ES2617339T3 - Derivados de pirrolopirimidina inhibidores de ASK1 - Google Patents
Derivados de pirrolopirimidina inhibidores de ASK1 Download PDFInfo
- Publication number
- ES2617339T3 ES2617339T3 ES11804756.2T ES11804756T ES2617339T3 ES 2617339 T3 ES2617339 T3 ES 2617339T3 ES 11804756 T ES11804756 T ES 11804756T ES 2617339 T3 ES2617339 T3 ES 2617339T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- group
- alkoxy
- halogen
- phenyl
- 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.)
- Active
Links
- 229940127254 ASK1 inhibitor Drugs 0.000 title 1
- 150000004944 pyrrolopyrimidines Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 11
- -1 and n is 0 or 1 Chemical group 0.000 abstract description 10
- 150000003839 salts Chemical class 0.000 abstract description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical group 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000002757 morpholinyl group Chemical group 0.000 abstract 2
- 125000003386 piperidinyl group Chemical group 0.000 abstract 2
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract 1
- 125000006164 6-membered heteroaryl group Chemical group 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 235000019256 formaldehyde Nutrition 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000000842 isoxazolyl group Chemical group 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002098 pyridazinyl group Chemical group 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 208000002193 Pain Diseases 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 230000036407 pain Effects 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 239000003643 water by type Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000004128 high performance liquid chromatography Methods 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 238000011321 prophylaxis Methods 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000004704 ultra performance liquid chromatography Methods 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 206010012289 Dementia Diseases 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 208000004296 neuralgia Diseases 0.000 description 4
- 208000021722 neuropathic pain Diseases 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 3
- 208000031225 myocardial ischemia Diseases 0.000 description 3
- JTZTWNBHJUZLIR-UHFFFAOYSA-N n-[1-[7-(benzenesulfonyl)-5-bromopyrrolo[2,3-d]pyrimidin-4-yl]piperidin-4-yl]benzamide Chemical compound C=12C(Br)=CN(S(=O)(=O)C=3C=CC=CC=3)C2=NC=NC=1N(CC1)CCC1NC(=O)C1=CC=CC=C1 JTZTWNBHJUZLIR-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 230000035807 sensation Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 208000008035 Back Pain Diseases 0.000 description 2
- 208000011231 Crohn disease Diseases 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- 208000001640 Fibromyalgia Diseases 0.000 description 2
- 208000007882 Gastritis Diseases 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 208000004454 Hyperalgesia Diseases 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 208000008930 Low Back Pain Diseases 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- 229910002666 PdCl2 Inorganic materials 0.000 description 2
- 208000010040 Sprains and Strains Diseases 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 206010027599 migraine Diseases 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- JMQDNLCNCDSHNC-UHFFFAOYSA-N n-piperidin-4-ylbenzamide Chemical compound C=1C=CC=CC=1C(=O)NC1CCNCC1 JMQDNLCNCDSHNC-UHFFFAOYSA-N 0.000 description 2
- 230000004770 neurodegeneration Effects 0.000 description 2
- 201000001119 neuropathy Diseases 0.000 description 2
- 230000007823 neuropathy Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 208000035824 paresthesia Diseases 0.000 description 2
- 208000033808 peripheral neuropathy Diseases 0.000 description 2
- 208000005987 polymyositis Diseases 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- 230000000638 stimulation Effects 0.000 description 2
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- AUYBSFAHQLKXSW-UHFFFAOYSA-N 1,2-dichloroethane;3-(ethyliminomethylideneamino)-n,n-dimethylpropan-1-amine;hydrochloride Chemical compound Cl.ClCCCl.CCN=C=NCCCN(C)C AUYBSFAHQLKXSW-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- MICMHFIQSAMEJG-UHFFFAOYSA-N 1-bromopyrrolidine-2,5-dione Chemical compound BrN1C(=O)CCC1=O.BrN1C(=O)CCC1=O MICMHFIQSAMEJG-UHFFFAOYSA-N 0.000 description 1
- BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 1
- KTBLRYUFNBABGO-UHFFFAOYSA-N 2-(furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=COC=C1 KTBLRYUFNBABGO-UHFFFAOYSA-N 0.000 description 1
- RXXKAAOHSXDYOT-UHFFFAOYSA-N 3,4,4-trimethoxypiperidine-1-carboxylic acid Chemical compound COC1CN(C(O)=O)CCC1(OC)OC RXXKAAOHSXDYOT-UHFFFAOYSA-N 0.000 description 1
- MGMHZGMGPRAHJA-UHFFFAOYSA-N 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylic acid Chemical compound COC1(OC)CCN(C(O)=O)CC1O MGMHZGMGPRAHJA-UHFFFAOYSA-N 0.000 description 1
- RRRCPCOJPQLWEP-UHFFFAOYSA-N 3-hydroxytriazolo[4,5-b]pyridine Chemical compound C1=CN=C2N(O)N=NC2=C1.C1=CN=C2N(O)N=NC2=C1 RRRCPCOJPQLWEP-UHFFFAOYSA-N 0.000 description 1
- MPKPNLWIOVPOBD-UHFFFAOYSA-N 3-methoxy-4-oxopiperidine-1-carboxylic acid Chemical compound COC1CN(CCC1=O)C(=O)O MPKPNLWIOVPOBD-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- IXXOMMSCNWTOPX-UHFFFAOYSA-N 7-(benzenesulfonyl)-5-bromo-4-chloropyrrolo[2,3-d]pyrimidine Chemical compound C1=C(Br)C=2C(Cl)=NC=NC=2N1S(=O)(=O)C1=CC=CC=C1 IXXOMMSCNWTOPX-UHFFFAOYSA-N 0.000 description 1
- 208000035939 Alveolitis allergic Diseases 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 description 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
- 208000032467 Aplastic anaemia Diseases 0.000 description 1
- 208000006820 Arthralgia Diseases 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 206010003645 Atopy Diseases 0.000 description 1
- 208000027496 Behcet disease Diseases 0.000 description 1
- 206010006811 Bursitis Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 206010007572 Cardiac hypertrophy Diseases 0.000 description 1
- 208000006029 Cardiomegaly Diseases 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- 208000015943 Coeliac disease Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- 206010010774 Constipation Diseases 0.000 description 1
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 description 1
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 description 1
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 description 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 206010013886 Dysaesthesia Diseases 0.000 description 1
- 208000005171 Dysmenorrhea Diseases 0.000 description 1
- 206010013935 Dysmenorrhoea Diseases 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 208000027445 Farmer Lung Diseases 0.000 description 1
- 208000004930 Fatty Liver Diseases 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 208000010412 Glaucoma Diseases 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 206010018634 Gouty Arthritis Diseases 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
- 101001018196 Homo sapiens Mitogen-activated protein kinase kinase kinase 5 Proteins 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 208000035154 Hyperesthesia Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 208000003456 Juvenile Arthritis Diseases 0.000 description 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- 208000026072 Motor neurone disease Diseases 0.000 description 1
- 206010028391 Musculoskeletal Pain Diseases 0.000 description 1
- 201000002481 Myositis Diseases 0.000 description 1
- 206010028836 Neck pain Diseases 0.000 description 1
- 206010029164 Nephrotic syndrome Diseases 0.000 description 1
- 206010062501 Non-cardiac chest pain Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 206010036376 Postherpetic Neuralgia Diseases 0.000 description 1
- 208000004550 Postoperative Pain Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 208000004756 Respiratory Insufficiency Diseases 0.000 description 1
- 206010038910 Retinitis Diseases 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- 206010039085 Rhinitis allergic Diseases 0.000 description 1
- 208000008765 Sciatica Diseases 0.000 description 1
- 206010039710 Scleroderma Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- 208000021386 Sjogren Syndrome Diseases 0.000 description 1
- 208000000491 Tendinopathy Diseases 0.000 description 1
- 206010043255 Tendonitis Diseases 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- 201000004810 Vascular dementia Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- UXRDAJMOOGEIAQ-CKOZHMEPSA-N [(8r,9s,10r,13s,14s,17r)-17-acetyl-10,13-dimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1=CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC(=C)[C@](OC(=O)C)(C(C)=O)[C@@]1(C)CC2 UXRDAJMOOGEIAQ-CKOZHMEPSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 201000010105 allergic rhinitis Diseases 0.000 description 1
- 206010053552 allodynia Diseases 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 238000002266 amputation Methods 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- 208000002399 aphthous stomatitis Diseases 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 208000020670 canker sore Diseases 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 208000037893 chronic inflammatory disorder Diseases 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- 201000006549 dyspepsia Diseases 0.000 description 1
- OLAMWIPURJGSKE-UHFFFAOYSA-N et2o diethylether Chemical compound CCOCC.CCOCC OLAMWIPURJGSKE-UHFFFAOYSA-N 0.000 description 1
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 208000022195 farmer lung disease Diseases 0.000 description 1
- 230000027950 fever generation Effects 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 208000007565 gingivitis Diseases 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-N h2o hydrate Chemical compound O.O JEGUKCSWCFPDGT-UHFFFAOYSA-N 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 208000014617 hemorrhoid Diseases 0.000 description 1
- 102000057989 human MAP3K5 Human genes 0.000 description 1
- 208000021731 hypoalgesia Diseases 0.000 description 1
- 230000036032 hypoalgesia Effects 0.000 description 1
- 208000034783 hypoesthesia Diseases 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- BCVXHSPFUWZLGQ-UHFFFAOYSA-N mecn acetonitrile Chemical compound CC#N.CC#N BCVXHSPFUWZLGQ-UHFFFAOYSA-N 0.000 description 1
- COTNUBDHGSIOTA-UHFFFAOYSA-N meoh methanol Chemical compound OC.OC COTNUBDHGSIOTA-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 208000005264 motor neuron disease Diseases 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- BLBUYQCDZOOMCC-UHFFFAOYSA-N n-[1-[7-(benzenesulfonyl)-5-(furan-3-yl)pyrrolo[2,3-d]pyrimidin-4-yl]piperidin-4-yl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(CC1)CCN1C(C1=2)=NC=NC=2N(S(=O)(=O)C=2C=CC=CC=2)C=C1C=1C=COC=1 BLBUYQCDZOOMCC-UHFFFAOYSA-N 0.000 description 1
- ZPRJZBSPXNMSBJ-UHFFFAOYSA-N n-[1-[7-(benzenesulfonyl)-5-ethylpyrrolo[2,3-d]pyrimidin-4-yl]piperidin-4-yl]benzamide Chemical compound C=12C(CC)=CN(S(=O)(=O)C=3C=CC=CC=3)C2=NC=NC=1N(CC1)CCC1NC(=O)C1=CC=CC=C1 ZPRJZBSPXNMSBJ-UHFFFAOYSA-N 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
- 201000006292 polyarteritis nodosa Diseases 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical group CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 238000007634 remodeling Methods 0.000 description 1
- 201000004193 respiratory failure Diseases 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 230000009155 sensory pathway Effects 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- WGRULTCAYDOGQK-UHFFFAOYSA-M sodium;sodium;hydroxide Chemical compound [OH-].[Na].[Na+] WGRULTCAYDOGQK-UHFFFAOYSA-M 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 description 1
- 201000004415 tendinitis Diseases 0.000 description 1
- DZSWWZASZDLNHB-UHFFFAOYSA-N tert-butyl 3-(methoxymethyl)-4-oxopiperidine-1-carboxylate Chemical compound COCC1CN(C(=O)OC(C)(C)C)CCC1=O DZSWWZASZDLNHB-UHFFFAOYSA-N 0.000 description 1
- DXHPWDBZWRHQRX-UHFFFAOYSA-N tert-butyl 3-methoxy-4-oxopiperidine-1-carboxylate Chemical compound COC1CN(C(=O)OC(C)(C)C)CCC1=O DXHPWDBZWRHQRX-UHFFFAOYSA-N 0.000 description 1
- QKOMXDVNSNZAEU-UHFFFAOYSA-N tert-butyl 4-amino-3-(methoxymethyl)piperidine-1-carboxylate Chemical compound COCC1CN(C(=O)OC(C)(C)C)CCC1N QKOMXDVNSNZAEU-UHFFFAOYSA-N 0.000 description 1
- QNGHCFVWYKWWMU-UHFFFAOYSA-N tert-butyl 4-amino-3-methoxypiperidine-1-carboxylate Chemical compound COC1CN(C(=O)OC(C)(C)C)CCC1N QNGHCFVWYKWWMU-UHFFFAOYSA-N 0.000 description 1
- ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- PHCBRBWANGJMHS-UHFFFAOYSA-J tetrasodium;disulfate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O PHCBRBWANGJMHS-UHFFFAOYSA-J 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 206010043778 thyroiditis Diseases 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- KPZYAGQLBFUTMA-UHFFFAOYSA-K tripotassium;phosphate;trihydrate Chemical compound O.O.O.[K+].[K+].[K+].[O-]P([O-])([O-])=O KPZYAGQLBFUTMA-UHFFFAOYSA-K 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 201000002282 venous insufficiency Diseases 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/10—Laxatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/04—Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Obesity (AREA)
- Ophthalmology & Optometry (AREA)
- Psychology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42386510P | 2010-12-16 | 2010-12-16 | |
| US423865P | 2010-12-16 | ||
| PCT/GB2011/052484 WO2012080735A1 (en) | 2010-12-16 | 2011-12-15 | Ask1 inhibiting pyrrolopyrimidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2617339T3 true ES2617339T3 (es) | 2017-06-16 |
Family
ID=45444639
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11804756.2T Active ES2617339T3 (es) | 2010-12-16 | 2011-12-15 | Derivados de pirrolopirimidina inhibidores de ASK1 |
Country Status (6)
| Country | Link |
|---|---|
| US (3) | US9045485B2 (enExample) |
| EP (1) | EP2651417B1 (enExample) |
| JP (1) | JP5927201B2 (enExample) |
| ES (1) | ES2617339T3 (enExample) |
| PL (1) | PL2651417T3 (enExample) |
| WO (1) | WO2012080735A1 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI598347B (zh) | 2009-07-13 | 2017-09-11 | 基利科學股份有限公司 | 調節細胞凋亡信號之激酶的抑制劑 |
| EP2651417B1 (en) | 2010-12-16 | 2016-11-30 | Calchan Limited | Ask1 inhibiting pyrrolopyrimidine derivatives |
| UY34573A (es) | 2012-01-27 | 2013-06-28 | Gilead Sciences Inc | Inhibidor de la quinasa que regula la señal de la apoptosis |
| CN104981247A (zh) * | 2012-09-06 | 2015-10-14 | 普莱希科公司 | 用于激酶调节的化合物和方法及其适应症 |
| CN104119342A (zh) * | 2013-04-25 | 2014-10-29 | 苏州科捷生物医药有限公司 | 一种制备高纯度4-氯-5-甲基-7H-吡咯[2,3-d]嘧啶的方法 |
| US20150342943A1 (en) * | 2014-06-03 | 2015-12-03 | Gilead Sciences, Inc. | Methods of treating liver disease |
| TW201618781A (zh) | 2014-08-13 | 2016-06-01 | 吉李德科學股份有限公司 | 治療肺高血壓之方法 |
| CA2960280A1 (en) * | 2014-09-10 | 2016-03-17 | Epizyme, Inc. | Substituted piperidine compounds |
| JP2017528471A (ja) | 2014-09-24 | 2017-09-28 | ギリアード サイエンシーズ, インコーポレイテッド | 肝疾患を処置する方法 |
| ES2842749T3 (es) | 2014-12-23 | 2021-07-14 | Gilead Sciences Inc | Procesos para preparar inhibidores de ASK1 |
| MA41252A (fr) | 2014-12-23 | 2017-10-31 | Gilead Sciences Inc | Formes solides d'un inhibiteur d'ask 1 |
| CA3021675C (en) | 2016-08-31 | 2024-06-25 | Eisai R&D Management Co., Ltd. | Pyrazolo[1,5-a]pyrimidine compound |
| JOP20190221A1 (ar) * | 2017-04-05 | 2019-09-23 | Seal Rock Therapeutics Inc | مركبات مثبطات كيناز منظم لإشارات الاستماتة 1 (ask1) واستخداماتها |
| AU2018266911C1 (en) | 2017-05-12 | 2022-10-20 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| WO2018218044A2 (en) | 2017-05-25 | 2018-11-29 | Enanta Pharmaceuticals Inc | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| US10450301B2 (en) | 2017-05-25 | 2019-10-22 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| US10253018B2 (en) | 2017-05-25 | 2019-04-09 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| GB201711234D0 (en) * | 2017-07-12 | 2017-08-23 | Galapagos Nv | Pyrrolopyrimidine and pyrrolopyridine derivatives |
| CN107556318B (zh) * | 2017-08-22 | 2020-08-11 | 山东大学 | 一种含哌啶的吡咯并嘧啶类化合物及其制备方法与应用 |
| US10597382B2 (en) | 2017-08-28 | 2020-03-24 | Enanta Pharmaceuticals, Inc. | Tetrazole containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| EP3735404B1 (en) | 2018-01-02 | 2023-11-29 | Seal Rock Therapeutics, Inc. | Ask1 inhibitor compounds and uses thereof |
| TW201936607A (zh) | 2018-02-26 | 2019-09-16 | 日商衛材R&D企管股份有限公司 | 吡唑并[1,5-a]嘧啶化合物的鹽及其晶體 |
| WO2019213239A1 (en) | 2018-05-02 | 2019-11-07 | Enanta Pharmaceuticals Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| ES3004523T3 (en) | 2018-05-02 | 2025-03-12 | Enanta Pharm Inc | Tetrazole containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| WO2020017569A1 (ja) * | 2018-07-17 | 2020-01-23 | 日本ケミファ株式会社 | T型カルシウムチャネル阻害剤 |
| WO2020041417A1 (en) | 2018-08-22 | 2020-02-27 | Enanta Pharmaceuticals, Inc. | Cycloalkyl-containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| WO2020106707A1 (en) | 2018-11-19 | 2020-05-28 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| US11466033B2 (en) | 2019-03-25 | 2022-10-11 | Enanta Pharmaceuticals, Inc. | Substituted pyridines as apoptosis signal-regulating kinase 1 inhibitors |
| JP2022081710A (ja) * | 2019-03-29 | 2022-06-01 | ユーティアイ リミテッド パートナーシップ | 関節リウマチを治療するためのt型カルシウムチャネル阻害剤の使用 |
| AU2020250468A1 (en) * | 2019-03-29 | 2021-11-04 | Kinki University | Use of T-type calcium channel blocker for treating pruritus |
| CN111303155A (zh) * | 2020-03-13 | 2020-06-19 | 深圳大学 | 靶向pak1抑制剂及其在抗肿瘤治疗药物中的应用 |
| WO2023246876A1 (zh) * | 2022-06-24 | 2023-12-28 | 上海科技大学 | 甲酰胺类衍生物的医药用途、甲酰胺类衍生物、包含其的药物组合物 |
Family Cites Families (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2065434C (en) | 1989-09-19 | 1999-11-30 | Yasuji Sakuma | Pyrrolo[2,3-d]pyrimidine derivatives, process for producing the same and pharmaceutical preparation comprising the same as active ingredient |
| YU76100A (sh) | 1998-06-02 | 2003-12-31 | Osi Pharmaceuticals Inc. | Pirolo(2,3-d) pirimidin preparati i njihova primena |
| US6878716B1 (en) | 1998-06-02 | 2005-04-12 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A1 receptor and uses thereof |
| PA8474101A1 (es) | 1998-06-19 | 2000-09-29 | Pfizer Prod Inc | Compuestos de pirrolo [2,3-d] pirimidina |
| CN1146562C (zh) * | 1999-10-25 | 2004-04-21 | 奥坦纳医药公司 | 作为pde4抑制剂的四氢噻喃2,3-二氮杂萘酮类衍生物 |
| US6680322B2 (en) | 1999-12-02 | 2004-01-20 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A1 receptors and uses thereof |
| US7160890B2 (en) | 1999-12-02 | 2007-01-09 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A3 receptor and uses thereof |
| AU784878B2 (en) | 1999-12-02 | 2006-07-13 | Osi Pharmaceuticals, Inc. | Compounds specific to adenosine A1 A2A and A3 receptors and uses thereof |
| WO2003037898A1 (en) | 2001-10-31 | 2003-05-08 | Bayer Healthcare Ag | Pyrimido [4,5-b] indole derivatives |
| US20040138238A1 (en) | 2002-08-08 | 2004-07-15 | Dhanoa Dale S. | Substituted aminopyrimidine compounds as neurokinin antagonists |
| WO2004048565A1 (ja) | 2002-11-22 | 2004-06-10 | Takeda Pharmaceutical Company Limited | アポトーシス関連蛋白質およびその用途 |
| US8076338B2 (en) | 2004-04-23 | 2011-12-13 | Exelixis, Inc. | Kinase modulators and methods of use |
| MY179032A (en) | 2004-10-25 | 2020-10-26 | Cancer Research Tech Ltd | Ortho-condensed pyridine and pyrimidine derivatives (e.g.purines) as protein kinase inhibitors |
| JP2009536620A (ja) | 2006-04-25 | 2009-10-15 | アステックス、セラピューティックス、リミテッド | 医薬組み合わせ物 |
| EP2029592A1 (en) | 2006-04-25 | 2009-03-04 | Astex Therapeutics Limited | Pharmaceutical compounds |
| DK3421471T3 (da) * | 2006-04-25 | 2021-06-14 | Astex Therapeutics Ltd | Purin- og deazapurinderivater som farmaceutiske forbindelser |
| WO2008012635A2 (en) | 2006-07-26 | 2008-01-31 | Pfizer Products Inc. | Amine derivatives useful as anticancer agents |
| WO2008016131A1 (en) | 2006-08-04 | 2008-02-07 | Takeda Pharmaceutical Company Limited | Fused heterocyclic compound |
| WO2008075172A2 (en) | 2006-12-19 | 2008-06-26 | Pfizer Products Inc. | Nicotinamide derivatives as inhibitors of h-pgds and their use for treating prostaglandin d2 mediated diseases |
| AR064415A1 (es) | 2006-12-21 | 2009-04-01 | Cancer Rec Tech Ltd | Derivados de pirrolo-piperidinas y purinas,composiciones farmaceuticas que los contienen y usos en trastornos y/o enfermedades mediadas por pka y pkb. |
| AR064416A1 (es) | 2006-12-21 | 2009-04-01 | Cancer Rec Tech Ltd | Derivados de purina, piridina y pirimidina condensadas con heterociclos, moduladores de pka y/o pkb, composiciones farmaceuticas que los contienen, y usos para el tratamiento de enfermedades hiperproliferativas. |
| EP2132196A1 (en) * | 2007-02-26 | 2009-12-16 | Pfizer Products Inc. | Nicotinamide derivatives as inhibitors of h-pgds and their use for treating prostaglandin d2 mediated diseases |
| WO2008117796A1 (ja) | 2007-03-28 | 2008-10-02 | Dainippon Sumitomo Pharma Co., Ltd. | 新規ムチリン誘導体 |
| EP2181112A1 (en) * | 2007-08-31 | 2010-05-05 | Merck Serono S.A. | Triazolopyridine compounds and their use as ask inhibitors |
| PT2201012E (pt) | 2007-10-11 | 2014-09-04 | Astrazeneca Ab | Derivados de pirrolo[2,3-d]piridina como inibidores da proteína quinase b |
| JP5432982B2 (ja) | 2008-03-31 | 2014-03-05 | 武田薬品工業株式会社 | アポトーシスシグナル調節キナーゼ1阻害剤 |
| MX2010011450A (es) | 2008-04-21 | 2010-11-10 | Lexicon Pharmaceuticals Inc | Inhibidores del limk2, composiciones que los comprenden y metodos para su uso. |
| US8178555B2 (en) | 2008-06-24 | 2012-05-15 | Takeda Pharmaceutical Company Limited | Apoptosis signal-regulating kinase 1 inhibitors |
| EP2320895A2 (en) | 2008-07-03 | 2011-05-18 | Exelixis, Inc. | Cdk modulators |
| WO2010019911A2 (en) | 2008-08-15 | 2010-02-18 | Board Of Regents, The University Of Texas System | 1,4-benzoxazine compounds and derivatives thereof as therapeutic drugs for the treatment of neurodegenerative conditions |
| DK2385832T3 (en) | 2009-01-08 | 2015-09-21 | Curis Inc | Phosphoinositid-3-kinase-inhibitorer med en zink-bindingsdel |
| US8987309B2 (en) | 2009-04-17 | 2015-03-24 | The Translational Genomics Research Institute | Compounds, pharmaceutical compositions and methods of use of 2-aryl pyridylazoles |
| CN102574857B (zh) | 2009-07-08 | 2015-06-10 | 利奥制药有限公司 | 作为jak受体和蛋白酪氨酸激酶抑制剂的杂环化合物 |
| TWI598347B (zh) | 2009-07-13 | 2017-09-11 | 基利科學股份有限公司 | 調節細胞凋亡信號之激酶的抑制劑 |
| TWI466885B (zh) | 2009-07-31 | 2015-01-01 | Japan Tobacco Inc | 含氮螺環化合物及其醫藥用途 |
| WO2011029043A1 (en) | 2009-09-04 | 2011-03-10 | Biogen Idec Ma Inc. | Heteroaryl btk inhibitors |
| WO2011041293A1 (en) | 2009-09-30 | 2011-04-07 | Takeda Pharmaceutical Company Limited | Pyrazolo [1, 5-a] pyrimidine derivatives as apoptosis signal-regulating kinase 1 inhibitors |
| PT2531501E (pt) | 2010-02-03 | 2014-02-17 | Takeda Pharmaceutical | Inibidores da cinase de regulação do sinal de apoptose 1 |
| JP2013518909A (ja) | 2010-02-08 | 2013-05-23 | キナゲン,インク. | アロステリックキナーゼ阻害が関係する治療方法および組成物 |
| MX345552B (es) | 2010-03-24 | 2017-02-02 | Amitech Therapeutic Solutions Inc | Compuestos heterocíclicos útiles para inhibición de cinasa. |
| SI2588475T1 (sl) | 2010-07-02 | 2015-12-31 | Gilead Sciences, Inc. | Kinazni inhibitorji za regulacijo apoptoznega signala |
| WO2012011548A1 (ja) | 2010-07-23 | 2012-01-26 | 国立大学法人 東京大学 | 含窒素複素環誘導体 |
| MX2013001970A (es) | 2010-08-20 | 2013-08-09 | Hutchison Medipharma Ltd | Compuestos de pirrolopirimidina y usos de los mismos. |
| CN102372717B (zh) | 2010-08-20 | 2014-06-18 | 和记黄埔医药(上海)有限公司 | 吡咯并嘧啶类化合物及其用途 |
| WO2012022045A1 (en) | 2010-08-20 | 2012-02-23 | Hutchison Medipharma Limited | Pyrrolopyrimidine compounds and uses thereof |
| WO2012054364A2 (en) | 2010-10-22 | 2012-04-26 | Merck Sharp & Dohme Corp. | Bicyclic diamines as janus kinase inhibitors |
| EP2632898A4 (en) | 2010-10-29 | 2014-04-02 | Biogen Idec Inc | HETEROCYCLIC TYROSINE KINASE HEMMER |
| EP2651417B1 (en) * | 2010-12-16 | 2016-11-30 | Calchan Limited | Ask1 inhibiting pyrrolopyrimidine derivatives |
| UY34573A (es) | 2012-01-27 | 2013-06-28 | Gilead Sciences Inc | Inhibidor de la quinasa que regula la señal de la apoptosis |
| EP2867236B1 (en) | 2012-06-29 | 2017-06-14 | Pfizer Inc | Novel 4-(substituted-amino)-7h-pyrrolo[2,3-d]pyrimidines as lrrk2 inhibitors |
| CN104981247A (zh) | 2012-09-06 | 2015-10-14 | 普莱希科公司 | 用于激酶调节的化合物和方法及其适应症 |
| CN105189505B (zh) | 2012-09-12 | 2019-03-22 | 默克夏普&多梅有限公司 | 用作抗菌剂的三环促旋酶抑制剂 |
| UY35212A (es) | 2012-12-21 | 2014-06-30 | Gilead Sciences Inc | Inhibidores de la quinasa que regula la señal de la apoptosis |
-
2011
- 2011-12-15 EP EP11804756.2A patent/EP2651417B1/en active Active
- 2011-12-15 US US13/994,691 patent/US9045485B2/en active Active
- 2011-12-15 JP JP2013543883A patent/JP5927201B2/ja not_active Expired - Fee Related
- 2011-12-15 PL PL11804756T patent/PL2651417T3/pl unknown
- 2011-12-15 WO PCT/GB2011/052484 patent/WO2012080735A1/en not_active Ceased
- 2011-12-15 ES ES11804756.2T patent/ES2617339T3/es active Active
-
2015
- 2015-04-28 US US14/698,489 patent/US9585886B2/en not_active Expired - Fee Related
-
2017
- 2017-01-30 US US15/420,000 patent/US20170210748A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| PL2651417T3 (pl) | 2017-08-31 |
| US9585886B2 (en) | 2017-03-07 |
| US20140038957A1 (en) | 2014-02-06 |
| US9045485B2 (en) | 2015-06-02 |
| EP2651417B1 (en) | 2016-11-30 |
| WO2012080735A1 (en) | 2012-06-21 |
| US20160067251A1 (en) | 2016-03-10 |
| US20170210748A1 (en) | 2017-07-27 |
| JP5927201B2 (ja) | 2016-06-01 |
| EP2651417A1 (en) | 2013-10-23 |
| JP2014505037A (ja) | 2014-02-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2617339T3 (es) | Derivados de pirrolopirimidina inhibidores de ASK1 | |
| ES2559528T3 (es) | Compuestos y composiciones como inhibidores de proteína cinasa | |
| CN106083891B (zh) | 具有hiv整合酶抑制活性的化合物的制造方法 | |
| JP6523566B2 (ja) | ジヒドロピリド環化合物の結晶形、製造方法および中間体 | |
| ES2651165T3 (es) | 2-aminopirimidin-6-onas y análogos que presentan actividades anti-cáncer y antiproliferativa | |
| ES2684309T3 (es) | Reactivo sulfamoilante | |
| CN113365631B (zh) | 布鲁顿酪氨酸激酶抑制剂 | |
| IL260691B (en) | Bruton's tyrosine kinase inhibitors | |
| WO2018039310A1 (en) | Amino-pyrrolopyrimidinone compounds and methods of use thereof | |
| ES2730942T3 (es) | Derivados de triazolopiridina como moduladores de la actividad de TNF | |
| EP2001872A1 (en) | Benzofuran compounds as ep1 receptor antagonists | |
| CA2725481A1 (en) | Nicotinamide derivatives | |
| TW201605814A (zh) | 用於合成經保護之n-烷基三唑甲醛的三唑中間體 | |
| KR20150093229A (ko) | P2x7 수용체 길항제로서의 인돌 카르복사미드 유도체 | |
| JP2023539275A (ja) | 新規なrho関連タンパク質キナーゼ阻害剤の調製方法およびその調製方法における中間体 | |
| RS57415B1 (sr) | Supstituisani tiazol ili oksazol antagonisti p2x7 receptora | |
| AU2005318372A1 (en) | Pyridine compounds for the treatment of prostaglandin mediated diseases | |
| CN102712641B (zh) | Mk2抑制剂 | |
| AU2020345000A1 (en) | 1,4-dihydrobenzo[d]pyrazolo[3,4-f][1,3]diazepine derivatives and related compounds as LRRK2, NUAK1 and/or TYK2 kinase modulators for the treatment of e.g. autoimmune disease | |
| AU2023270260A1 (en) | Novel processes and intermediates for the preparation of soluble guanylate cyclase stimulators | |
| KR102523786B1 (ko) | 트리아졸로피리딘 화합물의 제조 방법 | |
| ES2616883T3 (es) | Derivados amida heterocíclicos como antagonistas del receptor P2X7 | |
| EP1663238A1 (en) | HEXA- AND OCTAHYDRO-PYRIDO[1,2-a] PYRAZINE DERIVATIVES WITH NK1 ANTAGONISTIC ACTIVITY | |
| CA3115712A1 (en) | 6-mercaptopurine nucleoside analogues | |
| AU2024280048A1 (en) | Tricyclic compound, and preparation method therefor and use thereof |