KR20090042971A - 항미생물 활성을 갖는 신규한 마크로라이드 및 케토라이드 - Google Patents

Info

Publication number

KR20090042971A

KR20090042971A KR1020097005432A KR20097005432A KR20090042971A KR 20090042971 A KR20090042971 A KR 20090042971A KR 1020097005432 A KR1020097005432 A KR 1020097005432A KR 20097005432 A KR20097005432 A KR 20097005432A KR 20090042971 A KR20090042971 A KR 20090042971A

Authority

KR

South Korea

Prior art keywords

formula

compound

phenyl

substituted

pyridin

Prior art date

2006-08-24

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Ceased

Links

• Espacenet
• Global Dossier
• Discuss

• 239000003120 macrolide antibiotic agent Substances 0.000 title claims abstract description 33
• 229940041033 macrolides Drugs 0.000 title abstract description 10
• 230000000845 anti-microbial effect Effects 0.000 title abstract description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 404
• 238000000034 method Methods 0.000 claims abstract description 83
• 208000015181 infectious disease Diseases 0.000 claims abstract description 49
• 230000000813 microbial effect Effects 0.000 claims abstract description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
• -1 triethylsilyl Chemical group 0.000 claims description 578
• 239000002904 solvent Substances 0.000 claims description 57
• 238000006243 chemical reaction Methods 0.000 claims description 43
• 125000001072 heteroaryl group Chemical group 0.000 claims description 39
• 229920006395 saturated elastomer Polymers 0.000 claims description 36
• 239000003153 chemical reaction reagent Substances 0.000 claims description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims description 33
• 239000001257 hydrogen Substances 0.000 claims description 32
• 239000003835 ketolide antibiotic agent Substances 0.000 claims description 30
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
• 150000003839 salts Chemical class 0.000 claims description 29
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 24
• 125000003118 aryl group Chemical group 0.000 claims description 22
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 21
• 241001465754 Metazoa Species 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 19
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 17
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
• 150000002431 hydrogen Chemical class 0.000 claims description 16
• 239000002585 base Substances 0.000 claims description 15
• 229910052736 halogen Inorganic materials 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 125000001424 substituent group Chemical group 0.000 claims description 15
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 13
• 239000012453 solvate Substances 0.000 claims description 12
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 11
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 9
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 8
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 238000010511 deprotection reaction Methods 0.000 claims description 8
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 8
• 229910052760 oxygen Inorganic materials 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 7
• 239000003054 catalyst Substances 0.000 claims description 7
• 229910052763 palladium Inorganic materials 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 6
• 239000003937 drug carrier Substances 0.000 claims description 6
• 125000005842 heteroatom Chemical group 0.000 claims description 6
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
• 125000002883 imidazolyl group Chemical group 0.000 claims description 6
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
• 125000002971 oxazolyl group Chemical group 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
• 125000001425 triazolyl group Chemical group 0.000 claims description 6
• 241000894006 Bacteria Species 0.000 claims description 5
• 229910004013 NO 2 Inorganic materials 0.000 claims description 5
• 239000000460 chlorine Substances 0.000 claims description 5
• 238000005859 coupling reaction Methods 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• 125000003107 substituted aryl group Chemical group 0.000 claims description 5
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 150000001735 carboxylic acids Chemical class 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 125000003106 haloaryl group Chemical group 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 229910052740 iodine Inorganic materials 0.000 claims description 4
• 238000004519 manufacturing process Methods 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 3
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• 230000029936 alkylation Effects 0.000 claims description 3
• 238000005804 alkylation reaction Methods 0.000 claims description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 239000003795 chemical substances by application Substances 0.000 claims description 3
• 239000011630 iodine Substances 0.000 claims description 3
• 239000012948 isocyanate Substances 0.000 claims description 3
• 150000002513 isocyanates Chemical class 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
• 241001148470 aerobic bacillus Species 0.000 claims description 2
• 229910052799 carbon Inorganic materials 0.000 claims description 2
• 241001148471 unidentified anaerobic bacterium Species 0.000 claims description 2
• 150000003018 phosphorus compounds Chemical class 0.000 claims 8
• 125000003545 alkoxy group Chemical group 0.000 claims 5
• MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical class C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 claims 4
• SMYDMMALUBNVRU-UHFFFAOYSA-N CN(C)[P] Chemical group CN(C)[P] SMYDMMALUBNVRU-UHFFFAOYSA-N 0.000 claims 3
• 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
• 125000004193 piperazinyl group Chemical group 0.000 claims 2
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
• WTGIKPFXWZGKHW-UHFFFAOYSA-N [amino(methyl)phosphanyl]methane Chemical group CP(C)N WTGIKPFXWZGKHW-UHFFFAOYSA-N 0.000 claims 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
• 230000001590 oxidative effect Effects 0.000 claims 1
• 150000003003 phosphines Chemical class 0.000 claims 1
• 201000010099 disease Diseases 0.000 abstract description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 12
• 239000004480 active ingredient Substances 0.000 abstract description 5
• 238000002360 preparation method Methods 0.000 abstract description 5
• 230000002265 prevention Effects 0.000 abstract description 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 261
• 239000000243 solution Substances 0.000 description 173
• 239000011541 reaction mixture Substances 0.000 description 171
• 239000007787 solid Substances 0.000 description 165
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 141
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 129
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 117
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 111
• 239000012044 organic layer Substances 0.000 description 92
• 239000000047 product Substances 0.000 description 83
• 239000000203 mixture Substances 0.000 description 81
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 77
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 70
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 69
• 239000011734 sodium Substances 0.000 description 69
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 64
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 54
• 238000002844 melting Methods 0.000 description 54
• 230000008018 melting Effects 0.000 description 54
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 49
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
• 235000019439 ethyl acetate Nutrition 0.000 description 48
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
• 238000003756 stirring Methods 0.000 description 39
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
• 238000010898 silica gel chromatography Methods 0.000 description 38
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 35
• GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 31
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 30
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 24
• BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 24
• 229910052709 silver Inorganic materials 0.000 description 24
• 239000004332 silver Substances 0.000 description 24
• 235000017557 sodium bicarbonate Nutrition 0.000 description 24
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 24
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 23
• 239000012298 atmosphere Substances 0.000 description 23
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 22
• 229940086542 triethylamine Drugs 0.000 description 21
• 238000004440 column chromatography Methods 0.000 description 20
• 239000000376 reactant Substances 0.000 description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
• 239000012299 nitrogen atmosphere Substances 0.000 description 15
• KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 14
• 241000194017 Streptococcus Species 0.000 description 14
• 229910000040 hydrogen fluoride Inorganic materials 0.000 description 14
• 239000007788 liquid Substances 0.000 description 14
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 14
• 239000012043 crude product Substances 0.000 description 13
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 13
• 230000015572 biosynthetic process Effects 0.000 description 12
• 238000003786 synthesis reaction Methods 0.000 description 12
• 235000019270 ammonium chloride Nutrition 0.000 description 11
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• 229910052938 sodium sulfate Inorganic materials 0.000 description 9
• 235000011152 sodium sulphate Nutrition 0.000 description 9
• 235000000346 sugar Nutrition 0.000 description 9
• XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 8
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 8
• 239000012267 brine Substances 0.000 description 8
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 8
• 235000019345 sodium thiosulphate Nutrition 0.000 description 8
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• 239000003826 tablet Substances 0.000 description 8
• 241000283690 Bos taurus Species 0.000 description 7
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 7
• 229920002472 Starch Polymers 0.000 description 7
• 239000002253 acid Substances 0.000 description 7
• 239000010410 layer Substances 0.000 description 7
• PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• 125000006239 protecting group Chemical group 0.000 description 7
• 239000008107 starch Substances 0.000 description 7
• 235000019698 starch Nutrition 0.000 description 7
• OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 6
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
• 230000001580 bacterial effect Effects 0.000 description 6
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
• 238000003818 flash chromatography Methods 0.000 description 6
• 150000004677 hydrates Chemical class 0.000 description 6
• 239000007800 oxidant agent Substances 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 5
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 5
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 5
• ZOYWWAGVGBSJDL-UHFFFAOYSA-N D-desosamine Natural products CC1CC(N(C)C)C(O)C(O)O1 ZOYWWAGVGBSJDL-UHFFFAOYSA-N 0.000 description 5
• 241000194033 Enterococcus Species 0.000 description 5
• VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
• 241000191967 Staphylococcus aureus Species 0.000 description 5
• 241000193998 Streptococcus pneumoniae Species 0.000 description 5
• 239000004599 antimicrobial Substances 0.000 description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
• 239000000969 carrier Substances 0.000 description 5
• 229960002626 clarithromycin Drugs 0.000 description 5
• 239000000706 filtrate Substances 0.000 description 5
• NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 5
• 229910000105 potassium hydride Inorganic materials 0.000 description 5
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
• 238000000746 purification Methods 0.000 description 5
• 239000001632 sodium acetate Substances 0.000 description 5
• 235000017281 sodium acetate Nutrition 0.000 description 5
• 229940031000 streptococcus pneumoniae Drugs 0.000 description 5
• 238000012360 testing method Methods 0.000 description 5
• ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
• 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 4
• 208000035143 Bacterial infection Diseases 0.000 description 4
• 241000606125 Bacteroides Species 0.000 description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
• ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 4
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
• 108010010803 Gelatin Proteins 0.000 description 4
• 241000606768 Haemophilus influenzae Species 0.000 description 4
• 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 4
• ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 4
• FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 4
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
• 208000010362 Protozoan Infections Diseases 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• 208000022362 bacterial infectious disease Diseases 0.000 description 4
• 125000004432 carbon atom Chemical group C* 0.000 description 4
• DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 4
• AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@](C)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 4
• VTJCSBJRQLZNHE-CSMHCCOUSA-N desosamine Chemical compound C[C@@H](O)C[C@H](N(C)C)[C@@H](O)C=O VTJCSBJRQLZNHE-CSMHCCOUSA-N 0.000 description 4
• 125000004663 dialkyl amino group Chemical group 0.000 description 4
• 229960003276 erythromycin Drugs 0.000 description 4
• NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 4
• 150000002222 fluorine compounds Chemical group 0.000 description 4
• 239000008273 gelatin Substances 0.000 description 4
• 229920000159 gelatin Polymers 0.000 description 4
• 235000019322 gelatine Nutrition 0.000 description 4
• 235000011852 gelatine desserts Nutrition 0.000 description 4
• 239000008101 lactose Substances 0.000 description 4
• 230000004048 modification Effects 0.000 description 4
• 238000012986 modification Methods 0.000 description 4
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 4
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 4
• 230000004044 response Effects 0.000 description 4
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
• SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 4
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
• PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 3
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
• PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 3
• OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
• 229920001817 Agar Polymers 0.000 description 3
• 239000005995 Aluminium silicate Substances 0.000 description 3
• 241000282472 Canis lupus familiaris Species 0.000 description 3
• 239000004215 Carbon black (E152) Substances 0.000 description 3
• 241000193403 Clostridium Species 0.000 description 3
• 229930006677 Erythromycin A Natural products 0.000 description 3
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
• 241000282326 Felis catus Species 0.000 description 3
• 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 3
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
• 241000282412 Homo Species 0.000 description 3
• 208000016604 Lyme disease Diseases 0.000 description 3
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
• 241000186367 Mycobacterium avium Species 0.000 description 3
• IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• 241000606856 Pasteurella multocida Species 0.000 description 3
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
• 241000191940 Staphylococcus Species 0.000 description 3
• 244000299461 Theobroma cacao Species 0.000 description 3
• 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 3
• 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 3
• APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 3
• 239000008272 agar Substances 0.000 description 3
• 235000010419 agar Nutrition 0.000 description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
• 125000003282 alkyl amino group Chemical group 0.000 description 3
• BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
• 235000012211 aluminium silicate Nutrition 0.000 description 3
• 125000004429 atom Chemical group 0.000 description 3
• 230000008901 benefit Effects 0.000 description 3
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
• 239000011230 binding agent Substances 0.000 description 3
• 235000014121 butter Nutrition 0.000 description 3
• 235000001046 cacaotero Nutrition 0.000 description 3
• 229910000019 calcium carbonate Inorganic materials 0.000 description 3
• 235000010216 calcium carbonate Nutrition 0.000 description 3
• 239000002775 capsule Substances 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
• GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 3
• 239000007884 disintegrant Substances 0.000 description 3
• 239000003814 drug Substances 0.000 description 3
• 230000000694 effects Effects 0.000 description 3
• 239000003480 eluent Substances 0.000 description 3
• 239000012458 free base Substances 0.000 description 3
• 239000008103 glucose Substances 0.000 description 3
• 235000001727 glucose Nutrition 0.000 description 3
• 125000001188 haloalkyl group Chemical group 0.000 description 3
• 229930195733 hydrocarbon Natural products 0.000 description 3
• 238000000338 in vitro Methods 0.000 description 3
• 239000004615 ingredient Substances 0.000 description 3
• NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
• YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 3
• 150000007522 mineralic acids Chemical class 0.000 description 3
• 239000003921 oil Substances 0.000 description 3
• 230000003647 oxidation Effects 0.000 description 3
• 238000007254 oxidation reaction Methods 0.000 description 3
• 239000008177 pharmaceutical agent Substances 0.000 description 3
• 229920001223 polyethylene glycol Polymers 0.000 description 3
• IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 3
• 235000011118 potassium hydroxide Nutrition 0.000 description 3
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 3
• 238000010992 reflux Methods 0.000 description 3
• 239000000741 silica gel Substances 0.000 description 3
• 229910002027 silica gel Inorganic materials 0.000 description 3
• 239000011780 sodium chloride Substances 0.000 description 3
• 229910000104 sodium hydride Inorganic materials 0.000 description 3
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 2
• OZGSEIVTQLXWRO-UHFFFAOYSA-N 2,4,6-trichlorobenzoyl chloride Chemical compound ClC(=O)C1=C(Cl)C=C(Cl)C=C1Cl OZGSEIVTQLXWRO-UHFFFAOYSA-N 0.000 description 2
• FOTXWIFGVILZDM-UHFFFAOYSA-N 2-(chloromethyl)-5-pyridin-2-yl-1,3,4-oxadiazole Chemical compound O1C(CCl)=NN=C1C1=CC=CC=N1 FOTXWIFGVILZDM-UHFFFAOYSA-N 0.000 description 2
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 2
• KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 2
• JUHGYNTUFGSUQV-UHFFFAOYSA-N 2-bromo-n-(3-chlorophenyl)acetamide Chemical compound ClC1=CC=CC(NC(=O)CBr)=C1 JUHGYNTUFGSUQV-UHFFFAOYSA-N 0.000 description 2
• JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical compound NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 description 2
• LJXPWUAAAAXJBX-UHFFFAOYSA-N 2-methylallyl radical Chemical group [CH2]C(C)=C LJXPWUAAAAXJBX-UHFFFAOYSA-N 0.000 description 2
• RTMRFJFUZOPGML-UHFFFAOYSA-N 3-(chloromethyl)-5-pyridin-2-yl-1,2,4-oxadiazole Chemical compound ClCC1=NOC(C=2N=CC=CC=2)=N1 RTMRFJFUZOPGML-UHFFFAOYSA-N 0.000 description 2
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 2
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
• WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 2
• 241000251468 Actinopterygii Species 0.000 description 2
• 239000004475 Arginine Substances 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
• 241000589968 Borrelia Species 0.000 description 2
• 241001647372 Chlamydia pneumoniae Species 0.000 description 2
• 241000606153 Chlamydia trachomatis Species 0.000 description 2
• 101150065749 Churc1 gene Proteins 0.000 description 2
• 108010065152 Coagulase Proteins 0.000 description 2
• 241000186216 Corynebacterium Species 0.000 description 2
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
• GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 2
• 241000588724 Escherichia coli Species 0.000 description 2
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
• 241000590002 Helicobacter pylori Species 0.000 description 2
• 206010020751 Hypersensitivity Diseases 0.000 description 2
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 2
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
• QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 2
• 241001466453 Laminaria Species 0.000 description 2
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
• 239000004472 Lysine Substances 0.000 description 2
• 241000124008 Mammalia Species 0.000 description 2
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
• LFTLOKWAGJYHHR-UHFFFAOYSA-N N-methylmorpholine N-oxide Chemical compound CN1(=O)CCOCC1 LFTLOKWAGJYHHR-UHFFFAOYSA-N 0.000 description 2
• 241000588653 Neisseria Species 0.000 description 2
• 230000006179 O-acylation Effects 0.000 description 2
• 229910019142 PO4 Inorganic materials 0.000 description 2
• 241000191992 Peptostreptococcus Species 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
• 102100038239 Protein Churchill Human genes 0.000 description 2
• LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
• DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
• 206010062255 Soft tissue infection Diseases 0.000 description 2
• 241000191963 Staphylococcus epidermidis Species 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
• 241000282898 Sus scrofa Species 0.000 description 2
• QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 2
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• 230000001154 acute effect Effects 0.000 description 2
• 239000000443 aerosol Substances 0.000 description 2
• 150000001412 amines Chemical group 0.000 description 2
• 229940024606 amino acid Drugs 0.000 description 2
• 235000001014 amino acid Nutrition 0.000 description 2
• 150000001413 amino acids Chemical class 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
• 229960003121 arginine Drugs 0.000 description 2
• 235000009697 arginine Nutrition 0.000 description 2
• 125000003710 aryl alkyl group Chemical group 0.000 description 2
• YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 2
• MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 2
• 229960004099 azithromycin Drugs 0.000 description 2
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 2
• 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 2
• VBICKXHEKHSIBG-UHFFFAOYSA-N beta-monoglyceryl stearate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
• YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
• QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
• HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
• 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
• 150000003857 carboxamides Chemical class 0.000 description 2
• 229940038705 chlamydia trachomatis Drugs 0.000 description 2
• 239000013058 crude material Substances 0.000 description 2
• 125000004122 cyclic group Chemical group 0.000 description 2
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
• FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-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
• 239000002552 dosage form Substances 0.000 description 2
• 229940079593 drug Drugs 0.000 description 2
• 239000000839 emulsion Substances 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• 229910052731 fluorine Inorganic materials 0.000 description 2
• 239000006260 foam Substances 0.000 description 2
• 238000009472 formulation Methods 0.000 description 2
• 150000003278 haem Chemical class 0.000 description 2
• 229940047650 haemophilus influenzae Drugs 0.000 description 2
• 150000004820 halides Chemical class 0.000 description 2
• 229940037467 helicobacter pylori Drugs 0.000 description 2
• 125000004475 heteroaralkyl group Chemical group 0.000 description 2
• FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
• 229960002885 histidine Drugs 0.000 description 2
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 2
• 239000005457 ice water Substances 0.000 description 2
• 239000002054 inoculum Substances 0.000 description 2
• 150000007529 inorganic bases Chemical class 0.000 description 2
• 238000007918 intramuscular administration Methods 0.000 description 2
• 238000001990 intravenous administration Methods 0.000 description 2
• SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 2
• 230000007794 irritation Effects 0.000 description 2
• JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
• 229960003646 lysine Drugs 0.000 description 2
• 208000004396 mastitis Diseases 0.000 description 2
• 125000002950 monocyclic group Chemical group 0.000 description 2
• 238000000465 moulding Methods 0.000 description 2
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
• 150000007524 organic acids Chemical class 0.000 description 2
• 235000005985 organic acids Nutrition 0.000 description 2
• 125000003566 oxetanyl group Chemical group 0.000 description 2
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
• DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
• 235000021317 phosphate Nutrition 0.000 description 2
• 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
• 239000006187 pill Substances 0.000 description 2
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
• NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
• 238000002953 preparative HPLC Methods 0.000 description 2
• LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
• 125000001453 quaternary ammonium group Chemical group 0.000 description 2
• 208000023504 respiratory system disease Diseases 0.000 description 2
• YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
• 206010040872 skin infection Diseases 0.000 description 2
• 239000012312 sodium hydride Substances 0.000 description 2
• 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
• 241000894007 species Species 0.000 description 2
• 239000000126 substance Substances 0.000 description 2
• 150000008163 sugars Chemical class 0.000 description 2
• 239000000375 suspending agent Substances 0.000 description 2
• 150000003536 tetrazoles Chemical class 0.000 description 2
• 210000001519 tissue Anatomy 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
• LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
• 229960004799 tryptophan Drugs 0.000 description 2
• 208000019206 urinary tract infection Diseases 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
• VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical class CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
• QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-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
• LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
• MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
• BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
• WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
• BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
• HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
• SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
• WGVYCXYGPNNUQA-UHFFFAOYSA-N 1-(bromomethyl)-2-methylbenzene Chemical compound CC1=CC=CC=C1CBr WGVYCXYGPNNUQA-UHFFFAOYSA-N 0.000 description 1
• BIAAQBNMRITRDV-UHFFFAOYSA-N 1-(chloromethoxy)-2-methoxyethane Chemical compound COCCOCCl BIAAQBNMRITRDV-UHFFFAOYSA-N 0.000 description 1
• NOUAEJFAVOHNSY-UHFFFAOYSA-N 1-[4-(bromomethyl)phenyl]-1,2,4-triazole Chemical compound C1=CC(CBr)=CC=C1N1N=CN=C1 NOUAEJFAVOHNSY-UHFFFAOYSA-N 0.000 description 1
• XNAVOEMMUHOVRY-UHFFFAOYSA-N 1-bromo-2-methoxy-3-(2-methoxyphenyl)benzene Chemical compound COC1=CC=CC=C1C1=CC=CC(Br)=C1OC XNAVOEMMUHOVRY-UHFFFAOYSA-N 0.000 description 1
• CSFQWNRVYPNVBK-UHFFFAOYSA-N 1-bromo-3-fluoro-2-(3-fluorophenyl)benzene Chemical compound FC1=CC=CC(C=2C(=CC=CC=2F)Br)=C1 CSFQWNRVYPNVBK-UHFFFAOYSA-N 0.000 description 1
• LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 1
• UQGSABFRTVDREH-UHFFFAOYSA-N 1-bromo-4-(trifluoromethyl)-2-[4-(trifluoromethyl)phenyl]benzene Chemical compound FC(F)(F)c1ccc(cc1)-c1cc(ccc1Br)C(F)(F)F UQGSABFRTVDREH-UHFFFAOYSA-N 0.000 description 1
• JKXQKGNGJVZKFA-UHFFFAOYSA-N 1-chloro-3-methylbut-2-ene Chemical compound CC(C)=CCCl JKXQKGNGJVZKFA-UHFFFAOYSA-N 0.000 description 1
• YCQANBSROMMIQP-UHFFFAOYSA-N 1-chloropyrrolidine-2,5-dione;methylsulfanylmethane Chemical compound CSC.ClN1C(=O)CCC1=O YCQANBSROMMIQP-UHFFFAOYSA-N 0.000 description 1
• FWPYUSLQCQDLJR-UHFFFAOYSA-N 1-ethyl-4-isocyanatobenzene Chemical compound CCC1=CC=C(N=C=O)C=C1 FWPYUSLQCQDLJR-UHFFFAOYSA-N 0.000 description 1
• IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
• KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical group C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
• NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
• YSMYZCRBWWHNQW-UHFFFAOYSA-N 2,3-bis(3,4-dimethoxyphenyl)propanoic acid Chemical compound C1=C(OC)C(OC)=CC=C1CC(C(O)=O)C1=CC=C(OC)C(OC)=C1 YSMYZCRBWWHNQW-UHFFFAOYSA-N 0.000 description 1
• JPBRCFVCHHIZRR-UHFFFAOYSA-N 2,3-bis(4-methoxyphenyl)propanoic acid Chemical compound C1=CC(OC)=CC=C1CC(C(O)=O)C1=CC=C(OC)C=C1 JPBRCFVCHHIZRR-UHFFFAOYSA-N 0.000 description 1
• 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
• PCRICPYPVZKEBZ-UHFFFAOYSA-N 2,3-diphenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CC1=CC=CC=C1 PCRICPYPVZKEBZ-UHFFFAOYSA-N 0.000 description 1
• YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 1
• IBKCKUUZGWUBCE-UHFFFAOYSA-N 2-(chloromethyl)-5-(3,5-dimethoxyphenyl)-1,3,4-oxadiazole Chemical compound COC1=CC(OC)=CC(C=2OC(CCl)=NN=2)=C1 IBKCKUUZGWUBCE-UHFFFAOYSA-N 0.000 description 1
• YYEFHXOELYYOTP-UHFFFAOYSA-N 2-(chloromethyl)-5-(3-fluorophenyl)-1,3,4-oxadiazole Chemical compound FC1=CC=CC(C=2OC(CCl)=NN=2)=C1 YYEFHXOELYYOTP-UHFFFAOYSA-N 0.000 description 1
• GEHIXSKXGCIKJJ-UHFFFAOYSA-N 2-(chloromethyl)-5-(4-methoxyphenyl)-1,3,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1C1=NN=C(CCl)O1 GEHIXSKXGCIKJJ-UHFFFAOYSA-N 0.000 description 1
• RFUPSMVMTLALFF-UHFFFAOYSA-N 2-(chloromethyl)-5-(5-chloropyridin-2-yl)-1,3,4-oxadiazole Chemical compound O1C(CCl)=NN=C1C1=CC=C(Cl)C=N1 RFUPSMVMTLALFF-UHFFFAOYSA-N 0.000 description 1
• PJABODYOHXQREK-UHFFFAOYSA-N 2-(chloromethyl)-5-(5-fluoropyridin-2-yl)-1,3,4-oxadiazole Chemical compound ClCC1=NN=C(O1)C1=NC=C(C=C1)F PJABODYOHXQREK-UHFFFAOYSA-N 0.000 description 1
• GVBNJABCKFDKKD-UHFFFAOYSA-N 2-(chloromethyl)-5-cyclopropyl-1,3,4-oxadiazole Chemical compound O1C(CCl)=NN=C1C1CC1 GVBNJABCKFDKKD-UHFFFAOYSA-N 0.000 description 1
• NSRMLEGRKUNRDW-UHFFFAOYSA-N 2-(chloromethyl)-5-pyrazin-2-yl-1,3,4-oxadiazole Chemical compound O1C(CCl)=NN=C1C1=CN=CC=N1 NSRMLEGRKUNRDW-UHFFFAOYSA-N 0.000 description 1
• NPLSXBKXSGCGFE-UHFFFAOYSA-N 2-(chloromethyl)-5-pyrimidin-5-yl-1,3,4-oxadiazole Chemical compound ClCC1=NN=C(O1)C=1C=NC=NC=1 NPLSXBKXSGCGFE-UHFFFAOYSA-N 0.000 description 1
• FLQZMUXFJLKXGY-UHFFFAOYSA-N 2-(phenylcarbamoylamino)acetic acid Chemical compound OC(=O)CNC(=O)NC1=CC=CC=C1 FLQZMUXFJLKXGY-UHFFFAOYSA-N 0.000 description 1
• VFVKTYAMTRTZKZ-UHFFFAOYSA-N 2-(tetrazol-1-yl)acetonitrile Chemical compound N#CCN1C=NN=N1 VFVKTYAMTRTZKZ-UHFFFAOYSA-N 0.000 description 1
• ZVVKSWYVOHHOTQ-UHFFFAOYSA-N 2-(tetrazol-2-yl)acetamide Chemical compound NC(=O)CN1N=CN=N1 ZVVKSWYVOHHOTQ-UHFFFAOYSA-N 0.000 description 1
• YWTCGGHKHQPYIG-UHFFFAOYSA-N 2-(tetrazol-2-yl)acetonitrile Chemical compound N#CCN1N=CN=N1 YWTCGGHKHQPYIG-UHFFFAOYSA-N 0.000 description 1
• SZQQOCHTDPXUSE-UHFFFAOYSA-N 2-(tetrazol-2-yl)ethanol Chemical compound OCCN1N=CN=N1 SZQQOCHTDPXUSE-UHFFFAOYSA-N 0.000 description 1
• QPIOVNJLOVNTMW-UHFFFAOYSA-N 2-bromo-n,n-dimethylacetamide Chemical compound CN(C)C(=O)CBr QPIOVNJLOVNTMW-UHFFFAOYSA-N 0.000 description 1
• OVQAPIACPDDJBE-UHFFFAOYSA-N 2-bromo-n-(2,3,4-trifluorophenyl)acetamide Chemical compound FC1=CC=C(NC(=O)CBr)C(F)=C1F OVQAPIACPDDJBE-UHFFFAOYSA-N 0.000 description 1
• NFFFURNQKMXKPY-UHFFFAOYSA-N 2-bromo-n-(2,4-difluorophenyl)acetamide Chemical compound FC1=CC=C(NC(=O)CBr)C(F)=C1 NFFFURNQKMXKPY-UHFFFAOYSA-N 0.000 description 1
• JMRLQUWUFLVROJ-UHFFFAOYSA-N 2-bromo-n-(2-fluorophenyl)acetamide Chemical compound FC1=CC=CC=C1NC(=O)CBr JMRLQUWUFLVROJ-UHFFFAOYSA-N 0.000 description 1
• DMOPLFALZWOOTI-UHFFFAOYSA-N 2-bromo-n-(2-methoxyphenyl)acetamide Chemical compound COC1=CC=CC=C1NC(=O)CBr DMOPLFALZWOOTI-UHFFFAOYSA-N 0.000 description 1
• KVANKBIYHUPWBS-UHFFFAOYSA-N 2-bromo-n-(3,5-dimethoxyphenyl)acetamide Chemical compound COC1=CC(NC(=O)CBr)=CC(OC)=C1 KVANKBIYHUPWBS-UHFFFAOYSA-N 0.000 description 1
• MZXODXMRGJJHFM-UHFFFAOYSA-N 2-bromo-n-(3-fluorophenyl)-n-methylacetamide Chemical compound BrCC(=O)N(C)C1=CC=CC(F)=C1 MZXODXMRGJJHFM-UHFFFAOYSA-N 0.000 description 1
• OVNHSFQANYEQSS-UHFFFAOYSA-N 2-bromo-n-(3-fluorophenyl)acetamide Chemical compound FC1=CC=CC(NC(=O)CBr)=C1 OVNHSFQANYEQSS-UHFFFAOYSA-N 0.000 description 1
• JWGUWIRYYZPGHM-UHFFFAOYSA-N 2-bromo-n-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(NC(=O)CBr)=C1 JWGUWIRYYZPGHM-UHFFFAOYSA-N 0.000 description 1
• XTBCNAOHVGTORI-UHFFFAOYSA-N 2-bromo-n-(4-chlorophenyl)-n-methylacetamide Chemical compound BrCC(=O)N(C)C1=CC=C(Cl)C=C1 XTBCNAOHVGTORI-UHFFFAOYSA-N 0.000 description 1
• JXUWYCOGYOQUST-UHFFFAOYSA-N 2-bromo-n-(4-fluorophenyl)acetamide Chemical compound FC1=CC=C(NC(=O)CBr)C=C1 JXUWYCOGYOQUST-UHFFFAOYSA-N 0.000 description 1
• AFGORAFRNCMUJC-UHFFFAOYSA-N 2-bromo-n-cyclopropylacetamide Chemical compound BrCC(=O)NC1CC1 AFGORAFRNCMUJC-UHFFFAOYSA-N 0.000 description 1
• REXUYBKPWIPONM-UHFFFAOYSA-N 2-bromoacetonitrile Chemical compound BrCC#N REXUYBKPWIPONM-UHFFFAOYSA-N 0.000 description 1
• LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 description 1
• XCARGDPHZYJCMU-UHFFFAOYSA-N 2-chloro-n'-hydroxyethanimidamide Chemical compound ClCC(N)=NO XCARGDPHZYJCMU-UHFFFAOYSA-N 0.000 description 1
• 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
• FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 1
• CCZWSTFVHJPCEM-UHFFFAOYSA-N 2-iodopyridine Chemical compound IC1=CC=CC=N1 CCZWSTFVHJPCEM-UHFFFAOYSA-N 0.000 description 1
• 229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
• 125000004638 2-oxopiperazinyl group Chemical group O=C1N(CCNC1)* 0.000 description 1
• 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 description 1
• SECHDFHDDVELCV-UHFFFAOYSA-N 3-(2h-tetrazol-5-yl)pyridine Chemical compound C1=CN=CC(C2=NNN=N2)=C1 SECHDFHDDVELCV-UHFFFAOYSA-N 0.000 description 1
• UBLMRADOKLXLCD-UHFFFAOYSA-N 3-(3-fluorophenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=CC(F)=C1 UBLMRADOKLXLCD-UHFFFAOYSA-N 0.000 description 1
• UBSBRLFVQKHLPG-UHFFFAOYSA-N 3-(3-phenyl-1,2,4-oxadiazol-5-yl)propanoic acid Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=N1 UBSBRLFVQKHLPG-UHFFFAOYSA-N 0.000 description 1
• XFXBCTUNCOJZGA-UHFFFAOYSA-N 3-(3-pyridin-3-yl-1,2,4-oxadiazol-5-yl)propanoic acid Chemical compound O1C(CCC(=O)O)=NC(C=2C=NC=CC=2)=N1 XFXBCTUNCOJZGA-UHFFFAOYSA-N 0.000 description 1
• QQAOPUYDACUNLY-UHFFFAOYSA-N 3-(3-pyridin-4-yl-1,2,4-oxadiazol-5-yl)propanoic acid Chemical compound O1C(CCC(=O)O)=NC(C=2C=CN=CC=2)=N1 QQAOPUYDACUNLY-UHFFFAOYSA-N 0.000 description 1
• WDGXIUUWINKTGP-UHFFFAOYSA-N 3-(3-pyridinyl)propanoic acid Chemical compound OC(=O)CCC1=CC=CN=C1 WDGXIUUWINKTGP-UHFFFAOYSA-N 0.000 description 1
• OYBMOXCVIWAARB-UHFFFAOYSA-N 3-(chloromethyl)-5-(1H-pyridazin-2-yl)-1,2,4-oxadiazole Chemical compound ClCC1=NOC(=N1)N1NC=CC=C1 OYBMOXCVIWAARB-UHFFFAOYSA-N 0.000 description 1
• AKZMLMOXLCLUFD-UHFFFAOYSA-N 3-(chloromethyl)-5-(2-fluoropyridin-3-yl)-1,2,4-oxadiazole Chemical compound FC1=NC=CC=C1C1=NC(=NO1)CCl AKZMLMOXLCLUFD-UHFFFAOYSA-N 0.000 description 1
• SKRGPGUOAVKAMW-UHFFFAOYSA-N 3-(chloromethyl)-5-(2-methyl-1,3-oxazol-4-yl)-1,2,4-oxadiazole Chemical compound ClCC1=NOC(=N1)C=1N=C(OC=1)C SKRGPGUOAVKAMW-UHFFFAOYSA-N 0.000 description 1
• TUDMJGXXGOORCD-UHFFFAOYSA-N 3-(chloromethyl)-5-(3-chlorophenyl)-1,2,4-oxadiazole Chemical compound ClCC1=NOC(C=2C=C(Cl)C=CC=2)=N1 TUDMJGXXGOORCD-UHFFFAOYSA-N 0.000 description 1
• UZBVQWPOPDPSLX-UHFFFAOYSA-N 3-(chloromethyl)-5-(3-fluoro-4-methoxyphenyl)-1,2,4-oxadiazole Chemical compound C1=C(F)C(OC)=CC=C1C1=NC(CCl)=NO1 UZBVQWPOPDPSLX-UHFFFAOYSA-N 0.000 description 1
• BIZZRQCIHOUPJM-UHFFFAOYSA-N 3-(chloromethyl)-5-(6-methylpyridin-2-yl)-1,2,4-oxadiazole Chemical compound CC1=CC=CC(C=2ON=C(CCl)N=2)=N1 BIZZRQCIHOUPJM-UHFFFAOYSA-N 0.000 description 1
• UANFFSNPYKTHJF-UHFFFAOYSA-N 3-(chloromethyl)-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=NC(CCl)=NO1 UANFFSNPYKTHJF-UHFFFAOYSA-N 0.000 description 1
• VIIBOHRJBXNITD-UHFFFAOYSA-N 3-(chloromethyl)-5-cyclopropyl-1,2,4-oxadiazole Chemical compound ClCC1=NOC(C2CC2)=N1 VIIBOHRJBXNITD-UHFFFAOYSA-N 0.000 description 1
• FEXTXBAFBURKGS-UHFFFAOYSA-N 3-(chloromethyl)-5-methyl-1,2-oxazole Chemical compound CC1=CC(CCl)=NO1 FEXTXBAFBURKGS-UHFFFAOYSA-N 0.000 description 1
• MLJJRVMANUGETQ-UHFFFAOYSA-N 3-(chloromethyl)-5-phenyl-1,2-oxazole Chemical compound O1N=C(CCl)C=C1C1=CC=CC=C1 MLJJRVMANUGETQ-UHFFFAOYSA-N 0.000 description 1
• AHEIVQPKJWJKHI-UHFFFAOYSA-N 3-(chloromethyl)-5-pyridin-2-yl-1,2-oxazole Chemical compound O1N=C(CCl)C=C1C1=CC=CC=N1 AHEIVQPKJWJKHI-UHFFFAOYSA-N 0.000 description 1
• OIDBMRYRQPXSGO-UHFFFAOYSA-N 3-(chloromethyl)-5-pyridin-3-yl-1,2,4-oxadiazole Chemical compound ClCC1=NOC(C=2C=NC=CC=2)=N1 OIDBMRYRQPXSGO-UHFFFAOYSA-N 0.000 description 1
• AERBJSNWLXKMGF-UHFFFAOYSA-N 3-(chloromethyl)-5-pyridin-4-yl-1,2,4-oxadiazole Chemical compound ClCC1=NOC(C=2C=CN=CC=2)=N1 AERBJSNWLXKMGF-UHFFFAOYSA-N 0.000 description 1
• OTKMTEHKDDIBBB-UHFFFAOYSA-N 3-(chloromethyl)-5-pyrimidin-5-yl-1,2-oxazole Chemical compound ClCC1=NOC(=C1)C=1C=NC=NC=1 OTKMTEHKDDIBBB-UHFFFAOYSA-N 0.000 description 1
• XFJFFYVBKQJNLJ-UHFFFAOYSA-N 3-(iodomethyl)-5-pyridin-2-yl-1,2,4-oxadiazole Chemical compound ICC1=NOC(C=2N=CC=CC=2)=N1 XFJFFYVBKQJNLJ-UHFFFAOYSA-N 0.000 description 1
• OHXAOPZTJOUYKM-UHFFFAOYSA-N 3-Chloro-2-methylpropene Chemical compound CC(=C)CCl OHXAOPZTJOUYKM-UHFFFAOYSA-N 0.000 description 1
• XOYNFQNJDZCKQA-UHFFFAOYSA-N 3-[1-(2-methoxyphenyl)triazol-4-yl]propanoic acid Chemical compound COC1=CC=CC=C1N1N=NC(CCC(O)=O)=C1 XOYNFQNJDZCKQA-UHFFFAOYSA-N 0.000 description 1
• ZBGBUSRPVXIQNW-UHFFFAOYSA-N 3-[1-(3,5-difluorophenyl)triazol-4-yl]propanoic acid Chemical compound N1=NC(CCC(=O)O)=CN1C1=CC(F)=CC(F)=C1 ZBGBUSRPVXIQNW-UHFFFAOYSA-N 0.000 description 1
• AMQCGFFGAXGGJX-UHFFFAOYSA-N 3-[1-(4-fluorophenyl)triazol-4-yl]propanoic acid Chemical compound N1=NC(CCC(=O)O)=CN1C1=CC=C(F)C=C1 AMQCGFFGAXGGJX-UHFFFAOYSA-N 0.000 description 1
• CMJSVRXTMIPHNM-UHFFFAOYSA-N 3-[3-(3-fluorophenyl)-1,2,4-oxadiazol-5-yl]propanoic acid Chemical compound O1C(CCC(=O)O)=NC(C=2C=C(F)C=CC=2)=N1 CMJSVRXTMIPHNM-UHFFFAOYSA-N 0.000 description 1
• OAQGUCLRBDBMQR-UHFFFAOYSA-N 3-[3-(3-methoxyphenyl)-1,2,4-oxadiazol-5-yl]propanoic acid Chemical compound COC1=CC=CC(C=2N=C(CCC(O)=O)ON=2)=C1 OAQGUCLRBDBMQR-UHFFFAOYSA-N 0.000 description 1
• LBFLFJKKZLTGOV-UHFFFAOYSA-N 3-[3-(4-bromophenyl)-1,2,4-oxadiazol-5-yl]propanoic acid Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC(Br)=CC=2)=N1 LBFLFJKKZLTGOV-UHFFFAOYSA-N 0.000 description 1
• PZAHEYNFUFWABS-UHFFFAOYSA-N 3-[3-(4-chlorophenyl)-1,2,4-oxadiazol-5-yl]propanoic acid Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC(Cl)=CC=2)=N1 PZAHEYNFUFWABS-UHFFFAOYSA-N 0.000 description 1
• WRFNXLGYERRRTO-UHFFFAOYSA-N 3-[3-(4-methoxyphenyl)-1,2,4-oxadiazol-5-yl]propanoic acid Chemical compound C1=CC(OC)=CC=C1C1=NOC(CCC(O)=O)=N1 WRFNXLGYERRRTO-UHFFFAOYSA-N 0.000 description 1
• RUTZHBJOSPBPDQ-UHFFFAOYSA-N 3-[3-(chloromethyl)-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound ClCC1=NOC(C=2C=C(C=CC=2)C#N)=N1 RUTZHBJOSPBPDQ-UHFFFAOYSA-N 0.000 description 1
• PQVYFUCAVPVANQ-UHFFFAOYSA-N 3-[3-(chloromethyl)-4-methoxyphenyl]-1,2,4-oxadiazole Chemical compound ClCC=1C(=CC=C(C=1)C1=NOC=N1)OC PQVYFUCAVPVANQ-UHFFFAOYSA-N 0.000 description 1
• KAIFMXVOJITEON-UHFFFAOYSA-N 3-[3-(chloromethyl)-5-fluorophenyl]-1,2,4-oxadiazole Chemical compound ClCC=1C=C(C=C(C=1)C1=NOC=N1)F KAIFMXVOJITEON-UHFFFAOYSA-N 0.000 description 1
• WDAGGBREOPFEHG-UHFFFAOYSA-N 3-[3-chloro-5-(chloromethyl)phenyl]-1,2,4-oxadiazole Chemical compound ClCC=1C=C(C=C(C=1)C1=NOC=N1)Cl WDAGGBREOPFEHG-UHFFFAOYSA-N 0.000 description 1
• OSKJPAKEWVJCNA-UHFFFAOYSA-N 3-[4-(2-methylphenyl)piperazin-1-yl]propanoic acid Chemical compound CC1=CC=CC=C1N1CCN(CCC(O)=O)CC1 OSKJPAKEWVJCNA-UHFFFAOYSA-N 0.000 description 1
• DHYMMLJRQSLEGP-UHFFFAOYSA-N 3-[4-(4-methylpiperazin-4-ium-1-yl)phenyl]propanoate Chemical compound C1C[NH+](C)CCN1C1=CC=C(CCC([O-])=O)C=C1 DHYMMLJRQSLEGP-UHFFFAOYSA-N 0.000 description 1
• ANEJGWXXIMCUMZ-UHFFFAOYSA-N 3-[4-chloro-3-(chloromethyl)phenyl]-1,2,4-oxadiazole Chemical compound ClCC=1C(=CC=C(C=1)C1=NOC=N1)Cl ANEJGWXXIMCUMZ-UHFFFAOYSA-N 0.000 description 1
• USEGQJLHQSTGHW-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene Chemical compound CC(=C)CBr USEGQJLHQSTGHW-UHFFFAOYSA-N 0.000 description 1
• NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 1
• OOFDLUQVLPGWMM-UHFFFAOYSA-N 3-chloro-2-fluoroprop-1-ene Chemical compound FC(=C)CCl OOFDLUQVLPGWMM-UHFFFAOYSA-N 0.000 description 1
• PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 1
• FHYDHJXZZQCXOX-UHFFFAOYSA-N 3-fluoro-n-methylaniline Chemical compound CNC1=CC=CC(F)=C1 FHYDHJXZZQCXOX-UHFFFAOYSA-N 0.000 description 1
• BGARPMGQRREXLN-UHFFFAOYSA-N 3-iodobenzonitrile Chemical compound IC1=CC=CC(C#N)=C1 BGARPMGQRREXLN-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
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 description 1
• WAKFFQCNIIXFOV-UHFFFAOYSA-N 4-(bromomethyl)-1-(3-fluorophenyl)triazole Chemical compound FC1=CC=CC(N2N=NC(CBr)=C2)=C1 WAKFFQCNIIXFOV-UHFFFAOYSA-N 0.000 description 1
• VYVXBWRCEYHRTD-UHFFFAOYSA-N 4-bromo-2-(4-cyanophenyl)benzonitrile Chemical compound Brc1ccc(C#N)c(c1)-c1ccc(cc1)C#N VYVXBWRCEYHRTD-UHFFFAOYSA-N 0.000 description 1
• DMAYBPBPEUFIHJ-UHFFFAOYSA-N 4-bromobut-1-ene Chemical compound BrCCC=C DMAYBPBPEUFIHJ-UHFFFAOYSA-N 0.000 description 1
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
• YWRZTXKBYCOPMY-UHFFFAOYSA-N 5-(chloromethyl)-3-cyclopropyl-1,2,4-oxadiazole Chemical compound O1C(CCl)=NC(C2CC2)=N1 YWRZTXKBYCOPMY-UHFFFAOYSA-N 0.000 description 1
• JMMBCYRZDCWVIB-UHFFFAOYSA-N 5-(chloromethyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound O1C(CCl)=NC(C=2N=CC=CC=2)=N1 JMMBCYRZDCWVIB-UHFFFAOYSA-N 0.000 description 1
• RGRRKYQLLSVYGV-UHFFFAOYSA-N 5-(chloromethyl)-3-pyridin-3-yl-1,2,4-oxadiazole Chemical compound O1C(CCl)=NC(C=2C=NC=CC=2)=N1 RGRRKYQLLSVYGV-UHFFFAOYSA-N 0.000 description 1
• XCTINNFYFNYYSO-UHFFFAOYSA-N 5-(chloromethyl)-3-pyrimidin-2-yl-1,2,4-oxadiazole Chemical compound O1C(CCl)=NC(C=2N=CC=CN=2)=N1 XCTINNFYFNYYSO-UHFFFAOYSA-N 0.000 description 1
• OIQZXVJZGXTFDV-UHFFFAOYSA-N 5-(chloromethyl)-5-pyrimidin-5-yl-2H-1,2,4-oxadiazole Chemical compound ClCC1(N=CNO1)C=1C=NC=NC=1 OIQZXVJZGXTFDV-UHFFFAOYSA-N 0.000 description 1
• IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
• ZLVUVYOBVUTAIF-UHFFFAOYSA-N 5-fluoro-N-hydroxypyridine-2-carboximidoyl chloride Chemical compound FC=1C=CC(=NC=1)C(=NO)Cl ZLVUVYOBVUTAIF-UHFFFAOYSA-N 0.000 description 1
• XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
• XTDBQHJAWWPWNN-UHFFFAOYSA-N 6-[5-(chloromethyl)-1,2,4-oxadiazol-3-yl]pyridine-3-carbonitrile Chemical compound ClCC1=NC(=NO1)C1=NC=C(C=C1)C#N XTDBQHJAWWPWNN-UHFFFAOYSA-N 0.000 description 1
• BGBCTCAXFBKVRU-UHFFFAOYSA-N 6-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]pyridine-3-carbonitrile Chemical compound O1C(CCl)=NN=C1C1=CC=C(C#N)C=N1 BGBCTCAXFBKVRU-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
• OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
• 240000008025 Alternanthera ficoidea Species 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
• 239000005695 Ammonium acetate Substances 0.000 description 1
• DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 201000001320 Atherosclerosis Diseases 0.000 description 1
• 241000271566 Aves Species 0.000 description 1
• 241000606660 Bartonella Species 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
• 241000588832 Bordetella pertussis Species 0.000 description 1
• 241001148534 Brachyspira 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
• UYSBMCNWRPGTGJ-UHFFFAOYSA-N C1=CC(=C(N=C1)Cl)C2=NC(=NO2)CCl Chemical compound C1=CC(=C(N=C1)Cl)C2=NC(=NO2)CCl UYSBMCNWRPGTGJ-UHFFFAOYSA-N 0.000 description 1
• GGRVDUBOZKTHLW-UHFFFAOYSA-N CC(C)(C)c1n[n](CCO)nn1 Chemical compound CC(C)(C)c1n[n](CCO)nn1 GGRVDUBOZKTHLW-UHFFFAOYSA-N 0.000 description 1
• 241000589875 Campylobacter jejuni Species 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
• 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
• VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
• WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• DTYCMCPERVKSNW-UHFFFAOYSA-N ClCC1=NOC(=C1)C1=NC=C(C=C1)C Chemical compound ClCC1=NOC(=C1)C1=NC=C(C=C1)C DTYCMCPERVKSNW-UHFFFAOYSA-N 0.000 description 1
• 241001112696 Clostridia Species 0.000 description 1
• 241000193468 Clostridium perfringens Species 0.000 description 1
• 241000224483 Coccidia Species 0.000 description 1
• 206010010741 Conjunctivitis Diseases 0.000 description 1
• 206010011224 Cough Diseases 0.000 description 1
• 208000008953 Cryptosporidiosis Diseases 0.000 description 1
• DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-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
• 238000006646 Dess-Martin oxidation reaction Methods 0.000 description 1
• 108010016626 Dipeptides Proteins 0.000 description 1
• 241000588914 Enterobacter Species 0.000 description 1
• 241000186394 Eubacterium Species 0.000 description 1
• 239000004606 Fillers/Extenders Substances 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 206010016936 Folliculitis Diseases 0.000 description 1
• 206010016952 Food poisoning Diseases 0.000 description 1
• 208000019331 Foodborne disease Diseases 0.000 description 1
• BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
• 241000605909 Fusobacterium Species 0.000 description 1
• 241000605952 Fusobacterium necrophorum Species 0.000 description 1
• 208000005577 Gastroenteritis Diseases 0.000 description 1
• 206010018364 Glomerulonephritis Diseases 0.000 description 1
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
• 239000004471 Glycine Substances 0.000 description 1
• 244000068988 Glycine max Species 0.000 description 1
• 235000010469 Glycine max Nutrition 0.000 description 1
• 241000606790 Haemophilus Species 0.000 description 1
• 241000588748 Klebsiella 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
• ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-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
• DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-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
• ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-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
• AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
• KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
• JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
• 241001148567 Lawsonia intracellularis Species 0.000 description 1
• 241000589242 Legionella pneumophila Species 0.000 description 1
• ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
• 241000186781 Listeria Species 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
• 241000588622 Moraxella bovis Species 0.000 description 1
• 241000588655 Moraxella catarrhalis Species 0.000 description 1
• 241000186359 Mycobacterium Species 0.000 description 1
• 241000513886 Mycobacterium avium complex (MAC) Species 0.000 description 1
• 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
• 241000204031 Mycoplasma Species 0.000 description 1
• 241001138504 Mycoplasma bovis Species 0.000 description 1
• 241000202934 Mycoplasma pneumoniae Species 0.000 description 1
• TXCJVUKBUORCDV-UHFFFAOYSA-N N-(3-fluorophenyl)-N-methyltetrazole-2-carboxamide Chemical compound FC=1C=C(C=CC1)N(C(=O)N1N=CN=N1)C TXCJVUKBUORCDV-UHFFFAOYSA-N 0.000 description 1
• XBTPHBYKYXWYOZ-UHFFFAOYSA-N N-hydroxypyridine-2-carboximidoyl chloride Chemical compound ON=C(Cl)C1=CC=CC=N1 XBTPHBYKYXWYOZ-UHFFFAOYSA-N 0.000 description 1
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
• 206010048685 Oral infection Diseases 0.000 description 1
• 206010031252 Osteomyelitis Diseases 0.000 description 1
• 206010033078 Otitis media Diseases 0.000 description 1
• 241001494479 Pecora Species 0.000 description 1
• 201000007100 Pharyngitis Diseases 0.000 description 1
• 206010035664 Pneumonia Diseases 0.000 description 1
• 229920001214 Polysorbate 60 Polymers 0.000 description 1
• 241000605894 Porphyromonas Species 0.000 description 1
• 208000005107 Premature Birth Diseases 0.000 description 1
• 206010036590 Premature baby Diseases 0.000 description 1
• ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• 206010037660 Pyrexia Diseases 0.000 description 1
• IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
• 206010057190 Respiratory tract infections Diseases 0.000 description 1
• 241000187559 Saccharopolyspora erythraea Species 0.000 description 1
• 241000607142 Salmonella Species 0.000 description 1
• 206010040070 Septic Shock Diseases 0.000 description 1
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
• 229920001800 Shellac Polymers 0.000 description 1
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
• 241000191984 Staphylococcus haemolyticus Species 0.000 description 1
• 241001147691 Staphylococcus saprophyticus Species 0.000 description 1
• 241000194054 Streptococcus uberis Species 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
• AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
• 239000004473 Threonine Substances 0.000 description 1
• 206010044248 Toxic shock syndrome Diseases 0.000 description 1
• 231100000650 Toxic shock syndrome Toxicity 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• 241000589886 Treponema Species 0.000 description 1
• 208000025865 Ulcer Diseases 0.000 description 1
• 241000202898 Ureaplasma Species 0.000 description 1
• 208000006374 Uterine Cervicitis Diseases 0.000 description 1
• KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
• 208000000260 Warts Diseases 0.000 description 1
• KNEQOBGUNLFPOC-UHFFFAOYSA-N [3-[2-(4-bromophenyl)-2-oxoethyl]phenyl] acetate Chemical compound CC(=O)Oc1cccc(CC(=O)c2ccc(Br)cc2)c1 KNEQOBGUNLFPOC-UHFFFAOYSA-N 0.000 description 1
• XXVFAWZBVGRAKH-UHFFFAOYSA-N [O-]C(C[S+](C1=CC=CC=C1)C1=CC=CC=C1)=O Chemical compound [O-]C(C[S+](C1=CC=CC=C1)C1=CC=CC=C1)=O XXVFAWZBVGRAKH-UHFFFAOYSA-N 0.000 description 1
• SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 1
• 206010000269 abscess Diseases 0.000 description 1
• 239000003655 absorption accelerator Substances 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 235000011054 acetic acid Nutrition 0.000 description 1
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
• 239000012346 acetyl chloride Substances 0.000 description 1
• 230000021736 acetylation Effects 0.000 description 1
• 238000006640 acetylation reaction Methods 0.000 description 1
• 230000004913 activation Effects 0.000 description 1
• 125000000848 adenin-9-yl group Chemical group [H]N([H])C1=C2N=C([H])N(*)C2=NC([H])=N1 0.000 description 1
• WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
• 229960003767 alanine Drugs 0.000 description 1
• 235000004279 alanine Nutrition 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 229940072056 alginate Drugs 0.000 description 1
• 235000010443 alginic acid Nutrition 0.000 description 1
• 229920000615 alginic acid Polymers 0.000 description 1
• 125000003342 alkenyl group Chemical group 0.000 description 1
• 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
• 150000008052 alkyl sulfonates Chemical class 0.000 description 1
• 125000004414 alkyl thio group Chemical group 0.000 description 1
• 125000000304 alkynyl group Chemical group 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• AWUCVROLDVIAJX-UHFFFAOYSA-N alpha-glycerophosphate Natural products OCC(O)COP(O)(O)=O AWUCVROLDVIAJX-UHFFFAOYSA-N 0.000 description 1
• BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
• 230000004075 alteration Effects 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 229940043376 ammonium acetate Drugs 0.000 description 1
• 235000019257 ammonium acetate Nutrition 0.000 description 1
• VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
• 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
• 235000011130 ammonium sulphate Nutrition 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 230000000844 anti-bacterial effect Effects 0.000 description 1
• 229940088710 antibiotic agent Drugs 0.000 description 1
• 125000003435 aroyl group Chemical group 0.000 description 1
• 125000005228 aryl sulfonate group Chemical group 0.000 description 1
• 125000005110 aryl thio group Chemical group 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
• 229960001230 asparagine Drugs 0.000 description 1
• 235000009582 asparagine Nutrition 0.000 description 1
• 229940009098 aspartate Drugs 0.000 description 1
• 229960005261 aspartic acid Drugs 0.000 description 1
• 235000003704 aspartic acid Nutrition 0.000 description 1
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
• 239000000440 bentonite Substances 0.000 description 1
• 229910000278 bentonite Inorganic materials 0.000 description 1
• SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
• 229940077388 benzenesulfonate Drugs 0.000 description 1
• SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
• 229940050390 benzoate Drugs 0.000 description 1
• 125000004602 benzodiazinyl group Chemical group N1=NC(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 description 1
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 1
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
• HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-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
• 150000005347 biaryls Chemical group 0.000 description 1
• 125000002619 bicyclic group Chemical group 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
• KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
• 239000004327 boric acid Substances 0.000 description 1
• SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
• 125000005998 bromoethyl group Chemical group 0.000 description 1
• 206010006451 bronchitis Diseases 0.000 description 1
• KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
• 239000011575 calcium 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
• MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
• 239000004202 carbamide Substances 0.000 description 1
• 235000013877 carbamide Nutrition 0.000 description 1
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
• 239000001768 carboxy methyl cellulose Substances 0.000 description 1
• 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
• 150000007942 carboxylates Chemical class 0.000 description 1
• 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
• 239000001913 cellulose Substances 0.000 description 1
• 235000010980 cellulose Nutrition 0.000 description 1
• 229920002678 cellulose Polymers 0.000 description 1
• 206010008323 cervicitis Diseases 0.000 description 1
• PENDGIOBPJLVBT-AMXFZXBBSA-N cethromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)[C@@H](C)C(=O)O[C@@H]([C@]2(OC(=O)N[C@@H]2[C@@H](C)C(=O)[C@H](C)C[C@@]1(C)OCC=CC=1C=C2C=CC=CC2=NC=1)C)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O PENDGIOBPJLVBT-AMXFZXBBSA-N 0.000 description 1
• MTFJSAGADRTKCI-VMPITWQZSA-N chembl77510 Chemical compound O\N=C\C1=CC=CC=N1 MTFJSAGADRTKCI-VMPITWQZSA-N 0.000 description 1
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
• 230000001684 chronic effect Effects 0.000 description 1
• 235000013985 cinnamic acid Nutrition 0.000 description 1
• 229930016911 cinnamic acid Natural products 0.000 description 1
• 235000015165 citric acid Nutrition 0.000 description 1
• AJSDVNKVGFVAQU-BIIVOSGPSA-N cladinose Chemical compound O=CC[C@@](C)(OC)[C@@H](O)[C@H](C)O AJSDVNKVGFVAQU-BIIVOSGPSA-N 0.000 description 1
• 239000012050 conventional carrier Substances 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
• LBJNMUFDOHXDFG-UHFFFAOYSA-N copper;hydrate Chemical compound O.[Cu].[Cu] LBJNMUFDOHXDFG-UHFFFAOYSA-N 0.000 description 1
• 230000008878 coupling Effects 0.000 description 1
• 238000010168 coupling process Methods 0.000 description 1
• 239000006071 cream Substances 0.000 description 1
• YTKRILODNOEEPX-NSCUHMNNSA-N crotyl chloride Chemical compound C\C=C\CCl YTKRILODNOEEPX-NSCUHMNNSA-N 0.000 description 1
• XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
• 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
• XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
• 229960002433 cysteine Drugs 0.000 description 1
• 235000018417 cysteine Nutrition 0.000 description 1
• 238000001212 derivatisation Methods 0.000 description 1
• NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 1
• 150000001983 dialkylethers Chemical class 0.000 description 1
• 150000004985 diamines Chemical class 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
• FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
• ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
• MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical group C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
• 206010013023 diphtheria Diseases 0.000 description 1
• KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
• 239000002270 dispersing agent Substances 0.000 description 1
• POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
• 239000008298 dragée Substances 0.000 description 1
• 235000013601 eggs Nutrition 0.000 description 1
• 239000003974 emollient agent Substances 0.000 description 1
• XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 description 1
• CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
• NWGLEJPMJQYVOY-UHFFFAOYSA-N ethyl 2-(tetrazol-2-yl)acetate Chemical compound CCOC(=O)CN1N=CN=N1 NWGLEJPMJQYVOY-UHFFFAOYSA-N 0.000 description 1
• PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
• FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 238000000605 extraction Methods 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 239000011790 ferrous sulphate Substances 0.000 description 1
• 235000003891 ferrous sulphate Nutrition 0.000 description 1
• 239000000945 filler Substances 0.000 description 1
• 239000007941 film coated tablet Substances 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
• 239000001530 fumaric acid Substances 0.000 description 1
• 235000011087 fumaric acid Nutrition 0.000 description 1
• 125000004615 furo[2,3-b]pyridinyl group Chemical group O1C(=CC=2C1=NC=CC2)* 0.000 description 1
• 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 description 1
• 125000002541 furyl group Chemical group 0.000 description 1
• 239000007789 gas Substances 0.000 description 1
• 229940050410 gluconate Drugs 0.000 description 1
• 229960002989 glutamic acid Drugs 0.000 description 1
• 235000013922 glutamic acid Nutrition 0.000 description 1
• 239000004220 glutamic acid Substances 0.000 description 1
• ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
• 235000004554 glutamine Nutrition 0.000 description 1
• 229960002743 glutamine Drugs 0.000 description 1
• 125000005456 glyceride group Chemical group 0.000 description 1
• 229960002449 glycine Drugs 0.000 description 1
• 239000008187 granular material Substances 0.000 description 1
• 125000001475 halogen functional group Chemical group 0.000 description 1
• 230000002008 hemorrhagic effect Effects 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
• 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 1
• 239000003906 humectant Substances 0.000 description 1
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
• 238000005984 hydrogenation reaction Methods 0.000 description 1
• QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
• 230000007062 hydrolysis Effects 0.000 description 1
• 238000006460 hydrolysis reaction Methods 0.000 description 1
• 150000004679 hydroxides Chemical class 0.000 description 1
• RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
• 125000002632 imidazolidinyl group Chemical group 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 238000011065 in-situ storage Methods 0.000 description 1
• 238000011534 incubation Methods 0.000 description 1
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
• 125000001041 indolyl group Chemical group 0.000 description 1
• 239000003112 inhibitor Substances 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 208000028774 intestinal disease Diseases 0.000 description 1
• 230000000968 intestinal effect Effects 0.000 description 1
• 230000003834 intracellular effect Effects 0.000 description 1
• SURQXAFEQWPFPV-UHFFFAOYSA-L iron(2+) sulfate heptahydrate Chemical compound O.O.O.O.O.O.O.[Fe+2].[O-]S([O-])(=O)=O SURQXAFEQWPFPV-UHFFFAOYSA-L 0.000 description 1
• 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
• SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
• 229960000310 isoleucine Drugs 0.000 description 1
• AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
• 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 description 1
• 125000001786 isothiazolyl group Chemical group 0.000 description 1
• 125000003971 isoxazolinyl group Chemical group 0.000 description 1
• 206010023332 keratitis Diseases 0.000 description 1
• 125000000468 ketone group Chemical group 0.000 description 1
• 229940001447 lactate Drugs 0.000 description 1
• 239000004310 lactic acid Substances 0.000 description 1
• 235000014655 lactic acid Nutrition 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
• 229940115932 legionella pneumophila Drugs 0.000 description 1
• 229960003136 leucine Drugs 0.000 description 1
• 244000144972 livestock Species 0.000 description 1
• 239000006210 lotion Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
• 150000007931 macrolactones Chemical group 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
• 239000001630 malic acid Substances 0.000 description 1
• 235000011090 malic acid Nutrition 0.000 description 1
• 229960002510 mandelic acid Drugs 0.000 description 1
• 230000001404 mediated effect Effects 0.000 description 1
• 229940098779 methanesulfonic acid Drugs 0.000 description 1
• 229930182817 methionine Natural products 0.000 description 1
• 229960004452 methionine Drugs 0.000 description 1
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
• 229920000609 methyl cellulose Polymers 0.000 description 1
• WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
• 239000001923 methylcellulose Substances 0.000 description 1
• 235000010981 methylcellulose Nutrition 0.000 description 1
• 239000002480 mineral oil Substances 0.000 description 1
• 235000010446 mineral oil Nutrition 0.000 description 1
• 238000002156 mixing Methods 0.000 description 1
• 239000002808 molecular sieve Substances 0.000 description 1
• 125000002757 morpholinyl group Chemical group 0.000 description 1
• 229940013390 mycoplasma pneumoniae Drugs 0.000 description 1
• NNKPHNTWNILINE-UHFFFAOYSA-N n-cyclopropyl-3-fluoro-4-methyl-5-[3-[[1-[2-[2-(methylamino)ethoxy]phenyl]cyclopropyl]amino]-2-oxopyrazin-1-yl]benzamide Chemical compound CNCCOC1=CC=CC=C1C1(NC=2C(N(C=3C(=C(F)C=C(C=3)C(=O)NC3CC3)C)C=CN=2)=O)CC1 NNKPHNTWNILINE-UHFFFAOYSA-N 0.000 description 1
• 125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 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
• 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
• 230000017074 necrotic cell death Effects 0.000 description 1
• 235000001968 nicotinic acid Nutrition 0.000 description 1
• 239000011664 nicotinic acid Substances 0.000 description 1
• 150000002823 nitrates Chemical class 0.000 description 1
• 229910017604 nitric acid Inorganic materials 0.000 description 1
• 231100000252 nontoxic Toxicity 0.000 description 1
• 230000003000 nontoxic effect Effects 0.000 description 1
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
• 239000007764 o/w emulsion Substances 0.000 description 1
• 239000002674 ointment Substances 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
• 229940049964 oleate Drugs 0.000 description 1
• 238000000424 optical density measurement Methods 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 150000007530 organic bases Chemical class 0.000 description 1
• 239000003960 organic solvent Substances 0.000 description 1
• 235000006408 oxalic acid Nutrition 0.000 description 1
• SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 description 1
• 125000003145 oxazol-4-yl group Chemical group O1C=NC(=C1)* 0.000 description 1
• 125000000160 oxazolidinyl group Chemical group 0.000 description 1
• 125000005968 oxazolinyl group Chemical group 0.000 description 1
• AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
• 150000002921 oxetanes Chemical class 0.000 description 1
• 125000005476 oxopyrrolidinyl group Chemical group 0.000 description 1
• 239000001301 oxygen Substances 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
• MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
• YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
• FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
• 244000052769 pathogen Species 0.000 description 1
• 125000001147 pentyl group Chemical group C(CCCC)* 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
• 230000000144 pharmacologic effect Effects 0.000 description 1
• 239000003444 phase transfer catalyst Substances 0.000 description 1
• PJANUNZPZUHMPM-UHFFFAOYSA-N phenyl 2-phenoxyacetate Chemical compound C=1C=CC=CC=1OC(=O)COC1=CC=CC=C1 PJANUNZPZUHMPM-UHFFFAOYSA-N 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
• 229960005190 phenylalanine Drugs 0.000 description 1
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-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
• 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
• 229940075930 picrate Drugs 0.000 description 1
• OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
• 229950010765 pivalate Drugs 0.000 description 1
• 229920001184 polypeptide Polymers 0.000 description 1
• 229920000136 polysorbate Polymers 0.000 description 1
• 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
• 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
• 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
• 229910000027 potassium carbonate Inorganic materials 0.000 description 1
• 229910000160 potassium phosphate Inorganic materials 0.000 description 1
• 235000011009 potassium phosphates Nutrition 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 238000004237 preparative chromatography Methods 0.000 description 1
• 108090000765 processed proteins & peptides Proteins 0.000 description 1
• 102000004196 processed proteins & peptides Human genes 0.000 description 1
• 229960002429 proline Drugs 0.000 description 1
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
• 230000000069 prophylactic effect Effects 0.000 description 1
• 235000019260 propionic acid Nutrition 0.000 description 1
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
• 230000001681 protective effect Effects 0.000 description 1
• 125000003373 pyrazinyl group Chemical group 0.000 description 1
• 125000002755 pyrazolinyl group Chemical group 0.000 description 1
• ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
• NRTYMEPCRDJMPZ-UHFFFAOYSA-N pyridine;2,2,2-trifluoroacetic acid Chemical compound C1=CC=NC=C1.OC(=O)C(F)(F)F NRTYMEPCRDJMPZ-UHFFFAOYSA-N 0.000 description 1
• 125000006513 pyridinyl methyl group Chemical group 0.000 description 1
• 125000004076 pyridyl group Chemical group 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 229940107700 pyruvic acid Drugs 0.000 description 1
• 238000010791 quenching Methods 0.000 description 1
• 230000000171 quenching effect Effects 0.000 description 1
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
• IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 238000001953 recrystallisation Methods 0.000 description 1
• 238000012552 review Methods 0.000 description 1
• 201000003068 rheumatic fever Diseases 0.000 description 1
• 125000006413 ring segment Chemical group 0.000 description 1
• 229960004889 salicylic acid Drugs 0.000 description 1
• XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 229960001153 serine Drugs 0.000 description 1
• 229940099992 seromycin Drugs 0.000 description 1
• 239000002453 shampoo Substances 0.000 description 1
• 238000007493 shaping process Methods 0.000 description 1
• ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
• 239000004208 shellac Substances 0.000 description 1
• 235000013874 shellac Nutrition 0.000 description 1
• 229940113147 shellac Drugs 0.000 description 1
• RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
• 235000012239 silicon dioxide Nutrition 0.000 description 1
• 201000009890 sinusitis Diseases 0.000 description 1
• 201000010153 skin papilloma Diseases 0.000 description 1
• 208000021795 small intestine disease Diseases 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
• 235000010413 sodium alginate Nutrition 0.000 description 1
• 239000000661 sodium alginate Substances 0.000 description 1
• 229940005550 sodium alginate Drugs 0.000 description 1
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
• WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 235000009518 sodium iodide Nutrition 0.000 description 1
• UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical class [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
• 239000007909 solid dosage form Substances 0.000 description 1
• 238000000935 solvent evaporation Methods 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 229940115922 streptococcus uberis Drugs 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
• 239000011593 sulfur Substances 0.000 description 1
• 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
• 229910021653 sulphate ion Inorganic materials 0.000 description 1
• 239000000829 suppository Substances 0.000 description 1
• 239000004094 surface-active agent Substances 0.000 description 1
• 208000024891 symptom Diseases 0.000 description 1
• 208000011580 syndromic disease Diseases 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 230000009885 systemic effect Effects 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 239000011975 tartaric acid Substances 0.000 description 1
• 235000002906 tartaric acid Nutrition 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• LJVAJPDWBABPEJ-PNUFFHFMSA-N telithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)[C@@H](C)C(=O)O[C@@H]([C@]2(OC(=O)N(CCCCN3C=C(N=C3)C=3C=NC=CC=3)[C@@H]2[C@@H](C)C(=O)[C@H](C)C[C@@]1(C)OC)C)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O LJVAJPDWBABPEJ-PNUFFHFMSA-N 0.000 description 1
• 229960003250 telithromycin Drugs 0.000 description 1
• UJJDEOLXODWCGK-UHFFFAOYSA-N tert-butyl carbonochloridate Chemical compound CC(C)(C)OC(Cl)=O UJJDEOLXODWCGK-UHFFFAOYSA-N 0.000 description 1
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 238000010998 test method Methods 0.000 description 1
• DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
• 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
• 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 230000001225 therapeutic effect Effects 0.000 description 1
• 125000001113 thiadiazolyl group Chemical group 0.000 description 1
• AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
• 125000001984 thiazolidinyl group Chemical group 0.000 description 1
• 125000000335 thiazolyl group Chemical group 0.000 description 1
• 125000004589 thienofuryl group Chemical group O1C(=CC2=C1C=CS2)* 0.000 description 1
• 125000004587 thienothienyl group Chemical group S1C(=CC2=C1C=CS2)* 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 125000003396 thiol group Chemical class [H]S* 0.000 description 1
• 150000003573 thiols Chemical class 0.000 description 1
• 229960002898 threonine Drugs 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
• 206010044008 tonsillitis Diseases 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 239000012049 topical pharmaceutical composition Substances 0.000 description 1
• 231100000419 toxicity Toxicity 0.000 description 1
• 230000001988 toxicity Effects 0.000 description 1
• 239000003053 toxin Substances 0.000 description 1
• 231100000765 toxin Toxicity 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• 125000005208 trialkylammonium group Chemical group 0.000 description 1
• 125000004306 triazinyl group Chemical group 0.000 description 1
• DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
• 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
• UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 229960004441 tyrosine Drugs 0.000 description 1
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
• 231100000397 ulcer Toxicity 0.000 description 1
• JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
• ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
• 208000000143 urethritis Diseases 0.000 description 1
• 229960004295 valine Drugs 0.000 description 1
• 239000004474 valine Substances 0.000 description 1
• 235000013311 vegetables Nutrition 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
• 239000008096 xylene Substances 0.000 description 1