UA116534C2 - Піразолопіримідинілові інгібітори убіквітинактивуючого ферменту - Google Patents

Info

Publication number

UA116534C2

UA116534C2 UAA201409297A UAA201409297A UA116534C2 UA 116534 C2 UA116534 C2 UA 116534C2 UA A201409297 A UAA201409297 A UA A201409297A UA A201409297 A UAA201409297 A UA A201409297A UA 116534 C2 UA116534 C2 UA 116534C2

Authority

UA

Ukraine

Prior art keywords

methyl

sulfamate

ylamino

hei

dihydroxycyclopentyl

Prior art date

2012-02-17

Links

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• -1 Pyrazolopyrimidinyl Chemical group 0.000 title claims description 205
• 102000018478 Ubiquitin-Activating Enzymes Human genes 0.000 title abstract description 5
• 108010091546 Ubiquitin-Activating Enzymes Proteins 0.000 title abstract description 5
• 239000003112 inhibitor Substances 0.000 title description 15
• 150000001875 compounds Chemical class 0.000 claims abstract description 329
• 238000000034 method Methods 0.000 claims abstract description 69
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 53
• 150000003839 salts Chemical class 0.000 claims abstract description 44
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 35
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 30
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 275
• 208000010201 Exanthema Diseases 0.000 claims description 144
• 201000005884 exanthem Diseases 0.000 claims description 144
• 206010037844 rash Diseases 0.000 claims description 144
• 229910052736 halogen Inorganic materials 0.000 claims description 122
• 150000002367 halogens Chemical class 0.000 claims description 122
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 78
• FIYXUOWXHWJDAM-UHFFFAOYSA-N methyl sulfamate Chemical compound COS(N)(=O)=O FIYXUOWXHWJDAM-UHFFFAOYSA-N 0.000 claims description 74
• 125000000623 heterocyclic group Chemical group 0.000 claims description 55
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
• IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims description 33
• 125000003118 aryl group Chemical group 0.000 claims description 29
• 125000001072 heteroaryl group Chemical group 0.000 claims description 27
• 201000011510 cancer Diseases 0.000 claims description 26
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 25
• 125000005842 heteroatom Chemical group 0.000 claims description 20
• 238000011282 treatment Methods 0.000 claims description 20
• 201000010099 disease Diseases 0.000 claims description 18
• 230000005764 inhibitory process Effects 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 15
• 239000003937 drug carrier Substances 0.000 claims description 15
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 12
• 229920006395 saturated elastomer Polymers 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 8
• 125000001931 aliphatic group Chemical group 0.000 claims description 8
• 125000001424 substituent group Chemical group 0.000 claims description 8
• 206010009944 Colon cancer Diseases 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 208000029742 colonic neoplasm Diseases 0.000 claims description 6
• 239000013078 crystal Substances 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 6
• 206010006187 Breast cancer Diseases 0.000 claims description 5
• 208000026310 Breast neoplasm Diseases 0.000 claims description 5
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 5
• 206010033128 Ovarian cancer Diseases 0.000 claims description 5
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 5
• 201000005202 lung cancer Diseases 0.000 claims description 5
• 208000020816 lung neoplasm Diseases 0.000 claims description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
• 229940079593 drug Drugs 0.000 claims description 4
• 125000004076 pyridyl group Chemical group 0.000 claims description 4
• 125000003107 substituted aryl group Chemical group 0.000 claims description 4
• 125000001544 thienyl group Chemical group 0.000 claims description 4
• 125000005605 benzo group Chemical group 0.000 claims description 3
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000001624 naphthyl group Chemical group 0.000 claims description 3
• 125000002971 oxazolyl group Chemical group 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000000335 thiazolyl group Chemical group 0.000 claims description 3
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 238000003466 welding Methods 0.000 claims description 2
• 201000009613 breast lymphoma Diseases 0.000 claims 3
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
• 241000272201 Columbiformes Species 0.000 claims 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
• 239000002023 wood Substances 0.000 claims 1
• 150000005829 chemical entities Chemical class 0.000 abstract 4
• 208000035269 cancer or benign tumor Diseases 0.000 abstract 1
• 239000007858 starting material Substances 0.000 description 100
• 239000000203 mixture Substances 0.000 description 80
• HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 77
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 76
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 65
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 51
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
• 239000000243 solution Substances 0.000 description 43
• 239000011541 reaction mixture Substances 0.000 description 41
• 125000004432 carbon atom Chemical group C* 0.000 description 34
• 208000035475 disorder Diseases 0.000 description 34
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• 102000044159 Ubiquitin Human genes 0.000 description 31
• 108090000848 Ubiquitin Proteins 0.000 description 31
• 238000001069 Raman spectroscopy Methods 0.000 description 29
• 239000000047 product Substances 0.000 description 29
• 230000015572 biosynthetic process Effects 0.000 description 25
• 230000000694 effects Effects 0.000 description 25
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
• UFDGEFUTYSMTPD-UHFFFAOYSA-N 1-chloro-4-iodonaphthalene Chemical compound C1=CC=C2C(Cl)=CC=C(I)C2=C1 UFDGEFUTYSMTPD-UHFFFAOYSA-N 0.000 description 23
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
• 235000019439 ethyl acetate Nutrition 0.000 description 22
• 238000002411 thermogravimetry Methods 0.000 description 22
• 239000007787 solid Substances 0.000 description 20
• 238000003786 synthesis reaction Methods 0.000 description 20
• 239000000523 sample Substances 0.000 description 19
• 239000000725 suspension Substances 0.000 description 19
• 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 description 18
• 208000010833 Chronic myeloid leukaemia Diseases 0.000 description 18
• 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 description 18
• 229910052740 iodine Inorganic materials 0.000 description 18
• 239000012044 organic layer Substances 0.000 description 18
• 239000002904 solvent Substances 0.000 description 18
• 229910052770 Uranium Inorganic materials 0.000 description 17
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
• 239000002585 base Substances 0.000 description 15
• 210000004027 cell Anatomy 0.000 description 15
• 108090000623 proteins and genes Proteins 0.000 description 15
• 102000004169 proteins and genes Human genes 0.000 description 15
• 125000004452 carbocyclyl group Chemical group 0.000 description 14
• 239000013058 crude material Substances 0.000 description 13
• 102000004190 Enzymes Human genes 0.000 description 12
• 108090000790 Enzymes Proteins 0.000 description 12
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 238000006243 chemical reaction Methods 0.000 description 12
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
• 239000002244 precipitate Substances 0.000 description 12
• 125000006413 ring segment Chemical group 0.000 description 12
• 125000000217 alkyl group Chemical group 0.000 description 11
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• 238000004440 column chromatography Methods 0.000 description 11
• 239000002552 dosage form Substances 0.000 description 11
• 239000012071 phase Substances 0.000 description 11
• 239000000126 substance Substances 0.000 description 11
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 10
• 235000018102 proteins Nutrition 0.000 description 10
• 229940124597 therapeutic agent Drugs 0.000 description 10
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• 239000003480 eluent Substances 0.000 description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
• 210000001519 tissue Anatomy 0.000 description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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• 239000011780 sodium chloride Substances 0.000 description 8
• 238000001757 thermogravimetry curve Methods 0.000 description 8
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
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• 125000003396 thiol group Chemical group [H]S* 0.000 description 7
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• 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 description 6
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