GB1265332A - - Google Patents
Info
- Publication number
- GB1265332A GB1265332A GB1265332DA GB1265332A GB 1265332 A GB1265332 A GB 1265332A GB 1265332D A GB1265332D A GB 1265332DA GB 1265332 A GB1265332 A GB 1265332A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- formula
- cephalosporins
- phenyl
- atom
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 13
- -1 phenoxyacetyl Chemical group 0.000 abstract 9
- 229940124587 cephalosporin Drugs 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 4
- 229930186147 Cephalosporin Natural products 0.000 abstract 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 150000001780 cephalosporins Chemical class 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
- 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
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 abstract 1
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 abstract 1
- 238000006073 displacement reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000000262 haloalkenyl group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000000232 haloalkynyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000006502 nitrobenzyl group Chemical group 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 230000000269 nucleophilic effect Effects 0.000 abstract 1
- 239000012434 nucleophilic reagent Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 125000006413 ring segment Chemical group 0.000 abstract 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 229910052727 yttrium Inorganic materials 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—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, cefaclor, or cephalexine
-
- 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
-
- 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
- C07D501/60—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 3 and 4
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1,265,332. #<SP>2</SP>-Cephalosporins. ELI LILLEY & CO. 7 Feb., 1969 [7 Feb., 1968; 13 Jan., 1969 (2)], No. 6824/69. Heading C2A. Novel #<SP>2</SP>-cephalosporins of Formula I wherein R is trimethylsilyl, triphenylmethyl, butoxycarbonyl, phenoxyacetyl, phenylacetyl, phenylmercaptoacetyl or phenyl-α,α-dimethylacetyl, or a phenoxyacetyl, phenylacetyl, phenylmercaptoacetyl or phenyl - α,α - dimethylacetyl group ring substituted with F, Cl, Br, I, NO 2 , CN, CF 3 , C 1 to C 6 alkyl, C 1 to C 2 alkoxy or butoxycarbonylmethyl; R<SP>11</SP> is CN or XY where X is O or S and Y is C 1 to C 10 alkyl, C 3 to C 10 alkenyl, C 3 to C 15 alkynyl, C 5 to C 7 cycloalkyl, C 3 to C 6 cycloalkyl-C 1 to C 6 alkyl, C 2 to C 10 haloalkyl, C 3 to C 10 haloalkenyl, C 3 to C 10 haloalkynyl, C 1 to C 3 cyanoalkyl, C 1 to C 3 alkyl-X-C 1 to C 6 alkyl where X is O or S, C 1 to C 6 alkoxycarbonyl-C 1 to C 6 alkyl, C 2 to C 4 alkanoyl-C 1 to C 6 alkyl, C 2 to C 4 alkanoyloxy- C 1 -C 6 alkyl, (2<SP>1</SP>-tetrahydrofuryl)-C 1 to C 3 alkyl, 31-tetrahydrofuryl, (2<SP>1</SP>-thienyl)-C 1 to C 3 alkyl, phenyl-C 1 to C 3 alkyl, or a phenyl, benzyl or phenethyl group which may be substituted with CN, NO 2 , CF 3 , C 1 to C 3 alkyl, C 1 to C 3 alkoxy or C 1 to C 3 alkoxycarbonyl, or R<SP>11</SP> is where R<SP>3</SP> and R<SP>4</SP> are each C 1 to C 6 alkyl or together with the common N atom complete a 5 to 6 ring atom-containing heterocycle of formula in which n is 0 or 1 and Q is -CH 2 -, -O-, -S- or where R<SP>6</SP> is H or C 1 to C 4 alkyl, except that when n is 0, Q is -CH 2 -; and R<SP>1</SP> is C 4 to C 6 tert. alkyl, C 5 to C 7 tert. alkynyl, benzyl, methoxybenzyl, nitrobenzyl, phenacyl, trimethylsilyl, benzhydryl, phthalimidomethyl or succinimidomethyl, are prepared by reacting N-bromosuccinimide with a 3-desacetoxy-#<SP>2</SP>-cephalosporin of Formula III in an anhydrous organic solvent at about 40‹ to 100‹ C. to give a novel 3-bromomethyl-#<SP>2</SP>- cephalosporin of Formula IV which compound is then reacted with an appropriate nucleophilic reagent to replace the bromine atom by the group R<SP>11</SP>. The starting cephalosporins III may be prepared by hydrogenating a #<SP>3</SP>-cephalosporin ester to form the corresponding #<SP>3</SP>-desacetoxycephalosporin ester which is treated with a base such as pyridine in the cold to isomerize the #<SP>3</SP> double bond to the #<SP>2</SP> position. In addition to the #<SP>2</SP> compounds of Formula I, the inventive process may form some of the corresponding #<SP>3</SP> cephalosporins due to the basic conditions which may be used in the nucleophilic displacement of the Br atom. Alternatively the #<SP>2</SP> compounds may be converted to corresponding #<SP>3</SP> compounds by oxidation to the #<SP>3</SP> sulphoxide which is subsequently reduced, according to Specification 1,265,333.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70352368A | 1968-02-07 | 1968-02-07 | |
| US79088669A | 1969-01-13 | 1969-01-13 | |
| US79084269A | 1969-01-13 | 1969-01-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1265332A true GB1265332A (en) | 1972-03-01 |
Family
ID=27418758
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1265333D Expired GB1265333A (en) | 1968-02-07 | 1969-02-07 | |
| GB1265332D Expired GB1265332A (en) | 1968-02-07 | 1969-02-07 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1265333D Expired GB1265333A (en) | 1968-02-07 | 1969-02-07 |
Country Status (11)
| Country | Link |
|---|---|
| JP (3) | JPS524558B1 (en) |
| BE (1) | BE728053A (en) |
| CH (1) | CH534694A (en) |
| DK (1) | DK140726B (en) |
| FI (1) | FI56535C (en) |
| FR (3) | FR2001491B1 (en) |
| GB (2) | GB1265333A (en) |
| IL (2) | IL40447A (en) |
| LU (1) | LU57932A1 (en) |
| NL (1) | NL173407C (en) |
| SE (3) | SE384511B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2132883A1 (en) * | 1970-07-08 | 1972-01-13 | Ciba Geigy Ag | Cephem compounds |
| JPS53164082U (en) * | 1977-05-31 | 1978-12-22 | ||
| JPS5899787U (en) * | 1981-12-28 | 1983-07-07 | 奥野電器株式会社 | lamp socket |
| EP0300546B1 (en) * | 1987-07-10 | 1995-08-09 | Gist-Brocades N.V. | Process for the preparation of cephem compounds and cephalosporin derivatives |
-
1969
- 1969-02-04 FI FI326/69A patent/FI56535C/en active
- 1969-02-05 SE SE6901500A patent/SE384511B/en unknown
- 1969-02-06 IL IL40447A patent/IL40447A/en unknown
- 1969-02-06 LU LU57932D patent/LU57932A1/xx unknown
- 1969-02-06 DK DK63069AA patent/DK140726B/en not_active IP Right Cessation
- 1969-02-06 IL IL41553A patent/IL41553A/en unknown
- 1969-02-07 JP JP44009211A patent/JPS524558B1/ja active Pending
- 1969-02-07 FR FR696902897A patent/FR2001491B1/fr not_active Expired
- 1969-02-07 BE BE728053D patent/BE728053A/xx not_active IP Right Cessation
- 1969-02-07 GB GB1265333D patent/GB1265333A/en not_active Expired
- 1969-02-07 CH CH190469A patent/CH534694A/en not_active IP Right Cessation
- 1969-02-07 GB GB1265332D patent/GB1265332A/en not_active Expired
- 1969-02-07 NL NLAANVRAGE6902013,A patent/NL173407C/en not_active IP Right Cessation
-
1971
- 1971-03-03 FR FR7107345A patent/FR2085656B1/fr not_active Expired
- 1971-03-03 FR FR7107344A patent/FR2095486A5/fr not_active Expired
- 1971-08-13 JP JP46061594A patent/JPS4924076B1/ja active Pending
- 1971-08-13 JP JP46061595A patent/JPS524559B1/ja active Pending
-
1972
- 1972-01-14 SE SE7200411A patent/SE407064B/en unknown
-
1975
- 1975-11-14 SE SE7512818A patent/SE418616B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI56535C (en) | 1980-02-11 |
| JPS4924076B1 (en) | 1974-06-20 |
| FR2095486A5 (en) | 1972-02-11 |
| LU57932A1 (en) | 1969-09-17 |
| FR2001491B1 (en) | 1973-07-13 |
| IL40447A (en) | 1976-02-29 |
| SE407064B (en) | 1979-03-12 |
| NL6902013A (en) | 1969-08-11 |
| DK140726B (en) | 1979-11-05 |
| GB1265333A (en) | 1972-03-01 |
| DK140726C (en) | 1980-03-31 |
| FR2085656A1 (en) | 1971-12-31 |
| SE418616B (en) | 1981-06-15 |
| SE7512818L (en) | 1975-11-14 |
| FR2001491A1 (en) | 1969-09-26 |
| FR2085656B1 (en) | 1974-08-23 |
| JPS524558B1 (en) | 1977-02-04 |
| FI56535B (en) | 1979-10-31 |
| SE384511B (en) | 1976-05-10 |
| JPS524559B1 (en) | 1977-02-04 |
| BE728053A (en) | 1969-08-07 |
| CH534694A (en) | 1973-03-15 |
| NL173407C (en) | 1984-01-16 |
| IL41553A (en) | 1976-02-29 |
| NL173407B (en) | 1983-08-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |