SK83199A3 - Novel erythromycin derivatives, method of preparation and application as medicines - Google Patents

Novel erythromycin derivatives, method of preparation and application as medicines Download PDF

Info

Publication number: SK83199A3
Authority: SK; Slovakia
Prior art keywords: formula; compounds; compound; methyl; give
Prior art date: 1996-12-23

Application number

SK831-99A

Other languages

English (en)

Slovak (sk)

Inventor

Constantin Agouridas

Jean-Francois Chantot

Original Assignee

Hoechst Marion Roussel Inc

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.)

1996-12-23

Filing date

1997-12-22

Publication date

2000-05-16

1997-12-22 Application filed by Hoechst Marion Roussel Inc filed Critical Hoechst Marion Roussel Inc

2000-05-16 Publication of SK83199A3 publication Critical patent/SK83199A3/sk

Links

239000003814 drug Substances 0.000 title claims abstract 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 claims description 9
238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 8
229940079593 drug Drugs 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 59
150000003839 salts Chemical class 0.000 claims abstract description 13
125000003118 aryl group Chemical group 0.000 claims abstract description 11
239000002253 acid Substances 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 4
238000003776 cleavage reaction Methods 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
230000007017 scission Effects 0.000 claims description 4
239000000126 substance Substances 0.000 claims description 4
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
229960003276 erythromycin Drugs 0.000 claims description 3
125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
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 claims description 2
230000000903 blocking effect Effects 0.000 claims description 2
238000010504 bond cleavage reaction Methods 0.000 claims description 2
125000005587 carbonate group Chemical group 0.000 claims description 2
239000003638 chemical reducing agent Substances 0.000 claims description 2
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
230000003115 biocidal effect Effects 0.000 abstract description 3
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239000000654 additive Substances 0.000 abstract 1
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GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
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239000000203 mixture Substances 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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125000000623 heterocyclic group Chemical group 0.000 description 5
239000000243 solution Substances 0.000 description 5
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
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KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 2
AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 2
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical group C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
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241001134658 Streptococcus mitis Species 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
229940047650 haemophilus influenzae Drugs 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
239000007788 liquid Substances 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
IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 2
244000005700 microbiome Species 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 2
LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical class CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
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 description 1
229960000549 4-dimethylaminophenol Drugs 0.000 description 1
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241000894006 Bacteria Species 0.000 description 1
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206010006500 Brucellosis Diseases 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
241000606161 Chlamydia Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241000194032 Enterococcus faecalis Species 0.000 description 1
KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
206010018612 Gonorrhoea Diseases 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
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240000007472 Leucaena leucocephala Species 0.000 description 1
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IEMDOFXTVAPVLX-YWQHLDGFSA-N Leucomycin A1 Chemical compound CO[C@H]1[C@H](O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@@H](C)O1 IEMDOFXTVAPVLX-YWQHLDGFSA-N 0.000 description 1
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125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
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CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
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150000002460 imidazoles Chemical class 0.000 description 1
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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
235000019359 magnesium stearate Nutrition 0.000 description 1
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229940098779 methanesulfonic acid Drugs 0.000 description 1
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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
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- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P11/04—Drugs for disorders of the respiratory system for throat disorders
- 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
- 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
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
- 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
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- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis

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Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Biotechnology (AREA)
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SK831-99A 1996-12-23 1997-12-22 Novel erythromycin derivatives, method of preparation and application as medicines SK83199A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9615830A FR2757518B1 (fr)	1996-12-23	1996-12-23	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments
PCT/FR1997/002380 WO1998028316A1 (fr)	1996-12-23	1997-12-22	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments

Publications (1)

Publication Number	Publication Date
SK83199A3 true SK83199A3 (en)	2000-05-16

Family

ID=9498984

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK831-99A SK83199A3 (en)	1996-12-23	1997-12-22	Novel erythromycin derivatives, method of preparation and application as medicines

Country Status (24)

Country	Link
EP (1)	EP0946580B1 (cs)
JP (2)	JP4522496B2 (cs)
KR (1)	KR20000062286A (cs)
CN (1)	CN1246123A (cs)
AP (1)	AP9901566A0 (cs)
AT (1)	ATE215553T1 (cs)
AU (1)	AU726147B2 (cs)
BR (1)	BR9713618A (cs)
CA (1)	CA2275359A1 (cs)
CZ (1)	CZ293732B6 (cs)
DE (1)	DE69711689T2 (cs)
DK (1)	DK0946580T3 (cs)
EA (1)	EA199900589A1 (cs)
ES (1)	ES2172827T3 (cs)
FR (1)	FR2757518B1 (cs)
HU (1)	HUP0001452A3 (cs)
ID (1)	ID21883A (cs)
IL (1)	IL130510A0 (cs)
NO (1)	NO993124L (cs)
PL (1)	PL334134A1 (cs)
PT (1)	PT946580E (cs)
SK (1)	SK83199A3 (cs)
TR (1)	TR199901452T2 (cs)
WO (1)	WO1998028316A1 (cs)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2757518B1 (fr) *	1996-12-23	1999-06-11	Hoechst Marion Roussel Inc	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments
YU44900A (sh)	1998-01-31	2003-01-31	Glaxo Group Limited	Derivati 2-(purin-9-il)tetrahidrofuran-3,4-diola
US6720308B1 (en) *	2002-11-07	2004-04-13	Enanta Pharmaceuticals, Inc.	Anhydrolide derivatives having antibacterial activity
GB0514809D0 (en)	2005-07-19	2005-08-24	Glaxo Group Ltd	Compounds

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL99995A (en) *	1990-11-21	1997-11-20	Roussel Uclaf	Erythromycin derivatives, their preparation and pharmaceutical compositions containing them
JPH0853355A (ja) *	1994-08-12	1996-02-27	Taisho Pharmaceut Co Ltd	Ｉｌ−５産生抑制剤
DE69626040T2 (de) *	1995-11-08	2004-01-22	Abbott Laboratories, Abbott Park	3-deoxy-3-descladinosederivate von erythromycin a und b
AU710532B2 (en) *	1996-05-07	1999-09-23	Abbott Laboratories	3-descladinose-2,3-anhydroerythromycin derivatives
FR2757518B1 (fr) *	1996-12-23	1999-06-11	Hoechst Marion Roussel Inc	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments

1996
- 1996-12-23 FR FR9615830A patent/FR2757518B1/fr not_active Expired - Fee Related
1997
- 1997-12-22 BR BR9713618-2A patent/BR9713618A/pt not_active Application Discontinuation
- 1997-12-22 SK SK831-99A patent/SK83199A3/sk unknown
- 1997-12-22 EA EA199900589A patent/EA199900589A1/ru unknown
- 1997-12-22 CA CA002275359A patent/CA2275359A1/fr not_active Abandoned
- 1997-12-22 DE DE69711689T patent/DE69711689T2/de not_active Expired - Lifetime
- 1997-12-22 DK DK97952973T patent/DK0946580T3/da active
- 1997-12-22 TR TR1999/01452T patent/TR199901452T2/xx unknown
- 1997-12-22 PT PT97952973T patent/PT946580E/pt unknown
- 1997-12-22 CZ CZ19992279A patent/CZ293732B6/cs not_active IP Right Cessation
- 1997-12-22 AT AT97952973T patent/ATE215553T1/de not_active IP Right Cessation
- 1997-12-22 ID IDW990572A patent/ID21883A/id unknown
- 1997-12-22 WO PCT/FR1997/002380 patent/WO1998028316A1/fr not_active Ceased
- 1997-12-22 AU AU56679/98A patent/AU726147B2/en not_active Ceased
- 1997-12-22 KR KR1019997005682A patent/KR20000062286A/ko not_active Withdrawn
- 1997-12-22 CN CN97181784A patent/CN1246123A/zh active Pending
- 1997-12-22 ES ES97952973T patent/ES2172827T3/es not_active Expired - Lifetime
- 1997-12-22 JP JP52847498A patent/JP4522496B2/ja not_active Expired - Lifetime
- 1997-12-22 AP APAP/P/1999/001566A patent/AP9901566A0/en unknown
- 1997-12-22 EP EP97952973A patent/EP0946580B1/fr not_active Expired - Lifetime
- 1997-12-22 IL IL13051097A patent/IL130510A0/xx unknown
- 1997-12-22 PL PL97334134A patent/PL334134A1/xx unknown
- 1997-12-22 HU HU0001452A patent/HUP0001452A3/hu unknown
1999
- 1999-06-23 NO NO993124A patent/NO993124L/no not_active Application Discontinuation
2010
- 2010-02-01 JP JP2010020522A patent/JP5188520B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
HU0001452B (hu)	2000-09-28
DK0946580T3 (da)	2002-07-22
PT946580E (pt)	2002-09-30
WO1998028316A1 (fr)	1998-07-02
JP2001507011A (ja)	2001-05-29
DE69711689D1 (de)	2002-05-08
KR20000062286A (ko)	2000-10-25
IL130510A0 (en)	2000-06-01
DE69711689T2 (de)	2002-10-17
CA2275359A1 (fr)	1998-07-02
AU726147B2 (en)	2000-11-02
PL334134A1 (en)	2000-02-14
EA199900589A1 (ru)	2000-02-28
ID21883A (id)	1999-08-05
CN1246123A (zh)	2000-03-01
AU5667998A (en)	1998-07-17
CZ293732B6 (cs)	2004-07-14
EP0946580A1 (fr)	1999-10-06
NO993124D0 (no)	1999-06-23
JP4522496B2 (ja)	2010-08-11
EP0946580B1 (fr)	2002-04-03
BR9713618A (pt)	2000-04-11
HUP0001452A3 (en)	2000-10-30
JP2010132683A (ja)	2010-06-17
FR2757518A1 (fr)	1998-06-26
FR2757518B1 (fr)	1999-06-11
CZ227999A3 (cs)	1999-10-13
NO993124L (no)	1999-08-20
JP5188520B2 (ja)	2013-04-24
ATE215553T1 (de)	2002-04-15
TR199901452T2 (xx)	1999-10-21
AP9901566A0 (en)	1999-06-30
ES2172827T3 (es)	2002-10-01

Publication	Publication Date	Title
US5527780A (en)	1996-06-18	Erythromycin derivatives
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
US5543400A (en)	1996-08-06	Erythromycin compounds
US6664398B2 (en)	2003-12-16	Derivatives of erythromycin, their preparation process and their use as medicaments
US6313101B1 (en)	2001-11-06	Derivatives of erythromycin, their preparation process and their use as medicaments
US6433151B1 (en)	2002-08-13	Erythromycin derivatives, a process for their preparation and their use as medicaments
JP5188520B2 (ja)	2013-04-24	新規なエリスロマイシン誘導体、製造方法及び医薬としての利用
AU721732B2 (en)	2000-07-13	New derivatives of erythromycin, their preparation process and their use as medicaments
AU761551B2 (en)	2003-06-05	Novel 6-deoxy erythromycin derivatives, method for preparing same and use as medicines
MXPA99005840A (en)	2000-04-24	Novel erythromycin derivatives, method of preparation and application as medicines
MXPA99005226A (en)	2000-01-01	Novel erythromycin derivatives, method for preparing them and their use as medicine