JP2020533386A5 - - Google Patents
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- JP2020533386A5 JP2020533386A5 JP2020515184A JP2020515184A JP2020533386A5 JP 2020533386 A5 JP2020533386 A5 JP 2020533386A5 JP 2020515184 A JP2020515184 A JP 2020515184A JP 2020515184 A JP2020515184 A JP 2020515184A JP 2020533386 A5 JP2020533386 A5 JP 2020533386A5
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- Prior art keywords
- optionally substituted
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- 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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- 150000001875 compounds Chemical class 0.000 claims description 66
- 229940002612 prodrug Drugs 0.000 claims description 20
- 239000000651 prodrug Substances 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 16
- 108060001621 Isoprenylcysteine carboxyl methyltransferase Proteins 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 14
- 201000011510 cancer Diseases 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims description 11
- 208000025500 Hutchinson-Gilford progeria syndrome Diseases 0.000 claims description 9
- 208000007932 Progeria Diseases 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 7
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 7
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 206010006187 Breast cancer Diseases 0.000 claims description 4
- 208000026310 Breast neoplasm Diseases 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 206010033128 Ovarian cancer Diseases 0.000 claims description 4
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 4
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 4
- 230000004913 activation Effects 0.000 claims description 4
- 208000029742 colonic neoplasm Diseases 0.000 claims description 4
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 4
- 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 4
- 208000032839 leukemia Diseases 0.000 claims description 4
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- -1 methoxy, methyl Chemical group 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 201000002528 pancreatic cancer Diseases 0.000 claims description 4
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 4
- 208000030087 premature aging syndrome Diseases 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 102100035033 Protein-S-isoprenylcysteine O-methyltransferase Human genes 0.000 claims 4
- 206010063493 Premature ageing Diseases 0.000 claims 1
- 208000032038 Premature aging Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 238000000034 method Methods 0.000 description 11
- 102000029740 protein-S-isoprenylcysteine O-methyltransferase Human genes 0.000 description 10
- 239000003814 drug Substances 0.000 description 7
- 230000001594 aberrant effect Effects 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- 229940079593 drug Drugs 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- OFVRLVNCLJSKGW-ZETCQYMHSA-N (2R)-2-(3-methylbuta-1,3-dienylamino)-3-sulfanylpropanoic acid Chemical compound CC(=C)C=CN[C@@H](CS)C(O)=O OFVRLVNCLJSKGW-ZETCQYMHSA-N 0.000 description 1
- 150000001944 cysteine derivatives Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000035407 negative regulation of cell proliferation Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SG10201707444W | 2017-09-12 | ||
| SG10201707444W | 2017-09-12 | ||
| PCT/SG2018/050466 WO2019054944A1 (en) | 2017-09-12 | 2018-09-12 | COMPOUNDS USEFUL AS INHIBITORS OF ISOPRENYLCYSTEINE CARBOXYL METHYLTRANFERASE |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020533386A JP2020533386A (ja) | 2020-11-19 |
| JP2020533386A5 true JP2020533386A5 (enExample) | 2021-10-21 |
| JP7334979B2 JP7334979B2 (ja) | 2023-08-29 |
Family
ID=65722547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020515184A Active JP7334979B2 (ja) | 2017-09-12 | 2018-09-12 | イソプレニルシステインカルボキシルメチルトランスフェラーゼ阻害剤として有用な化合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US11834430B2 (enExample) |
| EP (1) | EP3681878A4 (enExample) |
| JP (1) | JP7334979B2 (enExample) |
| KR (1) | KR20200090747A (enExample) |
| CN (1) | CN111344284B (enExample) |
| AU (1) | AU2018332634A1 (enExample) |
| SG (1) | SG11202002267UA (enExample) |
| WO (1) | WO2019054944A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023086671A1 (en) * | 2021-11-15 | 2023-05-19 | The Broad Institute, Inc. | Compounds, compositions, and methods for inducing antimicrobial intracellular activity and for preventing and treating microbial infections |
| CN119487003A (zh) * | 2022-04-22 | 2025-02-18 | 沃泰克斯药物股份有限公司 | 用于治疗疼痛的杂芳基化合物 |
Family Cites Families (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2248491A (en) | 1941-07-08 | Chs-chs | ||
| US2196576A (en) | 1938-12-16 | 1940-04-09 | Dow Chemical Co | Glycol ether |
| DE3331692A1 (de) | 1983-09-02 | 1985-03-28 | Basf Ag, 6700 Ludwigshafen | 3-phenyl-4-methoxycarbonylpyrazole, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| IL111959A (en) | 1993-12-17 | 2000-07-16 | Tanabe Seiyaku Co | N-(polysubstituted pyrimidin-4-yl) benzenesulfonamide derivatives their preparation and pharmaceutical compositions containing them |
| US6204293B1 (en) * | 1995-11-06 | 2001-03-20 | University Of Pittsburgh | Inhibitors of protein isoprenyl transferases |
| US6465467B1 (en) | 1999-05-21 | 2002-10-15 | Biovitrum Ab | Certain aryl-aliphatic and heteroaryl-aliphatic piperazinyl pyrazines and their use in the treatment of serotonin-related diseases |
| US6958353B2 (en) | 2000-06-28 | 2005-10-25 | Hisamitsu Medical Co., Ltd. | Imidazole derivatives or salts thereof and drugs containing the derivatives or the salts |
| KR20030026979A (ko) * | 2000-07-18 | 2003-04-03 | 야마노우치세이야쿠 가부시키가이샤 | 디시아노피리딘 유도체를 포함하는 의약 |
| MY140724A (en) | 2000-07-21 | 2010-01-15 | Actelion Pharmaceuticals Ltd | Novel arylethene-sulfonamides |
| US6727364B2 (en) | 2001-04-30 | 2004-04-27 | The Procter & Gamble Company | Triazole compounds useful in treating diseases associated with unwanted cytokine activity |
| KR20050004155A (ko) | 2002-05-16 | 2005-01-12 | 파마시아 코포레이션 | 선택적 유도성 산화질소 신타아제 억제제를 이용한 호흡기질병 및 질환의 치료 방법 |
| JP2004262890A (ja) | 2003-03-04 | 2004-09-24 | Taisho Pharmaceut Co Ltd | ２０−ｈｅｔｅ産生阻害作用を有するアゾール誘導体 |
| US8088935B2 (en) * | 2003-12-23 | 2012-01-03 | Ironwood Pharmaceuticals, Inc. | Compounds and methods for the treatment of asthma |
| JP2005298406A (ja) | 2004-04-12 | 2005-10-27 | Fuji Photo Film Co Ltd | ５−アミノピラゾール化合物、及び該化合物を含む記録材料 |
| CN1944383A (zh) | 2005-01-11 | 2007-04-11 | 中国医学科学院药物研究所 | α－烷氧丙酸类化合物及其制法和药物用途 |
| JPWO2006109846A1 (ja) | 2005-04-06 | 2008-11-20 | 武田薬品工業株式会社 | トリアゾール誘導体およびその用途 |
| US20080070866A1 (en) | 2006-08-01 | 2008-03-20 | Praecis Pharmaceuticals Incorporated | Chemical compounds |
| DK2116530T3 (da) | 2007-02-26 | 2013-01-28 | Santen Pharmaceutical Co Ltd | Nyt pyrrolderivat, der har en ureidgruppe og en aminobonylgruppe som substituenter |
| CN101679244B (zh) * | 2007-04-11 | 2014-01-01 | 橘生药品工业株式会社 | 5元杂环衍生物及其医药用途 |
| KR20090077091A (ko) | 2008-01-10 | 2009-07-15 | 일동제약주식회사 | 신규 퍼옥시좀 증식자-활성화 수용체 효능제인 화합물 및그 제조방법 |
| US8883809B2 (en) | 2008-11-19 | 2014-11-11 | Council Of Scientific & Industrial Research | Isoxazole/isoxazoline/combretastatin linked dihydroquinazolinone hybrids as potential anticancer agents and process for the preparation thereof |
| US8742100B2 (en) | 2009-07-30 | 2014-06-03 | National University Of Singapore | Small molecule inhibitors of isoprenylcysteine carboxyl methyltransferase with potential anticancer activity |
| EP2670739B1 (en) | 2011-02-04 | 2015-04-01 | Council Of Scientific & Industrial Research | Benzothiazole hybrids useful as anticancer agents and process for the preparation thereof |
| WO2014041349A1 (en) | 2012-09-12 | 2014-03-20 | Cancer Therapeutics Crc Pty Ltd | Tetrahydropyran-4-ylethylamino- or tetrahydropyranyl-4-ethyloxy-pyrimidines or -pyridazines as isoprenylcysteincarboxymethyl transferase inhibitors |
| SG11201600108PA (en) * | 2013-07-17 | 2016-02-26 | Otsuka Pharma Co Ltd | Cyanotriazole compounds |
| US20170283400A1 (en) | 2014-09-17 | 2017-10-05 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| HK1245791A1 (zh) | 2015-01-20 | 2018-08-31 | 阿尔维纳斯运营股份有限公司 | 用於雄激素受体的靶向降解的化合物和方法 |
| WO2017136699A1 (en) | 2016-02-05 | 2017-08-10 | Epizyme, Inc | Arginine methyltransferase inhibitors and uses thereof |
| US11191741B2 (en) * | 2016-12-24 | 2021-12-07 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of enhancer of zeste homolog 2 polypeptide |
-
2018
- 2018-09-12 JP JP2020515184A patent/JP7334979B2/ja active Active
- 2018-09-12 AU AU2018332634A patent/AU2018332634A1/en not_active Abandoned
- 2018-09-12 SG SG11202002267UA patent/SG11202002267UA/en unknown
- 2018-09-12 CN CN201880072698.4A patent/CN111344284B/zh active Active
- 2018-09-12 WO PCT/SG2018/050466 patent/WO2019054944A1/en not_active Ceased
- 2018-09-12 US US16/646,693 patent/US11834430B2/en active Active
- 2018-09-12 KR KR1020207010540A patent/KR20200090747A/ko not_active Ceased
- 2018-09-12 EP EP18856093.2A patent/EP3681878A4/en active Pending