YU46147B - PROCEDURE FOR OBTAINING CARBAPENE DERIVATIVES - Google Patents
PROCEDURE FOR OBTAINING CARBAPENE DERIVATIVESInfo
- Publication number
- YU46147B YU46147B YU42084A YU42084A YU46147B YU 46147 B YU46147 B YU 46147B YU 42084 A YU42084 A YU 42084A YU 42084 A YU42084 A YU 42084A YU 46147 B YU46147 B YU 46147B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- formula
- defined above
- hydrogen
- protecting group
- group
- Prior art date
Links
Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
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- 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)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
ili grupa formule: gde su R10, R11, R12 i R13 svaki nezavisno vodonik ili C1-4alkil; R2 je vodonik, anjonski naboj ili karboksi-zaštitna grupa kao što je p-nitrobenzil, pri čemu je, kada R2 predstavlja vodonik ili zaštitnu grupu, takodje prisutan i suprotan anjon kao što je Cl, Br, CH3SO3- ili CF3SO3-; i R14 je heterociklična grupa koja sadrži kvaternerizovani aazotov atom, formule: gde su R i R" nezavisno odabrani od vodonika, CH3, CH2OH, OCH3, SCH3 i NH2; i B je odabrano od O, S, S------ O, N---- CH3 ili N+------CH3 CH3 i njihovih farmacutski prihvatljivih soli, naznačen time, što intermedijer formule: u kojoj su R1 i R8 kao što je definisano gore, R2 je karboksi-zaštitna grupa kao što je p-nitrobenzil i L je odlazeća grupa kao što je difenoksifosfiniloksi, reaguje sa tiolnim jedinjenjem formule: HS------A----R14 X-- u kojoj su A i R14 kao što je definisano gore i X-- 0 je suprotan anjon kao što je definisan gore, u inertnom rastvaraču kao što je acetonitril, dimetilformamid, tetrahidrofuran, voda ili njihove smeše, u prisustvu baze kao što je ne-nukleofilni amin ili tri (C1-4)alkilamin i na temperaturi od -15В°C do sobne temperature, da bi se dobio karbapenem proizvod formule: u kojoj su R1, R8, R2, A, R14 i X-- 0 kao što je definisano gore; što se, po potrebi, vrši uklanjanje zaštitne grupe R2 da bi se dobilo jedinjenje formule (I) u kojoj R2 predstavlja vodonik ili anjonski naboj; i što se, po potrebi, proizvod formule (I) prevodi u svoju farmaceutski prihvatljivu so.or a group of the formula: wherein R 10, R 11, R 12 and R 13 are each independently hydrogen or C 1-4 alkyl; R 2 is hydrogen, an anionic charge or a carboxy-protecting group such as p-nitrobenzyl, wherein when R 2 represents hydrogen or a protecting group, the opposite anion such as Cl, Br, CH 3 SO 3 - or CF 3 SO 3 - is also present; and R14 is a heterocyclic group containing a quaternized nitrogen atom, of formula: wherein R and R "are independently selected from hydrogen, CH3, CH2OH, OCH3, SCH3 and NH2; and B is selected from O, S, S ------ O, N ---- CH3 or N + ------ CH3 CH3 and pharmaceutically acceptable salts thereof, wherein the intermediate of formula: wherein R1 and R8 are as defined above, R2 is a carboxy-protecting group as which is p-nitrobenzyl and L is a leaving group such as diphenoxyphosphinyloxy, reacts with a thiol compound of formula: HS ------ A ---- R14 X-- in which A and R14 are as defined above and X - 0 is the opposite anion as defined above, in an inert solvent such as acetonitrile, dimethylformamide, tetrahydrofuran, water or mixtures thereof, in the presence of a base such as a non-nucleophilic amine or tri (C1-4) alkylamine and at a temperature from -15V ° C to room temperature, to give a carbapenem product of the formula: wherein R 1, R 8, R 2, A, R 14 and X - 0 as defined above; titanium groups R2 to give a compound of formula (I) wherein R2 represents hydrogen or an anionic charge; and that, if necessary, the product of formula (I) is converted into its pharmaceutically acceptable salt.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
YU49486A YU46305B (en) | 1983-03-08 | 1986-03-28 | PROCEDURE FOR OBTAINING QUATERNARY AMINE THIOLS |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US47137883A | 1983-03-08 | 1983-03-08 | |
US49969183A | 1983-06-07 | 1983-06-07 | |
US55729583A | 1983-12-01 | 1983-12-01 |
Publications (2)
Publication Number | Publication Date |
---|---|
YU42084A YU42084A (en) | 1986-08-31 |
YU46147B true YU46147B (en) | 1993-05-28 |
Family
ID=27413179
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
YU42084A YU46147B (en) | 1983-03-08 | 1984-03-08 | PROCEDURE FOR OBTAINING CARBAPENE DERIVATIVES |
YU49486A YU46305B (en) | 1983-03-08 | 1986-03-28 | PROCEDURE FOR OBTAINING QUATERNARY AMINE THIOLS |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
YU49486A YU46305B (en) | 1983-03-08 | 1986-03-28 | PROCEDURE FOR OBTAINING QUATERNARY AMINE THIOLS |
Country Status (31)
Country | Link |
---|---|
JP (1) | JPH05255250A (en) |
KR (1) | KR900002247B1 (en) |
AR (1) | AR241016A1 (en) |
AT (1) | AT387968B (en) |
AU (2) | AU572124B2 (en) |
CA (1) | CA1284324C (en) |
CH (1) | CH658248A5 (en) |
CY (1) | CY1546A (en) |
DD (1) | DD228258A5 (en) |
DE (1) | DE3408347A1 (en) |
DK (1) | DK140584A (en) |
ES (2) | ES8505205A1 (en) |
FI (1) | FI840863A (en) |
FR (1) | FR2542316B1 (en) |
GB (1) | GB2136802B (en) |
GR (1) | GR81871B (en) |
HK (1) | HK82990A (en) |
HU (1) | HU193895B (en) |
IE (1) | IE57098B1 (en) |
IL (1) | IL71149A (en) |
IT (1) | IT1178465B (en) |
LU (1) | LU85241A1 (en) |
NL (1) | NL8400702A (en) |
NO (1) | NO166038C (en) |
NZ (1) | NZ207346A (en) |
OA (1) | OA07674A (en) |
PT (1) | PT78211B (en) |
SE (2) | SE8401278L (en) |
SG (1) | SG35490G (en) |
YU (2) | YU46147B (en) |
ZW (1) | ZW3884A1 (en) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4683301A (en) * | 1982-04-08 | 1987-07-28 | Bristol-Myers Company | Carbapenem antibiotics |
US4552696A (en) * | 1982-04-09 | 1985-11-12 | Bristol-Myers Company | Carbapenem antibiotics |
CA1285940C (en) * | 1984-07-02 | 1991-07-09 | Merck & Co., Inc. | Carbapenems having a 2-quaternary heteroarylalkylthio substituent |
IE851586L (en) * | 1984-07-02 | 1986-01-02 | Interchem Internat S A | I methylcarbapenems having a 2-quaternary¹heteroarylalkylthio substituent |
US4665169A (en) * | 1985-09-11 | 1987-05-12 | Bristol-Myers Company | Carbapenem antibiotics |
US4880922A (en) * | 1985-11-22 | 1989-11-14 | Bristol-Myers Company | Carbapenems with quaternized heterothioalkylthio substitution at position 2 |
NZ219892A (en) * | 1986-04-15 | 1991-02-26 | Merck & Co Inc | N-amino quaternised heteroarylium carbapenem derivatives and pharmaceutical compositions thereof |
IE910606A1 (en) * | 1990-02-23 | 1991-08-28 | Sankyo Co | Carbapenem derivatives having antibiotic activity, their¹preparation and their use |
US5712267A (en) * | 1991-06-04 | 1998-01-27 | Sankyo Company,. Limited | Carbapenem derivatives, their preparation and their use as antibiotics |
KR20060018253A (en) | 2003-06-12 | 2006-02-28 | 비티지 인터내셔널 리미티드 | Cyclic Hydroxylamines As Psychotropic Compounds |
FR2921258A1 (en) * | 2007-09-24 | 2009-03-27 | Oreal | TINCTORIAL COMPOSITION COMPRISING AT LEAST ONE COLOR DISULFIDE / THIOL PRECURSOR, COLORING PROCESS FROM THE COMPOSITION |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS55147284A (en) * | 1979-04-17 | 1980-11-17 | Sanraku Inc | Novel beta-lactam derivative and its preparation |
IE52147B1 (en) * | 1980-03-27 | 1987-07-08 | Merck & Co Inc | 4-(3-carboxy-2-oxopropyl)-azetidin-2-ones and process for their preparation |
EP0038869A1 (en) * | 1980-04-30 | 1981-11-04 | Merck & Co. Inc. | Process for the preparation of 1-carbapenems, and intermediates for their preparation |
EP0060612A1 (en) * | 1981-02-04 | 1982-09-22 | Beecham Group Plc | Process for the preparation of azabicyclo(3.2.0)-hept-2-ene derivatives |
US4552873A (en) * | 1981-08-19 | 1985-11-12 | Sankyo Company Limited | Carbapenem compounds, and compositions containing them |
EP0074599A1 (en) * | 1981-09-09 | 1983-03-23 | Takeda Chemical Industries, Ltd. | 5,6-cis-Carbapenem derivatives, their production and use |
US4552696A (en) * | 1982-04-09 | 1985-11-12 | Bristol-Myers Company | Carbapenem antibiotics |
US4536335A (en) * | 1982-06-18 | 1985-08-20 | Bristol-Myers Company | Carbapenem antibiotics |
-
1984
- 1984-02-29 DK DK140584A patent/DK140584A/en not_active Application Discontinuation
- 1984-02-29 AR AR295877A patent/AR241016A1/en active
- 1984-03-01 NZ NZ207346A patent/NZ207346A/en unknown
- 1984-03-05 FI FI840863A patent/FI840863A/en not_active Application Discontinuation
- 1984-03-05 NL NL8400702A patent/NL8400702A/en not_active Application Discontinuation
- 1984-03-05 ZW ZW38/84A patent/ZW3884A1/en unknown
- 1984-03-05 IL IL71149A patent/IL71149A/en unknown
- 1984-03-06 GR GR73999A patent/GR81871B/el unknown
- 1984-03-06 CA CA000448904A patent/CA1284324C/en not_active Expired - Fee Related
- 1984-03-06 CH CH1103/84A patent/CH658248A5/en not_active IP Right Cessation
- 1984-03-07 LU LU85241A patent/LU85241A1/en unknown
- 1984-03-07 GB GB08405984A patent/GB2136802B/en not_active Expired
- 1984-03-07 IE IE549/84A patent/IE57098B1/en not_active IP Right Cessation
- 1984-03-07 HU HU84911A patent/HU193895B/en not_active IP Right Cessation
- 1984-03-07 DE DE19843408347 patent/DE3408347A1/en not_active Withdrawn
- 1984-03-07 PT PT78211A patent/PT78211B/en unknown
- 1984-03-07 OA OA58247A patent/OA07674A/en unknown
- 1984-03-07 AU AU25360/84A patent/AU572124B2/en not_active Ceased
- 1984-03-07 DD DD84260663A patent/DD228258A5/en not_active IP Right Cessation
- 1984-03-07 SE SE8401278A patent/SE8401278L/en not_active Application Discontinuation
- 1984-03-07 NO NO840865A patent/NO166038C/en unknown
- 1984-03-07 AT AT0076984A patent/AT387968B/en not_active IP Right Cessation
- 1984-03-07 IT IT19945/84A patent/IT1178465B/en active
- 1984-03-07 ES ES530337A patent/ES8505205A1/en not_active Expired
- 1984-03-07 FR FR8403553A patent/FR2542316B1/en not_active Expired
- 1984-03-08 KR KR1019840001243A patent/KR900002247B1/en not_active IP Right Cessation
- 1984-03-08 YU YU42084A patent/YU46147B/en unknown
- 1984-11-02 ES ES537349A patent/ES537349A0/en active Granted
-
1986
- 1986-03-28 YU YU49486A patent/YU46305B/en unknown
-
1987
- 1987-07-20 AU AU75924/87A patent/AU605491B2/en not_active Ceased
-
1989
- 1989-04-03 SE SE8901162A patent/SE8901162D0/en not_active Application Discontinuation
-
1990
- 1990-05-19 SG SG35490A patent/SG35490G/en unknown
- 1990-10-11 HK HK829/90A patent/HK82990A/en unknown
-
1991
- 1991-03-22 CY CY1546A patent/CY1546A/en unknown
- 1991-09-27 JP JP3274949A patent/JPH05255250A/en active Pending
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