JP2014514360A5 - - Google Patents
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- JP2014514360A5 JP2014514360A5 JP2014510416A JP2014510416A JP2014514360A5 JP 2014514360 A5 JP2014514360 A5 JP 2014514360A5 JP 2014510416 A JP2014510416 A JP 2014510416A JP 2014510416 A JP2014510416 A JP 2014510416A JP 2014514360 A5 JP2014514360 A5 JP 2014514360A5
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- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- independently selected
- optionally substituted
- compound
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims description 488
- 125000003545 alkoxy group Chemical group 0.000 claims description 237
- 150000001875 compounds Chemical class 0.000 claims description 131
- 229910052736 halogen Inorganic materials 0.000 claims description 75
- 150000002367 halogens Chemical class 0.000 claims description 72
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 61
- 150000003839 salts Chemical class 0.000 claims description 50
- 239000011780 sodium chloride Substances 0.000 claims description 50
- 125000005842 heteroatoms Chemical group 0.000 claims description 42
- 229910052760 oxygen Inorganic materials 0.000 claims description 41
- 229910052717 sulfur Inorganic materials 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- -1 hydroxycarbonyl Chemical group 0.000 claims description 36
- 239000012453 solvate Substances 0.000 claims description 34
- 239000000651 prodrug Substances 0.000 claims description 33
- 229940002612 prodrugs Drugs 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 32
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 30
- 230000000875 corresponding Effects 0.000 claims description 30
- PQIOSYKVBBWRRI-UHFFFAOYSA-N Methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 208000002193 Pain Diseases 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 125000004429 atoms Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 12
- 230000001808 coupling Effects 0.000 claims description 11
- 238000010168 coupling process Methods 0.000 claims description 11
- 238000005859 coupling reaction Methods 0.000 claims description 11
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000004433 nitrogen atoms Chemical group N* 0.000 claims description 9
- 201000011510 cancer Diseases 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 206010001935 American trypanosomiasis Diseases 0.000 claims description 7
- 201000003884 Chagas disease Diseases 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 7
- 206010053643 Neurodegenerative disease Diseases 0.000 claims description 7
- 230000004054 inflammatory process Effects 0.000 claims description 7
- 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 7
- NVBFHJWHLNUMCV-UHFFFAOYSA-N Sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 6
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N Carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 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
- 125000004422 alkyl sulphonamide group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 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
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 14
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 238000006467 substitution reaction Methods 0.000 claims 3
- 208000005298 Acute Pain Diseases 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 206010065390 Inflammatory pain Diseases 0.000 claims 1
- 208000004296 Neuralgia Diseases 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 239000002585 base Substances 0.000 description 8
- NTOIKDYVJIWVSU-WOJBJXKFSA-L (2R,3R)-2,3-dihydroxy-2,3-bis(4-methylbenzoyl)butanedioate Chemical compound C1=CC(C)=CC=C1C(=O)[C@@](O)(C([O-])=O)[C@](O)(C([O-])=O)C(=O)C1=CC=C(C)C=C1 NTOIKDYVJIWVSU-WOJBJXKFSA-L 0.000 description 4
- CMIBUZBMZCBCAT-HOTGVXAUSA-N (2S,3S)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)O[C@H](C(O)=O)[C@@H](C(O)=O)OC(=O)C1=CC=C(C)C=C1 CMIBUZBMZCBCAT-HOTGVXAUSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161485858P | 2011-05-13 | 2011-05-13 | |
| US61/485,858 | 2011-05-13 | ||
| PCT/US2012/037003 WO2012158413A2 (en) | 2011-05-13 | 2012-05-09 | Pyrrolidinyl urea and pyrrolidinyl thiourea compounds as trka kinase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016026184A Division JP6382867B2 (ja) | 2011-05-13 | 2016-02-15 | Ｔｒｋａキナーゼ阻害剤としてのピロリジニル尿素およびピロリジニルチオ尿素化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014514360A JP2014514360A (ja) | 2014-06-19 |
| JP2014514360A5 true JP2014514360A5 (US07794700-20100914-C00125.png) | 2015-05-21 |
| JP5933902B2 JP5933902B2 (ja) | 2016-06-15 |
Family
ID=46614580
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014510416A Active JP5933902B2 (ja) | 2011-05-13 | 2012-05-09 | Ｔｒｋａキナーゼ阻害剤としてのピロリジニル尿素およびピロリジニルチオ尿素化合物 |
| JP2016026184A Active JP6382867B2 (ja) | 2011-05-13 | 2016-02-15 | Ｔｒｋａキナーゼ阻害剤としてのピロリジニル尿素およびピロリジニルチオ尿素化合物 |
| JP2017090432A Withdrawn JP2017171672A (ja) | 2011-05-13 | 2017-04-28 | Ｔｒｋａキナーゼ阻害剤としてのピロリジニル尿素およびピロリジニルチオ尿素化合物 |
| JP2018172485A Pending JP2019001819A (ja) | 2011-05-13 | 2018-09-14 | Ｔｒｋａキナーゼ阻害剤としてのピロリジニル尿素およびピロリジニルチオ尿素化合物 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016026184A Active JP6382867B2 (ja) | 2011-05-13 | 2016-02-15 | Ｔｒｋａキナーゼ阻害剤としてのピロリジニル尿素およびピロリジニルチオ尿素化合物 |
| JP2017090432A Withdrawn JP2017171672A (ja) | 2011-05-13 | 2017-04-28 | Ｔｒｋａキナーゼ阻害剤としてのピロリジニル尿素およびピロリジニルチオ尿素化合物 |
| JP2018172485A Pending JP2019001819A (ja) | 2011-05-13 | 2018-09-14 | Ｔｒｋａキナーゼ阻害剤としてのピロリジニル尿素およびピロリジニルチオ尿素化合物 |
Country Status (34)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7439124B2 (ja) | 2019-11-14 | 2024-02-27 | ユニマテック株式会社 | 含フッ素ピラゾール化合物およびその製造方法 |
Families Citing this family (92)
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|---|---|---|---|---|
| EP2116539A1 (en) | 2008-04-25 | 2009-11-11 | Laboratorios Del. Dr. Esteve, S.A. | 1-aryl-3-aminoalkoxy-pyrazoles as sigma ligands enhancing analgesic effects of opioids and attenuating the dependency thereof |
| ES2464461T3 (es) | 2008-09-22 | 2014-06-02 | Array Biopharma, Inc. | Compuestos de imidazo[1,2B]piridazina sustituidos como inhibidores de la TRK cinasa |
| PL3372605T3 (pl) | 2008-10-22 | 2022-03-07 | Array Biopharma Inc. | Podstawione związki pirazolo[1,5-a]pirymidynowe jako inhibitory kinaz trk |
| AR077468A1 (es) | 2009-07-09 | 2011-08-31 | Array Biopharma Inc | Compuestos de pirazolo (1,5 -a) pirimidina sustituidos como inhibidores de trk- quinasa |
| EP2353598A1 (en) | 2010-02-04 | 2011-08-10 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for use in the prevention and/or treatment of postoperative pain |
| EP2353591A1 (en) | 2010-02-04 | 2011-08-10 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for potentiating the analgesic effect of opioids and opiates in post-operative pain and attenuating the dependency thereof |
| SG10201506591TA (en) | 2010-05-20 | 2015-09-29 | Array Biopharma Inc | Macrocyclic compounds as trk kinase inhibitors |
| EP2388005A1 (en) | 2010-05-21 | 2011-11-23 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for the prevention and/or treatment of emesis induced by chemotherapy or radiotherapy |
| EP2415471A1 (en) | 2010-08-03 | 2012-02-08 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in opioid-induced hyperalgesia |
| BR112013029201B1 (pt) | 2011-05-13 | 2022-08-09 | Array Biopharma Inc | Compostos de pirrolidinil ureia e pirrolidinil tioureia, seu processo de preparação, seu uso e composições farmacêuticas |
| EP2524694A1 (en) | 2011-05-19 | 2012-11-21 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in diabetes type-2 associated pain |
| WO2014078417A1 (en) * | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | Pyrazolyl urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
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| WO2014078325A1 (en) * | 2012-11-13 | 2014-05-22 | Array Biopharma Inc. | N-(monocyclic aryl),n'-pyrazolyl-urea, thiourea, guanidine and cyanoguanidine compounds as trka kinase inhibitors |
| CN104903310B (zh) | 2012-11-13 | 2018-08-14 | 阵列生物制药公司 | 可用于治疗疼痛的双环脲、硫脲、胍及氰基胍化合物 |
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| MY191956A (en) * | 2014-05-15 | 2022-07-20 | 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 |
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| JP6618120B2 (ja) * | 2014-08-06 | 2019-12-11 | 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 |
| FI3699181T3 (fi) | 2014-11-16 | 2023-03-28 | Array Biopharma Inc | Kiteinen muoto (s)-n-(5-((r)-2-(2,5-diluorifenyyli)-pyrrolidin-1-yyli)-pyratsolo[1,5-a]pyrimidin-3-yyli)-3-hydroksipyrrolidiini-1-karboksamidivetyysulfaatista |
| EP3230264B1 (en) | 2014-12-08 | 2019-09-11 | FMC Corporation | 3-oxo-3-(arylamino)propanoates, a process for their preparation, and their use in preparing pyrrolidinones |
| WO2016161572A1 (en) | 2015-04-08 | 2016-10-13 | Merck Sharp & Dohme Corp. | TrkA KINASE INHIBITORS, COMPOSITIONS AND METHODS THEREOF |
| CN107849049B (zh) * | 2015-05-27 | 2021-03-16 | 杏林制药株式会社 | 脲衍生物或其药用盐 |
| MA41667A1 (fr) | 2015-06-01 | 2018-08-31 | Loxo Oncology Inc | Procede de diagnostic et de traitement du cancer |
| WO2017006953A1 (ja) * | 2015-07-07 | 2017-01-12 | 塩野義製薬株式会社 | ＴｒｋＡ阻害活性を有する複素環誘導体 |
| EA035049B1 (ru) | 2015-07-16 | 2020-04-22 | Аррэй Байофарма Инк. | СОЕДИНЕНИЯ ЗАМЕЩЕННОГО ПИРАЗОЛО[1,5-a]ПИРИДИНА В КАЧЕСТВЕ ИНГИБИТОРОВ RET КИНАЗЫ |
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| 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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| JP2019026646A (ja) * | 2017-08-03 | 2019-02-21 | 塩野義製薬株式会社 | 含窒素複素環および炭素環誘導体を含有する、疼痛の治療および／または予防用医薬組成物 |
| 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 |
| TW202410896A (zh) | 2017-10-10 | 2024-03-16 | 美商絡速藥業公司 | 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-甲腈之調配物 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7439124B2 (ja) | 2019-11-14 | 2024-02-27 | ユニマテック株式会社 | 含フッ素ピラゾール化合物およびその製造方法 |
