HRP20030645A2 - Acylated 6,7,8,9-tetrahydro-5h-benzocycloheptenylamines and their use as pharmaceutical - Google Patents

Info

Publication number

HRP20030645A2

HRP20030645A2 HR20030645A HRP20030645A HRP20030645A2 HR P20030645 A2 HRP20030645 A2 HR P20030645A2 HR 20030645 A HR20030645 A HR 20030645A HR P20030645 A HRP20030645 A HR P20030645A HR P20030645 A2 HRP20030645 A2 HR P20030645A2

Authority

HR

Croatia

Prior art keywords

alkyl

group

phenyl

heteroaryl

tetrahydro

Prior art date

2001-02-13

Links

• Espacenet
• Global Dossier
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• RTSRUUJKIOUOCT-UHFFFAOYSA-N 6,7,8,9-tetrahydro-5h-benzo[7]annulen-4-amine Chemical class C1CCCCC2=C1C=CC=C2N RTSRUUJKIOUOCT-UHFFFAOYSA-N 0.000 title 1
• -1 6,7,8,9-tetrahydro-5H-benzocycloheptenyl amine Chemical class 0.000 claims description 280
• 125000001424 substituent group Chemical group 0.000 claims description 166
• 150000001875 compounds Chemical class 0.000 claims description 108
• 229910052736 halogen Inorganic materials 0.000 claims description 105
• 150000002367 halogens Chemical class 0.000 claims description 103
• 125000001072 heteroaryl group Chemical group 0.000 claims description 95
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
• 125000002577 pseudohalo group Chemical group 0.000 claims description 77
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 66
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 65
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 64
• 125000003118 aryl group Chemical group 0.000 claims description 52
• 150000003839 salts Chemical class 0.000 claims description 44
• 239000000203 mixture Substances 0.000 claims description 38
• 125000000623 heterocyclic group Chemical group 0.000 claims description 36
• 125000005842 heteroatom Chemical group 0.000 claims description 29
• 229910052757 nitrogen Inorganic materials 0.000 claims description 28
• 229910052760 oxygen Inorganic materials 0.000 claims description 25
• 229910052717 sulfur Inorganic materials 0.000 claims description 25
• 229910052731 fluorine Inorganic materials 0.000 claims description 23
• 238000000034 method Methods 0.000 claims description 21
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 15
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 15
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 14
• 238000011282 treatment Methods 0.000 claims description 14
• 239000000243 solution Substances 0.000 claims description 12
• RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 11
• 230000015572 biosynthetic process Effects 0.000 claims description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
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• 230000014509 gene expression Effects 0.000 claims description 11
• 239000002253 acid Substances 0.000 claims description 10
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
• 125000001931 aliphatic group Chemical group 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• 238000003786 synthesis reaction Methods 0.000 claims description 9
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 8
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• 125000004104 aryloxy group Chemical group 0.000 claims description 8
• 125000002950 monocyclic group Chemical group 0.000 claims description 8
• 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 8
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• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
• 229940079593 drug Drugs 0.000 claims description 7
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 7
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• 201000001320 Atherosclerosis Diseases 0.000 claims description 6
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• 201000010099 disease Diseases 0.000 claims description 6
• 229910052739 hydrogen Inorganic materials 0.000 claims description 6
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
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• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
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• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
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• 125000002883 imidazolyl group Chemical group 0.000 claims description 4
• 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
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• 239000007924 injection Substances 0.000 claims description 4
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• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
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• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 3
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• 239000002775 capsule Substances 0.000 claims description 3
• 239000008298 dragée Substances 0.000 claims description 3
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• 239000007940 sugar coated tablet Substances 0.000 claims description 3
• 239000000829 suppository Substances 0.000 claims description 3
• 239000006188 syrup Substances 0.000 claims description 3
• 235000020357 syrup Nutrition 0.000 claims description 3
• 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
• 125000004463 2,4-dimethyl-thiazol-5-yl group Chemical group CC=1SC(=C(N1)C)* 0.000 claims description 2
• GZHWABCBKGMLIE-UHFFFAOYSA-N 2-methyl-3h-benzimidazole-5-carboxylic acid Chemical compound C1=C(C(O)=O)C=C2NC(C)=NC2=C1 GZHWABCBKGMLIE-UHFFFAOYSA-N 0.000 claims description 2
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
• 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 2
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
• 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
• KKJUPNGICOCCDW-UHFFFAOYSA-N 7-N,N-Dimethylamino-1,2,3,4,5-pentathiocyclooctane Chemical compound CN(C)C1CSSSSSC1 KKJUPNGICOCCDW-UHFFFAOYSA-N 0.000 claims description 2
• 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 2
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• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
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• RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-N 0.000 claims 1
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