TWI574960B - 用於製備大環蛋白酶抑制劑ｔｍｃ４３５之中間體的改良方法 - Google Patents
用於製備大環蛋白酶抑制劑ｔｍｃ４３５之中間體的改良方法 Download PDFInfo
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- TWI574960B TWI574960B TW101139616A TW101139616A TWI574960B TW I574960 B TWI574960 B TW I574960B TW 101139616 A TW101139616 A TW 101139616A TW 101139616 A TW101139616 A TW 101139616A TW I574960 B TWI574960 B TW I574960B
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- iodide
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- reaction
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- 229960002091 simeprevir Drugs 0.000 title claims description 13
- JTZZSQYMACOLNN-VDWJNHBNSA-N simeprevir Chemical compound O=C([C@@]12C[C@H]1\C=C/CCCCN(C)C(=O)[C@H]1[C@H](C(N2)=O)C[C@H](C1)OC=1C2=CC=C(C(=C2N=C(C=1)C=1SC=C(N=1)C(C)C)C)OC)NS(=O)(=O)C1CC1 JTZZSQYMACOLNN-VDWJNHBNSA-N 0.000 title claims description 13
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
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- RXMRGBVLCSYIBO-UHFFFAOYSA-M tetramethylazanium;iodide Chemical compound [I-].C[N+](C)(C)C RXMRGBVLCSYIBO-UHFFFAOYSA-M 0.000 claims description 7
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 claims description 6
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 125000006684 polyhaloalkyl group Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 150000003304 ruthenium compounds Chemical class 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- SWGJCIMEBVHMTA-UHFFFAOYSA-K trisodium;6-oxido-4-sulfo-5-[(4-sulfonatonaphthalen-1-yl)diazenyl]naphthalene-2-sulfonate Chemical compound [Na+].[Na+].[Na+].C1=CC=C2C(N=NC3=C4C(=CC(=CC4=CC=C3O)S([O-])(=O)=O)S([O-])(=O)=O)=CC=C(S([O-])(=O)=O)C2=C1 SWGJCIMEBVHMTA-UHFFFAOYSA-K 0.000 description 1
- 150000003679 valine derivatives Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11187025 | 2011-10-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201323423A TW201323423A (zh) | 2013-06-16 |
| TWI574960B true TWI574960B (zh) | 2017-03-21 |
Family
ID=47221505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW101139616A TWI574960B (zh) | 2011-10-28 | 2012-10-26 | 用於製備大環蛋白酶抑制劑ｔｍｃ４３５之中間體的改良方法 |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US8981082B2 (enExample) |
| EP (1) | EP2771339B1 (enExample) |
| JP (1) | JP6231482B2 (enExample) |
| KR (1) | KR20140086967A (enExample) |
| CN (1) | CN104053658B (enExample) |
| AR (1) | AR088568A1 (enExample) |
| AU (1) | AU2012327934B2 (enExample) |
| BR (1) | BR112014009849A2 (enExample) |
| CA (1) | CA2848377A1 (enExample) |
| CL (1) | CL2014001043A1 (enExample) |
| EA (1) | EA201490892A1 (enExample) |
| ES (1) | ES2671732T3 (enExample) |
| HK (1) | HK1202120A1 (enExample) |
| IL (1) | IL231892A (enExample) |
| MX (1) | MX347650B (enExample) |
| TW (1) | TWI574960B (enExample) |
| WO (1) | WO2013061285A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2017064680A1 (en) * | 2015-10-16 | 2017-04-20 | Lupin Limited | An improved process for the preparation of simeprevir sodium and intermediate thereof |
| CN109846883A (zh) * | 2017-11-30 | 2019-06-07 | 常州寅盛药业有限公司 | 苯并呋喃衍生物与tmc435联合用药物 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007030656A1 (en) * | 2005-09-09 | 2007-03-15 | Boehringer Ingelheim International Gmbh | Ring-closing metathesis process for the preparation of macrocyclic peptides |
| TW201033205A (en) * | 2008-12-23 | 2010-09-16 | Ortho Mcneil Janssen Pharm | Processes and intermediates for preparing a macrocyclic protease inhibitor of HCV |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20060008877A (ko) | 2003-04-10 | 2006-01-27 | 베링거 인겔하임 인터내셔날 게엠베하 | 루테늄 착물 촉매 존재하의 복분해 반응에 의한거대사이클릭 화합물의 제조방법 |
| PE20070211A1 (es) * | 2005-07-29 | 2007-05-12 | Medivir Ab | Compuestos macrociclicos como inhibidores del virus de hepatitis c |
| EP2224920A4 (en) | 2007-12-06 | 2012-05-09 | Enanta Pharm Inc | PROCESS FOR THE PREPARATION OF MACROCYCLIC OXIMYL HEPATITIS C PROTEASE INHIBITORS |
| WO2010015545A1 (en) * | 2008-08-07 | 2010-02-11 | F. Hoffmann-La Roche Ag | Process for the preparation of a macrocycle |
-
2012
- 2012-10-26 JP JP2014537794A patent/JP6231482B2/ja not_active Expired - Fee Related
- 2012-10-26 AR ARP120104040A patent/AR088568A1/es unknown
- 2012-10-26 MX MX2014005070A patent/MX347650B/es active IP Right Grant
- 2012-10-26 ES ES12790677.4T patent/ES2671732T3/es active Active
- 2012-10-26 TW TW101139616A patent/TWI574960B/zh not_active IP Right Cessation
- 2012-10-26 CA CA2848377A patent/CA2848377A1/en not_active Abandoned
- 2012-10-26 HK HK15102687.7A patent/HK1202120A1/xx unknown
- 2012-10-26 KR KR1020147009887A patent/KR20140086967A/ko not_active Ceased
- 2012-10-26 WO PCT/IB2012/055900 patent/WO2013061285A1/en not_active Ceased
- 2012-10-26 CN CN201280052692.3A patent/CN104053658B/zh not_active Expired - Fee Related
- 2012-10-26 US US14/350,138 patent/US8981082B2/en not_active Expired - Fee Related
- 2012-10-26 EP EP12790677.4A patent/EP2771339B1/en active Active
- 2012-10-26 EA EA201490892A patent/EA201490892A1/ru unknown
- 2012-10-26 AU AU2012327934A patent/AU2012327934B2/en not_active Ceased
- 2012-10-26 BR BR112014009849A patent/BR112014009849A2/pt not_active IP Right Cessation
-
2014
- 2014-04-03 IL IL231892A patent/IL231892A/en not_active IP Right Cessation
- 2014-04-24 CL CL2014001043A patent/CL2014001043A1/es unknown
-
2015
- 2015-02-09 US US14/616,770 patent/US9328108B2/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007030656A1 (en) * | 2005-09-09 | 2007-03-15 | Boehringer Ingelheim International Gmbh | Ring-closing metathesis process for the preparation of macrocyclic peptides |
| TW201033205A (en) * | 2008-12-23 | 2010-09-16 | Ortho Mcneil Janssen Pharm | Processes and intermediates for preparing a macrocyclic protease inhibitor of HCV |
Non-Patent Citations (1)
| Title |
|---|
| Barry B. Snider, et al.,"Total Synthesis of (±)-Martinellic Acid", Org. Lett., 2001, Vol. 3, No. 26, 4217-4220 * |
Also Published As
| Publication number | Publication date |
|---|---|
| AR088568A1 (es) | 2014-06-18 |
| HK1202120A1 (en) | 2015-09-18 |
| ES2671732T3 (es) | 2018-06-08 |
| AU2012327934B2 (en) | 2017-06-01 |
| CN104053658A (zh) | 2014-09-17 |
| BR112014009849A2 (pt) | 2016-07-05 |
| US8981082B2 (en) | 2015-03-17 |
| JP2014530901A (ja) | 2014-11-20 |
| US20150152098A1 (en) | 2015-06-04 |
| WO2013061285A1 (en) | 2013-05-02 |
| EP2771339B1 (en) | 2018-04-18 |
| AU2012327934A1 (en) | 2014-03-20 |
| US9328108B2 (en) | 2016-05-03 |
| US20140235852A1 (en) | 2014-08-21 |
| JP6231482B2 (ja) | 2017-11-15 |
| CN104053658B (zh) | 2018-03-13 |
| EA201490892A1 (ru) | 2014-08-29 |
| EP2771339A1 (en) | 2014-09-03 |
| IL231892A (en) | 2017-09-28 |
| MX347650B (es) | 2017-05-05 |
| KR20140086967A (ko) | 2014-07-08 |
| TW201323423A (zh) | 2013-06-16 |
| IL231892A0 (en) | 2014-05-28 |
| CL2014001043A1 (es) | 2014-07-25 |
| CA2848377A1 (en) | 2013-05-02 |
| MX2014005070A (es) | 2014-08-22 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |