JP2017534669A5 - - Google Patents
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- JP2017534669A5 JP2017534669A5 JP2017527810A JP2017527810A JP2017534669A5 JP 2017534669 A5 JP2017534669 A5 JP 2017534669A5 JP 2017527810 A JP2017527810 A JP 2017527810A JP 2017527810 A JP2017527810 A JP 2017527810A JP 2017534669 A5 JP2017534669 A5 JP 2017534669A5
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- alkyl
- compound
- halo
- optionally substituted
- 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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- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 125000004494 ethyl ester group Chemical group 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000006345 epimerization reaction Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000004678 hydrides Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000012279 sodium borohydride Substances 0.000 claims description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 10
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 claims 2
- 125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000005647 linker group Chemical group 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000003827 glycol group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 230000000155 isotopic effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 229920001223 polyethylene glycol Polymers 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 0 C[C@](**)[C@@]([C@@](*)CC1C23)[C@@]1(C)C(*)CC2[C@@](C)(CCC(C1)=O)[C@]1(C)[C@@](*)C3=O Chemical compound C[C@](**)[C@@]([C@@](*)CC1C23)[C@@]1(C)C(*)CC2[C@@](C)(CCC(C1)=O)[C@]1(C)[C@@](*)C3=O 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 238000006772 olefination reaction Methods 0.000 description 4
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 2
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 description 2
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 2
- VRQGDXMQCBUIOE-VTQWOKCDSA-N CCOC(CCC[C@@H](CC1)C(C)(CC2)C1C(CCC1)C2[C@@](C)(CC2)C1=CC2=O)=O Chemical compound CCOC(CCC[C@@H](CC1)C(C)(CC2)C1C(CCC1)C2[C@@](C)(CC2)C1=CC2=O)=O VRQGDXMQCBUIOE-VTQWOKCDSA-N 0.000 description 2
- DNVPQKQSNYMLRS-NXVQYWJNSA-N Ergosterol Natural products CC(C)[C@@H](C)C=C[C@H](C)[C@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@]12C DNVPQKQSNYMLRS-NXVQYWJNSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- DNVPQKQSNYMLRS-SOWFXMKYSA-N ergosterol Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H](CC[C@]3([C@H]([C@H](C)/C=C/[C@@H](C)C(C)C)CC[C@H]33)C)C3=CC=C21 DNVPQKQSNYMLRS-SOWFXMKYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- -1 lithium aluminum hydride Chemical compound 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1420594.2A GB201420594D0 (en) | 2014-11-19 | 2014-11-19 | Compounds |
| GB1420593.4 | 2014-11-19 | ||
| GB1420594.2 | 2014-11-19 | ||
| GBGB1420593.4A GB201420593D0 (en) | 2014-11-19 | 2014-11-19 | Compounds |
| GBGB1505675.7A GB201505675D0 (en) | 2015-04-01 | 2015-04-01 | Compounds |
| GB1505675.7 | 2015-04-01 | ||
| PCT/GB2015/053519 WO2016079520A1 (en) | 2014-11-19 | 2015-11-19 | 6.alpha.-alkyl-6,7-dione steroids as intermediates for the production of steroidal fxr modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017534669A JP2017534669A (ja) | 2017-11-24 |
| JP2017534669A5 true JP2017534669A5 (https=) | 2019-01-10 |
| JP6698085B2 JP6698085B2 (ja) | 2020-05-27 |
Family
ID=54704022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017527810A Active JP6698085B2 (ja) | 2014-11-19 | 2015-11-19 | ステロイドＦＸＲモジュレーター製造のための中間体としての６α−アルキル−６，７−ジオン−ステロイド |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US20170327531A1 (https=) |
| EP (1) | EP3221334B1 (https=) |
| JP (1) | JP6698085B2 (https=) |
| KR (1) | KR102527821B1 (https=) |
| CN (1) | CN107207558B (https=) |
| CA (1) | CA2968310A1 (https=) |
| EA (1) | EA033603B1 (https=) |
| MX (1) | MX381239B (https=) |
| TW (1) | TWI688571B (https=) |
| WO (1) | WO2016079520A1 (https=) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107207559B (zh) | 2014-11-19 | 2019-10-25 | Nzp英国有限公司 | 作为制备类固醇fxr调节剂的中间体的6-烷基-7-羟基-4-烯-3-酮类固醇 |
| KR102527821B1 (ko) | 2014-11-19 | 2023-05-02 | 엔제트피 유케이 리미티드 | 스테로이드 FXR 조절인자를 제조하기 위한 중간체로서의 6α-알킬-6,7-다이온 스테로이드 |
| KR102546748B1 (ko) | 2014-11-19 | 2023-06-22 | 엔제트피 유케이 리미티드 | 스테로이드 FXR 조절인자를 제조하기 위한 중간체로서의 6α-알킬-3,7-다이온 스테로이드 |
| EA033445B1 (ru) | 2014-11-19 | 2019-10-31 | Nzp Uk Ltd | 5-бета-6-алкил-7-гидрокси-3-оновые стероиды в качестве промежуточных соединений для получения стероидных модуляторов fxr |
| JP2018538331A (ja) * | 2015-12-22 | 2018-12-27 | インターセプト ファーマシューティカルズ， インコーポレイテッド | オベチコール酸の多型結晶形態 |
| GB201608779D0 (en) * | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Methods and compounds |
| GB201608776D0 (en) | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Methods and compounds |
| GB201608777D0 (en) | 2016-05-18 | 2016-06-29 | Dextra Lab Ltd | Compounds |
| CN106046093A (zh) * | 2016-05-30 | 2016-10-26 | 华东师范大学 | 一种石胆酸的合成方法 |
| EP3431486A1 (en) | 2017-07-18 | 2019-01-23 | Bionice, S.L.U. | Process and intermediates for the synthesis of obeticholic acid and derivatives thereof |
| GB201812382D0 (en) | 2018-07-30 | 2018-09-12 | Nzp Uk Ltd | Compounds |
| CN116178473B (zh) * | 2018-12-10 | 2025-03-04 | 江西科睿药业有限公司 | 一种奥贝胆酸的制备方法 |
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| CN107207559B (zh) | 2014-11-19 | 2019-10-25 | Nzp英国有限公司 | 作为制备类固醇fxr调节剂的中间体的6-烷基-7-羟基-4-烯-3-酮类固醇 |
| EA033445B1 (ru) | 2014-11-19 | 2019-10-31 | Nzp Uk Ltd | 5-бета-6-алкил-7-гидрокси-3-оновые стероиды в качестве промежуточных соединений для получения стероидных модуляторов fxr |
| KR102527821B1 (ko) | 2014-11-19 | 2023-05-02 | 엔제트피 유케이 리미티드 | 스테로이드 FXR 조절인자를 제조하기 위한 중간체로서의 6α-알킬-6,7-다이온 스테로이드 |
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| JP6861703B2 (ja) | 2015-06-19 | 2021-04-21 | インターセプト ファーマシューティカルズ， インコーポレイテッド | Ｔｇｒ５修飾物質およびその使用方法 |
| CN106397522A (zh) | 2015-07-31 | 2017-02-15 | 中国人民解放军军事医学科学院毒物药物研究所 | 3,7‑二（叔丁基二甲基硅基氧基）‑6‑烯‑5β‑胆烷‑24‑酸甲酯 |
| CN106478759A (zh) | 2015-08-31 | 2017-03-08 | 陕西合成药业股份有限公司 | 奥贝胆酸衍生物及其制备方法和用途 |
| CN106478756A (zh) | 2015-09-02 | 2017-03-08 | 中美华世通生物医药科技（武汉）有限公司 | Oca-e单晶及其制备方法和用途 |
| CN106518946A (zh) | 2015-09-10 | 2017-03-22 | 上海迪诺医药科技有限公司 | 磺酰脲衍生物、其药物组合物及应用 |
-
2015
- 2015-11-19 KR KR1020177016858A patent/KR102527821B1/ko active Active
- 2015-11-19 US US15/528,341 patent/US20170327531A1/en not_active Abandoned
- 2015-11-19 WO PCT/GB2015/053519 patent/WO2016079520A1/en not_active Ceased
- 2015-11-19 EP EP15800912.6A patent/EP3221334B1/en active Active
- 2015-11-19 EA EA201790885A patent/EA033603B1/ru not_active IP Right Cessation
- 2015-11-19 MX MX2017006567A patent/MX381239B/es unknown
- 2015-11-19 TW TW104138186A patent/TWI688571B/zh not_active IP Right Cessation
- 2015-11-19 CA CA2968310A patent/CA2968310A1/en not_active Abandoned
- 2015-11-19 CN CN201580062901.6A patent/CN107207558B/zh active Active
- 2015-11-19 JP JP2017527810A patent/JP6698085B2/ja active Active
-
2018
- 2018-10-17 US US16/163,259 patent/US10597423B2/en active Active
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