DK2806873T3 - Amidin-substituerede beta-lactamforbindelser, deres fremstilling og anvendelse som antibakterielle midler - Google Patents

Amidin-substituerede beta-lactamforbindelser, deres fremstilling og anvendelse som antibakterielle midler Download PDF

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DK2806873T3
DK2806873T3 DK13701246.4T DK13701246T DK2806873T3 DK 2806873 T3 DK2806873 T3 DK 2806873T3 DK 13701246 T DK13701246 T DK 13701246T DK 2806873 T3 DK2806873 T3 DK 2806873T3
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amino
thiazol
imino
ethoxy
methyl
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Guido Schiffer
Heike Broetz-Oesterhelt
Samarendra N Maiti
Jehangir Khan
Andhe Reddy
Zhixiang Yang
Mostafa Hena
Guofeng Jia
Ou Ligong
Hong Liang
Judy Yip
Chuanjun Gao
Sabiha Tajammul
Rahim Mohammad
Ganguli Biswajeet
Burkhard Klenke
Irith Wiegand
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Aicuris Gmbh & Co Kg
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Claims (20)

1. Forbindelse med formel
(I) hvor R1 og R2 uafhængigt af hinanden betegner hydrogen, aminocarbonyl eller (Ci-C4)-alkyl, eller R1 og R2 sammen med det carbonatom til hvilket de er bundet danner en (C3-C8)-cycloalkyl, R3 betegner -(CH2)m-(S02)0H eller -0-(CH2)o-(S02)0H, hvor m og o uafhængigt af hinanden betegner et helt tal 0, 1, 2 eller 3, og hvor en hvilken som helst CH2-gruppe indeholdt i grupperne vist ved R3 kan være substitueret med en eller to (Ci-C4)-alkylgrupper, X betegner CR4 eller N, R4 betegner hydrogen eller halogen, Z betegner en binding eller en alkylkæde med én, to, tre eller fire carbonatomer, hvorved alkylkæden kan være substitueret med én, to, tre eller fire substituenter, valgt uafhængigt af hinanden fra gruppen bestående af carboxy, aminocarbonyl og (Ci-C4)-alkyl, hvorved alkyl skiftevis kan være substitueret med en substituent valgt fra gruppen bestående af hydroxy, carboxy og aminocarbonyl, Y betegner en binding, O, NH eller S, A betegner (Ce-Cio)-aryl eller 5- til 10-leddet heteroaryl, hvorved aryl og heteroaryl er substitueret med en substituent med følgende formel
eller hvor Rlb, R2b og R3b uafhængigt af hinanden betegner hydrogen, amino, hydroxy, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, (C3-C6)-cycloalkyl, 4-, 5- 6- eller 7-leddet heterocyclyl eller 5- eller 6-leddet heteroaryl, hvorved amino og hydroxy kan være substitueret med én eller to substituenter valgt uafhængigt af hinanden fra gruppen bestående af carbonyl, (Ci-C4)-alkylcarbonyl, mono- eller di-(Ci-C4)-alkylaminocarbonyl, og (Ci-C4)-alkyl, hvorved alkoxy, heterocyclyl og heteroaryl kan være substitueret med én, to eller tre substituenter valgt uafhængigt af hinanden fra gruppen bestående af halogen, hydroxy, amino, carbonyl, carboxy, (C1-C4)-alkylcarbonyl, (Ci-C4)-alkoxy, mono- eller di-(Ci-C4)-alkylamino, monoeller di-(Ci-C4)-alkylaminocarbonyl, -NH-CH(=NH), -NH-C(=NH)(NH2),-C(=NH)CH3 og (Ci-C4)-alkyl, og hvorved alkyl og cycloalkyl kan være substitueret med én, to eller tre substituenter valgt uafhængigt af hinanden fra gruppen bestående af halogen, hydroxy, amino, carbonyl, carboxy, carbonyloxy, aminocarbonyl, carbonylamino, (Ci-C4)-alkylcarbonyl, (Ci-C4)-alkoxy, mono- eller di-(Ci-C4)-alkylamino, mono- eller di-(Ci-C4)-alkylaminocarbonyl, -NH-CH(=NH), -NH-C(=NH)(NH2), -CH(=NH)CH3, (Ce-Cio)-aryl, 5- eller 6-leddet heteroaryl og 5- eller 6-leddet heterocyclyl, hvorved heteroaryl og heterocyclyl til gengæld kan være substitueret med (Ci-C4)-alkyl, og hvorved amino skiftevis kan være substitueret med 5- eller 6-leddet heteroaryl, eller R2b og R3b sammen med det nitrogenatom til hvilket de er bundet danner en 5- til 7-leddet heterocykel omfattende ét, to eller tre yderligere heteroatomer valgt fra serierne N, O og S og Rlb er som defineret ovenfor, R4b betegner hydrogen, amino, hydroxy, (Ci-C4)-alkyl eller (Ci-C4)-alkoxy, hvorved amino og hydroxy kan være substitueret med en eller to substituenter valgt uafhængigt af hinanden fra gruppen bestående af (Ci-C4)-alkylcarbonyl, mono- eller di-(Ci-C4)-alkylaminocarbonyl og (C1-C4)-alkyl, hvorved alkoxy kan være substitueret med én, to eller tre substituenter valgt uafhængigt af hinanden fra gruppen bestående af halogen, hydroxy, amino, carbonyl, carboxy, (Ci-C4)-alkylcarbonyl, (Ci-C4)-alkoxy, monoeller di-(Ci-C4)-alkylamino, mono- eller di-(Ci-C4)-alkylaminocarbonyl, -NH-CH(=NH),-NH-C(=NH)(NH2), -CH(=NH)CH3 og (Ci-C4)-alkyl, og hvorved alkyl kan være substitueret med én, to eller tre substituenter valgt uafhængigt af hinanden fra gruppen bestående af halogen, hydroxy, amino, carbonyl, carboxy, aminocarbonyl, (Ci-C4)-alkylcarbonyl, (Ci-C4)-alkoxy, mono- eller di-(Ci-C4)-alkylamino, mono- eller di-(Ci-C4)-alkylaminocarbonyl, -NH-CH(=NH), -NH-C(=NH)(NH2), -CH(=NH)CH3, (Ci-C4)-alkyl, (Ce-C io)-aryl og 5- eller 6-leddet heteroaryl, R5b betegner hydrogen eller (Ci-C4)-alkyl, Q betegner en binding, CH2 eller NH, k betegner et helt tal 1 eller 2, og * er bindingsstedet til gruppen vist ved A, og hvorved aryl og heteroaryl yderligere kan være substitueret med én eller to substituenter valgt uafhængigt af hinanden fra gruppen bestående af halogen, cyano, amino, hydroxy, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, mono- eller di-(Ci-C4)-alkylamino, amino-(Ci-C4)-alkyl, hydroxy-(Ci-C4)-alkyl eller carboxy, hvorved alkyl, alkoxy, alkylamino, aminoalkyl, hydroxyalkyl og carboxy skiftevis kan være substitueret med en substituent valgt fra gruppen bestående af halogen, (Ci-C4)-alkyl og carbonyl, og I betegner et helt tal 0, 1, 2 eller 3, og salte deraf, solvater deraf og solvater af saltene deraf.
2. Forbindelse ifølge krav 1, kendetegnet ved at R1 og R2 uafhængigt af hinanden betegner hydrogen eller (Ci-C4)-alkyl, eller R1 og R2 sammen med det carbonatom til hvilket de er bundet danner en (C3-C8)-cycloalkyl, R3 betegner -(CH2)m-(S02)0H eller -0-(CH2)0-(S02)0H, hvor m og o uafhængigt af hinanden betegner et helt tal 0 eller 1 og hvor en hvilken som helst CH2-gruppe indeholdt i grupperne vist ved R3 kan være substitueret med en eller to (Ci-C4)-alkylgrupper, X betegner CR4 eller N, R4 betegner hydrogen eller halogen, Z betegner en binding eller en alkylkæde med en, to eller tre carbonatomer, hvorved alkylkæden kan være substitueret med én, to eller tre substituenter, valgt uafhængigt af hinanden fra gruppen bestående af carboxy, aminocarbonyl og (Ci-C4)-alkyl, hvorved alkyl skiftevis kan være substitueret med en substituent valgt fra gruppen bestående af hydroxy og carboxy, Y betegner en binding, O, NH eller S, A betegner (Ce-Cio)-aryl eller 5- til 10-leddet heteroaryl, hvorved aryl og heteroaryl er substitueret med en substituent med følgende formel
eller hvor Rlb, R2b og R3b uafhængigt af hinanden betegner hydrogen, amino, hydroxy, (Ci-C4)-alkyl, 4-, 5-, 6- eller 7-leddet heterocyclyl eller 5- eller 6-leddet heteroaryl, hvorved heterocyclyl og heteroaryl kan være substitueret med én, to eller tre substituenter valgt uafhængigt af hinanden fra gruppen bestående af halogen, hydroxy, amino, carbonyl, carboxy, (Ci-C4)-alkylcarbonyl, (Ci-C4)-alkoxy, mono- eller di-(Ci-C4)-alkylamino, mono- eller di-(Ci-C4)-alkylamino-carbonyl, -NH-CH(=NH), -NH-C(=NH)(NH2),-C(=NH)CH3 og (Ci-C4)-alkyl, og hvorved alkyl kan være substitueret med én, to eller tre substituenter valgt uafhængigt af hinanden fra gruppen bestående af halogen, hydroxy, amino, carbonyl, carboxy, carbonyloxy, aminocarbonyl, carbonylamino, (C1-C4)-alkylcarbonyl, (Ci-C4)-alkoxy, mono- eller di-(Ci-C4)-alkylamino, monoeller di-(Ci-C4)-alkylaminocarbonyl, -NH-CH(=NH),-NH-C(=NH)(NH2), -CH(=NH)CH3, (C6-Cio)-aryl, 5- eller 6-leddet heteroaryl og 5- eller 6-leddet heterocyclyl, hvorved heteroaryl og heterocyclyl skiftevis kan være substitueret med (Ci-C4)-alkyl eller R2b og R3b sammen med det nitrogenatom til hvilket de er bundet danner en 5- til 7-leddet heterocykel omfattende ét, to eller tre yderligere heteroatomer valgt fra serierne N, O og S og Rlb er som defineret ovenfor, R4b betegner hydrogen, amino, hydroxy, (Ci-C4)-alkyl eller (Ci-C4)-alkoxy, hvorved amino og hydroxy kan være substitueret med én eller to substituenter valgt uafhængigt af hinanden fra gruppen bestående af (Ci-C4)-alkylcarbonyl, mono- eller di-(Ci-C4)-alkylaminocarbonyl og (C1-C4)-alkyl, og hvorved alkyl kan være substitueret med én, to eller tre substituenter valgt uafhængigt af hinanden fra gruppen bestående af halogen, hydroxy, amino, carbonyl, carboxy, aminocarbonyl, (Ci-C4)-alkylcarbonyl, (Ci-C4)-alkoxy, mono- eller di-(Ci-C4)-alkylamino, mono- eller di-(Ci-C4)-alkylaminocarbonyl, -NH-CH(=NH), -NH-C(=NH)(NH2), -CH(=NH)CH3, (Ci-C4)-alkyl, (C6-Cio)-aryl og 5- eller 6-leddet heteroaryl, R5b betegner hydrogen eller (Ci-C4)-alkyl, Q betegner en binding, CH2 eller NH, k betegner et helt tal 1 eller 2, og * er bindingsstedet til gruppen vist ved A, og hvorved aryl og heteroaryl yderligere kan være substitueret med en eller to substituenter valgt uafhængigt af hinanden fra gruppen bestående af halogen, cyano, amino, hydroxy, (Ci-C4)-alkyl, (Ci-C4)-alkoxy, mono- eller di-(Ci-C4)-alkylamino, amino-(Ci-C4)-alkyl, hydroxy-(Ci-C4)-alkyl eller carboxy, hvorved alkyl, alkoxy, alkylamino, aminoalkyl, hydroxyalkyl og carboxy skiftevis kan være substitueret med en substituent valgt fra gruppen bestående af halogen, (Ci-C4)-alkyl og carbonyl, og I betegner et helt tal 0 eller 1 og salte deraf, solvater deraf og solvater af saltene deraf.
3. Forbindelse ifølge krav 1 eller 2, kendetegnet ved at R1 og R2 uafhængigt af hinanden betegner hydrogen eller (Ci-C4)-alkyl, eller R1 og R2 sammen med det carbonatom til hvilket de er bundet danner en (C3-C8)-cycloalkyl, R3 betegner -(S02)0H eller -0-(CH2)o-(S02)OH, hvor o er et helt tal 0 eller 1, og hvor en hvilken som helst CH2-gruppe indeholdt resten hvor R3 betegner kan være substitueret med en eller to (Ci-C4)-alkylgrupper, X betegner CH, Z betegner en alkylkæde med to eller tre carbonatomer, hvorved alkylkæden kan være substitueret med én eller to substituenter valgt uafhængigt af hinanden fra gruppen bestående af carboxy, aminocarbonyl, methyl, hydroxymethyl, hydroxyethyl, Y betegner O A betegner phenyl eller 5- eller 6-leddet heteroaryl, hvorved phenyl og heteroaryl er substitueret med en substituent med følgende formel (eller indsættes (OK /LAR))
eller hvor Rlb, R2b og R3b uafhængigt af hinanden betegner hydrogen, amino, hydroxy, (Ci-C4)-alkyl eller 4-, 5-, 6- eller 7-leddet heterocyclyl, hvorved heterocyclyl kan være substitueret med én eller to substituenter valgt uafhængigt af hinanden fra gruppen bestående af amino, carboxy, mono- eller di-(Ci-C4)-alkylamino, og (Ci-C4)-alkyl, og hvorved alkyl kan være substitueret med én eller to substituenter valgt uafhængigt af hinanden fra gruppen bestående af hydroxy, amino, carboxy, carbonyloxy, aminocarbonyl, carbonylamino, mono- eller di-(Ci-C4)-alkylamino, mono- eller di-(Ci-C4)-alkylaminocarbonyl, -NH-CH(=NH), -NH-C(=NH)-(NH2), phenyl, 6-leddet heteroaryl og 5- eller 6-leddet heterocyclyl, eller, R2b og R3b sammen med det nitrogenatom til hvilket de er bundet danner en 6-leddet heterocykel omfattende et eller to nitrogenatomer og Rlb er hydrogen, R4b betegner hydrogen eller amino, hvorved amino kan være substitueret med en eller to (Ci-C4)-alkyl substituenter, R5b betegner hydrogen, Q betegner en binding, k betegner et helt tal 1 eller 2, og * er bindingsstedet til gruppen vist ved A, og hvorved phenyl und heteroaryl yderligere kan være substitueret med én eller to substituenter valgt uafhængigt af hinanden fra gruppen bestående af halogen, cyano, amino, hydroxy, (Ci-C4)-alkyl eller hydroxy-(Ci-C4)-alkyl, hvorved hydroxyalkyl skiftevis kan være susbstitueret med en carbonyl substituent, og I betegner 0 og salte deraf, solvater deraf og solvater af saltene deraf.
4. Forbindelse ifølge et hvilket som helst af kravene 1 til 3, kendetegnet ved at R1 og R2 uafhængigt af hinanden betegner hydrogen eller methyl, R3 betegner -(SChJOH eller -0-(S02)0H, X betegner CH, Z betegner en alkylkæde med to eller tre carbonatomer, hvorved alkylkæden kan være substitueret med én eller to substituenter, valgt uafhængigt af hinanden fra gruppen bestående af carboxy og methyl, Y betegner O, A betegner phenyl eller 6-leddet heteroaryl, hvorved phenyl og heteroaryl er substitueret med en substituent med følgende formel
hvor Rlb og R2b betegner hydrogen, R3b betegner hydrogen, amino, hydroxy, (Ci-C4)-alkyl eller 4-, 5- eller 6-leddet nitrogen-indeholdende heterocyclyl, hvorved alkyl kan være substitueret med en substituent valgt fra gruppen bestående af hydroxy, amino, carboxy, carbonyloxy, mono- eller di-(Ci-C4)-alkylamino, -NH-CH(=NH), -NH-C(=NH)(NH2), 5- eller 6-leddet nitrogen-indeholdende heteroaryl og 5- eller 6-leddet nitrogenindeholdende heterocyclyl, Q betegner en binding, * er bindingsstedet til gruppen vist ved A, og hvorved aryl og heteroaryl yderligere kan være substitueret med en substituent valgt fra gruppen bestående af halogen, cyano, amino, hydroxy, (Ci-C4)-alkyl eller hydroxy-(Ci-C4)-alkyl, og I betegner O og salte deraf, solvater deraf og solvater af saltene deraf.
5. Forbindelse ifølge et hvilket som helst af kravene 1 til 4, kendetegnet ved at R1 og R2 betegner methyl, R3 betegner -0-(S02)0H, X betegner CH, Z betegner en alkylkæde med to carbonatomer, hvorved alkylkæden kan være substitueret med en carboxysubstituent, Y betegner O, A betegner phenyl substitueret med en substituent med følgende formel
hvor Rlb og R2b betegner hydrogen, R3b betegner aminoethyl, azetidin, pyrrolidin eller piperidin, Q betegner en binding, * er bindingsstedet til gruppen vist ved A, og I betegner 0 og salte deraf, solvater deraf og solvater af saltene deraf.
6. Forbindelse ifølge et hvilket som helst af kravene 1 til 5, kendetegnet ved at R1 og R2 betegner methyl, R3 betegner -0-(S02)0H, X betegner CH, Z betegner en to-carbon alkylkæde, substitueret med en carboxysubstituent, Y betegner O, A betegner phenyl substitueret med en substituent med følgende formel
hvor Rlb og R2b betegner hydrogen, R3b betegner aminoethyl, azetidin, pyrrolidin eller piperidin, Q betegner en binding, * er bindingsstedet til gruppen vist ved A, og I betegner 0 og salte deraf, solvater deraf og solvater af saltene deraf.
7. Forbindelse ifølge krav 1, kendetegnet ved at A betegner en gruppe valgt fra følgende formel
og salte deraf, solvater deraf og solvater af saltene deraf.
8. Forbindelse ifølge krav 1, kendetegnet ved at denne forbindelse er (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(4-carbamimidoyl-3- hydroxyphenoxy)ethoxy]-imino}-N-[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]ethanamid (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(4-carbamimidoyl-3-hydroxyphenoxy)ethoxy]imino>acetyl]amino>-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(6-carbamimidoylpyridin-3-yl)oxy]-ethoxy>imino)acetyl]amino>-2-methyl-4-oxoazetidin-l-sulfonsyre (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(6-carbamimidoylpyridin-3- yl)oxy]ethoxy}imino)-N-[(3S)-2,2-dimethyl-4-oxo-l-(sulfooxy)azetidin-3- yl]ethanamid (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(5-carbamimidoylpyridin-2-yl)oxy]-ethoxy>imino)acetyl]amino)-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(4-carbamimidoylphenyl)sulfanyl]-ethoxy>imino)acetyl]amino>-2-methyl-4-oxoazetidin-l-sulfonsyre (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(4- carbamimidoylphenyl)sulfanyl]ethoxy>imino)-N-[(3S)-2,2-dimethyl-4-oxo- l-(sulfooxy)azetidin-3-yl]ethanamid (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(4-carbamimidoylphenyl)-amino]ethoxy>imino)acetyl]amino>-2-methyl-4-oxoazetidn-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2- {[2-(4-carbamimidoylphenoxy)-ethoxy]imino>acetyl]amino>-2-methyl-4-oxoazetidin-l-sulfonsyre (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{ [2-(4- carbamimidoylphenoxy)ethoxy]imino}-N-[(2R,3S)-2-methyl-4-oxo-l- (sulfooxy)azetidin-3-yl]ethanamid (2R,3S)-3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(4- carbamimidoylphenoxy)-ethoxy]imino}acetyl]amino>-2-methyl-4- oxoazetidin-l-sulfonsyre {[(2S,3S)-3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(4- carbamimidoylphenoxy)-ethoxy]imino}acetyl]amino}-2-methyl-4- oxoazetidin-l-yl]oxy}methansulfonsyre (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(4-carbamimidoyl-3-methylphenoxy)ethoxy]imino}-N-[(3S)-2,2-dimethyl-4-oxo-l-(sulfooxy)azetidin-3-yl] ethanamid (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(4-carbamimidoyl-3-methylphenoxy)ethoxy]imino}acetyl]amino>-2-methyl-4-oxoazetidin-l-sulfonsyre (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(2-carbamimidoylpyridin-4- yl)oxy]ethoxy>imino)-N-[(3S)-2,2-dimethyl-4-oxo-l-(sulfooxy)azetidin-3- yl]ethanamid (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(4- carbamimidoylphenoxy)ethoxy]imino>-N-[2-oxo-l-(sulfooxy)-l- azaspiro[3.4]oct-3-yl]ethanamid (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(4-carbamimidoylphenoxy)-2-methylpropoxy]imino>acetyl]amino>-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({[l-(4-carbamimidoylphenoxy)-2-methylpropan-2-yl]oxy>imino)acetyl]amino>2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(4-carbamimidoyl-2-fluorphenoxy)-ethoxy]imino}acetyl]amino}-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(4-carbamimidoyl-2-chlorphenoxy)ethoxy]imino}acetyl]amino}-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[4-(N-hydroxycarbamimidoyl)-phenoxy]ethoxy>imino)acetyl]amino>-2-methyl-4-oxoazetidin-l-sulfonsyre (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(4-carbamimidoylpyridin-2- yl)oxy]ethoxy}imino)-N-[(3S)-2,2-dimethyl-4-oxo-l-(sulfooxy)azetidin-3- yl]ethanamid (2Z)-2-(2-amino-l,3-thiazol-4-yl)-N-[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]-2-[(2-{4-[N-(piperidin-4- yl)carbamimidoyl]phenoxy>ethoxy)imino]ethanamid (2Z)-2-[(2-{4-[N-(2-aminoethyl)carbamimidoyl]phenoxy}ethoxy)imino]-2- (2-amino-l,3-thiazol-4-yl)-N-[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]ethanamid (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[4-(4,5-dihydro-lH-imidazol-2- yl)phenoxy]ethoxy}imino)-N-[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]ethanamid (2S og 2R)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(2S,3S)-2-methyl- 4-oxo-l-sulfoazetidin-3-yl]amino>-2-oxoethyliden]amino>oxy)-3-(4- carbamidinoyl-phenoxy)propanonsyre (2S og 2R)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl- 4-oxo-l-(sulfooxy)azetidin-3-yl]amino>-2-oxoethyliden]amino>oxy)-3-(4- carbamimidoyl-phenoxy)propanonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(6-carbamimidoylpyridazin-3-yl)oxy]ethoxy}imino)acetyl]amino}-2-methyl-4-oxoazetidin-l-sulfonsyre (2Z)-2-(2-amino-l,3-thiazo)-4-yl)-2-({2-[(6-carbamimidoylpyridazin-3- yl)oxy]-ethoxy}-imino)-N-[(3S)-2,2-dimethyl-4-oxo-l-(sulfooxy)azetidin- 3- yl]ethanamid (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(5-carbamimidoylpyrazin-2-yl)oxy]-ethoxy>imino)acetyl]amino>-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(4-carbamimidoyl-l,3-thiazol-2-yl)oxy]ethoxy}imino)acetyl]amino}-2-methyl-4-oxoazetidin-1-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-(2-[(4-carbamimidoylthiophen-2-yl)methoxy]imino)acetyl]amino>-2-methyl-4-oxoazetid in-1-sulfonsyre (2Z)-2-(2-armino-l,3-thiazol-4-yl)-2-({2-[(6-carbamimidoyl-5- hydroxypyridin-3-yl)oxy]-ethoxy}imino)-N-[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]ethanamid (2S og 2R)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl- 4- oxo-l-(sulfooxy)azetidin-3-yl]amino>-2-oxoethyliden]amino>oxy)-3 -(4-carbamimidoyl-3-hydroxyphenoxy)propanonsyre (25.35) -3-{[(2Z)-2-{[2-(2-amino-4- carbamimidoylphenoxy)ethoxy]imino>-2-(2-annino-l,3-thiazol-4- yl)acetyl]amino}-2-methyl-4-oxoazetidin-l-sulfonsyre (2S og 2R)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl- 4-oxo-l-(sulfooxy)-azetidin-3-yl]amino}-2-oxoethyliden]amino}oxy)-3- [(6-carbamimidoylpyridin-3-yl)oxy]propanonsyre (2S,3S)-3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-[{3-(4- carbamimidoylphenoxy)-propoxy]imino}-acetyl]-amino}-2-methyl-4- oxoazetidin-l-sulfonsyre (2Z)-2-(2-amino-l,3-thiazol-4-yl)-N-[(3S)-l-hydroxy-2,2-dimethyl-4- oxoazetidin-3-yl]-2-({2-[4-(N-{2- [(iminomethyl)amino]ethyl}carbamimidoyl)phenoxy]ethoxy}imino)- ethanamid (2Z)-2-(2-amino-l,3-thiazol-4-yl)-N-[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]-2-{[2-(4-{N-[(3S)-pyrrolidin-3- yl]carbamimidoyl>phenoxy)ethoxy]imino>ethanamid (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(4-{N-[2- (dimethylamino)ethyl]carbamimidoyl>-phenoxy)ethoxy]innino>-N-[(3S)- 2,2-dimethyl-4-oxo-l-(sulfooxy)azetidin-3-yl]ethanamid (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(4- carbamimidoylphenoxy)ethoxy]imino>-N-[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]ethanamid (4S)-4-{[{4-[2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2- dimethyl-4-oxo-l-(sulfooxy)-azet-idin-3-yl]amino>-2-oxo-ethyliden]- amino>-oxy)-ethoxy]-phenyl>(amino)-methyl]amino>-N,N-dimethyl-L- prolinamid (2Z)-2-(2-amino-l,3-thiazol-4-yl)-N-[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]-2-{[2-(4-{N-[(3S)-l-ethanimidoylpyrrolidin-3- yl]carbamimidoyl}phenoxy)ethoxy]imino}-ethanamid (2R og 2S)-3-{4-[N-(2-aminoethyl)carbamimidoyl]phenoxy}-2-({[(lZ)-l- (2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]amino>-2-oxo-ethyliden]amino>-oxy)-propanonsyre (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({[(2R og 2S)-l-(4- carbamimidoylphenoxy)-3-hydroxypropan-2-yl]oxy}imino)-N-[(3S)-2,2- dimethyl-4-oxo-l-(sulfooxy)azetidin-3-yl]ethanamid 3-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]amino}-2-oxoethyliden]amino}oxy)-4-(4- carbamimidoylphenoxy)butanonsyre (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(4- carbamimidoylphenoxy)ethoxy]imino}-N-[(2S,3S)-2-methyl-4-oxo-l- (sulfooxy)azetidin-3-yl]ethanamid (2R,3S)-3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[3-(4- carbamimidoylphenoxy)propoxy]imino>acetyl]amino>-2-methyl-4- oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(2-bromo-4-carbamimidoylphenoxy)ethoxy]imino}acetyl]amino}-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(4-carbamimidamidophenoxy)-ethoxy]imino>acetyl]amino>-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[3-(4-carbamimidamidophenoxy)-propoxy]imino>acetyl]amino>-2-methyl-4-oxoazetidin-l-sulfonsyre (2Z)-2-(5-amino-l,2,4-thiadiazol-3-yl)-2-{[2-(4- carbamimidoylphenoxy)ethoxy]imino>-N-[(2S,3S)-l-hydroxy-2-methyl-4- oxoazetidin-3-yl]ethanamid (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(3-carbamimidoylphenoxy)-ethoxy]imino}acetyl]amino>-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-({(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-[(2-{4-[N-(propan-2-yl)carbamimidoyl]-phenoxy}ethoxy)imino]acetyl}amino)-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[(4-carbamimidoylbenzyl)oxy]-imino>acetyl]amino}-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(4-carbamimidoylthiophen-2-yl)methoxy]ethoxy}imino)acetyl]amino>-2-methyl-4-oxoazetidin-l-sulfonsyre (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[(4- carbamimidoylbenzyl)oxy]imino>-N-[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]ethanamid (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[3-(4- carbamimidoylphenoxy)propoxy]imino>-N-[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]ethanamid (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[4-carbamimidoyl-2-(hydroxymethyl)phenoxy]ethoxy>imino)acetyl]amino>-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-({(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-[(2-{4-carbamimidoyl-2-[(formyloxy)-methyl]phenoxy}ethoxy)imino]acetyl>amino)-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-5-chlor-l,3-thiazol-4-yl)-2-{[2-(4-carbamimidoylphenoxy)ethoxy]imino}acetyl]amino}-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-({2-[4-(2-amino-2-iminoethyl)phenoxy]ethoxy}imino)-2-(2-amino-l,3-thiazol-4-yl)acetyl]amino}-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-({(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-[(2-{4-[(2-formylhydrazinyl)(imino)-methyl]phenoxy}ethoxy)imino]acetyl}amino)-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-({(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-[(2-{4-[hydrazinyl(imino)methyl]-phenoxy}ethoxy)imino]acetyl>amino)-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(5-carbamimidoyl-l,3,4-thiadiazol-2-yl)oxy]ethoxy}imino)acetyl]amino}-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(4-carbamimidoylphenoxy)ethoxy]-imino}acetyl]amino}-2-carbamoyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(3-carbamimidoyl- l,2-oxazol-5-yl)oxy]ethoxy}imino)acetyl]amino>-2-methyl-4-oxoazetidin-1-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[4-(N-methylcarbamimidoyl)phenoxy]ethoxy>imino)acetyl]amino>-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-({(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-[(2-{4-[N-(2-hydroxyethyl)carbamimidoyl]phenoxy>ethoxy)imino]acetyl>amino)-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[2-(4-{N-[2-(formyloxy)ethyl]carbamidoyl}phenoxy)ethoxy]imino>acetyl]amino}-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(3-carbamimidoyl-l-methyl-lH-pyrazol-5-yl)oxy]ethoxy}imino)acetyl]amino>-2-methyl-4-oxoazetidin-l-sulfonsyre (25.35) -3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(5-carbamimidoyl-l-methyl-lH-pyrazol-3-yl)oxy]ethoxy}imino)acetyl]amino}-2-methyl-4-oxoazetidin-l-sulfonsyre N-[{4-[2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4- oxo-l-(sulfooxy)-azetidin-3-yl]amino>-2- oxoethyliden]amino}oxy)ethoxy]phenyl}(imino)methyl]glycin (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({2-[(2-carbamimidoyl-5-methyl-l,3- thiazol-4-yl)oxy]ethoxy}imino)-N-[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]ethanamid 2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]amino}-2-oxoethyliden]amino>oxy)-3-(4- carbamimidoylphenoxy)propanamid (2Z)-2-(2-amino-l,3-thiazol-4-yl)-N-[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]-2-[(2-{4-[N-(pyridin-2- ylmethyl)carbamimidoyl]phenoxy}ethoxy)imino]ethanamid {[(2S,3S)-3-{[(2Z)-2-[(2-{4-[N-(2- aminoethyl)carbamimidoyl]phenoxy}ethoxy)imino]-2-(2-amino-l/3-thiazol- 4-yl)acetyl]amino}-2-methyl-4-oxoazetidin-l-yl]oxy>methansulfonsyre (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-[(2-{4-[N-(2- carbamimidamidoethyl)carbamimido-yl]phenoxy>ethoxy)imino]-N-[(3S)- 2,2-dimethyl-4-oxo-l-(sulfooxy)azetidin-3-yl]-ethanamid l-(2-{[{4-[2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl- 4-oxo-l-(sulfooxy)azetidin-3-yl]amino}-2- oxoethyliden]amino}oxy)ethoxy]phenyl>(imino)-methyl]-amino>ethyl)-l- methylpyrrolidiumchlorid (2Z)-2-(2-amino-l,3-thiazol-4-yl)-N-[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]-2-[(2-{4-[imino(piperazin-l- yl)methyl]phenoxy}ethoxy)iminoethanamid (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-({[l-(4-carbamimidoylphenoxy)-(2R og 2S)-4-hydroxybutan-2-yl]oxy>imino)-N-[(3S)-2,2-dimethyl-4-oxo-l-(sulfooxy)azetidin-3-yl] ethanamid (2Z)-2-{[2-({6-[N-(2-aminoethyl)carbamimidoyl]pyridin-3-yl}oxy)ethoxy]immo}-2-(2-amino-l,3-thiazol-4-yl)-N-[(3S)-2,2-dimethyl-4-oxo-l-(sulfooxy)azetidin-3-yl]ethanamid (2Z)-2-[(2-{4-[N-(3-aminopropyl)carbamimidoyl]phenoxy>ethoxy)imino]- 2-(2-amino-l,3-thiazol-4-yl)-N-[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]ethanamid (2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-[(2-{4-[N-(l,3-diaminopropan-2- yl)carbamimidoyl]-phenoxy}ethoxy)imino]-N-[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]ethanamid (2Z)-2-{[2-(4-{N-[(2R)-l-amino-3-hydroxypropan-2- yl]carbamimidoyl>phenoxy)-ethoxy]imino>-2-(2-amino-l,3-thiazol-4-yl)-N- [(3S)-2,2-dimethyl-4-oxo-l-(sulfooxy)-azetidin-3-yl]ethanamid (2Z)-2-({2-[4-(5-amino-l,4,5,6-tetrahydropyrimidin-2- yl)phenoxy]ethoxy}imino)-2-(2-amino-l,3-thiazol-4-yl)-N-[(3S)-2,2- dimethyl-4-oxo-l-(sulfooxy)azetidin-3-yl]ethanamid (2R og 2S) 3-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl- 4-oxo-l-(sulfooxy)azetidin-3-yl]amino}-2-oxoethyliden]amino>oxy)-2-(4- carbamimidoylphenoxy)propanonsyre (2S)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo- l-(sulfooxy)-azetidin-3-yl]amino}-2-oxoethyliden]amino}oxy)-3-(4-{/V- [(3R)-piperidin-3-yl]carbamimidoyl}phenoxy)propanonsyre (2R)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo- l-(sulfooxy)-azetidin-3-yl]amino}-2-oxoethyliden]amino}oxy)-3-(4-{N- [(3R)-piperidin-3-yl]-carbamimidoyl}phenoxy)propanonsyre {[(3S)-3-{[(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-{[(4- carbamimidoylbenzyl)oxy]imino}-acetyl]amino}-2,2-dimethyl-4- oxoazetidin-l-yl]oxy>methansulfonsyre (2Z)-2-[(2-{4-[5-(aminomethyl)-4,5-dihydro-lH-imidazol-2- yl]phenoxy}ethoxy)imino]-2-(2-amino-l,3-thiazol-4-yl)-N-[(3S)-2,2- dimethyl-4-oxo-l-(sulfooxy)azetidin-3-yl]ethanamid (3S)-3-({(2Z)-2-(2-amino-l,3-thiazol-4-yl)-2-[(2-{4-[N-(pyrazolidin-4- yl)carbamimido-yl]phenoxy>ethoxy)imino]acetyl>amino)-2,2-dimethyl-4- oxoazetidin-l-sulfonsyre (2S)-2-({[(lZ)-l-{2-amino-l,3-thiazol-4-yl}-2-{[(3S)-2,2-dimethyl-4- oxo-l-sulfoazetidin-3-yl]amino>-2-oxoethyliden]amino}oxy)-3-(4-{N- [(3S)-pyrrolidin-3-yl]carbamimidoyl>-phenoxy)propanonsyre (2S)-3-{4-[N-(2-amino-2-methylpropyl)carbamimidoyl]phenoxy>-2- ({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]amino>-2-oxoethyliden]amino>oxy)propanonsyre (2S)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo- l-(sulfooxy)-azetidin-3-yl]amino>-2-oxoethyliden]amino>oxy)-3-(4-{N-[2- (methylamino)ethyl]-carbamimidoyl}phenoxy)propanonsyre (2S)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo- l-sulfoazetidin-3-yl]amino>-2-oxoethyliden]amino}oxy)-3-(4-{N-[(3R)- pyrrolidin-3-yl]carbamimidoyl}-phenoxy)propanonsyre (2S)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo- l-(sulfooxy)-azetidin-3-yl]amino}-2-oxoethyliden]amino}oxy)-3-{4-[N- (piperidin-3-yl)carbamimido-yl]phenoxy>propanonsyre (2S)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo- l-(sulfooxy)-azetidin-3-yl]amino}-2-oxoethyliden]amino}oxy)-3-{4-[N- (pyrrolidin-2-ylmethyl)-carbamimidoyl]phenoxy}propanonsyre (2S)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo- l-(sulfooxy)-azetidin-3-yl]amino}-2-oxoethyliden]amino}oxy)-3-{4-[N- (piperidin-2-ylmethyl)-carbamimidoyl]phenoxy>propanonsyre (2S)-3-{4-[N-(trans-(R,R og S,S)-2- aminocyclopropyl)carbamimidoyl]phenoxy}-2-({[(lZ)-l-(2-amino-l,3- thiazol-4-yl)-2-{[(33S)-2,2-dimethyl-4-oxo-l-(sulfooxy)azetidin-3- yl]amino}-2-oxoethyliden]amino}oxy)propanonsyre (2S)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo- l-sulfoazetidin-3-yl]amino}-2-oxoethyliden]amino>oxy)-3-(4-{N-[(3S)-l- methylpyrrolidin-3-yl]-carbamimidoyl>-phenoxy)-propanonsyre (2S)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo- l-(sulfooxy)-azetidin-3-yl]amino}-2-oxoethyliden]amino}oxy)-3-{4-[N- (l,3-diaminopropan-2-yl)-carbamimidoyl]phenoxy>propanonsyre (2R)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo- l-(sulfooxy)-azetidin-3-yl]amino>-2-oxoethyliden]amino>oxy)-3-{4-[N- (l,3-diaminopropan-2-yl)-carbamimidoyl]phenoxy>propanonsyre (2S)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo- l-(sulfooxy)-azetidin-3-yl]amino>-2-oxoethyliden]amino>oxy)-3-{4-[N- (lH-imidazol-2-ylmethyl)-carbamimidoyl]phenoxy}propanonsyre (2R)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo- l-(sulfooxy}-azetidin-3-yl]amino}-2-oxoethyliden]amino}oxy)-3-{4-[N- (lH-imidazol-2-ylmethyl)-carbamimidoyl]phenoxy}propanonsyre (2S)-3-{4-[N-(4-aminopyrrolidin-3-yl)carbamimidoyl]phenoxy}-2-({[(lZ)- l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo-l- (sulfooxy)azetidin-3-yl]amino}-2-oxoethyliden]amino}oxy)propanonsyre (2S)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo- l-(sulfooxy)-azetidin-3-yl]amino}-2-oxoethyliden]amino}oxy)-3-{4-[N- (azetidin-3-yl)carbamimidoyl]phenoxy}propanonsyre (2S)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo- l-(sulfooxy)-azetidin-3-yl]amino>-2-oxoethyliden]amino}oxy)-3-{4-[N- (piperidin-4-yl)carbamimidoyl]phenoxy}propanonsyre (2S)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo- l-(sulfooxy)-azetidin-3-yl]amino}-2-oxoethyliden]amino}oxy)-3-{4-[N- (azetidin-3-yl)carbamimidoyl]phenoxy}propanonsyre (2S)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo-l-(sulfooxy)-azetidin-3-yl]amino}-2-oxoethyliden]amino}oxy)-3-(4-{N-[2-(pyrimidin-2-ylamino)-ethyl] carbamimidoyl>phenoxy)propanonsyre (2R)-2-({[(lZ)-l-(2-amino-l,3-thiazol-4-yl)-2-{[(3S)-2,2-dimethyl-4-oxo- l-(sulfooxy)azetidin-3-yl]amino}-2-oxoethyliden]amino}oxy)-3-(4-{/V-[2- (pyrimidin-2-ylamino)ethyl]carbamimidoyl}phenoxy)propanonsyre og salte deraf, solvater deraf og solvater af saltene deraf.
9. Forbindelse ifølge et hvilket som helst af kravene 1 til 8 til anvendelse i en fremgangsmåde til behandling og/eller forebyggelse af sygdomme.
10. Forbindelse til anvendelsen ifølge krav 9, hvor sygdommene er bakterielle infektioner.
11. Forbindelse til anvendelsen ifølge krav 10, hvor de bakterielle infektioner er med gram-negative bakterier.
12. Fremgangsmåde til fremstillingen af en forbindelse med formel (I) ifølge krav 1, omfattende fjernelse af beskyttelsesgruppen fra en forbindelse med formel
(II) hvor Pg betegner en beskyttelsesgruppe og R^R3, A, I, X, Y og Z er som defineret i krav 1.
13. Fremgangsmåde ifølge krav 12, kendetegnet ved at forbindelse (II) fremstilles ved omsætning af en forbindelse med formel
(Ill) hvor Pg betegner en beskyttelsesgruppe og A, I, X, Y og Z er som defineret i krav 1, med en forbindelse med formel
(IV), hvor R1, R2 og R3 er som defineret i krav 1.
14. Anvendelse af en forbindelse ifølge et hvilket som helst af kravene 1 til 8 til fremstillingen af et medikament til behandlingen og/eller profylakse af sygdomme.
15. Anvendelse af en forbindelse ifølge et hvilket som helst af kravene 1 til 8 til fremstillingen af et medikament til behandlingen og/eller profylakse af bakterielle infektioner
16. Medikament omfattende mindst én forbindelse ifølge et hvilket som helst af kravene 1 til 8 i kombination med mindst én yderligere aktiv forbindelse.
17. Medikament ifølge krav 16, kendetegnet ved at den yderligere aktive forbindelse er en /3-lactamaseinhibitor.
18. Medikament omfattende mindst én forbindelse ifølge et hvilket som helst af kravene 1 til 8 i kombination med mindst én inert, ikke-toxisk, farmaceutisk acceptabel excipiens.
19. Medikament ifølge et hvilket som helst af kravene 16 til 18 til anvendelse i en fremgangsmåde til behandling og/eller forebyggelse af bakterielle infektioner
20. Antibakteriel effektiv mængde af mindst én forbindelse ifølge et hvilket som helst af kravene 1 til 8 eller et medikament ifølge et hvilket som helst af kravene 16 til 18 til anvendelse i en fremgangsmåde til kontrahering af bakterieinfektioner hos mennesker og dyr.
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