SE469076B - Foerfarnde foer avlaegsnande av skyddsgrupper fraan allylestrar - Google Patents
Foerfarnde foer avlaegsnande av skyddsgrupper fraan allylestrarInfo
- Publication number
- SE469076B SE469076B SE8602555A SE8602555A SE469076B SE 469076 B SE469076 B SE 469076B SE 8602555 A SE8602555 A SE 8602555A SE 8602555 A SE8602555 A SE 8602555A SE 469076 B SE469076 B SE 469076B
- Authority
- SE
- Sweden
- Prior art keywords
- palladium
- minutes
- triphenylphosphine
- allyl ester
- tetrakis
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 30
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 18
- -1 allyl ester Chemical class 0.000 claims description 14
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 11
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical class C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000007787 solid Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 5
- 239000008363 phosphate buffer Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 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 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 description 1
- PBCJIPOGFJYBJE-UHFFFAOYSA-N acetonitrile;hydrate Chemical compound O.CC#N PBCJIPOGFJYBJE-UHFFFAOYSA-N 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000007275 deallylation reaction Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AGJSNMGHAVDLRQ-IWFBPKFRSA-N methyl (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-amino-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,3-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoate Chemical compound SC[C@H](N)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(=O)OC)CC1=CC=C(O)C(C)=C1C AGJSNMGHAVDLRQ-IWFBPKFRSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical group [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/02—Preparation
- C07D477/06—Preparation from compounds already containing the ring or condensed ring systems, e.g. by dehydrogenation of the ring, by introduction, elimination or modification of substituents
- C07D477/08—Modification of a carboxyl group directly attached in position 2, e.g. esterification
-
- 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
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
-
- 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)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Cephalosporin Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/742,495 US4788282A (en) | 1985-06-07 | 1985-06-07 | Deprotection of allylic esters and ethers |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE8602555D0 SE8602555D0 (sv) | 1986-06-06 |
| SE8602555L SE8602555L (sv) | 1986-12-08 |
| SE469076B true SE469076B (sv) | 1993-05-10 |
Family
ID=24985064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8602555A SE469076B (sv) | 1985-06-07 | 1986-06-06 | Foerfarnde foer avlaegsnande av skyddsgrupper fraan allylestrar |
Country Status (35)
| Country | Link |
|---|---|
| US (1) | US4788282A (cs) |
| JP (1) | JPH0637496B2 (cs) |
| KR (1) | KR900007246B1 (cs) |
| CN (1) | CN1015104B (cs) |
| AR (1) | AR241019A1 (cs) |
| AT (1) | AT390955B (cs) |
| BE (1) | BE904885A (cs) |
| CA (1) | CA1273630A (cs) |
| CH (1) | CH666678A5 (cs) |
| CS (1) | CS265220B2 (cs) |
| DD (1) | DD245433A5 (cs) |
| DE (1) | DE3619200C2 (cs) |
| DK (1) | DK268886A (cs) |
| EG (1) | EG18276A (cs) |
| ES (1) | ES8800684A1 (cs) |
| FI (1) | FI89486C (cs) |
| FR (1) | FR2583038B1 (cs) |
| GB (1) | GB2176478B (cs) |
| GR (1) | GR861432B (cs) |
| HU (1) | HU198167B (cs) |
| IE (1) | IE59187B1 (cs) |
| IL (1) | IL79023A (cs) |
| IT (1) | IT1190041B (cs) |
| LU (1) | LU86461A1 (cs) |
| NL (1) | NL191787C (cs) |
| NO (1) | NO165998C (cs) |
| NZ (1) | NZ216364A (cs) |
| OA (1) | OA08340A (cs) |
| PT (1) | PT82727B (cs) |
| SE (1) | SE469076B (cs) |
| SU (1) | SU1508959A3 (cs) |
| YU (1) | YU45330B (cs) |
| ZA (1) | ZA862749B (cs) |
| ZM (1) | ZM3786A1 (cs) |
| ZW (1) | ZW9286A1 (cs) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE60588B1 (en) * | 1986-07-30 | 1994-07-27 | Sumitomo Pharma | Carbapenem compound in crystalline form, and its production and use |
| JPS63154628A (ja) * | 1986-12-17 | 1988-06-27 | Nippon Zeon Co Ltd | 保護化アルコール化合物の脱保護方法 |
| EP0384732A3 (en) * | 1989-02-23 | 1991-12-04 | Merck & Co. Inc. | Deblocking process for allyl esters with regeneratable polymer supported pd (0) |
| AU670261B2 (en) * | 1992-04-15 | 1996-07-11 | Rhone-Poulenc Chimie | Reagent and catalytic process useful for cleaving a protected functional group |
| FR2690153A1 (fr) * | 1992-04-15 | 1993-10-22 | Rhone Poulenc Chimie | Réactif et procédé catalytique utile pour cliver une fonction protégée. |
| US5587474A (en) * | 1992-06-18 | 1996-12-24 | Tanabe Seiyaku Co., Ltd. | Method for removing the protecting group for carboxyl group |
| JP2847693B2 (ja) * | 1992-06-18 | 1999-01-20 | 田辺製薬株式会社 | カルボキシル基保護基の除去方法 |
| US5578740A (en) * | 1994-12-23 | 1996-11-26 | The Dow Chemical Company | Process for preparation of epoxy compounds essentially free of organic halides |
| WO2006060803A2 (en) * | 2004-12-03 | 2006-06-08 | Polnox Corporation | One pot process for making polymeric antioxidants |
| US8361802B2 (en) * | 2009-03-09 | 2013-01-29 | University of Pittsburgh—of the Commonwealth System of Higher Education | Fluorescent ozone sensor |
| US8550716B2 (en) | 2010-06-22 | 2013-10-08 | S.C. Johnson & Son, Inc. | Tactile enhancement mechanism for a closure mechanism |
| US8974118B2 (en) | 2010-10-29 | 2015-03-10 | S.C. Johnson & Son, Inc. | Reclosable bag having a sound producing zipper |
| US9327875B2 (en) | 2010-10-29 | 2016-05-03 | S.C. Johnson & Son, Inc. | Reclosable bag having a loud sound during closing |
| US11180286B2 (en) | 2010-10-29 | 2021-11-23 | S. C. Johnson & Son, Inc. | Reclosable bag having a loud sound during closing |
| US8568031B2 (en) | 2011-02-22 | 2013-10-29 | S.C. Johnson & Son, Inc. | Clicking closure device for a reclosable pouch |
| US8469593B2 (en) | 2011-02-22 | 2013-06-25 | S.C. Johnson & Son, Inc. | Reclosable bag having a press-to-vent zipper |
| EP3004134B1 (en) * | 2013-06-04 | 2019-02-27 | The University of Sydney | Peptide ligation |
| EP3071544B1 (en) | 2013-11-22 | 2022-07-06 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures methods of making and using the same |
| EP3498717B1 (en) * | 2016-08-12 | 2022-05-04 | The Catholic University of Korea Industry-Academic Cooperation Foundation | Composition for hardening soft tissue |
| US20180251695A1 (en) | 2017-03-01 | 2018-09-06 | Polnox Corporation | Macromolecular Corrosion (McIn) Inhibitors: Structures, Methods Of Making And Using The Same |
| CN108383848A (zh) * | 2018-03-27 | 2018-08-10 | 石家庄蒎格医药科技有限公司 | 聚乙二醇纳洛酮新杂质及其制备方法 |
| CN118851945A (zh) * | 2024-07-03 | 2024-10-29 | 中科全同(大连)医药科技有限公司 | 一种n-芴甲氧羰基-n',n',n'-三甲基-l-赖氨酸氯化物的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4314942A (en) * | 1979-01-10 | 1982-02-09 | Schering Corporation | Deprotection of allylic esters, carbonates and carbamates catalyzed by palladium compounds |
| US4536335A (en) * | 1982-06-18 | 1985-08-20 | Bristol-Myers Company | Carbapenem antibiotics |
| DE3443993A1 (de) * | 1984-12-01 | 1986-06-05 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von neuen indolderivaten und deren verwendung |
-
1985
- 1985-06-07 US US06/742,495 patent/US4788282A/en not_active Expired - Fee Related
-
1986
- 1986-04-10 CA CA000506363A patent/CA1273630A/en not_active Expired - Lifetime
- 1986-04-11 ZA ZA862749A patent/ZA862749B/xx unknown
- 1986-04-24 ZW ZW92/86A patent/ZW9286A1/xx unknown
- 1986-04-28 ZM ZM37/86A patent/ZM3786A1/xx unknown
- 1986-05-16 FR FR868607068A patent/FR2583038B1/fr not_active Expired
- 1986-05-23 CN CN86103521A patent/CN1015104B/zh not_active Expired
- 1986-05-28 YU YU904/86A patent/YU45330B/xx unknown
- 1986-05-30 NZ NZ216364A patent/NZ216364A/en unknown
- 1986-06-03 GR GR861432A patent/GR861432B/el unknown
- 1986-06-04 IL IL79023A patent/IL79023A/xx not_active IP Right Cessation
- 1986-06-04 FI FI862377A patent/FI89486C/fi not_active IP Right Cessation
- 1986-06-04 CS CS864119A patent/CS265220B2/cs unknown
- 1986-06-05 IT IT20691/86A patent/IT1190041B/it active
- 1986-06-05 EG EG350/86A patent/EG18276A/xx active
- 1986-06-05 JP JP61131047A patent/JPH0637496B2/ja not_active Expired - Lifetime
- 1986-06-05 KR KR1019860004452A patent/KR900007246B1/ko not_active Expired
- 1986-06-05 NO NO862237A patent/NO165998C/no unknown
- 1986-06-06 PT PT82727A patent/PT82727B/pt not_active IP Right Cessation
- 1986-06-06 DD DD86291080A patent/DD245433A5/de not_active IP Right Cessation
- 1986-06-06 SU SU864027586A patent/SU1508959A3/ru active
- 1986-06-06 LU LU86461A patent/LU86461A1/fr unknown
- 1986-06-06 IE IE151486A patent/IE59187B1/en not_active IP Right Cessation
- 1986-06-06 ES ES555840A patent/ES8800684A1/es not_active Expired
- 1986-06-06 DK DK268886A patent/DK268886A/da not_active Application Discontinuation
- 1986-06-06 GB GB08613738A patent/GB2176478B/en not_active Expired
- 1986-06-06 SE SE8602555A patent/SE469076B/sv not_active IP Right Cessation
- 1986-06-06 AR AR304252A patent/AR241019A1/es active
- 1986-06-06 CH CH2313/86A patent/CH666678A5/de not_active IP Right Cessation
- 1986-06-06 BE BE0/216754A patent/BE904885A/fr not_active IP Right Cessation
- 1986-06-06 OA OA58874A patent/OA08340A/xx unknown
- 1986-06-06 HU HU862400A patent/HU198167B/hu not_active IP Right Cessation
- 1986-06-06 NL NL8601469A patent/NL191787C/xx not_active IP Right Cessation
- 1986-06-07 DE DE3619200A patent/DE3619200C2/de not_active Expired - Fee Related
- 1986-06-09 AT AT0155586A patent/AT390955B/de not_active IP Right Cessation
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