JP2015526411A5 - - Google Patents
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- Publication number
- JP2015526411A5 JP2015526411A5 JP2015521942A JP2015521942A JP2015526411A5 JP 2015526411 A5 JP2015526411 A5 JP 2015526411A5 JP 2015521942 A JP2015521942 A JP 2015521942A JP 2015521942 A JP2015521942 A JP 2015521942A JP 2015526411 A5 JP2015526411 A5 JP 2015526411A5
- Authority
- JP
- Japan
- Prior art keywords
- alkoxy
- aliphatic
- alkyl
- aryl
- heteroaryl
- 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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- 125000003545 alkoxy group Chemical group 0.000 claims description 440
- 125000001931 aliphatic group Chemical group 0.000 claims description 279
- 125000000217 alkyl group Chemical group 0.000 claims description 273
- 125000000623 heterocyclic group Chemical group 0.000 claims description 180
- 125000003118 aryl group Chemical group 0.000 claims description 173
- 125000001072 heteroaryl group Chemical group 0.000 claims description 166
- -1 hydroxy, amino Chemical group 0.000 claims description 112
- 229910052731 fluorine Inorganic materials 0.000 claims description 94
- 229910052740 iodine Inorganic materials 0.000 claims description 89
- 229910052801 chlorine Inorganic materials 0.000 claims description 84
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 77
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 229910052794 bromium Inorganic materials 0.000 claims description 66
- 229910052717 sulfur Inorganic materials 0.000 claims description 66
- 229910052760 oxygen Inorganic materials 0.000 claims description 65
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 64
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 61
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 54
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 48
- 125000004104 aryloxy group Chemical group 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 40
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 36
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 34
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 26
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000003282 alkyl amino group Chemical group 0.000 claims description 23
- 125000004414 alkyl thio group Chemical group 0.000 claims description 22
- 206010016654 Fibrosis Diseases 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 19
- 125000001188 haloalkyl group Chemical group 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 230000004761 fibrosis Effects 0.000 claims description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 14
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 13
- 125000001769 aryl amino group Chemical group 0.000 claims description 12
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 12
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 10
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 10
- 210000000056 organ Anatomy 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 210000001519 tissue Anatomy 0.000 claims description 9
- 206010060932 Postoperative adhesion Diseases 0.000 claims description 8
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 8
- 125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 7
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 7
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 7
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 7
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 7
- 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 7
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
- 125000006719 (C6-C10) aryl (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 4
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 4
- 206010023421 Kidney fibrosis Diseases 0.000 claims description 4
- 206010048654 Muscle fibrosis Diseases 0.000 claims description 4
- 206010028594 Myocardial fibrosis Diseases 0.000 claims description 4
- 201000004404 Neurofibroma Diseases 0.000 claims description 4
- 206010034665 Peritoneal fibrosis Diseases 0.000 claims description 4
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 4
- 206010039710 Scleroderma Diseases 0.000 claims description 4
- 206010050207 Skin fibrosis Diseases 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
- 230000007882 cirrhosis Effects 0.000 claims description 4
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 4
- 206010061989 glomerulosclerosis Diseases 0.000 claims description 4
- 230000035876 healing Effects 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 231100000241 scar Toxicity 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 230000002792 vascular Effects 0.000 claims description 4
- 125000004450 alkenylene group Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
- 150000001204 N-oxides Chemical class 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000002207 metabolite Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000000651 prodrug Substances 0.000 claims description 2
- 229940002612 prodrug Drugs 0.000 claims description 2
- 239000003981 vehicle Substances 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims 4
- 238000007069 methylation reaction Methods 0.000 claims 4
- 230000005494 condensation Effects 0.000 claims 3
- 238000009833 condensation Methods 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 235000018936 Vitellaria paradoxa Nutrition 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 230000003510 anti-fibrotic effect Effects 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 230000003176 fibrotic effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 125000003003 spiro group Chemical group 0.000 claims 1
- 0 B**N(*=*CC)C(C(C)C=*)=* Chemical compound B**N(*=*CC)C(C(C)C=*)=* 0.000 description 101
- 125000004438 haloalkoxy group Chemical class 0.000 description 10
- 241000239366 Euphausiacea Species 0.000 description 5
- 125000003418 alkyl amino alkoxy group Chemical class 0.000 description 5
- 125000005241 heteroarylamino group Chemical group 0.000 description 5
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- 238000000034 method Methods 0.000 description 4
- 206010061692 Benign muscle neoplasm Diseases 0.000 description 3
- 201000004458 Myoma Diseases 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000005549 heteroarylene group Chemical group 0.000 description 3
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 description 3
- 229960003073 pirfenidone Drugs 0.000 description 3
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| EP3219705B1 (en) | 2005-12-28 | 2020-03-11 | Vertex Pharmaceuticals Incorporated | Pharmaceutical compositions of the amorphous form of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| AR092742A1 (es) | 2012-10-02 | 2015-04-29 | Intermune Inc | Piridinonas antifibroticas |
| ES2663806T3 (es) * | 2013-12-19 | 2018-04-17 | unshine Lake Pharma Co., Ltd. | Derivados heterocíclicos nitrogenados y su aplicación en el tratamiento de la fibrosis tisular |
| MX382781B (es) | 2014-04-02 | 2025-03-13 | Intermune Inc | Piridinonas anti-fibroticas. |
| CN107250113B (zh) | 2014-10-07 | 2019-03-29 | 弗特克斯药品有限公司 | 囊性纤维化跨膜传导调节蛋白的调节剂的共晶 |
| CN106397408B (zh) * | 2015-07-30 | 2019-04-02 | 四川大学 | 5-甲基-2(1h)吡啶酮衍生物及其制备方法和用途 |
| FR3046793B1 (fr) * | 2016-01-14 | 2018-01-05 | Les Laboratoires Servier | Nouveaux derives de phosphinanes et azaphosphinanes, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CN106083817B (zh) * | 2016-06-14 | 2019-01-18 | 四川大学 | 吡非尼酮衍生物及其制备方法 |
| CN106045971B (zh) * | 2016-06-16 | 2018-12-21 | 杨若一 | 吡非尼酮衍生物及其制备方法 |
| JP7030779B2 (ja) * | 2016-07-27 | 2022-03-07 | サンシャイン・レイク・ファーマ・カンパニー・リミテッド | ２，６－ジメチルピリミドン誘導体の塩及びその使用 |
| CN109311820B (zh) * | 2016-07-27 | 2022-09-27 | 广东东阳光药业有限公司 | 2,6-二甲基嘧啶酮衍生物的盐及其用途 |
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