CY1462A - An antibiotic compound,a method for its preparation,and compositions containing it - Google Patents

An antibiotic compound,a method for its preparation,and compositions containing it Download PDF

Info

Publication number: CY1462A
Authority: CY; Cyprus
Prior art keywords: stearate; erythromycin; ofthe; solvent; acetyl
Prior art date: 1984-01-06

Application number

CY1462A

Other languages

English (en)

Original Assignee

Orion Yhtymae Oy

Priority date (The priority date 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 date listed.)

1984-01-06

Filing date

1989-07-21

Publication date

1989-07-21

1989-07-21 Application filed by Orion Yhtymae Oy filed Critical Orion Yhtymae Oy

1989-07-21 Publication of CY1462A publication Critical patent/CY1462A/en

Links

238000000034 method Methods 0.000 title claims description 18
150000001875 compounds Chemical class 0.000 title claims description 17
238000002360 preparation method Methods 0.000 title claims description 17
239000000203 mixture Substances 0.000 title claims description 12
230000003115 biocidal effect Effects 0.000 title claims description 6
239000003242 anti bacterial agent Substances 0.000 title claims description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 39
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 description 28
229960004142 erythromycin stearate Drugs 0.000 claims description 27
-1 acetyl erythromycin stearate Chemical compound 0.000 claims description 25
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
239000004480 active ingredient Substances 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
229920000036 polyvinylpyrrolidone Polymers 0.000 claims description 5
239000001267 polyvinylpyrrolidone Substances 0.000 claims description 5
235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 5
229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 4
239000004615 ingredient Substances 0.000 claims description 4
239000003208 petroleum Substances 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
229920000168 Microcrystalline cellulose Polymers 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 3
239000001768 carboxy methyl cellulose Substances 0.000 claims description 3
235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 3
235000019813 microcrystalline cellulose Nutrition 0.000 claims description 3
239000008108 microcrystalline cellulose Substances 0.000 claims description 3
229940016286 microcrystalline cellulose Drugs 0.000 claims description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
229920002261 Corn starch Polymers 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
239000008120 corn starch Substances 0.000 claims description 2
235000021552 granulated sugar Nutrition 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 2
239000003960 organic solvent Substances 0.000 claims 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
150000001342 alkaline earth metals Chemical class 0.000 claims 1
239000000945 filler Substances 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
239000000314 lubricant Substances 0.000 claims 1
235000019359 magnesium stearate Nutrition 0.000 claims 1
238000000926 separation method Methods 0.000 claims 1
239000007787 solid Substances 0.000 claims 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
229960003276 erythromycin Drugs 0.000 description 12
238000010521 absorption reaction Methods 0.000 description 10
239000000243 solution Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
239000003814 drug Substances 0.000 description 6
241000894006 Bacteria Species 0.000 description 5
241001465754 Metazoa Species 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
229960003203 erythromycin estolate Drugs 0.000 description 4
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 4
239000008187 granular material Substances 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
231100000304 hepatotoxicity Toxicity 0.000 description 3
230000007056 liver toxicity Effects 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
210000002966 serum Anatomy 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
SPTSIOTYTJZTOG-UHFFFAOYSA-N acetic acid;octadecanoic acid Chemical compound CC(O)=O.CCCCCCCCCCCCCCCCCC(O)=O SPTSIOTYTJZTOG-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
210000004369 blood Anatomy 0.000 description 2
239000008280 blood Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000007888 film coating Substances 0.000 description 2
238000009501 film coating Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
235000012054 meals Nutrition 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
239000008213 purified water Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
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 1
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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241001530392 Aphos Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
238000011785 NMRI mouse Methods 0.000 description 1
241000193998 Streptococcus pneumoniae Species 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
238000009640 blood culture Methods 0.000 description 1
235000021152 breakfast Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000006378 damage Effects 0.000 description 1
230000007423 decrease Effects 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
229960004213 erythromycin lactobionate Drugs 0.000 description 1
210000003238 esophagus Anatomy 0.000 description 1
235000013305 food Nutrition 0.000 description 1
230000006870 function Effects 0.000 description 1
210000004211 gastric acid Anatomy 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
208000014674 injury Diseases 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
230000003908 liver function Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000002547 new drug Substances 0.000 description 1
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 1
238000011022 operating instruction Methods 0.000 description 1
239000008194 pharmaceutical composition 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
238000012216 screening Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet 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
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)

CY1462A 1984-01-06 1989-07-21 An antibiotic compound,a method for its preparation,and compositions containing it CY1462A (en)

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
CY1462A true CY1462A (en)	1989-07-21

Family

ID=8089251

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CY1462A CY1462A (en)	1984-01-06	1989-07-21	An antibiotic compound,a method for its preparation,and compositions containing it

Country Status (38)

Country	Link
US (1)	US4599326A (2)
JP (1)	JPS60158197A (2)
KR (1)	KR900006237B1 (2)
AT (1)	AT386414B (2)
AU (1)	AU565688B2 (2)
BE (1)	BE901411A (2)
BG (1)	BG43189A3 (2)
CA (1)	CA1224461A (2)
CH (1)	CH666275A5 (2)
CS (1)	CS247191B2 (2)
CY (1)	CY1462A (2)
DE (1)	DE3500179A1 (2)
DK (1)	DK149776C (2)
ES (1)	ES8605818A1 (2)
FI (1)	FI77249C (2)
FR (1)	FR2557878B1 (2)
GB (1)	GB2152502B (2)
HK (1)	HK11590A (2)
HU (1)	HU196221B (2)
IE (1)	IE57967B1 (2)
IL (1)	IL73885A (2)
IS (1)	IS2968A7 (2)
IT (1)	IT1184304B (2)
KE (1)	KE3841A (2)
LU (1)	LU85721A1 (2)
MA (1)	MA20316A1 (2)
MX (1)	MX156277A (2)
NL (1)	NL8403979A (2)
NO (1)	NO160263C (2)
NZ (1)	NZ210606A (2)
PH (1)	PH22471A (2)
PL (1)	PL144349B1 (2)
PT (1)	PT79777B (2)
RO (1)	RO91262B (2)
SE (1)	SE461854B (2)
SU (1)	SU1410866A3 (2)
YU (1)	YU44485B (2)
ZA (1)	ZA8410143B (2)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
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
US8840928B2 (en)	2002-07-05	2014-09-23	Collegium Pharmaceutical, Inc.	Tamper-resistant pharmaceutical compositions of opioids and other drugs
CA2491572C (en) *	2002-07-05	2010-03-23	Collegium Pharmaceutical, Inc.	Abuse-deterrent pharmaceutical compositions of opiods and other drugs
US10004729B2 (en)	2002-07-05	2018-06-26	Collegium Pharmaceutical, Inc.	Tamper-resistant pharmaceutical compositions of opioids and other drugs
EP1677758A1 (en) *	2003-10-31	2006-07-12	ALZA Corporation	Compositions and dosage forms for enhanced absorption of 3-amino-n-butyl-phosphinic acid
HUE037643T2 (hu)	2004-06-12	2018-09-28	Collegium Pharmaceutical Inc	Visszaélésre nem alkalmas gyógyszerkészítmények
US9895444B2 (en)	2004-08-25	2018-02-20	Aegis Therapeutics, Llc	Compositions for drug administration
WO2006025882A2 (en)	2004-08-25	2006-03-09	The Uab Research Foundation	Absorption enhancers for drug administration
EP2505189B1 (en)	2006-06-23	2018-08-08	Aegis Therapeutics, LLC	Stabilizing alkylglycoside compositions and method thereof
US10668060B2 (en)	2009-12-10	2020-06-02	Collegium Pharmaceutical, Inc.	Tamper-resistant pharmaceutical compositions of opioids and other drugs
WO2012158962A2 (en)	2011-05-18	2012-11-22	Eumederis Pharmaceuticals, Inc.	Improved peptide pharmaceuticals
AU2013347975B2 (en)	2012-11-20	2018-07-26	Mederis Diabetes, Llc	Improved peptide pharmaceuticals for insulin resistance
CA2891929C (en)	2012-11-20	2022-07-19	Eumederis Pharmaceuticals, Inc.	Improved peptide pharmaceuticals
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
HUE066179T2 (hu)	2014-05-28	2024-07-28	Mederis Diabetes Llc	Javított peptidek inzulinrezisztencia ellen
WO2017222575A1 (en)	2016-06-23	2017-12-28	Collegium Pharmaceutical, Inc.	Process of making more stable abuse-deterrent oral formulations
CN111315400A (zh)	2017-05-19	2020-06-19	卢内拉生物技术有限公司	Antimitoscin：用于根除癌症干细胞的线粒体生物发生的靶向抑制剂
EP3717015A4 (en)	2017-12-01	2021-07-28	Lunella Biotech, Inc.	REPURPOSCINS: TARGET MITOCHONDRIAL BIOGENESIS INHIBITORS TO ERADICATE CARCINOUS STEM CELLS
WO2019157099A1 (en)	2018-02-06	2019-08-15	Aegis Therapeutics, Llc	Intranasal epinephrine formulations and methods for the treatment of disease
IL276485B2 (en)	2018-02-06	2024-12-01	Aegis Therapeutics Llc	Intranasal epinephrine formulations and methods for the treatment of disease
CA3123838A1 (en) *	2018-12-17	2020-06-25	Lunella Biotech, Inc.	Triple combination therapies for targeting mitochondria and killing cancer stem cells
CN113453690A (zh) *	2018-12-17	2021-09-28	卢内拉生物技术有限公司	用于抗衰老的三联疗法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
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 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 IS IS2968A patent/IS2968A7/is unknown
- 1984-12-28 PT PT79777A patent/PT79777B/pt not_active IP Right Cessation
- 1984-12-28 ZA ZA8410143A patent/ZA8410143B/xx 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 FR FR8500005A patent/FR2557878B1/fr not_active Expired
- 1985-01-02 NO NO850007A patent/NO160263C/no unknown
- 1985-01-03 FI FI850023A patent/FI77249C/fi not_active IP Right Cessation
- 1985-01-03 AT AT0000985A patent/AT386414B/de not_active IP Right Cessation
- 1985-01-04 HU HU8537A patent/HU196221B/hu not_active IP Right Cessation
- 1985-01-04 CA CA000471563A patent/CA1224461A/en not_active Expired
- 1985-01-04 SU SU853836820A patent/SU1410866A3/ru active
- 1985-01-04 CS CS8596A patent/CS247191B2/cs unknown
- 1985-01-04 PL PL1985251457A patent/PL144349B1/pl unknown
- 1985-01-04 ES ES539349A patent/ES8605818A1/es not_active Expired
- 1985-01-04 LU LU85721A patent/LU85721A1/fr unknown
- 1985-01-04 KR KR1019850000008A patent/KR900006237B1/ko not_active Expired
- 1985-01-04 IT IT19012/85A patent/IT1184304B/it active
- 1985-01-04 YU YU20/85A patent/YU44485B/xx unknown
- 1985-01-04 IE IE22/85A patent/IE57967B1/en not_active IP Right Cessation
- 1985-01-04 DE DE19853500179 patent/DE3500179A1/de active Granted
- 1985-01-04 CH CH31/85A patent/CH666275A5/de not_active IP Right Cessation
- 1985-01-05 BG BG068285A patent/BG43189A3/xx unknown
- 1985-01-07 JP JP60000744A patent/JPS60158197A/ja active Granted
- 1985-01-07 PH PH31689A patent/PH22471A/en unknown
- 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

Also Published As

Publication number	Publication date
FI850023L (fi)	1985-07-07
SU1410866A3 (ru)	1988-07-15
AT386414B (de)	1988-08-25
GB2152502B (en)	1987-10-07
IE850022L (en)	1985-07-06
ES8605818A1 (es)	1986-04-01
AU3705984A (en)	1985-07-11
DE3500179A1 (de)	1985-07-18
LU85721A1 (fr)	1985-07-24
PL144349B1 (en)	1988-05-31
GB8432368D0 (en)	1985-02-06
HUT37628A (en)	1986-01-23
HK11590A (en)	1990-02-23
HU196221B (en)	1988-10-28
RO91262A (ro)	1987-06-30
YU2085A (en)	1987-12-31
JPS60158197A (ja)	1985-08-19
RO91262B (ro)	1987-07-01
CS247191B2 (en)	1986-12-18
ZA8410143B (en)	1985-08-28
IE57967B1 (en)	1993-06-02
IL73885A (en)	1988-10-31
NZ210606A (en)	1987-08-31
GB2152502A (en)	1985-08-07
PL251457A1 (en)	1985-11-05
PT79777A (en)	1985-01-01
NO160263C (no)	1989-03-29
BG43189A3 (en)	1988-04-15
KR850005452A (ko)	1985-08-26
DE3500179C2 (2)	1989-08-24
US4599326A (en)	1986-07-08
IL73885A0 (en)	1985-03-31
PH22471A (en)	1988-09-12
IT1184304B (it)	1987-10-28
NO850007L (no)	1985-07-08
KR900006237B1 (ko)	1990-08-27
BE901411A (fr)	1985-04-16
IS2968A7 (is)	1985-04-03
FI77249C (fi)	1989-02-10
FR2557878A1 (fr)	1985-07-12
SE8406671L (sv)	1985-07-07
ES539349A0 (es)	1986-04-01
ATA985A (de)	1988-01-15
JPH029040B2 (2)	1990-02-28
FI850023A0 (fi)	1985-01-03
DK5884A (da)	1985-07-07
YU44485B (en)	1990-08-31
CA1224461A (en)	1987-07-21
MA20316A1 (fr)	1985-10-01
SE461854B (sv)	1990-04-02
NL8403979A (nl)	1985-08-01
FR2557878B1 (fr)	1988-01-15
DK149776C (da)	1987-04-21
CH666275A5 (de)	1988-07-15
NO160263B (no)	1988-12-19
IT8519012A0 (it)	1985-01-04
DK5884D0 (da)	1984-01-06
AU565688B2 (en)	1987-09-24
FI77249B (fi)	1988-10-31
PT79777B (en)	1986-10-21
DK149776B (da)	1986-09-29
MX156277A (es)	1988-08-04
KE3841A (en)	1989-04-07
SE8406671D0 (sv)	1984-12-28

Publication	Publication Date	Title
CY1462A (en)	1989-07-21	An antibiotic compound,a method for its preparation,and compositions containing it
DK175544B1 (da)	2004-11-29	Anvendelse af azithromycin og derivater deraf til fremstilling af antiprotozoale lægemidler
US4115552A (en)	1978-09-19	Factor A and B of antibiotic A-4696
US3952095A (en)	1976-04-20	Novel antibiotic and a process for the production thereof
DK165436B (da)	1992-11-30	Dyrefoder
US4064233A (en)	1977-12-20	Antibiotic A-4696
US3873715A (en)	1975-03-25	Therapeutic agent for improving cardiovascular function
HU197770B (en)	1989-05-29	Process for producing the new 9-square brackets open (2'r, 3'r, 4's)-3',4'-bis(hydroxymethyl)-2'-oxetanyl square brackets closed-hypoxanthine and pharmaceutical compositions comprising same as active ingredient
JPH0645543B2 (ja)	1994-06-15	魚病の予防，治療剤
US3723423A (en)	1973-03-27	Novel alkoxytetrahydropyranol ethers of prostaglandins
PL87754B1 (2)	1976-07-31
JPS604189B2 (ja)	1985-02-01	抗菌剤およびその製法
JPS6234038B2 (2)	1987-07-24
PL88977B1 (2)	1976-10-30
CA1066303A (en)	1979-11-13	Aminobenzoic acid derivatives, process for preparing the same and pharmaceutical composition containing the same
US3962455A (en)	1976-06-08	Antibiotic ascofuranone and process for the production thereof
US4331658A (en)	1982-05-25	Method of treating swine dysentery with antibiotic A-32887
NO813411L (no)	1982-04-13	Nye prostaglandiner
GB1583408A (en)	1981-01-28	Antibiotic x-14547
JPH0481593B2 (2)	1992-12-24
JP2780828B2 (ja)	1998-07-30	ポリエーテル抗生物質ｍｉ２１５―ｎｆ３物質及びその製造法、並びに鶏のコクシジウム症の防除剤
SU528883A3 (ru)	1976-09-15	Способ получени антибиотиков
JPH07289273A (ja)	1995-11-07	ナフトキノン誘導体
JPS5950318B2 (ja)	1984-12-07	新規抗生物質ｓｙ−２物質
JPS5849386A (ja)	1983-03-23	セフアロスポリン誘導体及び該誘導体を含有する医薬