CS199662B2 - Process forpreparing 5,6-dehydropenicilanates - Google Patents
Process forpreparing 5,6-dehydropenicilanates Download PDFInfo
- Publication number
- CS199662B2 CS199662B2 CS771196A CS119677A CS199662B2 CS 199662 B2 CS199662 B2 CS 199662B2 CS 771196 A CS771196 A CS 771196A CS 119677 A CS119677 A CS 119677A CS 199662 B2 CS199662 B2 CS 199662B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- formula
- carried out
- compound
- process according
- cyclization reaction
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 41
- 238000002360 preparation method Methods 0.000 claims abstract description 27
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 56
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- 239000007858 starting material Substances 0.000 claims description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 150000007514 bases Chemical class 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000012298 atmosphere Substances 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000007848 Bronsted acid Substances 0.000 claims description 3
- 239000002841 Lewis acid Substances 0.000 claims description 3
- 239000003341 Bronsted base Substances 0.000 claims description 2
- 239000002879 Lewis base Substances 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 1
- 238000009283 thermal hydrolysis Methods 0.000 claims 1
- 230000001678 irradiating effect Effects 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 150000003952 β-lactams Chemical class 0.000 description 12
- KDERTRJFUUMBKU-UHFFFAOYSA-N 4-sulfanylideneazetidin-2-one Chemical class O=C1CC(=S)N1 KDERTRJFUUMBKU-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 150000002148 esters Chemical class 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 239000007787 solid Substances 0.000 description 10
- -1 bicyclic compound Chemical class 0.000 description 9
- 238000004809 thin layer chromatography Methods 0.000 description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical compound NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 150000002960 penicillins Chemical class 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229930182555 Penicillin Natural products 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003849 aromatic solvent Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000008034 disappearance Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000002798 spectrophotometry method Methods 0.000 description 3
- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 2
- PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 101100073357 Streptomyces halstedii sch2 gene Proteins 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 150000003951 lactams Chemical group 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 238000006552 photochemical reaction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FADJIMDKDQYNCG-UHFFFAOYSA-N 1h-azet-2-one Chemical group O=C1NC=C1 FADJIMDKDQYNCG-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 229930186147 Cephalosporin Chemical class 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical class 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 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- YIMOYMPVLAASMX-UHFFFAOYSA-N benzyl 3-methyl-2-[2-oxo-3-[(2-phenoxyacetyl)amino]-4-sulfanylideneazetidin-1-yl]but-2-enoate Chemical compound C=1C=CC=CC=1COC(=O)C(=C(C)C)N(C1=S)C(=O)C1NC(=O)COC1=CC=CC=C1 YIMOYMPVLAASMX-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000003460 beta-lactamyl group Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000006364 carbonyl oxy methylene group Chemical group [H]C([H])([*:2])OC([*:1])=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- MEJXDFQUPGDBSZ-UHFFFAOYSA-N methyl 2-(3-acetamido-2-oxo-4-sulfanylideneazetidin-1-yl)-3-methylbut-2-enoate Chemical compound COC(=O)C(=C(C)C)N1C(=O)C(NC(C)=O)C1=S MEJXDFQUPGDBSZ-UHFFFAOYSA-N 0.000 description 1
- IUKPKIUOQZVYOI-UHFFFAOYSA-N methyl 2-(3-acetamido-2-oxo-4-sulfanylideneazetidin-1-yl)-3-methylbut-3-enoate Chemical compound COC(=O)C(C(C)=C)N1C(=O)C(NC(C)=O)C1=S IUKPKIUOQZVYOI-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 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 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
- C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/10—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Polyamides (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20457/76A IT1058858B (it) | 1976-02-23 | 1976-02-23 | 5.6 deidropenicilline processo per la loro preparazione e intermdi ottenibili in detto processo |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199662B2 true CS199662B2 (en) | 1980-07-31 |
Family
ID=11167232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS771196A CS199662B2 (en) | 1976-02-23 | 1977-02-23 | Process forpreparing 5,6-dehydropenicilanates |
Country Status (21)
| Country | Link |
|---|---|
| US (3) | US4133807A (it) |
| JP (1) | JPS52102267A (it) |
| AU (1) | AU514741B2 (it) |
| BE (1) | BE851751A (it) |
| CA (1) | CA1090290A (it) |
| CH (1) | CH631180A5 (it) |
| CS (1) | CS199662B2 (it) |
| DD (1) | DD128359A5 (it) |
| DE (1) | DE2707404C3 (it) |
| DK (2) | DK77177A (it) |
| FR (1) | FR2341582A1 (it) |
| GB (2) | GB1572139A (it) |
| HU (2) | HU183632B (it) |
| IT (1) | IT1058858B (it) |
| LU (1) | LU76816A1 (it) |
| NL (1) | NL171159C (it) |
| NO (2) | NO770568L (it) |
| SE (1) | SE438506B (it) |
| SU (3) | SU683626A3 (it) |
| YU (3) | YU49377A (it) |
| ZA (1) | ZA77890B (it) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1058858B (it) * | 1976-02-23 | 1982-05-10 | Snam Progetti | 5.6 deidropenicilline processo per la loro preparazione e intermdi ottenibili in detto processo |
| JPS5398951A (en) * | 1977-02-08 | 1978-08-29 | Shionogi & Co Ltd | Azetidinone derivatives and process for their preparation |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4174318A (en) * | 1970-11-03 | 1979-11-13 | Glaxo Laboratories Ltd. | Alkylative cleavage of azetidinone disulfides |
| GB1368234A (en) | 1970-11-03 | 1974-09-25 | Glaxo Lab Ltd | Thiosubstituted szetidinones and other antibiotic precursors |
| BE791161A (fr) * | 1972-01-03 | 1973-05-09 | Beecham Group Ltd | Procede pour la preparation d'analogues des cephalosporines |
| BE791159A (fr) | 1972-01-03 | 1973-05-09 | Beecham Group Ltd | Procede pour la preparation de cephemes |
| DE2204105A1 (de) | 1972-01-28 | 1973-08-02 | Beecham Group Ltd | Seco-penicilline und verfahren zu ihrer herstellung |
| US4089963A (en) * | 1972-03-13 | 1978-05-16 | Astra Pharmaceutical Products, Inc. | Esters of amidinopenicillanic acids, pharmaceutical preparations and method for treating infectious diseases |
| US4219462A (en) * | 1974-07-29 | 1980-08-26 | Merck & Co., Inc. | 6-Methyl penicillins |
| IT1058858B (it) * | 1976-02-23 | 1982-05-10 | Snam Progetti | 5.6 deidropenicilline processo per la loro preparazione e intermdi ottenibili in detto processo |
| US4136096A (en) * | 1977-02-25 | 1979-01-23 | Pfizer Inc. | 6-amino-2,2-dimethyl-3-(5-tetrazolyl)penam process and intermediates therefor |
| US4168314A (en) * | 1977-11-17 | 1979-09-18 | Merck & Co., Inc. | 6-(1'-Hydroxyethyl)-2-aminoethylthio-pen-2-em-3-carboxylic acid |
| US4160091A (en) * | 1977-11-21 | 1979-07-03 | Eli Lilly And Company | Process for preparation of 3-halo-3-methylcephams |
-
1976
- 1976-02-23 IT IT20457/76A patent/IT1058858B/it active
-
1977
- 1977-02-15 ZA ZA770890A patent/ZA77890B/xx unknown
- 1977-02-17 US US05/769,527 patent/US4133807A/en not_active Expired - Lifetime
- 1977-02-18 AU AU22428/77A patent/AU514741B2/en not_active Ceased
- 1977-02-21 NO NO770568A patent/NO770568L/no unknown
- 1977-02-21 SE SE7701907A patent/SE438506B/xx not_active IP Right Cessation
- 1977-02-21 DE DE2707404A patent/DE2707404C3/de not_active Expired
- 1977-02-22 LU LU76816A patent/LU76816A1/xx unknown
- 1977-02-22 GB GB7500/77A patent/GB1572139A/en not_active Expired
- 1977-02-22 DD DD7700197507A patent/DD128359A5/xx unknown
- 1977-02-22 HU HU813040A patent/HU183632B/hu unknown
- 1977-02-22 FR FR7705128A patent/FR2341582A1/fr active Granted
- 1977-02-22 CH CH221077A patent/CH631180A5/it not_active IP Right Cessation
- 1977-02-22 HU HU77SA3016A patent/HU179786B/hu unknown
- 1977-02-22 DK DK77177A patent/DK77177A/da not_active Application Discontinuation
- 1977-02-22 YU YU00493/77A patent/YU49377A/xx unknown
- 1977-02-22 GB GB1747/79A patent/GB1572140A/en not_active Expired
- 1977-02-22 CA CA272,330A patent/CA1090290A/en not_active Expired
- 1977-02-23 NL NLAANVRAGE7701962,A patent/NL171159C/xx not_active IP Right Cessation
- 1977-02-23 SU SU772455688A patent/SU683626A3/ru active
- 1977-02-23 BE BE175195A patent/BE851751A/xx not_active IP Right Cessation
- 1977-02-23 JP JP1825877A patent/JPS52102267A/ja active Pending
- 1977-02-23 CS CS771196A patent/CS199662B2/cs unknown
- 1977-11-03 NO NO773766A patent/NO773766L/no unknown
-
1978
- 1978-02-13 SU SU782578098A patent/SU721004A3/ru active
- 1978-02-13 SU SU782580402A patent/SU712024A3/ru active
-
1979
- 1979-07-19 US US06/058,945 patent/US4288366A/en not_active Expired - Lifetime
-
1981
- 1981-02-19 US US06/236,029 patent/US4353825A/en not_active Expired - Fee Related
- 1981-12-16 DK DK558781A patent/DK558781A/da not_active Application Discontinuation
-
1982
- 1982-09-27 YU YU02149/82A patent/YU214982A/xx unknown
- 1982-09-27 YU YU02148/82A patent/YU214882A/xx unknown
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