CA1122973A - Cephalosporin antibiotics - Google Patents

Cephalosporin antibiotics

Info

Publication number: CA1122973A
Authority: CA; Canada
Prior art keywords: group; formula; compound; acid; ceph
Prior art date: 1978-05-26
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

CA328,415A

Other languages

English (en)

French (fr)

Inventor

Cynthia H. O'callaghan

David G. H. Livermore

Christopher E. Newall

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.)

1978-05-26

Filing date

1979-05-25

Publication date

1982-05-04

1978-05-26 Priority claimed from GB2304278A external-priority patent/GB1604724A/en

1978-05-26 Priority claimed from GB23041/78A external-priority patent/GB1604723A/en

1979-05-25 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1982-05-04 Application granted granted Critical

1982-05-04 Publication of CA1122973A publication Critical patent/CA1122973A/en

Status Expired legal-status Critical Current

Links

229940124587 cephalosporin Drugs 0.000 title claims abstract description 23
229930186147 Cephalosporin Natural products 0.000 title claims abstract description 22
239000003242 anti bacterial agent Substances 0.000 title claims abstract description 19
150000001780 cephalosporins Chemical class 0.000 title claims abstract description 18
229940088710 antibiotic agent Drugs 0.000 title claims abstract description 17
238000002360 preparation method Methods 0.000 claims abstract description 28
238000000034 method Methods 0.000 claims abstract description 25
230000003115 biocidal effect Effects 0.000 claims abstract description 20
229910052705 radium Inorganic materials 0.000 claims abstract description 14
229910052701 rubidium Inorganic materials 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052799 carbon Inorganic materials 0.000 claims abstract description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 4
150000001875 compounds Chemical class 0.000 claims description 97
239000002253 acid Substances 0.000 claims description 44
-1 ceph-3-em compound Chemical class 0.000 claims description 44
150000003839 salts Chemical class 0.000 claims description 36
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 25
238000006243 chemical reaction Methods 0.000 claims description 24
150000002148 esters Chemical class 0.000 claims description 20
231100000252 nontoxic Toxicity 0.000 claims description 18
230000003000 nontoxic effect Effects 0.000 claims description 18
230000000903 blocking effect Effects 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
239000007858 starting material Substances 0.000 claims description 12
239000003795 chemical substances by application Substances 0.000 claims description 11
239000012038 nucleophile Substances 0.000 claims description 10
239000005864 Sulphur Substances 0.000 claims description 8
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 8
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 8
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 5
150000004820 halides Chemical class 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[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
125000005843 halogen group Chemical group 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000004423 acyloxy group Chemical group 0.000 claims description 3
YDROWRWAIBYYQX-DYESRHJHSA-N benzhydryl (6r,7r)-7-amino-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound CN1N=NN=C1SCC1=C(C(=O)OC(C=2C=CC=CC=2)C=2C=CC=CC=2)N2C(=O)[C@@H](N)[C@H]2SC1 YDROWRWAIBYYQX-DYESRHJHSA-N 0.000 claims description 3
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 3
125000003831 tetrazolyl group Chemical group 0.000 claims description 3
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 3
125000003277 amino group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
230000001681 protective effect Effects 0.000 claims 2
RLIIROLYNCDXLI-RLANJUCJSA-N (2z)-2-[1-[(2-methylpropan-2-yl)oxycarbonyl]cyclobutyl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid Chemical compound C=1SC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=NC=1C(/C(O)=O)=N/OC1(C(=O)OC(C)(C)C)CCC1 RLIIROLYNCDXLI-RLANJUCJSA-N 0.000 claims 1
RACSQPAUTPPMLG-JYUHDHNASA-N (2z)-2-[2-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxopropan-2-yl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid Chemical compound CC(C)(C)OC(=O)C(C)(C)O\N=C(/C(O)=O)C1=CSC(NC(C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 RACSQPAUTPPMLG-JYUHDHNASA-N 0.000 claims 1
SOQOBRXKPNQOCL-HOYKSXRLSA-N (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxypropan-2-yloxyimino)acetyl]amino]-3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound CN1N=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)C(=N/OC(C)(C)C(O)=O)\C=3N=C(N)SC=3)[C@H]2SC1 SOQOBRXKPNQOCL-HOYKSXRLSA-N 0.000 claims 1
241000284466 Antarctothoa delta Species 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 29
230000000694 effects Effects 0.000 abstract description 10
229910052757 nitrogen Inorganic materials 0.000 abstract description 6
241000589516 Pseudomonas Species 0.000 abstract description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 abstract description 2
125000004070 6 membered heterocyclic group Chemical group 0.000 abstract description 2
125000004433 nitrogen atom Chemical group N* 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
150000007513 acids Chemical class 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
239000002585 base Substances 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
239000000047 product Substances 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
238000005917 acylation reaction Methods 0.000 description 10
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
125000000217 alkyl group Chemical group 0.000 description 8
239000000460 chlorine Substances 0.000 description 8
238000006073 displacement reaction Methods 0.000 description 8
241000282414 Homo sapiens Species 0.000 description 7
230000010933 acylation Effects 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
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239000007787 solid Substances 0.000 description 6
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229960000583 acetic acid Drugs 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
230000000269 nucleophilic effect Effects 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229960001760 dimethyl sulfoxide Drugs 0.000 description 4
238000006266 etherification reaction Methods 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
239000002904 solvent 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
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 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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125000001931 aliphatic group Chemical group 0.000 description 3
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239000000872 buffer Substances 0.000 description 3
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238000004587 chromatography analysis Methods 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
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NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
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IACSYDRIOYGJNH-ALCCZGGFSA-N ethyl (2z)-2-hydroxyimino-3-oxobutanoate Chemical compound CCOC(=O)C(=N/O)\C(C)=O IACSYDRIOYGJNH-ALCCZGGFSA-N 0.000 description 2
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ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 2
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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
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238000005866 tritylation reaction Methods 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Cephalosporin Compounds (AREA)

CA328,415A 1978-05-26 1979-05-25 Cephalosporin antibiotics Expired CA1122973A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB23042/78		1978-05-26
GB2304278A GB1604724A (en)	1978-05-26	1978-05-26	7-(2-aminothiazol-4-yl)-2-oxymino-acedamido)-cephem derivatives
GB23041/78A GB1604723A (en)	1978-05-26	1978-05-26	7-(2-aminothiazol-4-yl)-2-oxyimino-acetamido)-cephem derivatives
GB23041/78		1978-05-26

Publications (1)

Publication Number	Publication Date
CA1122973A true CA1122973A (en)	1982-05-04

Family

ID=26256274

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA328,415A Expired CA1122973A (en)	1978-05-26	1979-05-25	Cephalosporin antibiotics

Country Status (2)

Country	Link
AT (1)	AT365600B (de)
CA (1)	CA1122973A (de)

1979
- 1979-05-25 CA CA328,415A patent/CA1122973A/en not_active Expired
- 1979-05-25 AT AT0383779A patent/AT365600B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
AT365600B (de)	1982-01-25
ATA383779A (de)	1981-06-15

Legal Events

Date	Code	Title	Description
1999-05-04	MKEX	Expiry

Publication	Publication Date	Title
US4258041A (en)	1981-03-24	(6R,7R)-7-[(Z)-2-(2-Aminothiazol-4-yl)-2-(2-carboxyprop-2-oxyimino)acetamido]-3-(1-pyridiniummethyl)-ceph-3-em-4-carboxylate and salts thereof
CA1132538A (en)	1982-09-28	Cephalosporin antibiotics
US4621081A (en)	1986-11-04	Cephalosporin antibiotics
US4464368A (en)	1984-08-07	Cephalosporin antibiotics
CA1130280A (en)	1982-08-24	Cephalosporin compounds
US4315005A (en)	1982-02-09	Cephalosporin antibiotics
US4427675A (en)	1984-01-24	Cephalosporin antibiotics
CA1131618A (en)	1982-09-14	Cephalosporin compounds
IE49211B1 (en)	1985-08-21	Cephalosporin antibiotics
CA1122973A (en)	1982-05-04	Cephalosporin antibiotics
GB1604723A (en)	1981-12-16	7-(2-aminothiazol-4-yl)-2-oxyimino-acetamido)-cephem derivatives
GB1604724A (en)	1981-12-16	7-(2-aminothiazol-4-yl)-2-oxymino-acedamido)-cephem derivatives
US4560683A (en)	1985-12-24	Cephalosporin antibiotics
GB2037281A (en)	1980-07-09	7-( alpha -(2-amino.4-thiazolyl)- alpha - hydroximino-acetamido)- cephalosporins
GB2027691A (en)	1980-02-27	Cephalosporin Antibiotics
GB2046261A (en)	1980-11-12	Cephalosporin antibiotics
CA1130279A (en)	1982-08-24	Cephalosporin antibiotics
GB2027692A (en)	1980-02-27	Cephalosporin Antibiotics
GB1604722A (en)	1981-12-16	7-(2-(2-amino-4-thiozolyl)-2-oxymino-acetamido)-cephem derivatives
EP0095329A2 (de)	1983-11-30	Cephalosporin Antibiotika
IE49171B1 (en)	1985-08-21	Cephalosporin antibiotics
CA1129408A (en)	1982-08-10	Cephalosporin antibiotics
GB2062624A (en)	1981-05-28	Cephalosporin Antibiotics
GB2029824A (en)	1980-03-26	7-( alpha -oximino- alpha -2-amino-4-thiazolyl-acetamido)-cephens
GB2024808A (en)	1980-01-16	Cephalosporin antibiotics