WO2006119313A2 - Derives d'oxime d'erythromycine pontes 6-11 - Google Patents

Derives d'oxime d'erythromycine pontes 6-11 Download PDF

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Publication number
WO2006119313A2
WO2006119313A2 PCT/US2006/016882 US2006016882W WO2006119313A2 WO 2006119313 A2 WO2006119313 A2 WO 2006119313A2 US 2006016882 W US2006016882 W US 2006016882W WO 2006119313 A2 WO2006119313 A2 WO 2006119313A2
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WO
WIPO (PCT)
Prior art keywords
substituted
group
unsubstituted
compound
hydrogen
Prior art date
Application number
PCT/US2006/016882
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English (en)
Other versions
WO2006119313A3 (fr
Inventor
Guoqiang Wang
Ly Tam Phan
Yat Sun Or
Yao-Ling Qiu
Deqiang Niu
Yulin Peng
Marina Busuyek
Yanchun Wang
Suanne Nakajima
Original Assignee
Enanta Pharmaceuticals, 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.)
Filing date
Publication date
Priority claimed from US11/122,251 external-priority patent/US20060252710A1/en
Application filed by Enanta Pharmaceuticals, Inc. filed Critical Enanta Pharmaceuticals, Inc.
Priority to EP06769971A priority Critical patent/EP1885737A4/fr
Priority to CA002605295A priority patent/CA2605295A1/fr
Priority to CN2006800139709A priority patent/CN101166749B/zh
Priority to BRPI0610477-0A priority patent/BRPI0610477A2/pt
Priority to MX2007013730A priority patent/MX2007013730A/es
Priority to AU2006242188A priority patent/AU2006242188A1/en
Priority to JP2008510145A priority patent/JP2008540432A/ja
Publication of WO2006119313A2 publication Critical patent/WO2006119313A2/fr
Publication of WO2006119313A3 publication Critical patent/WO2006119313A3/fr

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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
    • A—HUMAN NECESSITIES
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • A61P27/02—Ophthalmic agents
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents

Definitions

  • the present invention relates to novel semisynthetic macrolides having antibacterial activity and useful in the treatment and prevention of bacterial infections. More particularly, the invention relates to 6-11 bicyclic macrolide, ketolide, and anhydrolide derivatives, compositions containing such compounds and methods for using the same, as well as processes for making such compounds.
  • Macrolides possessing a 3-oxo moiety in place of the 3-cladinose sugar are known as ketolides and have shown enhanced activity towards gram-negative bacteria and macrolide resistant gram- positive bacteria.
  • Macrolides possessing a degree of unsaturation between carbons 2 and 3 or between carbons 3 and 4 of the erythromycin macrocycle are known as anhydrolides.
  • novel bridged erythromycin compounds represented by the formulae as illustrated below:
  • W is NR 3 R 4 ;
  • Rp is hydrogen, hydroxy protecting group or hydroxy prodrug group; m is an integer; and n is 0, 1, or 2.
  • Q' is N, CH or CF
  • R 5 is independently selected from hydrogen, acyl, silane, a substituted or unsubstituted, saturated or unsaturated aliphatic group, a substituted or unsubstituted, saturated or unsaturated alicyclic group, a substituted or unsubstituted aromatic group, a substituted or unsubstituted heteroaromatic group, a substituted or unsubstituted heterocyclic group, NR 3 R 4 , OH, NHCORi or NHCONH 2 , and is preferably, NH 2 or NHRi.
  • A is:
  • A is:
  • A is:
  • Examples OfC 1 -C 3 alkyl radicals include methyl, ethyl, propyl and isopropyl radicals; examples OfC 1 -C 6 alkyl radicals include, but are not limited to, methyl, ethyl, propyl, propyl, butyl, pentyl, and hexyl radicals; and examples Of C 1 -C 12 alkyl radicals include, but are not limited to, ethyl, propyl, propyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl radicals and the like.
  • substituted alkenyl refers to a "C 2 -C 12 alkenyl” or “C 2 -C 6 alkenyl” group as previously defined, substituted by one, two, three or more aliphatic substituents.
  • C 2 -C 12 alkynyl or “C 2 -C 6 alkynyl,” as used herein, denote a monovalent group derived from a hydrocarbon moiety containing from two to twelve or two to six carbon atoms having at least one carbon-carbon triple bond by the removal of a single hydrogen atom.
  • substituted heteroarylalkyl refers to a heteroarylalkyl group, as previously defined, substituted by independent replacement of one, two, or three or more aromatic substituents.
  • carboxaldehyde refers to a group of formula - CHO.
  • carboxy refers to a group of formula -COOH.
  • carboxyamide refers to a group of formula - C(O)NH(C 1 -C 12 alkyl) or -C(O)N(C 1 -C 12 alkyl) (C 1 -C 12 alkyl), -C(O)NH 2 , -NHC(O)(C 1 -C 12 alkyl), -N(C 1 -C 12 alkyl)C(O)(C 1 -C 12 alkyl) and the like.
  • hydroxy prodrug group refers to a promoiety group which is known in the art to change the physicochemical, and hence the biological properties of a parent drug in a transient manner by covering or masking the hydroxy group. After said synthetic procedure(s), the hydroxy prodrug group as described herein must be capable of reverting back to hydroxy group in vivo. Hydroxy prodrug groups as known in the art are described generally in Kenneth B. Sloan, Prodrugs, Topical and Ocular Drug Delivery, (Drugs and the Pharmaceutical Sciences; Volume 53), Marcel Dekker, Inc., New York (1992).
  • MAU Mycobacterium avium complex
  • tuberculosis disease related to infection by Mycobacterium tuberculosis
  • gastroenteritis related to infection by Campylobacter jejuni
  • intestinal protozoa related to infection by Cryptosporidium spp.
  • odontogenic infection related to infection by viridans streptococci
  • persistent cough related to infection by Bordetella pertussis
  • gas gangrene related to infection by Clostridium perfringens or Bacteroides spp.
  • atherosclerosis related to infection by Helicobacter pylori or Chlamydia pneumoniae; or the like.
  • compositions of this invention may be administered orally, parenterally, by inhalation spray, topically, rectally, nasally, buccally, vaginally or via an implanted reservoir, preferably by oral administration or administration by injection.
  • the pharmaceutical compositions of this invention may contain any conventional non-toxic pharmaceutically-acceptable carriers, adjuvants or vehicles.
  • the pH of the formulation may be adjusted with pharmaceutically acceptable acids, bases or buffers to enhance the stability of the formulated compound or its delivery form.
  • parenteral as used herein includes subcutaneous, intracutaneous, intravenous, intramuscular, intraarticular, intraarterial, intrasynovial, intrasternal, intrathecal, intralesional and intracranial injection or infusion techniques.
  • bacterial infections, cystic fibrosis and inflammatory conditions are treated or prevented in a subject such as a human or another animal by administering to the subject a therapeutically effective amount of a compound of the invention, in such amounts and for such time as is necessary to achieve the desired result.
  • a “therapeutically effective amount” of a compound of the invention is meant an amount of the compound which confers a therapeutic effect on the treated subject, at a reasonable benefit/risk ratio applicable to any medical treatment.
  • the therapeutic effect may be objective (i.e., measurable by some test or marker) or subjective (i.e., subject gives an indication of or feels an effect).
  • An effective amount of the compound described above may range from about 0.1 mg/Kg to about 500 mg/Kg, preferably from about 1 to about 50 mg/Kg. Effective doses will also vary depending on route of administration, as well as the possibility of co-usage with other agents. It will be understood, however, that the total daily usage of the compounds and compositions of the present invention will be decided by the attending physician within the scope of sound medical judgment.
  • the specific therapeutically effective dose level for any particular subject will depend upon a variety of factors including the disorder being treated and the severity of the disorder; the activity of the specific compound employed; the specific composition employed; the age, body weight, general health, sex and diet of the subject; the time of administration, route of administration, and rate of excretion of the specific compound employed; the duration of the treatment; drugs used in combination or contemporaneously with the specific compound employed; and like factors well known in the medical arts.
  • the total daily dose of the compounds of this invention administered to a human or other animal in single or in divided doses can be in amounts, for example, from 0.01 to 50 mg/kg body weight or more usually from 0.1 to 25 mg/kg body weight.
  • Single dose compositions may contain such amounts or submultiples thereof to make up the daily dose.
  • treatment regimens according to the present invention comprise administration to a subject in need of such treatment from about 10 mg to about 1000 mg of the compound(s) of this invention per day in single or multiple doses.
  • Such administration can be used as a chronic or acute therapy.
  • the amount of active ingredient that may be combined with pharmaceutically excipients or carriers to produce a single dosage form will vary depending upon the host treated and the particular mode of administration.
  • a typical preparation will contain from about 5% to about 95% active compound (w/w).
  • such preparations may contain from about 20% to about 80% active compound.
  • the pharmaceutical compositions of this invention can be administered orally to fish by blending said pharmaceutical compositions into fish feed or said pharmaceutical compositions may be dissolved in water in which infected fish are placed, a method commonly referred to as a medicated bath.
  • the dosage for the treatment offish differs depending upon the purpose of administration (prevention or cure of disease) and type of administration, size and extent of infection of the fish to be treated. Generally, a dosage of 5 - 1000 mg, preferably 20 - 100 mg, per kg of body weight offish may be administered per day, either at one time or divided into several times. It will be recognized that the above-specified dosage is only a general range which may be reduced or increased depending upon the age, body weight, condition of disease, etc. of the fish.
  • THF for tetrahydrofuran
  • TPP or PPh 3 for triphenylphosphine
  • ester compounds of formula (2-2) can be prepared by treating compounds of formula (2-1) with acids of formula Rl-C(O)OH in the presence of bases such as but not limited to Et 3 N, Pyridine, DMAP and coupling agents such as but not limited to EDC, BOPCl, HATU, and the likes in aprotic solvents such as but not limited to dichloromethane, ethylene chloride, THF, DMF, acetonitrile and the like at a temperature from 25 °C to 80 °C and the reaction time is from 2 to 24 hours.
  • bases such as but not limited to Et 3 N, Pyridine, DMAP and coupling agents such as but not limited to EDC, BOPCl, HATU, and the likes in aprotic solvents such as but not limited to dichloromethane, ethylene chloride, THF, DMF, acetonitrile and the like at a temperature from 25 °C to 80 °C and the reaction time is from 2 to 24 hours.
  • step Ic To a solution of the compound of step Ic (57.3g, 0.185mol) in 450 ml of MeCN were added N-hydroxyphanthalimide (60.5 Ig, 0.371mol) and 80 ml of triethylamine. The reaction mixture was stirred at 50 0 C for 5 hours and cooled to room temperature. The reaction was added water (200 ml) and filtered. The pale yellow solid was collected, washed with 100ml of MeOH and ether in the 1:1 ratio. Dried on vacuum to give the title compound (48 g ) as pale solid. ESI MS m/e: 392 (M+H) + .
  • E-oxime isomer 13 C NMR (125 MHz, CDCl 3 ): ⁇ 218.5, 205.6, 191.7, 168.0, 162.0, 152.8, 148.6, 143.0, 134.0, 122.1, 117.0, 108.7, 103.3, 79.3, 79.0, 76.5, 75.8, 74.5, 70.5, 69.8, 66.1, 63.0, 61.5, 51.0, 47.0, 46.2, 40.5, 39.5, 39.3, 28.5, 23.5, 21.4, 20.0, 18.6, 18.0, 14.6, 14.2, 12.6, 12.2.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pulmonology (AREA)
  • Immunology (AREA)
  • Urology & Nephrology (AREA)
  • Rheumatology (AREA)
  • Communicable Diseases (AREA)
  • Genetics & Genomics (AREA)
  • Pain & Pain Management (AREA)
  • Ophthalmology & Optometry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Oncology (AREA)
  • Molecular Biology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

L'invention se rapporte à des composés de formule (I) ou à leurs sels pharmaceutiquement acceptables, leurs esters ou promédicaments (voir formule (I)) qui possèdent des propriétés antibactériennes. L'invention concerne également des compositions pharmaceutiques renfermant lesdits composés et qui sont destinées à être administrées à un sujet nécessitant un tel traitement antibiotique. L'invention concerne également des méthodes de traitement d'une infection bactérienne chez un sujet par administration d'une composition pharmaceutique renfermant les composés selon l'invention. L'invention concerne également des procédés de fabrication des composés selon l'invention.
PCT/US2006/016882 2005-05-04 2006-05-02 Derives d'oxime d'erythromycine pontes 6-11 WO2006119313A2 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
EP06769971A EP1885737A4 (fr) 2005-05-04 2006-05-02 Derives d'oxime d'erythromycine pontes 6-11
CA002605295A CA2605295A1 (fr) 2005-05-04 2006-05-02 Derives d'oxime d'erythromycine pontes 6-11
CN2006800139709A CN101166749B (zh) 2005-05-04 2006-05-02 6-11桥联的肟乙基琥珀酸红霉素酯衍生物
BRPI0610477-0A BRPI0610477A2 (pt) 2005-05-04 2006-05-02 composto, composição farmacêutica que compreende o mesmo, método de tratamento de uma infecção bacteriana, de uma inflamação e de fibrose cìstica em um paciente com necessidade do mesmo
MX2007013730A MX2007013730A (es) 2005-05-04 2006-05-02 Derivados de eritromicina oxima con puente 6-11.
AU2006242188A AU2006242188A1 (en) 2005-05-04 2006-05-02 6-11 bridged oxime erythromycin derivatives
JP2008510145A JP2008540432A (ja) 2005-05-04 2006-05-02 ６−１１橋かけオキシムエリスロマイシン誘導体

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US67767505P 2005-05-04 2005-05-04
US60/677,675 2005-05-04
US11/122,251 US20060252710A1 (en) 2005-05-04 2005-05-04 6-11 Bridged oxime erythromycin derivatives
US11/122,251 2005-05-04

Publications (2)

Publication Number Publication Date
WO2006119313A2 true WO2006119313A2 (fr) 2006-11-09
WO2006119313A3 WO2006119313A3 (fr) 2007-02-22

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Application Number Title Priority Date Filing Date
PCT/US2006/016882 WO2006119313A2 (fr) 2005-05-04 2006-05-02 Derives d'oxime d'erythromycine pontes 6-11

Country Status (8)

Country Link
EP (1) EP1885737A4 (fr)
JP (1) JP2008540432A (fr)
AU (1) AU2006242188A1 (fr)
BR (1) BRPI0610477A2 (fr)
CA (1) CA2605295A1 (fr)
MX (1) MX2007013730A (fr)
TW (1) TW200716143A (fr)
WO (1) WO2006119313A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018201076A3 (fr) * 2017-04-28 2019-02-14 Macrolide Pharmaceuticals Inc. Macrolides à sucres modifiés de type désosamine et utilisations de ceux-ci

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5780605A (en) * 1997-09-08 1998-07-14 Abbott Laboratories 6,9-bridged erythromycin derivatives
US6878691B2 (en) * 2002-05-13 2005-04-12 Enanta Pharmaceuticals, Inc. 6-11 bicyclic ketolide derivatives
US7064110B2 (en) * 2002-05-13 2006-06-20 Enanta Pharmaceuticals, Inc. 6-11 bicycle ketolide derivatives
CA2483678C (fr) * 2002-05-13 2010-01-12 Enanta Pharmaceuticals, Inc. Derives de cetolide 6-11 bicycliques
CA2483875C (fr) * 2002-05-13 2008-09-23 Enanta Pharmaceuticals, Inc. Derives de l'erythromycine 6,11 bicyclique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of EP1885737A4 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2018201076A3 (fr) * 2017-04-28 2019-02-14 Macrolide Pharmaceuticals Inc. Macrolides à sucres modifiés de type désosamine et utilisations de ceux-ci
US11673910B2 (en) 2017-04-28 2023-06-13 Zikani Therapeutics, Inc. Macrolides with modified desosamine sugars and uses thereof

Also Published As

Publication number Publication date
TW200716143A (en) 2007-05-01
CA2605295A1 (fr) 2006-11-09
BRPI0610477A2 (pt) 2010-06-22
AU2006242188A1 (en) 2006-11-09
EP1885737A4 (fr) 2010-11-24
JP2008540432A (ja) 2008-11-20
MX2007013730A (es) 2008-01-28
EP1885737A2 (fr) 2008-02-13
WO2006119313A3 (fr) 2007-02-22

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