JPWO2020128925A5 - - Google Patents

Info

Publication number

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

2022-11-07

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

Links

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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
• UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
• 238000007792 addition Methods 0.000 description 12
• 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
• 239000000460 chlorine Substances 0.000 description 10
• 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
• 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 9
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 9
• 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
• 229910052757 nitrogen Inorganic materials 0.000 description 9
• 239000000725 suspension Substances 0.000 description 9
• 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
• 239000002585 base Substances 0.000 description 8
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• 125000001072 heteroaryl group Chemical group 0.000 description 8
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• 238000006798 ring closing metathesis reaction Methods 0.000 description 8
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• 230000001225 therapeutic Effects 0.000 description 8
• FXLKGHMCRNENON-UHFFFAOYSA-N 6-chloro-5-(trifluoromethyl)pyridin-2-amine Chemical group NC1=CC=C(C(F)(F)F)C(Cl)=N1 FXLKGHMCRNENON-UHFFFAOYSA-N 0.000 description 7
• 239000005711 Benzoic acid Substances 0.000 description 7
• 229910019023 PtO Inorganic materials 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 125000004429 atoms Chemical group 0.000 description 7
• 235000010233 benzoic acid Nutrition 0.000 description 7
• 150000001642 boronic acid derivatives Chemical group 0.000 description 7
• 125000004432 carbon atoms Chemical group C* 0.000 description 7
• 230000003247 decreasing Effects 0.000 description 7
• 150000001975 deuterium Chemical group 0.000 description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
• 230000001965 increased Effects 0.000 description 7
• AMQJEAYHLZJPGS-UHFFFAOYSA-N n-pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 7
• 159000000001 potassium salts Chemical class 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• 125000001424 substituent group Chemical group 0.000 description 7
• 230000032258 transport Effects 0.000 description 7
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 7
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• KIDHWZJUCRJVML-UHFFFAOYSA-N Putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 6
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• RMVRSNDYEFQCLF-UHFFFAOYSA-N Thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
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• 238000005576 amination reaction Methods 0.000 description 6
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• AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 description 6
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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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• 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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• 125000004193 piperazinyl group Chemical group 0.000 description 5
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 5
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