FI85487B - Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 3- propenylaminotiazolylcefalosporansyror och estrar. - Google Patents

Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 3- propenylaminotiazolylcefalosporansyror och estrar. Download PDF

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Publication number
FI85487B
FI85487B FI862642A FI862642A FI85487B FI 85487 B FI85487 B FI 85487B FI 862642 A FI862642 A FI 862642A FI 862642 A FI862642 A FI 862642A FI 85487 B FI85487 B FI 85487B
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FI
Finland
Prior art keywords
cephem
aminothiazol
acetamido
carboxylate
carboxylic acid
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FI862642A
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English (en)
Finnish (fi)
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FI862642A (fi
FI862642A0 (fi
FI85487C (sv
Inventor
Seiji Iimura
Yoshio Abe
Jun Okumura
Takayuki Naito
Hajime Kamachi
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Squibb Bristol Myers Co
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Publication of FI862642A0 publication Critical patent/FI862642A0/fi
Publication of FI862642A publication Critical patent/FI862642A/fi
Publication of FI85487B publication Critical patent/FI85487B/fi
Application granted granted Critical
Publication of FI85487C publication Critical patent/FI85487C/sv

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/22—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with radicals containing only hydrogen and carbon atoms, attached in position 3
    • 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
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Claims (2)

1, Il (xvii) R -NH-Vc/ b \ 2a 0R^a 15 väri R1' är en vanlig inom cefalosporinkemin använd amino- skyddsgrupp; R2* är en vanlig inom cefalosporinkemin använd hydroxiskyddsgrupp, alkyl med 1-4 kolatomer, alkenyl eller alkinyl med 2-4 kolatomer, cykloalkyl med 3-6 kolatomer, eller alkanoyl med 2-4 kolatomer; och R4' är 20 en vanlig inom cefalosporinkemin använd karboxylskydds- grupp, bringas att reagera med en aldehyd med formeln R3CH2CHO 25 väri R3 betecknar samma som ovan, i ett inert organiskt reaktionsmedium, säsom diklormetan, N,N-dimetylformamid, isopropanol eller en blandning av dessa, eventuallt i när-varo av litiumklorid, litiumbromid eller litiumjodid, vid en reaktionstemperatur pä 0 - 25 °C, varvid en förening med 30 formeln
5 S R~| 1 I (XVIII) J Nv — CH=CHCH ~RJ : 35 of •: · 4 ' C00R 103 8 5 4 8 7 erhälles, och dä R5:n betecknar en bensylidengrupp (XVI), avlägsnas nämnda grupp selektivt, 3-(Z)-isomeren omvandlas tili (E)-isomeren medelst en fotokeraisk reaktion och en grupp med formeln XVII tillfogas, varvid en 5 förening med formeln N-— C-C0NH-- 1 li I II I 3
10 R —HN s y/ N 0^_-nVv^-CH=CHCH2R·3 (xix) C00R4 ' 15 erhälles och därefter avlägsnas skyddsgrupperna R1', R2* och R4', och om sä önskas separeras 3-(Z)- ja 3-(E)-iso-mererna varvid en förening med formeln 20 N-rr-C-CONH--f S ^ J I i I 3 <Ia> H2N“Vs^ N -N^x^CH^HCH^·3
2 I 25 0R C00H väri R2 och R3 betecknar samma som ovan erhälles, och om sä önskas bringas alkalimetallsaltet eller ammoniumsaltet av 30 föreningen Ia att reagera med en halogenid med formeln R4b-X väri X betecknar halogen säsom klor, brom eller jod, och ‘ 35 R4b pivaloyloximetyl, 1-acetoxietyl, acetoximetyl, 5-me- 104 8 5 4 87 tyl-2-oxo-l,3-dioksolen-4-ylmetyl, eller en grupp med formeln
5. M // (XXI) ° r°-nhch2c-o —r xVc-och2 vari R6 betecknar väte eller en inom cefalosporinikemin 10 vanlig aminoskyddsgrupp, och om sä önskas avlägsnas skyddsgruppen, varvld en ester med formeln
15 N-- C-CONH--S J 1 11 ' 3 ^2N ^ g/ N 0.^-NV'£'^~CH=CHCH2R'i Ub) 0R COOR D 20 erhälles, väri R4 betecknar samma som ovan.
1. Förfarande för framställning av nya terapeu-tiskt användbara 3-propenylaminotiazolylcefalosporansyror 5 och estrar med formeln I
10 J 0^N^>LcH=CHCH2R3 (i) or2 coor4 väri
15 R1 betecknar väte eller en vanlig aminoskyddsgrupp; R2 betecknar väte, rak eller förgrenad alkyl med 1-4 kol-atomer, alkenyl eller alkinyl med 2-4 kolatomer, cykloal-kyl med 3-6 kolatomer, cykloalkylalkyl med 3-6 ringatomer och 4-10 kolatomer, eller alkanoyl med 2-4 kolatomer;
20 R3 betecknar väte, lägre alkyl med 1-3 kolatomer, lägre alkoxi med 1-3 kolatomer, lägre alkanoyloxi med med 2-3 kolatomer; och R4 betecknar väte eller en fysiologiskt hydrolyserbar est-ergrupp; 25 kännetecknat därav, att en förening med formeln r5n_ . S
30 I Γ I JCH=PPh3 (XV) 35 4 · 2 COOR 102 8 5 487 väri R5 betecknar en grupp med formeln 5 ^ ^-CH=N- (XVI) eller en grupp med formeln 10 N-—CC0NH-
2. Förfarande enligt patentkravet 1, k ä n note c k n a t därav, att man framställer 76- [ (Z) -2- (2-aminotiazol-4-yl) -2- (hydroxiimino) -acetami-25 do]-3-(Z)-prop-l-en-l-y]-3-cefem-4-karboxylsyra, 78- [ (Z)-2-(2-aminotiazol-4-yl)-2-(hydroxiimino)-acetami-do]-3-[(E)-prop-1-en-l-yl]-3-cefem-4-karboxylsyra, l-acetoxietyl-78-[(Z)-2-(2-aminotiazol-4-yl)-2-hydroxi-imino)-acetamido]-3-[(Z)-prop-l-en-l-yl]-3-cefem-4-kar-30 boxylat, pivaloyloximetyl-78-[(Z)-2-(2-aminotiazol-4-yl)-2-(hyd-. . roxiimino)-acetamldo]-3-[(Z)-prop-1-en-l-yl]-3-cefem-4- karboxylat, pivaloyoximetyl-78-[(Z)-2-(2-aminotiazol-4-yl)-2-(hyd-’ 35 roxiimino)-acetamido]-3-[(E)-prop-l-en-l-yl]-3-cefem-4- karboxylat. 105 8 5 487 7β-[(Ζ)-2-(2-aminotiazol-4-yl)-2-(hydroxiimino)-acet-amido]—3—[(Z)-3-acetoxiprop-l-en-l-yl]-3-cefem-4-kar-boxylsyra, 78- [ (Z) -2- (2-aminotiazol-4-yl) -2- (hydroxiimino) -acet-5 amido]-3-[(E)-3-acetoxiprop-l-en-l-yl]-3-cefem-4-karboxylsyra, 78-[(Z)-2-(2-aminotiazol-4-yl)-2-(metoxiimino)-acet-amido]-3-[(Z)-prop-l-en-l-yl]-3-cefem-4-karboxylsyra, 78-[(Z)-2-(2-aminotiazol-4-yl)-2-(metoxiimino)-acet-10 amido]-3-[(E)-prop-l-en-l-yl]-3-cefem-4-karboxylsyra, l-acetoxietyl-78-[(Z)-2-(2-aminotiazol-4-yl)-2-(metoxiimino )-acetamido]-3-[(Z)-prop-1-en-1-yl]-3-cefem-4-kar-boxylat, l-acetoxietyl-78-[(Z)-2-(2-aminotiazol-4-yl)-2-(metoxi-15 imino)-acetamido]-3-[(E)-prop-l-en-l-yl]-3-cefem-4-kar- boxylat, pivaloyloximetyl-78-[(Z)-2-(2-aminotiazol-4-yl)-2-(metoxiimino )-acetamido]-3-[(Z)-prop-l-en-l-yl]-3-cefem-4-karboxylat, 20 78-[(Z)-2-(2-aminotiazol-4-yl)-2-(metoxiimino)-acetami do] -3-[(Z)-but-1-en-1-yl]-3-cefem-4-karboxylsyra, 78-[(Z)-2-(2-aminotiazol-4-yl)-2-(metoxiimino)-acetamido] -3-[(E)-but-1-en-1-yl]-3-cefem-4-karboxylsyra, acetoximety 1-78- [Z )-2-( 2-aminotiazol-4-yl )-2-(metoxiimi-25 no-acetamido-3-[(Z)-but-1-en-1-yl]-3-cefem-4-karboxylat, 1-acetoxietyl-78-[(Z)-2-(2-aminotiazol-4-yl)-2-(metoxiimino ) -acetamido] -3-[(Z)-but-1-en-1-yl]-3-cefem-4-karbox-ylat, 1 -acetoxietyl-78-[(Z)-2-(2-aminotiazol-4-yl)-2-(metoxi-30 imino)-acetamido]-3-[(E)-but-1-en-1-yl]-3-cefem-4-karbox- yiat, pivaloyloximetyl-78-[(Z)-2-(2-aminotiazol-4-yl)-2-(metoxiimino )-acetamido]-3-[(Z)-but-1-en-1-yl]-3-cefem-4-karboxylat, 35 78-[(Z)-2-(2-aminotiazol-4-yl)-2-(2-metoxiimino)-acetami do] -3-[(Z)-pent-1-en-1-yl]-3-cefem-4-karboxylsyra, 106 8 5 487 7S-[(Ζ)-2-(2-aminotiazol-4-yl)-2-(2-metoxiimino)-acetami-do]-3-[(E)-pent-1-en-l-yl]-3-cefem-4-karboxylsyra, l-acetoxsietyl-7B-[ (Z )-2-(2-aminotiazol-4-yl)-2-(metoxi-imino)-acetamido]-3-[(Z)-pent-1-en-l-yl]-3-cefem-4-kar-5 boxylat, 7B-[ (Z)-2-(2-aminotiazol-4-yl)-2-(metoxiimino)-acetamido] -3-[(Z)-3-acetoxiprop-l-en-l-yl]-3-cefem-4-karboxylsy-ra, 7B- [ (Z)-2-(2-aminotiazol-4-yl)-2-(metoxiimino)-acetami-10 do]-3-[(E)-3-acetoxiprop-l-en-l-yl]-3-cefem-4-karboxylsy- ra, acetoximetyl-7B-[(Z)-2-(2-aminotiazol-4-yl)-2-(metoxiimino)-acetamido] —3—[(Z)-3-acetoxiprop-l-en-l-yl]-3-ce-fem-4-karboxylat, acetoxietyl-7B- [ (Z) -2-( 2-aminotiazol-4-yl )-2-( metoxiimi-15 no)-acetamido]—3—[(Z)-acetoxiprop-1-en-l-yl]-3-cefem-4- karboxylat, acetoxietyl-76- [ ( Z )-2-(2-aminotiazol-4-yl)-2-(metoxiimi-no)-acetamido]-3-[(E)-acetoxiprop-1-en-l-yl]-3-cefem-4-karboxylat, 20 7B-tX Z)-2-(2-aminotiazol-4-yl)-2-(acetoxiimino)-acet amido] -3-[(Z)-prop-1-en-l-yl]-3-cefem-4-karboxylsyra, l-acetoxietyl-7B- [ (Z )-2- (2-aminotiazol-4-yl) -2-( acetoxiimino )-acetamido]-3-[(Z)-prop-l-en-l-yl]-3-cefem-4-kar-boxylat, 25 7B-[(Z)-2-(2-aminotiazol-4-yl)-2-(acetoxiimino)-acet amido] -3- [ (Z)-acetoxiprop-1-en-l-yl ] -3-cef em-4-karboxyl-syra, l-acetoxietyl-7B- [ (Z )-2-( 2-aminotiazol-4-yl) -2-( acetoxiimino) -acetamido]—3—[(Z)-3-acetoxiprop-1-en-l-yl]-3-ce-30 fem-4-karboxylat, l-axetoxietyl-7B- [ ( Z )-2-( 2-aminotiazol-4-yl) -2-( acetoxiimino)-acetamido] -3-[(E)-3-acetoxiprop-1-en-1-yl]-3-ce-fem-4-karboxylat, 78-[(Z)-2-(2-aminotiazol-4-yl)-2-(isopropyloxiimino)-35 acetamido]-3-[(Z)-prop-l-en-l-yl]-3-cefem-4-karboxylsyra, 107 8 5 4 8 7 75- [(Ζ)-2-(2-aminotiazol-4-yl)-2-(allyloxiimino)-acetami-do]-3-t(Z)-prop-l-en-l-yl]-3-cefem-4-karboxylsyra, 7β-C(Z)—2—(2-aminotlazol-4-yl)-2-(etoxiimino)-acetami-do]-3-[(Z)-prop-l-en-l-yl]-3-cefem-4-karboxylsyra, 5 7B-[(Z)-2-(2-aminotiazol-4-yl)-2-(cyklopropylmetoxiimi- no]-asetamidoj-3-[(Z)-prop-l-en-l-yl]-3-cefem-4-karboxyl-syra, 76- [(Z)-2-(2-aminotiazol-4-yl)-2-(propargyloxiimino)-acetamido]-3-[(Z )-prop-l-en-l-yl]-3-cefem-4-karboxylsy- 10 ra, (5-metyl-2-oxo-1,3-dioxolen-4-yl)-metyl-76-[(Z)-2-(2-ami-notiazol-4-yl)-2-(hydroxiimino)-acetamido]-3-[(Z)-prop-l-en-yl]-3-cefem-4-karboxylat, eller 15 1-(etoxikarbonyloxi)-etyl-70-[(Z)-2-(2-aminotiazol-4-yl)- 2-(hydroxiamlno)-acetamido] -3- [ ( Z )-prop-l-en-l-yl] -3-ce-fem-4-karboxylat. 1
FI862642A 1985-06-24 1986-06-19 Förfarande för framställning av nya terapeutiskt användbara 3-propenyl aminotiazolylcefalosporansyror och estrar FI85487C (sv)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US74835985 1985-06-24
US06/748,359 US4708955A (en) 1985-06-24 1985-06-24 3-(substituted)propenyl-7-aminothiazol-ylcephalosporanic acids and esters thereof

Publications (4)

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FI862642A0 FI862642A0 (fi) 1986-06-19
FI862642A FI862642A (fi) 1986-12-25
FI85487B true FI85487B (fi) 1992-01-15
FI85487C FI85487C (sv) 1992-04-27

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FI862642A FI85487C (sv) 1985-06-24 1986-06-19 Förfarande för framställning av nya terapeutiskt användbara 3-propenyl aminotiazolylcefalosporansyror och estrar

Country Status (36)

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US (1) US4708955A (sv)
JP (1) JPS62491A (sv)
KR (1) KR930007416B1 (sv)
AR (1) AR244233A1 (sv)
AT (1) AT390956B (sv)
AU (1) AU593557B2 (sv)
BE (1) BE904983A (sv)
CA (1) CA1279868C (sv)
CS (1) CS258142B2 (sv)
CY (1) CY1618A (sv)
DD (1) DD246112A5 (sv)
DE (1) DE3620995A1 (sv)
DK (1) DK295386A (sv)
EG (1) EG17868A (sv)
ES (1) ES8800680A1 (sv)
FI (1) FI85487C (sv)
FR (1) FR2583757B1 (sv)
GB (1) GB2178032B (sv)
GR (1) GR861611B (sv)
HK (1) HK106091A (sv)
HU (1) HU199484B (sv)
IE (1) IE59123B1 (sv)
IL (1) IL79181A0 (sv)
IT (1) IT1221767B (sv)
LU (1) LU86488A1 (sv)
MY (1) MY102073A (sv)
NL (1) NL8601645A (sv)
NZ (1) NZ216614A (sv)
OA (1) OA08349A (sv)
PH (2) PH21206A (sv)
PT (1) PT82836B (sv)
SE (1) SE500218C2 (sv)
SG (1) SG91691G (sv)
SU (1) SU1428204A3 (sv)
YU (1) YU45787B (sv)
ZA (1) ZA864297B (sv)

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US4874856A (en) * 1985-06-24 1989-10-17 Bristol-Myers Company 3-(substituted)propenyl-7-(aminothiazolylacetamido) ceph-3-em-4-carboxylic acids and esters thereof
GB8519606D0 (en) * 1985-08-05 1985-09-11 Fujisawa Pharmaceutical Co 3 7-d substituted-3-cephem compounds
US4870168A (en) * 1987-02-26 1989-09-26 Bristol-Myers Company 3-Unsaturated alkyl cephems from 3-triflyl cephems
FR2622585B1 (fr) * 1987-11-03 1991-04-19 Roussel Uclaf Nouvelles cephalosporines comportant en position 3 un radical vinyle substitue, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus
US4935508A (en) * 1988-08-23 1990-06-19 Bristol-Myers Company Process for cephem prodrug esters
US5143911A (en) * 1990-08-23 1992-09-01 Bristol-Myers Squibb Company Antibiotic c-3 di-hydroxyphenyl substituted cephalosporin compounds, compositions and method of use thereof
DK0630380T3 (da) 1992-02-05 2001-12-10 Biochemie Gmbh Fremgangsmåde til rensning af et 3-cephem-4-carboxylsyrederivat
JPH07173168A (ja) * 1993-07-14 1995-07-11 Sumitomo Chem Co Ltd セフェム系化合物、その製法、およびそれのセフェム系抗生物質製造への利用
KR100408430B1 (ko) * 2001-04-18 2003-12-06 한미약품 주식회사 3-(ｚ)-프로페닐 세펨 화합물의 선택적인 제조 방법
WO2005042543A1 (en) * 2003-10-30 2005-05-12 Cj Corporation Processes for the preparation of cephem derivatives

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ZA864297B (en) 1987-02-25
HU199484B (en) 1990-02-28
EG17868A (en) 1994-01-30
AR244233A1 (es) 1993-10-29
NZ216614A (en) 1990-03-27
SE500218C2 (sv) 1994-05-09
SE8602780L (sv) 1986-12-25
PH21879A (en) 1988-03-25
DK295386A (da) 1986-12-25
DK295386D0 (da) 1986-06-23
HUT43074A (en) 1987-09-28
OA08349A (fr) 1988-02-29
FI862642A (fi) 1986-12-25
GR861611B (en) 1986-10-30
YU45787B (sh) 1992-07-20
AU5882186A (en) 1987-01-08
AT390956B (de) 1990-07-25
JPS62491A (ja) 1987-01-06
SU1428204A3 (ru) 1988-09-30
FR2583757A1 (fr) 1986-12-26
CA1279868C (en) 1991-02-05
YU110086A (en) 1987-10-31
IT8620894A0 (it) 1986-06-24
GB8615253D0 (en) 1986-07-30
ATA171986A (de) 1990-01-15
BE904983A (fr) 1986-12-23
ES556465A0 (es) 1987-11-01
CS258142B2 (en) 1988-07-15
KR870000342A (ko) 1987-02-18
SG91691G (en) 1991-12-13
DE3620995A1 (de) 1987-01-08
FR2583757B1 (fr) 1989-01-13
KR930007416B1 (ko) 1993-08-10
FI862642A0 (fi) 1986-06-19
IT1221767B (it) 1990-07-12
HK106091A (en) 1992-01-03
DD246112A5 (de) 1987-05-27
PT82836B (pt) 1989-01-17
CY1618A (en) 1992-07-10
AU593557B2 (en) 1990-02-15
SE8602780D0 (sv) 1986-06-23
MY102073A (en) 1992-03-31
IL79181A0 (en) 1986-09-30
FI85487C (sv) 1992-04-27
CS462486A2 (en) 1987-11-12
IE861670L (en) 1986-12-24
LU86488A1 (fr) 1987-01-13
US4708955A (en) 1987-11-24
GB2178032A (en) 1987-02-04
NL8601645A (nl) 1987-01-16
PH21206A (en) 1987-08-19
IE59123B1 (en) 1994-01-12
PT82836A (en) 1986-07-01
GB2178032B (en) 1989-04-26
ES8800680A1 (es) 1987-11-01

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