KR20170103962A - 인자 xia 억제제 - Google Patents

Info

Publication number

KR20170103962A

KR20170103962A KR1020177022768A KR20177022768A KR20170103962A KR 20170103962 A KR20170103962 A KR 20170103962A KR 1020177022768 A KR1020177022768 A KR 1020177022768A KR 20177022768 A KR20177022768 A KR 20177022768A KR 20170103962 A KR20170103962 A KR 20170103962A

Authority

KR

South Korea

Prior art keywords

halo

dihydro

mmol

cyclopenta

hydroxy

Prior art date

2015-01-20

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.)

Withdrawn

Links

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• 229940122036 Factor XIa inhibitor Drugs 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 164
• 238000000034 method Methods 0.000 claims abstract description 44
• 208000007536 Thrombosis Diseases 0.000 claims abstract description 32
• 238000011282 treatment Methods 0.000 claims abstract description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
• 230000002265 prevention Effects 0.000 claims abstract description 5
• -1 OR 4 Chemical group 0.000 claims description 128
• 239000000203 mixture Substances 0.000 claims description 93
• 150000003839 salts Chemical class 0.000 claims description 61
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
• 229910052739 hydrogen Inorganic materials 0.000 claims description 35
• 239000001257 hydrogen Substances 0.000 claims description 35
• 230000015572 biosynthetic process Effects 0.000 claims description 32
• 125000001072 heteroaryl group Chemical group 0.000 claims description 32
• 125000000217 alkyl group Chemical group 0.000 claims description 29
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
• 125000001424 substituent group Chemical group 0.000 claims description 26
• 239000003814 drug Substances 0.000 claims description 25
• 125000003118 aryl group Chemical group 0.000 claims description 23
• 150000002431 hydrogen Chemical class 0.000 claims description 20
• 241000124008 Mammalia Species 0.000 claims description 18
• 239000008280 blood Substances 0.000 claims description 17
• 210000004369 blood Anatomy 0.000 claims description 17
• 230000005764 inhibitory process Effects 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 13
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 125000004043 oxo group Chemical group O=* 0.000 claims description 10
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 7
• 108090000190 Thrombin Proteins 0.000 claims description 6
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• 206010051055 Deep vein thrombosis Diseases 0.000 claims description 5
• 206010014522 Embolism venous Diseases 0.000 claims description 5
• 208000010378 Pulmonary Embolism Diseases 0.000 claims description 5
• 206010047249 Venous thrombosis Diseases 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 230000002401 inhibitory effect Effects 0.000 claims description 5
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• 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
• 238000002560 therapeutic procedure Methods 0.000 claims description 3
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• 125000001475 halogen functional group Chemical group 0.000 claims 19
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• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 119
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 106
• 235000019439 ethyl acetate Nutrition 0.000 description 57
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 55
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 50
• 239000000243 solution Substances 0.000 description 49
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 42
• 239000002904 solvent Substances 0.000 description 42
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 40
• 125000005843 halogen group Chemical group 0.000 description 37
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• 238000006243 chemical reaction Methods 0.000 description 35
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
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• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 29
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• 239000000047 product Substances 0.000 description 27
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
• 238000000746 purification Methods 0.000 description 22
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
• 239000011734 sodium Substances 0.000 description 21
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 20
• 239000012044 organic layer Substances 0.000 description 20
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 18
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 17
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
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• 229940079593 drug Drugs 0.000 description 15
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
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• 239000013058 crude material Substances 0.000 description 13
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
• 102000004190 Enzymes Human genes 0.000 description 12
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• 239000000543 intermediate Substances 0.000 description 12
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• 238000004808 supercritical fluid chromatography Methods 0.000 description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
• 229910052799 carbon Inorganic materials 0.000 description 11
• 230000037361 pathway Effects 0.000 description 11
• 229940002612 prodrug Drugs 0.000 description 11
• 239000000651 prodrug Substances 0.000 description 11
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 10
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
• 235000011054 acetic acid Nutrition 0.000 description 10
• 238000004007 reversed phase HPLC Methods 0.000 description 10
• 238000003786 synthesis reaction Methods 0.000 description 10
• PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• 125000004429 atom Chemical group 0.000 description 9
• 239000003795 chemical substances by application Substances 0.000 description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
• 229920006395 saturated elastomer Polymers 0.000 description 9
• 239000012453 solvate Substances 0.000 description 9
• 239000000758 substrate Substances 0.000 description 9
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 8
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• 239000007821 HATU Substances 0.000 description 8
• 102100035792 Kininogen-1 Human genes 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
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• 125000002619 bicyclic group Chemical group 0.000 description 8
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• 125000005493 quinolyl group Chemical group 0.000 description 8
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