CA2290136C - Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments - Google Patents
Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments Download PDFInfo
- Publication number
- CA2290136C CA2290136C CA2290136A CA2290136A CA2290136C CA 2290136 C CA2290136 C CA 2290136C CA 2290136 A CA2290136 A CA 2290136A CA 2290136 A CA2290136 A CA 2290136A CA 2290136 C CA2290136 C CA 2290136C
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- compound
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- alkenyl
- alkyl
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- 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 13
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 title description 2
- 229940126534 drug product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 239000002253 acid Substances 0.000 claims abstract description 17
- -1 heteroaryl radicals Chemical class 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 8
- 230000003115 biocidal effect Effects 0.000 claims abstract description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 8
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
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- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
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- 229960003276 erythromycin Drugs 0.000 claims description 13
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- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
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- WYQWOUSBDUZLRM-UHFFFAOYSA-N 4-(3-pyridin-3-ylpyrazol-1-yl)butan-1-amine Chemical compound NCCCCN1C=CC(C=2C=NC=CC=2)=N1 WYQWOUSBDUZLRM-UHFFFAOYSA-N 0.000 claims description 3
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- VAIKICJGHGNVQI-UHFFFAOYSA-N 4-(4-pyridin-3-ylpyrazol-1-yl)butan-1-amine Chemical compound C1=NN(CCCCN)C=C1C1=CC=CN=C1 VAIKICJGHGNVQI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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- 229930006677 Erythromycin A Natural products 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 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
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- OKRROXQXGNEUSS-UHFFFAOYSA-N 1h-imidazol-1-ium-1-carboxylate Chemical compound OC(=O)N1C=CN=C1 OKRROXQXGNEUSS-UHFFFAOYSA-N 0.000 description 1
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- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9814782 | 1998-11-24 | ||
| FR9814782A FR2786188B1 (fr) | 1998-11-24 | 1998-11-24 | Nouveaux derives de l'erythromycine, leur procede de preparation et leur applicaion comme medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2290136A1 CA2290136A1 (fr) | 2000-05-24 |
| CA2290136C true CA2290136C (fr) | 2010-07-20 |
Family
ID=9533122
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2290136A Expired - Lifetime CA2290136C (fr) | 1998-11-24 | 1999-11-18 | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US6440941B1 (https=) |
| EP (1) | EP1004592B1 (https=) |
| JP (1) | JP2000159790A (https=) |
| KR (1) | KR100587445B1 (https=) |
| CN (1) | CN1165546C (https=) |
| AR (1) | AR021388A1 (https=) |
| AT (1) | ATE245160T1 (https=) |
| AU (1) | AU772171B2 (https=) |
| BR (1) | BR9905735A (https=) |
| CA (1) | CA2290136C (https=) |
| DE (1) | DE69909577T2 (https=) |
| DK (1) | DK1004592T3 (https=) |
| ES (1) | ES2198867T3 (https=) |
| FR (1) | FR2786188B1 (https=) |
| HU (1) | HUP9904392A3 (https=) |
| IL (1) | IL133101A (https=) |
| MX (1) | MXPA99010813A (https=) |
| NO (1) | NO314729B1 (https=) |
| PL (1) | PL336736A1 (https=) |
| PT (1) | PT1004592E (https=) |
| RU (1) | RU2237672C2 (https=) |
| TR (1) | TR199902888A3 (https=) |
| TW (1) | TWI247747B (https=) |
| ZA (1) | ZA997176B (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2786188B1 (fr) * | 1998-11-24 | 2002-10-31 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur applicaion comme medicaments |
| CA2359708C (en) | 1999-01-27 | 2005-10-25 | Pfizer Products Inc. | Ketolide antibiotics |
| HUP0201516A3 (en) | 1999-05-24 | 2003-03-28 | Pfizer Prod Inc | 13-methyl-erythromycin derivatives, process for their preparation and pharmaceutical compositions containing them |
| EP1167376B1 (en) | 2000-06-30 | 2004-07-14 | Pfizer Products Inc. | Macrolide antibiotics |
| EP1638549A4 (en) * | 2003-03-10 | 2011-06-15 | Optimer Pharmaceuticals Inc | NEW ANTIBACTERIAL AGENTS |
| FR2862647B1 (fr) * | 2003-11-25 | 2008-07-04 | Aventis Pharma Sa | Derives de pyrazolyle, procede de preparation et intermediaires de ce procede a titre de medicaments et de compositions pharmaceutiques les renfermant |
| US20080287376A1 (en) * | 2004-07-28 | 2008-11-20 | Mohammad Salman | Ketolide Derivatives as Antibacterial Agents |
| EP2214484A4 (en) | 2007-10-25 | 2013-01-02 | Cempra Pharmaceuticals Inc | PROCESS FOR PREPARING ANTIBACTERIAL MAKROLIDE AGENTS |
| WO2009137787A1 (en) * | 2008-05-09 | 2009-11-12 | Enanta Pharmaceuticals, Inc. | Processes for the preparation of 2-fluoro 6-11 bicyclic erythromycin derivatives |
| JP5711135B2 (ja) | 2008-10-24 | 2015-04-30 | 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 | 胃腸疾患を治療するための方法 |
| US9937194B1 (en) | 2009-06-12 | 2018-04-10 | Cempra Pharmaceuticals, Inc. | Compounds and methods for treating inflammatory diseases |
| ES2608285T3 (es) | 2009-09-10 | 2017-04-07 | Cempra Pharmaceuticals, Inc. | Procedimientos para el tratamiento de paludismo, tuberculosis y enfermedades por MAC |
| MX361413B (es) | 2010-03-22 | 2018-12-05 | Cempra Pharmaceuticals Inc Star | Formas cristalinas de un macrólido y usos para las mismas. |
| CN102917708B (zh) | 2010-05-20 | 2015-11-25 | 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 (en) * | 2010-09-10 | 2014-01-15 | Cempra Pharmaceuticals Inc | HYDROGEN BOND FOR THE PREPARATION OF FLUOROCHETOLIDES FOR THE TREATMENT OF DISEASES |
| BR112013009823A2 (pt) | 2010-10-22 | 2016-07-05 | Bayer Ip Gmbh | novos compostos heterocíclicos como pesticidas |
| NZ700182A (en) | 2012-03-27 | 2017-02-24 | Cempra Pharmaceuticals Inc | Parenteral formulations for administering macrolide antibiotics |
| AU2014239959A1 (en) | 2013-03-14 | 2015-10-01 | Cempra Pharmaceuticals, Inc. | Methods for treating respiratory diseases and formulations therefor |
| CN105188712A (zh) | 2013-03-15 | 2015-12-23 | 森普拉制药公司 | 用于制备大环内酯抗菌剂的收敛方法 |
| CN106432383A (zh) * | 2016-09-14 | 2017-02-22 | 重庆两江药物研发中心有限公司 | 索利霉素及其中间体的制备方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1098527A (en) * | 1976-12-20 | 1981-03-31 | Denis M. Bailey | 1-amino-lower-alkyl-3,4-diphenyl-1h-pyrazoles |
| US4182895A (en) * | 1976-12-20 | 1980-01-08 | Sterling Drug Inc. | 1-Amino-lower-alkyl-3,4-diphenyl-1H-pyrazoles |
| JPH04234891A (ja) * | 1990-03-05 | 1992-08-24 | Fujisawa Pharmaceut Co Ltd | 新規セフェム化合物およびその塩 |
| FR2697524B1 (fr) * | 1992-11-05 | 1994-12-23 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| US5527780A (en) * | 1992-11-05 | 1996-06-18 | Roussel Uclaf | Erythromycin derivatives |
| FR2718450B1 (fr) * | 1994-04-08 | 1997-01-10 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| FR2719587B1 (fr) * | 1994-05-03 | 1996-07-12 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| FR2727969B1 (fr) * | 1994-12-09 | 1997-01-17 | Roussel Uclaf | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| FR2742757B1 (fr) * | 1995-12-22 | 1998-01-30 | Roussel Uclaf | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| EP0988308A1 (en) * | 1997-06-11 | 2000-03-29 | Pfizer Products Inc. | 9-oxime erythromycin derivatives |
| FR2786188B1 (fr) * | 1998-11-24 | 2002-10-31 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur applicaion comme medicaments |
-
1998
- 1998-11-24 FR FR9814782A patent/FR2786188B1/fr not_active Expired - Fee Related
-
1999
- 1999-11-16 TW TW088119939A patent/TWI247747B/zh not_active IP Right Cessation
- 1999-11-17 AU AU59522/99A patent/AU772171B2/en not_active Expired
- 1999-11-18 CA CA2290136A patent/CA2290136C/fr not_active Expired - Lifetime
- 1999-11-18 ZA ZA9907176A patent/ZA997176B/xx unknown
- 1999-11-18 US US09/442,681 patent/US6440941B1/en not_active Expired - Lifetime
- 1999-11-22 JP JP11331141A patent/JP2000159790A/ja active Pending
- 1999-11-23 ES ES99402907T patent/ES2198867T3/es not_active Expired - Lifetime
- 1999-11-23 RU RU99125547A patent/RU2237672C2/ru not_active IP Right Cessation
- 1999-11-23 DE DE69909577T patent/DE69909577T2/de not_active Expired - Lifetime
- 1999-11-23 IL IL133101A patent/IL133101A/en not_active IP Right Cessation
- 1999-11-23 PT PT99402907T patent/PT1004592E/pt unknown
- 1999-11-23 DK DK99402907T patent/DK1004592T3/da active
- 1999-11-23 CN CNB99127394XA patent/CN1165546C/zh not_active Expired - Lifetime
- 1999-11-23 NO NO19995745A patent/NO314729B1/no unknown
- 1999-11-23 HU HU9904392A patent/HUP9904392A3/hu unknown
- 1999-11-23 MX MXPA99010813A patent/MXPA99010813A/es active IP Right Grant
- 1999-11-23 AT AT99402907T patent/ATE245160T1/de active
- 1999-11-23 KR KR1019990052014A patent/KR100587445B1/ko not_active Expired - Lifetime
- 1999-11-23 EP EP99402907A patent/EP1004592B1/fr not_active Expired - Lifetime
- 1999-11-24 BR BR9905735-2A patent/BR9905735A/pt active Search and Examination
- 1999-11-24 PL PL99336736A patent/PL336736A1/xx not_active Application Discontinuation
- 1999-11-24 AR ARP990105985A patent/AR021388A1/es not_active Application Discontinuation
- 1999-11-24 TR TR1999/02888A patent/TR199902888A3/tr unknown
-
2002
- 2002-07-02 US US10/188,394 patent/US6664398B2/en not_active Expired - Lifetime
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20191118 |