IE914115A1

IE914115A1 - Quinoline, naphthyridine and pyridobenzoxazine derivatives

Quinoline, naphthyridine and pyridobenzoxazine derivatives

Info

Publication number: IE914115A1
Authority: IE; Ireland
Prior art keywords: dioxa; azaspiro; fluoro; amino; lower alkyl
Prior art date: 1990-12-12

Application number

IE411591A

Other languages

English (en)

Original Assignee

Abbott Lab

Priority date

1990-12-12

Filing date

1991-11-26

Publication date

1992-06-17

1991-11-26 Application filed by Abbott Lab filed Critical Abbott Lab

1992-06-17 Publication of IE914115A1 publication Critical patent/IE914115A1/en

Links

SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 5
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 title description 4
QDEJGQKJMKXYLM-UHFFFAOYSA-N 2h-pyrido[2,3-h][1,2]benzoxazine Chemical class C1=CC2=NC=CC=C2C2=C1C=CNO2 QDEJGQKJMKXYLM-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 291
125000000217 alkyl group Chemical group 0.000 claims abstract description 104
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 86
150000002148 esters Chemical class 0.000 claims abstract description 57
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 46
239000001257 hydrogen Substances 0.000 claims abstract description 46
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 18
150000003839 salts Chemical class 0.000 claims abstract description 17
239000000651 prodrug Substances 0.000 claims abstract description 16
229940002612 prodrug Drugs 0.000 claims abstract description 16
150000001408 amides Chemical class 0.000 claims abstract description 14
125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
150000002367 halogens Chemical class 0.000 claims abstract description 9
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
150000001768 cations Chemical class 0.000 claims abstract description 8
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
125000004185 ester group Chemical group 0.000 claims abstract description 6
125000000304 alkynyl group Chemical group 0.000 claims abstract description 5
125000004429 atom Chemical group 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
125000004434 sulfur atom Chemical group 0.000 claims abstract description 4
238000000034 method Methods 0.000 claims description 77
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 28
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
241001465754 Metazoa Species 0.000 claims description 10
SKENCOGHUZMTTF-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-7-[3-[(dimethylamino)methyl]-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl]-6-fluoro-2h-1,8-naphthyridine-3-carboxylic acid Chemical compound O1C(CN(C)C)COC11CN(C=2C(=CC=3C=C(CN(C=3N=2)C=2C(=CC(F)=CC=2)F)C(O)=O)F)CC1 SKENCOGHUZMTTF-UHFFFAOYSA-N 0.000 claims description 5
125000001475 halogen functional group Chemical group 0.000 claims description 5
UDSILKPSXBYCIC-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-7-(1,5-dioxa-9-azaspiro[5.5]undecan-9-yl)-6-fluoro-2h-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(C(=O)O)=CC2=CC(F)=C(N3CCC4(CC3)OCCCO4)N=C2N1C1=CC=C(F)C=C1F UDSILKPSXBYCIC-UHFFFAOYSA-N 0.000 claims description 4
208000035143 Bacterial infection Diseases 0.000 claims description 4
208000022362 bacterial infectious disease Diseases 0.000 claims description 4
HXOFONMRSDKAOY-UHFFFAOYSA-N 7-[3-(aminomethyl)-1,4-dioxa-8-azaspiro[4.5]decan-8-yl]-1-(2,4-difluorophenyl)-6-fluoro-2h-1,8-naphthyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.O1C(CN)COC11CCN(C=2C(=CC=3C=C(CN(C=3N=2)C=2C(=CC(F)=CC=2)F)C(O)=O)F)CC1 HXOFONMRSDKAOY-UHFFFAOYSA-N 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
WAYVLHAUOLNICN-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-6-fluoro-7-(3-methyl-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-2H-1,8-naphthyridine-3-carboxylic acid Chemical compound FC1=C(C=CC(=C1)F)N1CC(=CC2=CC(=C(N=C12)N1CC2(OCC(O2)C)CC1)F)C(=O)O WAYVLHAUOLNICN-UHFFFAOYSA-N 0.000 claims description 2
PQUGFFXYPNWZEP-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-6-fluoro-7-(3-methyl-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound O1C(C)COC11CN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C=2C(=CC(F)=CC=2)F)F)CC1 PQUGFFXYPNWZEP-UHFFFAOYSA-N 0.000 claims description 2
WAXQMYUKAAUCOT-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-6-fluoro-7-[3-(methylaminomethyl)-1,4-dioxa-8-azaspiro[4.5]decan-8-yl]-2h-1,8-naphthyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.O1C(CNC)COC11CCN(C=2C(=CC=3C=C(CN(C=3N=2)C=2C(=CC(F)=CC=2)F)C(O)=O)F)CC1 WAXQMYUKAAUCOT-UHFFFAOYSA-N 0.000 claims description 2
IRTQVHULMAHQBL-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-7-(3,3-dimethoxy-4-methylpyrrolidin-1-yl)-6-fluoro-2h-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(C)C(OC)(OC)CN1C(C(=C1)F)=NC2=C1C=C(C(O)=O)CN2C1=CC=C(F)C=C1F IRTQVHULMAHQBL-UHFFFAOYSA-N 0.000 claims description 2
OTGVPZDGAPQYDQ-UHFFFAOYSA-N 1-cyclopropyl-7-(3,3-dimethoxypyrrolidin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(OC)(OC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 OTGVPZDGAPQYDQ-UHFFFAOYSA-N 0.000 claims description 2
UMGPJMRVGBNRBB-UHFFFAOYSA-N 1-cyclopropyl-7-[3-[(dimethylamino)methyl]-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl]-6-fluoro-2h-1,8-naphthyridine-3-carboxylic acid Chemical compound O1C(CN(C)C)COC11CN(C=2C(=CC=3C=C(CN(C=3N=2)C2CC2)C(O)=O)F)CC1 UMGPJMRVGBNRBB-UHFFFAOYSA-N 0.000 claims description 2
CLOQCVPLBLVBBQ-UHFFFAOYSA-N 6-fluoro-1-(4-fluorophenyl)-7-(3-methyl-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-2H-1,8-naphthyridine-3-carboxylic acid Chemical compound CC1OC2(OC1)CN(CC2)C1=C(C=C2C=C(CN(C2=N1)C1=CC=C(C=C1)F)C(=O)O)F CLOQCVPLBLVBBQ-UHFFFAOYSA-N 0.000 claims description 2
KEVVEPFBZMUXHF-UHFFFAOYSA-N 7-(9-amino-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-1-(2,4-difluorophenyl)-6-fluoro-2h-1,8-naphthyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.NC1CN(C=2C(=CC=3C=C(CN(C=3N=2)C=2C(=CC(F)=CC=2)F)C(O)=O)F)CC11OCCO1 KEVVEPFBZMUXHF-UHFFFAOYSA-N 0.000 claims description 2
MCRDYVNIRAVHJG-UHFFFAOYSA-N 7-(9-amino-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound NC1CN(C=2C(=C3C(C(C(C(O)=O)=CN3C3CC3)=O)=CC=2F)F)CC11OCCO1 MCRDYVNIRAVHJG-UHFFFAOYSA-N 0.000 claims description 2
YKQQDKKZVSJPJK-UHFFFAOYSA-N 7-[3-(aminomethyl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl]-1-(2,4-difluorophenyl)-6-fluoro-2h-1,8-naphthyridine-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.O1C(CN)COC11CN(C=2C(=CC=3C=C(CN(C=3N=2)C=2C(=CC(F)=CC=2)F)C(O)=O)F)CC1 YKQQDKKZVSJPJK-UHFFFAOYSA-N 0.000 claims description 2
RPIHEQJRDMCZTL-UHFFFAOYSA-N 7-[3-(aminomethyl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl]-1-(2,4-difluorophenyl)-6-fluoro-4-oxoquinoline-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.O1C(CN)COC11CN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C=2C(=CC(F)=CC=2)F)F)CC1 RPIHEQJRDMCZTL-UHFFFAOYSA-N 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims 8
TZBZWKZHYNZMSS-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-7-(1,5-dioxa-9-azaspiro[5.5]undecan-9-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCC4(CC3)OCCCO4)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1F TZBZWKZHYNZMSS-UHFFFAOYSA-N 0.000 claims 1
VWOAOCNVHKQNHT-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-7-(3,3-dimethoxy-4-methylpyrrolidin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)C(OC)(OC)CN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1=CC=C(F)C=C1F VWOAOCNVHKQNHT-UHFFFAOYSA-N 0.000 claims 1
VHRZROQNZOFSFP-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-7-(3,3-dimethoxypyrrolidin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(OC)(OC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1=CC=C(F)C=C1F VHRZROQNZOFSFP-UHFFFAOYSA-N 0.000 claims 1
OOCICPQCCRHPIT-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-7-(6,10-dioxa-2-azaspiro[4.5]decan-2-yl)-6-fluoro-2h-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(C(=O)O)=CC2=CC(F)=C(N3CC4(CC3)OCCCO4)N=C2N1C1=CC=C(F)C=C1F OOCICPQCCRHPIT-UHFFFAOYSA-N 0.000 claims 1
QLXGNYQFXHHYDX-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-7-(6,10-dioxa-2-azaspiro[4.5]decan-2-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(N3CC4(CC3)OCCCO4)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1F QLXGNYQFXHHYDX-UHFFFAOYSA-N 0.000 claims 1
JEJDLUNOAUGMLS-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-7-[3-[(dimethylamino)methyl]-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound O1C(CN(C)C)COC11CN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C=2C(=CC(F)=CC=2)F)F)CC1 JEJDLUNOAUGMLS-UHFFFAOYSA-N 0.000 claims 1
QPGKXWFOQBGBGN-UHFFFAOYSA-N 1-cyclopropyl-7-(3,3-dimethoxy-4-methylpyrrolidin-1-yl)-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)C(OC)(OC)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F QPGKXWFOQBGBGN-UHFFFAOYSA-N 0.000 claims 1
GTZGLFDWVMCOII-UHFFFAOYSA-N 1-cyclopropyl-7-(6,10-dioxa-2-azaspiro[4.5]decan-2-yl)-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CC4(CC3)OCCCO4)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 GTZGLFDWVMCOII-UHFFFAOYSA-N 0.000 claims 1
VOFFQZCUWAJBLH-UHFFFAOYSA-N 7-(9-amino-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.NC1CN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)CC11OCCO1 VOFFQZCUWAJBLH-UHFFFAOYSA-N 0.000 claims 1
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 26
125000005843 halogen group Chemical group 0.000 abstract description 15
230000000844 anti-bacterial effect Effects 0.000 abstract description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 270
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 175
229910001868 water Inorganic materials 0.000 description 111
239000002904 solvent Substances 0.000 description 109
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 107
239000000243 solution Substances 0.000 description 94
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 87
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 84
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
238000005481 NMR spectroscopy Methods 0.000 description 76
-1 naphthyridine carboxylic acids Chemical class 0.000 description 69
238000006243 chemical reaction Methods 0.000 description 66
239000000047 product Substances 0.000 description 66
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 56
239000000203 mixture Substances 0.000 description 55
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 49
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 48
238000001704 evaporation Methods 0.000 description 43
230000008020 evaporation Effects 0.000 description 43
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 41
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 39
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 38
238000004458 analytical method Methods 0.000 description 35
239000002253 acid Substances 0.000 description 34
235000019441 ethanol Nutrition 0.000 description 32
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
125000006239 protecting group Chemical group 0.000 description 30
239000000741 silica gel Substances 0.000 description 30
229910002027 silica gel Inorganic materials 0.000 description 30
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 28
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
238000004440 column chromatography Methods 0.000 description 24
239000007787 solid Substances 0.000 description 24
239000012043 crude product Substances 0.000 description 23
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
125000003277 amino group Chemical group 0.000 description 20
238000003756 stirring Methods 0.000 description 20
238000001914 filtration Methods 0.000 description 19
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 18
150000001413 amino acids Chemical class 0.000 description 16
239000003054 catalyst Substances 0.000 description 16
239000000463 material Substances 0.000 description 16
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
238000001035 drying Methods 0.000 description 15
YRIFAJOXAYPQEN-UHFFFAOYSA-N ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-2h-1,8-naphthyridine-3-carboxylate Chemical compound C1C(C(=O)OCC)=CC2=CC(F)=C(Cl)N=C2N1C1=CC=C(F)C=C1F YRIFAJOXAYPQEN-UHFFFAOYSA-N 0.000 description 15
238000010438 heat treatment Methods 0.000 description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
238000002360 preparation method Methods 0.000 description 15
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
229940024606 amino acid Drugs 0.000 description 14
235000001014 amino acid Nutrition 0.000 description 14
229940079593 drug Drugs 0.000 description 14
239000003814 drug Substances 0.000 description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
125000006519 CCH3 Chemical group 0.000 description 13
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 13
235000017557 sodium bicarbonate Nutrition 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
241000191967 Staphylococcus aureus Species 0.000 description 11
229960000583 acetic acid Drugs 0.000 description 11
238000012360 testing method Methods 0.000 description 11
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
238000010992 reflux Methods 0.000 description 9
239000003153 chemical reaction reagent Substances 0.000 description 8
UCHJWSNOVHXTKU-UHFFFAOYSA-N ethyl 1-(2,4-difluorophenyl)-6,7-difluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=CC(F)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1=CC=C(F)C=C1F UCHJWSNOVHXTKU-UHFFFAOYSA-N 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 8
LTFKBIKLTHRUMR-UHFFFAOYSA-N 1,4-dioxa-7-azaspiro[4.4]nonan-9-amine Chemical compound NC1CNCC11OCCO1 LTFKBIKLTHRUMR-UHFFFAOYSA-N 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
229910000069 nitrogen hydride Inorganic materials 0.000 description 7
150000003413 spiro compounds Chemical class 0.000 description 7
239000000725 suspension Substances 0.000 description 7
JKGCAQYNUWOSSC-UHFFFAOYSA-N 6,10-dioxa-2-azaspiro[4.5]decane Chemical compound C1NCCC21OCCCO2 JKGCAQYNUWOSSC-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
241000589517 Pseudomonas aeruginosa Species 0.000 description 6
230000000694 effects Effects 0.000 description 6
125000004494 ethyl ester group Chemical group 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
239000000546 pharmaceutical excipient Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
238000011282 treatment Methods 0.000 description 6
241000588724 Escherichia coli Species 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
238000010790 dilution Methods 0.000 description 5
239000012895 dilution Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 5
208000015181 infectious disease Diseases 0.000 description 5
239000007788 liquid Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
YYRDURJDYWJGNC-UHFFFAOYSA-N (3,3-dimethoxypyrrolidin-2-yl)methanamine Chemical compound COC1(OC)CCNC1CN YYRDURJDYWJGNC-UHFFFAOYSA-N 0.000 description 4
229920001817 Agar Polymers 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
239000008272 agar Substances 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
IWRWUVCTKQAKDY-UHFFFAOYSA-N benzyl carbamate;pyrrolidin-3-one Chemical compound O=C1CCNC1.NC(=O)OCC1=CC=CC=C1 IWRWUVCTKQAKDY-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
239000003937 drug carrier Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000011521 glass Substances 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000012535 impurity Substances 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
239000008101 lactose Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
239000006187 pill Substances 0.000 description 4
229920001223 polyethylene glycol Polymers 0.000 description 4
108090000765 processed proteins & peptides Proteins 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
ZQGLEEFGEZLSAJ-UHFFFAOYSA-N 1,5-dioxa-9-azaspiro[5.5]undecane Chemical compound O1CCCOC11CCNCC1 ZQGLEEFGEZLSAJ-UHFFFAOYSA-N 0.000 description 3
BNYMEXVJUDGTJS-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-6,7-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(F)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1=CC=C(F)C=C1F BNYMEXVJUDGTJS-UHFFFAOYSA-N 0.000 description 3
IVKWISFZOAXSBT-UHFFFAOYSA-N 3,3-dimethoxy-4-methylpyrrolidine Chemical compound COC1(OC)CNCC1C IVKWISFZOAXSBT-UHFFFAOYSA-N 0.000 description 3
SIBFQOUHOCRXDL-UHFFFAOYSA-N 3-bromopropane-1,2-diol Chemical compound OCC(O)CBr SIBFQOUHOCRXDL-UHFFFAOYSA-N 0.000 description 3
BVVQASQTFWDLIU-UHFFFAOYSA-N 3-methyl-1,4-dioxa-7-azaspiro[4.4]nonane Chemical compound O1C(C)COC11CNCC1 BVVQASQTFWDLIU-UHFFFAOYSA-N 0.000 description 3
LDTOWPODZAMRKS-UHFFFAOYSA-N 4-(fluoromethyl)-6,10-dioxa-2-azaspiro[4.5]decane Chemical compound FCC1CNCC11OCCCO1 LDTOWPODZAMRKS-UHFFFAOYSA-N 0.000 description 3
ORGJLLKIMQNILF-UHFFFAOYSA-N 4-aminopyrrolidin-3-ol;benzyl carbamate Chemical compound NC1CNCC1O.NC(=O)OCC1=CC=CC=C1 ORGJLLKIMQNILF-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
231100000111 LD50 Toxicity 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
241000194017 Streptococcus Species 0.000 description 3
241000193996 Streptococcus pyogenes Species 0.000 description 3
239000003957 anion exchange resin Substances 0.000 description 3
239000003242 anti bacterial agent Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
230000008901 benefit Effects 0.000 description 3
PHNUBHADQATFMI-UHFFFAOYSA-N benzyl carbamate;3-(bromomethyl)-1,4-dioxa-8-azaspiro[4.5]decane Chemical compound NC(=O)OCC1=CC=CC=C1.O1C(CBr)COC11CCNCC1 PHNUBHADQATFMI-UHFFFAOYSA-N 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000000576 coating method Methods 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
IOPJCFSAGSLBQZ-UHFFFAOYSA-N ethyl 7-chloro-1-cyclopropyl-6-fluoro-2h-1,8-naphthyridine-3-carboxylate Chemical compound C1C(C(=O)OCC)=CC2=CC(F)=C(Cl)N=C2N1C1CC1 IOPJCFSAGSLBQZ-UHFFFAOYSA-N 0.000 description 3
239000000499 gel Substances 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
239000003701 inert diluent Substances 0.000 description 3
244000005700 microbiome Species 0.000 description 3
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
229960004063 propylene glycol Drugs 0.000 description 3
235000013772 propylene glycol Nutrition 0.000 description 3
150000003248 quinolines Chemical class 0.000 description 3
150000007660 quinolones Chemical class 0.000 description 3
239000011347 resin Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007909 solid dosage form Substances 0.000 description 3
239000007921 spray Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide-pyridine complex Substances O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
238000005406 washing Methods 0.000 description 3
239000001993 wax Substances 0.000 description 3
239000000080 wetting agent Substances 0.000 description 3
DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
MOEUBXOZXDIHFP-VCAIXKDPSA-N (2S,3S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-N-(1,4-dioxa-8-azaspiro[4.5]decan-3-ylmethyl)-3-methylpentanamide Chemical compound O1C(CNC(=O)[C@@H](NC(=O)[C@@H](N)CC(C)C)[C@@H](C)CC)COC11CCNCC1 MOEUBXOZXDIHFP-VCAIXKDPSA-N 0.000 description 2
BVAUMRCGVHUWOZ-ZETCQYMHSA-N (2s)-2-(cyclohexylazaniumyl)propanoate Chemical compound OC(=O)[C@H](C)NC1CCCCC1 BVAUMRCGVHUWOZ-ZETCQYMHSA-N 0.000 description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
NDYKYDJBRAWUEW-UHFFFAOYSA-N 1,4-dioxa-7-azaspiro[4.4]nonan-6-ylmethanamine Chemical compound NCC1NCCC11OCCO1 NDYKYDJBRAWUEW-UHFFFAOYSA-N 0.000 description 2
AINPGIUJEUEYLY-UHFFFAOYSA-N 1,4-dioxa-7-azaspiro[4.4]nonan-9-ylmethanamine Chemical compound NCC1CNCC11OCCO1 AINPGIUJEUEYLY-UHFFFAOYSA-N 0.000 description 2
BXKCELAVFSHSEU-UHFFFAOYSA-N 1,5-dioxa-9-azaspiro[5.5]undecan-11-amine Chemical compound NC1CNCCC11OCCCO1 BXKCELAVFSHSEU-UHFFFAOYSA-N 0.000 description 2
LIRQNYNGEGGCAY-UHFFFAOYSA-N 1,5-dioxa-9-azaspiro[5.5]undecan-3-ylmethanamine Chemical compound O1CC(CN)COC11CCNCC1 LIRQNYNGEGGCAY-UHFFFAOYSA-N 0.000 description 2
CWLUFVAFWWNXJZ-UHFFFAOYSA-N 1-hydroxypyrrolidine Chemical compound ON1CCCC1 CWLUFVAFWWNXJZ-UHFFFAOYSA-N 0.000 description 2
SVJYALIJZNNUFA-UHFFFAOYSA-N 11-methyl-1,5-dioxa-8-azaspiro[5.5]undecane Chemical compound CC1CCNCC11OCCCO1 SVJYALIJZNNUFA-UHFFFAOYSA-N 0.000 description 2
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 2
NGUZLZRQOZXVSQ-UHFFFAOYSA-N 3,3-dimethoxypyrrolidine Chemical compound COC1(OC)CCNC1 NGUZLZRQOZXVSQ-UHFFFAOYSA-N 0.000 description 2
OWEGEOVGBFXXTG-UHFFFAOYSA-N 3,6-dimethyl-1,4-dioxa-8-azaspiro[4.5]decane Chemical compound O1C(C)COC11C(C)CNCC1 OWEGEOVGBFXXTG-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
ADYCVJYQIRAOBD-UHFFFAOYSA-N 4-aminopyrrolidin-3-one Chemical compound NC1CNCC1=O ADYCVJYQIRAOBD-UHFFFAOYSA-N 0.000 description 2
YITVBLRFOBGJHT-UHFFFAOYSA-N 6,10-dioxa-2-azaspiro[4.5]decan-4-ylmethanamine Chemical compound NCC1CNCC11OCCCO1 YITVBLRFOBGJHT-UHFFFAOYSA-N 0.000 description 2
WGLVMVGZDXASBH-UHFFFAOYSA-N 8-chloro-6,10-dioxa-2-azaspiro[4.5]decane Chemical compound O1CC(Cl)COC11CNCC1 WGLVMVGZDXASBH-UHFFFAOYSA-N 0.000 description 2
CQWVIMUERMGRFT-UHFFFAOYSA-N 9-chloro-1,4-dioxa-7-azaspiro[4.4]nonane Chemical compound ClC1CNCC11OCCO1 CQWVIMUERMGRFT-UHFFFAOYSA-N 0.000 description 2
BGNVMMQGZQSGEL-UHFFFAOYSA-N 9-ethyl-6,10-dioxa-2-azaspiro[4.5]decane Chemical compound O1C(CC)CCOC11CNCC1 BGNVMMQGZQSGEL-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
241000589291 Acinetobacter Species 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
241000416162 Astragalus gummifer Species 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 2
ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
241000192041 Micrococcus Species 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229920001615 Tragacanth Polymers 0.000 description 2
KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 2
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
DDSZWBCJXDRQDU-UHFFFAOYSA-N [N].C1CCNCC1 Chemical group [N].C1CCNCC1 DDSZWBCJXDRQDU-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
235000010443 alginic acid Nutrition 0.000 description 2
229920000615 alginic acid Polymers 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
125000006242 amine protecting group Chemical group 0.000 description 2
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 2
238000003556 assay Methods 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
ONHLSUCKXQQKEU-UHFFFAOYSA-N benzyl carbamate;2,5-dihydro-1h-pyrrole Chemical compound C1NCC=C1.NC(=O)OCC1=CC=CC=C1 ONHLSUCKXQQKEU-UHFFFAOYSA-N 0.000 description 2
INJOQIZIOOUEQI-UHFFFAOYSA-N benzyl carbamate;3-(bromomethyl)-1,4-dioxa-7-azaspiro[4.4]nonane Chemical compound NC(=O)OCC1=CC=CC=C1.O1C(CBr)COC11CNCC1 INJOQIZIOOUEQI-UHFFFAOYSA-N 0.000 description 2
ZGSJBUIGFXESMW-UHFFFAOYSA-N benzyl carbamate;6-oxa-3-azabicyclo[3.1.0]hexane Chemical compound C1NCC2OC12.NC(=O)OCC1=CC=CC=C1 ZGSJBUIGFXESMW-UHFFFAOYSA-N 0.000 description 2
LDTADBQHBIWKOR-UHFFFAOYSA-N benzyl carbamate;piperidin-4-one Chemical compound O=C1CCNCC1.NC(=O)OCC1=CC=CC=C1 LDTADBQHBIWKOR-UHFFFAOYSA-N 0.000 description 2
WWKVGYJFOSCSEB-UHFFFAOYSA-N benzyl carbamate;pyrrolidin-3-ol Chemical compound OC1CCNC1.NC(=O)OCC1=CC=CC=C1 WWKVGYJFOSCSEB-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
229920002988 biodegradable polymer Polymers 0.000 description 2
239000004621 biodegradable polymer Substances 0.000 description 2
210000004556 brain Anatomy 0.000 description 2
239000006172 buffering agent Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
235000010980 cellulose Nutrition 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
229940110456 cocoa butter Drugs 0.000 description 2
235000019868 cocoa butter Nutrition 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000006071 cream Substances 0.000 description 2
230000001186 cumulative effect Effects 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
TXFOLHZMICYNRM-UHFFFAOYSA-N dichlorophosphoryloxybenzene Chemical compound ClP(Cl)(=O)OC1=CC=CC=C1 TXFOLHZMICYNRM-UHFFFAOYSA-N 0.000 description 2
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 2
229940043264 dodecyl sulfate Drugs 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000002702 enteric coating Substances 0.000 description 2
238000009505 enteric coating Methods 0.000 description 2
FGICMAMEHORFNK-UHFFFAOYSA-N ethyl 1-cyclopropyl-6,7,8-trifluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=C(F)C(F)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 FGICMAMEHORFNK-UHFFFAOYSA-N 0.000 description 2
QYGNYHKBMNUIJN-UHFFFAOYSA-N ethyl 1-cyclopropyl-6,7-difluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=CC(F)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 QYGNYHKBMNUIJN-UHFFFAOYSA-N 0.000 description 2
MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
239000008187 granular material Substances 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
238000011534 incubation Methods 0.000 description 2
238000001802 infusion Methods 0.000 description 2
238000005342 ion exchange Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
239000004530 micro-emulsion Substances 0.000 description 2
230000000813 microbial effect Effects 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
LXSXFHNTPZVYNR-UHFFFAOYSA-N n-[2-morpholin-4-yl-5-(trifluoromethyl)phenyl]-5-(3-nitrophenyl)furan-2-carboxamide Chemical compound [O-][N+](=O)C1=CC=CC(C=2OC(=CC=2)C(=O)NC=2C(=CC=C(C=2)C(F)(F)F)N2CCOCC2)=C1 LXSXFHNTPZVYNR-UHFFFAOYSA-N 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
239000000346 nonvolatile oil Substances 0.000 description 2
239000002674 ointment Substances 0.000 description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
NVKWWNNJFKZNJO-RXMQYKEDSA-N oxygen-fluorine acid Chemical compound N1([C@H](C)CO2)C=C(C(O)=O)C(=O)C3=C1C2=C(F)C(F)=C3 NVKWWNNJFKZNJO-RXMQYKEDSA-N 0.000 description 2
239000006072 paste Substances 0.000 description 2
238000010647 peptide synthesis reaction Methods 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000002304 perfume Substances 0.000 description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
229920000166 polytrimethylene carbonate Polymers 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
102000004196 processed proteins & peptides Human genes 0.000 description 2
238000011321 prophylaxis Methods 0.000 description 2
238000010791 quenching Methods 0.000 description 2
125000006413 ring segment Chemical group 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000008247 solid mixture Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
238000000967 suction filtration Methods 0.000 description 2
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
239000000196 tragacanth Substances 0.000 description 2
235000010487 tragacanth Nutrition 0.000 description 2
229940116362 tragacanth Drugs 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
229940066528 trichloroacetate Drugs 0.000 description 2
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
239000004474 valine Substances 0.000 description 2
LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
MLNMNKOLCHBUTC-DTIOYNMSSA-N (2s)-2-amino-n-(1,5-dioxa-8-azaspiro[5.5]undecan-10-yl)-3-methylbutanamide Chemical compound C1C(NC(=O)[C@@H](N)C(C)C)CNCC21OCCCO2 MLNMNKOLCHBUTC-DTIOYNMSSA-N 0.000 description 1
YKBOLMHAQUUWNK-LBPRGKRZSA-N (2s)-2-amino-n-(1,5-dioxa-9-azaspiro[5.5]undecan-3-yl)-4-methylpentanamide Chemical compound O1CC(NC(=O)[C@@H](N)CC(C)C)COC11CCNCC1 YKBOLMHAQUUWNK-LBPRGKRZSA-N 0.000 description 1
GFEKPHPLTPUCQF-BEEDKBRMSA-N (2s)-2-amino-n-[(2s)-1-(1,4-dioxa-7-azaspiro[4.4]nonan-9-ylmethylamino)-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]-3-methylbutanamide Chemical compound C([C@H](NC(=O)[C@@H](N)C(C)C)C(=O)NCC1C2(OCCO2)CNC1)C1=CC=C(O)C=C1 GFEKPHPLTPUCQF-BEEDKBRMSA-N 0.000 description 1
GSGOSSYBBHBFJS-VPCQXRJPSA-N (2s)-2-anilino-1-(3-ethyl-1,4-dioxa-7-azaspiro[4.4]nonan-8-yl)propan-1-one Chemical compound O1C(CC)COC11CC(C(=O)[C@H](C)NC=2C=CC=CC=2)NC1 GSGOSSYBBHBFJS-VPCQXRJPSA-N 0.000 description 1
WAMWSIDTKSNDCU-ZETCQYMHSA-N (2s)-2-azaniumyl-2-cyclohexylacetate Chemical compound OC(=O)[C@@H](N)C1CCCCC1 WAMWSIDTKSNDCU-ZETCQYMHSA-N 0.000 description 1
KVRUUGBEYKMGMJ-UHFFFAOYSA-N (3-ethyl-1,4-dioxa-7-azaspiro[4.4]nonan-8-yl)methanamine Chemical compound O1C(CC)COC11CC(CN)NC1 KVRUUGBEYKMGMJ-UHFFFAOYSA-N 0.000 description 1
LZGGUFLRKIMBDQ-YHYXMXQVSA-N (3z)-3-(1,3-benzodioxol-5-ylmethylidene)-2-oxopyrrolidine-1-carbaldehyde Chemical compound O=C1N(C=O)CC\C1=C\C1=CC=C(OCO2)C2=C1 LZGGUFLRKIMBDQ-YHYXMXQVSA-N 0.000 description 1
BWLZYVXJHWMPSX-UHFFFAOYSA-N (6-methyl-1,4-dioxa-8-azaspiro[4.5]decan-3-yl)methanamine Chemical compound CC1CNCCC11OC(CN)CO1 BWLZYVXJHWMPSX-UHFFFAOYSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
150000000185 1,3-diols Chemical class 0.000 description 1
GXKNEZHSYCYFDK-UHFFFAOYSA-N 1,4-dioxa-7-azaspiro[4.4]nonan-3-ylmethanamine Chemical compound O1C(CN)COC11CNCC1 GXKNEZHSYCYFDK-UHFFFAOYSA-N 0.000 description 1
ZCFOAMGPJARTCT-UHFFFAOYSA-N 1,4-dioxa-7-azaspiro[4.4]nonan-3-ylmethanol Chemical compound O1C(CO)COC11CNCC1 ZCFOAMGPJARTCT-UHFFFAOYSA-N 0.000 description 1
LPUQKQFLKKPWKD-UHFFFAOYSA-N 1,4-dioxa-8-azaspiro[4.5]decan-6-amine Chemical compound NC1CNCCC11OCCO1 LPUQKQFLKKPWKD-UHFFFAOYSA-N 0.000 description 1
GZGPRZYZKBQPBQ-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decane Chemical compound O1CCOC11CCCCC1 GZGPRZYZKBQPBQ-UHFFFAOYSA-N 0.000 description 1
XGHGIRGCABFNSG-UHFFFAOYSA-N 1,5-dioxa-8-azaspiro[5.5]undecan-10-amine Chemical compound C1C(N)CNCC21OCCCO2 XGHGIRGCABFNSG-UHFFFAOYSA-N 0.000 description 1
XNZDWJGSDKIZAJ-UHFFFAOYSA-N 1,5-dioxa-8-azaspiro[5.5]undecan-11-ylmethanamine Chemical compound NCC1CCNCC11OCCCO1 XNZDWJGSDKIZAJ-UHFFFAOYSA-N 0.000 description 1
OJOIYTZARWGDCW-UHFFFAOYSA-N 1-(1,4-dioxa-7-azaspiro[4.4]nonan-3-yl)-n,n-dimethylmethanamine Chemical compound O1C(CN(C)C)COC11CNCC1 OJOIYTZARWGDCW-UHFFFAOYSA-N 0.000 description 1
PNDHRWGPBCFCDS-UHFFFAOYSA-N 1-(1,4-dioxa-8-azaspiro[4.5]decan-3-yl)-n-methylmethanamine Chemical compound O1C(CNC)COC11CCNCC1 PNDHRWGPBCFCDS-UHFFFAOYSA-N 0.000 description 1
PHXIZEUIQYENPM-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-6-fluoro-7-[3-(methylaminomethyl)-1,4-dioxa-8-azaspiro[4.5]decan-8-yl]-2h-1,8-naphthyridine-3-carboxylic acid Chemical compound O1C(CNC)COC11CCN(C=2C(=CC=3C=C(CN(C=3N=2)C=2C(=CC(F)=CC=2)F)C(O)=O)F)CC1 PHXIZEUIQYENPM-UHFFFAOYSA-N 0.000 description 1
QGRBPNSCUZLDDE-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-7-(3,3-dimethoxypyrrolidin-1-yl)-6-fluoro-2h-1,8-naphthyridine-3-carboxylic acid Chemical compound C1C(OC)(OC)CCN1C(C(=C1)F)=NC2=C1C=C(C(O)=O)CN2C1=CC=C(F)C=C1F QGRBPNSCUZLDDE-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
NTDFIGIMQABQLD-UHFFFAOYSA-N 1-benzyl-4-methylpyrrolidin-3-ol Chemical compound C1C(O)C(C)CN1CC1=CC=CC=C1 NTDFIGIMQABQLD-UHFFFAOYSA-N 0.000 description 1
NSXHIJHCRCPVAS-UHFFFAOYSA-N 1-benzyl-4-methylpyrrolidin-3-one Chemical compound C1C(=O)C(C)CN1CC1=CC=CC=C1 NSXHIJHCRCPVAS-UHFFFAOYSA-N 0.000 description 1
UMHDYACNSPHNHV-UHFFFAOYSA-N 1-cyclopropyl-7-(1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(N3CC4(CC3)OCCO4)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 UMHDYACNSPHNHV-UHFFFAOYSA-N 0.000 description 1
NECINDRZUGAMDC-UHFFFAOYSA-N 1-hydroxypyrrolidin-2-amine Chemical compound NC1CCCN1O NECINDRZUGAMDC-UHFFFAOYSA-N 0.000 description 1
UZZAJLGYKHFJSU-UHFFFAOYSA-N 10-methyl-1,5-dioxa-8-azaspiro[5.5]undecane Chemical compound C1C(C)CNCC21OCCCO2 UZZAJLGYKHFJSU-UHFFFAOYSA-N 0.000 description 1
PUJNGYWQPYCGLL-UHFFFAOYSA-N 11-methyl-1,5-dioxa-9-azaspiro[5.5]undecane Chemical compound CC1CNCCC11OCCCO1 PUJNGYWQPYCGLL-UHFFFAOYSA-N 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
NQFPSOQXUDGJNV-ZQOBQRRWSA-N 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1.OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO NQFPSOQXUDGJNV-ZQOBQRRWSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
SNDPXSYFESPGGJ-UHFFFAOYSA-N 2-aminopentanoic acid Chemical compound CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 description 1
229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
XOQQVKDBGLYPGH-UHFFFAOYSA-N 2-oxo-1h-quinoline-3-carboxylic acid Chemical compound C1=CC=C2NC(=O)C(C(=O)O)=CC2=C1 XOQQVKDBGLYPGH-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
YXAAECJWBAEYDO-UHFFFAOYSA-N 3,3-dimethoxy-1-methylpyrrolidine Chemical compound COC1(OC)CCN(C)C1 YXAAECJWBAEYDO-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
NUVGKWXXLCDUAW-UHFFFAOYSA-N 3-ethyl-1,4-dioxa-8-azaspiro[4.5]decane Chemical compound O1C(CC)COC11CCNCC1 NUVGKWXXLCDUAW-UHFFFAOYSA-N 0.000 description 1
XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 1
JVQIKJMSUIMUDI-UHFFFAOYSA-N 3-pyrroline Chemical compound C1NCC=C1 JVQIKJMSUIMUDI-UHFFFAOYSA-N 0.000 description 1
BNTXFAWWPWXCAY-UHFFFAOYSA-N 4-(aminomethyl)pyrrolidin-3-ol;benzyl carbamate Chemical compound NCC1CNCC1O.NC(=O)OCC1=CC=CC=C1 BNTXFAWWPWXCAY-UHFFFAOYSA-N 0.000 description 1
CQDQACBVUQQHCK-UHFFFAOYSA-N 4-(aminomethyl)pyrrolidin-3-one Chemical compound NCC1CNCC1=O CQDQACBVUQQHCK-UHFFFAOYSA-N 0.000 description 1
ZCZJKVCIYONNJR-UHFFFAOYSA-N 4-aminopyrrolidin-3-ol Chemical compound NC1CNCC1O ZCZJKVCIYONNJR-UHFFFAOYSA-N 0.000 description 1
WCRIJBBHJYYUQN-UHFFFAOYSA-N 4-ethyl-11-methyl-1,5-dioxa-9-azaspiro[5.5]undecane Chemical compound O1C(CC)CCOC11C(C)CNCC1 WCRIJBBHJYYUQN-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
RVLMENDAPVFJBU-UHFFFAOYSA-N 4-methyl-6,10-dioxa-2-azaspiro[4.5]decane Chemical compound CC1CNCC11OCCCO1 RVLMENDAPVFJBU-UHFFFAOYSA-N 0.000 description 1
PTYCBNUHKXMSSA-UHFFFAOYSA-N 4-methylpyrrolidin-3-ol Chemical compound CC1CNCC1O PTYCBNUHKXMSSA-UHFFFAOYSA-N 0.000 description 1
DQLMVUOPWNWIHZ-UHFFFAOYSA-N 6,10-dioxa-2-azaspiro[4.5]decan-4-amine Chemical compound NC1CNCC11OCCCO1 DQLMVUOPWNWIHZ-UHFFFAOYSA-N 0.000 description 1
JVDBBJBWIXMAOV-UHFFFAOYSA-N 6,10-dioxa-2-azaspiro[4.5]decan-9-ylmethanamine Chemical compound O1C(CN)CCOC11CNCC1 JVDBBJBWIXMAOV-UHFFFAOYSA-N 0.000 description 1
LSBRKLPBANBCQD-UHFFFAOYSA-N 6-fluoro-1,4-dioxa-7-azaspiro[4.4]nonane Chemical compound FC1NCCC11OCCO1 LSBRKLPBANBCQD-UHFFFAOYSA-N 0.000 description 1
RZIXFSKHSPZGOU-UHFFFAOYSA-N 6-methyl-1,4-dioxa-8-azaspiro[4.5]decane Chemical compound CC1CNCCC11OCCO1 RZIXFSKHSPZGOU-UHFFFAOYSA-N 0.000 description 1
FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
IWTHMMNXADMKCZ-UHFFFAOYSA-N 7-[3-(aminomethyl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl]-1-cyclopropyl-6-fluoro-2h-1,8-naphthyridine-3-carboxylic acid;dihydrochloride Chemical compound Cl.Cl.O1C(CN)COC11CN(C=2C(=CC=3C=C(CN(C=3N=2)C2CC2)C(O)=O)F)CC1 IWTHMMNXADMKCZ-UHFFFAOYSA-N 0.000 description 1
IIKUJCXNRVCFBW-UHFFFAOYSA-N 7-[9-(aminomethyl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl]-1-(2,4-difluorophenyl)-6-fluoro-2h-1,8-naphthyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.NCC1CN(C=2C(=CC=3C=C(CN(C=3N=2)C=2C(=CC(F)=CC=2)F)C(O)=O)F)CC11OCCO1 IIKUJCXNRVCFBW-UHFFFAOYSA-N 0.000 description 1
CQYXZRGEPNBLAS-UHFFFAOYSA-N 7-[9-(aminomethyl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl]-1-cyclopropyl-6-fluoro-2h-1,8-naphthyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.NCC1CN(C=2C(=CC=3C=C(CN(C=3N=2)C2CC2)C(O)=O)F)CC11OCCO1 CQYXZRGEPNBLAS-UHFFFAOYSA-N 0.000 description 1
ISPVACVJFUIDPD-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 ISPVACVJFUIDPD-UHFFFAOYSA-N 0.000 description 1
ZRJFMEPDICYKGY-UHFFFAOYSA-N 9-(fluoromethyl)-1,4-dioxa-7-azaspiro[4.4]nonane Chemical compound FCC1CNCC11OCCO1 ZRJFMEPDICYKGY-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
BQHUSLNUTJWRAM-UHFFFAOYSA-N 9-methyl-6,10-dioxa-2-azaspiro[4.5]decan-8-amine Chemical compound O1CC(N)C(C)OC11CNCC1 BQHUSLNUTJWRAM-UHFFFAOYSA-N 0.000 description 1
229910000497 Amalgam Inorganic materials 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
244000186140 Asperula odorata Species 0.000 description 1
241000606125 Bacteroides Species 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
241000589562 Brucella Species 0.000 description 1
241000589513 Burkholderia cepacia Species 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
KZHFQNYYPYEHLG-UHFFFAOYSA-N C(N)(OCC1=CC=CC=C1)=O.CC1OC2(OC1)CNCC2 Chemical compound C(N)(OCC1=CC=CC=C1)=O.CC1OC2(OC1)CNCC2 KZHFQNYYPYEHLG-UHFFFAOYSA-N 0.000 description 1
IHYJETNYNFQAMX-UHFFFAOYSA-N C(N)(OCC1=CC=CC=C1)=O.N(=[N+]=[N-])C1C(CNC1)O Chemical compound C(N)(OCC1=CC=CC=C1)=O.N(=[N+]=[N-])C1C(CNC1)O IHYJETNYNFQAMX-UHFFFAOYSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
241000589876 Campylobacter Species 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
241000588923 Citrobacter Species 0.000 description 1
241000193403 Clostridium Species 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
241000588914 Enterobacter Species 0.000 description 1
241000305071 Enterobacterales Species 0.000 description 1
241000194033 Enterococcus Species 0.000 description 1
241000194031 Enterococcus faecium Species 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
241000588722 Escherichia Species 0.000 description 1
239000001856 Ethyl cellulose Substances 0.000 description 1
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
235000008526 Galium odoratum Nutrition 0.000 description 1
102000009338 Gastric Mucins Human genes 0.000 description 1
108010009066 Gastric Mucins Proteins 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Polymers OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
241000606790 Haemophilus Species 0.000 description 1
239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
101001100204 Homo sapiens Ras-related protein Rab-40A-like Proteins 0.000 description 1
239000003810 Jones reagent Substances 0.000 description 1
241000588748 Klebsiella Species 0.000 description 1
241000588915 Klebsiella aerogenes Species 0.000 description 1
241000588747 Klebsiella pneumoniae Species 0.000 description 1
241000196833 Kocuria rhizophila DC2201 Species 0.000 description 1
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
241000186660 Lactobacillus Species 0.000 description 1
241000589248 Legionella Species 0.000 description 1
208000007764 Legionnaires' Disease Diseases 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
PQMWYJDJHJQZDE-UHFFFAOYSA-M Methantheline bromide Chemical compound [Br-].C1=CC=C2C(C(=O)OCC[N+](C)(CC)CC)C3=CC=CC=C3OC2=C1 PQMWYJDJHJQZDE-UHFFFAOYSA-M 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
241001153358 Micrococcus luteus NCTC 2665 Species 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
ISOBPXBUVAPKAY-UHFFFAOYSA-N NC(=O)OCC1=CC=CC=C1.O1C(CN=[N+]=[N-])COC11CNCC1 Chemical compound NC(=O)OCC1=CC=CC=C1.O1C(CN=[N+]=[N-])COC11CNCC1 ISOBPXBUVAPKAY-UHFFFAOYSA-N 0.000 description 1
241001494457 Nemia Species 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
241000206591 Peptococcus Species 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
235000014676 Phragmites communis Nutrition 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
229920002732 Polyanhydride Polymers 0.000 description 1
229920000954 Polyglycolide Polymers 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
241000588768 Providencia Species 0.000 description 1
241000588778 Providencia stuartii Species 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
102100038416 Ras-related protein Rab-40A-like Human genes 0.000 description 1
235000019485 Safflower oil Nutrition 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
241000607720 Serratia Species 0.000 description 1
241000607768 Shigella Species 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
241000191940 Staphylococcus Species 0.000 description 1
241000191963 Staphylococcus epidermidis Species 0.000 description 1
241000194049 Streptococcus equinus Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
125000005076 adamantyloxycarbonyl group Chemical group C12(CC3CC(CC(C1)C3)C2)OC(=O)* 0.000 description 1
WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
238000002814 agar dilution Methods 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
229940072056 alginate Drugs 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000005210 alkyl ammonium group Chemical group 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
150000001371 alpha-amino acids Chemical class 0.000 description 1
235000008206 alpha-amino acids Nutrition 0.000 description 1
AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000006229 amino acid addition Effects 0.000 description 1
125000000539 amino acid group Chemical group 0.000 description 1
125000004103 aminoalkyl group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
238000013459 approach Methods 0.000 description 1
238000009360 aquaculture Methods 0.000 description 1
244000144974 aquaculture Species 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
229940072107 ascorbate Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229940009098 aspartate Drugs 0.000 description 1
IUKQLMGVFMDQDP-UHFFFAOYSA-N azane;piperidine Chemical compound N.C1CCNCC1 IUKQLMGVFMDQDP-UHFFFAOYSA-N 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
125000004069 aziridinyl group Chemical group 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
235000012216 bentonite Nutrition 0.000 description 1
150000001555 benzenes Chemical group 0.000 description 1
LSRYUMWMHYVXDN-UHFFFAOYSA-N benzyl carbamate;1,4-dioxa-8-azaspiro[4.5]decan-3-ylmethanamine Chemical compound NC(=O)OCC1=CC=CC=C1.O1C(CN)COC11CCNCC1 LSRYUMWMHYVXDN-UHFFFAOYSA-N 0.000 description 1
IWVRBUOYOBLWKQ-UHFFFAOYSA-N benzyl carbamate;1,5-dioxa-9-azaspiro[5.5]undecane Chemical compound O1CCCOC11CCNCC1.NC(=O)OCC1=CC=CC=C1 IWVRBUOYOBLWKQ-UHFFFAOYSA-N 0.000 description 1
JTFLSQVQLQYTGW-UHFFFAOYSA-N benzyl carbamate;3,3-dimethoxypyrrolidine Chemical compound COC1(OC)CCNC1.NC(=O)OCC1=CC=CC=C1 JTFLSQVQLQYTGW-UHFFFAOYSA-N 0.000 description 1
KUAVDFXITSYSDK-UHFFFAOYSA-N benzyl carbamate;4-hydroxypyrrolidine-3-carbonitrile Chemical compound OC1CNCC1C#N.NC(=O)OCC1=CC=CC=C1 KUAVDFXITSYSDK-UHFFFAOYSA-N 0.000 description 1
MKMZJSFMYFJGLS-UHFFFAOYSA-N benzyl carbamate;6,10-dioxa-2-azaspiro[4.5]decane Chemical compound C1NCCC21OCCCO2.NC(=O)OCC1=CC=CC=C1 MKMZJSFMYFJGLS-UHFFFAOYSA-N 0.000 description 1
CBHGSQHKLZHCDT-UHFFFAOYSA-N benzylcarbamic acid;piperidin-4-one Chemical compound O=C1CCNCC1.OC(=O)NCC1=CC=CC=C1 CBHGSQHKLZHCDT-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
XMIIGOLPHOKFCH-UHFFFAOYSA-N beta-phenylpropanoic acid Natural products OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000036760 body temperature Effects 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000000872 buffer Substances 0.000 description 1
FATUQANACHZLRT-KMRXSBRUSA-L calcium glucoheptonate Chemical compound [Ca+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C([O-])=O FATUQANACHZLRT-KMRXSBRUSA-L 0.000 description 1
235000012241 calcium silicate Nutrition 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
150000005827 chlorofluoro hydrocarbons Chemical class 0.000 description 1
229960001231 choline Drugs 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229940088516 cipro Drugs 0.000 description 1
229960003405 ciprofloxacin Drugs 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
230000001332 colony forming effect Effects 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
235000005687 corn oil Nutrition 0.000 description 1
239000002285 corn oil Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
230000034994 death Effects 0.000 description 1
231100000517 death Toxicity 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
125000005131 dialkylammonium group Chemical group 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000007865 diluting Methods 0.000 description 1
DKWOHBPRFZIUQL-UHFFFAOYSA-N dimethyl-methylidene-oxo-$l^{6}-sulfane Chemical compound C[S+](C)([CH2-])=O DKWOHBPRFZIUQL-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
238000009510 drug design Methods 0.000 description 1
239000003221 ear drop Substances 0.000 description 1
229940047652 ear drops Drugs 0.000 description 1
238000010828 elution Methods 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000003623 enhancer Substances 0.000 description 1
229940092559 enterobacter aerogenes Drugs 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
ZOEKKLFPDLSJFH-UHFFFAOYSA-N ethyl 1-(2,4-difluorophenyl)-7-(6,10-dioxa-2-azaspiro[4.5]decan-9-yl)-6-fluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=CC(C3OC4(CNCC4)OCC3)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1=CC=C(F)C=C1F ZOEKKLFPDLSJFH-UHFFFAOYSA-N 0.000 description 1
YEZWUOLOECOODA-UHFFFAOYSA-N ethyl 1-benzyl-4-methyl-3-oxopyrrolidine-2-carboxylate Chemical compound C1C(C)C(=O)C(C(=O)OCC)N1CC1=CC=CC=C1 YEZWUOLOECOODA-UHFFFAOYSA-N 0.000 description 1
MEKNJNYVMBSRQJ-UHFFFAOYSA-N ethyl 3,3,3-trifluoro-2-hydroxy-2-[3-methoxy-4-(naphthalen-2-ylcarbamoylamino)phenyl]propanoate Chemical compound COC1=CC(C(O)(C(=O)OCC)C(F)(F)F)=CC=C1NC(=O)NC1=CC=C(C=CC=C2)C2=C1 MEKNJNYVMBSRQJ-UHFFFAOYSA-N 0.000 description 1
CRLWGPSWMIFWRM-UHFFFAOYSA-N ethyl 3-(benzylamino)-2-methylpropanoate Chemical compound CCOC(=O)C(C)CNCC1=CC=CC=C1 CRLWGPSWMIFWRM-UHFFFAOYSA-N 0.000 description 1
MASHNFGGIMTCKZ-UHFFFAOYSA-N ethyl 6-fluoro-1,8-naphthyridine-3-carboxylate Chemical compound C(C)OC(=O)C=1C=NC2=NC=C(C=C2C1)F MASHNFGGIMTCKZ-UHFFFAOYSA-N 0.000 description 1
XCAAXKDRMWQITG-UHFFFAOYSA-N ethyl 7-chloro-6-fluoro-1-(4-fluorophenyl)-2h-1,8-naphthyridine-3-carboxylate Chemical compound C1C(C(=O)OCC)=CC2=CC(F)=C(Cl)N=C2N1C1=CC=C(F)C=C1 XCAAXKDRMWQITG-UHFFFAOYSA-N 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
230000029142 excretion Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000003885 eye ointment Substances 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
230000004907 flux Effects 0.000 description 1
229940050411 fumarate Drugs 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000007952 growth promoter Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000036541 health Effects 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical compound Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000007972 injectable composition Substances 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
229940102213 injectable suspension Drugs 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000007794 irritation Effects 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
229960000310 isoleucine Drugs 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
229940001447 lactate Drugs 0.000 description 1
229940039696 lactobacillus Drugs 0.000 description 1
229940099584 lactobionate Drugs 0.000 description 1
JYTUSYBCFIZPBE-AMTLMPIISA-N lactobionic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-N 0.000 description 1
229940070765 laurate Drugs 0.000 description 1
239000002502 liposome Substances 0.000 description 1
239000008297 liquid dosage form Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000006210 lotion Substances 0.000 description 1
229960003646 lysine Drugs 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
CXHHBNMLPJOKQD-UHFFFAOYSA-M methyl carbonate Chemical compound COC([O-])=O CXHHBNMLPJOKQD-UHFFFAOYSA-M 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
244000000010 microbial pathogen Species 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
YYTWEEOFRNSTKS-UHFFFAOYSA-N n,n'-dicyclohexylmethanediimine;1-hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1.C1CCCCC1N=C=NC1CCCCC1 YYTWEEOFRNSTKS-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
231100000344 non-irritating Toxicity 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000002905 orthoesters Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
244000052769 pathogen Species 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
ZAEQTGTVGUJEFV-UHFFFAOYSA-N phenylmethanesulfonate;pyridin-1-ium Chemical compound C1=CC=[NH+]C=C1.[O-]S(=O)(=O)CC1=CC=CC=C1 ZAEQTGTVGUJEFV-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
229950010765 pivalate Drugs 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
230000002265 prevention Effects 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
QGKLPGKXAVVPOJ-UHFFFAOYSA-N pyrrolidin-3-one Chemical compound O=C1CCNC1 QGKLPGKXAVVPOJ-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
235000005713 safflower oil Nutrition 0.000 description 1
239000003813 safflower oil Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
150000003334 secondary amides Chemical class 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000012289 standard assay Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229940114926 stearate Drugs 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
238000005556 structure-activity relationship Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
125000005208 trialkylammonium group Chemical group 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical class CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
235000014692 zinc oxide Nutrition 0.000 description 1