CA2782720A1

CA2782720A1 - Pyrrolo[2,3-d]pyrimidine compounds

Pyrrolo[2,3-d]pyrimidine compounds Download PDF

Info

Publication number: CA2782720A1
Authority: CA; Canada
Prior art keywords: alkyl; group; methyl; amino; cyclohexyl
Prior art date: 2009-12-18
Legal status : Abandoned

Application number

CA2782720A

Other languages

English (en)

French (fr)

Inventor

Jin Xie

Michele Ann Promo

Eric Jon Jacobsen

Horng-Chih Huang

Todd Maddux

Current Assignee

Pfizer Corp SRL

Original Assignee

Pfizer Corp SRL

Priority date

2009-12-18

Filing date

2010-12-06

Publication date

2011-06-23

2010-12-06 Application filed by Pfizer Corp SRL filed Critical Pfizer Corp SRL

2011-06-23 Publication of CA2782720A1 publication Critical patent/CA2782720A1/en

Status Abandoned legal-status Critical Current

Links

150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 title abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 197
238000000034 method Methods 0.000 claims abstract description 46
108010024121 Janus Kinases Proteins 0.000 claims abstract description 33
102000015617 Janus Kinases Human genes 0.000 claims abstract description 33
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 226
-1 3,4-dihydro-2H-benzo[b][1,4]dioxepinyl Chemical group 0.000 claims description 122
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 122
125000000217 alkyl group Chemical group 0.000 claims description 109
229910052739 hydrogen Inorganic materials 0.000 claims description 105
239000001257 hydrogen Substances 0.000 claims description 103
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 86
125000001424 substituent group Chemical group 0.000 claims description 84
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 description 80
125000005843 halogen group Chemical group 0.000 claims description 79
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 76
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 70
150000003839 salts Chemical class 0.000 claims description 62
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 58
125000000623 heterocyclic group Chemical group 0.000 claims description 46
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 44
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 41
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 40
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 40
238000011282 treatment Methods 0.000 claims description 33
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 21
125000001041 indolyl group Chemical group 0.000 claims description 21
125000003226 pyrazolyl group Chemical group 0.000 claims description 21
125000004076 pyridyl group Chemical group 0.000 claims description 21
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 20
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 20
125000004093 cyano group Chemical group *C#N 0.000 claims description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims description 16
125000005059 halophenyl group Chemical group 0.000 claims description 15
125000003373 pyrazinyl group Chemical group 0.000 claims description 15
125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 15
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 13
208000006673 asthma Diseases 0.000 claims description 13
206010052779 Transplant rejections Diseases 0.000 claims description 11
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 10
206010028980 Neoplasm Diseases 0.000 claims description 10
230000001404 mediated effect Effects 0.000 claims description 10
208000023275 Autoimmune disease Diseases 0.000 claims description 9
208000035475 disorder Diseases 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
201000010099 disease Diseases 0.000 claims description 8
125000001207 fluorophenyl group Chemical group 0.000 claims description 8
210000000056 organ Anatomy 0.000 claims description 8
125000006513 pyridinyl methyl group Chemical group 0.000 claims description 8
125000006633 tert-butoxycarbonylamino group Chemical group 0.000 claims description 8
206010020751 Hypersensitivity Diseases 0.000 claims description 7
206010012601 diabetes mellitus Diseases 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
201000006417 multiple sclerosis Diseases 0.000 claims description 7
230000001363 autoimmune Effects 0.000 claims description 6
125000006301 indolyl methyl group Chemical group 0.000 claims description 6
125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 claims description 6
208000006011 Stroke Diseases 0.000 claims description 5
230000007815 allergy Effects 0.000 claims description 5
201000011510 cancer Diseases 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 5
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206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 3
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