JPH0463878B2 - - Google Patents
Info
- Publication number
- JPH0463878B2 JPH0463878B2 JP59191167A JP19116784A JPH0463878B2 JP H0463878 B2 JPH0463878 B2 JP H0463878B2 JP 59191167 A JP59191167 A JP 59191167A JP 19116784 A JP19116784 A JP 19116784A JP H0463878 B2 JPH0463878 B2 JP H0463878B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- nax
- nitrobenzyloxycarbonyl
- reference example
- nitrobenzyl
- 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
Links
- -1 β-lactam compound Chemical class 0.000 claims description 66
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 125000006239 protecting group Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000000717 hydrazino group Chemical class [H]N([*])N([H])[H] 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 80
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 74
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 74
- 150000001875 compounds Chemical class 0.000 description 59
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 50
- 238000000034 method Methods 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 40
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 235000019439 ethyl acetate Nutrition 0.000 description 25
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 24
- 230000002829 reductive effect Effects 0.000 description 24
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 150000002148 esters Chemical class 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 238000003756 stirring Methods 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 16
- 238000001816 cooling Methods 0.000 description 15
- 125000003277 amino group Chemical group 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
- 238000010898 silica gel chromatography Methods 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000010410 layer Substances 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000010446 mirabilite Substances 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 229910052938 sodium sulfate Inorganic materials 0.000 description 9
- 235000011152 sodium sulphate Nutrition 0.000 description 9
- 238000004809 thin layer chromatography Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 239000002994 raw material Substances 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- DVLFYONBTKHTER-UHFFFAOYSA-N 3-(N-morpholino)propanesulfonic acid Chemical compound OS(=O)(=O)CCCN1CCOCC1 DVLFYONBTKHTER-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 239000007853 buffer solution Substances 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical class CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 description 4
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 4
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 4
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 description 4
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 4
- 229960002591 hydroxyproline Drugs 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- JMJMJDNHVXYAOC-MNOVXSKESA-N (2s,4r)-4-hydroxy-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound C1[C@H](O)C[C@@H](C(O)=O)N1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 JMJMJDNHVXYAOC-MNOVXSKESA-N 0.000 description 3
- DXQHKYRVYYIYPO-AAEUAGOBSA-N (2s,4s)-4-acetyl-1-[(4-nitrophenyl)methoxycarbonyl]pyrrolidine-2-carbothioic s-acid Chemical compound C1[C@@H](C(=O)C)C[C@@H](C(O)=S)N1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 DXQHKYRVYYIYPO-AAEUAGOBSA-N 0.000 description 3
- BSIMZHVOQZIAOY-SCSAIBSYSA-N 1-carbapenem-3-carboxylic acid Chemical compound OC(=O)C1=CC[C@@H]2CC(=O)N12 BSIMZHVOQZIAOY-SCSAIBSYSA-N 0.000 description 3
- HZAVSJRAODFHGF-UHFFFAOYSA-N 2-methyl-7-oxohept-2-enoic acid Chemical compound OC(=O)C(C)=CCCCC=O HZAVSJRAODFHGF-UHFFFAOYSA-N 0.000 description 3
- BDPKOVUGSUGVKQ-MJGOQNOKSA-N 2-o-[(4-methoxyphenyl)methyl] 1-o-[(4-nitrophenyl)methyl] (2s,4r)-4-hydroxypyrrolidine-1,2-dicarboxylate Chemical compound C1=CC(OC)=CC=C1COC(=O)[C@H]1N(C(=O)OCC=2C=CC(=CC=2)[N+]([O-])=O)C[C@H](O)C1 BDPKOVUGSUGVKQ-MJGOQNOKSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- GWHDKFODLYVMQG-UBHAPETDSA-N [(2r,3r)-3-[(1r)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate Chemical compound CC(C)(C)[Si](C)(C)O[C@H](C)[C@@H]1[C@@H](OC(C)=O)NC1=O GWHDKFODLYVMQG-UBHAPETDSA-N 0.000 description 3
- BHIIGRBMZRSDRI-UHFFFAOYSA-N [chloro(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(Cl)OC1=CC=CC=C1 BHIIGRBMZRSDRI-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000010531 catalytic reduction reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 3
- 150000002829 nitrogen Chemical class 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229960002429 proline Drugs 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- PMMYEEVYMWASQN-IMJSIDKUSA-N trans-4-Hydroxy-L-proline Natural products O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- QCLMPSJWFJZBIJ-SFTDATJTSA-N (4-methoxyphenyl)methyl (2s,4s)-4-acetylsulfanyl-2-(benzylcarbamoyl)pyrrolidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1COC(=O)N1[C@H](C(=O)NCC=2C=CC=CC=2)C[C@H](SC(C)=O)C1 QCLMPSJWFJZBIJ-SFTDATJTSA-N 0.000 description 2
- GNLDVGPVKPXIED-UHFFFAOYSA-N (4-methoxyphenyl)methyl 2-[1-[1,3-bis(4-methoxyphenyl)propan-2-yl]-3-[1-[(4-nitrophenyl)methoxycarbonyloxy]ethyl]-4-oxoazetidin-2-yl]acetate Chemical compound C1=CC(OC)=CC=C1COC(=O)CC1N(C(CC=2C=CC(OC)=CC=2)CC=2C=CC(OC)=CC=2)C(=O)C1C(C)OC(=O)OCC1=CC=C([N+]([O-])=O)C=C1 GNLDVGPVKPXIED-UHFFFAOYSA-N 0.000 description 2
- VGLBNJWGUYQZHD-CHWSQXEVSA-N (4-nitrophenyl)methyl (2r,4r)-2-(dimethylcarbamoyl)-4-sulfanylpyrrolidine-1-carboxylate Chemical compound CN(C)C(=O)[C@H]1C[C@@H](S)CN1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 VGLBNJWGUYQZHD-CHWSQXEVSA-N 0.000 description 2
- VGLBNJWGUYQZHD-STQMWFEESA-N (4-nitrophenyl)methyl (2s,4s)-2-(dimethylcarbamoyl)-4-sulfanylpyrrolidine-1-carboxylate Chemical compound CN(C)C(=O)[C@@H]1C[C@H](S)CN1C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 VGLBNJWGUYQZHD-STQMWFEESA-N 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
- MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 2
- ABRHEDIWWISHRH-UHFFFAOYSA-N 1-o-tert-butyl 3-o-[(4-nitrophenyl)methyl] 2-[2-[1-[1,3-bis(4-methoxyphenyl)propan-2-yl]-3-[1-[(4-nitrophenyl)methoxycarbonyloxy]ethyl]-4-oxoazetidin-2-yl]acetyl]propanedioate Chemical compound C1=CC(OC)=CC=C1CC(N1C(C(C(C)OC(=O)OCC=2C=CC(=CC=2)[N+]([O-])=O)C1CC(=O)C(C(=O)OCC=1C=CC(=CC=1)[N+]([O-])=O)C(=O)OC(C)(C)C)=O)CC1=CC=C(OC)C=C1 ABRHEDIWWISHRH-UHFFFAOYSA-N 0.000 description 2
- DVIHDPLIPZPRRR-UHFFFAOYSA-N 2-[1-[1,3-bis(4-methoxyphenyl)propan-2-yl]-3-ethenyl-4-oxoazetidin-2-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1CC(N1C(C(C=C)C1CC(O)=O)=O)CC1=CC=C(OC)C=C1 DVIHDPLIPZPRRR-UHFFFAOYSA-N 0.000 description 2
- BDULRHCUNZSLSK-VQTJNVASSA-N 2-o-[(4-methoxyphenyl)methyl] 1-o-[(4-nitrophenyl)methyl] (2r,4s)-4-formyloxypyrrolidine-1,2-dicarboxylate Chemical compound C1=CC(OC)=CC=C1COC(=O)[C@@H]1N(C(=O)OCC=2C=CC(=CC=2)[N+]([O-])=O)C[C@@H](OC=O)C1 BDULRHCUNZSLSK-VQTJNVASSA-N 0.000 description 2
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- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003147 proline derivatives Chemical class 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
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- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
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- 238000001953 recrystallisation Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- HCQRVJOVBGXTJS-STQMWFEESA-N s-[(3s,5s)-5-(benzylcarbamoyl)pyrrolidin-3-yl] ethanethioate Chemical compound C1[C@H](SC(=O)C)CN[C@@H]1C(=O)NCC1=CC=CC=C1 HCQRVJOVBGXTJS-STQMWFEESA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- 235000009518 sodium iodide Nutrition 0.000 description 1
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- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DUYAAUVXQSMXQP-UHFFFAOYSA-M thioacetate Chemical compound CC([S-])=O DUYAAUVXQSMXQP-UHFFFAOYSA-M 0.000 description 1
- 150000003573 thiols Chemical group 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 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
- JQZIKLPHXXBMCA-UHFFFAOYSA-N triphenylmethanethiol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(S)C1=CC=CC=C1 JQZIKLPHXXBMCA-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- 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
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000453478A CA1283906C (en) | 1983-05-09 | 1984-05-03 | .beta.-LACTAM COMPOUNDS AND PRODUCTION THEREOF |
| CA453478 | 1984-05-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60233076A JPS60233076A (ja) | 1985-11-19 |
| JPH0463878B2 true JPH0463878B2 (ru) | 1992-10-13 |
Family
ID=4127789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59191167A Granted JPS60233076A (ja) | 1984-05-03 | 1984-09-12 | 新規なβ−ラクタム化合物およびその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60233076A (ru) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0780883B2 (ja) * | 1986-03-27 | 1995-08-30 | 住友製薬株式会社 | 新規なβ−ラクタム化合物 |
| JPS6363680A (ja) * | 1986-09-05 | 1988-03-22 | Nippon Redarii Kk | （１ｒ）−１−メチルカルバペネム−３−カルボン酸誘導体 |
| GB9107341D0 (en) * | 1991-04-08 | 1991-05-22 | Ici Plc | Antibiotic compounds |
| NO302475B1 (no) * | 1991-06-04 | 1998-03-09 | Sankyo Co | 1-metylkarbapenemderivater og farmasöytisk preparat inneholdende disse |
| JP3048196B2 (ja) * | 1991-06-20 | 2000-06-05 | 第一製薬株式会社 | カルバペネム誘導体 |
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| CA2099811A1 (en) * | 1992-07-21 | 1994-01-22 | Frederic H. Jung | Antibiotic compounds |
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| GB9515975D0 (en) | 1995-08-04 | 1995-10-04 | Zeneca Ltd | Chemical compounds |
| WO1998007692A1 (en) | 1996-08-17 | 1998-02-26 | Zeneca Limited | 3-mercaptopyrrolidines as farnesyl protein transferase inhibitors |
| BR9910098A (pt) | 1998-05-01 | 2000-12-26 | Kyoto Pharma Ind | Derivados de carbapenem, utilização dos mesmos e compostos intermediários dos mesmos |
| GB9930317D0 (en) | 1999-12-22 | 2000-02-09 | Zeneca Ltd | Novel compounds |
| GB9930318D0 (en) | 1999-12-22 | 2000-02-09 | Zeneca Ltd | Novel compounds |
| ES2370829T3 (es) * | 2004-06-02 | 2011-12-23 | Sandoz Ag | Producto intermedio de meropenem en forma cristalina. |
| JP2006001841A (ja) * | 2004-06-15 | 2006-01-05 | Sumitomo Chemical Co Ltd | 含窒素へテロ環化合物の製造方法 |
| KR100599876B1 (ko) * | 2004-08-31 | 2006-07-13 | 한국화학연구원 | 2-아릴메틸아제티딘 카바페넴 유도체 및 그의 제조방법 |
| US11180504B2 (en) * | 2016-03-16 | 2021-11-23 | Orchid Pharma Ltd. | Substituted carbapenems for the treatment of bacterial infections |
| CN111960984B (zh) * | 2020-09-11 | 2023-04-28 | 江西如益科技发展有限公司 | 一种合成多尼培南侧链中间体的制备方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6019787A (ja) * | 1983-07-12 | 1985-01-31 | Sumitomo Chem Co Ltd | 新規なβ−ラクタム化合物及びその製造法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5287387U (ru) * | 1975-12-23 | 1977-06-29 |
-
1984
- 1984-09-12 JP JP59191167A patent/JPS60233076A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6019787A (ja) * | 1983-07-12 | 1985-01-31 | Sumitomo Chem Co Ltd | 新規なβ−ラクタム化合物及びその製造法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60233076A (ja) | 1985-11-19 |
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