JP2012513381A5 - - Google Patents
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- JP2012513381A5 JP2012513381A5 JP2011541509A JP2011541509A JP2012513381A5 JP 2012513381 A5 JP2012513381 A5 JP 2012513381A5 JP 2011541509 A JP2011541509 A JP 2011541509A JP 2011541509 A JP2011541509 A JP 2011541509A JP 2012513381 A5 JP2012513381 A5 JP 2012513381A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- solvent
- xxa
- salt
- 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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- 238000000034 method Methods 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 16
- KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical class C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 claims 11
- 239000002904 solvent Substances 0.000 claims 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 7
- -1 bicyclic lactone amide Chemical class 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- 239000011877 solvent mixture Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 2
- GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- 238000010640 amide synthesis reaction Methods 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 238000001953 recrystallisation Methods 0.000 claims 2
- 239000000725 suspension Substances 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000007822 coupling agent Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 239000003759 ester based solvent Substances 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims 1
- 125000000686 lactone group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- QLSTWGZDXAHREY-UHFFFAOYSA-N n-methylhex-1-en-1-amine Chemical compound CCCCC=CNC QLSTWGZDXAHREY-UHFFFAOYSA-N 0.000 claims 1
- UGLYZKRVGNAOLZ-UHFFFAOYSA-N propan-2-yl 2-propan-2-yloxy-2h-quinoline-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OC(C)C)C(OC(C)C)C=CC2=C1 UGLYZKRVGNAOLZ-UHFFFAOYSA-N 0.000 claims 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- 125000005500 uronium group Chemical group 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- 0 C=CC1*(CC2)CC(C3(CC3)c3ccnc4ccccc34)N2C1 Chemical compound C=CC1*(CC2)CC(C3(CC3)c3ccnc4ccccc34)N2C1 0.000 description 11
- YWHQIVJPIBHBSV-UHFFFAOYSA-N OC(C(CC(C1)O2)C1C2=O)=O Chemical compound OC(C(CC(C1)O2)C1C2=O)=O YWHQIVJPIBHBSV-UHFFFAOYSA-N 0.000 description 3
- JTZZSQYMACOLNN-VDWJNHBNSA-N CC(C)c1c[s]c(-c2cc(O[C@H](C[C@H]3C(N[C@](C4)([C@@H]4/C=C\CCCCN4C)C(NS(C5CC5)(=O)=O)=O)=O)C[C@H]3C4=O)c(ccc(OC)c3C)c3n2)n1 Chemical compound CC(C)c1c[s]c(-c2cc(O[C@H](C[C@H]3C(N[C@](C4)([C@@H]4/C=C\CCCCN4C)C(NS(C5CC5)(=O)=O)=O)=O)C[C@H]3C4=O)c(ccc(OC)c3C)c3n2)n1 JTZZSQYMACOLNN-VDWJNHBNSA-N 0.000 description 2
- KMPWYEUPVWOPIM-NAHPKXJFSA-N C=CC1C(CC2)CC([C@@H](c3c(cccc4)c4ncc3)O)N2C1 Chemical compound C=CC1C(CC2)CC([C@@H](c3c(cccc4)c4ncc3)O)N2C1 KMPWYEUPVWOPIM-NAHPKXJFSA-N 0.000 description 1
- XQOBFRSIHBMNMC-PLGQPLIWSA-N CC(C)c1c[s]c(-c2cc(O[C@H](C[C@H]3C(N[C@](C4)([C@@H]4/C=C\CCCCN4C)C(O)=O)=O)C[C@H]3C4=O)c(ccc(OC)c3C)c3n2)n1 Chemical compound CC(C)c1c[s]c(-c2cc(O[C@H](C[C@H]3C(N[C@](C4)([C@@H]4/C=C\CCCCN4C)C(O)=O)=O)C[C@H]3C4=O)c(ccc(OC)c3C)c3n2)n1 XQOBFRSIHBMNMC-PLGQPLIWSA-N 0.000 description 1
- KKEQTCOFLWKZOY-MDNUFGMLSA-N CC(C)c1c[s]c(-c2nc(c(C)c(cc3)OC)c3c(O[C@@H](C[C@H]3C(N(C)CCCCC=C)=O)C[C@H]3C(O)=O)c2)n1 Chemical compound CC(C)c1c[s]c(-c2nc(c(C)c(cc3)OC)c3c(O[C@@H](C[C@H]3C(N(C)CCCCC=C)=O)C[C@H]3C(O)=O)c2)n1 KKEQTCOFLWKZOY-MDNUFGMLSA-N 0.000 description 1
- UTIOQBMMOGSBEA-IJWPFNNMSA-N CC(C1)C=Cc2c1c([C@H](C(CC1CC3)N3CC1C=C)O)ccn2 Chemical compound CC(C1)C=Cc2c1c([C@H](C(CC1CC3)N3CC1C=C)O)ccn2 UTIOQBMMOGSBEA-IJWPFNNMSA-N 0.000 description 1
- SEKCMPWEKHOBBR-UHFFFAOYSA-N CN(CCCCC=C)C(C(CC(C1)O2)C1C2=O)=O Chemical compound CN(CCCCC=C)C(C(CC(C1)O2)C1C2=O)=O SEKCMPWEKHOBBR-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08172691 | 2008-12-23 | ||
| EP08172691.1 | 2008-12-23 | ||
| PCT/EP2009/067715 WO2010072742A1 (en) | 2008-12-23 | 2009-12-22 | Processes and intermediates for preparing a macrocyclic protease inhibitor of hcv |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012513381A JP2012513381A (ja) | 2012-06-14 |
| JP2012513381A5 true JP2012513381A5 (enExample) | 2013-10-24 |
| JP5687631B2 JP5687631B2 (ja) | 2015-03-18 |
Family
ID=40548041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011541509A Expired - Fee Related JP5687631B2 (ja) | 2008-12-23 | 2009-12-22 | Ｈｃｖのマクロ環状プロテアーゼ阻害剤を製造するための方法および中間体 |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US8927722B2 (enExample) |
| EP (1) | EP2382198B1 (enExample) |
| JP (1) | JP5687631B2 (enExample) |
| KR (1) | KR101734507B1 (enExample) |
| CN (1) | CN102264715B (enExample) |
| AR (1) | AR074863A1 (enExample) |
| AU (1) | AU2009331530B2 (enExample) |
| BR (1) | BRPI0923393B1 (enExample) |
| CA (1) | CA2745565C (enExample) |
| CY (1) | CY1114488T1 (enExample) |
| DK (1) | DK2382198T3 (enExample) |
| ES (1) | ES2429013T3 (enExample) |
| HR (1) | HRP20130906T1 (enExample) |
| IL (1) | IL213246A (enExample) |
| MX (1) | MX2011006764A (enExample) |
| PL (1) | PL2382198T3 (enExample) |
| PT (1) | PT2382198E (enExample) |
| RU (1) | RU2016120007A (enExample) |
| SI (1) | SI2382198T1 (enExample) |
| SM (1) | SMT201300116B (enExample) |
| TW (1) | TWI461424B (enExample) |
| WO (1) | WO2010072742A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0923393B1 (pt) | 2008-12-23 | 2018-06-19 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | "processos para preparar um inibidor de protease de hcv macrocíclico e intermediários e uso". |
| KR20140063726A (ko) * | 2011-09-22 | 2014-05-27 | 얀센 파마슈티칼즈, 인코포레이티드 | Hcv의 거대고리 단백질 분해효소 억제제의 제조 방법 및 중간물질 |
| MX347650B (es) | 2011-10-28 | 2017-05-05 | Janssen Pharmaceuticals Inc | Procedimiento mejorado para preparar un compuesto intermedio del inhibidor de proteasa macrociclico tmc 435. |
| CN103387509B (zh) * | 2012-05-11 | 2016-06-08 | 重庆博腾制药科技股份有限公司 | 一种hcv蛋白酶抑制剂中间体的制备方法 |
| PT2861604T (pt) | 2012-06-08 | 2017-05-05 | Gilead Sciences Inc | Inibidores macrocíclicos de vírus flaviridae |
| AR091279A1 (es) * | 2012-06-08 | 2015-01-21 | Gilead Sciences Inc | Inhibidores macrociclicos de virus flaviviridae |
| ES2656087T3 (es) * | 2012-06-08 | 2018-02-23 | Gilead Sciences, Inc. | Inhibidores macrocíclicos de virus Flaviviridae |
| UA119315C2 (uk) | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
| ES2735355T3 (es) | 2013-03-15 | 2019-12-18 | Gilead Sciences Inc | Inhibidores macrocíclicos y bicíclicos de virus de hepatitis C |
| CN105308043B (zh) * | 2014-05-29 | 2018-01-30 | 杭州普晒医药科技有限公司 | 丙型肝炎药物的晶型及其制备方法、其药物组合物和用途 |
| MA41812A (fr) | 2015-03-27 | 2018-01-30 | Janssen Pharmaceuticals Inc | Procédés et intermédiaires pour la préparation d'un inhibiteur de protéase macrocyclique du vhc |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8300536A (nl) | 1983-02-14 | 1984-09-03 | Oce Andeno Bv | Optisch actief alfa-azido-p-hydroxyfenylazijnzuur en zijn zouten alsmede de bereiding daarvan. |
| JPS6124539A (ja) | 1984-07-11 | 1986-02-03 | Sagami Chem Res Center | 光学活性（ｒ）−２，５，１２−トリヒドロキシ−１，２，３，４−テトラヒドロナフタセン−６，１１−ジオン−２−カルボン酸の取得方法 |
| JP4218040B2 (ja) | 1997-12-26 | 2009-02-04 | 曽田香料株式会社 | 有機酸とアミンの複合塩の製造法 |
| JP3844112B2 (ja) | 2000-08-23 | 2006-11-08 | 高砂香料工業株式会社 | ３，５，６−トリヒドロキシヘキサン酸アンモニウム塩誘導体、及びその製造方法 |
| SI1713823T1 (sl) | 2004-01-30 | 2010-04-30 | Medivir Ab | Inhibitorji HCV NS-3 serin proteaze |
| CN101146794A (zh) | 2005-01-21 | 2008-03-19 | 阿斯泰克斯治疗有限公司 | 用于抑制cdk和gsk的吡唑衍生物 |
| JP5171624B2 (ja) * | 2005-07-29 | 2013-03-27 | テイボテク・フアーマシユーチカルズ | Ｃ型肝炎ウイルスの大環状阻害剤 |
| PE20070211A1 (es) | 2005-07-29 | 2007-05-12 | Medivir Ab | Compuestos macrociclicos como inhibidores del virus de hepatitis c |
| HRP20100429T1 (hr) * | 2007-02-01 | 2010-09-30 | Tibotec Pharmaceuticals | Postupci i intermedijeri za pripravu makrocikličkog inhibitora proteaze za hcv |
| JP5554570B2 (ja) * | 2007-02-08 | 2014-07-23 | ヤンセン・アールアンドデイ・アイルランド | Ｈｃｖ阻害大環状フェニルカルバメート |
| BRPI0923393B1 (pt) | 2008-12-23 | 2018-06-19 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | "processos para preparar um inibidor de protease de hcv macrocíclico e intermediários e uso". |
-
2009
- 2009-12-22 BR BRPI0923393-8A patent/BRPI0923393B1/pt not_active IP Right Cessation
- 2009-12-22 PL PL09801447T patent/PL2382198T3/pl unknown
- 2009-12-22 MX MX2011006764A patent/MX2011006764A/es active IP Right Grant
- 2009-12-22 CA CA2745565A patent/CA2745565C/en not_active Expired - Fee Related
- 2009-12-22 CN CN200980152851.5A patent/CN102264715B/zh not_active Expired - Fee Related
- 2009-12-22 AU AU2009331530A patent/AU2009331530B2/en not_active Ceased
- 2009-12-22 WO PCT/EP2009/067715 patent/WO2010072742A1/en not_active Ceased
- 2009-12-22 US US13/141,715 patent/US8927722B2/en not_active Expired - Fee Related
- 2009-12-22 AR ARP090105059 patent/AR074863A1/es unknown
- 2009-12-22 PT PT09801447T patent/PT2382198E/pt unknown
- 2009-12-22 HR HRP20130906AT patent/HRP20130906T1/hr unknown
- 2009-12-22 RU RU2016120007A patent/RU2016120007A/ru not_active Application Discontinuation
- 2009-12-22 TW TW98144049A patent/TWI461424B/zh not_active IP Right Cessation
- 2009-12-22 EP EP09801447.5A patent/EP2382198B1/en active Active
- 2009-12-22 ES ES09801447T patent/ES2429013T3/es active Active
- 2009-12-22 SI SI200930731T patent/SI2382198T1/sl unknown
- 2009-12-22 KR KR1020117017333A patent/KR101734507B1/ko not_active Expired - Fee Related
- 2009-12-22 JP JP2011541509A patent/JP5687631B2/ja not_active Expired - Fee Related
- 2009-12-22 DK DK09801447.5T patent/DK2382198T3/da active
-
2011
- 2011-05-31 IL IL213246A patent/IL213246A/en not_active IP Right Cessation
-
2013
- 2013-10-10 SM SM201300116T patent/SMT201300116B/xx unknown
- 2013-10-10 CY CY20131100890T patent/CY1114488T1/el unknown
-
2014
- 2014-11-25 US US14/552,550 patent/US9115077B2/en not_active Expired - Fee Related
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