ZA200301064B - Pyrazole derivatives and their use as protein kinase inhibitors. - Google Patents
Pyrazole derivatives and their use as protein kinase inhibitors. Download PDFInfo
- Publication number
- ZA200301064B ZA200301064B ZA200301064A ZA200301064A ZA200301064B ZA 200301064 B ZA200301064 B ZA 200301064B ZA 200301064 A ZA200301064 A ZA 200301064A ZA 200301064 A ZA200301064 A ZA 200301064A ZA 200301064 B ZA200301064 B ZA 200301064B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyrazol
- cyclobutyl
- acetamide
- phenyl
- cis
- Prior art date
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- 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
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- -1 methoxy-phenyl Chemical group 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 230000002159 abnormal effect Effects 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 230000010261 cell growth Effects 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 101150053721 Cdk5 gene Proteins 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 241000124008 Mammalia Species 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 239000003112 inhibitor Substances 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- LTUUGSGSUZRPRV-UHFFFAOYSA-N 6-methylpyridine-2-carboxylic acid Chemical compound CC1=CC=CC(C(O)=O)=N1 LTUUGSGSUZRPRV-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- AHDDRJBFJBDEPW-UHFFFAOYSA-N 2-phenylcyclopropane-1-carboxylic acid Chemical compound OC(=O)C1CC1C1=CC=CC=C1 AHDDRJBFJBDEPW-UHFFFAOYSA-N 0.000 claims description 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 4
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229940080818 propionamide Drugs 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 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
- 201000004384 Alopecia Diseases 0.000 claims description 3
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 3
- 229940047889 isobutyramide Drugs 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 230000004770 neurodegeneration Effects 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
- 230000019100 sperm motility Effects 0.000 claims description 3
- 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
- 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 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
- 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 2
- 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 2
- YBRQKXYABHZLBT-UHFFFAOYSA-N 5-cyclobutyl-n-naphthalen-2-yl-1h-pyrazol-3-amine Chemical compound C1CCC1C1=NNC(NC=2C=C3C=CC=CC3=CC=2)=C1 YBRQKXYABHZLBT-UHFFFAOYSA-N 0.000 claims description 2
- ZLKMOIHCHCMSFW-UHFFFAOYSA-N 6-chloropyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC=CC(Cl)=N1 ZLKMOIHCHCMSFW-UHFFFAOYSA-N 0.000 claims description 2
- CJNAMFYYFJDGNQ-KDURUIRLSA-N C1=CC(O)=CC=C1[C@H]1C[C@@H](C=2NN=C(NC(=O)CC=3C=C4C=CC=NC4=CC=3)C=2)C1 Chemical compound C1=CC(O)=CC=C1[C@H]1C[C@@H](C=2NN=C(NC(=O)CC=3C=C4C=CC=NC4=CC=3)C=2)C1 CJNAMFYYFJDGNQ-KDURUIRLSA-N 0.000 claims description 2
- XJDWZCSYFDQADW-OYRHEFFESA-N C1=CC(OC)=CC=C1CC(=O)NC1=CC([C@@H]2C[C@@H](C2)C=2C=C(CN(C)C)C=CC=2)=NN1 Chemical compound C1=CC(OC)=CC=C1CC(=O)NC1=CC([C@@H]2C[C@@H](C2)C=2C=C(CN(C)C)C=CC=2)=NN1 XJDWZCSYFDQADW-OYRHEFFESA-N 0.000 claims description 2
- VCHAAEXLCHTUCS-KDURUIRLSA-N C1=CC(OC)=CC=C1CC(=O)NC1=CC([C@@H]2C[C@@H](C2)C=2C=C(CN)C=CC=2)=NN1 Chemical compound C1=CC(OC)=CC=C1CC(=O)NC1=CC([C@@H]2C[C@@H](C2)C=2C=C(CN)C=CC=2)=NN1 VCHAAEXLCHTUCS-KDURUIRLSA-N 0.000 claims description 2
- IIZBOPVDAGEFES-SZPZYZBQSA-N C1=CC(OC)=CC=C1CC(=O)NC1=CC([C@@H]2C[C@@H](C2)C=2C=C(CN3CCC3)C=CC=2)=NN1 Chemical compound C1=CC(OC)=CC=C1CC(=O)NC1=CC([C@@H]2C[C@@H](C2)C=2C=C(CN3CCC3)C=CC=2)=NN1 IIZBOPVDAGEFES-SZPZYZBQSA-N 0.000 claims description 2
- MPZJSNRIXXDLIV-KDURUIRLSA-N C1=CC(OC)=CC=C1CC(=O)NC1=CC([C@@H]2C[C@@H](C2)C=2C=C(CO)C=CC=2)=NN1 Chemical compound C1=CC(OC)=CC=C1CC(=O)NC1=CC([C@@H]2C[C@@H](C2)C=2C=C(CO)C=CC=2)=NN1 MPZJSNRIXXDLIV-KDURUIRLSA-N 0.000 claims description 2
- JVOCTXRAAATKPV-BGYRXZFFSA-N C1=CC(OC)=CC=C1[C@H]1C[C@@H](C=2NN=C(NC(=O)CC=3C=C4C=CC=NC4=CC=3)C=2)C1 Chemical compound C1=CC(OC)=CC=C1[C@H]1C[C@@H](C=2NN=C(NC(=O)CC=3C=C4C=CC=NC4=CC=3)C=2)C1 JVOCTXRAAATKPV-BGYRXZFFSA-N 0.000 claims description 2
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims description 2
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims description 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 2
- 229960003638 dopamine Drugs 0.000 claims description 2
- 208000024963 hair loss Diseases 0.000 claims description 2
- 230000003676 hair loss Effects 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
- 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 2
- QVDBUAZHHAMIOE-UHFFFAOYSA-N n-[3,5-bis(trifluoromethyl)phenyl]-5-cyclobutyl-1h-pyrazol-3-amine Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC=2NN=C(C=2)C2CCC2)=C1 QVDBUAZHHAMIOE-UHFFFAOYSA-N 0.000 claims description 2
- QUZWZXFAUSJHEL-UHFFFAOYSA-N n-[5-(2,3-dihydro-1h-inden-2-yl)-1h-pyrazol-3-yl]-2-quinolin-6-ylacetamide Chemical compound C1C2=CC=CC=C2CC1C1=CC(NC(CC=2C=C3C=CC=NC3=CC=2)=O)=NN1 QUZWZXFAUSJHEL-UHFFFAOYSA-N 0.000 claims description 2
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 2
- 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 1
- AYEGPMGNMOIHDL-UHFFFAOYSA-N 2-methylcyclopropane-1-carboxylic acid Chemical compound CC1CC1C(O)=O AYEGPMGNMOIHDL-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 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 1
- 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 1
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- 229940100578 Acetylcholinesterase inhibitor Drugs 0.000 claims 1
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- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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| WO2023239629A1 (en) * | 2022-06-06 | 2023-12-14 | Plexium, Inc. | Compounds and pharmaceutical compositions that degrade cdk2 |
| WO2024155710A1 (en) | 2023-01-18 | 2024-07-25 | Biomea Fusion, Inc. | Crystalline forms of n-[4-[4-(4-morpholinyl)-7h-pyrrolo[2,3-d]pyrimidin-6- yl]phenyl]-4-[[3(r)-[(l-oxo-2-propen-l-yl)amino]-l-piperidinyl]methyl]-2-pyridinecarboxamide as a covalent inhibitor of menin-mll interaction |
| WO2026024674A1 (en) | 2024-07-22 | 2026-01-29 | Genesis Therapeutics, Inc. | Methods of treating skp2-associated cancers |
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| NZ505844A (en) * | 1997-12-22 | 2003-10-31 | Bayer Ag | Inhibition of raf kinase using substituted heterocyclic ureas |
| KR100579792B1 (ko) * | 1998-05-13 | 2006-05-12 | 동화약품공업주식회사 | 신규 2,5-피리딘디카복실산 유도체 |
| GB9811427D0 (en) * | 1998-05-29 | 1998-07-22 | Zeneca Ltd | Chemical compounds |
| DE60024631T2 (de) * | 1999-07-26 | 2006-06-14 | Banyu Pharma Co Ltd | Biaryl-harnstoff-derivate |
| US6387900B1 (en) * | 1999-08-12 | 2002-05-14 | Pharmacia & Upjohn S.P.A. | 3(5)-ureido-pyrazole derivatives process for their preparation and their use as antitumor agents |
| EE200200065A (et) * | 1999-08-12 | 2003-04-15 | Pharmacia Italia S.P.A. | 3-aminopürasooli derivaadid, nende valmistamine ja kasutamine vähivastaste toimeainetena ning neid sisaldav farmatseutiline kompositsioon |
| CA2392971C (en) * | 1999-11-30 | 2008-10-07 | Pfizer Products Inc. | 2,4-diaminopyrimidine compounds useful as immunosuppressants |
| CA2398446A1 (en) * | 2000-04-18 | 2001-10-25 | Agouron Pharmaceuticals, Inc. | Pyrazoles for inhibiting protein kinases |
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