AP952A - Novel erthromycin derivatives, method for preparing same, and use thereof as drugs. - Google Patents

Novel erthromycin derivatives, method for preparing same, and use thereof as drugs. Download PDF

Info

Publication number: AP952A
Authority: AP; ARIPO
Prior art keywords: formula; radical; compounds; methyl; dideoxy
Prior art date: 1996-02-28

Application number

APAP/P/1998/001318A

Other languages

English (en)

Other versions

AP9801318A0 (en

Inventor

Constantin Agouridas

Jean-Francis Chantot (Deceased)

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.)

1996-02-28

Filing date

1997-02-27

Publication date

2001-03-29

1997-02-27 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

1998-09-30 Publication of AP9801318A0 publication Critical patent/AP9801318A0/xx

2001-03-29 Application granted granted Critical

2001-03-29 Publication of AP952A publication Critical patent/AP952A/en

Links

239000003814 drug Substances 0.000 title claims description 13
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 description 16
238000000034 method Methods 0.000 title description 8
229940079593 drug Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 32
150000003254 radicals Chemical class 0.000 claims abstract description 16
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
-1 CH2 radical Chemical group 0.000 claims description 27
229960003276 erythromycin Drugs 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
238000003776 cleavage reaction Methods 0.000 claims description 7
230000007017 scission Effects 0.000 claims description 7
150000007513 acids Chemical class 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 4
125000005638 hydrazono group Chemical group 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
YHVUVJYEERGYNU-UHFFFAOYSA-N 4',8-Di-Me ether-5,7,8-Trihydroxy-3-(4-hydroxybenzyl)-4-chromanone Natural products COC1(C)CC(O)OC(C)C1O YHVUVJYEERGYNU-UHFFFAOYSA-N 0.000 claims description 3
AJSDVNKVGFVAQU-BIIVOSGPSA-N cladinose Chemical compound O=CC[C@@](C)(OC)[C@@H](O)[C@H](C)O AJSDVNKVGFVAQU-BIIVOSGPSA-N 0.000 claims description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
230000032050 esterification Effects 0.000 claims 1
238000005886 esterification reaction Methods 0.000 claims 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
150000005840 aryl radicals Chemical class 0.000 abstract description 4
230000003115 biocidal effect Effects 0.000 abstract description 4
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical group NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 abstract 1
239000000047 product Substances 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
244000052616 bacterial pathogen Species 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
206010002383 Angina Pectoris Diseases 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
206010041925 Staphylococcal infections Diseases 0.000 description 2
241000191967 Staphylococcus aureus Species 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
241000193985 Streptococcus agalactiae Species 0.000 description 2
241001134658 Streptococcus mitis Species 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
238000013019 agitation Methods 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
239000007788 liquid Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
238000001819 mass spectrum Methods 0.000 description 2
238000004452 microanalysis Methods 0.000 description 2
GTJNQHWEJNBLLS-UHFFFAOYSA-N n,n-diethylethanamine;methanol;2-propan-2-yloxypropane Chemical compound OC.CCN(CC)CC.CC(C)OC(C)C GTJNQHWEJNBLLS-UHFFFAOYSA-N 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
MWBJRTBANFUBOX-SQYJNGITSA-N (3r,4s,5s,6r,7r,9r,10e,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclot Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N/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 MWBJRTBANFUBOX-SQYJNGITSA-N 0.000 description 1
244000215068 Acacia senegal Species 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
208000002874 Acne Vulgaris Diseases 0.000 description 1
241000193738 Bacillus anthracis Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
201000004813 Bronchopneumonia Diseases 0.000 description 1
206010006500 Brucellosis Diseases 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
206010007882 Cellulitis Diseases 0.000 description 1
241000606161 Chlamydia Species 0.000 description 1
241000194032 Enterococcus faecalis Species 0.000 description 1
241000194031 Enterococcus faecium Species 0.000 description 1
201000000297 Erysipelas Diseases 0.000 description 1
206010018612 Gonorrhoea Diseases 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
241000606768 Haemophilus influenzae Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
241000589248 Legionella Species 0.000 description 1
208000007764 Legionnaires' Disease Diseases 0.000 description 1
208000032376 Lung infection Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000186359 Mycobacterium Species 0.000 description 1
241000202934 Mycoplasma pneumoniae Species 0.000 description 1
208000005141 Otitis Diseases 0.000 description 1
208000035109 Pneumococcal Infections Diseases 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
206010039587 Scarlet Fever Diseases 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
241000295644 Staphylococcaceae Species 0.000 description 1
206010056430 Staphylococcal sepsis Diseases 0.000 description 1
241000191963 Staphylococcus epidermidis Species 0.000 description 1
206010061372 Streptococcal infection Diseases 0.000 description 1
241000194017 Streptococcus Species 0.000 description 1
241000193998 Streptococcus pneumoniae Species 0.000 description 1
241000193996 Streptococcus pyogenes Species 0.000 description 1
241000223996 Toxoplasma Species 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
206010000496 acne Diseases 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910000024 caesium carbonate Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000006071 cream Substances 0.000 description 1
230000006196 deacetylation Effects 0.000 description 1
238000003381 deacetylation reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
206010013023 diphtheria Diseases 0.000 description 1
239000002270 dispersing agent Substances 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
239000012374 esterification agent Substances 0.000 description 1
150000002148 esters Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
125000002541 furyl group Chemical group 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
238000010438 heat treatment Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
238000011534 incubation Methods 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000008101 lactose Substances 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
230000003211 malignant effect Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
CSYNQJPENMOLHR-UHFFFAOYSA-N n,n-diethylethanamine;ethyl acetate Chemical compound CCOC(C)=O.CCN(CC)CC CSYNQJPENMOLHR-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 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
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
201000009890 sinusitis Diseases 0.000 description 1
239000011734 sodium Substances 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
229940031000 streptococcus pneumoniae Drugs 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Oncology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Communicable Diseases (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

APAP/P/1998/001318A 1996-02-28 1997-02-27 Novel erthromycin derivatives, method for preparing same, and use thereof as drugs. AP952A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9602472A FR2745290B1 (fr)	1996-02-28	1996-02-28	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments
PCT/FR1997/000351 WO1997031929A1 (fr)	1996-02-28	1997-02-27	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments

Publications (2)

Publication Number	Publication Date
AP9801318A0 AP9801318A0 (en)	1998-09-30
AP952A true AP952A (en)	2001-03-29

Family

ID=9489659

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1998/001318A AP952A (en)	1996-02-28	1997-02-27	Novel erthromycin derivatives, method for preparing same, and use thereof as drugs.

Country Status (31)

Country	Link
US (1)	US6096714A (pl)
EP (1)	EP0885234B1 (pl)
JP (1)	JP4102440B2 (pl)
KR (1)	KR100486053B1 (pl)
CN (1)	CN1168734C (pl)
AP (1)	AP952A (pl)
AR (1)	AR005999A1 (pl)
AT (1)	ATE217633T1 (pl)
AU (1)	AU716204B2 (pl)
BG (1)	BG63207B1 (pl)
BR (1)	BR9707709B1 (pl)
CZ (1)	CZ293893B6 (pl)
DE (1)	DE69712610T2 (pl)
DK (1)	DK0885234T3 (pl)
EA (1)	EA001376B1 (pl)
EE (1)	EE9800265A (pl)
ES (1)	ES2176698T3 (pl)
FR (1)	FR2745290B1 (pl)
HU (1)	HU227567B1 (pl)
IL (1)	IL125622A (pl)
NO (1)	NO983955L (pl)
NZ (1)	NZ331600A (pl)
OA (1)	OA10845A (pl)
PL (1)	PL191736B1 (pl)
PT (1)	PT885234E (pl)
SK (1)	SK118498A3 (pl)
TR (1)	TR199801713T2 (pl)
UA (1)	UA58504C2 (pl)
WO (1)	WO1997031929A1 (pl)
YU (1)	YU37098A (pl)
ZA (1)	ZA971659B (pl)

Families Citing this family (27)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2004514643A (ja) *	1997-10-29	2004-05-20	大正製薬株式会社	エリスロマイシンａ誘導体
WO1999021869A1 (en) *	1997-10-29	1999-05-06	Taisho Pharmaceutical Co., Ltd.	Erythromycin a, 11,12-carbamate derivatives
FR2780977B1 (fr) *	1998-07-09	2000-09-01	Hoechst Marion Roussel Inc	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments
JP4573925B2 (ja) *	1998-07-09	2010-11-04	アベンティス・ファーマ・ソシエテ・アノニム	新規のエリスロマイシン誘導体、その製造方法及びその薬剤としての使用
FR2792637B1 (fr) *	1999-04-26	2001-06-01	Hoechst Marion Roussel Inc	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments
FR2781484B1 (fr) *	1998-07-21	2001-08-10	Hoechst Marion Roussel Inc	Nouveaux derives de la 6-deoxy erythromycine, leur procede de preparation et leur application comme medicaments
DK1147121T3 (da)	1999-01-27	2004-04-13	Pfizer Prod Inc	Ketolidantibiotika
EE200100613A (et) *	1999-05-24	2003-02-17	Pfizer Products Inc.	13-metüülerütromütsiini derivaadid
AU6183800A (en) *	1999-08-06	2001-03-05	Taisho Pharmaceutical Co., Ltd.	Erythromycin a derivatives
WO2001010878A1 (fr) *	1999-08-06	2001-02-15	Taisho Pharmaceutical Co., Ltd.	Derives d'erythromycine a
AU6316400A (en) *	1999-08-06	2001-03-05	Taisho Pharmaceutical Co., Ltd.	Erythromycin a derivatives
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- 1997-02-27 BR BRPI9707709-7A patent/BR9707709B1/pt not_active IP Right Cessation
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- 1997-02-27 DK DK97907141T patent/DK0885234T3/da active
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Also Published As

Publication number	Publication date
BG63207B1 (bg)	2001-06-29
PT885234E (pt)	2002-10-31
KR19990087324A (ko)	1999-12-27
NZ331600A (en)	1999-08-30
EP0885234A1 (fr)	1998-12-23
HU227567B1 (en)	2011-08-29
EA001376B1 (ru)	2001-02-26
CZ293893B6 (cs)	2004-08-18
HUP9902576A1 (hu)	1999-12-28
JP4102440B2 (ja)	2008-06-18
SK118498A3 (en)	1999-07-12
FR2745290A1 (fr)	1997-08-29
HUP9902576A3 (en)	2001-03-28
PL191736B1 (pl)	2006-06-30
CZ258798A3 (cs)	1998-12-16
DE69712610D1 (de)	2002-06-20
AU1929897A (en)	1997-09-16
ATE217633T1 (de)	2002-06-15
BG102691A (en)	1999-06-30
AR005999A1 (es)	1999-07-21
CN1168734C (zh)	2004-09-29
US6096714A (en)	2000-08-01
KR100486053B1 (ko)	2005-06-16
TR199801713T2 (xx)	1998-12-21
IL125622A0 (en)	1999-04-11
DK0885234T3 (da)	2002-08-26
WO1997031929A1 (fr)	1997-09-04
DE69712610T2 (de)	2002-11-28
EE9800265A (et)	1999-02-15
UA58504C2 (uk)	2003-08-15
FR2745290B1 (fr)	1998-04-03
IL125622A (en)	2003-10-31
EP0885234B1 (fr)	2002-05-15
ES2176698T3 (es)	2002-12-01
NO983955D0 (no)	1998-08-27
YU37098A (sh)	1999-07-28
OA10845A (fr)	2003-02-05
CN1212700A (zh)	1999-03-31
AP9801318A0 (en)	1998-09-30
JP2000505469A (ja)	2000-05-09
EA199800768A1 (ru)	1999-02-25
ZA971659B (en)	1998-02-26
BR9707709B1 (pt)	2014-10-14
BR9707709A (pt)	1999-04-06
AU716204B2 (en)	2000-02-24
NO983955L (no)	1998-08-27
PL328608A1 (en)	1999-02-01

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