# US 12,215,100 B2 · Anticancer compounds

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- Number: US 12,215,100 B2
- Document ID: US12215100B2
- Status: Granted
- Kind: B2
- Application number: 17/414,946
- Filed: 2019-12-17
- Published: 2022-02-24
- Granted: 2025-02-04
- Earliest claimed: 2018-12-17
- Assignees: Pharma Mar, S.A.
- Applicants: Pharma Mar, S.A.
- Inventors: María Jesús Martín López; Raquel Rodríguez Acebes; Patricia Gema Cruz López; Andrés M. Francesch Solloso; Maria del Carmen Cuevas Marchante
- Web page: https://patentgrep.com/patent/US12215100B2

## CPC

- C07D 417/12: linked by a chain containing hetero atoms as chain links
- A61P 35/00: Antineoplastic agents
- C07D 413/12: linked by a chain containing hetero atoms as chain links
- C07D 417/14: containing three or more hetero rings
- C07D 493/04: Ortho-condensed systems
- C07D 493/14: Ortho-condensed systems
- C07H 15/26: Acyclic or carbocyclic radicals, substituted by hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

Anticancer compounds of formula (I) and derivatives thereof are provided.

## Claims

### Claim 1

A compound of formula I or a pharmaceutically acceptable salt or ester thereof
wherein:
R1 is selected from hydrogen, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx;
R2 is selected from hydrogen, halogen, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C2-C24 alkenyl, substituted or unsubstituted C2-C24 alkynyl, —ORa, —OSO2Rb, —NRcRd, —NRc(C═O)Rf, and —NRcSO2Rb, wherein the optional substituents are one or more substituents Rx;
R3 is selected from halogen-substituted or unsubstituted C1-C12 alkyl, halogen-substituted or unsubstituted C2-C12 alkenyl, halogen-substituted or unsubstituted C2-C12 alkynyl and substituted or unsubstituted C3-C6 cycloalkyl-C1-C12 alkyl, wherein the optional substituents are one or more substituents Rx and the halogen substituents are one or more substituents independently selected from F, Cl, Br and I;
R4 is selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx;
R5 is selected from —C(ORe)2Rg, —C(SRe)2Rg, —CH(ORa)Rg, —CH(O—(C═O)Rf)Rg, —CH(NRcRd)Rg, —CH(NRc—(C═O)Rf)Rg, —CH(NRc—ORh)Rg, —(C═O)Rg, —(C═NRc)Rg, —(C═N—ORh)Rg, —(C═N—O—(C═O)Rf)Rg, —(C═N—O—(C═O)ORa)Rg, —(C═N—O—[(P═O)(ORa)2])Rg, —(C═N—NRcRd)Rg, —(C═O)ORa, —(C═O)NRc—ORh, —(C═O)NRcRd, —(C═CH2)Rg, and —(C═CH2)ORa; or R5 is a
group where m is 0, 1 or 2 and each E group is independently selected from O and S;
Y is —O—;
Z is —S—;
each group Ra is independently selected from hydrogen, a protecting group for OH, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C2-C24 alkenyl, substituted or unsubstituted C2-C24 alkynyl, substituted or unsubstituted C3-C6cycloalkyl-C1-C12alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, —(CH2CH2O)pCH2CH3, and —(CH2CH2O)pCH3 wherein p is from 1 to about 25 and the optional substituents are one or more substituents Rx;
each group Rb is independently selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heterocyclic group, wherein the optional substituents are one or more substituents Rx;
each group Rc and Rd is independently selected from hydrogen, a protecting group for amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx; or Rc and Rd together with the nitrogen atom to which they are attached form a heterocyclic group;
each group Re is substituted or unsubstituted C1-C12 alkyl group, wherein the optional substituents are one or more substituents Rx;
each group Rf is independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, —CH2O(CH2CH2O)pCH2CH3, —CH2O(CH2CH2O)pCH3 wherein p is from 1 to about 25 and the optional substituents are one or more substituents Rx, and a group of formula:
where each R group is, at each occurrence, independently selected from hydrogen, substituted or unsubstituted C1-C6 alkyl group, substituted or unsubstituted —(C═O)—(C1-C6)alkyl, and substituted or unsubstituted —(C═O)NH(C1-C6)alkyl, wherein the optional substituents are one or more substituents Rx; or two adjacent OR groups form an isopropylidene ketal or an acetal group selected from methylene-, methoxymethylene-, ethoxymethylene-, ethylidene-, benzylidene-, and p-methoxybenzylidene- acetals;
each group Rg is independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx;
each group Rh is independently selected from hydrogen, a protecting group for OH, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C3-C6cycloalkyl-C1-C12alkyl, substituted or unsubstituted heterocyclo-C1-C12alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, —(CH2CH2O)pCH2CH3, —(CH2CH2O)pCH3 wherein p is from 1 to about 25, and substituted or unsubstituted monosaccharide residue, wherein the optional substituents are one or more substituents Rx; and
substituents Rx are selected from the group consisting of C1-C12 alkyl groups which may be optionally substituted with at least one group Ry, C2-C12 alkenyl groups which may be optionally substituted with at least one group Ry, C2-C12 alkynyl groups which may be optionally substituted with at least one group Ry, halogen atoms, oxo groups, thio groups, cyano groups, nitro groups, ORy, OCORy, OCOORy, CORy, COORy, OCONRyRz, CONRyRz, SRy, S(═O)Ry, SO2Ry, OSO2ORy, SSRy, P(═O)(Ry)ORz, OP(═O)(ORy)2, NRyRz, NRyC(═O)Rz, NRyC(═O)ORz, NRyC(═O)NRyRz, NRyC(═NRy)NRyRz, aryl groups having from 6 to 18 carbon atoms in one or more rings which may optionally be substituted with one or more substituents which may be the same or different selected from the group consisting of Ry, ORy, OCORy, OCOORy, NRyRz, NRyCORz, and NRyC(═NRy)NRyRz, aralkyl groups comprising an alkyl groups having from 1 to 12 carbon atoms substituted with an optionally substituted aryl group as defined above, aralkyloxy groups comprising an alkoxy group having from 1 to 12 carbon atoms substituted with an optionally substituted aryl group as defined above, and a 5- to 14-membered saturated or unsaturated heterocyclic group having one or more rings and comprising at least one oxygen, nitrogen or sulphur atom in said ring(s), said heterocyclic group optionally being substituted with one or more substituents Ry, and where there is more than one optional substituents on any given group the optional substituents Ry may be the same or different; and
each Ry and Rz is independently selected from the group consisting of hydrogen, C1-C12 alkyl groups, C1-C12 alkyl groups that are substituted with at least one halogen atom, aralkyl groups comprising a C1-C12 alkyl group that is substituted with an aryl group having from 6 to 18 carbon atoms in one or more rings and heterocycloalkyl group comprising a C1-C12 alkyl group that is substituted with a 5- to 14-membered saturated or unsaturated heterocyclic group having one or more rings and comprising at least one oxygen, nitrogen or sulphur atom in said ring(s);
wherein the compound of formula I is not a natural product.

### Claim 2 (depends on 1)

The compound according to claim 1 which also has formula
wherein R1, R2, R3, R4, R5, Y, and Z are as defined in claim 1; or a pharmaceutically acceptable salt or ester thereof.

### Claim 3 (depends on 1)

The compound according to claim 1 wherein R1 is selected from hydrogen, halogen and substituted or unsubstituted C2-C6 alkynyl, wherein the optional substituents are one or more substituents Rx; or a pharmaceutically acceptable salt or ester thereof.

### Claim 4 (depends on 1)

The compound according to claim 1, which also have formula Ia:
wherein R2, R3, R4, R5, Y, and Z are as defined in claim 1; or a pharmaceutically acceptable salt or ester thereof wherein the compound of formula Ia is not a natural product.

### Claim 5 (depends on 1, 4)

The compound according to claim 4, which also has formula Ib:
wherein R2, R3, R4, R5, Y and Z are as defined in claim 1; or a pharmaceutically acceptable salt or ester thereof wherein the compound of formula Ib is not a natural product.

### Claim 6 (depends on 1)

The compound according to claim 1 wherein R2 is selected from hydrogen, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, wherein the optional substituents are one or more substituents Rx, —ORa, and —NRcRd, where Ra is selected from hydrogen, a silylether protecting group for OH, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C3-C6cycloalkyl-C1-C6alkyl, —(CH2CH2O)pCH2CH3 where p is from 1 to about 15 and the optional substituents are one or more substituents Rx; and Rc and Rd are independently selected from substituted or unsubstituted C1-C6 alkyl wherein the optional substituents are one or more substituents Rx; or a pharmaceutically acceptable salt or ester thereof.

### Claim 7 (depends on 6)

The compound according to claim 6, wherein R2 is selected from hydrogen, methyl, vinyl, allyl, NEt2, and ORa where Ra is selected from hydrogen, methyl, ethyl, n-butyl, n-heptyl, allyl, propargyl, cyclopropylmethyl, —(CH2)3NHBoc, —(CH2)3NH2, and —(CH2CH2O)3CH2CH3; or a pharmaceutically acceptable salt or ester thereof.

### Claim 8 (depends on 1)

The compound according to claim 1, wherein R3 is selected from halogen-substituted or unsubstituted C1-C6 alkyl and substituted or unsubstituted C3-C4 cycloalkyl-C1-C4 alkyl, wherein the optional substituents are one or more substituents Rx and the halogen substituents are one or more substituents independently selected from F, Cl, Br, and I;
or a pharmaceutically acceptable salt or ester thereof.

### Claim 9 (depends on 8)

The compound according to claim 8, wherein R3 is selected from n-propyl, 3,3,3-trifluoropropyl, and isobutyl; or pharmaceutically acceptable salt or ester thereof.

### Claim 10 (depends on 1)

The compound according to claim 1, wherein R4 is selected from hydrogen and substituted or unsubstituted C1-C6 alkyl, wherein the optional substituents are one or more substituents Rx; or a pharmaceutically acceptable salt or ester thereof.

### Claim 11 (depends on 10)

The compound according to claim 10, wherein R4 is hydrogen or methyl; or a pharmaceutically acceptable salt or ester thereof.

### Claim 12 (depends on 1)

The compound according to claim 1, wherein R5 is selected from —C(ORe)2Rg, —CH(NRcRd)Rg, —(C═O)Rg, —(C═NRc)Rg, —(C═N—ORh)Rg, —(C═N—O—(C═O)Rf)Rg, —(C═N—O—(C═O)ORa)Rg, —(C═N—O—[(P═O)(ORa)2])Rg, —(C═N—NRcRd)Rg, —(C═CH2)Rg, and —(C═CH2)ORa wherein:
Rh is selected from hydrogen, a protecting group for OH, substituted or unsubstituted C1-C6 alkyl, substituted or unsubstituted C2-C6 alkenyl, substituted or unsubstituted C2-C6 alkynyl, substituted or unsubstituted heterocyclo-C1-C6alkyl, —(CH2CH2O)pCH2CH3 where p is from 1 to about 15 and a substituted or unsubstituted monosaccharide residue of formula:
where each R group is, at each occurrence, independently selected from hydrogen, substituted or unsubstituted C1-C6 alkyl group, substituted or unsubstituted —(C═O)—(C1-C6)alkyl, and substituted or unsubstituted —(C═O)NH(C1-C6)alkyl; wherein the optional substituents are one or more substituents Rx; or two adjacent OR groups form an isopropylidene ketal or an acetal group selected from methylene-, methoxymethylene-, ethoxymethylene-, ethylidene-, benzylidene-, and p-methoxybenzylidene-acetals;
Rg is substituted or unsubstituted C1-C6 alkyl, wherein the optional substituents are one or more substituents Rx;
Rc and Rd are independently selected from hydrogen and substituted or unsubstituted C1-C6 alkyl, wherein the optional substituents are one or more substituents Rx;
Ra is substituted or unsubstituted C1-C6 alkyl, wherein the optional substituents are one or more substituents Rx;
Re is substituted or unsubstituted C1-C6 alkyl, wherein the optional substituents are one or more substituents Rx; and
Rf is selected from substituted or unsubstituted C1-C6 alkyl, —CH2O(CH2CH2O)pCH3 where p is from 1 to about 15 and the optional substituents are one or more substituents Rx, and a group of formula:
where each R group is, at each occurrence, independently selected from hydrogen, substituted or unsubstituted C1-C6 alkyl group, substituted or unsubstituted —(C═O)—(C1-C6)alkyl, and substituted or unsubstituted —(C═O)NH(C1-C6)alkyl, wherein the optional substituents are one or more substituents Rx; or two adjacent OR groups form an isopropylidene ketal or an acetal group selected from methylene-, methoxymethylene-, ethoxymethylene-, ethylidene-, benzylidene-, and p-methoxybenzylidene-acetals;
or a pharmaceutically acceptable salt or ester thereof.

### Claim 13 (depends on 12)

The compound according to claim 12 wherein R5 is selected from —CH(NH2)Me, —(C═O)Me, —(C═NRc)Me, —(C═N—ORh)Me, —(C═N—O—(C═O)Rf)Me, —(C═N—NH2)Me, —(C═N—O—(C═O)ORa)Me, —(C═N—O—[(P═O)(ORa)2])Me, —(C═CH2)Me, or —(C═CH2)ORa where Ra is ethyl or benzyl, Rc is —(CH2)3NHBoc, Rf is —(CH2)5—NHBoc, —CH2O(CH2CH2O)2Me or a group of formula:
and Rh is selected from hydrogen, methyl, allyl, propargyl, —(CH2)3NHBoc, —(CH2)3NH2, —(CH2)3SH, —(CH2)4OH, —(CH2)4OP(═O)(OH)2, —(CH2)4OP(═O)(Ot-Bu)2, —(CH2)4-[4λ2-morpholine], —(CH2)3-[1-methyl-4λ2-piperazine], —(CH2CH2O)3CH2CH3, and a monosaccharide residue of formula:
or a pharmaceutically acceptable salt or ester thereof.

### Claim 14 (depends on 1)

The compound according to claim 1 selected from
or a pharmaceutically acceptable salt or ester thereof.

### Claim 15 (depends on 1)

The compound according to claim 1,
wherein:
R5 is selected from —C(ORe)2Rg, —C(SRe)2Rg, —CH(ORa)Rg, —CH(O—(C═O)Rf)Rg, —CH(NRcRd)Rg, —CH(NRc—(C═O)Rf)Rg, —CH(NRc—ORh)Rg, —(C═O)Rg, —(C═NRc)Rg, —(C═N—ORh)Rg, —(C═N—O—(C═O)Rf)Rg, —(C═N—NRcRd)Rg, —(C═O)ORa, —(C═O)NRc—ORh, and —(C═O)NRcRd; or R5 is a
group where m is 0, 1 or 2 and each E group is independently selected from O and S;
each group Rf is independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, —CH2O(CH2CH2O)pCH2CH3 and —CH2O(CH2CH2O)pCH3 wherein p is from 1 to about 25 and the optional substituents are one or more substituents Rx;
each group Rh is independently selected from hydrogen, a protecting group for OH, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C3-C6cycloalkyl-C1-C12alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, —(CH2CH2O)pCH2CH3, —(CH2CH2O)pCH3 wherein p is from 1 to about 25, and substituted or unsubstituted monosaccharide residue, wherein the optional substituents are one or more substituents Rx; and
substituents Rx are selected from the group consisting of C1-C12 alkyl groups which may be optionally substituted with at least one group Ry, C2-C12 alkenyl groups which may be optionally substituted with at least one group Ry, C2-C12 alkynyl groups which may be optionally substituted with at least one group Ry, halogen atoms, oxo groups, thio groups, cyano groups, nitro groups, ORy, OCORy, OCOORy, CORy, COORy, OCONRyRz, CONRyRz, SRy, S(═O)Ry, SO2Ry, SSRy, P(═O)(Ry)ORz, NRyRz, NRyCORz, NRyC(═O)NRyRz, NRyC(═NRy)NRyRz, aryl groups having from 6 to 18 carbon atoms in one or more rings which may optionally be substituted with one or more substituents which may be the same or different selected from the group consisting of Ry, ORy, OCORy, OCOORy, NRyRz, NRyCORz, and NRyC(═NRy)NRyRz, aralkyl groups comprising an alkyl groups having from 1 to 12 carbon atoms substituted with an optionally substituted aryl group as defined above, aralkyloxy groups comprising an alkoxy group having from 1 to 12 carbon atoms substituted with an optionally substituted aryl group as defined above, and a 5- to 14-membered saturated or unsaturated heterocyclic group having one or more rings and comprising at least one oxygen, nitrogen or sulphur atom in said ring(s), said heterocyclic group optionally being substituted with one or more substituents Ry, and where there is more than one optional substituents on any given group the optional substituents Ry may be the same or different.

### Claim 16

A pharmaceutical composition comprising a compound of formula I or a pharmaceutically acceptable salt or ester thereof
wherein:
R1 is selected from hydrogen, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx;
R2 is selected from hydrogen, halogen, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C2-C24 alkenyl, substituted or unsubstituted C2-C24 alkynyl, —ORa, —OSO2Rb, —NRcRd, —NRc(C═O)Rf, and —NRcSO2Rb, wherein the optional substituents are one or more substituents Rx;
R3 is selected from halogen-substituted or unsubstituted C1-C12 alkyl, halogen-substituted or unsubstituted C2-C12 alkenyl, halogen-substituted or unsubstituted C2-C12 alkynyl and substituted or unsubstituted C3-C6 cycloalkyl-C1-C12 alkyl, wherein the optional substituents are one or more substituents Rx and the halogen substituents are one or more substituents independently selected from F, Cl, Br and I;
R4 is selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx;
R5 is selected from —C(ORe)2Rg, —C(SRe)2Rg, —CH(ORa)Rg, —CH(O—(C═O)Rf)Rg, —CH(NRcRd)Rg, —CH(NRc—(C═O)Rf)Rg, —CH(NRc—ORh)Rg, —(C═O)Rg, —(C═NRc)Rg, —(C═N—ORh)Rg, —(C═N—O—(C═O)Rf)Rg, —(C═N—O—(C═O)ORa)Rg, —(C═N—O—[(P═O)(ORa)2])Rg, —(C═N—NRcRd)Rg, —(C═O)ORa, —(C═O)NRc—ORh, —(C═O)NRcRd, —(C═CH2)Rg, and —(C═CH2)ORa; or R5 is a
m is 0, 1 or 2 and each E group is independently selected from O and S;
group where
Y is —O—;
Z is —S—;
each group Ra is independently selected from hydrogen, a protecting group for OH, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C2-C24 alkenyl, substituted or unsubstituted C2-C24 alkynyl, substituted or unsubstituted C3-C6cycloalkyl-C1-C12alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, —(CH2CH2O)pCH2CH3, and —(CH2CH2O)pCH3 wherein p is from 1 to about 25 and the optional substituents are one or more substituents Rx;
each group Rb is independently selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heterocyclic group, wherein the optional substituents are one or more substituents Rx;
each group Rc and Rd is independently selected from hydrogen, a protecting group for amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx; or Rc and Rd together with the nitrogen atom to which they are attached form a heterocyclic group;
each group Re is substituted or unsubstituted C1-C12 alkyl group, wherein the optional substituents are one or more substituents Rx;
each group Rf is independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, —CH2O(CH2CH2O)pCH2CH3, —CH2O(CH2CH2O)pCH3 wherein p is from 1 to about 25 and the optional substituents are one or more substituents Rx, and a group of formula:
where each R group is, at each occurrence, independently selected from hydrogen, substituted or unsubstituted C1-C6 alkyl group, substituted or unsubstituted —(C═O)—(C1-C6)alkyl, and substituted or unsubstituted —(C═O)NH(C1-C6)alkyl, wherein the optional substituents are one or more substituents Rx; or two adjacent OR groups form an isopropylidene ketal or an acetal group selected from methylene-, methoxymethylene-, ethoxymethylene-, ethylidene-, benzylidene-, and p-methoxybenzylidene-acetals;
each group Rg is independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx;
each group Rh is independently selected from hydrogen, a protecting group for OH, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C3-C6cycloalkyl-C1-C12alkyl, substituted or unsubstituted heterocyclo-C1-C12alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, —(CH2CH2O)pCH2CH3, —(CH2CH2O)pCH3 wherein p is from 1 to about 25, and substituted or unsubstituted monosaccharide residue, wherein the optional substituents are one or more substituents Rx;
substituents Rx are selected from the group consisting of C1-C12 alkyl groups which may be optionally substituted with at least one group Ry, C2-C12 alkenyl groups which may be optionally substituted with at least one group Ry, C2-C12 alkynyl groups which may be optionally substituted with at least one group Ry, halogen atoms, oxo groups, thio groups, cyano groups, nitro groups, ORy, OCORy, OCOORy, CORy, COORy, OCONRyRz, CONRyRz, SRy, S(═O)Ry, SO2Ry, OSO2ORy, SSRy, P(═O)(Ry)ORz, OP(═O)(ORy)2, NRyRz, NRyC(═O)Rz, NRyC(═O)ORz, NRyC(═O)NRyRz, NRyC(═NRy)NRyRz, aryl groups having from 6 to 18 carbon atoms in one or more rings which may optionally be substituted with one or more substituents which may be the same or different selected from the group consisting of Ry, ORy, OCORy, OCOORy, NRyRz, NRyCORz, and NRyC(═NRy)NRyRz, aralkyl groups comprising an alkyl groups having from 1 to 12 carbon atoms substituted with an optionally substituted aryl group as defined above, aralkyloxy groups comprising an alkoxy group having from 1 to 12 carbon atoms substituted with an optionally substituted aryl group as defined above, and a 5- to 14-membered saturated or unsaturated heterocyclic group having one or more rings and comprising at least one oxygen, nitrogen or sulphur atom in said ring(s), said heterocyclic group optionally being substituted with one or more substituents Ry, and where there is more than one optional substituents on any given group the optional substituents Ry may be the same or different; and
each Ry and Rz is independently selected from the group consisting of hydrogen, C1-C12 alkyl groups, C1-C12 alkyl groups that are substituted with at least one halogen atom, aralkyl groups comprising a C1-C12 alkyl group that is substituted with an aryl group having from 6 to 18 carbon atoms in one or more rings and heterocycloalkyl group comprising a C1-C12 alkyl group that is substituted with a 5- to 14-membered saturated or unsaturated heterocyclic group having one or more rings and comprising at least one oxygen, nitrogen or sulphur atom in said ring(s);
and a pharmaceutically acceptable carrier.

### Claim 17 (depends on 16)

A dosage form comprising a pharmaceutical composition as defined in claim 16.

### Claim 18

A method of treating cancer in a patient in need thereof, comprising administering a therapeutically acceptable amount of a compound of formula I or a pharmaceutically acceptable salt or ester thereof
wherein:
R1 is selected from hydrogen, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx;
R2 is selected from hydrogen, halogen, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C2-C24 alkenyl, substituted or unsubstituted C2-C24 alkynyl, —ORa, —OSO2Rb, —NRcRd, —NRc(C═O)Rf, and —NRcSO2Rb, wherein the optional substituents are one or more substituents Rx;
R3 is selected from halogen-substituted or unsubstituted C1-C12 alkyl, halogen-substituted or unsubstituted C2-C12 alkenyl, halogen-substituted or unsubstituted C2-C12 alkynyl and substituted or unsubstituted C3-C6 cycloalkyl-C1-C12 alkyl, wherein the optional substituents are one or more substituents Rx and the halogen substituents are one or more substituents independently selected from F, Cl, Br and I;
R4 is selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx;
R5 is selected from —C(ORe)2Rg, —C(SRe)2Rg, —CH(ORa)Rg, —CH(O—(C═O)Rf)Rg, —CH(NRcRd)Rg, —CH(NRc—(C═O)Rf)Rg, —CH(NRc—ORh)Rg, —(C═O)Rg, —(C═NRc)Rg, —(C═N—ORh)Rg, —(C═N—O—(C═O)Rf)Rg, —(C═N—O—(C═O)ORa)Rg, —(C═N—O—[(P═O)(ORa)2])Rg, —(C═N—NRcRd)Rg, —(C═O)ORa, —(C═O)NRc—ORh, —(C═O)NRcRd, —(C═CH2)Rg, and —(C═CH2)ORa; or R5 is a
group where m is 0, 1 or 2 and each E group is independently selected from O and S;
Y is —O—;
Z is —S—;
each group Ra is independently selected from hydrogen, a protecting group for OH, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C2-C24 alkenyl, substituted or unsubstituted C2-C24 alkynyl, substituted or unsubstituted C3-C6cycloalkyl-C1-C12alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, —(CH2CH2O)pCH2CH3, and —(CH2CH2O)pCH3 wherein p is from 1 to about 25 and the optional substituents are one or more substituents Rx;
each group Rb is independently selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heterocyclic group, wherein the optional substituents are one or more substituents Rx;
each group Rc and Rd is independently selected from hydrogen, a protecting group for amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx; or Rc and Rd together with the nitrogen atom to which they are attached form a heterocyclic group;
each group Re is substituted or unsubstituted C1-C12 alkyl group, wherein the optional substituents are one or more substituents Rx;
each group Rf is independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, —CH2O(CH2CH2O)pCH2CH3, —CH2O(CH2CH2O)pCH3 wherein p is from 1 to about 25 and the optional substituents are one or more substituents Rx, and a group of formula:
where each R group is, at each occurrence, independently selected from hydrogen, substituted or unsubstituted C1-C6 alkyl group, substituted or unsubstituted —(C═O)—(C1-C6)alkyl, and substituted or unsubstituted —(C═O)NH(C1-C6)alkyl, wherein the optional substituents are one or more substituents Rx; or two adjacent OR groups form an isopropylidene ketal or an acetal group selected from methylene-, methoxymethylene-, ethoxymethylene-, ethylidene-, benzylidene-, and p-methoxybenzylidene-acetals;
each group Rg is independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx;
each group Rx is independently selected from hydrogen, a protecting group for OH, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C3-C6cycloalkyl-C1-C12alkyl, substituted or unsubstituted heterocyclo-C1-C12alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, —(CH2CH2O)pCH2CH3, —(CH2CH2O)pCH3 wherein p is from 1 to about 25, and substituted or unsubstituted monosaccharide residue, wherein the optional substituents are one or more substituents Rx;
substituents Rx are selected from the group consisting of C1-C12 alkyl groups which may be optionally substituted with at least one group Ry, C2-C12 alkenyl groups which may be optionally substituted with at least one group Ry, C2-C12 alkynyl groups which may be optionally substituted with at least one group Ry, halogen atoms, oxo groups, thio groups, cyano groups, nitro groups, ORy, OCORy, OCOORy, CORy, COORy, OCONRyRz, CONRyRz, SRy, S(═O)Ry, SO2Ry, OSO2ORy, SSRy, P(═O)(Ry)ORz, OP(═O)(ORy)2, NRyRz, NRyC(═O)Rz, NRyC(═O)ORz, NRyC(═O)NRyRz, NRyC(═NRy)NRyRz, aryl groups having from 6 to 18 carbon atoms in one or more rings which may optionally be substituted with one or more substituents which may be the same or different selected from the group consisting of Ry, ORy, OCORy, OCOORy, NRyRz, NRyCORz, and NRyC(═NRy)NRyRz, aralkyl groups comprising an alkyl groups having from 1 to 12 carbon atoms substituted with an optionally substituted aryl group as defined above, aralkyloxy groups comprising an alkoxy group having from 1 to 12 carbon atoms substituted with an optionally substituted aryl group as defined above, and a 5- to 14-membered saturated or unsaturated heterocyclic group having one or more rings and comprising at least one oxygen, nitrogen or sulphur atom in said ring(s), said heterocyclic group optionally being substituted with one or more substituents Ry, and where there is more than one optional substituents on any given group the optional substituents Ry may be the same or different; and
each Ry and Rz is independently selected from the group consisting of hydrogen, C1-C12 alkyl groups, C1-C12 alkyl groups that are substituted with at least one halogen atom, aralkyl groups comprising a C1-C12 alkyl group that is substituted with an aryl group having from 6 to 18 carbon atoms in one or more rings and heterocycloalkyl group comprising a C1-C12 alkyl group that is substituted with a 5- to 14-membered saturated or unsaturated heterocyclic group having one or more rings and comprising at least one oxygen, nitrogen or sulphur atom in said ring(s).

### Claim 19 (depends on 18)

The method according to claim 18, wherein the cancer is selected from solid tumours, lung cancer, colon cancer, breast cancer and pancreas cancer.

### Claim 20

A process for obtaining a compound of formula I or a pharmaceutically acceptable salt or ester thereof comprising the coupling of a compound of formula II with a compound of formula III in accordance to Scheme 1
wherein
R1 is selected from hydrogen, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx;
R2 is selected from hydrogen, halogen, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C2-C24 alkenyl, substituted or unsubstituted C2-C24 alkynyl, —ORa, —OSO2Rb, —NRcRd, —NRc(C═O)Rf, and —NRcSO2Rb, wherein the optional substituents are one or more substituents Rx;
R3 is selected from halogen-substituted or unsubstituted C1-C12 alkyl, halogen-substituted or unsubstituted C2-C12 alkenyl, halogen-substituted or unsubstituted C2-C12 alkynyl and substituted or unsubstituted C3-C6 cycloalkyl-C1-C12 alkyl, wherein the optional substituents are one or more substituents Rx and the halogen substituents are one or more substituents independently selected from F, Cl, Br and I;
R4 is selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx;
R5 is selected from —C(ORe)2Rg, —C(SRe)2Rg, —CH(ORa)Rg, —CH(O—(C═O)Rf)Rg, —CH(NRcRd)Rg, —CH(NRc—(C═O)Rf)Rg, —CH(NRc—ORh)Rg, —(C═O)Rg, —(C═NRc)Rg, —(C═N—ORh)Rg, —(C═N—O—(C═O)Rf)Rg, —(C═N—O—(C═O)ORa)Rg, —(C═N—O—[(P═O)(ORa)2])Rg, —(C═N—NRcRd)Rg, —(C═O)ORa, —(C═O)NRc—ORh, —(C═O)NRcRd, —(C═CH2)Rg, and —(C═CH2)ORa; or R5 is a
group where m is 0, 1 or 2 and each E group is independently selected from O and S;
Y is —O—;
Z is —S—;
each group Ra is independently selected from hydrogen, a protecting group for OH, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C2-C24 alkenyl, substituted or unsubstituted C2-C24 alkynyl, substituted or unsubstituted C3-C6cycloalkyl-C1-C12alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, —(CH2CH2O)pCH2CH3, and —(CH2CH2O)pCH3 wherein p is from 1 to about 25 and the optional substituents are one or more substituents Rx;
each group Rb is independently selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heterocyclic group, wherein the optional substituents are one or more substituents Rx;
each group Rc and Rd is independently selected from hydrogen, a protecting group for amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx; or Rc and Rd together with the nitrogen atom to which they are attached form a heterocyclic group;
each group Re is substituted or unsubstituted C1-C12 alkyl group, wherein the optional substituents are one or more substituents Rx;
each group Rf is independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, —CH2O(CH2CH2O)pCH2CH3, —CH2O(CH2CH2O),CH3 wherein p is from 1 to about 25 and the optional substituents are one or more substituents Rx, and a group of formula:
where each R group is, at each occurrence, independently selected from hydrogen, substituted or unsubstituted C1-C6 alkyl group, substituted or unsubstituted —(C═O)—(C1-C6)alkyl, and substituted or unsubstituted —(C═O)NH(C1-C6)alkyl, wherein the optional substituents are one or more substituents Rx; or two adjacent OR groups form an isopropylidene ketal or an acetal group selected from methylene-, methoxymethylene-, ethoxymethylene-, ethylidene-, benzylidene-, and p-methoxybenzylidene-acetals;
each group Rg is independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx;
each group Rh is independently selected from hydrogen, a protecting group for OH, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C3-C6cycloalkyl-C1-C12alkyl, substituted or unsubstituted heterocyclo-C1-C12alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, —(CH2CH2O)pCH2CH3, —(CH2CH2O)pCH3 wherein p is from 1 to about 25, and substituted or unsubstituted monosaccharide residue, wherein the optional substituents are one or more substituents Rx;
substituents Rx are selected from the group consisting of C1-C12 alkyl groups which may be optionally substituted with at least one group Ry, C2-C12 alkenyl groups which may be optionally substituted with at least one group Ry, C2-C12 alkynyl groups which may be optionally substituted with at least one group Ry, halogen atoms, oxo groups, thio groups, cyano groups, nitro groups, ORy, OCORy, OCOORy, CORy, COORy, OCONRyRz, CONRyRz, SRy, S(═O)Ry, SO2Ry, OSO2ORy, SSRy, P(═O)(Ry)ORz, OP(═O)(ORy)2, NRyRz, NRyC(═O)Rz, NRyC(═O)ORz, NRyC(═O)NRyRz, NRyC(═NRy)NRyRz, aryl groups having from 6 to 18 carbon atoms in one or more rings which may optionally be substituted with one or more substituents which may be the same or different selected from the group consisting of Ry, ORy, OCORy, OCOORy, NRyRz, NRyCORz, and NRyC(═NRy)NRyRz, aralkyl groups comprising an alkyl groups having from 1 to 12 carbon atoms substituted with an optionally substituted aryl group as defined above, aralkyloxy groups comprising an alkoxy group having from 1 to 12 carbon atoms substituted with an optionally substituted aryl group as defined above, and a 5- to 14-membered saturated or unsaturated heterocyclic group having one or more rings and comprising at least one oxygen, nitrogen or sulphur atom in said ring(s), said heterocyclic group optionally being substituted with one or more substituents Ry, and where there is more than one optional substituents on any given group the optional substituents Ry may be the same or different; and
each Ry and Rz is independently selected from the group consisting of hydrogen, C1-C12 alkyl groups, C1-C12 alkyl groups that are substituted with at least one halogen atom, aralkyl groups comprising a C1-C12 alkyl group that is substituted with an aryl group having from 6 to 18 carbon atoms in one or more rings and heterocycloalkyl group comprising a C1-C12 alkyl group that is substituted with a 5- to 14-membered saturated or unsaturated heterocyclic group having one or more rings and comprising at least one oxygen, nitrogen or sulphur atom in said ring(s);
or an appropriately protected group as needed.

### Claim 21

An intermediate compound of formula IIa
wherein:
R1 is selected from hydrogen, halogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx;
R2 is selected from hydrogen, halogen, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C2-C24 alkenyl, substituted or unsubstituted C2-C24 alkynyl, —ORa, OSO2Rb, —NRcRd, —NRc(C═O)Rf, and —NRcSO2Rb, wherein the optional substituents are one or more substituents Rx;
R3 is selected from halogen-substituted or unsubstituted C1-C12 alkyl, halogen-substituted or unsubstituted C2-C12 alkenyl, halogen-substituted or unsubstituted C2-C12 alkynyl and substituted or unsubstituted C3-C6 cycloalkyl-C1-C12 alkyl, wherein the optional substituents are one or more substituents Rx and the halogen substituents are one or more substituents independently selected from F, Cl, Br, and I;
R6 is selected from hydrogen and a carbamate protecting group for amino;
Y is —O—;
Ra is selected from hydrogen, a protecting group for OH, substituted or unsubstituted C1-C24 alkyl, substituted or unsubstituted C2-C24 alkenyl, substituted or unsubstituted C2-C24 alkynyl, substituted or unsubstituted C3-C6cycloalkyl-C1-C12alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, —(CH2CH2O)pCH2CH3, and —(CH2CH2O)pCH3 wherein p is from 1 to about 25 and the optional substituents are one or more substituents Rx;
each group Rb is independently selected from substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted aryl, and substituted or unsubstituted heterocyclic group, wherein the optional substituents are one or more substituents Rx;
each group Rc and Rd are independently selected from hydrogen, a protecting group for amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx; or Rc and Rd together with the nitrogen atom to which they are attached form a heterocyclic group;
Rf is independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, —CH2O(CH2CH2O)pCH2CH3, and —CH2O(CH2CH2O)pCH3 wherein p is from 1 to about 25 and the optional substituents are one or more substituents Rx;
substituents Rx are selected from the group consisting of C1-C12 alkyl groups which may be optionally substituted with at least one group Ry, C2-C12 alkenyl groups which may be optionally substituted with at least one group Ry, C2-C12 alkynyl groups which may be optionally substituted with at least one group Ry, halogen atoms, oxo groups, thio groups, cyano groups, nitro groups, ORy, OCORy, OCOORy, CORy, COORy, OCONRyRz, CONRyRz, SRy, S(═O)Ry, SO2Ry, OSO2ORy, SSRy, P(═O)(Ry)ORz, OP(═O)(ORy)2, NRyRz, NRyC(═O)Rz, NRyC(═O)ORz, NRyC(═O)NRyRz, NRyC(═NRy)NRyRz, aryl groups having from 6 to 18 carbon atoms in one or more rings which may optionally be substituted with one or more substituents which may be the same or different selected from the group consisting of Ry, ORy, OCORy, OCOORy, NRyRz, NRyCORz, and NRyC(═NRy)NRyRz, aralkyl groups comprising an alkyl groups having from 1 to 12 carbon atoms substituted with an optionally substituted aryl group as defined above, aralkyloxy groups comprising an alkoxy group having from 1 to 12 carbon atoms substituted with an optionally substituted aryl group as defined above, and a 5- to 14-membered saturated or unsaturated heterocyclic group having one or more rings and comprising at least one oxygen, nitrogen or sulphur atom in said ring(s), said heterocyclic group optionally being substituted with one or more substituents Ry, and where there is more than one optional substituents on any given group the optional substituents Ry may be the same or different; and
each Ry and Rz is independently selected from the group consisting of hydrogen, C1-C12 alkyl groups, C1-C12 alkyl groups that are substituted with at least one halogen atom, aralkyl groups comprising a C1-C12 alkyl group that is substituted with an aryl group having from 6 to 18 carbon atoms in one or more rings and heterocycloalkyl group comprising a C1-C12 alkyl group that is substituted with a 5- to 14-membered saturated or unsaturated heterocyclic group having one or more rings and comprising at least one oxygen, nitrogen or sulphur atom in said ring(s);
or a salt thereof.

### Claim 22

An intermediate compound of formula IIIa
wherein R4 is selected from unsubstituted C1-C12 alkyl, unsubstituted C2-C12 alkenyl and unsubstituted C2-C12 alkynyl;
R5 is selected from —C(ORe)2Rg, —C(SRe)2Rg, —CH(ORa)Rg, —CH(O—(C═O)Rf)Rg, —CH(NRc—(C═O)Rf)Rg, —CH(NRc—ORh)Rg, —(C═O)Rg, —(C═NRc)Rg, —(C═N—ORh)Rg, —(C═N—O—(C═O)Rf)Rg, —(C═N—O—(C═O)ORa)Rg, —(C═N—O—[(P═O)(ORa)2])Rg, —(C═N—NRcRd)Rg, —(C═O)ORa, —(C═O)NRc—ORh, —(C═O)NRcRd, —(C═CH2)Rg, and —(C═CH2)ORa; or R5 is a
group where m is 0, 1, or 2 and each E group is independently selected from O and S;
Z is —S—;
each group Ra is independently selected from hydrogen, a protecting group for OH, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C3-C6cycloalkyl-C1-C12alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, —(CH2CH2O)pCH2CH3, and —(CH2CH2O)pCH3 wherein p is from 1 to about 25 and the optional substituents are one or more substituents Rx;
each group Rc and Rd is independently selected from hydrogen, a protecting group for amino, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx; or Rc and Rd together with the nitrogen atom to which they are attached form a heterocyclic group;
each group Re is substituted or unsubstituted C1-C12 alkyl group, wherein the optional substituents are one or more substituents Rx;
each group Rf is independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, —CH2O(CH2CH2O)pCH2CH3, —CH2O(CH2CH2O)pCH3 wherein p is from 1 to about 25 and the optional substituents are one or more substituents Rx, and a group of formula:
where each R group is, at each occurrence, independently selected from hydrogen, substituted or unsubstituted C1-C6 alkyl group, substituted or unsubstituted —(C═O)—(C1-C6)alkyl, and substituted or unsubstituted —(C═O)NH(C1-C6)alkyl, wherein the optional substituents are one or more substituents Rx; or two adjacent OR groups form an isopropylidene ketal or an acetal group selected from methylene-, methoxymethylene-, ethoxymethylene-, ethylidene-, benzylidene-, and p-methoxybenzylidene-acetals;
each group Rg is independently selected from hydrogen, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl and substituted or unsubstituted C2-C12 alkynyl, wherein the optional substituents are one or more substituents Rx;
each group Rh is independently selected from hydrogen, a protecting group for OH, substituted or unsubstituted C1-C12 alkyl, substituted or unsubstituted C2-C12 alkenyl, substituted or unsubstituted C2-C12 alkynyl, substituted or unsubstituted C3-C6cycloalkyl-C1-C12alkyl, substituted or unsubstituted heterocyclo-C1-C12alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclic group, —(CH2CH2O)pCH2CH3, —(CH2CH2O)pCH3, wherein p is from 1 to about 25, and substituted or unsubstituted monosaccharide residue, wherein the optional substituents are one or more substituents Rx;
substituents Rx are selected from the group consisting of C1-C12 alkyl groups which may be optionally substituted with at least one group Ry, C2-C12 alkenyl groups which may be optionally substituted with at least one group Ry, C2-C12 alkynyl groups which may be optionally substituted with at least one group Ry, halogen atoms, oxo groups, thio groups, cyano groups, nitro groups, ORy, OCORy, OCOORy, CORy, COORy, OCONRyRz, CONRyRz, SRy, S(═O)Ry, SO2Ry, OSO2ORy, SSRy, P(═O)(Ry)ORz, OP(═O)(ORy)2, NRyRz, NRyC(═O)Rz, NRyC(═O)ORz, NRyC(═O)NRyRz, NRyC(═NRy)NRyRz, aryl groups having from 6 to 18 carbon atoms in one or more rings which may optionally be substituted with one or more substituents which may be the same or different selected from the group consisting of Ry, ORy, OCORy, OCOORy, NRyRz, NRyCORz, and NRyC(═NRy)NRyRz, aralkyl groups comprising an alkyl groups having from 1 to 12 carbon atoms substituted with an optionally substituted aryl group as defined above, aralkyloxy groups comprising an alkoxy group having from 1 to 12 carbon atoms substituted with an optionally substituted aryl group as defined above, and a 5- to 14-membered saturated or unsaturated heterocyclic group having one or more rings and comprising at least one oxygen, nitrogen or sulphur atom in said ring(s), said heterocyclic group optionally being substituted with one or more substituents Ry, and where there is more than one optional substituents on any given group the optional substituents Ry may be the same or different; and
each Ry and Rz is independently selected from the group consisting of hydrogen, C1-C12 alkyl groups, C1-C12 alkyl groups that are substituted with at least one halogen atom, aralkyl groups comprising a C1-C12 alkyl group that is substituted with an aryl group having from 6 to 18 carbon atoms in one or more rings and heterocycloalkyl group comprising a C1-C12 alkyl group that is substituted with a 5- to 14-membered saturated or unsaturated heterocyclic group having one or more rings and comprising at least one oxygen, nitrogen or sulphur atom in said ring(s);
or a salt thereof.

### Claim 23 (depends on 1)

The compound according to claim 1, of formula
or a pharmaceutically acceptable salt or ester thereof.

### Claim 24 (depends on 1)

The compound according to claim 1, of formula
or a pharmaceutically acceptable salt or ester thereof.

### Claim 25 (depends on 1)

The compound according to claim 1, of formula
or a pharmaceutically acceptable salt or ester thereof.

### Claim 26 (depends on 1)

A method of inhibiting proliferation of cancer cells, comprising contacting cancer cells with an amount of a compound as defined in claim 1, wherein the amount is effective for inhibiting proliferation.

### Claim 27 (depends on 26)

The method according to claim 26, wherein the cancer cells are cells of a cancer type selected from lung cancer, colon cancer, breast cancer and pancreas cancer.

### Claim 28 (depends on 16)

A method of treating cancer in a patient in need thereof, comprising administering a pharmaceutical composition as defined in claim 16.