AU2001280009A1 - Pyrazole derivatives and their use as protein kinase inhibitors - Google Patents
Pyrazole derivatives and their use as protein kinase inhibitorsInfo
- Publication number
- AU2001280009A1 AU2001280009A1 AU2001280009A AU8000901A AU2001280009A1 AU 2001280009 A1 AU2001280009 A1 AU 2001280009A1 AU 2001280009 A AU2001280009 A AU 2001280009A AU 8000901 A AU8000901 A AU 8000901A AU 2001280009 A1 AU2001280009 A1 AU 2001280009A1
- Authority
- AU
- Australia
- Prior art keywords
- pyrazol
- cyclobutyl
- phenyl
- acetamide
- naphthalen
- 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.)
- Abandoned
Links
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title description 2
- 239000003909 protein kinase inhibitor Substances 0.000 title description 2
- 150000003217 pyrazoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 341
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 93
- 241000124008 Mammalia Species 0.000 claims description 73
- 201000010099 disease Diseases 0.000 claims description 73
- 239000008194 pharmaceutical composition Substances 0.000 claims description 51
- 230000000694 effects Effects 0.000 claims description 45
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 40
- 239000003112 inhibitor Substances 0.000 claims description 36
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 230000002159 abnormal effect Effects 0.000 claims description 25
- 239000003937 drug carrier Substances 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 230000010261 cell growth Effects 0.000 claims description 23
- 125000006239 protecting group Chemical group 0.000 claims description 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 17
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
- 108010040718 Neurokinin-1 Receptors Proteins 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 14
- 229960003638 dopamine Drugs 0.000 claims description 14
- 230000004770 neurodegeneration Effects 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 201000004384 Alopecia Diseases 0.000 claims description 13
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 230000005062 synaptic transmission Effects 0.000 claims description 13
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 12
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 12
- 208000001145 Metabolic Syndrome Diseases 0.000 claims description 12
- 239000000544 cholinesterase inhibitor Substances 0.000 claims description 12
- 230000001404 mediated effect Effects 0.000 claims description 12
- 125000006554 (C4-C8) cycloalkenyl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 claims description 11
- 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 claims description 10
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- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000003703 n methyl dextro aspartic acid receptor blocking agent Substances 0.000 claims description 8
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 7
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
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- VGIGHGMPMUCLIQ-UHFFFAOYSA-N LSM-2183 Chemical compound C1=CC(F)=CC=C1N1CCN(CCCN2S(C=3C=CC=C4C=CC=C2C=34)(=O)=O)CC1 VGIGHGMPMUCLIQ-UHFFFAOYSA-N 0.000 claims description 6
- 206010028289 Muscle atrophy Diseases 0.000 claims description 6
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- 102000004257 Potassium Channel Human genes 0.000 claims description 6
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- QOIGKGMMAGJZNZ-UHFFFAOYSA-N gepirone Chemical compound O=C1CC(C)(C)CC(=O)N1CCCCN1CCN(C=2N=CC=CN=2)CC1 QOIGKGMMAGJZNZ-UHFFFAOYSA-N 0.000 claims description 6
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- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 230000036314 physical performance Effects 0.000 claims description 6
- 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 6
- 108020001213 potassium channel Proteins 0.000 claims description 6
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims description 6
- 208000001076 sarcopenia Diseases 0.000 claims description 6
- 230000022379 skeletal muscle tissue development Effects 0.000 claims description 6
- 238000001356 surgical procedure Methods 0.000 claims description 6
- 210000000115 thoracic cavity Anatomy 0.000 claims description 6
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 claims description 6
- AHDDRJBFJBDEPW-UHFFFAOYSA-N 2-phenylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C1=CC=CC=C1 AHDDRJBFJBDEPW-UHFFFAOYSA-N 0.000 claims description 5
- XLJWJFKYRFPJSD-LZQZEXGQSA-N 3-[2-[(1s,5r,6s)-6-(4-fluorophenyl)-3-azabicyclo[3.2.0]heptan-3-yl]ethyl]-1h-quinazoline-2,4-dione Chemical compound C1=CC(F)=CC=C1[C@@H]1[C@H]2CN(CCN3C(C4=CC=CC=C4NC3=O)=O)C[C@H]2C1 XLJWJFKYRFPJSD-LZQZEXGQSA-N 0.000 claims description 5
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- NYSDRDDQELAVKP-SFHVURJKSA-N flesinoxan Chemical compound C([C@@H](O1)CO)OC2=C1C=CC=C2N(CC1)CCN1CCNC(=O)C1=CC=C(F)C=C1 NYSDRDDQELAVKP-SFHVURJKSA-N 0.000 claims description 5
- 229950003678 flesinoxan Drugs 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 229960000647 gepirone Drugs 0.000 claims description 5
- 229940047889 isobutyramide Drugs 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 5
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims description 5
- 229960005017 olanzapine Drugs 0.000 claims description 5
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 5
- 229960001534 risperidone Drugs 0.000 claims description 5
- WNUQCGWXPNGORO-NRFANRHFSA-N sonepiprazole Chemical compound C1=CC(S(=O)(=O)N)=CC=C1N1CCN(CC[C@H]2C3=CC=CC=C3CCO2)CC1 WNUQCGWXPNGORO-NRFANRHFSA-N 0.000 claims description 5
- 229950001013 sonepiprazole Drugs 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 229960000607 ziprasidone Drugs 0.000 claims description 5
- AZNRZRAFNYMLPE-UHFFFAOYSA-N 5-cyclobutyl-n-(4-nitrophenyl)-1h-pyrazol-3-amine Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1=NNC(C2CCC2)=C1 AZNRZRAFNYMLPE-UHFFFAOYSA-N 0.000 claims description 4
- MYBLWWXYFZDNBL-UHFFFAOYSA-N 5-cyclobutyl-n-[3-(trifluoromethoxy)phenyl]-1h-pyrazol-3-amine Chemical compound FC(F)(F)OC1=CC=CC(NC=2NN=C(C=2)C2CCC2)=C1 MYBLWWXYFZDNBL-UHFFFAOYSA-N 0.000 claims description 4
- ZLKMOIHCHCMSFW-UHFFFAOYSA-N 6-chloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(Cl)=N1 ZLKMOIHCHCMSFW-UHFFFAOYSA-N 0.000 claims description 4
- LTUUGSGSUZRPRV-UHFFFAOYSA-N 6-methylpyridine-2-carboxylic acid Chemical compound CC1=CC=CC(C(O)=O)=N1 LTUUGSGSUZRPRV-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- KOQYLLSJELNBIO-UHFFFAOYSA-N n-[3-[3-[3-(trifluoromethyl)anilino]-1h-pyrazol-5-yl]cyclopentyl]pyridine-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC(NC2=NNC(=C2)C2CC(CC2)NC(=O)C=2N=CC=CC=2)=C1 KOQYLLSJELNBIO-UHFFFAOYSA-N 0.000 claims description 4
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000005493 quinolyl group Chemical group 0.000 claims description 4
- IPPGMQFOEAVJNB-UHFFFAOYSA-N 1-n-(5-cyclobutyl-1h-pyrazol-3-yl)-3-n,3-n-dimethylbenzene-1,3-diamine Chemical compound CN(C)C1=CC=CC(NC=2NN=C(C=2)C2CCC2)=C1 IPPGMQFOEAVJNB-UHFFFAOYSA-N 0.000 claims description 3
- YWTVISKAZZLERG-UHFFFAOYSA-N 1-n-(5-cyclobutyl-1h-pyrazol-3-yl)-4-n,4-n-dimethylnaphthalene-1,4-diamine Chemical compound C12=CC=CC=C2C(N(C)C)=CC=C1NC(NN=1)=CC=1C1CCC1 YWTVISKAZZLERG-UHFFFAOYSA-N 0.000 claims description 3
- VTLAZVPCFNVDRL-UHFFFAOYSA-N 2,2,2-trifluoro-n-[3-[3-[3-(trifluoromethyl)anilino]-1h-pyrazol-5-yl]cyclopentyl]acetamide Chemical compound C1C(NC(=O)C(F)(F)F)CCC1C1=CC(NC=2C=C(C=CC=2)C(F)(F)F)=NN1 VTLAZVPCFNVDRL-UHFFFAOYSA-N 0.000 claims description 3
- OAVDLHAZBVVJMR-UHFFFAOYSA-N 2,2-dimethyl-n-[3-[3-[3-(trifluoromethyl)anilino]-1h-pyrazol-5-yl]cyclopentyl]propanamide Chemical compound C1C(NC(=O)C(C)(C)C)CCC1C1=CC(NC=2C=C(C=CC=2)C(F)(F)F)=NN1 OAVDLHAZBVVJMR-UHFFFAOYSA-N 0.000 claims description 3
- PCAFDDBWOWEQEK-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n-[5-[3-[3-(methylaminomethyl)phenyl]cyclobutyl]-1h-pyrazol-3-yl]acetamide Chemical compound CNCC1=CC=CC(C2CC(C2)C2=NNC(NC(=O)CC=3C=CC(OC)=CC=3)=C2)=C1 PCAFDDBWOWEQEK-UHFFFAOYSA-N 0.000 claims description 3
- ZCBWXPHHPJZBAZ-UHFFFAOYSA-N 2-n-(5-cyclobutyl-1h-pyrazol-3-yl)-6-n,6-n-dimethylpyridine-2,6-diamine Chemical compound CN(C)C1=CC=CC(NC=2NN=C(C=2)C2CCC2)=N1 ZCBWXPHHPJZBAZ-UHFFFAOYSA-N 0.000 claims description 3
- MMYJHIFAWFHUFJ-UHFFFAOYSA-N 4-[(5-cyclobutyl-1h-pyrazol-3-yl)amino]benzonitrile Chemical compound C1=CC(C#N)=CC=C1NC1=CC(C2CCC2)=NN1 MMYJHIFAWFHUFJ-UHFFFAOYSA-N 0.000 claims description 3
- QNSLMUPBIAEDHZ-UHFFFAOYSA-N 5-cyclobutyl-n-(3,5-dichlorophenyl)-1h-pyrazol-3-amine Chemical compound ClC1=CC(Cl)=CC(NC=2NN=C(C=2)C2CCC2)=C1 QNSLMUPBIAEDHZ-UHFFFAOYSA-N 0.000 claims description 3
- RMKZQZHBVMJWDU-UHFFFAOYSA-N 5-cyclobutyl-n-(3-fluorophenyl)-1h-pyrazol-3-amine Chemical compound FC1=CC=CC(NC=2NN=C(C=2)C2CCC2)=C1 RMKZQZHBVMJWDU-UHFFFAOYSA-N 0.000 claims description 3
- NOMROUXFFYEBJD-UHFFFAOYSA-N 5-cyclobutyl-n-(3-methoxyphenyl)-1h-pyrazol-3-amine Chemical compound COC1=CC=CC(NC=2NN=C(C=2)C2CCC2)=C1 NOMROUXFFYEBJD-UHFFFAOYSA-N 0.000 claims description 3
- QHEDHOHVFPSPGJ-UHFFFAOYSA-N 5-cyclobutyl-n-naphthalen-1-yl-1h-pyrazol-3-amine Chemical compound C1CCC1C1=NNC(NC=2C3=CC=CC=C3C=CC=2)=C1 QHEDHOHVFPSPGJ-UHFFFAOYSA-N 0.000 claims description 3
- RBPMIOJKPZSABD-UHFFFAOYSA-N 6-chloro-n-(5-cyclobutyl-1h-pyrazol-3-yl)pyridin-2-amine Chemical compound ClC1=CC=CC(NC=2NN=C(C=2)C2CCC2)=N1 RBPMIOJKPZSABD-UHFFFAOYSA-N 0.000 claims description 3
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 3
- LCZBHYUZCGMMCS-UHFFFAOYSA-N n-(3-bromophenyl)-5-cyclobutyl-1h-pyrazol-3-amine Chemical compound BrC1=CC=CC(NC=2NN=C(C=2)C2CCC2)=C1 LCZBHYUZCGMMCS-UHFFFAOYSA-N 0.000 claims description 3
- KBAJDNNZIIXNMS-UHFFFAOYSA-N n-(5-cyclobutyl-1h-pyrazol-3-yl)-6-(trifluoromethyl)pyridin-2-amine Chemical compound FC(F)(F)C1=CC=CC(NC=2NN=C(C=2)C2CCC2)=N1 KBAJDNNZIIXNMS-UHFFFAOYSA-N 0.000 claims description 3
- MOGPJBOKQCNFRX-UHFFFAOYSA-N n-(5-cyclobutyl-1h-pyrazol-3-yl)-6-methoxy-4-methylquinolin-2-amine Chemical compound C1=C(C)C2=CC(OC)=CC=C2N=C1NC(NN=1)=CC=1C1CCC1 MOGPJBOKQCNFRX-UHFFFAOYSA-N 0.000 claims description 3
- FWRSNDDEJVDPHU-UHFFFAOYSA-N n-(5-cyclobutyl-1h-pyrazol-3-yl)quinolin-2-amine Chemical compound C1CCC1C1=NNC(NC=2N=C3C=CC=CC3=CC=2)=C1 FWRSNDDEJVDPHU-UHFFFAOYSA-N 0.000 claims description 3
- HONMLEQTEHITQP-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-5-cyclobutyl-1h-pyrazol-3-amine Chemical compound C1=CC(Cl)=CC=C1CNC1=CC(C2CCC2)=NN1 HONMLEQTEHITQP-UHFFFAOYSA-N 0.000 claims description 3
- MGAQVFJHIBWKSS-UHFFFAOYSA-N n-[3-[3-[(2-naphthalen-1-ylacetyl)amino]-1h-pyrazol-5-yl]cyclopentyl]cyclopropanecarboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1CC(=O)NC(NN=1)=CC=1C(C1)CCC1NC(=O)C1CC1 MGAQVFJHIBWKSS-UHFFFAOYSA-N 0.000 claims description 3
- CVEHDRLRNLBHRC-UHFFFAOYSA-N n-[3-[3-[3-(trifluoromethyl)anilino]-1h-pyrazol-5-yl]cyclopentyl]cyclohexanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC2=NNC(=C2)C2CC(CC2)NC(=O)C2CCCCC2)=C1 CVEHDRLRNLBHRC-UHFFFAOYSA-N 0.000 claims description 3
- WEACOVDVWBGQCN-UHFFFAOYSA-N n-[3-[3-[3-(trifluoromethyl)anilino]-1h-pyrazol-5-yl]cyclopentyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC2=NNC(=C2)C2CC(CC2)NC(=O)C2CC2)=C1 WEACOVDVWBGQCN-UHFFFAOYSA-N 0.000 claims description 3
- SSDHICPKRUFVQN-UHFFFAOYSA-N n-[3-[3-[3-(trifluoromethyl)anilino]-1h-pyrazol-5-yl]cyclopentyl]propanamide Chemical compound C1C(NC(=O)CC)CCC1C1=CC(NC=2C=C(C=CC=2)C(F)(F)F)=NN1 SSDHICPKRUFVQN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000005495 pyridazyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 claims description 3
- VIPORHYIYLBZEF-UHFFFAOYSA-N 2,2,2-trifluoro-n-[3-[3-[(2-naphthalen-1-ylacetyl)amino]-1h-pyrazol-5-yl]cyclopentyl]acetamide Chemical compound C1C(NC(=O)C(F)(F)F)CCC1C1=NNC(NC(=O)CC=2C3=CC=CC=C3C=CC=2)=C1 VIPORHYIYLBZEF-UHFFFAOYSA-N 0.000 claims description 2
- AYEGPMGNMOIHDL-UHFFFAOYSA-N 2-methylcyclopropane-1-carboxylic acid Chemical compound CC1CC1C(O)=O AYEGPMGNMOIHDL-UHFFFAOYSA-N 0.000 claims description 2
- OHWRUAHELBIRDH-UHFFFAOYSA-N 2-naphthalen-1-yl-n-[5-[(1,3-thiazol-2-ylamino)methyl]-1h-pyrazol-3-yl]acetamide Chemical compound C=1C=CC2=CC=CC=C2C=1CC(=O)NC(=NN1)C=C1CNC1=NC=CS1 OHWRUAHELBIRDH-UHFFFAOYSA-N 0.000 claims description 2
- CZNBBEJUYLPARH-UHFFFAOYSA-N 2-naphthalen-1-yl-n-[5-[3-(5-nitropyridin-2-yl)oxycyclobutyl]-1h-pyrazol-3-yl]acetamide Chemical compound N1=CC([N+](=O)[O-])=CC=C1OC1CC(C=2NN=C(NC(=O)CC=3C4=CC=CC=C4C=CC=3)C=2)C1 CZNBBEJUYLPARH-UHFFFAOYSA-N 0.000 claims description 2
- UHABCSYGRLEECW-UHFFFAOYSA-N 2-naphthalen-1-yl-n-[5-[3-[5-(trifluoromethyl)pyridin-2-yl]oxycyclobutyl]-1h-pyrazol-3-yl]acetamide Chemical compound N1=CC(C(F)(F)F)=CC=C1OC1CC(C=2NN=C(NC(=O)CC=3C4=CC=CC=C4C=CC=3)C=2)C1 UHABCSYGRLEECW-UHFFFAOYSA-N 0.000 claims description 2
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- AUWSNGSIDLRGSL-UHFFFAOYSA-N 5-(1,4-dioxaspiro[4.4]nonan-8-yl)-n-[3-(trifluoromethyl)phenyl]-1h-pyrazol-3-amine Chemical compound FC(F)(F)C1=CC=CC(NC2=NNC(=C2)C2CC3(CC2)OCCO3)=C1 AUWSNGSIDLRGSL-UHFFFAOYSA-N 0.000 claims description 2
- CKKWZMUGVGRYOM-UHFFFAOYSA-N 5-cyclobutyl-n-(3-phenylmethoxyphenyl)-1h-pyrazol-3-amine Chemical compound C=1C=CC=CC=1COC(C=1)=CC=CC=1NC(NN=1)=CC=1C1CCC1 CKKWZMUGVGRYOM-UHFFFAOYSA-N 0.000 claims description 2
- BMFGAFAVMNOHPA-UHFFFAOYSA-N 5-cyclobutyl-n-(4-methoxyphenyl)-1h-pyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1NC1=NNC(C2CCC2)=C1 BMFGAFAVMNOHPA-UHFFFAOYSA-N 0.000 claims description 2
- SBVBRVGFZZOIDH-UHFFFAOYSA-N 5-cyclobutyl-n-[3-(trifluoromethyl)phenyl]-1h-pyrazol-3-amine Chemical compound FC(F)(F)C1=CC=CC(NC=2NN=C(C=2)C2CCC2)=C1 SBVBRVGFZZOIDH-UHFFFAOYSA-N 0.000 claims description 2
- 102000002002 Neurokinin-1 Receptors Human genes 0.000 claims description 2
- GTQPDABHYSLSQS-UHFFFAOYSA-N n-(5-ethyl-1h-pyrazol-3-yl)-6-methoxypyridin-2-amine Chemical compound N1N=C(CC)C=C1NC1=CC=CC(OC)=N1 GTQPDABHYSLSQS-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Hematology (AREA)
- Reproductive Health (AREA)
- Obesity (AREA)
- Neurosurgery (AREA)
- Endocrinology (AREA)
- Biomedical Technology (AREA)
- Gynecology & Obstetrics (AREA)
- Psychiatry (AREA)
- Oncology (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Communicable Diseases (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- Pregnancy & Childbirth (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22941500P | 2000-08-31 | 2000-08-31 | |
| US60229415 | 2000-08-31 | ||
| PCT/IB2001/001540 WO2002018346A1 (fr) | 2000-08-31 | 2001-08-24 | Derives pyrazole et leur utilisation en tant qu'inhibiteurs des proteines kinases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2001280009A1 true AU2001280009A1 (en) | 2002-03-13 |
Family
ID=22861151
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2001280009A Abandoned AU2001280009A1 (en) | 2000-08-31 | 2001-08-24 | Pyrazole derivatives and their use as protein kinase inhibitors |
Country Status (38)
| Country | Link |
|---|---|
| EP (1) | EP1313710A1 (fr) |
| JP (1) | JP2004507526A (fr) |
| KR (1) | KR20030027093A (fr) |
| CN (1) | CN1518543A (fr) |
| AP (1) | AP2001002266A0 (fr) |
| AR (1) | AR035345A1 (fr) |
| AU (1) | AU2001280009A1 (fr) |
| BG (1) | BG107455A (fr) |
| BR (1) | BR0113574A (fr) |
| CA (1) | CA2420363A1 (fr) |
| CR (1) | CR6881A (fr) |
| CZ (1) | CZ2003468A3 (fr) |
| DO (1) | DOP2001000243A (fr) |
| DZ (1) | DZ3398A1 (fr) |
| EA (1) | EA200300205A1 (fr) |
| EC (1) | ECSP034480A (fr) |
| EE (1) | EE200300085A (fr) |
| GT (1) | GT200100179A (fr) |
| HN (1) | HN2001000192A (fr) |
| HR (1) | HRP20030140A2 (fr) |
| HU (1) | HUP0302669A3 (fr) |
| IL (1) | IL154016A0 (fr) |
| IS (1) | IS6687A (fr) |
| MA (1) | MA26946A1 (fr) |
| MX (1) | MXPA03001785A (fr) |
| NO (1) | NO20030958L (fr) |
| NZ (1) | NZ523656A (fr) |
| OA (1) | OA12368A (fr) |
| PA (1) | PA8528101A1 (fr) |
| PE (1) | PE20020470A1 (fr) |
| PL (1) | PL360742A1 (fr) |
| SK (1) | SK2002003A3 (fr) |
| SV (1) | SV2002000618A (fr) |
| TN (1) | TNSN01132A1 (fr) |
| UY (1) | UY26909A1 (fr) |
| WO (1) | WO2002018346A1 (fr) |
| YU (1) | YU14703A (fr) |
| ZA (1) | ZA200301064B (fr) |
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| HK1042251B (en) | 1999-01-13 | 2012-07-20 | Bayer Healthcare Llc | Omega-carboxy aryl substituted diphenyl ureas as p38 kinase inhibitors |
| ME00275B (fr) | 1999-01-13 | 2011-02-10 | Bayer Corp | DIPHENYLUREES A SUBSTITUANTS ω-CARBOXYARYLES, INHIBITRICES DE KINASE RAF |
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| US7473691B2 (en) | 2000-09-15 | 2009-01-06 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US6610677B2 (en) | 2000-09-15 | 2003-08-26 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| EP1317450B1 (fr) | 2000-09-15 | 2006-11-22 | Vertex Pharmaceuticals Incorporated | Composes de pyrazole utiles comme inhibiteurs de proteine kinase |
| US6660731B2 (en) | 2000-09-15 | 2003-12-09 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| CA2432222C (fr) | 2000-12-21 | 2008-07-29 | Vertex Pharmaceuticals Incorporated | Composes de pyrazole utiles comme inhibiteurs de proteines kinases |
| ATE372114T1 (de) * | 2001-09-27 | 2007-09-15 | Applied Research Systems | Verfahren zur erhöhung des testosteronspiegels |
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| CN101037438A (zh) | 2002-08-02 | 2007-09-19 | 沃泰克斯药物股份有限公司 | 用作gsk-3的抑制剂的吡唑组合物 |
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| ATE410415T1 (de) | 2003-02-27 | 2008-10-15 | Smithkline Beecham Corp | Neue verbindungen |
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| HUE040136T2 (hu) | 2011-02-07 | 2019-02-28 | Plexxikon Inc | Vegyületek és eljárások kináz modulációra és azok indikációi |
| TWI558702B (zh) | 2011-02-21 | 2016-11-21 | 普雷辛肯公司 | 醫藥活性物質的固態形式 |
| US9150570B2 (en) | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| CA2921265C (fr) * | 2013-08-16 | 2021-03-23 | Merck Patent Gmbh | Derives de la cyclopentyleamine 3-substitues |
| CN106580986B (zh) * | 2016-11-28 | 2017-09-15 | 王保亮 | 一种治疗少弱精子症的药物组合物 |
| US11174263B2 (en) | 2018-12-31 | 2021-11-16 | Biomea Fusion, Inc. | Inhibitors of menin-MLL interaction |
| CN114040760B (zh) | 2018-12-31 | 2025-05-09 | 拜欧米富士恩公司 | Menin-mll相互作用的不可逆抑制剂 |
| UA128894C2 (uk) * | 2019-01-31 | 2024-11-20 | Пфайзер Інк. | 3-карбоніламіно-5-циклопентил-1н-піразолові сполуки, які мають інгібіторну активність на cdk2 |
| US12479816B2 (en) | 2019-02-08 | 2025-11-25 | University of Pittsburgh—of the Commonwealth System of Higher Education | 20-HETE formation inhibitors |
| EP4229037A2 (fr) * | 2020-10-16 | 2023-08-23 | CeMM - Forschungszentrum für Molekulare Medizin GmbH | Composés d'ubiquitine ligase cullin ring et utilisations associées |
| WO2022135442A1 (fr) * | 2020-12-22 | 2022-06-30 | 上海拓界生物医药科技有限公司 | Inhibiteur de cdk2 et son procédé de préparation |
| JP2024519215A (ja) | 2021-05-07 | 2024-05-09 | カイメラ セラピューティクス, インコーポレイテッド | Cdk2分解剤およびそれらの使用 |
| TW202317574A (zh) | 2021-06-28 | 2023-05-01 | 美商纜圖藥品公司 | Cdk2抑制劑 |
| WO2023274397A1 (fr) * | 2021-07-01 | 2023-01-05 | 上海拓界生物医药科技有限公司 | Inhibiteur de cdk2, son procédé de préparation et son utilisation |
| EP4384179A1 (fr) | 2021-08-11 | 2024-06-19 | Biomea Fusion, Inc. | Inhibiteurs covalents de l'interaction ménine-mll pour le diabète sucré |
| JP2024534014A (ja) | 2021-08-20 | 2024-09-18 | バイオメア フュージョン,インコーポレイテッド | 癌の処置のための不可逆的メニン-MLL阻害剤、N-[4-[4-(4-モルホリニル)-7H-ピロロ[2,3-d]ピリミジン-6-イル]フェニル]-4-[[3(R)-[(1-オキソ-2-プロペン-1-イル)アミノ]-1-ピペリジニル]メチル]-2-ピリジンカルボキサミドの結晶形態 |
| WO2023083201A1 (fr) * | 2021-11-09 | 2023-05-19 | 上海拓界生物医药科技有限公司 | Dérivé d'aminopyrazole, son procédé de préparation et son utilisation |
| WO2023092088A1 (fr) * | 2021-11-19 | 2023-05-25 | Blueprint Medicines Corporation | Inhibiteurs de cdk2 et leurs procédés de fabrication et d'utilisation |
| WO2023239629A1 (fr) * | 2022-06-06 | 2023-12-14 | Plexium, Inc. | Composés et compositions pharmaceutiques qui dégradent cdk2 |
| WO2024155710A1 (fr) | 2023-01-18 | 2024-07-25 | Biomea Fusion, Inc. | Formes cristallines de n-[4-[4-(4-morpholinyl)-7h-pyrrolo[2,3-d]pyrimidin-6-yl]phényl]-4-[[3(r)-[(l-oxo-2-propen-l-yl)amino]-l-pipéridinyl]méthyl]-2- pyridinecarboxamide en tant qu'inhibiteur covalent de l'interaction ménine-mll |
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|---|---|---|---|---|
| IL136767A0 (en) * | 1997-12-22 | 2001-06-14 | Bayer Ag | Inhibition of raf kinase using substituted heterocyclic ureas |
| KR100579792B1 (ko) * | 1998-05-13 | 2006-05-12 | 동화약품공업주식회사 | 신규 2,5-피리딘디카복실산 유도체 |
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| EA005373B1 (ru) * | 1999-08-12 | 2005-02-24 | Фармация Италия С.П.А. | Производные 3(5)-аминопиразола, способ их получения и их применение в качестве противоопухолевых средств |
| HUP0203300A3 (en) * | 1999-11-30 | 2003-10-28 | Pfizer Prod Inc | 2,4-diaminopyrimidine compounds useful as immunosuppressants, pharmaceutical compositions containing them and their use |
| CA2398446A1 (fr) * | 2000-04-18 | 2001-10-25 | Agouron Pharmaceuticals, Inc. | Pyrazoles permettant d'inhiber des proteines kinases |
-
2001
- 2001-08-24 NZ NZ523656A patent/NZ523656A/en unknown
- 2001-08-24 IL IL15401601A patent/IL154016A0/xx unknown
- 2001-08-24 HU HU0302669A patent/HUP0302669A3/hu unknown
- 2001-08-24 EE EEP200300085A patent/EE200300085A/xx unknown
- 2001-08-24 KR KR10-2003-7002894A patent/KR20030027093A/ko not_active Ceased
- 2001-08-24 AP APAP/P/2001/002266A patent/AP2001002266A0/en unknown
- 2001-08-24 CZ CZ2003468A patent/CZ2003468A3/cs unknown
- 2001-08-24 SK SK200-2003A patent/SK2002003A3/sk not_active Application Discontinuation
- 2001-08-24 HR HR20030140A patent/HRP20030140A2/hr not_active Application Discontinuation
- 2001-08-24 YU YU14703A patent/YU14703A/sh unknown
- 2001-08-24 BR BR0113574-0A patent/BR0113574A/pt not_active IP Right Cessation
- 2001-08-24 PL PL36074201A patent/PL360742A1/xx not_active Application Discontinuation
- 2001-08-24 CA CA002420363A patent/CA2420363A1/fr not_active Abandoned
- 2001-08-24 WO PCT/IB2001/001540 patent/WO2002018346A1/fr not_active Ceased
- 2001-08-24 MX MXPA03001785A patent/MXPA03001785A/es not_active Application Discontinuation
- 2001-08-24 EP EP01958287A patent/EP1313710A1/fr not_active Withdrawn
- 2001-08-24 CN CNA018147615A patent/CN1518543A/zh active Pending
- 2001-08-24 OA OA1200300050A patent/OA12368A/en unknown
- 2001-08-24 DZ DZ013398A patent/DZ3398A1/fr active
- 2001-08-24 EA EA200300205A patent/EA200300205A1/ru unknown
- 2001-08-24 AU AU2001280009A patent/AU2001280009A1/en not_active Abandoned
- 2001-08-24 JP JP2002523464A patent/JP2004507526A/ja active Pending
- 2001-08-27 UY UY26909A patent/UY26909A1/es not_active Application Discontinuation
- 2001-08-28 HN HN2001000192A patent/HN2001000192A/es unknown
- 2001-08-29 PE PE2001000872A patent/PE20020470A1/es not_active Application Discontinuation
- 2001-08-29 DO DO2001000243A patent/DOP2001000243A/es unknown
- 2001-08-29 AR ARP010104115A patent/AR035345A1/es unknown
- 2001-08-30 GT GT200100179A patent/GT200100179A/es unknown
- 2001-08-30 TN TNTNSN01132A patent/TNSN01132A1/fr unknown
- 2001-08-30 SV SV2001000618A patent/SV2002000618A/es unknown
- 2001-08-31 PA PA20018528101A patent/PA8528101A1/es unknown
-
2003
- 2003-01-13 BG BG107455A patent/BG107455A/xx unknown
- 2003-01-15 CR CR6881A patent/CR6881A/es not_active Application Discontinuation
- 2003-01-16 IS IS6687A patent/IS6687A/is unknown
- 2003-02-07 ZA ZA200301064A patent/ZA200301064B/en unknown
- 2003-02-17 EC EC2003004480A patent/ECSP034480A/es unknown
- 2003-02-21 MA MA27050A patent/MA26946A1/fr unknown
- 2003-02-28 NO NO20030958A patent/NO20030958L/no not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |