JP2023514188A

JP2023514188A - 抗がん剤としてのキヌクリジノン系化合物の応用

抗がん剤としてのキヌクリジノン系化合物の応用 Download PDF

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Publication number: JP2023514188A
Authority: JP; Japan
Prior art keywords: methoxymethyl; hydroxymethyl; methyl; quinuclidin; alkyl
Prior art date: 2020-02-09
Legal status : Withdrawn

Application number

JP2022548528A

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English (en)

Japanese (ja)

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JP2023514188A5 (https=

Inventor

チェン，イ

Original Assignee

ニューウェーブ・ファーマスーティカル・インコーポレイテッド

Priority date

2020-02-09

Filing date

2021-02-05

Publication date

2023-04-05

2021-02-05 Application filed by ニューウェーブ・ファーマスーティカル・インコーポレイテッド filed Critical ニューウェーブ・ファーマスーティカル・インコーポレイテッド

2023-04-05 Publication of JP2023514188A publication Critical patent/JP2023514188A/ja

2024-02-14 Publication of JP2023514188A5 publication Critical patent/JP2023514188A5/ja

Status Withdrawn legal-status Critical Current

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FJXLZNSVOSVTPH-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-2-one Chemical class C1CN2C(=O)CC1CC2 FJXLZNSVOSVTPH-UHFFFAOYSA-N 0.000 title claims 2
239000002246 antineoplastic agent Substances 0.000 title description 9
150000001875 compounds Chemical class 0.000 claims abstract description 142
238000000034 method Methods 0.000 claims abstract description 28
230000001613 neoplastic effect Effects 0.000 claims abstract description 12
208000023275 Autoimmune disease Diseases 0.000 claims abstract description 9
208000027866 inflammatory disease Diseases 0.000 claims abstract description 8
-1 spiroalkyl Chemical group 0.000 claims description 136
ZKMZPXWMMSBLNO-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octan-3-one Chemical compound C1CC2C(=O)CN1CC2 ZKMZPXWMMSBLNO-UHFFFAOYSA-N 0.000 claims description 111
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 91
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 90
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 70
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 67
125000000753 cycloalkyl group Chemical group 0.000 claims description 62
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 61
125000003118 aryl group Chemical group 0.000 claims description 59
125000000217 alkyl group Chemical group 0.000 claims description 57
125000001072 heteroaryl group Chemical group 0.000 claims description 53
125000000392 cycloalkenyl group Chemical group 0.000 claims description 49
125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 49
150000003839 salts Chemical class 0.000 claims description 49
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 45
125000003342 alkenyl group Chemical group 0.000 claims description 41
125000000304 alkynyl group Chemical group 0.000 claims description 41
229910052739 hydrogen Inorganic materials 0.000 claims description 27
150000001204 N-oxides Chemical class 0.000 claims description 25
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
229910052757 nitrogen Inorganic materials 0.000 claims description 25
229910052736 halogen Inorganic materials 0.000 claims description 24
150000002367 halogens Chemical class 0.000 claims description 24
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
229910052799 carbon Inorganic materials 0.000 claims description 21
229910052805 deuterium Inorganic materials 0.000 claims description 21
229940002612 prodrug Drugs 0.000 claims description 21
239000000651 prodrug Substances 0.000 claims description 21
239000012453 solvate Substances 0.000 claims description 18
201000010099 disease Diseases 0.000 claims description 16
125000004093 cyano group Chemical group *C#N 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
125000003282 alkyl amino group Chemical group 0.000 claims description 13
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000001188 haloalkyl group Chemical group 0.000 claims description 12
BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 claims description 12
239000008194 pharmaceutical composition Substances 0.000 claims description 11
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
125000004043 oxo group Chemical group O=* 0.000 claims description 10
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 9
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 9
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
125000004103 aminoalkyl group Chemical group 0.000 claims description 9
125000004992 haloalkylamino group Chemical group 0.000 claims description 9
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 6
WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 claims description 6
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 6
VUAXHMVRKOTJKP-UHFFFAOYSA-M 2,2-dimethylbutanoate Chemical compound CCC(C)(C)C([O-])=O VUAXHMVRKOTJKP-UHFFFAOYSA-M 0.000 claims description 5
102100025064 Cellular tumor antigen p53 Human genes 0.000 claims description 5
101000721661 Homo sapiens Cellular tumor antigen p53 Proteins 0.000 claims description 5
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 4
YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 claims description 4
CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical compound OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 3
208000037979 autoimmune inflammatory disease Diseases 0.000 claims description 2
230000008827 biological function Effects 0.000 claims description 2
230000001363 autoimmune Effects 0.000 abstract description 10
239000000203 mixture Substances 0.000 description 240
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 198
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 195
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 182
239000000243 solution Substances 0.000 description 171
230000015572 biosynthetic process Effects 0.000 description 130
238000003786 synthesis reaction Methods 0.000 description 129
239000007787 solid Substances 0.000 description 107
238000005160 1H NMR spectroscopy Methods 0.000 description 94
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 90
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 74
239000003921 oil Substances 0.000 description 74
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 67
229960001866 silicon dioxide Drugs 0.000 description 63
239000000741 silica gel Substances 0.000 description 62
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 55
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 49
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 45
229910000041 hydrogen chloride Inorganic materials 0.000 description 45
239000012267 brine Substances 0.000 description 43
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 43
239000012044 organic layer Substances 0.000 description 40
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 39
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 38
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 37
239000012043 crude product Substances 0.000 description 35
239000003208 petroleum Substances 0.000 description 34
239000011541 reaction mixture Substances 0.000 description 34
238000006243 chemical reaction Methods 0.000 description 29
238000001914 filtration Methods 0.000 description 29
238000002953 preparative HPLC Methods 0.000 description 29
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 28
BGBNULCRKBVAKL-UHFFFAOYSA-N 2-(hydroxymethyl)-2-(methoxymethyl)-1-azabicyclo[2.2.2]octan-3-one Chemical compound C1CC2CCN1C(COC)(CO)C2=O BGBNULCRKBVAKL-UHFFFAOYSA-N 0.000 description 27
206010028980 Neoplasm Diseases 0.000 description 25
239000003814 drug Substances 0.000 description 24
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
238000002360 preparation method Methods 0.000 description 24
238000003756 stirring Methods 0.000 description 22
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 20
239000002253 acid Substances 0.000 description 20
239000012298 atmosphere Substances 0.000 description 20
239000000706 filtrate Substances 0.000 description 20
235000015320 potassium carbonate Nutrition 0.000 description 19
229910000027 potassium carbonate Inorganic materials 0.000 description 19
229940079593 drug Drugs 0.000 description 18
JWOIOCYCJNBEQY-UHFFFAOYSA-N methyl 4-methylpiperidine-4-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1(C)CCNCC1 JWOIOCYCJNBEQY-UHFFFAOYSA-N 0.000 description 18
125000001424 substituent group Chemical group 0.000 description 18
238000010791 quenching Methods 0.000 description 17
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
125000004432 carbon atom Chemical group C* 0.000 description 16
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
238000010898 silica gel chromatography Methods 0.000 description 15
239000007832 Na2SO4 Substances 0.000 description 14
125000004429 atom Chemical group 0.000 description 14
210000004027 cell Anatomy 0.000 description 14
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 14
229910052938 sodium sulfate Inorganic materials 0.000 description 14
235000011152 sodium sulphate Nutrition 0.000 description 14
MMXIDBXJYAGBGW-UHFFFAOYSA-N CC(CC1)(CCN1C1)C1=O.Cl Chemical compound CC(CC1)(CCN1C1)C1=O.Cl MMXIDBXJYAGBGW-UHFFFAOYSA-N 0.000 description 13
BSVJRKHBKSVHAS-UHFFFAOYSA-N CC12C(C(N(CC1)CC2)C(=O)OCC)=O Chemical compound CC12C(C(N(CC1)CC2)C(=O)OCC)=O BSVJRKHBKSVHAS-UHFFFAOYSA-N 0.000 description 13
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 13
238000001953 recrystallisation Methods 0.000 description 13
125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 12
ZSJJPURXSUYHNS-UHFFFAOYSA-N C(C)OC(CN1CCC(CC1)(C(=O)OC)C)=O Chemical compound C(C)OC(CN1CCC(CC1)(C(=O)OC)C)=O ZSJJPURXSUYHNS-UHFFFAOYSA-N 0.000 description 12
239000004698 Polyethylene Substances 0.000 description 12
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 12
239000012230 colorless oil Substances 0.000 description 12
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YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 description 12
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
TZMUBDFQIZKHBC-UHFFFAOYSA-N C(O)C1(N2CCC(C1=O)(CC2)C)CO Chemical compound C(O)C1(N2CCC(C1=O)(CC2)C)CO TZMUBDFQIZKHBC-UHFFFAOYSA-N 0.000 description 11
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RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 10
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
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JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 9
SNBGURLVYHVYEB-UHFFFAOYSA-N 1-o-tert-butyl 4-o-methyl 4-methylpiperidine-1,4-dicarboxylate Chemical compound COC(=O)C1(C)CCN(C(=O)OC(C)(C)C)CC1 SNBGURLVYHVYEB-UHFFFAOYSA-N 0.000 description 8
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 8
HRJHQOXWONBAJC-UHFFFAOYSA-N ethyl 2-methyloctanoate Chemical compound CCCCCCC(C)C(=O)OCC HRJHQOXWONBAJC-UHFFFAOYSA-N 0.000 description 8
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VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
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