JP2007535565A - 癌の治療に有用な置換ピラゾリル尿素誘導体 - Google Patents

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Publication number

JP2007535565A

JP2007535565A JP2007511073A JP2007511073A JP2007535565A JP 2007535565 A JP2007535565 A JP 2007535565A JP 2007511073 A JP2007511073 A JP 2007511073A JP 2007511073 A JP2007511073 A JP 2007511073A JP 2007535565 A JP2007535565 A JP 2007535565A

Authority

JP

Japan

Prior art keywords

phenyl

amino

butyl

tert

pyrazol

Prior art date

2004-04-30

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.)

Pending

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• 206010028980 Neoplasm Diseases 0.000 title claims abstract description 67
• 201000011510 cancer Diseases 0.000 title claims abstract description 33
• 238000011282 treatment Methods 0.000 title description 22
• XAEGRAIWWBXIRR-UHFFFAOYSA-N 1h-pyrazol-5-ylurea Chemical class NC(=O)NC=1C=CNN=1 XAEGRAIWWBXIRR-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 209
• 238000000034 method Methods 0.000 claims abstract description 59
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
• -1 hydroxy, amino Chemical group 0.000 claims description 370
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 173
• 239000000203 mixture Substances 0.000 claims description 95
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 81
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 70
• XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 67
• 125000000217 alkyl group Chemical group 0.000 claims description 56
• 125000001424 substituent group Chemical group 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 45
• 239000001257 hydrogen Substances 0.000 claims description 43
• 239000011734 sodium Substances 0.000 claims description 39
• 239000004202 carbamide Substances 0.000 claims description 38
• 229920006395 saturated elastomer Polymers 0.000 claims description 38
• 150000003839 salts Chemical class 0.000 claims description 35
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 31
• 229910052736 halogen Inorganic materials 0.000 claims description 31
• 239000003814 drug Substances 0.000 claims description 30
• 150000002367 halogens Chemical class 0.000 claims description 29
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
• 229910052799 carbon Inorganic materials 0.000 claims description 27
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 26
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 26
• 125000006413 ring segment Chemical group 0.000 claims description 26
• 229910052757 nitrogen Inorganic materials 0.000 claims description 25
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 23
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 23
• 239000000460 chlorine Substances 0.000 claims description 23
• 229940079593 drug Drugs 0.000 claims description 22
• 125000001188 haloalkyl group Chemical group 0.000 claims description 22
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
• 239000002253 acid Substances 0.000 claims description 19
• 229940002612 prodrug Drugs 0.000 claims description 18
• 239000000651 prodrug Substances 0.000 claims description 18
• 150000002148 esters Chemical class 0.000 claims description 17
• 125000001153 fluoro group Chemical group F* 0.000 claims description 17
• 150000001721 carbon Chemical group 0.000 claims description 16
• BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 16
• 125000002950 monocyclic group Chemical group 0.000 claims description 16
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• 239000003795 chemical substances by application Substances 0.000 claims description 14
• 208000035475 disorder Diseases 0.000 claims description 14
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
• 229910052717 sulfur Inorganic materials 0.000 claims description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 239000002207 metabolite Substances 0.000 claims description 12
• 239000011737 fluorine Substances 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 11
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 11
• 150000002431 hydrogen Chemical class 0.000 claims description 11
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 241000124008 Mammalia Species 0.000 claims description 9
• 206010027476 Metastases Diseases 0.000 claims description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
• VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 7
• VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 7
• NDLQHWDYAQFRBU-UHFFFAOYSA-N 2-[4-[3-tert-butyl-5-[(4-pyridin-4-yloxyphenyl)carbamoylamino]pyrazol-1-yl]phenyl]acetic acid Chemical compound C=1C=C(CC(O)=O)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 NDLQHWDYAQFRBU-UHFFFAOYSA-N 0.000 claims description 7
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• 108010050904 Interferons Proteins 0.000 claims description 7
• 102000014150 Interferons Human genes 0.000 claims description 7
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 7
• 206010039491 Sarcoma Diseases 0.000 claims description 7
• IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 7
• 230000002491 angiogenic effect Effects 0.000 claims description 7
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 7
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
• 230000003463 hyperproliferative effect Effects 0.000 claims description 7
• 229940079322 interferon Drugs 0.000 claims description 7
• 229960001592 paclitaxel Drugs 0.000 claims description 7
• RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims description 7
• 150000003536 tetrazoles Chemical class 0.000 claims description 7
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 7
• FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 6
• XIEXRSUZWARTBD-UHFFFAOYSA-N 1-[2-[4-(aminomethyl)phenyl]-5-tert-butylpyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C=1C=C(CN)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 XIEXRSUZWARTBD-UHFFFAOYSA-N 0.000 claims description 6
• 108010074604 Epoetin Alfa Proteins 0.000 claims description 6
• NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 claims description 6
• NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 6
• DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 claims description 6
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
• RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 claims description 6
• 125000004432 carbon atom Chemical group C* 0.000 claims description 6
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
• KIIAVHWBIPNTGI-UHFFFAOYSA-N ethoxy-methoxy-propoxy-lambda3-bromane Chemical compound COBr(OCCC)OCC KIIAVHWBIPNTGI-UHFFFAOYSA-N 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 6
• GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• 125000004043 oxo group Chemical group O=* 0.000 claims description 6
• UCFGDBYHRUNTLO-QHCPKHFHSA-N topotecan Chemical compound C1=C(O)C(CN(C)C)=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 UCFGDBYHRUNTLO-QHCPKHFHSA-N 0.000 claims description 6
• FMEAFBHPDCBPPE-UHFFFAOYSA-N 1-[5-tert-butyl-2-[3-(3-hydroxypropylamino)phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C=1C=CC(NCCCO)=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 FMEAFBHPDCBPPE-UHFFFAOYSA-N 0.000 claims description 5
• PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 claims description 5
• AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 claims description 5
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 claims description 5
• ZDZOTLJHXYCWBA-VCVYQWHSSA-N N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C=4C=CC=CC=4)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 ZDZOTLJHXYCWBA-VCVYQWHSSA-N 0.000 claims description 5
• 229930012538 Paclitaxel Natural products 0.000 claims description 5
• 208000000453 Skin Neoplasms Diseases 0.000 claims description 5
• 210000000481 breast Anatomy 0.000 claims description 5
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• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 5
• 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 5
• 229960004768 irinotecan Drugs 0.000 claims description 5
• UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims description 5
• GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 claims description 5
• 229960004622 raloxifene Drugs 0.000 claims description 5
• 229960000303 topotecan Drugs 0.000 claims description 5
• ZXUWSRNPQZVPLR-UHFFFAOYSA-N 1-[5-tert-butyl-2-[3-(3-hydroxypropoxy)phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C=1C=CC(OCCCO)=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 ZXUWSRNPQZVPLR-UHFFFAOYSA-N 0.000 claims description 4
• BHSOBLOBORUXMS-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-methoxyethoxymethyl)phenyl]pyrazol-3-yl]-3-[2-fluoro-4-(2-methylpyridin-4-yl)oxyphenyl]urea Chemical compound C1=CC(COCCOC)=CC=C1N1C(NC(=O)NC=2C(=CC(OC=3C=C(C)N=CC=3)=CC=2)F)=CC(C(C)(C)C)=N1 BHSOBLOBORUXMS-UHFFFAOYSA-N 0.000 claims description 4
• JDAKOHHPPJZIIT-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-morpholin-4-ylethoxymethyl)phenyl]pyrazol-3-yl]-3-[2-fluoro-4-(2-methylpyridin-4-yl)oxyphenyl]urea Chemical compound C1=NC(C)=CC(OC=2C=C(F)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(COCCN4CCOCC4)=CC=3)=CC=2)=C1 JDAKOHHPPJZIIT-UHFFFAOYSA-N 0.000 claims description 4
• HHFPDBMETPOJST-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-piperidin-4-ylethoxy)phenyl]pyrazol-3-yl]-3-(4-pyridin-3-yloxyphenyl)urea Chemical compound C=1C=C(OCCC2CCNCC2)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=CN=C1 HHFPDBMETPOJST-UHFFFAOYSA-N 0.000 claims description 4
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• WKHJHKCWGIUMCP-UHFFFAOYSA-N 4-[4-[3-tert-butyl-5-[(4-pyridin-4-yloxyphenyl)carbamoylamino]pyrazol-1-yl]anilino]-2,2-dimethyl-4-oxobutanoic acid Chemical compound C=1C=C(NC(=O)CC(C)(C)C(O)=O)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 WKHJHKCWGIUMCP-UHFFFAOYSA-N 0.000 claims description 4
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• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 4
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• 210000004392 genitalia Anatomy 0.000 claims description 4
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• JZECSHSHTIPKLH-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-hydroxyethyl)phenyl]pyrazol-3-yl]-3-[2-fluoro-4-(2-methylpyridin-4-yl)oxyphenyl]urea Chemical compound C1=NC(C)=CC(OC=2C=C(F)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(CCO)=CC=3)=CC=2)=C1 JZECSHSHTIPKLH-UHFFFAOYSA-N 0.000 claims description 2
• LZRTWANPIKXPGB-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-hydroxyethylamino)phenyl]pyrazol-3-yl]-3-(4-pyridin-3-yloxyphenyl)urea Chemical compound C=1C=C(NCCO)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=CN=C1 LZRTWANPIKXPGB-UHFFFAOYSA-N 0.000 claims description 2
• IWJVQGOSCNTJTM-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-hydroxyethylamino)phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C=1C=C(NCCO)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 IWJVQGOSCNTJTM-UHFFFAOYSA-N 0.000 claims description 2
• PYFMDJILOWLTKE-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-hydroxyethylamino)phenyl]pyrazol-3-yl]-3-[2-fluoro-4-(2-methylpyridin-4-yl)oxyphenyl]urea Chemical compound C1=NC(C)=CC(OC=2C=C(F)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(NCCO)=CC=3)=CC=2)=C1 PYFMDJILOWLTKE-UHFFFAOYSA-N 0.000 claims description 2
• YSRYOEYJFNXKLM-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-methoxyethylamino)phenyl]pyrazol-3-yl]-3-[2-fluoro-4-(2-methylpyridin-4-yl)oxyphenyl]urea Chemical compound C1=CC(NCCOC)=CC=C1N1C(NC(=O)NC=2C(=CC(OC=3C=C(C)N=CC=3)=CC=2)F)=CC(C(C)(C)C)=N1 YSRYOEYJFNXKLM-UHFFFAOYSA-N 0.000 claims description 2
• NNOBAVIJDTWLOU-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-morpholin-4-yl-2-oxoethyl)phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C=1C=C(CC(=O)N2CCOCC2)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 NNOBAVIJDTWLOU-UHFFFAOYSA-N 0.000 claims description 2
• MJSHSPYDBYHGGS-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-morpholin-4-ylethyl)phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C=1C=C(CCN2CCOCC2)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MJSHSPYDBYHGGS-UHFFFAOYSA-N 0.000 claims description 2
• JJMQMWZNCNHZST-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-oxo-2-piperazin-1-ylethyl)phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C=1C=C(CC(=O)N2CCNCC2)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 JJMQMWZNCNHZST-UHFFFAOYSA-N 0.000 claims description 2
• BSPKVZSNFLDDRN-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-oxo-2-pyrrolidin-1-ylethyl)phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C=1C=C(CC(=O)N2CCCC2)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 BSPKVZSNFLDDRN-UHFFFAOYSA-N 0.000 claims description 2
• XLDPNPVNGPJRGL-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-piperazin-1-ylethyl)phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C=1C=C(CCN2CCNCC2)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 XLDPNPVNGPJRGL-UHFFFAOYSA-N 0.000 claims description 2
• DHNIQTXBUKETQP-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-piperidin-4-ylethoxy)phenyl]pyrazol-3-yl]-3-[2-fluoro-4-(2-methylpyridin-4-yl)oxyphenyl]urea Chemical compound C1=NC(C)=CC(OC=2C=C(F)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(OCCC4CCNCC4)=CC=3)=CC=2)=C1 DHNIQTXBUKETQP-UHFFFAOYSA-N 0.000 claims description 2
• KKPNCIBIIXJIJW-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrazol-3-yl]-3-(4-pyridin-3-yloxyphenyl)urea Chemical compound C=1C=C(OCCN2CCCC2)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=CN=C1 KKPNCIBIIXJIJW-UHFFFAOYSA-N 0.000 claims description 2
• DTQKTQIRVVJANJ-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C=1C=C(OCCN2CCCC2)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 DTQKTQIRVVJANJ-UHFFFAOYSA-N 0.000 claims description 2
• SRUJCVACIINUDZ-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-pyrrolidin-1-ylethoxy)phenyl]pyrazol-3-yl]-3-[2-fluoro-4-(2-methylpyridin-4-yl)oxyphenyl]urea Chemical compound C1=NC(C)=CC(OC=2C=C(F)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(OCCN4CCCC4)=CC=3)=CC=2)=C1 SRUJCVACIINUDZ-UHFFFAOYSA-N 0.000 claims description 2
• CYKMPDFAJNHZLP-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(2-pyrrolidin-1-ylethyl)phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C=1C=C(CCN2CCCC2)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 CYKMPDFAJNHZLP-UHFFFAOYSA-N 0.000 claims description 2
• BEFXPHGMOFMGRO-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(3-hydroxypropoxy)phenyl]pyrazol-3-yl]-3-(4-pyridin-3-yloxyphenyl)urea Chemical compound C=1C=C(OCCCO)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=CN=C1 BEFXPHGMOFMGRO-UHFFFAOYSA-N 0.000 claims description 2
• IOKXXPYJWBVTRC-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(3-hydroxypropoxy)phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C=1C=C(OCCCO)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 IOKXXPYJWBVTRC-UHFFFAOYSA-N 0.000 claims description 2
• UDJCREBRPUSTLP-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(3-hydroxypropoxy)phenyl]pyrazol-3-yl]-3-[2-fluoro-4-(2-methylpyridin-4-yl)oxyphenyl]urea Chemical compound C1=NC(C)=CC(OC=2C=C(F)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(OCCCO)=CC=3)=CC=2)=C1 UDJCREBRPUSTLP-UHFFFAOYSA-N 0.000 claims description 2
• IRWFZMZXGMGFEV-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(3-hydroxypropylamino)phenyl]pyrazol-3-yl]-3-(4-pyridin-3-yloxyphenyl)urea Chemical compound C=1C=C(NCCCO)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=CN=C1 IRWFZMZXGMGFEV-UHFFFAOYSA-N 0.000 claims description 2
• CCMKXZJIDTYJCY-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(3-hydroxypropylamino)phenyl]pyrazol-3-yl]-3-[2-fluoro-4-(2-methylpyridin-4-yl)oxyphenyl]urea Chemical compound C1=NC(C)=CC(OC=2C=C(F)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(NCCCO)=CC=3)=CC=2)=C1 CCMKXZJIDTYJCY-UHFFFAOYSA-N 0.000 claims description 2
• NCGUIFLZYSXFJZ-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(oxolan-2-ylmethylsulfamoyl)-3-(trifluoromethoxy)phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C=1C=C(S(=O)(=O)NCC2OCCC2)C(OC(F)(F)F)=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 NCGUIFLZYSXFJZ-UHFFFAOYSA-N 0.000 claims description 2
• XGRCTUPHXPXFSC-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-(oxolan-2-ylmethylsulfamoyl)-3-(trifluoromethoxy)phenyl]pyrazol-3-yl]-3-[2-fluoro-4-(2-methylpyridin-4-yl)oxyphenyl]urea Chemical compound C1=NC(C)=CC(OC=2C=C(F)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=C(OC(F)(F)F)C(=CC=3)S(=O)(=O)NCC3OCCC3)=CC=2)=C1 XGRCTUPHXPXFSC-UHFFFAOYSA-N 0.000 claims description 2
• FJZJQSMXSKSYTH-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-[(2-methoxyethylamino)methyl]phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C1=CC(CNCCOC)=CC=C1N1C(NC(=O)NC=2C=CC(OC=3C=CN=CC=3)=CC=2)=CC(C(C)(C)C)=N1 FJZJQSMXSKSYTH-UHFFFAOYSA-N 0.000 claims description 2
• MDVZQFPUAKENCZ-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-[(2-methoxyethylamino)methyl]phenyl]pyrazol-3-yl]-3-[2-fluoro-4-(2-methylpyridin-4-yl)oxyphenyl]urea Chemical compound C1=CC(CNCCOC)=CC=C1N1C(NC(=O)NC=2C(=CC(OC=3C=C(C)N=CC=3)=CC=2)F)=CC(C(C)(C)C)=N1 MDVZQFPUAKENCZ-UHFFFAOYSA-N 0.000 claims description 2
• CADFTZYMNPVRRQ-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-[(4-hydroxy-3,3-dimethylbutyl)amino]phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C1=CC(NCCC(C)(CO)C)=CC=C1N1C(NC(=O)NC=2C=CC(OC=3C=CN=CC=3)=CC=2)=CC(C(C)(C)C)=N1 CADFTZYMNPVRRQ-UHFFFAOYSA-N 0.000 claims description 2
• QFFHSPCOWRJBTH-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-[2-(2-methoxyethylamino)ethyl]phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C1=CC(CCNCCOC)=CC=C1N1C(NC(=O)NC=2C=CC(OC=3C=CN=CC=3)=CC=2)=CC(C(C)(C)C)=N1 QFFHSPCOWRJBTH-UHFFFAOYSA-N 0.000 claims description 2
• SHOXRHCWJDTZHP-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-[2-(2-morpholin-4-ylethylamino)ethyl]phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C=1C=C(CCNCCN2CCOCC2)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 SHOXRHCWJDTZHP-UHFFFAOYSA-N 0.000 claims description 2
• QAEPQYCYOULHKB-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-[2-(4-methylpiperazin-1-yl)-2-oxoethyl]phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C1CN(C)CCN1C(=O)CC1=CC=C(N2C(=CC(=N2)C(C)(C)C)NC(=O)NC=2C=CC(OC=3C=CN=CC=3)=CC=2)C=C1 QAEPQYCYOULHKB-UHFFFAOYSA-N 0.000 claims description 2
• DKEDTEYIOZMUAG-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-[2-(4-methylpiperazin-1-yl)ethyl]phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C1CN(C)CCN1CCC1=CC=C(N2C(=CC(=N2)C(C)(C)C)NC(=O)NC=2C=CC(OC=3C=CN=CC=3)=CC=2)C=C1 DKEDTEYIOZMUAG-UHFFFAOYSA-N 0.000 claims description 2
• OKNQYBVPDCLFJN-RUZDIDTESA-N 1-[5-tert-butyl-2-[4-[2-[(3r)-3-hydroxypyrrolidin-1-yl]ethyl]phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C=1C=C(CCN2C[C@H](O)CC2)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 OKNQYBVPDCLFJN-RUZDIDTESA-N 0.000 claims description 2
• OZOJRCNJURVGPS-UHFFFAOYSA-N 1-[5-tert-butyl-2-[4-[dimethylsulfamoyl(2-hydroxyethyl)amino]phenyl]pyrazol-3-yl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound C1=CC(N(CCO)S(=O)(=O)N(C)C)=CC=C1N1C(NC(=O)NC=2C=CC(OC=3C=CN=CC=3)=CC=2)=CC(C(C)(C)C)=N1 OZOJRCNJURVGPS-UHFFFAOYSA-N 0.000 claims description 2
• GCYFECCUPQKKIS-UHFFFAOYSA-N 2-[4-[3-tert-butyl-5-[[2-fluoro-4-(2-methylpyridin-4-yl)oxyphenyl]carbamoylamino]pyrazol-1-yl]phenyl]acetic acid Chemical compound C1=NC(C)=CC(OC=2C=C(F)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(CC(O)=O)=CC=3)=CC=2)=C1 GCYFECCUPQKKIS-UHFFFAOYSA-N 0.000 claims description 2
• UZFPOOOQHWICKY-UHFFFAOYSA-N 3-[13-[1-[1-[8,12-bis(2-carboxyethyl)-17-(1-hydroxyethyl)-3,7,13,18-tetramethyl-21,24-dihydroporphyrin-2-yl]ethoxy]ethyl]-18-(2-carboxyethyl)-8-(1-hydroxyethyl)-3,7,12,17-tetramethyl-22,23-dihydroporphyrin-2-yl]propanoic acid Chemical compound N1C(C=C2C(=C(CCC(O)=O)C(C=C3C(=C(C)C(C=C4N5)=N3)CCC(O)=O)=N2)C)=C(C)C(C(C)O)=C1C=C5C(C)=C4C(C)OC(C)C1=C(N2)C=C(N3)C(C)=C(C(O)C)C3=CC(C(C)=C3CCC(O)=O)=NC3=CC(C(CCC(O)=O)=C3C)=NC3=CC2=C1C UZFPOOOQHWICKY-UHFFFAOYSA-N 0.000 claims description 2
• ZPWKORUGOJSORB-UHFFFAOYSA-N 3-[3-tert-butyl-5-[(4-pyridin-4-yloxyphenyl)carbamoylamino]pyrazol-1-yl]-n-[[6-(trifluoromethyl)pyridin-3-yl]methyl]benzamide Chemical compound C=1C=CC(C(=O)NCC=2C=NC(=CC=2)C(F)(F)F)=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 ZPWKORUGOJSORB-UHFFFAOYSA-N 0.000 claims description 2
• WUIABRMSWOKTOF-OYALTWQYSA-N 3-[[2-[2-[2-[[(2s,3r)-2-[[(2s,3s,4r)-4-[[(2s,3r)-2-[[6-amino-2-[(1s)-3-amino-1-[[(2s)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[(2r,3s,4s,5s,6s)-3-[(2r,3s,4s,5r,6r)-4-carbamoyloxy-3,5-dihydroxy-6-(hydroxymethyl)ox Chemical compound OS([O-])(=O)=O.N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1NC=NC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C WUIABRMSWOKTOF-OYALTWQYSA-N 0.000 claims description 2
• CLPFFLWZZBQMAO-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-5-yl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1N2C=NC=C2CCC1 CLPFFLWZZBQMAO-UHFFFAOYSA-N 0.000 claims description 2
• YNGGGHFMBJCLNB-UHFFFAOYSA-N 4-[3-[3-tert-butyl-5-[(4-pyridin-3-yloxyphenyl)carbamoylamino]pyrazol-1-yl]anilino]-2,2-dimethyl-4-oxobutanoic acid Chemical compound C=1C=CC(NC(=O)CC(C)(C)C(O)=O)=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=CN=C1 YNGGGHFMBJCLNB-UHFFFAOYSA-N 0.000 claims description 2
• APZFKCZMJDYADH-UHFFFAOYSA-N 4-[3-[3-tert-butyl-5-[(4-pyridin-3-yloxyphenyl)carbamoylamino]pyrazol-1-yl]anilino]-4-oxobutanoic acid Chemical compound C=1C=CC(NC(=O)CCC(O)=O)=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=CN=C1 APZFKCZMJDYADH-UHFFFAOYSA-N 0.000 claims description 2
• PETPNBXTUIBDEX-UHFFFAOYSA-N 4-[3-[3-tert-butyl-5-[(4-pyridin-4-yloxyphenyl)carbamoylamino]pyrazol-1-yl]anilino]-2,2-dimethyl-4-oxobutanoic acid Chemical compound C=1C=CC(NC(=O)CC(C)(C)C(O)=O)=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 PETPNBXTUIBDEX-UHFFFAOYSA-N 0.000 claims description 2
• YVLMTWFYYGHPTE-UHFFFAOYSA-N 4-[3-[3-tert-butyl-5-[(4-pyridin-4-yloxyphenyl)carbamoylamino]pyrazol-1-yl]anilino]-4-oxobutanoic acid Chemical compound C=1C=CC(NC(=O)CCC(O)=O)=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 YVLMTWFYYGHPTE-UHFFFAOYSA-N 0.000 claims description 2
• XYJJOLQPUIHANP-UHFFFAOYSA-N 4-[4-[3-tert-butyl-5-[(4-pyridin-3-yloxyphenyl)carbamoylamino]pyrazol-1-yl]anilino]-2,2-dimethyl-4-oxobutanoic acid Chemical compound C=1C=C(NC(=O)CC(C)(C)C(O)=O)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=CN=C1 XYJJOLQPUIHANP-UHFFFAOYSA-N 0.000 claims description 2
• MWZVBHSUGPXOIH-UHFFFAOYSA-N 4-[4-[3-tert-butyl-5-[(4-pyridin-3-yloxyphenyl)carbamoylamino]pyrazol-1-yl]anilino]-4-oxobutanoic acid Chemical compound C=1C=C(NC(=O)CCC(O)=O)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=CN=C1 MWZVBHSUGPXOIH-UHFFFAOYSA-N 0.000 claims description 2
• QLOXNMRQTDBEJN-UHFFFAOYSA-N 4-[4-[3-tert-butyl-5-[(4-pyridin-4-yloxyphenyl)carbamoylamino]pyrazol-1-yl]anilino]-4-oxobutanoic acid Chemical compound C=1C=C(NC(=O)CCC(O)=O)C=CC=1N1N=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 QLOXNMRQTDBEJN-UHFFFAOYSA-N 0.000 claims description 2
• GDJYQPPXVFYADK-UHFFFAOYSA-N 4-[4-[3-tert-butyl-5-[[2-fluoro-4-(2-methylpyridin-4-yl)oxyphenyl]carbamoylamino]pyrazol-1-yl]phenoxy]butanoic acid Chemical compound C1=NC(C)=CC(OC=2C=C(F)C(NC(=O)NC=3N(N=C(C=3)C(C)(C)C)C=3C=CC(OCCCC(O)=O)=CC=3)=CC=2)=C1 GDJYQPPXVFYADK-UHFFFAOYSA-N 0.000 claims description 2
• TVZGACDUOSZQKY-LBPRGKRZSA-N 4-aminofolic acid Chemical compound C1=NC2=NC(N)=NC(N)=C2N=C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 TVZGACDUOSZQKY-LBPRGKRZSA-N 0.000 claims description 2
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