IP Library Granted Patent US 9,701,628
Granted Patent B2
US 9,701,628 · App. 15/111,390 · Granted Jul 11, 2017

12-epi pleuromutilins

Inventors: Klaus Thirring (Vienna, AT); Werner Heilmayer (Zillingtal, AT); Rosemarie Riedl (Vienna, AT); Hermann Kollmann (Linz, AT); Zrinka Ivezic-Schoenfeld (Korneuburg, AT); Wolfgang Wicha (Bruck an der Leitha, AT); Susanne Paukner (Vienna, AT); Dirk Strickmann (Purkersdorf, AT)
Assignee: Nabriva Therapeutics AG
C07C323/52A61K31/216A61K31/22A61K31/4196A61K31/44A61K31/445A61K31/4409A61K31/4458A61K31/4465A61K31/4468A61K31/495A61K31/52A61K31/5375C07C323/62C07D211/20C07D211/26C07D211/54C07D211/58C07D213/32C07D213/36C07D213/40C07D213/56C07D213/70C07D223/06C07D249/14C07D295/13C07D295/192C07D473/24C07D473/38C07C2101/02C07C2101/14C07C2103/82
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Quick Facts
Patent No.
US 9,701,628
App. No.
15/111,390
Granted
Jul 11, 2017
Kind
B2
Abstract

A compound selected from 14-O-[((Alkyl-, cycloalkyl-, heterocycloalkyl-, heteoroaryl-, or aryl)-sulfanyl)-acetyl]-12-epi-mutilins, or 14-O-[((Alkyl-, cycloalkyl-, heterocycloalkyl-, heteoroaryl-, or aryl)-oxy)-acetyl]-12-epi-mutilins, wherein 12-epi-mutilin is characterized in that the mutilin ring at position 12 is substituted by two substituents, the first substituent at position 12 of the mutilin ring is a methyl group which methyl group has the inverse stereochemistry compared with the stereochemistry of the methyl group at position 12 of the naturally occurring pleuromutilin ring, the second substituent at position 12 of the mutilin ring is a hydrocarbon group comprising at least one nitrogen atom and all other substituents of the mutilin ring having the same stereochemistry compared with the stereochemistry of the substituents at the corresponding positions in the naturally occurring pleuromutilin ring; optionally in the form of a salt and/or solvate, wherein the naturally occurring pleuromutilin is of formula processes for the preparation of such compounds and their use as pharmaceuticals.

Claims (293)

1. A compound selected from 14-O-[((Alkyl-, cycloalkyl-, heterocycloalkyl-, heteoroaryl-, or aryl)-sulfanyl)-acetyl]-12-epi-mutilins, or

14-O-[((Alkyl-, cycloalkyl-, heterocycloalkyl-, heteoroaryl-, or aryl)-oxy)-acetyl]-12-epi-mutilins,

wherein 12-epi-mutilin is characterized in that

the mutilin ring at position 12 is substituted by two substituents,

the first substituent at position 12 of the mutilin ring is a methyl group which methyl group has the inverse stereochemistry compared with the stereochemistry of the methyl group at position 12 of the naturally occurring pleuromutilin ring,

the second substituent at position 12 of the mutilin ring is a hydrocarbon group comprising at least one nitrogen atom,

and

all other substituents of the mutilin ring having the same stereochemistry compared with the stereochemistry of the substituents at the corresponding positions in the naturally occurring pleuromutilin ring;

optionally

in the form of a salt and/or solvate,

wherein the naturally occurring pleuromutilin is of formula

2. The compound according to claim 1 of formula

wherein

the methyl group at position 12 of the mutilin ring has the inverse stereochemistry compared with the stereochemistry of the methyl group at position 12 of the naturally occurring pleuromutilin ring,

all other substituents of the mutilin ring having the same stereochemistry compared with the stereochemistry of the substituents at the corresponding positions in the naturally occurring pleuromutilin ring,

R 1 is a hydrocarbon group comprising 1 to 16, in particular 1 to 12 carbon atoms comprising one N atom, optionally comprising one or more additional heteroatoms selected from N, O, S, halogen, in particular N,

X is sulfur or oxygen, in particular sulfur, and

R 2 is a hydrocarbon group comprising 1 to 22 carbon atoms, optionally comprising heteroatoms selected from N, O, S, halogen, in particular N or O.

3. The compound according to claim 2 , wherein

R 1 is either (C 1-16 )alkyl or (C 2-16 )alkenyl, substituted by heterocyclyl, including aliphatic heterocyclyl and aromatic heterocyclyl comprising 1 to 4 heteroatoms selected from N, O, S, with the proviso that at least one heteroatom is a nitrogen atom, or

R 1 is a group of formula

wherein Y—N(R 3 R 4 ) is

(C 1-16 )alkyl-N(R 3 R 4 ),

(C 1-16 )alkyl-(C 6-14 )aryl-N(R 3 R 4 ),

(C 1-16 )alkyl-(C 6-14 )aryl-(C 1-16 )alkyl-N(R 3 R 4 ),

(C 1-16 )alkyl-(C 1-13 )heterocyclyl —N(R 3 R 4 ),

(C 1-16 )alkyl-(C 1-13 )heterocyclyl-(C 1-16 )alkyl-N(R 3 R 4 ),

carbonyl-N(R 3 R 4 ),

(C 1-4 )alkyl-carbonyl-N(R 3 R 4 ),

(C 2-16 )alkenyl-N(R 3 R 4 ),

(C 2-16 )alkenyl-(C 6-14 )aryl-N(R 3 R 4 ),

(C 2-16 )alkenyl-(C 6-14 )aryl-(C 1-16 )alkyl-N(R 3 R 4 ),

(C 2-16 )alkenyl-(C 1-13 )heterocyclyl-N(R 3 R 4 ),

(C 2-16 )alkenyl-(C 1-13 )heterocyclyl-(C 1-16 )alkyl-N(R 3 R 4 ),

wherein heterocyclyl includes aliphatic and aromatic heterocyclyl comprising at least one heteroatom selected from N, O, S and wherein alkyl, aryl, heterocyclyl or alkenyl is optionally substituted comprising substituents which optionally having heteroatoms selected from O, N, S, halogen;

R 3 and R 4 independently of each other are

hydrogen,

(C 1-16 )alkyl,

(C 2-16 )alkenyl,

hydroxy(C 1-16 )alkyl,

amino-(C 1-16 )alkyl,

mono or di-(C 1-6 )alkylamino-(C 1-16 )alkyl,

guanidino(C 1-16 )alkyl, ureido(C 1-16 )alkyl or thioureido(C 1-16 )alkyl,

amino(C 1-6 )alkyl-(C 6-14 )aryl-(C 1-6 )alkyl,

amino(C 1-6 )alkyl-(C 6-14 )aryl,

guanidino(C 1-6 )alkyl-(C 6-14 )aryl-(C 1-6 )alkyl,

amino-(C 1-6 )alkyloxy-(C 1-6 )alkyl,

amino(C 3-8 )cycloalkyl,

amino(C 1-6 )alkyl-(C 3-8 )cycloalkyl,

amino(C 3-8 )cycloalkyl-(C 1-6 )alkyl,

amino(C 1-6 )alkyl-(C 3-8 )cycloalkyl-(C 1-6 )alkyl,

(C 1-13 )heterocyclyl-(C 1-16 )alkyl,

(C 6-14 )aryl-(C 1-6 )alkyl,

(C 1-13 )heterocyclyl,

amino-(C 6-14 )aryl-(C 1-16 )alkyl,

amino-(C 1-6 )alkyloxy-(C 6-14 )aryl-(C 1-6 )alkyl,

amino(C 1-6 )alkyl-(C 6-12 )aryl-carbonyl,

amino(C 1-6 )alkyl-amido-(C 6-12 )aryl(C 1-6 )alkyl,

(C 1-4 )alkylcarbonyl,

carbamimidoyl, carbamoyl, thiocarbamoyl,

wherein heterocyclyl includes aliphatic and aromatic heterocyclyl comprising at least one heteroatom selected from N, O, S,

and

wherein alkyl, cycloalkyl, heterocyclyl, alkenyl or aryl is optionally further substituted, by

amino(C 1-4 )alkyl, amido, mono or di-(C 1-4 )alkyl-amido, (C 1-6 )alkyloxy-carbonyl, halogen, oxo, hydroxy.

4. The compound according to claim 2 , wherein

R 2 is

(C 1-16 )alkyl,

(C 3-12 )cycloalkyl,

(C 1-13 )heterocyclyl,

(C 6-14 )aryl,

wherein heterocyclyl includes aliphatic and aromatic heterocyclyl comprising at least one heteroatom selected from N, O, S, and wherein alkyl, cycloalkyl, aryl, heterocyclyl is unsubstituted or substituted by substituents optionally having a heteroatom selected from O, N, S, and halogen.

5. The compound according to claim 4 ,

wherein R 2 is

alkyl,

optionally substituted by

hydroxy or amino,

(C 3-12 )cycloalkyl wherein the cycloalkyl group is optionally further substituted by amino or amino(C 1-4 )alkyl wherein the amino or aminoalkyl group is optionally further substituted by amino(C 1-6 )alkylcarbonyl and optionally (C 1-4 )alkyl,

(C 2-11 )heterocyclyl, wherein a nitrogen in the ring as a heteroatom optionally is further substituted by amino(C 1-6 )alkylcarbonyl,

cycloalkyl,

optionally substituted by

amino(C 1-4 )alkyl, wherein the amino group is optionally further substituted by amino(C 1-6 )alkylcarbonyl,

hydroxy,

amino, wherein the amino group is optionally further substituted by amino(C 1-6 )alkylcarbonyl and optionally (C 1-4 )alkyl,

amino and hydroxy, wherein the amino group is optionally further substituted by amino(C 1-6 )alkylcarbonyl and optionally (C 1-4 )alkyl,

(C 1-4 )alkylamino, wherein alkyl is optionally further substituted by one or more halogen atoms;

aliphatic (C 2-11 )heterocyclyl,

comprising 1 to 4 heteroatoms selected from N, O, S, wherein a nitrogen in the ring as heteroatom is optionally further substituted by

(C 1-4 )alkyl,

amino(C 1-6 )alkylcarbonyl,

aryl,

optionally substituted by

hydroxy, halogen, amino, hydroxy(C 1-4 )alkyl, bis-(hydroxy(C 1-4 )alkyl), amino(C 1-4 )alkyl, bis-(amino(C 1-4 )alkyl), wherein the amino group in amino(C 1-4 )alkyl optionally is further substituted,

aminocarbonyl, wherein the nitrogen optionally is substituted by

amino(C 1-12 )alkyl, bis-(amino(C 1-12 )alkyl), hydroxy(C 1-6 )alkyl, bis-(hydroxy(C 1-6 )alkyl) or diamino(C 1-6 )alkyl,

(C 1-12 )alkyl, which alkyl optionally is substituted by

amino, which amino optionally is acylated, particularly amino is substituted by formyl, (C 1-4 )alkylcarbonyl, saturated or unsaturated heterocyclyl comprising 1 to 3 heteroatoms, particularly N, and 4 to 8, particularly 5 to 6 ring members (C 6-14 )aryl, particularly phenyl, which aryl optionally is substituted by amino(C 1-4 )alkyl,

or

the nitrogen of the aminocarbonyl group is part of (C 3-8 )heterocyclyl, including aliphatic and aromatic heterocyclyl, comprising one or more heteroatoms selected from N, O, S preferably N, wherein the heterocycle is optionally further substituted by amino(C 1-4 )alkyl;

(C 1-6 )alkyl, which (C 1-6 )alkyl group is optionally substituted by aminocarbonyl, wherein the nitrogen of the aminocarbonyl group is optionally further substituted by amino(C 1-12 )alkyl, diamino-(C 1-12 )alkyl, bis-(amino(C 1-12 )alkyl), hydroxy(C 1-6 )alkyl, bis-(hydroxy(C 1-6 )alkyl),

acylated amino(C 1-4 )alkyl,

aromatic (C 1-13 )heterocyclyl, comprising 1 to 4 heteroatoms,

wherein the aromatic heterocyclyl is optionally substituted by (C 1-6 )alkyl, amino or hydroxy wherein the alkyl group is optionally further substituted by halogen or amino or the aromatic heterocyclyl is optionally substituted by aminocarbonyl wherein the amino group is optionally further substituted by amino(C 1-12 )alkyl, bis-(amino(C 1-12 )alkyl), hydroxy(C 1-6 )alkyl, bis-(hydroxy(C 1-6 )alkyl) or diamino(C 1-6 )alkyl.

6. The compound according to claim 2 , wherein

R 2 is amido-phenyl, amido(C 1-4 )alkyl-phenyl, wherein the nitrogen of the amido group is unsubstituted or substituted by amino(C 1-8 )alkyl, in which alkyl optionally is further substituted.

7. The compound according to claim 2 , wherein

R 2 is

amino(C 3-12 )cycloalkyl,

amino(C 1-4 )alkyl(C 3-12 )cycloalkyl,

amino(C 3-12 )cycloalkyl(C 1-4 )alkyl, or

amino(C 1-4 )alkyl(C 3-12 )cycloalkyl(C 1-4 )alkyl,

wherein the amino group is unsubstituted or substituted by amino(C 1-6 )alkylcarbonyl, or amino(C 1-6 )alkylcarbonyl and (C 1-4 )alkyl.

8. The compound according to claim 2 , wherein

R 2 is (C 2-11 )heterocyclyl comprising 1 to 4 heteroatoms selected from N, O, S, wherein, if a nitrogen in the ring as a heteroatom is present, said nitrogen is unsubstituted or optionally further substituted by

(C 1-4 )alkyl,

amino(C 1-6 )alkylcarbonyl.

9. The compound according to claim 2 , wherein

X is S,

and R 2 is

aminoethyl-amidomethyl-phenyl, aminopropyl-amidomethyl-phenyl, hydroxyphenyl-(amino)ethyl-amidomethyl-phenyl, aminomethyl-phenyl-(amino)ethyl-amidomethyl-phenyl, aminopropyl-amidophenyl, aminomethyl-phenylmethyl-amido-phenyl, aminomethyl-phenyl, aminoacetyl-aminomethyl-phenyl, bis(aminomethyl)phenyl, bisaminopropyl-amidomethyl-phenyl, (2-amino)-aminopropyl-amidomethyl-phenyl, aminoethyl-aminomethyl-phenyl, aminopropyl-aminomethyl-phenyl, allyl-aminomethyl-phenyl, aminomethyl-phenylmethyl-aminomethyl-phenyl, hydroxymethyl-phenyl, bis(hydroxymethyl)-phenyl, (tetrafluoro-hydroxymethyl)-phenyl, amino-hydroxy-cyclohexyl, hydroxyethyl, aminoethyl, piperazinocarbonyl-phenyl, aminomethyl-piperidine-carbonyl-phenyl,

piperidine-ylmethyl-amido-phenyl, pyridine-ylmethyl-amido-phenyl, acetyl-aminopropyl-amido-phenyl, formyl-aminopropyl-amido-phenyl, amido-phenyl, aminohexyl-amidophenyl, aminoethyl-amidophenyl, (5-Amino)-4H-[1,2,4]triazol-3-yl, pyridinyl, hydroxyphenyl, fluorophenyl, purinyl, aminophenyl, acetyl-aminomethyl-phenyl, cyclopropyl-aminomethyl-phenyl, aminopropyl-amidopyridinyl, hydroxypropyl-amidophenyl, amino-purinyl, difluoroethylamino-cyclohexyl, amino-hydroxy-cyclohexyl, azepanyl, aminomethylcyclohexylmethyl, N-methyl-piperidinyl, piperidinyl, aminomethylcyclohexyl, aminopropylphenyl, phenyl, N-aminomethylcarbonyl-piperidinyl, N-aminoethylcarbonyl-piperidinyl, N-aminomethylcarbonyl-piperidinylmethyl, aminomethylamidomethylcyclohexyl, aminomethyl-pyridinyl, aminomethylamidocyclohexyl.

10. The compound according to claim 2 , which is of formula

wherein

n is 1 to 12

R 3 is H, aminoethyl, aminopropyl, aminobutyl, aminopentyl, aminohexyl, aminooctyl, aminodecyl, dimethylaminopropyl, dimethylamidopentyl, guanidinobutyl, guanidinohexyl, carbamimidoyl, aminomethylcylcohexylmethyl, aminopropoxypropyl, aminocyclohexyl, hydroxyhexyl, dihydroxypropyl, aminomethylphenylmethyl, guanidinomethylphenylmethyl, phenylmethyl, morpholinopropyl, piperidinyl, hexyl, pyridinylethyl, allyl, amido-benzyl, aminopropyl-amidobenzyl, (2-amino)-amidoethyl-benzyl, (2-amino)-dimethylamidoethyl-benzyl, 2-amino-1-aminomethyl-ethyl, 5-amino-5-ethoxycarbonyl-pentyl, aminomethylphenylpropyl, aminomethylphenyl, aminophenymethyl, aminoethoxyphenylmethyl, aminomethyl-fluorophenyl-methyl, aminomethyl-difluorophenyl-methyl, and

R 4 is H(C 1-4 )alkylcarbonyl or aminomethylphenylcarbonyl.

11. The compound according to claim 2 , wherein

R 1 is aminomethylphenylpropyl, aminoethylaminomethylphenylethenyl, aminoethylaminomethylphenyl ethyl, aminomethylphenylethyl, aminomethylphenylethyl, pyridinylethenyl, aminoethylamino-fluorophenyl-ethenyl.

12. The compound according to claim 1 , selected from the group consisting of

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(2-Amino-ethylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-([Bis-(3-amino-propyl)-carbamoyl]-methyl})-phenylsulfanyl)-acetyl}-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(2,3-Diamino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{4-[(2-Amino-ethylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(2-amino-ethylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(2-amino-ethylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(4-amino-butylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(5-amino-pentylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(6-guanidino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(4-guanidino-butylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(allylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-aminomethyl mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(4-guanidinomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(6-hydroxy-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(2,3-dihydroxypropylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(4-piperidylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(3-morpholin-4-yl-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(3-dimethylamino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[(S)-5-amino-5-ethoxycarbonyl-pentylamino-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[4-(4-Aminomethyl-benzylcarbamoyl)-phenylsulfanyl]-acetyl}-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[4-(4-Aminomethyl-benzylcarbamoyl)-phenylsulfanyl]-acetyl}-12-[(6-guanidino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[(4-Piperazinylcarbamoyl)-phenylsulfanyl]-acetyl})-12-[(6-guanidino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[4-(4-Aminomethyl-piperidine-1-carbonyl)-phenylsulfanyl]-acetyl}-12-[(6-guanidino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{(4-[(Piperidin-4-ylmethyl)-carbamoyl]-phenylsulfanyl)-acetyl}-12-[(6-guanidino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{(4-[(Pyridin-4-ylmethyl)-carbamoyl]-phenylsulfanyl)-acetyl}-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[3-(3-Aminopropylcarbamoyl)-phenylsulfanyl]-acetyl})-12-[(6-guanidino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[4-(3-Acetylamino-propylcarbamoyl)-phenylsulfanyl]-acetyl}-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[4-(3-Formylamino-propylcarbamoyl)-phenylsulfanyl]-acetyl}-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[4-(3-Amino-propylcarbamoyl)-phenylsulfanyl]-acetyl}-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{(4-[(3-Aminopropylcarbamoyl)-phenylsulfanyl)-acetyl}-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{(4-[(3-Aminopropylcarbamoyl)-phenylsulfanyl)-acetyl}-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[4-(3-Aminopropylcarbamoyl)-phenylsulfanyl]-acetyl}-12-[(6-guanidino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[4-(3-Aminopropylcarbamoyl)-phenylsulfanyl]-acetyl}-12-[(8-amino-octylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[4-(3-Aminopropylcarbamoyl)-phenylsulfanyl]-acetyl}-12-[(10-amino-decylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{(4-Carbamoyl-phenylsulfanyl)-acetyl}-12-[(6-guanidino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[4-(3-Amino-propylcarbamoyl)-phenylsulfanyl]-acetyl}-12-{[3-(3-amino-propoxy)-propylamino)]-methyl} mutilin,

12-epi-12-desvinyl-14-O-{[4-(3-Amino-propylcarbamoyl)-phenylsulfanyl]-acetyl}-12 [(2-pyridin-4-yl-ethyl amino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[4-(6-Amino-hexylcarbamoyl)-phenylsulfanyl]-acetyl}-12-[(6-guanidino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[4-(2-Amino-ethylcarbamoyl)-phenylsulfanyl]-acetyl}-12-[(6-guanidino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[4-(3-Aminopropylcarbamoyl)-phenylsulfanyl]-acetyl}-12-{[3-(4-aminomethyl-phenyl)-propylamino]-methyl} mutilin,

12-epi-12-desvinyl-14-O-{[(4-Aminomethyl-cyclohexyl)-methylsulfanyl]-acetyl}-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-14-O-[(1-Methyl-piperidin-4-ylsulfanyl)-acetyl}-12-[(6-guanidino-hexylamino)-methyl] mutilin,

12-epi-14-O-[(Piperidin-4-ylsulfanyl)-acetyl]-12-[(6-amino-hexylamino)-methyl]mutilin,

12-epi-12-desvinyl-14-O-{[(4-Aminomethyl-cyclohexyl)-sulfanyl]-acetyl}-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[4-(3-Amino-propyl)-phenylsulfanyl]-acetyl}-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{(4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl)-acetyl}-12-{[(3-amino-propyl)-acetylamino]-methyl} mutilin,

12-epi-12-desvinyl-14-O-{(4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl)-acetyl}-12-(3-amino-propylcarbamoyl) mutilin,

12-epi-12-desvinyl-14-O-{[4-(3-Amino-propylcarbamoyl)-phenylsulfanyl]-acetyl}-12-(4-aminomethyl-benzylcarbamoyl) mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylcarbamoyl)-methyl]-phenylsulfanyl}-acetyl}-12-[2-(3-amino-propylamino)-ethyl] mutilin,

12-epi-12-desvinyl-14-O-[(3-Hydroxymethyl-phenylsulfanyl)-acetyl]-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(3-Hydroxymethyl-phenylsulfanyl)-acetyl]-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(3-Hydroxymethyl-phenylsulfanyl)-acetyl]-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(3-Hydroxymethyl-phenylsulfanyl)-acetyl]-12-[(6-guanidino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(4-Hydroxymethyl-phenylsulfanyl)-acetyl]-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(4-Hydroxymethyl-phenylsulfanyl)-acetyl]-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(4-Hydroxymethyl-phenylsulfanyl)-acetyl]-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(3,5-Bis-hydroxymethyl-phenylsulfanyl)-acetyl]-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[(2,3,5,6-Tetrafluoro-4-hydroxymethyl)-phenylsulfanyl]-acetyl}-12-[(4-aminomethyl-benzylamino)-methyl]-mutilin,

12-epi-12-desvinyl-14-O-{[(1R,2R,4R)-4-Amino-2-hydroxy-cyclohexylsulfanyl]-acetyl}-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[(1R,2R,4R)-4-Amino-2-hydroxy-cyclohexylsulfanyl]-acetyl}-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(2-Hydroxy-ethylsulfanyl)-acetyl]-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(2-Amino-ethylsulfanyl)-acetyl]-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[(5-Amino-4H-1,2,4-triazol-3-yl)-sulfanyl]-acetyl}-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(2-Amino-ethylsulfanyl)-acetyl]-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(Pyridin-4-ylsulfanyl)-acetyl]-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(Pyridin-4-ylsulfanyl)-acetyl]-12-[(6-guanidino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(3-Hydroxy-phenylsulfanyl)-acetyl]-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(4-Fluoro-phenylsulfanyl)-acetyl]-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[(7H-Purin-6-yl)-sulfanyl]-acetyl}-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(3-Amino-phenylsulfanyl)-acetyl]-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-(Phenylsulfanyl-acetyl)-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(4-Fluoro-phenylsulfanyl)-acetyl]-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(Pyridin-2-ylsulfanyl)-acetyl]-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(Pyridin-4-ylsulfanyl)-acetyl]-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[1-(2-Amino-acetyl)-piperidin-4-yl-sulfanyl)]-acetyl})-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[1-(3-Amino-propionyl)-piperidin-4-yl-sulfanyl)]-acetyl}-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[1-(3-Amino-propionyl)-piperidin-4-yl-sulfanyl]-acetyl}-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[1-(2-Amino-acetyl)-piperidin-4-yl-methylsulfanyl]-acetyl}-12-[(4-aminomethyl-phenylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[1-(2-Amino-acetyl)-piperidin-4-yl-methylsulfanyl]-acetyl}-12-[(4-amino-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[1-(2-Amino-acetyl)-piperidin-4-yl-sulfanyl]-acetyl}-12{2-[4-(2-amino-ethoxy)-benzylamino]-methyl} mutilin,

12-epi-12-desvinyl-14-O-{{4-[(2-Amino-acetylamino)-methyl]-cyclohexylsulfanyl}-acetyl}-12-[{4-[(2-amino-ethoxy)-benzylamino]-methyl} mutilin,

12-epi-12-desvinyl-14-O-[(4-Aminomethyl-phenylsulfanyl)-acetyl]-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(3-Aminomethyl-phenylsulfanyl)-acetyl]-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(3-Aminomethyl-phenylsulfanyl)-acetyl]-12-[(6-guanidino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(4-Aminomethyl-phenylsulfanyl)-acetyl]-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(4-Aminomethyl-phenylsulfanyl)-acetyl]-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(3-Aminomethyl-phenylsulfanyl)-acetyl]-12-[((4-aminomethyl-cyclohexyl)-methylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(4-Aminomethyl-phenylsulfanyl)-acetyl]-12-{[(4-aminocyclohexyl)-amino]-methyl} mutilin,

12-epi-12-desvinyl-14-O-[(4-Aminomethyl-phenylsulfanyl)-acetyl]-12-[(hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(4-Aminomethyl-phenylsulfanyl)-acetyl]-12-[(4-carbamoylphenyl)-methylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(4-Aminomethyl-phenylsulfanyl)-acetyl]-12-{[4-(3-amino-propylcarbamoyl)-benzylamino]-methyl} mutilin,

12-epi-12-desvinyl-14-O-[(4-Aminomethyl-phenylsulfanyl)-acetyl]-12-[(5-dimethylcarbamoyl-pentyl amino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(4-Aminomethyl-phenylsulfanyl)-acetyl]-12-{[4-(2-amino-2-carbamoyl-ethyl)-benzylamino]-methyl} mutilin,

12-epi-12-desvinyl-14-O-[(4-Aminomethyl-phenylsulfanyl)-acetyl]-12-{[4-(2-amino-2-dimethylcarbamoyl-ethyl)-benzylamino]-methyl} mutilin,

12-epi-12-desvinyl-14-O-{[5-Aminomethyl-pyridin-2-yl-sulfanyl)]-acetyl}-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-Desvinyl-14-O-{[5-aminomethyl-pyridin-2-yl-sulfanyl)]-acetyl}-12-[(4-aminomethyl-3-fluoro-benzyl amino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[(4-Aminomethyl-cyclohexyl)-methylsulfanyl)-acetyl]{[(4-Aminomethyl-cyclohexyl)-methyl sulfanyl]-acetyl}-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{1-(2-Amino-acetyl)-piperidin-4-yl-sulfanyl]-acetyl}-12-[(4-aminomethyl-3-fluoro-benzylamino)-methyl] mutilin,

12-epi-12-Desvinyl-14-O-{{4-[(2-Amino-acetylamino)-methyl]-cyclohexylsulfanyl)}-acetyl}-12-[(4-aminomethyl-3-fluoro-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[5-Aminomethyl-pyridin-2-yl-sulfanyl]-acetyl}-12-[(4-aminomethyl-2,5-difluoro-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(4-Aminomethyl-phenylsulfanyl)-acetyl]-12-[(2-amino-1-aminomethyl-ethylamino)-methyl] mutilin,

12-epi-12-Desvinyl-14-O-[(5-aminomethyl-pyridin-2-yl-sulfanyl)-acetyl]-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{(4-[(2-Amino-acetylamino)-methyl]-phenylsulfanyl)-acetyl}-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{(4-[(2-Amino-3-(4-hydroxy-phenyl)-propionylamino)-methyl]-phenylsulfanyl)-acetyl}-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{(4-[(3-Amino-propionylamino)-methyl]-phenylsulfanyl)-acetyl}-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{(4-[(2-Amino-acetylamino)-methyl]-phenylsulfanyl)-acetyl}-12-[4-aminomethyl-benzylamino-methyl] mutilin,

12-epi-12-desvinyl-14-O-{(4-[(2-Amino-acetylamino)-methyl]-phenylsulfanyl)-acetyl}-12-(6-amino-hexylamino-methyl) mutilin,

12-epi-12-desvinyl-14-O-{[(3-Acetylamino-methyl)-phenylsulfanyl]-acetyl}-12-[(3-amino-propyl amino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{(4-{[2-Amino-3-(4-aminomethyl-phenyl)-propionylamino]-methyl}-phenylsulfanyl)-acetyl}-12-[(3-amino-propylamino)-methyl]mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylamino)-methyl]-phenylsulfanyl}-acetyl}-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{3-[(3-Amino-propylamino)-methyl]-phenylsulfanyl}-acetyl}-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(4-Aminomethyl-benzylamino)-methyl]-phenylsulfanyl}-acetyl}-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(3-Allylaminomethyl-phenylsulfanyl)-acetyl]-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(3-Amino-propylamino)-methyl]-phenylsulfanyl}-acetyl}-12-{[3-(3-amino-propoxy)-propylamino]-methyl} mutilin,

12-epi-12-desvinyl-14-O-[(4-Cyclopropylaminomethyl-phenylsulfanyl)-acetyl]-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(4-Cyclopropylaminomethyl-phenylsulfanyl)-acetyl]-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(4-Aminomethyl-benzylamino)-methyl]-phenylsulfanyl}-acetyl}-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(4-Aminomethyl-benzylamino)-methyl]-phenylsulfanyl}-acetyl}-12-[(4-aminomethyl-benzylamino)-methyl]-mutilin,

12-epi-12-desvinyl-14-O-[5-(3-Amino-propylcarbamoyl)-pyridin-2-ylsulfanyl]-acetyl-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(2,5-Bis-aminomethyl-phenylsulfanyl)-acetyl]-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(3,5-Bis-aminomethyl-phenylsulfanyl)-acetyl]-12-[(3-amino-propylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[(3-Amino-propylcarbamoyl)-phenylsulfanyl]-acetyl}-12-[(2-guanidino-ethyl] mutilin,

12-epi-12-desvinyl-14-O-{[4-(3-Hydroxy-propylcarbamoyl)-phenylsulfanyl]-acetyl}-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(2-Hydroxy-ethylsulfanyl)-acetyl]-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[3-(2,2-Difluoro-ethylamino)-cyclohexylsulfanyl]-acetyl}-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(2-Amino-7H-purin-6-ylsulfanyl)-acetyl]-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(Azepan-4-ylsulfanyl)-acetyl]-12-[(6-amino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(Azepan-4-ylsulfanyl)-acetyl]-12-[(6-guanidino-hexylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(Azepan-4-ylsulfanyl)-acetyl]-12-[(4-aminomethyl-benzylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-[(Azepan-4-ylsulfanyl)-acetyl]-12-[(6-amino-octylamino)-methyl] mutilin,

12-epi-12-desvinyl-14-O-{[1-(2-Amino-acetyl)-piperidin-4-yl-sulfanyl)]-acetyl}-12-[(6-amino-hexylamino)-ethyl] mutilin,

12-epi-12-desvinyl-14-O-{[1-(2-Amino-acetyl)-piperidin-4-yl-sulfanyl)]-acetyl}-12-[(4-aminomethyl-benzylamino)-ethyl] mutilin,

12-epi-12-desvinyl-14-O-[5-Hydroxymethyl-pyridin-2-yl-sulfanylacetyl]-12-[(4-aminomethyl-3-fluoro-benzyl amino)-ethyl] mutilin,

12-epi-12-desvinyl-14-O-{4-[(2-Amino-acetylamino)-cyclohexylsulfanyl]-acetyl}-12-[(4-aminomethyl-3-fluoro-benzylamino)-ethyl] mutilin,

12-epi-12-desvinyl-14-O-{[1-(2-Amino-acetyl)-piperidin-4-yl-sulfanyl]-acetyl}-12-[(4-aminomethyl-3-fluoro-benzylamino)-ethyl] mutilin,

12-epi-12-desvinyl-14-O-[(5-Aminomethyl-pyridin-2-yl-sulfanyl)-acetyl]-12-[(4-aminomethyl-2,5-difluoro-benzylamino)-ethyl] mutilin,

12-epi-12-desvinyl-14-O-{[1-(2-Amino-acetyl)-piperidin-4-yl-sulfanyl]-acetyl}-12-[(4-aminomethyl-2,5-difluoro-benzylamino)-ethyl] mutilin,

12-epi-12-desvinyl-14-O-{[1-(2-Amino-acetyl)-piperidin-4-yl-sulfanyl]-acetyl}-12{2-[4-(2-amino-ethoxy)-benzylamino]-ethyl} mutilin,

12-epi-12-desvinyl-14-O-{{4-[(2-Amino-acetylamino)-methyl]-cyclohexylsulfanyl}-acetyl}-12-[(4-aminomethyl-3-fluoro-benzylamino)-ethyl] mutilin,

12-epi-12-desvinyl-14-O-[(Azepan-4-ylsulfanyl)-acetyl]-12-[(4-aminomethyl-phenylamino)-ethyl] mutilin,

12-epi-12-desvinyl-14-O-{{4-[(2-Amino-acetylamino)]-cyclohexylsulfanyl})-acetyl})-12-[(4-aminomethyl-phenylamino)-ethyl] mutilin,

12-epi-12-desvinyl-14-O-{[1-(2-Amino-acetyl)-piperidin-4-yl-methylsulfanyl]-acetyl})-12-[(4-aminomethyl-phenylamino)-ethyl] mutilin,

12-epi-12-desvinyl-14-O-{[1-(2-Amino-acetyl)-piperidin-4-yl-sulfanyl]-acetyl})-12-(8-amino-octyl) mutilin,

12-epi-12-desvinyl-14-O-{[1-(2-Amino-acetyl)-piperidin-4-yl-sulfanyl]-acetyl})-12-[3-(4-aminomethyl-phenyl)-propyl] mutilin,

12-epi-12-desvinyl-14-O-[(Azepan-4-yl-sulfanyl)-acetyl]-12-[3-(4-aminomethyl-phenyl)-propyl] mutilin,

12-epi-12-desvinyl-14-O-[(Azepan-4-yl-sulfanyl)-acetyl]-12-(6-amino-hexyl) mutilin,

12-epi-12-desvinyl-14-O-[(Azepan-4-yl-sulfanyl)-acetyl]-12-(8-amino-octyl) mutilin,

12-epi-12-desvinyl-14-O-{{4-[(2-Amino-acetylamino)-methyl]-cyclohexylsulfanyl}-acetyl})-12-[2-{4-[(2-amino-ethylamino)-methyl]-phenyl}-ethenyl) mutilin,

12-epi-12-desvinyl-14-O-{{4-[(2-Amino-acetylamino)-methyl]-cyclohexylsulfanyl}-acetyl})-12-[2-{4-[(2-amino-ethylamino)-methyl]-phenyl}-ethyl) mutilin,

12-epi-12-desvinyl-14-O-[(Azepan-4-ylsulfanyl)-acetyl]-12-[2-(4-Aminomethyl-phenyl)-ethyl]-mutilin,

12-epi-12-desvinyl-14-O-[(Azepan-4-ylsulfanyl)-acetyl]-12-((E)-2-pyridin-3-yl-ethenyl) mutilin,

12-epi-12-desvinyl-14-O-[(Azepan-4-ylsulfanyl)-acetyl]-12-((E)-2-{4-[(2-Amino-ethylamino)-methyl]-phenyl}-ethenyl) mutilin,

12-epi-12-desvinyl-14-O-[(Azepan-4-ylsulfanyl)-acetyl]-12-[2-{4-[(2-amino-ethylamino)-methyl]-phenyl}-ethyl) mutilin,

12-epi-12-desvinyl-14-O-[(Azepan-4-ylsulfanyl)-acetyl]-12-((E)-2-{4-[(2-amino-ethylamino)-methyl]-3-fluoro-phenyl}-ethenyl) mutilin,

12-epi-14-O-{[1-(2-Amino-acetyl)-piperidin-4-yl-sulfanyl]-acetyl}-12-((E)-2-{4-[(2-amino-ethylamino)-methyl]-phenyl}-ethenyl) mutilin,

12-epi-14-O-{[1-(2-Amino-acetyl)-piperidin-4-yl-sulfanyl]-acetyl}-12-[2-{4-[(2-amino-ethylamino)-methyl]-phenyl}-ethyl) mutilin,

12-epi-12-desvinyl-14-O-[(5-Aminomethyl-pyridin-2-ylsulfanyl)-acetyl]-12-[2-(4-aminomethyl-benzoylamino)-ethyl] mutilin.

13. The compound according to claim 12 , in the form of a salt and/or solvate.

14. The compound according to claim 1 , optionally in the form of a pharmaceutically acceptable salt, for use as a pharmaceutical drug substance, in particular for use in the treatment of diseases mediated by Gram negative bacteria, in particular Escherichia coli.

15. A pharmaceutical composition comprising a compound according to claim 1 optionally in the form of a pharmaceutically acceptable salt, in association with at least one pharmaceutical excipient, optionally further comprising another pharmaceutically active agent.

16. The compound according to claim 12 , optionally in the form of a pharmaceutically acceptable salt, for use as a pharmaceutical drug substance, in particular for use in the treatment of diseases mediated by Gram negative bacteria, in particular Escherichia coli.

17. A pharmaceutical composition comprising a compound according to claim 12 , optionally in the form of a pharmaceutically acceptable salt, in association with at least one pharmaceutical excipient, optionally further comprising another pharmaceutically active agent.

Assignments (6)
CHANGE OF NAME Recorded Dec 17, 2024
From: NABRIVA THERAPEUTICS AG
To: NABRIVA THERAPEUTICS GMBH
Reel/Frame 069727/0366 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 17, 2024
From: NABRIVA THERAPEUTICS GMBH
To: ARIVA MED GMBH
Reel/Frame 069613/0184 →
CORRECTIVE ASSIGNMENT TO CORRECT THE RECEIVING PARTY DATA AND THE ASSIGNMENT DOCUMENT PREVIOUSLY RECORDED AT REEL: 062881 FRAME: 0090. ASSIGNOR(S) HEREBY CONFIRMS THE RELEASE OF SECURITY INTEREST. Recorded Jun 20, 2023
From: HERCULES CAPITAL, INC.
To: NABRIVA THERAPEUTICS GMBH
Reel/Frame 064312/0350 →
RELEASE OF SECURITY INTEREST Recorded Mar 3, 2023
From: HERCULES CAPITAL, INC.
To: NABRIVA THERAPEUTICS GMBH; ZAVANTE THERAPEUTICS, INC.
Reel/Frame 062881/0090 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Dec 20, 2018
From: NABRIVA THERAPEUTICS GMBH
To: HERCULES CAPITAL, INC.
Reel/Frame 047973/0110 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 28, 2017
From: THIRRING, KLAUS; HEILMAYER, WERNER; RIEDL, ROSEMARIE; KOLLMANN, HERMANN; IVEZIC-SCHOENFELD, ZRINKA; WICHA, WOLFGANG; PAUKNER, SUSANNE; STRICKMANN, DIRK
To: NABRIVA THERAPEUTICS AG
Reel/Frame 041769/0725 →
Priority Claims (1)
EP 14152107 · Jan 22, 2014 · regional
Continuity (1)
Related Publication 20160332963A1 · Nov 17, 2016