HUP0002252A2 - 9-oxime erythromycin derivatives, process for preparing them and pharmaceutical compositions containing them - Google Patents
9-oxime erythromycin derivatives, process for preparing them and pharmaceutical compositions containing themInfo
- Publication number
- HUP0002252A2 HUP0002252A2 HU0002252A HUP0002252A HUP0002252A2 HU P0002252 A2 HUP0002252 A2 HU P0002252A2 HU 0002252 A HU0002252 A HU 0002252A HU P0002252 A HUP0002252 A HU P0002252A HU P0002252 A2 HUP0002252 A2 HU P0002252A2
- Authority
- HU
- Hungary
- Prior art keywords
- group
- general formula
- carbon atoms
- alkyl
- carbon
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 125000004432 carbon atom Chemical group C* 0.000 abstract 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 229910052799 carbon Inorganic materials 0.000 abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- 229910052717 sulfur Inorganic materials 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- -1 nitro- Chemical class 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 241000251468 Actinopterygii Species 0.000 abstract 1
- 241000271566 Aves Species 0.000 abstract 1
- 208000035143 Bacterial infection Diseases 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 abstract 1
- 208000010362 Protozoan Infections Diseases 0.000 abstract 1
- 230000001580 bacterial effect Effects 0.000 abstract 1
- 208000022362 bacterial infectious disease Diseases 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 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
- A61P31/04—Antibacterial agents
-
- 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
Abstract
A találmány tárgyát képezik az emlősök, halak és madarak bakteriálisés protozoa fertőzésének kezelésére vagy megelőzésére szolgáló (i)általános képletű - ahol X jelentése -CR7R8- vagy -NR7 általánosképletű csoport; vagy X1 és R2 együttesen egy -N=CR4R5 általánosképletű csoportot; vagy X1 és R2 együttesen egy, adott esetbenhelyettesített, (XVI) általános képletű heterociklusos csoportotképeznek, melyen belül r és p jelentése egymástól függetlenül 1-3közötti egész szám, q jelentése 0 vagy 1 és X1 jelentése -CH2-, -C(O)-, -C(S)-, -SO2-, -CH=CH-, -CH(OH)CH(OH)-, -NH- képletű csoportvagy oxigén- vagy kénatom. R1 jelentése hidrogénatom vagy 1-10szénatomos alkilcsoport, ahol a nevezett alkilcsoport 1-3 szénatomjátadott esetben O, S vagy N heteroatom helyettesítheti és a nevezettalkilcsoport adott esetben 1-3 szubsztituenssel helyettesített,melyeket egymástól függetlenül -C(O)O(1-10 szénatomos alkil) általánosképletű, 1-10 szénatomos alkoxi-, 1-10 szénatomos alkanoil-, nitro-,ciano-, 5-10-tagú heterociklusos, 1-10 szénatomos alkil-, -NR7R8általános képletű, 6-10 szénatomos aril-, -S(O)n(1-10 szénatomosalkil) - melyen belül n jelentése 0-2 közötti egész szám - általánosképletű, -SO2NR7R8 általános képletű csoportokból vagyhalogénatomokból választják meg; R2 jelentése (i) hidrogénatom, -C(O)R4, -C(O)OR4 vagy -(CR7R8)mR3 általános képletű csoport, amikor Xjelentése -NR7- általános képletű csoport, vagy (ii) hidrogénatom, R4vagy -(CR7R8)mR3 általános képletű csoport, amikor X jelentése -CR7R8általános képletű csoport R3 jelentése egymástól függetlenül 6-10szénatomos aril- vagy 5-10 tagszámú heterociklusos csoport, ahol anevezett arilcsoport és heterociklusos csoport adott esetben 1-3szubsztituenssel helyettesített, R4 és R5 jelentése egymástólfüggetlenül hidrogénatom vagy 1-12 szénatomos alkilcsoport, ahol anevezett alkilcsoport 1 vagy 2 szénatomját adott esetben O, S vagy Nheteroatom helyettesíti, és ahol a nevezett alkilcsoport adott esetben1-3 szubsztituenssel helyettesített, R6 jelentése hidrogénatom, -C(O)R3 általános képletű vagy 1-18szénatomos alkanoilcsoport, ahol a nevezett alkanoilcsoport alkilrészében 1 vagy 2 szénatomot adott esetben O, S vagy N heteroatomhelyettesít; és R7 és R8 jelentése egymástól függetlenül hidrogénatomvagy 1-6 szénatomos alkilcsoport - vegyületek és gyógyászatiszempontból alkalmazható sóik, a nevezett vegyületeket tartalmazógyógyszerkészítmények, továbbá az (I) általános képletű vegyületelőállítására szolgáló eljárások. ÓThe subject of the invention is for the treatment or prevention of bacterial and protozoan infections in mammals, fish and birds with the general formula (i) - where X is a group of the general formula -CR7R8- or -NR7; or X1 and R2 together represent a group of general formula -N=CR4R5; or X1 and R2 together form an optionally substituted heterocyclic group of general formula (XVI), in which r and p are independently an integer between 1 and 3, q is 0 or 1 and X1 is -CH2-, -C(O)- , -C(S)-, -SO2-, -CH=CH-, -CH(OH)CH(OH)-, -NH- or an oxygen or sulfur atom. R1 is a hydrogen atom or an alkyl group with 1-10 carbon atoms, where the said alkyl group can be replaced by an O, S or N heteroatom if 1-3 carbon atoms are present and the said alkyl group is optionally substituted with 1-3 substituents, which are independently -C(O)O(1-10 carbon atoms alkyl) of the general formula, 1-10 carbon-atom alkoxy-, 1-10 carbon-atom alkanoyl-, nitro-, cyano-, 5-10-membered heterocyclic, 1-10 carbon atom alkyl-, of the general formula -NR7R8, 6-10 carbon atom aryl-, - S(O)n(alkyl with 1-10 carbon atoms) - within which n is an integer between 0-2 - is selected from groups with the general formula -SO2NR7R8 or halogen atoms; R2 is (i) a hydrogen atom, -C(O)R4, -C(O)OR4 or -(CR7R8)mR3, when X is -NR7-, or (ii) a hydrogen atom, R4 or -(CR7R8) A group of the general formula mR3, when X means -CR7R8, a group of the general formula R3 independently means an aryl group with 6-10 carbon atoms or a heterocyclic group with 5-10 members, where the named aryl group and heterocyclic group are optionally substituted with 1-3 substituents, R4 and R5 independently mean a hydrogen atom or 1 -12-carbon alkyl group, where 1 or 2 carbon atoms of the named alkyl group are optionally replaced by O, S or Nheteroatom, and where the named alkyl group is optionally substituted with 1-3 substituents, R6 is a hydrogen atom, -C(O)R3 or an alkanoyl group with 1-18 carbon atoms , where 1 or 2 carbon atoms in the alkyl part of the named alkanoyl group are optionally replaced by O, S or N heteroatoms; and R7 and R8 are independently a hydrogen atom or a C1-C6 alkyl group - compounds and their salts that can be used from a medical point of view, pharmaceutical preparations containing the named compounds, and the processes for the production of compounds of general formula (I). HE
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4934997P | 1997-06-11 | 1997-06-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUP0002252A2 true HUP0002252A2 (en) | 2000-12-28 |
| HUP0002252A3 HUP0002252A3 (en) | 2002-01-28 |
Family
ID=21959341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0002252A HUP0002252A3 (en) | 1997-06-11 | 1998-05-15 | 9-oxime erythromycin derivatives, process for preparing them and pharmaceutical compositions containing them |
Country Status (31)
| Country | Link |
|---|---|
| EP (1) | EP0988308A1 (en) |
| JP (1) | JP2000513026A (en) |
| KR (1) | KR20010013660A (en) |
| CN (1) | CN1259135A (en) |
| AP (1) | AP9801253A0 (en) |
| AR (1) | AR012244A1 (en) |
| AU (1) | AU7226798A (en) |
| BG (1) | BG103947A (en) |
| BR (1) | BR9810021A (en) |
| CA (1) | CA2293335A1 (en) |
| CO (1) | CO4940506A1 (en) |
| CZ (1) | CZ9904388A3 (en) |
| EA (1) | EA199901016A1 (en) |
| GT (1) | GT199800074A (en) |
| HN (1) | HN1998000073A (en) |
| HR (1) | HRP980316A2 (en) |
| HU (1) | HUP0002252A3 (en) |
| ID (1) | ID24529A (en) |
| IL (1) | IL132767A0 (en) |
| IS (1) | IS5251A (en) |
| MA (1) | MA26505A1 (en) |
| NO (1) | NO996108L (en) |
| OA (1) | OA11225A (en) |
| PA (1) | PA8451801A1 (en) |
| PE (1) | PE79899A1 (en) |
| PL (1) | PL337606A1 (en) |
| TN (1) | TNSN98083A1 (en) |
| TR (1) | TR199902995T2 (en) |
| TW (1) | TW448174B (en) |
| WO (1) | WO1998056800A1 (en) |
| ZA (1) | ZA985018B (en) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HN1998000159A (en) * | 1997-10-29 | 1999-02-09 | Monsanto Co | DERIVATIVES OF 9- AMINO - 3 CETO ERITROMICINA |
| ATE298761T1 (en) | 1998-09-22 | 2005-07-15 | Pfizer Prod Inc | CARBAMAT AND CARBAZATE KETOLID ANTIBIOTICS |
| FR2786188B1 (en) * | 1998-11-24 | 2002-10-31 | Hoechst Marion Roussel Inc | NOVEL ERYTHROMYCIN DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR APPLICATION AS MEDICAMENTS |
| US6258785B1 (en) | 1998-12-02 | 2001-07-10 | Pfizer Inc. | Crystalline 9-E-(O-methyl)oxime of 11, 12-dideoxy-3-de(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribohexopyranosyloxy)-6-O-methyl-12,11-(iminocarbonyl-(2-(3-(4-(3-pyridinyl)1H-imadazol-1-yl)propyl)hydrazono))-3-oxoerythromycin |
| EP1298138B1 (en) * | 1998-12-10 | 2006-11-02 | Pfizer Products Inc. | Carbamate and Carbazate Ketolide Antibiotics |
| US6284732B1 (en) * | 1998-12-18 | 2001-09-04 | Bio-Rad Laboratories, Inc. | Peptides and peptide analogues designed from HFE protein and their uses in the treatment of iron overload diseases |
| ATE340183T1 (en) * | 1999-04-16 | 2006-10-15 | Kosan Biosciences Inc | ANTINIFECTIVE MACROLIDE DERIVATIVES |
| HUP0201516A3 (en) | 1999-05-24 | 2003-03-28 | Pfizer Prod Inc | 13-methyl-erythromycin derivatives, process for their preparation and pharmaceutical compositions containing them |
| WO2000075156A1 (en) * | 1999-06-07 | 2000-12-14 | Abbott Laboratories | 6-o-carbamate ketolide derivatives |
| ID27331A (en) * | 1999-09-29 | 2001-03-29 | Pfizer Prod Inc | MAKING ANTIBIOTIC-ANTIBIOTIC KETOLIDA CARBAMATE |
| EP1439186A3 (en) * | 1999-12-29 | 2004-11-03 | Pfizer Products Inc. | Intermediates for novel antibacterial and prokinetic macrolides |
| EP1114826A3 (en) * | 1999-12-29 | 2001-10-31 | Pfizer Products Inc. | Novel antibacterial and prokinetic macrolides |
| US6946446B2 (en) | 2000-02-24 | 2005-09-20 | Abbott Laboratories | Anti-infective agents useful against multidrug-resistant strains of bacteria |
| US6403776B1 (en) | 2000-07-05 | 2002-06-11 | Pfizer Inc. | Synthesis of carbamate ketolide antibiotics |
| WO2003090761A1 (en) * | 2002-04-25 | 2003-11-06 | Abbott Laboratories | 9-oxime macrolide antibacterials |
| US7091196B2 (en) | 2002-09-26 | 2006-08-15 | Rib-X Pharmaceuticals, Inc. | Bifunctional heterocyclic compounds and methods of making and using same |
| EP1638549A4 (en) * | 2003-03-10 | 2011-06-15 | Optimer Pharmaceuticals Inc | Novel antibacterial agents |
| EP1723159B1 (en) | 2004-02-27 | 2019-06-12 | Melinta Therapeutics, Inc. | Macrocyclic compounds and methods of making and using the same |
| EP2214484A4 (en) | 2007-10-25 | 2013-01-02 | Cempra Pharmaceuticals Inc | Process for the preparation of macrolide antibacterial agents |
| US8796232B2 (en) | 2008-10-24 | 2014-08-05 | Cempra Pharmaceuticals, Inc. | Methods for treating resistant diseases using triazole containing macrolides |
| US9937194B1 (en) | 2009-06-12 | 2018-04-10 | Cempra Pharmaceuticals, Inc. | Compounds and methods for treating inflammatory diseases |
| AU2010292010B2 (en) | 2009-09-10 | 2016-01-07 | Cempra Pharmaceuticals, Inc. | Methods for treating malaria, tuberculosis and MAC diseases |
| CN102146085B (en) * | 2010-02-09 | 2014-03-26 | 北京理工大学 | 9-oxime-ether ketolide derivative, and preparation method and medical composite thereof |
| CN103080122A (en) | 2010-03-22 | 2013-05-01 | 森普拉制药公司 | Crystalline forms of a macrolide, and uses therefor |
| US9051346B2 (en) | 2010-05-20 | 2015-06-09 | Cempra Pharmaceuticals, Inc. | Process for preparing triazole-containing ketolide antibiotics |
| JP6042334B2 (en) | 2010-09-10 | 2016-12-14 | センプラ ファーマシューティカルズ，インコーポレイテッド | Hydrogen bond forming fluoroketolides for disease treatment |
| CN104470527B (en) | 2012-03-27 | 2019-05-28 | 森普拉制药公司 | For applying the parenteral administration of macrolide antibiotic |
| WO2014152326A1 (en) | 2013-03-14 | 2014-09-25 | Cempra Pharmaceuticals, Inc. | Methods for treating respiratory diseases and formulations therefor |
| US9751908B2 (en) | 2013-03-15 | 2017-09-05 | Cempra Pharmaceuticals, Inc. | Convergent processes for preparing macrolide antibacterial agents |
Family Cites Families (3)
| 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 |
| US5527780A (en) * | 1992-11-05 | 1996-06-18 | Roussel Uclaf | Erythromycin derivatives |
| FR2718450B1 (en) * | 1994-04-08 | 1997-01-10 | Roussel Uclaf | New erythromycin derivatives, their preparation process and their use as drugs. |
-
1998
- 1998-05-15 EA EA199901016A patent/EA199901016A1/en unknown
- 1998-05-15 IL IL13276798A patent/IL132767A0/en unknown
- 1998-05-15 CA CA002293335A patent/CA2293335A1/en not_active Abandoned
- 1998-05-15 HU HU0002252A patent/HUP0002252A3/en unknown
- 1998-05-15 CZ CZ19994388A patent/CZ9904388A3/en unknown
- 1998-05-15 PL PL98337606A patent/PL337606A1/en unknown
- 1998-05-15 EP EP98919394A patent/EP0988308A1/en not_active Withdrawn
- 1998-05-15 AU AU72267/98A patent/AU7226798A/en not_active Abandoned
- 1998-05-15 BR BR9810021-1A patent/BR9810021A/en not_active IP Right Cessation
- 1998-05-15 TR TR1999/02995T patent/TR199902995T2/en unknown
- 1998-05-15 KR KR1019997011672A patent/KR20010013660A/en not_active Application Discontinuation
- 1998-05-15 ID IDW991570A patent/ID24529A/en unknown
- 1998-05-15 JP JP11501928A patent/JP2000513026A/en active Pending
- 1998-05-15 CN CN98805848A patent/CN1259135A/en active Pending
- 1998-05-15 WO PCT/IB1998/000741 patent/WO1998056800A1/en not_active Application Discontinuation
- 1998-05-19 HN HN1998000073A patent/HN1998000073A/en unknown
- 1998-05-21 PA PA19988451801A patent/PA8451801A1/en unknown
- 1998-06-04 AP APAP/P/1998/001253A patent/AP9801253A0/en unknown
- 1998-06-05 GT GT199800074A patent/GT199800074A/en unknown
- 1998-06-08 PE PE1998000470A patent/PE79899A1/en not_active Application Discontinuation
- 1998-06-08 TW TW087109086A patent/TW448174B/en active
- 1998-06-09 AR ARP980102703A patent/AR012244A1/en unknown
- 1998-06-10 MA MA25105A patent/MA26505A1/en unknown
- 1998-06-10 ZA ZA9805018A patent/ZA985018B/en unknown
- 1998-06-10 TN TNTNSN98083A patent/TNSN98083A1/en unknown
- 1998-06-11 CO CO98033538A patent/CO4940506A1/en unknown
- 1998-06-11 HR HR60/049,349A patent/HRP980316A2/en not_active Application Discontinuation
-
1999
- 1999-11-16 IS IS5251A patent/IS5251A/en unknown
- 1999-12-03 OA OA9900269A patent/OA11225A/en unknown
- 1999-12-03 BG BG103947A patent/BG103947A/en unknown
- 1999-12-10 NO NO996108A patent/NO996108L/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| TW448174B (en) | 2001-08-01 |
| KR20010013660A (en) | 2001-02-26 |
| HN1998000073A (en) | 1999-01-08 |
| BG103947A (en) | 2000-07-31 |
| TNSN98083A1 (en) | 2005-03-15 |
| BR9810021A (en) | 2000-09-19 |
| NO996108L (en) | 2000-02-10 |
| PE79899A1 (en) | 1999-08-25 |
| AP9801253A0 (en) | 1999-12-04 |
| HUP0002252A3 (en) | 2002-01-28 |
| AR012244A1 (en) | 2000-09-27 |
| NO996108D0 (en) | 1999-12-10 |
| CA2293335A1 (en) | 1998-12-17 |
| CZ9904388A3 (en) | 2002-10-16 |
| GT199800074A (en) | 1999-11-27 |
| EA199901016A1 (en) | 2000-06-26 |
| ID24529A (en) | 2000-07-20 |
| IS5251A (en) | 1999-11-16 |
| EP0988308A1 (en) | 2000-03-29 |
| AU7226798A (en) | 1998-12-30 |
| HRP980316A2 (en) | 1999-04-30 |
| TR199902995T2 (en) | 2000-02-21 |
| PA8451801A1 (en) | 2000-05-24 |
| PL337606A1 (en) | 2000-08-28 |
| ZA985018B (en) | 1999-12-10 |
| IL132767A0 (en) | 2001-03-19 |
| OA11225A (en) | 2003-07-17 |
| JP2000513026A (en) | 2000-10-03 |
| WO1998056800A1 (en) | 1998-12-17 |
| CO4940506A1 (en) | 2000-07-24 |
| MA26505A1 (en) | 2004-12-20 |
| CN1259135A (en) | 2000-07-05 |
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