JP2017503838A5 - - Google Patents
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- JP2017503838A5 JP2017503838A5 JP2016548152A JP2016548152A JP2017503838A5 JP 2017503838 A5 JP2017503838 A5 JP 2017503838A5 JP 2016548152 A JP2016548152 A JP 2016548152A JP 2016548152 A JP2016548152 A JP 2016548152A JP 2017503838 A5 JP2017503838 A5 JP 2017503838A5
- Authority
- JP
- Japan
- Prior art keywords
- indazol
- amino
- benzamide
- yloxy
- pyran
- 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.)
- Pending
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- -1 tetrahydro-2H-pyran-4-yloxy Chemical group 0.000 claims 92
- 208000002193 Pain Diseases 0.000 claims 38
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 229910052736 halogen Inorganic materials 0.000 claims 19
- 150000002367 halogens Chemical class 0.000 claims 19
- 125000001424 substituent group Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 17
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 15
- 150000002431 hydrogen Chemical class 0.000 claims 15
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 13
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 12
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 125000004043 oxo group Chemical group O=* 0.000 claims 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 8
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 7
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 7
- 125000001188 haloalkyl group Chemical group 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 208000011580 syndromic disease Diseases 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 4
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 4
- 206010019233 Headaches Diseases 0.000 claims 4
- 201000001883 cholelithiasis Diseases 0.000 claims 4
- 208000001130 gallstones Diseases 0.000 claims 4
- 231100000869 headache Toxicity 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 208000006820 Arthralgia Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 208000008035 Back Pain Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 206010058019 Cancer Pain Diseases 0.000 claims 2
- 206010064012 Central pain syndrome Diseases 0.000 claims 2
- 208000006561 Cluster Headache Diseases 0.000 claims 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims 2
- 208000005171 Dysmenorrhea Diseases 0.000 claims 2
- 201000009273 Endometriosis Diseases 0.000 claims 2
- 208000001640 Fibromyalgia Diseases 0.000 claims 2
- 208000007514 Herpes zoster Diseases 0.000 claims 2
- 208000004454 Hyperalgesia Diseases 0.000 claims 2
- 208000035154 Hyperesthesia Diseases 0.000 claims 2
- 206010065390 Inflammatory pain Diseases 0.000 claims 2
- 208000005615 Interstitial Cystitis Diseases 0.000 claims 2
- 208000000913 Kidney Calculi Diseases 0.000 claims 2
- 208000008930 Low Back Pain Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 206010027452 Metastases to bone Diseases 0.000 claims 2
- 206010029148 Nephrolithiasis Diseases 0.000 claims 2
- 208000001294 Nociceptive Pain Diseases 0.000 claims 2
- 206010068319 Oropharyngeal pain Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 206010034620 Peripheral sensory neuropathy Diseases 0.000 claims 2
- 208000004983 Phantom Limb Diseases 0.000 claims 2
- 206010056238 Phantom pain Diseases 0.000 claims 2
- 201000007100 Pharyngitis Diseases 0.000 claims 2
- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims 2
- 208000004550 Postoperative Pain Diseases 0.000 claims 2
- 206010037779 Radiculopathy Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 206010042496 Sunburn Diseases 0.000 claims 2
- 206010043269 Tension headache Diseases 0.000 claims 2
- 208000008548 Tension-Type Headache Diseases 0.000 claims 2
- 206010046798 Uterine leiomyoma Diseases 0.000 claims 2
- 125000002619 bicyclic group Chemical group 0.000 claims 2
- 208000003295 carpal tunnel syndrome Diseases 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 238000002512 chemotherapy Methods 0.000 claims 2
- 208000022371 chronic pain syndrome Diseases 0.000 claims 2
- 208000018912 cluster headache syndrome Diseases 0.000 claims 2
- 206010009887 colitis Diseases 0.000 claims 2
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 2
- 239000012634 fragment Substances 0.000 claims 2
- 201000010260 leiomyoma Diseases 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 201000005572 sensory peripheral neuropathy Diseases 0.000 claims 2
- 208000020431 spinal cord injury Diseases 0.000 claims 2
- 230000002123 temporal effect Effects 0.000 claims 2
- 208000004371 toothache Diseases 0.000 claims 2
- 206010044652 trigeminal neuralgia Diseases 0.000 claims 2
- 208000009935 visceral pain Diseases 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- FFJQNSAJQHATIO-UHFFFAOYSA-N 1-[4-[3-amino-4-(oxan-4-yloxy)-1H-indazol-6-yl]-2-(4-cyclohexylpiperazin-1-yl)phenyl]ethanone Chemical compound NC1=NNC2=CC(=CC(=C12)OC1CCOCC1)C1=CC(=C(C=C1)C(C)=O)N1CCN(CC1)C1CCCCC1 FFJQNSAJQHATIO-UHFFFAOYSA-N 0.000 claims 1
- SBIHAUVDEWDHBY-UHFFFAOYSA-N 1-[4-[3-amino-4-(oxan-4-yloxy)-1H-indazol-6-yl]-2-(4-cyclopropylpiperazin-1-yl)phenyl]ethanone Chemical compound NC1=NNC2=CC(=CC(=C12)OC1CCOCC1)C1=CC(=C(C=C1)C(C)=O)N1CCN(CC1)C1CC1 SBIHAUVDEWDHBY-UHFFFAOYSA-N 0.000 claims 1
- CYLWFEBCVOYLRN-UHFFFAOYSA-N 1-[4-[3-amino-4-(oxan-4-yloxy)-1H-indazol-6-yl]-2-(4-phenylpiperazin-1-yl)phenyl]ethanone Chemical compound NC1=NNC2=CC(=CC(=C12)OC1CCOCC1)C1=CC(=C(C=C1)C(C)=O)N1CCN(CC1)C1=CC=CC=C1 CYLWFEBCVOYLRN-UHFFFAOYSA-N 0.000 claims 1
- QDEAGLCYQMZVBB-UHFFFAOYSA-N 1-[4-[3-amino-4-(oxan-4-yloxy)-1H-indazol-6-yl]-2-(4-pyridin-3-ylpiperazin-1-yl)phenyl]ethanone Chemical compound CC(=O)C1=C(C=C(C=C1)C1=CC2=C(C(N)=NN2)C(OC2CCOCC2)=C1)N1CCN(CC1)C1=CC=CN=C1 QDEAGLCYQMZVBB-UHFFFAOYSA-N 0.000 claims 1
- ZFPMHGWAZNXJTL-UHFFFAOYSA-N 1-[4-[3-amino-4-(oxan-4-yloxy)-1H-indazol-6-yl]-2-(4-pyrimidin-2-ylpiperazin-1-yl)phenyl]ethanone Chemical compound CC(=O)C1=C(C=C(C=C1)C1=CC2=C(C(N)=NN2)C(OC2CCOCC2)=C1)N1CCN(CC1)C1=NC=CC=N1 ZFPMHGWAZNXJTL-UHFFFAOYSA-N 0.000 claims 1
- JSQWTLKKWLBQRE-UHFFFAOYSA-N 1-[4-[3-amino-4-(oxan-4-yloxy)-1H-indazol-6-yl]-2-[4-(1,3-thiazol-2-yl)piperazin-1-yl]phenyl]ethanone Chemical compound CC(=O)C1=C(C=C(C=C1)C1=CC2=C(C(N)=NN2)C(OC2CCOCC2)=C1)N1CCN(CC1)C1=NC=CS1 JSQWTLKKWLBQRE-UHFFFAOYSA-N 0.000 claims 1
- CXJDAQUJBXVNNZ-UHFFFAOYSA-N 1-[4-[3-amino-4-(oxan-4-yloxy)-1H-indazol-6-yl]-2-[4-(4-fluorophenyl)piperazin-1-yl]phenyl]ethanone Chemical compound CC(=O)C1=C(C=C(C=C1)C1=CC2=C(C(N)=NN2)C(OC2CCOCC2)=C1)N1CCN(CC1)C1=CC=C(F)C=C1 CXJDAQUJBXVNNZ-UHFFFAOYSA-N 0.000 claims 1
- BBOZIECPBRYBFE-UHFFFAOYSA-N 1-[4-[3-amino-4-(oxan-4-yloxy)-1H-indazol-6-yl]-2-[4-(cyclopropanecarbonyl)piperazin-1-yl]phenyl]ethanone Chemical compound CC(=O)C1=C(C=C(C=C1)C1=CC2=C(C(N)=NN2)C(OC2CCOCC2)=C1)N1CCN(CC1)C(=O)C1CC1 BBOZIECPBRYBFE-UHFFFAOYSA-N 0.000 claims 1
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 1
- BTSFZAMTPAYEPC-UHFFFAOYSA-N 2-(4-cyclohexylpiperazin-1-yl)-4-(4-cyclopentyloxy-3-methyl-2H-indazol-6-yl)-N-methylbenzamide Chemical compound C1(CCCCC1)N1CCN(CC1)C1=C(C(=O)NC)C=CC(=C1)C1=CC(=C2C(=NNC2=C1)C)OC1CCCC1 BTSFZAMTPAYEPC-UHFFFAOYSA-N 0.000 claims 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 claims 1
- FBGPYBSHDQTNKA-UHFFFAOYSA-N 4-(3-amino-1H-indazol-6-yl)-2-(4-benzylpiperazin-1-yl)benzamide Chemical compound NC1=NNC2=CC(=CC=C12)C1=CC(=C(C(=O)N)C=C1)N1CCN(CC1)CC1=CC=CC=C1 FBGPYBSHDQTNKA-UHFFFAOYSA-N 0.000 claims 1
- JBYOMAZBHMCUFO-UHFFFAOYSA-N 4-(3-amino-1H-indazol-6-yl)-2-(4-cyclohexylpiperazin-1-yl)benzamide Chemical compound NC1=NNC2=CC(=CC=C12)C1=CC(=C(C(=O)N)C=C1)N1CCN(CC1)C1CCCCC1 JBYOMAZBHMCUFO-UHFFFAOYSA-N 0.000 claims 1
- LFIMNFUTBNTWGR-UHFFFAOYSA-N 4-(3-amino-1H-indazol-6-yl)-2-(4-phenylpiperazin-1-yl)benzamide Chemical compound NC1=NNC2=CC(=CC=C12)C1=CC(=C(C(=O)N)C=C1)N1CCN(CC1)C1=CC=CC=C1 LFIMNFUTBNTWGR-UHFFFAOYSA-N 0.000 claims 1
- NEJGAGHHFAYHGV-UHFFFAOYSA-N 4-(3-amino-4-propan-2-yloxy-1H-indazol-6-yl)-2-(4-cyclohexylpiperazin-1-yl)-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)OC(C)C)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)C1CCCCC1 NEJGAGHHFAYHGV-UHFFFAOYSA-N 0.000 claims 1
- NGYPNUGWYQTWFD-UHFFFAOYSA-N 4-[2-acetamido-5-[3-methyl-4-(oxan-4-yloxy)-2H-indazol-6-yl]phenyl]-N-propan-2-ylpiperazine-1-carboxamide Chemical compound C(C)(=O)NC1=C(C=C(C=C1)C1=CC(=C2C(=NNC2=C1)C)OC1CCOCC1)N1CCN(CC1)C(=O)NC(C)C NGYPNUGWYQTWFD-UHFFFAOYSA-N 0.000 claims 1
- MGUKGLFLLCYSDU-UHFFFAOYSA-N 4-[3-amino-4-(1,1,1-trifluoropropan-2-yloxy)-1H-indazol-6-yl]-2-(4-cyclohexylpiperazin-1-yl)-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)OC(C(F)(F)F)C)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)C1CCCCC1 MGUKGLFLLCYSDU-UHFFFAOYSA-N 0.000 claims 1
- YUBUAAPGSZXETH-UHFFFAOYSA-N 4-[3-amino-4-(1,1,1-trifluoropropan-2-yloxy)-1H-indazol-6-yl]-2-(4-cyclopropylpiperazin-1-yl)-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)OC(C(F)(F)F)C)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)C1CC1 YUBUAAPGSZXETH-UHFFFAOYSA-N 0.000 claims 1
- QLRPXVWKEWQCQV-UHFFFAOYSA-N 4-[3-amino-4-(oxan-4-yloxy)-1H-indazol-6-yl]-2-(4-cyclohexylpiperazin-1-yl)-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)OC1CCOCC1)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)C1CCCCC1 QLRPXVWKEWQCQV-UHFFFAOYSA-N 0.000 claims 1
- BZGDFUFRSOYCMX-UHFFFAOYSA-N 4-[3-amino-4-(oxan-4-yloxy)-1H-indazol-6-yl]-2-[4-(2,2-difluoroethyl)piperazin-1-yl]-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)OC1CCOCC1)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)CC(F)F BZGDFUFRSOYCMX-UHFFFAOYSA-N 0.000 claims 1
- CUIGWPBONZZLHD-UHFFFAOYSA-N 4-[3-amino-4-(oxan-4-yloxy)-1H-indazol-6-yl]-2-[4-(5-fluoropyrimidin-2-yl)piperazin-1-yl]-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)OC1CCOCC1)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)C1=NC=C(C=N1)F CUIGWPBONZZLHD-UHFFFAOYSA-N 0.000 claims 1
- WJQDTAQMAYNIQM-UHFFFAOYSA-N 4-[3-amino-4-(oxan-4-yloxy)-1H-indazol-6-yl]-2-[4-(cyclopentylmethyl)piperazin-1-yl]-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)OC1CCOCC1)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)CC1CCCC1 WJQDTAQMAYNIQM-UHFFFAOYSA-N 0.000 claims 1
- MTMBZJGLXDIRGR-UHFFFAOYSA-N 4-[3-amino-4-(oxan-4-yloxy)-1H-indazol-6-yl]-2-[4-[(3,3-difluorocyclobutyl)methyl]piperazin-1-yl]-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)OC1CCOCC1)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)CC1CC(C1)(F)F MTMBZJGLXDIRGR-UHFFFAOYSA-N 0.000 claims 1
- ZOECYGJRBZDTOU-OAHLLOKOSA-N 4-[3-amino-4-[(2R)-1,1,1-trifluoropropan-2-yl]oxy-1H-indazol-6-yl]-2-(2-cyclohexyloxyethoxy)-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)O[C@@H](C(F)(F)F)C)C1=CC(=C(C(=O)NC)C=C1)OCCOC1CCCCC1 ZOECYGJRBZDTOU-OAHLLOKOSA-N 0.000 claims 1
- SRXOFBPYMAEIJT-OAHLLOKOSA-N 4-[3-amino-4-[(2R)-1,1,1-trifluoropropan-2-yl]oxy-1H-indazol-6-yl]-2-(4-cyclobutylpiperazin-1-yl)-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)O[C@@H](C(F)(F)F)C)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)C1CCC1 SRXOFBPYMAEIJT-OAHLLOKOSA-N 0.000 claims 1
- MGUKGLFLLCYSDU-QGZVFWFLSA-N 4-[3-amino-4-[(2R)-1,1,1-trifluoropropan-2-yl]oxy-1H-indazol-6-yl]-2-(4-cyclohexylpiperazin-1-yl)-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)O[C@@H](C(F)(F)F)C)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)C1CCCCC1 MGUKGLFLLCYSDU-QGZVFWFLSA-N 0.000 claims 1
- CVOJYADDGGNLSP-QGZVFWFLSA-N 4-[3-amino-4-[(2R)-1,1,1-trifluoropropan-2-yl]oxy-1H-indazol-6-yl]-2-(4-cyclohexylpiperidin-1-yl)-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)O[C@@H](C(F)(F)F)C)C1=CC(=C(C(=O)NC)C=C1)N1CCC(CC1)C1CCCCC1 CVOJYADDGGNLSP-QGZVFWFLSA-N 0.000 claims 1
- BPFHPPYQSGUXTH-MRXNPFEDSA-N 4-[3-amino-4-[(2R)-1,1,1-trifluoropropan-2-yl]oxy-1H-indazol-6-yl]-2-(4-cyclopentylpiperazin-1-yl)-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)O[C@@H](C(F)(F)F)C)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)C1CCCC1 BPFHPPYQSGUXTH-MRXNPFEDSA-N 0.000 claims 1
- SLMVPLWHMMAGAI-QGZVFWFLSA-N 4-[3-amino-4-[(2R)-1,1,1-trifluoropropan-2-yl]oxy-1H-indazol-6-yl]-2-(4-hydroxy-4-phenylpiperidin-1-yl)-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)O[C@@H](C(F)(F)F)C)C1=CC(=C(C(=O)NC)C=C1)N1CCC(CC1)(C1=CC=CC=C1)O SLMVPLWHMMAGAI-QGZVFWFLSA-N 0.000 claims 1
- AFUXDBICISLFOZ-OAHLLOKOSA-N 4-[3-amino-4-[(2R)-1,1,1-trifluoropropan-2-yl]oxy-1H-indazol-6-yl]-2-[4-(2,2-dimethylpropanoyl)piperazin-1-yl]-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)O[C@@H](C(F)(F)F)C)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)C(C(C)(C)C)=O AFUXDBICISLFOZ-OAHLLOKOSA-N 0.000 claims 1
- DPQIPDOIQUZATG-QGZVFWFLSA-N 4-[3-amino-4-[(2R)-1,1,1-trifluoropropan-2-yl]oxy-1H-indazol-6-yl]-2-[4-(3,3-dimethylbutyl)piperazin-1-yl]-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)O[C@@H](C(F)(F)F)C)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)CCC(C)(C)C DPQIPDOIQUZATG-QGZVFWFLSA-N 0.000 claims 1
- AAAHKUPAUUYLSY-NNJIEVJOSA-N 4-[3-amino-4-[(2R)-1,1,1-trifluoropropan-2-yl]oxy-1H-indazol-6-yl]-N-methyl-2-[2-(2-methylpropyl)morpholin-4-yl]benzamide Chemical compound NC1=NNC2=CC(=CC(=C12)O[C@@H](C(F)(F)F)C)C1=CC(=C(C(=O)NC)C=C1)N1CC(OCC1)CC(C)C AAAHKUPAUUYLSY-NNJIEVJOSA-N 0.000 claims 1
- SRXOFBPYMAEIJT-HNNXBMFYSA-N 4-[3-amino-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxy-1H-indazol-6-yl]-2-(4-cyclobutylpiperazin-1-yl)-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)O[C@H](C(F)(F)F)C)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)C1CCC1 SRXOFBPYMAEIJT-HNNXBMFYSA-N 0.000 claims 1
- MGUKGLFLLCYSDU-KRWDZBQOSA-N 4-[3-amino-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxy-1H-indazol-6-yl]-2-(4-cyclohexylpiperazin-1-yl)-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)O[C@H](C(F)(F)F)C)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)C1CCCCC1 MGUKGLFLLCYSDU-KRWDZBQOSA-N 0.000 claims 1
- BPFHPPYQSGUXTH-INIZCTEOSA-N 4-[3-amino-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxy-1H-indazol-6-yl]-2-(4-cyclopentylpiperazin-1-yl)-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)O[C@H](C(F)(F)F)C)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)C1CCCC1 BPFHPPYQSGUXTH-INIZCTEOSA-N 0.000 claims 1
- AFUXDBICISLFOZ-HNNXBMFYSA-N 4-[3-amino-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxy-1H-indazol-6-yl]-2-[4-(2,2-dimethylpropanoyl)piperazin-1-yl]-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)O[C@H](C(F)(F)F)C)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)C(C(C)(C)C)=O AFUXDBICISLFOZ-HNNXBMFYSA-N 0.000 claims 1
- DPQIPDOIQUZATG-KRWDZBQOSA-N 4-[3-amino-4-[(2S)-1,1,1-trifluoropropan-2-yl]oxy-1H-indazol-6-yl]-2-[4-(3,3-dimethylbutyl)piperazin-1-yl]-N-methylbenzamide Chemical compound NC1=NNC2=CC(=CC(=C12)O[C@H](C(F)(F)F)C)C1=CC(=C(C(=O)NC)C=C1)N1CCN(CC1)CCC(C)(C)C DPQIPDOIQUZATG-KRWDZBQOSA-N 0.000 claims 1
- JILUYFWGVQRKQK-UHFFFAOYSA-N 4-[3-methyl-4-(oxan-4-yloxy)-2H-indazol-6-yl]-2-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]benzonitrile Chemical compound CC1=NNC2=CC(=CC(=C12)OC1CCOCC1)C1=CC(=C(C#N)C=C1)N1CCN(CC1)CC(F)(F)F JILUYFWGVQRKQK-UHFFFAOYSA-N 0.000 claims 1
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| US201461931137P | 2014-01-24 | 2014-01-24 | |
| US61/931,137 | 2014-01-24 | ||
| PCT/US2015/011760 WO2015112445A1 (en) | 2014-01-24 | 2015-01-16 | 6-phenyl- or 6-(pyridin-3-yl)indazole derivatives and methods of use |
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| EP3233840B1 (en) | 2014-12-16 | 2018-11-21 | Eudendron S.r.l. | Heterocyclic derivatives modulating activity of certain protein kinases |
| CN111032646B (zh) | 2017-08-01 | 2023-01-03 | 施万生物制药研发Ip有限责任公司 | 作为jak激酶抑制剂的吡唑并和三唑并双环化合物 |
| JP7192104B2 (ja) | 2018-05-16 | 2022-12-19 | スウォープ マンデー，ジョージ | 縫合装置 |
| US11969472B2 (en) | 2018-08-22 | 2024-04-30 | Cullgen (Shanghai), Inc. | Tropomyosin receptor kinase (TRK) degradation compounds and methods of use |
| MX2021001957A (es) * | 2018-08-22 | 2021-07-15 | Cullgen Shanghai Inc | Compuestos de degradacion y metodos de uso del receptor de tropomiosina quinasa (trk). |
| CN113498352A (zh) | 2019-01-23 | 2021-10-12 | 施万生物制药研发Ip有限责任公司 | 作为jak抑制剂的咪唑并[1,5-a]吡啶、1,2,4-三唑并[4,3-a]吡啶和咪唑并[1,5-a]吡嗪 |
| BR112022016901A2 (pt) | 2020-02-26 | 2022-12-06 | Cullgen Shanghai Inc | Compostos de degradação do receptor de tropomiosina quinase (trk) e métodos de uso |
| US12471911B2 (en) | 2022-01-10 | 2025-11-18 | George Swope Munday | Apparatus for closing a surgical site |
| US11701104B2 (en) | 2021-06-08 | 2023-07-18 | George Swope MUNDAY | Apparatus for closing a surgical site |
| US20220387023A1 (en) | 2021-06-08 | 2022-12-08 | George Swope MUNDAY | Apparatus for closing a surgical site |
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| AU2002353186A1 (en) * | 2001-12-19 | 2003-06-30 | Smithkline Beecham P.L.C. | (1-h-indazol-3-yl) -amide derivatives as gsk-3 inhibitors |
| FR2836915B1 (fr) * | 2002-03-11 | 2008-01-11 | Aventis Pharma Sa | Derives d'aminoindazoles, procede de preparation et intermediaires de ce procede a titre de medicaments et compositions pharmaceutiques les renfermant |
| WO2003097610A1 (en) * | 2002-05-17 | 2003-11-27 | Pharmacia Italia S.P.A. | Aminoindazole derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| DE102004028862A1 (de) * | 2004-06-15 | 2005-12-29 | Merck Patent Gmbh | 3-Aminoindazole |
| EP2280946B1 (en) * | 2008-06-05 | 2016-02-10 | Glaxo Group Limited | 4-carboxamide indazole derivatives useful as inhibitors of p13-kinases |
| RS53830B1 (sr) * | 2009-04-30 | 2015-06-30 | Glaxo Group Limited | Indazoli supstituisani oksazolom kao inhibitori pi3-kinaze |
| WO2013176970A1 (en) * | 2012-05-22 | 2013-11-28 | Merck Sharp & Dohme Corp. | TrkA KINASE INHIBITORS, COMPOSITIONS AND METHODS THEREOF |
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