JPS6261984A - β−ラクタム化合物の製法 - Google Patents

β−ラクタム化合物の製法

Info

Publication number: JPS6261984A
Authority: JP; Japan
Prior art keywords: group; groups; formula; substituted; compound
Prior art date: 1985-09-11
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.): Pending

Application number

JP61212833A

Other languages

English (en)

Japanese (ja)

Inventor

エルンスト　フンゲルビューラー

ヤロスラフ　カルボダ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy AG

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.)

1985-09-11

Filing date

1986-09-11

Publication date

1987-03-18

1986-09-11 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1987-03-18 Publication of JPS6261984A publication Critical patent/JPS6261984A/ja

Status Pending legal-status Critical Current

Links

-1 beta-lactam compound Chemical class 0.000 title claims description 238
238000004519 manufacturing process Methods 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 72
125000000217 alkyl group Chemical group 0.000 claims description 65
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 44
150000003839 salts Chemical class 0.000 claims description 36
125000006239 protecting group Chemical group 0.000 claims description 32
238000000034 method Methods 0.000 claims description 29
125000003545 alkoxy group Chemical group 0.000 claims description 26
125000000623 heterocyclic group Chemical group 0.000 claims description 21
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 18
229910052757 nitrogen Inorganic materials 0.000 claims description 18
125000004434 sulfur atom Chemical group 0.000 claims description 18
125000003118 aryl group Chemical group 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 14
229910052717 sulfur Inorganic materials 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
125000004430 oxygen atom Chemical group O* 0.000 claims description 11
125000005843 halogen group Chemical group 0.000 claims description 10
239000007858 starting material Substances 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
125000000962 organic group Chemical group 0.000 claims description 7
229910052698 phosphorus Inorganic materials 0.000 claims description 7
239000011574 phosphorus Substances 0.000 claims description 7
239000000126 substance Substances 0.000 claims description 7
125000004423 acyloxy group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
125000003342 alkenyl group Chemical group 0.000 claims description 5
125000004185 ester group Chemical group 0.000 claims description 5
125000000524 functional group Chemical group 0.000 claims description 5
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 4
125000005110 aryl thio group Chemical group 0.000 claims description 4
150000002894 organic compounds Chemical class 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 3
125000003431 oxalo group Chemical group 0.000 claims description 3
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 3
125000004149 thio group Chemical group *S* 0.000 claims description 3
125000002217 penem group Chemical group 0.000 claims description 2
HNOLIWBAJVIBOU-UHFFFAOYSA-N prop-2-enyl 2-chloro-2-oxoacetate Chemical compound ClC(=O)C(=O)OCC=C HNOLIWBAJVIBOU-UHFFFAOYSA-N 0.000 claims description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
AWIJRPNMLHPLNC-UHFFFAOYSA-N thiocarboxylic acid group Chemical group C(=S)O AWIJRPNMLHPLNC-UHFFFAOYSA-N 0.000 claims description 2
RGFGLOSXLUDSAD-UHFFFAOYSA-N 2-(3-phenylprop-2-enoxycarbonylamino)ethanethioic s-acid Chemical compound SC(=O)CNC(=O)OCC=CC1=CC=CC=C1 RGFGLOSXLUDSAD-UHFFFAOYSA-N 0.000 claims 1
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 1
125000005002 aryl methyl group Chemical group 0.000 claims 1
IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 1
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 1
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 61
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
125000003277 amino group Chemical group 0.000 description 40
239000002253 acid Substances 0.000 description 38
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 37
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
125000002252 acyl group Chemical group 0.000 description 25
239000000243 solution Substances 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
125000001424 substituent group Chemical group 0.000 description 22
235000019439 ethyl acetate Nutrition 0.000 description 21
125000004429 atom Chemical group 0.000 description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 description 19
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
150000002148 esters Chemical class 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
238000003756 stirring Methods 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
125000003282 alkyl amino group Chemical group 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 13
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
125000004453 alkoxycarbonyl group Chemical group 0.000 description 12
229910001868 water Inorganic materials 0.000 description 12
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
150000007513 acids Chemical class 0.000 description 10
229910052801 chlorine Inorganic materials 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
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 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 9
125000005103 alkyl silyl group Chemical group 0.000 description 9
239000008346 aqueous phase Substances 0.000 description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
125000001309 chloro group Chemical group Cl* 0.000 description 9
239000012043 crude product Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
235000011121 sodium hydroxide Nutrition 0.000 description 9
125000003638 stannyl group Chemical group [H][Sn]([H])([H])* 0.000 description 9
125000001931 aliphatic group Chemical group 0.000 description 8
125000002947 alkylene group Chemical group 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
150000001735 carboxylic acids Chemical class 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
229910052739 hydrogen Inorganic materials 0.000 description 8
239000002904 solvent Substances 0.000 description 8
125000003396 thiol group Chemical group [H]S* 0.000 description 8
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
229910052783 alkali metal Inorganic materials 0.000 description 7
239000002585 base Substances 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
229910052731 fluorine Inorganic materials 0.000 description 7
229910052751 metal Inorganic materials 0.000 description 7
239000002184 metal Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 7
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 7
125000004043 oxo group Chemical group O=* 0.000 description 7
238000006722 reduction reaction Methods 0.000 description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000004414 alkyl thio group Chemical group 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
125000001475 halogen functional group Chemical group 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
125000002950 monocyclic group Chemical group 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 5
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
229910000147 aluminium phosphate Inorganic materials 0.000 description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 5
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
238000003797 solvolysis reaction Methods 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical class F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
239000000370 acceptor Substances 0.000 description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
125000005236 alkanoylamino group Chemical group 0.000 description 4
150000003973 alkyl amines Chemical class 0.000 description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
235000010233 benzoic acid Nutrition 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
125000004093 cyano group Chemical group *C#N 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
238000001914 filtration Methods 0.000 description 4
125000001153 fluoro group Chemical group F* 0.000 description 4
125000005842 heteroatom Chemical group 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
229910052705 radium Inorganic materials 0.000 description 4
HCWPIIXVSYCSAN-UHFFFAOYSA-N radium atom Chemical compound [Ra] HCWPIIXVSYCSAN-UHFFFAOYSA-N 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 3
125000004442 acylamino group Chemical group 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000006136 alcoholysis reaction Methods 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 3
125000005237 alkyleneamino group Chemical group 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000003638 chemical reducing agent Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
125000000392 cycloalkenyl group Chemical group 0.000 description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
125000001072 heteroaryl group Chemical group 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
238000007327 hydrogenolysis reaction Methods 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 3
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
230000004962 physiological condition Effects 0.000 description 3
239000011591 potassium Substances 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
235000011118 potassium hydroxide Nutrition 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
238000006467 substitution reaction Methods 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
229910052718 tin Inorganic materials 0.000 description 3
238000007738 vacuum evaporation Methods 0.000 description 3
NJYFRQQXXXRJHK-UHFFFAOYSA-N (4-aminophenyl) thiocyanate Chemical group NC1=CC=C(SC#N)C=C1 NJYFRQQXXXRJHK-UHFFFAOYSA-N 0.000 description 2
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 2
OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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ZYBWTEQKHIADDQ-UHFFFAOYSA-N ethanol;methanol Chemical compound OC.CCO ZYBWTEQKHIADDQ-UHFFFAOYSA-N 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
125000006627 ethoxycarbonylamino group Chemical group 0.000 description 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
150000002222 fluorine compounds Chemical class 0.000 description 1
150000003948 formamides Chemical class 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
239000010931 gold Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
125000006331 halo benzoyl group Chemical group 0.000 description 1
231100001261 hazardous Toxicity 0.000 description 1
UTFBGYDHJGSHCK-UHFFFAOYSA-G heptasodium heptafluoride Chemical compound [F-].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[F-].[F-].[F-].[F-].[F-].[F-] UTFBGYDHJGSHCK-UHFFFAOYSA-G 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical class [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 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
239000000852 hydrogen donor Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
239000005457 ice water Substances 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
125000006302 indol-3-yl methyl group Chemical group [H]N1C([H])=C(C2=C([H])C([H])=C([H])C([H])=C12)C([H])([H])* 0.000 description 1
125000006301 indolyl methyl group Chemical group 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
125000000686 lactone group Chemical group 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229940099690 malic acid Drugs 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000002004 n-butylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
125000004708 n-butylthio group Chemical group C(CCC)S* 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001298 n-hexoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004706 n-propylthio group Chemical group C(CC)S* 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012434 nucleophilic reagent Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
150000002941 palladium compounds Chemical class 0.000 description 1
HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 description 1
150000002961 penems Chemical class 0.000 description 1
125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
229940117803 phenethylamine Drugs 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
125000005543 phthalimide group Chemical group 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
235000007686 potassium Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000004224 protection Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000004308 pyranonyl group Chemical group O1C(C(=CC=C1)*)=O 0.000 description 1
125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 description 1
150000003256 radium compounds Chemical class 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
238000010517 secondary reaction Methods 0.000 description 1
230000028327 secretion Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000004523 tetrazol-1-yl group Chemical group N1(N=NN=C1)* 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 description 1
150000003566 thiocarboxylic acids Chemical class 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
230000017105 transposition Effects 0.000 description 1
125000006168 tricyclic group Chemical group 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
125000002348 vinylic group Chemical group 0.000 description 1
239000003021 water soluble solvent Substances 0.000 description 1

JP61212833A 1985-09-11 1986-09-11 β−ラクタム化合物の製法 Pending JPS6261984A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH392885		1985-09-11
CH03928/85-3		1985-09-11
CH00919/86-5		1986-03-06

Publications (1)

Publication Number	Publication Date
JPS6261984A true JPS6261984A (ja)	1987-03-18

Family

ID=4266505

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP61212833A Pending JPS6261984A (ja)	1985-09-11	1986-09-11	β−ラクタム化合物の製法

Country Status (2)

Country	Link
JP (1)	JPS6261984A (de)
DD (1)	DD258235A5 (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH06220054A (ja) *	1992-06-18	1994-08-09	Tanabe Seiyaku Co Ltd	カルボキシル基保護基の除去方法

1986
- 1986-09-09 DD DD29426286A patent/DD258235A5/de not_active IP Right Cessation
- 1986-09-11 JP JP61212833A patent/JPS6261984A/ja active Pending

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH06220054A (ja) *	1992-06-18	1994-08-09	Tanabe Seiyaku Co Ltd	カルボキシル基保護基の除去方法

Also Published As

Publication number	Publication date
DD258235A5 (de)	1988-07-13

Publication	Publication Date	Title
US4576749A (en)	1986-03-18	3-Acylamino-1-carboxymethylaminocarbonyl-2-azetidinones
TWI498115B (zh)	2015-09-01	咪唑羰基化合物
JPS6284082A (ja)	1987-04-17	２−オキソ−１−〔〔（置換スルホニル）アミノ〕カルボニル〕アゼチジン類
EP0540609A1 (de)	1993-05-12	Cephalosporine und ihre homologen, zubereitungen und pharmazeutsiche präparate
JPH0196181A (ja)	1989-04-14	２−オキソ−１−［［（置換スルホニル）アミノ］カルボニル］アゼチジン類
KR900006449B1 (ko)	1990-08-31	아제티디논 화합물의 제조방법
IE57609B1 (en)	1993-01-27	Process for the production of penems
US5153315A (en)	1992-10-06	Intermediates for β-lactam compounds
JPS59108789A (ja)	1984-06-23	ペネム化合物の製法
EP0110826B1 (de)	1987-08-19	6-Hydroxyniederalkyl-penem-Verbindungen, Verfahren zu ihrer Herstellung, pharmazeutische Präparate, welche diese Verbindungen enthalten, und Verwendung von letzteren
HU198067B (en)	1989-07-28	Process for producing tautomer thiones
FR2499081A1 (fr)	1982-08-06	Derives de 7-oxo-1-azabicyclo (3-2-0) hept-2-ene, leur preparation et leur application en tant que medicaments
JPS6254427B2 (de)	1987-11-14
JPS6261984A (ja)	1987-03-18	β−ラクタム化合物の製法
DE4019960C2 (de)	2001-06-07	Neue Penamderivate und deren Salze, Verfahren zu ihrer Herstellung und antibakterielles Mittel mit einem Gehalt derselben
EP0416810A2 (de)	1991-03-13	Cephalosporinderivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate und Zwischenverbindungen
EP0109362A1 (de)	1984-05-23	Heterocyclylverbindungen, Verfahren zu ihrer Herstellung, pharmazeutische Präparate, welche diese Verbindungen enthalten, und Verwendung von letzteren
JPS5846066A (ja)	1983-03-17	β−ラクタム類
US5215997A (en)	1993-06-01	Synthesis of beta-lactam compounds
EP0112283B1 (de)	1987-08-12	Heterocyclylthioverbindungen, Verfahren zu ihrer Herstellung, pharmazeutische Präparate, welche diese Verbindungen enthalten, und Verwendung von letzteren
DE3888127T2 (de)	1994-07-07	6-(Substituiertes Methylen)peneme.
JPS62158282A (ja)	1987-07-14	１−カルバセフアロスポリン抗生物質
JPS6034970A (ja)	1985-02-22	２―ヘテロサイクリル―低級アルキル―２―ペネム化合物、その製法および該化合物を含有する医薬製剤
JPS61212588A (ja)	1986-09-20	８‐オキソ‐２‐オキサ‐１‐アザビシクロ〔４．２．０〕オクタン‐３‐カルボン酸類
JPH0129185B2 (de)	1989-06-08

JPS6261984A - β−ラクタム化合物の製法 - Google Patents

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Links

Applications Claiming Priority (3)

Publications (1)

Family

ID=4266505

Family Applications (1)

Country Status (2)

Cited By (1)

Cited By (1)

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