CA1131618A - Composes de cephalosporine - Google Patents

Composes de cephalosporine

Info

Publication number: CA1131618A
Authority: CA; Canada
Prior art keywords: formula; group; compound; compounds; preparation
Prior art date: 1978-10-27
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA338,568A

Other languages

English (en)

Inventor

Cynthia H. O'callaghan

Niall G. Weir

Christopher E. Newall

Barry E. Ayres

Derek R. Sutherland

David G.H. Livermore

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.)

Glaxo Group Ltd

Original Assignee

Glaxo Group Ltd

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.)

1978-10-27

Filing date

1979-10-26

Publication date

1982-09-14

1979-10-26 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1982-09-14 Application granted granted Critical

1982-09-14 Publication of CA1131618A publication Critical patent/CA1131618A/fr

Status Expired legal-status Critical Current

Links

229940124587 cephalosporin Drugs 0.000 title claims abstract description 25
229930186147 Cephalosporin Natural products 0.000 title claims abstract description 24
-1 Cephalosporin compounds Chemical class 0.000 title claims description 54
150000001875 compounds Chemical class 0.000 claims abstract description 113
150000003839 salts Chemical class 0.000 claims abstract description 35
238000002360 preparation method Methods 0.000 claims abstract description 34
238000000034 method Methods 0.000 claims abstract description 29
150000002148 esters Chemical class 0.000 claims abstract description 24
231100000252 nontoxic Toxicity 0.000 claims abstract description 23
230000003000 nontoxic effect Effects 0.000 claims abstract description 23
239000003242 anti bacterial agent Substances 0.000 claims abstract description 20
230000003115 biocidal effect Effects 0.000 claims abstract description 19
150000001780 cephalosporins Chemical class 0.000 claims abstract description 19
229940088710 antibiotic agent Drugs 0.000 claims abstract description 18
229910052705 radium Inorganic materials 0.000 claims abstract description 11
229910052701 rubidium Inorganic materials 0.000 claims abstract description 11
229910052799 carbon Inorganic materials 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 4
239000002253 acid Substances 0.000 claims description 44
238000006243 chemical reaction Methods 0.000 claims description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 28
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
230000000903 blocking effect Effects 0.000 claims description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
239000003795 chemical substances by application Substances 0.000 claims description 11
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 10
125000006239 protecting group Chemical group 0.000 claims description 6
150000003842 bromide salts Chemical class 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical compound S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 claims description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
150000001450 anions Chemical class 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 claims description 2
230000002152 alkylating effect Effects 0.000 claims description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
241000284466 Antarctothoa delta Species 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 40
230000000694 effects Effects 0.000 abstract description 12
241000589516 Pseudomonas Species 0.000 abstract description 4
241000588921 Enterobacteriaceae Species 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
239000000243 solution Substances 0.000 description 42
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
239000007787 solid Substances 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
239000000047 product Substances 0.000 description 22
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
239000006260 foam Substances 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
150000007513 acids Chemical class 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 12
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 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
238000005917 acylation reaction Methods 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
239000007858 starting material Substances 0.000 description 10
229960000583 acetic acid Drugs 0.000 description 9
125000000217 alkyl group Chemical group 0.000 description 9
239000000460 chlorine Substances 0.000 description 9
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 8
239000000725 suspension Substances 0.000 description 8
241000282414 Homo sapiens Species 0.000 description 7
230000010933 acylation Effects 0.000 description 7
238000006073 displacement reaction Methods 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
238000011282 treatment Methods 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
238000007792 addition Methods 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 5
239000012346 acetyl chloride Substances 0.000 description 5
125000004423 acyloxy group Chemical group 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 5
230000000269 nucleophilic effect Effects 0.000 description 5
239000000843 powder Substances 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
229940126575 aminoglycoside Drugs 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 4
239000003814 drug Substances 0.000 description 4
238000006266 etherification reaction Methods 0.000 description 4
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 4
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000012258 stirred mixture Substances 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical class CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
125000004429 atom Chemical group 0.000 description 3
239000012267 brine Substances 0.000 description 3
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
238000011161 development Methods 0.000 description 3
230000018109 developmental process Effects 0.000 description 3
229960001760 dimethyl sulfoxide Drugs 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000012038 nucleophile Substances 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000011347 resin Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229960001407 sodium bicarbonate Drugs 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring 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
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
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 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
239000004472 Lysine Substances 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
241000588769 Proteus <enterobacteria> Species 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
150000001242 acetic acid derivatives Chemical class 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
125000005042 acyloxymethyl group Chemical group 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
125000000676 alkoxyimino group Chemical group 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
244000052616 bacterial pathogen Species 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
150000001649 bromium compounds Chemical class 0.000 description 2
239000000872 buffer Substances 0.000 description 2
QHTOIDKCEPKVCM-ZCFIWIBFSA-N cepham Chemical compound S1CCCN2C(=O)C[C@H]21 QHTOIDKCEPKVCM-ZCFIWIBFSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 2
229940106681 chloroacetic acid Drugs 0.000 description 2
239000012043 crude product Substances 0.000 description 2
JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical compound OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 2
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000000284 extract Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 2
238000009472 formulation Methods 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229960003646 lysine Drugs 0.000 description 2
239000000463 material Substances 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
244000005700 microbiome Species 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
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 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
159000000001 potassium salts Chemical class 0.000 description 2
238000012746 preparative thin layer chromatography Methods 0.000 description 2
239000002516 radical scavenger Substances 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000000926 separation method Methods 0.000 description 2
SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229960001866 silicon dioxide Drugs 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
235000017550 sodium carbonate Nutrition 0.000 description 2
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
239000004296 sodium metabisulphite Substances 0.000 description 2
235000010262 sodium metabisulphite Nutrition 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
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 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
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239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
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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
229960004919 procaine Drugs 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
230000005588 protonation Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
208000020029 respiratory tract infectious disease Diseases 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
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239000000377 silicon dioxide Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
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239000012312 sodium hydride Substances 0.000 description 1
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235000010288 sodium nitrite Nutrition 0.000 description 1
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235000011152 sodium sulphate Nutrition 0.000 description 1
239000012453 solvate Substances 0.000 description 1
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241000894007 species Species 0.000 description 1
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AAMCVENDCXWDPJ-UHFFFAOYSA-N sulfanyl acetate Chemical class CC(=O)OS AAMCVENDCXWDPJ-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
IGVNJALYNQVQIT-UHFFFAOYSA-N tert-butyl 2-bromo-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)Br IGVNJALYNQVQIT-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
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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 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/587—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with aliphatic hydrocarbon radicals substituted by 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, said aliphatic radicals being substituted in the alpha-position to the ring by a hetero atom, e.g. with m >= 0, Z being a singly or a doubly bound hetero atom

Landscapes

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

CA338,568A 1978-10-27 1979-10-26 Composes de cephalosporine Expired CA1131618A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB7842162		1978-10-27
GB7842163		1978-10-27
GB42162/78		1978-10-27
GB42163/78		1978-10-27

Publications (1)

Publication Number	Publication Date
CA1131618A true CA1131618A (fr)	1982-09-14

Family

ID=26269349

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA338,568A Expired CA1131618A (fr)	1978-10-27	1979-10-26	Composes de cephalosporine

Country Status (13)

Country	Link
AT (1)	AT367765B (fr)
CA (1)	CA1131618A (fr)
CH (1)	CH644867A5 (fr)
DE (1)	DE2943437A1 (fr)
DK (1)	DK452579A (fr)
ES (3)	ES485434A1 (fr)
FR (1)	FR2439787A1 (fr)
GB (1)	GB2040921B (fr)
IE (1)	IE49099B1 (fr)
IT (1)	IT1164746B (fr)
NL (1)	NL7907881A (fr)
NZ (1)	NZ191936A (fr)
SE (1)	SE7908895L (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GR78245B (fr) *	1980-09-12	1984-09-26	Ciba Geigy Ag
CA1213882A (fr) *	1982-03-04	1986-11-12	Jun Okumura	Cephalosporines
US4457929A (en) *	1982-03-29	1984-07-03	Bristol-Myers Company	3-Quaternary ammonium methyl)-substituted cephalosporin derivatives
US4486586A (en) *	1983-02-10	1984-12-04	Bristol-Myers Company	Cephalosporin derivatives
DE3409431A1 (de) *	1983-10-08	1985-04-18	Hoechst Ag, 6230 Frankfurt	Cephalosporinderivate und verfahren zu ihrer herstellung
DE3404906A1 (de) *	1984-02-11	1985-08-14	Bayer Ag, 5090 Leverkusen	1-oxadethiacephalosporinderivate sowie verfahren zu ihrer herstellung

1979
- 1979-10-26 IE IE2069/79A patent/IE49099B1/en unknown
- 1979-10-26 FR FR7926640A patent/FR2439787A1/fr active Granted
- 1979-10-26 DE DE19792943437 patent/DE2943437A1/de not_active Withdrawn
- 1979-10-26 ES ES485434A patent/ES485434A1/es not_active Expired
- 1979-10-26 SE SE7908895A patent/SE7908895L/xx not_active Application Discontinuation
- 1979-10-26 DK DK452579A patent/DK452579A/da not_active Application Discontinuation
- 1979-10-26 ES ES485435A patent/ES485435A1/es not_active Expired
- 1979-10-26 ES ES485433A patent/ES485433A1/es not_active Expired
- 1979-10-26 NZ NZ191936A patent/NZ191936A/xx unknown
- 1979-10-26 NL NL7907881A patent/NL7907881A/nl not_active Application Discontinuation
- 1979-10-26 IT IT50681/79A patent/IT1164746B/it active
- 1979-10-26 CA CA338,568A patent/CA1131618A/fr not_active Expired
- 1979-10-26 GB GB7937306A patent/GB2040921B/en not_active Expired
- 1979-10-26 CH CH964479A patent/CH644867A5/de not_active IP Right Cessation
- 1979-10-29 AT AT0698179A patent/AT367765B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK452579A (da)	1980-04-28
IT1164746B (it)	1987-04-15
NL7907881A (nl)	1980-04-29
DE2943437A1 (de)	1980-05-08
IE49099B1 (en)	1985-07-24
ATA698179A (de)	1981-12-15
SE7908895L (sv)	1980-04-28
GB2040921B (en)	1982-12-22
FR2439787B1 (fr)	1983-04-29
ES485435A1 (es)	1980-07-01
IT7950681A0 (it)	1979-10-26
IE792069L (en)	1980-04-27
CH644867A5 (de)	1984-08-31
ES485433A1 (es)	1980-07-01
GB2040921A (en)	1980-09-03
ES485434A1 (es)	1980-07-01
NZ191936A (en)	1982-09-07
AT367765B (de)	1982-07-26
FR2439787A1 (fr)	1980-05-23

Legal Events

Date	Code	Title	Description
1999-09-14	MKEX	Expiry

Publication	Publication Date	Title
US4600772A (en)	1986-07-15	Cephalosporin antibiotics
KR890001196B1 (ko)	1989-04-27	세팔로스포린 화합물의 제조방법
CA1132538A (fr)	1982-09-28	Cephalosporine
US4621081A (en)	1986-11-04	Cephalosporin antibiotics
US4464368A (en)	1984-08-07	Cephalosporin antibiotics
CA1130280A (fr)	1982-08-24	Cephalosporines
CA1131618A (fr)	1982-09-14	Composes de cephalosporine
CA1131216A (fr)	1982-09-07	Cephalosporine
US4315005A (en)	1982-02-09	Cephalosporin antibiotics
US4427675A (en)	1984-01-24	Cephalosporin antibiotics
GB1604723A (en)	1981-12-16	7-(2-aminothiazol-4-yl)-2-oxyimino-acetamido)-cephem derivatives
GB2027691A (en)	1980-02-27	Cephalosporin Antibiotics
GB1604724A (en)	1981-12-16	7-(2-aminothiazol-4-yl)-2-oxymino-acedamido)-cephem derivatives
GB2037281A (en)	1980-07-09	7-( alpha -(2-amino.4-thiazolyl)- alpha - hydroximino-acetamido)- cephalosporins
GB2036738A (en)	1980-07-02	Cephalosporin antibiotics
GB2046261A (en)	1980-11-12	Cephalosporin antibiotics
CA1130279A (fr)	1982-08-24	Cephalosporine
CA1122973A (fr)	1982-05-04	Cephalosporines
GB2027692A (en)	1980-02-27	Cephalosporin Antibiotics
CA1129408A (fr)	1982-08-10	Cephalosporine
GB2062624A (en)	1981-05-28	Cephalosporin Antibiotics
IE49171B1 (en)	1985-08-21	Cephalosporin antibiotics
EP0095329A2 (fr)	1983-11-30	Céphalosporines antibiotiques
GB2132193A (en)	1984-07-04	Cephalosporin antibiotics
GB2024808A (en)	1980-01-16	Cephalosporin antibiotics