CA1121360A - COMPOSES DE .beta.-LACTAM - Google Patents

COMPOSES DE .beta.-LACTAM

Info

Publication number: CA1121360A
Authority: CA; Canada
Prior art keywords: formula; compound; ester; benzyl; preparation
Prior art date: 1977-08-04
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

CA000368746A

Other languages

English (en)

Inventor

Brian C. Gasson

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.)

Beecham Group PLC

Original Assignee

Beecham Group PLC

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.)

1977-08-04

Filing date

1981-01-16

Publication date

1982-04-06

1978-07-27 Priority claimed from CA308,302A external-priority patent/CA1107739A/fr

1981-01-16 Application filed by Beecham Group PLC filed Critical Beecham Group PLC

1981-01-16 Priority to CA000368746A priority Critical patent/CA1121360A/fr

1982-04-06 Application granted granted Critical

1982-04-06 Publication of CA1121360A publication Critical patent/CA1121360A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 41
150000002148 esters Chemical class 0.000 claims abstract description 26
238000000034 method Methods 0.000 claims abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 14
238000002360 preparation method Methods 0.000 claims abstract description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 4
239000002253 acid Substances 0.000 claims abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 15
HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 claims description 11
229940090805 clavulanate Drugs 0.000 claims description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
-1 methoxymethyl ester Chemical class 0.000 claims description 9
239000003054 catalyst Substances 0.000 claims description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 4
229910052763 palladium Inorganic materials 0.000 claims description 4
238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
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 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
229910052723 transition metal Inorganic materials 0.000 claims description 2
150000003624 transition metals Chemical class 0.000 claims description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical group [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims 1
229910003446 platinum oxide Inorganic materials 0.000 claims 1
239000000243 solution Substances 0.000 description 20
239000000203 mixture Substances 0.000 description 17
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
239000002904 solvent Substances 0.000 description 12
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 8
HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 7
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical group CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 5
229960003324 clavulanic acid Drugs 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
239000010410 layer Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 2
244000166102 Eucalyptus leucoxylon Species 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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
229940022663 acetate Drugs 0.000 description 2
AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 2
229960000723 ampicillin Drugs 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
XDHOEHJVXXTEDV-HWKANZROSA-N (e)-1-ethoxyprop-1-ene Chemical compound CCO\C=C\C XDHOEHJVXXTEDV-HWKANZROSA-N 0.000 description 1
UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
ZKJNETINGMOHJG-UHFFFAOYSA-N 1-prop-1-enoxyprop-1-ene Chemical class CC=COC=CC ZKJNETINGMOHJG-UHFFFAOYSA-N 0.000 description 1
JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
101100167062 Caenorhabditis elegans chch-3 gene Proteins 0.000 description 1
229930186147 Cephalosporin Natural products 0.000 description 1
OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000588915 Klebsiella aerogenes Species 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
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 1
241000588770 Proteus mirabilis Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
AZUFHGGGPUUXKI-FLFDDASRSA-N benzyl (2r,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound O=C([C@@H]1N2C(=O)C[C@H]2O\C1=C/CO)OCC1=CC=CC=C1 AZUFHGGGPUUXKI-FLFDDASRSA-N 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000013058 crude material Substances 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical class CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
125000006502 nitrobenzyl group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000368746A 1977-08-04 1981-01-16 COMPOSES DE .beta.-LACTAM Expired CA1121360A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000368746A CA1121360A (fr)	1977-08-04	1981-01-16	COMPOSES DE .beta.-LACTAM

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB3269977		1977-08-04
GB32699/77		1977-08-04
CA308,302A CA1107739A (fr)	1977-08-04	1978-07-27	COMPOSES DE TYPE .beta.-LACTAME
CA000368746A CA1121360A (fr)	1977-08-04	1981-01-16	COMPOSES DE .beta.-LACTAM

Publications (1)

Publication Number	Publication Date
CA1121360A true CA1121360A (fr)	1982-04-06

Family

ID=27165773

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000368746A Expired CA1121360A (fr)	1977-08-04	1981-01-16	COMPOSES DE .beta.-LACTAM

Country Status (1)

Country	Link
CA (1)	CA1121360A (fr)

1981
- 1981-01-16 CA CA000368746A patent/CA1121360A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-04-06	MKEX	Expiry

Publication	Publication Date	Title
US4207323A (en)	1980-06-10	6-Substituted methyl penicillins, derivatives and analogues thereof
EP0008497B1 (fr)	1984-10-24	Composés de bêta-lactame, leur préparation et compositions pharmaceutiques les contenant
DD156533A5 (de)	1982-09-01	Verfahren zur herstellung von 3-iodmethylcephalosporinen
US4237051A (en)	1980-12-02	Stereospecific production of 6- or 7-carbon-substituted-β-lactams
EP0008514B1 (fr)	1982-01-20	Dérivés antibactériens de bêta-lactames, compositions les contenant et un procédé pour leur préparation
US4122262A (en)	1978-10-24	Intermediates and methods for preparing 7-acylamino-8-oxo-oxa-1-azabicyclo[4.2.0]octane-2-carboxylic acid derivatives
US4347355A (en)	1982-08-31	Inhibitors of transpeptidase
CA1121360A (fr)	1982-04-06	COMPOSES DE .beta.-LACTAM
US4122086A (en)	1978-10-24	Isopenicillins
CA1136138A (fr)	1982-11-23	Analogues de la cephalosporine et methodes de preparation
EP0013067A1 (fr)	1980-07-09	Agents antibactériens à cycle bêta-lactame bicyclique, leur utilisation dans des compositions pharmaceutiques, procédés pour leur préparation et intermédiaires à utiliser dans de tels procédés
CA1107739A (fr)	1981-08-25	COMPOSES DE TYPE .beta.-LACTAME
CH648850A5 (de)	1985-04-15	Penicillansaeure-derivate, verfahren zu ihrer herstellung und solche derivate enthaltende arzneimittel.
HU193460B (en)	1987-10-28	Process for production of peneme derivatives
KR870000325B1 (ko)	1987-02-27	치환된 2-페넴-3-카복실산 화합물의 제조방법
US4172895A (en)	1979-10-30	6-(1'-Hydroxyethyl)-2-aminoethylthio-oxapen-2-em-3-carboxylic acid
EP0185221A2 (fr)	1986-06-25	Procédé pour la préparation de dérivés d'aminothiazolylacide acétique
EP0002370B1 (fr)	1983-05-11	Procédé pour la préparation de derivés ether de l'acide clavulanique
EP0104010B1 (fr)	1986-04-30	Intermédiaires pour dérivés d'acide clavulanique
CH641448A5 (de)	1984-02-29	Verfahren zur herstellung von beta-lactamen.
FI71562B (fi)	1986-10-10	Foerfarande foer framstaellning av 6-beta-substituerade penicillansyra derivat och saosom mellanprodukter anvaendbara 6-perfluoralkylsulfonyloxipenicillansyraderivat
US4397784A (en)	1983-08-09	Inhibitors of transpeptidase
EP0117872A1 (fr)	1984-09-12	Procede de preparation de composes de cephalosporine
EP0009302B1 (fr)	1983-10-26	Dérivés de l'acide clavulanique et procédé pour leur préparation
US4187228A (en)	1980-02-05	Antibacterial agents 5R, 2S-hydroxymethyl-3Z (2-hydroxy- or 2-alkoxyethylidene-1-aza-4-oxabicyclo[3,2,0]heptanone