HRP20010306A2 - Novel macrolide antibiotics - Google Patents
Novel macrolide antibiotics Download PDFInfo
- Publication number
- HRP20010306A2 HRP20010306A2 HR20010306A HRP20010306A HRP20010306A2 HR P20010306 A2 HRP20010306 A2 HR P20010306A2 HR 20010306 A HR20010306 A HR 20010306A HR P20010306 A HRP20010306 A HR P20010306A HR P20010306 A2 HRP20010306 A2 HR P20010306A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- infection
- aryl
- methyl
- heteroaryl
- Prior art date
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- 239000003120 macrolide antibiotic agent Substances 0.000 title description 15
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- -1 4-(4-(3-pyridinyl)-1H-imidazol-1-yl)butylimino Chemical group 0.000 claims description 72
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 65
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 64
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- 125000005843 halogen group Chemical group 0.000 claims description 58
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Classifications
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- 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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- 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
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Urology & Nephrology (AREA)
- Biotechnology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Communicable Diseases (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10683698P | 1998-11-03 | 1998-11-03 | |
| PCT/IB1999/001701 WO2000026224A2 (en) | 1998-11-03 | 1999-10-18 | Novel macrolide antibiotics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20010306A2 true HRP20010306A2 (en) | 2002-06-30 |
Family
ID=22313524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20010306A HRP20010306A2 (en) | 1998-11-03 | 2001-04-30 | Novel macrolide antibiotics |
Country Status (34)
| Country | Link |
|---|---|
| US (3) | US20020040007A1 (xx) |
| EP (1) | EP1124837A2 (xx) |
| JP (1) | JP4043191B2 (xx) |
| KR (1) | KR20010083944A (xx) |
| CN (1) | CN1376160A (xx) |
| AP (1) | AP2001002131A0 (xx) |
| AU (1) | AU5995299A (xx) |
| BG (1) | BG105543A (xx) |
| BR (1) | BR9914998A (xx) |
| CA (1) | CA2349338C (xx) |
| CO (1) | CO5140110A1 (xx) |
| CZ (1) | CZ20011512A3 (xx) |
| EA (1) | EA200100396A1 (xx) |
| EE (1) | EE200100245A (xx) |
| GT (1) | GT199900192A (xx) |
| HK (1) | HK1049010A1 (xx) |
| HR (1) | HRP20010306A2 (xx) |
| HU (1) | HUP0104192A3 (xx) |
| ID (1) | ID28286A (xx) |
| IL (1) | IL142628A0 (xx) |
| IS (1) | IS5919A (xx) |
| MA (1) | MA26703A1 (xx) |
| NO (1) | NO20012155L (xx) |
| OA (1) | OA11670A (xx) |
| PA (1) | PA8485101A1 (xx) |
| PE (1) | PE20001289A1 (xx) |
| PL (1) | PL348114A1 (xx) |
| SK (1) | SK5812001A3 (xx) |
| SV (1) | SV1999000188A (xx) |
| TN (1) | TNSN99205A1 (xx) |
| TR (4) | TR200101241T2 (xx) |
| UY (1) | UY25780A1 (xx) |
| WO (1) | WO2000026224A2 (xx) |
| ZA (1) | ZA200103289B (xx) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AP9801420A0 (en) * | 1998-01-02 | 1998-12-31 | Pfizer Prod Inc | Novel macrolides. |
| ID28286A (id) | 1998-11-03 | 2001-05-10 | Pfizer Prod Inc | Antibiotik-antibiotik makrolida baru |
| JP3947360B2 (ja) | 1999-01-27 | 2007-07-18 | ファイザー・プロダクツ・インク | ケトリド抗生物質 |
| CN1241931C (zh) | 1999-04-16 | 2006-02-15 | 高山生物科学股份有限公司 | 大环内酯抗感染药物 |
| US6939861B2 (en) | 1999-04-16 | 2005-09-06 | Kosan Biosciences, Inc. | Amido macrolides |
| US6590083B1 (en) | 1999-04-16 | 2003-07-08 | Ortho-Mcneil Pharmaceutical, Inc. | Ketolide antibacterials |
| US6514944B2 (en) | 1999-04-16 | 2003-02-04 | Kosan Biosciences, Inc. | Macrolide antiinfective agents |
| US6451768B1 (en) | 1999-04-16 | 2002-09-17 | Kosan Biosciences, Inc. | Macrolide antiinfective agents |
| MXPA01010521A (es) | 1999-04-16 | 2003-08-19 | Johnson & Johnson | Antibacteriales de cetolidos. |
| IL145739A0 (en) | 1999-05-24 | 2002-07-25 | Pfizer Prod Inc | 13-methyl-erythromycin derivatives |
| EP1114826A3 (en) * | 1999-12-29 | 2001-10-31 | Pfizer Products Inc. | Novel antibacterial and prokinetic macrolides |
| EP1146051A3 (en) * | 2000-04-10 | 2001-10-31 | Pfizer Products Inc. | Erythromycin A derivatives |
| ATE271062T1 (de) | 2000-06-30 | 2004-07-15 | Pfizer Prod Inc | Makrolid-antibiotika |
| US20080287376A1 (en) * | 2004-07-28 | 2008-11-20 | Mohammad Salman | Ketolide Derivatives as Antibacterial Agents |
| WO2006046112A2 (en) * | 2004-10-25 | 2006-05-04 | Ranbaxy Laboratories Limited | Ketolide derivatives as antibacterial agents |
| PL1836211T3 (pl) * | 2004-12-21 | 2010-07-30 | Pfizer Prod Inc | Makrolidy |
| WO2007060518A2 (en) * | 2005-11-23 | 2007-05-31 | Ranbaxy Laboratories Limited | Ketolide derivatives as antibacterial agents |
| US20090130225A1 (en) * | 2005-11-23 | 2009-05-21 | Anjan Chakrabarti | Macrolides derivatives as antibacterial agents |
| US7801502B2 (en) * | 2006-12-18 | 2010-09-21 | Aai Corporation | Method for implementing continuous radio frequency (RF) alignment in advanced electronic warfare (EW) signal stimulation systems |
| US8409628B2 (en) | 2010-02-04 | 2013-04-02 | Penguin IP Holdings, Inc. | Methods and compositions for oxygenation of skin to treat skin disorders |
| WO2011123619A2 (en) | 2010-03-31 | 2011-10-06 | Penguin Ip Holdings Inc. | Permeable mixtures, methods and compositions for the skin |
| CN112656782A (zh) * | 2013-05-01 | 2021-04-16 | 尼奥酷里私人有限公司 | 治疗细菌感染的方法 |
| RU2537143C1 (ru) * | 2013-11-08 | 2014-12-27 | Государственное научное учреждение Ставропольский научно-исследовательский институт животноводства и кормопроизводства РАСХН | Препарат для лечения и профилактики мастита у коров |
| WO2018080072A2 (ko) * | 2016-10-27 | 2018-05-03 | 한국생명공학연구원 | 신규한 매크로라이드계 화합물, 이의 제조방법 및 이를 유효성분으로 함유하는 말라리아의 예방 또는 치료용 약학적 조성물 |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU43006B (en) * | 1981-03-06 | 1989-02-28 | Pliva Pharm & Chem Works | Process for preparing n-methyl-11-aza-10-deoxo-10-dihydro erythromycin and derivatives thereof |
| US4474768A (en) * | 1982-07-19 | 1984-10-02 | Pfizer Inc. | N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor |
| IL99995A (en) * | 1990-11-21 | 1997-11-20 | Roussel Uclaf | Erythromycin derivatives, their preparation and pharmaceutical compositions containing them |
| 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 |
| US5332807A (en) | 1993-04-14 | 1994-07-26 | Merck & Co., Inc. | Process of producing 8A- and 9A-azalide antibiotics |
| FR2702480B1 (fr) * | 1993-03-09 | 1995-04-28 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| HRP931480B1 (en) | 1993-12-08 | 1997-08-31 | Sour Pliva | 9a-N-(N'-CARBAMONYL) and 9a-N-(N'-THIOCARBAMONYL) DERIVATES OF 9-DEOXO-9a-HOMOERYTHROMYCIN A |
| HRP950145A2 (en) | 1995-03-27 | 1997-08-31 | Sour Pliva | New compounds of the secomacrolide and secoazalide class and a process for the preparation thereof |
| HN1996000101A (es) | 1996-02-28 | 1997-06-26 | Inc Pfizer | Terapia combinada para la osteoporosis |
| JP2000509712A (ja) | 1996-05-07 | 2000-08-02 | アボツト・ラボラトリーズ | ６―ｏ―置換エリスロマイシン及びその製造方法 |
| EA001744B1 (ru) | 1996-07-05 | 2001-08-27 | Байотика Текнолоджи Лимитед (Gb) | Новые эритромицины и способы их получения |
| EP1291352B1 (en) * | 1996-09-04 | 2005-05-25 | Abbott Laboratories | 6-O-substituted ketolides having antibacterial activity |
| UA51730C2 (uk) | 1996-09-04 | 2002-12-16 | Ебботт Лабораторіз | 6-o-заміщені кетоліди з антибактеріальною активністю, спосіб їх одержання (варіанти), фармацевтична композиція та спосіб регулювання бактеріальної інфекції у ссавців |
| HRP960497B1 (en) | 1996-10-28 | 2003-08-31 | Pliva Pharm & Chem Works | 9-n-ethenyl derivatives of 9(s)-erythromycylamine |
| US6407074B1 (en) | 1997-06-11 | 2002-06-18 | Pfizer Inc | C-4″-substituted macrolide derivatives |
| HN1998000074A (es) | 1997-06-11 | 1999-01-08 | Pfizer Prod Inc | Derivados de macrolidos c-4 sustituidos |
| EP0895999A1 (en) | 1997-08-06 | 1999-02-10 | Pfizer Products Inc. | C-4" substituted macrolide antibiotics |
| US6339063B1 (en) | 1997-09-10 | 2002-01-15 | Merck & Co., Inc. | 9a-azalides as veterinary antimicrobial agents |
| KR100554549B1 (ko) | 1997-10-16 | 2006-03-03 | 플리바 파마세우츠카 인두스트리야, 디오닉코, 드러스트보 | 9ａ-아잘리드류로부터 유래한 신규한 3,6-헤미케탈 |
| ATE275151T1 (de) | 1998-03-03 | 2004-09-15 | Pfizer Prod Inc | 3,6-ketal-makrolidantibiotika |
| ID28286A (id) | 1998-11-03 | 2001-05-10 | Pfizer Prod Inc | Antibiotik-antibiotik makrolida baru |
| IL145739A0 (en) | 1999-05-24 | 2002-07-25 | Pfizer Prod Inc | 13-methyl-erythromycin derivatives |
| EP1114826A3 (en) | 1999-12-29 | 2001-10-31 | Pfizer Products Inc. | Novel antibacterial and prokinetic macrolides |
| EP1122261A3 (en) | 2000-01-31 | 2001-09-26 | Pfizer Products Inc. | 13 and 14-membered antibacterial macrolides |
| ATE271062T1 (de) | 2000-06-30 | 2004-07-15 | Pfizer Prod Inc | Makrolid-antibiotika |
| CA2451391A1 (en) | 2001-07-03 | 2003-01-16 | Chiron Corporation | C12 modified erythromycin macrolides and ketolides having antibacterial activity |
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1999
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