IE36192L - 3-carbamoyloxymethylcephalosporins - Google Patents
3-carbamoyloxymethylcephalosporinsInfo
- Publication number
- IE36192L IE36192L IE8972A IE8972A IE36192L IE 36192 L IE36192 L IE 36192L IE 8972 A IE8972 A IE 8972A IE 8972 A IE8972 A IE 8972A IE 36192 L IE36192 L IE 36192L
- Authority
- IE
- Ireland
- Prior art keywords
- acid
- group
- benzyl
- compounds
- chloride
- Prior art date
Links
- 229930186147 Cephalosporin Natural products 0.000 abstract 4
- 229940124587 cephalosporin Drugs 0.000 abstract 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 abstract 3
- -1 Cephalosporin compounds Chemical class 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- QAMQBROWEMDMOK-CQSZACIVSA-N (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxo-6-phenylmethoxyhexanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](CCCC(=O)OCC1=CC=CC=C1)C(O)=O QAMQBROWEMDMOK-CQSZACIVSA-N 0.000 abstract 1
- UQLRAAASUFVOLL-LLVKDONJSA-N (2R)-2-amino-6-oxo-6-phenylmethoxyhexanoic acid Chemical compound N[C@H](CCCC(=O)OCC1=CC=CC=C1)C(O)=O UQLRAAASUFVOLL-LLVKDONJSA-N 0.000 abstract 1
- FZBNFTSTPLZIOZ-MRVPVSSYSA-N (5R)-5-[(2-methylpropan-2-yl)oxycarbonylamino]-6-oxo-6-(2,2,2-trichloroethoxy)hexanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](CCCC(O)=O)C(=O)OCC(Cl)(Cl)Cl FZBNFTSTPLZIOZ-MRVPVSSYSA-N 0.000 abstract 1
- KPWDGTGXUYRARH-UHFFFAOYSA-N 2,2,2-trichloroethanol Chemical compound OCC(Cl)(Cl)Cl KPWDGTGXUYRARH-UHFFFAOYSA-N 0.000 abstract 1
- QXAJNNROHSRLNQ-UHFFFAOYSA-N 2-benzhydryl-2-phenylpropanedioyl dichloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)(C(Cl)=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 QXAJNNROHSRLNQ-UHFFFAOYSA-N 0.000 abstract 1
- AVBHHECXXFKOHS-UHFFFAOYSA-N 3-benzhydryloxy-3-oxo-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)C(=O)OC(C=1C=CC=CC=1)C1=CC=CC=C1 AVBHHECXXFKOHS-UHFFFAOYSA-N 0.000 abstract 1
- OYIFNHCXNCRBQI-SCSAIBSYSA-N D-2-aminoadipic acid Chemical compound OC(=O)[C@H](N)CCCC(O)=O OYIFNHCXNCRBQI-SCSAIBSYSA-N 0.000 abstract 1
- ITLHXEGAYQFOHJ-UHFFFAOYSA-N [diazo(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(=[N+]=[N-])C1=CC=CC=C1 ITLHXEGAYQFOHJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 239000011260 aqueous acid Substances 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 235000019445 benzyl alcohol Nutrition 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- OPEBOTYCWHBJJL-UHFFFAOYSA-N bromoformonitrile oxide Chemical compound [O-][N+]#CBr OPEBOTYCWHBJJL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 239000000645 desinfectant Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000003495 polar organic solvent Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 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
- C07D501/02—Preparation
- C07D501/04—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
-
- 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
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
-
- 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
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
-
- 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
- C07D501/57—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with a further substituent in position 7, e.g. cephamycines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1350772 Cephalosporin compounds MERCK & CO Inc 14 Jan 1972 [27 Jan 1971 17 June 1971 24 Aug 1971 29 Nov 1971] 3295/71 28522/71 39654/71 and 1829/72 Divided out of 1350772 Headings C2A and C2C 3 - Carbamoyloxymethyl - cephalosporin compounds having the general Formula (I) and the corresponding #<SP>2</SP> compounds, and salts and esters thereof, wherein R<SP>1</SP> is hydrogen or an acyl group and R 1 is hydrogen or methoxy, the said compounds being novel when R 1 is hydrogen, are prepared by reacting a corresponding 3- hydroxymethyl - cephalosporin compound, in which if necessary any isocyanate-reactive group other than the 3-hydroxymethyl group is suitably blocked, the bromo- or chloro-sulphonyl isocyanate and hydrolysing the product and if necessary removing any blocking group. The reaction is preferably effected in a polar organic solvent and the hydrolysis is carried out by treatment with aqueous acid. Monobenzhydryl phenylmalonyl chloride is prepared by treating phenylmalonic acid with diphenyldiazomethane followed by alkaline hydrolysis to give monobenzhydryl phenylmalonate which is converted to the acid chloride with oxalyl chloride. Benzyl alcohol is esterified with D-α-aminoadipic acid in the presence of c.H 2 SO 4 to give benzyl - D - 5 - amino - 5 - carboxypentanoate, which is then N-protected by reacting with tbutyloxycarbonyl azide in the presence of MgO giving benzyl - D - 5 - t - butyloxycarbonylamino - 5 - carboxypentanoate. The carboxyl group is protected by reacting the latter with 2,2,2 - trichloroethanol in pyridine, and the resulting benzyl D - 5 - t - butoxycarbonylamino - 5 - (2,2,2 - trichloroethoxy)carbonylpentanoate is catalytically hydrogenated to remove the benzyl ester group. The product, D- 5 - t - butoxy - carbonylamino - 5 - (2,2,2 - trichloroethoxy)carbonylpentanoic acid is reacted with oxalyl chloride to give the corresponding acid chloride. The cephalosporin compounds of Formula I and their #<SP>2</SP> isomers, salts and esters, wherein R<SP>1</SP> is an acyl group, have antibacterial activity and may be used with a suitable carrier, diluent or coating to provide pharmaceutical and disinfectant compositions.
[GB1350772A]
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB329571A GB1350772A (en) | 1971-01-27 | 1971-01-27 | Antibiotics and processes for their production |
| GB2852271 | 1971-06-17 | ||
| GB3965471 | 1971-08-24 | ||
| GB182972 | 1972-01-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE36192L true IE36192L (en) | 1972-07-27 |
| IE36192B1 IE36192B1 (en) | 1976-09-15 |
Family
ID=27447180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE8972A IE36192B1 (en) | 1971-01-27 | 1972-01-24 | Antibiotics and processes for their production |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5418274B1 (en) |
| AR (1) | AR204899A1 (en) |
| AU (1) | AU468248B2 (en) |
| BE (1) | BE778508A (en) |
| CA (1) | CA1003404A (en) |
| CH (1) | CH569021A5 (en) |
| DE (1) | DE2203653C3 (en) |
| FR (1) | FR2161866B1 (en) |
| GB (1) | GB1350772A (en) |
| IE (1) | IE36192B1 (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3905963A (en) * | 1972-01-25 | 1975-09-16 | Lilly Co Eli | Process for preparing primary 3-carbamoyloxymethyl cephalosporins |
| US3994875A (en) * | 1974-06-24 | 1976-11-30 | Yeda Research & Development Co. Ltd. | Antibiotics |
| CA1128930A (en) | 1978-04-07 | 1982-08-03 | Stuart B. Laing | Cephalosporin compounds |
| WO1992019286A1 (en) * | 1991-05-03 | 1992-11-12 | University Technologies International, Inc. | Biofilm reduction method |
| WO2004083217A1 (en) * | 2003-03-20 | 2004-09-30 | Orchid Chemicals & Pharmaceuticals Ltd | An improved process for the preparation of cefoxitin |
| CN101830913B (en) * | 2010-04-09 | 2012-10-31 | 烟台宝华生物技术有限公司 | Cephalosporins parent nucleus derived compound, cephem onium salt compound prepared by same and method for preparing cephalosporins pyrazol sulfate by adopting same |
| CN103848851B (en) * | 2012-11-29 | 2016-03-02 | 上海交通大学 | A kind of synthetic method of Method of cefcapene pivoxil hydrochloride |
| WO2020158777A1 (en) | 2019-01-29 | 2020-08-06 | ニプロ株式会社 | Artificial lung device |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1445633A1 (en) | 1963-10-07 | 1968-12-05 | Ciba Geigy | Process for the preparation of new amides |
| CH480365A (en) * | 1965-01-18 | 1969-10-31 | Ciba Geigy | Process for the preparation of new derivatives of 7-aminocephalosporanic acid |
-
1971
- 1971-01-27 GB GB329571A patent/GB1350772A/en not_active Expired
-
1972
- 1972-01-01 AR AR24020972A patent/AR204899A1/en active
- 1972-01-18 CA CA132,726A patent/CA1003404A/en not_active Expired
- 1972-01-24 IE IE8972A patent/IE36192B1/en unknown
- 1972-01-26 CH CH112472A patent/CH569021A5/xx not_active IP Right Cessation
- 1972-01-26 DE DE19722203653 patent/DE2203653C3/en not_active Expired
- 1972-01-26 BE BE778508A patent/BE778508A/en unknown
- 1972-01-26 AU AU38356/72A patent/AU468248B2/en not_active Expired
- 1972-01-27 JP JP7210183A patent/JPS5418274B1/ja active Pending
- 1972-01-27 FR FR7202751A patent/FR2161866B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AR204899A1 (en) | 1976-03-19 |
| GB1350772A (en) | 1974-04-24 |
| DE2203653A1 (en) | 1972-08-10 |
| DE2203653B2 (en) | 1974-12-19 |
| JPS5418274B1 (en) | 1979-07-06 |
| DE2203653C3 (en) | 1975-07-31 |
| AU3835672A (en) | 1973-08-02 |
| AU468248B2 (en) | 1976-01-08 |
| BE778508A (en) | 1972-07-26 |
| CA1003404A (en) | 1977-01-11 |
| CH569021A5 (en) | 1975-11-14 |
| FR2161866A1 (en) | 1973-07-13 |
| IE36192B1 (en) | 1976-09-15 |
| FR2161866B1 (en) | 1975-08-01 |
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