SA05260357B1 - مشتقات 3_فينيل_بيرازول كمعدلات لمستقبل سيروتينين 5_ht2a مفيدة في علاج الاضطرابات المتعلقه به - Google Patents

Info

Publication number

SA05260357B1

SA05260357B1 SA05260357A SA05260357A SA05260357B1 SA 05260357 B1 SA05260357 B1 SA 05260357B1 SA 05260357 A SA05260357 A SA 05260357A SA 05260357 A SA05260357 A SA 05260357A SA 05260357 B1 SA05260357 B1 SA 05260357B1

Authority

SA

Saudi Arabia

Prior art keywords

phenyl

methyl

pyrazol

ethoxy

compound

Prior art date

2004-11-19

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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 172
• 208000035475 disorder Diseases 0.000 title claims abstract description 139
• 238000011282 treatment Methods 0.000 title claims abstract description 115
• 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 title abstract 2
• 108010072564 5-HT2A Serotonin Receptor Proteins 0.000 title abstract 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 391
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• 206010003658 Atrial Fibrillation Diseases 0.000 claims abstract description 19
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• 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 11
• 206010036807 progressive multifocal leukoencephalopathy Diseases 0.000 claims abstract description 8
• 208000032109 Transient ischaemic attack Diseases 0.000 claims abstract description 4
• 201000010875 transient cerebral ischemia Diseases 0.000 claims abstract description 4
• 200000000007 Arterial disease Diseases 0.000 claims abstract 2
• -1 cyanos carboxys carboxamide Chemical class 0.000 claims description 412
• 125000000217 alkyl group Chemical group 0.000 claims description 147
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 114
• 239000004202 carbamide Substances 0.000 claims description 112
• 125000003545 alkoxy group Chemical group 0.000 claims description 100
• 238000006467 substitution reaction Methods 0.000 claims description 97
• 229910052736 halogen Inorganic materials 0.000 claims description 72
• 239000003814 drug Substances 0.000 claims description 64
• 229940079593 drug Drugs 0.000 claims description 62
• 125000002252 acyl group Chemical group 0.000 claims description 61
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 53
• 125000001072 heteroaryl group Chemical group 0.000 claims description 53
• 125000001424 substituent group Chemical group 0.000 claims description 52
• 125000004423 acyloxy group Chemical group 0.000 claims description 51
• 150000003839 salts Chemical class 0.000 claims description 47
• 125000003342 alkenyl group Chemical group 0.000 claims description 42
• 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 42
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 41
• 125000001188 haloalkyl group Chemical group 0.000 claims description 38
• 125000003118 aryl group Chemical group 0.000 claims description 37
• 150000002367 halogens Chemical class 0.000 claims description 37
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 32
• 208000020685 sleep-wake disease Diseases 0.000 claims description 32
• 125000003282 alkyl amino group Chemical group 0.000 claims description 31
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 31
• 125000000623 heterocyclic group Chemical group 0.000 claims description 31
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
• KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 28
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
• 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 25
• 125000004429 atom Chemical group 0.000 claims description 25
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 23
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 22
• 125000000304 alkynyl group Chemical group 0.000 claims description 22
• 125000005432 dialkylcarboxamide group Chemical group 0.000 claims description 20
• 150000003857 carboxamides Chemical class 0.000 claims description 19
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 18
• 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 18
• 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 17
• 239000012453 solvate Substances 0.000 claims description 17
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 16
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 16
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 15
• 239000001301 oxygen Substances 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
• 150000004677 hydrates Chemical class 0.000 claims description 14
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 14
• PAMCRRDMORMCSM-UHFFFAOYSA-N n-(trifluoromethyl)benzamide Chemical compound FC(F)(F)NC(=O)C1=CC=CC=C1 PAMCRRDMORMCSM-UHFFFAOYSA-N 0.000 claims description 14
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 14
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• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 13
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• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 12
• 125000004414 alkyl thio group Chemical group 0.000 claims description 12
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• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
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• 210000004204 blood vessel Anatomy 0.000 claims description 10
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 10
• 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 10
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• 239000003937 drug carrier Substances 0.000 claims description 8
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 8
• 230000036407 pain Effects 0.000 claims description 8
• 229940124530 sulfonamide Drugs 0.000 claims description 8
• 150000003573 thiols Chemical class 0.000 claims description 8
• 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 8
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 7
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 7
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 7
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 6
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• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 6
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 6
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
• 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
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• 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 6
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