CA1100406A - Compose pharmaceutique synergique contenant des derives de l'acide clavulanique et de la penicilline ou de la cephalosporine - Google Patents

Compose pharmaceutique synergique contenant des derives de l'acide clavulanique et de la penicilline ou de la cephalosporine

Info

Publication number: CA1100406A
Authority: CA; Canada
Prior art keywords: group; pharmaceutical composition; formula; carbon atoms; ampicillin
Prior art date: 1975-10-13
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

CA353,771A

Other languages

English (en)

Inventor

Irene Stirling

Thomas T. Howarth

Roger J. Ponsford

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.)

1975-10-13

Filing date

1980-06-11

Publication date

1981-05-05

1975-10-13 Priority claimed from GB41887/75A external-priority patent/GB1566706A/en

1980-06-11 Application filed by Beecham Group PLC filed Critical Beecham Group PLC

1980-06-11 Priority to CA353,771A priority Critical patent/CA1100406A/fr

1981-05-05 Application granted granted Critical

1981-05-05 Publication of CA1100406A publication Critical patent/CA1100406A/fr

Status Expired legal-status Critical Current

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 22
229930186147 Cephalosporin Natural products 0.000 title claims abstract description 9
229930182555 Penicillin Natural products 0.000 title claims abstract description 9
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 title claims abstract description 9
229940124587 cephalosporin Drugs 0.000 title claims abstract description 9
150000001780 cephalosporins Chemical class 0.000 title claims abstract description 9
229940049954 penicillin Drugs 0.000 title claims abstract description 7
HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical class OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 title description 8
230000002195 synergetic effect Effects 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 40
150000002148 esters Chemical class 0.000 claims abstract description 36
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 29
-1 acetoxymethyl Chemical group 0.000 claims abstract description 28
125000000217 alkyl group Chemical group 0.000 claims abstract description 25
150000003839 salts Chemical class 0.000 claims abstract description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
229910052736 halogen Inorganic materials 0.000 claims abstract description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
239000002253 acid Substances 0.000 claims abstract description 10
125000005843 halogen group Chemical group 0.000 claims abstract description 10
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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 claims description 17
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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 4
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XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
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QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
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239000007884 disintegrant Substances 0.000 description 1
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238000001914 filtration Methods 0.000 description 1
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235000019634 flavors Nutrition 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
DXVUYOAEDJXBPY-NFFDBFGFSA-N hetacillin Chemical compound C1([C@@H]2C(=O)N(C(N2)(C)C)[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 DXVUYOAEDJXBPY-NFFDBFGFSA-N 0.000 description 1
229960003884 hetacillin Drugs 0.000 description 1
239000005457 ice water Substances 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
208000004396 mastitis Diseases 0.000 description 1
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HVAAHUDGWQAAOJ-UHFFFAOYSA-N n-benzylethanamine Chemical compound CCNCC1=CC=CC=C1 HVAAHUDGWQAAOJ-UHFFFAOYSA-N 0.000 description 1
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235000019371 penicillin G benzathine Nutrition 0.000 description 1
229940056360 penicillin g Drugs 0.000 description 1
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239000003208 petroleum Substances 0.000 description 1
BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
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239000000843 powder Substances 0.000 description 1
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239000003755 preservative agent Substances 0.000 description 1
HOCWPKXKMNXINF-XQERAMJGSA-N propicillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C(CC)OC1=CC=CC=C1 HOCWPKXKMNXINF-XQERAMJGSA-N 0.000 description 1
229960003672 propicillin Drugs 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
210000004872 soft tissue Anatomy 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
150000004684 trihydrates Chemical class 0.000 description 1
210000001635 urinary tract Anatomy 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA353,771A 1975-10-13 1980-06-11 Compose pharmaceutique synergique contenant des derives de l'acide clavulanique et de la penicilline ou de la cephalosporine Expired CA1100406A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA353,771A CA1100406A (fr)	1975-10-13	1980-06-11	Compose pharmaceutique synergique contenant des derives de l'acide clavulanique et de la penicilline ou de la cephalosporine

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB41887/75A GB1566706A (en)	1975-10-13	1975-10-13	Clavulanic acid derivatives
GB41887/75		1975-10-13
CA263,103A CA1094563A (fr)	1975-10-13	1976-10-12	Derives de l'acide clavulanique
CA353,771A CA1100406A (fr)	1975-10-13	1980-06-11	Compose pharmaceutique synergique contenant des derives de l'acide clavulanique et de la penicilline ou de la cephalosporine

Publications (1)

Publication Number	Publication Date
CA1100406A true CA1100406A (fr)	1981-05-05

Family

ID=27164685

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA353,771A Expired CA1100406A (fr)	1975-10-13	1980-06-11	Compose pharmaceutique synergique contenant des derives de l'acide clavulanique et de la penicilline ou de la cephalosporine

Country Status (1)

Country	Link
CA (1)	CA1100406A (fr)

1980
- 1980-06-11 CA CA353,771A patent/CA1100406A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-05-05	MKEX	Expiry

Publication	Publication Date	Title
CA1094563A (fr)	1981-01-27	Derives de l'acide clavulanique
US4650795A (en)	1987-03-17	Amine salts of clavulanic acid as antibacterial agents
US6037469A (en)	2000-03-14	6-(substituted methylene) penems and intermediates
CA1081699A (fr)	1980-07-15	Derives de l'acide clavulanique
EP0008877B1 (fr)	1983-10-26	Dérivés d'acide clavulanique, un procédé pour leur préparation et leurs compositions
US4562182A (en)	1985-12-31	Compounds containing beta-lactams
US4571392A (en)	1986-02-18	6-Substituted derivatives of clavulanic acid
US4388300A (en)	1983-06-14	Clavulanic acid derivatives, a process for their preparation and their use in pharmaceutical compositions
EP0008884B1 (fr)	1983-08-17	Dérivés de l'acide clavulanique, un procédé pour leur préparation et leurs compositions
US4426389A (en)	1984-01-17	Derivatives of clavulanic acid, a process for their preparation and their use
US4036969A (en)	1977-07-19	2,12-Dioxo-7-hydroxymethyl-9-phenyl-1-aza-5,8,11-trioxotetracyclo[9.2.0.06,13 0.6.9 ]tridecane
CA1132548A (fr)	1982-09-28	Derives de l'acide clavulanique; methode pour les preparer et leur utilisation
EP0112685B1 (fr)	1986-04-23	Composés contenant des bêta-lactames
US4303665A (en)	1981-12-01	Methylaminodeoxy-clavulanic acid derivatives, their production and use
EP0002319A1 (fr)	1979-06-13	Dérivés de l'acide clavulanique, procédé pour leur préparation et compositions les contenant
EP0000615B1 (fr)	1981-04-29	Composés béta-lactame, préparation et utilisation dans compositions pharmaceutiques et comme produits chimiques intermédiaires
CA1077843A (fr)	1980-05-20	Derives d'acide clavulanique
EP0027323B1 (fr)	1984-03-14	Dérivés de l'acide clavulanique, procédés pour leur préparation et compositions pharmaceutiques les contenant
AT352873B (de)	1979-10-10	Verfahren zur herstellung von neuen clavulan- saeureaethern
GB1572259A (en)	1980-07-30	Clavulanic acid derivatives
GB2086890A (en)	1982-05-19	Derivatives of 2-(2'-oxo-ethylidene)-3-clavancarboxylic acid
IE46023B1 (en)	1983-01-26	Amine salts of clavulanic acid, methods for their preparations and compositions containing them
EP0021836A1 (fr)	1981-01-07	Dérivés de l'acide clavulanique, procédé pour leur préparation et compositions pharmaceutiques les contenant
WO1984003092A1 (fr)	1984-08-16	Derives de clavame