HRP20161370T1 - Postupak za pripremanje eritromicin tiocijanata - Google Patents
Postupak za pripremanje eritromicin tiocijanata Download PDFInfo
- Publication number
- HRP20161370T1 HRP20161370T1 HRP20161370TT HRP20161370T HRP20161370T1 HR P20161370 T1 HRP20161370 T1 HR P20161370T1 HR P20161370T T HRP20161370T T HR P20161370TT HR P20161370 T HRP20161370 T HR P20161370T HR P20161370 T1 HRP20161370 T1 HR P20161370T1
- Authority
- HR
- Croatia
- Prior art keywords
- erythromycin
- thiocyanate
- solvent
- combination
- solution
- Prior art date
Links
- PGNYNCTUBKSHHL-UHFFFAOYSA-N 2,3-diaminobutanedioic acid Chemical compound OC(=O)C(N)C(N)C(O)=O PGNYNCTUBKSHHL-UHFFFAOYSA-N 0.000 title claims 6
- 238000002360 preparation method Methods 0.000 title 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 claims 13
- 238000000034 method Methods 0.000 claims 10
- 239000002904 solvent Substances 0.000 claims 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 7
- 229960003276 erythromycin Drugs 0.000 claims 4
- 150000003567 thiocyanates Chemical class 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 claims 2
- 150000002576 ketones Chemical class 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 239000011877 solvent mixture Substances 0.000 claims 2
- KKCMGMIPHDNPQL-YZPBMOCRSA-N (3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione;2-hyd Chemical compound CC(O)C(O)=O.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 KKCMGMIPHDNPQL-YZPBMOCRSA-N 0.000 claims 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 235000011114 ammonium hydroxide Nutrition 0.000 claims 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- 239000012535 impurity Substances 0.000 claims 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 1
- 229940011051 isopropyl acetate Drugs 0.000 claims 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 239000011736 potassium bicarbonate Substances 0.000 claims 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims 1
- 235000015497 potassium bicarbonate Nutrition 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 235000011181 potassium carbonates Nutrition 0.000 claims 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims 1
- 235000011118 potassium hydroxide Nutrition 0.000 claims 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 claims 1
- 229940116357 potassium thiocyanate Drugs 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 235000017550 sodium carbonate Nutrition 0.000 claims 1
- 235000011121 sodium hydroxide Nutrition 0.000 claims 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical group [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
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)
Claims (11)
1. Postupak za pripremanje eritromicin tiocijanata, naznačen time da sadrži:
a) otapanje eritromicina ili soli eritromicina ili njihove smjese u acetonu ili smjesi otapala koja sadrži aceton pod alkalnim uvjetima da nastane otopina eritromicina ili sol eritromicina;
b) dodavanje soli tiocijanata u otopinu; i
c) podešavanje pH otopine na od 6.0 do 8.0; te
d) nastajanje kristala eritromicin tiocijanata.
2. Postupak prema zahtjevu 1, naznačen time da sol eritromicina je eritromicin tiocijanat ili eritromicin laktat.
3. Postupak prema zahtjevu 1 ili 2, naznačen time da alkalni uvjeti su uvjeti kod pH otopine od 7.5 do 11.0, ili od 8.5 do 10.0, ili od 9.0 do 9.5.
4. Postupak prema zahtjevu 3, naznačen time da se za podešavanje pH u koraku a) koriste natrijev hidroksid, kalijev hidroksid, amonijev hidroksid, natrijev karbonat, kalijev karbonat, natrijev bikarbonat, kalijev bikarbonat ili njihova kombinacija.
5. Postupak prema bilo kojem od zahtjeva 1-4, naznačen time da je količina eritromicina ili soli eritromicina u koraku a) od 5% do 35%, ili od 10% do 30%, ili od 10% do 25%.
6. Postupak prema bilo kojem od zahtjeva 1-5, naznačen time da je udio acetona u smjesi otapala veći od 40%, ili veći od 50%, ili veći od 60%, ili veći od 70%, ili veći od 80%, ili veći od 90% po volumenu; pri čemu drugo otapalo je alkoholno otapalo, etersko otapalo, halogenirano otapalo, estersko otapalo, ketonsko otapalo osim acetona, voda ili njihova kombinacija; pri čemu alkoholno otapalo je C1-C6 alkohol; etersko otapalo je tetrahidrofuran, dietil eter, dioksan, metil tert-butil eter, dimetoksietan, dietilen glikol dimetil eter, trietilen glikol dimetil eter ili njihova kombinacija; halogenirano otapalo je diklormetan, 1,2-dikloretan, kloroform ili njihova kombinacija; estersko otapalo je etil acetat, izopropil acetat, butil acetate ili njihova kombinacija; i ketonsko otapalo je butanon.
7. Postupak prema bilo kojem od zahtjeva 1-6, naznačen time da sol tiocijanata je natrijev tiocijanat, kalijev tiocijanat, amonijev tiocijanat ili njihova kombinacija, je molarni omjer soli tiocijanata i eritromicina ili soli eritromicina je od 0.1:1 do 5:1, ili od 0.1:1 do 3:1, ili od 0.2:1 do 2:1.
8. Postupak prema bilo kojem od zahtjeva 1-7, naznačen time da se pH otopine u koraku c) podešava na od 6.0 do 7.5, ili od 7.0 do 7.5 sa slabom kiselinom, te pri čemu slaba kiselina je anorganska kiselina, organska kiselina ili njihova kombinacija, ili slaba kiselina je razrijeđena octena kiselina, razrijeđena solna kiselina, razrijeđena sumporna kiselina, razrijeđena fosforna kiselina, razrijeđena dušična kiselina ili njihova kombinacija.
9. Postupak prema bilo kojem od zahtjeva 1-8, naznačen time da se temperatura postupno smanjuje, te pri čemu se otopina u koraku a) i koraku b) drži na temperaturi od 35 °C do 50 °C, ili od 40 °C do 50 °C, ili od 40 °C do 45 °C; i pri čemu temperatura otopine u koraku c se smanjuje na od 0 °C do 10 °C, ili od 0 °C do 5 °C.
10. Postupak prema bilo kojem od zahtjeva 1-9, naznačen time da se otopina prije dodavanja tiocijanatne soli filtrira radi uklanjanja netopljivih krutih nečistoća.
11. Postupak prema bilo kojem od zahtjeva 1-9, naznačen time da je sadržaj eritromicin tiocijanata A je veći od 79%, u odnosu na ukupnu težinu eritromicin tiocijanata.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201110248968 | 2011-08-26 | ||
| PCT/CN2012/080554 WO2013029497A1 (zh) | 2011-08-26 | 2012-08-24 | 一种硫氰酸红霉素的制备方法 |
| EP12827355.4A EP2749564B1 (en) | 2011-08-26 | 2012-08-24 | Preparation process of erythromycin thiocyanate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20161370T1 true HRP20161370T1 (hr) | 2016-12-02 |
Family
ID=47755317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20161370TT HRP20161370T1 (hr) | 2011-08-26 | 2016-10-19 | Postupak za pripremanje eritromicin tiocijanata |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9409940B2 (hr) |
| EP (1) | EP2749564B1 (hr) |
| CN (1) | CN103764664B (hr) |
| ES (1) | ES2602171T3 (hr) |
| HR (1) | HRP20161370T1 (hr) |
| PL (1) | PL2749564T3 (hr) |
| SI (1) | SI2749564T1 (hr) |
| WO (1) | WO2013029497A1 (hr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105601687B (zh) * | 2016-03-28 | 2019-05-24 | 四川新迪医药化工有限公司 | 一种硫氰酸红霉素的精制方法 |
| CN109912671B (zh) * | 2019-04-12 | 2022-04-26 | 宁夏泰益欣生物科技有限公司 | 一种利用阿维菌素结晶母液提取阿维菌素B2a的方法 |
| CN110003295B (zh) * | 2019-04-29 | 2020-05-12 | 宜昌东阳光药业股份有限公司 | 一种硫氰酸红霉素的制备方法 |
| CN113201038B (zh) * | 2021-04-13 | 2022-07-26 | 宜昌东阳光生化制药有限公司 | 一种降低硫氰酸红霉素溶剂残留的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2791531A (en) * | 1953-10-22 | 1957-05-07 | Lilly Co Eli | Erythromycin thiocyanate and compositions containing same |
| GB1013837A (en) | 1962-12-07 | 1965-12-22 | Pierrel Spa | Erythromycin salts and esters |
| FR1367842A (fr) * | 1963-07-24 | 1964-07-24 | Pierrel Spa | Procédé de fabrication d'un nouveau sel d'érythromycine soluble dans l'eau |
| CN1099039A (zh) * | 1994-05-17 | 1995-02-22 | 陕西省六星科工贸有限公司 | 一种提取红霉素碱的生产工艺 |
| CN101624412B (zh) | 2008-07-10 | 2012-07-04 | 刘力 | 大环内酯类衍生物及其制备和用途 |
| CN101407533B (zh) | 2008-11-28 | 2011-06-08 | 宁夏启元药业有限公司 | 一种红霉素硫氰酸盐的生产方法 |
-
2012
- 2012-08-24 SI SI201230739A patent/SI2749564T1/sl unknown
- 2012-08-24 ES ES12827355.4T patent/ES2602171T3/es active Active
- 2012-08-24 EP EP12827355.4A patent/EP2749564B1/en active Active
- 2012-08-24 WO PCT/CN2012/080554 patent/WO2013029497A1/zh active Application Filing
- 2012-08-24 US US14/240,031 patent/US9409940B2/en active Active
- 2012-08-24 CN CN201280035956.4A patent/CN103764664B/zh active Active
- 2012-08-24 PL PL12827355T patent/PL2749564T3/pl unknown
-
2016
- 2016-10-19 HR HRP20161370TT patent/HRP20161370T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2602171T3 (es) | 2017-02-17 |
| PL2749564T3 (pl) | 2017-07-31 |
| US20140228555A1 (en) | 2014-08-14 |
| EP2749564B1 (en) | 2016-10-12 |
| SI2749564T1 (sl) | 2016-11-30 |
| CN103764664A (zh) | 2014-04-30 |
| WO2013029497A1 (zh) | 2013-03-07 |
| US9409940B2 (en) | 2016-08-09 |
| EP2749564A1 (en) | 2014-07-02 |
| CN103764664B (zh) | 2016-03-02 |
| EP2749564A4 (en) | 2015-01-14 |
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