SK302004A3 - Heterocyklické zlúčeniny a ich použitie ako inhibítory D-Ala-D-Ala ligázy - Google Patents

Heterocyklické zlúčeniny a ich použitie ako inhibítory D-Ala-D-Ala ligázy Download PDF

Info

Publication number: SK302004A3
Authority: SK; Slovakia
Prior art keywords: group; alkyl; aryl; compound; hydrogen
Prior art date: 2001-06-28

Application number

SK30-2004A

Other languages

English (en)

Slovak (sk)

Inventor

Scott T. Moe

Paul J. Ala

Emanuele Perola

Carlos H. Faerman

Jacob J. Clement

Janid A. Ali

Paul M. Will

Salvatore A. Marchese

Andrew S. Magee

John V. Gazzaniga

Christopher Farady

Manuel A. Navia

Patrick R. Connelly

Original Assignee

Pliva, D.D.

Priority date (The priority date 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 date listed.)

2001-06-28

Filing date

2002-06-28

Publication date

2005-07-01

2002-06-28 Application filed by Pliva, D.D. filed Critical Pliva, D.D.

2005-07-01 Publication of SK302004A3 publication Critical patent/SK302004A3/sk

Links

108020003338 D-alanine-D-alanine ligase Proteins 0.000 title claims abstract description 25
150000002391 heterocyclic compounds Chemical class 0.000 title abstract description 10
239000000436 ligase inhibitor Substances 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 239
230000001580 bacterial effect Effects 0.000 claims abstract description 35
238000000034 method Methods 0.000 claims description 84
125000000524 functional group Chemical group 0.000 claims description 46
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 44
-1 amino, hydroxyl Chemical group 0.000 claims description 43
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 40
229910052739 hydrogen Inorganic materials 0.000 claims description 40
229910052760 oxygen Inorganic materials 0.000 claims description 40
239000001301 oxygen Substances 0.000 claims description 40
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 38
239000001257 hydrogen Substances 0.000 claims description 38
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical compound [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 34
239000008194 pharmaceutical composition Substances 0.000 claims description 34
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 28
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
125000003118 aryl group Chemical group 0.000 claims description 25
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 23
241000588724 Escherichia coli Species 0.000 claims description 21
208000015181 infectious disease Diseases 0.000 claims description 16
230000002401 inhibitory effect Effects 0.000 claims description 16
239000000543 intermediate Substances 0.000 claims description 15
241001465754 Metazoa Species 0.000 claims description 14
241000194031 Enterococcus faecium Species 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 12
241000606768 Haemophilus influenzae Species 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
230000012010 growth Effects 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 10
230000008569 process Effects 0.000 claims description 10
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
150000002431 hydrogen Chemical class 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 6
229910052736 halogen Chemical group 0.000 claims description 6
150000002367 halogens Chemical group 0.000 claims description 6
230000000813 microbial effect Effects 0.000 claims description 6
125000001624 naphthyl group Chemical group 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
239000011593 sulfur Chemical group 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
241000588832 Bordetella pertussis Species 0.000 claims description 3
241000606153 Chlamydia trachomatis Species 0.000 claims description 3
241000588653 Neisseria Species 0.000 claims description 3
241000606834 [Haemophilus] ducreyi Species 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000003282 alkyl amino group Chemical group 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 3
125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
241000893512 Aquifex aeolicus Species 0.000 claims description 2
241000193830 Bacillus <bacterium> Species 0.000 claims description 2
241001647372 Chlamydia pneumoniae Species 0.000 claims description 2
241000192091 Deinococcus radiodurans Species 0.000 claims description 2
241000193385 Geobacillus stearothermophilus Species 0.000 claims description 2
241000589517 Pseudomonas aeruginosa Species 0.000 claims description 2
241000589776 Pseudomonas putida Species 0.000 claims description 2
241000192581 Synechocystis sp. Species 0.000 claims description 2
241000607479 Yersinia pestis Species 0.000 claims description 2
241000588902 Zymomonas mobilis Species 0.000 claims description 2
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
229940038705 chlamydia trachomatis Drugs 0.000 claims description 2
229940125904 compound 1 Drugs 0.000 claims description 2
229940047650 haemophilus influenzae Drugs 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
241000191967 Staphylococcus aureus Species 0.000 claims 1
239000013043 chemical agent Substances 0.000 claims 1
241000894007 species Species 0.000 claims 1
102000004190 Enzymes Human genes 0.000 abstract description 33
108090000790 Enzymes Proteins 0.000 abstract description 33
230000000694 effects Effects 0.000 abstract description 22
230000000844 anti-bacterial effect Effects 0.000 abstract description 12
210000000170 cell membrane Anatomy 0.000 abstract description 3
230000004260 plant-type cell wall biogenesis Effects 0.000 abstract description 2
229940124350 antibacterial drug Drugs 0.000 abstract 1
230000037361 pathway Effects 0.000 abstract 1
239000000243 solution Substances 0.000 description 101
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
239000000203 mixture Substances 0.000 description 61
239000000047 product Substances 0.000 description 61
108090000364 Ligases Proteins 0.000 description 40
102000003960 Ligases Human genes 0.000 description 40
239000011541 reaction mixture Substances 0.000 description 38
ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 36
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 36
238000012360 testing method Methods 0.000 description 34
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 27
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
230000005764 inhibitory process Effects 0.000 description 24
235000002639 sodium chloride Nutrition 0.000 description 23
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 22
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 22
238000005481 NMR spectroscopy Methods 0.000 description 22
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 22
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 21
239000007787 solid Substances 0.000 description 21
238000004128 high performance liquid chromatography Methods 0.000 description 19
239000002904 solvent Substances 0.000 description 18
239000000126 substance Substances 0.000 description 18
239000000725 suspension Substances 0.000 description 18
238000003786 synthesis reaction Methods 0.000 description 17
239000002609 medium Substances 0.000 description 16
238000004809 thin layer chromatography Methods 0.000 description 16
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
241000894006 Bacteria Species 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
150000001412 amines Chemical class 0.000 description 15
230000015572 biosynthetic process Effects 0.000 description 15
239000012043 crude product Substances 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
238000004458 analytical method Methods 0.000 description 14
244000005700 microbiome Species 0.000 description 14
238000002360 preparation method Methods 0.000 description 14
150000003839 salts Chemical class 0.000 description 14
238000011282 treatment Methods 0.000 description 14
239000012044 organic layer Substances 0.000 description 13
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 11
206010035664 Pneumonia Diseases 0.000 description 11
239000003153 chemical reaction reagent Substances 0.000 description 11
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 11
229960004198 guanidine Drugs 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
238000010898 silica gel chromatography Methods 0.000 description 11
230000000845 anti-microbial effect Effects 0.000 description 10
125000005842 heteroatom Chemical group 0.000 description 10
239000003112 inhibitor Substances 0.000 description 10
150000002576 ketones Chemical group 0.000 description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
125000001424 substituent group Chemical group 0.000 description 10
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 10
QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
201000010099 disease Diseases 0.000 description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
208000024891 symptom Diseases 0.000 description 9
208000035143 Bacterial infection Diseases 0.000 description 8
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
238000000338 in vitro Methods 0.000 description 8
239000002054 inoculum Substances 0.000 description 8
239000000523 sample Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
102000003855 L-lactate dehydrogenase Human genes 0.000 description 7
108700023483 L-lactate dehydrogenases Proteins 0.000 description 7
241000124008 Mammalia Species 0.000 description 7
102000013009 Pyruvate Kinase Human genes 0.000 description 7
108020005115 Pyruvate Kinase Proteins 0.000 description 7
239000003242 anti bacterial agent Substances 0.000 description 7
238000003556 assay Methods 0.000 description 7
125000004429 atom Chemical group 0.000 description 7
208000022362 bacterial infectious disease Diseases 0.000 description 7
239000002585 base Substances 0.000 description 7
230000037396 body weight Effects 0.000 description 7
239000003814 drug Substances 0.000 description 7
239000000651 prodrug Substances 0.000 description 7
229940002612 prodrug Drugs 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
239000011550 stock solution Substances 0.000 description 7
238000006467 substitution reaction Methods 0.000 description 7
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
208000035473 Communicable disease Diseases 0.000 description 6
QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
229940088710 antibiotic agent Drugs 0.000 description 6
239000012298 atmosphere Substances 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
239000003937 drug carrier Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000000463 material Substances 0.000 description 6
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 6
BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 6
239000000843 powder Substances 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
239000000758 substrate Substances 0.000 description 6
QQLIGMASAVJVON-UHFFFAOYSA-N 1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=CC2=C1 QQLIGMASAVJVON-UHFFFAOYSA-N 0.000 description 5
229920001817 Agar Polymers 0.000 description 5
239000006137 Luria-Bertani broth Substances 0.000 description 5
241000295644 Staphylococcaceae Species 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
239000008272 agar Substances 0.000 description 5
230000008901 benefit Effects 0.000 description 5
125000002619 bicyclic group Chemical group 0.000 description 5
125000004122 cyclic group Chemical group 0.000 description 5
238000010790 dilution Methods 0.000 description 5
239000012895 dilution Substances 0.000 description 5
238000001704 evaporation Methods 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
239000012458 free base Substances 0.000 description 5
229960000789 guanidine hydrochloride Drugs 0.000 description 5
PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 5
125000000623 heterocyclic group Chemical group 0.000 description 5
125000002950 monocyclic group Chemical group 0.000 description 5
238000000746 purification Methods 0.000 description 5
JOZPEVMCAKXSEY-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine Chemical class N1=CN=CC2=NC=NC=C21 JOZPEVMCAKXSEY-UHFFFAOYSA-N 0.000 description 5
239000007858 starting material Substances 0.000 description 5
238000011269 treatment regimen Methods 0.000 description 5
239000003981 vehicle Substances 0.000 description 5
239000011592 zinc chloride Substances 0.000 description 5
235000005074 zinc chloride Nutrition 0.000 description 5
HNXQXTQTPAJEJL-UHFFFAOYSA-N 2-aminopteridin-4-ol Chemical class C1=CN=C2NC(N)=NC(=O)C2=N1 HNXQXTQTPAJEJL-UHFFFAOYSA-N 0.000 description 4
CXYLLFGNJJCGHM-UHFFFAOYSA-N 4-amino-2-bromopyrimidine-5-carbonitrile Chemical compound NC1=NC(Br)=NC=C1C#N CXYLLFGNJJCGHM-UHFFFAOYSA-N 0.000 description 4
XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 4
XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 4
241000589562 Brucella Species 0.000 description 4
239000002126 C01EB10 - Adenosine Substances 0.000 description 4
208000027418 Wounds and injury Diseases 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
229960005305 adenosine Drugs 0.000 description 4
150000001408 amides Chemical group 0.000 description 4
239000004599 antimicrobial Substances 0.000 description 4
230000003115 biocidal effect Effects 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
239000008280 blood Substances 0.000 description 4
239000000872 buffer Substances 0.000 description 4
229960005091 chloramphenicol Drugs 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
238000011161 development Methods 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
125000001072 heteroaryl group Chemical group 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
230000007246 mechanism Effects 0.000 description 4
230000004048 modification Effects 0.000 description 4
238000012986 modification Methods 0.000 description 4
229950006238 nadide Drugs 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
DRYYOLGDWVJUCL-UHFFFAOYSA-N pyrimidin-2-ylcyanamide Chemical compound N#CNC1=NC=CC=N1 DRYYOLGDWVJUCL-UHFFFAOYSA-N 0.000 description 4
238000006268 reductive amination reaction Methods 0.000 description 4
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 4
238000010561 standard procedure Methods 0.000 description 4
230000002194 synthesizing effect Effects 0.000 description 4
230000009885 systemic effect Effects 0.000 description 4
229940124597 therapeutic agent Drugs 0.000 description 4
230000000699 topical effect Effects 0.000 description 4
208000019206 urinary tract infection Diseases 0.000 description 4
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 description 3
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
229920000858 Cyclodextrin Polymers 0.000 description 3
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 3
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
241000589516 Pseudomonas Species 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000002835 absorbance Methods 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
229960000723 ampicillin Drugs 0.000 description 3
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 3
230000002421 anti-septic effect Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
150000003940 butylamines Chemical group 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
230000002860 competitive effect Effects 0.000 description 3
229940126214 compound 3 Drugs 0.000 description 3
238000010511 deprotection reaction Methods 0.000 description 3
239000000645 desinfectant Substances 0.000 description 3
ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
150000002148 esters Chemical group 0.000 description 3
230000029142 excretion Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
150000002611 lead compounds Chemical class 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000012038 nucleophile Substances 0.000 description 3
230000000269 nucleophilic effect Effects 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
DTBNBXWJWCWCIK-UHFFFAOYSA-N phosphoenolpyruvic acid Chemical compound OC(=O)C(=C)OP(O)(O)=O DTBNBXWJWCWCIK-UHFFFAOYSA-N 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
239000003206 sterilizing agent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000005556 structure-activity relationship Methods 0.000 description 3
239000003826 tablet Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
BMUDPLZKKRQECS-UHFFFAOYSA-K 3-[18-(2-carboxyethyl)-8,13-bis(ethenyl)-3,7,12,17-tetramethylporphyrin-21,24-diid-2-yl]propanoic acid iron(3+) hydroxide Chemical compound [OH-].[Fe+3].[N-]1C2=C(C)C(CCC(O)=O)=C1C=C([N-]1)C(CCC(O)=O)=C(C)C1=CC(C(C)=C1C=C)=NC1=CC(C(C)=C1C=C)=NC1=C2 BMUDPLZKKRQECS-UHFFFAOYSA-K 0.000 description 2
LWCXZSDKANNOAR-UHFFFAOYSA-N 4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzoic acid Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(O)=O)C=C1 LWCXZSDKANNOAR-UHFFFAOYSA-N 0.000 description 2
241000251468 Actinopterygii Species 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-N 0.000 description 2
DYDCUQKUCUHJBH-UHFFFAOYSA-N D-Cycloserine Natural products NC1CONC1=O DYDCUQKUCUHJBH-UHFFFAOYSA-N 0.000 description 2
DEFJQIDDEAULHB-QWWZWVQMSA-N D-alanyl-D-alanine Chemical compound C[C@@H]([NH3+])C(=O)N[C@H](C)C([O-])=O DEFJQIDDEAULHB-QWWZWVQMSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N DL-isoserine Natural products NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
241000588921 Enterobacteriaceae Species 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
206010017964 Gastrointestinal infection Diseases 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
241000405147 Hermes Species 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
206010061218 Inflammation Diseases 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 2
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 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
229920003091 Methocel™ Polymers 0.000 description 2
MSFSPUZXLOGKHJ-UHFFFAOYSA-N Muraminsaeure Natural products OC(=O)C(C)OC1C(N)C(O)OC(CO)C1O MSFSPUZXLOGKHJ-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
DEFJQIDDEAULHB-UHFFFAOYSA-N N-D-alanyl-D-alanine Natural products CC(N)C(=O)NC(C)C(O)=O DEFJQIDDEAULHB-UHFFFAOYSA-N 0.000 description 2
241000588650 Neisseria meningitidis Species 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
108010013639 Peptidoglycan Proteins 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 2
206010057190 Respiratory tract infections Diseases 0.000 description 2
241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 2
208000019802 Sexually transmitted disease Diseases 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
206010048038 Wound infection Diseases 0.000 description 2
230000009471 action Effects 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
108010056243 alanylalanine Proteins 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001299 aldehydes Chemical group 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
238000010171 animal model Methods 0.000 description 2
238000009635 antibiotic susceptibility testing Methods 0.000 description 2
239000003429 antifungal agent Substances 0.000 description 2
229940121375 antifungal agent Drugs 0.000 description 2
239000002246 antineoplastic agent Substances 0.000 description 2
229940064004 antiseptic throat preparations Drugs 0.000 description 2
239000003443 antiviral agent Substances 0.000 description 2
238000013459 approach Methods 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
235000019445 benzyl alcohol Nutrition 0.000 description 2
RSDOASZYYCOXIB-UHFFFAOYSA-N beta-alaninamide Chemical class NCCC(N)=O RSDOASZYYCOXIB-UHFFFAOYSA-N 0.000 description 2
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical group NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 2
238000002306 biochemical method Methods 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
239000006161 blood agar Substances 0.000 description 2
206010006451 bronchitis Diseases 0.000 description 2
238000002815 broth microdilution Methods 0.000 description 2
QVYARBLCAHCSFJ-UHFFFAOYSA-N butane-1,1-diamine Chemical compound CCCC(N)N QVYARBLCAHCSFJ-UHFFFAOYSA-N 0.000 description 2
229940041514 candida albicans extract Drugs 0.000 description 2
239000002775 capsule Substances 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
230000008859 change Effects 0.000 description 2
WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
206010009887 colitis Diseases 0.000 description 2
230000001332 colony forming effect Effects 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
229960003077 cycloserine Drugs 0.000 description 2
230000006378 damage Effects 0.000 description 2
230000007423 decrease Effects 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
238000013461 design Methods 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
230000001804 emulsifying effect Effects 0.000 description 2
239000003623 enhancer Substances 0.000 description 2
AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
235000019688 fish Nutrition 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
229940124307 fluoroquinolone Drugs 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
125000005456 glyceride group Chemical group 0.000 description 2
229940109738 hematin Drugs 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
238000011534 incubation Methods 0.000 description 2
230000002458 infectious effect Effects 0.000 description 2
230000004054 inflammatory process Effects 0.000 description 2
238000001802 infusion Methods 0.000 description 2
238000003780 insertion Methods 0.000 description 2
230000037431 insertion Effects 0.000 description 2
238000001361 intraarterial administration Methods 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000008101 lactose Substances 0.000 description 2
210000004324 lymphatic system Anatomy 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000003760 magnetic stirring Methods 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
238000005259 measurement Methods 0.000 description 2
230000010534 mechanism of action Effects 0.000 description 2
230000001404 mediated effect Effects 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
238000012544 monitoring process Methods 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000000346 nonvolatile oil Substances 0.000 description 2
230000035515 penetration Effects 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
229920000136 polysorbate Polymers 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
230000000069 prophylactic effect Effects 0.000 description 2
238000011321 prophylaxis Methods 0.000 description 2
229940126409 proton pump inhibitor Drugs 0.000 description 2
239000000612 proton pump inhibitor Substances 0.000 description 2
150000003195 pteridines Chemical class 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
SURZBXMKNNZTLE-UHFFFAOYSA-N pyrimido[4,5-d]pyrimidine-2,4,7-triamine Chemical compound NC1=NC(N)=NC2=NC(N)=NC=C21 SURZBXMKNNZTLE-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000006215 rectal suppository Substances 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
208000020029 respiratory tract infectious disease Diseases 0.000 description 2
230000007017 scission Effects 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
238000013207 serial dilution Methods 0.000 description 2
238000009097 single-agent therapy Methods 0.000 description 2
206010040872 skin infection Diseases 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
UIICPZFWHBJNIG-UHFFFAOYSA-N sodium;2-methoxyethanolate Chemical compound [Na+].COCC[O-] UIICPZFWHBJNIG-UHFFFAOYSA-N 0.000 description 2
238000004659 sterilization and disinfection Methods 0.000 description 2
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 2
238000007920 subcutaneous administration Methods 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
230000009897 systematic effect Effects 0.000 description 2
238000010998 test method Methods 0.000 description 2
125000001544 thienyl group Chemical group 0.000 description 2
238000011200 topical administration Methods 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
241001148471 unidentified anaerobic bacterium Species 0.000 description 2
208000000143 urethritis Diseases 0.000 description 2
239000013598 vector Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000001993 wax Substances 0.000 description 2
239000012224 working solution Substances 0.000 description 2
239000012138 yeast extract Substances 0.000 description 2
150000003952 β-lactams Chemical class 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
CHHHXKFHOYLYRE-UHFFFAOYSA-M 2,4-Hexadienoic acid, potassium salt (1:1), (2E,4E)- Chemical compound [K+].CC=CC=CC([O-])=O CHHHXKFHOYLYRE-UHFFFAOYSA-M 0.000 description 1
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
WHPPYWZHBUBHST-UHFFFAOYSA-N 2-amino-7-(chloromethyl)-1h-pteridin-4-one Chemical compound C1=C(CCl)N=C2NC(N)=NC(=O)C2=N1 WHPPYWZHBUBHST-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
JXPDNDHCMMOJPC-UHFFFAOYSA-N 2-hydroxybutanedinitrile Chemical compound N#CC(O)CC#N JXPDNDHCMMOJPC-UHFFFAOYSA-N 0.000 description 1
URBTWXDXVSOVKE-UHFFFAOYSA-N 2-n-(2-aminoethyl)pyrimido[4,5-d]pyrimidine-2,5,7-triamine Chemical compound NC1=NC(N)=NC2=NC(NCCN)=NC=C21 URBTWXDXVSOVKE-UHFFFAOYSA-N 0.000 description 1
NSIBULQOMYMLCB-UHFFFAOYSA-N 2-n-methyl-2-n-(1-naphthalen-1-ylpropyl)pyrimido[4,5-d]pyrimidine-2,5,7-triamine Chemical compound C1=CC=C2C(C(N(C)C=3N=C4N=C(N)N=C(N)C4=CN=3)CC)=CC=CC2=C1 NSIBULQOMYMLCB-UHFFFAOYSA-N 0.000 description 1
ICJGICHYKQVUDD-UHFFFAOYSA-N 2-n-methyl-2-n-[1-(4-methylnaphthalen-1-yl)ethyl]pyrimido[4,5-d]pyrimidine-2,5,7-triamine Chemical compound C1=CC=C2C(C(N(C)C=3N=C4N=C(N)N=C(N)C4=CN=3)C)=CC=C(C)C2=C1 ICJGICHYKQVUDD-UHFFFAOYSA-N 0.000 description 1
229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
FEFMOQWNOBLEMK-UHFFFAOYSA-N 3-[(5,7-diaminopyrimido[4,5-d]pyrimidin-2-yl)-[(2-ethoxynaphthalen-1-yl)methyl]amino]-2-hydroxypropanoic acid Chemical compound NC1=NC(N)=NC2=NC(N(CC(O)C(O)=O)CC3=C4C=CC=CC4=CC=C3OCC)=NC=C21 FEFMOQWNOBLEMK-UHFFFAOYSA-N 0.000 description 1
VLGQINWTEKPERU-UHFFFAOYSA-N 3-[(5,7-diaminopyrimido[4,5-d]pyrimidin-2-yl)-[(2-ethoxynaphthalen-1-yl)methyl]amino]propanoic acid Chemical compound NC1=NC(N)=NC2=NC(N(CCC(O)=O)CC3=C4C=CC=CC4=CC=C3OCC)=NC=C21 VLGQINWTEKPERU-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
OPUUPOZRLORBMU-UHFFFAOYSA-N 4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]-n-(4-hydroxyphenyl)benzamide Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C(C=C1)=CC=C1C(=O)NC1=CC=C(O)C=C1 OPUUPOZRLORBMU-UHFFFAOYSA-N 0.000 description 1
WDHFCSOENXEMRC-UHFFFAOYSA-N 4-amino-2-chloropyrimidine-5-carbonitrile Chemical compound NC1=NC(Cl)=NC=C1C#N WDHFCSOENXEMRC-UHFFFAOYSA-N 0.000 description 1
WZRJTRPJURQBRM-UHFFFAOYSA-N 4-amino-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide;5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1.COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 WZRJTRPJURQBRM-UHFFFAOYSA-N 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
NTFCCOHTRTUMFR-UHFFFAOYSA-N 6-[[benzyl(methyl)amino]methyl]pteridine-2,4-diamine Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)CC1=CC=CC=C1 NTFCCOHTRTUMFR-UHFFFAOYSA-N 0.000 description 1
RVSAWQINKRHSOP-UHFFFAOYSA-N 6-[[methyl-[1-(4-methylphenyl)ethyl]amino]methyl]pteridine-2,4-diamine Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C(C)C1=CC=C(C)C=C1 RVSAWQINKRHSOP-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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241001430312 Amycolatopsis orientalis Species 0.000 description 1
241000272525 Anas platyrhynchos Species 0.000 description 1
241000272814 Anser sp. Species 0.000 description 1
241000972773 Aulopiformes Species 0.000 description 1
208000031729 Bacteremia Diseases 0.000 description 1
241000606124 Bacteroides fragilis Species 0.000 description 1
241001148536 Bacteroides sp. Species 0.000 description 1
102000004506 Blood Proteins Human genes 0.000 description 1
108010017384 Blood Proteins Proteins 0.000 description 1
241000589969 Borreliella burgdorferi Species 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
206010006458 Bronchitis chronic Diseases 0.000 description 1
241000894010 Buchnera aphidicola 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
JNRZNAGCSGWZMY-UHFFFAOYSA-N C(C(=O)C)(=O)OP(=O)=O Chemical compound C(C(=O)C)(=O)OP(=O)=O JNRZNAGCSGWZMY-UHFFFAOYSA-N 0.000 description 1
LBMSELKXMGXSNW-UHFFFAOYSA-N CCCCOC(=O)NCCCCN(CC1=C(C=CC2=CC=CC=C21)OCC)C3=NC=C4C(=NC(=NC4=N3)N)N Chemical compound CCCCOC(=O)NCCCCN(CC1=C(C=CC2=CC=CC=C21)OCC)C3=NC=C4C(=NC(=NC4=N3)N)N LBMSELKXMGXSNW-UHFFFAOYSA-N 0.000 description 1
WPWDUXBDEOKART-UHFFFAOYSA-N CCCCOC(=O)NCCNC1=NC=C(C(=N1)N)C#N Chemical compound CCCCOC(=O)NCCNC1=NC=C(C(=N1)N)C#N WPWDUXBDEOKART-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
208000035484 Cellulite Diseases 0.000 description 1
241000606161 Chlamydia Species 0.000 description 1
241001647378 Chlamydia psittaci Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
206010008631 Cholera Diseases 0.000 description 1
241000723346 Cinnamomum camphora Species 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
241001112696 Clostridia Species 0.000 description 1
241000193163 Clostridioides difficile Species 0.000 description 1
241000186227 Corynebacterium diphtheriae Species 0.000 description 1
241000186427 Cutibacterium acnes Species 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
108010016626 Dipeptides Proteins 0.000 description 1
241000792859 Enema Species 0.000 description 1
208000004232 Enteritis Diseases 0.000 description 1
241000588914 Enterobacter Species 0.000 description 1
241000194033 Enterococcus Species 0.000 description 1
241000194029 Enterococcus hirae Species 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
206010016936 Folliculitis Diseases 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
241000207201 Gardnerella vaginalis Species 0.000 description 1
CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
229930182566 Gentamicin Natural products 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
206010018612 Gonorrhoea Diseases 0.000 description 1
206010018691 Granuloma Diseases 0.000 description 1
241000590002 Helicobacter pylori Species 0.000 description 1
102000008100 Human Serum Albumin Human genes 0.000 description 1
108091006905 Human Serum Albumin Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010021531 Impetigo Diseases 0.000 description 1
239000003810 Jones reagent Substances 0.000 description 1
241000588748 Klebsiella Species 0.000 description 1
241001534216 Klebsiella granulomatis Species 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
235000019687 Lamb Nutrition 0.000 description 1
239000004166 Lanolin Substances 0.000 description 1
241000589242 Legionella pneumophila Species 0.000 description 1
241000192130 Leuconostoc mesenteroides Species 0.000 description 1
241000186781 Listeria Species 0.000 description 1
241001490312 Lithops pseudotruncatella Species 0.000 description 1
206010024971 Lower respiratory tract infections Diseases 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
241000588655 Moraxella catarrhalis Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000186367 Mycobacterium avium Species 0.000 description 1
241000187480 Mycobacterium smegmatis Species 0.000 description 1
241000187479 Mycobacterium tuberculosis Species 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
206010028885 Necrotising fasciitis Diseases 0.000 description 1
241000588652 Neisseria gonorrhoeae Species 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
241000187654 Nocardia Species 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
206010068319 Oropharyngeal pain Diseases 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
206010033078 Otitis media Diseases 0.000 description 1
206010033645 Pancreatitis Diseases 0.000 description 1
206010034016 Paronychia Diseases 0.000 description 1
206010034133 Pathogen resistance Diseases 0.000 description 1
206010049752 Peau d'orange Diseases 0.000 description 1
241001494479 Pecora Species 0.000 description 1
208000029082 Pelvic Inflammatory Disease Diseases 0.000 description 1
229930195708 Penicillin V Natural products 0.000 description 1
241000009328 Perro Species 0.000 description 1
208000037581 Persistent Infection Diseases 0.000 description 1
201000005702 Pertussis Diseases 0.000 description 1
201000007100 Pharyngitis Diseases 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
102000007327 Protamines Human genes 0.000 description 1
108010007568 Protamines Proteins 0.000 description 1
241000588769 Proteus <enterobacteria> Species 0.000 description 1
239000005700 Putrescine Substances 0.000 description 1
206010037596 Pyelonephritis Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229930189077 Rifamycin Natural products 0.000 description 1
241000531795 Salmonella enterica subsp. enterica serovar Paratyphi A Species 0.000 description 1
241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
241000277331 Salmonidae Species 0.000 description 1
206010049677 Salpingo-oophoritis Diseases 0.000 description 1
206010040047 Sepsis Diseases 0.000 description 1
241000607720 Serratia Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
208000007107 Stomach Ulcer Diseases 0.000 description 1
206010061372 Streptococcal infection Diseases 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
241000546283 Streptomyces toyocaensis Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241000282898 Sus scrofa Species 0.000 description 1
241000204666 Thermotoga maritima Species 0.000 description 1
WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
241000589886 Treponema Species 0.000 description 1
208000037386 Typhoid Diseases 0.000 description 1
206010046306 Upper respiratory tract infection Diseases 0.000 description 1
241000202921 Ureaplasma urealyticum Species 0.000 description 1
206010046477 Urethral syndrome Diseases 0.000 description 1
208000006374 Uterine Cervicitis Diseases 0.000 description 1
241000607626 Vibrio cholerae Species 0.000 description 1
206010052428 Wound Diseases 0.000 description 1
241000204362 Xylella fastidiosa Species 0.000 description 1
FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical class NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000002814 agar dilution Methods 0.000 description 1
125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 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
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
229940063655 aluminum stearate Drugs 0.000 description 1
125000000320 amidine group Chemical group 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
229940126575 aminoglycoside Drugs 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 1
229960003022 amoxicillin Drugs 0.000 description 1
239000003926 antimycobacterial agent Substances 0.000 description 1
PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
150000008365 aromatic ketones Chemical class 0.000 description 1
229940009098 aspartate Drugs 0.000 description 1
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 1
229960004099 azithromycin Drugs 0.000 description 1
230000003385 bacteriostatic effect Effects 0.000 description 1
208000002479 balanitis Diseases 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 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
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
239000003781 beta lactamase inhibitor Substances 0.000 description 1
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
229940000635 beta-alanine Drugs 0.000 description 1
229940126813 beta-lactamase inhibitor Drugs 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
238000010256 biochemical assay Methods 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
210000000133 brain stem Anatomy 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
125000005997 bromomethyl group Chemical group 0.000 description 1
239000006172 buffering agent Substances 0.000 description 1
244000309464 bull Species 0.000 description 1
WGHSDRQEAZJFHH-UHFFFAOYSA-N butyl n-(2-aminoethyl)carbamate Chemical compound CCCCOC(=O)NCCN WGHSDRQEAZJFHH-UHFFFAOYSA-N 0.000 description 1
AQJLIWCXXYZELT-UHFFFAOYSA-N butyl n-(3-aminopropyl)carbamate Chemical compound CCCCOC(=O)NCCCN AQJLIWCXXYZELT-UHFFFAOYSA-N 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
229960000846 camphor Drugs 0.000 description 1
229930008380 camphor Natural products 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
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
150000007942 carboxylates Chemical group 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
241001233037 catfish Species 0.000 description 1
QYIYFLOTGYLRGG-GPCCPHFNSA-N cefaclor Chemical compound C1([C@H](C(=O)N[C@@H]2C(N3C(=C(Cl)CS[C@@H]32)C(O)=O)=O)N)=CC=CC=C1 QYIYFLOTGYLRGG-GPCCPHFNSA-N 0.000 description 1
229960005361 cefaclor Drugs 0.000 description 1
ORFOPKXBNMVMKC-DWVKKRMSSA-N ceftazidime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 ORFOPKXBNMVMKC-DWVKKRMSSA-N 0.000 description 1
229960000484 ceftazidime Drugs 0.000 description 1
230000010261 cell growth Effects 0.000 description 1
210000002421 cell wall Anatomy 0.000 description 1
230000036232 cellulite Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
206010008323 cervicitis Diseases 0.000 description 1
229940081733 cetearyl alcohol Drugs 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
238000011208 chromatographic data Methods 0.000 description 1
208000007451 chronic bronchitis Diseases 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
229960002626 clarithromycin Drugs 0.000 description 1
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 1
238000004140 cleaning Methods 0.000 description 1
229960002227 clindamycin Drugs 0.000 description 1
KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 description 1
229940047766 co-trimoxazole Drugs 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
229940075614 colloidal silicon dioxide Drugs 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000002648 combination therapy Methods 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
238000005094 computer simulation Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
229940097362 cyclodextrins Drugs 0.000 description 1
BALGDZWGNCXXES-UHFFFAOYSA-N cyclopentane;propanoic acid Chemical compound CCC(O)=O.C1CCCC1 BALGDZWGNCXXES-UHFFFAOYSA-N 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
201000003146 cystitis Diseases 0.000 description 1
230000034994 death Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000008260 defense mechanism Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
GXGAKHNRMVGRPK-UHFFFAOYSA-N dimagnesium;dioxido-bis[[oxido(oxo)silyl]oxy]silane Chemical compound [Mg+2].[Mg+2].[O-][Si](=O)O[Si]([O-])([O-])O[Si]([O-])=O GXGAKHNRMVGRPK-UHFFFAOYSA-N 0.000 description 1
125000000532 dioxanyl group Chemical group 0.000 description 1
206010013023 diphtheria Diseases 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
235000019797 dipotassium phosphate Nutrition 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
229940043264 dodecyl sulfate Drugs 0.000 description 1
239000012154 double-distilled water Substances 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
208000000718 duodenal ulcer Diseases 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000008387 emulsifying waxe Substances 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940095399 enema Drugs 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
229960000285 ethambutol Drugs 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
210000003527 eukaryotic cell Anatomy 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000013305 food Nutrition 0.000 description 1
230000006870 function Effects 0.000 description 1
210000000232 gallbladder Anatomy 0.000 description 1
GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 description 1
229940080345 gamma-cyclodextrin Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000008103 glucose Substances 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
229960002449 glycine Drugs 0.000 description 1
150000002333 glycines Chemical class 0.000 description 1
208000001786 gonorrhea Diseases 0.000 description 1
230000036541 health Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229940025294 hemin Drugs 0.000 description 1
BTIJJDXEELBZFS-QDUVMHSLSA-K hemin Chemical compound CC1=C(CCC(O)=O)C(C=C2C(CCC(O)=O)=C(C)\C(N2[Fe](Cl)N23)=C\4)=N\C1=C/C2=C(C)C(C=C)=C3\C=C/1C(C)=C(C=C)C/4=N\1 BTIJJDXEELBZFS-QDUVMHSLSA-K 0.000 description 1
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 description 1
229960002182 imipenem Drugs 0.000 description 1
239000012535 impurity Substances 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
206010022000 influenza Diseases 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
229940102213 injectable suspension Drugs 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
238000007917 intracranial administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000007919 intrasynovial administration Methods 0.000 description 1
238000007913 intrathecal administration Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
238000010829 isocratic elution Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229960003350 isoniazid Drugs 0.000 description 1
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
BPHPUYQFMNQIOC-NXRLNHOXSA-N isopropyl beta-D-thiogalactopyranoside Chemical compound CC(C)S[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O BPHPUYQFMNQIOC-NXRLNHOXSA-N 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
238000011005 laboratory method Methods 0.000 description 1
235000019388 lanolin Nutrition 0.000 description 1
229940039717 lanolin Drugs 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
229940115932 legionella pneumophila Drugs 0.000 description 1
231100001231 less toxic Toxicity 0.000 description 1
239000003446 ligand Substances 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
125000005647 linker group Chemical group 0.000 description 1
244000144972 livestock Species 0.000 description 1
230000007774 longterm Effects 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
208000001581 lymphogranuloma venereum Diseases 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229940099273 magnesium trisilicate Drugs 0.000 description 1
229910000386 magnesium trisilicate Inorganic materials 0.000 description 1
235000019793 magnesium trisilicate Nutrition 0.000 description 1
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
238000012423 maintenance Methods 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
210000004962 mammalian cell Anatomy 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
229940042472 mineral oil Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000000302 molecular modelling Methods 0.000 description 1
125000002757 morpholinyl group Chemical group 0.000 description 1
239000004570 mortar (masonry) Substances 0.000 description 1
238000003541 multi-stage reaction Methods 0.000 description 1
LCTZWNAKISMPCD-UHFFFAOYSA-N n-(4-aminobutyl)-4-[(2,4-diaminopteridin-6-yl)methyl-methylamino]benzamide Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)NCCCCN)C=C1 LCTZWNAKISMPCD-UHFFFAOYSA-N 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
YGXDJFKCOBYLFG-UHFFFAOYSA-N n-methyl-2-naphthalen-1-ylethanamine Chemical compound C1=CC=C2C(CCNC)=CC=CC2=C1 YGXDJFKCOBYLFG-UHFFFAOYSA-N 0.000 description 1
150000004002 naphthaldehydes Chemical class 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
239000007922 nasal spray Substances 0.000 description 1
201000007970 necrotizing fasciitis Diseases 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 1
229960000564 nitrofurantoin Drugs 0.000 description 1
231100000344 non-irritating Toxicity 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
229960000381 omeprazole Drugs 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000002018 overexpression Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
239000002245 particle Substances 0.000 description 1
244000052769 pathogen Species 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
229940056367 penicillin v Drugs 0.000 description 1
150000002960 penicillins Chemical class 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
235000019271 petrolatum Nutrition 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
229930029653 phosphoenolpyruvate Natural products 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
238000011197 physicochemical method Methods 0.000 description 1
229960002292 piperacillin Drugs 0.000 description 1
WCMIIGXFCMNQDS-IDYPWDAWSA-M piperacillin sodium Chemical compound [Na+].O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@@H]21 WCMIIGXFCMNQDS-IDYPWDAWSA-M 0.000 description 1
239000013612 plasmid Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229940113124 polysorbate 60 Drugs 0.000 description 1
229920000053 polysorbate 80 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
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
239000004302 potassium sorbate Substances 0.000 description 1
235000010241 potassium sorbate Nutrition 0.000 description 1
229940069338 potassium sorbate Drugs 0.000 description 1
244000144977 poultry Species 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
239000001294 propane Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229950008679 protamine sulfate Drugs 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
150000008518 pyridopyrimidines Chemical class 0.000 description 1
150000008520 pyrimidinopyrimidines Chemical class 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
NFHMDRANESJFQS-UHFFFAOYSA-N pyrimido[5,4-d]pyrimidine-2,4-diamine Chemical group N1=CN=CC2=NC(N)=NC(N)=C21 NFHMDRANESJFQS-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000005956 quaternization reaction Methods 0.000 description 1
150000003246 quinazolines Chemical class 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
230000005855 radiation Effects 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
239000012088 reference solution Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000010076 replication Effects 0.000 description 1
JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 description 1
229960001225 rifampicin Drugs 0.000 description 1
BTVYFIMKUHNOBZ-QXMMDKDBSA-N rifamycin s Chemical class O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C\C(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C(C)C(OC)\C=C/OC1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-QXMMDKDBSA-N 0.000 description 1
229940081192 rifamycins Drugs 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
229960001860 salicylate Drugs 0.000 description 1
235000019515 salmon Nutrition 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
201000009890 sinusitis Diseases 0.000 description 1
238000010512 small scale reaction Methods 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000006104 solid solution Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
238000000527 sonication Methods 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000001587 sorbitan monostearate Substances 0.000 description 1
235000011076 sorbitan monostearate Nutrition 0.000 description 1
229940035048 sorbitan monostearate Drugs 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
208000006379 syphilis Diseases 0.000 description 1
230000008685 targeting Effects 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
ZFQWJXFJJZUVPI-UHFFFAOYSA-N tert-butyl n-(4-aminobutyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCCN ZFQWJXFJJZUVPI-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
150000007970 thio esters Chemical group 0.000 description 1
125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 1
229960004659 ticarcillin Drugs 0.000 description 1
229960000707 tobramycin Drugs 0.000 description 1
NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000005924 transacylation reaction Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
229960001082 trimethoprim Drugs 0.000 description 1
IEDVJHCEMCRBQM-UHFFFAOYSA-N trimethoprim Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(N)=NC=2)N)=C1 IEDVJHCEMCRBQM-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
201000008297 typhoid fever Diseases 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
229940046010 vitamin k Drugs 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
WHGYBXFWUBPSRW-FEYSZYNQSA-N β-dextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)C(O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FEYSZYNQSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/06—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4
- C07D475/08—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Tropical Medicine & Parasitology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

SK30-2004A 2001-06-28 2002-06-28 Heterocyklické zlúčeniny a ich použitie ako inhibítory D-Ala-D-Ala ligázy SK302004A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US30168501P	2001-06-28	2001-06-28
PCT/US2002/020567 WO2003001887A2 (en)	2001-06-28	2002-06-28	Fused pyrimidines as d-alanyl-d-alanine ligase inhibitors

Publications (1)

Publication Number	Publication Date
SK302004A3 true SK302004A3 (sk)	2005-07-01

Family

ID=23164426

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK30-2004A SK302004A3 (sk)	2001-06-28	2002-06-28	Heterocyklické zlúčeniny a ich použitie ako inhibítory D-Ala-D-Ala ligázy

Country Status (16)

Country	Link
US (3)	US7345048B2 (pl)
EP (2)	EP1432713A4 (pl)
CN (2)	CN1547472A (pl)
BG (1)	BG108548A (pl)
BR (1)	BR0211310A (pl)
CA (2)	CA2451840A1 (pl)
CZ (2)	CZ200442A3 (pl)
EA (1)	EA200400094A1 (pl)
EE (2)	EE200400042A (pl)
HU (2)	HUP0700040A2 (pl)
IL (2)	IL159538A0 (pl)
MX (1)	MXPA04000159A (pl)
PL (2)	PL374259A1 (pl)
SK (1)	SK302004A3 (pl)
WO (2)	WO2003001887A2 (pl)
YU (2)	YU102503A (pl)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB0217703D0 (en) *	2002-07-31	2002-09-11	Univ Liverpool	Pharmaceutical composition
WO2006050843A1 (en) *	2004-11-09	2006-05-18	F. Hoffmann-La Roche Ag	Aminoquinazolines compounds
ES2336603T3 (es) *	2005-07-21	2010-04-14	F. Hoffmann-La Roche Ag	Compuestos de pirido(2,3-d)pirimidina-2,4-diamina como inhibidores de ptp1b.
GB0608822D0 (en) *	2006-05-04	2006-06-14	Chroma Therapeutics Ltd	Inhibitors of DHFR
SI22338A (sl) *	2006-08-18	2008-02-29	Univerza V Ljubljani, Fakulteta Za Farmacijo	Diazendikarboksamidi kot inhibitorji d-alanil-d-alanin ligaze
TW200831528A (en)	2006-11-30	2008-08-01	Astrazeneca Ab	Compounds
CN101084901B (zh) *	2007-06-22	2011-12-21	复旦大学	一种葡萄球菌抑制剂
SG187502A1 (en)	2008-02-01	2013-02-28	Takeda Pharmaceutical	Oxim derivatives as hsp90 inhibitors
JP2012520745A (ja) *	2009-03-20	2012-09-10	ボード・オブ・リージエンツ，ザ・ユニバーシテイ・オブ・テキサス・システム	医療装置に抗菌活性を付与するための方法
UA107806C2 (uk) *	2009-08-31	2015-02-25	ДАУ АГРОСАЙЄНСІЗ ЕлЕлСі	Птеридини і їх застосування як агрохімікатів
US9670205B2 (en)	2015-03-04	2017-06-06	Gilead Sciences, Inc.	Toll like receptor modulator compounds
CN106316966A (zh) *	2015-06-15	2017-01-11	董运勤	医药中间体n-(2-吡嗪甲基)苄胺磷酸盐化合物制备方法
AU2017318601B2 (en)	2016-09-02	2020-09-03	Gilead Sciences, Inc.	Toll like receptor modulator compounds
WO2018045150A1 (en)	2016-09-02	2018-03-08	Gilead Sciences, Inc.	4,6-diamino-pyrido[3,2-d]pyrimidine derivaties as toll like receptor modulators
KR20200012823A (ko)	2017-02-01	2020-02-05	예일 유니버시티	이뇨제 내성의 치료
EP3735421A4 (en)	2018-01-05	2021-09-22	Corvidia Therapeutics, Inc.	METHOD OF TREATMENT OF IL-6 MEDIATED INFLAMMATION WITHOUT IMMUNSUPPRESSION
EP3917914A1 (en) *	2019-02-01	2021-12-08	Fmc Corporation	Diamino-substituted pyridines and pyrimidines as herbicides
TWI751516B (zh)	2019-04-17	2022-01-01	美商基利科學股份有限公司	類鐸受體調節劑之固體形式
TW202212339A (zh)	2019-04-17	2022-04-01	美商基利科學股份有限公司	類鐸受體調節劑之固體形式
TWI879779B (zh)	2019-06-28	2025-04-11	美商基利科學股份有限公司	類鐸受體調節劑化合物的製備方法
GB2626567A (en) *	2023-01-26	2024-07-31	De Montfort Univ	Quinazoline derivatives for use as a medicament

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2949466A (en) *	1958-03-04	1960-08-16	Parke Davis & Co	Pyrimidine compounds and means of producing the same
US3134778A (en) *	1963-08-20	1964-05-26	Smith Kline French Lab	2,5,7-triamino-4-phenyl (or thienyl)-pyrimido[4,5-d]pyrimidines
RO56210A2 (pl)	1970-12-28	1974-08-01
US4079056A (en) *	1975-03-31	1978-03-14	The United States Of America As Represented By The Department Of Health, Education And Welfare	Method of making pteridine compounds
DE2750288A1 (de) *	1977-11-10	1979-05-17	Thomae Gmbh Dr K	Neue 9-(omega-heteroarylamino- alkylamino)-erythromycine, ihre salze, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
DE3445298A1 (de) *	1984-12-12	1986-06-12	Dr. Karl Thomae Gmbh, 7950 Biberach	Neue pteridine, verfahren zu ihrer herstellung und deren verwendung als zwischenprodukte oder als arzneimittel
WO1992017478A1 (en)	1991-04-08	1992-10-15	Duquesne University Of The Holy Ghost	5-ALKYL-6-[[AMINO]METHYL]PYRIDO[2,3-d]PYRIMIDINE DERIVATIVES AND METHODS OF PREPARING AND USING THESE DERIVATIVES
US5547954A (en) *	1994-05-26	1996-08-20	Fmc Corporation	2,4-Diamino-5,6-disubstituted-and 5,6,7-trisubstituted-5-deazapteridines as insecticides
DE59610771D1 (de) *	1995-02-27	2003-11-20	Hoffmann La Roche	Dioxopyrrolo-pyrrolderivate
AU2960599A (en)	1998-03-30	1999-10-18	Akira Karasawa	Quinazoline derivatives
JP2000239277A (ja) *	1999-02-19	2000-09-05	Kyowa Hakko Kogyo Co Ltd	イミダゾキナゾリン誘導体
GB0219893D0 (en)	2002-08-27	2002-10-02	Melacure Therapeutics Ab	Pharmaceutically active compounds

2002
- 2002-06-28 PL PL02374259A patent/PL374259A1/pl unknown
- 2002-06-28 HU HU0700040A patent/HUP0700040A2/hu unknown
- 2002-06-28 CA CA002451840A patent/CA2451840A1/en not_active Abandoned
- 2002-06-28 US US10/185,059 patent/US7345048B2/en not_active Expired - Fee Related
- 2002-06-28 WO PCT/US2002/020567 patent/WO2003001887A2/en not_active Ceased
- 2002-06-28 EP EP02753353A patent/EP1432713A4/en not_active Withdrawn
- 2002-06-28 CN CNA028166604A patent/CN1547472A/zh active Pending
- 2002-06-28 EA EA200400094A patent/EA200400094A1/ru unknown
- 2002-06-28 CN CNA028150651A patent/CN1543465A/zh active Pending
- 2002-06-28 PL PL02374589A patent/PL374589A1/pl not_active Application Discontinuation
- 2002-06-28 US US10/184,855 patent/US20030176436A1/en not_active Abandoned
- 2002-06-28 CZ CZ200442A patent/CZ200442A3/cs unknown
- 2002-06-28 CZ CZ200443A patent/CZ200443A3/cs unknown
- 2002-06-28 EE EEP200400042A patent/EE200400042A/xx unknown
- 2002-06-28 MX MXPA04000159A patent/MXPA04000159A/es not_active Application Discontinuation
- 2002-06-28 IL IL15953802A patent/IL159538A0/xx unknown
- 2002-06-28 WO PCT/US2002/020479 patent/WO2003002064A2/en not_active Ceased
- 2002-06-28 SK SK30-2004A patent/SK302004A3/sk not_active Application Discontinuation
- 2002-06-28 HU HU0700061A patent/HUP0700061A2/hu unknown
- 2002-06-28 YU YU102503A patent/YU102503A/sh unknown
- 2002-06-28 IL IL15954002A patent/IL159540A0/xx unknown
- 2002-06-28 BR BRPI0211310-4A patent/BR0211310A/pt not_active IP Right Cessation
- 2002-06-28 EE EEP200400043A patent/EE200400043A/xx unknown
- 2002-06-28 YU YU102303A patent/YU102303A/sh unknown
- 2002-06-28 CA CA002451800A patent/CA2451800A1/en not_active Abandoned
- 2002-06-28 EP EP02759101A patent/EP1411949A4/en not_active Withdrawn
2004
- 2004-01-28 BG BG108548A patent/BG108548A/bg unknown
2007
- 2007-12-05 US US11/951,214 patent/US20080090847A1/en not_active Abandoned

Also Published As

Publication number	Publication date
EE200400043A (et)	2004-10-15
BG108548A (bg)	2005-05-31
CZ200443A3 (cs)	2004-08-18
HUP0700061A2 (en)	2007-05-02
EP1411949A4 (en)	2004-11-24
CA2451800A1 (en)	2003-01-09
WO2003002064A3 (en)	2003-10-23
WO2003002064A2 (en)	2003-01-09
PL374259A1 (pl)	2005-10-03
WO2003001887A3 (en)	2003-08-21
EA200400094A1 (ru)	2005-08-25
HUP0700040A2 (en)	2007-05-29
EP1411949A2 (en)	2004-04-28
CN1547472A (zh)	2004-11-17
CA2451840A1 (en)	2003-01-09
EE200400042A (et)	2004-10-15
CN1543465A (zh)	2004-11-03
EP1432713A2 (en)	2004-06-30
IL159538A0 (en)	2004-06-01
YU102303A (sh)	2006-08-17
WO2003001887A2 (en)	2003-01-09
EP1432713A4 (en)	2005-05-11
US20030176436A1 (en)	2003-09-18
BR0211310A (pt)	2006-10-31
IL159540A0 (en)	2004-06-01
CZ200442A3 (cs)	2004-10-13
YU102503A (sh)	2006-08-17
PL374589A1 (pl)	2005-10-31
US20080090847A1 (en)	2008-04-17
US7345048B2 (en)	2008-03-18
MXPA04000159A (es)	2005-01-07
US20030181470A1 (en)	2003-09-25

Legal Events

Date	Code	Title	Description
2012-01-04	FC9A	Refused patent application

Publication	Publication Date	Title
SK302004A3 (sk)	2005-07-01	Heterocyklické zlúčeniny a ich použitie ako inhibítory D-Ala-D-Ala ligázy
US20200140460A1 (en)	2020-05-07	Antibacterial therapeutics and prophylactics
JP6114275B2 (ja)	2017-04-12	窒素含有化合物及びその使用
JP2002505689A (ja)	2002-02-19	キノリン−インドール抗菌剤、それらに関する用途及び組成物
US20090042927A1 (en)	2009-02-12	Salts, Prodrugs and Polymorphs of Fab I Inhibitors
JP5897566B2 (ja)	2016-03-30	環式ｎ，ｎ’−ジアリールチオ尿素及びｎ，ｎ’−ジアリール尿素−アンドロゲン受容体アンタゴニスト、抗癌剤、その調製のための方法及び使用
RU2625305C2 (ru)	2017-07-13	Твердые формы ингибитора гиразы (r)-1-этил-3-[6-фтор-5[2-(1-гидрокси-1-метил-этил) пиримидин-5-ил]-7-(тетрагидрофуран-2-ил)-1н-бензимидазол-2-ил] мочевины
CN101263146A (zh)	2008-09-10	抗感染试剂8-甲氧基-9h-异噻唑并[5,4-b]喹啉-3,4-二酮及相关化合物
CA2824401A1 (en)	2012-07-19	Solid forms of gyrase inhibitor (r)-1-ethyl-3-[5-[2-(1-hydroxy-1-methyl-ethyl)pyrimidin-5-yl]-7-(tetrahydrofuran-2-yl)-1h-benzimidazol-2-yl]urea
US20090137681A1 (en)	2009-05-28	Sirtuin Inhibiting Compounds
CN103130686B (zh)	2016-09-14	N，n′-不对称二芳基取代脲类化合物及其制备方法和用途
US12522598B2 (en)	2026-01-13	3-(2-(heteroaryl)-pyridin-4-yl)-5-(trifluoromethyl)-1,2,4-oxadiazole derivatives as HDAC6 inhibitors
WO2018045313A1 (en)	2018-03-08	Substituted urea depsipeptide analogs as activators of the clpp endopeptidase
US20030166645A1 (en)	2003-09-04	Novel nitrofuran-containing heterocyclic compounds and uses thereof
WO2023114366A2 (en)	2023-06-22	Sulfonamide derivatives and their use as soluble epoxide hydrolase inhibitors
JP2001515072A (ja)	2001-09-18	ベンゾオキサゾール類およびベンゾチアゾール類の固相および液相合成ならびにそれらの使用
AU2002324455A1 (en)	2003-03-03	Fused pyrimidines as d-alanyl-d-alanine ligase inhibitors
Ahmed et al.	2021	Synthesis and in vitro antibacterial activity of morpholine derived benzenesulphonamides
KR20060002915A (ko)	2006-01-09	결정성 ｎ-포르밀 히드록실아민 화합물
US12503476B2 (en)	2025-12-23	Ring-fused 2-pyridone compounds, methods for preparation thereof and their use in the treatment and/or prevention of a disease involving gram-positive bacteria
JP2004137185A (ja)	2004-05-13	チオフェン骨格を有する抗菌剤
US20230095547A1 (en)	2023-03-30	Method for inhibiting growth of bacteria
US20110230533A1 (en)	2011-09-22	Imidazolidinedione derivatives as antimalarial agents, preparation thereof, and methods of use
JP2017105714A (ja)	2017-06-15	多剤排出ポンプ阻害剤
CN118666840A (zh)	2024-09-20	螺[吡咯烷-3,3′-喹啉]-2,2′-二酮哌啶甲酰胺类化合物的设计合成与应用