JP2010513527A5

JP2010513527A5 -

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Publication number: JP2010513527A5
Authority: JP; Japan
Prior art keywords: hydrogen; compound; alkyl; item; alkoxy
Prior art date: 2007-12-21
Legal status : Granted

Application number

JP2009542938A

Other languages

English (en)

Japanese (ja)

Other versions

JP2010513527A (ja

JP5583411B2 (ja

Filing date

2007-12-21

Publication date

2011-02-17

2007-12-21 Application filed filed Critical

2007-12-21 Priority claimed from PCT/US2007/026178 external-priority patent/WO2008079339A2/en

2010-04-30 Publication of JP2010513527A publication Critical patent/JP2010513527A/ja

2011-02-17 Publication of JP2010513527A5 publication Critical patent/JP2010513527A5/ja

2014-09-03 Application granted granted Critical

2014-09-03 Publication of JP5583411B2 publication Critical patent/JP5583411B2/ja

Status Active legal-status Critical Current

2027-12-21 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims description 518
229910052739 hydrogen Inorganic materials 0.000 claims description 465
239000001257 hydrogen Substances 0.000 claims description 463
125000000217 alkyl group Chemical group 0.000 claims description 408
-1 complex A ring Chemical group 0.000 claims description 403
239000004098 Tetracycline Substances 0.000 claims description 269
235000019364 tetracycline Nutrition 0.000 claims description 269
229930101283 tetracycline Natural products 0.000 claims description 251
229960002180 tetracycline Drugs 0.000 claims description 250
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 229
125000003545 alkoxy group Chemical group 0.000 claims description 215
150000002431 hydrogen Chemical group 0.000 claims description 212
125000003282 alkyl amino group Chemical group 0.000 claims description 162
125000000304 alkynyl group Chemical group 0.000 claims description 159
125000003342 alkenyl group Chemical group 0.000 claims description 156
125000003118 aryl group Chemical group 0.000 claims description 151
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 146
150000003839 salts Chemical class 0.000 claims description 143
125000003710 aryl alkyl group Chemical group 0.000 claims description 131
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 127
125000004414 alkyl thio group Chemical group 0.000 claims description 127
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 120
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 93
125000001072 heteroaryl group Chemical group 0.000 claims description 87
125000004103 aminoalkyl group Chemical group 0.000 claims description 80
229910052736 halogen Inorganic materials 0.000 claims description 75
150000002367 halogens Chemical class 0.000 claims description 72
125000002252 acyl group Chemical group 0.000 claims description 60
150000003522 tetracyclines Chemical class 0.000 claims description 58
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 50
229910052760 oxygen Inorganic materials 0.000 claims description 42
239000000651 prodrug Chemical group 0.000 claims description 42
229940002612 prodrug Drugs 0.000 claims description 42
125000003386 piperidinyl group Chemical group 0.000 claims description 41
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 39
125000000623 heterocyclic group Chemical group 0.000 claims description 39
125000003396 thiol group Chemical class [H]S* 0.000 claims description 39
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 35
125000000753 cycloalkyl group Chemical group 0.000 claims description 34
125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 30
229910052717 sulfur Inorganic materials 0.000 claims description 30
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 27
150000001408 amides Chemical class 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 24
150000007942 carboxylates Chemical class 0.000 claims description 22
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 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 20
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 18
125000005129 aryl carbonyl group Chemical group 0.000 claims description 15
239000003814 drug Substances 0.000 claims description 15
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 14
125000003435 aroyl group Chemical group 0.000 claims description 14
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 8
125000005197 alkyl carbonyloxy alkyl group Chemical group 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 88
238000000034 method Methods 0.000 description 49
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 42
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 33
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 30
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 30
239000000543 intermediate Substances 0.000 description 27
206010028980 Neoplasm Diseases 0.000 description 23
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 22
230000001154 acute effect Effects 0.000 description 21
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 21
125000004663 dialkyl amino group Chemical group 0.000 description 20
208000035475 disorder Diseases 0.000 description 19
229940040944 tetracyclines Drugs 0.000 description 19
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 18
229910052757 nitrogen Inorganic materials 0.000 description 18
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 16
239000000203 mixture Substances 0.000 description 16
238000011282 treatment Methods 0.000 description 16
125000003806 alkyl carbonyl amino group Chemical group 0.000 description 15
230000004054 inflammatory process Effects 0.000 description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
201000011510 cancer Diseases 0.000 description 13
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 13
229910052763 palladium Inorganic materials 0.000 description 13
125000004432 carbon atom Chemical group C* 0.000 description 12
125000001424 substituent group Chemical group 0.000 description 12
208000035143 Bacterial infection Diseases 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
208000022362 bacterial infectious disease Diseases 0.000 description 11
201000010099 disease Diseases 0.000 description 11
229910052731 fluorine Inorganic materials 0.000 description 11
239000001301 oxygen Substances 0.000 description 11
239000000047 product Substances 0.000 description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 11
125000004457 alkyl amino carbonyl group Chemical group 0.000 description 10
125000004658 aryl carbonyl amino group Chemical group 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
230000001684 chronic effect Effects 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
239000011737 fluorine Substances 0.000 description 10
125000002971 oxazolyl group Chemical group 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-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
210000000988 bone and bone Anatomy 0.000 description 9
229910052799 carbon Inorganic materials 0.000 description 9
125000002541 furyl group Chemical group 0.000 description 9
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 9
125000001715 oxadiazolyl group Chemical group 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
125000003226 pyrazolyl group Chemical group 0.000 description 9
125000000168 pyrrolyl group Chemical group 0.000 description 9
239000000126 substance Substances 0.000 description 9
210000001519 tissue Anatomy 0.000 description 9
241001465754 Metazoa Species 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 8
125000004947 alkyl aryl amino group Chemical group 0.000 description 8
125000002877 alkyl aryl group Chemical group 0.000 description 8
125000001769 aryl amino group Chemical group 0.000 description 8
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
125000004986 diarylamino group Chemical group 0.000 description 8
125000005842 heteroatom Chemical group 0.000 description 8
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 8
150000003335 secondary amines Chemical class 0.000 description 8
125000000547 substituted alkyl group Chemical group 0.000 description 8
230000002194 synthesizing effect Effects 0.000 description 8
239000002253 acid Substances 0.000 description 7
125000004442 acylamino group Chemical group 0.000 description 7
125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 7
125000004691 alkyl thio carbonyl group Chemical group 0.000 description 7
125000003277 amino group Chemical group 0.000 description 7
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 7
125000005110 aryl thio group Chemical group 0.000 description 7
125000005200 aryloxy carbonyloxy group Chemical group 0.000 description 7
KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical group [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 description 7
150000002430 hydrocarbons Chemical group 0.000 description 7
ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 7
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 7
239000000243 solution Substances 0.000 description 7
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical group [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 7
229940124597 therapeutic agent Drugs 0.000 description 7
229910052721 tungsten Inorganic materials 0.000 description 7
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 6
206010002329 Aneurysm Diseases 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
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AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 6
206010061218 Inflammation Diseases 0.000 description 6
102000002274 Matrix Metalloproteinases Human genes 0.000 description 6
108010000684 Matrix Metalloproteinases Proteins 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
125000004694 alkoxyaminocarbonyl group Chemical group 0.000 description 6
125000005907 alkyl ester group Chemical group 0.000 description 6
239000003638 chemical reducing agent Substances 0.000 description 6
125000000392 cycloalkenyl group Chemical group 0.000 description 6
206010012601 diabetes mellitus Diseases 0.000 description 6
125000004473 dialkylaminocarbonyl group Chemical group 0.000 description 6
229940079593 drug Drugs 0.000 description 6
235000019441 ethanol Nutrition 0.000 description 6
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 6
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125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
230000002829 reductive effect Effects 0.000 description 6
125000004434 sulfur atom Chemical group 0.000 description 6
230000001225 therapeutic effect Effects 0.000 description 6
241000894006 Bacteria Species 0.000 description 5
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231100000252 nontoxic Toxicity 0.000 description 5
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
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GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 4
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KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
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125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
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JP2009542938A 2006-12-21 2007-12-21 細菌感染、ウイルス感染、および寄生虫感染の治療のためのテトラサイクリン誘導体 Active JP5583411B2 (ja)