GB1334964A - Process for the demethylation of 3-amino macrolides - Google Patents
Process for the demethylation of 3-amino macrolidesInfo
- Publication number
- GB1334964A GB1334964A GB4590571A GB4590571A GB1334964A GB 1334964 A GB1334964 A GB 1334964A GB 4590571 A GB4590571 A GB 4590571A GB 4590571 A GB4590571 A GB 4590571A GB 1334964 A GB1334964 A GB 1334964A
- Authority
- GB
- United Kingdom
- Prior art keywords
- solvent
- macrolide
- sodium
- bromine
- iodine
- 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
- 239000003120 macrolide antibiotic agent Substances 0.000 title abstract 4
- 230000017858 demethylation Effects 0.000 title 1
- 238000010520 demethylation reaction Methods 0.000 title 1
- 229940041033 macrolides Drugs 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- -1 griseomycin Chemical compound 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- 229910052740 iodine Inorganic materials 0.000 abstract 2
- 239000011630 iodine Substances 0.000 abstract 2
- HUKYPYXOBINMND-UHFFFAOYSA-N methymycin Natural products CC1CC(C)C(=O)C=CC(O)(C)C(CC)OC(=O)C(C)C1OC1C(O)C(N(C)C)CC(C)O1 HUKYPYXOBINMND-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- ACTOXUHEUCPTEW-BWHGAVFKSA-N 2-[(4r,5s,6s,7r,9r,10r,11e,13e,16r)-6-[(2s,3r,4r,5s,6r)-5-[(2s,4r,5s,6s)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[(2s,5s,6r)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-o Chemical compound O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@@H](O)[C@@H]([C@H]([C@@H](CC=O)C[C@H]1C)O[C@H]1[C@@H]([C@H]([C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1)N(C)C)O)OC)[C@@H]1CC[C@H](N(C)C)[C@@H](C)O1 ACTOXUHEUCPTEW-BWHGAVFKSA-N 0.000 abstract 1
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 abstract 1
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 abstract 1
- UKXFZNMZXWBSGH-UHFFFAOYSA-N Carbomycin A Natural products COC1C(OC2OC(C)C(OC3CC(C)(O)C(OC(=O)CC(C)C)C(C)O3)C(C2O)N(C)C)C(CC=O)CC(C)C(=O)C=CC4OC4CC(C)OC(=O)CC1C(=O)C UKXFZNMZXWBSGH-UHFFFAOYSA-N 0.000 abstract 1
- ZRNXEMIDBIPJDC-UHFFFAOYSA-N Carbomycin B Natural products COC1C(OC(C)=O)CC(=O)OC(C)CC=CC=CC(=O)C(C)CC(CC=O)C1OC1C(O)C(N(C)C)C(OC2OC(C)C(OC(=O)CC(C)C)C(C)(O)C2)C(C)O1 ZRNXEMIDBIPJDC-UHFFFAOYSA-N 0.000 abstract 1
- ZOYWWAGVGBSJDL-UHFFFAOYSA-N D-desosamine Natural products CC1CC(N(C)C)C(O)C(O)O1 ZOYWWAGVGBSJDL-UHFFFAOYSA-N 0.000 abstract 1
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 abstract 1
- 229930006677 Erythromycin A Natural products 0.000 abstract 1
- IDRYSCOQVVUBIJ-UHFFFAOYSA-N Erythromycin-B Natural products CC1C(OC2C(C(CC(C)O2)N(C)C)O)C(C)(O)CC(C)C(=O)C(C)C(O)C(C)C(CC)OC(=O)C(C)C1OC1CC(C)(OC)C(O)C(C)O1 IDRYSCOQVVUBIJ-UHFFFAOYSA-N 0.000 abstract 1
- MWFRKHPRXPSWNT-UHFFFAOYSA-N Erythromycin-C Natural products CC1C(OC2C(C(CC(C)O2)N(C)C)O)C(C)(O)CC(C)C(=O)C(C)C(O)C(O)(C)C(CC)OC(=O)C(C)C1OC1CC(C)(O)C(O)C(C)O1 MWFRKHPRXPSWNT-UHFFFAOYSA-N 0.000 abstract 1
- IEMDOFXTVAPVLX-YWQHLDGFSA-N Leucomycin A1 Chemical compound CO[C@H]1[C@H](O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@@H](C)O1 IEMDOFXTVAPVLX-YWQHLDGFSA-N 0.000 abstract 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 abstract 1
- UEIVQYHYALXCBD-UHFFFAOYSA-N Neomethymycin Natural products CC1CC(C)C(=O)C=CC(C)C(C(O)C)OC(=O)C(C)C1OC1C(O)C(N(C)C)CC(C)O1 UEIVQYHYALXCBD-UHFFFAOYSA-N 0.000 abstract 1
- 239000004104 Oleandomycin Substances 0.000 abstract 1
- RZPAKFUAFGMUPI-UHFFFAOYSA-N Oleandomycin Natural products O1C(C)C(O)C(OC)CC1OC1C(C)C(=O)OC(C)C(C)C(O)C(C)C(=O)C2(OC2)CC(C)C(OC2C(C(CC(C)O2)N(C)C)O)C1C RZPAKFUAFGMUPI-UHFFFAOYSA-N 0.000 abstract 1
- UZQBOFAUUTZOQE-UHFFFAOYSA-N Pikromycin Natural products CC1CC(C)C(=O)C=CC(O)(C)C(CC)OC(=O)C(C)C(=O)C(C)C1OC1C(O)C(N(C)C)CC(C)O1 UZQBOFAUUTZOQE-UHFFFAOYSA-N 0.000 abstract 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 abstract 1
- ZPCCSZFPOXBNDL-LWXQEXJOSA-N Spiramycin-II Natural products CO[C@H]1[C@@H](CC(=O)O[C@H](C)CC=CC=C[C@H](O[C@H]2CC[C@@H]([C@@H](C)O2)N(C)C)[C@H](C)C[C@@H](CC=O)[C@@H]1O[C@@H]3O[C@H](C)[C@@H](O[C@H]4C[C@@](C)(O)[C@@H](O)[C@H](C)O4)[C@@H]([C@H]3O)N(C)C)OC(=O)C ZPCCSZFPOXBNDL-LWXQEXJOSA-N 0.000 abstract 1
- HSZLKTCKAYXVBX-VPIGJTHDSA-N Spiramycin-III Natural products CCC(=O)O[C@@H]1CC(=O)O[C@H](C)CC=CC=C[C@H](O[C@H]2CC[C@@H]([C@@H](C)O2)N(C)C)[C@H](C)C[C@H](CC=O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O[C@H]4C[C@@](C)(O)[C@@H](O)[C@H](C)O4)[C@@H]([C@H]3O)N(C)C)[C@H]1OC HSZLKTCKAYXVBX-VPIGJTHDSA-N 0.000 abstract 1
- FQVHOULQCKDUCY-OGHXVOSASA-N [(2s,3s,4r,6s)-6-[(2r,3s,4r,5r,6s)-6-[[(1s,3r,7r,8s,9s,10r,12r,14e,16s)-7-acetyloxy-8-methoxy-3,12-dimethyl-5,13-dioxo-10-(2-oxoethyl)-4,17-dioxabicyclo[14.1.0]heptadec-14-en-9-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimeth Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@H]1[C@@H](CC=O)C[C@@H](C)C(=O)/C=C/[C@@H]2O[C@H]2C[C@@H](C)OC(=O)C[C@H]([C@@H]1OC)OC(C)=O)[C@H]1C[C@@](C)(O)[C@@H](OC(=O)CC(C)C)[C@H](C)O1 FQVHOULQCKDUCY-OGHXVOSASA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 239000003125 aqueous solvent Substances 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- DDQFXRYVNIPXRQ-UHFFFAOYSA-L cyclopenta-1,3-diene;dichlorozirconium(2+);1,2,3,5,5-pentamethylcyclopenta-1,3-diene Chemical compound Cl[Zr+2]Cl.C1C=CC=[C-]1.CC1=[C-]C(C)(C)C(C)=C1C DDQFXRYVNIPXRQ-UHFFFAOYSA-L 0.000 abstract 1
- VTJCSBJRQLZNHE-CSMHCCOUSA-N desosamine Chemical compound C[C@@H](O)C[C@H](N(C)C)[C@@H](O)C=O VTJCSBJRQLZNHE-CSMHCCOUSA-N 0.000 abstract 1
- 229960003276 erythromycin Drugs 0.000 abstract 1
- IDRYSCOQVVUBIJ-PPGFLMPOSA-N erythromycin B Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@H]([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)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 IDRYSCOQVVUBIJ-PPGFLMPOSA-N 0.000 abstract 1
- MWFRKHPRXPSWNT-QNPWSHAKSA-N erythromycin C Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 MWFRKHPRXPSWNT-QNPWSHAKSA-N 0.000 abstract 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 abstract 1
- HUKYPYXOBINMND-HYUJHOPRSA-N methymycin Chemical compound C[C@H]1C[C@@H](C)C(=O)\C=C\[C@@](O)(C)[C@@H](CC)OC(=O)[C@H](C)[C@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)C[C@@H](C)O1 HUKYPYXOBINMND-HYUJHOPRSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- IJUPCLYLISRDRA-ULAWRXDQSA-N mycaminose Chemical group C[C@@H](O)[C@@H](O)[C@H](N(C)C)[C@@H](O)C=O IJUPCLYLISRDRA-ULAWRXDQSA-N 0.000 abstract 1
- OXFYAOOMMKGGAI-JLTOUBQASA-N narbomycin Chemical compound C[C@H]1C[C@@H](C)C(=O)\C=C\[C@@H](C)[C@@H](CC)OC(=O)[C@H](C)C(=O)[C@H](C)[C@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)C[C@@H](C)O1 OXFYAOOMMKGGAI-JLTOUBQASA-N 0.000 abstract 1
- OXFYAOOMMKGGAI-UHFFFAOYSA-N narbomycin Natural products CC1CC(C)C(=O)C=CC(C)C(CC)OC(=O)C(C)C(=O)C(C)C1OC1C(O)C(N(C)C)CC(C)O1 OXFYAOOMMKGGAI-UHFFFAOYSA-N 0.000 abstract 1
- UEIVQYHYALXCBD-OTUJEKPESA-N neomethymycin Chemical compound C[C@H]1C[C@@H](C)C(=O)\C=C\[C@@H](C)[C@@H]([C@H](O)C)OC(=O)[C@H](C)[C@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)C[C@@H](C)O1 UEIVQYHYALXCBD-OTUJEKPESA-N 0.000 abstract 1
- RZPAKFUAFGMUPI-KGIGTXTPSA-N oleandomycin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]2(OC2)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C RZPAKFUAFGMUPI-KGIGTXTPSA-N 0.000 abstract 1
- 229960002351 oleandomycin Drugs 0.000 abstract 1
- 235000019367 oleandomycin Nutrition 0.000 abstract 1
- UZQBOFAUUTZOQE-VSLWXVDYSA-N pikromycin Chemical compound C[C@H]1C[C@@H](C)C(=O)\C=C\[C@@](O)(C)[C@@H](CC)OC(=O)[C@H](C)C(=O)[C@H](C)[C@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)C[C@@H](C)O1 UZQBOFAUUTZOQE-VSLWXVDYSA-N 0.000 abstract 1
- NFOMJDXALJABQF-DDNYSEEGSA-N plicacetin Chemical compound O([C@H]1CC[C@@H](O[C@@H]1C)N1C(N=C(NC(=O)C=2C=CC(N)=CC=2)C=C1)=O)[C@H]1O[C@H](C)[C@@H](N(C)C)[C@H](O)[C@H]1O NFOMJDXALJABQF-DDNYSEEGSA-N 0.000 abstract 1
- NFOMJDXALJABQF-UHFFFAOYSA-N plicacetin Natural products CC1OC(N2C(N=C(NC(=O)C=3C=CC(N)=CC=3)C=C2)=O)CCC1OC1OC(C)C(N(C)C)C(O)C1O NFOMJDXALJABQF-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000001632 sodium acetate Substances 0.000 abstract 1
- 235000017281 sodium acetate Nutrition 0.000 abstract 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 abstract 1
- 239000004299 sodium benzoate Substances 0.000 abstract 1
- 235000010234 sodium benzoate Nutrition 0.000 abstract 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 abstract 1
- 239000004324 sodium propionate Substances 0.000 abstract 1
- 235000010334 sodium propionate Nutrition 0.000 abstract 1
- 229960003212 sodium propionate Drugs 0.000 abstract 1
- ACTOXUHEUCPTEW-ZOTSFZJCSA-N spiramycin I Natural products CO[C@H]1[C@H](O)CC(=O)O[C@H](C)CC=CC=C[C@H](O[C@H]2CC[C@@H]([C@@H](C)O2)N(C)C)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]3O[C@H](C)[C@@H](O[C@H]4C[C@@](C)(O)[C@@H](O)[C@H](C)O4)[C@@H]([C@H]3O)N(C)C ACTOXUHEUCPTEW-ZOTSFZJCSA-N 0.000 abstract 1
- ZPCCSZFPOXBNDL-RSMXASMKSA-N spiramycin II Chemical compound O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@H]([C@@H]([C@H]([C@@H](CC=O)C[C@H]1C)O[C@H]1[C@@H]([C@H]([C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1)N(C)C)O)OC)OC(C)=O)[C@H]1CC[C@H](N(C)C)[C@H](C)O1 ZPCCSZFPOXBNDL-RSMXASMKSA-N 0.000 abstract 1
- 229950001955 spiramycin i Drugs 0.000 abstract 1
- 229950006796 spiramycin ii Drugs 0.000 abstract 1
- 229950003659 spiramycin iii Drugs 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8631470A | 1970-11-02 | 1970-11-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1334964A true GB1334964A (en) | 1973-10-24 |
Family
ID=22197754
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4590571A Expired GB1334964A (en) | 1970-11-02 | 1971-10-01 | Process for the demethylation of 3-amino macrolides |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3725385A (enExample) |
| CA (1) | CA960654A (enExample) |
| DE (1) | DE2154032C3 (enExample) |
| FR (1) | FR2113423A5 (enExample) |
| GB (1) | GB1334964A (enExample) |
| ZA (1) | ZA716324B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX3676E (es) * | 1975-07-15 | 1981-04-23 | Abbott Lab | Procedimiento para obtener derivados del antibiotico xk-62-2 |
| OA09249A (fr) * | 1988-12-19 | 1992-06-30 | Lilly Co Eli | Composés de macrolides. |
| DE4200145A1 (de) | 1992-01-07 | 1993-07-08 | Kali Chemie Pharma Gmbh | 7,10-epoxy-oxacyclododecan-derivate, verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US5591606A (en) * | 1992-11-06 | 1997-01-07 | Dowelanco | Process for the production of A83543 compounds with Saccharopolyspora spinosa |
| JP4258575B2 (ja) * | 1993-03-12 | 2009-04-30 | ダウ・アグロサイエンス・エル・エル・シー | 新規ａ８３５４３化合物及びそれらの製造法 |
| US6001981A (en) * | 1996-06-13 | 1999-12-14 | Dow Agrosciences Llc | Synthetic modification of Spinosyn compounds |
| DE19644195A1 (de) * | 1996-10-24 | 1998-04-30 | Solvay Pharm Gmbh | 10,13,15-Trioxatricyclo[9.2.1.1.·9·.·6·]-pentadecanon-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
| US5922849A (en) * | 1996-11-22 | 1999-07-13 | Abbott Laboratories | Process for preparation of N-demethyl-4"-deoxy-erthromycins A and B |
| US5883236A (en) * | 1997-11-19 | 1999-03-16 | Abbott Laboratories | Process for N-desmethylating erythromycins and derivatives thereof |
| US6084079A (en) * | 1998-05-15 | 2000-07-04 | Keyes; Robert F. | Process for preparing N-demethyl-N-alkyl erythromycin derivatives |
| JP4573925B2 (ja) * | 1998-07-09 | 2010-11-04 | アベンティス・ファーマ・ソシエテ・アノニム | 新規のエリスロマイシン誘導体、その製造方法及びその薬剤としての使用 |
| US7348309B2 (en) | 2001-03-30 | 2008-03-25 | Wisconsin Alumni Research Foundation | Glycorandomization and production of novel vancomycin analogs |
| ITMI20021726A1 (it) * | 2002-08-01 | 2004-02-02 | Zambon Spa | Macrolidi ad attivita' antiinfiammatoria. |
| EP1622922A2 (en) * | 2003-04-17 | 2006-02-08 | Sandoz AG | Derivatives of azithromycin |
| WO2005000233A2 (en) * | 2003-06-23 | 2005-01-06 | Auspex Pharmaceuticals | Novel therapeautic agents for the treatment of cancer, metabolic diseases and skin disorders |
| JP2009506066A (ja) | 2005-08-24 | 2009-02-12 | リブ−エックス ファーマシューティカルズ，インコーポレイテッド | トリアゾール化合物ならびにこれを作製する方法および使用する方法 |
| NZ568763A (en) * | 2005-12-08 | 2010-04-30 | Pfizer | Method for demethylating the 3'-dimethylamino group of erythromycin compounds |
| EP2023721A2 (en) * | 2006-06-05 | 2009-02-18 | Auspex Pharmaceuticals Inc. | Preparation and utility of substituted erythromycin analogs |
| EA017878B1 (ru) * | 2006-12-12 | 2013-03-29 | Замбон С.П.А. | Макролидные соединения, обладающие противовоспалительной активностью |
| WO2009006403A2 (en) * | 2007-06-29 | 2009-01-08 | Georgia Tech Research Corporation | Non-peptide macrocyclic histone deacetylase (hdac) inhibitors and methods of making and using thereof |
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| CN102378763A (zh) | 2009-01-30 | 2012-03-14 | 葛兰素集团有限公司 | 消炎的大环内酯 |
| JP2012516305A (ja) | 2009-01-30 | 2012-07-19 | グラクソ グループ リミテッド | 好中球優位の炎症性疾患の治療のための９−デオキソ−９ａ−メチル−９ａ−アザ−９ａ−ホモエリスロマイシンａ誘導体 |
| WO2011131749A1 (en) | 2010-04-23 | 2011-10-27 | Glaxo Group Limited | New 14 and 15 membered macrolides for the treatment of neutrophil dominated inflammatory diseases |
| GB201520419D0 (en) | 2015-11-19 | 2016-01-06 | Epi Endo Pharmaceuticals Ehf | Compounds |
| GB201608236D0 (en) | 2016-05-11 | 2016-06-22 | Fidelta D O O | Seco macrolide compounds |
| CN108727445B (zh) * | 2018-06-29 | 2021-06-11 | 宜昌东阳光生化制药有限公司 | 一种阿奇霉素杂质f的合成方法 |
| JP2026512285A (ja) | 2023-03-22 | 2026-04-15 | エピエンド ファーマシューティカルズ イーエッチエフ． | 好酸球関連疾患の治療における使用のためのアジスロマイシン誘導体 |
| GB202412461D0 (en) | 2024-08-23 | 2024-10-09 | Epiendo Pharmaceuticals Ehf | Medial use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2812323A (en) * | 1954-11-03 | 1957-11-05 | Lilly Co Eli | Des-n-methyl erythromycin |
| US3583972A (en) * | 1969-06-11 | 1971-06-08 | Upjohn Co | N-dealkylation of cyclic tertiary amines |
-
1970
- 1970-11-02 US US00086314A patent/US3725385A/en not_active Expired - Lifetime
-
1971
- 1971-09-20 CA CA123,226A patent/CA960654A/en not_active Expired
- 1971-09-21 ZA ZA716324A patent/ZA716324B/xx unknown
- 1971-10-01 GB GB4590571A patent/GB1334964A/en not_active Expired
- 1971-10-29 DE DE2154032A patent/DE2154032C3/de not_active Expired
- 1971-10-29 FR FR7139103A patent/FR2113423A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2113423A5 (enExample) | 1972-06-23 |
| CA960654A (en) | 1975-01-07 |
| DE2154032C3 (de) | 1980-01-03 |
| DE2154032A1 (de) | 1972-05-04 |
| US3725385A (en) | 1973-04-03 |
| AU3385571A (en) | 1973-03-29 |
| ZA716324B (en) | 1972-05-31 |
| DE2154032B2 (de) | 1979-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |