SE438331B - Azetidinylbutenoatforeningar som mellanprodukter for framstellning av 3-substituerade cefalosporinderivat - Google Patents

Azetidinylbutenoatforeningar som mellanprodukter for framstellning av 3-substituerade cefalosporinderivat

Info

Publication number: SE438331B
Authority: SE; Sweden
Prior art keywords: group; preparation; nitrobenzyl; mixture; formula
Prior art date: 1974-12-24

Application number

SE7810962A

Other languages

English (en)

Swedish (sv)

Other versions

SE7810962L (sv

Inventor

S P Kukolja

Original Assignee

Lilly Co Eli

Priority date (The priority date 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 date listed.)

1974-12-24

Filing date

1978-10-20

Publication date

1985-04-15

1978-10-20 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1978-10-20 Publication of SE7810962L publication Critical patent/SE7810962L/xx

1985-04-15 Publication of SE438331B publication Critical patent/SE438331B/sv

Links

238000002360 preparation method Methods 0.000 title claims description 16
239000000543 intermediate Substances 0.000 title description 5
239000000126 substance Substances 0.000 title description 4
XWDRXSGGVYUPHM-UHFFFAOYSA-N 2-(azetidin-1-yl)but-2-enoic acid Chemical compound CC=C(C(O)=O)N1CCC1 XWDRXSGGVYUPHM-UHFFFAOYSA-N 0.000 title 1
HOKIDJSKDBPKTQ-UHFFFAOYSA-N 3-(acetyloxymethyl)-7-[(5-amino-5-carboxypentanoyl)amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C(NC(=O)CCCC(N)C(O)=O)C12 HOKIDJSKDBPKTQ-UHFFFAOYSA-N 0.000 title 1
-1 4-nitrobenzyloxy Chemical group 0.000 claims description 26
150000001875 compounds Chemical class 0.000 claims description 20
239000000047 product Substances 0.000 claims description 19
125000006239 protecting group Chemical group 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
150000001782 cephems Chemical class 0.000 claims description 4
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000002843 carboxylic acid group Chemical group 0.000 claims description 2
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
239000013067 intermediate product Substances 0.000 claims 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
239000000203 mixture Substances 0.000 description 23
239000000243 solution Substances 0.000 description 18
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 14
238000010992 reflux Methods 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 8
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
238000005481 NMR spectroscopy Methods 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
239000012267 brine Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical class ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
239000000499 gel Substances 0.000 description 4
238000000034 method Methods 0.000 description 4
150000003462 sulfoxides Chemical class 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
229930182555 Penicillin Natural products 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229940049954 penicillin Drugs 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
FCZNNHHXCFARDY-WQRUCBPWSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical class N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)CC1=CC=CC=C1 FCZNNHHXCFARDY-WQRUCBPWSA-N 0.000 description 2
WIMGCNFCFYONPX-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-[2-chlorosulfinyl-4-oxo-3-[(2-phenoxyacetyl)amino]azetidin-1-yl]-3-methylbut-3-enoate Chemical compound C=1C=C([N+]([O-])=O)C=CC=1COC(=O)C(C(=C)C)N(C1=O)C(S(Cl)=O)C1NC(=O)COC1=CC=CC=C1 WIMGCNFCFYONPX-UHFFFAOYSA-N 0.000 description 2
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
125000004442 acylamino group Chemical group 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000006244 carboxylic acid protecting group Chemical group 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
LADXFZKPGFVWEF-PXTXNPLLSA-N (4-nitrophenyl)methyl (5r)-6-acetamido-3,3-dimethyl-4,7-dioxo-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound N1([C@H](S(C2(C)C)=O)C(C1=O)NC(=O)C)C2C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 LADXFZKPGFVWEF-PXTXNPLLSA-N 0.000 description 1
BJYNEWYPMMYDKH-BDPMCISCSA-N (4-nitrophenyl)methyl (6r)-3-chloro-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1=CC([N+](=O)[O-])=CC=C1COC(=O)C1=C(Cl)CS[C@H]2N1C(=O)C2NC(=O)COC1=CC=CC=C1 BJYNEWYPMMYDKH-BDPMCISCSA-N 0.000 description 1
WCRKZNRTRADCRA-QRDQUSRPSA-N (4-nitrophenyl)methyl (6r)-3-hydroxy-5,8-dioxo-7-[(2-phenoxyacetyl)amino]-5$l^{4}-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2=O)O)C(=O)OCC=1C=CC(=CC=1)[N+]([O-])=O)NC(=O)COC1=CC=CC=C1 WCRKZNRTRADCRA-QRDQUSRPSA-N 0.000 description 1
BFSXROKQPGUERI-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-(3-acetamido-2-chlorosulfinyl-4-oxoazetidin-1-yl)-3-methylbut-3-enoate Chemical compound O=C1C(NC(=O)C)C(S(Cl)=O)N1C(C(C)=C)C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 BFSXROKQPGUERI-UHFFFAOYSA-N 0.000 description 1
UCBAURXLMISMMB-AXRAFADPSA-N (5R)-2-benzhydryl-3,3-dimethyl-4,7-dioxo-6-[(2-phenoxyacetyl)amino]-4lambda4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound CC1(C(N2[C@H](S1=O)C(C2=O)NC(=O)COC3=CC=CC=C3)(C(C4=CC=CC=C4)C5=CC=CC=C5)C(=O)O)C UCBAURXLMISMMB-AXRAFADPSA-N 0.000 description 1
ARXCQCNOQIGXDG-CBQMELLWSA-N (6R)-3-hydroxy-4-[(4-nitrophenyl)methyl]-5,8-dioxo-7-[(2-phenoxyacetyl)amino]-5lambda4-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1=CC=C(C=C1)OCC(=O)NC2[C@@H]3N(C2=O)C(=C(C(S3=O)CC4=CC=C(C=C4)[N+](=O)[O-])O)C(=O)O ARXCQCNOQIGXDG-CBQMELLWSA-N 0.000 description 1
MDTNTKLGRUURFT-RXMQYKEDSA-N (6r)-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=C(Cl)CS[C@@H]2CC(=O)N12 MDTNTKLGRUURFT-RXMQYKEDSA-N 0.000 description 1
ZUBXPSDFPQTKQN-ZCFIWIBFSA-N (6r)-3-hydroxy-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical class S1CC(O)=CN2C(=O)C[C@H]21 ZUBXPSDFPQTKQN-ZCFIWIBFSA-N 0.000 description 1
WDRFYIPWHMGQPN-UHFFFAOYSA-N 2-chloroisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Cl)C(=O)C2=C1 WDRFYIPWHMGQPN-UHFFFAOYSA-N 0.000 description 1
KDXFMMHNGFNJFA-UHFFFAOYSA-N 4-oxoazetidine-2-sulfinyl chloride Chemical compound ClS(=O)C1CC(=O)N1 KDXFMMHNGFNJFA-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
229930195708 Penicillin V Natural products 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
125000002393 azetidinyl group Chemical group 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000006260 foam Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
GWLOGZRVYXAHRE-UHFFFAOYSA-N n,4-dimethylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(C)C=C1 GWLOGZRVYXAHRE-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229940056367 penicillin v Drugs 0.000 description 1
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 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
239000012264 purified product Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- 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
- C07D205/06—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
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Cephalosporin Compounds (AREA)

SE7810962A 1974-12-24 1978-10-20 Azetidinylbutenoatforeningar som mellanprodukter for framstellning av 3-substituerade cefalosporinderivat SE438331B (sv)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US53627374A	1974-12-24	1974-12-24
US63273275A	1975-11-19	1975-11-19

Publications (2)

Publication Number	Publication Date
SE7810962L SE7810962L (sv)	1978-10-20
SE438331B true SE438331B (sv)	1985-04-15

Family

ID=27065078

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7810962A SE438331B (sv)	1974-12-24	1978-10-20	Azetidinylbutenoatforeningar som mellanprodukter for framstellning av 3-substituerade cefalosporinderivat

Country Status (14)

Country	Link
AR (2)	AR213084A1 (es)
CS (1)	CS192522B2 (es)
DD (1)	DD123601A5 (es)
DK (1)	DK585775A (es)
ES (1)	ES443828A1 (es)
GR (1)	GR58604B (es)
IE (1)	IE42189B1 (es)
IL (1)	IL48564A (es)
PH (1)	PH20183A (es)
PL (1)	PL108419B1 (es)
RO (1)	RO68210A (es)
SE (1)	SE438331B (es)
SU (1)	SU644383A3 (es)
YU (1)	YU324775A (es)

1975
- 1975-11-27 GR GR49472A patent/GR58604B/el unknown
- 1975-11-28 IE IE2595/75A patent/IE42189B1/en unknown
- 1975-11-28 IL IL48564A patent/IL48564A/xx unknown
- 1975-12-17 DD DD190223A patent/DD123601A5/xx unknown
- 1975-12-19 YU YU03247/75A patent/YU324775A/xx unknown
- 1975-12-22 DK DK585775A patent/DK585775A/da unknown
- 1975-12-23 AR AR261749A patent/AR213084A1/es active
- 1975-12-23 SU SU752301603A patent/SU644383A3/ru active
- 1975-12-23 ES ES443828A patent/ES443828A1/es not_active Expired
- 1975-12-23 CS CS758834A patent/CS192522B2/cs unknown
- 1975-12-23 PL PL1975185933A patent/PL108419B1/pl unknown
- 1975-12-24 RO RO7584302A patent/RO68210A/ro unknown
1977
- 1977-12-09 AR AR270300A patent/AR229151A1/es active
1978
- 1978-10-20 SE SE7810962A patent/SE438331B/sv not_active IP Right Cessation
1979
- 1979-07-05 PH PH22740A patent/PH20183A/en unknown

Also Published As

Publication number	Publication date
PH20183A (en)	1986-10-16
RO68210A (ro)	1981-08-30
DD123601A5 (es)	1977-01-05
AR213084A1 (es)	1978-12-15
GR58604B (en)	1977-11-10
CS192522B2 (en)	1979-08-31
IE42189B1 (en)	1980-06-18
IE42189L (en)	1976-06-24
AR229151A1 (es)	1983-06-30
PL108419B1 (en)	1980-04-30
IL48564A0 (en)	1976-01-30
SU644383A3 (ru)	1979-01-25
YU324775A (en)	1982-10-31
DK585775A (da)	1976-06-25
IL48564A (en)	1979-09-30
ES443828A1 (es)	1977-04-16
SE7810962L (sv)	1978-10-20

Publication	Publication Date	Title
CA1136132A (en)	1982-11-23	Cyclization to form cephem ring and intermediates therefor
CA1080713A (en)	1980-07-01	Process for the manufacture of 3-substituted-hydroxy-crotonic and isocrotonic acid derivatives
SE449489B (sv)	1987-05-04	Beta-laktam foreningar med antibakteriell och beta-laktam inhiberande aktivitet
US4081440A (en)	1978-03-28	Sulfinyl halides and their preparation from penicillin sulfoxides
US4115643A (en)	1978-09-19	Process for 3-chloro cephalosporins
SE405857B (sv)	1979-01-08	Forfarande for substituerande av en grupp i 6-resp 7-stellning hos en penicillansyraforening eller cefalosporansyraforening
CA1099715A (en)	1981-04-21	1-oxadethiacepham compounds
IE43845B1 (en)	1981-06-17	4-thia-1-azabicyclo/4.2.0/oct-2-ene derivatives
SU546282A3 (ru)	1977-02-05	Способ получени 7- -амино-7 метокси-цефалоспориновых эфиров
CA1042873A (en)	1978-11-21	Azetidine derivatives
KR840000865B1 (ko)	1984-06-20	β-락탐-함유 항균제의 제조방법
US4093800A (en)	1978-06-06	Process for preparing cepham compounds
US4713450A (en)	1987-12-15	2-thiacephems and (5R) penems derivatives
US4007202A (en)	1977-02-08	Azetidine derivatives
SE438331B (sv)	1985-04-15	Azetidinylbutenoatforeningar som mellanprodukter for framstellning av 3-substituerade cefalosporinderivat
US4057540A (en)	1977-11-08	4-Chloroazetidinone-1-(2',3'-dichloroisopropyl) acetates and process for preparing same
US4647558A (en)	1987-03-03	Antibacterial agents, their preparation and use
CH636617A5 (en)	1983-06-15	Process for preparing cephalosporin analogues
US4534898A (en)	1985-08-13	1-Oxa-1-dethia-cephalosporin derivatives
US4103086A (en)	1978-07-25	8-Oxo-4-thia-1-azabicyclo (4.2.0)-oct-2-ene derivatives
US3941779A (en)	1976-03-02	Method for producing 2-(substituted thio)-3-cephem derivatives
DE2429166A1 (de)	1975-01-09	Verfahren zur selektiven spaltung der amidsaeurefunktion eines 7-(amidsaeure)cephalosporins
US4960880A (en)	1990-10-02	Alkenylsilylazetidinone intermediates for carbapenems
US4362880A (en)	1982-12-07	Chemical process
FI71562C (fi)	1987-01-19	Foerfarande foer framstaellning av 6- - substituerade penicillansyraderivat och saosom mellanprodukter anvaendbara 6-perfluoralkylsulfonyloxipenicillansyraderivat.

Legal Events

Date	Code	Title	Description
1995-01-31	NAL	Patent in force	Ref document number: 7810962-6 Format of ref document f/p: F
1996-03-04	NUG	Patent has lapsed	Ref document number: 7810962-6 Format of ref document f/p: F

Date

Code

Title

Description

1995-01-31

NAL

Patent in force

Ref document number: 7810962-6

Format of ref document f/p: F

1996-03-04

NUG

Patent has lapsed