GB1298295A - Improvements in or relating to antibiotic derivatives and the preparation thereof - Google Patents
Improvements in or relating to antibiotic derivatives and the preparation thereofInfo
- Publication number
- GB1298295A GB1298295A GB2565571A GB2565571A GB1298295A GB 1298295 A GB1298295 A GB 1298295A GB 2565571 A GB2565571 A GB 2565571A GB 2565571 A GB2565571 A GB 2565571A GB 1298295 A GB1298295 A GB 1298295A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- acetyl
- deoxy
- compound
- thiolincosaminide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 230000003115 biocidal effect Effects 0.000 title 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 30
- 150000001875 compounds Chemical class 0.000 abstract 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 7
- FMCAFXHLMUOIGG-JTJHWIPRSA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-JTJHWIPRSA-N 0.000 abstract 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 4
- 238000000855 fermentation Methods 0.000 abstract 4
- 230000004151 fermentation Effects 0.000 abstract 4
- -1 2-(2-hydroxyphenylcarbonyloxy)ethylthio Chemical group 0.000 abstract 3
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 3
- 229960000583 acetic acid Drugs 0.000 abstract 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- DRTQHJPVMGBUCF-XVFCMESISA-N Uridine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-XVFCMESISA-N 0.000 abstract 2
- 239000002250 absorbent Substances 0.000 abstract 2
- 230000002745 absorbent Effects 0.000 abstract 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine group Chemical group [C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C=NC=2C(N)=NC=NC12 OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 abstract 2
- 239000003957 anion exchange resin Substances 0.000 abstract 2
- 239000012362 glacial acetic acid Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 2
- KOFBVFFPLADGGO-DUSUDKPKSA-N (3r,4s,5r,6r)-6-[(1r,2r)-1-amino-2-hydroxypropyl]oxane-2,3,4,5-tetrol Chemical compound C[C@@H](O)[C@@H](N)[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O KOFBVFFPLADGGO-DUSUDKPKSA-N 0.000 abstract 1
- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002126 C01EB10 - Adenosine Substances 0.000 abstract 1
- MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 abstract 1
- UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 abstract 1
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- OJMMVQQUTAEWLP-UHFFFAOYSA-N Lincomycin Natural products CN1CC(CCC)CC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 OJMMVQQUTAEWLP-UHFFFAOYSA-N 0.000 abstract 1
- 241000187747 Streptomyces Species 0.000 abstract 1
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 abstract 1
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 229960005305 adenosine Drugs 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- DRTQHJPVMGBUCF-PSQAKQOGSA-N beta-L-uridine Natural products O[C@H]1[C@@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-PSQAKQOGSA-N 0.000 abstract 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 239000012458 free base Substances 0.000 abstract 1
- 229940029575 guanosine Drugs 0.000 abstract 1
- 238000006698 hydrazinolysis reaction Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 239000012535 impurity Substances 0.000 abstract 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 abstract 1
- OJMMVQQUTAEWLP-KIDUDLJLSA-N lincomycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 OJMMVQQUTAEWLP-KIDUDLJLSA-N 0.000 abstract 1
- 229960005287 lincomycin Drugs 0.000 abstract 1
- 229960001595 lincomycin hydrochloride Drugs 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000002777 nucleoside Substances 0.000 abstract 1
- 150000003833 nucleoside derivatives Chemical class 0.000 abstract 1
- 239000002773 nucleotide Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 abstract 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 abstract 1
- 229940045145 uridine Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
- C07H15/16—Lincomycin; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Biotechnology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3025470A | 1970-04-20 | 1970-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1298295A true GB1298295A (en) | 1972-11-29 |
Family
ID=21853299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2565571A Expired GB1298295A (en) | 1970-04-20 | 1971-04-19 | Improvements in or relating to antibiotic derivatives and the preparation thereof |
Country Status (4)
| Country | Link |
|---|---|
| BE (1) | BE766008A (enrdf_load_stackoverflow) |
| DE (1) | DE2118636A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2092060B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1298295A (enrdf_load_stackoverflow) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005012320A3 (en) * | 2003-06-17 | 2005-10-20 | Vicuron Pharm Inc | Novel lincomycin derivatives possessing antimicrobial activity |
| US7164011B2 (en) | 2002-08-15 | 2007-01-16 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
| US7199106B2 (en) | 2003-06-17 | 2007-04-03 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antimicrobial activity |
| US7199105B2 (en) | 2002-08-15 | 2007-04-03 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
| US7256177B2 (en) | 2003-06-17 | 2007-08-14 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
| US7361743B2 (en) | 2004-02-11 | 2008-04-22 | Pfizer Inc | Lincomycin derivatives possessing antibacterial activity |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3544552A (en) * | 1968-10-18 | 1970-12-01 | Upjohn Co | 3-phosphate esters of lincomycin |
-
1971
- 1971-04-17 DE DE19712118636 patent/DE2118636A1/de active Pending
- 1971-04-19 FR FR7113813A patent/FR2092060B1/fr not_active Expired
- 1971-04-19 GB GB2565571A patent/GB1298295A/en not_active Expired
- 1971-04-20 BE BE766008A patent/BE766008A/xx unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7164011B2 (en) | 2002-08-15 | 2007-01-16 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
| US7199105B2 (en) | 2002-08-15 | 2007-04-03 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
| WO2005012320A3 (en) * | 2003-06-17 | 2005-10-20 | Vicuron Pharm Inc | Novel lincomycin derivatives possessing antimicrobial activity |
| US7199106B2 (en) | 2003-06-17 | 2007-04-03 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antimicrobial activity |
| JP2007516172A (ja) * | 2003-06-17 | 2007-06-21 | ビキュロン・ファーマシューティカルズ・インコーポレイテッド | 抗菌活性を有する新規リンコマイシン誘導体 |
| US7256177B2 (en) | 2003-06-17 | 2007-08-14 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
| US7361743B2 (en) | 2004-02-11 | 2008-04-22 | Pfizer Inc | Lincomycin derivatives possessing antibacterial activity |
Also Published As
| Publication number | Publication date |
|---|---|
| BE766008A (fr) | 1971-09-16 |
| FR2092060A1 (enrdf_load_stackoverflow) | 1972-01-21 |
| DE2118636A1 (de) | 1971-11-04 |
| FR2092060B1 (enrdf_load_stackoverflow) | 1974-10-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |