CA2463084C - Preparation and use of carbohydrate-based bicyclic ring structures with antimicrobial and cytostatic activity - Google Patents
Preparation and use of carbohydrate-based bicyclic ring structures with antimicrobial and cytostatic activity Download PDFInfo
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- CA2463084C CA2463084C CA2463084A CA2463084A CA2463084C CA 2463084 C CA2463084 C CA 2463084C CA 2463084 A CA2463084 A CA 2463084A CA 2463084 A CA2463084 A CA 2463084A CA 2463084 C CA2463084 C CA 2463084C
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- 238000006460 hydrolysis reaction Methods 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
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- XJSFLOJWULLJQS-NGVXBBESSA-N josamycin Chemical compound CO[C@H]1[C@H](OC(C)=O)CC(=O)O[C@H](C)C\C=C\C=C\[C@H](O)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O[C@@H]2O[C@@H](C)[C@H](OC(=O)CC(C)C)[C@](C)(O)C2)[C@@H](C)O1 XJSFLOJWULLJQS-NGVXBBESSA-N 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
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- 230000002045 lasting effect Effects 0.000 description 1
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- 238000011068 loading method Methods 0.000 description 1
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- QGEFGPVWRJCFQP-UHFFFAOYSA-M magnesium;methanidylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C1=CC=CC=C1 QGEFGPVWRJCFQP-UHFFFAOYSA-M 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- MHWLWQUZZRMNGJ-UHFFFAOYSA-N nalidixic acid Chemical compound C1=C(C)N=C2N(CC)C=C(C(O)=O)C(=O)C2=C1 MHWLWQUZZRMNGJ-UHFFFAOYSA-N 0.000 description 1
- 229960000210 nalidixic acid Drugs 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
- 229960003255 natamycin Drugs 0.000 description 1
- NCXMLFZGDNKEPB-FFPOYIOWSA-N natamycin Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C[C@@H](C)OC(=O)/C=C/[C@H]2O[C@@H]2C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 NCXMLFZGDNKEPB-FFPOYIOWSA-N 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000474 nursing effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
- 150000002972 pentoses Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
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- 230000035755 proliferation Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
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- 230000005855 radiation Effects 0.000 description 1
- 230000010322 reactivation of latent virus Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
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- 230000002269 spontaneous effect Effects 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- 150000005672 tetraenes Chemical class 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- NQPHMXWPDCSHTE-UHFFFAOYSA-N trifluoromethanesulfonyl azide Chemical compound FC(F)(F)S(=O)(=O)N=[N+]=[N-] NQPHMXWPDCSHTE-UHFFFAOYSA-N 0.000 description 1
- 210000000427 trigeminal ganglion Anatomy 0.000 description 1
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- MZFGYVZYLMNXGL-UHFFFAOYSA-N undec-10-enoyl chloride Chemical compound ClC(=O)CCCCCCCCC=C MZFGYVZYLMNXGL-UHFFFAOYSA-N 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/10—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical containing unsaturated carbon-to-carbon bonds
-
- 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
-
- 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
- A61P31/10—Antimycotics
-
- 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
- A61P31/12—Antivirals
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/02—Acyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H7/00—Compounds containing non-saccharide radicals linked to saccharide radicals by a carbon-to-carbon bond
- C07H7/04—Carbocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H9/00—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical
- C07H9/02—Compounds containing a hetero ring sharing at least two hetero atoms with a saccharide radical the hetero ring containing only oxygen as ring hetero atoms
- C07H9/04—Cyclic acetals
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)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Crystallography & Structural Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA002684419A CA2684419A1 (en) | 2001-10-15 | 2002-10-15 | Preparation and use of carbohydrate-based bicyclic ring structures with antimicrobial and cytostatic activity |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/977,478 | 2001-10-15 | ||
| US09/977,478 US7138531B2 (en) | 2001-10-15 | 2001-10-15 | Preparation and use of carbohydrate-based bicyclic ring structures with antimicrobial and cytostatic activity |
| PCT/US2002/032817 WO2003032905A2 (en) | 2001-10-15 | 2002-10-15 | Preparation and use of carbohydrate-based ring structures with antimicrobial and cytostatic activity |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002684419A Division CA2684419A1 (en) | 2001-10-15 | 2002-10-15 | Preparation and use of carbohydrate-based bicyclic ring structures with antimicrobial and cytostatic activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2463084A1 CA2463084A1 (en) | 2003-04-24 |
| CA2463084C true CA2463084C (en) | 2010-07-27 |
Family
ID=25525177
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2463084A Expired - Fee Related CA2463084C (en) | 2001-10-15 | 2002-10-15 | Preparation and use of carbohydrate-based bicyclic ring structures with antimicrobial and cytostatic activity |
| CA002684419A Abandoned CA2684419A1 (en) | 2001-10-15 | 2002-10-15 | Preparation and use of carbohydrate-based bicyclic ring structures with antimicrobial and cytostatic activity |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002684419A Abandoned CA2684419A1 (en) | 2001-10-15 | 2002-10-15 | Preparation and use of carbohydrate-based bicyclic ring structures with antimicrobial and cytostatic activity |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7138531B2 (enExample) |
| EP (3) | EP1446391A4 (enExample) |
| JP (1) | JP4504018B2 (enExample) |
| AU (1) | AU2002335813A1 (enExample) |
| CA (2) | CA2463084C (enExample) |
| WO (1) | WO2003032905A2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7101908B2 (en) * | 2001-10-15 | 2006-09-05 | Kemin Pharma Europe B.V.B.A. | Bicyclic carbohydrate compounds useful in the treatment of infections caused by herpesviridae |
| AU2002950657A0 (en) * | 2002-08-08 | 2002-09-12 | Alchemia Limited | Derivatives of monosaccharides for drug discovery |
| AU2002951995A0 (en) * | 2002-10-11 | 2002-10-31 | Alchemia Limited | Classes of compounds that interact with gpcrs |
| US7125854B2 (en) * | 2003-01-07 | 2006-10-24 | Kemin Pharma B.V.B.A. | Bicyclic carbohydrates as antiprotozoal bioactive for the treatment of infections caused by parasites |
| WO2004062575A2 (en) | 2003-01-07 | 2004-07-29 | Kemin Pharma Europe Bvba | Bicyclic carbohydrate compounds useful in the treatment of infections caused by flaviviridae sp., such as hepatitis c and bovine viral diarrhea viruses |
| WO2009055779A1 (en) * | 2007-10-26 | 2009-04-30 | Redox Pharmaceutical Corporation | A method for reversal of bacterial resistance to metallo-b-lactamase antibiotics and vancomycin |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5116821A (en) * | 1990-11-20 | 1992-05-26 | The Procter & Gamble Company | Sulfated glyceroglucolipids as inhibitors of bacterial adherence |
| US5212075A (en) * | 1991-04-15 | 1993-05-18 | The Regents Of The University Of California | Compositions and methods for introducing effectors to pathogens and cells |
| EP0524439A1 (en) * | 1991-07-24 | 1993-01-27 | F.Hoffmann-La Roche & Co. Aktiengesellschaft | Novel cyclohexane and tetrahydropyran derivatives and antifungal compositions containing these derivatives |
| NL9300058A (nl) * | 1992-06-18 | 1994-01-17 | Stichting Rega V Z W | 1,5-anhydrohexitol nucleoside analoga en farmaceutisch gebruik daarvan. |
| EP0601417A3 (de) * | 1992-12-11 | 1998-07-01 | Hoechst Aktiengesellschaft | Physiologisch verträglicher und physiologisch abbaubarer, Kohlenhydratrezeptorblocker auf Polymerbasis, ein Verfahren zu seiner Herstellung und seine Verwendung |
| US5627194A (en) * | 1993-11-17 | 1997-05-06 | Allelix Biopharmaceuticals Inc. | Anti-viral guanidino-substituted compounds |
| JPH07238080A (ja) * | 1994-02-25 | 1995-09-12 | Sagami Chem Res Center | ４−（１，２−ジヒドロキシ−３−ブテニル）−１，３−ジオキサン誘導体 |
| JPH0881490A (ja) * | 1994-09-12 | 1996-03-26 | Sagami Chem Res Center | ３−ｏ−（３−ｏ−カルバモイルマンノピラノシル）ヘプテノール誘導体、及びマンノグロース誘導体の製造法 |
| WO1997034623A1 (en) * | 1996-03-21 | 1997-09-25 | Transcell Technologies, Inc. | Solid phase lipoglycopeptide library, compositions and methods |
| FR2751334B1 (fr) * | 1996-07-19 | 1998-10-16 | Sanofi Sa | Polysaccharides synthetiques, procede pour leur preparation et compositions pharmaceutiques les contenant |
| FR2802536B1 (fr) * | 1999-11-23 | 2003-06-13 | Chru Lille | Oligomannosides de synthese, leur preparation et leur utilisation a la detection d'anticorps et a la prevention d'infections |
| KR100464917B1 (ko) * | 2001-09-25 | 2005-01-06 | 정재민 | 간 기능 영상화를 위한 디설파이드 환원형 갈락토즈 결합혈청알부민 및 이를 포함한 방사성 동위원소 표지 화합물 |
| AUPS143402A0 (en) | 2002-03-28 | 2002-05-09 | Alchemia Pty Ltd | Anomeric derivatives of monosaccharides |
| AU2002950657A0 (en) | 2002-08-08 | 2002-09-12 | Alchemia Limited | Derivatives of monosaccharides for drug discovery |
-
2001
- 2001-10-15 US US09/977,478 patent/US7138531B2/en not_active Expired - Fee Related
-
2002
- 2002-10-15 JP JP2003535711A patent/JP4504018B2/ja not_active Expired - Fee Related
- 2002-10-15 CA CA2463084A patent/CA2463084C/en not_active Expired - Fee Related
- 2002-10-15 AU AU2002335813A patent/AU2002335813A1/en not_active Abandoned
- 2002-10-15 WO PCT/US2002/032817 patent/WO2003032905A2/en not_active Ceased
- 2002-10-15 CA CA002684419A patent/CA2684419A1/en not_active Abandoned
- 2002-10-15 EP EP02770578A patent/EP1446391A4/en not_active Withdrawn
- 2002-10-15 EP EP10185546A patent/EP2361920A3/en not_active Withdrawn
- 2002-10-15 EP EP09160439A patent/EP2168972A3/en not_active Withdrawn
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2004
- 2004-06-04 US US10/861,768 patent/US7534871B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003032905A2 (en) | 2003-04-24 |
| EP1446391A2 (en) | 2004-08-18 |
| EP2168972A2 (en) | 2010-03-31 |
| US7138531B2 (en) | 2006-11-21 |
| US20040224904A1 (en) | 2004-11-11 |
| JP4504018B2 (ja) | 2010-07-14 |
| JP2005509615A (ja) | 2005-04-14 |
| CA2684419A1 (en) | 2003-04-24 |
| EP2168972A3 (en) | 2010-06-02 |
| EP2361920A3 (en) | 2011-10-12 |
| US7534871B2 (en) | 2009-05-19 |
| CA2463084A1 (en) | 2003-04-24 |
| EP2361920A2 (en) | 2011-08-31 |
| AU2002335813A1 (en) | 2003-04-28 |
| US20030158243A1 (en) | 2003-08-21 |
| EP1446391A4 (en) | 2008-02-20 |
| WO2003032905A3 (en) | 2004-01-29 |
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