JP2005539037A - ベータ−ラクタマーゼ阻害剤プロドラッグ - Google Patents
ベータ−ラクタマーゼ阻害剤プロドラッグ Download PDFInfo
- Publication number
- JP2005539037A JP2005539037A JP2004530453A JP2004530453A JP2005539037A JP 2005539037 A JP2005539037 A JP 2005539037A JP 2004530453 A JP2004530453 A JP 2004530453A JP 2004530453 A JP2004530453 A JP 2004530453A JP 2005539037 A JP2005539037 A JP 2005539037A
- Authority
- JP
- Japan
- Prior art keywords
- prodrug
- beta
- hydroxymethyl
- oxo
- heptane
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
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- 229940002612 prodrug Drugs 0.000 title claims abstract description 166
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- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 35
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- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 56
- NNYHKYDYHWSHKQ-UHFFFAOYSA-N 4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound OC(=O)C1CSC2CCN12 NNYHKYDYHWSHKQ-UHFFFAOYSA-N 0.000 claims description 53
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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- 238000012423 maintenance Methods 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
- ILVPFTMKCHREDJ-UHFFFAOYSA-N methyl 5-amino-2-fluorobenzoate Chemical compound COC(=O)C1=CC(N)=CC=C1F ILVPFTMKCHREDJ-UHFFFAOYSA-N 0.000 description 1
- 229960003085 meticillin Drugs 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 229940041009 monobactams Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000010172 mouse model Methods 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 238000002663 nebulization Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229940100692 oral suspension Drugs 0.000 description 1
- 239000006174 pH buffer Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229950009506 penicillinase Drugs 0.000 description 1
- 210000004303 peritoneum Anatomy 0.000 description 1
- 206010034674 peritonitis Diseases 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000002467 phosphate group Chemical class [H]OP(=O)(O[H])O[*] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 210000003240 portal vein Anatomy 0.000 description 1
- ABVRVIZBZKUTMK-JSYANWSFSA-M potassium clavulanate Chemical compound [K+].[O-]C(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 ABVRVIZBZKUTMK-JSYANWSFSA-M 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000005464 sample preparation method Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000002098 selective ion monitoring Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 210000004872 soft tissue Anatomy 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000007892 solid unit dosage form Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LPQZKKCYTLCDGQ-WEDXCCLWSA-N tazobactam Chemical compound C([C@]1(C)S([C@H]2N(C(C2)=O)[C@H]1C(O)=O)(=O)=O)N1C=CN=N1 LPQZKKCYTLCDGQ-WEDXCCLWSA-N 0.000 description 1
- 229960003865 tazobactam Drugs 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- 210000002438 upper gastrointestinal tract Anatomy 0.000 description 1
- 208000011479 upper respiratory tract disease Diseases 0.000 description 1
- 206010051250 ureteritis Diseases 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40564002P | 2002-08-23 | 2002-08-23 | |
| PCT/IB2003/003582 WO2004018484A1 (en) | 2002-08-23 | 2003-08-11 | Beta-lactamase inhibitor prodrug |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005539037A true JP2005539037A (ja) | 2005-12-22 |
| JP2005539037A5 JP2005539037A5 (https=) | 2006-09-14 |
Family
ID=31946909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004530453A Abandoned JP2005539037A (ja) | 2002-08-23 | 2003-08-11 | ベータ−ラクタマーゼ阻害剤プロドラッグ |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US7091197B2 (https=) |
| EP (1) | EP1534717B1 (https=) |
| JP (1) | JP2005539037A (https=) |
| KR (1) | KR20050037583A (https=) |
| CN (1) | CN1688589A (https=) |
| AP (1) | AP2005003231A0 (https=) |
| AR (1) | AR041028A1 (https=) |
| AT (1) | ATE349452T1 (https=) |
| AU (1) | AU2003250489A1 (https=) |
| BR (1) | BR0313683A (https=) |
| CA (1) | CA2494953A1 (https=) |
| DE (1) | DE60310733D1 (https=) |
| EA (1) | EA007540B1 (https=) |
| EC (1) | ECSP055625A (https=) |
| GT (1) | GT200300179A (https=) |
| HR (1) | HRP20050162A2 (https=) |
| IL (1) | IL166719A0 (https=) |
| IS (1) | IS7693A (https=) |
| MA (1) | MA27387A1 (https=) |
| MX (1) | MXPA05001446A (https=) |
| NO (1) | NO20051497D0 (https=) |
| NZ (1) | NZ538340A (https=) |
| OA (1) | OA12909A (https=) |
| PA (1) | PA8579701A1 (https=) |
| PE (1) | PE20040899A1 (https=) |
| PL (1) | PL375988A1 (https=) |
| TN (1) | TNSN05054A1 (https=) |
| TW (1) | TWI250162B (https=) |
| UY (1) | UY27947A1 (https=) |
| WO (1) | WO2004018484A1 (https=) |
| ZA (1) | ZA200501513B (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004108733A1 (en) * | 2003-06-05 | 2004-12-16 | Pfizer Products Inc. | Beta-lactamase inhibitor prodrug |
| US20060105941A1 (en) * | 2004-11-12 | 2006-05-18 | Allergan, Inc. | Mixed antibiotic codrugs |
| EP1913378A1 (de) * | 2005-07-29 | 2008-04-23 | Sigma-Aldrich Production GmbH | Ionisierungsadditive enthaltende lc/ms-blends |
| WO2010118968A1 (en) | 2009-04-16 | 2010-10-21 | Nicox S.A. | No-donor aspirin derivatives |
| WO2013056163A1 (en) * | 2011-10-14 | 2013-04-18 | The Regents Of The University Of California | Beta-lactamase inhibitors |
| CN104159587A (zh) * | 2012-01-06 | 2014-11-19 | 南佛罗里达大学 | 组合物、使用方法、以及治疗方法 |
| CN109422765B (zh) * | 2017-09-05 | 2020-08-28 | 香港理工大学深圳研究院 | C类β-内酰胺酶抑制剂及其制备方法和应用 |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE34011B1 (en) | 1969-03-13 | 1975-01-08 | Leo Pharm Prod Ltd | New penicillin esters |
| IE34019B1 (en) | 1969-03-18 | 1975-01-08 | Leo Pharm Prod Ltd | New semi-synthetic penicillin esters |
| GB1267936A (en) | 1969-05-28 | 1972-03-22 | Beecham Group Ltd | DERIVATIVES OF alpha-AMINOPENICILLINS |
| US3957764A (en) | 1969-11-11 | 1976-05-18 | Lovens Kemiske Fabrik Produktionsaktieselskab | 6-aminopenicillanic acid derivatives |
| US3862181A (en) | 1970-10-28 | 1975-01-21 | Squibb & Sons Inc | Process for preparing cephalosporins |
| GB1315566A (en) | 1970-11-06 | 1973-05-02 | Leo Pharm Prod Ltd | Penicillanic acid derivatives |
| CA996929A (en) | 1971-04-05 | 1976-09-14 | Kohzi Nakano | Acyloxyalkyl ester derivatives of penicillin |
| GB1433131A (en) | 1972-03-13 | 1976-04-22 | Astra Laekemedel Ab | Penicillins |
| GB1426717A (en) | 1972-03-13 | 1976-03-03 | Astra Laekemedel Ab | Penicillins |
| US4397783A (en) | 1979-03-05 | 1983-08-09 | Pfizer Inc. | Process for converting 6,6-disubstituted penicillanic acid derivatives to the 6-β-congeners |
| DE2927004A1 (de) * | 1979-07-04 | 1981-05-27 | Bayer Ag, 5090 Leverkusen | Penicillansaeure-1,1-dioxide, ihre herstellung und ihre verwendung als arzneimittel als arzneimittel |
| US4287181A (en) * | 1979-10-22 | 1981-09-01 | Pfizer Inc. | Derivatives of 6β-hydroxyalkylpenicillanic acids as β-lactamase inhibitors |
| US4432970A (en) | 1979-11-23 | 1984-02-21 | Pfizer Inc. | 6-beta-Halopenicillanic acid 1,1-dioxides as beta-lactamase inhibitors |
| GB2076812A (en) * | 1980-05-22 | 1981-12-09 | Ciba Geigy Ag | Penam-dioxide compounds, processes for their manufacture, and their use |
| JPS5849387A (ja) | 1981-09-17 | 1983-03-23 | Sankyo Co Ltd | ７−メトキシセフアロスポリン化合物およびその製法 |
| DE3274453D1 (en) * | 1981-09-22 | 1987-01-15 | Kureha Chemical Ind Co Ltd | Penicillin derivatives |
| US4406887A (en) | 1981-10-13 | 1983-09-27 | Bristol-Myers Company | Method for treating resistant bacteria including anaerobes |
| US4428935A (en) * | 1982-05-24 | 1984-01-31 | Pfizer Inc. | Penicillanic acid dioxide prodrug |
| US4521533A (en) | 1984-07-12 | 1985-06-04 | Pfizer Inc. | Salts of 6-alpha-(aminomethyl)penicillanic acid 1,1-dioxide esters and beta-lactam antibiotics |
| DE3901405A1 (de) | 1989-01-19 | 1990-07-26 | Hoechst Ag | Cephalosporinderivate und verfahren zu ihrer herstellung |
| JPH03206038A (ja) | 1990-01-08 | 1991-09-09 | Yoshitomi Pharmaceut Ind Ltd | 抗菌剤 |
| GB9001405D0 (en) | 1990-01-22 | 1990-03-21 | Leo Pharm Prod Ltd | New intermediates,their production and use |
| GB9208492D0 (en) | 1992-04-16 | 1992-06-03 | Glaxo Spa | Heterocyclic compounds |
| WO2004108733A1 (en) | 2003-06-05 | 2004-12-16 | Pfizer Products Inc. | Beta-lactamase inhibitor prodrug |
-
2003
- 2003-08-06 PA PA20038579701A patent/PA8579701A1/es unknown
- 2003-08-11 MX MXPA05001446A patent/MXPA05001446A/es unknown
- 2003-08-11 KR KR1020057002983A patent/KR20050037583A/ko not_active Abandoned
- 2003-08-11 DE DE60310733T patent/DE60310733D1/de not_active Expired - Lifetime
- 2003-08-11 PL PL03375988A patent/PL375988A1/xx unknown
- 2003-08-11 EP EP03792574A patent/EP1534717B1/en not_active Expired - Lifetime
- 2003-08-11 NZ NZ538340A patent/NZ538340A/en unknown
- 2003-08-11 WO PCT/IB2003/003582 patent/WO2004018484A1/en not_active Ceased
- 2003-08-11 HR HR20050162A patent/HRP20050162A2/xx not_active Application Discontinuation
- 2003-08-11 AU AU2003250489A patent/AU2003250489A1/en not_active Abandoned
- 2003-08-11 CA CA002494953A patent/CA2494953A1/en not_active Abandoned
- 2003-08-11 JP JP2004530453A patent/JP2005539037A/ja not_active Abandoned
- 2003-08-11 CN CNA038243164A patent/CN1688589A/zh active Pending
- 2003-08-11 AT AT03792574T patent/ATE349452T1/de not_active IP Right Cessation
- 2003-08-11 AP AP2005003231A patent/AP2005003231A0/xx unknown
- 2003-08-11 BR BR0313683-3A patent/BR0313683A/pt not_active IP Right Cessation
- 2003-08-11 EA EA200500398A patent/EA007540B1/ru unknown
- 2003-08-11 OA OA1200500051A patent/OA12909A/en unknown
- 2003-08-19 PE PE2003000840A patent/PE20040899A1/es not_active Application Discontinuation
- 2003-08-21 UY UY27947A patent/UY27947A1/es not_active Application Discontinuation
- 2003-08-21 AR ARP030103023A patent/AR041028A1/es unknown
- 2003-08-22 TW TW092123156A patent/TWI250162B/zh not_active IP Right Cessation
- 2003-08-22 GT GT200300179A patent/GT200300179A/es unknown
- 2003-08-25 US US10/648,408 patent/US7091197B2/en not_active Expired - Fee Related
-
2005
- 2005-02-07 IL IL16671905A patent/IL166719A0/xx unknown
- 2005-02-10 IS IS7693A patent/IS7693A/is unknown
- 2005-02-21 ZA ZA200501513A patent/ZA200501513B/en unknown
- 2005-02-23 EC EC2005005625A patent/ECSP055625A/es unknown
- 2005-02-23 MA MA28119A patent/MA27387A1/fr unknown
- 2005-02-23 TN TNP2005000054A patent/TNSN05054A1/fr unknown
- 2005-03-21 NO NO20051497A patent/NO20051497D0/no not_active Application Discontinuation
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