DK171404B1 - C63-Amidderivater af 34-de-(acetylglucosaminyl)-34-deoxy-teicoplaniner, fremgangsmåde til fremstilling heraf, anvendelse af sådanne forbindelser til fremstilling af medikamenter samt farmaceutiske præparater indeholdende forbindelserne - Google Patents

C63-Amidderivater af 34-de-(acetylglucosaminyl)-34-deoxy-teicoplaniner, fremgangsmåde til fremstilling heraf, anvendelse af sådanne forbindelser til fremstilling af medikamenter samt farmaceutiske præparater indeholdende forbindelserne Download PDF

Info

Publication number: DK171404B1
Authority: DK; Denmark
Prior art keywords: group; hydrogen; formula; decanoyl; branched
Prior art date: 1988-12-27

Application number

DK640489A

Other languages

Danish (da)

English (en)

Other versions

DK640489A (da

DK640489D0 (da

Inventor

Adriano Malabarba

Juergen Kurt Kettenring

Original Assignee

Lepetit Spa

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.)

1988-12-27

Filing date

1989-12-18

Publication date

1996-10-14

1989-12-18 Application filed by Lepetit Spa filed Critical Lepetit Spa

1989-12-18 Publication of DK640489D0 publication Critical patent/DK640489D0/da

1990-06-28 Publication of DK640489A publication Critical patent/DK640489A/da

1996-10-14 Application granted granted Critical

1996-10-14 Publication of DK171404B1 publication Critical patent/DK171404B1/da

Links

-1 acetylglucosaminyl Chemical group 0.000 title claims abstract description 71
150000001875 compounds Chemical class 0.000 title claims description 65
238000000034 method Methods 0.000 title claims description 26
238000002360 preparation method Methods 0.000 title claims description 15
239000003814 drug Substances 0.000 title claims description 4
239000008194 pharmaceutical composition Substances 0.000 title claims description 3
229940079593 drug Drugs 0.000 title 1
239000002253 acid Substances 0.000 claims abstract description 35
150000003839 salts Chemical class 0.000 claims abstract description 29
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
239000001257 hydrogen Substances 0.000 claims abstract description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 18
125000006239 protecting group Chemical group 0.000 claims abstract description 18
150000001412 amines Chemical class 0.000 claims abstract description 17
150000002148 esters Chemical class 0.000 claims abstract description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 8
150000007513 acids Chemical class 0.000 claims abstract description 8
230000001588 bifunctional effect Effects 0.000 claims abstract description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
125000001424 substituent group Chemical group 0.000 claims abstract description 5
241001505901 Streptococcus sp. 'group A' Species 0.000 claims abstract description 4
150000002431 hydrogen Chemical class 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
239000007858 starting material Substances 0.000 claims description 18
DDTDNCYHLGRFBM-YZEKDTGTSA-N chembl2367892 Chemical class CC(=O)N[C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1O[C@@H]([C@H]1C(N[C@@H](C2=CC(O)=CC(O[C@@H]3[C@H]([C@H](O)[C@H](O)[C@@H](CO)O3)O)=C2C=2C(O)=CC=C(C=2)[C@@H](NC(=O)[C@@H]2NC(=O)[C@@H]3C=4C=C(O)C=C(C=4)OC=4C(O)=CC=C(C=4)[C@@H](N)C(=O)N[C@H](CC=4C=C(Cl)C(O5)=CC=4)C(=O)N3)C(=O)N1)C(O)=O)=O)C(C=C1Cl)=CC=C1OC1=C(O[C@H]3[C@H]([C@@H](O)[C@H](O)[C@H](CO)O3)NC(C)=O)C5=CC2=C1 DDTDNCYHLGRFBM-YZEKDTGTSA-N 0.000 claims description 15
229920000768 polyamine Polymers 0.000 claims description 11
229960001608 teicoplanin Drugs 0.000 claims description 11
108010053950 Teicoplanin Proteins 0.000 claims description 10
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
125000002252 acyl group Chemical group 0.000 claims description 9
125000003074 decanoyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C(*)=O 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
241000295644 Staphylococcaceae Species 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([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 claims description 3
125000001402 nonanoyl group Chemical group O=C([*])C([H])([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 claims description 3
239000002798 polar solvent Substances 0.000 claims description 3
CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 2
CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims description 2
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 2
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 2
238000011938 amidation process Methods 0.000 claims description 2
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
208000015181 infectious disease Diseases 0.000 claims description 2
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
125000004193 piperazinyl group Chemical group 0.000 claims 1
150000001408 amides Chemical class 0.000 abstract description 7
239000003153 chemical reaction reagent Substances 0.000 abstract description 7
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract description 5
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 abstract description 4
125000003277 amino group Chemical group 0.000 abstract description 4
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125000005842 heteroatom Chemical group 0.000 abstract description 3
239000000203 mixture Substances 0.000 description 30
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
238000006243 chemical reaction Methods 0.000 description 21
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000002904 solvent Substances 0.000 description 12
125000001931 aliphatic group Chemical group 0.000 description 10
239000002585 base Substances 0.000 description 9
241000193996 Streptococcus pyogenes Species 0.000 description 8
238000004128 high performance liquid chromatography Methods 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
238000009903 catalytic hydrogenation reaction Methods 0.000 description 7
239000007795 chemical reaction product Substances 0.000 description 7
239000012458 free base Substances 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
230000000694 effects Effects 0.000 description 6
LCTCUBQFWLTHNS-MDZDMXLPSA-N 61036-64-4 Chemical compound CCCCC\C=C\CCC(=O)NC1C(O)C(O)C(CO)OC1OC(C(=C1)OC=2C(=CC(=CC=2)C(OC2C(C(O)C(O)C(CO)O2)NC(C)=O)C2C(NC(C3=CC(O)=CC(OC4C(C(O)C(O)C(CO)O4)O)=C3C=3C(O)=CC=C(C=3)C(NC3=O)C(=O)N2)C(=O)OC)=O)Cl)=C(OC=2C(=CC(=CC=2)C(O)C(C(N2)=O)NC(=O)C(N)C=4C=C(O5)C(O)=CC=4)Cl)C=C1C3NC(=O)C2C1=CC(O)=C(C)C5=C1 LCTCUBQFWLTHNS-MDZDMXLPSA-N 0.000 description 5
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
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KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 5
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WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
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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
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
239000005639 Lauric acid Substances 0.000 description 1
101100107522 Mus musculus Slc1a5 gene Proteins 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
229920005654 Sephadex Polymers 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
241000191963 Staphylococcus epidermidis Species 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
238000002814 agar dilution Methods 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
150000005215 alkyl ethers Chemical class 0.000 description 1
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230000002862 amidating effect Effects 0.000 description 1
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230000000844 anti-bacterial effect Effects 0.000 description 1
238000011482 antibacterial activity assay Methods 0.000 description 1
239000008365 aqueous carrier Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
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SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
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239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
235000019416 cholic acid Nutrition 0.000 description 1
229960002471 cholic acid Drugs 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000003245 coal Substances 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
230000001332 colony forming effect Effects 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
238000010612 desalination reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
206010014665 endocarditis Diseases 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
125000004404 heteroalkyl group Chemical group 0.000 description 1
PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229940033355 lauric acid Drugs 0.000 description 1
239000006193 liquid solution Substances 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
201000008383 nephritis Diseases 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
150000008039 phosphoramides Chemical class 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011148 porous material Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000012958 reprocessing Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
201000003068 rheumatic fever Diseases 0.000 description 1
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960004274 stearic acid Drugs 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
229950002929 trinitrophenol Drugs 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/006—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure
- C07K9/008—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure directly attached to a hetero atom of the saccharide radical, e.g. actaplanin, avoparcin, ristomycin, vancomycin
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Genetics & Genomics (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Oncology (AREA)
Public Health (AREA)
Communicable Diseases (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Cephalosporin Compounds (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Electric Stoves And Ranges (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

DK640489A 1988-12-27 1989-12-18 C63-Amidderivater af 34-de-(acetylglucosaminyl)-34-deoxy-teicoplaniner, fremgangsmåde til fremstilling heraf, anvendelse af sådanne forbindelser til fremstilling af medikamenter samt farmaceutiske præparater indeholdende forbindelserne DK171404B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP88121708		1988-12-27
EP88121708		1988-12-27

Publications (3)

Publication Number	Publication Date
DK640489D0 DK640489D0 (da)	1989-12-18
DK640489A DK640489A (da)	1990-06-28
DK171404B1 true DK171404B1 (da)	1996-10-14

Family

ID=8199722

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK640489A DK171404B1 (da)	1988-12-27	1989-12-18	C63-Amidderivater af 34-de-(acetylglucosaminyl)-34-deoxy-teicoplaniner, fremgangsmåde til fremstilling heraf, anvendelse af sådanne forbindelser til fremstilling af medikamenter samt farmaceutiske præparater indeholdende forbindelserne

Country Status (19)

Country	Link
EP (1)	EP0376041B1 (de)
JP (1)	JPH02221298A (de)
CN (1)	CN1043941A (de)
AT (1)	ATE134646T1 (de)
AU (1)	AU629883B2 (de)
CA (1)	CA2006379A1 (de)
DE (1)	DE68925806T2 (de)
DK (1)	DK171404B1 (de)
ES (1)	ES2083374T3 (de)
FI (1)	FI91076C (de)
GR (1)	GR3020070T3 (de)
HU (1)	HU209939B (de)
IE (1)	IE71942B1 (de)
IL (1)	IL92827A (de)
NO (1)	NO178664C (de)
NZ (1)	NZ231863A (de)
PT (1)	PT92672B (de)
RU (1)	RU2068418C1 (de)
ZA (1)	ZA899772B (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU647122B2 (en) *	1990-05-28	1994-03-17	Gruppo Lepetit S.P.A.	C63-amide derivatives of 34-de(acetylglucosaminyl)-34-deoxy- teicoplanin and their use as medicaments against bacteria resistant to glycopeptide antibiotics
US5606036A (en) *	1991-03-27	1997-02-25	Gruppo Lepetit Spa	Antibiotic A 40926 ester derivatives
CZ285703B6 (cs) *	1991-07-29	1999-10-13	Biosearch Italia S. P. A.	Amidové deriváty antibiotika A 40926
US5750509A (en) *	1991-07-29	1998-05-12	Gruppo Lepetit S.P.A.	Amide derivatives of antibiotic A 40926
SG87877A1 (en) *	1998-12-23	2002-04-16	Advanced Medicine Inc	Glycopeptide derivatives and pharmaceutical compositions containing the same
US6392012B1 (en)	1998-12-23	2002-05-21	Advanced Medicine, Inc.	Glycopeptide derivatives and pharmaceutical compositions containing the same
TWI312785B (en)	2001-08-24	2009-08-01	Theravance Inc	Process for preparing vancomycin derivatives
TWI275594B (en)	2001-08-24	2007-03-11	Theravance Inc	Process for preparing vancomycin phosphonate derivatives
AU2003294262B2 (en)	2002-11-18	2007-08-23	Vicuron Pharmaceuticals Inc.	Methods of administering dalbavancin for treatment of bacterial infections
RU2333766C2 (ru) *	2002-11-18	2008-09-20	Вайкьюрон Фармасьютикалз Инк.	Способы введения далбаванцина для лечения бактериальных инфекций
US7119061B2 (en)	2002-11-18	2006-10-10	Vicuron Pharmaceuticals, Inc.	Dalbavancin compositions for treatment of bacterial infections
US20060074014A1 (en)	2002-11-18	2006-04-06	Vicuron Pharmaceuticals Inc.	Dalbavancin compositions for treatment of bacterial infections

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8522574D0 (en) *	1985-09-12	1985-10-16	Lepetit Spa	Amides of teicoplanin compounds
GB8529272D0 (en) *	1985-11-28	1986-01-02	Lepetit Spa	Teicoplanin derivatives
GB8704847D0 (en) *	1987-03-02	1987-04-08	Lepetit Spa	Substituted alkylamides of teicoplanin compounds
GB8711066D0 (en) *	1987-05-11	1987-06-17	Lepetit Spa	Teicoplanin derivatives
GB8827202D0 (en) *	1988-11-22	1988-12-29	Lepetit Spa	Process for preparing 63-carboxyamides of teicoplanin antibiotics

1989
- 1989-12-12 AT AT89122874T patent/ATE134646T1/de not_active IP Right Cessation
- 1989-12-12 EP EP89122874A patent/EP0376041B1/de not_active Expired - Lifetime
- 1989-12-12 ES ES89122874T patent/ES2083374T3/es not_active Expired - Lifetime
- 1989-12-12 DE DE68925806T patent/DE68925806T2/de not_active Expired - Fee Related
- 1989-12-18 DK DK640489A patent/DK171404B1/da not_active IP Right Cessation
- 1989-12-19 AU AU46984/89A patent/AU629883B2/en not_active Ceased
- 1989-12-19 NO NO895123A patent/NO178664C/no unknown
- 1989-12-19 NZ NZ231863A patent/NZ231863A/en unknown
- 1989-12-20 IL IL9282789A patent/IL92827A/en not_active IP Right Cessation
- 1989-12-20 ZA ZA899772A patent/ZA899772B/xx unknown
- 1989-12-21 CA CA002006379A patent/CA2006379A1/en not_active Abandoned
- 1989-12-21 PT PT92672A patent/PT92672B/pt not_active IP Right Cessation
- 1989-12-21 IE IE414389A patent/IE71942B1/en not_active IP Right Cessation
- 1989-12-22 FI FI896199A patent/FI91076C/fi not_active IP Right Cessation
- 1989-12-22 HU HU896772A patent/HU209939B/hu not_active IP Right Cessation
- 1989-12-26 RU SU894742809A patent/RU2068418C1/ru active
- 1989-12-27 CN CN89109576A patent/CN1043941A/zh active Pending
- 1989-12-27 JP JP1336811A patent/JPH02221298A/ja active Pending
1996
- 1996-05-27 GR GR960401434T patent/GR3020070T3/el unknown

Also Published As

Publication number	Publication date
CA2006379A1 (en)	1990-06-27
ES2083374T3 (es)	1996-04-16
EP0376041A2 (de)	1990-07-04
DE68925806D1 (de)	1996-04-04
AU629883B2 (en)	1992-10-15
NO178664B (no)	1996-01-29
IL92827A (en)	1994-08-26
FI896199A0 (fi)	1989-12-22
DE68925806T2 (de)	1996-09-26
HU896772D0 (en)	1990-03-28
EP0376041B1 (de)	1996-02-28
IE894143L (en)	1990-06-27
NO178664C (no)	1996-05-08
CN1043941A (zh)	1990-07-18
NO895123L (no)	1990-06-28
HU209939B (en)	1994-12-28
PT92672B (pt)	1996-09-30
ATE134646T1 (de)	1996-03-15
EP0376041A3 (de)	1991-11-13
GR3020070T3 (en)	1996-08-31
HUT53376A (en)	1990-10-28
IE71942B1 (en)	1997-03-12
DK640489A (da)	1990-06-28
FI91076C (fi)	1994-05-10
IL92827A0 (en)	1990-09-17
PT92672A (pt)	1990-06-29
FI91076B (fi)	1994-01-31
NO895123D0 (no)	1989-12-19
DK640489D0 (da)	1989-12-18
RU2068418C1 (ru)	1996-10-27
JPH02221298A (ja)	1990-09-04
AU4698489A (en)	1990-07-05
NZ231863A (en)	1992-08-26
ZA899772B (en)	1991-01-30

Legal Events

Date	Code	Title	Description
1996-10-14	B1	Patent granted (law 1993)
1999-08-23	PBP	Patent lapsed

Publication	Publication Date	Title
Funabashi et al.	1993	A new anti-MRSA dipeptide, TAN-1057 A
IE920005A1 (en)	1992-07-15	Amides of antibiotic ge 2270 factors
CA2742753A1 (en)	2010-05-27	Lantibiotic carboxyamide derivatives with enhanced antibacterial activity
CA2337923A1 (en)	2001-08-25	Peptide antibiotics
HU205146B (en)	1992-03-30	Process for producing teicoplanine amide derivatives and pharmaceutical compositions comprising same
JPH06509347A (ja)	1994-10-20	抗生物質ａ４０９２６のアミド誘導体類
KR960014104B1 (ko)	1996-10-14	테이코플라닌 화합물의 치환 알킬아미드
KR20190093600A (ko)	2019-08-09	항균 펩타이드
EP0376041B1 (de)	1996-02-28	C63-Amidderivate von 34-de(acetylglucosaminyl)-34-deoxy-teicoplaninen
JPS61502335A (ja)	1986-10-16	デグルコテイコプラニンのカルボン酸エステル誘導体
HU217074B (hu)	1999-11-29	Eljárás teikoplanin szubsztituált alkil-amid-származékai és ezeket tartalmazó gyógyszerkészítmények előállítására
WO1997030078A1 (en)	1997-08-21	DERIVATIVES OF ANTIBIOTIC GE2270 FACTORS C2a, D2 AND E
JPH0570495A (ja)	1993-03-23	環式ヘキサペプチド化合物
EP0460448B1 (de)	1995-10-04	Verwendung von C63-Amidderivaten von 34-de(Acetylglucosaminyl)-34-deoxy-teicoplanin gegen Glykopeptid-Antibiotika resistente Bakterien
US5438117A (en)	1995-08-01	Hexapeptides deriving from aglucoteicoplanin and a process for preparing them
US5674840A (en)	1997-10-07	Synthetic aglucodalbaheptide antibiotics
EP2925342A1 (de)	2015-10-07	Neue lantibiotische derivate und verfahren zu deren herstellung
JPS6228154B2 (de)	1987-06-18
EP0563062B1 (de)	1996-01-10	Hexapeptidderivate von teicoplanin und verfahren zu deren herstellung
EP0050856A2 (de)	1982-05-05	Neues Peptid, Verfahren zu dessen Herstellung und pharmazeutische Zusammensetzung