GB1187323A - Sydnone and Sydnone Imine Derivatives of 7-Aminocephalosporanic Acids and Preparation thereof - Google Patents
Sydnone and Sydnone Imine Derivatives of 7-Aminocephalosporanic Acids and Preparation thereofInfo
- Publication number
- GB1187323A GB1187323A GB2946567A GB2946567A GB1187323A GB 1187323 A GB1187323 A GB 1187323A GB 2946567 A GB2946567 A GB 2946567A GB 2946567 A GB2946567 A GB 2946567A GB 1187323 A GB1187323 A GB 1187323A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sydnone
- aryl
- alkyl
- formula
- compound
- Prior art date
- 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
Links
- -1 Sydnone Imine Chemical class 0.000 title abstract 5
- NVRSPIKUPKOSIY-UHFFFAOYSA-N chembl1743348 Chemical class CC=1N=NOC=1O NVRSPIKUPKOSIY-UHFFFAOYSA-N 0.000 title abstract 4
- 239000002253 acid Substances 0.000 title 1
- 150000007513 acids Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 8
- 125000006356 alkylene carbonyl group Chemical group 0.000 abstract 6
- 125000003118 aryl group Chemical group 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- BPIDXHXOZOWFTJ-UHFFFAOYSA-N (1-azidopyridin-1-ium-2-yl) acetate Chemical compound C(C)(=O)OC1=[N+](C=CC=C1)N=[N+]=[N-] BPIDXHXOZOWFTJ-UHFFFAOYSA-N 0.000 abstract 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 abstract 1
- CLZGUNRCTGMKLX-UHFFFAOYSA-N 2,2,2-tributoxyethanamine Chemical compound C(CCC)OC(CN)(OCCCC)OCCCC CLZGUNRCTGMKLX-UHFFFAOYSA-N 0.000 abstract 1
- MYGXGCCFTPKWIH-UHFFFAOYSA-N 4-chloro-1-methylpiperidine Chemical compound CN1CCC(Cl)CC1 MYGXGCCFTPKWIH-UHFFFAOYSA-N 0.000 abstract 1
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 229930186147 Cephalosporin Natural products 0.000 abstract 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- SQSPRWMERUQXNE-UHFFFAOYSA-N Guanylurea Chemical compound NC(=N)NC(N)=O SQSPRWMERUQXNE-UHFFFAOYSA-N 0.000 abstract 1
- HZEPPWXWIXVEEL-UHFFFAOYSA-N N,N-dibutoxy-1-phenylpropan-1-amine Chemical compound C(CCC)ON(OCCCC)C(C1=CC=CC=C1)CC HZEPPWXWIXVEEL-UHFFFAOYSA-N 0.000 abstract 1
- CZARYASYHXNRKF-UHFFFAOYSA-N N-benzyl-2-butoxy-N-methylethanamine Chemical compound CN(CCOCCCC)CC1=CC=CC=C1 CZARYASYHXNRKF-UHFFFAOYSA-N 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 125000005035 acylthio group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000004947 alkyl aryl amino group Chemical group 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 125000005110 aryl thio group Chemical group 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 229940124587 cephalosporin Drugs 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000012038 nucleophile Substances 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 150000003573 thiols Chemical class 0.000 abstract 1
Classifications
-
- 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)
- Cephalosporin Compounds (AREA)
Abstract
1,187,323. Cephalosporins. FUJISAWA PHARMACEUTICAL CO. Ltd. 26 June, 1967 [29 June, 1966; 2 Nov., 1966 (3); 7 Nov., 1966; 12 Nov., 1966; 18 Feb., 1967], No. 29465/67. Heading C2A. The invention comprises a sydnone and sydnone imine derivative of 7-aminocephalosporanic acid, and pharmaceutically acceptable salts thereof, of Formula I: wherein R 1 is O, imino, acylimino, C 1 -C 4 alkylcarbamoylimino, arylcarbamoylimino, C 1 -C 4 alkylthiocarbamoylimino or arylthiocarbamoylimino; R 2 is C 1 -C 4 alkyl, aryl or aryl C 1 -C 4 alkyl; R 3 is H, halogen, C 1 -C 4 alkyl, aryl or aryl C 1 -C 4 alkyl; Z is carbonyl, C 1 -C 4 alkylenecarbonyl, aryl C 1 -C 4 alkylene carbonyl or arylene C 1 -C 4 alkylene carbonyl when it is attached to the 4-position of the sydnone ring, or Z is C 1 -C 4 alkylene carbonyl, aryl C 1 -C 4 alkylene carbonyl or arylene-C 1 -C 4 alkylene carbonyl when it is attached to the 3-position of the sydnone ring; R 4 is acetoxy, azido, pyridinium, arylamino, N-C 1 -C 4 alkylarylamino, C 1 -C 4 alkylthio, arylthio, acylthio, heterocyclic-carbonylthio, heterocyclicthio, C 1 - C 4 alkylimidoylthio, arylimidoylthio, amidinothio, di-C 1 -C 4 alkylamidinothio, diarylamidinothio, C 1 -C 4 alkoxy-C 1 -C 4 alkoxythiocarbonylthio, aryloxy-C 1 -C 4 alkoxy thiocarbonylthio, N - C 1 -C 4 alkylaminothiocarbonylthio, N- arylaminothiocarbonylthio, N - C 1 -C 4 - alkyl- N - arylaminothiocarbonylthio, N,N - di - lower alkylaminothiocarbonylthio where the di-C 1 - C 4 -alkylamino groups may form a monocyclic heterocyclic radical with or without an oxygen atom or an additional N atom in the ring so formed; R 5 is OH, O-, alkoxy, aryloxy, heterocyolic-C 1 -C 4 alkoxy, hydroxyamino, alkylamino, C 1 -C 4 alkylthio or heterocyclicthio. The compounds are prepared by (A) acylating 7-aminocephalosporanic acid with a sydnone compound of Formula III in which R 1 , R 2 , R 3 and Z have the above meanings, or a reactive derivative thereof to obtain the corresponding 7-substituted compound of Formula IV in which R 1 , R 2 , R 3 and Z have the above meanings; and, if needed, (B) reacting compound IV with the appropriate nucleophile to obtain the 3-substituted compound of Formula V in which R 1 , R 2 , R 3 and Z have the above meanings, R 4 <SP>1</SP> is the same as R 4 except acetoxy; and then, if needed, (C) treating the 7-substituted compound (IV) or the 3-substituted compound (V) with the appropriate alcohol, thiol, alkyl halide or amine to obtain the corresponding 4-substituted compound of Formula I; and, if needed, (D) forming the salt of compound I. The salts are the alkali metal salts, ammonium, and salts of diphenylenediamine, dicyclohexylamine, N - methyl - N - n - butoxyethylbenzylamine, N,N - di - n - butoxyethylbenzylamine, tri - n - butoxyethylamine, N - methylpiperazine, N - methyl - 4 - chloropiperidine, N- methylmorpholine, guanyl urea, triethylamine and others. The compounds of Formula I are active against both gram-positive and gramnegative organisms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2946567A GB1187323A (en) | 1967-06-26 | 1967-06-26 | Sydnone and Sydnone Imine Derivatives of 7-Aminocephalosporanic Acids and Preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2946567A GB1187323A (en) | 1967-06-26 | 1967-06-26 | Sydnone and Sydnone Imine Derivatives of 7-Aminocephalosporanic Acids and Preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1187323A true GB1187323A (en) | 1970-04-08 |
Family
ID=10291977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2946567A Expired GB1187323A (en) | 1967-06-26 | 1967-06-26 | Sydnone and Sydnone Imine Derivatives of 7-Aminocephalosporanic Acids and Preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1187323A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989010926A1 (en) * | 1988-05-13 | 1989-11-16 | Farmitalia Carlo Erba S.R.L. | 1,1-dioxo-cephem-4-carbothiolic acid derivatives |
| JP2022545749A (en) * | 2019-08-29 | 2022-10-28 | ザ リージェンツ オブ ザ ユニヴァーシティ オブ カリフォルニア | Compounds and methods of use thereof for identifying beta-lactamases |
-
1967
- 1967-06-26 GB GB2946567A patent/GB1187323A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989010926A1 (en) * | 1988-05-13 | 1989-11-16 | Farmitalia Carlo Erba S.R.L. | 1,1-dioxo-cephem-4-carbothiolic acid derivatives |
| GR890100309A (en) * | 1988-05-13 | 1990-03-12 | Erba Carlo Spa | A process for preparing 1,1-dixo-cephem-carbothiolic acid derivatives |
| US5356888A (en) * | 1988-05-13 | 1994-10-18 | Farmitalia Carlo Erba | 1,1-dioxo-cephem-4-carbothiolic acid derivatives |
| JP2022545749A (en) * | 2019-08-29 | 2022-10-28 | ザ リージェンツ オブ ザ ユニヴァーシティ オブ カリフォルニア | Compounds and methods of use thereof for identifying beta-lactamases |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |