CS245753B2 - Production method of 7 beta-acylamido-3-cefem-4-carboxyle acids - Google Patents

Info

Publication number

CS245753B2

CS245753B2 CS723209A CS320972A CS245753B2 CS 245753 B2 CS245753 B2 CS 245753B2 CS 723209 A CS723209 A CS 723209A CS 320972 A CS320972 A CS 320972A CS 245753 B2 CS245753 B2 CS 245753B2

Authority

CS

Czechoslovakia

Prior art keywords

group

formula

carbon atoms

alkyl

acid

Prior art date

1971-05-14

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• 239000002253 acid Substances 0.000 title claims abstract description 168
• 150000007513 acids Chemical class 0.000 title description 19
• 238000004519 manufacturing process Methods 0.000 title description 7
• -1 Cephalosporin compounds Chemical class 0.000 claims abstract description 248
• 239000000203 mixture Substances 0.000 claims abstract description 201
• 150000001875 compounds Chemical class 0.000 claims abstract description 162
• 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 114
• 150000002148 esters Chemical class 0.000 claims abstract description 58
• 150000003839 salts Chemical class 0.000 claims abstract description 44
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 33
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 29
• 239000003795 chemical substances by application Substances 0.000 claims abstract description 27
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
• 239000001257 hydrogen Substances 0.000 claims abstract description 18
• 125000000962 organic group Chemical group 0.000 claims abstract description 16
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 15
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 340
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 178
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 132
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 131
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 127
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 106
• 238000000034 method Methods 0.000 claims description 97
• 125000000217 alkyl group Chemical group 0.000 claims description 95
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 65
• 125000003118 aryl group Chemical group 0.000 claims description 65
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
• 238000002360 preparation method Methods 0.000 claims description 61
• 229910052717 sulfur Inorganic materials 0.000 claims description 52
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
• 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 44
• 235000017557 sodium bicarbonate Nutrition 0.000 claims description 44
• 238000006243 chemical reaction Methods 0.000 claims description 42
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 40
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 37
• 229910052760 oxygen Inorganic materials 0.000 claims description 37
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 36
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 33
• 239000001301 oxygen Substances 0.000 claims description 33
• 239000002904 solvent Substances 0.000 claims description 33
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 32
• 125000003545 alkoxy group Chemical group 0.000 claims description 30
• 239000011734 sodium Substances 0.000 claims description 29
• 229910052708 sodium Inorganic materials 0.000 claims description 29
• 125000004434 sulfur atom Chemical group 0.000 claims description 29
• 229910052757 nitrogen Inorganic materials 0.000 claims description 27
• 125000001544 thienyl group Chemical group 0.000 claims description 27
• 125000001624 naphthyl group Chemical group 0.000 claims description 25
• 231100000252 nontoxic Toxicity 0.000 claims description 25
• 230000003000 nontoxic effect Effects 0.000 claims description 25
• 125000004076 pyridyl group Chemical group 0.000 claims description 25
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
• 230000008569 process Effects 0.000 claims description 23
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 21
• 229910052794 bromium Inorganic materials 0.000 claims description 21
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
• 125000000623 heterocyclic group Chemical group 0.000 claims description 21
• 239000011593 sulfur Substances 0.000 claims description 21
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
• 239000000460 chlorine Substances 0.000 claims description 20
• 229910052801 chlorine Inorganic materials 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 19
• 150000002367 halogens Chemical group 0.000 claims description 19
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
• 125000002541 furyl group Chemical group 0.000 claims description 18
• 125000005842 heteroatom Chemical group 0.000 claims description 17
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 16
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 15
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 15
• 229910052740 iodine Inorganic materials 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 14
• 150000003462 sulfoxides Chemical class 0.000 claims description 14
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 14
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 13
• 125000004414 alkyl thio group Chemical group 0.000 claims description 13
• 125000002252 acyl group Chemical group 0.000 claims description 12
• 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 12
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 12
• 125000001424 substituent group Chemical group 0.000 claims description 12
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 12
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 11
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 11
• 125000003884 phenylalkyl group Chemical group 0.000 claims description 11
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 10
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 10
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 10
• 125000001841 imino group Chemical group [H]N=* 0.000 claims description 10
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
• 125000006239 protecting group Chemical group 0.000 claims description 10
• 229920002554 vinyl polymer Polymers 0.000 claims description 10
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
• 125000004423 acyloxy group Chemical group 0.000 claims description 9
• 229910052731 fluorine Inorganic materials 0.000 claims description 9
• 239000011630 iodine Substances 0.000 claims description 9
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 9
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 9
• 125000000335 thiazolyl group Chemical group 0.000 claims description 9
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 8
• 125000003342 alkenyl group Chemical group 0.000 claims description 8
• 125000003277 amino group Chemical group 0.000 claims description 8
• 150000008064 anhydrides Chemical class 0.000 claims description 8
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 8
• 125000005605 benzo group Chemical group 0.000 claims description 8
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
• 125000006501 nitrophenyl group Chemical group 0.000 claims description 8
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 7
• 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 7
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 7
• 125000005042 acyloxymethyl group Chemical group 0.000 claims description 7
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 7
• 125000005110 aryl thio group Chemical group 0.000 claims description 7
• 125000004104 aryloxy group Chemical group 0.000 claims description 7
• 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 claims description 7
• 125000002720 diazolyl group Chemical group 0.000 claims description 7
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 7
• 125000002971 oxazolyl group Chemical group 0.000 claims description 7
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 7
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
• 125000005307 thiatriazolyl group Chemical group S1N=NN=C1* 0.000 claims description 7
• 125000001425 triazolyl group Chemical group 0.000 claims description 7
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
• 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims description 6
• GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 6
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 6
• 150000001408 amides Chemical class 0.000 claims description 6
• 150000001412 amines Chemical class 0.000 claims description 6
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 6
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 5
• 125000003368 amide group Chemical group 0.000 claims description 5
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 5
• 125000001153 fluoro group Chemical group F* 0.000 claims description 5
• 125000005059 halophenyl group Chemical group 0.000 claims description 5
• 125000001041 indolyl group Chemical group 0.000 claims description 5
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 5
• 125000003431 oxalo group Chemical group 0.000 claims description 5
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
• VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
• 125000004849 alkoxymethyl group Chemical group 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
• 239000011230 binding agent Substances 0.000 claims description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
• 239000003153 chemical reaction reagent Substances 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 150000002825 nitriles Chemical class 0.000 claims description 4
• 125000002071 phenylalkoxy group Chemical group 0.000 claims description 4
• 239000011591 potassium Substances 0.000 claims description 4
• 229910052700 potassium Inorganic materials 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 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 claims description 4
• 125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims description 3
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
• 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
• 125000005037 alkyl phenyl group Chemical group 0.000 claims description 3
• IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 3
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 3
• 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 claims description 3
• 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 3
• 125000003438 dodecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 3
• 125000001207 fluorophenyl group Chemical group 0.000 claims description 3
• 150000007529 inorganic bases Chemical class 0.000 claims description 3
• 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 claims description 3
• 125000006626 methoxycarbonylamino group Chemical group 0.000 claims description 3
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
• 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 3
• VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 claims description 3
• 150000003512 tertiary amines Chemical class 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
• JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims description 2
• JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 2
• 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
• 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
• 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 2
• 150000001718 carbodiimides Chemical class 0.000 claims description 2
• 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
• 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
• 150000002576 ketones Chemical class 0.000 claims description 2
• 125000002560 nitrile group Chemical group 0.000 claims description 2
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
• 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
• 239000012429 reaction media Substances 0.000 claims description 2
• 125000003944 tolyl group Chemical group 0.000 claims description 2
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 8
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 2
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
• 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 2
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 2
• 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 1
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
• YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims 1
• AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims 1
• WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical class C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 claims 1
• YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
• AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims 1
• 125000006243 carbonyl protecting group Chemical group 0.000 claims 1
• FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 claims 1
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
• 125000000842 isoxazolyl group Chemical group 0.000 claims 1
• 125000000547 substituted alkyl group Chemical group 0.000 claims 1
• 229940124587 cephalosporin Drugs 0.000 abstract description 21
• 229930186147 Cephalosporin Natural products 0.000 abstract description 20
• 238000000926 separation method Methods 0.000 abstract description 3
• NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 abstract 2
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• MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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• MBVGZSSYNIBAKI-UHFFFAOYSA-N pyridine-2-carbothioic s-acid Chemical compound OC(=S)C1=CC=CC=N1 MBVGZSSYNIBAKI-UHFFFAOYSA-N 0.000 description 1
• JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical group C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
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• YWIVKILSMZOHHF-QJZPQSOGSA-N sodium;(2s,3s,4s,5r,6r)-6-[(2s,3r,4r,5s,6r)-3-acetamido-2-[(2s,3s,4r,5r,6r)-6-[(2r,3r,4r,5s,6r)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2- Chemical compound [Na+].CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 YWIVKILSMZOHHF-QJZPQSOGSA-N 0.000 description 1
• AYGJDUHQRFKLBG-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;dihydrate Chemical compound O.O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 AYGJDUHQRFKLBG-UHFFFAOYSA-M 0.000 description 1
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• 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
• ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 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
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• 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
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• YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
• 125000000101 thioether group Chemical group 0.000 description 1
• 150000003573 thiols Chemical class 0.000 description 1
• FFVJAVUSCJCRPT-UHFFFAOYSA-N thiophen-2-yl acetate Chemical compound CC(=O)OC1=CC=CS1 FFVJAVUSCJCRPT-UHFFFAOYSA-N 0.000 description 1
• 150000004764 thiosulfuric acid derivatives Chemical class 0.000 description 1
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• 125000005270 trialkylamine group Chemical group 0.000 description 1
• 150000003852 triazoles Chemical class 0.000 description 1
• QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
• 239000005051 trimethylchlorosilane Substances 0.000 description 1
• 238000001665 trituration Methods 0.000 description 1
• 238000001291 vacuum drying Methods 0.000 description 1
• 229910052720 vanadium Inorganic materials 0.000 description 1
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• 239000000341 volatile oil Substances 0.000 description 1
• 239000008215 water for injection Substances 0.000 description 1
• 239000000080 wetting agent Substances 0.000 description 1
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• 229940102001 zinc bromide Drugs 0.000 description 1