NO751338L

NO751338L -

Info

Publication number: NO751338L
Authority: NO; Norway
Prior art keywords: methyl; amino; cephem; carboxylic acid; alkanoylamino
Prior art date: 1973-03-15

Application number

NO751338A

Other languages

English (en)

Norwegian (no)

Inventor

T Kamiya

T Teraji

M Hashimoto

O Nakaguti

T Oku

Original Assignee

Fujisawa Pharmaceutical Co

Priority date

1973-03-15

Filing date

1975-04-15

Publication date

1974-09-17

1973-03-15 Priority claimed from JP3071873A external-priority patent/JPS5930715B2/ja

1973-03-15 Priority claimed from JP48030719A external-priority patent/JPS5932472B2/ja

1973-03-15 Priority claimed from JP48030720A external-priority patent/JPS6024109B2/ja

1973-08-02 Priority claimed from JP8785373A external-priority patent/JPS5036486A/ja

1973-08-02 Priority claimed from JP8785273A external-priority patent/JPS5036485A/ja

1974-09-17 Publication of NO751338L publication Critical patent/NO751338L/no

1975-04-15 Application filed by Fujisawa Pharmaceutical Co filed Critical Fujisawa Pharmaceutical Co

Links

-1 and 3 R is lower Chemical group 0.000 claims description 322
150000001875 compounds Chemical class 0.000 claims description 72
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 57
125000005236 alkanoylamino group Chemical group 0.000 claims description 42
125000003277 amino group Chemical group 0.000 claims description 41
238000000034 method Methods 0.000 claims description 39
125000006239 protecting group Chemical group 0.000 claims description 38
238000003379 elimination reaction Methods 0.000 claims description 32
125000004442 acylamino group Chemical group 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 20
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 18
125000000217 alkyl group Chemical group 0.000 claims description 18
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
230000007062 hydrolysis Effects 0.000 claims description 16
238000006460 hydrolysis reaction Methods 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
125000005108 alkenylthio group Chemical group 0.000 claims description 2
125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
125000003831 tetrazolyl group Chemical group 0.000 claims description 2
125000001950 (p-hydroxyphenyl)glycinamido group Chemical group 0.000 claims 1
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
125000005518 carboxamido group Chemical group 0.000 claims 1
125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims 1
238000002844 melting Methods 0.000 description 269
230000008018 melting Effects 0.000 description 269
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 245
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 234
239000000243 solution Substances 0.000 description 211
239000000203 mixture Substances 0.000 description 140
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 136
238000000354 decomposition reaction Methods 0.000 description 126
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 114
238000006243 chemical reaction Methods 0.000 description 112
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 108
125000002252 acyl group Chemical group 0.000 description 96
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 82
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 78
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 77
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 76
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 74
239000002904 solvent Substances 0.000 description 73
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 61
238000001816 cooling Methods 0.000 description 58
229920006395 saturated elastomer Polymers 0.000 description 56
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
239000000843 powder Substances 0.000 description 53
239000011541 reaction mixture Substances 0.000 description 53
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 44
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 44
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
238000001914 filtration Methods 0.000 description 43
239000013078 crystal Substances 0.000 description 39
229910052943 magnesium sulfate Inorganic materials 0.000 description 39
235000019341 magnesium sulphate Nutrition 0.000 description 39
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 37
235000017557 sodium bicarbonate Nutrition 0.000 description 37
229910000030 sodium bicarbonate Inorganic materials 0.000 description 37
239000002253 acid Substances 0.000 description 36
238000003756 stirring Methods 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
239000011780 sodium chloride Substances 0.000 description 31
ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 description 30
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 30
229960000583 acetic acid Drugs 0.000 description 28
239000000706 filtrate Substances 0.000 description 27
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
239000000284 extract Substances 0.000 description 23
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 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 22
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 22
239000008346 aqueous phase Substances 0.000 description 22
235000019253 formic acid Nutrition 0.000 description 22
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 22
239000003795 chemical substances by application Substances 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
125000000623 heterocyclic group Chemical group 0.000 description 20
125000005907 alkyl ester group Chemical group 0.000 description 19
239000012071 phase Substances 0.000 description 19
230000009467 reduction Effects 0.000 description 19
238000006722 reduction reaction Methods 0.000 description 19
150000002148 esters Chemical class 0.000 description 18
244000063299 Bacillus subtilis Species 0.000 description 17
235000014469 Bacillus subtilis Nutrition 0.000 description 17
241000191967 Staphylococcus aureus Species 0.000 description 17
UPGDAUPREQILOQ-PWZJBWDHSA-N 2,2,2-trichloroethyl (6r)-7-amino-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;hydrochloride Chemical compound Cl.ClC(Cl)(Cl)COC(=O)C1=CC(C)S[C@@H]2C(N)C(=O)N21 UPGDAUPREQILOQ-PWZJBWDHSA-N 0.000 description 15
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 15
239000007788 liquid Substances 0.000 description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
239000002585 base Substances 0.000 description 13
239000000725 suspension Substances 0.000 description 13
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-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
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 12
IAWZWHRCAHYFIK-DARSQCIJSA-N 2,2,2-trichloroethyl (6r)-4-methyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@H]2SC(C=C(N2C1=O)C(=O)OCC(Cl)(Cl)Cl)C)NC(=O)CC1=CC=CC=C1 IAWZWHRCAHYFIK-DARSQCIJSA-N 0.000 description 11
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 11
125000001931 aliphatic group Chemical group 0.000 description 11
229910052717 sulfur Inorganic materials 0.000 description 11
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 10
238000003776 cleavage reaction Methods 0.000 description 10
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 10
230000007017 scission Effects 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
229910052751 metal Inorganic materials 0.000 description 9
239000002184 metal Substances 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
230000007306 turnover Effects 0.000 description 9
NHVZYCWHYPMYHF-FLHMCOGYSA-N (6r)-4-methyl-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@H]2SC(C=C(N2C1=O)C(O)=O)C)NC(=O)CC1=CC=CC=C1 NHVZYCWHYPMYHF-FLHMCOGYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
150000008064 anhydrides Chemical class 0.000 description 8
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
230000004992 fission Effects 0.000 description 8
239000002198 insoluble material Substances 0.000 description 8
125000004433 nitrogen atom Chemical group N* 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
239000000047 product Substances 0.000 description 8
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 8
238000005406 washing Methods 0.000 description 8
229910052725 zinc Inorganic materials 0.000 description 8
239000011701 zinc Substances 0.000 description 8
ILYFQIRZHAPFLB-MBOVBSECSA-N (6r)-7-amino-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CC(C)S[C@@H]2C(N)C(=O)N21 ILYFQIRZHAPFLB-MBOVBSECSA-N 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
150000008065 acid anhydrides Chemical class 0.000 description 7
229910052783 alkali metal Inorganic materials 0.000 description 7
125000003545 alkoxy group Chemical group 0.000 description 7
239000003054 catalyst Substances 0.000 description 7
238000001035 drying Methods 0.000 description 7
239000005457 ice water Substances 0.000 description 7
125000002911 monocyclic heterocycle group Chemical group 0.000 description 7
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 7
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
239000007858 starting material Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
125000004434 sulfur atom Chemical group 0.000 description 7
YBFSLVNVCUDZDT-FLHMCOGYSA-N (6R)-4-methyl-8-oxo-7-[(2-phenylethanethioyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CC1S[C@H]2N(C(=C1)C(=O)O)C(C2NC(CC1=CC=CC=C1)=S)=O YBFSLVNVCUDZDT-FLHMCOGYSA-N 0.000 description 6
MDWJPFAIEGPWBZ-WQGVUGBDSA-N (6r)-4-methyl-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@H]2SC(C=C(N2C1=O)C(O)=O)C)NC(=O)CC1=CC=CS1 MDWJPFAIEGPWBZ-WQGVUGBDSA-N 0.000 description 6
JNZXTVGPJBITIP-UNMJTNCTSA-N (6r)-4-methyl-8-oxo-7-[[2-(1,3,4-thiadiazol-2-ylsulfanyl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@H]2SC(C=C(N2C1=O)C(O)=O)C)NC(=O)CSC1=NN=CS1 JNZXTVGPJBITIP-UNMJTNCTSA-N 0.000 description 6
PDESBMWDCRWFIM-UNMJTNCTSA-N (6r)-4-methyl-8-oxo-7-[[2-(tetrazol-1-yl)acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@H]2SC(C=C(N2C1=O)C(O)=O)C)NC(=O)CN1C=NN=N1 PDESBMWDCRWFIM-UNMJTNCTSA-N 0.000 description 6
VVUJWONRXMWKAB-UNMJTNCTSA-N (6r)-7-[(2-cyanoacetyl)amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CC(C)S[C@@H]2C(NC(=O)CC#N)C(=O)N21 VVUJWONRXMWKAB-UNMJTNCTSA-N 0.000 description 6
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
230000002411 adverse Effects 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
239000003863 metallic catalyst Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
229910052760 oxygen Inorganic materials 0.000 description 6
239000001301 oxygen Substances 0.000 description 6
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000011734 sodium Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 6
ALITVBHEANJHAL-VVJTWVHASA-N (6r)-7-[(2-hydroxy-2-thiophen-2-ylacetyl)amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@H]2SC(C=C(N2C1=O)C(O)=O)C)NC(=O)C(O)C1=CC=CS1 ALITVBHEANJHAL-VVJTWVHASA-N 0.000 description 5
YTFMDRSFSRMAAR-KLSKTNFXSA-N (6r)-7-[[2-(3,6-dihydro-2h-pyran-5-yl)acetyl]amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@H]2SC(C=C(N2C1=O)C(O)=O)C)NC(=O)CC1=CCCOC1 YTFMDRSFSRMAAR-KLSKTNFXSA-N 0.000 description 5
JPUWCVTYBFVYTJ-VYZQMCHSSA-N (6r)-7-[[2-(3-chlorophenyl)acetyl]amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@H]2SC(C=C(N2C1=O)C(O)=O)C)NC(=O)CC1=CC=CC(Cl)=C1 JPUWCVTYBFVYTJ-VYZQMCHSSA-N 0.000 description 5
WPSOKYIPJIFXIP-ZUSWXSMMSA-N 2,2,2-trichloroethyl (6r)-4-methyl-7-[[2-[(5-methyl-1,3,4-thiadiazol-2-yl)oxy]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@H]2SC(C=C(N2C1=O)C(=O)OCC(Cl)(Cl)Cl)C)NC(=O)COC1=NN=C(C)S1 WPSOKYIPJIFXIP-ZUSWXSMMSA-N 0.000 description 5
HXLWTTDQTLYOLF-KLSKTNFXSA-N 2,2,2-trichloroethyl (6r)-4-methyl-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@H]2SC(C=C(N2C1=O)C(=O)OCC(Cl)(Cl)Cl)C)NC(=O)CC1=CC=CS1 HXLWTTDQTLYOLF-KLSKTNFXSA-N 0.000 description 5
JRAUSVNASSMOLN-PPACVUAOSA-N 2,2,2-trichloroethyl (6r)-7-[(2-cyanoacetyl)amino]-4-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound ClC(Cl)(Cl)COC(=O)C1=CC(C)S[C@@H]2C(NC(=O)CC#N)C(=O)N21 JRAUSVNASSMOLN-PPACVUAOSA-N 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
238000000862 absorption spectrum Methods 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
238000005917 acylation reaction Methods 0.000 description 5
230000000845 anti-microbial effect Effects 0.000 description 5
238000010531 catalytic reduction reaction Methods 0.000 description 5
238000007796 conventional method Methods 0.000 description 5
230000008030 elimination Effects 0.000 description 5
239000002038 ethyl acetate fraction Substances 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
125000004430 oxygen atom Chemical group O* 0.000 description 5
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 5
239000011591 potassium Substances 0.000 description 5
229910052700 potassium Inorganic materials 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
125000003396 thiol group Chemical group [H]S* 0.000 description 5
CHSGJWJASYITAB-UNMJTNCTSA-N (6R)-4-methyl-8-oxo-7-(propanethioylamino)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CC1S[C@H]2N(C(=C1)C(=O)O)C(C2NC(CC)=S)=O CHSGJWJASYITAB-UNMJTNCTSA-N 0.000 description 4
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230000008569 process Effects 0.000 description 3
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150000001721 carbon Chemical group 0.000 description 2
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201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
DWYUSIUKGQJEFM-UHFFFAOYSA-N ethoxy hydrogen carbonate Chemical compound CCOOC(O)=O DWYUSIUKGQJEFM-UHFFFAOYSA-N 0.000 description 2
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238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
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BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
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HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
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KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 2
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 2
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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LSWWNKUULMMMIL-UHFFFAOYSA-J zirconium(iv) bromide Chemical compound Br[Zr](Br)(Br)Br LSWWNKUULMMMIL-UHFFFAOYSA-J 0.000 description 1