KR20090029181A - 티아졸릴-디하이드로퀴나졸린 - Google Patents

Info

Publication number

KR20090029181A

KR20090029181A KR1020087027076A KR20087027076A KR20090029181A KR 20090029181 A KR20090029181 A KR 20090029181A KR 1020087027076 A KR1020087027076 A KR 1020087027076A KR 20087027076 A KR20087027076 A KR 20087027076A KR 20090029181 A KR20090029181 A KR 20090029181A

Authority

KR

South Korea

Prior art keywords

alkyl

formula

quinazolin

cycloalkyl

optionally

Prior art date

2006-04-06

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.)

Ceased

Links

• Espacenet
• Global Dossier
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• 238000000034 method Methods 0.000 claims abstract description 27
• 238000002360 preparation method Methods 0.000 claims abstract description 18
• 239000003814 drug Substances 0.000 claims abstract description 7
• 230000008569 process Effects 0.000 claims abstract description 6
• 229940079593 drug Drugs 0.000 claims abstract description 5
• -1 -C 1 -4 - alkyl Chemical group 0.000 claims description 119
• 150000001875 compounds Chemical class 0.000 claims description 89
• 229910052739 hydrogen Inorganic materials 0.000 claims description 67
• 239000001257 hydrogen Substances 0.000 claims description 61
• 150000002431 hydrogen Chemical class 0.000 claims description 46
• 239000000203 mixture Substances 0.000 claims description 42
• 239000000460 chlorine Substances 0.000 claims description 33
• 150000003839 salts Chemical class 0.000 claims description 33
• 229910052801 chlorine Inorganic materials 0.000 claims description 32
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 30
• 125000003118 aryl group Chemical group 0.000 claims description 30
• 125000000217 alkyl group Chemical group 0.000 claims description 29
• 125000004432 carbon atom Chemical group C* 0.000 claims description 29
• 125000005842 heteroatom Chemical group 0.000 claims description 29
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• 239000013543 active substance Substances 0.000 claims description 27
• 201000010099 disease Diseases 0.000 claims description 26
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
• 239000002253 acid Substances 0.000 claims description 25
• 125000001072 heteroaryl group Chemical group 0.000 claims description 23
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims description 22
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims description 22
• 230000002757 inflammatory effect Effects 0.000 claims description 22
• 239000008194 pharmaceutical composition Substances 0.000 claims description 22
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 21
• 229910052794 bromium Inorganic materials 0.000 claims description 20
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
• 229910052799 carbon Inorganic materials 0.000 claims description 16
• 230000000694 effects Effects 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
• 208000027866 inflammatory disease Diseases 0.000 claims description 15
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 14
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 230000000172 allergic effect Effects 0.000 claims description 14
• 206010006451 bronchitis Diseases 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 125000003003 spiro group Chemical group 0.000 claims description 14
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 239000001301 oxygen Substances 0.000 claims description 13
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
• 239000005557 antagonist Substances 0.000 claims description 12
• 230000003454 betamimetic effect Effects 0.000 claims description 12
• 229910052740 iodine Inorganic materials 0.000 claims description 12
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 12
• 239000012453 solvate Substances 0.000 claims description 12
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 11
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• 150000004677 hydrates Chemical class 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 206010035664 Pneumonia Diseases 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 229940121647 egfr inhibitor Drugs 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 7
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• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
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• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
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• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
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• 125000004434 sulfur atom Chemical group 0.000 claims description 5
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• 241000233866 Fungi Species 0.000 claims description 3
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• 208000029523 Interstitial Lung disease Diseases 0.000 claims description 3
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• 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 3
• 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 3
• 208000006311 Pyoderma Diseases 0.000 claims description 3
• 206010039710 Scleroderma Diseases 0.000 claims description 3
• 206010042033 Stevens-Johnson syndrome Diseases 0.000 claims description 3
• 231100000168 Stevens-Johnson syndrome Toxicity 0.000 claims description 3
• 201000009594 Systemic Scleroderma Diseases 0.000 claims description 3
• 206010042953 Systemic sclerosis Diseases 0.000 claims description 3
• 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
• 206010046851 Uveitis Diseases 0.000 claims description 3
• 208000036142 Viral infection Diseases 0.000 claims description 3
• 206010047642 Vitiligo Diseases 0.000 claims description 3
• 208000002205 allergic conjunctivitis Diseases 0.000 claims description 3
• 208000004631 alopecia areata Diseases 0.000 claims description 3
• 208000006682 alpha 1-Antitrypsin Deficiency Diseases 0.000 claims description 3
• 229940125715 antihistaminic agent Drugs 0.000 claims description 3
• 239000000739 antihistaminic agent Substances 0.000 claims description 3
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• 201000008937 atopic dermatitis Diseases 0.000 claims description 3
• 230000001580 bacterial effect Effects 0.000 claims description 3
• 201000009267 bronchiectasis Diseases 0.000 claims description 3
• 208000029771 childhood onset asthma Diseases 0.000 claims description 3
• 208000007451 chronic bronchitis Diseases 0.000 claims description 3
• 208000027157 chronic rhinosinusitis Diseases 0.000 claims description 3
• 208000010247 contact dermatitis Diseases 0.000 claims description 3
• 229960001334 corticosteroids Drugs 0.000 claims description 3
• 229940052760 dopamine agonists Drugs 0.000 claims description 3
• 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 3
• 230000003325 follicular Effects 0.000 claims description 3
• 230000002538 fungal effect Effects 0.000 claims description 3
• 208000024963 hair loss Diseases 0.000 claims description 3
• 230000003676 hair loss Effects 0.000 claims description 3
• 208000006454 hepatitis Diseases 0.000 claims description 3
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• 238000004519 manufacturing process Methods 0.000 claims description 3
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• 208000016366 nasal cavity polyp Diseases 0.000 claims description 3
• 208000037916 non-allergic rhinitis Diseases 0.000 claims description 3
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• 230000002062 proliferating effect Effects 0.000 claims description 3
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• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
• 102000008186 Collagen Human genes 0.000 claims description 2
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• 230000006472 autoimmune response Effects 0.000 claims description 2
• 230000008901 benefit Effects 0.000 claims description 2
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• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
• 125000005717 substituted cycloalkylene group Chemical group 0.000 claims description 2
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
• 201000004624 Dermatitis Diseases 0.000 claims 1
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• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 1
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• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
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• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
• 239000000243 solution Substances 0.000 description 27
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
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