TWI461424B - 製備ｈｃｖ之巨環蛋白酶抑制劑的方法及中間體 - Google Patents

製備ｈｃｖ之巨環蛋白酶抑制劑的方法及中間體 Download PDF

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Publication number
TWI461424B
TWI461424B TW98144049A TW98144049A TWI461424B TW I461424 B TWI461424 B TW I461424B TW 98144049 A TW98144049 A TW 98144049A TW 98144049 A TW98144049 A TW 98144049A TW I461424 B TWI461424 B TW I461424B
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TW
Taiwan
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formula
solvent
compound
mixture
salt
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TW98144049A
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English (en)
Chinese (zh)
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TW201033205A (en
Inventor
Andras Horvath
Dominic John Ormerod
Dominique Paul Michel Depre
Veronioue Cerpentier
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Ortho Mcneil Janssen Pharm
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Publication of TW201033205A publication Critical patent/TW201033205A/zh
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • 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
    • 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
    • C07C235/40—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/475—Preparation of carboxylic acid esters by splitting of carbon-to-carbon bonds and redistribution, e.g. disproportionation or migration of groups between different molecules
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/32—Oxygen atoms
    • C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
    • C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
    • C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Virology (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Peptides Or Proteins (AREA)
  • Furan Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
TW98144049A 2008-12-23 2009-12-22 製備ｈｃｖ之巨環蛋白酶抑制劑的方法及中間體 TWI461424B (zh)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP08172691 2008-12-23

Publications (2)

Publication Number Publication Date
TW201033205A TW201033205A (en) 2010-09-16
TWI461424B true TWI461424B (zh) 2014-11-21

Family

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Family Applications (1)

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TW98144049A TWI461424B (zh) 2008-12-23 2009-12-22 製備ｈｃｖ之巨環蛋白酶抑制劑的方法及中間體

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)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK2382198T3 (da) 2008-12-23 2013-09-30 Janssen Pharmaceuticals Inc Fremgangsmåder og mellemprodukter til fremstilling af en makrocyklisk inhibitor af hcv-protease
TWI565704B (zh) 2011-09-22 2017-01-11 健生醫藥公司 用於製備ｈｃｖ巨環蛋白酶抑制劑之方法及中間物
JP6231482B2 (ja) 2011-10-28 2017-11-15 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 大環状プロテアーゼ阻害剤ｔｍｃ４３５の中間体の改善された製造方法
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
IN2014MN02652A (enExample) 2012-06-08 2015-08-21 Gilead Sciences Inc
AR091279A1 (es) * 2012-06-08 2015-01-21 Gilead Sciences Inc Inhibidores macrociclicos de virus flaviviridae
SI2859009T1 (sl) * 2012-06-08 2017-12-29 Gilead Sciences, Inc. Makrociklični inhibitorji flaviviridae virusov
UA119315C2 (uk) 2012-07-03 2019-06-10 Гіліад Фармассет Елелсі Інгібітори вірусу гепатиту с
JP6511432B2 (ja) 2013-03-15 2019-05-15 ギリアード サイエンシーズ， インコーポレイテッド Ｃ型肝炎ウイルスの大環状二環式阻害剤
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

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005073195A2 (en) * 2004-01-30 2005-08-11 Medivir Ab Hcv ns-3 serine protease inhibitors
WO2008092955A1 (en) * 2007-02-01 2008-08-07 Tibotec Pharmaceuticals Ltd. Processes and intermediates for preparing a macrocyclic protease inhibitor of hcv

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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
CN101146806A (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
EP1919904B1 (en) * 2005-07-29 2014-01-08 Janssen R&D Ireland 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
MX2009008541A (es) * 2007-02-08 2009-08-18 Tibotec Pharm Ltd Fenilcarbamatos macrociclicos que inhiben el virus de hepatitis c.
DK2382198T3 (da) 2008-12-23 2013-09-30 Janssen Pharmaceuticals Inc Fremgangsmåder og mellemprodukter til fremstilling af en makrocyklisk inhibitor af hcv-protease

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005073195A2 (en) * 2004-01-30 2005-08-11 Medivir Ab Hcv ns-3 serine protease inhibitors
WO2008092955A1 (en) * 2007-02-01 2008-08-07 Tibotec Pharmaceuticals Ltd. Processes and intermediates for preparing a macrocyclic protease inhibitor of hcv

Non-Patent Citations (1)

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Title
ROSENQUIST, A et al.," SYNTHESIS OF ENANTIOMERICALLY PURE TRANS-3,4-SUBSTITUTED CYCLOPENTANOLS BY ENZYMATIC RESOLUTION", ACTA CHEMICA SCANDINAVICA, 卷: 46, 期: 11, 頁碼: 1127-1129, 出版日期: NOV 1992 *

Also Published As

Publication number Publication date
KR20110099048A (ko) 2011-09-05
MX2011006764A (es) 2011-08-03
CA2745565C (en) 2017-03-07
US20110257403A1 (en) 2011-10-20
EP2382198A1 (en) 2011-11-02
DK2382198T3 (da) 2013-09-30
CN102264715A (zh) 2011-11-30
TW201033205A (en) 2010-09-16
RU2016120007A (ru) 2018-11-13
SI2382198T1 (sl) 2013-11-29
JP2012513381A (ja) 2012-06-14
BRPI0923393B1 (pt) 2018-06-19
IL213246A0 (en) 2011-07-31
US20150080577A1 (en) 2015-03-19
BRPI0923393A2 (pt) 2015-07-28
PL2382198T3 (pl) 2013-11-29
AU2009331530B2 (en) 2015-04-09
AU2009331530A1 (en) 2011-06-23
SMT201300116B (it) 2013-11-08
US8927722B2 (en) 2015-01-06
PT2382198E (pt) 2013-10-01
WO2010072742A1 (en) 2010-07-01
HRP20130906T1 (hr) 2013-10-25
EP2382198B1 (en) 2013-07-10
AR074863A1 (es) 2011-02-16
CA2745565A1 (en) 2010-07-01
CN102264715B (zh) 2015-12-02
CY1114488T1 (el) 2016-10-05
KR101734507B1 (ko) 2017-05-11
HK1164839A1 (zh) 2012-09-28
ES2429013T3 (es) 2013-11-12
IL213246A (en) 2017-10-31
JP5687631B2 (ja) 2015-03-18
RU2011130895A (ru) 2013-01-27
US9115077B2 (en) 2015-08-25

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