JPWO2020128925A5 - - Google Patents
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- JPWO2020128925A5 JPWO2020128925A5 JP2021534681A JP2021534681A JPWO2020128925A5 JP WO2020128925 A5 JPWO2020128925 A5 JP WO2020128925A5 JP 2021534681 A JP2021534681 A JP 2021534681A JP 2021534681 A JP2021534681 A JP 2021534681A JP WO2020128925 A5 JPWO2020128925 A5 JP WO2020128925A5
- Authority
- JP
- Japan
- Prior art keywords
- thia
- dioxide
- dipyridina
- trifluoromethyl
- diaza
- Prior art date
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims description 360
- -1 alkoxylen Chemical group 0.000 claims description 320
- 239000011780 sodium chloride Substances 0.000 claims description 317
- 150000003839 salts Chemical class 0.000 claims description 313
- 125000000217 alkyl group Chemical group 0.000 claims description 221
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butanoic acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 148
- 108010079245 Cystic Fibrosis Transmembrane Conductance Regulator Proteins 0.000 claims description 135
- 201000010099 disease Diseases 0.000 claims description 90
- 125000003545 alkoxy group Chemical group 0.000 claims description 83
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 74
- 235000019260 propionic acid Nutrition 0.000 claims description 72
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 239000008194 pharmaceutical composition Substances 0.000 claims description 61
- 239000003814 drug Substances 0.000 claims description 59
- 201000003883 cystic fibrosis Diseases 0.000 claims description 55
- 125000002947 alkylene group Chemical group 0.000 claims description 54
- 206010033645 Pancreatitis Diseases 0.000 claims description 51
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 39
- 208000006673 Asthma Diseases 0.000 claims description 38
- 239000003937 drug carrier Substances 0.000 claims description 35
- 229910052805 deuterium Inorganic materials 0.000 claims description 34
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 33
- 230000001404 mediated Effects 0.000 claims description 32
- 206010006451 Bronchitis Diseases 0.000 claims description 31
- YZCKVEUIGOORGS-OUBTZVSYSA-N deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 27
- 125000000732 arylene group Chemical group 0.000 claims description 25
- 230000000051 modifying Effects 0.000 claims description 25
- 206010014561 Emphysema Diseases 0.000 claims description 24
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 23
- 208000007451 Chronic Bronchitis Diseases 0.000 claims description 23
- 125000005549 heteroarylene group Chemical group 0.000 claims description 23
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 22
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 22
- 150000002825 nitriles Chemical class 0.000 claims description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 20
- 125000005551 pyridylene group Chemical group 0.000 claims description 20
- 239000008177 pharmaceutical agent Substances 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 17
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 17
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
- FUZZWVXGSFPDMH-UHFFFAOYSA-N Hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 16
- 125000006294 amino alkylene group Chemical group 0.000 claims description 16
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 15
- 102000012605 Cystic Fibrosis Transmembrane Conductance Regulator Human genes 0.000 claims description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 11
- DHMQDGOQFOQNFH-UHFFFAOYSA-M aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 10
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000003242 anti bacterial agent Substances 0.000 claims description 7
- 230000003115 biocidal Effects 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 1-butanal Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 6
- 229940064005 Antibiotic throat preparations Drugs 0.000 claims description 6
- 229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 claims description 6
- 229940042052 Antibiotics for systemic use Drugs 0.000 claims description 6
- 229940042786 Antitubercular Antibiotics Drugs 0.000 claims description 6
- 229940093922 Gynecological Antibiotics Drugs 0.000 claims description 6
- 229940024982 Topical Antifungal Antibiotics Drugs 0.000 claims description 6
- 230000003182 bronchodilatating Effects 0.000 claims description 6
- 239000003172 expectorant agent Substances 0.000 claims description 6
- 229940079866 intestinal antibiotics Drugs 0.000 claims description 6
- 229940005935 ophthalmologic Antibiotics Drugs 0.000 claims description 6
- 239000004471 Glycine Substances 0.000 claims description 5
- XKJCHHZQLQNZHY-UHFFFAOYSA-N Phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 5
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 5
- 239000000168 bronchodilator agent Substances 0.000 claims description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 5
- 229940116904 ANTIINFLAMMATORY THERAPEUTIC RADIOPHARMACEUTICALS Drugs 0.000 claims description 4
- 229940066491 Mucolytics Drugs 0.000 claims description 4
- 229940074726 OPHTHALMOLOGIC ANTIINFLAMMATORY AGENTS Drugs 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 230000000510 mucolytic Effects 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- WLDMPODMCFGWAA-UHFFFAOYSA-N 3a,4,5,6,7,7a-hexahydroisoindole-1,3-dione Chemical compound C1CCCC2C(=O)NC(=O)C21 WLDMPODMCFGWAA-UHFFFAOYSA-N 0.000 claims description 3
- 229940074728 ANTIINFECTIVE OPHTHALMOLOGICS Drugs 0.000 claims description 3
- 229940021383 Antiinfective irrigating solutions Drugs 0.000 claims description 3
- 229960005475 Antiinfectives Drugs 0.000 claims description 3
- 230000002924 anti-infective Effects 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- FDDDEECHVMSUSB-UHFFFAOYSA-N Sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- 229960001663 sulfanilamide Drugs 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 13
- 239000000543 intermediate Substances 0.000 description 388
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 256
- 238000003786 synthesis reaction Methods 0.000 description 228
- 230000015572 biosynthetic process Effects 0.000 description 224
- 230000002194 synthesizing Effects 0.000 description 223
- 239000000203 mixture Substances 0.000 description 213
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 198
- 102100019896 CFTR Human genes 0.000 description 123
- 238000000034 method Methods 0.000 description 120
- 235000019439 ethyl acetate Nutrition 0.000 description 99
- 238000006243 chemical reaction Methods 0.000 description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 56
- 239000007787 solid Substances 0.000 description 56
- 239000000243 solution Substances 0.000 description 53
- 239000000047 product Substances 0.000 description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 47
- 125000005843 halogen group Chemical group 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 44
- 238000002560 therapeutic procedure Methods 0.000 description 42
- 208000000668 Chronic Pancreatitis Diseases 0.000 description 34
- 206010033649 Pancreatitis chronic Diseases 0.000 description 34
- 238000009472 formulation Methods 0.000 description 33
- 230000000306 recurrent Effects 0.000 description 31
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N DMSO-d6 Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 30
- 206010033647 Pancreatitis acute Diseases 0.000 description 28
- 201000003229 acute pancreatitis Diseases 0.000 description 28
- YVGGHNCTFXOJCH-UHFFFAOYSA-N DDT Chemical compound C1=CC(Cl)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(Cl)C=C1 YVGGHNCTFXOJCH-UHFFFAOYSA-N 0.000 description 27
- 230000035772 mutation Effects 0.000 description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
- 239000012267 brine Substances 0.000 description 25
- 239000007832 Na2SO4 Substances 0.000 description 24
- 229910052938 sodium sulfate Inorganic materials 0.000 description 24
- 235000011152 sodium sulphate Nutrition 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 23
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 22
- PURKAOJPTOLRMP-UHFFFAOYSA-N Ivacaftor Chemical compound C1=C(O)C(C(C)(C)C)=CC(C(C)(C)C)=C1NC(=O)C1=CNC2=CC=CC=C2C1=O PURKAOJPTOLRMP-UHFFFAOYSA-N 0.000 description 21
- 238000000746 purification Methods 0.000 description 20
- 230000002829 reduced Effects 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- 239000000706 filtrate Substances 0.000 description 19
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 18
- 230000000694 effects Effects 0.000 description 17
- LPNANKDXVBMDKE-UHFFFAOYSA-N 5-bromopent-1-ene Chemical compound BrCCCC=C LPNANKDXVBMDKE-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 239000010410 layer Substances 0.000 description 16
- 238000003818 flash chromatography Methods 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 14
- 206010033628 Pancreatic insufficiency Diseases 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 14
- 201000007089 exocrine pancreatic insufficiency Diseases 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N 3-aminopropanol Chemical group NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- RIMXEJYJXDBLIE-UHFFFAOYSA-N 6-bromohex-1-ene Chemical compound BrCCCCC=C RIMXEJYJXDBLIE-UHFFFAOYSA-N 0.000 description 12
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- 239000003054 catalyst Substances 0.000 description 12
- OKKJLVBELUTLKV-MZCSYVLQSA-N cd3od Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 12
- BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Inorganic materials [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- 229960000583 Acetic Acid Drugs 0.000 description 10
- 125000004406 C3-C8 cycloalkylene group Chemical group 0.000 description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- RWIVICVCHVMHMU-UHFFFAOYSA-N N-Aminoethylmorpholine Chemical group NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 10
- 235000011054 acetic acid Nutrition 0.000 description 10
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- DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 description 10
- 159000000000 sodium salts Chemical class 0.000 description 10
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 10
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 9
- UFSKUSARDNFIRC-UHFFFAOYSA-N Lumacaftor Chemical compound N1=C(C=2C=C(C=CC=2)C(O)=O)C(C)=CC=C1NC(=O)C1(C=2C=C3OC(F)(F)OC3=CC=2)CC1 UFSKUSARDNFIRC-UHFFFAOYSA-N 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 9
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- NKLCNNUWBJBICK-UHFFFAOYSA-N Dess–Martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 8
- 206010013774 Dry eye Diseases 0.000 description 8
- QIQXTHQIDYTFRH-UHFFFAOYSA-N Stearic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
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- 239000005711 Benzoic acid Substances 0.000 description 7
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- 150000001412 amines Chemical class 0.000 description 7
- 125000004429 atoms Chemical group 0.000 description 7
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- 239000007858 starting material Substances 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
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- 125000004169 (C1-C6) alkyl group Chemical class 0.000 description 5
- USHQRIKZLHNPQR-JTQLQIEISA-N 3-amino-6-methoxy-N-[(2S)-3,3,3-trifluoro-2-hydroxy-2-methylpropyl]-5-(trifluoromethyl)pyridine-2-carboxamide Chemical compound COC1=NC(C(=O)NC[C@](C)(O)C(F)(F)F)=C(N)C=C1C(F)(F)F USHQRIKZLHNPQR-JTQLQIEISA-N 0.000 description 5
- ASVKKRLMJCWVQF-UHFFFAOYSA-N 3-buten-1-amine Chemical compound NCCC=C ASVKKRLMJCWVQF-UHFFFAOYSA-N 0.000 description 5
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- 241000124008 Mammalia Species 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000001246 bromo group Chemical group Br* 0.000 description 5
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- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 238000002648 combination therapy Methods 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
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TW202120517A (zh) | 2019-08-14 | 2021-06-01 | 美商維泰克斯製藥公司 | 製備cftr調節劑之方法 |
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- 2019-12-18 EP EP19836572.8A patent/EP3898621A1/en active Pending
- 2019-12-18 KR KR1020217022294A patent/KR20210107046A/ko unknown
- 2019-12-18 CN CN201980083703.6A patent/CN113227087A/zh active Pending
- 2019-12-18 BR BR112021011643-5A patent/BR112021011643A2/pt unknown
- 2019-12-18 US US17/415,335 patent/US20220071971A1/en active Pending
- 2019-12-18 AU AU2019404934A patent/AU2019404934B2/en not_active Ceased
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