IL166476A - Lincomycin derivatives possessing antibacterial activity - Google Patents

Info

Publication number

IL166476A

IL166476A IL166476A IL16647605A IL166476A IL 166476 A IL166476 A IL 166476A IL 166476 A IL166476 A IL 166476A IL 16647605 A IL16647605 A IL 16647605A IL 166476 A IL166476 A IL 166476A

Authority

IL

Israel

Prior art keywords

mmol

added

stirred

compound

equiv

Prior art date

2002-08-15

Links

• Espacenet
• Global Dossier
• Discuss

• OJMMVQQUTAEWLP-KIDUDLJLSA-N lincomycin Chemical class CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 OJMMVQQUTAEWLP-KIDUDLJLSA-N 0.000 title description 11
• 230000000844 anti-bacterial effect Effects 0.000 title description 6
• 150000001875 compounds Chemical class 0.000 claims description 203
• -1 4-fluorobutyl Chemical group 0.000 claims description 93
• 125000000217 alkyl group Chemical group 0.000 claims description 38
• 150000003839 salts Chemical class 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
• 239000000651 prodrug Substances 0.000 claims description 15
• 229940002612 prodrug Drugs 0.000 claims description 15
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
• HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 6
• 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 claims 1
• 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
• 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
• 125000006678 phenoxycarbonyl group Chemical group 0.000 claims 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 501
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 460
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 242
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 216
• 239000011541 reaction mixture Substances 0.000 description 182
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 174
• 239000000203 mixture Substances 0.000 description 172
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 134
• 229910001868 water Inorganic materials 0.000 description 134
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 130
• 239000000047 product Substances 0.000 description 128
• 239000000243 solution Substances 0.000 description 125
• 239000002904 solvent Substances 0.000 description 118
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 117
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 99
• 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 99
• 238000000034 method Methods 0.000 description 98
• 235000019439 ethyl acetate Nutrition 0.000 description 91
• 238000005160 1H NMR spectroscopy Methods 0.000 description 79
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 78
• 238000002360 preparation method Methods 0.000 description 70
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 66
• 238000004587 chromatography analysis Methods 0.000 description 65
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 64
• 229940093499 ethyl acetate Drugs 0.000 description 60
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 59
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
• 239000012043 crude product Substances 0.000 description 55
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 53
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 53
• 238000005481 NMR spectroscopy Methods 0.000 description 51
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 49
• 229940086542 triethylamine Drugs 0.000 description 49
• 239000012267 brine Substances 0.000 description 47
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 47
• 238000006243 chemical reaction Methods 0.000 description 45
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 44
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 43
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 42
• 239000002253 acid Substances 0.000 description 41
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 41
• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 40
• 239000007787 solid Substances 0.000 description 40
• 239000011347 resin Substances 0.000 description 39
• 229920005989 resin Polymers 0.000 description 39
• 101150041968 CDC13 gene Proteins 0.000 description 37
• 235000020357 syrup Nutrition 0.000 description 37
• 239000006188 syrup Substances 0.000 description 37
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 36
• 239000003480 eluent Substances 0.000 description 36
• 239000012044 organic layer Substances 0.000 description 36
• 239000000543 intermediate Substances 0.000 description 35
• 239000007821 HATU Substances 0.000 description 33
• 239000000706 filtrate Substances 0.000 description 33
• 238000004809 thin layer chromatography Methods 0.000 description 33
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
• 230000015572 biosynthetic process Effects 0.000 description 32
• 238000003786 synthesis reaction Methods 0.000 description 32
• 239000003960 organic solvent Substances 0.000 description 31
• 238000010898 silica gel chromatography Methods 0.000 description 31
• XCOBLONWWXQEBS-KPKJPENVSA-N N,O-bis(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)O\C(C(F)(F)F)=N\[Si](C)(C)C XCOBLONWWXQEBS-KPKJPENVSA-N 0.000 description 29
• 239000003153 chemical reaction reagent Substances 0.000 description 29
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 28
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
• 239000004480 active ingredient Substances 0.000 description 28
• 238000001914 filtration Methods 0.000 description 27
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
• 235000015165 citric acid Nutrition 0.000 description 26
• 239000011734 sodium Substances 0.000 description 26
• 238000000746 purification Methods 0.000 description 25
• 239000000741 silica gel Substances 0.000 description 25
• 229910002027 silica gel Inorganic materials 0.000 description 25
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
• 238000007429 general method Methods 0.000 description 23
• 229910052757 nitrogen Inorganic materials 0.000 description 23
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
• 239000003921 oil Substances 0.000 description 22
• 235000019198 oils Nutrition 0.000 description 22
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 22
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 21
• 238000009472 formulation Methods 0.000 description 21
• KOFBVFFPLADGGO-DUSUDKPKSA-N (3r,4s,5r,6r)-6-[(1r,2r)-1-amino-2-hydroxypropyl]oxane-2,3,4,5-tetrol Chemical compound C[C@@H](O)[C@@H](N)[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O KOFBVFFPLADGGO-DUSUDKPKSA-N 0.000 description 20
• 229920006395 saturated elastomer Polymers 0.000 description 19
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 18
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 17
• 238000003756 stirring Methods 0.000 description 17
• 239000003814 drug Substances 0.000 description 16
• 125000001072 heteroaryl group Chemical group 0.000 description 16
• 239000001257 hydrogen Substances 0.000 description 16
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 239000000843 powder Substances 0.000 description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 201000010099 disease Diseases 0.000 description 15
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
• 239000004615 ingredient Substances 0.000 description 15
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
• 125000003118 aryl group Chemical group 0.000 description 14
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
• 229920001467 poly(styrenesulfonates) Polymers 0.000 description 14
• 235000017557 sodium bicarbonate Nutrition 0.000 description 14
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 13
• 150000001299 aldehydes Chemical class 0.000 description 13
• CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 13
• 239000010410 layer Substances 0.000 description 13
• 239000003495 polar organic solvent Substances 0.000 description 13
• 238000005406 washing Methods 0.000 description 13
• SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 12
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
• 241000191967 Staphylococcus aureus Species 0.000 description 12
• 125000003342 alkenyl group Chemical group 0.000 description 12
• SRVFFFJZQVENJC-IHRRRGAJSA-N aloxistatin Chemical compound CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C SRVFFFJZQVENJC-IHRRRGAJSA-N 0.000 description 12
• 125000004432 carbon atom Chemical group C* 0.000 description 12
• 238000004440 column chromatography Methods 0.000 description 12
• 229940079593 drug Drugs 0.000 description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
• 150000007530 organic bases Chemical class 0.000 description 12
• MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 12
• 229910003446 platinum oxide Inorganic materials 0.000 description 12
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
• 239000000725 suspension Substances 0.000 description 12
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
• 238000005859 coupling reaction Methods 0.000 description 11
• 235000019341 magnesium sulphate Nutrition 0.000 description 11
• 239000008194 pharmaceutical composition Substances 0.000 description 11
• 239000000546 pharmaceutical excipient Substances 0.000 description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
• 229910052938 sodium sulfate Inorganic materials 0.000 description 11
• 235000011152 sodium sulphate Nutrition 0.000 description 11
• 229920002472 Starch Polymers 0.000 description 10
• 239000002168 alkylating agent Substances 0.000 description 10
• 229940100198 alkylating agent Drugs 0.000 description 10
• 239000002585 base Substances 0.000 description 10
• 229910052799 carbon Inorganic materials 0.000 description 10
• 239000000377 silicon dioxide Substances 0.000 description 10
• 235000019698 starch Nutrition 0.000 description 10
• LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 10
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• 241000699670 Mus sp. Species 0.000 description 9
• 239000003054 catalyst Substances 0.000 description 9
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• 238000010168 coupling process Methods 0.000 description 9
• 150000003951 lactams Chemical class 0.000 description 9
• 235000013930 proline Nutrition 0.000 description 9
• 125000006239 protecting group Chemical group 0.000 description 9
• 239000008107 starch Substances 0.000 description 9
• 125000000547 substituted alkyl group Chemical group 0.000 description 9
• 239000003826 tablet Substances 0.000 description 9
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
• MXXLHBCSVDDTIX-UHFFFAOYSA-N 4-oxo-1h-pyridine-2-carboxylic acid Chemical compound OC(=O)C1=CC(O)=CC=N1 MXXLHBCSVDDTIX-UHFFFAOYSA-N 0.000 description 8
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• 241000894006 Bacteria Species 0.000 description 8
• XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 8
• 241000193998 Streptococcus pneumoniae Species 0.000 description 8
• YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 8
• 239000003242 anti bacterial agent Substances 0.000 description 8
• 239000002775 capsule Substances 0.000 description 8
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 8
• 239000012230 colorless oil Substances 0.000 description 8
• 235000019359 magnesium stearate Nutrition 0.000 description 8
• 239000000463 material Substances 0.000 description 8
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• 229910000027 potassium carbonate Inorganic materials 0.000 description 8
• 235000011181 potassium carbonates Nutrition 0.000 description 8
• 230000009467 reduction Effects 0.000 description 8
• 229940031000 streptococcus pneumoniae Drugs 0.000 description 8
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• 125000001424 substituent group Chemical group 0.000 description 8
• 208000024891 symptom Diseases 0.000 description 8
• DPRJPRMZJGWLHY-HNGSOEQISA-N (e,3r,5s)-7-[5-(4-fluorophenyl)-3-propan-2-yl-1-pyrazin-2-ylpyrazol-4-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound OC(=O)C[C@H](O)C[C@H](O)/C=C/C=1C(C(C)C)=NN(C=2N=CC=NC=2)C=1C1=CC=C(F)C=C1 DPRJPRMZJGWLHY-HNGSOEQISA-N 0.000 description 7
• JVYSADGFOWESAS-UHFFFAOYSA-N 4-pentylpyridine-2-carboxylic acid Chemical compound CCCCCC1=CC=NC(C(O)=O)=C1 JVYSADGFOWESAS-UHFFFAOYSA-N 0.000 description 7
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 7
• 239000004215 Carbon black (E152) Substances 0.000 description 7
• YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 7
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• 241000124008 Mammalia Species 0.000 description 7
• 125000000304 alkynyl group Chemical group 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 238000003556 assay Methods 0.000 description 7
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• 229960001760 dimethyl sulfoxide Drugs 0.000 description 7
• 239000002552 dosage form Substances 0.000 description 7
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• 125000000623 heterocyclic group Chemical group 0.000 description 7
• 229930195733 hydrocarbon Natural products 0.000 description 7
• 229940040692 lithium hydroxide monohydrate Drugs 0.000 description 7
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
• YRCHYHRCBXNYNU-UHFFFAOYSA-N n-[[3-fluoro-4-[2-[5-[(2-methoxyethylamino)methyl]pyridin-2-yl]thieno[3,2-b]pyridin-7-yl]oxyphenyl]carbamothioyl]-2-(4-fluorophenyl)acetamide Chemical compound N1=CC(CNCCOC)=CC=C1C1=CC2=NC=CC(OC=3C(=CC(NC(=S)NC(=O)CC=4C=CC(F)=CC=4)=CC=3)F)=C2S1 YRCHYHRCBXNYNU-UHFFFAOYSA-N 0.000 description 7
• 239000001301 oxygen Substances 0.000 description 7
• SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 7
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
• 229960002429 proline Drugs 0.000 description 7
• 150000003222 pyridines Chemical class 0.000 description 7
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• 230000001225 therapeutic effect Effects 0.000 description 7
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
• YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 6
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• 241000606790 Haemophilus Species 0.000 description 6
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 150000007513 acids Chemical class 0.000 description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
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• 125000000753 cycloalkyl group Chemical group 0.000 description 6
• 238000001704 evaporation Methods 0.000 description 6
• 230000008020 evaporation Effects 0.000 description 6
• 125000005843 halogen group Chemical group 0.000 description 6
• 150000002374 hemiaminals Chemical class 0.000 description 6
• 238000001727 in vivo Methods 0.000 description 6
• 208000015181 infectious disease Diseases 0.000 description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
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