NZ545157A - Isothiazoloquinolones and related compounds as anti-infective agents - Google Patents

Info

Publication number

NZ545157A

NZ545157A NZ545157A NZ54515704A NZ545157A NZ 545157 A NZ545157 A NZ 545157A NZ 545157 A NZ545157 A NZ 545157A NZ 54515704 A NZ54515704 A NZ 54515704A NZ 545157 A NZ545157 A NZ 545157A

Authority

NZ

New Zealand

Prior art keywords

cyclopropyl

fluoro

isothiazolo

dione

quinoline

Prior art date

2003-08-12

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 345
• 239000004599 antimicrobial Substances 0.000 title claims description 13
• QXHKKCITURTUFC-UHFFFAOYSA-N [1,2]thiazolo[3,4-h]quinoline 8-oxide Chemical class C1=CN=C2C3=CS(=O)N=C3C=CC2=C1 QXHKKCITURTUFC-UHFFFAOYSA-N 0.000 title description 3
• 229960005475 antiinfective agent Drugs 0.000 title description 2
• 150000003839 salts Chemical class 0.000 claims abstract description 175
• 239000000203 mixture Substances 0.000 claims abstract description 105
• 208000015181 infectious disease Diseases 0.000 claims abstract description 35
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 28
• 241001465754 Metazoa Species 0.000 claims abstract description 23
• 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 18
• 230000001580 bacterial effect Effects 0.000 claims abstract description 16
• 239000003085 diluting agent Substances 0.000 claims abstract description 14
• KTUXZCJQJNQPPH-UHFFFAOYSA-N quinoline-3,4-dione Chemical compound C1=CC=C2C(=O)C(=O)C=NC2=C1 KTUXZCJQJNQPPH-UHFFFAOYSA-N 0.000 claims description 451
• -1 or R2 is C1 -C^alkyl Chemical group 0.000 claims description 264
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 210
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 126
• 125000001424 substituent group Chemical group 0.000 claims description 116
• 229910052736 halogen Inorganic materials 0.000 claims description 111
• 150000002367 halogens Chemical class 0.000 claims description 111
• 125000003118 aryl group Chemical group 0.000 claims description 109
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 91
• 125000003282 alkyl amino group Chemical group 0.000 claims description 82
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 65
• 125000004076 pyridyl group Chemical group 0.000 claims description 56
• 239000001257 hydrogen Substances 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 125000001544 thienyl group Chemical group 0.000 claims description 50
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
• 229910052799 carbon Inorganic materials 0.000 claims description 47
• 229910052757 nitrogen Inorganic materials 0.000 claims description 45
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 43
• 125000003386 piperidinyl group Chemical group 0.000 claims description 39
• 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 34
• 229920006395 saturated elastomer Polymers 0.000 claims description 33
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 32
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 31
• 150000002431 hydrogen Chemical group 0.000 claims description 31
• 125000001624 naphthyl group Chemical group 0.000 claims description 31
• 125000002541 furyl group Chemical group 0.000 claims description 30
• 125000004193 piperazinyl group Chemical group 0.000 claims description 30
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 30
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 30
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 28
• 125000002757 morpholinyl group Chemical group 0.000 claims description 28
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 28
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 28
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 27
• 125000002883 imidazolyl group Chemical group 0.000 claims description 27
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 27
• 125000001041 indolyl group Chemical group 0.000 claims description 24
• 125000004043 oxo group Chemical group O=* 0.000 claims description 24
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 24
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 24
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 22
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 21
• 244000005700 microbiome Species 0.000 claims description 21
• 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 20
• 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 20
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 20
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 20
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 20
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 20
• 150000001721 carbon Chemical group 0.000 claims description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 229910052717 sulfur Inorganic materials 0.000 claims description 19
• 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 18
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 17
• 241000588724 Escherichia coli Species 0.000 claims description 17
• 125000002619 bicyclic group Chemical group 0.000 claims description 16
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
• 208000035143 Bacterial infection Diseases 0.000 claims description 15
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 15
• 239000003937 drug carrier Substances 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 12
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 11
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 11
• 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 10
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 10
• 125000001153 fluoro group Chemical group F* 0.000 claims description 10
• 230000000844 anti-bacterial effect Effects 0.000 claims description 9
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• 239000003112 inhibitor Substances 0.000 claims description 9
• 239000006188 syrup Substances 0.000 claims description 9
• 235000020357 syrup Nutrition 0.000 claims description 9
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 9
• 229940121375 antifungal agent Drugs 0.000 claims description 8
• 125000002837 carbocyclic group Chemical group 0.000 claims description 8
• 125000005046 dihydronaphthyl 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
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 8
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
• 239000003781 beta lactamase inhibitor Substances 0.000 claims description 7
• 229940126813 beta-lactamase inhibitor Drugs 0.000 claims description 7
• 239000006071 cream Substances 0.000 claims description 7
• 208000028172 protozoa infectious disease Diseases 0.000 claims description 7
• 229920002554 vinyl polymer Polymers 0.000 claims description 7
• PITNYQCGMBCGQX-UHFFFAOYSA-N [1,2]thiazolo[5,4-b]quinoline Chemical compound C1=CC=C2C=C3C=NSC3=NC2=C1 PITNYQCGMBCGQX-UHFFFAOYSA-N 0.000 claims description 6
• 239000003242 anti bacterial agent Substances 0.000 claims description 6
• 239000003443 antiviral agent Substances 0.000 claims description 6
• 239000002775 capsule Substances 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
• 102000014150 Interferons Human genes 0.000 claims description 5
• 108010050904 Interferons Proteins 0.000 claims description 5
• 239000003429 antifungal agent Substances 0.000 claims description 5
• 239000003904 antiprotozoal agent Substances 0.000 claims description 5
• 229940079322 interferon Drugs 0.000 claims description 5
• 229940126085 β‑Lactamase Inhibitor Drugs 0.000 claims description 5
• 239000000443 aerosol Substances 0.000 claims description 4
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
• 239000012530 fluid Substances 0.000 claims description 3
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 3
• 229940054534 ophthalmic solution Drugs 0.000 claims description 3
• 239000002997 ophthalmic solution Substances 0.000 claims description 3
• 239000006187 pill Substances 0.000 claims description 3
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 3
• 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 3
• 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 3
• YMFUFNCNIHAZOD-UHFFFAOYSA-N (9-cyclopropyl-6-fluoro-4-oxo-7-pyridin-4-yl-[1,2]thiazolo[5,4-b]quinolin-3-yl) acetate Chemical compound C12=CC(C=3C=CN=CC=3)=C(F)C=C2C(=O)C=2C(OC(=O)C)=NSC=2N1C1CC1 YMFUFNCNIHAZOD-UHFFFAOYSA-N 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• VFPBQKKMMFDEGW-UHFFFAOYSA-N 3-[6-fluoro-9-(2-fluorocyclopropyl)-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl]benzonitrile Chemical compound FC1CC1N1C2=CC(C=3C=C(C=CC=3)C#N)=C(F)C=C2C(=O)C2=C1SNC2=O VFPBQKKMMFDEGW-UHFFFAOYSA-N 0.000 claims description 2
• OUAOQRPICPBFFR-UHFFFAOYSA-N 4-(9-cyclopropyl-6-fluoro-3,4-dioxo-7-pyridin-4-yl-[1,2]thiazolo[5,4-b]quinolin-2-yl)butanoic acid Chemical compound C12=CC(C=3C=CN=CC=3)=C(F)C=C2C(=O)C=2C(=O)N(CCCC(=O)O)SC=2N1C1CC1 OUAOQRPICPBFFR-UHFFFAOYSA-N 0.000 claims description 2
• KRGWTBPYXBSDKE-UHFFFAOYSA-N 9-(2,4-difluorophenyl)-7-[4-(dimethylamino)phenyl]-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=CC(N(C)C)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1=CC=C(F)C=C1F KRGWTBPYXBSDKE-UHFFFAOYSA-N 0.000 claims description 2
• VSJDXWLCKGBBNW-UHFFFAOYSA-N 9-cyclopropyl-7-(2,6-dimethylpyridin-4-yl)-6-fluoro-5-(2-methylhydrazinyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=2SNC(=O)C=2C(=O)C=2C(NNC)=C(F)C(C=3C=C(C)N=C(C)C=3)=CC=2N1C1CC1 VSJDXWLCKGBBNW-UHFFFAOYSA-N 0.000 claims description 2
• 229940080818 propionamide Drugs 0.000 claims description 2
• MDGXQGMSNOEFRL-UHFFFAOYSA-N quinoline-3,4-dione;hydrochloride Chemical compound Cl.C1=CC=C2C(=O)C(=O)C=NC2=C1 MDGXQGMSNOEFRL-UHFFFAOYSA-N 0.000 claims 2
• GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims 1
• ZRCJWJQMAZNENO-UHFFFAOYSA-N 5-(9-cyclopropyl-6-fluoro-8-methoxy-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)pyridine-3-carbonitrile Chemical compound COC1=C(C=2C=C(C=NC=2)C#N)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 ZRCJWJQMAZNENO-UHFFFAOYSA-N 0.000 claims 1
• NTUOATLYEYSMOS-UHFFFAOYSA-N 5-(9-cyclopropyl-8-methoxy-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)pyridine-3-carbonitrile Chemical compound COC1=C(C=2C=C(C=NC=2)C#N)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 NTUOATLYEYSMOS-UHFFFAOYSA-N 0.000 claims 1
• BBEQQKBWUHCIOU-UHFFFAOYSA-N 5-(dimethylamino)-1-naphthalenesulfonic acid(dansyl acid) Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(O)(=O)=O BBEQQKBWUHCIOU-UHFFFAOYSA-N 0.000 claims 1
• LNYWHTDBPMBNAO-UHFFFAOYSA-N 7-(3-amino-4-fluorophenyl)-9-cyclopropyl-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=C(N)C(F)=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 LNYWHTDBPMBNAO-UHFFFAOYSA-N 0.000 claims 1
• PIDLDQFJQGROER-UHFFFAOYSA-N 7-(4-aminophenyl)-9-cyclopropyl-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=CC(N)=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 PIDLDQFJQGROER-UHFFFAOYSA-N 0.000 claims 1
• VOAQVXWNOGWSFO-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-fluoropyridin-3-yl)-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C(=NC=CC=2)F)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 VOAQVXWNOGWSFO-UHFFFAOYSA-N 0.000 claims 1
• NQSXOHVUWDFYMG-NUGSKGIGSA-N 9-cyclopropyl-6-fluoro-7-[2-[(e)-methoxyiminomethyl]pyridin-4-yl]-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=NC(/C=N/OC)=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 NQSXOHVUWDFYMG-NUGSKGIGSA-N 0.000 claims 1
• LYOJRODQNKBRCL-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-8-methoxy-7-(1,2,3,4-tetrahydroisoquinolin-6-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=C3CCNCC3=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 LYOJRODQNKBRCL-UHFFFAOYSA-N 0.000 claims 1
• XWDPBLFYPNKPFN-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-8-methoxy-7-(2-methylpyridin-4-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=C(C)N=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 XWDPBLFYPNKPFN-UHFFFAOYSA-N 0.000 claims 1
• HGYNYEDGSXCFRE-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-8-methoxy-7-pyridin-3-yl-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=NC=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 HGYNYEDGSXCFRE-UHFFFAOYSA-N 0.000 claims 1
• GNXNNHJBAIQWRQ-UHFFFAOYSA-N 9-cyclopropyl-7-(2-fluoropyridin-4-yl)-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=C(F)N=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 GNXNNHJBAIQWRQ-UHFFFAOYSA-N 0.000 claims 1
• ZGOQRPMSUJXOCY-UHFFFAOYSA-N 9-cyclopropyl-7-(3-hydroxyphenyl)-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=C(O)C=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 ZGOQRPMSUJXOCY-UHFFFAOYSA-N 0.000 claims 1
• KDIOWONNUCSWJF-UHFFFAOYSA-N 9-cyclopropyl-7-isoquinolin-6-yl-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=C3C=CN=CC3=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 KDIOWONNUCSWJF-UHFFFAOYSA-N 0.000 claims 1
• WBWUYPBFCIMNRV-UHFFFAOYSA-N 9-cyclopropyl-8-(difluoromethoxy)-7-(3-methyl-2,3-dihydro-1h-isoindol-5-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C2C(C)NCC2=CC=C1C(C=1OC(F)F)=CC=C(C(C=2C(=O)NSC=22)=O)C=1N2C1CC1 WBWUYPBFCIMNRV-UHFFFAOYSA-N 0.000 claims 1
• BLSBIMBTHJSKBO-UHFFFAOYSA-N 9-cyclopropyl-8-methoxy-7-(1,2,3,4-tetrahydroisoquinolin-6-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=C3CCNCC3=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 BLSBIMBTHJSKBO-UHFFFAOYSA-N 0.000 claims 1
• IKXBSMDTDLPARG-UHFFFAOYSA-N 9-cyclopropyl-8-methoxy-7-pyridin-3-yl-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=NC=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 IKXBSMDTDLPARG-UHFFFAOYSA-N 0.000 claims 1
• 229920006358 Fluon Polymers 0.000 claims 1
• QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims 1
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
• MMCIXNVRVDTQSG-UHFFFAOYSA-N quinoline-7-carboxamide Chemical compound C1=CC=NC2=CC(C(=O)N)=CC=C21 MMCIXNVRVDTQSG-UHFFFAOYSA-N 0.000 claims 1
• 230000000845 anti-microbial effect Effects 0.000 abstract description 18
• 230000000813 microbial effect Effects 0.000 abstract description 16
• 239000000543 intermediate Substances 0.000 abstract description 15
• 239000013543 active substance Substances 0.000 abstract description 13
• 239000000969 carrier Substances 0.000 abstract description 6
• 230000003389 potentiating effect Effects 0.000 abstract description 5
• 108020000946 Bacterial DNA Proteins 0.000 abstract description 2
• 230000006820 DNA synthesis Effects 0.000 abstract description 2
• 229940124639 Selective inhibitor Drugs 0.000 abstract description 2
• 230000010076 replication Effects 0.000 abstract description 2
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 245
• 238000005481 NMR spectroscopy Methods 0.000 description 81
• 238000005160 1H NMR spectroscopy Methods 0.000 description 76
• 239000000243 solution Substances 0.000 description 65
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 46
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 38
• 238000000034 method Methods 0.000 description 36
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 35
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 35
• 125000000217 alkyl group Chemical group 0.000 description 35
• 239000007787 solid Substances 0.000 description 32
• 210000004027 cell Anatomy 0.000 description 30
• 238000002360 preparation method Methods 0.000 description 28
• 239000011541 reaction mixture Substances 0.000 description 26
• 239000000047 product Substances 0.000 description 24
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 23
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 23
• 125000004432 carbon atom Chemical group C* 0.000 description 21
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 21
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