JP2019524702A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2019524702A5 JP2019524702A5 JP2019500301A JP2019500301A JP2019524702A5 JP 2019524702 A5 JP2019524702 A5 JP 2019524702A5 JP 2019500301 A JP2019500301 A JP 2019500301A JP 2019500301 A JP2019500301 A JP 2019500301A JP 2019524702 A5 JP2019524702 A5 JP 2019524702A5
- Authority
- JP
- Japan
- Prior art keywords
- hydrocarbyl
- compound according
- hydroxy
- nhc
- alkylamino
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- -1 cyano, acetoxy, nitro, amino Chemical group 0.000 claims 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 15
- 125000006657 (C1-C10) hydrocarbyl group Chemical group 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 9
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000002252 acyl group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 3
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims 3
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 3
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims 3
- 125000005518 carboxamido group Chemical group 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 2
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[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
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004175 fluorobenzyl group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- CQIUQKLZKFYVSE-UHFFFAOYSA-N 5-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)pentanoic acid;hydrochloride Chemical compound Cl.C1CCNC2=NC(CCCCC(=O)O)=CC=C21 CQIUQKLZKFYVSE-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- BMZFBGUUHVSOSB-UHFFFAOYSA-N methyl 4-amino-2-phenylbutanoate;hydrochloride Chemical compound Cl.COC(=O)C(CCN)C1=CC=CC=C1 BMZFBGUUHVSOSB-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662358330P | 2016-07-05 | 2016-07-05 | |
| US62/358,330 | 2016-07-05 | ||
| US201662374234P | 2016-08-12 | 2016-08-12 | |
| US62/374,234 | 2016-08-12 | ||
| PCT/US2017/040657 WO2018009501A1 (en) | 2016-07-05 | 2017-07-05 | Tetrahydronaphthyridinepentanamide integrin antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2019524702A JP2019524702A (ja) | 2019-09-05 |
| JP2019524702A5 true JP2019524702A5 (https=) | 2020-08-13 |
Family
ID=60912284
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019500301A Pending JP2019524702A (ja) | 2016-07-05 | 2017-07-05 | テトラヒドロナフチルリジンペンタンアミドインテグリンアンタゴニスト |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US11192889B2 (https=) |
| EP (1) | EP3481814B1 (https=) |
| JP (1) | JP2019524702A (https=) |
| KR (1) | KR20190026001A (https=) |
| CN (1) | CN109476632A (https=) |
| AU (1) | AU2017292754B2 (https=) |
| CA (1) | CA3029829A1 (https=) |
| MX (1) | MX2019000043A (https=) |
| WO (1) | WO2018009501A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3509590A4 (en) | 2016-09-07 | 2020-12-02 | Pliant Therapeutics, Inc. | N-ACYL AMINO ACID COMPOUNDS AND METHODS OF USE |
| MX394210B (es) | 2017-02-28 | 2025-03-04 | Morphic Therapeutic Inc | INHIBIDORES DE INTEGRINA AVß6. |
| MA52117A (fr) | 2017-02-28 | 2022-04-06 | Morphic Therapeutic Inc | Inhibiteurs de l'intégrine (alpha-v) (bêta-6) |
| FI3761980T3 (fi) * | 2018-03-07 | 2024-02-21 | Pliant Therapeutics Inc | Aminohappoyhdisteitä ja käyttömenetelmiä |
| TWI841573B (zh) | 2018-06-27 | 2024-05-11 | 美商普萊恩醫療公司 | 具有未分支連接子之胺基酸化合物及使用方法 |
| AU2019318538B2 (en) | 2018-08-08 | 2025-02-06 | The General Hospital Corporation | Polypeptide integrin antagonists |
| WO2020047208A1 (en) | 2018-08-29 | 2020-03-05 | Morphic Therapeutic, Inc. | Inhibitors of (alpha-v)(beta-6) integrin |
| WO2020047239A1 (en) | 2018-08-29 | 2020-03-05 | Morphic Therapeutic, Inc. | INHIBITING αV β6 INTEGRIN |
| SI3844162T1 (sl) | 2018-08-29 | 2025-06-30 | Morphic Therapeutic, Inc. | Zaviralci integrina alfa v beta6 |
| TW202028179A (zh) | 2018-10-08 | 2020-08-01 | 美商普萊恩醫療公司 | 胺基酸化合物及使用方法 |
| CN114173803A (zh) * | 2019-04-08 | 2022-03-11 | 普利安特治疗公司 | 氨基酸化合物的剂型和方案 |
| TW202329973A (zh) * | 2021-10-14 | 2023-08-01 | 美商普萊恩醫療公司 | 整合素抑制劑及其與其他藥劑併用之用途 |
| WO2024125634A1 (zh) * | 2022-12-16 | 2024-06-20 | 西藏海思科制药有限公司 | 一种四氢萘啶类化合物及其在医药上的应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6048861A (en) * | 1997-12-17 | 2000-04-11 | Merck & Co., Inc. | Integrin receptor antagonists |
| KR20010033248A (ko) * | 1997-12-17 | 2001-04-25 | 폴락 돈나 엘. | 인테그린 수용체 길항제 |
| CN1589145A (zh) * | 1999-06-02 | 2005-03-02 | 麦克公司 | αv整联蛋白受体拮抗剂 |
| FR2808798A1 (fr) | 2000-05-09 | 2001-11-16 | Hoechst Marion Roussel Inc | Nouveaux derives antagonistes du recepteur de la vitronectine |
| AU7793501A (en) * | 2000-07-26 | 2002-02-05 | Merck & Co Inc | Alpha v integrin receptor antagonists |
| EP1389205B1 (en) * | 2001-04-09 | 2005-12-21 | Ortho-McNeil Pharmaceutical Research Inc. | Quinazoline and quinazoline-like compounds for the treatment of integrin-mediated disorders |
| JP2003277340A (ja) * | 2002-03-22 | 2003-10-02 | Toray Ind Inc | 接着分子阻害剤及び新規アミノ酸誘導体 |
| EP2456460A4 (en) | 2009-07-24 | 2013-02-20 | Univ California | METHOD AND COMPOSITIONS FOR TREATING AND PREVENTING DISEASES ASSOCIATED WITH AVB5 INTEGRIN |
| PT2953948T (pt) * | 2013-02-07 | 2017-12-12 | Scifluor Life Sciences Inc | Antagonistas de integrina fluorada |
| US8901144B2 (en) | 2013-02-07 | 2014-12-02 | Scifluor Life Sciences, Llc | Fluorinated 3-(2-oxo-3-(3-arylpropyl)imidazolidin-1-yl)-3-arylpropanoic acid derivatives |
-
2017
- 2017-07-05 US US16/315,093 patent/US11192889B2/en active Active
- 2017-07-05 WO PCT/US2017/040657 patent/WO2018009501A1/en not_active Ceased
- 2017-07-05 EP EP17824775.5A patent/EP3481814B1/en not_active Not-in-force
- 2017-07-05 AU AU2017292754A patent/AU2017292754B2/en active Active
- 2017-07-05 KR KR1020197003579A patent/KR20190026001A/ko not_active Ceased
- 2017-07-05 CN CN201780042122.9A patent/CN109476632A/zh active Pending
- 2017-07-05 JP JP2019500301A patent/JP2019524702A/ja active Pending
- 2017-07-05 CA CA3029829A patent/CA3029829A1/en not_active Abandoned
- 2017-07-05 MX MX2019000043A patent/MX2019000043A/es unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2019524702A5 (https=) | ||
| RU2764243C2 (ru) | Гетероциклические соединения в качестве ингибиторов PAD | |
| JP7646632B2 (ja) | 甲状腺ホルモン受容体ベータアゴニスト化合物 | |
| JP4150672B2 (ja) | ナフチリジン誘導体、その製造およびそのホスホジエステラーゼイソ酵素４（ｐｄｅ４）阻害剤としての使用 | |
| KR100908155B1 (ko) | 히스타민 ｈ3 수용체 리간드로서 유용한테트라하이드로나프티리딘 유도체 | |
| US9382226B2 (en) | Aldosterone synthase inhibitors | |
| TWI494309B (zh) | Ｃ型肝炎病毒（ｈｃｖ）nｓ５ａ抑制劑 | |
| US20040229889A1 (en) | HDAC inhibitor | |
| JP2020507595A (ja) | ベンゾジアゼピン誘導体の製造プロセス | |
| KR20190031203A (ko) | 통합 스트레스 경로의 조정제 | |
| TW201825476A (zh) | Pad4之雜芳基抑制劑 | |
| RS50621B2 (sr) | Inhibitori dipeptidil peptidaze | |
| CA2938280A1 (en) | 4-amino-imidazoquinoline compounds | |
| JP2009517383A (ja) | 新規な３−ビシクロカルボニルアミノピリジン−２−カルボキサミド又は３−ビシクロカルボニルアミノピラジン−２−カルボキサミド | |
| KR20150033645A (ko) | 호흡기 합포체 바이러스의 항바이러스제로서의 벤즈이미다졸로 치환된 1,3-디하이드로-2h-벤즈이미다졸-2-온 유도체 | |
| RU2728823C1 (ru) | Фенильные производные в качестве агонистов каннабиноидного рецептора 2 | |
| KR20150138214A (ko) | (1s,4s,5s)-4-브로모-6-옥사비시클로[3.2.1]옥탄-7-온의 제조 방법 | |
| KR20090042973A (ko) | 바이러스 폴리머라제 억제제 | |
| JP2021102645A (ja) | メプリンアルファ及びベータの新規な阻害剤 | |
| KR20060130123A (ko) | 프로스타글란딘 ｅ2 작용제 또는 길항제로서의 오르니틴유도체 | |
| JP2002533338A (ja) | 非ペプチドｎｋ１レセプターアンタゴニスト | |
| JP2014516917A (ja) | ペプチドデホルミラーゼ阻害剤 | |
| CN120204220A (zh) | 治疗及/或预防纤维性疾病的胺基萘醌化合物 | |
| AU2006311786A1 (en) | Diphenylmethane derivatives as inhibitors of leukotriene biosynthesis | |
| EP4274572B1 (en) | Novel inhibitors of autotaxin |