GB998265A - New cephalosporin compounds and method for preparing same - Google Patents
New cephalosporin compounds and method for preparing sameInfo
- Publication number
- GB998265A GB998265A GB12401/62A GB1240162A GB998265A GB 998265 A GB998265 A GB 998265A GB 12401/62 A GB12401/62 A GB 12401/62A GB 1240162 A GB1240162 A GB 1240162A GB 998265 A GB998265 A GB 998265A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- reacting
- prepared
- cephalosporins
- alkyl
- 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
- 229930186147 Cephalosporin Natural products 0.000 title abstract 4
- 229940124587 cephalosporin Drugs 0.000 title abstract 4
- -1 cephalosporin compounds Chemical class 0.000 title 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- 150000001780 cephalosporins Chemical class 0.000 abstract 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- XVGQHRKNXSUPEF-UHFFFAOYSA-N 2-(trifluoromethyl)benzenethiol Chemical compound FC(F)(F)C1=CC=CC=C1S XVGQHRKNXSUPEF-UHFFFAOYSA-N 0.000 abstract 2
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 abstract 2
- 125000001302 tertiary amino group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 abstract 1
- AYZIBBGBPJQOLI-UHFFFAOYSA-N 2-[2-(trifluoromethyl)phenyl]sulfanylacetic acid Chemical compound OC(=O)CSC1=CC=CC=C1C(F)(F)F AYZIBBGBPJQOLI-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001450 anions Chemical class 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 235000010288 sodium nitrite Nutrition 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B23—MACHINE TOOLS; METAL-WORKING NOT OTHERWISE PROVIDED FOR
- B23C—MILLING
- B23C3/00—Milling particular work; Special milling operations; Machines therefor
- B23C3/28—Grooving workpieces
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
-
- 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)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Shaping By String And By Release Of Stress In Plastics And The Like (AREA)
- Cephalosporin Compounds (AREA)
Abstract
Relates to cephalosporins having the structural formula <FORM:0998265/C2/1> wherein R1, taken alone, is -OH, C1-C8 acyloxy, or tertiary amino; R2 is -OH when R1 is -OH; R2 is -OH when R1 is C1-C8 acyloxy; R2 is O- when R1 is tertiary amino; R1 and R2, when taken together, are -O-; R3 and R4 are hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C5-C7 cycloalkyl, or C2-C6 alkoxyalkyl; n is 0, 1, 2, 3 or 4; R5 is C1-C6 alkyl, C2 -C6 alkenyl, C2-C6 alkinyl, C5-C6 cycloalkyl, phenyl, b -furyl, b -thienyl, thenyl or naphthyl or a fluoro, chloro, bromo, nitro, trifluoromethyl, C1-C4 alkyl, C1-C4 alkylmercapto, or C1-C4 alkoxy substitution product thereof; the salts thereof with pharmaceutically acceptable cations and anions and the pharmaceutically acceptable esters and amides of the cephalosporins. The cephalosporins may be prepared by reacting the relevant nucleus with the appropriate acylating agent. Examples describe the preparation of 7-phenyl-, 7-p-chlorophenyl-, 7 - (51 - chloro - 21 - methyl), 7 - benzyl -, 7 - n - butyl and 7 - isoamylmercaptoacetamidocephalosporanic acid, 7-a -m-tolylmercaptopropionamido- and 7 - (a - methyl - a - phenylmercaptopropionamido) - cephalosporanic acid. a -Methyl-a - phenylmercaptopropionic acid may be prepared by reacting chloroform with a solution of thiophenol and potassium hydroxide in acetone, and may be converted to the acid chloride by reaction with thionyl chloride. o - Trifluoromethylthiophenol may be prepared by reacting o-trifluoromethylaniline with sodium nitrite, treating the reaction product with potassium ethyl xanthate, and refluxing with alcoholic potassium hydroxide. o-Trifluoromethylphenylmercaptoacetic acid is prepared by reacting o-trifluoromethylthiophenol with monochloroacetic acid in the presence of sodium hydride, and may be converted to the acid chloride by reaction with thionyl chloride. Specifications 810,196 and 953,695 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9999861A | 1961-04-03 | 1961-04-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB998265A true GB998265A (en) | 1965-07-14 |
Family
ID=22277606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12401/62A Expired GB998265A (en) | 1961-04-03 | 1962-03-30 | New cephalosporin compounds and method for preparing same |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE615956A (en) |
| BR (1) | BR6237696D0 (en) |
| CH (1) | CH410954A (en) |
| DK (1) | DK132533C (en) |
| FR (1) | FR1508878A (en) |
| GB (1) | GB998265A (en) |
| LU (1) | LU41472A1 (en) |
| NO (1) | NO132691C (en) |
| OA (1) | OA02696A (en) |
| SE (1) | SE321680B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0699681A1 (en) * | 1994-09-02 | 1996-03-06 | Bristol-Myers Company | Cephalosporin derivatives |
| US5567698A (en) * | 1995-02-15 | 1996-10-22 | Bristol-Myers Squibb Company | Pyridinium thiomethyl substituted chepholosporin derivatives |
| US5620969A (en) * | 1995-04-25 | 1997-04-15 | Bristol-Myers Squibb Company | Cephalosporin derviatives |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE638034A (en) * | 1962-10-03 | |||
| US3503967A (en) * | 1968-08-26 | 1970-03-31 | Bristol Myers Co | Process for the preparation of 7 - (alpha-(4 - pyridylthio)acetamido)cephalosporanic acid |
-
1962
- 1962-03-28 NO NO143833A patent/NO132691C/no unknown
- 1962-03-30 GB GB12401/62A patent/GB998265A/en not_active Expired
- 1962-03-31 LU LU41472D patent/LU41472A1/xx unknown
- 1962-04-02 DK DK150362A patent/DK132533C/en active
- 1962-04-03 BE BE615956A patent/BE615956A/en unknown
- 1962-04-03 BR BR137696/62A patent/BR6237696D0/en unknown
- 1962-04-03 SE SE3692/62A patent/SE321680B/xx unknown
- 1962-04-03 CH CH399662A patent/CH410954A/en unknown
- 1962-06-29 FR FR92398A patent/FR1508878A/en not_active Expired
-
1967
- 1967-03-30 OA OA52870A patent/OA02696A/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0699681A1 (en) * | 1994-09-02 | 1996-03-06 | Bristol-Myers Company | Cephalosporin derivatives |
| US5567698A (en) * | 1995-02-15 | 1996-10-22 | Bristol-Myers Squibb Company | Pyridinium thiomethyl substituted chepholosporin derivatives |
| US5668284A (en) * | 1995-02-15 | 1997-09-16 | Bristol-Myers Squibb Company | Cephalosporin derivatives |
| US5620969A (en) * | 1995-04-25 | 1997-04-15 | Bristol-Myers Squibb Company | Cephalosporin derviatives |
Also Published As
| Publication number | Publication date |
|---|---|
| BE615956A (en) | 1962-10-03 |
| LU41472A1 (en) | 1962-10-01 |
| DK132533C (en) | 1976-05-24 |
| NO132691C (en) | 1975-12-17 |
| FR3123M (en) | 1965-02-15 |
| NO132691B (en) | 1975-09-08 |
| FR1508878A (en) | 1968-01-05 |
| CH410954A (en) | 1966-04-15 |
| SE321680B (en) | 1970-03-16 |
| DK132533B (en) | 1975-12-22 |
| OA02696A (en) | 1970-12-15 |
| BR6237696D0 (en) | 1973-05-31 |
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