CS247191B2 - Method of acetylerythromycinstearate preparation - Google Patents
Method of acetylerythromycinstearate preparation Download PDFInfo
- Publication number
- CS247191B2 CS247191B2 CS8596A CS9685A CS247191B2 CS 247191 B2 CS247191 B2 CS 247191B2 CS 8596 A CS8596 A CS 8596A CS 9685 A CS9685 A CS 9685A CS 247191 B2 CS247191 B2 CS 247191B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- stearate
- erythromycin
- acetylerythromycin
- preparation
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 16
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims abstract description 31
- 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 abstract description 21
- -1 acetyl erythromycin stearate Chemical compound 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 39
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 235000021355 Stearic acid Nutrition 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 239000008117 stearic acid Substances 0.000 claims description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 21
- 229960004142 erythromycin stearate Drugs 0.000 abstract description 17
- 239000003814 drug Substances 0.000 abstract description 8
- 229960003276 erythromycin Drugs 0.000 abstract description 6
- 150000002148 esters Chemical class 0.000 abstract description 6
- 239000003242 anti bacterial agent Substances 0.000 abstract description 2
- 229940088710 antibiotic agent Drugs 0.000 abstract description 2
- 230000003115 biocidal effect Effects 0.000 abstract description 2
- 210000004211 gastric acid Anatomy 0.000 abstract 1
- YAVZHCFFUATPRK-YZPBMOCRSA-N Erythromycin stearate Chemical compound CCCCCCCCCCCCCCCCCC(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 YAVZHCFFUATPRK-YZPBMOCRSA-N 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- AWMFUEJKWXESNL-JZBHMOKNSA-N erythromycin estolate Chemical compound CCCCCCCCCCCCOS(O)(=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)OC(=O)CC)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AWMFUEJKWXESNL-JZBHMOKNSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 229960003203 erythromycin estolate Drugs 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 206010019851 Hepatotoxicity Diseases 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 231100000304 hepatotoxicity Toxicity 0.000 description 3
- 230000007686 hepatotoxicity Effects 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- RJUFATJOENABQE-UHFFFAOYSA-N (2,2,2-trichloro-1-diphenoxyphosphorylethyl) acetate Chemical compound C=1C=CC=CC=1OP(=O)(C(C(Cl)(Cl)Cl)OC(=O)C)OC1=CC=CC=C1 RJUFATJOENABQE-UHFFFAOYSA-N 0.000 description 2
- 241001530392 Aphos Species 0.000 description 2
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000003908 liver function Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- NNRXCKZMQLFUPL-WBMZRJHASA-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;(2r,3 Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O.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 NNRXCKZMQLFUPL-WBMZRJHASA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- 238000011785 NMRI mouse Methods 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006161 blood agar Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 235000021152 breakfast Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 229960001681 croscarmellose sodium Drugs 0.000 description 1
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
- 229960004213 erythromycin lactobionate Drugs 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 235000021552 granulated sugar Nutrition 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 231100000334 hepatotoxic Toxicity 0.000 description 1
- 230000003082 hepatotoxic effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000011022 operating instruction Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 238000005303 weighing Methods 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Coloring (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK5884A DK149776C (da) | 1984-01-06 | 1984-01-06 | Antibiotisk virksom erytromycinforbindelse og praeparat indeholdende forbindelsen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS247191B2 true CS247191B2 (en) | 1986-12-18 |
Family
ID=8089251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS8596A CS247191B2 (en) | 1984-01-06 | 1985-01-04 | Method of acetylerythromycinstearate preparation |
Country Status (38)
| Country | Link |
|---|---|
| US (1) | US4599326A (de) |
| JP (1) | JPS60158197A (de) |
| KR (1) | KR900006237B1 (de) |
| AT (1) | AT386414B (de) |
| AU (1) | AU565688B2 (de) |
| BE (1) | BE901411A (de) |
| BG (1) | BG43189A3 (de) |
| CA (1) | CA1224461A (de) |
| CH (1) | CH666275A5 (de) |
| CS (1) | CS247191B2 (de) |
| CY (1) | CY1462A (de) |
| DE (1) | DE3500179A1 (de) |
| DK (1) | DK149776C (de) |
| ES (1) | ES8605818A1 (de) |
| FI (1) | FI77249C (de) |
| FR (1) | FR2557878B1 (de) |
| GB (1) | GB2152502B (de) |
| HK (1) | HK11590A (de) |
| HU (1) | HU196221B (de) |
| IE (1) | IE57967B1 (de) |
| IL (1) | IL73885A (de) |
| IS (1) | IS2968A7 (de) |
| IT (1) | IT1184304B (de) |
| KE (1) | KE3841A (de) |
| LU (1) | LU85721A1 (de) |
| MA (1) | MA20316A1 (de) |
| MX (1) | MX156277A (de) |
| NL (1) | NL8403979A (de) |
| NO (1) | NO160263C (de) |
| NZ (1) | NZ210606A (de) |
| PH (1) | PH22471A (de) |
| PL (1) | PL144349B1 (de) |
| PT (1) | PT79777B (de) |
| RO (1) | RO91262B (de) |
| SE (1) | SE461854B (de) |
| SU (1) | SU1410866A3 (de) |
| YU (1) | YU44485B (de) |
| ZA (1) | ZA8410143B (de) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4874614A (en) * | 1985-03-25 | 1989-10-17 | Abbott Laboratories | Pharmaceutical tableting method |
| US4863741A (en) * | 1985-03-25 | 1989-09-05 | Abbott Laboratories | Tablet composition for drug combinations |
| JP3382159B2 (ja) * | 1998-08-05 | 2003-03-04 | 株式会社東芝 | 情報記録媒体とその再生方法及び記録方法 |
| WO2004004693A1 (en) * | 2002-07-05 | 2004-01-15 | Collgegium Pharmaceutical | Abuse-deterrent pharmaceutical compositions of opiods and other drugs |
| US8840928B2 (en) | 2002-07-05 | 2014-09-23 | Collegium Pharmaceutical, Inc. | Tamper-resistant pharmaceutical compositions of opioids and other drugs |
| US10004729B2 (en) | 2002-07-05 | 2018-06-26 | Collegium Pharmaceutical, Inc. | Tamper-resistant pharmaceutical compositions of opioids and other drugs |
| JP2007509975A (ja) * | 2003-10-31 | 2007-04-19 | アルザ・コーポレーシヨン | ギャバペンチン及びプレギャバリンの増加された吸収のための組成物及び投与形態物 |
| LT1765292T (lt) | 2004-06-12 | 2018-01-10 | Collegium Pharmaceutical, Inc. | Nuo piktnaudžiavimo apsaugotos vaistų formos |
| WO2006025882A2 (en) | 2004-08-25 | 2006-03-09 | The Uab Research Foundation | Absorption enhancers for drug administration |
| US9895444B2 (en) | 2004-08-25 | 2018-02-20 | Aegis Therapeutics, Llc | Compositions for drug administration |
| EP2505189B1 (de) | 2006-06-23 | 2018-08-08 | Aegis Therapeutics, LLC | Stabilisierung von Alkylglykosidzusammensetzungen und zugehöriges Verfahren |
| US10668060B2 (en) | 2009-12-10 | 2020-06-02 | Collegium Pharmaceutical, Inc. | Tamper-resistant pharmaceutical compositions of opioids and other drugs |
| CN103796666B (zh) | 2011-05-18 | 2018-07-06 | 欧莫德里斯制药公司 | 改良的肽药物 |
| EP3444281B1 (de) | 2012-11-20 | 2021-11-03 | Eumederis Pharmaceuticals, Inc. | Verbesserte peptidarzneimittel |
| AU2013347975B2 (en) | 2012-11-20 | 2018-07-26 | Mederis Diabetes, Llc | Improved peptide pharmaceuticals for insulin resistance |
| WO2014140699A1 (en) * | 2013-03-13 | 2014-09-18 | Calyx Chemicals And Pharmaceuticals Ltd | A novel process of liberation of erythromycin and preparation of its salts |
| FI3155017T3 (fi) | 2014-05-28 | 2024-04-17 | Mederis Diabetes Llc | Parannettuja peptidilääkkeitä insuliiniresistenssiin |
| WO2017222575A1 (en) | 2016-06-23 | 2017-12-28 | Collegium Pharmaceutical, Inc. | Process of making more stable abuse-deterrent oral formulations |
| KR20200010343A (ko) | 2017-05-19 | 2020-01-30 | 루넬라 바이오테크 인코포레이티드 | 안티미토신: 암 줄기 세포를 근절하기 위한 미토콘드리아 생물발생의 표적화 억제제 |
| WO2019108729A1 (en) | 2017-12-01 | 2019-06-06 | Lunella Biotech, Inc. | Repurposcins: targeted inhibitors of mitochondrial biogenesis for eradicating cancer stem cells |
| JP6941224B2 (ja) | 2018-02-06 | 2021-09-29 | イージス セラピューティクス，エルエルシー | 疾患の処置のための鼻腔内エピネフリン製剤及び方法 |
| AU2019217643B2 (en) | 2018-02-06 | 2021-10-28 | ARS Pharmaceuticals Operations, Inc. | Intranasal epinephrine formulations and methods for the treatment of disease |
| MX2021007345A (es) * | 2018-12-17 | 2021-07-15 | Lunella Biotech Inc | Terapias de combinacion triple para fijar como objetivo mitocondrias y aniquilar celulas madre cancerosas. |
| BR112021011964A2 (pt) * | 2018-12-17 | 2021-09-08 | Lunella Biotech, Inc. | Terapias de combinação tripla para antienvelhecimento |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1011117B (de) * | 1953-11-16 | 1957-06-27 | Abbott Lab | Verfahren zur Herstellung von reinen stabilen Erythromycin-Saeure-Additionssalzen |
| FR1179208A (fr) * | 1953-11-16 | 1959-05-21 | Abbott Lab | Procédé de préparation de sels d'érythromycine |
| GB834397A (en) * | 1958-07-29 | 1960-05-04 | Lilly Co Eli | Therapeutic compositions comprising erythromycin esters |
| US4150220A (en) * | 1977-02-04 | 1979-04-17 | Pfizer Inc. | Semi-synthetic 4"-erythromycin A derivatives |
| FR2473525A1 (fr) * | 1980-01-11 | 1981-07-17 | Roussel Uclaf | Nouvelles oximes derivees de l'erythromycine, leur procede de preparation et leur application comme medicaments |
-
1984
- 1984-01-06 DK DK5884A patent/DK149776C/da not_active IP Right Cessation
- 1984-12-18 NZ NZ210606A patent/NZ210606A/en unknown
- 1984-12-20 IL IL73885A patent/IL73885A/xx not_active IP Right Cessation
- 1984-12-21 GB GB08432368A patent/GB2152502B/en not_active Expired
- 1984-12-21 AU AU37059/84A patent/AU565688B2/en not_active Ceased
- 1984-12-27 US US06/686,753 patent/US4599326A/en not_active Expired - Fee Related
- 1984-12-28 ZA ZA8410143A patent/ZA8410143B/xx unknown
- 1984-12-28 SE SE8406671A patent/SE461854B/sv not_active IP Right Cessation
- 1984-12-28 BE BE0/214265A patent/BE901411A/fr not_active IP Right Cessation
- 1984-12-28 PT PT79777A patent/PT79777B/pt not_active IP Right Cessation
- 1984-12-28 IS IS2968A patent/IS2968A7/is unknown
- 1984-12-31 NL NL8403979A patent/NL8403979A/nl not_active Application Discontinuation
-
1985
- 1985-01-02 MA MA20540A patent/MA20316A1/fr unknown
- 1985-01-02 NO NO850007A patent/NO160263C/no unknown
- 1985-01-02 FR FR8500005A patent/FR2557878B1/fr not_active Expired
- 1985-01-03 AT AT0000985A patent/AT386414B/de not_active IP Right Cessation
- 1985-01-03 FI FI850023A patent/FI77249C/fi not_active IP Right Cessation
- 1985-01-04 IE IE22/85A patent/IE57967B1/en not_active IP Right Cessation
- 1985-01-04 CH CH31/85A patent/CH666275A5/de not_active IP Right Cessation
- 1985-01-04 SU SU853836820A patent/SU1410866A3/ru active
- 1985-01-04 CS CS8596A patent/CS247191B2/cs unknown
- 1985-01-04 KR KR1019850000008A patent/KR900006237B1/ko not_active Expired
- 1985-01-04 HU HU8537A patent/HU196221B/hu not_active IP Right Cessation
- 1985-01-04 ES ES539349A patent/ES8605818A1/es not_active Expired
- 1985-01-04 CA CA000471563A patent/CA1224461A/en not_active Expired
- 1985-01-04 LU LU85721A patent/LU85721A1/fr unknown
- 1985-01-04 YU YU20/85A patent/YU44485B/xx unknown
- 1985-01-04 IT IT19012/85A patent/IT1184304B/it active
- 1985-01-04 DE DE19853500179 patent/DE3500179A1/de active Granted
- 1985-01-04 PL PL1985251457A patent/PL144349B1/pl unknown
- 1985-01-05 BG BG068285A patent/BG43189A3/xx unknown
- 1985-01-07 PH PH31689A patent/PH22471A/en unknown
- 1985-01-07 JP JP60000744A patent/JPS60158197A/ja active Granted
- 1985-01-07 RO RO117230A patent/RO91262B/ro unknown
- 1985-01-07 MX MX203973A patent/MX156277A/es unknown
-
1988
- 1988-10-28 KE KE3841A patent/KE3841A/xx unknown
-
1989
- 1989-07-21 CY CY1462A patent/CY1462A/en unknown
-
1990
- 1990-02-15 HK HK115/90A patent/HK11590A/xx unknown
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