FI78094C - Förfarande för framställning av antibiotiskt aktiva karbapenemförening ar - Google Patents

Förfarande för framställning av antibiotiskt aktiva karbapenemförening ar Download PDF

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Publication number
FI78094C
FI78094C FI833417A FI833417A FI78094C FI 78094 C FI78094 C FI 78094C FI 833417 A FI833417 A FI 833417A FI 833417 A FI833417 A FI 833417A FI 78094 C FI78094 C FI 78094C
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FI
Finland
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solution
mmol
compound
methyl
formula
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FI833417A
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English (en)
Finnish (fi)
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FI833417A0 (fi
FI833417A (fi
FI78094B (fi
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Choung Un Kim
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Bristol Myers Co
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Publication of FI833417A publication Critical patent/FI833417A/fi
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Application granted granted Critical
Publication of FI78094C publication Critical patent/FI78094C/sv

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    • 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
    • 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
    • C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • 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
    • C07D213/32—Sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/26—Radicals substituted by sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
    • 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
    • C07D477/10—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 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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
    • C07D477/12—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 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
    • C07D477/16—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 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with 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 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms 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 3
    • C07D477/20—Sulfur atoms
    • 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
    • C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
    • C07F9/65611—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. penicillins and analogs

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Cephalosporin Compounds (AREA)

Claims (7)

1. Förfarande för framställning av antibiotiskt aktiva karbapenemderivat med formeln (I) 5 R15 OH H | Jl __ ch3(!:h--(I—S-A-n®-r5 1
10. N-\ 2
0 XOOR^ väri är en alkyl med 1-3 kolatomer, karboximetyl eller allyl, A är en rakkedjad eller förgrenad C^-Cg-alkylen; R 15 är väte, en anjonisk laddning eller en konventionell lätt avlägsningsbar skyddsgrupp för kaboxyl förutsatt att när R2 är väte eller en skyddsgrupp, det Sven är närvarande en motjon; R^ är väte eller metyl; och 20 -O- 25 är en med gruppen R^ kvartärniserad heteroaromatisk grupp, vilken är en pyridinium-, tetrazolium-, imidazolium-, tri-azolium-, tiazolium- eller tiadiazoliumgrupp som kan vara substituerad med 1-3 metylgrupper, karboximetyl eller ben-syl och som är bunden tili gruppen A via en ringkolatom, 30 kännetecknat därav, att man a) omsätter en föreing med formeln (II) R15 _ OH H Hl ch3<!:h4-J^V^“A V J 35 '1
1-N-L CT ^COOR2' 179 7 8 0 9 4 väri R^ och A är som ovan definierats och O är en heteroaromatisk radikal som är pyridyl, tetrazolyl, imida-zolyl, triazolyl, tiazolyl eller tiadiazolyl och som kan vara substituerad med 1-3 metylgrupper, karboximetyl el-5 ler bensyl och som är bunden tili gruppen A via en ring-kolatom, och R är en konventionell lätt avlägsningsbar skyddsgrupp för karboxyl, i ett inert organiskt lösnings-medel med ett alkyleringsmedel som formeln 10 r5-x' väri R^ är ovan definierad och X' är en konventionell av-gäende grupp säsom halogen, sä att gruppen R^ kvatärnise-rar ringkväveatomen i substituenten -O i föreningen med formeln II och bildar en förening med for-20 meln H H f' CHjCH--f^Sp-3- “X'® 1—n-2, x' cr ^coor*4 väri R15, R2', A, -O®- R^ och X' är ovan definierade, 30 och att man, om sä önskas, ersätter motjonen X' med en annan motjon och, om sä önskas, avlägsnar karboxylskydds-gruppen R för erhällande av den önskade oskyddade föreningen med formeln I eller ett farmaceutiskt godtagbart sait därav, eller 35 b) (1) omsätter en förening med formeln (III) 180 7 8 0 9 4 R15 YH H vXo
5 CH3CH--[ Y )-"-k 2' O x ^ COOR^
1. II väri R och R är som ovan definierats, i ett inert or-10 ganiskt lösningsmedel med en reagens, som har förmäga att införa en konventionell avgäende grupp L säsom en difenyl-fosforyloxigrupp i 2-positionen i föreningen med formeln III för erhällande av en förening med formeln (IV) 15 15 R15 on H SI ch3ch--Ϋ'
20. N:oor2' 7 1 van L och R Mr som ovan definierats; (2) omsätter den erhällna föreningen med formeln IV i ett inert organiskt lösningsmedel och i närvaro av en bas 25 med en merkaptanreagens med formeln HS-A- 30 väri A och Mr som ovan definierats, och omvandlar den erhällna föreningen med formeln II säsom angivits ovan i punkt a) tili den önskade föreningen med formeln I, eller c) omsätter en förening med formeln (IV)
FI833417A 1982-09-28 1983-09-23 Förfarande för framställning av antibiotiskt aktiva karbapenemförening ar FI78094C (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US42575582A 1982-09-28 1982-09-28
US42575582 1982-09-28
US53001183A 1983-09-09 1983-09-09
US53001183 1983-09-09

Publications (4)

Publication Number Publication Date
FI833417A0 FI833417A0 (fi) 1983-09-23
FI833417A FI833417A (fi) 1984-03-29
FI78094B FI78094B (fi) 1989-02-28
FI78094C true FI78094C (sv) 1989-06-12

Family

ID=27026797

Family Applications (1)

Application Number Title Priority Date Filing Date
FI833417A FI78094C (sv) 1982-09-28 1983-09-23 Förfarande för framställning av antibiotiskt aktiva karbapenemförening ar

Country Status (29)

Country Link
KR (1) KR890002228B1 (sv)
AR (1) AR241785A1 (sv)
AT (1) AT382621B (sv)
AU (1) AU575541B2 (sv)
CA (1) CA1269978A (sv)
CH (1) CH656130A5 (sv)
CS (1) CS247168B2 (sv)
DD (1) DD212255A5 (sv)
DE (1) DE3334937A1 (sv)
DK (1) DK442383A (sv)
ES (1) ES525983A0 (sv)
FI (1) FI78094C (sv)
FR (1) FR2533568B1 (sv)
GB (1) GB2128187B (sv)
GR (1) GR78696B (sv)
HU (1) HU191066B (sv)
IE (1) IE55947B1 (sv)
IL (1) IL69824A (sv)
IT (1) IT1163944B (sv)
LU (1) LU85021A1 (sv)
NL (1) NL8303310A (sv)
NO (1) NO163284C (sv)
NZ (1) NZ205626A (sv)
OA (1) OA07548A (sv)
PT (1) PT77404B (sv)
SE (1) SE461734B (sv)
SU (1) SU1493108A3 (sv)
YU (1) YU43196B (sv)
ZW (1) ZW20783A1 (sv)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4683296A (en) * 1983-03-07 1987-07-28 Bristol-Myers Company Carbapenem intermediates
CA1273011A (en) * 1984-07-02 1990-08-21 Susan M. Schmitt Carbapenems having an externally alkylated mono- or bicyclic 2-quaternary heteroarylalkylthio substituent
CA1273012A (en) * 1984-07-02 1990-08-21 Burton G. Christensen 1-methylcarbapenems having an externally alkylated mono- of bicyclic 2-quarternary heteroarylalkylthio substituent
US4680292A (en) * 1984-12-13 1987-07-14 Merck & Co., Inc. Carbapenems and 1-methylcarbapenems having a 2-heteroaryliumaliphatic substituent
US4725594A (en) * 1984-12-13 1988-02-16 Merck & Co., Inc. Carbapenems having an internally or externally alkylated mono- or bicyclic 2-quaternary heteroarylalxyl heteromethyl substituent
US4729993A (en) * 1984-12-13 1988-03-08 Merck & Co., Inc. Carbapenems and 1-methylcarbapenems having an externally alkylated mono- or bicyclic 2-quaternary heteroarylalkyl 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
DK168047B1 (da) * 1987-12-07 1994-01-24 Lederle Japan Ltd (1r,5s,6s)-2-substitueret thio-6-oe(r)-1-hydroxyethylaa-1-methyl-carbapenem-3-carboxylsyrederivater, fremgangsmaade til remstilling deraf, midler og praeparater indeholdende den krystallinske forbindelse samt dens anvendelse.
WO1997025325A1 (en) * 1996-01-12 1997-07-17 Takeda Chemical Industries, Ltd. Carbapenem compounds, their production and use

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK165280A (da) * 1979-04-19 1980-10-20 Merck & Co Inc Fremgangsmaade til fremstilling af 2- og 6-substituerede 1-carbadethiapen-2-em-3-carboxylsyrer og mellemprodukter til brug ved udoevelse af fremgangsmaaden
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
PT73791B (en) * 1980-10-17 1983-10-14 Merck & Co Inc Process for preparing 2-carbamimidoyl-6-substituted-1- -carbadethiapen-2-em-3-carboxylic acids
GB2089340B (en) * 1980-10-25 1984-09-19 Beecham Group Ltd -lactam antibiotics their preparation and their use
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

Also Published As

Publication number Publication date
LU85021A1 (fr) 1984-04-24
DK442383D0 (da) 1983-09-27
IT8323022A0 (it) 1983-09-27
GB2128187A (en) 1984-04-26
ZW20783A1 (en) 1984-11-28
SE8305217D0 (sv) 1983-09-27
CA1269978A (en) 1990-06-05
FI833417A0 (fi) 1983-09-23
KR890002228B1 (ko) 1989-06-24
NL8303310A (nl) 1984-04-16
DK442383A (da) 1984-03-29
FI833417A (fi) 1984-03-29
NZ205626A (en) 1986-12-05
PT77404A (en) 1983-10-01
ES8503354A1 (es) 1985-02-16
CH656130A5 (de) 1986-06-13
YU190683A (en) 1985-10-31
SE8305217L (sv) 1984-03-29
KR840006249A (ko) 1984-11-22
HU191066B (en) 1987-01-28
DE3334937A1 (de) 1984-04-05
GB2128187B (en) 1986-06-18
AU1934283A (en) 1984-04-05
DD212255A5 (de) 1984-08-08
IE832266L (en) 1984-03-28
IL69824A0 (en) 1983-12-30
GR78696B (sv) 1984-09-27
GB8325744D0 (en) 1983-10-26
SE461734B (sv) 1990-03-19
CS247168B2 (en) 1986-12-18
IT1163944B (it) 1987-04-08
FI78094B (fi) 1989-02-28
YU43196B (en) 1989-04-30
NO163284C (no) 1990-05-02
OA07548A (fr) 1985-03-31
DE3334937C2 (sv) 1991-05-02
SU1493108A3 (ru) 1989-07-07
FR2533568A1 (fr) 1984-03-30
PT77404B (en) 1986-06-26
ES525983A0 (es) 1985-02-16
FR2533568B1 (fr) 1990-01-26
AU575541B2 (en) 1988-08-04
AR241785A1 (es) 1992-12-30
AT382621B (de) 1987-03-25
NO163284B (no) 1990-01-22
IE55947B1 (en) 1991-02-27
ATA344983A (de) 1986-08-15
NO833479L (no) 1984-03-29
IL69824A (en) 1991-04-15

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