ZA200303558B - Novel carbapenem derivatives. - Google Patents
Novel carbapenem derivatives. Download PDFInfo
- Publication number
- ZA200303558B ZA200303558B ZA200303558A ZA200303558A ZA200303558B ZA 200303558 B ZA200303558 B ZA 200303558B ZA 200303558 A ZA200303558 A ZA 200303558A ZA 200303558 A ZA200303558 A ZA 200303558A ZA 200303558 B ZA200303558 B ZA 200303558B
- Authority
- ZA
- South Africa
- Prior art keywords
- optionally substituted
- carbamoyl
- group
- amino
- hydroxyl
- Prior art date
Links
- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical class C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 title description 11
- -1 cyano, hydroxyl Chemical group 0.000 claims description 137
- 125000000217 alkyl group Chemical group 0.000 claims description 65
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 63
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 56
- 125000004414 alkyl thio group Chemical group 0.000 claims description 55
- 125000005843 halogen group Chemical group 0.000 claims description 55
- 125000003282 alkyl amino group Chemical group 0.000 claims description 53
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 48
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 125000005842 heteroatom Chemical group 0.000 claims description 27
- 125000004434 sulfur atom Chemical group 0.000 claims description 26
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 25
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 24
- 125000002950 monocyclic group Chemical group 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 239000001301 oxygen Substances 0.000 claims description 24
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 21
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 230000003115 biocidal effect Effects 0.000 claims description 12
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000002619 bicyclic group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000002757 morpholinyl group Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 6
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 150000001540 azides Chemical class 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000005045 dihydroisoquinolinyl group Chemical group C1(NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000004193 piperazinyl group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 241000894006 Bacteria Species 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- 101150116596 dhp-1 gene Proteins 0.000 description 5
- 102100025142 Beta-microseminoprotein Human genes 0.000 description 4
- 101100185029 Homo sapiens MSMB gene Proteins 0.000 description 4
- 206010041925 Staphylococcal infections Diseases 0.000 description 4
- 208000015688 methicillin-resistant staphylococcus aureus infectious disease Diseases 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 241000712461 unidentified influenza virus Species 0.000 description 4
- 208000035473 Communicable disease Diseases 0.000 description 3
- TYMABNNERDVXID-DLYFRVTGSA-N Panipenem Chemical compound C([C@@H]1[C@H](C(N1C=1C(O)=O)=O)[C@H](O)C)C=1S[C@H]1CCN(C(C)=N)C1 TYMABNNERDVXID-DLYFRVTGSA-N 0.000 description 3
- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 3
- ZSKVGTPCRGIANV-ZXFLCMHBSA-N imipenem Chemical compound C1C(SCC\N=C\N)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 ZSKVGTPCRGIANV-ZXFLCMHBSA-N 0.000 description 3
- 229960002182 imipenem Drugs 0.000 description 3
- DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 description 3
- 229960002260 meropenem Drugs 0.000 description 3
- 229950011346 panipenem Drugs 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- 241000192125 Firmicutes Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 238000011321 prophylaxis Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical class CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- 206010029155 Nephropathy toxic Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005588 carbonic acid salt group Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- IIUBFCZXGSJIJX-UHFFFAOYSA-N imidazo[5,1-b][1,3]thiazole Chemical group C1=NC=C2SC=CN21 IIUBFCZXGSJIJX-UHFFFAOYSA-N 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000004552 isoquinolin-4-yl group Chemical group C1=NC=C(C2=CC=CC=C12)* 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229960003085 meticillin Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007694 nephrotoxicity Effects 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 1
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- 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
- C07D477/14—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 hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 3
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000356997 | 2000-11-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200303558B true ZA200303558B (en) | 2004-09-06 |
Family
ID=18829133
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200303558A ZA200303558B (en) | 2000-11-24 | 2001-11-22 | Novel carbapenem derivatives. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6908913B2 (da) |
| EP (1) | EP1336612B1 (da) |
| JP (1) | JP3878131B2 (da) |
| KR (1) | KR100841125B1 (da) |
| CN (1) | CN1275970C (da) |
| AU (2) | AU2408802A (da) |
| BR (1) | BR0115615A (da) |
| CA (1) | CA2429675A1 (da) |
| DE (1) | DE60126125T2 (da) |
| DK (1) | DK1336612T3 (da) |
| ES (1) | ES2278819T3 (da) |
| HU (1) | HUP0400652A2 (da) |
| IL (2) | IL155990A0 (da) |
| MX (1) | MXPA03004331A (da) |
| PL (1) | PL362694A1 (da) |
| PT (1) | PT1336612E (da) |
| RU (1) | RU2276154C2 (da) |
| WO (1) | WO2002042312A1 (da) |
| ZA (1) | ZA200303558B (da) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6458780B1 (en) * | 1998-07-27 | 2002-10-01 | Meiji Seika Kaisha, Ltd. | Carbapenem derivatives |
| ES2228896T3 (es) * | 2000-01-26 | 2005-04-16 | Meiji Seika Kaisha, Ltd. | Nuevos derivados de carbapenem. |
| CN101255171A (zh) | 2002-12-13 | 2008-09-03 | 明治制果株式会社 | 2-位取代碳青霉烯衍生物的中间体及其制备方法 |
| US20070265242A1 (en) * | 2004-09-03 | 2007-11-15 | Makoto Sunagawa | Novel Carbapenem Compound |
| US20090036685A1 (en) | 2005-07-22 | 2009-02-05 | Dai Kubota | Process for Producing Imidazothiazole Derivatives |
| JP2010013356A (ja) * | 2006-10-26 | 2010-01-21 | Meiji Seika Kaisha Ltd | 結晶性カルバペネム化合物 |
| SI2097400T1 (sl) * | 2007-01-05 | 2013-10-30 | Daiichi Sankyo Company, Limited | Zliti substituirani aminopirolidinski derivat |
| CN102133527A (zh) * | 2010-12-23 | 2011-07-27 | 西安凯立化工有限公司 | 一种用于美罗培南合成的钯锡炭催化剂及制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69807722T2 (de) | 1997-01-28 | 2003-04-30 | Meiji Seika Kaisha | Carbapenemderivate |
| US6458780B1 (en) * | 1998-07-27 | 2002-10-01 | Meiji Seika Kaisha, Ltd. | Carbapenem derivatives |
| ES2228896T3 (es) | 2000-01-26 | 2005-04-16 | Meiji Seika Kaisha, Ltd. | Nuevos derivados de carbapenem. |
| WO2001055155A1 (fr) * | 2000-01-26 | 2001-08-02 | Meiji Seika Kaisha, Ltd. | Nouveaux derives de carbapenem de type sel quaternaire |
-
2001
- 2001-11-22 ZA ZA200303558A patent/ZA200303558B/en unknown
- 2001-11-22 RU RU2003118640/04A patent/RU2276154C2/ru not_active IP Right Cessation
- 2001-11-22 BR BR0115615-2A patent/BR0115615A/pt not_active Application Discontinuation
- 2001-11-22 AU AU2408802A patent/AU2408802A/xx active Pending
- 2001-11-22 JP JP2002544445A patent/JP3878131B2/ja not_active Expired - Fee Related
- 2001-11-22 CA CA002429675A patent/CA2429675A1/en not_active Abandoned
- 2001-11-22 PL PL01362694A patent/PL362694A1/xx not_active Application Discontinuation
- 2001-11-22 EP EP01997496A patent/EP1336612B1/en not_active Expired - Lifetime
- 2001-11-22 US US10/344,729 patent/US6908913B2/en not_active Expired - Fee Related
- 2001-11-22 HU HU0400652A patent/HUP0400652A2/hu unknown
- 2001-11-22 IL IL15599001A patent/IL155990A0/xx unknown
- 2001-11-22 KR KR1020037006827A patent/KR100841125B1/ko not_active IP Right Cessation
- 2001-11-22 CN CNB018221742A patent/CN1275970C/zh not_active Expired - Fee Related
- 2001-11-22 WO PCT/JP2001/010252 patent/WO2002042312A1/ja active IP Right Grant
- 2001-11-22 ES ES01997496T patent/ES2278819T3/es not_active Expired - Lifetime
- 2001-11-22 AU AU2002224088A patent/AU2002224088B2/en not_active Ceased
- 2001-11-22 DE DE60126125T patent/DE60126125T2/de not_active Expired - Fee Related
- 2001-11-22 PT PT01997496T patent/PT1336612E/pt unknown
- 2001-11-22 MX MXPA03004331A patent/MXPA03004331A/es active IP Right Grant
- 2001-11-22 DK DK01997496T patent/DK1336612T3/da active
-
2003
- 2003-05-19 IL IL155990A patent/IL155990A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| RU2276154C2 (ru) | 2006-05-10 |
| US6908913B2 (en) | 2005-06-21 |
| HUP0400652A2 (hu) | 2004-06-28 |
| CN1486322A (zh) | 2004-03-31 |
| CN1275970C (zh) | 2006-09-20 |
| DE60126125D1 (de) | 2007-03-08 |
| JP3878131B2 (ja) | 2007-02-07 |
| KR100841125B1 (ko) | 2008-06-24 |
| PL362694A1 (en) | 2004-11-02 |
| DE60126125T2 (de) | 2007-11-15 |
| BR0115615A (pt) | 2004-02-03 |
| US20040038967A1 (en) | 2004-02-26 |
| MXPA03004331A (es) | 2003-08-19 |
| PT1336612E (pt) | 2007-04-30 |
| KR20040029310A (ko) | 2004-04-06 |
| WO2002042312A1 (fr) | 2002-05-30 |
| DK1336612T3 (da) | 2007-05-07 |
| AU2002224088B2 (en) | 2007-06-14 |
| EP1336612A4 (en) | 2004-03-03 |
| JPWO2002042312A1 (ja) | 2004-03-25 |
| EP1336612B1 (en) | 2007-01-17 |
| IL155990A0 (en) | 2003-12-23 |
| IL155990A (en) | 2009-09-22 |
| EP1336612A1 (en) | 2003-08-20 |
| CA2429675A1 (en) | 2002-05-30 |
| ES2278819T3 (es) | 2007-08-16 |
| AU2408802A (en) | 2002-06-03 |
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