NL8100539A - Nieuwe thiolesters, de bereiding daarvan en hun gebruik bij syntheses. - Google Patents

Nieuwe thiolesters, de bereiding daarvan en hun gebruik bij syntheses. Download PDF

Info

Publication number: NL8100539A
Authority: NL; Netherlands
Prior art keywords: radical; alkyl; substituted; general formula; dioxo
Prior art date: 1980-02-12

Application number

NL8100539A

Other languages

English (en)

Dutch (nl)

Original Assignee

Rhone Poulenc Ind

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.)

1980-02-12

Filing date

1981-02-04

Publication date

1981-09-01

1980-02-12 Priority claimed from FR8003057A external-priority patent/FR2475545A1/fr

1980-05-13 Priority claimed from FR8010706A external-priority patent/FR2482594A2/fr

1981-02-04 Application filed by Rhone Poulenc Ind filed Critical Rhone Poulenc Ind

1981-09-01 Publication of NL8100539A publication Critical patent/NL8100539A/nl

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150000007970 thio esters Chemical class 0.000 title claims description 15
238000002360 preparation method Methods 0.000 title description 10
238000003786 synthesis reaction Methods 0.000 title description 2
230000015572 biosynthetic process Effects 0.000 title 1
-1 alkyl radical Chemical class 0.000 claims description 218
150000003254 radicals Chemical class 0.000 claims description 136
238000000034 method Methods 0.000 claims description 73
239000000203 mixture Substances 0.000 claims description 59
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 39
239000002253 acid Substances 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 36
125000004432 carbon atom Chemical group C* 0.000 claims description 34
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
229920002554 vinyl polymer Polymers 0.000 claims description 22
125000003282 alkyl amino group Chemical group 0.000 claims description 20
230000001681 protective effect Effects 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
125000006239 protecting group Chemical group 0.000 claims description 17
125000004442 acylamino group Chemical group 0.000 claims description 16
229910052757 nitrogen Inorganic materials 0.000 claims description 16
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 16
239000002585 base Substances 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
125000004663 dialkyl amino group Chemical group 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
125000002252 acyl group Chemical group 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 12
239000003513 alkali Substances 0.000 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 9
125000004103 aminoalkyl group Chemical group 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 7
150000008064 anhydrides Chemical class 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 7
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 claims description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 6
150000002923 oximes Chemical class 0.000 claims description 6
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims description 5
125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 5
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
OHSJPLSEQNCRLW-UHFFFAOYSA-N triphenylmethyl radical Chemical compound C1=CC=CC=C1[C](C=1C=CC=CC=1)C1=CC=CC=C1 OHSJPLSEQNCRLW-UHFFFAOYSA-N 0.000 claims description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
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 4
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 4
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
125000001477 organic nitrogen group Chemical group 0.000 claims description 4
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 4
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
125000005281 alkyl ureido group Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
230000032050 esterification Effects 0.000 claims description 3
238000005886 esterification reaction Methods 0.000 claims description 3
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
125000003396 thiol group Chemical class [H]S* 0.000 claims description 3
ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims description 3
GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 claims description 2
HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
125000004181 carboxyalkyl group Chemical group 0.000 claims description 2
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
125000006633 tert-butoxycarbonylamino group Chemical group 0.000 claims description 2
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
150000001204 N-oxides Chemical class 0.000 claims 1
125000002098 pyridazinyl group Chemical group 0.000 claims 1
125000004076 pyridyl group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 97
239000000047 product Substances 0.000 description 83
239000000243 solution Substances 0.000 description 58
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 44
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 43
229910052753 mercury Inorganic materials 0.000 description 43
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 27
238000002329 infrared spectrum Methods 0.000 description 24
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 21
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
229910052938 sodium sulfate Inorganic materials 0.000 description 19
235000011152 sodium sulphate Nutrition 0.000 description 19
239000002904 solvent Substances 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
239000000741 silica gel Substances 0.000 description 15
229910002027 silica gel Inorganic materials 0.000 description 15
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000012141 concentrate Substances 0.000 description 14
235000008504 concentrate Nutrition 0.000 description 14
238000010992 reflux Methods 0.000 description 14
239000002609 medium Substances 0.000 description 13
235000017557 sodium bicarbonate Nutrition 0.000 description 13
229910000030 sodium bicarbonate Inorganic materials 0.000 description 13
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 12
229910002091 carbon monoxide Inorganic materials 0.000 description 12
235000019253 formic acid Nutrition 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
238000003756 stirring Methods 0.000 description 12
ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 11
229940124587 cephalosporin Drugs 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
239000003960 organic solvent Substances 0.000 description 10
239000000843 powder Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 9
239000006260 foam Substances 0.000 description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
229930186147 Cephalosporin Natural products 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
239000004202 carbamide Substances 0.000 description 7
150000001780 cephalosporins Chemical class 0.000 description 7
238000001914 filtration Methods 0.000 description 7
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
229940113088 dimethylacetamide Drugs 0.000 description 6
238000010828 elution Methods 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
239000000725 suspension Substances 0.000 description 6
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 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
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 5
101100113485 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) chs-3 gene Proteins 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
229910052698 phosphorus Inorganic materials 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
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 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 4
244000309464 bull Species 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
238000001035 drying Methods 0.000 description 4
125000004967 formylalkyl group Chemical group 0.000 description 4
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 4
150000003573 thiols Chemical class 0.000 description 4
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 3
NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical class CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
229950003476 aminothiazole Drugs 0.000 description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
150000002081 enamines Chemical class 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
229940056360 penicillin g Drugs 0.000 description 3
239000012047 saturated solution Substances 0.000 description 3
239000011734 sodium Chemical class 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 3
125000004434 sulfur atom Chemical group 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
239000011701 zinc Substances 0.000 description 3
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
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YQCIWBXEVYWRCW-UHFFFAOYSA-N methane;sulfane Chemical compound C.S YQCIWBXEVYWRCW-UHFFFAOYSA-N 0.000 description 1
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
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125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 description 1
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QCIBHTJSNLWOJP-UHFFFAOYSA-O oxo-[(1-prop-2-enylpyridin-2-ylidene)methyl]azanium Chemical compound C=CCN1C=CC=CC1=C[NH+]=O QCIBHTJSNLWOJP-UHFFFAOYSA-O 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
230000037361 pathway Effects 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
125000005544 phthalimido group Chemical group 0.000 description 1
238000000053 physical method Methods 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D253/075—Two hetero atoms, in positions 3 and 5
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Cephalosporin Compounds (AREA)

NL8100539A 1980-02-12 1981-02-04 Nieuwe thiolesters, de bereiding daarvan en hun gebruik bij syntheses. NL8100539A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
FR8003057A FR2475545A1 (fr)	1980-02-12	1980-02-12	Nouveaux thioloesters, leur preparation et leur utilisation en synthese
FR8003057		1980-02-12
FR8010706		1980-05-13
FR8010706A FR2482594A2 (fr)	1980-05-13	1980-05-13	Nouveaux thioloesters, leur preparation et leur utilisation en synthese

Publications (1)

Publication Number	Publication Date
NL8100539A true NL8100539A (nl)	1981-09-01

Family

ID=26221601

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8100539A NL8100539A (nl)	1980-02-12	1981-02-04	Nieuwe thiolesters, de bereiding daarvan en hun gebruik bij syntheses.

Country Status (11)

Country	Link
US (1)	US4385181A (da)
BE (1)	BE887474A (da)
CA (1)	CA1187496A (da)
CH (1)	CH646963A5 (da)
DE (1)	DE3105136A1 (da)
DK (1)	DK58581A (da)
GB (1)	GB2068957B (da)
HU (1)	HU185627B (da)
IT (1)	IT1141966B (da)
NL (1)	NL8100539A (da)
SE (1)	SE8100954L (da)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CY1365A (en) *	1980-03-28	1987-08-07	Biochemie Gmbh	New process for the production of cephalosporin antibiotics, and novel intermediates used in such process and their production
AU564150B2 (en) *	1982-04-30	1987-08-06	Takeda Chemical Industries Ltd.	1-sulfo-2-azetidinone derivatives
US4948898A (en) *	1982-06-03	1990-08-14	Hoffmann-La Roche Inc.	Process for the manufacture of 1-sulpho-2-oxoazetidine derivatives
AU542287B2 (en) *	1982-06-17	1985-02-14	Toyama Chemical Co. Ltd.	Process for producing 2-(2-aminothiazol-4-yl) glyoxylic acid derivative, it:s salt and intermediates therefor
JPS6064986A (ja) *	1983-09-20	1985-04-13	Toyama Chem Co Ltd	セファロスポリン類の製造法
JPS60132983A (ja) *	1983-12-21	1985-07-16	Tanabe Seiyaku Co Ltd	チアゾ−ル酢酸誘導体及びその製法
US5698703A (en) *	1991-09-10	1997-12-16	Bristol-Myers Squibb Company	Syn-isomer of thiazolyl intermediate and process for the preparation thereof
US5594129A (en) *	1991-09-10	1997-01-14	Bristol-Myers Squibb Company	Process for the preparation of a cephalosporin antibiotic
US6610845B1 (en) *	2002-01-04	2003-08-26	Orchid Chemicals & Pharmaceuticals Limited, India	Thioester derivatives of thiazolyl acetic acid and their use in the preparation of cephalosporin compounds
CA2702257C (en)	2007-10-09	2016-07-12	Sopharmia, Inc.	Broad spectrum beta-lactamase inhibitors
US9975905B2 (en)	2013-03-12	2018-05-22	Gladius Pharmaceuticals Corporation	Derivatized 3-styryl-cephalosporins

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2346014A1 (fr)	1976-01-23	1977-10-28	Roussel Uclaf	Nouvelles oximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et leur application comme medicaments
NL7714319A (nl)	1976-12-27	1978-06-29	Fujisawa Pharmaceutical Co	Cefalosporineverbindingen en werkwijzen om deze te bereiden.
DE2804040C3 (de)	1978-01-31	1981-03-19	Hoechst Ag, 6000 Frankfurt	Verfahren zur Herstellung von Cephemverbindungen

1981
- 1981-02-04 NL NL8100539A patent/NL8100539A/nl not_active Application Discontinuation
- 1981-02-09 CH CH85681A patent/CH646963A5/fr not_active IP Right Cessation
- 1981-02-10 GB GB8103963A patent/GB2068957B/en not_active Expired
- 1981-02-10 US US06/233,109 patent/US4385181A/en not_active Expired - Fee Related
- 1981-02-11 SE SE8100954A patent/SE8100954L/xx not_active Application Discontinuation
- 1981-02-11 CA CA000370640A patent/CA1187496A/fr not_active Expired
- 1981-02-11 HU HU81334A patent/HU185627B/hu unknown
- 1981-02-11 BE BE0/203768A patent/BE887474A/fr not_active IP Right Cessation
- 1981-02-11 DK DK58581A patent/DK58581A/da not_active Application Discontinuation
- 1981-02-12 IT IT19703/81A patent/IT1141966B/it active
- 1981-02-12 DE DE3105136A patent/DE3105136A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
DK58581A (da)	1981-08-13
DE3105136A1 (de)	1981-12-10
IT8119703A0 (it)	1981-02-12
CH646963A5 (fr)	1984-12-28
BE887474A (fr)	1981-08-11
SE8100954L (sv)	1981-08-13
CA1187496A (fr)	1985-05-21
HU185627B (en)	1985-03-28
US4385181A (en)	1983-05-24
GB2068957A (en)	1981-08-19
GB2068957B (en)	1984-02-01
IT1141966B (it)	1986-10-08

Legal Events

Date	Code	Title
1983-01-03	BV	The patent application has lapsed
1985-01-01	A85	Still pending on 85-01-01
1986-10-01	BV	The patent application has lapsed

Publication	Publication Date	Title
CA1316171C (en)	1993-04-13	Cephalosporin derivatives
DE2716677C2 (de)	1985-10-10	Cephemderivate und Verfahren zu ihrer Herstellung
CA1259606A (en)	1989-09-19	Cephem derivatives and processes for their manufacture
KR100585240B1 (ko)	2006-06-01	질소함유 복소환 카르복사미드 유도체 또는 그 염 및 이를함유하는 항바이러스제
US5064953A (en)	1991-11-12	Intermediates cephalosporin derivatives
LU82479A1 (fr)	1980-12-16	Nouvelles thiovinyl-3 cephalosporines,leur preparation et les compositions qui les contiennent
NO801503L (no)	1980-11-24	Nye 3-vinylcefalosporiner og fremgangsmaate for fremstilling av disse.
HU187812B (en)	1986-02-28	Process for the preparation of new pyridinium-thio-methyl-cephem-carboxilic acid derivatives
NL193284C (nl)	1999-05-06	Antibacterieel preparaat en een voor toepassing in dit preparaat geschikt 7-[(Z)-2-(veretherd oxyimino)-2-(2-aminothiazol-4-yl)- aceetamido]-3-ammoniomethyl-3-cefem-4-carbonzuur derivaat.
DE2415402A1 (de)	1974-10-03	Cephalosporansaeurederivate, verfahren zu ihrer herstellung und ihre verwendung in pharmazeutischen zubereitungen
US5013730A (en)	1991-05-07	Cephem derivatives
DE3019462A1 (de)	1980-12-04	Neue 3-vinyl-cephalosporin-derivate und verfahren zu deren herstellung
US5329002A (en)	1994-07-12	Antibacterial cephalosporin compounds
US4888332A (en)	1989-12-19	Cephalosporin derivatives
FI89490B (fi)	1993-06-30	Foerfarande foer framstaellning av 2-metoximetyl-penemderivat
HU185644B (en)	1985-03-28	Process for producing 7-beta-square bracket-alpha-syn-methoxy-imino-alpha-bracket-2-amino-thiazol-4-yl-bracket closed-acetamido-square bracket closed-3-bracket-1,2,3-thiazol-5-yl-thio-nethyl-aracket closed-3-cepheme-4-carboxylic acid derivatives
DE3105136A1 (de)	1981-12-10	"neue thioloester, ihre herstellung und ihre verwendung zur synthese"
YASUDA et al.	1983	Synthesis and antibacterial activity of 6-and 7-[2-(5-carboxyimidazole-4-carboxamido) phenylacetamido]-penicillins and cephalosporins
DE2715038A1 (de)	1977-11-24	Neue antibakterielle verbindungen
CH647524A5 (de)	1985-01-31	7alpha-methoxycephalosporine und verfahren zur herstellung derselben.
US4868173A (en)	1989-09-19	Cephalosporin derivatives
IE54173B1 (en)	1989-07-05	New derivatives of cephalosporins substituted in 3 position by a thiomethyl heterocycle group; process for preparing these compounds and pharmaceutical compositions containing them
DE2527291A1 (de)	1976-01-08	Acylderivate
NO810144L (no)	1981-07-20	Nye tioler og fremgangsmaate for fremstilling derav
DE2737066A1 (de)	1978-02-23	7-(n-substituierte-2-phenylglycinamido)-3-substituierte-3-cephem-4-carbonsaeure-verbindungen, verfahren zu ihrer herstellung und sie enthaltende arzneimittel