CA2960324A1 - Substituted n,2-diarylquinoline-4-carboxamides and the use thereof as anti-inflammatory agents - Google Patents

Info

Publication number

CA2960324A1

CA2960324A1 CA2960324A CA2960324A CA2960324A1 CA 2960324 A1 CA2960324 A1 CA 2960324A1 CA 2960324 A CA2960324 A CA 2960324A CA 2960324 A CA2960324 A CA 2960324A CA 2960324 A1 CA2960324 A1 CA 2960324A1

Authority

CA

Canada

Prior art keywords

mmol

mixture

methyl

compound

added

Prior art date

2014-09-09

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 239000002260 anti-inflammatory agent Substances 0.000 title description 3
• 229940121363 anti-inflammatory agent Drugs 0.000 title description 2
• 238000000034 method Methods 0.000 claims abstract description 170
• 238000011282 treatment Methods 0.000 claims abstract description 57
• 230000002265 prevention Effects 0.000 claims abstract description 27
• 230000003176 fibrotic effect Effects 0.000 claims abstract description 22
• 239000003814 drug Substances 0.000 claims abstract description 19
• 230000006806 disease prevention Effects 0.000 claims abstract description 5
• 150000001875 compounds Chemical class 0.000 claims description 336
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 75
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 71
• 208000035475 disorder Diseases 0.000 claims description 59
• -1 pentafluorosulfanyl Chemical group 0.000 claims description 57
• 150000003839 salts Chemical class 0.000 claims description 57
• 239000011737 fluorine Substances 0.000 claims description 55
• 229910052731 fluorine Inorganic materials 0.000 claims description 55
• 239000012453 solvate Substances 0.000 claims description 45
• 239000000460 chlorine Substances 0.000 claims description 39
• 229910052801 chlorine Inorganic materials 0.000 claims description 39
• 229910052739 hydrogen Inorganic materials 0.000 claims description 39
• 239000001257 hydrogen Substances 0.000 claims description 39
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 38
• 239000002904 solvent Substances 0.000 claims description 36
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 30
• 208000002815 pulmonary hypertension Diseases 0.000 claims description 28
• 150000002431 hydrogen Chemical class 0.000 claims description 27
• 239000005557 antagonist Substances 0.000 claims description 25
• 125000001153 fluoro group Chemical group F* 0.000 claims description 25
• 229910052757 nitrogen Inorganic materials 0.000 claims description 24
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
• 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims description 21
• 208000036971 interstitial lung disease 2 Diseases 0.000 claims description 21
• 230000002757 inflammatory effect Effects 0.000 claims description 18
• 208000011580 syndromic disease Diseases 0.000 claims description 18
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 15
• 229910052794 bromium Inorganic materials 0.000 claims description 15
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 13
• 239000002253 acid Substances 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
• 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 9
• 208000030533 eye disease Diseases 0.000 claims description 9
• 206010029888 Obliterative bronchiolitis Diseases 0.000 claims description 8
• 201000003848 bronchiolitis obliterans Diseases 0.000 claims description 8
• 208000023367 bronchiolitis obliterans with obstructive pulmonary disease Diseases 0.000 claims description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
• 208000017520 skin disease Diseases 0.000 claims description 8
• 150000001204 N-oxides Chemical class 0.000 claims description 7
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 230000004913 activation Effects 0.000 claims description 6
• 239000004480 active ingredient Substances 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 229940044601 receptor agonist Drugs 0.000 claims description 6
• 239000000018 receptor agonist Substances 0.000 claims description 6
• 230000019491 signal transduction Effects 0.000 claims description 6
• 210000001835 viscera Anatomy 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000004076 pyridyl group Chemical group 0.000 claims description 5
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
• 108050009340 Endothelin Proteins 0.000 claims description 4
• 102000002045 Endothelin Human genes 0.000 claims description 4
• 150000007513 acids Chemical class 0.000 claims description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
• ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 claims description 4
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
• 150000003815 prostacyclins Chemical class 0.000 claims description 4
• 229940123333 Phosphodiesterase 5 inhibitor Drugs 0.000 claims description 3
• 108091006335 Prostaglandin I receptors Proteins 0.000 claims description 3
• 239000012190 activator Substances 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 150000003857 carboxamides Chemical class 0.000 claims description 3
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
• 231100000252 nontoxic Toxicity 0.000 claims description 3
• 230000003000 nontoxic effect Effects 0.000 claims description 3
• 239000002590 phosphodiesterase V inhibitor Substances 0.000 claims description 3
• ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 claims description 3
• 229960003073 pirfenidone Drugs 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 241001465754 Metazoa Species 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 229940127296 soluble guanylate cyclase stimulator Drugs 0.000 claims description 2
• 125000001544 thienyl group Chemical group 0.000 claims description 2
• 102220480121 H/ACA ribonucleoprotein complex subunit DKC1_R10A_mutation Human genes 0.000 claims 1
• 125000001309 chloro group Chemical group Cl* 0.000 claims 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
• 208000027866 inflammatory disease Diseases 0.000 abstract description 7
• 229940079593 drug Drugs 0.000 abstract description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 325
• 239000000203 mixture Substances 0.000 description 241
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 177
• 208000035183 Benign hereditary chorea Diseases 0.000 description 142
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 142
• 208000012601 choreatic disease Diseases 0.000 description 142
• 239000000243 solution Substances 0.000 description 138
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 130
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 129
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 125
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 108
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 94
• 230000002829 reductive effect Effects 0.000 description 82
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical class CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 77
• 239000003480 eluent Substances 0.000 description 77
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 60
• 238000005160 1H NMR spectroscopy Methods 0.000 description 58
• 239000007787 solid Substances 0.000 description 58
• 239000011541 reaction mixture Substances 0.000 description 52
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 49
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
• 239000012074 organic phase Substances 0.000 description 45
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
• 238000003756 stirring Methods 0.000 description 41
• 229910052796 boron Inorganic materials 0.000 description 39
• 238000002953 preparative HPLC Methods 0.000 description 39
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
• 239000000741 silica gel Substances 0.000 description 37
• 229910002027 silica gel Inorganic materials 0.000 description 37
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 36
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 36
• 238000004440 column chromatography Methods 0.000 description 35
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 34
• 238000001816 cooling Methods 0.000 description 33
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 33
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 32
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 31
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 31
• 239000008346 aqueous phase Substances 0.000 description 31
• 238000006243 chemical reaction Methods 0.000 description 31
• 229910052938 sodium sulfate Inorganic materials 0.000 description 31
• 235000011152 sodium sulphate Nutrition 0.000 description 31
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 29
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 28
• 238000005481 NMR spectroscopy Methods 0.000 description 27
• 239000003112 inhibitor Substances 0.000 description 26
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
• KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 23
• 201000004624 Dermatitis Diseases 0.000 description 22
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
• 210000004072 lung Anatomy 0.000 description 21
• DOMJYWCXCVFKCA-UHFFFAOYSA-N methyl 4-amino-3-fluorobenzoate Chemical compound COC(=O)C1=CC=C(N)C(F)=C1 DOMJYWCXCVFKCA-UHFFFAOYSA-N 0.000 description 21
• 239000012071 phase Substances 0.000 description 21
• 235000015165 citric acid Nutrition 0.000 description 20
• PXGPLTODNUVGFL-UHFFFAOYSA-N prostaglandin F2alpha Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CC=CCCCC(O)=O PXGPLTODNUVGFL-UHFFFAOYSA-N 0.000 description 20
• PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 description 19
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• 239000002585 base Substances 0.000 description 19
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• 235000019341 magnesium sulphate Nutrition 0.000 description 18
• 239000000047 product Substances 0.000 description 18
• 108050008995 Prostaglandin F receptors Proteins 0.000 description 17
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• 229910052786 argon Inorganic materials 0.000 description 17
• 235000019253 formic acid Nutrition 0.000 description 17
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 16
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• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 16
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• 238000002360 preparation method Methods 0.000 description 15
• CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 description 14
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• OCKGFTQIICXDQW-ZEQRLZLVSA-N 5-[(1r)-1-hydroxy-2-[4-[(2r)-2-hydroxy-2-(4-methyl-1-oxo-3h-2-benzofuran-5-yl)ethyl]piperazin-1-yl]ethyl]-4-methyl-3h-2-benzofuran-1-one Chemical compound C1=C2C(=O)OCC2=C(C)C([C@@H](O)CN2CCN(CC2)C[C@H](O)C2=CC=C3C(=O)OCC3=C2C)=C1 OCKGFTQIICXDQW-ZEQRLZLVSA-N 0.000 description 13
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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 13
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• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
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• 125000001246 bromo group Chemical group Br* 0.000 description 8
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• 239000000706 filtrate Substances 0.000 description 7
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 7
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• 239000000523 sample Substances 0.000 description 7
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• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 7
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
• 230000001225 therapeutic effect Effects 0.000 description 7
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