IL40143A - The preparation of cephalosporins from penicillin sulphoxides and new mixed anhydrides of penicillin sulphoxides - Google Patents
The preparation of cephalosporins from penicillin sulphoxides and new mixed anhydrides of penicillin sulphoxidesInfo
- Publication number
- IL40143A IL40143A IL40143A IL4014372A IL40143A IL 40143 A IL40143 A IL 40143A IL 40143 A IL40143 A IL 40143A IL 4014372 A IL4014372 A IL 4014372A IL 40143 A IL40143 A IL 40143A
- Authority
- IL
- Israel
- Prior art keywords
- process according
- group
- acid
- carbon
- atom
- Prior art date
Links
- 150000008064 anhydrides Chemical class 0.000 title claims 9
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 title claims 5
- 229930182555 Penicillin Natural products 0.000 title claims 3
- 229940049954 penicillin Drugs 0.000 title claims 3
- 238000002360 preparation method Methods 0.000 title claims 2
- 229930186147 Cephalosporin Natural products 0.000 title 1
- 229940124587 cephalosporin Drugs 0.000 title 1
- 150000001780 cephalosporins Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 claims 31
- 239000002253 acid Substances 0.000 claims 19
- 229910052799 carbon Inorganic materials 0.000 claims 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 125000004432 carbon atom Chemical group C* 0.000 claims 11
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 5
- 239000005864 Sulphur Substances 0.000 claims 5
- 150000008065 acid anhydrides Chemical class 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- 229910052698 phosphorus Inorganic materials 0.000 claims 5
- 239000011574 phosphorus Substances 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 claims 4
- 229930195708 Penicillin V Natural products 0.000 claims 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 150000001721 carbon Chemical group 0.000 claims 3
- 239000003153 chemical reaction reagent Substances 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 229940056367 penicillin v Drugs 0.000 claims 3
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 claims 3
- 125000002071 phenylalkoxy group Chemical group 0.000 claims 3
- 125000003884 phenylalkyl group Chemical group 0.000 claims 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 2
- 241000282320 Panthera leo Species 0.000 claims 2
- 125000004018 acid anhydride group Chemical group 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 229910052782 aluminium Inorganic materials 0.000 claims 2
- 239000004411 aluminium Substances 0.000 claims 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 229940126214 compound 3 Drugs 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 150000003377 silicon compounds Chemical class 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims 2
- 229910052721 tungsten Inorganic materials 0.000 claims 2
- 239000010937 tungsten Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims 1
- 101100515517 Arabidopsis thaliana XI-I gene Proteins 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 claims 1
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 claims 1
- 125000002015 acyclic group Chemical group 0.000 claims 1
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Chemical group 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- 229910052732 germanium Inorganic materials 0.000 claims 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 230000007935 neutral effect Effects 0.000 claims 1
- -1 nitro carbonyl Chemical group 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- WSHJJCPTKWSMRR-RXMQYKEDSA-N penam group Chemical group S1CCN2[C@H]1CC2=O WSHJJCPTKWSMRR-RXMQYKEDSA-N 0.000 claims 1
- 235000019371 penicillin G benzathine Nutrition 0.000 claims 1
- 229940056360 penicillin g Drugs 0.000 claims 1
- SZRONZXSOSCLOK-UHFFFAOYSA-N pentacyanocyclopentadiene Chemical compound N#CC1C(C#N)=C(C#N)C(C#N)=C1C#N SZRONZXSOSCLOK-UHFFFAOYSA-N 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000006049 ring expansion reaction Methods 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 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
- C07D501/08—Preparation by forming the ring or condensed ring systems
- C07D501/10—Preparation by forming the ring or condensed ring systems from compounds containing the penicillin ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Claims (1)
1. Process for the preparation of derivat comprising converting a acid salt thereof an anhydride of a penicillanic acid heating this acid anhydride intermediate at a temperature up to at most in 1 a dry inert organic solvent with an anhydrous acid which is capable of causing ring expansion of the ring to a in the presence of a compound capable of removing water formed during the ring the penam structure fast enough to prevent the water hydrolysis of the acid anhydride moiety present and forming neutral or basic products on the aforesaid acid being stron enough no or not to a substantial extent to oilylated under the reaction conditions and hydrolysing the resulting compound s tu and separating the formed acid as such or as a calcium or amine Process according to claim 1 for the of acid derivatives of from corresponding suiphoxxdes of the general wherein represents a hydrogen atom or a group linked to the nitrogen atom by a carbon or sulphur optionally having not being affected by the represents a hydrogen atom or a lower alkyl or lowe alkyl or and together with the nitrogen atom to which they are attached collectively represent a heterocyclic a succinirnido oxazolidinyl or imidazolidinyl which may carry not being affected by the one or more and the group represents an acid anhydride wherein is a group of the general wherein R and are the same of different each 5 represents a lower alkyl a a radical containing 5 to 8 carbon henyl a alkyl group aining 1 or 2 carbon atoms in the alkyl a lower lower or phenoxy or a 1 or 2 carbon atoms in the alkox a halogen atom or a group or onyloxy or R and together represent the residue of a 4 ring including and represents a or phosphorus or an acid anhydride group wherein is of the general wherein and are the same or different and each 4 5 represents a lower alkyl a cycloalkyl radical containing 5 to 8 carbon a phenylalkyl group containing 1 or 2 carbon atoms in the alkyl a lower alkylthio or phenoxy or a phenylalkoxy group containing 1 or 2 carbon atoms in the alkoxy a halogen atom or aminopenicillanyl group or or and together represent the residue of a ring including or R and together represent an atom or a sulphur atom and 2 represents a or tin or a carbon atom when and together represent an oxygen or sulphur or an acid anhydride group wherein is of the general sents a haloge a radical containing 5 to 8 carbon a a phenylalkyl group cont 1 to 2 carbon atoms in the a lower lower alkylthio or a phenylalkoxy group containing 1 or 2 carbon atoms the alkoxy or a and and are the or different and each represents a halogen a tuted or or Ry and together represent the residue of a ring including or together represent an oxygen or sulphur represents a phosphorus or tungsten or an acid anhydride wherein is of the general wherein lower alkyl a cycloalkyl radical containing 5 to 8 carbon a or a phenylalkyl group containing 1 or 2 carbon in the alkyl a lower lower or a phenylalkoxy group containing 1 or 2 carbon atoms in the alkoxy and represents a sulphur according to 1 or lower groups to 6 carbon Process according to claim the phenyl groups moieties within the definitions of and Rg carry one or more halogen lower lower and groups Process according to claim wherein the group in the compounds of general formulae III and IV is an acid anhydride in which general formula wherein and are as hereinbefore defined and represents a aluminium or boron or is of general formula and are as hereinbefore defined and represents a germanium o tin or and represent an oxygen atom and represents a carbon and is on alkyl Process according to claim when is a is a l radical of the formula and are the same or different and each of them represents a or halogen or lower alkyl phenyl or alkyl grou containing 1 or 2 carbon atoms in the alkyl group containing 5 to carbon atoms or a or the groups and when not representing or being optionally substituted with one or more halogen lower lower alkoxy or di o Process according to claim wherein the radical is preferably a Process according to claim wherein reagents used for the protection of the carboxylic function of starting materials of general formula IV are those of general formulae VII VIII and of which the free bonds linked to the atoms by the symbols have been saturated by an anhydride preferably a halogen Process according to claim wherein the reagent is selected from the group of and Process according to claim wherein the containing compound is a compound of the IX X XI I X XVI 0 XVII or and are as hereinbefore defined excluding the possibility that any of the represents a or and separately each represent a hydrogen or a hydrocarbon group no aliphatic containing 1 to 8 carbon or and together with the nitrogen to which they are attached a or heterocyclic group which may contain a second he atom selected h the 18 carbon when is an group with a tertiary carbon atom to depicted nitrogen is hydrogen together i the nitrogen to which they are tached and carbonyl group a or group an or X in the and each a h no ic unsaturation containing 1 to 8 carbon represents a hydrogen atom or a hydrocarbon group with no aliphatic unsaturation containing 1 to 8 carbon atoms or a group represents an group containing 1 to 8 carbon Y represents an alkylene group containing 3 to 18 carbon atom at least 3 and not more than 5 carbon atoms between the nitrogen atom and the carbonyl group to which Y is attachedj and n is X or Process according to claim wherein the silicon compound of the general formulae IX to XVII is selected from the group of acetarnide trifluoroacetaxnide trimethylsilyi acetarnide ure trimethylsilyi Process according to claim wherein the silicon compound of the general formulae and XIX are selected from the group of i and e Process according to claim wherein the containing compound is or 1 Process according to claim wherein the amount of compound used is at least one and a half molecular equivalent per mole of penicillanic or at least one molecular equivalent per mole of penicillanic acid anhydride Process according to claim wherein the amount of compound used is at least 2 to 4 molecular equivalent per mole of penicillin Process according to claim wherein the anhydrous acid is an acid which is not or not to a substantial extent by the compound added to the reaction under the reaction conditions Process according to claim wherein the acid hydrogen hydrogen and concentrated sulphuric hydrogen perchloric periodic nitric chloric iodic selenic substituted acetic acids such as bromoacetic trichloroacetic or trifiuoroacetic substituted sulphonic acids such as acid and trifluoromethylsulphonic naphthalcnesulphonic oxalic picric and OH acids such as pentacyanocyclopentadien and and and in containing nitro carbonyl Process according to claim wherein the acid is hydrogen Process according to claim the acid is orated as such in the reaction or is combined with a base forming an acid addition salt Process according to claim wherein the base is selected from the group of cycloaliphatic or heterocyclic hexamethylonetotramine pyridine and and pyridine or substituted for one or more lower or or lowe mino groups such the 2 2 2 and and also or Process according to claim wherein the base is a substituted a substituted or a substituted Process accessing to claim wherein an excess of the base is employed in relation Process according to claim wherein the complex is formed in in the reaction mixture by initially protecting a penicillanic acid sulphoxide starting material in solution in the dry inert organic solvent by reaction with an acid Process according to claim wherein bases being soluble in the employed and having a p a between 4 and are Process according to claim wherein the of substances reaction in relation to each of acid sulphoxide employed to 4 moles of acid about to 1 to equivalents of protecting reagent to 1 at least 2 equivalents of compound 3 to 7 when an acid complex is to 10 moles of complex to about 4 to 2 equivalents of carboxylic protecting to 1 at least 2 of compound 3 to 7 additional quantity of the base itself for from 1 to 10 the quantity of additional base erably increasing in direct relationship with the amount of complex Process according to claim wherein the inert organic solvent used is dimethylacetamide dioxan glycol diethyl tetraethyleneglycol diethyl benzylcyanide butyl isoamylacetat diethyloxalate carbon methyl ethyl methyl or isobutyl or a such as 1 hylenechlorid and Process according to claim the dry organic inert solvent is Process according to claim wherein the ture employed during ring enlargement is between 50 and Process according to claim wherein the ture employed during ring enlargement is between 60 and 130 preferably between 70 and 110 Process according to claim wherein for each mole of penicillanic acid sulphoxide bcn ylpenicillin there is employed 1 to 4 moles of preferably hydrogen bromide or hydrogen to 15 moles of preferably the amount of base always exceeding that of and 2 to 4 moles of rimethylsilyl and the is carried out at a temperature of to in a dry inert organic preferably Process according to claim wherein for of peneillanic acid employed to 1 of acetyl bromide or phosphorus to 15 moles of the amount of exceeding that of the developing to 3 moles of derivatives whenever prepared by the process according to one of the preceding aminopenicillanic acid anhydrides Wherein the symbols R to R are the same or different and each represents a halogen or R and together represent an oxygen or sulphur represents a halogen atom or a lower lower haloalkyl or aryl is a aluminium or phosphorus is ium or tin and is a phosphorus or tungsten represents a group or a group or wherein X represents a chlorine or bromine 34 The mixed anhydride of phenoxymethylpenicillin sulphoxide and acetic 35 e mixed anhydride of benzylpeniciULn sulphoxide and acetic 36 The mixed anhydride of benzylpenicillin sulphoxide and propionic 37 The mixed anhydride of benzylprnicillin sulphoxide and benzoic 38 The mixed anhydride of phenoxymethylpenicillin sulphoxide and benzoic 39 The mixed anhydride phenoxymethylpenicillin sulphoxide insufficientOCRQuality
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3863771 | 1971-08-17 | ||
| GB5951671A GB1409415A (en) | 1971-08-17 | 1971-12-21 | Penicillin sulphoxides and their use in preparing delta3-7- substituted amino-descetoxy-cephalosporins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL40143A0 IL40143A0 (en) | 1972-10-29 |
| IL40143A true IL40143A (en) | 1976-03-31 |
Family
ID=26263869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL40143A IL40143A (en) | 1971-08-17 | 1972-08-16 | The preparation of cephalosporins from penicillin sulphoxides and new mixed anhydrides of penicillin sulphoxides |
Country Status (25)
| Country | Link |
|---|---|
| JP (1) | JPS5438117B2 (en) |
| AR (1) | AR193426A1 (en) |
| AT (1) | AT336181B (en) |
| BE (1) | BE787618A (en) |
| CA (1) | CA1014146A (en) |
| CH (1) | CH576982A5 (en) |
| CS (1) | CS197212B2 (en) |
| DD (1) | DD100263A5 (en) |
| DE (2) | DE2240224C3 (en) |
| DK (1) | DK142174B (en) |
| ES (1) | ES405883A1 (en) |
| FI (1) | FI58643C (en) |
| FR (1) | FR2150785B1 (en) |
| GB (1) | GB1409415A (en) |
| HU (1) | HU169534B (en) |
| IE (1) | IE36638B1 (en) |
| IL (1) | IL40143A (en) |
| LU (1) | LU65904A1 (en) |
| NL (1) | NL177597C (en) |
| NO (2) | NO144153C (en) |
| PH (2) | PH13845A (en) |
| RO (1) | RO63401A (en) |
| SE (1) | SE404927B (en) |
| SU (1) | SU500754A3 (en) |
| YU (1) | YU39899B (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2222094A1 (en) * | 1972-05-05 | 1973-11-15 | Hoechst Ag | PROCESS FOR THE PRODUCTION OF AMINOACETIDINONES |
| GB1472866A (en) * | 1974-06-12 | 1977-05-11 | Farmaceutici Italia | Cephalosporins and intermediates therefor |
| GB1467355A (en) * | 1974-08-07 | 1977-03-16 | Lepetit Spa | Preparation of 6-aminopenicillanic acid 7-aminocephalospo ranic acid and derivatives thereof |
| ES431585A1 (en) * | 1974-11-02 | 1976-11-16 | Gema Sa | Process for the conversion of 6-aminopenicillanic acid (6-APA) in 7-aminodesacetoxycephalosporanic acid (7-ADCA) |
| PL94023B1 (en) * | 1974-12-18 | 1977-07-30 | Politechnika Gdanska | |
| GB1472864A (en) * | 1975-04-05 | 1977-05-11 | Farmaceutici Italia | Method of preparing cephalosporins |
| US4008231A (en) * | 1975-09-15 | 1977-02-15 | Eli Lilly And Company | Preparation of 3-methoxymethylcephalosporins |
| IT1063088B (en) * | 1976-06-01 | 1985-02-11 | Dobfar Spa | AZETIDINONIC DERIVATIVES AND PROCEDURE FOR THE PREPARATION OF CEPHALOSPORINE |
| US4426520A (en) | 1978-04-03 | 1984-01-17 | Bristol-Myers Company | 3-Carbamoyloxy-cepham-4-carboxylic acid derivatives |
| US4518773A (en) * | 1978-04-03 | 1985-05-21 | Bristol-Myers Company | "3-Carbamoyloxy cephalosporins" |
| US4310459A (en) * | 1978-04-03 | 1982-01-12 | Bristol-Myers Company | Process for producing carbamoyl substituted penams and carbamoyl substituted cephams from penicillin sulfoxide esters |
| US4322347A (en) | 1978-04-03 | 1982-03-30 | Bristol-Myers Company | 2-Carbamoyloxymethyl-penicillin derivatives |
| IT1124802B (en) * | 1979-10-29 | 1986-05-14 | Dobfar Spa | BORONATED DERIVATIVES OF 6-PENICILLANIC ACID AND PROCEDURE FOR THEIR PREPARATION |
| US4374982A (en) | 1979-11-07 | 1983-02-22 | Bristol-Myers Company | Cepham compounds |
| JPS5716006A (en) * | 1980-07-03 | 1982-01-27 | Mitsui Toatsu Chem Inc | Suspension polymerization of vinyl chloride |
-
0
- BE BE787618D patent/BE787618A/en not_active IP Right Cessation
-
1971
- 1971-12-21 GB GB5951671A patent/GB1409415A/en not_active Expired
-
1972
- 1972-08-03 SU SU1817032A patent/SU500754A3/en active
- 1972-08-15 IE IE1136/72A patent/IE36638B1/en unknown
- 1972-08-15 PH PH13802A patent/PH13845A/en unknown
- 1972-08-16 CH CH1216172A patent/CH576982A5/xx not_active IP Right Cessation
- 1972-08-16 IL IL40143A patent/IL40143A/en unknown
- 1972-08-16 DD DD165088A patent/DD100263A5/xx unknown
- 1972-08-16 FI FI2271/72A patent/FI58643C/en active
- 1972-08-16 CA CA149,545A patent/CA1014146A/en not_active Expired
- 1972-08-16 ES ES405883A patent/ES405883A1/en not_active Expired
- 1972-08-16 FR FR7229365A patent/FR2150785B1/fr not_active Expired
- 1972-08-16 DE DE2240224A patent/DE2240224C3/en not_active Expired
- 1972-08-16 AR AR243595A patent/AR193426A1/en active
- 1972-08-16 NO NO2942/72A patent/NO144153C/en unknown
- 1972-08-16 LU LU65904A patent/LU65904A1/xx unknown
- 1972-08-16 DK DK406072AA patent/DK142174B/en not_active IP Right Cessation
- 1972-08-16 YU YU2100/72A patent/YU39899B/en unknown
- 1972-08-16 SE SE7210625A patent/SE404927B/en unknown
- 1972-08-16 AT AT704072A patent/AT336181B/en not_active IP Right Cessation
- 1972-08-16 RO RO7200071975A patent/RO63401A/en unknown
- 1972-08-16 HU HUGI178A patent/HU169534B/hu unknown
- 1972-08-16 DE DE2264648*A patent/DE2264648A1/en active Pending
- 1972-08-16 JP JP8204972A patent/JPS5438117B2/ja not_active Expired
- 1972-08-16 CS CS725688A patent/CS197212B2/en unknown
- 1972-08-17 NL NLAANVRAGE7211213,A patent/NL177597C/en not_active IP Right Cessation
-
1973
- 1973-05-30 NO NO2262/73A patent/NO144152C/en unknown
-
1977
- 1977-12-06 PH PH20519A patent/PH15675A/en unknown
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