AU2001271556A1 - 7,8 and 9-substituted tetracycline compounds - Google Patents

7,8 and 9-substituted tetracycline compounds

Info

Publication number: AU2001271556A1
Authority: AU; Australia
Prior art keywords: doxycycline; compound; phenyl; hydrogen; tetracycline
Prior art date: 2000-07-07
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

AU2001271556A

Other languages

English (en)

Inventor

Darrell Koza

Mark L Nelson

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Tufts University

Original Assignee

Tufts University

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.)

2000-07-07

Filing date

2001-06-29

Publication date

2002-01-21

2000-08-04 Priority claimed from PCT/US2000/021366 external-priority patent/WO2002012170A1/fr

2001-06-29 Application filed by Tufts University filed Critical Tufts University

2002-01-21 Publication of AU2001271556A1 publication Critical patent/AU2001271556A1/en

Status Abandoned legal-status Critical Current

Links

-1 tetracycline compounds Chemical class 0.000 title claims abstract description 151
239000004098 Tetracycline Substances 0.000 title claims abstract description 124
235000019364 tetracycline Nutrition 0.000 title claims abstract description 124
229960002180 tetracycline Drugs 0.000 title claims abstract description 116
229930101283 tetracycline Natural products 0.000 title claims abstract description 116
150000003522 tetracyclines Chemical class 0.000 claims abstract description 32
238000000034 method Methods 0.000 claims abstract description 25
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
229960003722 doxycycline Drugs 0.000 claims description 116
150000001875 compounds Chemical class 0.000 claims description 82
SGKRLCUYIXIAHR-AKNGSSGZSA-N (4s,4ar,5s,5ar,6r,12ar)-4-(dimethylamino)-1,5,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1=CC=C2[C@H](C)[C@@H]([C@H](O)[C@@H]3[C@](C(O)=C(C(N)=O)C(=O)[C@H]3N(C)C)(O)C3=O)C3=C(O)C2=C1O SGKRLCUYIXIAHR-AKNGSSGZSA-N 0.000 claims description 68
239000001257 hydrogen Substances 0.000 claims description 63
229910052739 hydrogen Inorganic materials 0.000 claims description 63
125000000304 alkynyl group Chemical group 0.000 claims description 42
150000002431 hydrogen Chemical group 0.000 claims description 36
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 36
125000003342 alkenyl group Chemical group 0.000 claims description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
125000001072 heteroaryl group Chemical group 0.000 claims description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 13
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 12
125000002252 acyl group Chemical group 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 9
208000035143 Bacterial infection Diseases 0.000 claims description 8
208000022362 bacterial infectious disease Diseases 0.000 claims description 8
125000005843 halogen group Chemical group 0.000 claims description 8
FMTDIUIBLCQGJB-UHFFFAOYSA-N Demethylchlortetracyclin Natural products C1C2C(O)C3=C(Cl)C=CC(O)=C3C(=O)C2=C(O)C2(O)C1C(N(C)C)C(O)=C(C(N)=O)C2=O FMTDIUIBLCQGJB-UHFFFAOYSA-N 0.000 claims description 7
229960002398 demeclocycline Drugs 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
125000005059 halophenyl group Chemical group 0.000 claims description 7
229960004023 minocycline Drugs 0.000 claims description 7
125000006501 nitrophenyl group Chemical group 0.000 claims description 7
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 6
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 5
125000002541 furyl group Chemical group 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000003373 pyrazinyl group Chemical group 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
229940072172 tetracycline antibiotic Drugs 0.000 claims description 4
BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical group NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims description 3
241000194032 Enterococcus faecalis Species 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
125000001207 fluorophenyl group Chemical group 0.000 claims 1
125000000217 alkyl group Chemical group 0.000 description 39
125000003118 aryl group Chemical group 0.000 description 26
239000000203 mixture Substances 0.000 description 18
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 15
239000000243 solution Substances 0.000 description 15
229910052757 nitrogen Inorganic materials 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
125000004432 carbon atom Chemical group C* 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
125000001424 substituent group Chemical group 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
125000003545 alkoxy group Chemical group 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
125000004448 alkyl carbonyl group Chemical group 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 10
229910052736 halogen Inorganic materials 0.000 description 10
150000002367 halogens Chemical group 0.000 description 10
125000000623 heterocyclic group Chemical group 0.000 description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
229910019142 PO4 Inorganic materials 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
125000004442 acylamino group Chemical group 0.000 description 9
125000003282 alkyl amino group Chemical group 0.000 description 9
239000002585 base Substances 0.000 description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 9
239000010452 phosphate Substances 0.000 description 9
125000004947 alkyl aryl amino group Chemical group 0.000 description 8
125000002877 alkyl aryl group Chemical group 0.000 description 8
125000003806 alkyl carbonyl amino group Chemical group 0.000 description 8
125000001769 aryl amino group Chemical group 0.000 description 8
125000004658 aryl carbonyl amino group Chemical group 0.000 description 8
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 8
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
239000003153 chemical reaction reagent Substances 0.000 description 8
125000004663 dialkyl amino group Chemical group 0.000 description 8
125000004986 diarylamino group Chemical group 0.000 description 8
125000005842 heteroatom Chemical group 0.000 description 8
239000000651 prodrug Substances 0.000 description 8
229940002612 prodrug Drugs 0.000 description 8
239000000047 product Substances 0.000 description 8
229910052717 sulfur Inorganic materials 0.000 description 8
229940040944 tetracyclines Drugs 0.000 description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 7
125000004457 alkyl amino carbonyl group Chemical group 0.000 description 7
125000005196 alkyl carbonyloxy group Chemical group 0.000 description 7
125000004644 alkyl sulfinyl group Chemical group 0.000 description 7
125000004691 alkyl thio carbonyl group Chemical group 0.000 description 7
125000004414 alkyl thio group Chemical group 0.000 description 7
125000005199 aryl carbonyloxy group Chemical group 0.000 description 7
125000005110 aryl thio group Chemical group 0.000 description 7
125000005200 aryloxy carbonyloxy group Chemical group 0.000 description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 7
150000007942 carboxylates Chemical class 0.000 description 7
125000004093 cyano group Chemical group *C#N 0.000 description 7
125000000753 cycloalkyl group Chemical group 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
150000002430 hydrocarbons Chemical group 0.000 description 7
229910052760 oxygen Inorganic materials 0.000 description 7
239000001301 oxygen Substances 0.000 description 7
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 7
150000003467 sulfuric acid derivatives Chemical group 0.000 description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
GUXHBMASAHGULD-SEYHBJAFSA-N (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical class C1([C@H]2O)=C(Cl)C=CC(O)=C1C(O)=C1[C@@H]2C[C@H]2[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]2(O)C1=O GUXHBMASAHGULD-SEYHBJAFSA-N 0.000 description 6
125000005129 aryl carbonyl group Chemical group 0.000 description 6
230000008878 coupling Effects 0.000 description 6
238000010168 coupling process Methods 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 6
125000000392 cycloalkenyl group Chemical group 0.000 description 6
239000003814 drug Substances 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
125000004434 sulfur atom Chemical group 0.000 description 6
230000001225 therapeutic effect Effects 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
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 5
241001465754 Metazoa Species 0.000 description 5
125000005907 alkyl ester group Chemical group 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
238000001727 in vivo Methods 0.000 description 5
208000015181 infectious disease Diseases 0.000 description 5
125000004433 nitrogen atom Chemical group N* 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
230000000699 topical effect Effects 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
FFTVPQUHLQBXQZ-KVUCHLLUSA-N (4s,4as,5ar,12ar)-4,7-bis(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=C(N(C)C)C=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O FFTVPQUHLQBXQZ-KVUCHLLUSA-N 0.000 description 4
241000894006 Bacteria Species 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
239000003242 anti bacterial agent Substances 0.000 description 4
229940088710 antibiotic agent Drugs 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000000969 carrier Substances 0.000 description 4
125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
125000004430 oxygen atom Chemical group O* 0.000 description 4
239000011593 sulfur Substances 0.000 description 4
238000002560 therapeutic procedure Methods 0.000 description 4
229910052723 transition metal Inorganic materials 0.000 description 4
150000003624 transition metals Chemical class 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
241000283690 Bos taurus Species 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
206010028980 Neoplasm Diseases 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
125000002723 alicyclic group Chemical group 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
230000037396 body weight Effects 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
150000001768 cations Chemical class 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000012954 diazonium Substances 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000002674 ointment Substances 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
125000004437 phosphorous atom Chemical group 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
238000000746 purification Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
241000894007 species Species 0.000 description 3
238000006467 substitution reaction Methods 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000003826 tablet Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
238000012360 testing method Methods 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 3
MTCQOMXDZUULRV-ADOAZJKMSA-N (4s,4as,5ar,12ar)-4-(dimethylamino)-1,10,11,12a-tetrahydroxy-3,12-dioxo-4a,5,5a,6-tetrahydro-4h-tetracene-2-carboxamide Chemical compound C1C2=CC=CC(O)=C2C(O)=C2[C@@H]1C[C@H]1[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]1(O)C2=O MTCQOMXDZUULRV-ADOAZJKMSA-N 0.000 description 2
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
241000272517 Anseriformes Species 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
241000283707 Capra Species 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
241000283086 Equidae Species 0.000 description 2
241000588724 Escherichia coli Species 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
241000282412 Homo Species 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
229910002666 PdCl2 Inorganic materials 0.000 description 2
241001494479 Pecora Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
206010037151 Psittacosis Diseases 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
241000607142 Salmonella Species 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000005089 alkenylaminocarbonyl group Chemical group 0.000 description 2
125000005090 alkenylcarbonyl group Chemical group 0.000 description 2
125000004183 alkoxy alkyl group Chemical group 0.000 description 2
125000003435 aroyl group Chemical group 0.000 description 2
125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 description 2
125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 2
150000001502 aryl halides Chemical class 0.000 description 2
238000003556 assay Methods 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 2
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
QQHZPQUHCAKSOL-UHFFFAOYSA-N butyl nitrate Chemical compound CCCCO[N+]([O-])=O QQHZPQUHCAKSOL-UHFFFAOYSA-N 0.000 description 2
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 2
239000011575 calcium Substances 0.000 description 2
201000011510 cancer Diseases 0.000 description 2
239000002775 capsule Substances 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
238000004040 coloring Methods 0.000 description 2
239000006071 cream Substances 0.000 description 2
238000011161 development Methods 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
230000006870 function Effects 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
150000004795 grignard reagents Chemical class 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
238000010255 intramuscular injection Methods 0.000 description 2
239000007927 intramuscular injection Substances 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
239000006210 lotion Substances 0.000 description 2
239000000314 lubricant Substances 0.000 description 2
208000001581 lymphogranuloma venereum Diseases 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
244000005700 microbiome Species 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
125000001979 organolithium group Chemical group 0.000 description 2
201000000901 ornithosis Diseases 0.000 description 2
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
125000005981 pentynyl group Chemical group 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000002953 preparative HPLC Methods 0.000 description 2
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
229950000614 sancycline Drugs 0.000 description 2
235000019333 sodium laurylsulphate Nutrition 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
125000005017 substituted alkenyl group Chemical group 0.000 description 2
125000005415 substituted alkoxy group Chemical group 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
125000004426 substituted alkynyl group Chemical group 0.000 description 2
239000000829 suppository Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
150000003568 thioethers Chemical class 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
SYUVAXDZVWPKSI-UHFFFAOYSA-N tributyl(phenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=CC=C1 SYUVAXDZVWPKSI-UHFFFAOYSA-N 0.000 description 2
125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 2
BPLUKJNHPBNVQL-UHFFFAOYSA-N triphenylarsine Chemical compound C1=CC=CC=C1[As](C=1C=CC=CC=1)C1=CC=CC=C1 BPLUKJNHPBNVQL-UHFFFAOYSA-N 0.000 description 2
NDQQRRVKUBPTHQ-QBIQUQHTSA-N (2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO NDQQRRVKUBPTHQ-QBIQUQHTSA-N 0.000 description 1
GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
PEPBFCOIJRULGJ-UHFFFAOYSA-N 3h-1,2,3-benzodioxazole Chemical compound C1=CC=C2NOOC2=C1 PEPBFCOIJRULGJ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241000588626 Acinetobacter baumannii Species 0.000 description 1
206010067484 Adverse reaction Diseases 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
229920000856 Amylose Polymers 0.000 description 1
238000009631 Broth culture Methods 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
239000004099 Chlortetracycline Substances 0.000 description 1
206010010741 Conjunctivitis Diseases 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
241000194031 Enterococcus faecium Species 0.000 description 1
241000194029 Enterococcus hirae Species 0.000 description 1
241001495410 Enterococcus sp. Species 0.000 description 1
108090000371 Esterases Proteins 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
241000287828 Gallus gallus Species 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
241000282575 Gorilla Species 0.000 description 1
241000606768 Haemophilus influenzae Species 0.000 description 1
239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
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 1
206010061218 Inflammation Diseases 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
240000003183 Manihot esculenta Species 0.000 description 1
235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
241000588655 Moraxella catarrhalis Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241000282339 Mustela Species 0.000 description 1
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
239000004100 Oxytetracycline Substances 0.000 description 1
241000282579 Pan Species 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
108091005804 Peptidases Proteins 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
241000286209 Phasianidae Species 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000288906 Primates Species 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
239000004365 Protease Substances 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
241000282887 Suidae 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
238000006069 Suzuki reaction reaction Methods 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
206010046306 Upper respiratory tract infection Diseases 0.000 description 1
206010048038 Wound infection Diseases 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
RBYGDVHOECIAFC-UHFFFAOYSA-L acetonitrile;palladium(2+);dichloride Chemical compound [Cl-].[Cl-].[Pd+2].CC#N.CC#N RBYGDVHOECIAFC-UHFFFAOYSA-L 0.000 description 1
230000009471 action Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
230000006838 adverse reaction Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000005233 alkylalcohol group Chemical group 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000012080 ambient air Substances 0.000 description 1
230000001668 ameliorated effect Effects 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
235000006708 antioxidants Nutrition 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000005128 aryl amino alkyl group Chemical group 0.000 description 1
150000007860 aryl ester derivatives Chemical class 0.000 description 1
229940072107 ascorbate Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
239000012752 auxiliary agent Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
230000003385 bacteriostatic effect Effects 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
229940077388 benzenesulfonate 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
125000002619 bicyclic group Chemical group 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
125000005620 boronic acid group Chemical class 0.000 description 1
238000002815 broth microdilution Methods 0.000 description 1
239000000872 buffer Substances 0.000 description 1
244000309464 bull Species 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229960003563 calcium carbonate Drugs 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
235000013330 chicken meat Nutrition 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
CYDMQBQPVICBEU-UHFFFAOYSA-N chlorotetracycline Natural products C1=CC(Cl)=C2C(O)(C)C3CC4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-UHFFFAOYSA-N 0.000 description 1
229960004475 chlortetracycline Drugs 0.000 description 1
CYDMQBQPVICBEU-XRNKAMNCSA-N chlortetracycline Chemical compound C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O CYDMQBQPVICBEU-XRNKAMNCSA-N 0.000 description 1
235000019365 chlortetracycline Nutrition 0.000 description 1
229940001468 citrate Drugs 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000007423 decrease Effects 0.000 description 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005070 decynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
230000006735 deficit Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
230000009429 distress Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000009510 drug design Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
SKCMXSHCLAODMQ-UHFFFAOYSA-N ethenyl(trimethyl)stannane Chemical compound C[Sn](C)(C)C=C SKCMXSHCLAODMQ-UHFFFAOYSA-N 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
GINAGCMIRYVIQT-UHFFFAOYSA-N ethynyl(trimethyl)stannane Chemical compound C[Sn](C)(C)C#C GINAGCMIRYVIQT-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
229930195712 glutamate Natural products 0.000 description 1
229960002449 glycine Drugs 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000002390 heteroarenes Chemical class 0.000 description 1
125000006038 hexenyl group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005980 hexynyl group Chemical group 0.000 description 1
239000003906 humectant Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000007943 implant Substances 0.000 description 1
201000001371 inclusion conjunctivitis Diseases 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Chemical group 0.000 description 1
239000011630 iodine Chemical group 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
229940075495 isopropyl palmitate Drugs 0.000 description 1
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
235000015110 jellies Nutrition 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
244000144972 livestock Species 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910001425 magnesium ion Inorganic materials 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
208000004396 mastitis Diseases 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
239000002609 medium Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
231100000417 nephrotoxicity Toxicity 0.000 description 1
125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005071 nonynyl group Chemical group C(#CCCCCCCC)* 0.000 description 1
125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000008203 oral pharmaceutical composition Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
229960000625 oxytetracycline Drugs 0.000 description 1
IWVCMVBTMGNXQD-PXOLEDIWSA-N oxytetracycline Chemical compound C1=CC=C2[C@](O)(C)[C@H]3[C@H](O)[C@H]4[C@H](N(C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-PXOLEDIWSA-N 0.000 description 1
235000019366 oxytetracycline Nutrition 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
229940014662 pantothenate Drugs 0.000 description 1
235000019161 pantothenic acid Nutrition 0.000 description 1
239000011713 pantothenic acid Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000006072 paste Substances 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
239000002304 perfume Substances 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
125000003367 polycyclic group 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
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
244000144977 poultry Species 0.000 description 1
235000013594 poultry meat Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Chemical group COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000006894 reductive elimination reaction Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
230000004044 response Effects 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
239000012266 salt solution Substances 0.000 description 1
238000012216 screening Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
229960001790 sodium citrate Drugs 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003536 tetrazoles Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000005300 thiocarboxy group Chemical group C(=S)(O)* 0.000 description 1
229930192474 thiophene Chemical group 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000006478 transmetalation reaction Methods 0.000 description 1
150000003626 triacylglycerols Chemical class 0.000 description 1
150000003852 triazoles Chemical group 0.000 description 1
QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
YEMJHNYABQHWHL-UHFFFAOYSA-N tributyl(ethynyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C#C YEMJHNYABQHWHL-UHFFFAOYSA-N 0.000 description 1
125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
- C07C237/26—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton of a ring being part of a condensed ring system formed by at least four rings, e.g. tetracycline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- 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
- A61P35/00—Antineoplastic agents

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Diabetes (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Emergency Medicine (AREA)
Obesity (AREA)
Oncology (AREA)
Endocrinology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Hematology (AREA)
Communicable Diseases (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyridine Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Furan Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

AU2001271556A 2000-07-07 2001-06-29 7,8 and 9-substituted tetracycline compounds Abandoned AU2001271556A1 (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US21665600P	2000-07-07	2000-07-07
US60216656		2000-07-07
PCT/US2000/021366 WO2002012170A1 (fr)	2000-08-04	2000-08-04	Composes de tetracycline substitues en 8
WOUS00/21366		2000-08-04
PCT/US2001/020558 WO2002004404A2 (fr)	2000-07-07	2001-06-29	Composes de tetracycline substitues en 7, 8 et 9

Publications (1)

Publication Number	Publication Date
AU2001271556A1 true AU2001271556A1 (en)	2002-01-21

Family

ID=26680300

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU2001271556A Abandoned AU2001271556A1 (en)	2000-07-07	2001-06-29	7,8 and 9-substituted tetracycline compounds

Country Status (8)

Country	Link
US (1)	US6624168B2 (fr)
EP (2)	EP1303479B1 (fr)
JP (1)	JP4963771B2 (fr)
AT (1)	ATE504562T1 (fr)
AU (1)	AU2001271556A1 (fr)
CA (1)	CA2415086A1 (fr)
DE (1)	DE60144375D1 (fr)
WO (1)	WO2002004404A2 (fr)

Families Citing this family (63)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6756365B2 (en) *	1991-11-06	2004-06-29	Trustees Of Tufts College	Reducing tetracycline resistance in living cells
US8106225B2 (en) *	1999-09-14	2012-01-31	Trustees Of Tufts College	Methods of preparing substituted tetracyclines with transition metal-based chemistries
CN1399627A (zh) *	1999-09-14	2003-02-26	塔夫茨大学信托人	用基于过渡金属的化学制备取代四环素的方法
WO2001052858A1 (fr) *	2000-01-24	2001-07-26	Trustees Of Tufts College	Composes de tetracycline pour le traitement de troubles afferents au cryptosporidium parvum
HUP0300082A2 (en) *	2000-03-31	2003-05-28	Paratek Pharmaceuticals	7- and 9-carbamate, urea, thiourea, thiocarbamate, and heteroaryl-amino substituted tetracycline derivatives, process for their preparation and use and pharmaceutical compositions containing them
US6642270B2 (en) *	2000-05-15	2003-11-04	Paratek Pharmaceuticals, Inc.	7-substituted fused ring tetracycline compounds
WO2001098236A2 (fr) *	2000-06-16	2001-12-27	Trustees Of Tufts College	Composes de tetracycline 7-phenyl-substituee
US20040224927A1 (en) *	2000-06-16	2004-11-11	Trustees Of Tufts College	7-N-substituted phenyl tetracycline compounds
US20020132798A1 (en)	2000-06-16	2002-09-19	Nelson Mark L.	7-phenyl-substituted tetracycline compounds
US7094806B2 (en) *	2000-07-07	2006-08-22	Trustees Of Tufts College	7, 8 and 9-substituted tetracycline compounds
BRPI0112269B8 (pt)	2000-07-07	2021-05-25	Paratek Pharm Innc	composto de minociclina 9-aminometila substituída, e, composição farmacêutica
BR0112265A (pt) *	2000-07-07	2003-06-24	Tufts College	Compostos de tetraciclina substituìda, e de sanciclina 7-substituìda, método para tratar um estado responsivo à tetraciclina em um indivìduo, e, composição farmacêutica
HRP20030743A2 (en) *	2001-03-13	2005-06-30	Paratek Pharmaceuticals	7,9-substituted tetracycline compounds
EP1241160A1 (fr) *	2001-03-13	2002-09-18	Glaxo Group Limited	Dérivés de tétracyclines et leur utilisation comme agents antibiotiques
AU2002250331A1 (en) *	2001-03-13	2002-09-24	Paratek Pharmaceuticals, Inc.	7-pyrollyl tetracycline compounds and methods of use thereof
US7553828B2 (en) *	2001-03-13	2009-06-30	Paratek Pharmaceuticals, Inc.	9-aminomethyl substituted minocycline compounds
EP1381372A2 (fr)	2001-03-14	2004-01-21	Paratek Pharmaceuticals, Inc.	Composes de tetracycline substitue utilises en tant qu'antifongiques synergiques
US8088820B2 (en) *	2001-04-24	2012-01-03	Paratek Pharmaceuticals, Inc.	Substituted tetracycline compounds for the treatment of malaria
EP2329828A1 (fr)	2001-07-13	2011-06-08	Paratek Pharmaceuticals, Inc.	Tetracyclines pour le traitement de l'ischémie
US20060194773A1 (en) *	2001-07-13	2006-08-31	Paratek Pharmaceuticals, Inc.	Tetracyline compounds having target therapeutic activities
AU2002365120A1 (en)	2001-08-02	2003-07-15	Paratek Pharmaceuticals, Inc.	Medicaments
EP2311798A1 (fr) *	2002-01-08	2011-04-20	Paratek Pharmaceuticals, Inc.	Composés de tétracycline 4-dedimethylamino
EP1482926A4 (fr) *	2002-03-08	2006-04-12	Paratek Pharm Innc	Composes a base de tetracycline a substitution aminomethyle
WO2003079984A2 (fr) *	2002-03-21	2003-10-02	Paratek Pharmaceuticals, Inc.	Composes de tetracycline substituee
WO2004006850A2 (fr) *	2002-07-12	2004-01-22	Paratek Pharmaceuticals, Inc	Composes de tetracycline substituee en 3, 10, et 12a
EP1562608A4 (fr)	2002-10-24	2010-09-01	Paratek Pharm Innc	Procedes d'utilisation de composes tetracycline substituee pour moduler l'arn
US20060287283A1 (en) *	2003-07-09	2006-12-21	Paratek Pharmaceuticals, Inc.	Prodrugs of 9-aminomethyl tetracycline compounds
CN1845897A (zh) *	2003-07-09	2006-10-11	帕拉特克药品公司	取代的四环素化合物
EP1716101A1 (fr)	2004-01-15	2006-11-02	Paratek Pharmaceuticals, Inc.	Derives a cycle aromatique a provenant de composes de tetracycline
AU2014250722B2 (en) *	2004-05-21	2016-05-26	President And Fellows Of Harvard College	Synthesis of tetracyclines and analogues thereof
CN101027279B (zh)	2004-05-21	2013-03-27	哈佛大学校长及研究员协会	四环素及其类似物的合成
AU2012202559B2 (en) *	2004-05-21	2014-07-17	President And Fellows Of Harvard College	Synthesis of tetracyclines and analogues thereof
TWI261038B (en) *	2004-08-11	2006-09-01	Bo-Cheng Chen	Bicycle gear-shifting handgrip
WO2006047671A2 (fr)	2004-10-25	2006-05-04	Paratek Pharmaceuticals, Inc.	4-aminotetracyclines et procedes d'utilisation
US8466132B2 (en)	2004-10-25	2013-06-18	Paratek Pharmaceuticals, Inc.	Substituted tetracycline compounds
AU2006210406C1 (en)	2005-02-04	2013-03-07	Paratek Pharmaceuticals, Inc.	11a, 12-derivatives of tetracycline compounds
WO2006088720A2 (fr) *	2005-02-15	2006-08-24	Wyeth	Tetracyclines 9-substituees
AR057324A1 (es) *	2005-05-27	2007-11-28	Wyeth Corp	Tigeciclina y metodos para preparar 9-aminominociclina
AR057033A1 (es) *	2005-05-27	2007-11-14	Wyeth Corp	Tigeciclina y metodos para preparar 9-nitrominociclina
AR057032A1 (es) *	2005-05-27	2007-11-14	Wyeth Corp	Tigeciclina y metodos de preparacion
EP1910273A2 (fr) *	2005-07-21	2008-04-16	Paratek Pharmaceuticals, Inc.	Tetracyclines 10-substituees et leurs procedes d'utilisation
JP5335664B2 (ja) *	2006-04-07	2013-11-06	プレジデントアンドフェロウズオブハーバードカレッジ	テトラサイクリンおよびその類似体の合成
EP2431469A3 (fr)	2006-05-15	2012-05-30	Paratek Pharmaceuticals, Inc.	Procédés de régulation de l'expression des gènes ou produits génétiques utilisant des composés tétracyclines substitués
WO2008127361A2 (fr)	2006-10-11	2008-10-23	President And Fellows Of Harvard College	Synthèse d'un intermédiaire d'énone
US8440646B1 (en)	2006-10-11	2013-05-14	Paratek Pharmaceuticals, Inc.	Substituted tetracycline compounds for treatment of Bacillus anthracis infections
PL2109602T3 (pl)	2006-12-21	2014-09-30	Paratek Pharm Innc	Pochodne tetracyliny do leczenia zakażeń bakteryjnych, wirusowych i pasożytniczych
SI2120963T1 (sl)	2006-12-21	2019-02-28	Paratek Pharmaceuticals, Inc.	Substituirane spojine tetraciklina za zdravljenje vnetnih kožnih motenj
EP2144614A1 (fr)	2007-04-12	2010-01-20	Paratek Pharmaceuticals, Inc.	Procédés pour le traitement de l'amyotrophie spinale à l'aide de composés tétracyclines.
EP2144870A2 (fr) *	2007-04-27	2010-01-20	Paratek Pharmaceuticals, Inc.	Procedes de synthese et de purification de composes d'aminoalkyltetracycline
KR20100042276A (ko)	2007-07-06	2010-04-23	파라테크 파마슈티컬스, 인크.	치환 테트라사이클린 화합물의 합성방법
HRP20120735T1 (hr)	2007-11-29	2012-10-31	Actelion Pharmaceuticals Ltd.	Derivati fosfonske kiseline i njihova uporaba kao antagonista p2y12 receptora
WO2009111064A2 (fr)	2008-03-05	2009-09-11	Paratek Pharmaceuticals, Inc.	Composés de minocycline et procédés d’utilisation de ceux-ci
EP2276342A4 (fr) *	2008-04-14	2012-02-22	Paratek Pharm Innc	Composés à base de tétracyclines substituées
SI2323972T1 (sl)	2008-08-08	2013-11-29	Tetraphase Pharmaceuticals, Inc.	C7-fluoro substituirane tetraciklinske spojine
CN102215681A (zh) *	2008-09-19	2011-10-12	帕拉特克药品公司	用于治疗类风湿性关节炎的四环素化合物和相关的治疗方法
US9073829B2 (en)	2009-04-30	2015-07-07	President And Fellows Of Harvard College	Synthesis of tetracyclines and intermediates thereto
CN107021887A (zh)	2009-05-08	2017-08-08	四相制药公司	四环素类化合物
IN2012DN02502A (fr)	2009-08-28	2015-08-28	Tetraphase Pharmaceuticals Inc
WO2012021712A1 (fr) *	2010-08-12	2012-02-16	Tetraphase Pharmaceuticals, Inc.	Analogues de tétracycline
CN108276404A (zh)	2012-08-31	2018-07-13	四相制药公司	四环素化合物
RU2668535C2 (ru) *	2016-09-22	2018-10-01	Федеральное государственное бюджетное научное учреждение "Уральский федеральный аграрный научно-исследовательский центр Уральского отделения Российской академии наук" (ФГБНУ УрФАНИЦ УрО РАН)	Способ профилактики маститов у высокопродуктивных коров
CN110582486B (zh)	2016-10-19	2024-01-12	四相制药公司	艾若威四环素的结晶形式
AU2017353588B2 (en)	2016-11-01	2022-07-14	Paratek Pharmaceuticals, Inc.	9-aminomethyl minocycline compounds and use thereof in treating Community-Acquired Bacterial Pneumonia (CABP)

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2990331A (en)	1956-11-23	1961-06-27	Pfizer & Co C	Stable solutions of salts of tetracyclines for parenteral administration
US2980584A (en)	1957-10-29	1961-04-18	Pfizer & Co C	Parenteral magnesium oxytetracycline acetic or lactic acid carboxamide vehicle preparation
US3062717A (en)	1958-12-11	1962-11-06	Pfizer & Co C	Intramuscular calcium tetracycline acetic or lactic acid carboxamide vehicle preparation
US3165531A (en)	1962-03-08	1965-01-12	Pfizer & Co C	13-substituted-6-deoxytetracyclines and process utilizing the same
US3454697A (en)	1965-06-08	1969-07-08	American Cyanamid Co	Tetracycline antibiotic compositions for oral use
US3388162A (en) *	1966-03-14	1968-06-11	American Cyanamid Co	7-and/or 9-nitro or amino tetracyclines
NL6607516A (fr)	1966-05-31	1967-12-01
DE1767891C3 (de)	1968-06-28	1980-10-30	Pfizer	Verfahren zur Herstellung von wäßrigen arzneilichen Lösungen für die parenterale, perorale und lokale Anwendung mit einem Gehalt an einem Tetracyclinderivat
US3957980A (en)	1972-10-26	1976-05-18	Pfizer Inc.	Doxycycline parenteral compositions
DE2442829A1 (de)	1974-09-06	1976-03-18	Merck Patent Gmbh	Tetracyclische verbindungen und verfahren zu ihrer herstellung
US4018889A (en)	1976-01-02	1977-04-19	Pfizer Inc.	Oxytetracycline compositions
US4126680A (en)	1977-04-27	1978-11-21	Pfizer Inc.	Tetracycline antibiotic compositions
US5064821A (en) *	1982-11-18	1991-11-12	Trustees Of Tufts College	Method and compositions for overcoming tetracycline resistance within living cells
SG47520A1 (en) *	1992-08-13	1998-04-17	American Cyanamid Co	New method for the production of 9-amino-6-demethyl-6-deoxytetracycline
DK0599397T3 (da)	1992-11-17	1996-09-16	Univ New York State Res Found	Tetracycliner, herunder non-mikrobielle, kemisk-modificerede tetracycliner, inhiberer overdreven collagentværbinding ved diabetes
WO1995022529A1 (fr)	1994-02-17	1995-08-24	Pfizer Inc.	Derives de 9-(amino-substitues)-alpha-6-deoxy-5-oxy tetracycline, leur preparation et leur utilisation comme antibiotiques
US5789395A (en)	1996-08-30	1998-08-04	The Research Foundation Of State University Of New York	Method of using tetracycline compounds for inhibition of endogenous nitric oxide production
AU766200B2 (en) *	1998-11-18	2003-10-09	Collagenex Pharmaceuticals, Inc.	Novel 4-dedimethy laminotetra cycline derivatives

2001
- 2001-06-29 WO PCT/US2001/020558 patent/WO2002004404A2/fr not_active Ceased
- 2001-06-29 EP EP01950582A patent/EP1303479B1/fr not_active Expired - Lifetime
- 2001-06-29 JP JP2002509072A patent/JP4963771B2/ja not_active Expired - Fee Related
- 2001-06-29 DE DE60144375T patent/DE60144375D1/de not_active Expired - Lifetime
- 2001-06-29 EP EP09175818A patent/EP2166000A1/fr not_active Withdrawn
- 2001-06-29 CA CA002415086A patent/CA2415086A1/fr not_active Abandoned
- 2001-06-29 AT AT01950582T patent/ATE504562T1/de not_active IP Right Cessation
- 2001-06-29 US US09/894,805 patent/US6624168B2/en not_active Expired - Lifetime
- 2001-06-29 AU AU2001271556A patent/AU2001271556A1/en not_active Abandoned

Also Published As

Publication number	Publication date
ATE504562T1 (de)	2011-04-15
EP2166000A1 (fr)	2010-03-24
DE60144375D1 (de)	2011-05-19
US6624168B2 (en)	2003-09-23
CA2415086A1 (fr)	2002-01-17
JP2004502750A (ja)	2004-01-29
EP1303479B1 (fr)	2011-04-06
EP1303479A2 (fr)	2003-04-23
JP4963771B2 (ja)	2012-06-27
WO2002004404A2 (fr)	2002-01-17
WO2002004404A3 (fr)	2002-06-13
US20020111335A1 (en)	2002-08-15

Publication	Publication Date	Title
EP1303479B1 (fr)	2011-04-06	Composes de tetracycline substitues en 7, 8 et 9
US7696188B2 (en)	2010-04-13	7,8 and 9-substituted tetracycline compounds
US8012951B2 (en)	2011-09-06	7-N-substituted phenyl tetracycline compounds
US8288570B2 (en)	2012-10-16	7-iodo tetracyclines and related methods
US20080306032A1 (en)	2008-12-11	7-Phenyl-Substituted Tetracycline Compounds
US20020128237A1 (en)	2002-09-12	7-N-substituted phenyl tetracycline compounds
WO2001098260A1 (fr)	2001-12-27	Composes de phenyl tetracycline 7-n-substituee
WO2002012170A1 (fr)	2002-02-14	Composes de tetracycline substitues en 8
EP1301465A2 (fr)	2003-04-16	Composes methacycline 13-substitues
HK1142058A (en)	2010-11-26	7-, 8- and 9-substituted tetracycline compounds
HK1156023A (en)	2012-06-01	7-substituted fused ring tetracycline compounds
EP1426369A1 (fr)	2004-06-09	Composés tétracycline substitués en 7 par cycle condensé