TWI712603B - 作為ｂｅｔ蛋白抑制劑之三環雜環 - Google Patents

Info

Publication number

TWI712603B

TWI712603B TW104130337A TW104130337A TWI712603B TW I712603 B TWI712603 B TW I712603B TW 104130337 A TW104130337 A TW 104130337A TW 104130337 A TW104130337 A TW 104130337A TW I712603 B TWI712603 B TW I712603B

Authority

TW

Taiwan

Prior art keywords

compound

cancer

pharmaceutically acceptable

acceptable salt

methyl

Prior art date

2014-09-15

Links

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• 125000000169 tricyclic heterocycle group Chemical group 0.000 title abstract description 3
• 229940121649 protein inhibitor Drugs 0.000 title 1
• 239000012268 protein inhibitor Substances 0.000 title 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 63
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 54
• 201000010099 disease Diseases 0.000 claims abstract description 50
• 201000011510 cancer Diseases 0.000 claims abstract description 30
• 238000011282 treatment Methods 0.000 claims abstract description 28
• 150000001875 compounds Chemical class 0.000 claims description 236
• -1 N-butyl Chemical group 0.000 claims description 81
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 79
• 150000003839 salts Chemical class 0.000 claims description 73
• 125000000217 alkyl group Chemical group 0.000 claims description 55
• 238000000034 method Methods 0.000 claims description 37
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 33
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 33
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 30
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 29
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 28
• 239000003814 drug Substances 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 22
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 21
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 20
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 20
• 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 19
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 19
• 125000003545 alkoxy group Chemical group 0.000 claims description 17
• 229910052799 carbon Inorganic materials 0.000 claims description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 13
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 13
• 208000035475 disorder Diseases 0.000 claims description 13
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 13
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 12
• GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 12
• 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 12
• 125000006001 difluoroethyl group Chemical group 0.000 claims description 12
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 12
• 229910052731 fluorine Inorganic materials 0.000 claims description 12
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
• 230000001363 autoimmune Effects 0.000 claims description 11
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 11
• 230000002062 proliferating effect Effects 0.000 claims description 10
• PVTXJGJDOHYFOX-UHFFFAOYSA-N 2h-1,4-benzoxazine Chemical compound C1=CC=C2N=CCOC2=C1 PVTXJGJDOHYFOX-UHFFFAOYSA-N 0.000 claims description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
• 230000002401 inhibitory effect Effects 0.000 claims description 9
• 206010035226 Plasma cell myeloma Diseases 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• 210000001519 tissue Anatomy 0.000 claims description 8
• 201000009030 Carcinoma Diseases 0.000 claims description 7
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• 206010042971 T-cell lymphoma Diseases 0.000 claims description 7
• 208000027585 T-cell non-Hodgkin lymphoma Diseases 0.000 claims description 7
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• 206010017758 gastric cancer Diseases 0.000 claims description 6
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• 230000009385 viral infection Effects 0.000 claims description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 208000017604 Hodgkin disease Diseases 0.000 claims description 5
• 208000021519 Hodgkin lymphoma Diseases 0.000 claims description 5
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• DLGYNVMUCSTYDQ-UHFFFAOYSA-N azane;pyridine Chemical group N.C1=CC=NC=C1 DLGYNVMUCSTYDQ-UHFFFAOYSA-N 0.000 claims description 5
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• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims description 4
• 206010040047 Sepsis Diseases 0.000 claims description 4
• 206010051379 Systemic Inflammatory Response Syndrome Diseases 0.000 claims description 4
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 4
• 238000000338 in vitro Methods 0.000 claims description 4
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• 206010006187 Breast cancer Diseases 0.000 claims description 3
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• OZALPVLVYBXRKE-JOCHJYFZSA-N CC1=NOC(=C1C1=CC=C2C=3N([C@H](COC=31)C1=NC=CC=C1)C(=N2)N1CCN(CC1)C(C(C)C)=O)C Chemical compound CC1=NOC(=C1C1=CC=C2C=3N([C@H](COC=31)C1=NC=CC=C1)C(=N2)N1CCN(CC1)C(C(C)C)=O)C OZALPVLVYBXRKE-JOCHJYFZSA-N 0.000 claims description 3
• 206010008342 Cervix carcinoma Diseases 0.000 claims description 3
• 206010009944 Colon cancer Diseases 0.000 claims description 3
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 3
• 208000000461 Esophageal Neoplasms Diseases 0.000 claims description 3
• 208000022072 Gallbladder Neoplasms Diseases 0.000 claims description 3
• 206010017993 Gastrointestinal neoplasms Diseases 0.000 claims description 3
• 241000701806 Human papillomavirus Species 0.000 claims description 3
• 206010020751 Hypersensitivity Diseases 0.000 claims description 3
• 208000008839 Kidney Neoplasms Diseases 0.000 claims description 3
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
• 206010027406 Mesothelioma Diseases 0.000 claims description 3
• 208000003445 Mouth Neoplasms Diseases 0.000 claims description 3
• 206010033128 Ovarian cancer Diseases 0.000 claims description 3
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
• 208000009565 Pharyngeal Neoplasms Diseases 0.000 claims description 3
• 206010060862 Prostate cancer Diseases 0.000 claims description 3
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
• 201000004681 Psoriasis Diseases 0.000 claims description 3
• 208000015634 Rectal Neoplasms Diseases 0.000 claims description 3
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• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 3
• 208000008385 Urogenital Neoplasms Diseases 0.000 claims description 3
• 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 3
• 208000002495 Uterine Neoplasms Diseases 0.000 claims description 3
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• 241000701044 Human gammaherpesvirus 4 Species 0.000 claims description 2
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• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 3
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• BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 1
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