US 2006/0135488 A1Published application

PTP1b inhibitors

AssigneeWyeth

InventorsJinbo Lee, Michael Smith, Alessandro Moretto, Zhao-Kui Wan, Eva Binnun, Weixin Xu, Kenneth Foreman, Diane Joseph-McCarthy, David Erbe, Steve Tam

Life of this patent

Estimating the term…

Abstract

This invention relates to modulating (e.g., inhibiting) protein tyrosine phosphatase 1B (PTP1B).

Claims70

Dependent claims

A compound having formula (I):

wherein:
X is C(Ra)(Rb), NRc, or S;
Y is C(Rd)(Re), NRf, or a bond;
provided that when X is S, Y is a bond, and further provided that X and Y are not simultaneously NRc and NRf, respectively
ring C is:
(i) a fused C6-C16 aryl or a fused heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 R3;
or
(ii) a fused C3-C10 cycloalkyl, a fused C3-C10 cycloalkenyl, a fused heterocyclyl including 5-10 atoms, or a fused heterocycloalkenyl including 5-10 atoms, each of which is optionally substituted with from 1-5 R4;
R1 is:
(i) C6-C16 aryl or heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 Rg;
or
(ii) C3-C16 cycloalkyl or C3-C16 halocycloalkyl, each of which is optionally substituted with from 1-5 Rh;
or
(iii) C3-C10 cycloalkenyl, heterocyclyl including 5-10 atoms, or heterocycloalkenyl including 5-10 atoms, each of which is optionally substituted with from 1-5 Ri;
or
(iv) cyano, —C(O)Rj, —C(O)ORj, —OC(O)Rj, —C(O)SRj, —SC(O)Rj, —C(S)SRj, —SC(S)Rj, —NRkC(O)Rj, —C(O)NRmRn;
or —C(NRo)Rj;
W is O or S;
each of Z and Z′ is, independently:
(i) O, NRp, S, SO, or SO2;
or
(ii) C1-C12 alkylene, C2-C12 alkenylene, C2-C12 alkynylene, O(C1-C12 alkylene), O(C2-C12 alkenylene), O(C2-C12 alkynylene), NRp(C1-C12 alkylene), NRp(C2-C12 alkenylene), NRp(C2-C12 alkynylene), S(C1-C12 alkylene), S(C2-C12 alkenylene), S(C2-C12 alkynylene), SO(C2-C12 alkylene), SO(C2-C12 alkenylene), S0(C2-C12 alkynylene), SO2(C1-C12 alkylene), SO2(C2-C12 alkenylene), or 502(C2-C12 alkynylene), each of which is optionally substituted with 1-5 Rq;
R2 is:
(i) hydrogen;
or
(ii) C1-C20 alkyl, optionally substituted with from 1-10 Rr and/or optionally inserted with from 1-10 heteroatoms selected from the group consisting of nitrogen, oxygen or sulfur;
or
(iii) C1-C20 haloalkyl, optionally substituted with from 1-10 Rr;
or
(iv) C3-C20 cycloalkyl or C3-C20 halocycloalkyl, optionally substituted with from 1-10 Rh;
or
(v) C3-C20 cycloalkenyl, heterocyclyl including 3-20 atoms, or heterocycloalkenyl including 3-20 atoms, each of which is optionally substituted with from 1-10 Ri;
or
(vi) C2-C20 alkenyl or C2-C20 alkynyl, each of which is optionally substituted with from 1-10 Rs;
(vii) C7-C20 aralkyl, heteroaralkyl including 6-20 atoms, C8-C20 arylcycloalkyl, C8-C20 arylcycloalkenyl, arylheterocyclyl including 8-20 atoms, or arylheterocycloalkenyl including 8-20 atoms, each of which is optionally substituted with from 1-10 Rt;
or
(viii) C6-C16 aryl or heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 Rg;
each of R3 and R4, is, independently:
(i) halo;
NRmRn;
nitro;
azido, hydroxy;
oxo;
thioxo;
═NRo;
C1-C12 alkoxy, optionally substituted with 1-5 Rr;
C1-C12 haloalkoxy;
C6-C16 aryloxy, optionally substituted with 1-5 Rg;
C2-C12 alkenyloxy or C2-C12 alkynyloxy, each of which is optionally substituted with 1-5 RS;
C3-C16 cycloalkyloxy or C3-C16 halocycloalkyloxy, each of which is optionally substituted with 1-5 Rh;
heterocyclyloxy including 3-16 atoms, optionally substituted with 1-5 Ri;
C7-C20 aralkoxy, optionally substituted with 1-5 Rt;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Rj;
—C(O)NRmRn;
NRkC(O)Rj;
—C(NRo)Rj;
—OC(O)NRmRn;
—NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRu;
—NR kS(O)nRj;
or —P(O)(ORm)(ORn);
or
(ii) C1-C20 alkyl, optionally substituted with from 1-10 Rr and/or optionally inserted with from 1-10 heteroatoms selected from the group consisting of nitrogen, oxygen or sulfur;
or
(iii) C1-C20 haloalkyl, optionally substituted with from 1-10 Rr;
or
(iv) C3-C20 cycloalkyl or C3-C20 halocycloalkyl, optionally substituted with from 1-10 Rh;
or
(v) C3-C20 cycloalkenyl, heterocyclyl including 3-20 atoms, or heterocycloalkenyl including 3-20 atoms, each of which is optionally substituted with from 1-10 Ri;
or
(vi) C2-C20 alkenyl or C2-C20 alkynyl, each of which is optionally substituted with from 1-10 Rs;
(vii) C7-C20 aralkyl, heteroaralkyl including 6-20 atoms, C8-C20 arylcycloalkyl, C8-C20 arylcycloalkenyl, arylheterocyclyl including 8-20 atoms, or arylheterocycloalkenyl including 8-20 atoms, each of which is optionally substituted with from 1-10 Rt;
or
(viii) C6-C16 aryl or heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 Rg;
each of Ra and Rb is, independently, hydrogen or C1-C10 alkyl;
or one of Ra and Rb is hydrogen or C1-C10 alkyl, and the other together with Rd, Re, or Rf is a bond;
Rc is hydrogen or C1-C6 alkyl;
or Rc together with Rd or Re is a bond;
each of Rd and Re is, independently, hydrogen or C1-C10 alkyl;
or one of Rd and Re is hydrogen or C1-C6 alkyl, and the other together with Ra, Rb, or Rc is a bond;
Rf is hydrogen or C1-C6 alkyl;
or Rf together with Ra or Rb is a bond;
Rg at each occurrence is, independently:
(i) halo;
NRmRn;
nitro;
azido, hydroxy;
C1-C12 alkoxy, optionally substituted with 1-5 Rr;
C1-C12 haloalkoxy;
C6-C16 aryloxy, optionally substituted with 1-5 Rg or Rg′;
C2-C12 alkenyloxy or C2-C12 alkynyloxy, each of which is optionally substituted with 1-5 Rs;
C3-C16 cycloalkyloxy or C3-C16 halocycloalkyloxy, each of which is optionally substituted with 1-5 Rh;
heterocyclyloxy including 3-16 atoms, optionally substituted with 1-5 Ri;
C7-C20 aralkoxy, optionally substituted with 1-5 Rt;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Ri;
—C(O)NRmRn;
—NRkC(O)Rj;
—C(NRO)Rj;
—OC(O)NRmRn;
—NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRu;
—NRkS(O)nRj;
or —P(O)(ORm)(ORn);
or
(ii) C1-C12 alkyl, optionally substituted with from 1-10 Rr and/or optionally inserted with from 1-6 heteroatoms selected from the group consisting of nitrogen, oxygen or sulfur;
or
(iii) C3-C20 cycloalkyl or C3-C20 halocycloalkyl, optionally substituted with from 1-10 Rh;
or
(iv) C3-C20 cycloalkenyl, heterocyclyl including 3-20 atoms, or heterocycloalkenyl including 3-20 atoms, each of which is optionally substituted with from 1-10 Ri;
or
(v) C2-C20 alkenyl or C2-C20 alkynyl, each of which is optionally substituted with from 1-10 Rs;
or
(vi) C1-C12 haloalkyl;
or
(vii) C7-C20 aralkyl or heteroaralkyl including 6-20 atoms, each of which is optionally substituted with from 1-10 Rt;
or
(viii) C6-C16 aryl or heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 Rg or Rg′;
Rg′ at each occurrence is, independently, C1-C12 alkyl, C1-C12 haloalkyl, C2-C12 alkenyl;
C2-C12 alkynyl;
C3-C20 cycloalkyl;
C3-C20 halocycloalkyl;
C3-C20 cycloalkenyl, heterocyclyl including 3-20 atoms, or heterocycloalkenyl including 3-20 atoms;
C7-C20 aralkyl;
C6-C16 aryl or heteroaryl including 5-16 atoms;
halo;
NRmRn;
nitro;
azido, hydroxy;
C1-C12 alkoxy;
C1-C12 haloalkoxy;
C6-C16 aryloxy;
C2-C12 alkenyloxy;
C2-C12 alkynyloxy;
C3-C16 cycloalkyloxy;
C3-C16 halocycloalkyloxy;
heterocyclyloxy including 3-16 atoms;
C7-C20 aralkoxy;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Rj;
—C(O)NRmRn;
—NRkC(O)Ri;
—C(NRO)Rj;
—OC(O)NRmRn;
—NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRj;
—NRkS(O)nRj;
or —P(O)(ORm)(ORn);
Rh at each occurrence is, independently:
(i) NRmRn;
nitro;
azido;
hydroxy;
oxo;
thioxo;
═NRo;
C1-C12 alkoxy, optionally substituted with 1-5 Rr;
C1-C12 haloalkoxy;
C6-C16 aryloxy, optionally substituted with 1-5 Rg;
C2-C12 alkenyloxy or C2-C12 alkynyloxy, each of which is optionally substituted with 1-5 Rs;
C3-C16 cycloalkyloxy or C3-C16 halocycloalkyloxy, each of which is optionally substituted with 1-5 Rh;
heterocyclyloxy including 3-16 atoms, optionally substituted with 1-5 Rh;
C7-C20 aralkoxy, optionally substituted with 1-5 Rt;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Rj;
—C(O)NRmRn;
—NRkC(O)Rj;
—C(NRo)Rj;
—OC(O)NRmRn;
—NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRu;
—NRkS(O)nRj;
or —P(O)(ORm)(ORn);
or
(ii) C2-C20 alkenyl or C2-C20 alkynyl, each of which is optionally substituted with from 1-10 Rs;
or
(iii) C6-C16 aryl or heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 Rg;
Ri at each occurrence is, independently:
(i) halo, NRmRn;
nitro;
azido, hydroxy;
oxo, thioxo, ═NRo, C1-C12 alkoxy, optionally substituted with 1-5 Rr;
C1-C12 haloalkoxy;
C6-C16 aryloxy, optionally substituted with 1-5 Rg;
C2-C12 alkenyloxy or C2-C12 alkynyloxy, each of which is optionally substituted with 1-5 Rs;
C3-C16 cycloalkyloxy or C3-C16 halocycloalkyloxy, each of which is optionally substituted with 1-5 Rh;
heterocyclyloxy including 3-16 atoms, optionally substituted with 1-5 Ri;
C7-C20 aralkoxy, optionally substituted with 1-5 Rt;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Rj;
—C(O)NRmRn;
NRkC(O)Rj;
—C(NRO)Rj;
—OC(O)NRmRn;
NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRu;
—NRkS(O)nRj;
or —P(O)(ORm)(ORn);
or
(ii) C2-C20 alkenyl or C2-C20 alkynyl, each of which is optionally substituted with from 1-10 Rs;
or
(iii) C6-C16 aryl or heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 Rg;
each of Ri, Rk, Rm, and Rn, at each occurrence is, independently:
(i) hydrogen;
or
(ii) C1-C20 alkyl, optionally substituted with from 1-10 Rr and/or optionally inserted with from 1-6 heteroatoms selected from the group consisting of nitrogen, oxygen or sulfur;
(iii) C1-C20 haloalkyl;
or
(iv) C2-C20 alkenyl or C2-C20 alkynyl, each of which is optionally substituted with from 1-10 Rs;
or
(v) C3-C20 cycloalkyl or C3-C20 halocycloalkyl, each of which is optionally substituted with from 1-10 Rh;
or
(vi) C3-C20 cycloalkenyl, heterocyclyl including 3-16 atoms, or heterocycloalkenyl including 3-16 atoms, each of which is optionally substituted with from 1-10 Ri;
or
(vii) C7-C20 aralkyl, heteroaralkyl including 6-20 atoms, C8-C20 arylcycloalkyl, C8-C20 arylcycloalkenyl, arylheterocyclyl including 8-20 atoms, or arylheterocycloalkenyl including 8-20 atoms, each of which is optionally substituted with from 1-10 Rt;
or
(viii) C6-C16 aryl or heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 Rg;
Ro is hydrogen;
C1-C12 alkyl optionally inserted with from 1-6 heteroatoms selected from the group consisting of nitrogen, oxygen or sulfur;
C2-C20 alkenyl;
C2-C20 alkynyl;
C7-C20 aralkyl;
heteroaralkyl including 6-20 atoms;
C3-C16 cycloalkyl;
C3-C16 cycloalkenyl;
heterocyclyl including 3-16 atoms;
heterocycloalkenyl including 3-16 atoms;
C8-C20 arylcycloalkyl;
C8-C20 arylcycloalkenyl;
arylheterocyclyl including 8-20 atoms;
or arylheterocycloalkenyl including 8-20 atoms;
C6-C16 aryl;
heteroaryl including 5-16 atoms;
NRmRn, or ORj;
Rp is hydrogen or C1-C12 alkyl;
Rq at each occurrence is, independently, halo, NRmRn;
nitro;
azido, hydroxy;
oxo, thioxo, ═NRo, C1-C12 alkoxy, optionally substituted with 1-5 Rr;
C1-C2 haloalkoxy;
C6-C16 aryloxy, optionally substituted with 1-5 Rg;
C2-C12 alkenyloxy or C2-C12 alkynyloxy, each of which is optionally substituted with 1-5 Rs;
C3-C16 cycloalkyloxy or C3-C16 halocycloalkyloxy, each of which is optionally substituted with 1-5 Rh;
heterocyclyloxy including 3-16 atoms, optionally substituted with 1-5 R1;
C7-C20 aralkoxy, optionally substituted with 1-5 Rt;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Rj;
—C(O)NRmRn;
—NRkC(O)Rj;
—C(NRO)Rj;
—OC(O)NRnRn;
—NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRu;
—NRkS(O),Rj;
or —P(O)(ORm)(ORn);
Rr at each occurrence is, independently, NRmRn;
nitro;
azido, hydroxy;
oxo, thioxo, ═NRo, C1-C12 alkoxy, optionally substituted with 1-5 Rr;
C1-C12 haloalkoxy;
C6-C16 aryloxy, optionally substituted with 1-5 Rg;
C2-C12 alkenyloxy or C2-C12 alkynyloxy, each of which is optionally substituted with 1-5 Rs;
C3-C16 cycloalkyloxy or C3-C16 halocycloalkyloxy, each of which is optionally substituted with 1-5 Rh;
heterocyclyloxy including 3-16 atoms, optionally substituted with 1-5 Ri;
C7-C20 aralkoxy, optionally substituted with 1-5 Rt;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Rj;
—C(O)NRmRn;
—NRkC(O)Rj;
—C(NRo)Rj;
—OC(O)NRmRn;
—NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRu;
—NRkS(O)nRj;
or —P(O)(ORm)(ORn);
Rs at each occurrence is, independently, halo, NRmRn;
nitro;
azido, hydroxy;
oxo, thioxo, ═NRo, C1-C12 alkoxy, optionally substituted with 1-5 Rr;
C1-C12 haloalkoxy;
C6-C16 aryloxy, optionally substituted with 1-5 Rg;
C2-C12 alkenyloxy or C2-C12 alkynyloxy, each of which is optionally substituted with 1-5 Rs;
C3-C16 cycloalkyloxy or C3-C16 halocycloalkyloxy, each of which is optionally substituted with 1-5 Rh;
heterocyclyloxy including 3-16 atoms, optionally substituted with 1-5 Rj;
C7-C20 aralkoxy, optionally substituted with 1-5 Rt;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Rj;
—C(O)NRmRn;
—NRkC(O)Rj;
—C(NRo)Rj;
—OC(O)NRmRn;
—NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRu;
—NRkS(O)nRj;
or —P(O)(ORm)(ORn);
Rt at each occurrence is, independently:
(i) C1-C12 alkyl, C1-C12 haloalkyl, halo, NRmRn;
nitro;
azido, hydroxy;
oxo, thioxo, ═NRo, C1-C12 alkoxy, optionally substituted with 1-5 Rr;
C1-C12 haloalkoxy;
C6-C16 aryloxy, optionally substituted with 1-5 Rg;
C2-C12 alkenyloxy or C2-C12 alkynyloxy, each of which is optionally substituted with 1-5 Rs;
C3-C16 cycloalkyloxy or C3-C16 halocycloalkyloxy, each of which is optionally substituted with 1-5 Rh;
heterocyclyloxy including 3-16 atoms, optionally substituted with 1-5 Ri;
C7-C20 aralkoxy, optionally substituted with 1-5 Rt;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Rj;
—C(O)NRmRn;
—NRkC(O)Rj;
—C(NRo)Rj;
—OC(O)NRmRn;
—NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRu;
—NRkS(O)nRi;
or —P(O)(ORm)(ORn);
or
(ii) C2-C20 alkenyl or C2-C20 alkynyl, each of which is optionally substituted with from 1-10 Rs;
or
(iii) C6-C16 aryl or heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 Rg;
Ru is Rj, ORj, or NRmRn;
n is 0, 1 or 2;
or a salt thereof.

420 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/285,223Filed 22 Nov 2005
Priority: 24 Nov 2004
Published: 22 Jun 2006
Term ends: Not estimatedThe source records don’t support an estimate.

Classification4 codes

C07D 495/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07D 333/70
Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen: attached in position 2
C07D 333/74
Condensed with carbocyclic rings or ring systems: naphthothiophenes
C07D
Heterocyclic compounds

Family

Application60/630,623Us provisional application · filed 24 Nov 2004
US 7,674,822 B2Related patent
US 2006/0135488 A1This patent

From the US filing history. Foreign family members aren’t listed.

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A compound having formula (I):

wherein:
X is C(Ra)(Rb), NRc, or S;
Y is C(Rd)(Re), NRf, or a bond;
provided that when X is S, Y is a bond, and further provided that X and Y are not simultaneously NRc and NRf, respectively
ring C is:
(i) a fused C6-C16 aryl or a fused heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 R3;
or
(ii) a fused C3-C10 cycloalkyl, a fused C3-C10 cycloalkenyl, a fused heterocyclyl including 5-10 atoms, or a fused heterocycloalkenyl including 5-10 atoms, each of which is optionally substituted with from 1-5 R4;
R1 is:
(i) C6-C16 aryl or heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 Rg;
or
(ii) C3-C16 cycloalkyl or C3-C16 halocycloalkyl, each of which is optionally substituted with from 1-5 Rh;
or
(iii) C3-C10 cycloalkenyl, heterocyclyl including 5-10 atoms, or heterocycloalkenyl including 5-10 atoms, each of which is optionally substituted with from 1-5 Ri;
or
(iv) cyano, —C(O)Rj, —C(O)ORj, —OC(O)Rj, —C(O)SRj, —SC(O)Rj, —C(S)SRj, —SC(S)Rj, —NRkC(O)Rj, —C(O)NRmRn;
or —C(NRo)Rj;
W is O or S;
each of Z and Z′ is, independently:
(i) O, NRp, S, SO, or SO2;
or
(ii) C1-C12 alkylene, C2-C12 alkenylene, C2-C12 alkynylene, O(C1-C12 alkylene), O(C2-C12 alkenylene), O(C2-C12 alkynylene), NRp(C1-C12 alkylene), NRp(C2-C12 alkenylene), NRp(C2-C12 alkynylene), S(C1-C12 alkylene), S(C2-C12 alkenylene), S(C2-C12 alkynylene), SO(C2-C12 alkylene), SO(C2-C12 alkenylene), S0(C2-C12 alkynylene), SO2(C1-C12 alkylene), SO2(C2-C12 alkenylene), or 502(C2-C12 alkynylene), each of which is optionally substituted with 1-5 Rq;
R2 is:
(i) hydrogen;
or
(ii) C1-C20 alkyl, optionally substituted with from 1-10 Rr and/or optionally inserted with from 1-10 heteroatoms selected from the group consisting of nitrogen, oxygen or sulfur;
or
(iii) C1-C20 haloalkyl, optionally substituted with from 1-10 Rr;
or
(iv) C3-C20 cycloalkyl or C3-C20 halocycloalkyl, optionally substituted with from 1-10 Rh;
or
(v) C3-C20 cycloalkenyl, heterocyclyl including 3-20 atoms, or heterocycloalkenyl including 3-20 atoms, each of which is optionally substituted with from 1-10 Ri;
or
(vi) C2-C20 alkenyl or C2-C20 alkynyl, each of which is optionally substituted with from 1-10 Rs;
(vii) C7-C20 aralkyl, heteroaralkyl including 6-20 atoms, C8-C20 arylcycloalkyl, C8-C20 arylcycloalkenyl, arylheterocyclyl including 8-20 atoms, or arylheterocycloalkenyl including 8-20 atoms, each of which is optionally substituted with from 1-10 Rt;
or
(viii) C6-C16 aryl or heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 Rg;
each of R3 and R4, is, independently:
(i) halo;
NRmRn;
nitro;
azido, hydroxy;
oxo;
thioxo;
═NRo;
C1-C12 alkoxy, optionally substituted with 1-5 Rr;
C1-C12 haloalkoxy;
C6-C16 aryloxy, optionally substituted with 1-5 Rg;
C2-C12 alkenyloxy or C2-C12 alkynyloxy, each of which is optionally substituted with 1-5 RS;
C3-C16 cycloalkyloxy or C3-C16 halocycloalkyloxy, each of which is optionally substituted with 1-5 Rh;
heterocyclyloxy including 3-16 atoms, optionally substituted with 1-5 Ri;
C7-C20 aralkoxy, optionally substituted with 1-5 Rt;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Rj;
—C(O)NRmRn;
NRkC(O)Rj;
—C(NRo)Rj;
—OC(O)NRmRn;
—NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRu;
—NR kS(O)nRj;
or —P(O)(ORm)(ORn);
or
(ii) C1-C20 alkyl, optionally substituted with from 1-10 Rr and/or optionally inserted with from 1-10 heteroatoms selected from the group consisting of nitrogen, oxygen or sulfur;
or
(iii) C1-C20 haloalkyl, optionally substituted with from 1-10 Rr;
or
(iv) C3-C20 cycloalkyl or C3-C20 halocycloalkyl, optionally substituted with from 1-10 Rh;
or
(v) C3-C20 cycloalkenyl, heterocyclyl including 3-20 atoms, or heterocycloalkenyl including 3-20 atoms, each of which is optionally substituted with from 1-10 Ri;
or
(vi) C2-C20 alkenyl or C2-C20 alkynyl, each of which is optionally substituted with from 1-10 Rs;
(vii) C7-C20 aralkyl, heteroaralkyl including 6-20 atoms, C8-C20 arylcycloalkyl, C8-C20 arylcycloalkenyl, arylheterocyclyl including 8-20 atoms, or arylheterocycloalkenyl including 8-20 atoms, each of which is optionally substituted with from 1-10 Rt;
or
(viii) C6-C16 aryl or heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 Rg;
each of Ra and Rb is, independently, hydrogen or C1-C10 alkyl;
or one of Ra and Rb is hydrogen or C1-C10 alkyl, and the other together with Rd, Re, or Rf is a bond;
Rc is hydrogen or C1-C6 alkyl;
or Rc together with Rd or Re is a bond;
each of Rd and Re is, independently, hydrogen or C1-C10 alkyl;
or one of Rd and Re is hydrogen or C1-C6 alkyl, and the other together with Ra, Rb, or Rc is a bond;
Rf is hydrogen or C1-C6 alkyl;
or Rf together with Ra or Rb is a bond;
Rg at each occurrence is, independently:
(i) halo;
NRmRn;
nitro;
azido, hydroxy;
C1-C12 alkoxy, optionally substituted with 1-5 Rr;
C1-C12 haloalkoxy;
C6-C16 aryloxy, optionally substituted with 1-5 Rg or Rg′;
C2-C12 alkenyloxy or C2-C12 alkynyloxy, each of which is optionally substituted with 1-5 Rs;
C3-C16 cycloalkyloxy or C3-C16 halocycloalkyloxy, each of which is optionally substituted with 1-5 Rh;
heterocyclyloxy including 3-16 atoms, optionally substituted with 1-5 Ri;
C7-C20 aralkoxy, optionally substituted with 1-5 Rt;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Ri;
—C(O)NRmRn;
—NRkC(O)Rj;
—C(NRO)Rj;
—OC(O)NRmRn;
—NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRu;
—NRkS(O)nRj;
or —P(O)(ORm)(ORn);
or
(ii) C1-C12 alkyl, optionally substituted with from 1-10 Rr and/or optionally inserted with from 1-6 heteroatoms selected from the group consisting of nitrogen, oxygen or sulfur;
or
(iii) C3-C20 cycloalkyl or C3-C20 halocycloalkyl, optionally substituted with from 1-10 Rh;
or
(iv) C3-C20 cycloalkenyl, heterocyclyl including 3-20 atoms, or heterocycloalkenyl including 3-20 atoms, each of which is optionally substituted with from 1-10 Ri;
or
(v) C2-C20 alkenyl or C2-C20 alkynyl, each of which is optionally substituted with from 1-10 Rs;
or
(vi) C1-C12 haloalkyl;
or
(vii) C7-C20 aralkyl or heteroaralkyl including 6-20 atoms, each of which is optionally substituted with from 1-10 Rt;
or
(viii) C6-C16 aryl or heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 Rg or Rg′;
Rg′ at each occurrence is, independently, C1-C12 alkyl, C1-C12 haloalkyl, C2-C12 alkenyl;
C2-C12 alkynyl;
C3-C20 cycloalkyl;
C3-C20 halocycloalkyl;
C3-C20 cycloalkenyl, heterocyclyl including 3-20 atoms, or heterocycloalkenyl including 3-20 atoms;
C7-C20 aralkyl;
C6-C16 aryl or heteroaryl including 5-16 atoms;
halo;
NRmRn;
nitro;
azido, hydroxy;
C1-C12 alkoxy;
C1-C12 haloalkoxy;
C6-C16 aryloxy;
C2-C12 alkenyloxy;
C2-C12 alkynyloxy;
C3-C16 cycloalkyloxy;
C3-C16 halocycloalkyloxy;
heterocyclyloxy including 3-16 atoms;
C7-C20 aralkoxy;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Rj;
—C(O)NRmRn;
—NRkC(O)Ri;
—C(NRO)Rj;
—OC(O)NRmRn;
—NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRj;
—NRkS(O)nRj;
or —P(O)(ORm)(ORn);
Rh at each occurrence is, independently:
(i) NRmRn;
nitro;
azido;
hydroxy;
oxo;
thioxo;
═NRo;
C1-C12 alkoxy, optionally substituted with 1-5 Rr;
C1-C12 haloalkoxy;
C6-C16 aryloxy, optionally substituted with 1-5 Rg;
C2-C12 alkenyloxy or C2-C12 alkynyloxy, each of which is optionally substituted with 1-5 Rs;
C3-C16 cycloalkyloxy or C3-C16 halocycloalkyloxy, each of which is optionally substituted with 1-5 Rh;
heterocyclyloxy including 3-16 atoms, optionally substituted with 1-5 Rh;
C7-C20 aralkoxy, optionally substituted with 1-5 Rt;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Rj;
—C(O)NRmRn;
—NRkC(O)Rj;
—C(NRo)Rj;
—OC(O)NRmRn;
—NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRu;
—NRkS(O)nRj;
or —P(O)(ORm)(ORn);
or
(ii) C2-C20 alkenyl or C2-C20 alkynyl, each of which is optionally substituted with from 1-10 Rs;
or
(iii) C6-C16 aryl or heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 Rg;
Ri at each occurrence is, independently:
(i) halo, NRmRn;
nitro;
azido, hydroxy;
oxo, thioxo, ═NRo, C1-C12 alkoxy, optionally substituted with 1-5 Rr;
C1-C12 haloalkoxy;
C6-C16 aryloxy, optionally substituted with 1-5 Rg;
C2-C12 alkenyloxy or C2-C12 alkynyloxy, each of which is optionally substituted with 1-5 Rs;
C3-C16 cycloalkyloxy or C3-C16 halocycloalkyloxy, each of which is optionally substituted with 1-5 Rh;
heterocyclyloxy including 3-16 atoms, optionally substituted with 1-5 Ri;
C7-C20 aralkoxy, optionally substituted with 1-5 Rt;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Rj;
—C(O)NRmRn;
NRkC(O)Rj;
—C(NRO)Rj;
—OC(O)NRmRn;
NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRu;
—NRkS(O)nRj;
or —P(O)(ORm)(ORn);
or
(ii) C2-C20 alkenyl or C2-C20 alkynyl, each of which is optionally substituted with from 1-10 Rs;
or
(iii) C6-C16 aryl or heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 Rg;
each of Ri, Rk, Rm, and Rn, at each occurrence is, independently:
(i) hydrogen;
or
(ii) C1-C20 alkyl, optionally substituted with from 1-10 Rr and/or optionally inserted with from 1-6 heteroatoms selected from the group consisting of nitrogen, oxygen or sulfur;
(iii) C1-C20 haloalkyl;
or
(iv) C2-C20 alkenyl or C2-C20 alkynyl, each of which is optionally substituted with from 1-10 Rs;
or
(v) C3-C20 cycloalkyl or C3-C20 halocycloalkyl, each of which is optionally substituted with from 1-10 Rh;
or
(vi) C3-C20 cycloalkenyl, heterocyclyl including 3-16 atoms, or heterocycloalkenyl including 3-16 atoms, each of which is optionally substituted with from 1-10 Ri;
or
(vii) C7-C20 aralkyl, heteroaralkyl including 6-20 atoms, C8-C20 arylcycloalkyl, C8-C20 arylcycloalkenyl, arylheterocyclyl including 8-20 atoms, or arylheterocycloalkenyl including 8-20 atoms, each of which is optionally substituted with from 1-10 Rt;
or
(viii) C6-C16 aryl or heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 Rg;
Ro is hydrogen;
C1-C12 alkyl optionally inserted with from 1-6 heteroatoms selected from the group consisting of nitrogen, oxygen or sulfur;
C2-C20 alkenyl;
C2-C20 alkynyl;
C7-C20 aralkyl;
heteroaralkyl including 6-20 atoms;
C3-C16 cycloalkyl;
C3-C16 cycloalkenyl;
heterocyclyl including 3-16 atoms;
heterocycloalkenyl including 3-16 atoms;
C8-C20 arylcycloalkyl;
C8-C20 arylcycloalkenyl;
arylheterocyclyl including 8-20 atoms;
or arylheterocycloalkenyl including 8-20 atoms;
C6-C16 aryl;
heteroaryl including 5-16 atoms;
NRmRn, or ORj;
Rp is hydrogen or C1-C12 alkyl;
Rq at each occurrence is, independently, halo, NRmRn;
nitro;
azido, hydroxy;
oxo, thioxo, ═NRo, C1-C12 alkoxy, optionally substituted with 1-5 Rr;
C1-C2 haloalkoxy;
C6-C16 aryloxy, optionally substituted with 1-5 Rg;
C2-C12 alkenyloxy or C2-C12 alkynyloxy, each of which is optionally substituted with 1-5 Rs;
C3-C16 cycloalkyloxy or C3-C16 halocycloalkyloxy, each of which is optionally substituted with 1-5 Rh;
heterocyclyloxy including 3-16 atoms, optionally substituted with 1-5 R1;
C7-C20 aralkoxy, optionally substituted with 1-5 Rt;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Rj;
—C(O)NRmRn;
—NRkC(O)Rj;
—C(NRO)Rj;
—OC(O)NRnRn;
—NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRu;
—NRkS(O),Rj;
or —P(O)(ORm)(ORn);
Rr at each occurrence is, independently, NRmRn;
nitro;
azido, hydroxy;
oxo, thioxo, ═NRo, C1-C12 alkoxy, optionally substituted with 1-5 Rr;
C1-C12 haloalkoxy;
C6-C16 aryloxy, optionally substituted with 1-5 Rg;
C2-C12 alkenyloxy or C2-C12 alkynyloxy, each of which is optionally substituted with 1-5 Rs;
C3-C16 cycloalkyloxy or C3-C16 halocycloalkyloxy, each of which is optionally substituted with 1-5 Rh;
heterocyclyloxy including 3-16 atoms, optionally substituted with 1-5 Ri;
C7-C20 aralkoxy, optionally substituted with 1-5 Rt;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Rj;
—C(O)NRmRn;
—NRkC(O)Rj;
—C(NRo)Rj;
—OC(O)NRmRn;
—NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRu;
—NRkS(O)nRj;
or —P(O)(ORm)(ORn);
Rs at each occurrence is, independently, halo, NRmRn;
nitro;
azido, hydroxy;
oxo, thioxo, ═NRo, C1-C12 alkoxy, optionally substituted with 1-5 Rr;
C1-C12 haloalkoxy;
C6-C16 aryloxy, optionally substituted with 1-5 Rg;
C2-C12 alkenyloxy or C2-C12 alkynyloxy, each of which is optionally substituted with 1-5 Rs;
C3-C16 cycloalkyloxy or C3-C16 halocycloalkyloxy, each of which is optionally substituted with 1-5 Rh;
heterocyclyloxy including 3-16 atoms, optionally substituted with 1-5 Rj;
C7-C20 aralkoxy, optionally substituted with 1-5 Rt;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Rj;
—C(O)NRmRn;
—NRkC(O)Rj;
—C(NRo)Rj;
—OC(O)NRmRn;
—NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRu;
—NRkS(O)nRj;
or —P(O)(ORm)(ORn);
Rt at each occurrence is, independently:
(i) C1-C12 alkyl, C1-C12 haloalkyl, halo, NRmRn;
nitro;
azido, hydroxy;
oxo, thioxo, ═NRo, C1-C12 alkoxy, optionally substituted with 1-5 Rr;
C1-C12 haloalkoxy;
C6-C16 aryloxy, optionally substituted with 1-5 Rg;
C2-C12 alkenyloxy or C2-C12 alkynyloxy, each of which is optionally substituted with 1-5 Rs;
C3-C16 cycloalkyloxy or C3-C16 halocycloalkyloxy, each of which is optionally substituted with 1-5 Rh;
heterocyclyloxy including 3-16 atoms, optionally substituted with 1-5 Ri;
C7-C20 aralkoxy, optionally substituted with 1-5 Rt;
mercapto;
C1-C6 thioalkoxy;
C6-C16 thioaryloxy;
cyano;
formyl;
—C(O)Rj, C1-C3 alkylenedioxy;
—C(O)ORj;
—OC(O)Rj;
—C(O)SRj;
—SC(O)Rj;
—C(S)SRj;
—SC(S)Rj;
—C(O)NRmRn;
—NRkC(O)Rj;
—C(NRo)Rj;
—OC(O)NRmRn;
—NRkC(O)NRmRn;
—NRkC(O)ORj;
—S(O)nRu;
—NRkS(O)nRi;
or —P(O)(ORm)(ORn);
or
(ii) C2-C20 alkenyl or C2-C20 alkynyl, each of which is optionally substituted with from 1-10 Rs;
or
(iii) C6-C16 aryl or heteroaryl including 5-16 atoms, each of which is optionally substituted with from 1-10 Rg;
Ru is Rj, ORj, or NRmRn;
n is 0, 1 or 2;
or a salt thereof.

420 more elements

Facts

Application

11/285,223Filed 22 Nov 2005

Priority

24 Nov 2004

Published

22 Jun 2006

Term ends

Not estimatedThe source records don’t support an estimate.

Classification4 codes

C07D 495/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07D 333/70
Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen: attached in position 2
C07D 333/74
Condensed with carbocyclic rings or ring systems: naphthothiophenes
C07D
Heterocyclic compounds