JP2016535051A5 - - Google Patents
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- Publication number
- JP2016535051A5 JP2016535051A5 JP2016527397A JP2016527397A JP2016535051A5 JP 2016535051 A5 JP2016535051 A5 JP 2016535051A5 JP 2016527397 A JP2016527397 A JP 2016527397A JP 2016527397 A JP2016527397 A JP 2016527397A JP 2016535051 A5 JP2016535051 A5 JP 2016535051A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolidine
- hydroxy
- carboxamide
- propan
- pyrrolidin
- 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
Links
- IQHXABCGSFAKPN-UHFFFAOYSA-N pyrrolidine-3-carboxamide Chemical compound NC(=O)C1CCNC1 IQHXABCGSFAKPN-UHFFFAOYSA-N 0.000 claims 135
- -1 cyano, nitro, amino Chemical group 0.000 claims 77
- 125000000217 alkyl group Chemical group 0.000 claims 51
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 41
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 36
- 125000005843 halogen group Chemical group 0.000 claims 27
- 125000003118 aryl group Chemical group 0.000 claims 21
- 125000001188 haloalkyl group Chemical group 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims 19
- 125000001072 heteroaryl group Chemical group 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 19
- 125000003545 alkoxy group Chemical group 0.000 claims 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 18
- 239000000203 mixture Substances 0.000 claims 18
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 125000003282 alkyl amino group Chemical group 0.000 claims 12
- 125000004663 dialkyl amino group Chemical group 0.000 claims 12
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 11
- 125000004438 haloalkoxy group Chemical group 0.000 claims 11
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 10
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 6
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 6
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 150000001721 carbon Chemical group 0.000 claims 5
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 5
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 4
- 229930186217 Glycolipid Natural products 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 229910052805 deuterium Inorganic materials 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000006584 (C3-C10) heterocycloalkyl group Chemical group 0.000 claims 3
- HVCOBJNICQPDBP-UHFFFAOYSA-N 3-[3-[3,5-dihydroxy-6-methyl-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxyoxan-2-yl]oxydecanoyloxy]decanoic acid;hydrate Chemical group O.OC1C(OC(CC(=O)OC(CCCCCCC)CC(O)=O)CCCCCCC)OC(C)C(O)C1OC1C(O)C(O)C(O)C(C)O1 HVCOBJNICQPDBP-UHFFFAOYSA-N 0.000 claims 3
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 3
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- AVACWWJFNDKORC-WHSBFGAESA-N (3R)-1-(4-chlorophenyl)-N-[(1R,2R)-1-(5-fluoro-2,3-dihydro-1,4-benzodioxin-7-yl)-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]-3-hydroxypyrrolidine-3-carboxamide Chemical compound ClC1=CC=C(C=C1)N1C[C@](CC1)(C(=O)N[C@@H]([C@H](O)C1=CC2=C(OCCO2)C(=C1)F)CN1CCCC1)O AVACWWJFNDKORC-WHSBFGAESA-N 0.000 claims 2
- UMOKDDPWSNBDKO-LPPUWEFUSA-N (3R)-N-[(1R,2R)-1-(4-cyclopropyloxyphenyl)-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]-1-phenylpyrrolidine-3-carboxamide Chemical compound C1(CC1)OC1=CC=C(C=C1)[C@H]([C@@H](CN1CCCC1)NC(=O)[C@H]1CN(CC1)C1=CC=CC=C1)O UMOKDDPWSNBDKO-LPPUWEFUSA-N 0.000 claims 2
- GAKNHDHPMOMSTC-UEVCKROQSA-N (3R)-N-[(1R,2R)-1-[4-(difluoromethoxy)phenyl]-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]-1-phenylpyrrolidine-3-carboxamide Chemical compound FC(OC1=CC=C(C=C1)[C@H]([C@@H](CN1CCCC1)NC(=O)[C@H]1CN(CC1)C1=CC=CC=C1)O)F GAKNHDHPMOMSTC-UEVCKROQSA-N 0.000 claims 2
- AVACWWJFNDKORC-HNVPCBRESA-N (3S)-1-(4-chlorophenyl)-N-[(1R,2R)-1-(5-fluoro-2,3-dihydro-1,4-benzodioxin-7-yl)-1-hydroxy-3-pyrrolidin-1-ylpropan-2-yl]-3-hydroxypyrrolidine-3-carboxamide Chemical compound ClC1=CC=C(C=C1)N1C[C@@](CC1)(C(=O)N[C@@H]([C@H](O)C1=CC2=C(OCCO2)C(=C1)F)CN1CCCC1)O AVACWWJFNDKORC-HNVPCBRESA-N 0.000 claims 2
- UEEAOPCMWZATAG-UHFFFAOYSA-N 1-(4-chlorophenyl)pyrrolidine-3-carboxamide Chemical compound NC(=O)C1CCN(C1)C1=CC=C(Cl)C=C1 UEEAOPCMWZATAG-UHFFFAOYSA-N 0.000 claims 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000001537 neural effect Effects 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- 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 1
- 102100022548 Beta-hexosaminidase subunit alpha Human genes 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 206010006187 Breast cancer Diseases 0.000 claims 1
- 208000026310 Breast neoplasm Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000024720 Fabry Disease Diseases 0.000 claims 1
- 201000008892 GM1 Gangliosidosis Diseases 0.000 claims 1
- 208000015872 Gaucher disease Diseases 0.000 claims 1
- 206010060378 Hyperinsulinaemia Diseases 0.000 claims 1
- 208000005016 Intestinal Neoplasms Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010029260 Neuroblastoma Diseases 0.000 claims 1
- 208000014060 Niemann-Pick disease Diseases 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 1
- 206010038468 Renal hypertrophy Diseases 0.000 claims 1
- 208000021811 Sandhoff disease Diseases 0.000 claims 1
- 208000022292 Tay-Sachs disease Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 238000009825 accumulation Methods 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 150000002305 glucosylceramides Chemical class 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 201000001421 hyperglycemia Diseases 0.000 claims 1
- 230000003451 hyperinsulinaemic effect Effects 0.000 claims 1
- 201000008980 hyperinsulinism Diseases 0.000 claims 1
- 206010020718 hyperplasia Diseases 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 201000002313 intestinal cancer Diseases 0.000 claims 1
- 201000008627 kidney hypertrophy Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- ACHUFWJUNLHTDL-UHFFFAOYSA-N n-(4-chlorophenyl)pyrrolidine-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C1CNCC1 ACHUFWJUNLHTDL-UHFFFAOYSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361897110P | 2013-10-29 | 2013-10-29 | |
| US61/897,110 | 2013-10-29 | ||
| PCT/US2014/062516 WO2015065937A1 (en) | 2013-10-29 | 2014-10-28 | N-(1-hydroxy-3-(pyrrolidinyl)propan-2-yl)pyrrolidine-3-carboxamide derivatives as glucosylceramide synthase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016535051A JP2016535051A (ja) | 2016-11-10 |
| JP2016535051A5 true JP2016535051A5 (enExample) | 2017-11-16 |
| JP6526652B2 JP6526652B2 (ja) | 2019-06-05 |
Family
ID=51947476
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016527397A Active JP6526652B2 (ja) | 2013-10-29 | 2014-10-28 | グルコシルセラミドシンターゼ阻害剤としてのｎ−（１−ヒドロキシ−３−（ピロリジニル）プロパン−２−イル）ピロリジン−３−カルボキサミド誘導体 |
Country Status (15)
| Country | Link |
|---|---|
| US (2) | US10239832B2 (enExample) |
| EP (1) | EP3063141B1 (enExample) |
| JP (1) | JP6526652B2 (enExample) |
| CN (1) | CN105849102B (enExample) |
| AU (1) | AU2014342593B2 (enExample) |
| CA (1) | CA2927798C (enExample) |
| HR (1) | HRP20181197T1 (enExample) |
| HU (1) | HUE040220T2 (enExample) |
| IL (1) | IL245208B (enExample) |
| MX (1) | MX376685B (enExample) |
| NZ (1) | NZ719028A (enExample) |
| SI (1) | SI3063141T1 (enExample) |
| SM (1) | SMT201800411T1 (enExample) |
| TW (1) | TWI655185B (enExample) |
| WO (1) | WO2015065937A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107635980A (zh) | 2015-03-11 | 2018-01-26 | 生物马林药物股份有限公司 | 用于治疗疾病的葡糖神经酰胺合酶抑制剂 |
| TW201726675A (zh) | 2015-12-23 | 2017-08-01 | 默沙東藥廠 | M4毒蕈鹼乙醯膽鹼受體之異位調節劑6,7-二氫-5h-吡咯并[3,4-b]吡啶-5-酮 |
| WO2018112843A1 (en) | 2016-12-22 | 2018-06-28 | Merck Sharp & Dohme Corp. | Heteroaryl piperidine ether allosteric modulators of the m4 muscarinic acetylcholine receptor |
| CN107011251B (zh) * | 2017-03-29 | 2020-08-11 | 温州医科大学 | 一种2-(2-氯苯氧基)吡啶化合物的合成方法及其用途 |
| CN110068638B (zh) * | 2019-05-21 | 2021-11-26 | 中山大学孙逸仙纪念医院 | 一种特异分离富集人血清中酸性鞘脂及糖鞘脂的方法 |
| JP7725076B2 (ja) * | 2020-04-28 | 2025-08-19 | ザ・リージェンツ・オブ・ザ・ユニバーシティ・オブ・ミシガン | グルコシルセラミド合成酵素のピリジン阻害剤及びそれらを使用する治療方法 |
| MX2024003127A (es) * | 2021-09-15 | 2024-05-31 | Celloram Inc | Inhibidores de fabp4/5, metodos de uso y metodos de elaboración. |
| CN115433157B (zh) * | 2022-11-09 | 2023-02-07 | 苏州凯瑞医药科技有限公司 | 一种依利格鲁司特中间体的制备方法 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6159938A (en) * | 1994-11-21 | 2000-12-12 | Cortech, Inc. | Serine protease inhibitors comprising α-keto heterocycles |
| US5756528A (en) | 1995-06-06 | 1998-05-26 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| SK10742001A3 (sk) * | 1999-01-27 | 2002-08-06 | Ortho-Mcneil Pharmaceutical, Inc. | Peptidylové heterocyklické ketóny použiteľné ako inhibítory tryptázy |
| US7226991B1 (en) * | 1999-03-23 | 2007-06-05 | United States Of America, Represented By The Secretary, Department Of Health And Human Services | Phenylalanine derivatives |
| JP5009459B2 (ja) * | 1999-12-06 | 2012-08-22 | 生化学工業株式会社 | アミノアルコール誘導体及びそれを含有する医薬 |
| US6407064B2 (en) * | 1999-12-06 | 2002-06-18 | Seikagaku Corporation | Aminoalcohol derivative and medicament comprising the same |
| WO2002080920A1 (en) | 2001-04-06 | 2002-10-17 | Axys Pharmaceuticals, Inc. | Arylacetamido-ketobenzoxazole as cysteine protease inhibitors |
| ES2399323T3 (es) | 2001-07-16 | 2013-03-27 | Genzyme Corporation | Síntesis de inhibidores de la UDP-glucosa:N-acilesfingosina glucosiltransferasa |
| US6835831B2 (en) | 2001-11-26 | 2004-12-28 | Genzyme Corporation | Diastereoselective synthesis of UDP-glucose: N-acylsphingosine glucosyltransferase inhibitors |
| AU2004220087A1 (en) | 2003-03-06 | 2004-09-23 | Seneb Biosciences, Inc. | Methods and compositions for the enzymatic synthesis of gangliosides |
| GB0400812D0 (en) | 2004-01-14 | 2004-02-18 | Celltech R&D Ltd | Novel compounds |
| WO2006053043A2 (en) | 2004-11-10 | 2006-05-18 | Genzyme Corporation | Methods of treating diabetes mellitus |
| HUE026057T2 (en) | 2006-05-09 | 2016-05-30 | Genzyme Corp | Procedures for the Treatment of Fatty Liver Disease, which comprises inhibition of glycosphingolipid synthesis |
| WO2008011483A2 (en) | 2006-07-19 | 2008-01-24 | Allergan, Inc. | Methods for treating chronic pain using 1- (hetero) aryl-1-hydroxy 2,3-diamino-propyl amines and related compounds |
| EP2117541A1 (en) * | 2007-02-09 | 2009-11-18 | Irm Llc | Compounds and compositions as channel activating protease inhibitors |
| US20100105687A1 (en) | 2007-03-06 | 2010-04-29 | Allergan, Inc. | Methods for treating cognitive disorders using 1-aryl-1-hydroxy-2,3-diamino-propyl amines, 1-heteroaryl-1-hydroxy-2,3-diamino-propyl amines and related compounds |
| EP2167485B1 (en) * | 2007-05-31 | 2015-09-30 | Genzyme Corporation | 2-acylaminopropoanol-type glucosylceramide synthase inhibitors |
| EP2209473B1 (en) | 2007-10-05 | 2017-11-22 | Genzyme Corporation | Method of treating polycystic kidney diseases with ceramide derivatives |
| WO2009117150A2 (en) | 2008-03-20 | 2009-09-24 | Genzyme Corporation | Method of treating lupus with ceramide derivatives |
| US8389517B2 (en) | 2008-07-28 | 2013-03-05 | Genzyme Corporation | Glucosylceramide synthase inhibition for the treatment of collapsing glomerulopathy and other glomerular disease |
| WO2010098145A1 (en) * | 2009-02-27 | 2010-09-02 | Raqualia Pharma Inc. | Oxyindole derivatives with motilin receptor agonistic activity |
| US8961959B2 (en) * | 2011-10-17 | 2015-02-24 | The Regents Of The University Of Michigan | Glucosylceramide synthase inhibitors and therapeutic methods using the same |
-
2014
- 2014-10-28 US US15/032,613 patent/US10239832B2/en active Active
- 2014-10-28 MX MX2016005437A patent/MX376685B/es active IP Right Grant
- 2014-10-28 CA CA2927798A patent/CA2927798C/en active Active
- 2014-10-28 EP EP14802535.6A patent/EP3063141B1/en active Active
- 2014-10-28 CN CN201480071429.8A patent/CN105849102B/zh active Active
- 2014-10-28 SM SM20180411T patent/SMT201800411T1/it unknown
- 2014-10-28 AU AU2014342593A patent/AU2014342593B2/en active Active
- 2014-10-28 NZ NZ719028A patent/NZ719028A/en unknown
- 2014-10-28 HR HRP20181197TT patent/HRP20181197T1/hr unknown
- 2014-10-28 HU HUE14802535A patent/HUE040220T2/hu unknown
- 2014-10-28 WO PCT/US2014/062516 patent/WO2015065937A1/en not_active Ceased
- 2014-10-28 SI SI201430808T patent/SI3063141T1/sl unknown
- 2014-10-28 TW TW103137304A patent/TWI655185B/zh active
- 2014-10-28 JP JP2016527397A patent/JP6526652B2/ja active Active
-
2016
- 2016-04-19 IL IL245208A patent/IL245208B/en active IP Right Grant
-
2019
- 2019-02-12 US US16/274,117 patent/US11358932B2/en active Active
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