JP2015537001A5 - - Google Patents
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- JP2015537001A5 JP2015537001A5 JP2015542038A JP2015542038A JP2015537001A5 JP 2015537001 A5 JP2015537001 A5 JP 2015537001A5 JP 2015542038 A JP2015542038 A JP 2015542038A JP 2015542038 A JP2015542038 A JP 2015542038A JP 2015537001 A5 JP2015537001 A5 JP 2015537001A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- optionally substituted
- pharmaceutically acceptable
- acceptable salt
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims description 299
- 125000003545 alkoxy group Chemical group 0.000 claims description 203
- 150000001875 compounds Chemical class 0.000 claims description 107
- 125000001153 fluoro group Chemical group F* 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 46
- 229910052736 halogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
- 125000005842 heteroatom Chemical group 0.000 claims description 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 39
- 239000012453 solvate Substances 0.000 claims description 34
- 125000004429 atom Chemical group 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- -1 hydroxyl-carbonyl Chemical group 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 208000002193 Pain Diseases 0.000 claims description 17
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 14
- 230000008878 coupling Effects 0.000 claims description 13
- 238000010168 coupling process Methods 0.000 claims description 13
- 238000005859 coupling reaction Methods 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 11
- 201000011510 cancer Diseases 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 125000004043 oxo group Chemical group O=* 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 6
- 201000009273 Endometriosis Diseases 0.000 claims description 6
- 208000000450 Pelvic Pain Diseases 0.000 claims description 6
- 208000021386 Sjogren Syndrome Diseases 0.000 claims description 6
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 6
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 6
- 125000002393 azetidinyl group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 6
- 208000027866 inflammatory disease Diseases 0.000 claims description 6
- 230000004770 neurodegeneration Effects 0.000 claims description 6
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000003566 oxetanyl group Chemical group 0.000 claims description 6
- 201000007094 prostatitis Diseases 0.000 claims description 6
- 208000011580 syndromic disease Diseases 0.000 claims description 6
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000004694 alkoxyaminocarbonyl group Chemical group 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 2
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- 208000035473 Communicable disease Diseases 0.000 claims description 2
- 201000010915 Glioblastoma multiforme Diseases 0.000 claims description 2
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 2
- 101150111783 NTRK1 gene Proteins 0.000 claims description 2
- 206010029260 Neuroblastoma Diseases 0.000 claims description 2
- 206010033701 Papillary thyroid cancer Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 230000004913 activation Effects 0.000 claims description 2
- SIISYXWWQBUDOP-UHFFFAOYSA-N bis(1h-imidazol-2-yl)methanethione Chemical compound N=1C=CNC=1C(=S)C1=NC=CN1 SIISYXWWQBUDOP-UHFFFAOYSA-N 0.000 claims description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
- 201000010989 colorectal carcinoma Diseases 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 230000008482 dysregulation Effects 0.000 claims description 2
- 208000021045 exocrine pancreatic carcinoma Diseases 0.000 claims description 2
- 206010017758 gastric cancer Diseases 0.000 claims description 2
- 208000010749 gastric carcinoma Diseases 0.000 claims description 2
- 208000005017 glioblastoma Diseases 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 201000002120 neuroendocrine carcinoma Diseases 0.000 claims description 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 206010041823 squamous cell carcinoma Diseases 0.000 claims description 2
- 201000000498 stomach carcinoma Diseases 0.000 claims description 2
- 208000030045 thyroid gland papillary carcinoma Diseases 0.000 claims description 2
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 15
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 125000004422 alkyl sulphonamide group Chemical group 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000004950 trifluoroalkyl group Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261725925P | 2012-11-13 | 2012-11-13 | |
| US61/725,925 | 2012-11-13 | ||
| PCT/US2013/069951 WO2014078454A1 (en) | 2012-11-13 | 2013-11-13 | Bicyclic urea, thiourea, guanidine and cyanoguanidine compounds useful for the treatment of pain |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017211949A Division JP2018016649A (ja) | 2012-11-13 | 2017-11-01 | 疼痛の治療に有用な二環式尿素、チオ尿素、グアニジン、およびシアノグアニジン化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015537001A JP2015537001A (ja) | 2015-12-24 |
| JP2015537001A5 true JP2015537001A5 (https=) | 2016-12-08 |
| JP6345684B2 JP6345684B2 (ja) | 2018-06-20 |
Family
ID=49667614
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015542038A Expired - Fee Related JP6345684B2 (ja) | 2012-11-13 | 2013-11-13 | 疼痛の治療に有用な二環式尿素、チオ尿素、グアニジン、およびシアノグアニジン化合物 |
| JP2017211949A Withdrawn JP2018016649A (ja) | 2012-11-13 | 2017-11-01 | 疼痛の治療に有用な二環式尿素、チオ尿素、グアニジン、およびシアノグアニジン化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017211949A Withdrawn JP2018016649A (ja) | 2012-11-13 | 2017-11-01 | 疼痛の治療に有用な二環式尿素、チオ尿素、グアニジン、およびシアノグアニジン化合物 |
Country Status (30)
| Country | Link |
|---|---|
| US (2) | US10351575B2 (https=) |
| EP (1) | EP2920166B1 (https=) |
| JP (2) | JP6345684B2 (https=) |
| KR (1) | KR102181913B1 (https=) |
| CN (1) | CN104903310B (https=) |
| AU (3) | AU2013344886B2 (https=) |
| BR (1) | BR112015011010B1 (https=) |
| CA (1) | CA2891334C (https=) |
| CL (1) | CL2015001282A1 (https=) |
| CR (1) | CR20150264A (https=) |
| CY (1) | CY1118468T1 (https=) |
| DK (1) | DK2920166T3 (https=) |
| ES (1) | ES2610975T3 (https=) |
| HR (1) | HRP20161613T1 (https=) |
| HU (1) | HUE031557T2 (https=) |
| IL (1) | IL238498A (https=) |
| LT (1) | LT2920166T (https=) |
| ME (1) | ME02879B (https=) |
| MX (1) | MX366761B (https=) |
| PH (1) | PH12015500938B1 (https=) |
| PL (1) | PL2920166T3 (https=) |
| PT (1) | PT2920166T (https=) |
| RS (1) | RS55593B1 (https=) |
| RU (1) | RU2664541C2 (https=) |
| SG (1) | SG11201503731SA (https=) |
| SI (1) | SI2920166T1 (https=) |
| SM (2) | SMT201700034T1 (https=) |
| UA (1) | UA117573C2 (https=) |
| WO (1) | WO2014078454A1 (https=) |
| ZA (1) | ZA201503580B (https=) |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2350075E (pt) | 2008-09-22 | 2014-06-09 | Array Biopharma Inc | Compostos imidazo[1,2b]piridazina substituídos como inibidores da trk cinase |
| AR074052A1 (es) | 2008-10-22 | 2010-12-22 | Array Biopharma Inc | Compuestos pirazolo{1,5-a}pirimidina sustituida como inhibidores de trk cinasa |
| AR077468A1 (es) | 2009-07-09 | 2011-08-31 | Array Biopharma Inc | Compuestos de pirazolo (1,5 -a) pirimidina sustituidos como inhibidores de trk- quinasa |
| NZ604708A (en) | 2010-05-20 | 2015-05-29 | Array Biopharma Inc | Macrocyclic compounds as trk kinase inhibitors |
| AU2012256237B2 (en) | 2011-05-13 | 2017-01-05 | Array Biopharma Inc. | Pyrrolidinyl urea and pyrrolidinyl thiourea compounds as TrkA kinase inhibitors |
| US9981959B2 (en) | 2012-11-13 | 2018-05-29 | Array Biopharma Inc. | Thiazolyl and oxazolyl urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| WO2014078378A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| WO2014078408A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Bicyclic heteroaryl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| HRP20161613T1 (hr) | 2012-11-13 | 2017-01-13 | Array Biopharma, Inc. | Tvari bicikličke ureje, tioureje, gvanidina i cijanogvanidina korisne za liječenje boli |
| US9969694B2 (en) | 2012-11-13 | 2018-05-15 | Array Biopharma Inc. | N-(arylalkyl)-N′-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
| WO2014078372A1 (en) | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| MY178262A (en) | 2012-11-13 | 2020-10-07 | Array Biopharma Inc | Pyrrolidinyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
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| US9790210B2 (en) | 2012-11-13 | 2017-10-17 | Array Biopharma Inc. | N-(monocyclic aryl),N'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as TrkA kinase inhibitors |
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| CA2949160C (en) | 2014-05-15 | 2023-03-21 | Array Biopharma Inc. | 1-((3s,4r)-4-(3-fluorophenyl)-1-(2-methoxyethyl)pyrrolidin-3-yl)-3-(4-methyl-3-(2-methylpyrimidin-5-yl)-1-phenyl-1h-pyrazol-5-yl)urea as a trka kinase inhibitor |
| WO2016021629A1 (ja) | 2014-08-06 | 2016-02-11 | 塩野義製薬株式会社 | ＴｒｋＡ阻害活性を有する複素環および炭素環誘導体 |
| HUE061448T2 (hu) | 2014-11-16 | 2023-07-28 | Array Biopharma Inc | (S)-N-(5-((R)-2-(2,5-difluorofenil)-pirrolidin-1-il)-pirazolo[1,5-A]pirimidin-3-il) -3-hidroxipirrolidin-1-karboxamid-hidrogénszulfát kristályos formája |
| JP6812059B2 (ja) | 2015-07-07 | 2021-01-13 | 塩野義製薬株式会社 | ＴｒｋＡ阻害活性を有する複素環誘導体 |
| BR112018000808A2 (pt) | 2015-07-16 | 2018-09-04 | Array Biopharma Inc | compostos de pirazolo[1,5-a]piridina substituída como inibidores de ret cinase |
| HUE048032T2 (hu) | 2015-10-15 | 2020-05-28 | Jiangsu Hengrui Medicine Co | Oxaspiro-származék, elõállítási eljárása és alkalmazásai gyógyszerekben |
| CN108697708A (zh) | 2015-10-26 | 2018-10-23 | 洛克索肿瘤学股份有限公司 | Trk抑制剂抗性癌症中的点突变以及与此相关的方法 |
| EP3412663B1 (en) | 2016-02-04 | 2022-09-07 | Shionogi & Co., Ltd. | Nitrogen-containing heterocycle and carbocycle derivatives having trka inhibitory activity |
| ES2987474T3 (es) | 2016-04-04 | 2024-11-15 | Loxo Oncology Inc | Formulaciones líquidas de (S)-N-(5-((R)-2-(2,5-difluorofenil)-pirrolidin-1-IL)-pirazolo[1,5-A]pirimidin-3-IL)-3-hidroxipirrolidina-1-carboxamida |
| US10045991B2 (en) | 2016-04-04 | 2018-08-14 | Loxo Oncology, Inc. | Methods of treating pediatric cancers |
| RS65988B1 (sr) | 2016-04-04 | 2024-10-31 | Loxo Oncology Inc | Postupak lečenja pedijatrijskih karcinoma |
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| UA125519C2 (uk) | 2016-07-29 | 2022-04-13 | Суновіон Фармасьютікалз Інк. | Сполуки і композиції і їх застосування |
| CA3032141A1 (en) | 2016-07-29 | 2018-02-01 | Vadim ALEXANDROV | Compounds and compositions and uses thereof |
| TWI752098B (zh) | 2016-10-10 | 2022-01-11 | 美商亞雷生物製藥股份有限公司 | 作為ret激酶抑制劑之經取代吡唑并[1,5-a]吡啶化合物 |
| TWI704148B (zh) | 2016-10-10 | 2020-09-11 | 美商亞雷生物製藥股份有限公司 | 作為ｒｅｔ激酶抑制劑之經取代吡唑并[1,5-a]吡啶化合物 |
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| KR102771305B1 (ko) | 2017-09-15 | 2025-02-24 | 모찌다 세이야쿠 가부시끼가이샤 | 테트라히드로나프틸우레아 유도체의 결정 |
| TWI791053B (zh) | 2017-10-10 | 2023-02-01 | 美商亞雷生物製藥股份有限公司 | 6-(2-羥基-2-甲基丙氧基)-4-(6-(6-((6-甲氧基吡啶-3-基)甲基)-3,6-二氮雜雙環[3.1.1]庚-3-基)吡啶-3-基)吡唑并[1,5-a]吡啶-3-甲腈之結晶形式及其醫藥組合物 |
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| EP3898615A1 (en) | 2018-12-19 | 2021-10-27 | Array Biopharma, Inc. | 7-((3,5-dimethoxyphenyl)amino)quinoxaline derivatives as fgfr inhibitors for treating cancer |
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