FI63244C - Foerfarande foer framstaellning av antibakteriska erytromysinderivater - Google Patents

Foerfarande foer framstaellning av antibakteriska erytromysinderivater Download PDF

Info

Publication number: FI63244C
Authority: FI; Finland
Prior art keywords: group; erythromycylamine; formula; condensation product; decomposes
Prior art date: 1975-04-07

Application number

FI760845A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI760845A (xx

FI63244B (fi

Inventor

Roland Maier

Eberhard Woitun

Bernd Wetzel

Wolfgang Reuter

Hanns Goeth

Uwe Lechner

Original Assignee

Thomae Gmbh Dr K

Priority date (The priority date 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 date listed.)

1975-04-07

Filing date

1976-03-30

Publication date

1983-05-10

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=25768725&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=FI63244(C) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1975-04-07 Priority claimed from DE2515075A external-priority patent/DE2515075C2/de

1976-02-14 Priority claimed from DE19762606030 external-priority patent/DE2606030A1/de

1976-03-30 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1976-10-08 Publication of FI760845A publication Critical patent/FI760845A/fi

1983-01-31 Application granted granted Critical

1983-01-31 Publication of FI63244B publication Critical patent/FI63244B/fi

1983-05-10 Publication of FI63244C publication Critical patent/FI63244C/fi

Links

-1 hydroxyethoxy, methoxyethoxy, dimethylaminoethoxy, carbethoxy methoxy group Chemical group 0.000 claims description 40
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 claims description 36
150000001875 compounds Chemical class 0.000 claims description 25
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 10
238000000034 method Methods 0.000 claims description 9
125000000217 alkyl group Chemical group 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 7
238000006243 chemical reaction Methods 0.000 claims description 7
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 claims description 6
239000002253 acid Substances 0.000 claims description 6
150000002500 ions Chemical class 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 5
230000000844 anti-bacterial effect Effects 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
150000001241 acetals Chemical class 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
239000000375 suspending agent Substances 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000004414 alkyl thio group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000003368 amide group Chemical group 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
238000011065 in-situ storage Methods 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
235000005985 organic acids Nutrition 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
239000000460 chlorine Substances 0.000 claims 1
125000004076 pyridyl group Chemical group 0.000 claims 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
239000007859 condensation product Substances 0.000 description 59
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 15
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UYWQUFXKFGHYNT-UHFFFAOYSA-N Benzylformate Chemical compound O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
238000009833 condensation Methods 0.000 description 8
239000000243 solution Substances 0.000 description 8
230000005494 condensation Effects 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000001299 aldehydes Chemical class 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000000203 mixture Substances 0.000 description 6
WGCNASOHLSPBMP-UHFFFAOYSA-N Glycolaldehyde Chemical compound OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
239000013078 crystal Substances 0.000 description 5
229920005989 resin Polymers 0.000 description 5
239000011347 resin Substances 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 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
238000004440 column chromatography Methods 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
LRIFVZYCVBCSMF-UHFFFAOYSA-N ethyl 4-sulfanylidenebutanoate Chemical compound CCOC(=O)CCC=S LRIFVZYCVBCSMF-UHFFFAOYSA-N 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000000284 extract Substances 0.000 description 3
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 3
229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
YSEFYOVWKJXNCH-UHFFFAOYSA-N 2-methoxyacetaldehyde Chemical compound COCC=O YSEFYOVWKJXNCH-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241000194017 Streptococcus Species 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
125000004663 dialkyl amino group Chemical group 0.000 description 2
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 2
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000035784 germination Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002243 precursor Substances 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
239000007858 starting material Substances 0.000 description 2
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 2
NCNSBFDGXBKAKB-UHFFFAOYSA-N (methylsulfanyl)acetaldehyde Chemical compound CSCC=O NCNSBFDGXBKAKB-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
GEUZCLYZVBWYRQ-UHFFFAOYSA-N 1,1-diethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOC(OCC)COCCOC GEUZCLYZVBWYRQ-UHFFFAOYSA-N 0.000 description 1
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 1
UUBOQGZIYKWPRN-UHFFFAOYSA-N 2-(2,2-diethoxyethoxy)ethanol Chemical compound CCOC(OCC)COCCO UUBOQGZIYKWPRN-UHFFFAOYSA-N 0.000 description 1
DSGGHBUAHUMMHN-UHFFFAOYSA-N 2-(2-hydroxyethoxy)acetaldehyde Chemical compound OCCOCC=O DSGGHBUAHUMMHN-UHFFFAOYSA-N 0.000 description 1
KEAGYJMKALOSDP-UHFFFAOYSA-N 2-(2-methoxyethoxy)acetaldehyde Chemical compound COCCOCC=O KEAGYJMKALOSDP-UHFFFAOYSA-N 0.000 description 1
YGFIFLUMYCKCIO-UHFFFAOYSA-N 2-(2-methylanilino)acetaldehyde Chemical compound CC1=CC=CC=C1NCC=O YGFIFLUMYCKCIO-UHFFFAOYSA-N 0.000 description 1
GOOISZUMBYZVEU-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]acetic acid Chemical compound CN(C)CCOCC(O)=O GOOISZUMBYZVEU-UHFFFAOYSA-N 0.000 description 1
LYIIBVSRGJSHAV-UHFFFAOYSA-N 2-aminoacetaldehyde Chemical compound NCC=O LYIIBVSRGJSHAV-UHFFFAOYSA-N 0.000 description 1
125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
MINDNVLLOCEDPP-UHFFFAOYSA-N 2-cyclohexylethanethial Chemical compound S=CCC1CCCCC1 MINDNVLLOCEDPP-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
ZZWQVTBJLLXLPJ-UHFFFAOYSA-N 2-diethoxyphosphorylacetaldehyde Chemical compound CCOP(=O)(CC=O)OCC ZZWQVTBJLLXLPJ-UHFFFAOYSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
GIDOBZXUXDNRDY-UHFFFAOYSA-N 2-hydroxy-3-oxohexanal Chemical compound CCCC(=O)C(O)C=O GIDOBZXUXDNRDY-UHFFFAOYSA-N 0.000 description 1
XFFILAFLGDUMBF-UHFFFAOYSA-N 2-phenoxyacetaldehyde Chemical compound O=CCOC1=CC=CC=C1 XFFILAFLGDUMBF-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
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
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
101100221077 Arabidopsis thaliana CML12 gene Proteins 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000901842 Escherichia coli W Species 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000589516 Pseudomonas Species 0.000 description 1
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
238000010171 animal model Methods 0.000 description 1
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230000000721 bacterilogical effect Effects 0.000 description 1
WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 1
229910001626 barium chloride Inorganic materials 0.000 description 1
ZGKWCFPCDVSLFE-UHFFFAOYSA-N benzyl 2-(dimethylamino)acetate Chemical compound CN(C)CC(=O)OCC1=CC=CC=C1 ZGKWCFPCDVSLFE-UHFFFAOYSA-N 0.000 description 1
LIMZVUINGDYQLL-UHFFFAOYSA-N benzyl 2-[(2-methoxybenzoyl)amino]acetate Chemical compound COC1=CC=CC=C1C(=O)NCC(=O)OCC1=CC=CC=C1 LIMZVUINGDYQLL-UHFFFAOYSA-N 0.000 description 1
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ORSXISLPWNELTJ-UHFFFAOYSA-N benzyl 2-phenoxyacetate Chemical compound C=1C=CC=CC=1COC(=O)COC1=CC=CC=C1 ORSXISLPWNELTJ-UHFFFAOYSA-N 0.000 description 1
BSLUQBYUQFPAHC-UHFFFAOYSA-N benzyl 3-amino-2-hydroxyprop-2-enoate Chemical compound C(C1=CC=CC=C1)OC(C(=CN)O)=O BSLUQBYUQFPAHC-UHFFFAOYSA-N 0.000 description 1
239000012267 brine Substances 0.000 description 1
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238000001035 drying Methods 0.000 description 1
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125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
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HMERBDKSEBSVGJ-UHFFFAOYSA-N ethyl 3,3-diethoxy-2-methoxypropanoate Chemical compound CCOC(OCC)C(OC)C(=O)OCC HMERBDKSEBSVGJ-UHFFFAOYSA-N 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 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
KCRRYOSHXIMXSZ-UHFFFAOYSA-N n-(2-oxoethyl)acetamide Chemical compound CC(=O)NCC=O KCRRYOSHXIMXSZ-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000005441 o-toluyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
239000012085 test solution Substances 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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)

FI760845A 1975-04-07 1976-03-30 Foerfarande foer framstaellning av antibakteriska erytromysinderivater FI63244C (fi)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE2515075		1975-04-07
DE2515075A DE2515075C2 (de)	1975-04-07	1975-04-07	Erythromycinderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2606030		1976-02-14
DE19762606030 DE2606030A1 (de)	1976-02-14	1976-02-14	Neue erythromycinderivate und verfahren zu ihrer herstellung

Publications (3)

Publication Number	Publication Date
FI760845A FI760845A (xx)	1976-10-08
FI63244B FI63244B (fi)	1983-01-31
FI63244C true FI63244C (fi)	1983-05-10

Family

ID=25768725

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI760845A FI63244C (fi)	1975-04-07	1976-03-30	Foerfarande foer framstaellning av antibakteriska erytromysinderivater

Country Status (29)

Country	Link
US (1)	US4048306A (xx)
JP (1)	JPS51128991A (xx)
AT (1)	AT342770B (xx)
AU (1)	AU498418B2 (xx)
BG (1)	BG27380A3 (xx)
CA (1)	CA1060005A (xx)
CH (2)	CH621800A5 (xx)
CS (1)	CS196304B2 (xx)
DD (1)	DD125218A5 (xx)
DK (1)	DK138656C (xx)
ES (2)	ES446737A1 (xx)
FI (1)	FI63244C (xx)
FR (1)	FR2306703A1 (xx)
GB (1)	GB1520963A (xx)
GR (1)	GR60374B (xx)
HU (1)	HU175186B (xx)
IE (1)	IE43598B1 (xx)
IL (1)	IL49359A (xx)
LU (2)	LU88563I2 (xx)
MX (1)	MX3277E (xx)
NL (1)	NL180107C (xx)
NO (1)	NO141411C (xx)
NZ (1)	NZ180529A (xx)
PL (1)	PL101880B1 (xx)
PT (1)	PT64977B (xx)
RO (1)	RO68441B (xx)
SE (1)	SE425566B (xx)
SU (1)	SU682134A3 (xx)
YU (1)	YU87676A (xx)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT82162B (en)	1985-03-12	1987-08-06	Beecham Group Plc	Chemical compounds
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
WO1992009614A1 (fr) *	1990-11-28	1992-06-11	Taisho Pharmaceutical Co., Ltd.	Derive de 6-o-methylerythromycine a
US5556839A (en) *	1991-04-29	1996-09-17	Eli Lilly And Company	Form II Dirithromycin
ZA922777B (en) *	1991-04-29	1993-10-15	Lilly Co Eli	Pharmaceutical formulation containing dirithromycin
CZ281664B6 (cs) *	1991-09-30	1996-12-11	Eli Lilly And Company Patent Division Lilly Corporate Center	Způsob jednostupňové přípravy dirithromycinu
DE4410637C1 (de) *	1994-03-26	1995-09-21	Boehringer Ingelheim Vetmed	Injizierbare Lösungen von Dirithromycin
WO1999021867A1 (fr) *	1997-10-29	1999-05-06	Taisho Pharmaceutical Co., Ltd.	Derives d'erythromycine a
US6544555B2 (en)	2000-02-24	2003-04-08	Advancis Pharmaceutical Corp.	Antibiotic product, use and formulation thereof
US6565882B2 (en)	2000-02-24	2003-05-20	Advancis Pharmaceutical Corp	Antibiotic composition with inhibitor
US6541014B2 (en)	2000-10-13	2003-04-01	Advancis Pharmaceutical Corp.	Antiviral product, use and formulation thereof
US20020068078A1 (en)	2000-10-13	2002-06-06	Rudnic Edward M.	Antifungal product, use and formulation thereof
US6436906B1 (en)	2001-04-02	2002-08-20	Enanta Pharmaceuticals, Inc.	9-amino-14-membered macrolides derived from leucomycins
EP1648418A4 (en)	2003-07-21	2011-11-16	Middlebrook Pharmaceuticals Inc	ANTIBIOTIC PRODUCT, ITS USE AND FORMULATION
CA2533178C (en)	2003-07-21	2014-03-11	Advancis Pharmaceutical Corporation	Antibiotic product, use and formulation thereof
EP1648407A4 (en)	2003-07-21	2011-08-31	Middlebrook Pharmaceuticals Inc	ANTIBIOTIC PRODUCT, CORRESPONDING USE AND FORMULATION
JP2007502296A (ja)	2003-08-11	2007-02-08	アドバンシスファーマスーティカルコーポレイション	ロバストペレット
EP1653924A4 (en)	2003-08-12	2009-09-09	Middlebrook Pharmaceuticals In	ANTIBIOTICS, USE AND FORMULATION ASSOCIATED
EP1658034A4 (en) *	2003-08-29	2011-06-22	Middlebrook Pharmaceuticals Inc	ANTIBIOTIC PRODUCT, ITS USE AND FORMULATION
WO2005027877A1 (en)	2003-09-15	2005-03-31	Advancis Pharmaceutical Corporation	Antibiotic product, use and formulation thereof
AU2005269981A1 (en)	2004-07-02	2006-02-09	Bonck, John A	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)

* Cited by examiner, † Cited by third party
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 BG BG032727A patent/BG27380A3/xx unknown
- 1976-03-29 US US05/671,421 patent/US4048306A/en not_active Expired - Lifetime
- 1976-03-30 FI FI760845A patent/FI63244C/fi not_active IP Right Cessation
- 1976-03-30 DK DK145276A patent/DK138656C/da not_active IP Right Cessation
- 1976-04-02 CH CH417476A patent/CH621800A5/de not_active IP Right Cessation
- 1976-04-05 DD DD192208A patent/DD125218A5/xx unknown
- 1976-04-05 LU LU88563C patent/LU88563I2/fr unknown
- 1976-04-05 LU LU74702A patent/LU74702A1/xx unknown
- 1976-04-06 MX MX000145U patent/MX3277E/es unknown
- 1976-04-06 NZ NZ180529A patent/NZ180529A/xx unknown
- 1976-04-06 PL PL1976188538A patent/PL101880B1/pl unknown
- 1976-04-06 IL IL49359A patent/IL49359A/xx unknown
- 1976-04-06 RO RO85433A patent/RO68441B/ro unknown
- 1976-04-06 YU YU00876/76A patent/YU87676A/xx unknown
- 1976-04-06 ES ES446737A patent/ES446737A1/es not_active Expired
- 1976-04-06 NO NO761172A patent/NO141411C/no unknown
- 1976-04-06 HU HU76TO1026A patent/HU175186B/hu unknown
- 1976-04-06 AU AU12722/76A patent/AU498418B2/en not_active Expired
- 1976-04-06 SE SE7604052A patent/SE425566B/xx not_active IP Right Cessation
- 1976-04-06 PT PT64977A patent/PT64977B/pt 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 GB GB13942/76A patent/GB1520963A/en not_active Expired
- 1976-04-06 CS CS762265A patent/CS196304B2/cs unknown
- 1976-04-06 SU SU762343016A patent/SU682134A3/ru active
- 1976-04-06 CA CA249,700A patent/CA1060005A/en not_active Expired
- 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

Publication number	Publication date
CA1060005A (en)	1979-08-07
NO141411C (no)	1980-03-05
SE7604052L (sv)	1976-10-08
YU87676A (en)	1982-08-31
LU88563I2 (fr)	1995-03-21
PL101880B1 (pl)	1979-02-28
NL7603569A (nl)	1976-10-11
SU682134A3 (ru)	1979-08-25
ES456567A1 (es)	1978-03-01
NL180107C (nl)	1987-01-02
NZ180529A (en)	1978-09-20
FI760845A (xx)	1976-10-08
DK138656C (da)	1979-04-02
NO141411B (no)	1979-11-26
RO68441A (ro)	1983-04-29
US4048306A (en)	1977-09-13
DD125218A5 (de)	1977-04-06
AU1272276A (en)	1977-10-13
MX3277E (es)	1980-08-15
AU498418B2 (en)	1979-03-15
HU175186B (hu)	1980-05-28
PT64977B (de)	1978-04-03
BG27380A3 (en)	1979-10-12
JPS62158B2 (xx)	1987-01-06
JPS51128991A (en)	1976-11-10
CH621800A5 (xx)	1981-02-27
LU74702A1 (xx)	1977-06-03
RO68441B (ro)	1983-04-30
PT64977A (de)	1976-05-01
NL180107B (nl)	1986-08-01
GR60374B (en)	1978-05-23
IE43598B1 (en)	1981-04-08
DK145276A (da)	1976-10-08
SE425566B (sv)	1982-10-11
NO761172L (xx)	1976-10-08
GB1520963A (en)	1978-08-09
DK138656B (da)	1978-10-09
FR2306703A1 (fr)	1976-11-05
FR2306703B1 (xx)	1979-10-12
FI63244B (fi)	1983-01-31
IL49359A (en)	1979-07-25
IE43598L (en)	1976-10-07
ATA149976A (de)	1977-08-15
CH624413A5 (xx)	1981-07-31
CS196304B2 (en)	1980-03-31
AT342770B (de)	1978-04-25
ES446737A1 (es)	1977-10-16
IL49359A0 (en)	1976-06-30

Publication	Publication Date	Title
FI63244C (fi)	1983-05-10	Foerfarande foer framstaellning av antibakteriska erytromysinderivater
SU1424732A3 (ru)	1988-09-15	Способ получени 2,4-диамино-5-(замещенных)пиримидинов или их солей
JPH01193292A (ja)	1989-08-03	Ｎ−メチル１１−アザ−１０−デオキソ−１０−ジヒドロエリスロマイシンａ製造用中間体
FI70699B (fi)	1986-06-26	Foerfarande foer framstaellning av antivirala substituerade actofenoner
FR2555584A1 (fr)	1985-05-31	Derives de l'acide fluoro-6-dihydro-1,4-oxo-4-piperazinyl substitue-7-quinoline-carboxylique-3 et procede pour leur preparation et compositions pharmaceutiques a action anti-bacteriennes a base desdits derives
FR2476088A2 (fr)	1981-08-21	Nouveaux derives du nor-tropane, leur procede de preparation et leur application en therapeutique
EP0019081A1 (de)	1980-11-26	Neue Flavonderivate, deren Herstellung, diese neuen und bekannte Flavone als antivirale Wirkstoffe und sie enthaltende pharmazeutische Präparate
FI72322B (fi)	1987-01-30	Foerfarande foer framstaellning av terapeutiskt anvaendbara marolider
CA1112649A (en)	1981-11-17	4-spectinomycylamine and salts thereof
US4090017A (en)	1978-05-16	4-Deoxy-4-substituted amino derivatives of oleandomycin
US4882316A (en)	1989-11-21	Pyrimidine derivatives
US4085119A (en)	1978-04-18	4-Substituted amino derivatives of oleandomycin
US4232023A (en)	1980-11-04	Novel soluble derivatives of 2,4-diamino pyrimidine
FR2458556A1 (fr)	1981-01-02	Derives de la paromomycine, procede pour les preparer et leur usage comme medicament
EP0080819A1 (en)	1983-06-08	11-0-Alkylerythromycin A derivatives
US4327088A (en)	1982-04-27	Phosphonooxy- or glycosyloxy-substituted acrylophenones, compositions and uses thereof
GB2083022A (en)	1982-03-17	Phenethylamine derivatives and their production
US4954485A (en)	1990-09-04	2',3'-dideoxy-4-thio-uridine derivatives, process for their preparation and antivirus agents using them
CH618677A5 (en)	1980-08-15	Process for the preparation of phenylalkylamines
DK152133B (da)	1988-02-01	Analogifremgangsmaade til fremstilling af oleandomycinderivater eller farmaceutisk acceptable syreadditionssalte deraf
US5668168A (en)	1997-09-16	1,2-dithiin antiinfective agents
CS200536B2 (en)	1980-09-15	Method of producing epimeric 4-amino oleandomycin derivatives
US5233029A (en)	1993-08-03	Elaiophylin derivatives and a process for the preparation thereof
JP2840334B2 (ja)	1998-12-24	抗ウイルス化合物
US4985451A (en)	1991-01-15	Elaiophylin derivatives, the use thereof as pharmaceuticals, and pharmaceuticals containing them

Legal Events

Date	Code	Title	Description
1976-03-30	MA	Patent expired
2004-08-31	MA	Patent expired	Owner name: DR. KARL THOMAE GMBH