JP2006524706A

JP2006524706A - 新規なケトライド誘導体

新規なケトライド誘導体 Download PDF

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Publication number: JP2006524706A
Authority: JP; Japan
Prior art keywords: substituted; alkyl; hydrogen; aryl; heteroaryl
Prior art date: 2003-04-25
Legal status : Pending

Application number

JP2006513319A

Other languages

English (en)

Japanese (ja)

Other versions

JP2006524706A5 (OSRAM

Inventor

マシューバーガー，

ダニエルチュー，

Original Assignee

カイロンコーポレイション

Priority date

2003-04-25

Filing date

2004-04-23

Publication date

2006-11-02

2004-04-23 Application filed by カイロンコーポレイション filed Critical カイロンコーポレイション

2006-11-02 Publication of JP2006524706A publication Critical patent/JP2006524706A/ja

2007-05-10 Publication of JP2006524706A5 publication Critical patent/JP2006524706A5/ja

Status Pending legal-status Critical Current

Links

239000003835 ketolide antibiotic agent Substances 0.000 title abstract description 37
150000001875 compounds Chemical class 0.000 claims abstract description 114
150000003839 salts Chemical class 0.000 claims abstract description 49
150000002148 esters Chemical class 0.000 claims abstract description 44
239000000651 prodrug Substances 0.000 claims abstract description 42
229940002612 prodrug Drugs 0.000 claims abstract description 42
238000000034 method Methods 0.000 claims abstract description 40
208000035143 Bacterial infection Diseases 0.000 claims abstract description 17
208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 17
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims abstract description 6
-1 wherein Chemical compound 0.000 claims description 122
229910052739 hydrogen Inorganic materials 0.000 claims description 97
239000001257 hydrogen Substances 0.000 claims description 97
125000001072 heteroaryl group Chemical group 0.000 claims description 85
125000003118 aryl group Chemical group 0.000 claims description 57
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 53
125000000217 alkyl group Chemical group 0.000 claims description 47
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
125000003107 substituted aryl group Chemical group 0.000 claims description 33
229910052736 halogen Inorganic materials 0.000 claims description 30
150000002367 halogens Chemical class 0.000 claims description 30
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
239000003814 drug Substances 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 20
229910052799 carbon Inorganic materials 0.000 claims description 16
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 10
125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
239000003937 drug carrier Substances 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 8
125000002883 imidazolyl group Chemical group 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 7
XBPASXLWMTZZFC-UHFFFAOYSA-N 4-[4-(6-chloropyridin-3-yl)-2-methyl-1h-imidazol-5-yl]butan-1-amine Chemical compound N1C(C)=NC(C=2C=NC(Cl)=CC=2)=C1CCCCN XBPASXLWMTZZFC-UHFFFAOYSA-N 0.000 claims description 6
OIKYGVHOAKNOIT-UHFFFAOYSA-N 4-[4-(6-chloropyridin-3-yl)-5-methyl-1h-imidazol-2-yl]butan-1-amine Chemical compound N1C(CCCCN)=NC(C=2C=NC(Cl)=CC=2)=C1C OIKYGVHOAKNOIT-UHFFFAOYSA-N 0.000 claims description 6
LZPSNHQTMJQMHZ-UHFFFAOYSA-N 4-[5-(4-chloropyridin-3-yl)-1h-imidazol-2-yl]butan-1-amine Chemical compound N1C(CCCCN)=NC=C1C1=CN=CC=C1Cl LZPSNHQTMJQMHZ-UHFFFAOYSA-N 0.000 claims description 6
125000001843 C4-C10 alkenyl group Chemical group 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 6
DFAGLOLGEMMVPT-UHFFFAOYSA-N 4-[5-(4-methoxypyridin-3-yl)-1h-imidazol-2-yl]butan-1-amine Chemical compound COC1=CC=NC=C1C1=CN=C(CCCCN)N1 DFAGLOLGEMMVPT-UHFFFAOYSA-N 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
FMZZOIPURNVGLD-UHFFFAOYSA-N 4-[4-(6-methylpyridin-3-yl)imidazol-1-yl]butan-1-amine Chemical compound C1=NC(C)=CC=C1C1=CN(CCCCN)C=N1 FMZZOIPURNVGLD-UHFFFAOYSA-N 0.000 claims description 4
FWMIGRYEXUCAOR-UHFFFAOYSA-N 5-[1-(4-aminobutyl)imidazol-4-yl]-n-methylpyridin-2-amine Chemical compound C1=NC(NC)=CC=C1C1=CN(CCCCN)C=N1 FWMIGRYEXUCAOR-UHFFFAOYSA-N 0.000 claims description 4
UGBFATORHKYKHA-UHFFFAOYSA-N 5-[1-(4-aminobutyl)imidazol-4-yl]pyridin-2-amine Chemical compound NCCCCN1C=NC(C=2C=NC(N)=CC=2)=C1 UGBFATORHKYKHA-UHFFFAOYSA-N 0.000 claims description 4
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 3
125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims description 3
SKSZYTFXIDNVRR-UHFFFAOYSA-N 4-[4-(6-chloropyridin-3-yl)imidazol-1-yl]butan-1-amine Chemical compound NCCCCN1C=NC(C=2C=NC(Cl)=CC=2)=C1 SKSZYTFXIDNVRR-UHFFFAOYSA-N 0.000 claims description 3
KQPJSTREOMVENQ-UHFFFAOYSA-N 4-[4-(6-ethoxypyridin-3-yl)imidazol-1-yl]butan-1-amine Chemical compound C1=NC(OCC)=CC=C1C1=CN(CCCCN)C=N1 KQPJSTREOMVENQ-UHFFFAOYSA-N 0.000 claims description 3
VYBHXZVSJYBFMA-UHFFFAOYSA-N 4-[4-(6-fluoropyridin-3-yl)imidazol-1-yl]butan-1-amine Chemical compound NCCCCN1C=NC(C=2C=NC(F)=CC=2)=C1 VYBHXZVSJYBFMA-UHFFFAOYSA-N 0.000 claims description 3
IYWJLGFXMICCGN-UHFFFAOYSA-N 4-[4-(6-methoxypyridin-3-yl)imidazol-1-yl]butan-1-amine Chemical compound C1=NC(OC)=CC=C1C1=CN(CCCCN)C=N1 IYWJLGFXMICCGN-UHFFFAOYSA-N 0.000 claims description 3
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
230000002265 prevention Effects 0.000 claims description 3
ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 3
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 claims description 2
125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 34
239000000203 mixture Substances 0.000 abstract description 48
230000000844 anti-bacterial effect Effects 0.000 abstract description 6
238000000968 medical method and process Methods 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 198
239000000243 solution Substances 0.000 description 97
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 81
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 62
239000011541 reaction mixture Substances 0.000 description 56
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
239000003921 oil Substances 0.000 description 48
235000019198 oils Nutrition 0.000 description 48
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 43
238000003756 stirring Methods 0.000 description 38
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 34
238000006243 chemical reaction Methods 0.000 description 33
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
239000002904 solvent Substances 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 24
239000012043 crude product Substances 0.000 description 23
229920006395 saturated elastomer Polymers 0.000 description 23
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 22
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 22
235000019441 ethanol Nutrition 0.000 description 21
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 20
238000001816 cooling Methods 0.000 description 20
239000010410 layer Substances 0.000 description 20
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
229940079593 drug Drugs 0.000 description 17
239000012044 organic layer Substances 0.000 description 17
239000011780 sodium chloride Substances 0.000 description 17
229910052938 sodium sulfate Inorganic materials 0.000 description 17
235000011152 sodium sulphate Nutrition 0.000 description 17
239000007787 solid Substances 0.000 description 17
239000000460 chlorine Substances 0.000 description 13
230000000694 effects Effects 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Natural products 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 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 12
UXFWTIGUWHJKDD-UHFFFAOYSA-N 2-(4-bromobutyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCBr)C(=O)C2=C1 UXFWTIGUWHJKDD-UHFFFAOYSA-N 0.000 description 11
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 11
238000009472 formulation Methods 0.000 description 11
239000011592 zinc chloride Substances 0.000 description 11
235000005074 zinc chloride Nutrition 0.000 description 11
DXJZJYPLPZEYBH-UHFFFAOYSA-N 4-iodo-1-tritylimidazole Chemical compound C1=NC(I)=CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DXJZJYPLPZEYBH-UHFFFAOYSA-N 0.000 description 10
WHFMNQBQNLCUAP-UHFFFAOYSA-N C(N)(OC=1NC=C(N=1)C)=O Chemical compound C(N)(OC=1NC=C(N=1)C)=O WHFMNQBQNLCUAP-UHFFFAOYSA-N 0.000 description 10
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 10
FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 10
229910000027 potassium carbonate Inorganic materials 0.000 description 10
0 CC(C1)[C@@](*)C(C)OC1*=C=C Chemical compound CC(C1)[C@@](*)C(C)OC1*=C=C 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
239000013058 crude material Substances 0.000 description 8
239000000463 material Substances 0.000 description 8
125000004043 oxo group Chemical group O=* 0.000 description 8
239000000546 pharmaceutical excipient Substances 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
125000000547 substituted alkyl group Chemical group 0.000 description 8
HIDHQZBPBJIEFC-UHFFFAOYSA-N 4-[5-(6-chloropyridin-3-yl)-1h-imidazol-2-yl]butan-1-amine Chemical compound N1C(CCCCN)=NC=C1C1=CC=C(Cl)N=C1 HIDHQZBPBJIEFC-UHFFFAOYSA-N 0.000 description 7
239000000443 aerosol Substances 0.000 description 7
239000000872 buffer Substances 0.000 description 7
238000003818 flash chromatography Methods 0.000 description 7
238000001990 intravenous administration Methods 0.000 description 7
229920001223 polyethylene glycol Polymers 0.000 description 7
239000000843 powder Substances 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
241000894006 Bacteria Species 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
125000003282 alkyl amino group Chemical group 0.000 description 6
125000004663 dialkyl amino group Chemical group 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
238000010438 heat treatment Methods 0.000 description 6
239000008101 lactose Substances 0.000 description 6
210000004072 lung Anatomy 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
239000012265 solid product Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
241000124008 Mammalia Species 0.000 description 5
229920002472 Starch Polymers 0.000 description 5
230000009102 absorption Effects 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
239000002253 acid Substances 0.000 description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
125000002619 bicyclic group Chemical group 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
210000003123 bronchiole Anatomy 0.000 description 5
239000002775 capsule Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
238000000576 coating method Methods 0.000 description 5
239000002552 dosage form Substances 0.000 description 5
125000001188 haloalkyl group Chemical group 0.000 description 5
125000001183 hydrocarbyl group Chemical group 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
IUEBEACSGQRJBB-UHFFFAOYSA-N methyl n-(1h-imidazol-2-yl)carbamate Chemical compound COC(=O)NC1=NC=CN1 IUEBEACSGQRJBB-UHFFFAOYSA-N 0.000 description 5
239000006199 nebulizer Substances 0.000 description 5
231100000252 nontoxic Toxicity 0.000 description 5
230000003000 nontoxic effect Effects 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
239000006187 pill Substances 0.000 description 5
125000004076 pyridyl group Chemical group 0.000 description 5
239000007909 solid dosage form Substances 0.000 description 5
235000019698 starch Nutrition 0.000 description 5
239000003826 tablet Substances 0.000 description 5
125000005309 thioalkoxy group Chemical group 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
239000001993 wax Substances 0.000 description 5
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
SMHOWQXDCNFLQY-UHFFFAOYSA-N 2-methoxy-5-(5-methyl-1h-imidazol-4-yl)pyridine Chemical compound C1=NC(OC)=CC=C1C1=C(C)NC=N1 SMHOWQXDCNFLQY-UHFFFAOYSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
XKSVJEIDWNGLPU-UHFFFAOYSA-N 4-[4-(6-methoxypyridin-3-yl)-2-methyl-1h-imidazol-5-yl]butan-1-amine Chemical compound C1=NC(OC)=CC=C1C1=C(CCCCN)NC(C)=N1 XKSVJEIDWNGLPU-UHFFFAOYSA-N 0.000 description 4
PPRSDMPJYFFMPE-UHFFFAOYSA-N 4-[5-(2-chloropyridin-3-yl)-1h-imidazol-2-yl]butan-1-amine Chemical compound N1C(CCCCN)=NC=C1C1=CC=CN=C1Cl PPRSDMPJYFFMPE-UHFFFAOYSA-N 0.000 description 4
QJUWCCQVNSGPBX-UHFFFAOYSA-N 4-[5-(6-chloro-5-methylpyridin-3-yl)-1h-imidazol-2-yl]butan-1-amine Chemical compound N1=C(Cl)C(C)=CC(C=2NC(CCCCN)=NC=2)=C1 QJUWCCQVNSGPBX-UHFFFAOYSA-N 0.000 description 4
PEAOEIWYQVXZMB-UHFFFAOYSA-N 5-bromo-2-chloropyridine Chemical compound ClC1=CC=C(Br)C=N1 PEAOEIWYQVXZMB-UHFFFAOYSA-N 0.000 description 4
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 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
239000002202 Polyethylene glycol Substances 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
229930006000 Sucrose Natural products 0.000 description 4
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 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
235000010443 alginic acid Nutrition 0.000 description 4
229920000615 alginic acid Polymers 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
230000008901 benefit Effects 0.000 description 4
229960003276 erythromycin Drugs 0.000 description 4
125000004185 ester group Chemical group 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
239000000945 filler Substances 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
239000008263 liquid aerosol Substances 0.000 description 4
239000002609 medium Substances 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
125000004430 oxygen atom Chemical group O* 0.000 description 4
239000002245 particle Substances 0.000 description 4
125000006413 ring segment Chemical group 0.000 description 4
239000005720 sucrose Substances 0.000 description 4
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
239000000725 suspension Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
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