TW200524930A - Quinolone antibacterial agents - Google Patents

Quinolone antibacterial agents Download PDF

Info

Publication number: TW200524930A
Authority: TW; Taiwan
Prior art keywords: ethyl; methyl; cyclopropyl; dihydro; cyano
Prior art date: 2003-11-18

Application number

TW093135213A

Other languages

English (en)

Chinese (zh)

Inventor

Edmund Lee Ellsworth

Clarke Bentley Taylor

Sean Timothy Murphy

Mark Ryan Rauckhorst

Jeremy Tyson Starr

Kim Marie Hutchings

Chris Limberakis

Denton Wade Hoyer

Original Assignee

Warner Lambert Co

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.)

2003-11-18

Filing date

2004-11-17

Publication date

2005-08-01

2004-11-17 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2005-08-01 Publication of TW200524930A publication Critical patent/TW200524930A/zh

Links

239000003242 anti bacterial agent Substances 0.000 title abstract description 5
229940072132 quinolone antibacterials Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 234
238000000034 method Methods 0.000 claims abstract description 50
-1 alkyl nitrile Chemical class 0.000 claims description 240
125000000217 alkyl group Chemical group 0.000 claims description 194
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 184
239000002253 acid Substances 0.000 claims description 133
229910052799 carbon Inorganic materials 0.000 claims description 63
125000003118 aryl group Chemical group 0.000 claims description 59
125000001072 heteroaryl group Chemical group 0.000 claims description 54
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 50
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 42
125000005843 halogen group Chemical group 0.000 claims description 41
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 37
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 36
RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 36
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 30
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
RPHIBDCSJKDQPG-UHFFFAOYSA-N OC(C1=CNC=CC1)=O.[O] Chemical compound OC(C1=CNC=CC1)=O.[O] RPHIBDCSJKDQPG-UHFFFAOYSA-N 0.000 claims description 27
125000000753 cycloalkyl group Chemical group 0.000 claims description 24
125000000623 heterocyclic group Chemical group 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 20
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 17
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 17
229910052760 oxygen Inorganic materials 0.000 claims description 17
239000001301 oxygen Substances 0.000 claims description 16
229910052702 rhenium Inorganic materials 0.000 claims description 12
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
229910021481 rutherfordium Inorganic materials 0.000 claims description 11
239000011734 sodium Substances 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
239000007789 gas Substances 0.000 claims description 10
125000005842 heteroatom Chemical group 0.000 claims description 10
150000002825 nitriles Chemical class 0.000 claims description 10
229910052708 sodium Inorganic materials 0.000 claims description 10
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 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
150000001735 carboxylic acids Chemical class 0.000 claims description 8
WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
208000035143 Bacterial infection Diseases 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
125000000304 alkynyl group Chemical group 0.000 claims description 7
208000022362 bacterial infectious disease Diseases 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
241000124008 Mammalia Species 0.000 claims description 6
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000001188 haloalkyl group Chemical group 0.000 claims description 6
229910052705 radium Inorganic materials 0.000 claims description 6
229910052701 rubidium Inorganic materials 0.000 claims description 6
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 5
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
229910021529 ammonia Inorganic materials 0.000 claims description 4
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
125000000842 isoxazolyl group Chemical group 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
150000003254 radicals Chemical class 0.000 claims description 4
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
235000001258 Cinchona calisaya Nutrition 0.000 claims description 3
ZRQIANXWARFGEJ-UHFFFAOYSA-N N1C=C(CC2=CC=CC=C12)C(=O)O.[O] Chemical compound N1C=C(CC2=CC=CC=C12)C(=O)O.[O] ZRQIANXWARFGEJ-UHFFFAOYSA-N 0.000 claims description 3
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 3
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
125000006419 fluorocyclopropyl group Chemical group 0.000 claims description 3
125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 3
150000007857 hydrazones Chemical class 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
229960000948 quinine Drugs 0.000 claims description 3
SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 claims description 2
LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims description 2
CYPMPLFWQTUXLR-UHFFFAOYSA-N C1=CC=CC=2C3=CC=CC=C3CC12.[O] Chemical compound C1=CC=CC=2C3=CC=CC=C3CC12.[O] CYPMPLFWQTUXLR-UHFFFAOYSA-N 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
229960004488 linolenic acid Drugs 0.000 claims description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
UNIJBMUBHBAUET-UHFFFAOYSA-N 3-(methylamino)propanenitrile Chemical compound CNCCC#N UNIJBMUBHBAUET-UHFFFAOYSA-N 0.000 claims 3
125000000168 pyrrolyl group Chemical group 0.000 claims 3
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
GOLXRNDWAUTYKT-UHFFFAOYSA-N 3-(1H-indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(CCC(=O)O)=CNC2=C1 GOLXRNDWAUTYKT-UHFFFAOYSA-N 0.000 claims 1
101000797951 Anguilla japonica Galactose-binding lectin l-1 Proteins 0.000 claims 1
DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 claims 1
LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
AYHPSSYMLCQJJG-UHFFFAOYSA-N N1C=CCC2=CC=CC=C12.[O] Chemical compound N1C=CCC2=CC=CC=C12.[O] AYHPSSYMLCQJJG-UHFFFAOYSA-N 0.000 claims 1
235000006040 Prunus persica var persica Nutrition 0.000 claims 1
240000006413 Prunus persica var. persica Species 0.000 claims 1
GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical group N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims 1
229940000488 arsenic acid Drugs 0.000 claims 1
125000005418 aryl aryl group Chemical group 0.000 claims 1
229960004251 hydroquinine Drugs 0.000 claims 1
JUNOWSHJELIDQP-UHFFFAOYSA-N morpholin-4-ium-3-carboxylate Chemical compound OC(=O)C1COCCN1 JUNOWSHJELIDQP-UHFFFAOYSA-N 0.000 claims 1
IJYBECNDMZQOGA-UHFFFAOYSA-N naphthalene pyridine-3-carboxylic acid Chemical compound C(C1=CN=CC=C1)(=O)O.C1=CC=CC2=CC=CC=C12 IJYBECNDMZQOGA-UHFFFAOYSA-N 0.000 claims 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 claims 1
CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical group O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims 1
229930006728 pinane Natural products 0.000 claims 1
XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane of uncertain configuration Natural products CC1CCC2C(C)(C)C1C2 XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 76
238000002360 preparation method Methods 0.000 abstract description 57
239000000243 solution Substances 0.000 description 198
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 171
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 140
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 100
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 99
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 92
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
235000019439 ethyl acetate Nutrition 0.000 description 51
239000007787 solid Substances 0.000 description 40
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 36
230000002829 reductive effect Effects 0.000 description 35
238000005859 coupling reaction Methods 0.000 description 34
239000012043 crude product Substances 0.000 description 33
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238000010168 coupling process Methods 0.000 description 28
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CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
229920006395 saturated elastomer Polymers 0.000 description 23
150000001412 amines Chemical class 0.000 description 22
239000002904 solvent Substances 0.000 description 21
229910052943 magnesium sulfate Inorganic materials 0.000 description 20
239000012044 organic layer Substances 0.000 description 20
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 19
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239000012267 brine Substances 0.000 description 17
150000001732 carboxylic acid derivatives Chemical class 0.000 description 17
239000002244 precipitate Substances 0.000 description 17
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
239000003921 oil Substances 0.000 description 16
235000019198 oils Nutrition 0.000 description 16
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
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239000002585 base Substances 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
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239000000047 product Substances 0.000 description 13
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239000010410 layer Substances 0.000 description 12
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238000004587 chromatography analysis Methods 0.000 description 10
229910052739 hydrogen Inorganic materials 0.000 description 10
238000005984 hydrogenation reaction Methods 0.000 description 10
229910052763 palladium Inorganic materials 0.000 description 10
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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 6
239000012071 phase Substances 0.000 description 6
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239000008215 water for injection Substances 0.000 description 6
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 5
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 description 5
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235000019333 sodium laurylsulphate Nutrition 0.000 description 1
OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
KQJWHIKPAMMQFZ-UHFFFAOYSA-M sodium;phenylmethanesulfinate Chemical compound [Na+].[O-]S(=O)CC1=CC=CC=C1 KQJWHIKPAMMQFZ-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
241000894007 species Species 0.000 description 1
229940063675 spermine Drugs 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
235000021286 stilbenes Nutrition 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
239000004575 stone Substances 0.000 description 1
TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-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
CQZHFXWBLGKORH-UHFFFAOYSA-N tert-butyl n-(2-cyano-1-pyrrolidin-3-ylethyl)carbamate Chemical compound CC(C)(C)OC(=O)NC(CC#N)C1CCNC1 CQZHFXWBLGKORH-UHFFFAOYSA-N 0.000 description 1
WIEJVMZWPIUWHO-UHFFFAOYSA-N tert-butyl n-(pyrrolidin-3-ylmethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC1CCNC1 WIEJVMZWPIUWHO-UHFFFAOYSA-N 0.000 description 1
MHRKPCRXBAHJGS-OAHLLOKOSA-N tert-butyl n-[[(3r)-1-benzylpyrrolidin-3-yl]methyl]carbamate Chemical compound C1[C@@H](CNC(=O)OC(C)(C)C)CCN1CC1=CC=CC=C1 MHRKPCRXBAHJGS-OAHLLOKOSA-N 0.000 description 1
KRRBFUJMQBDDPR-UHFFFAOYSA-N tetrabutylazanium;cyanide Chemical compound N#[C-].CCCC[N+](CCCC)(CCCC)CCCC KRRBFUJMQBDDPR-UHFFFAOYSA-N 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000004897 thiazines Chemical class 0.000 description 1
125000004149 thio group Chemical group *S* 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
DUDAKCCDHRNMDJ-UHFFFAOYSA-N thiophen-3-ylmethanamine Chemical compound NCC=1C=CSC=1 DUDAKCCDHRNMDJ-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
210000002105 tongue Anatomy 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
241001148471 unidentified anaerobic bacterium Species 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical group CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
238000009941 weaving Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229910052727 yttrium Inorganic materials 0.000 description 1
VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

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

TW093135213A 2003-11-18 2004-11-17 Quinolone antibacterial agents TW200524930A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US52307103P	2003-11-18	2003-11-18
US60549604P	2004-08-31	2004-08-31

Publications (1)

Publication Number	Publication Date
TW200524930A true TW200524930A (en)	2005-08-01

Family

ID=34623167

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW093135213A TW200524930A (en)	2003-11-18	2004-11-17	Quinolone antibacterial agents

Country Status (6)

Country	Link
AR (1)	AR046638A1 (es)
NL (1)	NL1027545C2 (es)
PE (1)	PE20050582A1 (es)
TW (1)	TW200524930A (es)
UY (1)	UY28622A1 (es)
WO (1)	WO2005049602A1 (es)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TWI382980B (zh) *	2006-02-09	2013-01-21	Aicuris Gmbh & Co Kg	經取代之喹諾酮類iii

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JP4639149B2 (ja)	2003-09-10	2011-02-23	杏林製薬株式会社	７−（４−置換−３−シクロプロピルアミノメチル−１−ピロリジニル）キノロンカルボン酸誘導体
WO2007019416A1 (en)	2005-08-04	2007-02-15	Sirtris Pharmaceuticals, Inc.	Benzimidazole derivatives as sirtuin modulators
CN101622240B (zh) *	2007-01-05	2014-07-23	第一三共株式会社	稠合取代氨基吡咯烷衍生物
RU2443698C2 (ru)	2007-01-05	2012-02-27	Дайити Санкио Компани, Лимитед	Конденсированное замещенное производное аминопирролидина
CA2688008A1 (en)	2007-05-24	2008-11-27	Kyorin Pharmaceutical Co., Ltd.	Mutilin derivative having heterocyclic aromatic ring carboxylic acid structure in substituent at 14-position
DE102007036068A1 (de)	2007-08-01	2009-02-05	Wacker Chemie Ag	Verfahren zur Herstellung von Alkyl-methoxymethyl-trimethylsilanylmethylaminen
RU2490257C2 (ru)	2008-05-30	2013-08-20	Такеда Фармасьютикал Компани Лимитед	Гетероциклическое соединение
HRP20140265T1 (hr)	2009-02-06	2014-04-25	Nippon Shinyaku Co., Ltd.	Derivat aminopirazina i odgovarajuä†i lijek
AR091858A1 (es) *	2012-07-25	2015-03-04	Sova Pharmaceuticals Inc	INHIBIDORES DE CISTATIONIN-g-LIASA (CSE)
UY36714A (es)	2015-06-09	2016-12-30	Bayer Pharma Akttiengesellschaft	Moduladores alostéricos positivos del receptor muscarínico m2
CA3030204A1 (en)	2016-07-11	2018-01-18	Bayer Pharma Aktiengesellschaft	7-substituted 1-pyridyl-naphthyridine-3-carboxylic acid amides and use thereof
JOP20190045A1 (ar)	2016-09-14	2019-03-14	Bayer Ag	مركبات أميد حمض 1- أريل-نفثيريدين-3-كربوكسيليك مستبدلة في الموضع 7 واستخدامها.
EP3296298A1 (de)	2016-09-14	2018-03-21	Bayer Pharma Aktiengesellschaft	7-substituierte 1-aryl-naphthyridin-3-carbonsäureamide und ihre verwendung
WO2018060073A1 (en)	2016-09-29	2018-04-05	Bayer Cropscience Aktiengesellschaft	Novel 5-substituted imidazole derivatives

2004
- 2004-11-05 WO PCT/IB2004/003666 patent/WO2005049602A1/en not_active Ceased
- 2004-11-16 PE PE2004001119A patent/PE20050582A1/es not_active Application Discontinuation
- 2004-11-17 TW TW093135213A patent/TW200524930A/zh unknown
- 2004-11-17 UY UY28622A patent/UY28622A1/es not_active Application Discontinuation
- 2004-11-18 AR ARP040104261A patent/AR046638A1/es unknown
- 2004-11-18 NL NL1027545A patent/NL1027545C2/nl not_active IP Right Cessation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TWI382980B (zh) *	2006-02-09	2013-01-21	Aicuris Gmbh & Co Kg	經取代之喹諾酮類iii

Also Published As

Publication number	Publication date
PE20050582A1 (es)	2005-08-25
UY28622A1 (es)	2005-06-30
WO2005049602A1 (en)	2005-06-02
NL1027545C2 (nl)	2006-01-17
NL1027545A1 (nl)	2005-05-23
AR046638A1 (es)	2005-12-14

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TW200524930A - Quinolone antibacterial agents - Google Patents

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Links

Classifications

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=34623167

Family Applications (1)

Country Status (6)

Cited By (1)

Families Citing this family (14)

Cited By (1)

Also Published As

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