FI81085B - Foerfarande foer framstaellning av nya, farmaceutiskt aktiva 1-sulfo-2-oxoazetidinderivat. - Google Patents

Foerfarande foer framstaellning av nya, farmaceutiskt aktiva 1-sulfo-2-oxoazetidinderivat. Download PDF

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FI81085B
FI81085B FI813852A FI813852A FI81085B FI 81085 B FI81085 B FI 81085B FI 813852 A FI813852 A FI 813852A FI 813852 A FI813852 A FI 813852A FI 81085 B FI81085 B FI 81085B
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amino
thiazolyl
group
sulfonate
cis
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FI813852A
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English (en)
Finnish (fi)
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FI813852L (fi
FI81085C (sv
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Shoji Kishimoto
Taisuke Matsuo
Michiyuki Sendai
Mitsumi Tomimoto
Michihiko Ochiai
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Takeda Chemical Industries Ltd
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
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    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
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    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
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    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
    • C07D205/095—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4 and with a nitrogen atom directly attached in position 3
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    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
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    • 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
    • C07D277/32—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 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
    • C07D277/38—Nitrogen atoms
    • C07D277/44—Acylated amino or imino radicals
    • C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
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    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
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    • 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
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
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    • C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
    • C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom

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Claims (3)

1. Förfarande för framställning av ett farmaceutiskt aktivt l-sulfo-2-oxoazetidinderivat med formeln X R Rl--( I (I) \-N O xS03H där R1 är (1) en grupp med formeln O R« ib där Ra och bP, som kan vara lika eller olika, betecknar Cj.g-alkyl, (2) en grupp med formeln R7 r6-nh-ch-conh- där R6 är väte, karbamoyl, en alifatisk acyl, Ci-g-alkylsulfo-nyl, aromatisk acyl, arylsulfonyl, metoxiacetyl, esterifierad karboxyl, 1-metyl-l-karboxietylkarbonyl, karboxietylkarbonyl, karboxietenylkarbonyl eller en grupp med formeln R8-CO- (där R8 är (i) en grupp med formeln —— Rc-/ N- <f~\ där Rc är Ci-g-alkyl, eller 310 81085 (ii) en grupp med formeln d R°-CH*=N-N H- Y O där R^ är furyl eller tienyl) och \ R7 är fenyl, tienyl eller en grupp med formeln ”11 där Re är amino, (3) en grupp med formeln ‘Vy N-LI-C-CONH- M OR12 där R^ är amino, amino, som är skyddad med en ekyddegrupp som konventionellt används inom ^»-laktam- eller peptidisynte-sens omräde, Cj-g-alkyl eller hydroxyl, R9 är väte eller halogen, oCh R*2 är Cj_5-alkyl, C2-6-alkenyl eller en grupp med formeln -r!3_r14 (där R*3 är Cj_3-alkylen och R** är fenyl, karboxyl eller esterifierad karbonyl), (4) en grupp med formeln ^"^-(pHCONH- där R16 är hydroxyl, sulfo, karboxyl eller karboxyl, som är skyddad med en skyddsgrupp som konventionellt används i -laktamkemin eller inom den övriga organiska kemin, (5) en grupp med formeln R18-CH2CONH- 311 81085 där R18 är cyano, trietylsilylmetyl, tienyl, tetrazolyl eller en grupp med formeIn ^ 'YL (där Re är amino eller amino, som är skyddad pä det sätt som definierades vid R^), (6) en grupp med formeln "Yn N!-Li-CHCONH- OP-OC2H5 oc2h5 där Re är samma som ovan definierades, (7) ami,no, (8) amino, som är skyddad säsom definierades vid R^, eller (9) azido, R är (1)' en grupp med formeln -COQ5 där Q5 är Cj.g-alkoxi, p-nitrobensyloxi, hydroxyl eller Ci_g-alkoxikarbonyl-Cj-g-alkyloxi, ,->' en grupp med formeln 312 81 085 r2" -C-(CH2)n-R4" (A) R3" där n är ett helt tai mellan 0...3, R2" och R3", som kan vara lika eller olika, betecknar väte eller Cj-g-alkyl, och R4" är väte, Ci_6~alkyl, fenyl, halogen, cyano, hydroxyl, karbamoyl-oxi, Ci-g-alkylsulfonyloxi, hydroxisulfonyloxi, amino, azido, Ci_g-alkoxikarbonyl, Cj-g-alkyltio, kvaternär ammonium, Ci_g-alkylkarbonyloxi, halogen-Ci_g-alkylkarbonyloxi, l-Cj.g-alkyl-tetrazolyltio, bensoyloxi, Ci_g-alkylkarbonylamino, bensoyl-amino, trifluoracetylamino, Ci_g-alkylsulfonyl-Ci_g-alkyloxi-karbonylamino, p-nitrobensyloxikarbonylamino, eller en grupp med formeIn -OCO-X'-Q1 (där X' är -CH2-, -CH2S- eller -C- ), N«»Q2 och Q* är tienyl, l-Cj.g-alkyltetrazolyl eller 2-aminotiazolyl eller 2-aminotiazolyl, där aminon är skyddad s&som definiera-des vid R^, och Q2 är Ci_g-alkoxi, under förutsättningen att gruppen (A) inte repreeenterar en osubstituerad rak eller förgrenad alkylgrupp, (3) ' en grupp med formeln Q3 -CON^ ^Q4 där Q3 och Q4 , som kan vara lika eller olika, betecknar väte, Ci-g-alkyl, Ci_g-alkoxi, fenyl, karboxi-Ci_g-alkyl, där kar-boxylen är skyddad säsom definierades vid karboxi-Cj-g- alkyl eller sulfo, (4) ' en Cj.g-alkylkarbonylgrupp, (5) ' en fenyl-C2_g-alkenylgrupp, (6) ' p-halogenfenyl, och X är väte, il 313 81 085 eller dess farmaceutiskt acceptable salt eller ester, k ä n -netecknat av att a) man sulfonerar en förening med formeln x>— f UI) __NH där respektive symboler betecknar samma som ovan definierades, eller dess salt eller ester, varefter vid behov följer av-lägsnande av skyddsgruppen, eller b) man acylerar en förening med formeln W H2N I (III) o \o3h där R och X betecknar samma som definierades ovan, eller dess salt eller ester, och vid behov överför den sä erhällna föreningen i fri form eller i sin farmaceutiskt acceptable salt- eller esterform.
2. Förfarande enligt patentkravet 1, kännetecknat av att utgängsföreningen (II) silyleras med ett silylerings-medel.
3. Förfarande enligt patentkravet 1, kännetecknat av att man framställer 3-(2-(2-amino-4-tiaz olyl)-2-metoxi-iminoacetamido)-4-etoxikarbonyl-2-oxo-azetidin-l-sulfonsyra (syn-isomer).
FI813852A 1980-12-05 1981-12-02 Förfarande för framställning av nya, farmaceutiskt aktiva 1-sulfo-2-ox oazetidinderivat FI81085C (sv)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
PCT/JP1980/000297 WO1982001873A1 (en) 1980-12-05 1980-12-05 1-sulfo-2-oxoazetidine derivatives and process for their preparation
JP8100103 1981-04-30
PCT/JP1981/000103 WO1982003859A1 (en) 1980-12-05 1981-04-30 1-sulfo-2-oxoazetidine derivatives and process for their preparation
JP8100183 1981-08-21
PCT/JP1981/000183 WO1983000689A1 (en) 1980-12-05 1981-08-21 1-sulfo-2-oxoazetidine derivatives and process for their preparation
PCT/JP1981/000252 WO1983001063A1 (en) 1980-12-05 1981-09-24 1-sulfo-2-oxoazetidine derivatives and process for their preparation
JP8100252 1981-09-24
JP8000297 1981-12-05

Publications (3)

Publication Number Publication Date
FI813852L FI813852L (fi) 1982-06-06
FI81085B true FI81085B (fi) 1990-05-31
FI81085C FI81085C (sv) 1990-09-10

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FI813852A FI81085C (sv) 1980-12-05 1981-12-02 Förfarande för framställning av nya, farmaceutiskt aktiva 1-sulfo-2-ox oazetidinderivat

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US (3) US4550105A (sv)
EP (1) EP0053816B1 (sv)
AR (1) AR240171A1 (sv)
AT (1) AT378768B (sv)
AU (1) AU557689B2 (sv)
BE (1) BE891366A (sv)
BR (1) BR8107866A (sv)
CH (1) CH657610A5 (sv)
DE (2) DE3148021A1 (sv)
DK (1) DK534481A (sv)
ES (2) ES507715A0 (sv)
FI (1) FI81085C (sv)
FR (1) FR2495613B1 (sv)
GB (1) GB2091724B (sv)
GR (1) GR77295B (sv)
IE (1) IE53314B1 (sv)
IL (1) IL64315A (sv)
IT (1) IT1139919B (sv)
LU (1) LU83819A1 (sv)
MY (1) MY8700314A (sv)
NL (1) NL8105470A (sv)
NO (1) NO160577C (sv)
NZ (1) NZ199167A (sv)
PH (1) PH25221A (sv)
PT (1) PT74088B (sv)
SE (1) SE457256B (sv)
WO (5) WO1982001873A1 (sv)
YU (2) YU43051B (sv)

Families Citing this family (64)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ196202A (en) * 1980-02-07 1984-07-31 Squibb & Sons Inc Beta-lactam antibiotics (of azetidine-sulphonic acid type)
EP0048953B1 (en) * 1980-09-29 1988-03-09 E.R. Squibb &amp; Sons, Inc. Beta-lactam antibiotics
WO1982001873A1 (en) * 1980-12-05 1982-06-10 Takeda Chemical Industries Ltd 1-sulfo-2-oxoazetidine derivatives and process for their preparation
US4673739A (en) * 1980-12-05 1987-06-16 Takeda Chemical Industries, Ltd. 4-carbamoyloxymethyl-1-sulfo-2-oxoazetidine derivatives and their production
US4675397A (en) * 1980-12-05 1987-06-23 Takeda Chemical Industries, Ltd. 1-sulfo-2-oxoazetidine derivatives and their production
US4782147A (en) * 1980-12-05 1988-11-01 Takeda Chemical Industries, Ltd. 1-sulfo-2-oxoazetidine derivatives and their production
US4572801A (en) * 1981-04-30 1986-02-25 Takeda Chemical Industries, Ltd. 4-Carbamoyloxymethyl-1-sulfo-2-oxoazetidine derivatives and their production
EP0187355A1 (en) * 1981-09-23 1986-07-16 E.R. Squibb &amp; Sons, Inc. Process for preparing beta-lactam antibiotics
GB2151628B (en) * 1981-10-23 1986-05-21 Roussel Uclaf Azetidine intermediates
FR2558467B2 (fr) * 1981-10-23 1987-03-20 Roussel Uclaf Nouveau produit derive de l'acide 3-amino 2-oxo azetidine 1-sulfamique, son procede de preparation, son application comme medicament et un produit intermediaire necessaire a sa preparation
FR2515182B1 (fr) * 1981-10-23 1986-05-09 Roussel Uclaf Nouveaux produits derives de l'acide 3-amino 2-oxo azetidine 1-sulfamique, leur procede de preparation, leur application comme medicaments et les produits intermediaires necessaires a leur preparation
FR2538389B2 (fr) * 1981-10-23 1986-05-16 Roussel Uclaf Nouveaux produits derives de l'acide 3-amino 2-oxo azetidine-1-sulfamique, nouveau procede de preparation de produits optiquement actifs, application des nouveaux produits comme medicaments et produits necessaires a leur preparation
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IL64315A (en) 1988-04-29
AU557689B2 (en) 1987-01-08
SE457256B (sv) 1988-12-12
NZ199167A (en) 1985-08-30
EP0053816A1 (en) 1982-06-16
GB2091724A (en) 1982-08-04
WO1983000689A1 (en) 1983-03-03
ES8303328A1 (es) 1983-02-01
WO1982001873A1 (en) 1982-06-10
IE812860L (en) 1982-06-05
ES516254A0 (es) 1983-10-16
IT1139919B (it) 1986-09-24
NO160577B (no) 1989-01-23
MY8700314A (en) 1987-12-31
US4822788A (en) 1989-04-18
GB2091724B (en) 1985-07-31
FR2495613A1 (fr) 1982-06-11
PT74088B (en) 1983-05-23
ES8400400A1 (es) 1983-10-16
AT378768B (de) 1985-09-25
BR8107866A (pt) 1982-09-08
WO1982002043A1 (en) 1982-06-24
AR240171A1 (es) 1990-02-28
YU43051B (en) 1989-02-28
EP0053816B1 (en) 1988-05-04
IL64315A0 (en) 1982-02-28
FR2495613B1 (fr) 1985-08-09
IT8125464A0 (it) 1981-12-04
IE53314B1 (en) 1988-10-12
ES507715A0 (es) 1983-02-01
DK534481A (da) 1982-06-06
NL8105470A (nl) 1982-07-01
GR77295B (sv) 1984-09-11
LU83819A1 (fr) 1982-05-07
AU7782981A (en) 1982-06-10
DE3176731D1 (en) 1988-06-09
WO1982003859A1 (en) 1982-11-11
FI813852L (fi) 1982-06-06
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US4665067A (en) 1987-05-12
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FI81085C (sv) 1990-09-10
WO1983001063A1 (en) 1983-03-31
SE8107274L (sv) 1982-06-06
PT74088A (en) 1982-01-01
PH25221A (en) 1991-03-27
BE891366A (fr) 1982-06-04
CH657610A5 (de) 1986-09-15
ATA520881A (de) 1985-02-15
DE3148021A1 (de) 1982-10-21
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