AP558A - New erythromycin derivatives, their preparation process and their use as medicaments. - Google Patents

New erythromycin derivatives, their preparation process and their use as medicaments. Download PDF

Info

Publication number: AP558A
Authority: AP; ARIPO
Prior art keywords: butanamine; methyl; dideoxy; oxy; formula
Prior art date: 1994-05-03

Application number

APAP/P/1995/000744A

Other languages

English (en)

Other versions

AP9500744A0 (en

Inventor

Constantin Agouridas

Jean-Francis Chantot (Deceased)

Alexis Denis

Solange Gouin D'ambrieres

Martret Odile Le

Original Assignee

Aventis Pharma Sa

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.)

1994-05-03

Filing date

1995-05-02

Publication date

1996-11-07

1995-05-02 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

1995-07-31 Publication of AP9500744A0 publication Critical patent/AP9500744A0/xx

1996-11-07 Application granted granted Critical

1996-11-07 Publication of AP558A publication Critical patent/AP558A/en

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 claims description 114
238000002360 preparation method Methods 0.000 title claims description 36
239000003814 drug Substances 0.000 title claims description 13
229960003276 erythromycin Drugs 0.000 claims description 57
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 49
150000001875 compounds Chemical class 0.000 claims description 42
-1 heterocyclic radical Chemical class 0.000 claims description 35
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 27
125000001841 imino group Chemical group [H]N=* 0.000 claims description 24
150000003254 radicals Chemical class 0.000 claims description 22
239000002253 acid Substances 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 13
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims description 10
150000007513 acids Chemical class 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 claims description 4
229960005038 quinisocaine Drugs 0.000 claims description 4
241001334574 Erythromyces Species 0.000 claims description 3
239000004305 biphenyl Substances 0.000 claims description 3
SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 claims description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 2
239000012964 benzotriazole Substances 0.000 claims description 2
HWFXUWJTXXPEBY-UHFFFAOYSA-N butan-1-amine;1h-1,2,4-triazole Chemical compound CCCCN.C=1N=CNN=1 HWFXUWJTXXPEBY-UHFFFAOYSA-N 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
239000000047 product Substances 0.000 description 99
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125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000002704 decyl 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])* 0.000 description 1
HFPGRVHMFSJMOL-UHFFFAOYSA-N dibromomethane Chemical compound Br[CH]Br HFPGRVHMFSJMOL-UHFFFAOYSA-N 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
206010013023 diphtheria Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
125000003438 dodecyl 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 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
208000019258 ear infection Diseases 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
VOEPIFVLNUODAC-UHFFFAOYSA-N ethyl 2-pyridin-2-yl-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(C=2N=CC=CC=2)=N1 VOEPIFVLNUODAC-UHFFFAOYSA-N 0.000 description 1
VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000009036 growth inhibition Effects 0.000 description 1
229940047650 haemophilus influenzae Drugs 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000003211 malignant effect Effects 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
230000000050 nutritive effect Effects 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
229940081066 picolinic acid Drugs 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
HYKQYVSNFPWGKQ-UHFFFAOYSA-N pyridine-2-carbothioamide Chemical compound NC(=S)C1=CC=CC=N1 HYKQYVSNFPWGKQ-UHFFFAOYSA-N 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
201000009890 sinusitis Diseases 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
DCGLONGLPGISNX-UHFFFAOYSA-N trimethyl(prop-1-ynyl)silane Chemical compound CC#C[Si](C)(C)C DCGLONGLPGISNX-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 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
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- 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
- 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
- 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
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Virology (AREA)
Bioinformatics & Cheminformatics (AREA)
Tropical Medicine & Parasitology (AREA)
Dermatology (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Quinoline Compounds (AREA)
Indole Compounds (AREA)
Pyrrole Compounds (AREA)
Thiazole And Isothizaole Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)

APAP/P/1995/000744A 1994-05-03 1995-05-02 New erythromycin derivatives, their preparation process and their use as medicaments. AP558A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9405368A FR2719587B1 (fr)	1994-05-03	1994-05-03	Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments.

Publications (2)

Publication Number	Publication Date
AP9500744A0 AP9500744A0 (en)	1995-07-31
AP558A true AP558A (en)	1996-11-07

Family

ID=9462785

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1995/000744A AP558A (en)	1994-05-03	1995-05-02	New erythromycin derivatives, their preparation process and their use as medicaments.

Country Status (42)

Country	Link
US (2)	US5635485A (pl)
EP (1)	EP0680967B1 (pl)
JP (4)	JP2992540B2 (pl)
KR (1)	KR100312267B1 (pl)
CN (2)	CN1052984C (pl)
AP (1)	AP558A (pl)
AT (1)	ATE172203T1 (pl)
AU (1)	AU684027B2 (pl)
BG (1)	BG63087B1 (pl)
BR (1)	BR9507700A (pl)
CA (1)	CA2189271C (pl)
CZ (1)	CZ293455B6 (pl)
DE (2)	DE10299001I2 (pl)
DK (1)	DK0680967T3 (pl)
DZ (1)	DZ1878A1 (pl)
EE (1)	EE03263B1 (pl)
ES (1)	ES2122472T3 (pl)
FI (1)	FI111263B (pl)
FR (1)	FR2719587B1 (pl)
GE (1)	GEP19991538B (pl)
HU (2)	HU219599B (pl)
IL (1)	IL113245A (pl)
LU (1)	LU90872I2 (pl)
LV (1)	LV11739B (pl)
MA (1)	MA23534A1 (pl)
MD (1)	MD1233C2 (pl)
NL (1)	NL300077I1 (pl)
NO (2)	NO308853B1 (pl)
NZ (1)	NZ285416A (pl)
OA (1)	OA10319A (pl)
PL (1)	PL182034B1 (pl)
RO (1)	RO113350B1 (pl)
RU (1)	RU2144036C1 (pl)
SI (1)	SI0680967T1 (pl)
SK (1)	SK281707B6 (pl)
TJ (1)	TJ313B (pl)
TN (1)	TNSN95049A1 (pl)
TW (1)	TW341573B (pl)
UA (1)	UA51618C2 (pl)
WO (1)	WO1995029929A1 (pl)
YU (1)	YU49235B (pl)
ZA (1)	ZA953501B (pl)

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Also Published As

Publication number	Publication date
CN1052984C (zh)	2000-05-31
JP4658902B2 (ja)	2011-03-23
CZ293455B6 (cs)	2004-05-12
LV11739A (lv)	1997-04-20
NL300077I1 (nl)	2002-03-01
MX9605208A (es)	1997-09-30
DE69505296T2 (de)	1999-04-22
PL182034B1 (pl)	2001-10-31
FI964395L (fi)	1996-10-31
HUT75698A (en)	1997-05-28
NO308853B1 (no)	2000-11-06
EP0680967A1 (fr)	1995-11-08
CN1088709C (zh)	2002-08-07
EE03263B1 (et)	2000-04-17
IL113245A0 (en)	1995-07-31
JPH11152296A (ja)	1999-06-08
KR100312267B1 (ko)	2002-06-22
FI964395A0 (fi)	1996-10-31
CN1229082A (zh)	1999-09-22
AU2449995A (en)	1995-11-29
CN1151746A (zh)	1997-06-11
MA23534A1 (fr)	1995-12-31
DE69505296D1 (de)	1998-11-19
YU49235B (sh)	2004-12-31
ZA953501B (en)	1996-05-02
DE10299001I1 (de)	2012-07-05
DZ1878A1 (fr)	2002-02-17
ES2122472T3 (es)	1998-12-16
SK281707B6 (sk)	2001-07-10
HU219599B (hu)	2001-05-28
HU9904687D0 (en)	2000-03-28
JP2007045847A (ja)	2007-02-22
BG100951A (en)	1997-08-29
TNSN95049A1 (fr)	1996-02-06
AP9500744A0 (en)	1995-07-31
UA51618C2 (uk)	2002-12-16
US5635485A (en)	1997-06-03
FR2719587B1 (fr)	1996-07-12
NO964654L (no)	1996-11-04
BG63087B1 (bg)	2001-03-30
RU2144036C1 (ru)	2000-01-10
BR9507700A (pt)	1997-08-19
PL317071A1 (en)	1997-03-03
DE10299001I2 (de)	2012-07-05
JP3998828B2 (ja)	2007-10-31
NO2001027I1 (no)	2002-01-28
SI0680967T1 (en)	1999-02-28
EP0680967B1 (fr)	1998-10-14
JP2007269810A (ja)	2007-10-18
JP4750755B2 (ja)	2011-08-17
DK0680967T3 (da)	1999-06-23
CZ321496A3 (en)	1997-08-13
HK1010732A1 (en)	1999-06-25
CA2189271C (fr)	2005-12-27
ATE172203T1 (de)	1998-10-15
OA10319A (fr)	1997-10-07
NZ285416A (en)	1997-07-27
IL113245A (en)	1999-11-30
MD1233C2 (ro)	2000-10-31
AU684027B2 (en)	1997-11-27
GEP19991538B (en)	1999-03-05
LU90872I2 (fr)	2002-03-12
JP2992540B2 (ja)	1999-12-20
HU227493B1 (en)	2011-07-28
HU9603038D0 (en)	1997-01-28
TW341573B (en)	1998-10-01
MD1233B1 (en)	1999-05-31
WO1995029929A1 (fr)	1995-11-09
LV11739B (en)	1997-08-20
FI111263B (fi)	2003-06-30
YU27095A (sh)	1998-05-15
SK140296A3 (en)	1998-04-08
FR2719587A1 (fr)	1995-11-10
JPH0853489A (ja)	1996-02-27
US6100404A (en)	2000-08-08
RO113350B1 (ro)	1998-06-30
CA2189271A1 (fr)	1995-11-09
TJ313B (en)	2001-08-06
NO964654D0 (no)	1996-11-04

Publication	Publication Date	Title
AP558A (en)	1996-11-07	New erythromycin derivatives, their preparation process and their use as medicaments.
JP3000023B2 (ja)	2000-01-17	新規なエリスロマイシン誘導体、それらの製造法及び薬剤としての使用
JP4102440B2 (ja)	2008-06-18	新規なエリスロマイシン誘導体、それらの調製方法及びそれらの医薬品としての使用
US5786339A (en)	1998-07-28	Erythromycins
US6313101B1 (en)	2001-11-06	Derivatives of erythromycin, their preparation process and their use as medicaments
FR2732684A1 (fr)	1996-10-11	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments
MXPA96005208A (en)	1998-07-03	New derivatives of erythromycin, its procedure of preparation and its application as medicamen
HK1010732B (en)	2000-05-19	Erythromycin derivatives, their process of preparation and their use as medicaments