DE69909098T2 - C-2 s/o- und s/n-formaldehydacetal-derivate von carbapenem-3-carbonsäuren und deren verwendung als antibiotika und beta-lactamas-inhibitoren - Google Patents
C-2 s/o- und s/n-formaldehydacetal-derivate von carbapenem-3-carbonsäuren und deren verwendung als antibiotika und beta-lactamas-inhibitoren Download PDFInfo
- Publication number
- DE69909098T2 DE69909098T2 DE69909098T DE69909098T DE69909098T2 DE 69909098 T2 DE69909098 T2 DE 69909098T2 DE 69909098 T DE69909098 T DE 69909098T DE 69909098 T DE69909098 T DE 69909098T DE 69909098 T2 DE69909098 T2 DE 69909098T2
- Authority
- DE
- Germany
- Prior art keywords
- heterocyclyl
- hydroxyethyl
- methyl
- hydrogen
- pharmaceutically acceptable
- 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.)
- Expired - Lifetime
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- 229910052760 oxygen Inorganic materials 0.000 title claims description 18
- 229910052717 sulfur Inorganic materials 0.000 title claims description 15
- 239000003242 anti bacterial agent Substances 0.000 title abstract description 19
- 229940088710 antibiotic agent Drugs 0.000 title abstract description 16
- 239000003112 inhibitor Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000001408 amides Chemical class 0.000 claims abstract description 11
- 150000002148 esters Chemical class 0.000 claims abstract description 11
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 7
- CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 claims abstract description 5
- OBOXTJCIIVUZEN-UHFFFAOYSA-N [C].[O] Chemical compound [C].[O] OBOXTJCIIVUZEN-UHFFFAOYSA-N 0.000 claims abstract description 5
- -1 N-heterocyclyl Chemical group 0.000 claims description 148
- 238000000034 method Methods 0.000 claims description 32
- 238000002360 preparation method Methods 0.000 claims description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000004442 acylamino group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 230000000844 anti-bacterial effect Effects 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000006413 ring segment Chemical group 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 125000004423 acyloxy group Chemical group 0.000 claims description 10
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 10
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 10
- 125000002950 monocyclic group Chemical group 0.000 claims description 10
- 125000003441 thioacyl group Chemical group 0.000 claims description 10
- 102000006635 beta-lactamase Human genes 0.000 claims description 9
- 241000894006 Bacteria Species 0.000 claims description 8
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 8
- 108090000204 Dipeptidase 1 Proteins 0.000 claims description 7
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims description 7
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 239000002132 β-lactam antibiotic Substances 0.000 claims description 7
- 229940124586 β-lactam antibiotics Drugs 0.000 claims description 7
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 5
- 125000005277 alkyl imino group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 5
- 125000005122 aminoalkylamino group Chemical group 0.000 claims description 5
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 5
- 125000005518 carboxamido group Chemical group 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 5
- 125000005646 oximino group Chemical group 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- 125000005035 acylthio group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000012351 deprotecting agent Substances 0.000 claims 1
- 229910017053 inorganic salt Inorganic materials 0.000 claims 1
- 239000003781 beta lactamase inhibitor Substances 0.000 abstract description 6
- 229940126813 beta-lactamase inhibitor Drugs 0.000 abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 51
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 25
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000007787 solid Substances 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 19
- 229940093499 ethyl acetate Drugs 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 229930186147 Cephalosporin Natural products 0.000 description 10
- 229930182555 Penicillin Natural products 0.000 description 10
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 10
- 229940124587 cephalosporin Drugs 0.000 description 10
- 239000011591 potassium Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 150000001780 cephalosporins Chemical class 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 229910052700 potassium Inorganic materials 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 7
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- 239000002585 base Chemical class 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
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- 238000002211 ultraviolet spectrum Methods 0.000 description 7
- FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 150000002960 penicillins Chemical class 0.000 description 6
- 239000002798 polar solvent Substances 0.000 description 6
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- 239000008346 aqueous phase Substances 0.000 description 5
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- 229940041011 carbapenems Drugs 0.000 description 5
- ORFOPKXBNMVMKC-DWVKKRMSSA-N ceftazidime Chemical compound S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 ORFOPKXBNMVMKC-DWVKKRMSSA-N 0.000 description 5
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- 229910052708 sodium Inorganic materials 0.000 description 5
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- BSIMZHVOQZIAOY-SCSAIBSYSA-N 1-carbapenem-3-carboxylic acid Chemical class OC(=O)C1=CC[C@@H]2CC(=O)N12 BSIMZHVOQZIAOY-SCSAIBSYSA-N 0.000 description 4
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- 239000002511 suppository base Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 229940100615 topical ointment Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms 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 3
- C07D477/20—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98114067 | 1998-07-28 | ||
| EP98114067A EP0976752A1 (en) | 1998-07-28 | 1998-07-28 | C-2 S/O- and S/N-Formaldehyde acetal derivatives of carbapenem antibiotics |
| PCT/EP1999/005295 WO2000006574A1 (en) | 1998-07-28 | 1999-07-23 | NOVEL C-2 S/O- AND S/N FORMALDEHYDE ACETAL DERIVATIVES OF CARBAPENEM-3-CARBOXYLIC ACIDS AND THEIR USE AS ANTIBIOTICS AND β-LACTAMASE INHIBITORS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69909098D1 DE69909098D1 (de) | 2003-07-31 |
| DE69909098T2 true DE69909098T2 (de) | 2004-04-08 |
Family
ID=8232355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69909098T Expired - Lifetime DE69909098T2 (de) | 1998-07-28 | 1999-07-23 | C-2 s/o- und s/n-formaldehydacetal-derivate von carbapenem-3-carbonsäuren und deren verwendung als antibiotika und beta-lactamas-inhibitoren |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US6482818B2 (enExample) |
| EP (2) | EP0976752A1 (enExample) |
| JP (1) | JP4598273B2 (enExample) |
| KR (1) | KR20010086351A (enExample) |
| CN (1) | CN1154649C (enExample) |
| AT (1) | ATE243696T1 (enExample) |
| AU (1) | AU760249B2 (enExample) |
| CA (1) | CA2338776C (enExample) |
| DE (1) | DE69909098T2 (enExample) |
| ES (1) | ES2203164T3 (enExample) |
| HU (1) | HUP0102729A3 (enExample) |
| IL (1) | IL141114A (enExample) |
| MX (1) | MXPA01000905A (enExample) |
| NZ (1) | NZ509578A (enExample) |
| PT (1) | PT1100800E (enExample) |
| WO (1) | WO2000006574A1 (enExample) |
| ZA (1) | ZA200100737B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE464280T1 (de) * | 2004-08-23 | 2010-04-15 | Sicor Inc | Synthese von idarubin-aglycon |
| AU2008253257B2 (en) | 2007-05-21 | 2013-10-03 | Hans Rudolf Pfaendler | Bactericidal anti-MRSA active pharmaceutical composition containing carbapenems |
| CN101412718B (zh) * | 2007-10-19 | 2011-04-27 | 山东轩竹医药科技有限公司 | 含有硫基杂环胺甲酰基的碳青霉烯衍生物 |
| CN103059028B (zh) * | 2013-01-30 | 2014-05-07 | 山东罗欣药业股份有限公司 | 一种替比培南匹伏酯的制备方法 |
| CN114957258A (zh) * | 2021-02-25 | 2022-08-30 | 华东理工大学 | 基于碳青霉烯结构的广谱丝氨酸β-内酰胺酶抑制剂的合成及其在耐药细菌抑制中的应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58116485A (ja) * | 1981-12-29 | 1983-07-11 | Shionogi & Co Ltd | 新規抗生物質カルバペネム誘導体およびその製造法 |
| JPS58124785A (ja) * | 1982-01-20 | 1983-07-25 | Shionogi & Co Ltd | プルラシドマイシンｂおよびｃのデオキシ体ならびにその製造法 |
| EP0079244B1 (en) * | 1981-11-10 | 1986-12-30 | Shionogi & Co., Ltd. | Pluracidomycin b,c, and d and analogs thereof, their production and a microorganism for use therein |
| JPS6054387A (ja) * | 1983-08-03 | 1985-03-28 | メルク エンド カムパニ− インコ−ポレ−テツド | チエナマイシンの誘導体製造法 |
| CA1285940C (en) * | 1984-07-02 | 1991-07-09 | Merck & Co., Inc. | Carbapenems having a 2-quaternary heteroarylalkylthio substituent |
| IE851586L (en) * | 1984-07-02 | 1986-01-02 | Interchem Internat S A | I methylcarbapenems having a 2-quaternary¹heteroarylalkylthio substituent |
| JPS63255283A (ja) * | 1987-04-11 | 1988-10-21 | Nippon Redarii Kk | （１ｒ，５ｓ，６ｓ）−２−〔（３−置換イミダゾリニウム−１−イル）アルキル〕チオ−６−〔（ｒ）−１−ヒドロキシエチル〕−１−メチル−カルバペネム−３−カルボキシレ−ト |
| US5116833A (en) * | 1990-10-19 | 1992-05-26 | Bristol-Myers Squibb Company | Antibiotic c-3 dithioacetal-substituted carbapenem compounds, compositions, and methods of use thereof |
-
1998
- 1998-07-28 EP EP98114067A patent/EP0976752A1/en not_active Withdrawn
-
1999
- 1999-07-23 EP EP99936602A patent/EP1100800B1/en not_active Expired - Lifetime
- 1999-07-23 NZ NZ509578A patent/NZ509578A/xx not_active IP Right Cessation
- 1999-07-23 AU AU51639/99A patent/AU760249B2/en not_active Ceased
- 1999-07-23 CN CNB998091634A patent/CN1154649C/zh not_active Expired - Fee Related
- 1999-07-23 CA CA002338776A patent/CA2338776C/en not_active Expired - Fee Related
- 1999-07-23 WO PCT/EP1999/005295 patent/WO2000006574A1/en not_active Ceased
- 1999-07-23 KR KR1020017001122A patent/KR20010086351A/ko not_active Ceased
- 1999-07-23 AT AT99936602T patent/ATE243696T1/de not_active IP Right Cessation
- 1999-07-23 HU HU0102729A patent/HUP0102729A3/hu unknown
- 1999-07-23 JP JP2000562374A patent/JP4598273B2/ja not_active Expired - Fee Related
- 1999-07-23 DE DE69909098T patent/DE69909098T2/de not_active Expired - Lifetime
- 1999-07-23 MX MXPA01000905A patent/MXPA01000905A/es not_active IP Right Cessation
- 1999-07-23 IL IL14111499A patent/IL141114A/en not_active IP Right Cessation
- 1999-07-23 ES ES99936602T patent/ES2203164T3/es not_active Expired - Lifetime
- 1999-07-23 PT PT99936602T patent/PT1100800E/pt unknown
-
2001
- 2001-01-25 ZA ZA200100737A patent/ZA200100737B/en unknown
- 2001-01-25 US US09/770,536 patent/US6482818B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US6482818B2 (en) | 2002-11-19 |
| HUP0102729A2 (hu) | 2002-01-28 |
| MXPA01000905A (es) | 2002-06-04 |
| JP4598273B2 (ja) | 2010-12-15 |
| EP1100800B1 (en) | 2003-06-25 |
| EP1100800A1 (en) | 2001-05-23 |
| NZ509578A (en) | 2003-06-30 |
| CA2338776C (en) | 2008-04-29 |
| CN1154649C (zh) | 2004-06-23 |
| HUP0102729A3 (en) | 2002-09-30 |
| DE69909098D1 (de) | 2003-07-31 |
| IL141114A (en) | 2004-02-08 |
| CA2338776A1 (en) | 2000-02-10 |
| WO2000006574A1 (en) | 2000-02-10 |
| AU760249B2 (en) | 2003-05-08 |
| US20010031749A1 (en) | 2001-10-18 |
| JP2002521484A (ja) | 2002-07-16 |
| ES2203164T3 (es) | 2004-04-01 |
| IL141114A0 (en) | 2002-02-10 |
| AU5163999A (en) | 2000-02-21 |
| CN1311790A (zh) | 2001-09-05 |
| ATE243696T1 (de) | 2003-07-15 |
| EP0976752A1 (en) | 2000-02-02 |
| KR20010086351A (ko) | 2001-09-10 |
| ZA200100737B (en) | 2002-07-25 |
| PT1100800E (pt) | 2003-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |