JP2019520415A5 - - Google Patents
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- Publication number
- JP2019520415A5 JP2019520415A5 JP2019500810A JP2019500810A JP2019520415A5 JP 2019520415 A5 JP2019520415 A5 JP 2019520415A5 JP 2019500810 A JP2019500810 A JP 2019500810A JP 2019500810 A JP2019500810 A JP 2019500810A JP 2019520415 A5 JP2019520415 A5 JP 2019520415A5
- Authority
- JP
- Japan
- Prior art keywords
- quinoline
- difluorophenyl
- fluoro
- aminopiperidin
- methylphenyl
- 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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- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 183
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 163
- 229910052739 hydrogen Inorganic materials 0.000 claims description 94
- 239000001257 hydrogen Substances 0.000 claims description 94
- 150000002431 hydrogen Chemical class 0.000 claims description 89
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 71
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
- 229910052731 fluorine Inorganic materials 0.000 claims description 49
- 229910052801 chlorine Inorganic materials 0.000 claims description 48
- 229910052794 bromium Inorganic materials 0.000 claims description 35
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 24
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- CUYKNJBYIJFRCU-UHFFFAOYSA-N pyridine-3-amine Natural products NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
- CGWOEOXQHIMZEQ-UHFFFAOYSA-N 3-[1-[[4-(2-phenylquinolin-3-yl)phenyl]methyl]piperidin-4-yl]-1h-benzimidazol-2-one Chemical compound OC1=NC2=CC=CC=C2N1C(CC1)CCN1CC(C=C1)=CC=C1C1=CC2=CC=CC=C2N=C1C1=CC=CC=C1 CGWOEOXQHIMZEQ-UHFFFAOYSA-N 0.000 claims description 10
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- 125000002393 azetidinyl group Chemical group 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000003386 piperidinyl group Chemical group 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
- 150000003857 carboxamides Chemical class 0.000 claims description 4
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- XNOGDVQTUUVEKD-DNQXCXABSA-N (3R,4R)-4-amino-1-[6-(3-cyano-2-hydroxyphenyl)-3-(3,5-difluorophenyl)quinolin-4-yl]piperidine-3-carboxylic acid Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC=C1)C#N)O)C1=CC(=CC(=C1)F)F)C(=O)O XNOGDVQTUUVEKD-DNQXCXABSA-N 0.000 claims description 2
- IOLPVDHOVAVWTN-UHFFFAOYSA-N 1-[2-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-4,6-difluorophenyl]-3-methoxyurea Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(C(=CC(=C1)F)F)NC(=O)NOC)C1=CC(=CC(=C1)F)F IOLPVDHOVAVWTN-UHFFFAOYSA-N 0.000 claims description 2
- REMZNDYFYZWVDV-UHFFFAOYSA-N 1-[3-(3,5-difluorophenyl)-6-[5-fluoro-4-(oxetan-3-yloxy)pyridin-3-yl]quinolin-4-yl]piperidin-4-amine Chemical compound FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C=1C=NC=C(C=1OC1COC1)F REMZNDYFYZWVDV-UHFFFAOYSA-N 0.000 claims description 2
- WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims description 2
- LWTIGYSPAXKMDG-UHFFFAOYSA-N 2,3-dihydro-1h-imidazole Chemical compound C1NC=CN1 LWTIGYSPAXKMDG-UHFFFAOYSA-N 0.000 claims description 2
- CAXDTJAYDWXHLK-UHFFFAOYSA-N 2-(methoxyiminomethyl)pyridin-4-amine Chemical compound CON=CC1=NC=CC(=C1)N CAXDTJAYDWXHLK-UHFFFAOYSA-N 0.000 claims description 2
- UZODABKGIQHGPB-UHFFFAOYSA-N 2-[2-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-6-cyanophenoxy]acetic acid Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C1=C(OCC(=O)O)C(=CC=C1)C#N)C1=CC(=CC(=C1)F)F UZODABKGIQHGPB-UHFFFAOYSA-N 0.000 claims description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 2
- POBRHBKAXUQOGD-UHFFFAOYSA-N 2-cyclopropylpyridin-4-amine Chemical compound NC1=CC=NC(C2CC2)=C1 POBRHBKAXUQOGD-UHFFFAOYSA-N 0.000 claims description 2
- BJQZVISGHDIVCW-UHFFFAOYSA-N 3-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-2-(2-hydroxyethoxy)benzonitrile Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OCCO)C1=CC(=CC(=C1)F)F BJQZVISGHDIVCW-UHFFFAOYSA-N 0.000 claims description 2
- TVSPGTRFDXDRHW-UHFFFAOYSA-N 3-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-2-(2-methoxyethoxymethoxy)benzonitrile Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OCOCCOC)C1=CC(=CC(=C1)F)F TVSPGTRFDXDRHW-UHFFFAOYSA-N 0.000 claims description 2
- ULUQRQOMEBQOIC-UHFFFAOYSA-N 3-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-2-(methoxymethoxy)benzonitrile Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OCOC)C1=CC(=CC(=C1)F)F ULUQRQOMEBQOIC-UHFFFAOYSA-N 0.000 claims description 2
- GHILNKWBALQPDP-UHFFFAOYSA-N 3-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-2-hydroxybenzonitrile Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F GHILNKWBALQPDP-UHFFFAOYSA-N 0.000 claims description 2
- MCEDWFWPINMPTJ-UHFFFAOYSA-N 3-[4-(4-aminopiperidin-1-yl)-3-(3,5-difluorophenyl)quinolin-6-yl]-5-chloro-4-fluoro-2-hydroxybenzonitrile Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=C(C=1F)Cl)O)C1=CC(=CC(=C1)F)F MCEDWFWPINMPTJ-UHFFFAOYSA-N 0.000 claims description 2
- BIEAVTSOLIAZKF-UHFFFAOYSA-N 3-[4-(4-aminopiperidin-1-yl)-3-[3-fluoro-5-(oxetan-3-yloxy)phenyl]quinolin-6-yl]-2-hydroxybenzonitrile Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)OC1COC1)F BIEAVTSOLIAZKF-UHFFFAOYSA-N 0.000 claims description 2
- BDMILXDVJXNJCW-AABVJFSESA-N 3-[4-(4-aminopiperidin-1-yl)-3-[3-fluoro-5-[(E)-methoxyiminomethyl]phenyl]quinolin-6-yl]-2-hydroxybenzonitrile Chemical compound NC1CCN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)/C=N/OC)F BDMILXDVJXNJCW-AABVJFSESA-N 0.000 claims description 2
- HWLUDPGRVTYPHZ-DNQXCXABSA-N 3-[4-[(3R,4R)-4-amino-3-fluoropiperidin-1-yl]-3-(3,5-difluorophenyl)quinolin-6-yl]-2-hydroxybenzonitrile Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)O)C1=CC(=CC(=C1)F)F)F HWLUDPGRVTYPHZ-DNQXCXABSA-N 0.000 claims description 2
- YZICXZWMZPMDCN-IXCJQBJRSA-N 3-[4-[(3R,4R)-4-amino-3-methoxypiperidin-1-yl]-3-(3,5-difluorophenyl)quinolin-6-yl]-2-(methoxymethoxy)benzonitrile Chemical compound N[C@H]1[C@@H](CN(CC1)C1=C(C=NC2=CC=C(C=C12)C=1C(=C(C#N)C=CC=1)OCOC)C1=CC(=CC(=C1)F)F)OC YZICXZWMZPMDCN-IXCJQBJRSA-N 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- JVSLFJAHSXCAAZ-UHFFFAOYSA-N ClC=1C(=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N)C=NO Chemical compound ClC=1C(=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N)C=NO JVSLFJAHSXCAAZ-UHFFFAOYSA-N 0.000 claims description 2
- CVWAYYSYVJGJQN-UHFFFAOYSA-N ClC=1C(=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N)C=NOC Chemical compound ClC=1C(=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N)C=NOC CVWAYYSYVJGJQN-UHFFFAOYSA-N 0.000 claims description 2
- MIZXKKWBPVKUEJ-UHFFFAOYSA-N ClC=1C(=C(C=NC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N)C=NO Chemical compound ClC=1C(=C(C=NC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)F)F)N1CCC(CC1)N)C=NO MIZXKKWBPVKUEJ-UHFFFAOYSA-N 0.000 claims description 2
- KPHYYFOYKPKVHA-IXCJQBJRSA-N FC=1C(=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1C[C@H]([C@@H](CC1)N)OC)C=NO Chemical compound FC=1C(=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1C[C@H]([C@@H](CC1)N)OC)C=NO KPHYYFOYKPKVHA-IXCJQBJRSA-N 0.000 claims description 2
- MFXJWJYASCWNOL-UHFFFAOYSA-N FC=1C(=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)OC)F)N1CCC(CC1)N)C=NO Chemical compound FC=1C(=C(C=CC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)OC)F)N1CCC(CC1)N)C=NO MFXJWJYASCWNOL-UHFFFAOYSA-N 0.000 claims description 2
- HZGJPRHVRRPXNX-UHFFFAOYSA-N FC=1C(=C(C=NC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CCC(CC1)N)C=NO Chemical compound FC=1C(=C(C=NC=1)C=1C=C2C(=C(C=NC2=CC=1)C1=CC(=CC(=C1)C)F)N1CCC(CC1)N)C=NO HZGJPRHVRRPXNX-UHFFFAOYSA-N 0.000 claims description 2
- FGDFFXABWRUDRT-UHFFFAOYSA-N FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C1=C(C(=CC=C1)F)C=NO Chemical compound FC=1C=C(C=C(C=1)F)C=1C=NC2=CC=C(C=C2C=1N1CCC(CC1)N)C1=C(C(=CC=C1)F)C=NO FGDFFXABWRUDRT-UHFFFAOYSA-N 0.000 claims description 2
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- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 2
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| RS63776B1 (sr) * | 2016-07-14 | 2022-12-30 | Crinetics Pharmaceuticals Inc | Modulatori somatostatina i njihove upotrebe |
| KR20190121404A (ko) * | 2017-03-16 | 2019-10-25 | 크리네틱스 파마슈티칼스, 인크. | 소마토스타틴 조절제 및 이의 용도 |
| US11028068B2 (en) | 2017-07-25 | 2021-06-08 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| RS63387B1 (sr) * | 2018-01-17 | 2022-08-31 | Crinetics Pharmaceuticals Inc | Postupak proizvodnje modulatora somatostatina |
| JP7365347B2 (ja) * | 2018-02-12 | 2023-10-19 | クリネティックス ファーマシューティカルズ，インク． | ソマトスタチンモジュレーターおよびその使用 |
| EP3807248A4 (en) * | 2018-05-29 | 2021-10-27 | Council of Scientific and Industrial Research | BICYCLIC TOPOISOMERASE I INHIBITOR COMPOUNDS, THEIR PREPARATION AND USE |
| US10696689B2 (en) | 2018-09-18 | 2020-06-30 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| EP3999509A4 (en) | 2019-07-17 | 2023-07-19 | Crinetics Pharmaceuticals, Inc. | Crystalline forms of somatostatin modulators |
| TWI841768B (zh) | 2019-08-14 | 2024-05-11 | 美商克林提克斯醫藥股份有限公司 | 非肽生長抑制素(somatostatin)5型受體激動劑及其用途 |
| MA66139B1 (fr) * | 2020-09-09 | 2025-09-30 | Crinetics Pharmaceuticals, Inc. | Formulations d'un modulateur de somatostatine |
| US11773076B2 (en) | 2021-02-17 | 2023-10-03 | Crinetics Pharmaceuticals, Inc. | Crystalline forms of a somatostatin modulator |
| WO2022251212A2 (en) * | 2021-05-25 | 2022-12-01 | Crinetics Pharmaceuticals, Inc. | Uses of a somatostatin modulator for the treatment of disease |
| JP7784437B2 (ja) | 2021-09-28 | 2025-12-11 | デンカ株式会社 | クロロプレン系ブロック共重合体、ラテックス、ラテックス組成物、及びゴム組成物 |
| MX2024008598A (es) * | 2022-01-11 | 2024-07-23 | Crinetics Pharmaceuticals Inc | Usos de un modulador de somatostatina para el tratamiento del sindrome carcinoide. |
| WO2023238112A1 (en) | 2022-06-10 | 2023-12-14 | Assia Chemical Industries Ltd. | Solid state forms of paltusotine and process for preparation thereof |
| CR20250214A (es) * | 2022-10-28 | 2025-08-22 | Basecamp Bio Inc | Agonistas del receptor 2 de somatostatina y sus usos |
| WO2024129614A1 (en) | 2022-12-13 | 2024-06-20 | Crinetics Pharmaceuticals, Inc. | Somatostatin subtype-2 receptor (sst2r) targeted therapeutics and uses thereof |
| US12208092B2 (en) | 2023-03-28 | 2025-01-28 | Crinetics Pharmaceuticals, Inc. | Compositions and methods for administering paltusotine to patients with hepatic impairment |
| WO2025111318A1 (en) * | 2023-11-22 | 2025-05-30 | Crinetics Pharmaceuticals, Inc. | Somatostatin subtype receptor 3 (sstr3) agonists and uses thereof |
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| FR2802206B1 (fr) | 1999-12-14 | 2005-04-22 | Sod Conseils Rech Applic | Derives de 4-aminopiperidine et leur utilisation en tant que medicament |
| AU2002352868A1 (en) | 2001-11-27 | 2003-06-10 | Merck & Co., Inc. | 4-aminoquinoline compounds |
| KR100659428B1 (ko) | 2002-02-04 | 2006-12-19 | 에프. 호프만-라 로슈 아게 | Ｎｐｙ 길항제로서의 퀴놀린 유도체 |
| US7767817B2 (en) | 2003-09-05 | 2010-08-03 | Binghe Wang | Water soluble boronic acid fluorescent reporter compounds and methods of use thereof |
| WO2006017326A1 (en) * | 2004-07-13 | 2006-02-16 | Glaxo Group Limited | Antibacterial agents |
| US20060183763A1 (en) | 2004-12-31 | 2006-08-17 | Pfizer Inc | Novel pyrrolidyl derivatives of heteroaromatic compounds |
| US7563821B2 (en) | 2005-12-05 | 2009-07-21 | Xenoport, Inc. | Levodopa prodrug mesylate, compositions thereof, and uses thereof |
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| EP2726465A1 (en) | 2011-05-23 | 2014-05-07 | Elan Pharmaceuticals Inc. | Inhibitors of lrrk2 kinase activity |
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| JO3805B1 (ar) | 2013-10-10 | 2021-01-31 | Araxes Pharma Llc | مثبطات كراس جي12سي |
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| US10011600B2 (en) | 2014-09-25 | 2018-07-03 | Araxes Pharma Llc | Methods and compositions for inhibition of Ras |
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| MX2019000246A (es) | 2016-07-07 | 2019-05-27 | Plantex Ltd | Formas en estado solido del dimesilato de palbociclib. |
| RS63776B1 (sr) * | 2016-07-14 | 2022-12-30 | Crinetics Pharmaceuticals Inc | Modulatori somatostatina i njihove upotrebe |
| RS63387B1 (sr) | 2018-01-17 | 2022-08-31 | Crinetics Pharmaceuticals Inc | Postupak proizvodnje modulatora somatostatina |
| US10696689B2 (en) | 2018-09-18 | 2020-06-30 | Crinetics Pharmaceuticals, Inc. | Somatostatin modulators and uses thereof |
| EP3999509A4 (en) | 2019-07-17 | 2023-07-19 | Crinetics Pharmaceuticals, Inc. | Crystalline forms of somatostatin modulators |
| MA66139B1 (fr) | 2020-09-09 | 2025-09-30 | Crinetics Pharmaceuticals, Inc. | Formulations d'un modulateur de somatostatine |
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