ES2687393T3 - Derivados del ácido hidroxámico de isoxazolina como inhibidores de LpxC - Google Patents

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Publication number

ES2687393T3

ES2687393T3 ES15721435.4T ES15721435T ES2687393T3 ES 2687393 T3 ES2687393 T3 ES 2687393T3 ES 15721435 T ES15721435 T ES 15721435T ES 2687393 T3 ES2687393 T3 ES 2687393T3

Authority

ES

Spain

Prior art keywords

mmol

equiv

methyl

methylsulfonyl

dihydroisoxazol

Prior art date

2014-04-22

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.)

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• 239000003112 inhibitor Substances 0.000 title description 10
• WWCXTTVDOOAWMK-UHFFFAOYSA-N N-hydroxy-4,5-dihydro-1,2-oxazole-3-carboxamide Chemical class O1N=C(CC1)C(=O)NO WWCXTTVDOOAWMK-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 278
• -1 amino, hydroxy Chemical group 0.000 claims abstract description 95
• 150000003839 salts Chemical class 0.000 claims abstract description 92
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 67
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 51
• 125000005843 halogen group Chemical group 0.000 claims abstract description 33
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 26
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 25
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 24
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 23
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 20
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 13
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 11
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 11
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 10
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims abstract description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims abstract description 4
• 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 4
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract 5
• 239000000203 mixture Substances 0.000 claims description 89
• 238000011282 treatment Methods 0.000 claims description 31
• 239000003814 drug Substances 0.000 claims description 28
• 239000008194 pharmaceutical composition Substances 0.000 claims description 27
• 241000894006 Bacteria Species 0.000 claims description 20
• 230000000844 anti-bacterial effect Effects 0.000 claims description 17
• 208000035143 Bacterial infection Diseases 0.000 claims description 11
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 11
• 208000027096 gram-negative bacterial infections Diseases 0.000 claims description 11
• MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims description 10
• 239000003981 vehicle Substances 0.000 claims description 10
• 239000003937 drug carrier Substances 0.000 claims description 9
• 229940124597 therapeutic agent Drugs 0.000 claims description 9
• 208000015181 infectious disease Diseases 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 claims description 7
• 241000589291 Acinetobacter Species 0.000 claims description 6
• ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 6
• 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 6
• 241001673062 Achromobacter xylosoxidans Species 0.000 claims description 5
• 241000588921 Enterobacteriaceae Species 0.000 claims description 5
• 241000588769 Proteus <enterobacteria> Species 0.000 claims description 5
• 241000607142 Salmonella Species 0.000 claims description 5
• 241000122973 Stenotrophomonas maltophilia Species 0.000 claims description 5
• 229960003405 ciprofloxacin Drugs 0.000 claims description 5
• 229910052731 fluorine Inorganic materials 0.000 claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 5
• WZPBZJONDBGPKJ-UHFFFAOYSA-N Antibiotic SQ 26917 Natural products O=C1N(S(O)(=O)=O)C(C)C1NC(=O)C(=NOC(C)(C)C(O)=O)C1=CSC(N)=N1 WZPBZJONDBGPKJ-UHFFFAOYSA-N 0.000 claims description 4
• CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 claims description 4
• 229930182566 Gentamicin Natural products 0.000 claims description 4
• 241000606790 Haemophilus Species 0.000 claims description 4
• 241000588653 Neisseria Species 0.000 claims description 4
• 108010040201 Polymyxins Proteins 0.000 claims description 4
• 241000589516 Pseudomonas Species 0.000 claims description 4
• 241000607768 Shigella Species 0.000 claims description 4
• 239000004098 Tetracycline Substances 0.000 claims description 4
• 108010059993 Vancomycin Proteins 0.000 claims description 4
• 229960004099 azithromycin Drugs 0.000 claims description 4
• MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 claims description 4
• 229960003644 aztreonam Drugs 0.000 claims description 4
• WZPBZJONDBGPKJ-VEHQQRBSSA-N aztreonam Chemical compound O=C1N(S([O-])(=O)=O)[C@@H](C)[C@@H]1NC(=O)C(=N/OC(C)(C)C(O)=O)\C1=CSC([NH3+])=N1 WZPBZJONDBGPKJ-VEHQQRBSSA-N 0.000 claims description 4
• 229960002518 gentamicin Drugs 0.000 claims description 4
• 229960001225 rifampicin Drugs 0.000 claims description 4
• 235000019364 tetracycline Nutrition 0.000 claims description 4
• 150000003522 tetracyclines Chemical class 0.000 claims description 4
• 229960000707 tobramycin Drugs 0.000 claims description 4
• NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 claims description 4
• 229960003165 vancomycin Drugs 0.000 claims description 4
• MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 claims description 4
• SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 claims description 3
• 241001453380 Burkholderia Species 0.000 claims description 3
• 241000589513 Burkholderia cepacia Species 0.000 claims description 3
• GSDSWSVVBLHKDQ-JTQLQIEISA-N Levofloxacin Chemical compound C([C@@H](N1C2=C(C(C(C(O)=O)=C1)=O)C=C1F)C)OC2=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-JTQLQIEISA-N 0.000 claims description 3
• 241000588621 Moraxella Species 0.000 claims description 3
• 241000607720 Serratia Species 0.000 claims description 3
• 241000607598 Vibrio Species 0.000 claims description 3
• 229960004821 amikacin Drugs 0.000 claims description 3
• LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 claims description 3
• 229960000723 ampicillin Drugs 0.000 claims description 3
• AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 claims description 3
• 229960004261 cefotaxime Drugs 0.000 claims description 3
• AZZMGZXNTDTSME-JUZDKLSSSA-M cefotaxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 AZZMGZXNTDTSME-JUZDKLSSSA-M 0.000 claims description 3
• 229960004755 ceftriaxone Drugs 0.000 claims description 3
• VAAUVRVFOQPIGI-SPQHTLEESA-N ceftriaxone Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC1=NC(=O)C(=O)NN1C VAAUVRVFOQPIGI-SPQHTLEESA-N 0.000 claims description 3
• 229960002227 clindamycin Drugs 0.000 claims description 3
• KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 229960003722 doxycycline Drugs 0.000 claims description 3
• 229960003276 erythromycin Drugs 0.000 claims description 3
• 229960003376 levofloxacin Drugs 0.000 claims description 3
• 229940056360 penicillin g Drugs 0.000 claims description 3
• 229960002292 piperacillin Drugs 0.000 claims description 3
• WCMIIGXFCMNQDS-IDYPWDAWSA-M piperacillin sodium Chemical compound [Na+].O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@@H]21 WCMIIGXFCMNQDS-IDYPWDAWSA-M 0.000 claims description 3
• 229960002180 tetracycline Drugs 0.000 claims description 3
• 229930101283 tetracycline Natural products 0.000 claims description 3
• 229960004659 ticarcillin Drugs 0.000 claims description 3
• OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 claims description 3
• 241000588923 Citrobacter Species 0.000 claims description 2
• WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 claims description 2
• 229960002100 cefepime Drugs 0.000 claims description 2
• 229960002182 imipenem Drugs 0.000 claims description 2
• ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 claims description 2
• DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 claims description 2
• 229960002260 meropenem Drugs 0.000 claims description 2
• MMRINLZOZVAPDZ-LSGRDSQZSA-N (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(1-methylpyrrolidin-1-ium-1-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;chloride Chemical compound Cl.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1C[N+]1(C)CCCC1 MMRINLZOZVAPDZ-LSGRDSQZSA-N 0.000 claims 1
• JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 claims 1
• MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 271
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 249
• 239000011541 reaction mixture Substances 0.000 description 233
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 219
• 238000003786 synthesis reaction Methods 0.000 description 212
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 210
• 230000015572 biosynthetic process Effects 0.000 description 206
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 171
• 238000000034 method Methods 0.000 description 154
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 150
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 139
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 134
• 235000019439 ethyl acetate Nutrition 0.000 description 133
• 239000000047 product Substances 0.000 description 107
• QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 105
• 238000005160 1H NMR spectroscopy Methods 0.000 description 98
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 93
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 87
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 86
• 238000005481 NMR spectroscopy Methods 0.000 description 85
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 82
• 239000012044 organic layer Substances 0.000 description 82
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 81
• 229910052938 sodium sulfate Inorganic materials 0.000 description 81
• 235000011152 sodium sulphate Nutrition 0.000 description 81
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 78
• 239000012267 brine Substances 0.000 description 78
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 78
• 239000000243 solution Substances 0.000 description 56
• 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 53
• 239000002253 acid Substances 0.000 description 51
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 47
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 39
• 238000010898 silica gel chromatography Methods 0.000 description 37
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 37
• 239000002904 solvent Substances 0.000 description 37
• 229910002666 PdCl2 Inorganic materials 0.000 description 36
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 36
• PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 36
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 32
• 239000003153 chemical reaction reagent Substances 0.000 description 32
• YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 31
• GQHTUMJGOHRCHB-UHFFFAOYSA-N DBU Substances C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 31
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• 230000008569 process Effects 0.000 description 25
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• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 23
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• NTEURBORARLYJB-UHFFFAOYSA-N n-methylsulfonylpropanamide Chemical compound CCC(=O)NS(C)(=O)=O NTEURBORARLYJB-UHFFFAOYSA-N 0.000 description 22
• 239000000741 silica gel Substances 0.000 description 22
• 229910002027 silica gel Inorganic materials 0.000 description 22
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 21
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• 230000002829 reductive effect Effects 0.000 description 20
• 238000004440 column chromatography Methods 0.000 description 19
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• BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 description 18
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• 229910052805 deuterium Inorganic materials 0.000 description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 18
• 239000003242 anti bacterial agent Substances 0.000 description 17
• OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 17
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