CA2651072A1

CA2651072A1 - Substituted 2-amino-fused heterocyclic compounds

Substituted 2-amino-fused heterocyclic compounds Download PDF

Info

Publication number: CA2651072A1
Authority: CA; Canada
Prior art keywords: cr8r9; trans; amino; cr5r6; carboxamide
Prior art date: 2006-05-01
Legal status : Abandoned

Application number

CA002651072A

Other languages

English (en)

French (fr)

Inventor

Liming Huang

Song Liu

Elizabeth Ann Lunney

Simon Paul Planken

Current Assignee

Pfizer Products Inc

Original Assignee

Individual

Priority date

2006-05-01

Filing date

2007-04-19

Publication date

2007-11-08

2007-04-19 Application filed by Individual filed Critical Individual

2007-11-08 Publication of CA2651072A1 publication Critical patent/CA2651072A1/en

Status Abandoned legal-status Critical Current

Links

150000002391 heterocyclic compounds Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 299
238000000034 method Methods 0.000 claims abstract description 52
150000003839 salts Chemical class 0.000 claims abstract description 39
239000012453 solvate Substances 0.000 claims abstract description 18
241000124008 Mammalia Species 0.000 claims abstract description 10
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 8
230000001404 mediated effect Effects 0.000 claims abstract description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 908
-1 azido, hydroxy Chemical group 0.000 claims description 275
125000000623 heterocyclic group Chemical group 0.000 claims description 84
125000000753 cycloalkyl group Chemical group 0.000 claims description 61
229910052757 nitrogen Inorganic materials 0.000 claims description 41
125000000217 alkyl group Chemical group 0.000 claims description 30
125000003118 aryl group Chemical group 0.000 claims description 30
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 23
125000005843 halogen group Chemical group 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
208000008589 Obesity Diseases 0.000 claims description 9
235000020824 obesity Nutrition 0.000 claims description 9
125000001424 substituent group Chemical group 0.000 claims description 9
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125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
201000010099 disease Diseases 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
230000001684 chronic effect Effects 0.000 claims description 5
208000027866 inflammatory disease Diseases 0.000 claims description 5
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230000001154 acute effect Effects 0.000 claims description 4
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201000008980 hyperinsulinism Diseases 0.000 claims description 4
210000005240 left ventricle Anatomy 0.000 claims description 4
210000004185 liver Anatomy 0.000 claims description 4
210000000056 organ Anatomy 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
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201000001320 Atherosclerosis Diseases 0.000 claims description 3
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206010020772 Hypertension Diseases 0.000 claims description 3
208000031773 Insulin resistance syndrome Diseases 0.000 claims description 3
208000001145 Metabolic Syndrome Diseases 0.000 claims description 3
201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
201000001421 hyperglycemia Diseases 0.000 claims description 3
206010003210 Arteriosclerosis Diseases 0.000 claims description 2
206010007572 Cardiac hypertrophy Diseases 0.000 claims description 2
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206010056370 Congestive cardiomyopathy Diseases 0.000 claims description 2
206010012289 Dementia Diseases 0.000 claims description 2
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125000004043 oxo group Chemical group O=* 0.000 claims description 2
208000037803 restenosis Diseases 0.000 claims description 2
201000008827 tuberculosis Diseases 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 243
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 232
238000005481 NMR spectroscopy Methods 0.000 description 189
150000003857 carboxamides Chemical class 0.000 description 162
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 154
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239000000203 mixture Substances 0.000 description 98
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238000001819 mass spectrum Methods 0.000 description 48
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GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 30
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TYHCBIKGTCZFTK-UHFFFAOYSA-N quinazoline-7-carboxamide Chemical compound C1=NC=NC2=CC(C(=O)N)=CC=C21 TYHCBIKGTCZFTK-UHFFFAOYSA-N 0.000 description 28
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239000012044 organic layer Substances 0.000 description 26
238000004809 thin layer chromatography Methods 0.000 description 26
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