JP2013522273A5 - - Google Patents
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- JP2013522273A5 JP2013522273A5 JP2012557537A JP2012557537A JP2013522273A5 JP 2013522273 A5 JP2013522273 A5 JP 2013522273A5 JP 2012557537 A JP2012557537 A JP 2012557537A JP 2012557537 A JP2012557537 A JP 2012557537A JP 2013522273 A5 JP2013522273 A5 JP 2013522273A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- alkyl
- oxo
- quin
- 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 17
- -1 bicyclic lactone Chemical class 0.000 claims 12
- 238000000034 method Methods 0.000 claims 12
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 238000006243 chemical reaction Methods 0.000 claims 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- KWGRBVOPPLSCSI-PSASIEDQSA-N (1s,2r)-2-(methylamino)-1-phenylpropan-1-ol Chemical compound CN[C@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-PSASIEDQSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 claims 3
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 claims 3
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims 3
- 238000002360 preparation method Methods 0.000 claims 3
- FKSHZARYGBOZDO-UHFFFAOYSA-N 4,5-dichloro-6-methoxytriazine Chemical compound COC1=NN=NC(Cl)=C1Cl FKSHZARYGBOZDO-UHFFFAOYSA-N 0.000 claims 2
- CJSMOECOKYPHSC-UHFFFAOYSA-N 4-oxocyclopentane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CC(=O)CC1C(O)=O CJSMOECOKYPHSC-UHFFFAOYSA-N 0.000 claims 2
- WMWOMMJQVXRFAP-UHFFFAOYSA-N 5-chloro-4,6-dimethoxytriazine Chemical compound COC1=NN=NC(OC)=C1Cl WMWOMMJQVXRFAP-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 claims 2
- QLSTWGZDXAHREY-UHFFFAOYSA-N n-methylhex-1-en-1-amine Chemical compound CCCCC=CNC QLSTWGZDXAHREY-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical class CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims 1
- CJSMOECOKYPHSC-RFZPGFLSSA-N (1r,2r)-4-oxocyclopentane-1,2-dicarboxylic acid Chemical compound OC(=O)[C@@H]1CC(=O)C[C@H]1C(O)=O CJSMOECOKYPHSC-RFZPGFLSSA-N 0.000 claims 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- MGNCLNQXLYJVJD-VMIGTVKRSA-N 2,4,6-trichloro-1,3,5-triazine Chemical group Cl[13C]1=N[13C](Cl)=N[13C](Cl)=N1 MGNCLNQXLYJVJD-VMIGTVKRSA-N 0.000 claims 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- NQVRMIOCJAWYNB-UHFFFAOYSA-N 3-oxocyclopentane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCC(=O)C1 NQVRMIOCJAWYNB-UHFFFAOYSA-N 0.000 claims 1
- BMTZEAOGFDXDAD-UHFFFAOYSA-M 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholin-4-ium;chloride Chemical compound [Cl-].COC1=NC(OC)=NC([N+]2(C)CCOCC2)=N1 BMTZEAOGFDXDAD-UHFFFAOYSA-M 0.000 claims 1
- RJLBLEIPNSPREJ-UHFFFAOYSA-N 4-hydroxycyclopentane-1,2-dicarboxylic acid Chemical compound OC1CC(C(O)=O)C(C(O)=O)C1 RJLBLEIPNSPREJ-UHFFFAOYSA-N 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 1
- 239000004280 Sodium formate Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000005604 azodicarboxylate group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 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
- 150000001940 cyclopentanes Chemical class 0.000 claims 1
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001033 ether group Chemical group 0.000 claims 1
- RUDVQBCFUZDOTA-UHFFFAOYSA-N hex-1-en-1-amine Chemical compound CCCCC=CN RUDVQBCFUZDOTA-UHFFFAOYSA-N 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 125000000686 lactone group Chemical group 0.000 claims 1
- 150000002596 lactones Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims 1
- 235000019254 sodium formate Nutrition 0.000 claims 1
- 238000005809 transesterification reaction Methods 0.000 claims 1
- 150000003918 triazines Chemical class 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10156681 | 2010-03-16 | ||
| EP10156681.8 | 2010-03-16 | ||
| PCT/EP2011/053957 WO2011113859A1 (en) | 2010-03-16 | 2011-03-16 | Processes and intermediates for preparing a macrocyclic protease inhibitor of hcv |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016021576A Division JP2016164143A (ja) | 2010-03-16 | 2016-02-08 | Ｈｃｖの大環状プロテアーゼ阻害剤の製造のための方法及び中間体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013522273A JP2013522273A (ja) | 2013-06-13 |
| JP2013522273A5 true JP2013522273A5 (enExample) | 2014-06-19 |
Family
ID=42342793
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012557537A Withdrawn JP2013522273A (ja) | 2010-03-16 | 2011-03-16 | Ｈｃｖの大環状プロテアーゼ阻害剤の製造のための方法及び中間体 |
| JP2016021576A Pending JP2016164143A (ja) | 2010-03-16 | 2016-02-08 | Ｈｃｖの大環状プロテアーゼ阻害剤の製造のための方法及び中間体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016021576A Pending JP2016164143A (ja) | 2010-03-16 | 2016-02-08 | Ｈｃｖの大環状プロテアーゼ阻害剤の製造のための方法及び中間体 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US9586893B2 (enExample) |
| EP (2) | EP3239129A1 (enExample) |
| JP (2) | JP2013522273A (enExample) |
| KR (1) | KR20130034012A (enExample) |
| CN (1) | CN103249708A (enExample) |
| AU (1) | AU2011229164B2 (enExample) |
| BR (1) | BR112012023296B1 (enExample) |
| CA (1) | CA2793129A1 (enExample) |
| IL (1) | IL221242A (enExample) |
| MX (1) | MX2012010678A (enExample) |
| RU (1) | RU2628081C2 (enExample) |
| WO (1) | WO2011113859A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2012010678A (es) * | 2010-03-16 | 2012-10-15 | Janssen Pharmaceuticals Inc | Procedimientos e intermediarios para preparar un inhibidor macrociclico de proteasa del virus de la hepatitis c. |
| JP6235473B2 (ja) * | 2011-09-22 | 2017-11-22 | ヤンセン ファーマシューティカルズ，インコーポレーテッド | 大環状ｈｃｖ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 |
| MX2017007854A (es) * | 2014-12-22 | 2017-09-19 | Colgate Palmolive Co | Suavizante para telas de dosis unitaria. |
| 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 (12)
| 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 |
| JPH06124539A (ja) | 1992-10-08 | 1994-05-06 | Sony Corp | ディジタルｖｔｒ |
| JPH08231469A (ja) * | 1995-02-23 | 1996-09-10 | Nippon Kayaku Co Ltd | シクロペンタンカルボン酸誘導体及びその製造法 |
| JPH11180930A (ja) * | 1997-12-22 | 1999-07-06 | Sumitomo Chem Co Ltd | 光学活性ｔｒａｎｓ−シクロブタンジカルボン酸類の製造方法 |
| DE10029139A1 (de) * | 2000-06-14 | 2002-01-03 | Sueddeutsche Kalkstickstoff | Verfahren zur Herstellung von Amiden oder Estern |
| MY153011A (en) | 2004-01-30 | 2014-12-31 | Medivir Ab | Hcv ns-3 serine protease inhibitors |
| CA2617099C (en) * | 2005-07-29 | 2014-03-25 | Tibotec Pharmaceuticals Ltd. | Macrocyclic inhibitors of hepatitis c virus |
| PE20070211A1 (es) * | 2005-07-29 | 2007-05-12 | Medivir Ab | Compuestos macrociclicos como inhibidores del virus de hepatitis c |
| US20070185346A1 (en) * | 2006-02-03 | 2007-08-09 | Vaidya Niteen A | Kit for automated resolving agent selection and method thereof |
| TWI455936B (zh) * | 2007-02-01 | 2014-10-11 | Tibotec Pharm Ltd | 用於製備ｈｃｖ之大環蛋白酶抑制劑之方法及中間物 |
| MX2012010678A (es) * | 2010-03-16 | 2012-10-15 | Janssen Pharmaceuticals Inc | Procedimientos e intermediarios para preparar un inhibidor macrociclico de proteasa del virus de la hepatitis c. |
-
2011
- 2011-03-16 MX MX2012010678A patent/MX2012010678A/es active IP Right Grant
- 2011-03-16 KR KR1020127024789A patent/KR20130034012A/ko not_active Ceased
- 2011-03-16 EP EP17166514.4A patent/EP3239129A1/en not_active Withdrawn
- 2011-03-16 CN CN2011800140694A patent/CN103249708A/zh active Pending
- 2011-03-16 RU RU2012143977A patent/RU2628081C2/ru not_active IP Right Cessation
- 2011-03-16 WO PCT/EP2011/053957 patent/WO2011113859A1/en not_active Ceased
- 2011-03-16 BR BR112012023296-7A patent/BR112012023296B1/pt not_active IP Right Cessation
- 2011-03-16 EP EP11709692.5A patent/EP2547645B1/en active Active
- 2011-03-16 CA CA2793129A patent/CA2793129A1/en not_active Abandoned
- 2011-03-16 JP JP2012557537A patent/JP2013522273A/ja not_active Withdrawn
- 2011-03-16 US US13/634,996 patent/US9586893B2/en not_active Expired - Fee Related
- 2011-03-16 AU AU2011229164A patent/AU2011229164B2/en not_active Ceased
-
2012
- 2012-08-01 IL IL221242A patent/IL221242A/en not_active IP Right Cessation
-
2016
- 2016-02-08 JP JP2016021576A patent/JP2016164143A/ja active Pending
-
2017
- 2017-02-10 US US15/429,250 patent/US20170152253A1/en not_active Abandoned
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