UA78524C2 - A process for preparation of carbapenem compounds - Google Patents

A process for preparation of carbapenem compounds Download PDF

Info

Publication number: UA78524C2
Authority: UA; Ukraine
Prior art keywords: water; solid; compound; formula; propanol
Prior art date: 2001-09-26

Application number

UA20040403037A

Other languages

English (en)

Ukrainian (uk)

Inventor

John Williams

Brian K Johnson

Original Assignee

Merck & Co 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.)

2001-09-26

Filing date

2002-09-20

Publication date

2007-04-10

2002-09-20 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

2007-04-10 Publication of UA78524C2 publication Critical patent/UA78524C2/uk

Links

238000000034 method Methods 0.000 title abstract description 50
YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical class C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 title abstract description 37
239000007787 solid Substances 0.000 abstract description 96
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 79
239000003960 organic solvent Substances 0.000 abstract description 69
150000001875 compounds Chemical class 0.000 abstract description 52
238000005406 washing Methods 0.000 abstract description 25
125000003118 aryl group Chemical group 0.000 abstract description 16
239000011261 inert gas Substances 0.000 abstract description 16
125000000217 alkyl group Chemical group 0.000 abstract description 13
125000001072 heteroaryl group Chemical group 0.000 abstract description 9
150000003839 salts Chemical class 0.000 abstract description 8
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 77
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 62
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 49
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
239000000126 substance Substances 0.000 description 49
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 44
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 42
239000000203 mixture Substances 0.000 description 30
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 29
239000002904 solvent Substances 0.000 description 29
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 28
229910052757 nitrogen Inorganic materials 0.000 description 26
229940044613 1-propanol Drugs 0.000 description 24
239000007789 gas Substances 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 11
239000000243 solution Substances 0.000 description 11
101100206695 Rattus norvegicus Thoc6 gene Proteins 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
-1 carboxyphenyl Chemical group 0.000 description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000013078 crystal Substances 0.000 description 9
239000000843 powder Substances 0.000 description 9
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
238000004128 high performance liquid chromatography Methods 0.000 description 8
FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 description 7
229960005335 propanol Drugs 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 6
159000000000 sodium salts Chemical class 0.000 description 6
229940041011 carbapenems Drugs 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
230000007423 decrease Effects 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
239000000047 product Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
230000006378 damage Effects 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 3
229940011051 isopropyl acetate Drugs 0.000 description 3
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
238000000634 powder X-ray diffraction Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
235000014101 wine Nutrition 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
238000005388 cross polarization Methods 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000000605 extraction Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
150000002961 penems Chemical class 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000013049 sediment Substances 0.000 description 2
238000001228 spectrum Methods 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 1
GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
PLQZQEVQLGHUET-NUBCRITNSA-N C1C=CN2[C@H]1CC2=O.[Na] Chemical compound C1C=CN2[C@H]1CC2=O.[Na] PLQZQEVQLGHUET-NUBCRITNSA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
241001024304 Mino Species 0.000 description 1
241000283965 Ochotona princeps Species 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
229910003986 SicO Inorganic materials 0.000 description 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000005456 alcohol based solvent Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004457 alkyl amino carbonyl group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000003368 amide group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000012491 analyte Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
125000004657 aryl sulfonyl amino group Chemical group 0.000 description 1
125000004391 aryl sulfonyl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003245 coal Substances 0.000 description 1
239000002826 coolant Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000002993 cycloalkylene group Chemical group 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
230000009089 cytolysis Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000004475 heteroaralkyl group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000009434 installation Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
238000012423 maintenance Methods 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
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 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
238000004321 preservation Methods 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011946 reduction process Methods 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
238000007790 scraping Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000008259 solid foam Substances 0.000 description 1
238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical group C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
238000005496 tempering 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
150000003536 tetrazoles Chemical class 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
229910052726 zirconium Inorganic materials 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
- 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
- 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
- C07D477/02—Preparation

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
General Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Molecular Biology (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

UA20040403037A 2001-09-26 2002-09-20 A process for preparation of carbapenem compounds UA78524C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US32513001P	2001-09-26	2001-09-26
PCT/US2002/029879 WO2003027067A2 (fr)	2001-09-26	2002-09-20	Processus de fabrication de composes carbapeneme

Publications (1)

Publication Number	Publication Date
UA78524C2 true UA78524C2 (en)	2007-04-10

Family

ID=23266556

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA20040403037A UA78524C2 (en)	2001-09-26	2002-09-20	A process for preparation of carbapenem compounds

Country Status (22)

Country	Link
US (1)	US7022841B2 (fr)
EP (1)	EP1474426B8 (fr)
JP (1)	JP4480396B2 (fr)
KR (1)	KR100628676B1 (fr)
CN (2)	CN100387599C (fr)
AT (1)	ATE518864T1 (fr)
AU (1)	AU2002341747B2 (fr)
BR (1)	BRPI0212411B8 (fr)
CA (1)	CA2461565C (fr)
CY (1)	CY1112092T1 (fr)
DK (1)	DK1474426T3 (fr)
EA (1)	EA008168B1 (fr)
ES (1)	ES2368997T3 (fr)
HU (1)	HU230700B1 (fr)
IL (1)	IL160413A0 (fr)
MX (1)	MXPA04002797A (fr)
NZ (1)	NZ531174A (fr)
PL (1)	PL218808B1 (fr)
PT (1)	PT1474426E (fr)
RS (1)	RS52410B (fr)
UA (1)	UA78524C2 (fr)
WO (1)	WO2003027067A2 (fr)

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CN100457760C (zh) *	2005-10-20	2009-02-04	上海交通大学	尔他培南钠盐的制备方法
WO2008062279A2 (fr) *	2006-11-20	2008-05-29	Orchid Chemicals & Pharmaceuticals Limited	Procédé amélioré de préparation d'un antibiotique de type carbapénème
CN101367812B (zh) *	2007-06-28	2011-04-27	山东轩竹医药科技有限公司	被巯基吡咯烷甲酰胺基环戊烯酸取代的培南衍生物
CN101372490B (zh) *	2007-08-15	2011-02-09	山东轩竹医药科技有限公司	含有巯基氮杂环乙烯基氮杂环的培南衍生物
EP2303225B1 (fr) *	2008-06-11	2013-11-20	Ranbaxy Laboratories Limited	Compositions D'Adduit de Dioxide de Carbone D'Ertapénem et Formes Polymorphiques du Sel Monosodium d'Ertapénem
CN102558182B (zh) *	2010-12-31	2015-02-11	石药集团中奇制药技术（石家庄）有限公司	一种厄他培南钠晶型及其制备方法
CN102363617B (zh) *	2011-11-09	2013-09-18	上海希迈医药科技有限公司	一种厄他培南单钠盐结晶体及其制备方法
WO2013150550A2 (fr) *	2012-04-04	2013-10-10	Orchid Chemicals & Pharmaceuticals Limited	Procédé amélioré de préparation de l'antibiotique carbapénem
IN2013MU03862A (fr)	2013-12-11	2015-07-31	Unimark Remedies Ltd
CN113416193B (zh) *	2021-08-23	2021-12-17	凯莱英医药集团（天津）股份有限公司	厄他培南钠新晶型及其制备方法

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Also Published As

Publication number	Publication date
CN1602312A (zh)	2005-03-30
NZ531174A (en)	2005-09-30
PL218808B1 (pl)	2015-01-30
JP4480396B2 (ja)	2010-06-16
BRPI0212411B1 (pt)	2015-10-27
HU230700B1 (hu)	2017-09-28
KR100628676B1 (ko)	2006-09-27
CN100387599C (zh)	2008-05-14
MXPA04002797A (es)	2004-07-02
CA2461565A1 (fr)	2003-04-03
WO2003027067A2 (fr)	2003-04-03
CY1112092T1 (el)	2015-11-04
RS52410B (sr)	2013-02-28
EP1474426B8 (fr)	2011-10-12
ATE518864T1 (de)	2011-08-15
HUP0500329A2 (hu)	2005-07-28
CA2461565C (fr)	2009-09-15
CN1821248A (zh)	2006-08-23
AU2002341747B2 (en)	2007-10-18
JP2005508334A (ja)	2005-03-31
EP1474426B1 (fr)	2011-08-03
EP1474426A4 (fr)	2005-01-05
US20040176351A1 (en)	2004-09-09
EA200400474A1 (ru)	2004-08-26
BR0212411A (pt)	2004-08-03
PL371666A1 (en)	2005-06-27
IL160413A0 (en)	2004-07-25
BRPI0212411B8 (pt)	2021-07-27
RS22404A (sr)	2007-02-05
KR20040039437A (ko)	2004-05-10
CN100338064C (zh)	2007-09-19
WO2003027067A3 (fr)	2004-09-10
ES2368997T3 (es)	2011-11-24
PT1474426E (pt)	2011-10-07
US7022841B2 (en)	2006-04-04
EP1474426A2 (fr)	2004-11-10
HUP0500329A3 (en)	2012-09-28
EA008168B1 (ru)	2007-04-27
DK1474426T3 (da)	2011-11-21

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