CN101541331A - 具有抗微生物活性的新颖大环内酯和酮内酯 - Google Patents

Info

Publication number

CN101541331A

CN101541331A CNA2007800373931A CN200780037393A CN101541331A CN 101541331 A CN101541331 A CN 101541331A CN A2007800373931 A CNA2007800373931 A CN A2007800373931A CN 200780037393 A CN200780037393 A CN 200780037393A CN 101541331 A CN101541331 A CN 101541331A

Authority

CN

China

Prior art keywords

general formula

chemical compound

phenyl

oxadiazole

yls

Prior art date

2006-08-24

Legal status (The legal status 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 status listed.)

Pending

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• 239000003120 macrolide antibiotic agent Substances 0.000 title claims abstract description 25
• 239000003835 ketolide antibiotic agent Substances 0.000 title abstract description 14
• 230000000845 anti-microbial effect Effects 0.000 title abstract description 11
• 229940041033 macrolides Drugs 0.000 title abstract 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 662
• 238000000034 method Methods 0.000 claims abstract description 38
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
• -1 triethylsilyl Chemical group 0.000 claims description 222
• 239000002585 base Substances 0.000 claims description 140
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 89
• 229910052739 hydrogen Inorganic materials 0.000 claims description 53
• 239000002904 solvent Substances 0.000 claims description 45
• 125000001072 heteroaryl group Chemical group 0.000 claims description 44
• 238000006243 chemical reaction Methods 0.000 claims description 35
• 239000001257 hydrogen Substances 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 30
• 125000003118 aryl group Chemical group 0.000 claims description 27
• 229910052731 fluorine Inorganic materials 0.000 claims description 25
• 239000011737 fluorine Substances 0.000 claims description 24
• 125000000217 alkyl group Chemical group 0.000 claims description 23
• 238000011282 treatment Methods 0.000 claims description 22
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 19
• 241001465754 Metazoa Species 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 239000003513 alkali Substances 0.000 claims description 17
• 125000000623 heterocyclic group Chemical group 0.000 claims description 17
• 150000002431 hydrogen Chemical class 0.000 claims description 17
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 16
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 239000000460 chlorine Substances 0.000 claims description 15
• 150000002367 halogens Chemical class 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 15
• 229920006395 saturated elastomer Polymers 0.000 claims description 15
• 229910052801 chlorine Inorganic materials 0.000 claims description 14
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
• 239000012453 solvate Substances 0.000 claims description 12
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 239000003153 chemical reaction reagent Substances 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 229910052717 sulfur Inorganic materials 0.000 claims description 10
• 125000002769 thiazolinyl group Chemical group 0.000 claims description 10
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
• 238000010511 deprotection reaction Methods 0.000 claims description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
• 241000894006 Bacteria Species 0.000 claims description 7
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
• 230000002265 prevention Effects 0.000 claims description 7
• ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 239000003054 catalyst Substances 0.000 claims description 6
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 6
• 125000002971 oxazolyl group Chemical group 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000001425 triazolyl group Chemical group 0.000 claims description 6
• 229910004013 NO 2 Inorganic materials 0.000 claims description 5
• MUCRYNWJQNHDJH-OADIDDRXSA-N Ursonic acid Chemical class C1CC(=O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C MUCRYNWJQNHDJH-OADIDDRXSA-N 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000005842 heteroatom Chemical group 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 229910052763 palladium Inorganic materials 0.000 claims description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• AJSDVNKVGFVAQU-BIIVOSGPSA-N cladinose Chemical compound O=CC[C@@](C)(OC)[C@@H](O)[C@H](C)O AJSDVNKVGFVAQU-BIIVOSGPSA-N 0.000 claims description 4
• 238000005859 coupling reaction Methods 0.000 claims description 4
• MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 238000007254 oxidation reaction Methods 0.000 claims description 4
• YHVUVJYEERGYNU-UHFFFAOYSA-N 4',8-Di-Me ether-5,7,8-Trihydroxy-3-(4-hydroxybenzyl)-4-chromanone Natural products COC1(C)CC(O)OC(C)C1O YHVUVJYEERGYNU-UHFFFAOYSA-N 0.000 claims description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
• 230000002152 alkylating effect Effects 0.000 claims description 3
• 230000000844 anti-bacterial effect Effects 0.000 claims description 3
• 239000012948 isocyanate Substances 0.000 claims description 3
• 150000002513 isocyanates Chemical class 0.000 claims description 3
• 230000003647 oxidation Effects 0.000 claims description 3
• 125000004193 piperazinyl group Chemical group 0.000 claims description 3
• 241000192125 Firmicutes Species 0.000 claims description 2
• 241001148470 aerobic bacillus Species 0.000 claims description 2
• 238000005984 hydrogenation reaction Methods 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 5
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 5
• 125000004432 carbon atom Chemical group C* 0.000 claims 4
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 4
• 125000003106 haloaryl group Chemical group 0.000 claims 2
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
• 239000012445 acidic reagent Substances 0.000 claims 1
• 150000001735 carboxylic acids Chemical class 0.000 claims 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 16
• 201000010099 disease Diseases 0.000 abstract description 15
• 230000008569 process Effects 0.000 abstract description 7
• 208000015181 infectious disease Diseases 0.000 abstract description 6
• 230000000813 microbial effect Effects 0.000 abstract description 3
• 239000004480 active ingredient Substances 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 193
• 239000000203 mixture Substances 0.000 description 178
• 239000000376 reactant Substances 0.000 description 127
• 239000007787 solid Substances 0.000 description 111
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 87
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 82
• 239000000243 solution Substances 0.000 description 80
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 69
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 58
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
• 239000000047 product Substances 0.000 description 57
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 53
• 239000012044 organic layer Substances 0.000 description 53
• 238000003756 stirring Methods 0.000 description 50
• 239000011734 sodium Substances 0.000 description 48
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 45
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
• 238000000746 purification Methods 0.000 description 35
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• 238000001819 mass spectrum Methods 0.000 description 31
• 235000002639 sodium chloride Nutrition 0.000 description 31
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
• 238000010898 silica gel chromatography Methods 0.000 description 29
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 27
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
• RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
• 239000012043 crude product Substances 0.000 description 23
• 235000019439 ethyl acetate Nutrition 0.000 description 23
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 22
• GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 22
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 21
• 238000005406 washing Methods 0.000 description 19
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• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 16
• 239000007788 liquid Substances 0.000 description 16
• 239000007864 aqueous solution Substances 0.000 description 15
• 238000000605 extraction Methods 0.000 description 15
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 12
• 239000000284 extract Substances 0.000 description 12
• 230000002829 reductive effect Effects 0.000 description 12
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
• 229910052740 iodine Inorganic materials 0.000 description 11
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
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