IL199081A - Quinoline history of antibacterial - Google Patents

Info

Publication number

IL199081A

IL199081A IL199081A IL19908109A IL199081A IL 199081 A IL199081 A IL 199081A IL 199081 A IL199081 A IL 199081A IL 19908109 A IL19908109 A IL 19908109A IL 199081 A IL199081 A IL 199081A

Authority

IL

Israel

Prior art keywords

alkyl

aryl

compound according

het

mono

Prior art date

2006-12-06

Links

• Espacenet
• Global Dossier
• Discuss

• 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 title claims description 20
• 230000000844 anti-bacterial effect Effects 0.000 title description 12
• 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 title description 10
• 150000001875 compounds Chemical class 0.000 claims description 284
• -1 cyano, formyl Chemical group 0.000 claims description 223
• 125000001424 substituent group Chemical group 0.000 claims description 80
• 125000005843 halogen group Chemical group 0.000 claims description 75
• 125000000217 alkyl group Chemical group 0.000 claims description 74
• 125000003118 aryl group Chemical group 0.000 claims description 69
• 229910052739 hydrogen Inorganic materials 0.000 claims description 50
• 239000001257 hydrogen Substances 0.000 claims description 50
• 238000000034 method Methods 0.000 claims description 47
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 46
• 239000002904 solvent Substances 0.000 claims description 43
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
• 239000003814 drug Substances 0.000 claims description 40
• 239000000203 mixture Substances 0.000 claims description 40
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 39
• 238000011282 treatment Methods 0.000 claims description 36
• 125000003545 alkoxy group Chemical group 0.000 claims description 35
• 125000004076 pyridyl group Chemical group 0.000 claims description 32
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 32
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 31
• 238000002360 preparation method Methods 0.000 claims description 31
• 229910052757 nitrogen Inorganic materials 0.000 claims description 29
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 28
• 125000001188 haloalkyl group Chemical group 0.000 claims description 28
• 208000035143 Bacterial infection Diseases 0.000 claims description 27
• 241000894006 Bacteria Species 0.000 claims description 26
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 25
• 125000004414 alkyl thio group Chemical group 0.000 claims description 24
• 239000002585 base Substances 0.000 claims description 24
• 239000003242 anti bacterial agent Substances 0.000 claims description 23
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
• 125000002883 imidazolyl group Chemical group 0.000 claims description 22
• 208000015181 infectious disease Diseases 0.000 claims description 22
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
• 239000002253 acid Substances 0.000 claims description 21
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 21
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 20
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 20
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 20
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 20
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 15
• 125000001246 bromo group Chemical group Br* 0.000 claims description 15
• 125000001624 naphthyl group Chemical group 0.000 claims description 15
• 125000001425 triazolyl group Chemical group 0.000 claims description 15
• 150000001204 N-oxides Chemical class 0.000 claims description 14
• 241000191967 Staphylococcus aureus Species 0.000 claims description 14
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
• 239000008194 pharmaceutical composition Substances 0.000 claims description 14
• 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 14
• 125000004306 triazinyl group Chemical group 0.000 claims description 14
• 125000005943 1,2,3,6-tetrahydropyridyl group Chemical group 0.000 claims description 13
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 13
• 125000003386 piperidinyl group Chemical group 0.000 claims description 13
• 125000001422 pyrrolinyl group Chemical group 0.000 claims description 13
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 13
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 12
• 239000012453 solvate Substances 0.000 claims description 11
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 10
• 125000002757 morpholinyl group Chemical group 0.000 claims description 10
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 9
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 9
• 239000004480 active ingredient Substances 0.000 claims description 8
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 8
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 8
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000002541 furyl group Chemical group 0.000 claims description 8
• 125000002950 monocyclic group Chemical group 0.000 claims description 8
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
• 125000001544 thienyl group Chemical group 0.000 claims description 8
• 241000193998 Streptococcus pneumoniae Species 0.000 claims description 7
• 150000001412 amines Chemical group 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
• RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims description 6
• 125000004104 aryloxy group Chemical group 0.000 claims description 6
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
• 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
• 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
• 125000005605 benzo group Chemical group 0.000 claims description 6
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 125000000597 dioxinyl group Chemical group 0.000 claims description 6
• 125000001041 indolyl group Chemical group 0.000 claims description 6
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
• 229960003085 meticillin Drugs 0.000 claims description 6
• 125000002971 oxazolyl group Chemical group 0.000 claims description 6
• 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 5
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
• 125000005418 aryl aryl group Chemical group 0.000 claims description 5
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 5
• 231100000252 nontoxic Toxicity 0.000 claims description 5
• 230000003000 nontoxic effect Effects 0.000 claims description 5
• 229940031000 streptococcus pneumoniae Drugs 0.000 claims description 5
• 125000002393 azetidinyl group Chemical group 0.000 claims description 4
• 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 3
• 239000003513 alkali Substances 0.000 claims description 3
• 125000005094 alkyl carbonyl amino alkyl group Chemical group 0.000 claims description 3
• 201000005010 Streptococcus pneumonia Diseases 0.000 claims description 2
• 239000012458 free base Substances 0.000 claims description 2
• UXAWXZDXVOYLII-UHFFFAOYSA-N tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate Chemical compound C1C2N(C(=O)OC(C)(C)C)CC1NC2 UXAWXZDXVOYLII-UHFFFAOYSA-N 0.000 claims description 2
• 230000009466 transformation Effects 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 claims 1
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
• 125000000815 N-oxide group Chemical group 0.000 claims 1
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims 1
• 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims 1
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
• 238000000844 transformation Methods 0.000 claims 1
• 239000000543 intermediate Substances 0.000 description 74
• 238000006243 chemical reaction Methods 0.000 description 49
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 32
• 201000008827 tuberculosis Diseases 0.000 description 30
• 229940079593 drug Drugs 0.000 description 28
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 230000001580 bacterial effect Effects 0.000 description 21
• 125000004432 carbon atom Chemical group C* 0.000 description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
• 239000003795 chemical substances by application Substances 0.000 description 14
• 244000052616 bacterial pathogen Species 0.000 description 13
• 125000004122 cyclic group Chemical group 0.000 description 13
• 230000000694 effects Effects 0.000 description 13
• 229930195734 saturated hydrocarbon Natural products 0.000 description 13
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
• 239000002054 inoculum Substances 0.000 description 11
• 230000002285 radioactive effect Effects 0.000 description 11
• 229910052799 carbon Inorganic materials 0.000 description 10
• 239000003054 catalyst Substances 0.000 description 10
• 229940126214 compound 3 Drugs 0.000 description 10
• 239000000243 solution Substances 0.000 description 10
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
• 238000010790 dilution Methods 0.000 description 9
• 239000012895 dilution Substances 0.000 description 9
• 201000010099 disease Diseases 0.000 description 9
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
• 201000009671 multidrug-resistant tuberculosis Diseases 0.000 description 9
• 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 description 8
• 238000012360 testing method Methods 0.000 description 8
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
• 241000295644 Staphylococcaceae Species 0.000 description 7
• 239000003153 chemical reaction reagent Substances 0.000 description 7
• 229940073584 methylene chloride Drugs 0.000 description 7
• 208000027531 mycobacterial infectious disease Diseases 0.000 description 7
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• 206010062207 Mycobacterial infection Diseases 0.000 description 6
• 241000187479 Mycobacterium tuberculosis Species 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 125000004429 atom Chemical group 0.000 description 6
• 125000001309 chloro group Chemical group Cl* 0.000 description 6
• 150000002978 peroxides Chemical class 0.000 description 6
• XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical group OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 6
• IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 6
• XXQBEVHPUKOQEO-UHFFFAOYSA-N potassium superoxide Chemical compound [K+].[K+].[O-][O-] XXQBEVHPUKOQEO-UHFFFAOYSA-N 0.000 description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
• 150000007513 acids Chemical class 0.000 description 5
• 125000003277 amino group Chemical group 0.000 description 5
• 238000003556 assay Methods 0.000 description 5
• 230000003115 biocidal effect Effects 0.000 description 5
• 150000001721 carbon Chemical group 0.000 description 5
• 125000004093 cyano group Chemical group *C#N 0.000 description 5
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 5
• 229930195733 hydrocarbon Natural products 0.000 description 5
• 239000003120 macrolide antibiotic agent Substances 0.000 description 5
• 229940041033 macrolides Drugs 0.000 description 5
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
• 239000000725 suspension Substances 0.000 description 5
• WMFHVNYOCKTDMX-UHFFFAOYSA-N 3-benzyl-6-bromo-2-methoxyquinoline Chemical compound COC1=NC2=CC=C(Br)C=C2C=C1CC1=CC=CC=C1 WMFHVNYOCKTDMX-UHFFFAOYSA-N 0.000 description 4
• 108010065839 Capreomycin Proteins 0.000 description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
• DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-N 0.000 description 4
• DYDCUQKUCUHJBH-UHFFFAOYSA-N D-Cycloserine Natural products NC1CONC1=O DYDCUQKUCUHJBH-UHFFFAOYSA-N 0.000 description 4
• MVTQIFVKRXBCHS-SMMNFGSLSA-N N-[(3S,6S,12R,15S,16R,19S,22S)-3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentazatricyclo[20.4.0.06,10]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide (10R,11R,12E,17E,19E,21S)-21-hydroxy-11,19-dimethyl-10-propan-2-yl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.03,7]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone Chemical compound CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)c2coc(CC(=O)C[C@H](O)\C=C(/C)\C=C\CNC(=O)\C=C\[C@H]1C)n2.CC[C@H]1NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@@H]2CC(=O)CCN2C(=O)[C@H](Cc2ccccc2)N(C)C(=O)[C@@H]2CCCN2C1=O)c1ccccc1 MVTQIFVKRXBCHS-SMMNFGSLSA-N 0.000 description 4
• 229930182555 Penicillin Natural products 0.000 description 4
• JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
• 150000001298 alcohols Chemical class 0.000 description 4
• 229960003077 cycloserine Drugs 0.000 description 4
• 230000034994 death Effects 0.000 description 4
• 231100000517 death Toxicity 0.000 description 4
• 239000002552 dosage form Substances 0.000 description 4
• AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 description 4
• 238000011534 incubation Methods 0.000 description 4
• 230000002401 inhibitory effect Effects 0.000 description 4
• 230000005764 inhibitory process Effects 0.000 description 4
• 238000011081 inoculation Methods 0.000 description 4
• 150000002576 ketones Chemical class 0.000 description 4
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
• 239000002547 new drug Substances 0.000 description 4
• 239000002777 nucleoside Substances 0.000 description 4
• 239000012044 organic layer Substances 0.000 description 4
• 229910052760 oxygen Inorganic materials 0.000 description 4
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
• 239000000047 product Substances 0.000 description 4
• QJBZDBLBQWFTPZ-UHFFFAOYSA-N pyrrolnitrin Chemical compound [O-][N+](=O)C1=C(Cl)C=CC=C1C1=CNC=C1Cl QJBZDBLBQWFTPZ-UHFFFAOYSA-N 0.000 description 4
• 239000007787 solid Substances 0.000 description 4
• 239000007858 starting material Substances 0.000 description 4
• UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
• 239000003826 tablet Substances 0.000 description 4
• VCOPTHOUUNAYKQ-WBTCAYNUSA-N (3s)-3,6-diamino-n-[[(2s,5s,8e,11s,15s)-15-amino-11-[(6r)-2-amino-1,4,5,6-tetrahydropyrimidin-6-yl]-8-[(carbamoylamino)methylidene]-2-(hydroxymethyl)-3,6,9,12,16-pentaoxo-1,4,7,10,13-pentazacyclohexadec-5-yl]methyl]hexanamide;(3s)-3,6-diamino-n-[[(2s,5s,8 Chemical compound N1C(=O)\C(=C/NC(N)=O)NC(=O)[C@H](CNC(=O)C[C@@H](N)CCCN)NC(=O)[C@H](C)NC(=O)[C@@H](N)CNC(=O)[C@@H]1[C@@H]1NC(N)=NCC1.N1C(=O)\C(=C/NC(N)=O)NC(=O)[C@H](CNC(=O)C[C@@H](N)CCCN)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CNC(=O)[C@@H]1[C@@H]1NC(N)=NCC1 VCOPTHOUUNAYKQ-WBTCAYNUSA-N 0.000 description 3
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 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
• 241000186362 Mycobacterium leprae Species 0.000 description 3
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
• KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 3
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
• 229910052783 alkali metal Inorganic materials 0.000 description 3
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