CA1025442A - Process for preparing new erythromycin salt - Google Patents
Process for preparing new erythromycin saltInfo
- Publication number
- CA1025442A CA1025442A CA230,434A CA230434A CA1025442A CA 1025442 A CA1025442 A CA 1025442A CA 230434 A CA230434 A CA 230434A CA 1025442 A CA1025442 A CA 1025442A
- Authority
- CA
- Canada
- Prior art keywords
- érythromycine
- pyroglutamate
- eau
- que
- procédé
- 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
- 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 title abstract description 8
- 238000004519 manufacturing process Methods 0.000 title 1
- 229940043131 pyroglutamate Drugs 0.000 claims abstract description 30
- ODHCTXKNWHHXJC-VKHMYHEASA-N 5-oxo-L-proline Chemical compound OC(=O)[C@@H]1CCC(=O)N1 ODHCTXKNWHHXJC-VKHMYHEASA-N 0.000 claims abstract description 29
- ODHCTXKNWHHXJC-UHFFFAOYSA-N acide pyroglutamique Natural products OC(=O)C1CCC(=O)N1 ODHCTXKNWHHXJC-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229960003276 erythromycin Drugs 0.000 abstract 2
- ODHCTXKNWHHXJC-GSVOUGTGSA-N Pyroglutamic acid Natural products OC(=O)[C@H]1CCC(=O)N1 ODHCTXKNWHHXJC-GSVOUGTGSA-N 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000003385 bacteriostatic effect Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- YKQOSKADJPQZHB-RGYSVOEGSA-N n-[(2s)-4-amino-1-[[(2s,3r)-1-[[(2s)-4-amino-1-oxo-1-[[(6r,9s,12r,15r,18s,21s)-6,9,18-tris(2-aminoethyl)-3-[(1r)-1-hydroxyethyl]-12,15-bis(2-methylpropyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclotricos-21-yl]amino]butan-2-yl]amino]-3-hydr Chemical compound CCC(C)CCCC(=O)N[C@@H](CCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCN)C(=O)N[C@H]1CCNC(=O)C([C@@H](C)O)NC(=O)[C@@H](CCN)NC(=O)[C@H](CCN)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@H](CCN)NC1=O YKQOSKADJPQZHB-RGYSVOEGSA-N 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000191940 Staphylococcus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 241001080024 Telles Species 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 101100421144 Danio rerio selenoo1 gene Proteins 0.000 description 1
- 241001644893 Entandrophragma utile Species 0.000 description 1
- 241000588697 Enterobacter cloacae Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 101100354203 Escherichia coli (strain K12) crr gene Proteins 0.000 description 1
- 241000588748 Klebsiella Species 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
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000219470 Mirabilis Species 0.000 description 1
- 101100001347 Mus musculus Akt1s1 gene Proteins 0.000 description 1
- 101100202896 Mus musculus Selenoo gene Proteins 0.000 description 1
- 102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 1
- 241000277263 Salmo Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940096118 ella Drugs 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 235000002020 sage Nutrition 0.000 description 1
- OOLLAFOLCSJHRE-ZHAKMVSLSA-N ulipristal acetate Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(OC(C)=O)C(C)=O)[C@]2(C)C1 OOLLAFOLCSJHRE-ZHAKMVSLSA-N 0.000 description 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D207/28—2-Pyrrolidone-5- carboxylic acids; Functional derivatives thereof, e.g. esters, nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7423013A FR2302084A1 (fr) | 1974-07-02 | 1974-07-02 | Nouveau sel d'erythromycine, son procede de preparation et son application a titre de medicament |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1025442A true CA1025442A (en) | 1978-01-31 |
Family
ID=9140790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA230,434A Expired CA1025442A (en) | 1974-07-02 | 1975-06-30 | Process for preparing new erythromycin salt |
Country Status (11)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5633353A (en) * | 1979-08-20 | 1981-04-03 | Toray Ind Inc | Reeling-out method for thread |
| DK0804088T3 (da) * | 1994-06-29 | 2000-11-20 | Meiji Seika Kaisha | Stabiliseret sammensætning, der omfatter solisinsulfat |
-
1974
- 1974-07-02 FR FR7423013A patent/FR2302084A1/fr active Granted
-
1975
- 1975-06-30 CA CA230,434A patent/CA1025442A/en not_active Expired
- 1975-06-30 LU LU72866A patent/LU72866A1/xx unknown
- 1975-06-30 BE BE157851A patent/BE830842A/xx not_active IP Right Cessation
- 1975-07-01 CH CH856875A patent/CH599152A5/xx not_active IP Right Cessation
- 1975-07-01 JP JP8055475A patent/JPS5129217A/ja active Pending
- 1975-07-02 DK DK299375A patent/DK299375A/da unknown
- 1975-07-02 IE IE147275A patent/IE41628B1/en unknown
- 1975-07-02 DE DE19752529538 patent/DE2529538A1/de not_active Ceased
- 1975-07-02 GB GB2780975A patent/GB1485210A/en not_active Expired
- 1975-07-02 NL NL7507863A patent/NL7507863A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| GB1485210A (en) | 1977-09-08 |
| BE830842A (fr) | 1975-12-30 |
| DK299375A (da) | 1976-01-03 |
| LU72866A1 (enrdf_load_stackoverflow) | 1976-04-13 |
| DE2529538A1 (de) | 1976-01-22 |
| IE41628B1 (en) | 1980-02-13 |
| FR2302084B1 (enrdf_load_stackoverflow) | 1979-05-18 |
| NL7507863A (nl) | 1976-01-06 |
| CH599152A5 (enrdf_load_stackoverflow) | 1978-05-12 |
| IE41628L (en) | 1976-01-02 |
| FR2302084A1 (fr) | 1976-09-24 |
| JPS5129217A (en) | 1976-03-12 |
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