SE458684B - Foerfarande foer framstaellning av azetidin-2-oner vilka anvaends som mellanprodukter foer framstaellning av penemer - Google Patents
Foerfarande foer framstaellning av azetidin-2-oner vilka anvaends som mellanprodukter foer framstaellning av penemerInfo
- Publication number
- SE458684B SE458684B SE8207092A SE8207092A SE458684B SE 458684 B SE458684 B SE 458684B SE 8207092 A SE8207092 A SE 8207092A SE 8207092 A SE8207092 A SE 8207092A SE 458684 B SE458684 B SE 458684B
- Authority
- SE
- Sweden
- Prior art keywords
- group
- tert
- butylsilyl
- formula
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000000543 intermediate Substances 0.000 title description 2
- HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 13
- -1 hydroxyethyl group Chemical class 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 7
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 claims description 4
- 238000005949 ozonolysis reaction Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[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 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical group CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 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 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- RCCPEORTSYDPMB-UHFFFAOYSA-N hydroxy benzenecarboximidothioate Chemical compound OSC(=N)C1=CC=CC=C1 RCCPEORTSYDPMB-UHFFFAOYSA-N 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000002217 penem group Chemical group 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003462 sulfoxides Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 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
- C07D499/88—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/568—Four-membered rings
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
458 684 O H Ri Sflßoec III fiNw/ï coon vari Rl, R och PG definieras som ovan, med fosfortribromid, och ozonolysering av den resulterande föreningen med formel IV R s i om Iv O N / COOR vari Rl, R och PG definieras som ovan, i ett lösningsmedel vid en temperatur av från -80°C till -50°C. 6-substituenten kan antingen uppvisa alfa- eller beta-oriente- ring, varvid alfa-orientering är föredragen. När Rl är lägre hydroxíalkyl kan kolatomen som bär hydroxifunktionen såväl vara R som även S men är emellertid företrädesvis R.
Kolatomen i ställning 5 uppvisar endast R-konfigurationen.
Föreningarna med formeln (IVa) framställes sålunda enligt föreliggande uppfinning enligt följande reaktionsschema i vilket PG är en dimetyl-tert.butylsílyl-, difenyl-tert.butyl- silyl- eller trimetylsilyl-grupp. 458 684 458 684 Förfarandet enligt uppfinningen omfattar skyddandet av den fria hydroxigruppen hos förening (II) (framställd såsom besk- rives i GB-PS 2 043 639) med en skyddsgrupp, reduktion av sulfoxidfunktionen hos den erhållna föreningen (III), ozonolys av båda kol-kol-dubbelbindníngarna i den erhållna föreningen (IV).
Reduktionen kan genomföras under användning av fosfortribromíd vid en temperatur av -40 till -20°C i ett lösningsmedel, såsom vattenfri dimetylformamid. Ozonolysen kan åstadkommas vid en temperatur av -80 till -50°C i ett lösningsmedel, såsom dietyleter, metanol eller - företrädesvis - diklormetan.
Tvà kännetecken hos föreliggande uppfinning fordrar en ytter- ligare kommentar. Kolatomen i ställning 5 vars R-konfiguration "den enda väsentliga stereokemiska fordran för antibiotisk verkan" (H.R. Pfaendler, J. Gosteli och R.B. Woodward, J.Am.Chem.Soc. l0l, 1979, är 6306) behåller sin konfiguration fràn föreningen (II) ända fram till den önskade slutförening- en. Kol-svavelbindningen förstöres icke i något steg.
Föreningar med den allmänna formeln IVa som erhålles enligt föreliggande uppfinning är lämpliga mellanprodukter vid fram- ställning av penemer som besitter anti-bakteriell aktivitet som beskrives i GB-PS 2 043 639.
Uppfinníngen àskàdliggöres närmare medelst följande exempel varvid följande förkortningar användes, PNB för p-nitrobensyl, TBDPS för tert.-butyldifenylsilyl och TBDMS för tert.-butyldi- metylsilyl.
Exempel l 4(R)-(I-cert_-butyldimetylsílyloximetyl-vinyltio)-3(S)-/l(R)-p- -nitrobensyloxikarbonyloxietyl/-l-(l-metoxikarbonyl-2 -metyl-l- -propenyl)-azetidin-2-on-S-oxid 458 684 5 / 5\/\ U5\/\ i: /_C , H OH , O~S1 C H 1 r r e., f »x f ny L___. 04* /,__\ 04?""ï>=x< QCH3 coocfl 3 coocna 1,9 g 4(R)-(l-hydroximetylvinyltio)~3(S)~/l(R)-p-nitrobensyl- oxikarbonyloxietyl/-l-(1-metoxikarbonyl-2-metyl-l-propenyl)- § -azetídin-2-on-S-oxid löstes i 2 ml díklormetan. 0,7 ml tri- É etylamin, 640 mg tert.-butyldimetylsilylklorid och 20 mg di- metylaminopyridin tillsattes under kväveatmosfär. Efter omrö- ríng över natten vid rumstemperatur tvättades lösningen med vatten och ammoníumkloridlösning och lösníngsmedlet avdunsta- des. Aterstoden kromatograferades på silikagel med cyklo- hexan/etylacetat (l;l), varvid man erhöll 0,83 g av föreningen i rubriken.
PMR (CDC13) : âíppm) 0,07 (s, 6H, si(g§3)2), 0,88 (s, 9HéH SiC(§§3)3), 1,41 (d, J=6,5H2, 3H, §§3CH), 2,14 (s, 3H, = -~3), 2,30 (S, an, =/933), 3,75 (5, sn, coogg3), 3,7-3,9 (m, ln, 1 §:§), 4,48 (brett s, ZH, §§2OSi), 5,25 (s, 2H, §§2Ph), 5,1-5,2 f» (m, za, g¿§, cH3gg), 5,85 (brett S, ln, =/3), 5,98 (brett S, ln, =/5), 7,4-8,4 (m, 4n, ggmoz), IR (cH2c12): 0 (cm"l)= 1730 c=o omättad, ester, 1755 c=o ocoo, 17so c=o B-lakfam.
Masspektrum (FD): m/e 624.
Exemgel 2 4(R)-(l-tert.-butyldimetylsilyloxímetyl-vinyltio)-3(S)-/l1R)- -pnitrobensyloxikarbonyloxietyl/-1-(1-metoxikarbonyl-2-metyl- -l-propenyl)-azetidín-2-on 0 OCOZPNB 1 _oco2PNB ÄH g mm S L-¶/ \\í//,\\0/ 1 I OTBDMS i ___----+> d%____Ü>F=<Ä 047 .:É== CQQCH3 CÛOCHS TBDMS betyder tert.-butyldimetylsilyl 458 684 En lösning av 0,8 g 4(R)-(1-tert_-butyldimetylsilyloximetyl- vinyltio)-3(S)-/l(R)-p-nítrobensyloxikarbonyloxietyl/-l-(l- -metoxíkanbonyl-2-metyl-l-propenyl)-azetidin-2-on-S-oxid i 30 ml vattenfri dimetylformamid kyldes till -20°C och 0,25 ml fosfortribromid tillsattes. Efter 15 minuter utspäddes bland- ningen med etylacetat, tvättades två gånger med mättad NaHCO3-lösning och därefter med vatten och torkades (Na2SO4).
Avdunstning av lösningsmedlet gav 0,7 g av föreningen i rubriken.
PMR (CDCI3) 6 (ppm)= o,o5 (S, sn, si(gg3)2), o,9o (S, 9n, sic(gn3>3>, 1,48 (d, J=e,5nz, an, _c¿i3cn>, 2,01 (s, an, =/-C-*-1a>, 2,24 (s, an, = 953), a,a5 (aa, J=z,5, 7,onz, in, BH, coogg3), 4,08 (t, J=2,onz, zn, gnzrm, s,2-5,a5 (m, an, cn n-e), 3,73 (s, ggzosi), 5,26 (s, zn, 3gn, n-s, =/5>, 5,56 (a, J=2,o, in, =/5), 7,4-s,4 (m, 4n, gnoz).
Exemgel 3 4(R)-tert.-butyldimetylsilyloxiacetyltio-3(S)-/l(R)-p- -nítrobensyloxikarbonyloxietyl/-l-metoxioxaloylazetidin- -2-on CCO PNB OCO PNB 2% 2 gsvm ons ÅLl/Sñrorsnns °47-__M\\_~/ o47r__4ñ)==0 V Coofšf coocnå 0,7 g 4(R)-(l-tert.-butyldimetylsilyloximetylvínyltio)-3(S)- -/l(R)-p-nitrobensyloxikarbonyloxíetyl/-l-(l-metoxikarbonyl-2- -metyl-l-propenyl)-azetidin-2~on löstes i 30 ml diklormetan och l0 ml metanol. Lösningen kyldes till -78°C och ozon i syre blåstes genom lösningen tills en blágärníng uppträdde. Efter skakning med en vattenhaltig Na 28205-lösning och torkning över Na2SO4 och avdunstning av lösningsmedlet erhölls 0,6 g av föreningen i rubriken.
Claims (1)
1. 7 458 684 PATENTKRAV Förfarande för framställning av en förening med formeln IVa= R S r\___T/ \íç/\\CHä}G ___ IVa o/f Ny QIR vari R betecknar en väteatom eller en p-nitrobensylgrupp, Rl betecknar en l-hydroxietylgrupp, varvid alkoholfunktionen hos denna hydroxi-etylgrupp är fri eller skyddad av dimetyl-tert.butylsilyl~, difenyl-tert.butylsilyl-, trimetylsilyl eller p-nitrobensyloxikarbonylgrupp och PG betecknar en dimetyl-tert.butylsilyl-, difenyl-tert.butyl- silyl- eller trimetylsilyl-grupp, k ä n n e t e C K H ä t därav, att förfarandet omfattar skyddande av den fria hydroxigruppen hos en förening med formeln II: H1 9 Wim H i ”fL ,// COOR vari Rl och R definieras som ovan med en grupp PG, som definieras som ovan, reduktion av sulfoxidfunktionen i den resulterande föreningen med formeln III: O H RI sïßopg III r--N\T4%l UHF vari Rl, R och PG definieras som ovan, med fosfortribromid, och ozonolysering av den resulterande föreningen med formel IV 458 684 1 Sñß GE IV // /'__N CGE O vari Rl, R och PG definieras som ovan, i ett lösningsmedel vid en temperatur av från -80°C till -50°C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8137513 | 1981-12-11 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8207092D0 SE8207092D0 (sv) | 1982-12-10 |
| SE8207092L SE8207092L (sv) | 1983-06-12 |
| SE458684B true SE458684B (sv) | 1989-04-24 |
Family
ID=10526562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8207092A SE458684B (sv) | 1981-12-11 | 1982-12-10 | Foerfarande foer framstaellning av azetidin-2-oner vilka anvaends som mellanprodukter foer framstaellning av penemer |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4508649A (sv) |
| JP (2) | JPS58126888A (sv) |
| AT (1) | AT379399B (sv) |
| AU (1) | AU556854B2 (sv) |
| BE (1) | BE895322A (sv) |
| CA (1) | CA1215705A (sv) |
| CH (1) | CH655504B (sv) |
| DE (1) | DE3245270C2 (sv) |
| DK (1) | DK160311C (sv) |
| FI (1) | FI76347C (sv) |
| FR (2) | FR2518098B1 (sv) |
| GB (1) | GB2111496B (sv) |
| GR (1) | GR77078B (sv) |
| HU (1) | HU187807B (sv) |
| IE (1) | IE54513B1 (sv) |
| IL (1) | IL67434A (sv) |
| IT (1) | IT1206106B (sv) |
| NL (2) | NL8204720A (sv) |
| SE (1) | SE458684B (sv) |
| SU (1) | SU1389680A3 (sv) |
| ZA (1) | ZA829063B (sv) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NO831160L (no) * | 1982-04-08 | 1983-10-10 | Erba Farmitalia | Fremstilling av substituerte penem-derivater |
| GB8300295D0 (en) * | 1983-01-06 | 1983-02-09 | Erba Farmitalia | Penem esters |
| GB8321677D0 (en) * | 1983-08-11 | 1983-09-14 | Erba Farmitalia | Preparation of penems |
| JPS62501556A (ja) * | 1984-07-13 | 1987-06-25 | メルシャン株式会社 | 新規２↓−オキソアゼチジン類、その製造方法および応用 |
| GB8713515D0 (en) * | 1987-06-10 | 1987-07-15 | Erba Farmitalia | Methoxymethyl compounds |
| GB8818789D0 (en) * | 1988-08-08 | 1988-09-07 | Erba Carlo Spa | Crystalline(5r 6s)-2-carbamoyloxymethyl-6-((1r)-hydroxyethyl)-2-penem-carboxylic acid & pharmaceutical formulation |
| US5204460A (en) * | 1988-11-29 | 1993-04-20 | Takasago International Corporation | Ruthenium catalyzed process for preparing 4-acetoxyazetidinones |
| EP0371875B1 (en) * | 1988-11-29 | 1994-12-28 | Takasago International Corporation | Process for preparing 4-acetoxyazetidinones |
| EP0597401A3 (en) * | 1992-11-11 | 1995-07-26 | Takeda Chemical Industries Ltd | Preparation of penemes. |
| JP4512651B2 (ja) * | 2008-06-18 | 2010-07-28 | 三井金属鉱業株式会社 | 車両用開閉体の開閉装置 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4348320A (en) * | 1976-11-19 | 1982-09-07 | Merck & Co., Inc. | Substituted azetidiones |
| EP0003960B1 (de) * | 1978-02-02 | 1983-06-29 | Ciba-Geigy Ag | 6-Substituierte Thia-Azaverbindungen, ihre Herstellung und diese enthaltende pharmazeutische Präparate |
| AT365594B (de) * | 1978-11-24 | 1982-01-25 | Erba Farmitalia | Verfahren zur herstellung von neuen 7-oxo-4-thia1-aza-bicyclo-(3,2,0)heptanderivaten |
| EP0013067A1 (en) * | 1978-12-22 | 1980-07-09 | Beecham Group Plc | Bicyclic beta-lactam antibacterial agents, their use in pharmaceutical compositions, processes for their preparation and intermediates for use in such processes |
| GB2037277B (en) * | 1978-12-22 | 1983-05-05 | Beecham Group Ltd | -lactam antibacterial agents their use in pharmaceutical compositions processes for their preparation and intermediates for use in such processes |
| FI75163C (sv) * | 1979-02-24 | 1988-05-09 | Erba Farmitalia | Förfarande för framställning av nya penemkarboxylsyror eller -estrar. |
| US4269771A (en) * | 1979-04-06 | 1981-05-26 | Farmitalia Carlo Erba | Total synthesis of 7-oxo-4-thia-1-azabicyclo-[3,2,0]-heptane-2-carboxyl derivatives useful as β-lactamase inhibitors and antibacterial agents |
| JPS55153789A (en) * | 1979-04-11 | 1980-11-29 | Sankyo Co Ltd | Penem-3-carboxylic acid derivative and its preparation |
| US4482565A (en) * | 1980-02-22 | 1984-11-13 | Farmitalia Carlo Erba S.P.A. | β-Lactam-containing antibacterial agents and β-lactamase inhibitors |
| GB2079744A (en) * | 1980-07-04 | 1982-01-27 | Erba Farmitalia | 6-Alkyl-2-functionalized penems |
-
1982
- 1982-12-06 SU SU823522502A patent/SU1389680A3/ru active
- 1982-12-06 NL NL8204720A patent/NL8204720A/nl not_active Application Discontinuation
- 1982-12-06 AT AT0443582A patent/AT379399B/de not_active IP Right Cessation
- 1982-12-06 US US06/447,187 patent/US4508649A/en not_active Expired - Lifetime
- 1982-12-06 AU AU91156/82A patent/AU556854B2/en not_active Ceased
- 1982-12-07 DE DE3245270A patent/DE3245270C2/de not_active Expired - Lifetime
- 1982-12-07 FI FI824192A patent/FI76347C/sv not_active IP Right Cessation
- 1982-12-07 FR FR8220490A patent/FR2518098B1/fr not_active Expired
- 1982-12-07 CA CA000417133A patent/CA1215705A/en not_active Expired
- 1982-12-07 IL IL67434A patent/IL67434A/xx not_active IP Right Cessation
- 1982-12-08 CH CH714982A patent/CH655504B/de unknown
- 1982-12-08 GB GB08235059A patent/GB2111496B/en not_active Expired
- 1982-12-08 IE IE2917/82A patent/IE54513B1/en not_active IP Right Cessation
- 1982-12-09 GR GR70033A patent/GR77078B/el unknown
- 1982-12-09 IT IT8224650A patent/IT1206106B/it active
- 1982-12-09 JP JP57214750A patent/JPS58126888A/ja active Granted
- 1982-12-09 ZA ZA829063A patent/ZA829063B/xx unknown
- 1982-12-10 BE BE0/209711A patent/BE895322A/fr not_active IP Right Cessation
- 1982-12-10 DK DK551182A patent/DK160311C/da not_active IP Right Cessation
- 1982-12-10 SE SE8207092A patent/SE458684B/sv not_active IP Right Cessation
- 1982-12-10 HU HU823997A patent/HU187807B/hu not_active IP Right Cessation
-
1985
- 1985-06-17 FR FR8509167A patent/FR2567888B1/fr not_active Expired
- 1985-11-27 JP JP60265183A patent/JPS61178987A/ja active Granted
-
1986
- 1986-02-24 NL NL8600460A patent/NL8600460A/xx not_active Application Discontinuation
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