ES2401731T3 - Compuestos macrocíclicos como inhibidores del virus de la hepatitis C - Google Patents

Compuestos macrocíclicos como inhibidores del virus de la hepatitis C Download PDF

Info

Publication number: ES2401731T3
Authority: ES; Spain
Prior art keywords: mmol; alkyl; compound; solvent; hcv
Prior art date: 2008-09-29
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.): Active

Application number

ES09792995T

Other languages

English (en)

Spanish (es)

Inventor

Sheldon Hiebert

Ramkumar Rajamani

Paul Michael Scola

Michael S. Bowsher

Rongti Li

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bristol Myers Squibb Co

Original Assignee

Bristol Myers Squibb Co

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.)

2008-09-29

Filing date

2009-09-25

Publication date

2013-04-24

2009-09-25 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

2013-04-24 Application granted granted Critical

2013-04-24 Publication of ES2401731T3 publication Critical patent/ES2401731T3/es

Status Active legal-status Critical Current

2029-09-25 Anticipated expiration legal-status Critical

Links

239000003112 inhibitor Substances 0.000 title description 27
241000711549 Hepacivirus C Species 0.000 title description 4
150000002678 macrocyclic compounds Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 152
125000000217 alkyl group Chemical group 0.000 claims abstract description 72
150000003839 salts Chemical class 0.000 claims abstract description 53
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 46
125000005843 halogen group Chemical group 0.000 claims abstract description 23
239000001257 hydrogen Substances 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 21
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 18
125000003342 alkenyl group Chemical group 0.000 claims abstract description 16
125000003118 aryl group Chemical group 0.000 claims abstract description 16
150000002431 hydrogen Chemical group 0.000 claims abstract description 13
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 10
125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 10
229920006395 saturated elastomer Polymers 0.000 claims abstract description 10
125000004415 heterocyclylalkyl group Chemical group 0.000 claims abstract description 8
229910003827 NRaRb Inorganic materials 0.000 claims abstract description 7
229910052799 carbon Inorganic materials 0.000 claims abstract description 6
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 4
125000004966 cyanoalkyl group Chemical group 0.000 claims abstract description 4
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
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229960000329 ribavirin Drugs 0.000 claims description 17
HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 17
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SVSAEDMUQANHDP-GMAHTHKFSA-N methyl (2s,4r)-4-[4-[4-(dimethylamino)-2-ethenylphenyl]phenyl]-4-methoxypyrrolidine-2-carboxylate Chemical compound C1N[C@H](C(=O)OC)C[C@@]1(OC)C1=CC=C(C=2C(=CC(=CC=2)N(C)C)C=C)C=C1 SVSAEDMUQANHDP-GMAHTHKFSA-N 0.000 description 1
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239000007858 starting material Substances 0.000 description 1
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229940086735 succinate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
235000011044 succinic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid group Chemical group C(CCC(=O)O)(=O)O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
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NHKZSTHOYNWEEZ-AFCXAGJDSA-N taribavirin Chemical compound N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NHKZSTHOYNWEEZ-AFCXAGJDSA-N 0.000 description 1
229950006081 taribavirin Drugs 0.000 description 1
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CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
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JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
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IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
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YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
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GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
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ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/18—Bridged systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Virology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Molecular Biology (AREA)
Gastroenterology & Hepatology (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

ES09792995T 2008-09-29 2009-09-25 Compuestos macrocíclicos como inhibidores del virus de la hepatitis C Active ES2401731T3 (es)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US10090108P	2008-09-29	2008-09-29
US100901P		2008-09-29
US566441		2009-09-24
US12/566,441 US8563505B2 (en)	2008-09-29	2009-09-24	Hepatitis C virus inhibitors
PCT/US2009/058342 WO2010036871A1 (en)	2008-09-29	2009-09-25	Macrocyclic compounds as hepatitis c virus inhibitors

Publications (1)

Publication Number	Publication Date
ES2401731T3 true ES2401731T3 (es)	2013-04-24

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ES09792995T Active ES2401731T3 (es)	2008-09-29	2009-09-25	Compuestos macrocíclicos como inhibidores del virus de la hepatitis C

Country Status (6)

Country	Link
US (1)	US8563505B2 (2)
EP (1)	EP2337784B1 (2)
JP (1)	JP2012504129A (2)
CN (1)	CN102227436A (2)
ES (1)	ES2401731T3 (2)
WO (1)	WO2010036871A1 (2)

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WO2009142842A2 (en) *	2008-04-15	2009-11-26	Intermune, Inc.	Novel macrocyclic inhibitors of hepatitis c virus replication
US8207341B2 (en)	2008-09-04	2012-06-26	Bristol-Myers Squibb Company	Process or synthesizing substituted isoquinolines
UY32099A (es)	2008-09-11	2010-04-30	Enanta Pharm Inc	Inhibidores macrocíclicos de serina proteasas de hepatitis c
KR20110075019A (ko) *	2008-10-15	2011-07-05	인터뮨, 인크.	치료용 항바이러스성 펩티드
AR075584A1 (es)	2009-02-27	2011-04-20	Intermune Inc	COMPOSICIONES TERAPEUTICAS QUE COMPRENDEN beta-D-2'-DESOXI-2'-FLUORO-2'-C-METILCITIDINA Y UN DERIVADO DE ACIDO ISOINDOL CARBOXILICO Y SUS USOS. COMPUESTO.
US8936781B2 (en)	2009-05-13	2015-01-20	Enanta Pharmaceuticals, Inc.	Macrocyclic compounds as hepatitis C virus inhibitors
CN102741270B (zh) *	2009-09-28	2015-07-22	英特穆恩公司	C型肝炎病毒复制的环肽抑制剂
US9193740B2 (en) *	2009-10-19	2015-11-24	Enanta Pharmaceuticals, Inc.	Bismacrocyclic compounds as hepatitis C virus inhibitors
CA2822357A1 (en)	2010-12-22	2012-06-28	Abbvie Inc.	Hepatitis c inhibitors and uses thereof
KR20140003521A (ko)	2010-12-30	2014-01-09	이난타 파마슈티칼스, 인코포레이티드	페난트리딘 매크로사이클릭 ｃ형 간염 세린 프로테아제 억제제
EP2658859A4 (en)	2010-12-30	2014-07-30	Enanta Pharm Inc	MACROCYCLIC HEPATITIS C SERIN PROTEASE INHIBITORS
US8957203B2 (en)	2011-05-05	2015-02-17	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
US10201584B1 (en)	2011-05-17	2019-02-12	Abbvie Inc.	Compositions and methods for treating HCV
US8691757B2 (en)	2011-06-15	2014-04-08	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
JP6068505B2 (ja) *	2012-01-11	2017-01-25	エフ．ホフマン−ラロシュアーゲーＦ．Ｈｏｆｆｍａｎｎ−ＬａＲｏｃｈｅＡｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ	プロテアーゼ阻害剤としてのマクロ環式アミド
UA119315C2 (uk)	2012-07-03	2019-06-10	Гіліад Фармассет Елелсі	Інгібітори вірусу гепатиту с
EA025560B1 (ru)	2012-10-19	2017-01-30	Бристол-Майерс Сквибб Компани	Ингибиторы вируса гепатита с
WO2014071007A1 (en)	2012-11-02	2014-05-08	Bristol-Myers Squibb Company	Hepatitis c virus inhibitors
US9643999B2 (en)	2012-11-02	2017-05-09	Bristol-Myers Squibb Company	Hepatitis C virus inhibitors
WO2014070964A1 (en)	2012-11-02	2014-05-08	Bristol-Myers Squibb Company	Hepatitis c virus inhibitors
EP2914614B1 (en)	2012-11-05	2017-08-16	Bristol-Myers Squibb Company	Hepatitis c virus inhibitors
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- 2009-09-25 EP EP09792995A patent/EP2337784B1/en not_active Not-in-force
- 2009-09-25 JP JP2011529247A patent/JP2012504129A/ja not_active Ceased
- 2009-09-25 CN CN2009801479542A patent/CN102227436A/zh active Pending

Also Published As

Publication number	Publication date
EP2337784A1 (en)	2011-06-29
CN102227436A (zh)	2011-10-26
US8563505B2 (en)	2013-10-22
EP2337784B1 (en)	2013-01-16
WO2010036871A1 (en)	2010-04-01
US20100080771A1 (en)	2010-04-01
JP2012504129A (ja)	2012-02-16

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