IL188794A

IL188794A - 10-substituted tetracyclines, pharmaceutical compositions comprising them and use thereof in the preparation of medicaments

10-substituted tetracyclines, pharmaceutical compositions comprising them and use thereof in the preparation of medicaments

Info

Publication number: IL188794A
Authority: IL; Israel
Prior art keywords: tetracycline compound; alkyl; hydrogen; tetracycline; aryl
Prior art date: 2005-07-21

Application number

IL188794A

Other languages

English (en)

Other versions

IL188794A0 (en

Original Assignee

Paratek Pharm Innc

Priority date

2005-07-21

Filing date

2008-01-15

Publication date

2012-10-31

2008-01-15 Application filed by Paratek Pharm Innc filed Critical Paratek Pharm Innc

2008-08-07 Publication of IL188794A0 publication Critical patent/IL188794A0/en

2012-10-31 Publication of IL188794A publication Critical patent/IL188794A/en

Links

239000004098 Tetracycline Substances 0.000 title claims description 287
235000019364 tetracycline Nutrition 0.000 title claims description 286
150000003522 tetracyclines Chemical class 0.000 title claims description 76
239000003814 drug Substances 0.000 title claims description 18
238000002360 preparation method Methods 0.000 title claims description 18
239000008194 pharmaceutical composition Chemical class 0.000 title claims description 8
229940040944 tetracyclines Drugs 0.000 title description 33
-1 tetracycline compound Chemical class 0.000 claims description 547
229930101283 tetracycline Natural products 0.000 claims description 255
229960002180 tetracycline Drugs 0.000 claims description 254
125000000217 alkyl group Chemical group 0.000 claims description 197
229910052739 hydrogen Inorganic materials 0.000 claims description 173
239000001257 hydrogen Substances 0.000 claims description 172
125000003342 alkenyl group Chemical group 0.000 claims description 168
125000003118 aryl group Chemical group 0.000 claims description 162
125000000304 alkynyl group Chemical group 0.000 claims description 150
125000003545 alkoxy group Chemical group 0.000 claims description 122
150000002431 hydrogen Chemical group 0.000 claims description 119
125000003282 alkyl amino group Chemical group 0.000 claims description 113
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 113
125000004414 alkyl thio group Chemical group 0.000 claims description 109
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 101
125000003710 aryl alkyl group Chemical group 0.000 claims description 94
125000000623 heterocyclic group Chemical group 0.000 claims description 91
229910052736 halogen Inorganic materials 0.000 claims description 89
150000002367 halogens Chemical class 0.000 claims description 85
150000001875 compounds Chemical class 0.000 claims description 84
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 81
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 65
125000002252 acyl group Chemical group 0.000 claims description 63
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 56
125000001072 heteroaryl group Chemical group 0.000 claims description 56
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 54
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 53
125000005129 aryl carbonyl group Chemical group 0.000 claims description 44
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 44
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 42
125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 42
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
229910052760 oxygen Inorganic materials 0.000 claims description 38
125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 37
125000001769 aryl amino group Chemical group 0.000 claims description 37
229910052717 sulfur Inorganic materials 0.000 claims description 37
150000003839 salts Chemical class 0.000 claims description 35
229910019142 PO4 Inorganic materials 0.000 claims description 34
125000004442 acylamino group Chemical group 0.000 claims description 34
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 34
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 34
239000010452 phosphate Chemical group 0.000 claims description 34
150000007942 carboxylates Chemical group 0.000 claims description 33
125000004663 dialkyl amino group Chemical group 0.000 claims description 33
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 32
125000004986 diarylamino group Chemical group 0.000 claims description 30
125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 29
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 29
206010028980 Neoplasm Diseases 0.000 claims description 28
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
125000005089 alkenylaminocarbonyl group Chemical group 0.000 claims description 26
125000004947 alkyl aryl amino group Chemical group 0.000 claims description 26
125000005110 aryl thio group Chemical group 0.000 claims description 26
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 25
125000004103 aminoalkyl group Chemical group 0.000 claims description 25
125000005200 aryloxy carbonyloxy group Chemical group 0.000 claims description 25
125000002877 alkyl aryl group Chemical group 0.000 claims description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
125000003368 amide group Chemical group 0.000 claims description 21
125000005018 aryl alkenyl group Chemical group 0.000 claims description 20
125000005015 aryl alkynyl group Chemical group 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 18
150000002148 esters Chemical class 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 17
125000005087 alkynylcarbonyl group Chemical group 0.000 claims description 16
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 15
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 14
125000005095 alkynylaminocarbonyl group Chemical group 0.000 claims description 14
201000011510 cancer Diseases 0.000 claims description 14
125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 13
125000004670 alkyl amino thio carbonyl group Chemical group 0.000 claims description 13
125000005225 alkynyloxycarbonyl group Chemical group 0.000 claims description 13
125000003435 aroyl group Chemical group 0.000 claims description 13
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 12
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 12
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 12
230000004054 inflammatory process Effects 0.000 claims description 12
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 10
241000894006 Bacteria Species 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 8
241000700605 Viruses Species 0.000 claims description 7
206010061218 Inflammation Diseases 0.000 claims description 6
201000006417 multiple sclerosis Diseases 0.000 claims description 6
241000124008 Mammalia Species 0.000 claims description 5
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 5
125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
208000007118 chronic progressive multiple sclerosis Diseases 0.000 claims description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical group CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
206010063401 primary progressive multiple sclerosis Diseases 0.000 claims description 2
201000008628 secondary progressive multiple sclerosis Diseases 0.000 claims description 2
239000012678 infectious agent Substances 0.000 claims 2
241000233866 Fungi Species 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
244000045947 parasite Species 0.000 claims 1
125000003386 piperidinyl group Chemical group 0.000 claims 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 1
239000000243 solution Substances 0.000 description 85
239000000651 prodrug Chemical group 0.000 description 45
229940002612 prodrug Drugs 0.000 description 45
150000003573 thiols Chemical group 0.000 description 44
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 39
238000000034 method Methods 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
125000001424 substituent group Chemical group 0.000 description 33
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 30
208000035475 disorder Diseases 0.000 description 29
239000003795 chemical substances by application Substances 0.000 description 24
239000003480 eluent Substances 0.000 description 23
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 22
230000001154 acute effect Effects 0.000 description 21
BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 20
QMEQBOSUJUOXMX-UHFFFAOYSA-N 2h-oxadiazine Chemical compound N1OC=CC=N1 QMEQBOSUJUOXMX-UHFFFAOYSA-N 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
230000002829 reductive effect Effects 0.000 description 19
150000003467 sulfuric acid derivatives Chemical class 0.000 description 19
239000002585 base Substances 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 18
239000007787 solid Substances 0.000 description 18
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 17
125000004093 cyano group Chemical group *C#N 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 description 16
125000000278 alkyl amino alkyl group Chemical group 0.000 description 16
229910052731 fluorine Inorganic materials 0.000 description 16
239000000203 mixture Substances 0.000 description 16
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 14
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 14
229910052794 bromium Inorganic materials 0.000 description 14
239000000460 chlorine Substances 0.000 description 14
229910052801 chlorine Inorganic materials 0.000 description 14
230000001684 chronic effect Effects 0.000 description 14
239000011737 fluorine Substances 0.000 description 14
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 14
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 14
238000011282 treatment Methods 0.000 description 14
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 13
125000005099 aryl alkyl carbonyl group Chemical group 0.000 description 13
125000005128 aryl amino alkyl group Chemical group 0.000 description 13
210000000988 bone and bone Anatomy 0.000 description 13
229910052757 nitrogen Inorganic materials 0.000 description 13
AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 12
238000005481 NMR spectroscopy Methods 0.000 description 12
125000005125 aryl alkyl amino carbonyl group Chemical group 0.000 description 12
125000004432 carbon atom Chemical group C* 0.000 description 12
230000005764 inhibitory process Effects 0.000 description 12
210000001519 tissue Anatomy 0.000 description 12
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 11
229910052799 carbon Inorganic materials 0.000 description 11
210000004027 cell Anatomy 0.000 description 11
229960004023 minocycline Drugs 0.000 description 11
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 11
150000003852 triazoles Chemical class 0.000 description 11
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
239000003638 chemical reducing agent Substances 0.000 description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
230000006870 function Effects 0.000 description 10
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 10
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 10
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
239000000126 substance Substances 0.000 description 10
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 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
241000186427 Cutibacterium acnes Species 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
125000004658 aryl carbonyl amino group Chemical group 0.000 description 9
206010012601 diabetes mellitus Diseases 0.000 description 9
201000010099 disease Diseases 0.000 description 9
239000012153 distilled water Substances 0.000 description 9
239000011347 resin Substances 0.000 description 9
229920005989 resin Polymers 0.000 description 9
229950000614 sancycline Drugs 0.000 description 9
XVGVNOVEJAWYEO-UHFFFAOYSA-N 3,4-dihydro-2h-oxadiazine Chemical compound C1NNOC=C1 XVGVNOVEJAWYEO-UHFFFAOYSA-N 0.000 description 8
WSXNRJXPTNQJBH-UHFFFAOYSA-N 5,6-dihydro-4h-thiazine Chemical compound C1CSN=CC1 WSXNRJXPTNQJBH-UHFFFAOYSA-N 0.000 description 8
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 8
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 8
239000002253 acid Substances 0.000 description 8
125000003806 alkyl carbonyl amino group Chemical group 0.000 description 8
125000003277 amino group Chemical group 0.000 description 8
238000003556 assay Methods 0.000 description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 8
239000012458 free base Substances 0.000 description 8
125000005842 heteroatom Chemical group 0.000 description 8
AZHVQJLDOFKHPZ-UHFFFAOYSA-N oxathiazine Chemical compound O1SN=CC=C1 AZHVQJLDOFKHPZ-UHFFFAOYSA-N 0.000 description 8
239000001301 oxygen Substances 0.000 description 8
108091032973 (ribonucleotides)n+m Proteins 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
206010002329 Aneurysm Diseases 0.000 description 7
102000002274 Matrix Metalloproteinases Human genes 0.000 description 7
108010000684 Matrix Metalloproteinases Proteins 0.000 description 7
125000005103 alkyl silyl group Chemical group 0.000 description 7
230000001580 bacterial effect Effects 0.000 description 7
238000001816 cooling Methods 0.000 description 7
125000000753 cycloalkyl group Chemical group 0.000 description 7
150000002430 hydrocarbons Chemical group 0.000 description 7
208000015181 infectious disease Diseases 0.000 description 7
208000027866 inflammatory disease Diseases 0.000 description 7
208000014674 injury Diseases 0.000 description 7
125000001624 naphthyl group Chemical group 0.000 description 7
239000000047 product Substances 0.000 description 7
238000012360 testing method Methods 0.000 description 7
229940124597 therapeutic agent Drugs 0.000 description 7
230000001225 therapeutic effect Effects 0.000 description 7
GBVSVMWJIRXRLT-UHFFFAOYSA-N 3,4-dihydro-2h-thiadiazine Chemical compound C1NNSC=C1 GBVSVMWJIRXRLT-UHFFFAOYSA-N 0.000 description 6
BYVSMDBDTBXASR-UHFFFAOYSA-N 5,6-dihydro-4h-oxazine Chemical compound C1CON=CC1 BYVSMDBDTBXASR-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
241000588724 Escherichia coli Species 0.000 description 6
208000019693 Lung disease Diseases 0.000 description 6
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000001356 alkyl thiols Chemical class 0.000 description 6
125000005104 aryl silyl group Chemical group 0.000 description 6
150000001504 aryl thiols Chemical class 0.000 description 6
125000004104 aryloxy group Chemical group 0.000 description 6
125000005843 halogen group Chemical group 0.000 description 6
231100000252 nontoxic Toxicity 0.000 description 6
230000003000 nontoxic effect Effects 0.000 description 6
125000004434 sulfur atom Chemical group 0.000 description 6
238000002560 therapeutic procedure Methods 0.000 description 6
230000003612 virological effect Effects 0.000 description 6
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 description 5
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PPSZHCXTGRHULJ-UHFFFAOYSA-N dioxazine Chemical compound O1ON=CC=C1 PPSZHCXTGRHULJ-UHFFFAOYSA-N 0.000 description 5
229960003722 doxycycline Drugs 0.000 description 5
229940079593 drug Drugs 0.000 description 5
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 5
238000000338 in vitro Methods 0.000 description 5
238000001727 in vivo Methods 0.000 description 5
230000007935 neutral effect Effects 0.000 description 5
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical group [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
125000000714 pyrimidinyl group Chemical group 0.000 description 5
230000000699 topical effect Effects 0.000 description 5
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 5
LOZWAPSEEHRYPG-UHFFFAOYSA-N 1,4-dithiane Chemical compound C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 description 4
QBYTXRKLVZHFND-UHFFFAOYSA-N 2h-thiadiazine Chemical compound N1SC=CC=N1 QBYTXRKLVZHFND-UHFFFAOYSA-N 0.000 description 4
KWIVRAVCZJXOQC-UHFFFAOYSA-N 3h-oxathiazole Chemical compound N1SOC=C1 KWIVRAVCZJXOQC-UHFFFAOYSA-N 0.000 description 4
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