 (en) | 2010-12-30 | 2015-07-28 | AbbVie Deutschland GmbH & Co. KG | Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors |
| MY173181A (en) | 2011-05-13 | 2020-01-02 | Array Biopharma Inc | Pyrrolidinyl urea, pyrrolidinyl thiourea and pyrrolidinyl guanidine compounds as trka kinase inhibitors |
| AR087701A1 (es) * | 2011-08-31 | 2014-04-09 | Japan Tobacco Inc | Derivados de pirazol con actividad inhibidora de sglt1 |
| US9822118B2 (en) | 2012-11-13 | 2017-11-21 | Array Biopharma Inc. | Bicyclic heteroaryl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| US9790178B2 (en) | 2012-11-13 | 2017-10-17 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| UA116455C2 (uk) | 2012-11-13 | 2018-03-26 | Еррей Біофарма Інк. | Сполуки n-піролідинілсечовини, n'-піразолілсечовини, тіосечовини, гуанідину та ціаногуанідину як інгібітори кінази trka |
| US9828360B2 (en) | 2012-11-13 | 2017-11-28 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| WO2014078331A1 (en) * | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-(arylalkyl)-n'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| HUE031557T2 (en) | 2012-11-13 | 2017-07-28 | Array Biopharma Inc | Bicyclic urea, thiourea, guanidine, and cyanoguadinine compounds used to treat pain |
| US9546156B2 (en) | 2012-11-13 | 2017-01-17 | Array Biopharma Inc. | N-bicyclic aryl,N'-pyrazolyl urea, thiourea, guanidine cyanoguanidine compounds as TrkA kinase inhibitors |
| US9809578B2 (en) | 2012-11-13 | 2017-11-07 | Array Biopharma Inc. | Pyrazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trkA kinase inhibitors |
| WO2014078322A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Thiazolyl and oxazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| WO2014078325A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-(monocyclic aryl),n'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| RS59790B1 (sr) | 2013-03-15 | 2020-02-28 | G1 Therapeutics Inc | Privremena zaštita normalnih ćelija tokom hemoterapije |
| JP6435315B2 (ja) | 2013-03-15 | 2018-12-05 | ジー１、セラピューティクス、インコーポレイテッドＧ１ Ｔｈｅｒａｐｅｕｔｉｃｓ， Ｉｎｃ． | 高活性抗新生物薬及び抗増殖剤 |
| US20150297606A1 (en) | 2014-04-17 | 2015-10-22 | G1 Therapeutics, Inc. | Tricyclic Lactams for Use in the Protection of Hematopoietic Stem and Progenitor Cells Against Ionizing Radiation |
| SI3154959T1 (sl) | 2014-05-15 | 2019-10-30 | Array Biopharma Inc | 1-((3S,4R)-4-(3-fluorofenil)-1-(2-metoksietil)pirolidin-3-il)-3-(4- metil-3-(2-metilpirimidin-5-il)-1-fenil-1H-pirazol-5-il)urea kot inhibitor TrkA kinaze |
| WO2016040848A1 (en) | 2014-09-12 | 2016-03-17 | G1 Therapeutics, Inc. | Treatment of rb-negative tumors using topoisomerase inhibitors in combination with cyclin dependent kinase 4/6 inhibitors |
| EP3191098A4 (en) | 2014-09-12 | 2018-04-25 | G1 Therapeutics, Inc. | Combinations and dosing regimes to treat rb-positive tumors |
| US10988479B1 (en) | 2020-06-15 | 2021-04-27 | G1 Therapeutics, Inc. | Morphic forms of trilaciclib and methods of manufacture thereof |
| TW202229268A (zh) * | 2020-12-22 | 2022-08-01 | 大陸商上海拓界生物醫藥科技有限公司 | Ｃｄｋ２抑制劑及其製備方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3646059A (en) * | 1969-05-05 | 1972-02-29 | Du Pont | Plant growth regulatory ureidopyrazoles |
| US3754887A (en) * | 1969-05-05 | 1973-08-28 | Du Pont | Ureidopyrazoles defoliants |
| CN1165482A (zh) | 1994-11-10 | 1997-11-19 | 科西雷佩蒂斯公司 | 用作蛋白激酶抑制剂的吡唑药物组合物 |
| AU5135998A (en) | 1996-12-03 | 1998-06-29 | Banyu Pharmaceutical Co., Ltd. | Novel urea derivatives |
| AU7726898A (en) | 1997-05-22 | 1998-12-11 | G.D. Searle & Co. | Pyrazole derivatives as p38 kinase inhibitors |
| CA2315720A1 (en) | 1997-12-22 | 1999-07-01 | Bayer Corporation | Inhibition of p38 kinase activity using substituted heterocyclic ureas |
-
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 IL IL14792500A patent/IL147925A0/xx unknown
- 2000-08-11 CA CA002380786A patent/CA2380786A1/en not_active Abandoned
- 2000-08-11 PL PL00354058A patent/PL354058A1/xx not_active Application Discontinuation
- 2000-08-11 DE DE60034683T patent/DE60034683T2/de not_active Expired - Fee Related
- 2000-08-11 KR KR1020027001815A patent/KR20020060158A/ko not_active Application Discontinuation
- 2000-08-11 BR BR0013277-2A patent/BR0013277A/pt not_active Application Discontinuation
- 2000-08-11 AT AT00955241T patent/ATE361070T1/de not_active IP Right Cessation
- 2000-08-11 SK SK208-2002A patent/SK2082002A3/sk unknown
- 2000-08-11 WO PCT/US2000/017878 patent/WO2001012188A1/en active IP Right Grant
- 2000-08-11 AU AU67470/00A patent/AU6747000A/en not_active Abandoned
- 2000-08-11 JP JP2001516534A patent/JP2003507328A/ja not_active Withdrawn
- 2000-08-11 ES ES00955241T patent/ES2284518T3/es not_active Expired - Lifetime
- 2000-08-11 MX MXPA02001497A patent/MXPA02001497A/es active IP Right Grant
- 2000-08-11 EP EP00955241A patent/EP1202734B1/en not_active Expired - Lifetime
- 2000-08-11 HU HU0301857A patent/HUP0301857A2/hu unknown
- 2000-08-11 EA EA200200249A patent/EA200200249A1/ru unknown
- 2000-08-11 NZ NZ517238A patent/NZ517238A/en unknown
- 2000-08-11 CN CN00812736A patent/CN1379668A/zh active Pending
-
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
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2003507328A5 (US20050059668A1-20050317-C00061.png) | ||
| RU2388750C2 (ru) | Ингибиторы фосфодиэстеразы 4, включая аналоги n-замещенного диариламина | |
| RU2326869C2 (ru) | Производные пиридазин-3(2h)-она в качестве ингибиторов фосфодиэстеразы 4 (pde4), способ их получения, фармацевтическая композиция и способ лечения | |
| RU2007114125A (ru) | Замещенные гидантоины для лечения рака | |
| JP2021011495A5 (US20050059668A1-20050317-C00061.png) | ||
| RU2436776C2 (ru) | ДИАРИЛАМИН-СОДЕРЖАЩИЕ СОЕДИНЕНИЯ, КОМПОЗИЦИИ И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ МОДУЛЯТОРОВ РЕЦЕПТОРОВ с-КIT | |
| RU2355683C2 (ru) | Производные 1-бензоилпиперазина в качестве ингибиторов поглощения глицина для лечения психозов | |
| JP2007519754A5 (US20050059668A1-20050317-C00061.png) | ||
| JP2007513957A5 (US20050059668A1-20050317-C00061.png) | ||
| US9096571B2 (en) | Picolinamide and pyrimidine-4-carboxamide compounds, process for preparing and pharmaceutical composition comprising the same | |
| RU2368604C2 (ru) | Ингибиторы фосфодиэстеразы 4, включающие n-замещенные аналоги анилина и дифениламина | |
| RU2008112221A (ru) | Соединения ряда изоиндолимидов, их композиции и способы применения | |
| RU2005137403A (ru) | Новые замещенные 3-сера-индолы | |
| JP2002540204A5 (US20050059668A1-20050317-C00061.png) | ||
| JP2005538955A5 (US20050059668A1-20050317-C00061.png) | ||
| RU2009106722A (ru) | 2,4-замещенные хиназолины в качестве ингибиторов липидной киназы | |
| RU2002101935A (ru) | Аминовые и амидные производные как лиганды для рецептора Y5 нейропептида Y, используемые для лечения ожирения и других расстройств | |
| RU2003129502A (ru) | Соединение, фармацевтическая композиция, применение, способ предупреждения или лечения заболеваний | |
| RU2003115612A (ru) | Производные амидоалкилпиперидинов и амидоалкилпиперазинов, пригодные для лечения нарушений нервной системы | |
| RU2003100518A (ru) | Производные бензотиазола | |
| RU2004135064A (ru) | Новые замещенные индолы | |
| RU2003121018A (ru) | Производные карбоксамида и их использование в лечении тромбоэмболических заболеваний и опухолей | |
| JP2005533803A5 (US20050059668A1-20050317-C00061.png) | ||
| RU2007118632A (ru) | Ингибиторы митотического кинезина и способы их использования | |
| RU2005119627A (ru) | Ингибиторы фосфодиэстеразы 4 |
