KR20070064660A - Ｐｉ３ 키나제 - Google Patents
Ｐｉ３ 키나제Info
- Publication number
- KR20070064660A KR20070064660A KR1020077010387A KR20077010387A KR20070064660A KR 20070064660 A KR20070064660 A KR 20070064660A KR 1020077010387 A KR1020077010387 A KR 1020077010387A KR 20077010387 A KR20077010387 A KR 20077010387A KR 20070064660 A KR20070064660 A KR 20070064660A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- optionally substituted
- methyl
- formula
- aryl
- Prior art date
- 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.)
- Withdrawn
Links
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 title claims abstract description 27
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 title claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 237
- 201000010099 disease Diseases 0.000 claims abstract description 30
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 30
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 23
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 16
- 230000000172 allergic effect Effects 0.000 claims abstract description 15
- 208000010668 atopic eczema Diseases 0.000 claims abstract description 13
- 208000026935 allergic disease Diseases 0.000 claims abstract description 8
- 210000002850 nasal mucosa Anatomy 0.000 claims abstract description 5
- 208000017520 skin disease Diseases 0.000 claims abstract description 5
- 208000024891 symptom Diseases 0.000 claims abstract description 5
- 201000008383 nephritis Diseases 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 629
- -1 diastereomers Chemical class 0.000 claims description 323
- 229910052739 hydrogen Inorganic materials 0.000 claims description 228
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 215
- 229910052799 carbon Inorganic materials 0.000 claims description 200
- 125000003118 aryl group Chemical group 0.000 claims description 158
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 115
- 125000001072 heteroaryl group Chemical group 0.000 claims description 105
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 103
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 89
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 88
- 150000003839 salts Chemical class 0.000 claims description 84
- 229910052736 halogen Inorganic materials 0.000 claims description 82
- 150000002367 halogens Chemical group 0.000 claims description 82
- 239000000203 mixture Substances 0.000 claims description 82
- 229910052757 nitrogen Inorganic materials 0.000 claims description 79
- 239000012453 solvate Substances 0.000 claims description 71
- 125000000304 alkynyl group Chemical group 0.000 claims description 69
- 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 66
- 239000000460 chlorine Substances 0.000 claims description 62
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 61
- 150000004677 hydrates Chemical class 0.000 claims description 58
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 49
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 46
- 239000000126 substance Substances 0.000 claims description 46
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 45
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 41
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 40
- 125000003342 alkenyl group Chemical group 0.000 claims description 40
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 38
- 229910052801 chlorine Inorganic materials 0.000 claims description 37
- 125000002947 alkylene group Chemical group 0.000 claims description 34
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 31
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 30
- 125000003003 spiro group Chemical group 0.000 claims description 30
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 27
- 229910052794 bromium Inorganic materials 0.000 claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 125000005842 heteroatom Chemical group 0.000 claims description 27
- 229910052717 sulfur Chemical group 0.000 claims description 27
- 239000011593 sulfur Chemical group 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 25
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 24
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 24
- 239000001301 oxygen Substances 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 18
- ONQBOTKLCMXPOF-UHFFFAOYSA-N 1-ethylpyrrolidine Chemical compound CCN1CCCC1 ONQBOTKLCMXPOF-UHFFFAOYSA-N 0.000 claims description 17
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 15
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 15
- 125000005024 alkenyl aryl group Chemical group 0.000 claims description 15
- 125000005025 alkynylaryl group Chemical group 0.000 claims description 15
- 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 15
- 238000002360 preparation method Methods 0.000 claims description 14
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 13
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 13
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 11
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 11
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 claims description 10
- 206010006451 bronchitis Diseases 0.000 claims description 10
- 150000001721 carbon Chemical group 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 9
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 8
- 206010061218 Inflammation Diseases 0.000 claims description 8
- 230000004054 inflammatory process Effects 0.000 claims description 8
- 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 8
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 8
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 7
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 206010010741 Conjunctivitis Diseases 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 125000004419 alkynylene group Chemical group 0.000 claims description 6
- 125000005622 butynylene group Chemical group 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 206010025135 lupus erythematosus Diseases 0.000 claims description 6
- 206010035664 Pneumonia Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 5
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 4
- 206010001889 Alveolitis Diseases 0.000 claims description 4
- 241000233866 Fungi Species 0.000 claims description 4
- 208000000592 Nasal Polyps Diseases 0.000 claims description 4
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 4
- 206010000496 acne Diseases 0.000 claims description 4
- 201000010105 allergic rhinitis Diseases 0.000 claims description 4
- 201000001155 extrinsic allergic alveolitis Diseases 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 208000022098 hypersensitivity pneumonitis Diseases 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 230000009885 systemic effect Effects 0.000 claims description 4
- 231100000331 toxic Toxicity 0.000 claims description 4
- 230000002588 toxic effect Effects 0.000 claims description 4
- 241000894006 Bacteria Species 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 206010023230 Joint stiffness Diseases 0.000 claims description 3
- 206010037423 Pulmonary oedema Diseases 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 210000002478 hand joint Anatomy 0.000 claims description 3
- 208000005333 pulmonary edema Diseases 0.000 claims description 3
- 206010052613 Allergic bronchitis Diseases 0.000 claims description 2
- 206010049153 Allergic sinusitis Diseases 0.000 claims description 2
- 201000004384 Alopecia Diseases 0.000 claims description 2
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 2
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 2
- 206010008909 Chronic Hepatitis Diseases 0.000 claims description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 2
- 206010009137 Chronic sinusitis Diseases 0.000 claims description 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
- 102000008186 Collagen Human genes 0.000 claims description 2
- 108010035532 Collagen Proteins 0.000 claims description 2
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 2
- 206010011224 Cough Diseases 0.000 claims description 2
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 2
- 206010012442 Dermatitis contact Diseases 0.000 claims description 2
- 206010014561 Emphysema Diseases 0.000 claims description 2
- 206010015150 Erythema Diseases 0.000 claims description 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 2
- 206010062639 Herpes dermatitis Diseases 0.000 claims description 2
- 208000029523 Interstitial Lung disease Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims description 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims description 2
- 208000006311 Pyoderma Diseases 0.000 claims description 2
- 206010042033 Stevens-Johnson syndrome Diseases 0.000 claims description 2
- 231100000168 Stevens-Johnson syndrome Toxicity 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- 206010046851 Uveitis Diseases 0.000 claims description 2
- 208000036142 Viral infection Diseases 0.000 claims description 2
- 206010047642 Vitiligo Diseases 0.000 claims description 2
- 208000002205 allergic conjunctivitis Diseases 0.000 claims description 2
- 208000004631 alopecia areata Diseases 0.000 claims description 2
- 208000006682 alpha 1-Antitrypsin Deficiency Diseases 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 208000024998 atopic conjunctivitis Diseases 0.000 claims description 2
- 201000008937 atopic dermatitis Diseases 0.000 claims description 2
- 201000009267 bronchiectasis Diseases 0.000 claims description 2
- 208000029771 childhood onset asthma Diseases 0.000 claims description 2
- 208000007451 chronic bronchitis Diseases 0.000 claims description 2
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims description 2
- 229920001436 collagen Polymers 0.000 claims description 2
- 208000010247 contact dermatitis Diseases 0.000 claims description 2
- 231100000321 erythema Toxicity 0.000 claims description 2
- 230000003325 follicular Effects 0.000 claims description 2
- 208000024963 hair loss Diseases 0.000 claims description 2
- 230000003676 hair loss Effects 0.000 claims description 2
- 208000006454 hepatitis Diseases 0.000 claims description 2
- 208000016036 idiopathic nephrotic syndrome Diseases 0.000 claims description 2
- 230000002458 infectious effect Effects 0.000 claims description 2
- 201000006334 interstitial nephritis Diseases 0.000 claims description 2
- 206010023332 keratitis Diseases 0.000 claims description 2
- 230000003902 lesion Effects 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 208000037916 non-allergic rhinitis Diseases 0.000 claims description 2
- 201000008482 osteoarthritis Diseases 0.000 claims description 2
- 230000002062 proliferating effect Effects 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 201000000306 sarcoidosis Diseases 0.000 claims description 2
- 230000009385 viral infection Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 230000006472 autoimmune response Effects 0.000 claims 1
- 210000000795 conjunctiva Anatomy 0.000 claims 1
- 208000003906 hydrocephalus Diseases 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 abstract description 4
- 208000028004 allergic respiratory disease Diseases 0.000 abstract description 3
- 208000030533 eye disease Diseases 0.000 abstract description 3
- 210000005095 gastrointestinal system Anatomy 0.000 abstract 1
- 230000003137 locomotive effect Effects 0.000 abstract 1
- 230000004526 pharmaceutical effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 192
- 239000000543 intermediate Substances 0.000 description 117
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 116
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 110
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 83
- 239000000243 solution Substances 0.000 description 83
- 239000011541 reaction mixture Substances 0.000 description 82
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 81
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- 238000002844 melting Methods 0.000 description 71
- 230000008018 melting Effects 0.000 description 71
- 239000012074 organic phase Substances 0.000 description 65
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 60
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
- 239000000047 product Substances 0.000 description 46
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- 239000002244 precipitate Substances 0.000 description 41
- 238000001704 evaporation Methods 0.000 description 40
- 230000008020 evaporation Effects 0.000 description 40
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 38
- 238000001816 cooling Methods 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 30
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 30
- 239000000725 suspension Substances 0.000 description 24
- 238000004587 chromatography analysis Methods 0.000 description 23
- 239000007787 solid Substances 0.000 description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 108091007960 PI3Ks Proteins 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- 239000002253 acid Substances 0.000 description 20
- 238000003756 stirring Methods 0.000 description 20
- 229960000583 acetic acid Drugs 0.000 description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 17
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 238000004440 column chromatography Methods 0.000 description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 description 15
- 235000011181 potassium carbonates Nutrition 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 239000012043 crude product Substances 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- 239000008346 aqueous phase Substances 0.000 description 13
- 239000012452 mother liquor Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- ADODRSVGNHNKAT-UHFFFAOYSA-N 2-Chlorophenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1Cl ADODRSVGNHNKAT-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 239000012362 glacial acetic acid Substances 0.000 description 12
- FIMXSEMBHGTNKT-UHFFFAOYSA-N Scopine Natural products CN1C2CC(O)CC1C1C2O1 FIMXSEMBHGTNKT-UHFFFAOYSA-N 0.000 description 11
- 239000000808 adrenergic beta-agonist Substances 0.000 description 11
- 150000008064 anhydrides Chemical class 0.000 description 11
- 230000003454 betamimetic effect Effects 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- 239000013543 active substance Substances 0.000 description 10
- 239000005557 antagonist Substances 0.000 description 10
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 10
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 9
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 9
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Classifications
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- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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Landscapes
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
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| DE102004048877A DE102004048877A1 (de) | 2004-10-07 | 2004-10-07 | PI3-Kinasen |
| DE102004048877.0 | 2004-10-07 | ||
| DE102005005813A DE102005005813A1 (de) | 2005-02-09 | 2005-02-09 | PI3-Kinasen |
| DE102005005813.2 | 2005-02-09 |
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| KR20070064660A true KR20070064660A (ko) | 2007-06-21 |
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| KR1020077010387A Withdrawn KR20070064660A (ko) | 2004-10-07 | 2005-10-05 | Ｐｉ３ 키나제 |
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| AU2005293607A1 (en) * | 2004-10-07 | 2006-04-20 | Boehringer Ingelheim International Gmbh | PI3 kinases |
| US7691868B2 (en) | 2006-04-06 | 2010-04-06 | Boehringer Ingelheim International Gmbh | Thiazolyl-dihydro-quinazoline |
| US20070238746A1 (en) * | 2006-04-06 | 2007-10-11 | Trixi Brandl | Thiazolyl-dihydro-chinazoline |
| US20070238718A1 (en) * | 2006-04-06 | 2007-10-11 | Matthias Grauert | Thiazolyl-dihydro-indazole |
| MX2008012535A (es) * | 2006-04-06 | 2008-10-10 | Boehringer Ingelheim Int | Tiazolil-dihidro-indazoles. |
| US7517995B2 (en) * | 2006-04-06 | 2009-04-14 | Boehringer Ingelheim International Gmbh | Thiazolyl-dihydro-cyclopentapyrazole |
| US20070259855A1 (en) * | 2006-04-06 | 2007-11-08 | Udo Maier | Thiazolyl-dihydro-indazole |
| DE602006002385D1 (de) * | 2006-06-26 | 2008-10-02 | Helm Ag | Verfahren zur Herstellung von Pramipexole |
| EP2045253A4 (en) * | 2006-06-29 | 2013-01-23 | Nissan Chemical Ind Ltd | alpha-amino acid derivative and pharmaceutical agent containing it as an active ingredient |
| US8779154B2 (en) | 2006-09-26 | 2014-07-15 | Qinglin Che | Fused ring compounds for inflammation and immune-related uses |
| GB0619611D0 (en) * | 2006-10-04 | 2006-11-15 | Ark Therapeutics Ltd | Compounds and their use |
| WO2009039140A1 (en) * | 2007-09-17 | 2009-03-26 | Smithkline Beecham Corporation | Pyridopyrimidine derivatives as pi3 kinase inhibitors |
| US20110052643A1 (en) * | 2008-01-07 | 2011-03-03 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| PE20091617A1 (es) * | 2008-03-13 | 2009-11-12 | Boehringer Ingelheim Int | Tiazolil-dihidro-indazoles |
| WO2009120826A1 (en) * | 2008-03-27 | 2009-10-01 | Wyeth | 2-aryl- and 2-heteroarylthiazolyl compounds, methods for their preparation and use thereof |
| RU2506267C2 (ru) | 2008-03-31 | 2014-02-10 | Дженентек, Инк. | Бензопирановые и бензоксепиновые ингибиторы рi3k и их применение |
| WO2010007943A1 (ja) * | 2008-07-17 | 2010-01-21 | 旭化成ファーマ株式会社 | 含窒素複素環化合物 |
| US20110230472A1 (en) * | 2008-08-29 | 2011-09-22 | Shionogi & Co., Ltd. | Ring-fused azole derivative having pi3k-inhibiting activity |
| EP2350084B1 (en) * | 2008-10-17 | 2015-06-24 | Boehringer Ingelheim International GmbH | Tetra-aza-heterocycles as phosphatidylinositol-3-kinases (pi3-kinases) inhibitor |
| GB0900404D0 (en) | 2009-01-12 | 2009-02-11 | Addex Pharmaceuticals Sa | New compounds 4 |
| US8278302B2 (en) | 2009-04-08 | 2012-10-02 | Boehringer Ingelheim International Gmbh | Substituted piperidines as CCR3 antagonists |
| EP2421872B1 (en) * | 2009-04-22 | 2015-06-10 | Boehringer Ingelheim International GmbH | Thia-triaza-as-indacenes as pi3-kinases inhibitors for the treatment of cancer |
| US8288379B2 (en) | 2009-04-22 | 2012-10-16 | Boehringer Ingelheim International Gmbh | Thia-triaza-cyclopentazulenes |
| ES2432671T3 (es) * | 2009-07-02 | 2013-12-04 | Novartis Ag | 2-carboxamida cicloamino ureas útiles como inhibidores de PI3K |
| UA111579C2 (uk) | 2009-08-17 | 2016-05-25 | Інтеллікіне Ллк | ГЕТЕРОЦИКЛІЧНІ ПОХІДНІ 2-АМІНОБЕНЗО[d]ОКСАЗОЛУ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ НА ЇХ ОСНОВІ ТА ЇХ ЗАСТОСУВАННЯ ДЛЯ ЛІКУВАННЯ ЗАХВОРЮВАННЯ, ПОВ'АНОГО З РІ3-КІНАЗОЮ |
| EP2483277B1 (en) * | 2009-09-28 | 2015-12-02 | F. Hoffmann-La Roche AG | Benzoxepin pi3k inhibitor compounds and methods of use |
| EP2845592A1 (en) * | 2009-09-28 | 2015-03-11 | F. Hoffmann-La Roche AG | Benzoxazepin PI3K inhibitor compounds and methods of use |
| CN102695710B (zh) * | 2009-11-13 | 2015-08-19 | 默克雪兰诺有限公司 | 三环吡唑胺衍生物 |
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2005
- 2005-10-05 AU AU2005293607A patent/AU2005293607A1/en not_active Abandoned
- 2005-10-05 RU RU2007116858/04A patent/RU2403258C2/ru not_active IP Right Cessation
- 2005-10-05 RU RU2007116861/04A patent/RU2007116861A/ru not_active Application Discontinuation
- 2005-10-05 EP EP05805652A patent/EP1802636B1/de not_active Expired - Lifetime
- 2005-10-05 EP EP11158787A patent/EP2343303A1/de not_active Withdrawn
- 2005-10-05 KR KR1020077010387A patent/KR20070064660A/ko not_active Withdrawn
- 2005-10-05 WO PCT/EP2005/055015 patent/WO2006040279A1/de not_active Ceased
- 2005-10-05 US US11/243,796 patent/US7691888B2/en not_active Expired - Lifetime
- 2005-10-05 BR BRPI0516557-1A patent/BRPI0516557A/pt not_active IP Right Cessation
- 2005-10-05 MX MX2007004051A patent/MX2007004051A/es not_active Application Discontinuation
- 2005-10-05 CN CNA2005800344060A patent/CN101048418A/zh active Pending
- 2005-10-05 CA CA2579279A patent/CA2579279C/en not_active Expired - Lifetime
- 2005-10-05 JP JP2007535159A patent/JP5122287B2/ja not_active Expired - Lifetime
- 2005-10-05 US US11/244,299 patent/US20060106013A1/en not_active Abandoned
- 2005-10-06 TW TW094134899A patent/TW200628475A/zh unknown
- 2005-10-07 AR ARP050104225A patent/AR055273A1/es unknown
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- 2007-04-10 IL IL182398A patent/IL182398A0/en unknown
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- 2009-02-05 US US12/366,248 patent/US8232286B2/en active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| RU2403258C2 (ru) | 2010-11-10 |
| US20090156554A1 (en) | 2009-06-18 |
| AU2005293607A1 (en) | 2006-04-20 |
| EP1802636B1 (de) | 2013-03-27 |
| US20100113414A1 (en) | 2010-05-06 |
| US20060100254A1 (en) | 2006-05-11 |
| WO2006040279A1 (de) | 2006-04-20 |
| JP2008515852A (ja) | 2008-05-15 |
| TW200628475A (en) | 2006-08-16 |
| CA2579279C (en) | 2013-10-01 |
| US20060106013A1 (en) | 2006-05-18 |
| MX2007004051A (es) | 2007-05-24 |
| AR055273A1 (es) | 2007-08-15 |
| CN101048418A (zh) | 2007-10-03 |
| RU2007116858A (ru) | 2008-12-27 |
| CA2579279A1 (en) | 2006-04-20 |
| BRPI0516557A (pt) | 2008-09-09 |
| IL182398A0 (en) | 2007-07-24 |
| JP5122287B2 (ja) | 2013-01-16 |
| US8232286B2 (en) | 2012-07-31 |
| EP2343303A1 (de) | 2011-07-13 |
| EP1802636A1 (de) | 2007-07-04 |
| US8207349B2 (en) | 2012-06-26 |
| RU2007116861A (ru) | 2009-03-20 |
| US7691888B2 (en) | 2010-04-06 |
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