CA2973602A1 - Tgf-.beta. inhibitors - Google Patents
Tgf-.beta. inhibitorsInfo
- Publication number
- CA2973602A1 CA2973602A1 CA2973602A CA2973602A CA2973602A1 CA 2973602 A1 CA2973602 A1 CA 2973602A1 CA 2973602 A CA2973602 A CA 2973602A CA 2973602 A CA2973602 A CA 2973602A CA 2973602 A1 CA2973602 A1 CA 2973602A1
- Authority
- CA
- Canada
- Prior art keywords
- imidazol
- c6alkyl
- imidazo
- fluorophenyl
- pyridazine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- 150000001875 compounds Chemical class 0.000 claims abstract description 345
- 238000000034 method Methods 0.000 claims abstract description 71
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- 201000010099 disease Diseases 0.000 claims abstract description 52
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- 239000012453 solvate Substances 0.000 claims abstract description 36
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 210
- 229910052736 halogen Inorganic materials 0.000 claims description 204
- 229910052739 hydrogen Inorganic materials 0.000 claims description 184
- 239000001257 hydrogen Substances 0.000 claims description 179
- 150000002367 halogens Chemical class 0.000 claims description 165
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 159
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 155
- -1 C1-6alkenyl Chemical group 0.000 claims description 148
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 144
- 125000000217 alkyl group Chemical group 0.000 claims description 127
- 150000002431 hydrogen Chemical group 0.000 claims description 119
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- 125000001188 haloalkyl group Chemical group 0.000 claims description 101
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 73
- 229910052757 nitrogen Inorganic materials 0.000 claims description 72
- YLXWTAXPOOYRSL-UHFFFAOYSA-N imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound C1=CC=NN2C(C#N)=CN=C21 YLXWTAXPOOYRSL-UHFFFAOYSA-N 0.000 claims description 63
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- WIRTYVGMQVIVDM-UHFFFAOYSA-N pyridine-3-carbonitrile Chemical compound N#CC1=C=NC=C[CH]1 WIRTYVGMQVIVDM-UHFFFAOYSA-N 0.000 claims description 39
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 38
- 125000002619 bicyclic group Chemical group 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
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- 125000004429 atom Chemical group 0.000 claims description 27
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- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 24
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
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- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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