CS196304B2 - Process for preparing new derivatives of erythromycine - Google Patents
Process for preparing new derivatives of erythromycine Download PDFInfo
- Publication number
- CS196304B2 CS196304B2 CS762265A CS226576A CS196304B2 CS 196304 B2 CS196304 B2 CS 196304B2 CS 762265 A CS762265 A CS 762265A CS 226576 A CS226576 A CS 226576A CS 196304 B2 CS196304 B2 CS 196304B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- carbon atoms
- erythromycylamine
- formula
- phenyl
- Prior art date
Links
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class 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 title claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- -1 phenylmercapto group Chemical group 0.000 claims abstract description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 3
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 125000003368 amide group Chemical group 0.000 claims abstract description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 3
- 125000002541 furyl group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims abstract description 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 101100280057 Brucella abortus (strain 2308) eryI gene Proteins 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 14
- 239000000243 solution Substances 0.000 abstract description 8
- 150000003839 salts Chemical class 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 3
- 125000003277 amino group Chemical group 0.000 abstract description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract description 2
- 125000004076 pyridyl group Chemical group 0.000 abstract description 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 abstract description 2
- 239000004480 active ingredient Substances 0.000 abstract 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract 2
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000003826 tablet Substances 0.000 abstract 2
- 229930008281 A03AD01 - Papaverine Natural products 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000004450 alkenylene group Chemical group 0.000 abstract 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 229960001789 papaverine Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 125000005359 phenoxyalkyl group Chemical group 0.000 abstract 1
- 125000002071 phenylalkoxy group Chemical group 0.000 abstract 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 abstract 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- XCLJRCAJSCMIND-JCTYMORFSA-N (9S)-erythromycyclamine Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)[C@@H](N)[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 XCLJRCAJSCMIND-JCTYMORFSA-N 0.000 description 90
- 239000007859 condensation product Substances 0.000 description 79
- 239000000047 product Substances 0.000 description 68
- 239000000155 melt Substances 0.000 description 57
- 238000000354 decomposition reaction Methods 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- 150000001875 compounds Chemical class 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 150000001299 aldehydes Chemical class 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 150000002500 ions Chemical class 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- ZZWQVTBJLLXLPJ-UHFFFAOYSA-N 2-diethoxyphosphorylacetaldehyde Chemical compound CCOP(=O)(CC=O)OCC ZZWQVTBJLLXLPJ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- NCNSBFDGXBKAKB-UHFFFAOYSA-N (methylsulfanyl)acetaldehyde Chemical compound CSCC=O NCNSBFDGXBKAKB-UHFFFAOYSA-N 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- LYIIBVSRGJSHAV-UHFFFAOYSA-N 2-aminoacetaldehyde Chemical compound NCC=O LYIIBVSRGJSHAV-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001241 acetals Chemical class 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- LRIFVZYCVBCSMF-UHFFFAOYSA-N ethyl 4-sulfanylidenebutanoate Chemical compound CCOC(=O)CCC=S LRIFVZYCVBCSMF-UHFFFAOYSA-N 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
- KEAGYJMKALOSDP-UHFFFAOYSA-N 2-(2-methoxyethoxy)acetaldehyde Chemical compound COCCOCC=O KEAGYJMKALOSDP-UHFFFAOYSA-N 0.000 description 2
- MINDNVLLOCEDPP-UHFFFAOYSA-N 2-cyclohexylethanethial Chemical compound S=CCC1CCCCC1 MINDNVLLOCEDPP-UHFFFAOYSA-N 0.000 description 2
- YSEFYOVWKJXNCH-UHFFFAOYSA-N 2-methoxyacetaldehyde Chemical compound COCC=O YSEFYOVWKJXNCH-UHFFFAOYSA-N 0.000 description 2
- XFFILAFLGDUMBF-UHFFFAOYSA-N 2-phenoxyacetaldehyde Chemical compound O=CCOC1=CC=CC=C1 XFFILAFLGDUMBF-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- OFBNJEUAEZLKHY-UHFFFAOYSA-N ethyl 2-methoxy-3-oxopropanoate Chemical compound CCOC(=O)C(OC)C=O OFBNJEUAEZLKHY-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- DYOZNCVZPFIXLU-UHFFFAOYSA-N 1,1,2-trimethoxyethane Chemical compound COCC(OC)OC DYOZNCVZPFIXLU-UHFFFAOYSA-N 0.000 description 1
- OBNSVFHYXVTTKN-UHFFFAOYSA-N 2,2-dichloro-n-(2-oxoethyl)acetamide Chemical compound ClC(Cl)C(=O)NCC=O OBNSVFHYXVTTKN-UHFFFAOYSA-N 0.000 description 1
- DSGGHBUAHUMMHN-UHFFFAOYSA-N 2-(2-hydroxyethoxy)acetaldehyde Chemical compound OCCOCC=O DSGGHBUAHUMMHN-UHFFFAOYSA-N 0.000 description 1
- MQEQHTPCRWWOIZ-UHFFFAOYSA-N 2-(2-methoxyphenyl)ethanethial Chemical compound COC1=CC=CC=C1CC=S MQEQHTPCRWWOIZ-UHFFFAOYSA-N 0.000 description 1
- HQNDOOMQQOYEOM-UHFFFAOYSA-N 2-(4-methylphenyl)ethanethial Chemical compound CC1=CC=C(CC=S)C=C1 HQNDOOMQQOYEOM-UHFFFAOYSA-N 0.000 description 1
- KZMQZFPRPILIHO-UHFFFAOYSA-N 2-(methylamino)acetaldehyde Chemical compound CNCC=O KZMQZFPRPILIHO-UHFFFAOYSA-N 0.000 description 1
- IODYXSKLZFZLSS-UHFFFAOYSA-N 2-[benzyl(methyl)amino]acetaldehyde Chemical compound O=CCN(C)CC1=CC=CC=C1 IODYXSKLZFZLSS-UHFFFAOYSA-N 0.000 description 1
- RPLPGIHCAYAYKX-UHFFFAOYSA-N 2-butoxyacetaldehyde Chemical compound CCCCOCC=O RPLPGIHCAYAYKX-UHFFFAOYSA-N 0.000 description 1
- WMOIWCQTFQGVAF-UHFFFAOYSA-N 2-chloro-n-(2-oxoethyl)acetamide Chemical compound ClCC(=O)NCC=O WMOIWCQTFQGVAF-UHFFFAOYSA-N 0.000 description 1
- FAKKEVPNKACVPM-UHFFFAOYSA-N 2-chloro-n-(2-oxoethyl)benzamide Chemical compound ClC1=CC=CC=C1C(=O)NCC=O FAKKEVPNKACVPM-UHFFFAOYSA-N 0.000 description 1
- XMORGWRBGODJMM-UHFFFAOYSA-N 2-diethoxyphosphoryl-1,1-dimethoxyethane Chemical compound CCOP(=O)(OCC)CC(OC)OC XMORGWRBGODJMM-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- HFBNUVNBTPEIRY-UHFFFAOYSA-N 2-ethylsulfanylacetaldehyde Chemical compound CCSCC=O HFBNUVNBTPEIRY-UHFFFAOYSA-N 0.000 description 1
- DPZXGASNLDDAIU-UHFFFAOYSA-N 2-hydroxy-n-(2-oxoethyl)benzamide Chemical compound OC1=CC=CC=C1C(=O)NCC=O DPZXGASNLDDAIU-UHFFFAOYSA-N 0.000 description 1
- XDJKCIVJWAWRQC-UHFFFAOYSA-N 2-methyl-n-(2-oxoethyl)benzamide Chemical compound CC1=CC=CC=C1C(=O)NCC=O XDJKCIVJWAWRQC-UHFFFAOYSA-N 0.000 description 1
- QAKXPQSVKFRFHD-UHFFFAOYSA-N 2-methylsulfonylacetaldehyde Chemical compound CS(=O)(=O)CC=O QAKXPQSVKFRFHD-UHFFFAOYSA-N 0.000 description 1
- ODNFQADBSZFWFO-UHFFFAOYSA-N 2-phenylethanethial Chemical compound S=CCC1=CC=CC=C1 ODNFQADBSZFWFO-UHFFFAOYSA-N 0.000 description 1
- NFNOAHXEQXMCGT-UHFFFAOYSA-N 2-phenylmethoxyacetaldehyde Chemical compound O=CCOCC1=CC=CC=C1 NFNOAHXEQXMCGT-UHFFFAOYSA-N 0.000 description 1
- ZMQKVTSIRCJPOE-UHFFFAOYSA-N 2-piperidin-1-ylacetaldehyde Chemical compound O=CCN1CCCCC1 ZMQKVTSIRCJPOE-UHFFFAOYSA-N 0.000 description 1
- QIQRCPPUXQAGLN-UHFFFAOYSA-N 2-pyrrolidin-1-ylacetaldehyde Chemical compound O=CCN1CCCC1 QIQRCPPUXQAGLN-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RAPFWIVDXSMGAP-UHFFFAOYSA-N 3-methylbutanethial Chemical compound CC(C)CC=S RAPFWIVDXSMGAP-UHFFFAOYSA-N 0.000 description 1
- UAMDWTCVJDBESC-UHFFFAOYSA-N 3-phenylpropanethial Chemical compound S=CCCC1=CC=CC=C1 UAMDWTCVJDBESC-UHFFFAOYSA-N 0.000 description 1
- UABJCXFZCYLSSK-UHFFFAOYSA-N 4,4-diethoxy-3-hydroxybutan-2-one Chemical compound CCOC(OCC)C(O)C(C)=O UABJCXFZCYLSSK-UHFFFAOYSA-N 0.000 description 1
- HPFQZLCLFMJMRD-UHFFFAOYSA-N 4-hydroxybutanethial Chemical compound OCCCC=S HPFQZLCLFMJMRD-UHFFFAOYSA-N 0.000 description 1
- KCXGZIHEIWFWCR-UHFFFAOYSA-N 4-methyl-n-(2-oxoethyl)benzenesulfonamide Chemical compound CC1=CC=C(S(=O)(=O)NCC=O)C=C1 KCXGZIHEIWFWCR-UHFFFAOYSA-N 0.000 description 1
- MTFCVJMDVAVESS-UHFFFAOYSA-N 4-nitro-n-(2-oxoethyl)benzamide Chemical compound [O-][N+](=O)C1=CC=C(C(=O)NCC=O)C=C1 MTFCVJMDVAVESS-UHFFFAOYSA-N 0.000 description 1
- OTRAXLZRENDKQJ-UHFFFAOYSA-N 4-sulfanylidenebutanenitrile Chemical compound S=CCCC#N OTRAXLZRENDKQJ-UHFFFAOYSA-N 0.000 description 1
- XPINPERFSVZKFZ-UHFFFAOYSA-N 5-phenylpentanethial Chemical compound S=CCCCCC1=CC=CC=C1 XPINPERFSVZKFZ-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- UTVCRIGSBBSUGM-UHFFFAOYSA-N C(#N)CC(=O)NCC=O Chemical compound C(#N)CC(=O)NCC=O UTVCRIGSBBSUGM-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 238000002768 Kirby-Bauer method Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003275 alpha amino acid group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000011482 antibacterial activity assay Methods 0.000 description 1
- 230000000721 bacterilogical effect Effects 0.000 description 1
- ZBDOVHVJWVWSPQ-UHFFFAOYSA-N benzylpenilloaldehyde Chemical compound O=CCNC(=O)CC1=CC=CC=C1 ZBDOVHVJWVWSPQ-UHFFFAOYSA-N 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- VTWSAUBAZJVTLS-UHFFFAOYSA-N heptanethial Chemical compound CCCCCCC=S VTWSAUBAZJVTLS-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- KOHBQRYQVXRNAZ-UHFFFAOYSA-N methyl 5-sulfanylidenepentanoate Chemical compound COC(=O)CCCC=S KOHBQRYQVXRNAZ-UHFFFAOYSA-N 0.000 description 1
- YGEAEJNJEVNVLG-UHFFFAOYSA-N n-(2,2-dimethoxyethyl)acetamide Chemical compound COC(OC)CNC(C)=O YGEAEJNJEVNVLG-UHFFFAOYSA-N 0.000 description 1
- DBLOBYLAOPVZBH-UHFFFAOYSA-N n-(2-oxoethyl)-3-phenylprop-2-enamide Chemical compound O=CCNC(=O)C=CC1=CC=CC=C1 DBLOBYLAOPVZBH-UHFFFAOYSA-N 0.000 description 1
- KCRRYOSHXIMXSZ-UHFFFAOYSA-N n-(2-oxoethyl)acetamide Chemical compound CC(=O)NCC=O KCRRYOSHXIMXSZ-UHFFFAOYSA-N 0.000 description 1
- XEIWWWPDOUQNJF-UHFFFAOYSA-N n-(2-oxoethyl)benzamide Chemical compound O=CCNC(=O)C1=CC=CC=C1 XEIWWWPDOUQNJF-UHFFFAOYSA-N 0.000 description 1
- KDFVKSQEBDZWIS-UHFFFAOYSA-N n-(2-oxoethyl)hexanamide Chemical compound CCCCCC(=O)NCC=O KDFVKSQEBDZWIS-UHFFFAOYSA-N 0.000 description 1
- HMHQZWUZRCHGIZ-UHFFFAOYSA-N n-(2-oxoethyl)methanesulfonamide Chemical compound CS(=O)(=O)NCC=O HMHQZWUZRCHGIZ-UHFFFAOYSA-N 0.000 description 1
- NBSUHOKXCZGPBO-UHFFFAOYSA-N n-(2-oxoethyl)propanamide Chemical compound CCC(=O)NCC=O NBSUHOKXCZGPBO-UHFFFAOYSA-N 0.000 description 1
- MCEWGFLAIVCDHR-UHFFFAOYSA-N n-(2-oxoethyl)pyridine-3-carboxamide Chemical compound O=CCNC(=O)C1=CC=CN=C1 MCEWGFLAIVCDHR-UHFFFAOYSA-N 0.000 description 1
- YFSZXMKBLOKLRL-UHFFFAOYSA-N n-(2-oxoethyl)thiophene-2-carboxamide Chemical compound O=CCNC(=O)C1=CC=CS1 YFSZXMKBLOKLRL-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65586—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system at least one of the hetero rings does not contain nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- 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)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2515075A DE2515075C2 (de) | 1975-04-07 | 1975-04-07 | Erythromycinderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE19762606030 DE2606030A1 (de) | 1976-02-14 | 1976-02-14 | Neue erythromycinderivate und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS196304B2 true CS196304B2 (en) | 1980-03-31 |
Family
ID=25768725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS762265A CS196304B2 (en) | 1975-04-07 | 1976-04-06 | Process for preparing new derivatives of erythromycine |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4048306A (de) |
| JP (1) | JPS51128991A (de) |
| AT (1) | AT342770B (de) |
| AU (1) | AU498418B2 (de) |
| BG (1) | BG27380A3 (de) |
| CA (1) | CA1060005A (de) |
| CH (2) | CH621800A5 (de) |
| CS (1) | CS196304B2 (de) |
| DD (1) | DD125218A5 (de) |
| DK (1) | DK138656C (de) |
| ES (2) | ES446737A1 (de) |
| FI (1) | FI63244C (de) |
| FR (1) | FR2306703A1 (de) |
| GB (1) | GB1520963A (de) |
| GR (1) | GR60374B (de) |
| HU (1) | HU175186B (de) |
| IE (1) | IE43598B1 (de) |
| IL (1) | IL49359A (de) |
| LU (2) | LU88563I2 (de) |
| MX (1) | MX3277E (de) |
| NL (1) | NL180107C (de) |
| NO (1) | NO141411C (de) |
| NZ (1) | NZ180529A (de) |
| PL (1) | PL101880B1 (de) |
| PT (1) | PT64977B (de) |
| RO (1) | RO68441B (de) |
| SE (1) | SE425566B (de) |
| SU (1) | SU682134A3 (de) |
| YU (1) | YU87676A (de) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0201166B1 (de) | 1985-03-12 | 1990-02-07 | Beecham Group Plc | Erythromycin-Derivate |
| DE3524572A1 (de) * | 1985-07-10 | 1987-01-15 | Thomae Gmbh Dr K | Feste arzneimittelformen zur peroralen anwendung enthaltend 9-deoxo-11-deoxy-9,11-(imino(2-(2-methoxyethoxy)ethyliden)-oxy)-(9s)-erythromycin und verfahren zu ihrer herstellung |
| US5110800A (en) * | 1986-02-18 | 1992-05-05 | Eli Lilly And Company | Derivatives of erythromycylamine |
| US4945080A (en) * | 1987-05-26 | 1990-07-31 | Eli Lilly And Company | Dirithromycin metabolite |
| US5075289A (en) * | 1988-06-07 | 1991-12-24 | Abbott Laboratories | 9-r-azacyclic erythromycin antibiotics |
| DE69127457T2 (de) * | 1990-11-28 | 1998-01-22 | Taisho Pharmaceutical Co., Ltd., Tokio/Tokyo | 6-0-methylerythromycin a-derivat |
| ZA922777B (en) * | 1991-04-29 | 1993-10-15 | Lilly Co Eli | Pharmaceutical formulation containing dirithromycin |
| US5556839A (en) * | 1991-04-29 | 1996-09-17 | Eli Lilly And Company | Form II Dirithromycin |
| ZA927328B (en) * | 1991-09-30 | 1994-03-24 | Lilly Co Eli | One step process for production of dirithromycin |
| DE4410637C1 (de) * | 1994-03-26 | 1995-09-21 | Boehringer Ingelheim Vetmed | Injizierbare Lösungen von Dirithromycin |
| AU9645998A (en) * | 1997-10-29 | 1999-05-17 | Taisho Pharmaceutical Co., Ltd. | Erythromycin a derivatives |
| US6565882B2 (en) | 2000-02-24 | 2003-05-20 | Advancis Pharmaceutical Corp | Antibiotic composition with inhibitor |
| US6544555B2 (en) | 2000-02-24 | 2003-04-08 | Advancis Pharmaceutical Corp. | Antibiotic product, use and formulation thereof |
| US20020068078A1 (en) | 2000-10-13 | 2002-06-06 | Rudnic Edward M. | Antifungal product, use and formulation thereof |
| US6541014B2 (en) | 2000-10-13 | 2003-04-01 | Advancis Pharmaceutical Corp. | Antiviral product, use and formulation thereof |
| US6436906B1 (en) | 2001-04-02 | 2002-08-20 | Enanta Pharmaceuticals, Inc. | 9-amino-14-membered macrolides derived from leucomycins |
| AU2004258949B2 (en) | 2003-07-21 | 2011-02-10 | Shionogi, Inc. | Antibiotic product, use and formulation thereof |
| EP1648418A4 (de) | 2003-07-21 | 2011-11-16 | Middlebrook Pharmaceuticals Inc | Antibiotisches produkt, seine verwendung und formulierung |
| CA2533292C (en) | 2003-07-21 | 2013-12-31 | Advancis Pharmaceutical Corporation | Antibiotic product, use and formulation thereof |
| CA2535177A1 (en) | 2003-08-11 | 2005-02-24 | Advancis Pharmaceutical Corporation | Robust pellet |
| EP1653924A4 (de) | 2003-08-12 | 2009-09-09 | Middlebrook Pharmaceuticals In | Antibiotisches produkt, seine verwendung und formulierung |
| CA2535780A1 (en) * | 2003-08-29 | 2005-03-17 | Advancis Pharmaceuticals Corporation | Antibiotic product, use and formulation thereof |
| US8460710B2 (en) | 2003-09-15 | 2013-06-11 | Shionogi, Inc. | Antibiotic product, use and formulation thereof |
| CA2572292A1 (en) | 2004-07-02 | 2006-02-09 | Advancis Pharmaceutical Corporation | Tablet for pulsed delivery |
| US8778924B2 (en) | 2006-12-04 | 2014-07-15 | Shionogi Inc. | Modified release amoxicillin products |
| US8357394B2 (en) | 2005-12-08 | 2013-01-22 | Shionogi Inc. | Compositions and methods for improved efficacy of penicillin-type antibiotics |
| US8299052B2 (en) * | 2006-05-05 | 2012-10-30 | Shionogi Inc. | Pharmaceutical compositions and methods for improved bacterial eradication |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3660376A (en) * | 1970-09-30 | 1972-05-02 | Lilly Co Eli | N-arylidene erythromycylamines |
-
1976
- 1976-03-01 AT AT149976A patent/AT342770B/de not_active IP Right Cessation
- 1976-03-26 GR GR50399A patent/GR60374B/el unknown
- 1976-03-29 US US05/671,421 patent/US4048306A/en not_active Expired - Lifetime
- 1976-03-29 BG BG032727A patent/BG27380A3/xx unknown
- 1976-03-30 DK DK145276A patent/DK138656C/da not_active IP Right Cessation
- 1976-03-30 FI FI760845A patent/FI63244C/fi not_active IP Right Cessation
- 1976-04-02 CH CH417476A patent/CH621800A5/de not_active IP Right Cessation
- 1976-04-05 LU LU88563C patent/LU88563I2/fr unknown
- 1976-04-05 LU LU74702A patent/LU74702A1/xx unknown
- 1976-04-05 DD DD192208A patent/DD125218A5/de unknown
- 1976-04-06 SU SU762343016A patent/SU682134A3/ru active
- 1976-04-06 HU HU76TO1026A patent/HU175186B/hu unknown
- 1976-04-06 ES ES446737A patent/ES446737A1/es not_active Expired
- 1976-04-06 NO NO761172A patent/NO141411C/no unknown
- 1976-04-06 CA CA249,700A patent/CA1060005A/en not_active Expired
- 1976-04-06 CS CS762265A patent/CS196304B2/cs unknown
- 1976-04-06 AU AU12722/76A patent/AU498418B2/en not_active Expired
- 1976-04-06 IL IL49359A patent/IL49359A/xx unknown
- 1976-04-06 MX MX000145U patent/MX3277E/es unknown
- 1976-04-06 NL NLAANVRAGE7603569,A patent/NL180107C/xx not_active IP Right Cessation
- 1976-04-06 JP JP51038681A patent/JPS51128991A/ja active Granted
- 1976-04-06 PL PL1976188538A patent/PL101880B1/pl unknown
- 1976-04-06 GB GB13942/76A patent/GB1520963A/en not_active Expired
- 1976-04-06 SE SE7604052A patent/SE425566B/xx not_active IP Right Cessation
- 1976-04-06 NZ NZ180529A patent/NZ180529A/xx unknown
- 1976-04-06 YU YU00876/76A patent/YU87676A/xx unknown
- 1976-04-06 PT PT64977A patent/PT64977B/de unknown
- 1976-04-06 RO RO85433A patent/RO68441B/ro unknown
- 1976-04-07 IE IE732/76A patent/IE43598B1/en not_active IP Right Cessation
- 1976-04-07 FR FR7610144A patent/FR2306703A1/fr active Granted
-
1977
- 1977-03-05 ES ES456567A patent/ES456567A1/es not_active Expired
-
1980
- 1980-04-10 CH CH277580A patent/CH624413A5/de not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CS196304B2 (en) | Process for preparing new derivatives of erythromycine | |
| DE69225500T2 (de) | Chinazolinone als mittel gegen angina | |
| DE69305344T2 (de) | Antianginale purinone | |
| Zhang et al. | Synthesis of novel sulfonamide azoles via C–N cleavage of sulfonamides by azole ring and relational antimicrobial study | |
| DE69428142T2 (de) | Quinolin- oder Quinazolinderivate, deren Herstellung und Verwendung | |
| CH645100A5 (de) | Substituierte 3-aryl-pyrazole und 5-aryl-isoxazole und verfahren zu ihrer herstellung. | |
| DE69915487T2 (de) | Erythromycin-derivate mit antibiotischer wirkung | |
| US4423046A (en) | Antibacterial and antiprotozoal 1-methyl-5-nitro-2-(2-phenylvinyl)imidazoles | |
| EP3655394B1 (de) | Neuartige albicidinderivate, deren verwendung und synthese | |
| US4080380A (en) | 2-Naphthyl-lower-alkylamines | |
| DE3880874T2 (de) | Morpholin-Derivate, deren Verfahren zur Herstellung und sie enthaltende pharmazeutische Zusammensetzungen. | |
| PT90337B (pt) | Processo para a preparacao de derivados de 6-oxo--piridazina e de composicoes farmaceuticas que os contem | |
| FR2461705A1 (fr) | Nouveaux derives de 1-(4-aminobenzyl)-2,3-dioxopiperazine et leurs sels d'addition d'acides, a action carcinostatique, et procedes pour les preparer | |
| US3231574A (en) | Piperazine derivatives | |
| US3378564A (en) | Certain pyridyl tetrazole derivatives | |
| HU197003B (en) | Process for producing new isoxazole derivatives and pharmaceuticals comprising same | |
| US2762805A (en) | 3-ethyl-3-phenyl-2, 6-piperazinedione and derivatives thereof | |
| US3946031A (en) | 2-Substituted-1,2,4-thiadiazolo-[2,3-a]-benzimidazoles | |
| US3128273A (en) | 4-amino-pteridine-7-carboxamides and method of preparation | |
| JPH0437073B2 (de) | ||
| JPS5935400B2 (ja) | ５−ニトロイミダゾ−ル誘導体の製造法 | |
| KR810001654B1 (ko) | 7-(치환된)-7H-피롤로〔3, 2-f〕퀴나졸린-1, 3-디아민 유도체의 제조방법 | |
| Vagadia et al. | SYNTHESIS AND ANTIMICROBIAL EVALUTION OF SOME NOVEL SUBSTITUTED THIAZOLE DERIVATIVES. | |
| EP3974416A1 (de) | Neuartige albicidinderivate, deren verwendung und synthese | |
| KR100491100B1 (ko) | 신규테레프탈산아미드유도체 |