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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- JP
- Japan
- Prior art keywords
- optionally substituted
- ring
- compound according
- formula
- ceremony
- 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 (https=) | 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 (https=) |
| EP (1) | EP3681878A4 (https=) |
| JP (1) | JP7334979B2 (https=) |
| KR (1) | KR20200090747A (https=) |
| CN (1) | CN111344284B (https=) |
| AU (1) | AU2018332634A1 (https=) |
| SG (1) | SG11202002267UA (https=) |
| WO (1) | WO2019054944A1 (https=) |
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 |
| CA3257285A1 (en) * | 2022-04-22 | 2023-10-26 | Vertex Pharmaceuticals Incorporated | HETEROARYL COMPOUNDS FOR PAIN RELIEF |
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 |
| WO2002000648A1 (en) * | 2000-06-28 | 2002-01-03 | Ssp Co., Ltd. | Imidazole derivatives or salts thereof and drugs containing the derivatives or the salts |
| CA2415899A1 (en) * | 2000-07-18 | 2003-01-13 | Chikashi Saitoh | Medicine comprising dicyanopyridine derivative |
| 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 |
| IL164826A0 (en) | 2002-05-16 | 2005-12-18 | Pharmacia Corp | Methods for the treatment of respiratory diseases and conditions using a selective inos inhibitor |
| 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 |
| EP1867331A4 (en) | 2005-04-06 | 2009-04-08 | Takeda Pharmaceutical | TRIAZOLE DERIVATIVE AND USE THEREOF |
| EP2046766A1 (en) | 2006-08-01 | 2009-04-15 | Praecis Pharmaceuticals Incorporated | Agonists of the sphingosine- 1- phosphate receptor (slp) |
| KR20090115749A (ko) | 2007-02-26 | 2009-11-05 | 산텐 세이야꾸 가부시키가이샤 | 우레이드기와 아미노카르보닐기를 치환기로서 갖는 신규 피롤 유도체 |
| MX2009010491A (es) * | 2007-04-11 | 2009-11-09 | Kissei Pharmaceutical | Derivado heterociclico de 5 miembros y su uso para propositos medicos. |
| KR20090077091A (ko) | 2008-01-10 | 2009-07-15 | 일동제약주식회사 | 신규 퍼옥시좀 증식자-활성화 수용체 효능제인 화합물 및그 제조방법 |
| WO2010058417A1 (en) | 2008-11-19 | 2010-05-27 | Council Of Scientific & Industrial Research | Isoxazole/isoxazoline/combretastatin linked dihydroquinazolinone hybrids as potential anticancer agents and process for the preparation thereof |
| EP2459533A4 (en) | 2009-07-30 | 2013-01-16 | Univ Singapore | SMALL MOLECULAR ISOPRENYLCYSTONE CARBOXYL METHYLTRANSFERASE HEMMER WITH POTENTIAL ANTIBODY EFFECT |
| 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 |
| AU2014291142B2 (en) | 2013-07-17 | 2018-10-11 | Otsuka Pharmaceutical Co., Ltd. | Cyanotriazole compounds |
| EP3200588A4 (en) | 2014-09-17 | 2018-04-25 | Epizyme, Inc. | Arginine methyltransferase inhibitors and uses thereof |
| JP6817962B2 (ja) | 2015-01-20 | 2021-01-20 | アルビナス・オペレーションズ・インコーポレイテッドＡｒｖｉｎａｓ Ｏｐｅｒａｔｉｏｎｓ， Ｉｎｃ． | ターゲティングされたアンドロゲン受容体分解のための化合物および方法 |
| 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 CN CN201880072698.4A patent/CN111344284B/zh active Active
- 2018-09-12 US US16/646,693 patent/US11834430B2/en active Active
- 2018-09-12 SG SG11202002267UA patent/SG11202002267UA/en unknown
- 2018-09-12 WO PCT/SG2018/050466 patent/WO2019054944A1/en not_active Ceased
- 2018-09-12 KR KR1020207010540A patent/KR20200090747A/ko not_active Ceased
- 2018-09-12 AU AU2018332634A patent/AU2018332634A1/en not_active Abandoned
- 2018-09-12 EP EP18856093.2A patent/EP3681878A4/en active Pending
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