IE34055L - 3-halomethyl-cephalosporin derivatives - Google Patents
3-halomethyl-cephalosporin derivativesInfo
- Publication number
- IE34055L IE34055L IE700337A IE33770A IE34055L IE 34055 L IE34055 L IE 34055L IE 700337 A IE700337 A IE 700337A IE 33770 A IE33770 A IE 33770A IE 34055 L IE34055 L IE 34055L
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- cephalosporin
- tribromide
- sulphoxide
- esters
- Prior art date
Links
- 229940124587 cephalosporin Drugs 0.000 title abstract 5
- -1 Cephalosporin esters Chemical class 0.000 abstract 4
- 229930186147 Cephalosporin Natural products 0.000 abstract 3
- GPWHDDKQSYOYBF-UHFFFAOYSA-N ac1l2u0q Chemical compound Br[Br-]Br GPWHDDKQSYOYBF-UHFFFAOYSA-N 0.000 abstract 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 abstract 3
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 abstract 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 abstract 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 abstract 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 150000001875 compounds Chemical class 0.000 abstract 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- OHZZTXYKLXZFSZ-UHFFFAOYSA-I manganese(3+) 5,10,15-tris(1-methylpyridin-1-ium-4-yl)-20-(1-methylpyridin-4-ylidene)porphyrin-22-ide pentachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mn+3].C1=CN(C)C=CC1=C1C(C=C2)=NC2=C(C=2C=C[N+](C)=CC=2)C([N-]2)=CC=C2C(C=2C=C[N+](C)=CC=2)=C(C=C2)N=C2C(C=2C=C[N+](C)=CC=2)=C2N=C1C=C2 OHZZTXYKLXZFSZ-UHFFFAOYSA-I 0.000 abstract 1
- 125000006502 nitrobenzyl group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 abstract 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000000126 substance Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000003512 tertiary amines 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
1295908 Cephalosporin esters and sulphoxides ELI LILLY & CO 26 March 1970 [28 March 1969 8 Dec 1969] 14835/70 Headings C2A and C2C Novel cephalosporin sulphoxide esters of Formula (I). and also cephalosporin esters of Formula (II) wherein X is Cl, Br or I, R has the formula in which m is 0-4, n is 1-4, Z is oxygen, sulphur or a chemical bond, R<SP>3</SP> and R<SP>4</SP> are each H or CH 3 , Y is H or a substituent on the phenyl ring and z is 1 or 2; and R<SP>1</SP> is 2,2,2-trichloroethyl, C 4 -C 6 tert-alkyl, C 5 -C 7 tent.alkenyl, C 5 -C 7 tert-alkynyl, benzyl, methoxybenzyl, nitrobenzyl, phenacyl, phthalimidomethyl or succinimidoniethyl, are prepared by reacting phosphorus trichloride, tribromide, pentachloride, pentabromide, oxychloride or oxybromide with a corresponding 3-hydroxymethyl #<SP>3</SP>-cephalosporin sulphoxide ester in the presence of a tertiary amine in an anhydrous aprotic organic liquid diluent at a temperature of -75 C. to 50 C. When temperatures above -25 C. are employed and the reactant is phosphorus trichloride or tribromide in excess of the theoretical equimolar amount, the product has the Formula (II) above. Use of (a) an equimolar amount of phosphorus trichloride or tribromide at below -25 C., and (b) phosphorus penta-bromide or -chloride or oxybromide or - chloride, results in a sulphoxide product of Formula (I). The resulting 3-chloro- or 3- bromomethyl compounds may be -converted to the 3-iodomethyl compound by treatment with alkali metal iodide.
[GB1295908A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81164069A | 1969-03-28 | 1969-03-28 | |
| US88323169A | 1969-12-08 | 1969-12-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE34055L true IE34055L (en) | 1970-09-28 |
| IE34055B1 IE34055B1 (en) | 1975-01-22 |
Family
ID=27123508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE337/70A IE34055B1 (en) | 1969-03-28 | 1970-03-16 | 3-halomethyl-delta3-cephalosporin esters and sulfoxides thereof useful in the production of antibiotics,and process for preparing the intermediates and antibiotics |
Country Status (14)
| Country | Link |
|---|---|
| JP (2) | JPS5112635B1 (en) |
| BE (1) | BE748055A (en) |
| CA (1) | CA986094A (en) |
| CH (2) | CH562828A5 (en) |
| DE (1) | DE2065708C3 (en) |
| ES (1) | ES377938A1 (en) |
| FR (1) | FR2035977A1 (en) |
| GB (1) | GB1295908A (en) |
| IE (1) | IE34055B1 (en) |
| IL (1) | IL34093A (en) |
| NL (1) | NL7004479A (en) |
| PL (2) | PL83186B1 (en) |
| RO (1) | RO56339A (en) |
| SE (1) | SE412237B (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE755256A (en) * | 1969-08-26 | 1971-02-25 | Glaxo Lab Ltd | |
| IL59395A (en) | 1979-03-06 | 1983-07-31 | Gist Brocades Nv | Bromo-substituted deacetoxycephalosporin derivatives and their preparation |
| JPS5832884A (en) * | 1981-08-20 | 1983-02-25 | Otsuka Chem Co Ltd | Production of 3-exomethylenecepham derivative |
-
1970
- 1970-03-16 IE IE337/70A patent/IE34055B1/en unknown
- 1970-03-16 CA CA077,518A patent/CA986094A/en not_active Expired
- 1970-03-18 IL IL34093A patent/IL34093A/en unknown
- 1970-03-26 GB GB1295908D patent/GB1295908A/en not_active Expired
- 1970-03-26 CH CH466570A patent/CH562828A5/xx not_active IP Right Cessation
- 1970-03-26 NL NL7004479A patent/NL7004479A/xx unknown
- 1970-03-26 SE SE7004235A patent/SE412237B/en unknown
- 1970-03-27 BE BE748055D patent/BE748055A/en not_active IP Right Cessation
- 1970-03-27 FR FR7011274A patent/FR2035977A1/fr active Pending
- 1970-03-27 PL PL1970139661A patent/PL83186B1/en unknown
- 1970-03-27 PL PL1970176080A patent/PL92638B1/en unknown
- 1970-03-27 RO RO62914A patent/RO56339A/ro unknown
- 1970-03-28 JP JP45026434A patent/JPS5112635B1/ja active Pending
- 1970-03-31 DE DE2065708A patent/DE2065708C3/en not_active Expired
-
1971
- 1971-03-25 ES ES377938A patent/ES377938A1/en not_active Expired
-
1975
- 1975-01-20 CH CH466570D patent/CH564023A5/xx not_active IP Right Cessation
- 1975-08-27 JP JP50103874A patent/JPS5136277B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2065708A1 (en) | 1975-04-10 |
| IL34093A (en) | 1975-10-15 |
| CH564023A5 (en) | 1975-07-15 |
| RO56339A (en) | 1975-03-15 |
| PL83186B1 (en) | 1975-12-31 |
| JPS5112635B1 (en) | 1976-04-21 |
| GB1295908A (en) | 1972-11-08 |
| DE2065708B2 (en) | 1977-10-20 |
| IL34093A0 (en) | 1970-05-21 |
| SE412237B (en) | 1980-02-25 |
| CH562828A5 (en) | 1975-06-13 |
| DE2015317A1 (en) | 1971-02-18 |
| ES377938A1 (en) | 1973-01-01 |
| CA986094A (en) | 1976-03-23 |
| DE2015317B2 (en) | 1975-08-28 |
| DE2065708C3 (en) | 1978-06-08 |
| PL92638B1 (en) | 1977-04-30 |
| FR2035977A1 (en) | 1970-12-24 |
| IE34055B1 (en) | 1975-01-22 |
| JPS5136277B1 (en) | 1976-10-07 |
| NL7004479A (en) | 1970-09-30 |
| BE748055A (en) | 1970-09-28 |
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