RU2014110400A - Способ и промежуточные соединения для получения макролактамов - Google Patents
Способ и промежуточные соединения для получения макролактамов Download PDFInfo
- Publication number
- RU2014110400A RU2014110400A RU2014110400/04A RU2014110400A RU2014110400A RU 2014110400 A RU2014110400 A RU 2014110400A RU 2014110400/04 A RU2014110400/04 A RU 2014110400/04A RU 2014110400 A RU2014110400 A RU 2014110400A RU 2014110400 A RU2014110400 A RU 2014110400A
- Authority
- RU
- Russia
- Prior art keywords
- compound
- salt
- solvate
- compounds
- pyridine
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract 31
- 238000000034 method Methods 0.000 title claims abstract 18
- 150000003839 salts Chemical class 0.000 claims abstract 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract 8
- 239000012453 solvate Substances 0.000 claims abstract 8
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims abstract 6
- 239000003795 chemical substances by application Substances 0.000 claims abstract 6
- 229940126543 compound 14 Drugs 0.000 claims abstract 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 229910052802 copper Inorganic materials 0.000 claims abstract 4
- 239000010949 copper Substances 0.000 claims abstract 4
- 238000004519 manufacturing process Methods 0.000 claims abstract 4
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract 4
- 230000005855 radiation Effects 0.000 claims abstract 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract 3
- 229940126062 Compound A Drugs 0.000 claims abstract 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 230000005494 condensation Effects 0.000 claims abstract 2
- 238000009833 condensation Methods 0.000 claims abstract 2
- 150000003222 pyridines Chemical class 0.000 claims abstract 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 2
- 229940125758 compound 15 Drugs 0.000 claims 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 claims 1
- LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 claims 1
- 238000005384 cross polarization magic-angle spinning Methods 0.000 claims 1
- 238000010930 lactamization Methods 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 0 COc1ccc2nc(*)c(O[C@@]3C[C@@](*)*C3)nc2c1 Chemical compound COc1ccc2nc(*)c(O[C@@]3C[C@@](*)*C3)nc2c1 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/04—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a three or four-membered 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
- A61P31/14—Antivirals for RNA viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/04—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups from amines with formation of carbamate groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/32—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C271/34—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of rings other than six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/14—Preparation of carboxylic acid esters from carboxylic acid halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/013—Esters of alcohols having the esterified hydroxy group 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
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D498/16—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
- C07K5/126—Tetrapeptides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161525462P | 2011-08-19 | 2011-08-19 | |
| US61/525,462 | 2011-08-19 | ||
| US201161533439P | 2011-09-12 | 2011-09-12 | |
| US61/533,439 | 2011-09-12 | ||
| US201161533915P | 2011-09-13 | 2011-09-13 | |
| US61/533,915 | 2011-09-13 | ||
| US201161539540P | 2011-09-27 | 2011-09-27 | |
| US61/539,540 | 2011-09-27 | ||
| PCT/US2012/051177 WO2013028470A1 (en) | 2011-08-19 | 2012-08-16 | Process and intermediates for preparing macrolactams |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2014110400A true RU2014110400A (ru) | 2015-09-27 |
Family
ID=47746773
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2014110399/04A RU2014110399A (ru) | 2011-08-19 | 2012-08-16 | Кристаллические формы вгс протеазного ингибитора |
| RU2014110400/04A RU2014110400A (ru) | 2011-08-19 | 2012-08-16 | Способ и промежуточные соединения для получения макролактамов |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2014110399/04A RU2014110399A (ru) | 2011-08-19 | 2012-08-16 | Кристаллические формы вгс протеазного ингибитора |
Country Status (11)
| Country | Link |
|---|---|
| US (3) | US9242917B2 (enExample) |
| EP (3) | EP2744331A4 (enExample) |
| JP (2) | JP2014524442A (enExample) |
| KR (2) | KR20140053330A (enExample) |
| CN (2) | CN103889439A (enExample) |
| AU (2) | AU2012299218A1 (enExample) |
| BR (2) | BR112014003798A2 (enExample) |
| CA (2) | CA2844388A1 (enExample) |
| MX (2) | MX2014001944A (enExample) |
| RU (2) | RU2014110399A (enExample) |
| WO (3) | WO2013028470A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2459582B1 (en) | 2009-07-30 | 2015-05-27 | Merck Sharp & Dohme Corp. | Hepatitis c virus ns3 protease inhibitors |
| US8957203B2 (en) | 2011-05-05 | 2015-02-17 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| KR20140053330A (ko) | 2011-08-19 | 2014-05-07 | 머크 샤프 앤드 돔 코포레이션 | 마크로락탐의 제조를 위한 방법 및 중간체 |
| UA119315C2 (uk) | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
| WO2014062196A1 (en) | 2012-10-19 | 2014-04-24 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| US9643999B2 (en) | 2012-11-02 | 2017-05-09 | Bristol-Myers Squibb Company | Hepatitis C virus inhibitors |
| WO2014071007A1 (en) | 2012-11-02 | 2014-05-08 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| EP2914613B1 (en) | 2012-11-02 | 2017-11-22 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| WO2014070974A1 (en) | 2012-11-05 | 2014-05-08 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| EP2764866A1 (en) | 2013-02-07 | 2014-08-13 | IP Gesellschaft für Management mbH | Inhibitors of nedd8-activating enzyme |
| EP2964664B1 (en) | 2013-03-07 | 2017-01-11 | Bristol-Myers Squibb Company | Hepatitis c virus inhibitors |
| EA029088B1 (ru) | 2013-03-15 | 2018-02-28 | Джилид Сайэнс, Инк. | Макроциклические и бициклические ингибиторы вируса гепатита c |
| SG11201602693QA (en) | 2013-10-18 | 2016-05-30 | Merck Sharp & Dohme | Methods and intermediates for preparing macrolactams |
| WO2015095437A1 (en) * | 2013-12-20 | 2015-06-25 | Merck Sharp & Dohme Corp. | Methods and intermediates for the preparation of macrolactams |
| LT3636649T (lt) * | 2014-01-24 | 2024-04-10 | Turning Point Therapeutics, Inc. | Diarilo makrociklai kaip proteinkinazių moduliatoriai |
| US9321807B2 (en) | 2014-06-06 | 2016-04-26 | Abbvie Inc. | Crystal forms |
| US10316044B2 (en) | 2015-07-02 | 2019-06-11 | Tp Therapeutics, Inc. | Chiral diaryl macrocycles as modulators of protein kinases |
| SMT202400213T1 (it) * | 2015-07-06 | 2024-07-09 | Turning Point Therapeutics Inc | Polimorfo di diaril macrociclo |
| ES2818528T3 (es) * | 2015-07-21 | 2021-04-13 | Turning Point Therapeutics Inc | Macrociclo de diarilo quiral y uso del mismo en el tratamiento del cáncer |
| WO2017197051A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Amine-linked c3-glutarimide degronimers for target protein degradation |
| WO2017197036A1 (en) | 2016-05-10 | 2017-11-16 | C4 Therapeutics, Inc. | Spirocyclic degronimers for target protein degradation |
| EP3454856B1 (en) | 2016-05-10 | 2024-09-11 | C4 Therapeutics, Inc. | Heterocyclic degronimers for target protein degradation |
| EP3455218A4 (en) | 2016-05-10 | 2019-12-18 | C4 Therapeutics, Inc. | C3 CARBON-BASED GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN REDUCTION |
| EP3490564A4 (en) | 2016-07-28 | 2020-02-26 | Turning Point Therapeutics, Inc. | MACRO CYCLE Kinase Inhibitors |
| TWI808958B (zh) | 2017-01-25 | 2023-07-21 | 美商特普醫葯公司 | 涉及二芳基巨環化合物之組合療法 |
| CN110769822A (zh) | 2017-06-20 | 2020-02-07 | C4医药公司 | 用于蛋白降解的n/o-连接的降解决定子和降解决定子体 |
| EP3658148B1 (en) | 2017-07-28 | 2024-07-10 | Turning Point Therapeutics, Inc. | Macrocyclic compounds and uses thereof |
| MX2020006490A (es) | 2017-12-19 | 2020-08-17 | Turning Point Therapeutics Inc | Compuestos macrociclicos para tratar enfermedades. |
| CN111057045A (zh) * | 2019-12-18 | 2020-04-24 | 安徽红杉生物医药科技有限公司 | Hcv ns3/4a蛋白酶抑制剂中间体及其合成方法、应用 |
| CN112174982A (zh) * | 2020-09-10 | 2021-01-05 | 上海希迈医药科技有限公司 | 一种洛普替尼晶型及其制备方法 |
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| CA2714604A1 (en) | 2008-02-25 | 2009-09-03 | Merck Sharp & Dohme Corp. | Macrocyclic hcv ns3 protease inhibitors |
| WO2009131196A1 (ja) * | 2008-04-24 | 2009-10-29 | 武田薬品工業株式会社 | 置換ピロリジン誘導体およびその用途 |
| EP2274288A2 (en) | 2008-04-24 | 2011-01-19 | Incyte Corporation | Macrocyclic compounds and their use as kinase inhibitors |
| CA2720850A1 (en) | 2008-04-28 | 2009-11-05 | Merck Sharp & Dohme Corp. | Hcv ns3 protease inhibitors |
| KR101313675B1 (ko) | 2008-07-22 | 2013-10-02 | 이스티투토 디 리세르쉐 디 비올로지아 몰레콜라레 피. 안젤레티 에스.알.엘. | Ｈｃｖ ｎｓ3 프로테아제 억제제로서의 마크로사이클릭 퀴녹살린 화합물 |
| EP2459582B1 (en) | 2009-07-30 | 2015-05-27 | Merck Sharp & Dohme Corp. | Hepatitis c virus ns3 protease inhibitors |
| CN102470158A (zh) * | 2009-08-27 | 2012-05-23 | 默沙东公司 | 制备丙型肝炎病毒的蛋白酶抑制剂的工艺方法 |
| KR20140053330A (ko) | 2011-08-19 | 2014-05-07 | 머크 샤프 앤드 돔 코포레이션 | 마크로락탐의 제조를 위한 방법 및 중간체 |
-
2012
- 2012-08-16 KR KR1020147006858A patent/KR20140053330A/ko not_active Withdrawn
- 2012-08-16 EP EP12825726.8A patent/EP2744331A4/en not_active Withdrawn
- 2012-08-16 KR KR1020147006888A patent/KR20140059236A/ko not_active Withdrawn
- 2012-08-16 MX MX2014001944A patent/MX2014001944A/es unknown
- 2012-08-16 RU RU2014110399/04A patent/RU2014110399A/ru not_active Application Discontinuation
- 2012-08-16 MX MX2014001945A patent/MX2014001945A/es unknown
- 2012-08-16 BR BR112014003798A patent/BR112014003798A2/pt not_active IP Right Cessation
- 2012-08-16 AU AU2012299218A patent/AU2012299218A1/en not_active Abandoned
- 2012-08-16 CN CN201280050382.8A patent/CN103889439A/zh active Pending
- 2012-08-16 EP EP12825540.3A patent/EP2744507A4/en not_active Withdrawn
- 2012-08-16 JP JP2014526215A patent/JP2014524442A/ja active Pending
- 2012-08-16 CA CA2844388A patent/CA2844388A1/en not_active Abandoned
- 2012-08-16 EP EP12826404.1A patent/EP2744336B1/en not_active Not-in-force
- 2012-08-16 WO PCT/US2012/051177 patent/WO2013028470A1/en not_active Ceased
- 2012-08-16 WO PCT/US2012/051168 patent/WO2013028465A1/en not_active Ceased
- 2012-08-16 RU RU2014110400/04A patent/RU2014110400A/ru not_active Application Discontinuation
- 2012-08-16 CA CA2844386A patent/CA2844386A1/en not_active Abandoned
- 2012-08-16 BR BR112014003802A patent/BR112014003802A2/pt not_active IP Right Cessation
- 2012-08-16 CN CN201280050361.6A patent/CN103874414A/zh active Pending
- 2012-08-16 JP JP2014526217A patent/JP2014521750A/ja active Pending
- 2012-08-16 US US14/239,389 patent/US9242917B2/en active Active
- 2012-08-16 US US14/239,391 patent/US9073825B2/en active Active
- 2012-08-16 WO PCT/US2012/051182 patent/WO2013028471A1/en not_active Ceased
- 2012-08-16 AU AU2012299223A patent/AU2012299223A1/en not_active Abandoned
- 2012-08-16 US US14/239,393 patent/US9238604B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| RU2014110399A (ru) | 2015-09-27 |
| WO2013028465A1 (en) | 2013-02-28 |
| EP2744507A4 (en) | 2015-01-28 |
| BR112014003798A2 (pt) | 2017-03-01 |
| EP2744336A4 (en) | 2014-12-31 |
| US9238604B2 (en) | 2016-01-19 |
| US20140206605A1 (en) | 2014-07-24 |
| JP2014521750A (ja) | 2014-08-28 |
| WO2013028470A1 (en) | 2013-02-28 |
| MX2014001945A (es) | 2014-03-27 |
| EP2744507A1 (en) | 2014-06-25 |
| CN103874414A (zh) | 2014-06-18 |
| US20140200343A1 (en) | 2014-07-17 |
| US9242917B2 (en) | 2016-01-26 |
| AU2012299218A1 (en) | 2014-02-20 |
| EP2744336A1 (en) | 2014-06-25 |
| EP2744331A4 (en) | 2015-01-21 |
| CA2844386A1 (en) | 2013-02-28 |
| WO2013028471A1 (en) | 2013-02-28 |
| KR20140053330A (ko) | 2014-05-07 |
| CN103889439A (zh) | 2014-06-25 |
| US20140243519A1 (en) | 2014-08-28 |
| EP2744331A1 (en) | 2014-06-25 |
| CA2844388A1 (en) | 2013-02-28 |
| MX2014001944A (es) | 2014-03-27 |
| EP2744336B1 (en) | 2017-07-05 |
| JP2014524442A (ja) | 2014-09-22 |
| KR20140059236A (ko) | 2014-05-15 |
| US9073825B2 (en) | 2015-07-07 |
| AU2012299223A1 (en) | 2014-02-27 |
| BR112014003802A2 (pt) | 2017-06-13 |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
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