JP2006519772A5

JP2006519772A5 -

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Publication number: JP2006519772A5
Authority: JP; Japan
Prior art keywords: alkyl; substituted; phenyl; group; mmol
Prior art date: 2004-01-08
Legal status : Granted

Application number

JP2006500858A

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English (en)

Japanese (ja)

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JP5086635B2 (ja

JP2006519772A (ja

Filing date

2004-01-08

Publication date

2010-09-09

2004-01-08 Application filed filed Critical

2004-01-08 Priority claimed from PCT/US2004/000433 external-priority patent/WO2004062601A2/en

2006-08-31 Publication of JP2006519772A publication Critical patent/JP2006519772A/ja

2010-09-09 Publication of JP2006519772A5 publication Critical patent/JP2006519772A5/ja

2012-11-28 Application granted granted Critical

2012-11-28 Publication of JP5086635B2 publication Critical patent/JP5086635B2/ja

2024-01-08 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

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150000001875 compounds Chemical class 0.000 claims description 177
-1 6 - cyclohexyl Chemical group 0.000 claims description 103
125000000217 alkyl group Chemical group 0.000 claims description 55
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
125000004429 atom Chemical group 0.000 claims description 37
150000003839 salts Chemical class 0.000 claims description 37
229910052799 carbon Inorganic materials 0.000 claims description 29
229910052794 bromium Inorganic materials 0.000 claims description 24
229910052801 chlorine Inorganic materials 0.000 claims description 24
239000008194 pharmaceutical composition Substances 0.000 claims description 24
239000003795 chemical substances by application Substances 0.000 claims description 21
229910052731 fluorine Inorganic materials 0.000 claims description 21
229910052740 iodine Inorganic materials 0.000 claims description 20
125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
125000004093 cyano group Chemical group *C#N 0.000 claims description 17
125000004076 pyridyl group Chemical group 0.000 claims description 15
125000003386 piperidinyl group Chemical group 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 12
208000015181 infectious disease Diseases 0.000 claims description 12
125000004193 piperazinyl group Chemical group 0.000 claims description 12
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
125000001544 thienyl group Chemical group 0.000 claims description 12
125000002883 imidazolyl group Chemical group 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 10
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 9
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
125000004043 oxo group Chemical group O=* 0.000 claims description 7
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 4
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 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
125000003373 pyrazinyl group Chemical group 0.000 claims description 4
125000003226 pyrazolyl group Chemical group 0.000 claims description 4
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
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 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000000168 pyrrolyl group Chemical group 0.000 claims description 3
125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
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 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
125000000896 monocarboxylic acid group Chemical group 0.000 claims 7
125000003725 azepanyl group Chemical group 0.000 claims 4
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 3
ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims 3
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 1
125000005036 alkoxyphenyl group Chemical group 0.000 claims 1
125000002785 azepinyl group Chemical group 0.000 claims 1
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
150000001602 bicycloalkyls Chemical group 0.000 claims 1
125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims 1
OTXBWGUYZNKPMG-UHFFFAOYSA-N isofulminic acid Chemical compound O[N+]#[C-] OTXBWGUYZNKPMG-UHFFFAOYSA-N 0.000 claims 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 229
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 188
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 175
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 171
125000000623 heterocyclic group Chemical group 0.000 description 156
239000011347 resin Substances 0.000 description 126
229920005989 resin Polymers 0.000 description 126
239000000243 solution Substances 0.000 description 106
238000006243 chemical reaction Methods 0.000 description 97
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 91
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 75
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 74
125000003118 aryl group Chemical group 0.000 description 68
239000000203 mixture Substances 0.000 description 67
125000006413 ring segment Chemical group 0.000 description 67
238000002360 preparation method Methods 0.000 description 62
238000000034 method Methods 0.000 description 60
239000007787 solid Substances 0.000 description 50
239000000047 product Substances 0.000 description 49
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
230000015572 biosynthetic process Effects 0.000 description 45
235000019439 ethyl acetate Nutrition 0.000 description 44
241000894006 Bacteria Species 0.000 description 40
229910052760 oxygen Inorganic materials 0.000 description 40
238000003786 synthesis reaction Methods 0.000 description 40
125000001072 heteroaryl group Chemical group 0.000 description 37
229910052717 sulfur Inorganic materials 0.000 description 37
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 34
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 34
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
239000000460 chlorine Substances 0.000 description 33
XEIKPDKXLLNYRR-SFHVURJKSA-N n-[(2s)-3-acetamido-1-(hydroxyamino)-1-oxopropan-2-yl]-4-(4-ethylphenyl)benzamide Chemical compound C1=CC(CC)=CC=C1C1=CC=C(C(=O)N[C@@H](CNC(C)=O)C(=O)NO)C=C1 XEIKPDKXLLNYRR-SFHVURJKSA-N 0.000 description 33
ZTURJQJRIAZNFM-NXEZZACHSA-N (2r,3r)-n,3-dihydroxy-1-[4-(trifluoromethoxy)benzoyl]pyrrolidine-2-carboxamide Chemical compound ONC(=O)[C@H]1[C@H](O)CCN1C(=O)C1=CC=C(OC(F)(F)F)C=C1 ZTURJQJRIAZNFM-NXEZZACHSA-N 0.000 description 32
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 32
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 32
238000004128 high performance liquid chromatography Methods 0.000 description 31
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 30
PZLQMTHMDBGSTL-UHFFFAOYSA-N n-[3-(dimethylcarbamoylamino)-1-(hydroxyamino)-1-oxopropan-2-yl]-4-(4-ethylphenyl)benzamide Chemical compound C1=CC(CC)=CC=C1C1=CC=C(C(=O)NC(CNC(=O)N(C)C)C(=O)NO)C=C1 PZLQMTHMDBGSTL-UHFFFAOYSA-N 0.000 description 29
239000002253 acid Substances 0.000 description 28
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 27
239000003814 drug Substances 0.000 description 27
239000000651 prodrug Substances 0.000 description 26
229940002612 prodrug Drugs 0.000 description 26
238000011282 treatment Methods 0.000 description 25
239000012043 crude product Substances 0.000 description 24
150000002148 esters Chemical class 0.000 description 24
230000002829 reductive effect Effects 0.000 description 24
INYFYSNGHZBBOI-IAGOWNOFSA-N (2r,3r)-3-hydroxy-n-phenylmethoxy-1-[4-(trifluoromethoxy)benzoyl]pyrrolidine-2-carboxamide Chemical compound O=C([C@@H]1N(CC[C@H]1O)C(=O)C=1C=CC(OC(F)(F)F)=CC=1)NOCC1=CC=CC=C1 INYFYSNGHZBBOI-IAGOWNOFSA-N 0.000 description 23
239000004599 antimicrobial Substances 0.000 description 23
239000000843 powder Substances 0.000 description 22
238000004007 reversed phase HPLC Methods 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
230000002401 inhibitory effect Effects 0.000 description 21
239000003826 tablet Substances 0.000 description 21
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 20
239000003242 anti bacterial agent Substances 0.000 description 20
238000000746 purification Methods 0.000 description 20
229920006395 saturated elastomer Polymers 0.000 description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 19
239000002775 capsule Substances 0.000 description 19
229940079593 drug Drugs 0.000 description 19
238000002953 preparative HPLC Methods 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 19
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
229910052786 argon Inorganic materials 0.000 description 17
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 17
239000000725 suspension Substances 0.000 description 17
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
238000004809 thin layer chromatography Methods 0.000 description 16
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
230000000844 anti-bacterial effect Effects 0.000 description 15
125000004446 heteroarylalkyl group Chemical group 0.000 description 15
BBYXSYZAUDTWAK-UHFFFAOYSA-N n-[3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]-4-[4-(6-morpholin-4-ylpyridin-3-yl)buta-1,3-diynyl]benzamide Chemical compound C1=CC(C(=O)NC(C(O)C)C(=O)NO)=CC=C1C#CC#CC1=CC=C(N2CCOCC2)N=C1 BBYXSYZAUDTWAK-UHFFFAOYSA-N 0.000 description 15
238000002390 rotary evaporation Methods 0.000 description 15
239000011734 sodium Substances 0.000 description 15
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
239000002904 solvent Substances 0.000 description 15
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 14
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
230000000694 effects Effects 0.000 description 14
229910052757 nitrogen Inorganic materials 0.000 description 14
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 13
125000004122 cyclic group Chemical group 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
238000003756 stirring Methods 0.000 description 13
FNXZMSTTYAYLEQ-UHFFFAOYSA-N 4-[4-[4-[[2-(dimethylamino)acetyl]amino]phenyl]buta-1,3-diynyl]-N-[2-hydroxy-4-(hydroxyamino)-4-oxobutyl]benzamide Chemical compound CN(CC(=O)NC1=CC=C(C=C1)C#CC#CC1=CC=C(C(=O)NCC(CC(NO)=O)O)C=C1)C FNXZMSTTYAYLEQ-UHFFFAOYSA-N 0.000 description 12
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
101150003085 Pdcl gene Proteins 0.000 description 12
238000004458 analytical method Methods 0.000 description 12
230000001580 bacterial effect Effects 0.000 description 12
238000003776 cleavage reaction Methods 0.000 description 12
239000002552 dosage form Substances 0.000 description 12
125000005842 heteroatom Chemical group 0.000 description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 description 12
239000003112 inhibitor Substances 0.000 description 12
239000003921 oil Substances 0.000 description 12
235000019198 oils Nutrition 0.000 description 12
125000004430 oxygen atom Chemical group O* 0.000 description 12
230000007017 scission Effects 0.000 description 12
125000000547 substituted alkyl group Chemical group 0.000 description 12
JFLSOKIMYBSASW-UHFFFAOYSA-N 1-chloro-2-[chloro(diphenyl)methyl]benzene Chemical compound ClC1=CC=CC=C1C(Cl)(C=1C=CC=CC=1)C1=CC=CC=C1 JFLSOKIMYBSASW-UHFFFAOYSA-N 0.000 description 11
208000035143 Bacterial infection Diseases 0.000 description 11
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 11
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 11
AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 11
208000022362 bacterial infectious disease Diseases 0.000 description 11
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 11
239000006260 foam Substances 0.000 description 11
239000000463 material Substances 0.000 description 11
238000010898 silica gel chromatography Methods 0.000 description 11
125000004434 sulfur atom Chemical group 0.000 description 11
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
239000003937 drug carrier Substances 0.000 description 10
238000009472 formulation Methods 0.000 description 10
229920000728 polyester Polymers 0.000 description 10
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
241000588724 Escherichia coli Species 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 8
NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 8
108090000790 Enzymes Proteins 0.000 description 8
102000004190 Enzymes Human genes 0.000 description 8
239000007821 HATU Substances 0.000 description 8
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 8
241000589517 Pseudomonas aeruginosa Species 0.000 description 8
239000004473 Threonine Substances 0.000 description 8
239000000443 aerosol Substances 0.000 description 8
230000000845 anti-microbial effect Effects 0.000 description 8
239000012267 brine Substances 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
238000004108 freeze drying Methods 0.000 description 8
230000005764 inhibitory process Effects 0.000 description 8
239000008101 lactose Substances 0.000 description 8
229960002898 threonine Drugs 0.000 description 8
CTRPJLKJIOQGCI-UHFFFAOYSA-N 4-[4-[4-[(2-amino-4-methylpentanoyl)amino]phenyl]buta-1,3-diynyl]-n-[3-hydroxy-1-(hydroxyamino)-1-oxobutan-2-yl]benzamide Chemical compound C1=CC(NC(=O)C(N)CC(C)C)=CC=C1C#CC#CC1=CC=C(C(=O)NC(C(C)O)C(=O)NO)C=C1 CTRPJLKJIOQGCI-UHFFFAOYSA-N 0.000 description 7
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 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
239000002158 endotoxin Substances 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
NZCRJKRKKOLAOJ-XRCRFVBUSA-N rifaximin Chemical compound OC1=C(C(O)=C2C)C3=C4N=C5C=C(C)C=CN5C4=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O NZCRJKRKKOLAOJ-XRCRFVBUSA-N 0.000 description 7
239000000126 substance Substances 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 6
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
241000589291 Acinetobacter Species 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000004809 Teflon Substances 0.000 description 6
229920006362 Teflon® Polymers 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 6
125000003342 alkenyl group Chemical group 0.000 description 6
150000001412 amines Chemical group 0.000 description 6
229940024606 amino acid Drugs 0.000 description 6
235000001014 amino acid Nutrition 0.000 description 6
150000001413 amino acids Chemical class 0.000 description 6
206010006451 bronchitis Diseases 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000011888 foil Substances 0.000 description 6
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JP2006500858A 2003-01-08 2004-01-08 抗菌剤 Expired - Fee Related JP5086635B2 (ja)