CA2587797A1

CA2587797A1 - Novel lincomycin derivatives possessing antibacterial activity

Novel lincomycin derivatives possessing antibacterial activity Download PDF

Info

Publication number: CA2587797A1
Authority: CA; Canada
Prior art keywords: substituted; alkyl; methyl; propyl; compound
Prior art date: 2004-11-17
Legal status : Abandoned

Application number

CA002587797A

Other languages

English (en)

French (fr)

Inventor

Jason G. Lewis

Sampath K. Anandan

Hardwin O'dowd

Mikhail F. Gordeev

Liansheng Li

Current Assignee

Vicuron Pharmaceuticals LLC

Original Assignee

Individual

Priority date

2004-11-17

Filing date

2005-09-01

Publication date

2006-05-26

2004-11-17 Priority claimed from US10/992,564 external-priority patent/US7256177B2/en

2005-09-01 Application filed by Individual filed Critical Individual

2006-05-26 Publication of CA2587797A1 publication Critical patent/CA2587797A1/en

Status Abandoned legal-status Critical Current

Links

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 abstract description 19
230000000844 anti-bacterial effect Effects 0.000 title abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 482
-1 5-methyl-[1,3]dioxol-2-one-4-yl-methoxy-carbonyl Chemical group 0.000 claims description 376
229910052739 hydrogen Inorganic materials 0.000 claims description 304
239000000651 prodrug Substances 0.000 claims description 107
229940002612 prodrug Drugs 0.000 claims description 107
125000005843 halogen group Chemical group 0.000 claims description 97
229910052736 halogen Inorganic materials 0.000 claims description 83
150000003839 salts Chemical class 0.000 claims description 58
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
229910002091 carbon monoxide Inorganic materials 0.000 claims description 16
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
230000015572 biosynthetic process Effects 0.000 abstract description 73
238000003786 synthesis reaction Methods 0.000 abstract description 67
238000000034 method Methods 0.000 abstract description 64
241000894006 Bacteria Species 0.000 abstract description 11
230000000694 effects Effects 0.000 abstract description 8
239000004599 antimicrobial Substances 0.000 abstract description 2
230000003389 potentiating effect Effects 0.000 abstract description 2
125000000217 alkyl group Chemical group 0.000 description 360
239000001257 hydrogen Substances 0.000 description 230
125000004435 hydrogen atom Chemical class [H]* 0.000 description 211
125000000547 substituted alkyl group Chemical group 0.000 description 171
125000004414 alkyl thio group Chemical group 0.000 description 160
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 158
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 144
125000000753 cycloalkyl group Chemical group 0.000 description 122
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 109
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 98
239000000047 product Substances 0.000 description 90
239000000543 intermediate Substances 0.000 description 82
125000003342 alkenyl group Chemical group 0.000 description 81
239000000203 mixture Substances 0.000 description 78
125000001072 heteroaryl group Chemical class 0.000 description 76
125000005346 substituted cycloalkyl group Chemical group 0.000 description 73
125000000623 heterocyclic group Chemical class 0.000 description 71
238000006243 chemical reaction Methods 0.000 description 68
229910052760 oxygen Inorganic materials 0.000 description 67
239000001301 oxygen Substances 0.000 description 67
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
125000005017 substituted alkenyl group Chemical group 0.000 description 66
125000002887 hydroxy group Chemical group [H]O* 0.000 description 62
150000002926 oxygen Chemical class 0.000 description 60
150000002367 halogens Chemical class 0.000 description 55
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
125000003118 aryl group Chemical class 0.000 description 51
239000003153 chemical reaction reagent Substances 0.000 description 49
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 49
125000003545 alkoxy group Chemical group 0.000 description 46
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 44
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
239000003960 organic solvent Substances 0.000 description 42
125000003107 substituted aryl group Chemical class 0.000 description 42
125000001153 fluoro group Chemical group F* 0.000 description 40
125000005415 substituted alkoxy group Chemical group 0.000 description 39
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 38
229910052757 nitrogen Inorganic materials 0.000 description 38
239000011541 reaction mixture Substances 0.000 description 36
229910001868 water Inorganic materials 0.000 description 36
241000194032 Enterococcus faecalis Species 0.000 description 35
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 35
229940032049 enterococcus faecalis Drugs 0.000 description 34
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 33
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 33
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
239000002585 base Substances 0.000 description 32
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 32
125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 32
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 31
125000001424 substituent group Chemical group 0.000 description 31
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 30
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 29
239000004480 active ingredient Substances 0.000 description 28
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 27
125000001118 alkylidene group Chemical group 0.000 description 27
125000004093 cyano group Chemical group *C#N 0.000 description 27
229910052799 carbon Inorganic materials 0.000 description 26
125000001309 chloro group Chemical group Cl* 0.000 description 26
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
150000002829 nitrogen Chemical class 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
235000019439 ethyl acetate Nutrition 0.000 description 23
239000002904 solvent Substances 0.000 description 23
241000606768 Haemophilus influenzae Species 0.000 description 22
229920006395 saturated elastomer Polymers 0.000 description 22
238000009472 formulation Methods 0.000 description 21
229940047650 haemophilus influenzae Drugs 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
229910020008 S(O) Inorganic materials 0.000 description 20
239000008194 pharmaceutical composition Substances 0.000 description 20
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
125000000304 alkynyl group Chemical group 0.000 description 19
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 19
239000000243 solution Substances 0.000 description 19
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 18
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 18
150000007530 organic bases Chemical class 0.000 description 18
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
150000001412 amines Chemical class 0.000 description 17
241000124008 Mammalia Species 0.000 description 16
125000005083 alkoxyalkoxy group Chemical group 0.000 description 16
239000003054 catalyst Substances 0.000 description 16
208000015181 infectious disease Diseases 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
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
150000001409 amidines Chemical class 0.000 description 15
239000003242 anti bacterial agent Substances 0.000 description 15
125000004432 carbon atom Chemical group C* 0.000 description 15
201000010099 disease Diseases 0.000 description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 15
150000002148 esters Chemical class 0.000 description 15
239000012634 fragment Substances 0.000 description 15
125000002768 hydroxyalkyl group Chemical group 0.000 description 15
229920005989 resin Polymers 0.000 description 15
239000011347 resin Substances 0.000 description 15
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 14
239000012043 crude product Substances 0.000 description 14
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 14
IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 14
229910052698 phosphorus Inorganic materials 0.000 description 14
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 14
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 13
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 13
238000005859 coupling reaction Methods 0.000 description 13
239000012038 nucleophile Substances 0.000 description 13
238000011282 treatment Methods 0.000 description 13
229910019142 PO4 Inorganic materials 0.000 description 12
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 12
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 12
239000010452 phosphate Substances 0.000 description 12
239000011574 phosphorus Substances 0.000 description 12
125000006239 protecting group Chemical group 0.000 description 12
125000004426 substituted alkynyl group Chemical group 0.000 description 12
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 12
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
150000001336 alkenes Chemical class 0.000 description 11
229940024606 amino acid Drugs 0.000 description 11
235000001014 amino acid Nutrition 0.000 description 11
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 11
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 11
238000010511 deprotection reaction Methods 0.000 description 11
239000000546 pharmaceutical excipient Substances 0.000 description 11
239000003826 tablet Substances 0.000 description 11
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 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
238000005481 NMR spectroscopy Methods 0.000 description 10
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 10
229920002472 Starch Polymers 0.000 description 10
125000005163 aryl sulfanyl group Chemical group 0.000 description 10
125000001188 haloalkyl group Chemical group 0.000 description 10
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
150000004714 phosphonium salts Chemical class 0.000 description 10
239000003495 polar organic solvent Substances 0.000 description 10
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 10
125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 10
229910052707 ruthenium Inorganic materials 0.000 description 10
235000019698 starch Nutrition 0.000 description 10
ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 9
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
230000008878 coupling Effects 0.000 description 9
238000010168 coupling process Methods 0.000 description 9
239000003814 drug Substances 0.000 description 9
OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 9
239000008107 starch Substances 0.000 description 9
238000004809 thin layer chromatography Methods 0.000 description 9
238000005406 washing Methods 0.000 description 9
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
MEOZFUYXLCDYGA-UHFFFAOYSA-N azepane-1-carboxylic acid Chemical compound OC(=O)N1CCCCCC1 MEOZFUYXLCDYGA-UHFFFAOYSA-N 0.000 description 8
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 8
239000004615 ingredient Substances 0.000 description 8
235000019359 magnesium stearate Nutrition 0.000 description 8
235000013930 proline Nutrition 0.000 description 8
238000006798 ring closing metathesis reaction Methods 0.000 description 8
125000006413 ring segment Chemical group 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
239000000377 silicon dioxide Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
208000024891 symptom Diseases 0.000 description 8
125000004001 thioalkyl group Chemical group 0.000 description 8
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 8
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 7
238000005160 1H NMR spectroscopy Methods 0.000 description 7
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
241000192125 Firmicutes Species 0.000 description 7
229910003827 NRaRb Inorganic materials 0.000 description 7
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
150000007513 acids Chemical class 0.000 description 7
238000007792 addition Methods 0.000 description 7
238000005804 alkylation reaction Methods 0.000 description 7
150000001413 amino acids Chemical class 0.000 description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
239000002552 dosage form Substances 0.000 description 7
229940079593 drug Drugs 0.000 description 7
239000003937 drug carrier Substances 0.000 description 7
238000005984 hydrogenation reaction Methods 0.000 description 7
230000005764 inhibitory process Effects 0.000 description 7
239000000463 material Substances 0.000 description 7
125000001979 organolithium group Chemical group 0.000 description 7
239000000843 powder Substances 0.000 description 7
150000003222 pyridines Chemical class 0.000 description 7
125000000719 pyrrolidinyl group Chemical group 0.000 description 7
238000003756 stirring Methods 0.000 description 7
239000000126 substance Substances 0.000 description 7
238000010626 work up procedure Methods 0.000 description 7
RUKVGXGTVPPWDD-UHFFFAOYSA-N 1,3-bis(2,4,6-trimethylphenyl)imidazolidine Chemical group CC1=CC(C)=CC(C)=C1N1CN(C=2C(=CC(C)=CC=2C)C)CC1 RUKVGXGTVPPWDD-UHFFFAOYSA-N 0.000 description 6
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
229910015900 BF3 Inorganic materials 0.000 description 6
239000004215 Carbon black (E152) Substances 0.000 description 6
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 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
150000001299 aldehydes Chemical class 0.000 description 6
239000003513 alkali Substances 0.000 description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
239000006184 cosolvent Substances 0.000 description 6
125000003963 dichloro group Chemical group Cl* 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
229930195733 hydrocarbon Natural products 0.000 description 6
150000002576 ketones Chemical class 0.000 description 6
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 6
LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
229960002429 proline Drugs 0.000 description 6
229910052717 sulfur Inorganic materials 0.000 description 6
239000011593 sulfur Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 6
230000001225 therapeutic effect Effects 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
230000009466 transformation Effects 0.000 description 6
DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 description 5
101150041968 CDC13 gene Proteins 0.000 description 5
241000194031 Enterococcus faecium Species 0.000 description 5
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
239000002168 alkylating agent Substances 0.000 description 5
229940100198 alkylating agent Drugs 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
230000037396 body weight Effects 0.000 description 5
239000012267 brine Substances 0.000 description 5
239000002775 capsule Substances 0.000 description 5
125000004966 cyanoalkyl group Chemical group 0.000 description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 5
229910052731 fluorine Inorganic materials 0.000 description 5
150000002222 fluorine compounds Chemical class 0.000 description 5
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