SE7906899L - SULFINYLAZETIDINONE COMPOUNDS - Google Patents

SULFINYLAZETIDINONE COMPOUNDS

Info

Publication number
SE7906899L
SE7906899L SE7906899A SE7906899A SE7906899L SE 7906899 L SE7906899 L SE 7906899L SE 7906899 A SE7906899 A SE 7906899A SE 7906899 A SE7906899 A SE 7906899A SE 7906899 L SE7906899 L SE 7906899L
Authority
SE
Sweden
Prior art keywords
formula
group
alkyl
given above
meanings given
Prior art date
Application number
SE7906899A
Other languages
Swedish (sv)
Other versions
SE444810B (en
Inventor
S P Kukolja
Original Assignee
Lilly Co Eli
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 Lilly Co Eli filed Critical Lilly Co Eli
Publication of SE7906899L publication Critical patent/SE7906899L/en
Publication of SE444810B publication Critical patent/SE444810B/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • 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
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

3-Methylenecepham 1-sulphoxides of the formula <IMAGE> in which the substituents are defined in Claim 1 are prepared. These compounds are prepared by bringing about ring closure in a corresponding sulphinylazetidinone of the formula <IMAGE> in which X is chlorine or bromine, an alcohol or thioalcohol residue, an ester or a thioester residue, or an amino radical. If X is chlorine or bromine, the compound II is reacted with a Friedel-Crafts catalyst of the Lewis acid type, with a Friedel-Crafts catalyst of the Bronsted protonic acid type or with a metathetical cation former in a dry inert organic solvent, or is dissolved in an organic Bronsted acid. If X in compounds II is an alcohol, thioalcohol, ester or thioester residue or an amino radical, reaction is carried out with a Friedel-Crafts catalyst of the Bronsted protonic acid type in a dry inert organic solvent, or the compound is dissolved in an organic Bronsted acid. The resulting compounds can be used for the preparation of cephem antibiotics.

Claims (5)

Patentkrav 1. Sulfinylazetidinonforeningar avsedda f6r 3-metylencefamsulfoxider cch cefemantibiotika, made av formeln:0 r/SX 0)—Nyt, COCR vdri R betecknar en karboxylsyragruppen akyddande grupp; Hi betecknar (1) en imidogrupp med formeln: R2 •.„ van i 112 betecknar C2-C4-a1 nylen, 22-C4-alkylen, , 2-feny1 ,2-cyklcheen; eller (4) en imidazolidinylgrupp med formeln: 0 /I 3 i vilken R" bar ovan angivna betydelser och Y betecknar acetyl eller nitroso; och X betecknarClaims 1. Sulfinylazetidinone compounds for 3-methylenecepham sulfoxides and cephem antibiotics, made from the formula: 0 r / SX 0) -New, COCR wherein R represents a carboxylic acid protecting group; H 1 represents (1) an imido group of the formula: R 2 • of 112 represents C 2 -C 4 -alkylene, 22-C 4 -alkylene, 2-phenyl, 2-cyclchene; or (4) an imidazolidinyl group of the formula: O / I 3 in which R "had the meanings given above and Y represents acetyl or nitroso; and X represents 1. en grupp med formeln -0R4, dar R4 betecknar vAte, C1-0-alkyl, aryl(C1-03-alkyl) oiler Ci-C6- -halogenalkyl; 2. en grupp med formeln -SR, (Jar R betecknar 01,06-alkyl, aryl eller aryi-(01-03-alkyl); eller 3. en grupp med formeln: 6 -N R7 ,NH3 CH (2) en amidogrupp med formeln: 0 4NH- vari 23 betecknar (o) vRte, C1-C3-alkyl, halogenmetyl eller 3-(2-klorfeny1)-5-metyl-isoxasoly1;A group of the formula -OR 4, wherein R 4 represents vAte, C 1-10 alkyl, aryl (C 1-3 alkyl) or C 1 -C 6 haloalkyl; 2. a group of the formula -SR, (Jar R represents 01.06-alkyl, aryl or ary- (01-03-alkyl); or 3. a group of the formula: 6 -N R7, NH3 CH (2) a amido group of the formula: 4NH- wherein 23 represents (o) vRte, C 1 -C 3 alkyl, halomethyl or 3- (2-chlorophenyl) -5-methyl-isoxasolyl; 2. bensyloxi, 4-nitrobensyloxi, 2,2,2-trikloretoxi, t-butoxi eller 4-metoxibensyloxi;Benzyloxy, 4-nitrobenzyloxy, 2,2,2-trichloroethoxy, t-butoxy or 4-methoxybenzyloxy; 3. gruppen R" dKr R" betecknar 1,4-cyklohexadienyl, fenyl, eller fenyl substituerad med 1 eller 2 substituenter valda oberoende am varandra bland: halogen, skyddad hydroxi, nitro, cyano, trifluormetyl, 01-04-alkoxi, C1-04-, fOretrEdesvis C1-C3-alkyl;The group R "dKr R" represents 1,4-cyclohexadienyl, phenyl, or phenyl substituted with 1 or 2 substituents independently selected from: halogen, protected hydroxy, nitro, cyano, trifluoromethyl, 01-04-alkoxy, C1- 04-, preferably C1-C3-alkyl; 4. en grupp med formeln: R" - (0)-022- marl R" bar oven angivna betydelser och m Kr 0 eller 1;4. a group of the formula: R "- (0) -022- marl R" had the meanings given above and m Kr 0 or 1; 5. en substituerad arylalkylgrupp med formeln: dar (a) R6 betecknar mate och 27 betecknar site, R" med oven angivna betydelser, eller en grupp med formeln -NHR8, dAr R8 betecknar aminokaroonyl, C1-03-alkylaminokarbonYl, C1-03-alkylkarbonyl, C1-03-alkoxikarbonyl eller tosyl; eller (b) 26, 27 och den kvaveatom, mid silken de in bundna, tillsammans betecknar en imidogrupp med formeln: 0 dRr R2 bar oven angivna betydelser. w dgr R'" betecknar R" med ovan angivna betydelser och W betecknar skyddad hydroxi eller skyddad amino; (3) en imidogrupp med formeln: 0 R2 'C N- R"-(0) CH CZ/ m OR/. R" och m har oven angivna betydelser och R2' betecknar C1-C3-alkyl, C2-C3-halogenalkyl, C1-C3-alkoxi eller trikloretoxi; eller Ri betecknar5. a substituted arylalkyl group of the formula: wherein (a) R 6 represents mate and 27 represents site, R "having the meanings given above, or a group of the formula -NHR8, where R8 represents aminocaroonyl, C1-03-alkylaminocarbonyl, C1-03- alkylcarbonyl, C 1 -C 3 alkoxycarbonyl or tosyl; or (b) 26, 27 and the nitrogen atom, with the silks they bind together, represent an imido group of the formula: 0 dRr R 2 had the meanings given above. w dgr R '"denotes R" with the meanings given above and W represents protected hydroxy or protected amino; (3) an imido group of the formula: O R 2 'C N-R "- (O) CH C 2 / m OR /. R "and m have the meanings given above and R 2 'represents C 1 -C 3 alkyl, C 2 -C 3 haloalkyl, C 1 -C 3 alkoxy or trichloroethoxy; or R 1 represents
SE7906899A 1974-12-24 1979-08-17 SULFINYAZETIDINONE COMPOUNDS FOR USING THE PREPARATION OF 3-METHYLENCEFAMSULPHOXIDES SE444810B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US53628074A 1974-12-24 1974-12-24
US63273375A 1975-11-19 1975-11-19

Publications (2)

Publication Number Publication Date
SE7906899L true SE7906899L (en) 1979-08-17
SE444810B SE444810B (en) 1986-05-12

Family

ID=27065082

Family Applications (2)

Application Number Title Priority Date Filing Date
SE7514550A SE431547B (en) 1974-12-24 1975-12-22 PROCEDURE FOR THE PREPARATION OF 3-METHYLENCEFAM SULPHOXIDES
SE7906899A SE444810B (en) 1974-12-24 1979-08-17 SULFINYAZETIDINONE COMPOUNDS FOR USING THE PREPARATION OF 3-METHYLENCEFAMSULPHOXIDES

Family Applications Before (1)

Application Number Title Priority Date Filing Date
SE7514550A SE431547B (en) 1974-12-24 1975-12-22 PROCEDURE FOR THE PREPARATION OF 3-METHYLENCEFAM SULPHOXIDES

Country Status (25)

Country Link
JP (1) JPS606960B2 (en)
AR (1) AR220505A1 (en)
AT (1) AT341672B (en)
AU (1) AU503202B2 (en)
BE (1) BE837041A (en)
BG (2) BG31072A4 (en)
CA (1) CA1056372A (en)
CH (3) CH625528A5 (en)
CS (1) CS191291B2 (en)
DD (2) DD124985A5 (en)
DE (1) DE2556045A1 (en)
DK (1) DK157137C (en)
ES (2) ES443829A1 (en)
FR (2) FR2333804A1 (en)
GB (1) GB1536288A (en)
GR (1) GR59922B (en)
HU (2) HU177431B (en)
IE (1) IE42190B1 (en)
IL (1) IL48565A (en)
NL (1) NL182880C (en)
PL (2) PL114521B1 (en)
RO (2) RO74273A (en)
SE (2) SE431547B (en)
SU (1) SU799667A3 (en)
YU (2) YU324875A (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4289695A (en) * 1978-11-13 1981-09-15 Eli Lilly And Company Process for preparing 2-chlorosulfinylazetidinones
US4190724A (en) * 1978-11-13 1980-02-26 Eli Lilly And Company Process for 3-exomethylenecepham sulfoxides
GB2099817B (en) * 1981-04-10 1985-05-15 Otsuka Kagaku Yakuhin Azetidinone derivatives and process for the preparation of the same
US4436596A (en) * 1982-11-16 1984-03-13 Eli Lilly And Company N-Substituted-2-(R)-(sulfinic acid)-3-(S)-(acylamido)-4-oxo-azetidines and process
DE4230053A1 (en) * 1992-09-08 1994-03-10 Pliva Handels Gmbh 4-oxo-azetidine-2-sulfonic acid amides and their salts, process for their preparation and their use

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3843682A (en) * 1972-05-15 1974-10-22 Lilly Co Eli 2-chlorosulfinyl-3-imido-azetedin-4-ones

Also Published As

Publication number Publication date
YU324875A (en) 1982-02-28
ATA980475A (en) 1977-06-15
JPS606960B2 (en) 1985-02-21
FR2333804A1 (en) 1977-07-01
IE42190B1 (en) 1980-06-18
FR2300080A1 (en) 1976-09-03
FR2300080B1 (en) 1979-06-15
DD124985A5 (en) 1977-03-23
NL182880C (en) 1988-06-01
SE431547B (en) 1984-02-13
YU206481A (en) 1983-06-30
HU177431B (en) 1981-10-28
NL182880B (en) 1988-01-04
BE837041A (en) 1976-06-23
DK585875A (en) 1976-06-25
BG27236A3 (en) 1979-09-14
PL114521B1 (en) 1981-02-28
CA1056372A (en) 1979-06-12
NL7515069A (en) 1976-06-28
SE7514550L (en) 1976-06-25
CH626604A5 (en) 1981-11-30
RO74273A (en) 1981-08-17
BG31072A4 (en) 1981-10-15
DD130933A5 (en) 1978-05-17
RO68478A (en) 1981-08-30
DE2556045A1 (en) 1976-07-08
AT341672B (en) 1978-02-27
CH628620A5 (en) 1982-03-15
JPS5188992A (en) 1976-08-04
PL113883B1 (en) 1981-01-31
GR59922B (en) 1978-03-20
GB1536288A (en) 1978-12-20
HU175226B (en) 1980-06-28
SU799667A3 (en) 1981-01-23
IL48565A (en) 1979-09-30
AR220505A1 (en) 1980-11-14
ES443829A1 (en) 1978-03-01
SE444810B (en) 1986-05-12
AU503202B2 (en) 1979-08-30
DE2556045C2 (en) 1990-08-09
DK157137B (en) 1989-11-13
IL48565A0 (en) 1976-01-30
DK157137C (en) 1990-04-16
IE42190L (en) 1976-06-24
FR2333804B1 (en) 1979-05-18
AU8708475A (en) 1977-06-02
CS191291B2 (en) 1979-06-29
CH625528A5 (en) 1981-09-30
ES457884A1 (en) 1978-08-16

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