HRP20100429T1 - Postupci i intermedijeri za pripravu makrocikličkog inhibitora proteaze za hcv - Google Patents

Postupci i intermedijeri za pripravu makrocikličkog inhibitora proteaze za hcv Download PDF

Info

Publication number: HRP20100429T1
Authority: HR; Croatia
Prior art keywords: formula; compound; reaction; ester; bis
Prior art date: 2007-02-01

Application number

HR20100429T

Other languages

English (en)

Croatian (hr)

Inventor

Horvath Andras

Paul Michel Depr� Dominique

John Ormerod Dominic

Original Assignee

Tibotec Pharmaceuticals

Priority date (The priority date 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 date listed.)

2007-02-01

Filing date

2010-08-02

Publication date

2010-09-30

2010-08-02 Application filed by Tibotec Pharmaceuticals filed Critical Tibotec Pharmaceuticals

2010-09-30 Publication of HRP20100429T1 publication Critical patent/HRP20100429T1/hr

Links

238000000034 method Methods 0.000 title claims abstract 22
229940124158 Protease/peptidase inhibitor Drugs 0.000 title 1
239000000543 intermediate Substances 0.000 title 1
239000000137 peptide hydrolase inhibitor Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract 32
238000006243 chemical reaction Methods 0.000 claims abstract 12
-1 cyclopropylamino ester Chemical class 0.000 claims abstract 12
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 8
239000002253 acid Substances 0.000 claims abstract 4
239000012467 final product Substances 0.000 claims abstract 3
150000003839 salts Chemical class 0.000 claims 7
239000003054 catalyst Substances 0.000 claims 5
239000002585 base Substances 0.000 claims 4
239000003638 chemical reducing agent Substances 0.000 claims 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
229910052782 aluminium Inorganic materials 0.000 claims 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 3
150000001408 amides Chemical class 0.000 claims 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
229910052739 hydrogen Inorganic materials 0.000 claims 3
239000001257 hydrogen Substances 0.000 claims 3
229910052751 metal Inorganic materials 0.000 claims 3
239000002184 metal Substances 0.000 claims 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
239000000203 mixture Substances 0.000 claims 3
BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
239000011230 binding agent Substances 0.000 claims 2
125000002843 carboxylic acid group Chemical group 0.000 claims 2
239000003245 coal Substances 0.000 claims 2
235000019253 formic acid Nutrition 0.000 claims 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
239000012442 inert solvent Substances 0.000 claims 2
150000002763 monocarboxylic acids Chemical class 0.000 claims 2
150000007530 organic bases Chemical class 0.000 claims 2
239000003960 organic solvent Substances 0.000 claims 2
229910052697 platinum Inorganic materials 0.000 claims 2
150000004322 quinolinols Chemical class 0.000 claims 2
229910052703 rhodium Inorganic materials 0.000 claims 2
239000010948 rhodium Substances 0.000 claims 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical group [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims 2
238000000926 separation method Methods 0.000 claims 2
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims 2
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 1
JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 1
GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical group C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 1
239000003377 acid catalyst Substances 0.000 claims 1
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
150000003973 alkyl amines Chemical class 0.000 claims 1
125000005604 azodicarboxylate group Chemical group 0.000 claims 1
235000019445 benzyl alcohol Nutrition 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
239000003795 chemical substances by application Substances 0.000 claims 1
239000007822 coupling agent Substances 0.000 claims 1
BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 claims 1
125000004185 ester group Chemical group 0.000 claims 1
125000001033 ether group Chemical group 0.000 claims 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
125000000468 ketone group Chemical group 0.000 claims 1
150000002596 lactones Chemical class 0.000 claims 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
XDYRBRLMIGIKQW-UHFFFAOYSA-N n-cyclopentylhydroxylamine Chemical compound ONC1CCCC1 XDYRBRLMIGIKQW-UHFFFAOYSA-N 0.000 claims 1
KKIMETYRXLWWSD-UHFFFAOYSA-N n-methylhex-5-en-1-amine Chemical compound CNCCCCC=C KKIMETYRXLWWSD-UHFFFAOYSA-N 0.000 claims 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 claims 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 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
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims 1
PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 claims 1
229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
229920001843 polymethylhydrosiloxane Polymers 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical compound C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims 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
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/58—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/82—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/56—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Virology (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Communicable Diseases (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

HR20100429T 2007-02-01 2010-08-02 Postupci i intermedijeri za pripravu makrocikličkog inhibitora proteaze za hcv HRP20100429T1 (hr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP07101571		2007-02-01
PCT/EP2008/051269 WO2008092955A1 (en)	2007-02-01	2008-02-01	Processes and intermediates for preparing a macrocyclic protease inhibitor of hcv

Publications (1)

Publication Number	Publication Date
HRP20100429T1 true HRP20100429T1 (hr)	2010-09-30

Family

ID=38337997

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR20100429T HRP20100429T1 (hr)	2007-02-01	2010-08-02	Postupci i intermedijeri za pripravu makrocikličkog inhibitora proteaze za hcv

Country Status (25)

Country	Link
US (2)	US8212043B2 (es)
EP (1)	EP2121674B1 (es)
JP (1)	JP5563830B2 (es)
KR (1)	KR101598135B1 (es)
CN (3)	CN105111200A (es)
AR (1)	AR065137A1 (es)
AT (1)	ATE467630T1 (es)
AU (1)	AU2008209697B2 (es)
BR (1)	BRPI0806853B1 (es)
CA (1)	CA2677173C (es)
CL (1)	CL2008000322A1 (es)
CY (1)	CY1110893T1 (es)
DE (1)	DE602008001251D1 (es)
DK (1)	DK2121674T3 (es)
ES (1)	ES2345857T3 (es)
HK (3)	HK1137442A1 (es)
HR (1)	HRP20100429T1 (es)
IL (1)	IL199276A (es)
MX (1)	MX2009008271A (es)
PL (1)	PL2121674T3 (es)
PT (1)	PT2121674E (es)
RU (1)	RU2483067C2 (es)
SI (1)	SI2121674T1 (es)
TW (1)	TWI455936B (es)
WO (1)	WO2008092955A1 (es)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MY140680A (en)	2002-05-20	2010-01-15	Bristol Myers Squibb Co	Hepatitis c virus inhibitors
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
US8207341B2 (en)	2008-09-04	2012-06-26	Bristol-Myers Squibb Company	Process or synthesizing substituted isoquinolines
KR101734507B1 (ko) *	2008-12-23	2017-05-11	얀센 파마슈티칼스 인코포레이티드	Ｈｃｖ의 마크로시클릭 프로테아제 억제제를 제조하기 위한 방법 및 중간체
DK2401272T3 (en) *	2009-02-27	2017-02-27	Janssen Pharmaceuticals Inc	AMORF SALT OF A MACROCYCLIC INHIBITOR OF HCV
CA2758072A1 (en)	2009-04-08	2010-10-14	Idenix Pharmaceuticals, Inc.	Macrocyclic serine protease inhibitors
WO2011017389A1 (en)	2009-08-05	2011-02-10	Idenix Pharmaceuticals, Inc.	Macrocyclic serine protease inhibitors useful against viral infections, particularly hcv
ES2644804T3 (es)	2010-01-27	2017-11-30	Ab Pharma Ltd	Compuestos poliheterocíclicos como inhibidores de HCV
KR20130034012A (ko) *	2010-03-16	2013-04-04	얀센 파마슈티칼즈, 인코포레이티드	Ｈｃｖ의 마크로사이클릭 프로테아제 저해제를 제조하기 위한 방법 및 중간체
TW201309690A (zh)	2011-02-10	2013-03-01	Idenix Pharmaceuticals Inc	巨環絲胺酸蛋白酶抑制劑，其醫藥組合物及其於治療ｈｃｖ感染之用途
US8957203B2 (en)	2011-05-05	2015-02-17	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US8691757B2 (en)	2011-06-15	2014-04-08	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
WO2012171332A1 (zh)	2011-06-16	2012-12-20	爱博新药研发(上海)有限公司	抑制丙型肝炎病毒的大环状杂环化合物及其制备和应用
AR087993A1 (es) *	2011-09-22	2014-04-30	Janssen Pharmaceuticals Inc	Procesos e intermediarios para la preparacion de un inhibidor macrociclico de la proteasa del hcv
RS61500B1 (sr)	2012-03-01	2021-03-31	Array Biopharma Inc	Inhibitori serinske/treoninske kinaze
JP6158168B2 (ja) *	2012-03-14	2017-07-05	積水メディカル株式会社	光学活性２−ビニルシクロプロパン−１，１−ジカルボン酸エステルの製造法
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
BR112015007879A2 (pt)	2012-10-19	2017-07-04	Bristol Myers Squibb Co	inibidores do vírus da hepatite c
US9643999B2 (en)	2012-11-02	2017-05-09	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
EP2914613B1 (en)	2012-11-02	2017-11-22	Bristol-Myers Squibb Company	Hepatitis c virus inhibitors
EP2914598B1 (en)	2012-11-02	2017-10-18	Bristol-Myers Squibb Company	Hepatitis c virus inhibitors
EP2914614B1 (en)	2012-11-05	2017-08-16	Bristol-Myers Squibb Company	Hepatitis c virus inhibitors
FR2998892B1 (fr)	2012-12-04	2015-01-02	Pf Medicament	Derives d'aminocyclobutane, leur procede de preparation et leur utilisation a titre de medicaments
JP6342922B2 (ja)	2013-03-07	2018-06-13	ブリストル−マイヤーズスクイブカンパニーＢｒｉｓｔｏｌ−ＭｙｅｒｓＳｑｕｉｂｂＣｏｍｐａｎｙ	Ｃ型肝炎ウイルス阻害剤
CN105237528B (zh) *	2014-06-09	2019-06-04	深圳翰宇药业股份有限公司	Hcv抑制剂的中间体以及由其制备hcv抑制剂的方法
CN105175406B (zh) *	2014-06-09	2019-06-04	深圳翰宇药业股份有限公司	Hcv抑制剂的中间体以及由其制备hcv抑制剂的方法
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
CN107098805A (zh) *	2017-05-17	2017-08-29	盐城同泰化工科技有限公司	一种4‑环戊酮‑1，2‑二甲酸的制备方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
UA74546C2 (en)	1999-04-06	2006-01-16	Boehringer Ingelheim Ca Ltd	Macrocyclic peptides having activity relative to hepatitis c virus, a pharmaceutical composition and use of the pharmaceutical composition
US7125845B2 (en)	2003-07-03	2006-10-24	Enanta Pharmaceuticals, Inc.	Aza-peptide macrocyclic hepatitis C serine protease inhibitors
US7608590B2 (en)	2004-01-30	2009-10-27	Medivir Ab	HCV NS-3 serine protease inhibitors
PE20070211A1 (es) *	2005-07-29	2007-05-12	Medivir Ab	Compuestos macrociclicos como inhibidores del virus de hepatitis c
PE20070343A1 (es) *	2005-07-29	2007-05-12	Medivir Ab	Inhibidores macrociclicos del virus de la hepatitis c
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

2008
- 2008-02-01 TW TW097103908A patent/TWI455936B/zh not_active IP Right Cessation
- 2008-02-01 BR BRPI0806853-4A patent/BRPI0806853B1/pt not_active IP Right Cessation
- 2008-02-01 DE DE602008001251T patent/DE602008001251D1/de active Active
- 2008-02-01 AU AU2008209697A patent/AU2008209697B2/en not_active Ceased
- 2008-02-01 CN CN201510477307.5A patent/CN105111200A/zh active Pending
- 2008-02-01 MX MX2009008271A patent/MX2009008271A/es active IP Right Grant
- 2008-02-01 PL PL08708576T patent/PL2121674T3/pl unknown
- 2008-02-01 AT AT08708576T patent/ATE467630T1/de active
- 2008-02-01 EP EP08708576A patent/EP2121674B1/en active Active
- 2008-02-01 RU RU2009132673/04A patent/RU2483067C2/ru not_active IP Right Cessation
- 2008-02-01 DK DK08708576.7T patent/DK2121674T3/da active
- 2008-02-01 US US12/441,927 patent/US8212043B2/en not_active Expired - Fee Related
- 2008-02-01 KR KR1020097015349A patent/KR101598135B1/ko not_active IP Right Cessation
- 2008-02-01 PT PT08708576T patent/PT2121674E/pt unknown
- 2008-02-01 JP JP2009547703A patent/JP5563830B2/ja not_active Expired - Fee Related
- 2008-02-01 CA CA2677173A patent/CA2677173C/en not_active Expired - Fee Related
- 2008-02-01 ES ES08708576T patent/ES2345857T3/es active Active
- 2008-02-01 CL CL200800322A patent/CL2008000322A1/es unknown
- 2008-02-01 SI SI200830052T patent/SI2121674T1/sl unknown
- 2008-02-01 WO PCT/EP2008/051269 patent/WO2008092955A1/en active Application Filing
- 2008-02-01 CN CN201310036125.5A patent/CN103145699B/zh not_active Expired - Fee Related
- 2008-02-01 AR ARP080100428A patent/AR065137A1/es unknown
- 2008-02-01 CN CN200880003655.7A patent/CN101600713B/zh not_active Expired - Fee Related
2009
- 2009-06-10 IL IL199276A patent/IL199276A/en active IP Right Grant
2010
- 2010-02-04 HK HK10101245.9A patent/HK1137442A1/xx not_active IP Right Cessation
- 2010-08-02 HR HR20100429T patent/HRP20100429T1/hr unknown
- 2010-08-09 CY CY20101100740T patent/CY1110893T1/el unknown
2012
- 2012-05-31 US US13/484,881 patent/US8722892B2/en not_active Expired - Fee Related
2013
- 2013-12-11 HK HK13113792.8A patent/HK1186458A1/zh not_active IP Right Cessation
2016
- 2016-05-26 HK HK16106009.8A patent/HK1217952A1/zh unknown

Also Published As

Publication number	Publication date
KR20090107038A (ko)	2009-10-12
TW200846346A (en)	2008-12-01
AU2008209697A1 (en)	2008-08-07
US20100041889A1 (en)	2010-02-18
KR101598135B1 (ko)	2016-02-26
CN101600713A (zh)	2009-12-09
CA2677173A1 (en)	2008-08-07
AU2008209697B2 (en)	2014-02-20
CN103145699B (zh)	2015-09-09
IL199276A (en)	2014-12-31
JP2010517972A (ja)	2010-05-27
HK1186458A1 (zh)	2014-03-14
TWI455936B (zh)	2014-10-11
MX2009008271A (es)	2009-08-12
HK1217952A1 (zh)	2017-01-27
DE602008001251D1 (de)	2010-06-24
RU2009132673A (ru)	2011-03-10
DK2121674T3 (da)	2010-09-13
CL2008000322A1 (es)	2008-09-05
CN105111200A (zh)	2015-12-02
EP2121674A1 (en)	2009-11-25
CA2677173C (en)	2017-12-12
CY1110893T1 (el)	2015-06-10
US20120238746A1 (en)	2012-09-20
WO2008092955A1 (en)	2008-08-07
PT2121674E (pt)	2010-09-03
BRPI0806853B1 (pt)	2018-03-20
ES2345857T3 (es)	2010-10-04
AR065137A1 (es)	2009-05-20
ATE467630T1 (de)	2010-05-15
US8212043B2 (en)	2012-07-03
PL2121674T3 (pl)	2010-10-29
CN101600713B (zh)	2014-11-12
HK1137442A1 (en)	2010-07-30
JP5563830B2 (ja)	2014-07-30
EP2121674B1 (en)	2010-05-12
RU2483067C2 (ru)	2013-05-27
SI2121674T1 (sl)	2010-09-30
CN103145699A (zh)	2013-06-12
BRPI0806853A2 (pt)	2014-04-29
US8722892B2 (en)	2014-05-13

Publication	Publication Date	Title
HRP20100429T1 (hr)	2010-09-30	Postupci i intermedijeri za pripravu makrocikličkog inhibitora proteaze za hcv
CN100355732C (zh)	2007-12-19	2－氯－5－氟－烟酸酯及酸的制备方法
CN102264715B (zh)	2015-12-02	用于制备hcv的大环蛋白酶抑制剂的方法及中间体
NZ598172A (en)	2013-08-30	Synthesis of boronic ester and acid compounds
CA2598347A1 (en)	2006-08-31	Isoxazoline derivative and novel process for its preparation
CN110204486B (zh)	2022-12-23	一种喹啉衍生物的合成方法
CN103649086A (zh)	2014-03-19	制备萘啶的方法
JP2675992B2 (ja)	1997-11-12	二環式アミノカルボン酸誘導体の製造方法
CN108148044B (zh)	2024-05-14	酰胺类化合物及该化合物制备富马酸沃诺拉赞的方法
CN111320577B (zh)	2023-06-23	一种吡啶酰胺的制备方法及其应用
JPH0764838B2 (ja)	1995-07-12	２ｒ−ベンジルクロマン−６−カルバルデヒド製造用中間体
CN109422685A (zh)	2019-03-05	一种n-乙酰基菲啶-6-酰胺及其衍生物的合成方法
JP4491412B2 (ja)	2010-06-30	Ｌ−γ−メチレングルタミン酸とその類似化合物の合成方法
CN106866463B (zh)	2018-08-28	艾沙度林中间体的制备方法
KR101585077B1 (ko)	2016-01-13	산쇼올류의 제조 방법
CN105481865A (zh)	2016-04-13	一种嘧啶并[1,6-a]吲哚杂环衍生物的制备方法
CN107383033A (zh)	2017-11-24	顺式5‑叔丁氧羰基‑四氢呋喃并[3,4‑c]吡咯‑3A‑羧酸甲酯的合成方法
US6258956B1 (en)	2001-07-10	Synthesis of 3-amino-3-aryl propanoates
CN103739606A (zh)	2014-04-23	2-氨基-5,8-二取代[1,2,4]***[1,5-c]嘧啶的环保合成方法
JP2011520876A (ja)	2011-07-21	ＨＭＧ−ＣｏＡ還元阻害剤の製造のためのキラル中間体の製造方法
KR20070082985A (ko)	2007-08-23	오셀타미비르의 제조방법
CN109317195B (zh)	2021-08-13	一种含有酸基的金鸡纳碱伯胺催化剂及其合成方法和在不对称反应中的应用
CN114773256B (zh)	2024-05-03	一种4-氰基哌啶的合成方法
CN115677639B (zh)	2024-02-06	一种四氢-3-氧代-2h-吡喃-4-羧酸甲酯中间体的制备方法
CN110981795B (zh)	2021-02-12	一种利用2-氰基异烟酸甲酯制备2-氨酰基异烟酸的方法