CA1284324C - Carbapenem process - Google Patents

Carbapenem process

Info

Publication number
CA1284324C
CA1284324C CA000448904A CA448904A CA1284324C CA 1284324 C CA1284324 C CA 1284324C CA 000448904 A CA000448904 A CA 000448904A CA 448904 A CA448904 A CA 448904A CA 1284324 C CA1284324 C CA 1284324C
Authority
CA
Canada
Prior art keywords
alkyl
pyridinium
mmol
group
carbon atoms
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Fee Related
Application number
CA000448904A
Other languages
English (en)
French (fr)
Inventor
Pierre Dextraze
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bristol Myers Co
Original Assignee
Bristol Myers Co
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.)
Filing date
Publication date
Application filed by Bristol Myers Co filed Critical Bristol Myers Co
Application granted granted Critical
Publication of CA1284324C publication Critical patent/CA1284324C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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
    • 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

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Molecular Biology (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)
CA000448904A 1983-03-08 1984-03-06 Carbapenem process Expired - Fee Related CA1284324C (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US47137883A 1983-03-08 1983-03-08
US471,378 1983-03-08
US49969183A 1983-06-07 1983-06-07
US499,691 1983-06-07
US55729583A 1983-12-01 1983-12-01
US557,295 1983-12-01

Publications (1)

Publication Number Publication Date
CA1284324C true CA1284324C (en) 1991-05-21

Family

ID=27413179

Family Applications (1)

Application Number Title Priority Date Filing Date
CA000448904A Expired - Fee Related CA1284324C (en) 1983-03-08 1984-03-06 Carbapenem process

Country Status (31)

Country Link
JP (1) JPH05255250A (es)
KR (1) KR900002247B1 (es)
AR (1) AR241016A1 (es)
AT (1) AT387968B (es)
AU (2) AU572124B2 (es)
CA (1) CA1284324C (es)
CH (1) CH658248A5 (es)
CY (1) CY1546A (es)
DD (1) DD228258A5 (es)
DE (1) DE3408347A1 (es)
DK (1) DK140584A (es)
ES (2) ES530337A0 (es)
FI (1) FI840863A (es)
FR (1) FR2542316B1 (es)
GB (1) GB2136802B (es)
GR (1) GR81871B (es)
HK (1) HK82990A (es)
HU (1) HU193895B (es)
IE (1) IE57098B1 (es)
IL (1) IL71149A (es)
IT (1) IT1178465B (es)
LU (1) LU85241A1 (es)
NL (1) NL8400702A (es)
NO (1) NO166038C (es)
NZ (1) NZ207346A (es)
OA (1) OA07674A (es)
PT (1) PT78211B (es)
SE (2) SE8401278L (es)
SG (1) SG35490G (es)
YU (2) YU46147B (es)
ZW (1) ZW3884A1 (es)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
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
IE851586L (en) * 1984-07-02 1986-01-02 Interchem Internat S A I methylcarbapenems having a 2-quaternary¹heteroarylalkylthio substituent
CA1285940C (en) * 1984-07-02 1991-07-09 Merck & Co., Inc. Carbapenems having a 2-quaternary heteroarylalkylthio 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
NZ237191A (en) * 1990-02-23 1992-12-23 Sankyo Co 2-((substituted amide) substituted heterocyclylthio) carbpen-2-em derivatives and pharmaceutical compositions
US5712267A (en) * 1991-06-04 1998-01-27 Sankyo Company,. Limited Carbapenem derivatives, their preparation and their use as antibiotics
AU2004247462B2 (en) 2003-06-12 2010-09-02 Btg International Limited Cyclic hydroxylamine as psychoactive compounds
FR2921258A1 (fr) * 2007-09-24 2009-03-27 Oreal Composition tinctoriale comprenant au moins un precurseur incolore disulfures/thiol, proced de coloration a partir de la composition

Family Cites Families (8)

* Cited by examiner, † Cited by third party
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

Also Published As

Publication number Publication date
ES8505205A1 (es) 1985-05-16
IE840549L (en) 1984-09-08
ES8507145A1 (es) 1985-08-16
YU42084A (en) 1986-08-31
NL8400702A (nl) 1984-10-01
SE8901162D0 (sv) 1989-04-03
DE3408347A1 (de) 1984-09-13
PT78211A (en) 1984-04-01
AU7592487A (en) 1987-10-22
HUT34980A (en) 1985-05-28
GB2136802B (en) 1987-05-20
ZW3884A1 (en) 1984-10-10
NO166038B (no) 1991-02-11
YU46305B (sh) 1993-05-28
ES537349A0 (es) 1985-08-16
YU49486A (en) 1987-12-31
AT387968B (de) 1989-04-10
FI840863A0 (fi) 1984-03-05
SE8401278D0 (sv) 1984-03-07
IL71149A0 (en) 1984-06-29
IT1178465B (it) 1987-09-09
AU2536084A (en) 1984-09-13
NZ207346A (en) 1987-01-23
JPH05255250A (ja) 1993-10-05
SG35490G (en) 1990-07-13
KR840008157A (ko) 1984-12-13
NO166038C (no) 1991-05-22
ES530337A0 (es) 1985-05-16
DK140584D0 (da) 1984-02-29
YU46147B (sh) 1993-05-28
FI840863A (fi) 1984-09-09
OA07674A (fr) 1985-05-23
DK140584A (da) 1984-09-09
AR241016A2 (es) 1991-04-30
CH658248A5 (de) 1986-10-31
KR900002247B1 (ko) 1990-04-07
SE8401278L (sv) 1984-09-09
ATA76984A (de) 1988-09-15
AU605491B2 (en) 1991-01-17
FR2542316B1 (fr) 1988-10-07
PT78211B (en) 1986-08-12
GR81871B (es) 1984-12-12
HU193895B (en) 1987-12-28
AU572124B2 (en) 1988-05-05
GB2136802A (en) 1984-09-26
FR2542316A1 (fr) 1984-09-14
IT8419945A0 (it) 1984-03-07
IE57098B1 (en) 1992-04-22
GB8405984D0 (en) 1984-04-11
LU85241A1 (fr) 1984-11-14
NO840865L (no) 1984-09-10
SE8901162L (sv) 1989-04-03
IL71149A (en) 1990-03-19
AR241016A1 (es) 1991-04-30
CY1546A (en) 1991-03-22
HK82990A (en) 1990-10-19
DD228258A5 (de) 1985-10-09

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