JP5687631B2 - Ｈｃｖのマクロ環状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 - Google Patents
Ｈｃｖのマクロ環状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 Download PDFInfo
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- JP5687631B2 JP5687631B2 JP2011541509A JP2011541509A JP5687631B2 JP 5687631 B2 JP5687631 B2 JP 5687631B2 JP 2011541509 A JP2011541509 A JP 2011541509A JP 2011541509 A JP2011541509 A JP 2011541509A JP 5687631 B2 JP5687631 B2 JP 5687631B2
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- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XDYRBRLMIGIKQW-UHFFFAOYSA-N n-cyclopentylhydroxylamine Chemical compound ONC1CCCC1 XDYRBRLMIGIKQW-UHFFFAOYSA-N 0.000 description 1
- OHDXDNUPVVYWOV-UHFFFAOYSA-N n-methyl-1-(2-naphthalen-1-ylsulfanylphenyl)methanamine Chemical compound CNCC1=CC=CC=C1SC1=CC=CC2=CC=CC=C12 OHDXDNUPVVYWOV-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011403 purification operation Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 150000003248 quinolines Chemical group 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 229960000329 ribavirin Drugs 0.000 description 1
- 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 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 239000003001 serine protease inhibitor Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MYXKPFMQWULLOH-UHFFFAOYSA-M tetramethylazanium;hydroxide;pentahydrate Chemical compound O.O.O.O.O.[OH-].C[N+](C)(C)C MYXKPFMQWULLOH-UHFFFAOYSA-M 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- 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
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- 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
Landscapes
- 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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08172691 | 2008-12-23 | ||
| EP08172691.1 | 2008-12-23 | ||
| PCT/EP2009/067715 WO2010072742A1 (en) | 2008-12-23 | 2009-12-22 | Processes and intermediates for preparing a macrocyclic protease inhibitor of hcv |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012513381A JP2012513381A (ja) | 2012-06-14 |
| JP2012513381A5 JP2012513381A5 (enExample) | 2013-10-24 |
| JP5687631B2 true JP5687631B2 (ja) | 2015-03-18 |
Family
ID=40548041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011541509A Expired - Fee Related JP5687631B2 (ja) | 2008-12-23 | 2009-12-22 | Ｈｃｖのマクロ環状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 |
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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0923393B1 (pt) | 2008-12-23 | 2018-06-19 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | "processos para preparar um inibidor de protease de hcv macrocíclico e intermediários e uso". |
| KR20140063726A (ko) * | 2011-09-22 | 2014-05-27 | 얀센 파마슈티칼즈, 인코포레이티드 | Hcv의 거대고리 단백질 분해효소 억제제의 제조 방법 및 중간물질 |
| MX347650B (es) | 2011-10-28 | 2017-05-05 | Janssen Pharmaceuticals Inc | Procedimiento mejorado para preparar un compuesto intermedio del inhibidor de proteasa macrociclico tmc 435. |
| 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 |
| PT2861604T (pt) | 2012-06-08 | 2017-05-05 | Gilead Sciences Inc | Inibidores macrocíclicos de vírus flaviridae |
| AR091279A1 (es) * | 2012-06-08 | 2015-01-21 | Gilead Sciences Inc | Inhibidores macrociclicos de virus flaviviridae |
| ES2656087T3 (es) * | 2012-06-08 | 2018-02-23 | Gilead Sciences, Inc. | Inhibidores macrocíclicos de virus Flaviviridae |
| UA119315C2 (uk) | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
| ES2735355T3 (es) | 2013-03-15 | 2019-12-18 | Gilead Sciences Inc | Inhibidores macrocíclicos y bicíclicos de virus de hepatitis C |
| 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 |
Family Cites Families (11)
| 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 |
| 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 |
| SI1713823T1 (sl) | 2004-01-30 | 2010-04-30 | Medivir Ab | Inhibitorji HCV NS-3 serin proteaze |
| CN101146794A (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 |
| JP5171624B2 (ja) * | 2005-07-29 | 2013-03-27 | テイボテク・フアーマシユーチカルズ | Ｃ型肝炎ウイルスの大環状阻害剤 |
| PE20070211A1 (es) | 2005-07-29 | 2007-05-12 | Medivir Ab | Compuestos macrociclicos como inhibidores del virus de hepatitis c |
| HRP20100429T1 (hr) * | 2007-02-01 | 2010-09-30 | Tibotec Pharmaceuticals | Postupci i intermedijeri za pripravu makrocikličkog inhibitora proteaze za hcv |
| JP5554570B2 (ja) * | 2007-02-08 | 2014-07-23 | ヤンセン・アールアンドデイ・アイルランド | Ｈｃｖ阻害大環状フェニルカルバメート |
| BRPI0923393B1 (pt) | 2008-12-23 | 2018-06-19 | Ortho-Mcneil-Janssen Pharmaceuticals, Inc. | "processos para preparar um inibidor de protease de hcv macrocíclico e intermediários e uso". |
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2009
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- 2009-12-22 PL PL09801447T patent/PL2382198T3/pl unknown
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- 2009-12-22 CA CA2745565A patent/CA2745565C/en not_active Expired - Fee Related
- 2009-12-22 CN CN200980152851.5A patent/CN102264715B/zh not_active Expired - Fee Related
- 2009-12-22 AU AU2009331530A patent/AU2009331530B2/en not_active Ceased
- 2009-12-22 WO PCT/EP2009/067715 patent/WO2010072742A1/en not_active Ceased
- 2009-12-22 US US13/141,715 patent/US8927722B2/en not_active Expired - Fee Related
- 2009-12-22 AR ARP090105059 patent/AR074863A1/es unknown
- 2009-12-22 PT PT09801447T patent/PT2382198E/pt unknown
- 2009-12-22 HR HRP20130906AT patent/HRP20130906T1/hr unknown
- 2009-12-22 RU RU2016120007A patent/RU2016120007A/ru not_active Application Discontinuation
- 2009-12-22 TW TW98144049A patent/TWI461424B/zh not_active IP Right Cessation
- 2009-12-22 EP EP09801447.5A patent/EP2382198B1/en active Active
- 2009-12-22 ES ES09801447T patent/ES2429013T3/es active Active
- 2009-12-22 SI SI200930731T patent/SI2382198T1/sl unknown
- 2009-12-22 KR KR1020117017333A patent/KR101734507B1/ko not_active Expired - Fee Related
- 2009-12-22 JP JP2011541509A patent/JP5687631B2/ja not_active Expired - Fee Related
- 2009-12-22 DK DK09801447.5T patent/DK2382198T3/da active
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