RU2008143547A - Тиазолилдигидроциклопентапиразолы для применения в качестве ингибиторов pi3-киназы - Google Patents
Тиазолилдигидроциклопентапиразолы для применения в качестве ингибиторов pi3-киназы Download PDFInfo
- Publication number
- RU2008143547A RU2008143547A RU2008143547/04A RU2008143547A RU2008143547A RU 2008143547 A RU2008143547 A RU 2008143547A RU 2008143547/04 A RU2008143547/04 A RU 2008143547/04A RU 2008143547 A RU2008143547 A RU 2008143547A RU 2008143547 A RU2008143547 A RU 2008143547A
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- Prior art keywords
- alkyl
- group
- aryl
- cycloalkyl
- optionally
- Prior art date
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- 239000002935 phosphatidylinositol 3 kinase inhibitor Substances 0.000 title claims 2
- 125000000335 thiazolyl group Chemical group 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 27
- 239000001257 hydrogen Substances 0.000 claims abstract 27
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 22
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 16
- 150000001875 compounds Chemical class 0.000 claims abstract 16
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims abstract 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 14
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract 13
- 125000005842 heteroatom Chemical group 0.000 claims abstract 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 12
- 229910052757 nitrogen Chemical group 0.000 claims abstract 12
- 239000001301 oxygen Substances 0.000 claims abstract 12
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims abstract 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 10
- 239000011593 sulfur Chemical group 0.000 claims abstract 10
- 150000002431 hydrogen Chemical group 0.000 claims abstract 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
- 229910052799 carbon Inorganic materials 0.000 claims 28
- 125000003118 aryl group Chemical group 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 201000010099 disease Diseases 0.000 claims 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 10
- 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 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 125000003003 spiro group Chemical group 0.000 claims 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 5
- 230000000172 allergic effect Effects 0.000 claims 5
- 206010006451 bronchitis Diseases 0.000 claims 5
- 230000002757 inflammatory effect Effects 0.000 claims 5
- 206010010741 Conjunctivitis Diseases 0.000 claims 4
- 208000010668 atopic eczema Diseases 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- 206010035664 Pneumonia Diseases 0.000 claims 3
- 125000004450 alkenylene group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000004419 alkynylene group Chemical group 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- -1 (4-phenyl-4,7-dihydro-3-thia-1,4,5-triazacyclopenta [a] pentalen-2-yl) piperidine-1-carboxylic acid amide Chemical compound 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 206010001889 Alveolitis Diseases 0.000 claims 2
- 208000035143 Bacterial infection Diseases 0.000 claims 2
- 208000000592 Nasal Polyps Diseases 0.000 claims 2
- 206010035742 Pneumonitis Diseases 0.000 claims 2
- 206010039085 Rhinitis allergic Diseases 0.000 claims 2
- 208000024780 Urticaria Diseases 0.000 claims 2
- 208000026935 allergic disease Diseases 0.000 claims 2
- 201000010105 allergic rhinitis Diseases 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 201000001155 extrinsic allergic alveolitis Diseases 0.000 claims 2
- 208000022098 hypersensitivity pneumonitis Diseases 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 206010025135 lupus erythematosus Diseases 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical group [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 2
- 208000017520 skin disease Diseases 0.000 claims 2
- GHCDBLUSMWICFZ-UHFFFAOYSA-N (1-phenyl-4h-pyrazolo[2,3]cyclopenta[2,4-b][1,3]thiazol-6-yl)urea Chemical compound C1=2C=3SC(NC(=O)N)=NC=3CC=2C=NN1C1=CC=CC=C1 GHCDBLUSMWICFZ-UHFFFAOYSA-N 0.000 claims 1
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 1
- NLLLVYJRMPOMHK-UHFFFAOYSA-N 1,1-dimethyl-3-(1-phenyl-4h-pyrazolo[2,3]cyclopenta[2,4-b][1,3]thiazol-6-yl)urea Chemical compound C1=2C=3SC(NC(=O)N(C)C)=NC=3CC=2C=NN1C1=CC=CC=C1 NLLLVYJRMPOMHK-UHFFFAOYSA-N 0.000 claims 1
- SDEPTIVHTKQAGI-UHFFFAOYSA-N 1-[1-(2-chlorophenyl)-4h-pyrazolo[2,3]cyclopenta[2,4-b][1,3]thiazol-6-yl]-3-(2-imidazol-1-ylethyl)urea Chemical compound ClC1=CC=CC=C1N1C(C=2SC(NC(=O)NCCN3C=NC=C3)=NC=2C2)=C2C=N1 SDEPTIVHTKQAGI-UHFFFAOYSA-N 0.000 claims 1
- BFLPDEYEZXKONJ-UHFFFAOYSA-N 1-[1-(2-chlorophenyl)-4h-pyrazolo[2,3]cyclopenta[2,4-b][1,3]thiazol-6-yl]-3-[2-(dimethylamino)ethyl]urea Chemical compound C1=2C=3SC(NC(=O)NCCN(C)C)=NC=3CC=2C=NN1C1=CC=CC=C1Cl BFLPDEYEZXKONJ-UHFFFAOYSA-N 0.000 claims 1
- CDOOKMRFXJNCSN-UHFFFAOYSA-N 1-[1-(2-chlorophenyl)-4h-pyrazolo[2,3]cyclopenta[2,4-b][1,3]thiazol-6-yl]-3-methylurea Chemical compound C1=2C=3SC(NC(=O)NC)=NC=3CC=2C=NN1C1=CC=CC=C1Cl CDOOKMRFXJNCSN-UHFFFAOYSA-N 0.000 claims 1
- TWNUSNAYQHSIRM-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-1-methyl-3-(1-phenyl-4h-pyrazolo[2,3]cyclopenta[2,4-b][1,3]thiazol-6-yl)urea Chemical compound C1=2C=3SC(NC(=O)N(C)CCN(C)C)=NC=3CC=2C=NN1C1=CC=CC=C1 TWNUSNAYQHSIRM-UHFFFAOYSA-N 0.000 claims 1
- LGPUVMRVIOMSPE-UHFFFAOYSA-N 1-[2-(dimethylamino)ethyl]-3-(1-phenyl-4h-pyrazolo[2,3]cyclopenta[2,4-b][1,3]thiazol-6-yl)urea Chemical compound C1=2C=3SC(NC(=O)NCCN(C)C)=NC=3CC=2C=NN1C1=CC=CC=C1 LGPUVMRVIOMSPE-UHFFFAOYSA-N 0.000 claims 1
- HGMMYUDBIWTQPU-UHFFFAOYSA-N 3-[1-(2-chlorophenyl)-4h-pyrazolo[2,3]cyclopenta[2,4-b][1,3]thiazol-6-yl]-1,1-dimethylurea Chemical compound C1=2C=3SC(NC(=O)N(C)C)=NC=3CC=2C=NN1C1=CC=CC=C1Cl HGMMYUDBIWTQPU-UHFFFAOYSA-N 0.000 claims 1
- DAJHPOGIFXGBTL-UHFFFAOYSA-N 3-[1-(2-chlorophenyl)-4h-pyrazolo[2,3]cyclopenta[2,4-b][1,3]thiazol-6-yl]-1-[2-(dimethylamino)ethyl]-1-methylurea Chemical compound C1=2C=3SC(NC(=O)N(C)CCN(C)C)=NC=3CC=2C=NN1C1=CC=CC=C1Cl DAJHPOGIFXGBTL-UHFFFAOYSA-N 0.000 claims 1
- FYJORSKXVAOJFZ-UHFFFAOYSA-N 4-methylpiperazine-1-carboxamide Chemical compound CN1CCN(C(N)=O)CC1 FYJORSKXVAOJFZ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 208000002874 Acne Vulgaris Diseases 0.000 claims 1
- 206010052613 Allergic bronchitis Diseases 0.000 claims 1
- 206010049153 Allergic sinusitis Diseases 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- 206010008909 Chronic Hepatitis Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009137 Chronic sinusitis Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 206010010744 Conjunctivitis allergic Diseases 0.000 claims 1
- 206010011224 Cough Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- 206010015218 Erythema multiforme Diseases 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- 206010017533 Fungal infection Diseases 0.000 claims 1
- 241000233866 Fungi Species 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 229940124056 Histamine H1 receptor antagonist Drugs 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000029523 Interstitial Lung disease Diseases 0.000 claims 1
- 208000031888 Mycoses Diseases 0.000 claims 1
- 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 claims 1
- 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 claims 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 1
- 206010037423 Pulmonary oedema Diseases 0.000 claims 1
- 208000006311 Pyoderma Diseases 0.000 claims 1
- 206010037765 Radiation pneumonitis Diseases 0.000 claims 1
- 206010039710 Scleroderma Diseases 0.000 claims 1
- 201000009594 Systemic Scleroderma Diseases 0.000 claims 1
- 206010042953 Systemic sclerosis Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 206010047642 Vitiligo Diseases 0.000 claims 1
- 208000016807 X-linked intellectual disability-macrocephaly-macroorchidism syndrome Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 206010000496 acne Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 239000000808 adrenergic beta-agonist Substances 0.000 claims 1
- 208000002205 allergic conjunctivitis Diseases 0.000 claims 1
- 208000004631 alopecia areata Diseases 0.000 claims 1
- 208000006682 alpha 1-Antitrypsin Deficiency Diseases 0.000 claims 1
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000024998 atopic conjunctivitis Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 230000001363 autoimmune Effects 0.000 claims 1
- 230000001580 bacterial effect Effects 0.000 claims 1
- 230000003454 betamimetic effect Effects 0.000 claims 1
- 201000009267 bronchiectasis Diseases 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 208000029771 childhood onset asthma Diseases 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 229960001334 corticosteroids Drugs 0.000 claims 1
- 229940052760 dopamine agonists Drugs 0.000 claims 1
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 229940121647 egfr inhibitor Drugs 0.000 claims 1
- 208000030533 eye disease Diseases 0.000 claims 1
- 230000003325 follicular Effects 0.000 claims 1
- 230000002538 fungal effect Effects 0.000 claims 1
- 244000000013 helminth Species 0.000 claims 1
- 208000006454 hepatitis Diseases 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 239000000938 histamine H1 antagonist Substances 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 208000016036 idiopathic nephrotic syndrome Diseases 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 201000006334 interstitial nephritis Diseases 0.000 claims 1
- 206010023332 keratitis Diseases 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- YEESKJGWJFYOOK-IJHYULJSSA-N leukotriene D4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@H](N)C(=O)NCC(O)=O YEESKJGWJFYOOK-IJHYULJSSA-N 0.000 claims 1
- 238000002483 medication Methods 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 210000002850 nasal mucosa Anatomy 0.000 claims 1
- 208000037916 non-allergic rhinitis Diseases 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 125000004140 pentalen-2-yl group Chemical group [H]C1=C([H])C2=C([H])C(*)=C([H])C2=C1[H] 0.000 claims 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
- 231100000614 poison Toxicity 0.000 claims 1
- 239000013312 porous aromatic framework Substances 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 208000005333 pulmonary edema Diseases 0.000 claims 1
- 230000009257 reactivity Effects 0.000 claims 1
- 210000002345 respiratory system Anatomy 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000004700 rosacea Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 101150101156 slc51a gene Proteins 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 239000003440 toxic substance Substances 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 4
- 125000005915 C6-C14 aryl group Chemical group 0.000 abstract 3
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
- 0 CN(*)S(*IC)=O Chemical compound CN(*)S(*IC)=O 0.000 description 2
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—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
- 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
- C07D513/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Gastroenterology & Hepatology (AREA)
- Urology & Nephrology (AREA)
- Ophthalmology & Optometry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Otolaryngology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06112298 | 2006-04-06 | ||
| EP06112298.2 | 2006-04-06 |
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| RU2008143547A true RU2008143547A (ru) | 2010-05-20 |
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| EP (1) | EP2007382A1 (enExample) |
| JP (1) | JP2009532415A (enExample) |
| KR (1) | KR20080111118A (enExample) |
| CN (1) | CN101460167A (enExample) |
| AR (1) | AR060267A1 (enExample) |
| AU (1) | AU2007236045A1 (enExample) |
| BR (1) | BRPI0710306A2 (enExample) |
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| IL (1) | IL194494A0 (enExample) |
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| WO (1) | WO2007115931A1 (enExample) |
| ZA (1) | ZA200807713B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004016179A1 (de) * | 2004-03-30 | 2005-10-20 | Boehringer Ingelheim Pharma | Verbindungen zur Behandlung von proliferativen Prozessen |
| US7691868B2 (en) | 2006-04-06 | 2010-04-06 | Boehringer Ingelheim International Gmbh | Thiazolyl-dihydro-quinazoline |
| US20070259855A1 (en) * | 2006-04-06 | 2007-11-08 | Udo Maier | Thiazolyl-dihydro-indazole |
| US20070238746A1 (en) * | 2006-04-06 | 2007-10-11 | Trixi Brandl | Thiazolyl-dihydro-chinazoline |
| JPWO2010024258A1 (ja) * | 2008-08-29 | 2012-01-26 | 塩野義製薬株式会社 | Pi3k阻害活性を有する縮環アゾール誘導体 |
| AU2009299927B2 (en) | 2008-10-01 | 2013-05-30 | Novartis Ag | Smoothened antagonism for the treatment of hedgehog pathway-related disorders |
| US8653097B2 (en) | 2008-10-17 | 2014-02-18 | Boehringer Ingelheim International Gmbh | Tetra-aza-heterocycles as phosphatidylinositol-3-kinases (P13-kinases) inhibitor |
| TW201103943A (en) * | 2009-04-27 | 2011-02-01 | Shionogi & Co | Urea derivative having pi3k inhibitory activity |
| KR20120046723A (ko) | 2009-07-02 | 2012-05-10 | 노파르티스 아게 | Pi3k 억제제로서 유용한 2-카르복스아미드 시클로아미노 우레아 |
| WO2012121953A1 (en) * | 2011-03-08 | 2012-09-13 | The Trustees Of Columbia University In The City Of New York | Methods and pharmaceutical compositions for treating lymphoid malignancy |
| JP2014114212A (ja) * | 2011-03-29 | 2014-06-26 | Dainippon Sumitomo Pharma Co Ltd | 新規ベンズイミダゾール誘導体 |
| SI2838900T1 (sl) * | 2012-04-17 | 2019-10-30 | Gilead Sciences Inc | Spojine in postopki za protivirusno zdravljenje |
| US11633399B2 (en) | 2018-12-25 | 2023-04-25 | Sol-Gel Technologies Ltd. | Treatment of skin disorders with compositions comprising an EGFR inhibitor |
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| AU2001236698A1 (en) | 2000-02-07 | 2001-08-14 | Abbott Gesellschaft Mit Beschrankter Haftung & Company Kommanditgesellschaft | 2-benzothiazolyl urea derivatives and their use as protein kinase inhibitors |
| US6608053B2 (en) | 2000-04-27 | 2003-08-19 | Yamanouchi Pharmaceutical Co., Ltd. | Fused heteroaryl derivatives |
| AR038703A1 (es) | 2002-02-28 | 2005-01-26 | Novartis Ag | Derivados de 5-feniltiazol y uso como inhibidor de quinasa p i 3 |
| US7846925B2 (en) | 2002-07-10 | 2010-12-07 | Merck Serono Sa | Azolidinone-vinyl fused-benzene derivatives |
| PT2042504E (pt) | 2002-09-30 | 2011-09-07 | Bayer Schering Pharma Ag | Derivados da azolepirimidina fundida |
| EP1557661A1 (en) | 2002-10-30 | 2005-07-27 | Toppan Printing Co., Ltd. | Inspection apparatus of wiring pattern, inspection method, detection apparatus, detection method |
| WO2004052373A1 (en) | 2002-12-06 | 2004-06-24 | Warner-Lambert Company Llc | Benzoxazin-3-ones and derivatives thereof as inhibitors of pi3k |
| AU2003303231A1 (en) | 2002-12-20 | 2004-07-14 | Warner-Lambert Company Llc | Benzoxazines and derivatives thereof as inhibitors of pi3ks |
| RU2006100484A (ru) | 2003-06-13 | 2006-06-10 | Центарис ГмбХ, Германи (DE) | Соединения, обладающие ингибирующей активностью в отношении фосфатидилинозит-3-киназы, фармацевтическая композиция, способ определения эффективности этих соединений, способ лечения нарушений (варианты) и способ изменения передачи сигнала в клетках |
| GB0315966D0 (en) | 2003-07-08 | 2003-08-13 | Cyclacel Ltd | Compounds |
| DE10344223A1 (de) | 2003-09-24 | 2005-04-21 | Merck Patent Gmbh | 1,3-Benzoxazolylderivate als Kinase-Inhibitoren |
| AU2005293607A1 (en) | 2004-10-07 | 2006-04-20 | Boehringer Ingelheim International Gmbh | PI3 kinases |
| UY29149A1 (es) | 2004-10-07 | 2006-05-31 | Boehringer Ingelheim Int | Tiazolil-dihidro-indazoles |
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- 2007-03-27 RU RU2008143547/04A patent/RU2008143547A/ru not_active Application Discontinuation
- 2007-03-27 CA CA002647292A patent/CA2647292A1/en not_active Abandoned
- 2007-03-27 EP EP07727387A patent/EP2007382A1/de not_active Withdrawn
- 2007-03-27 JP JP2009503534A patent/JP2009532415A/ja active Pending
- 2007-03-27 WO PCT/EP2007/052914 patent/WO2007115931A1/de not_active Ceased
- 2007-03-27 AU AU2007236045A patent/AU2007236045A1/en not_active Abandoned
- 2007-03-27 KR KR1020087027183A patent/KR20080111118A/ko not_active Withdrawn
- 2007-03-27 BR BRPI0710306-9A patent/BRPI0710306A2/pt not_active IP Right Cessation
- 2007-03-27 MX MX2008012534A patent/MX2008012534A/es active IP Right Grant
- 2007-03-27 CN CNA2007800207541A patent/CN101460167A/zh active Pending
- 2007-04-03 AR ARP070101385A patent/AR060267A1/es unknown
- 2007-04-04 TW TW096111947A patent/TW200806679A/zh unknown
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2008
- 2008-09-08 ZA ZA200807713A patent/ZA200807713B/xx unknown
- 2008-10-02 IL IL194494A patent/IL194494A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007115931A8 (de) | 2008-06-12 |
| WO2007115931A1 (de) | 2007-10-18 |
| KR20080111118A (ko) | 2008-12-22 |
| EP2007382A1 (de) | 2008-12-31 |
| JP2009532415A (ja) | 2009-09-10 |
| ZA200807713B (en) | 2009-08-26 |
| AU2007236045A1 (en) | 2007-10-18 |
| AR060267A1 (es) | 2008-06-04 |
| CN101460167A (zh) | 2009-06-17 |
| CA2647292A1 (en) | 2007-10-18 |
| BRPI0710306A2 (pt) | 2011-08-09 |
| IL194494A0 (en) | 2009-08-03 |
| MX2008012534A (es) | 2008-10-10 |
| US20070238730A1 (en) | 2007-10-11 |
| US7517995B2 (en) | 2009-04-14 |
| TW200806679A (en) | 2008-02-01 |
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Legal Events
| Date | Code | Title | Description |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20110602 |