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)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
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 (it) |
| JP (2) | JPS58126888A (it) |
| AT (1) | AT379399B (it) |
| AU (1) | AU556854B2 (it) |
| BE (1) | BE895322A (it) |
| CA (1) | CA1215705A (it) |
| CH (1) | CH655504B (it) |
| DE (1) | DE3245270C2 (it) |
| DK (1) | DK160311C (it) |
| FI (1) | FI76347C (it) |
| FR (2) | FR2518098B1 (it) |
| GB (1) | GB2111496B (it) |
| GR (1) | GR77078B (it) |
| HU (1) | HU187807B (it) |
| IE (1) | IE54513B1 (it) |
| IL (1) | IL67434A (it) |
| IT (1) | IT1206106B (it) |
| NL (2) | NL8204720A (it) |
| SE (1) | SE458684B (it) |
| SU (1) | SU1389680A3 (it) |
| ZA (1) | ZA829063B (it) |
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 |
| DE68920298T2 (de) * | 1988-11-29 | 1995-07-27 | Takasago Perfumery Co Ltd | Verfahren zur Herstellung von 4-Acetoxyazetidinonen. |
| 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 |
| EP0042026B1 (de) * | 1978-02-02 | 1986-01-08 | Ciba-Geigy Ag | 3,4-Disubstituierte Azetidin-2-onverbindungen und Verfahren zu ihrer Herstellung |
| US4331677A (en) * | 1978-11-24 | 1982-05-25 | Farmitalia Carlo Erba S.P.A. | 7-Oxo-4-1-aza-bicyclo-[3,2,0]-heptane derivatives |
| 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 |
| 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 |
| NL192265C (nl) * | 1979-02-24 | 1997-04-03 | Erba Carlo Spa | Penemcarbonzuur-verbindingen en farmaceutische preparaten die deze verbindingen bevatten. |
| 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 NL NL8204720A patent/NL8204720A/nl not_active Application Discontinuation
- 1982-12-06 US US06/447,187 patent/US4508649A/en not_active Expired - Lifetime
- 1982-12-06 SU SU823522502A patent/SU1389680A3/ru active
- 1982-12-06 AT AT0443582A patent/AT379399B/de not_active IP Right Cessation
- 1982-12-06 AU AU91156/82A patent/AU556854B2/en not_active Ceased
- 1982-12-07 CA CA000417133A patent/CA1215705A/en not_active Expired
- 1982-12-07 FI FI824192A patent/FI76347C/fi not_active IP Right Cessation
- 1982-12-07 IL IL67434A patent/IL67434A/xx not_active IP Right Cessation
- 1982-12-07 FR FR8220490A patent/FR2518098B1/fr not_active Expired
- 1982-12-07 DE DE3245270A patent/DE3245270C2/de not_active Expired - Lifetime
- 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
- 1982-12-08 CH CH714982A patent/CH655504B/de unknown
- 1982-12-09 ZA ZA829063A patent/ZA829063B/xx unknown
- 1982-12-09 JP JP57214750A patent/JPS58126888A/ja active Granted
- 1982-12-09 IT IT8224650A patent/IT1206106B/it active
- 1982-12-09 GR GR70033A patent/GR77078B/el unknown
- 1982-12-10 DK DK551182A patent/DK160311C/da not_active IP Right Cessation
- 1982-12-10 HU HU823997A patent/HU187807B/hu not_active IP Right Cessation
- 1982-12-10 SE SE8207092A patent/SE458684B/sv not_active IP Right Cessation
- 1982-12-10 BE BE0/209711A patent/BE895322A/fr 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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NAL | Patent in force |
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| NUG | Patent has lapsed |