HRP980571A2 - 9-amino-3-keto erythromycin derivatives - Google Patents

9-amino-3-keto erythromycin derivatives

Info

Publication number: HRP980571A2
Authority: HR; Croatia
Prior art keywords: alkyl; methyl; propyl; carbamate; desosaminyl
Prior art date: 1997-10-29

Application number

HR60/063,676A

Other languages

English (en)

Croatian (hr)

Inventor

Yong-Jin Wu

Original Assignee

Yong-Jin Wu

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.)

1997-10-29

Filing date

1998-10-29

Publication date

1999-08-31

1998-10-29 Application filed by Yong-Jin Wu filed Critical Yong-Jin Wu

1999-08-31 Publication of HRP980571A2 publication Critical patent/HRP980571A2/hr

Links

150000001875 compounds Chemical class 0.000 claims description 145
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 128
125000001424 substituent group Chemical group 0.000 claims description 44
125000000623 heterocyclic group Chemical group 0.000 claims description 43
208000015181 infectious disease Diseases 0.000 claims description 40
150000003839 salts Chemical class 0.000 claims description 32
-1 -NR5R6 Chemical group 0.000 claims description 31
229910052757 nitrogen Inorganic materials 0.000 claims description 31
125000001589 carboacyl group Chemical group 0.000 claims description 29
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 29
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 24
125000005843 halogen group Chemical group 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 20
125000004093 cyano group Chemical group *C#N 0.000 claims description 20
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
238000000034 method Methods 0.000 claims description 14
125000005842 heteroatom Chemical group 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 13
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
241000251468 Actinopterygii Species 0.000 claims description 10
241000124008 Mammalia Species 0.000 claims description 10
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 8
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 8
229910010062 TiCl3 Inorganic materials 0.000 claims description 8
239000003638 chemical reducing agent Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical group Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
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125000003118 aryl group Chemical group 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
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125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
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239000000825 pharmaceutical preparation Substances 0.000 claims description 2
YFOKBFRTGLSZLU-UHFFFAOYSA-N 3-(1h-imidazol-5-yl)pyridine Chemical compound N1C=NC=C1C1=CC=CN=C1 YFOKBFRTGLSZLU-UHFFFAOYSA-N 0.000 claims 1
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239000012044 organic layer Substances 0.000 description 52
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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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

HR60/063,676A 1997-10-29 1998-10-29 9-amino-3-keto erythromycin derivatives HRP980571A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US6367697P	1997-10-29	1997-10-29

Publications (1)

Publication Number	Publication Date
HRP980571A2 true HRP980571A2 (en)	1999-08-31

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ID=22050768

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR60/063,676A HRP980571A2 (en)	1997-10-29	1998-10-29	9-amino-3-keto erythromycin derivatives

Country Status (13)

Country	Link
US (1)	US6159945A (fr)
AP (1)	AP9801378A0 (fr)
AR (1)	AR017177A1 (fr)
AU (1)	AU9277698A (fr)
CO (1)	CO4810375A1 (fr)
GT (1)	GT199800163A (fr)
HN (1)	HN1998000159A (fr)
HR (1)	HRP980571A2 (fr)
MA (1)	MA26558A1 (fr)
PA (1)	PA8461701A1 (fr)
PE (1)	PE122499A1 (fr)
TN (1)	TNSN98194A1 (fr)
WO (1)	WO1999021866A1 (fr)

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Publication number	Priority date	Publication date	Assignee	Title
US6710033B1 (en)	1996-08-14	2004-03-23	Vanderbilt University	Methods and treatment of multiple sclerosis
US6890526B2 (en)	1997-05-06	2005-05-10	Vanderbilt University	Methods and reagents for the treatment of multiple sclerosis
AP9801420A0 (en) *	1998-01-02	1998-12-31	Pfizer Prod Inc	Novel macrolides.
AU3439899A (en) *	1998-06-03	1999-12-20	Pfizer Products Inc.	Tricyclic 3-keto derivatives of 6-o-methylerythromycin
TR200102129T2 (tr)	1998-12-10	2002-01-21	Pfizer Products Inc.	Karbamat ve karbazat ketolid antibiyotikleri.
EP1298138B1 (fr) *	1998-12-10	2006-11-02	Pfizer Products Inc.	Dérivés anitiobiotiques de Carbamate et de Carbazate Kètolides
CA2359708C (fr)	1999-01-27	2005-10-25	Pfizer Products Inc.	Antibiotiques cetolides
EA200100983A1 (ru) *	1999-05-24	2002-10-31	Пфайзер Продактс Инк.	Производные 13-метилэритромицина
ID27331A (id) *	1999-09-29	2001-03-29	Pfizer Prod Inc	Pembuatan antibiotik-antibiotik ketolida karbamat
US6498146B1 (en) *	1999-10-28	2002-12-24	Pfizer Inc	Erythromycin derivatives
EP1146051A3 (fr) *	2000-04-10	2001-10-31	Pfizer Products Inc.	Dérivées de l' érythromycine A
US20020115621A1 (en) *	2000-08-07	2002-08-22	Wei-Gu Su	Macrolide antibiotics
US20040208842A1 (en) *	2001-09-18	2004-10-21	Ritchie Branson W.	Antimicrobial cleansing compositions and methods of use
US20070003508A1 (en)	2005-07-01	2007-01-04	Wooley Richard E	Methods and compositions for promoting wound healing
US20040151765A1 (en) *	2001-09-18	2004-08-05	Ritchie Branson W.	Methods and compositions for wound management
ES2552682T3 (es)	2003-03-10	2015-12-01	Merck Sharp & Dohme Corp.	Agentes antibacterianos novedosos
WO2005091967A2 (fr) *	2004-03-03	2005-10-06	University Of Georgia Research Foundation, Inc.	Procedes et compositions destines au traitement ophtalmique d'infections fongiques et bacteriennes
UA85937C2 (uk)	2004-12-21	2009-03-10	Пфайзер Продактс Інк.	Макроліди
CN105732745A (zh)	2007-10-25	2016-07-06	森普拉制药公司	大环内酯类抗菌剂的制备方法
AU2009308182B2 (en)	2008-10-24	2016-05-19	Cempra Pharmaceuticals, Inc.	Biodefenses using triazole-containing macrolides
US9937194B1 (en)	2009-06-12	2018-04-10	Cempra Pharmaceuticals, Inc.	Compounds and methods for treating inflammatory diseases
US9480679B2 (en)	2009-09-10	2016-11-01	Cempra Pharmaceuticals, Inc.	Methods for treating malaria, tuberculosis and MAC diseases
DK2550286T3 (en)	2010-03-22	2016-02-29	Cempra Pharmaceuticals Inc	CRYSTALLINE FORMS OF A MACROLID AND APPLICATIONS THEREOF
CN105198944B (zh)	2010-05-20	2018-06-01	森普拉制药公司	制备大环内酯和酮内酯及其中间体的方法
EP2613630A4 (fr)	2010-09-10	2014-01-15	Cempra Pharmaceuticals Inc	Fluorocétolides formant des liaisons hydrogène pour traiter les maladies
MX2014011537A (es)	2012-03-27	2015-02-10	Cempra Pharmaceuticals Inc	Formulaciones parenterales para la administracion de antibioticos macrolidos.
HK1217665A1 (zh)	2013-03-14	2017-01-20	森普拉制药公司	用於治療呼吸道疾病的方法及其製劑
RU2015138797A (ru)	2013-03-15	2017-04-24	Семпра Фармасьютикалс, Инк.	Конвергентные способы получения макролидных антибактериальных агентов
US9982005B2 (en) *	2013-04-04	2018-05-29	President And Fellows Of Harvard College	Macrolides and methods of their preparation and use
US10633407B2 (en)	2014-10-08	2020-04-28	President And Fellows Of Harvard College	14-membered ketolides and methods of their preparation and use
JP2018509452A (ja)	2015-03-25	2018-04-05	プレジデントアンドフェローズオブハーバードカレッジ	修飾デソサミン糖をもつマクロライドおよびその使用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL114589A (en) *	1990-11-21	1999-12-22	Roussel Uclaf	Intermediates for the preparation of erythromycin derivatives
US6060234A (en) *	1991-01-17	2000-05-09	Abbott Laboratories	Polyketide derivatives and recombinant methods for making same
ATE135707T1 (de) *	1992-04-22	1996-04-15	Taisho Pharmaceutical Co Ltd	5-0-desosaminylerythronolid a derivate
WO1998051696A1 (fr) *	1997-05-09	1998-11-19	Pfizer Products Inc.	Derives d'erythromycine
CZ9904388A3 (cs) *	1997-06-11	2002-10-16	Pfizer Products Inc.	9-Oximové deriváty erythromycinu

1998
- 1998-10-08 HN HN1998000159A patent/HN1998000159A/es unknown
- 1998-10-09 US US09/402,338 patent/US6159945A/en not_active Expired - Fee Related
- 1998-10-09 AU AU92776/98A patent/AU9277698A/en not_active Abandoned
- 1998-10-09 WO PCT/IB1998/001578 patent/WO1999021866A1/fr not_active Ceased
- 1998-10-16 PA PA19988461701A patent/PA8461701A1/es unknown
- 1998-10-22 PE PE1998000993A patent/PE122499A1/es not_active Application Discontinuation
- 1998-10-23 GT GT199800163A patent/GT199800163A/es unknown
- 1998-10-26 MA MA25314A patent/MA26558A1/fr unknown
- 1998-10-26 TN TNTNSN98194A patent/TNSN98194A1/fr unknown
- 1998-10-27 AR ARP980105379A patent/AR017177A1/es not_active Application Discontinuation
- 1998-10-29 CO CO98063687A patent/CO4810375A1/es unknown
- 1998-10-29 HR HR60/063,676A patent/HRP980571A2/hr not_active Application Discontinuation
- 1998-10-29 AP APAP/P/1998/001378A patent/AP9801378A0/en unknown

Also Published As

Publication number	Publication date
US6159945A (en)	2000-12-12
AU9277698A (en)	1999-05-17
GT199800163A (es)	2000-04-15
AR017177A1 (es)	2001-08-22
PE122499A1 (es)	1999-12-02
MA26558A1 (fr)	2004-12-20
TNSN98194A1 (fr)	2005-03-15
PA8461701A1 (es)	2000-05-24
AP9801378A0 (en)	2000-04-29
WO1999021866A1 (fr)	1999-05-06
CO4810375A1 (es)	1999-06-30
HN1998000159A (es)	1999-02-09

Legal Events

Date	Code	Title	Description
1998-10-29	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
1999-08-31	A1OB	Publication of a patent application
1999-10-29	ODRP	Renewal fee for the maintenance of a patent	Payment date: 19991029 Year of fee payment: 2
2005-09-19	ODBC	Application rejected

Publication	Publication Date	Title
HRP980571A2 (en)	1999-08-31	9-amino-3-keto erythromycin derivatives
US6833444B2 (en)	2004-12-21	Ketolide antibiotics
HRP980316A2 (en)	1999-04-30	9-oxime erythromycin derivatives
US6664238B1 (en)	2003-12-16	Carbamate and carbazate ketolide antibiotics
EP1132392B1 (fr)	2004-03-03	Kétolides antibiotiques
EP0992509B1 (fr)	2004-09-22	Nouveaux dérivés macrolides
US6291656B1 (en)	2001-09-18	Tricyclic erythromycin derivatives
US6727352B2 (en)	2004-04-27	Methods of making macrolides
US6262030B1 (en)	2001-07-17	Erythromycin derivatives
EP1114826A2 (fr)	2001-07-11	Macrolides antibactériennes et prokinétiques
EP1167376B1 (fr)	2004-07-14	Macrolides antibiotiques
US20030100742A1 (en)	2003-05-29	Erythromycin a derivatives
EP1122261A2 (fr)	2001-08-08	Macrolides antibactériennes à 13 ou 14 chainons
US6162794A (en)	2000-12-19	Erythromycin derivatives
US20020061856A1 (en)	2002-05-23	Novel tricyclic erythromycin derivatives
US20020151507A1 (en)	2002-10-17	9-oxime erythromycin derivatives
EP1439186A2 (fr)	2004-07-21	Intermédiaires pour macrolides antibactérielles et procinétiques
MXPA01002355A (en)	2002-06-05	Ketolide antibiotics
MXPA01007584A (en)	2002-05-09	Ketolide antibiotics