WO1992006991A1 - Erythromycine modifiee en 2' ou derive de cette substance - Google Patents
Erythromycine modifiee en 2' ou derive de cette substance Download PDFInfo
- Publication number
- WO1992006991A1 WO1992006991A1 PCT/JP1991/001368 JP9101368W WO9206991A1 WO 1992006991 A1 WO1992006991 A1 WO 1992006991A1 JP 9101368 W JP9101368 W JP 9101368W WO 9206991 A1 WO9206991 A1 WO 9206991A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- ethoxy
- ethyl
- methylerythromycin
- acid
- erythromycin
- Prior art date
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- 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 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 229960003276 erythromycin Drugs 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- -1 N —Benzylaminoethyl Chemical group 0.000 claims description 26
- AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin 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)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 claims description 24
- 150000002923 oximes Chemical class 0.000 claims description 10
- 229930006677 Erythromycin A Natural products 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000006508 2,6-difluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C(F)=C1[H])C([H])([H])* 0.000 claims description 3
- 229960002626 clarithromycin Drugs 0.000 claims description 3
- 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 claims description 2
- 229960004099 azithromycin Drugs 0.000 claims description 2
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[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 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 claims description 2
- 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 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- RXZBMPWDPOLZGW-XMRMVWPWSA-N (E)-roxithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N/OCOCCOC)/[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 RXZBMPWDPOLZGW-XMRMVWPWSA-N 0.000 claims 1
- 229960005224 roxithromycin Drugs 0.000 claims 1
- 235000019658 bitter taste Nutrition 0.000 abstract description 7
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
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- 238000004440 column chromatography Methods 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- PIZLBWGMERQCOC-UHFFFAOYSA-N dibenzyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OCC1=CC=CC=C1 PIZLBWGMERQCOC-UHFFFAOYSA-N 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 229940069417 doxy Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 235000019285 ethoxyquin Nutrition 0.000 description 1
- DECIPOUIJURFOJ-UHFFFAOYSA-N ethoxyquin Chemical compound N1C(C)(C)C=C(C)C2=CC(OCC)=CC=C21 DECIPOUIJURFOJ-UHFFFAOYSA-N 0.000 description 1
- 229940093500 ethoxyquin Drugs 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229940099563 lactobionic acid Drugs 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- KTEDZFORYFITAF-UHFFFAOYSA-K rhodium(3+);trihydroxide Chemical compound [OH-].[OH-].[OH-].[Rh+3] KTEDZFORYFITAF-UHFFFAOYSA-K 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-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
Definitions
- the present invention relates to the 2'-modified erythromycin compound of the present invention. More specifically, when used as a drug, the 2'-position of the erythromycin compound has significantly reduced bitterness when taken and improved in vivo absorbability. Min to the modified compound.
- Erythromycins used for chemotherapy of various bacterial infections are mainly used in oral administration. These generally have a unique bitter taste, and as a result, when used as an oral medicine, the necessity of using capsules or coated tablets has arisen, but in children and the elderly who have difficulty swallowing these drugs. Is desirably a liquid or granule, in which case simple masking did not sufficiently reduce bitterness. Therefore, in order to solve these problems, various esters that have no bitterness at the time of administration of the drug but exhibit antibacterial activity by returning to the active substance at the time of in vivo absorption or after absorption have been studied. Has been open II.
- the present invention provides a compound represented by the formula
- erythromycins mean those having an erythromycin skeleton or those derived from erythromycin, such as erythromycin
- alkyl group having 1 to 12 carbon atoms means a linear or branched one.
- Salts include acetic acid, brobionic acid, butyric acid, formic acid, trifluoroacetic acid, maleic acid, fumaric acid, lactic acid, tartaric acid, citric acid, stearic acid, succinic acid, ethyl succinic acid, lactobionic acid, glycolic acid, dalcoheptonic acid, Benzoic acid, methanesulfonic acid, ethanesulfonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, para-toluenesulfonic acid, lauryl sulfate, malic acid, aspartic acid, glutamic acid, adibic acid, cysteine, N— Acetyl cysteine, thiomaleic acid, hydrochloric acid, hydrobromic acid, phosphoric acid, sulfuric acid, hydroiodic acid, nicotinic acid, oxalic acid, picric acid, thiocyanic acid,
- the compound of the present invention can be produced as follows.
- erythromycins in which the 2′-position is a hydroxyl group, are prepared in an inert solvent in the presence of a dehydrochlorinating agent by the formula
- examples of the compound of formula (H) include 2-ethoxyhexyl chloroformate, 2- (2-methoxyethoxy) ethylile chloroformate, and 2- (2-ethoxyethoxy) ethyl.
- Black mouth hole remate, 2- [2- (2-methoxyethoxy) ethoxy] ethyl ⁇ mouth formate, 2- [2- (2-ethoxyethoxyethoxy) ethyl] Black mouth formate, 2- [2- (2 —Isobroviroki Shetoxy) ethoxy] ethyl chromium pi formate, 2- ⁇ 2- [2- (2-methoxetoxy) ethoxy] ethoxy ⁇ ethyl chloroformate, 2- (2-n-butoxyethoxy) ethyl chloroformate, 2- ( 2-dodecyloxyethoxy) ethyl chromate formate, 2- [2-n-hexyloxetoxy)
- sodium hydroxide, sodium hydroxide, sodium bicarbonate, potassium carbonate, sodium carbonate, triethylamine, etc. can be used, and the amount of these used is erythromycin. 1 to 2 equivalents, preferably 1.1 to 1.3 equivalents, in the case of sodium hydroxide or rhodium hydroxide, relative to the compound having a hydroxyl group at the 2′-position and the compound of formula I), The amount is 3 to 8 equivalents, preferably 5 equivalents for sodium or sodium carbonate, and 1 to 5 equivalents, preferably 3 equivalents for triethylamine.
- the inert solvent acetone, ethyl ethyl drone, dichloromethane, chloroform, toluene, ether, tetrahydrofuran and the like can be used, and preferably acetone, ethyl acetate, dichloromethane and tetrahydrofuran are used.
- the reaction time is usually 30 minutes to 4 hours at ambient temperature, but if the progress of the reaction is slow, the reaction is carried out for a longer time. If the progress of the reaction is insufficient in some cases, the reaction can be continued by further adding a dehydrochlorinating agent and a compound of the formula (H).
- the foamy substance was purified by silica gel column chromatography (elution solvent: acetone: black form: 2: 25 to 1: 2), and then crystallized from chlorophorem-n-hexane to give 6-0-methylerythromycin A 2 ′ — ⁇ 2-—2- (2-Methoxyethoxy) ethoxy] ethyl ⁇ White powder (11.2 g) of potassium carbonate was obtained.
- the obtained foam was purified by silica gel column chromatography (elution solvent; methanol: porcine form 1: 99 to 3: 97), and 6-0-methylerythromycin A 2 '-[2- (2 [1-n-hexyloxetoxy) ethyl] carbonate (16.03 g) was obtained as a colorless foam. Crystallization from petroleum ether gave 14.12 g of a white powder.
- the dichloromethane layer was washed with a saturated sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.
- Example 7 After further reacting at room temperature for 15 hours, a post-treatment was carried out in the same manner as in Example 7.
- crystallized from chloroform- n- hexane By converting to 60- methylerythr ⁇ -mycin A2 *- ⁇ 2- [2- (2- (2-methoxetoxy) ethoxy) ethoxy] ethyl] power (8.44 g) as a white powder As obtained.
- Triethylamine 17.34 mC
- 2- [2- (2-methoxyethoxy) ethoxy] ethylcycloformate 22.73 g
- triethylamine 8.67 m ⁇ 2>
- 2- [2- (2-methoxhetoxy) ethoxy] ethylcycloformate 15.15 g
- a compound of the present invention (samples 1 to 6) and a known ester of a macrolide compound as a control (control samples 1 to 4 :) were suspended in 5% gum arabic water, and the ICR male mouse was suspended. (12 animals per group) were orally administered at a dose of 100 mg / kg. Thereafter, three mice were exsanguinated and killed at predetermined time intervals, and the amount of antibacterial activity in the serum was measured. The antibacterial activity was measured by the paper disk method using Micrococcus * Luteus' ATCC 9341 as a test bacterium. Table 1 shows the results.
- Control sample 1 6-0-methylerythromycin A 2 ethyl succinate
- Control sample 2 6-0 0-methyl erythromycin A 2 ethyl carbonate
- Control sample 3 6-0—Methylerythromycin A2'-benzyl carbonate
- Control sample 4 Erythromycin A2'-ethyl carbonate
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002094060A CA2094060A1 (en) | 1990-10-15 | 1991-10-08 | 2'-position modified compound of erythromycin or its derivative |
KR1019930701117A KR930702369A (ko) | 1990-10-15 | 1991-10-08 | 에리쓰로마이신 또는 그의 유도체의 2'위치 수식 화합물 |
US08/039,121 US5350839A (en) | 1990-10-15 | 1991-10-08 | 2'-position modified compound of erythromycin or its derivative |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP27602990 | 1990-10-15 | ||
JP2/276029 | 1990-10-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1992006991A1 true WO1992006991A1 (fr) | 1992-04-30 |
Family
ID=17563804
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1991/001368 WO1992006991A1 (fr) | 1990-10-15 | 1991-10-08 | Erythromycine modifiee en 2' ou derive de cette substance |
Country Status (5)
Country | Link |
---|---|
US (1) | US5350839A (ja) |
EP (1) | EP0553353A1 (ja) |
KR (1) | KR930702369A (ja) |
CA (1) | CA2094060A1 (ja) |
WO (1) | WO1992006991A1 (ja) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5795871A (en) * | 1994-04-26 | 1998-08-18 | Nobuhiro Narita | Pharmaceutical composition for treatment of non-small cell lung cancer |
US5605889A (en) * | 1994-04-29 | 1997-02-25 | Pfizer Inc. | Method of administering azithromycin |
US5719272A (en) * | 1996-04-02 | 1998-02-17 | Abbott Laboratories | 2'-protected 3'-dimethylamine, 9-etheroxime erythromycin A derivatives |
US5766622A (en) * | 1996-08-14 | 1998-06-16 | The Procter & Gamble Company | Inhibiting undesirable taste in oral compositions |
UA51730C2 (uk) * | 1996-09-04 | 2002-12-16 | Ебботт Лабораторіз | 6-o-заміщені кетоліди з антибактеріальною активністю, спосіб їх одержання (варіанти), фармацевтична композиція та спосіб регулювання бактеріальної інфекції у ссавців |
EP1291352B1 (en) * | 1996-09-04 | 2005-05-25 | Abbott Laboratories | 6-O-substituted ketolides having antibacterial activity |
EP1437360A3 (en) * | 1998-08-19 | 2005-04-06 | Pfizer Products Inc. | C11 Carbamates of macrolide antibacterials |
US6043227A (en) * | 1998-08-19 | 2000-03-28 | Pfizer Inc. | C11 carbamates of macrolide antibacterials |
US6054435A (en) * | 1999-03-19 | 2000-04-25 | Abbott Laboratories | 6-O-substituted macrolides having antibacterial activity |
HRP990130B1 (en) * | 1999-05-03 | 2004-06-30 | Pliva D D | HALOGEN DERIVATIVES 9a-N-(N'-ARYLCARBAMOYL)- AND 9a-N-(N'-ARYLTHIOCARBAMOYL)-9-DEOXO-9a-AZA-9a OF HOMOERYTHROMYCIN A |
GB9914346D0 (en) | 1999-06-19 | 1999-08-18 | Univ Manchester | Antibiotic agents |
MXPA02009587A (es) * | 2000-03-28 | 2003-05-14 | Biochemie Gmbh | Particulas granuladas con sabor enmascarado. |
AU2001214115A1 (en) * | 2000-08-01 | 2002-02-13 | Habil F. Khorakiwala | Process for the preparation of anhydrous azithromycin |
AU2001280000A1 (en) * | 2000-08-23 | 2002-03-04 | Jaweed Mukarram, Siddiqui Mohammed | Process for preparation of anhydrous azithromycin |
US8680226B1 (en) | 2012-12-21 | 2014-03-25 | Saudi Basic Industries Corporation | Method for alcoholysis of acrylonitrile-butadiene-styrene-containing polycarbonate compositions |
EP2746249B1 (en) | 2012-12-21 | 2017-06-07 | Saudi Basic Industries Corporation | Manufacture of dihydroxy aromatic compounds by alcoholysis of flame retardant-containing polycarbonate compositions |
US8680227B1 (en) | 2012-12-21 | 2014-03-25 | Saudi Basic Industries Corporation | Manufacture of dihydroxy aromatic compounds by alcoholysis of polycarbonate-containing compositions |
US8846858B2 (en) | 2012-12-21 | 2014-09-30 | Saudi Basic Industries Corporation | Method for alcoholysis of polycarbonate compositions containing flame retardant or acrylonitrile-butadiene-styrene |
CN104177457A (zh) * | 2013-05-23 | 2014-12-03 | 长春海悦药业有限公司 | 一种阿奇霉素药物原料及其制剂和用途 |
AU2020259997A1 (en) * | 2019-04-18 | 2021-11-25 | Azura Ophthalmics Ltd. | Compounds and methods for the treatment of ocular disorders |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS53144589A (en) * | 1977-05-21 | 1978-12-15 | Taisho Pharmaceut Co Ltd | Erythromycin a derivatives |
JPS61200998A (ja) * | 1985-03-01 | 1986-09-05 | Taisho Pharmaceut Co Ltd | エリスロマイシンエステル誘導体 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4382086A (en) * | 1982-03-01 | 1983-05-03 | Pfizer Inc. | 9-Dihydro-11,12-ketal derivatives of erythromycin A and epi-erythromycin A |
JPS6187625A (ja) * | 1984-10-05 | 1986-05-06 | Satoshi Omura | 消化管収縮運動促進剤 |
FR2582000B1 (fr) * | 1985-05-14 | 1987-06-26 | Oreal | Esters gras bi ou tri-eniques d'erythromycine a, leur procede de preparation et compositions pharmaceutiques et cosmetiques les contenant |
MY103197A (en) * | 1987-02-20 | 1993-05-29 | Kitasato Inst | A growth promoting composition and production thereof |
-
1991
- 1991-10-08 CA CA002094060A patent/CA2094060A1/en not_active Abandoned
- 1991-10-08 EP EP91917071A patent/EP0553353A1/en not_active Ceased
- 1991-10-08 WO PCT/JP1991/001368 patent/WO1992006991A1/ja not_active Application Discontinuation
- 1991-10-08 US US08/039,121 patent/US5350839A/en not_active Expired - Fee Related
- 1991-10-08 KR KR1019930701117A patent/KR930702369A/ko not_active Application Discontinuation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS53144589A (en) * | 1977-05-21 | 1978-12-15 | Taisho Pharmaceut Co Ltd | Erythromycin a derivatives |
JPS61200998A (ja) * | 1985-03-01 | 1986-09-05 | Taisho Pharmaceut Co Ltd | エリスロマイシンエステル誘導体 |
Also Published As
Publication number | Publication date |
---|---|
EP0553353A1 (en) | 1993-08-04 |
EP0553353A4 (ja) | 1994-02-02 |
CA2094060A1 (en) | 1992-04-16 |
KR930702369A (ko) | 1993-09-08 |
US5350839A (en) | 1994-09-27 |
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