KR20160020403A - 매크로라이드 항세균제들을 제조하기 위한 수렴 프로세스들 - Google Patents
매크로라이드 항세균제들을 제조하기 위한 수렴 프로세스들 Download PDFInfo
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- KR20160020403A KR20160020403A KR1020157026223A KR20157026223A KR20160020403A KR 20160020403 A KR20160020403 A KR 20160020403A KR 1020157026223 A KR1020157026223 A KR 1020157026223A KR 20157026223 A KR20157026223 A KR 20157026223A KR 20160020403 A KR20160020403 A KR 20160020403A
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- 238000000034 method Methods 0.000 title claims abstract description 142
- 239000003242 anti bacterial agent Substances 0.000 title abstract description 3
- 239000003120 macrolide antibiotic agent Substances 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims description 177
- 150000003839 salts Chemical class 0.000 claims description 79
- -1 pentafluorophenoxy Chemical group 0.000 claims description 38
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 32
- 239000003795 chemical substances by application Substances 0.000 claims description 27
- 239000012351 deprotecting agent Substances 0.000 claims description 27
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000002252 acyl group Chemical group 0.000 claims description 19
- 125000006239 protecting group Chemical group 0.000 claims description 19
- 239000002585 base Substances 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical group FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 11
- 239000007800 oxidant agent Substances 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
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- 150000001408 amides Chemical class 0.000 claims description 8
- 125000006242 amine protecting group Chemical group 0.000 claims description 8
- 239000012025 fluorinating agent Substances 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylene diamine Substances C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 6
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 239000006184 cosolvent Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 4
- RLKHFSNWQCZBDC-UHFFFAOYSA-N n-(benzenesulfonyl)-n-fluorobenzenesulfonamide Chemical group C=1C=CC=CC=1S(=O)(=O)N(F)S(=O)(=O)C1=CC=CC=C1 RLKHFSNWQCZBDC-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 238000005675 Corey-Kim oxidation reaction Methods 0.000 claims description 3
- ZOYWWAGVGBSJDL-UHFFFAOYSA-N D-desosamine Natural products CC1CC(N(C)C)C(O)C(O)O1 ZOYWWAGVGBSJDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 3
- VTJCSBJRQLZNHE-CSMHCCOUSA-N desosamine Chemical compound C[C@@H](O)C[C@H](N(C)C)[C@@H](O)C=O VTJCSBJRQLZNHE-CSMHCCOUSA-N 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- 238000006809 Jones oxidation reaction Methods 0.000 claims description 2
- 229910019093 NaOCl Inorganic materials 0.000 claims description 2
- 238000006859 Swern oxidation reaction Methods 0.000 claims description 2
- 125000003158 alcohol group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 2
- 230000000640 hydroxylating effect Effects 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 2
- 239000011388 polymer cement concrete Substances 0.000 claims description 2
- 239000012363 selectfluor Substances 0.000 claims description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 32
- 239000003835 ketolide antibiotic agent Substances 0.000 abstract description 9
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 55
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 239000011541 reaction mixture Substances 0.000 description 32
- 206010057190 Respiratory tract infections Diseases 0.000 description 30
- 239000000243 solution Substances 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- 239000000203 mixture Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- 239000012043 crude product Substances 0.000 description 16
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 16
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical group C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 15
- 238000004128 high performance liquid chromatography Methods 0.000 description 14
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
- 239000013067 intermediate product Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical group ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 9
- 125000004450 alkenylene group Chemical group 0.000 description 9
- 125000004419 alkynylene group Chemical group 0.000 description 9
- IXXFZUPTQVDPPK-ZAWHAJPISA-N (1r,2r,4r,6r,7r,8r,10s,13r,14s)-17-[4-[4-(3-aminophenyl)triazol-1-yl]butyl]-7-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-13-ethyl-10-fluoro-6-methoxy-2,4,6,8,10,14-hexamethyl-12,15-dioxa-17-azabicyclo[12.3.0]heptadecane-3,9,11,16-tet Chemical compound O([C@@H]1[C@@H](C)C(=O)[C@](C)(F)C(=O)O[C@@H]([C@]2(OC(=O)N(CCCCN3N=NC(=C3)C=3C=C(N)C=CC=3)[C@@H]2[C@@H](C)C(=O)[C@H](C)C[C@@]1(C)OC)C)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O IXXFZUPTQVDPPK-ZAWHAJPISA-N 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- 125000003107 substituted aryl group Chemical group 0.000 description 8
- 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 description 7
- 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 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
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- 235000011114 ammonium hydroxide Nutrition 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 229960002626 clarithromycin Drugs 0.000 description 6
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- 239000012535 impurity Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
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- 125000001188 haloalkyl group Chemical group 0.000 description 5
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- 239000012453 solvate Substances 0.000 description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
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- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 3
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- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 2
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- 229940035429 isobutyl alcohol Drugs 0.000 description 1
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- 125000002757 morpholinyl group Chemical group 0.000 description 1
- WSIOIZZCGNOQAK-UHFFFAOYSA-N n,n-dimethylacetamide;2-methylpropanoic acid Chemical compound CC(C)C(O)=O.CN(C)C(C)=O WSIOIZZCGNOQAK-UHFFFAOYSA-N 0.000 description 1
- MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- AKRYBBWYDSDZHG-UHFFFAOYSA-N nitrosobis(2-oxopropyl)amine Chemical compound CC(=O)CN(N=O)CC(C)=O AKRYBBWYDSDZHG-UHFFFAOYSA-N 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 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 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
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- 150000002989 phenols Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
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- 229920000570 polyether Polymers 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
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- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
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- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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| EP3738591A3 (en) | 2003-03-10 | 2021-03-24 | Merck Sharp & Dohme Corp. | Novel antibacterial agents |
| AU2008316830B2 (en) | 2007-10-25 | 2016-03-17 | Cempra Pharmaceuticals, Inc. | Process for the preparation of macrolide antibacterial agents |
| US9072759B2 (en) | 2008-10-24 | 2015-07-07 | Cempra Pharmaceuticals, Inc. | Biodefenses using triazole-containing macrolides |
| US9937194B1 (en) | 2009-06-12 | 2018-04-10 | Cempra Pharmaceuticals, Inc. | Compounds and methods for treating inflammatory diseases |
| ES2608285T3 (es) | 2009-09-10 | 2017-04-07 | Cempra Pharmaceuticals, Inc. | Procedimientos para el tratamiento de paludismo, tuberculosis y enfermedades por MAC |
| ES2636948T3 (es) | 2010-05-20 | 2017-10-10 | Cempra Pharmaceuticals, Inc. | Procesos para preparar macrólidos y cetólidos e intermediarios para los mismos |
| WO2012034058A1 (en) | 2010-09-10 | 2012-03-15 | Cempra Pharmaceuticals, Inc. | Hydrogen bond forming fluoro ketolides for treating diseases |
| IN2014DN08939A (enExample) | 2012-03-27 | 2015-05-22 | Cempra Pharmaceuticals Inc | |
| CN105163785A (zh) | 2013-03-14 | 2015-12-16 | 森普拉制药公司 | 用于治疗呼吸道疾病的方法及其制剂 |
| RU2015138797A (ru) | 2013-03-15 | 2017-04-24 | Семпра Фармасьютикалс, Инк. | Конвергентные способы получения макролидных антибактериальных агентов |
| MX377459B (es) | 2013-04-04 | 2025-03-10 | Harvard College | Macrolidos y metodos para su preparacion y uso. |
| WO2016057798A1 (en) | 2014-10-08 | 2016-04-14 | President And Fellows Of Harvard College | 14-membered ketolides and methods of their preparation and use |
| CN104650166B (zh) * | 2014-11-17 | 2017-12-05 | 广东东阳光药业有限公司 | 一种大环内酯的制备方法 |
| MX2017011454A (es) * | 2015-03-06 | 2018-01-23 | Cempra Pharmaceuticals Inc | Procesos para preparar fluorocetólidos. |
| CN107530365A (zh) | 2015-03-25 | 2018-01-02 | 哈佛大学的校长及成员们 | 具有修饰的脱氧糖胺糖的大环内酯及其用途 |
| CN106554381A (zh) * | 2015-09-25 | 2017-04-05 | 苏州鹏旭医药科技有限公司 | 酮内酯类抗生素中间体及其制备方法和应用 |
| CN105503976B (zh) * | 2015-12-04 | 2018-02-06 | 浙江京新药业股份有限公司 | 一种索利霉素中间体 |
| EP3190122A1 (en) | 2016-01-08 | 2017-07-12 | LEK Pharmaceuticals d.d. | A novel synthetic pathway towards solithromycin and purification thereof |
| CN106432383A (zh) * | 2016-09-14 | 2017-02-22 | 重庆两江药物研发中心有限公司 | 索利霉素及其中间体的制备方法 |
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- 2014-03-15 CN CN201480025203.4A patent/CN105188712A/zh active Pending
- 2014-03-15 HK HK16106891.9A patent/HK1218864A1/zh unknown
- 2014-03-15 MX MX2015012465A patent/MX356772B/es active IP Right Grant
- 2014-03-15 HK HK16108554.3A patent/HK1220394A1/zh unknown
- 2014-03-15 US US14/774,843 patent/US9751908B2/en not_active Expired - Fee Related
- 2014-03-15 WO PCT/US2014/029932 patent/WO2014145210A1/en not_active Ceased
- 2014-03-15 CA CA2907085A patent/CA2907085A1/en not_active Abandoned
- 2014-03-15 EP EP14763625.2A patent/EP2968384A4/en not_active Withdrawn
- 2014-03-15 AU AU2014233240A patent/AU2014233240B2/en not_active Ceased
- 2014-03-15 JP JP2016503284A patent/JP6675973B2/ja not_active Expired - Fee Related
- 2014-03-15 BR BR112015023670A patent/BR112015023670A2/pt not_active Application Discontinuation
- 2014-03-15 KR KR1020157026223A patent/KR20160020403A/ko not_active Withdrawn
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2015
- 2015-10-12 ZA ZA2015/07551A patent/ZA201507551B/en unknown
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2018
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2019
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Also Published As
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|---|---|
| WO2014145210A1 (en) | 2014-09-18 |
| EP2968384A4 (en) | 2017-02-15 |
| US20190023731A1 (en) | 2019-01-24 |
| ZA201507551B (en) | 2017-11-29 |
| HK1218864A1 (zh) | 2017-03-17 |
| US20160046660A1 (en) | 2016-02-18 |
| JP6675973B2 (ja) | 2020-04-08 |
| RU2015138797A3 (enExample) | 2018-02-28 |
| JP2016514699A (ja) | 2016-05-23 |
| CN105188712A (zh) | 2015-12-23 |
| MX2015012465A (es) | 2016-05-31 |
| AU2014233240B2 (en) | 2018-08-09 |
| US9751908B2 (en) | 2017-09-05 |
| RU2015138797A (ru) | 2017-04-24 |
| BR112015023670A2 (pt) | 2017-07-18 |
| AU2014233240A1 (en) | 2015-10-01 |
| EP2968384A1 (en) | 2016-01-20 |
| HK1220394A1 (zh) | 2017-05-05 |
| MX356772B (es) | 2018-06-13 |
| US20200040024A1 (en) | 2020-02-06 |
| CA2907085A1 (en) | 2014-09-18 |
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