ZA200410108B - N-subsituted tricyclic 3-aminopyrazoles as PDGF receptor inhibitors - Google Patents
N-subsituted tricyclic 3-aminopyrazoles as PDGF receptor inhibitors Download PDFInfo
- Publication number
- ZA200410108B ZA200410108B ZA200410108A ZA200410108A ZA200410108B ZA 200410108 B ZA200410108 B ZA 200410108B ZA 200410108 A ZA200410108 A ZA 200410108A ZA 200410108 A ZA200410108 A ZA 200410108A ZA 200410108 B ZA200410108 B ZA 200410108B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- indeno
- dihydro
- pyrazol
- phenyl
- Prior art date
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- 108091008606 PDGF receptors Proteins 0.000 title claims description 54
- 102000011653 Platelet-Derived Growth Factor Receptors Human genes 0.000 title claims description 39
- 239000003112 inhibitor Substances 0.000 title claims description 11
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 title description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 730
- -1 -OH Chemical group 0.000 claims description 265
- 125000003545 alkoxy group Chemical group 0.000 claims description 172
- 150000001875 compounds Chemical class 0.000 claims description 146
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 130
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 123
- 125000003118 aryl group Chemical group 0.000 claims description 100
- 125000004001 thioalkyl group Chemical group 0.000 claims description 99
- 229910052736 halogen Inorganic materials 0.000 claims description 91
- 150000002367 halogens Chemical class 0.000 claims description 88
- 125000001072 heteroaryl group Chemical group 0.000 claims description 87
- 125000003342 alkenyl group Chemical group 0.000 claims description 79
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 66
- 208000035475 disorder Diseases 0.000 claims description 62
- 238000000034 method Methods 0.000 claims description 62
- 125000003282 alkyl amino group Chemical group 0.000 claims description 55
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 54
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 51
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 38
- 230000002062 proliferating effect Effects 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 32
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- 150000003839 salts Chemical class 0.000 claims description 21
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- 229940043355 kinase inhibitor Drugs 0.000 claims description 4
- 230000008692 neointimal formation Effects 0.000 claims description 4
- 239000003757 phosphotransferase inhibitor Substances 0.000 claims description 4
- 229920001184 polypeptide Polymers 0.000 claims description 4
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 58
- 239000000203 mixture Substances 0.000 claims 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 38
- 239000000126 substance Substances 0.000 claims 38
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 34
- 150000002825 nitriles Chemical class 0.000 claims 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 20
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 16
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 15
- 125000005647 linker group Chemical group 0.000 claims 15
- 239000004146 Propane-1,2-diol Substances 0.000 claims 14
- 229960004063 propylene glycol Drugs 0.000 claims 14
- 229910052799 carbon Inorganic materials 0.000 claims 13
- 238000004519 manufacturing process Methods 0.000 claims 11
- 125000001153 fluoro group Chemical group F* 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000004043 oxo group Chemical group O=* 0.000 claims 9
- 239000000010 aprotic solvent Substances 0.000 claims 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 6
- 150000002148 esters Chemical class 0.000 claims 6
- 150000002431 hydrogen Chemical group 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- 150000001412 amines Chemical class 0.000 claims 5
- 125000001246 bromo group Chemical group Br* 0.000 claims 5
- OAWDKVYBPOBVDX-UHFFFAOYSA-N n-(3-bromophenyl)-4-ethyl-6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-amine Chemical compound C=12C(CC)C3=CC(OC)=C(OC)C=C3C2=NNC=1NC1=CC=CC(Br)=C1 OAWDKVYBPOBVDX-UHFFFAOYSA-N 0.000 claims 5
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 4
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 4
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 4
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 4
- 208000036676 acute undifferentiated leukemia Diseases 0.000 claims 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 4
- UHWIDKLVNCNELW-UHFFFAOYSA-N n-(3-bromophenyl)-6,7-dimethoxy-4-methyl-1,4-dihydroindeno[1,2-c]pyrazol-3-amine Chemical compound N1N=C2C=3C=C(OC)C(OC)=CC=3C(C)C2=C1NC1=CC=CC(Br)=C1 UHWIDKLVNCNELW-UHFFFAOYSA-N 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
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- UJNOQRXHHURQIA-UHFFFAOYSA-N 3-[(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)amino]benzamide Chemical compound N1N=C2C=3C=C(OC)C(OC)=CC=3CC2=C1NC1=CC=CC(C(N)=O)=C1 UJNOQRXHHURQIA-UHFFFAOYSA-N 0.000 claims 3
- LTHHVICNTIDADD-UHFFFAOYSA-N 3-[[3-(3-chloroanilino)-6-ethoxy-1,4-dihydroindeno[1,2-c]pyrazol-7-yl]oxy]propan-1-ol Chemical compound N1N=C2C=3C=C(OCCCO)C(OCC)=CC=3CC2=C1NC1=CC=CC(Cl)=C1 LTHHVICNTIDADD-UHFFFAOYSA-N 0.000 claims 3
- KNOZFTPWIIJZKT-UHFFFAOYSA-N 3-[[3-(3-ethoxyanilino)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]oxy]propane-1,2-diol Chemical compound CCOC1=CC=CC(NC2=C3C(C4=CC(OC)=C(OCC(O)CO)C=C4C3)=NN2)=C1 KNOZFTPWIIJZKT-UHFFFAOYSA-N 0.000 claims 3
- PUEOTDYZSCXIGG-UHFFFAOYSA-N 3-[[3-[(2-chlorophenyl)methylamino]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]oxy]propane-1,2-diol Chemical compound C1=C(OCC(O)CO)C(OC)=CC(C2=NN3)=C1CC2=C3NCC1=CC=CC=C1Cl PUEOTDYZSCXIGG-UHFFFAOYSA-N 0.000 claims 3
- KFQJLNWLDUNWPZ-UHFFFAOYSA-N 3-[[3-[(2-fluorophenyl)methylamino]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]oxy]propan-1-ol Chemical compound C1=C(OCCCO)C(OC)=CC(C2=NN3)=C1CC2=C3NCC1=CC=CC=C1F KFQJLNWLDUNWPZ-UHFFFAOYSA-N 0.000 claims 3
- YFWLPZBFHVXJIU-UHFFFAOYSA-N 3-[[7-ethoxy-3-(pyridin-3-ylamino)-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]oxy]propan-1-ol Chemical compound C1=C(OCCCO)C(OCC)=CC(C2=NN3)=C1CC2=C3NC1=CC=CN=C1 YFWLPZBFHVXJIU-UHFFFAOYSA-N 0.000 claims 3
- AOADOOVLHRPJSK-UHFFFAOYSA-N 3-n-(3-chlorophenyl)-1,4-dihydroindeno[1,2-c]pyrazole-3,6-diamine Chemical compound C=1C(N)=CC=C(C2=NN3)C=1CC2=C3NC1=CC=CC(Cl)=C1 AOADOOVLHRPJSK-UHFFFAOYSA-N 0.000 claims 3
- XJGDBYIMZFONIL-UHFFFAOYSA-N 3-n-(3-fluorophenyl)-6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazole-3,5-diamine Chemical compound NC1=C(OC)C(OC)=CC(C2=NN3)=C1CC2=C3NC1=CC=CC(F)=C1 XJGDBYIMZFONIL-UHFFFAOYSA-N 0.000 claims 3
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- WDJRVICSQLWOGN-UHFFFAOYSA-N 6,7-dimethoxy-n-(3-methylphenyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-amine Chemical compound N1N=C2C=3C=C(OC)C(OC)=CC=3CC2=C1NC1=CC=CC(C)=C1 WDJRVICSQLWOGN-UHFFFAOYSA-N 0.000 claims 3
- ZRXAZBRPNWLZRX-UHFFFAOYSA-N 6,7-dimethoxy-n-pyridin-3-yl-1,4-dihydroindeno[1,2-c]pyrazol-3-amine Chemical compound N1N=C2C=3C=C(OC)C(OC)=CC=3CC2=C1NC1=CC=CN=C1 ZRXAZBRPNWLZRX-UHFFFAOYSA-N 0.000 claims 3
- WGFXBODETPLQCU-UHFFFAOYSA-N 6-fluoro-7-methoxy-n-[(2-methylphenyl)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-amine Chemical compound C1=C(F)C(OC)=CC(C2=NN3)=C1CC2=C3NCC1=CC=CC=C1C WGFXBODETPLQCU-UHFFFAOYSA-N 0.000 claims 3
- NUQUNCWBUDTVNX-UHFFFAOYSA-N 7-methoxy-n-phenyl-1,4-dihydroindeno[1,2-c]pyrazol-3-amine Chemical compound N1N=C2C3=CC(OC)=CC=C3CC2=C1NC1=CC=CC=C1 NUQUNCWBUDTVNX-UHFFFAOYSA-N 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000003114 inden-1-yl group Chemical group [H]C1=C([H])C([H])(*)C2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 3
- SMLHMBXAZLBCAX-UHFFFAOYSA-N methyl 3-[(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC2=C3C(C4=CC(OC)=C(OC)C=C4C3)=NN2)=C1 SMLHMBXAZLBCAX-UHFFFAOYSA-N 0.000 claims 3
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- NBYDULGXUZFZBJ-UHFFFAOYSA-N n-(3,5-difluorophenyl)-6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-amine Chemical compound N1N=C2C=3C=C(OC)C(OC)=CC=3CC2=C1NC1=CC(F)=CC(F)=C1 NBYDULGXUZFZBJ-UHFFFAOYSA-N 0.000 claims 3
- ATZDBNUUGJIZHE-UHFFFAOYSA-N n-(3-bromophenyl)-6-fluoro-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-amine Chemical compound C1=C(F)C(OC)=CC(C2=NN3)=C1CC2=C3NC1=CC=CC(Br)=C1 ATZDBNUUGJIZHE-UHFFFAOYSA-N 0.000 claims 3
- HHTRCCIBFRBQJO-UHFFFAOYSA-N n-(3-chlorophenyl)-6-(4-methylpiperazin-1-yl)-1,4-dihydroindeno[1,2-c]pyrazol-3-amine Chemical compound C1CN(C)CCN1C1=CC=C2C3=NNC(NC=4C=C(Cl)C=CC=4)=C3CC2=C1 HHTRCCIBFRBQJO-UHFFFAOYSA-N 0.000 claims 3
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- VCYMYPGYAYHIHD-UHFFFAOYSA-N 1-[3-(3-fluoroanilino)-6,7-dimethoxy-4h-indeno[1,2-c]pyrazol-1-yl]-2-methoxyethanone Chemical compound C1=2CC3=CC(OC)=C(OC)C=C3C=2N(C(=O)COC)N=C1NC1=CC=CC(F)=C1 VCYMYPGYAYHIHD-UHFFFAOYSA-N 0.000 claims 2
- FXDFGRFRPQXYIZ-UHFFFAOYSA-N 1-[[3-(3-chloro-4-fluoroanilino)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]oxy]-3-pyrrolidin-1-ylpropan-2-ol Chemical compound C1=C(OCC(O)CN2CCCC2)C(OC)=CC(C2=NN3)=C1CC2=C3NC1=CC=C(F)C(Cl)=C1 FXDFGRFRPQXYIZ-UHFFFAOYSA-N 0.000 claims 2
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- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims 2
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2003
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- 2003-05-13 NZ NZ548796A patent/NZ548796A/en unknown
- 2003-05-13 PL PL03374062A patent/PL374062A1/xx not_active Application Discontinuation
- 2003-05-13 EP EP03728909A patent/EP1506175B1/en not_active Expired - Lifetime
- 2003-05-13 DE DE60326950T patent/DE60326950D1/de not_active Expired - Fee Related
- 2003-05-13 MX MXPA04011320A patent/MXPA04011320A/es active IP Right Grant
- 2003-05-13 JP JP2004505342A patent/JP2006502097A/ja not_active Withdrawn
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- 2003-05-13 KR KR10-2004-7018454A patent/KR20040106554A/ko not_active Application Discontinuation
- 2003-05-13 AT AT03728909T patent/ATE427301T1/de not_active IP Right Cessation
- 2003-05-13 MY MYPI20031800A patent/MY138268A/en unknown
- 2003-05-13 CN CNB038164884A patent/CN100396670C/zh not_active Expired - Fee Related
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- 2003-05-13 UA UA20041109391A patent/UA80820C2/uk unknown
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- 2003-05-13 WO PCT/US2003/015193 patent/WO2003097609A1/en active Application Filing
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- 2004-12-14 NO NO20045451A patent/NO20045451L/no unknown
- 2004-12-14 HR HR20041188A patent/HRP20041188A2/xx not_active Application Discontinuation
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Also Published As
Publication number | Publication date |
---|---|
CA2486097A1 (en) | 2003-11-27 |
CN1668601A (zh) | 2005-09-14 |
DE60326950D1 (de) | 2009-05-14 |
NZ548796A (en) | 2008-01-31 |
PL374062A1 (en) | 2005-09-19 |
CR7574A (es) | 2008-09-10 |
EP1506175A1 (en) | 2005-02-16 |
US7196110B2 (en) | 2007-03-27 |
CN100396670C (zh) | 2008-06-25 |
BRPI0311179A2 (pt) | 2016-06-21 |
MY138268A (en) | 2009-05-29 |
MXPA04011320A (es) | 2005-08-16 |
EP1506175B1 (en) | 2009-04-01 |
AR040079A1 (es) | 2005-03-16 |
UY27811A1 (es) | 2003-10-31 |
RS98804A (en) | 2006-10-27 |
EA200401378A1 (ru) | 2005-06-30 |
JP2006502097A (ja) | 2006-01-19 |
KR20040106554A (ko) | 2004-12-17 |
UA80820C2 (en) | 2007-11-12 |
ATE427301T1 (de) | 2009-04-15 |
TW200407311A (en) | 2004-05-16 |
SA03240431A (ar) | 2005-12-03 |
AU2003234567A1 (en) | 2003-12-02 |
US20070142305A1 (en) | 2007-06-21 |
US20040082639A1 (en) | 2004-04-29 |
IL165197A0 (en) | 2005-12-18 |
PE20040758A1 (es) | 2005-01-01 |
WO2003097609A1 (en) | 2003-11-27 |
US7795440B2 (en) | 2010-09-14 |
ES2323952T3 (es) | 2009-07-28 |
NO20045451L (no) | 2005-02-09 |
HRP20041188A2 (en) | 2007-03-31 |
EA008770B1 (ru) | 2007-08-31 |
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