CN100352819C - 作为ns3-丝氨酸蛋白酶抑制剂的脯氨酸化合物用于制备治疗丙型肝炎病毒感染的药物 - Google Patents

作为ns3-丝氨酸蛋白酶抑制剂的脯氨酸化合物用于制备治疗丙型肝炎病毒感染的药物 Download PDF

Info

Publication number
CN100352819C
CN100352819C CNB038026600A CN03802660A CN100352819C CN 100352819 C CN100352819 C CN 100352819C CN B038026600 A CNB038026600 A CN B038026600A CN 03802660 A CN03802660 A CN 03802660A CN 100352819 C CN100352819 C CN 100352819C
Authority
CN
China
Prior art keywords
compound
interferon
alkyl
pharmaceutical composition
compounds
Prior art date
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.)
Expired - Fee Related
Application number
CNB038026600A
Other languages
English (en)
Chinese (zh)
Other versions
CN1692109A (zh
Inventor
A·阿拉萨潘
F·本内特
S·L·博根
K·X·陈
E·姚
Y·-T·刘
R·G·罗维
V·S·马迪森
L·G·奈尔
F·G·诺罗格
A·K·萨克塞纳
M·桑尼格拉希
S·文卡特拉曼
V·M·吉里亚瓦拉班
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.)
Merck Sharp and Dohme LLC
Original Assignee
Schering Corp
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.)
Filing date
Publication date
Application filed by Schering Corp filed Critical Schering Corp
Publication of CN1692109A publication Critical patent/CN1692109A/zh
Application granted granted Critical
Publication of CN100352819C publication Critical patent/CN100352819C/zh
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D207/24Oxygen or sulfur atoms
    • C07D207/262-Pyrrolidones
    • C07D207/2632-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/272-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4965Non-condensed pyrazines
    • A61K31/497Non-condensed pyrazines containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • A61P31/14Antivirals for RNA viruses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
    • C07D207/16Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/08Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/30Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/42Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/34Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D211/00Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/72Nitrogen atoms
    • C07D213/75Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D217/00Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C07D217/26Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
    • C07D233/68Halogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D243/00Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/10Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D243/121,5-Benzodiazepines; Hydrogenated 1,5-benzodiazepines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D253/00Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/061,2,4-Triazines
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D271/00Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/061,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/04Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D277/06Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/38Nitrogen atoms
    • C07D277/44Acylated amino or imino radicals
    • C07D277/46Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D277/00Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D277/56Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D295/00Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/15Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
    • C07D307/68Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D317/00Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/58Radicals substituted by nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D335/00Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/10Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/12Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Virology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Molecular Biology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Epidemiology (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Plural Heterocyclic Compounds (AREA)
CNB038026600A 2002-01-23 2003-01-21 作为ns3-丝氨酸蛋白酶抑制剂的脯氨酸化合物用于制备治疗丙型肝炎病毒感染的药物 Expired - Fee Related CN100352819C (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US35093102P 2002-01-23 2002-01-23
US60/350,931 2002-01-23

Publications (2)

Publication Number Publication Date
CN1692109A CN1692109A (zh) 2005-11-02
CN100352819C true CN100352819C (zh) 2007-12-05

Family

ID=27613440

Family Applications (1)

Application Number Title Priority Date Filing Date
CNB038026600A Expired - Fee Related CN100352819C (zh) 2002-01-23 2003-01-21 作为ns3-丝氨酸蛋白酶抑制剂的脯氨酸化合物用于制备治疗丙型肝炎病毒感染的药物

Country Status (18)

Country Link
US (1) US6894072B2 (enExample)
EP (1) EP1467989B1 (enExample)
JP (1) JP4301953B2 (enExample)
KR (1) KR20040077767A (enExample)
CN (1) CN100352819C (enExample)
AR (1) AR038214A1 (enExample)
AT (1) ATE443703T1 (enExample)
AU (1) AU2003207625B2 (enExample)
CA (1) CA2473070C (enExample)
DE (1) DE60329367D1 (enExample)
ES (1) ES2332778T3 (enExample)
IL (1) IL162828A0 (enExample)
MX (1) MXPA04007163A (enExample)
NZ (1) NZ533861A (enExample)
PE (1) PE20030857A1 (enExample)
TW (1) TWI265927B (enExample)
WO (1) WO2003062228A1 (enExample)
ZA (1) ZA200405341B (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103387510A (zh) * 2013-08-08 2013-11-13 苏州永健生物医药有限公司 一种β-氨基-alpha-羟基环丁基丁酰胺盐酸盐的合成方法

Families Citing this family (67)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SG185140A1 (en) * 2003-06-17 2012-11-29 Merck Sharp & Dohme Enantiomer forms of boc protected 3-amino-3-cyclobutylmethyl-2-hydroxy-propionamide
US7449447B2 (en) * 2003-08-26 2008-11-11 Schering Corporation Peptidomimetic NS3-serine protease inhibitors of hepatitis C virus
CN1894274A (zh) * 2003-09-26 2007-01-10 先灵公司 丙肝病毒ns3丝氨酸蛋白酶的大环抑制剂
PE20050940A1 (es) 2003-12-11 2005-11-08 Schering Corp Nuevos inhibidores de la ns3/ns4a serina proteasa del virus de la hepatitis c
EP1713822B1 (en) 2004-01-30 2010-03-17 Medivir AB Hcv ns-3 serine protease inhibitors
CN1946718A (zh) * 2004-02-27 2007-04-11 先灵公司 用作丙型肝炎病毒ns3丝氨酸蛋白酶抑制剂的具有环p4′s的新型酮酰胺
CN1946691A (zh) 2004-02-27 2007-04-11 先灵公司 作为丙型肝炎病毒ns3丝氨酸蛋白酶抑制剂的化合物
US20060252698A1 (en) * 2005-04-20 2006-11-09 Malcolm Bruce A Compounds for inhibiting cathepsin activity
WO2006130552A2 (en) * 2005-06-02 2006-12-07 Schering Corporation Methods of treating hepatitis c virus
EP1898941A2 (en) * 2005-06-02 2008-03-19 Schering Corporation Controlled-release formulation useful for treating disorders associated with hepatitis c virus
US20060281689A1 (en) * 2005-06-02 2006-12-14 Schering Corporation Method for modulating activity of HCV protease through use of a novel HCV protease inhibitor to reduce duration of treatment period
US20060276404A1 (en) * 2005-06-02 2006-12-07 Anima Ghosal Medicaments and methods combining a HCV protease inhibitor and an AKR competitor
US20070237818A1 (en) * 2005-06-02 2007-10-11 Malcolm Bruce A Controlled-release formulation of HCV protease inhibitor and methods using the same
US20070021351A1 (en) * 2005-06-02 2007-01-25 Schering Corporation Liver/plasma concentration ratio for dosing hepatitis C virus protease inhibitor
WO2006130554A2 (en) * 2005-06-02 2006-12-07 Schering Corporation Methods of treating hepatitis c virus
US20060276405A1 (en) * 2005-06-02 2006-12-07 Schering Corporation Methods for treating hepatitis C
US20060275366A1 (en) * 2005-06-02 2006-12-07 Schering Corporation Controlled-release formulation
EP1891089B1 (en) 2005-06-02 2014-11-05 Merck Sharp & Dohme Corp. HCV protease inhibitors in combination with food
JP5160415B2 (ja) * 2005-06-02 2013-03-13 メルク・シャープ・アンド・ドーム・コーポレーション 医薬処方物およびそれを用いる治療方法
PE20070211A1 (es) 2005-07-29 2007-05-12 Medivir Ab Compuestos macrociclicos como inhibidores del virus de hepatitis c
AR055395A1 (es) 2005-08-26 2007-08-22 Vertex Pharma Compuestos inhibidores de la actividad de la serina proteasa ns3-ns4a del virus de la hepatitis c
JP5409008B2 (ja) 2005-11-11 2014-02-05 バーテックス ファーマシューティカルズ インコーポレイテッド C型肝炎ウイルス改変体
US7705138B2 (en) * 2005-11-11 2010-04-27 Vertex Pharmaceuticals Incorporated Hepatitis C virus variants
JP5473334B2 (ja) 2005-12-23 2014-04-16 ジーランド ファーマ アクティーゼルスカブ 修飾リジン模倣化合物
US7816348B2 (en) 2006-02-03 2010-10-19 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
WO2007120595A2 (en) * 2006-04-11 2007-10-25 Novartis Ag Amines for the treatment of hcv
US20070265281A1 (en) * 2006-04-11 2007-11-15 Sylvain Cottens Organic Compounds and Their Uses
US20080045530A1 (en) * 2006-04-11 2008-02-21 Trixi Brandl Organic Compounds and Their Uses
WO2007133865A2 (en) * 2006-04-11 2007-11-22 Novartis Ag Hcv/hiv inhibitors an their uses
CA2660555A1 (en) 2006-08-17 2008-02-21 Boehringer Ingelheim International Gmbh Viral polymerase inhibitors
WO2008057995A2 (en) * 2006-11-02 2008-05-15 Taigen Biotechnology Co., Ltd. Hcv protease inhibitors
WO2008073282A2 (en) * 2006-12-07 2008-06-19 Schering Corporation Ph sensitive matrix formulation
MX2009006720A (es) 2006-12-19 2009-08-28 Schering Corp Preparacion de clorhidrato de 3-amino-3-(ciclobutilmetil)-2(hidrox i)-propionamida.
US20080188545A1 (en) 2006-12-21 2008-08-07 Alimardanov Asaf R Synthesis of pyrrolidine compounds
TWI400042B (zh) * 2007-06-08 2013-07-01 Tci Co Ltd 食品錠劑
JP2010535156A (ja) 2007-08-03 2010-11-18 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング ウイルスポリメラーゼ阻害剤
AU2008309589B2 (en) * 2007-10-10 2012-07-05 Novartis Ag Spiropyrrolidines and their use against HCV and HIV infection
US20090111757A1 (en) * 2007-10-25 2009-04-30 Taigen Biotechnology Co., Ltd. Hcv protease inhibitors
MX2010006313A (es) 2007-12-19 2010-06-25 Boehringer Ingelheim Int Inhibidores de la polimerasa virica.
US8293705B2 (en) 2007-12-21 2012-10-23 Avila Therapeutics, Inc. HCV protease inhibitors and uses thereof
CN104557861A (zh) * 2007-12-21 2015-04-29 阿维拉制药公司 Hcv蛋白酶抑制剂和其用途
US8309685B2 (en) 2007-12-21 2012-11-13 Celgene Avilomics Research, Inc. HCV protease inhibitors and uses thereof
EP2237666A4 (en) 2007-12-21 2012-05-16 Avila Therapeutics Inc HCV PROTEASE INHIBITORS AND USES THEREOF
CN101580535B (zh) * 2008-05-16 2012-10-03 太景生物科技股份有限公司 丙型肝炎病毒蛋白酶抑制剂
WO2010021717A2 (en) * 2008-08-20 2010-02-25 Sequoia Pharmaceuticals, Inc. Hcv protease inhibitors
JP2012514605A (ja) 2009-01-07 2012-06-28 サイネクシス,インコーポレーテッド Hcvおよびhiv感染の治療への使用におけるシクロスポリン誘導体
US20110182850A1 (en) * 2009-04-10 2011-07-28 Trixi Brandl Organic compounds and their uses
US8512690B2 (en) 2009-04-10 2013-08-20 Novartis Ag Derivatised proline containing peptide compounds as protease inhibitors
AU2010253791A1 (en) 2009-05-29 2011-11-24 Merck Sharp & Dohme Corp. Antiviral compounds composed of three linked Aryl moieties to treat diseases such as Hepatitis C
HUE030402T2 (en) * 2009-09-15 2017-05-29 Taigen Biotechnology Co Ltd HCV protease inhibitors
WO2011066241A1 (en) 2009-11-25 2011-06-03 Schering Corporation Fused tricyclic compounds and derivatives thereof useful for the treatment of viral diseases
US20130156731A1 (en) 2009-12-22 2013-06-20 Kevin X. Chen Fused tricyclic compounds and methods of use thereof for the treatment of viral diseas
US20110178107A1 (en) * 2010-01-20 2011-07-21 Taigen Biotechnology Co., Ltd. Hcv protease inhibitors
CN102140100B (zh) 2010-01-27 2014-06-11 爱博新药研发(上海)有限公司 高效抑制丙型肝炎病毒的多环化合物及其制备方法和用途
AR080676A1 (es) 2010-03-09 2012-05-02 Schering Corp Compuestos de sililo triciclicos fusionados y metodos de uso de los mismos para el tratamiento de enfermedades virales
CA2805440A1 (en) 2010-07-26 2012-02-09 Merck Sharp & Dohme Corp. Substituted biphenylene compounds and methods of use thereof for the treatment of viral diseases
JP2013540122A (ja) 2010-09-29 2013-10-31 メルク・シャープ・エンド・ドーム・コーポレイション 縮合四環式化合物誘導体およびウィルス疾患治療のためのそれの使用方法
WO2012142075A1 (en) 2011-04-13 2012-10-18 Merck Sharp & Dohme Corp. 2'-azido substituted nucleoside derivatives and methods of use thereof for the treatment of viral diseases
EA201391519A1 (ru) 2011-04-13 2014-03-31 Мерк Шарп И Доум Корп. 2'-замещенные нуклеозидные производные и способы их применения для лечения вирусных заболеваний
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
WO2013033899A1 (en) 2011-09-08 2013-03-14 Merck Sharp & Dohme Corp. Substituted benzofuran compounds and methods of use thereof for the treatment of viral diseases
WO2013033900A1 (en) 2011-09-08 2013-03-14 Merck Sharp & Dohme Corp. Tetracyclic heterocycle compounds and methods of use thereof for the treatment of viral diseases
WO2013033901A1 (en) 2011-09-08 2013-03-14 Merck Sharp & Dohme Corp. Heterocyclic-substituted benzofuran derivatives and methods of use thereof for the treatment of viral diseases
WO2013039876A1 (en) 2011-09-14 2013-03-21 Merck Sharp & Dohme Corp. Silyl-containing heterocyclic compounds and methods of use thereof for the treatment of viral diseases
WO2015065817A1 (en) 2013-10-30 2015-05-07 Merck Sharp & Dohme Corp. Pseudopolymorphs of an hcv ns5a inhibitor and uses thereof
WO2018202865A1 (en) 2017-05-05 2018-11-08 Zealand Pharma A/S Gap junction intercellular communication modulators and their use for the treatment of diabetic eye disease
US11351149B2 (en) 2020-09-03 2022-06-07 Pfizer Inc. Nitrile-containing antiviral compounds

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1315965A (zh) * 1998-08-10 2001-10-03 贝林格尔·英格海姆加拿大有限公司 丙型肝炎肽抑制剂
WO2001074768A2 (en) * 2000-04-03 2001-10-11 Vertex Pharmaceuticals Incorporated Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1989004669A1 (en) 1987-11-18 1989-06-01 Chiron Corporation Nanbv diagnostics and vaccines
DE69024378T2 (de) 1989-02-01 1996-09-12 Asahi Glass Co. Ltd., Tokio/Tokyo Azeotrope oder azeotropähnliche Zusammensetzung auf der Basis von Chlorfluorkohlenwasserstoffen
US5371017A (en) 1990-04-04 1994-12-06 Chiron Corporation Hepatitis C virus protease
US5922757A (en) 1996-09-30 1999-07-13 The Regents Of The University Of California Treatment and prevention of hepatic disorders
HU227742B1 (en) 1996-10-18 2012-02-28 Vertex Pharma Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease
GB9623908D0 (en) 1996-11-18 1997-01-08 Hoffmann La Roche Amino acid derivatives
NZ503263A (en) 1997-08-11 2002-10-25 Boehringer Ingelheim Ca Ltd Hepatitis C NS3 protease inhibitor peptides and peptide analogues
US6323180B1 (en) 1998-08-10 2001-11-27 Boehringer Ingelheim (Canada) Ltd Hepatitis C inhibitor tri-peptides
AR034127A1 (es) * 2000-07-21 2004-02-04 Schering Corp Imidazolidinonas como inhibidores de ns3-serina proteasa del virus de hepatitis c, composicion farmaceutica, un metodo para su preparacion, y el uso de las mismas para la manufactura de un medicamento
RU2355700C9 (ru) 2000-07-21 2010-03-20 Шеринг Корпорейшн Новые пептиды как ингибиторы ns3-серинпротеазы вируса гепатита с
AR029851A1 (es) 2000-07-21 2003-07-16 Dendreon Corp Nuevos peptidos como inhibidores de ns3-serina proteasa del virus de hepatitis c

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1315965A (zh) * 1998-08-10 2001-10-03 贝林格尔·英格海姆加拿大有限公司 丙型肝炎肽抑制剂
WO2001074768A2 (en) * 2000-04-03 2001-10-11 Vertex Pharmaceuticals Incorporated Inhibitors of serine proteases, particularly hepatitis c virus ns3 protease

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103387510A (zh) * 2013-08-08 2013-11-13 苏州永健生物医药有限公司 一种β-氨基-alpha-羟基环丁基丁酰胺盐酸盐的合成方法
CN103387510B (zh) * 2013-08-08 2015-09-09 苏州永健生物医药有限公司 一种β-氨基-alpha-羟基环丁基丁酰胺盐酸盐的合成方法

Also Published As

Publication number Publication date
CA2473070A1 (en) 2003-07-31
TW200306311A (en) 2003-11-16
MXPA04007163A (es) 2004-10-29
NZ533861A (en) 2006-03-31
US6894072B2 (en) 2005-05-17
ZA200405341B (en) 2005-09-09
ATE443703T1 (de) 2009-10-15
DE60329367D1 (de) 2009-11-05
IL162828A0 (en) 2005-11-20
AR038214A1 (es) 2005-01-05
JP2005515255A (ja) 2005-05-26
JP4301953B2 (ja) 2009-07-22
KR20040077767A (ko) 2004-09-06
EP1467989A1 (en) 2004-10-20
ES2332778T3 (es) 2010-02-12
EP1467989B1 (en) 2009-09-23
CN1692109A (zh) 2005-11-02
TWI265927B (en) 2006-11-11
AU2003207625B2 (en) 2006-09-07
CA2473070C (en) 2009-10-13
PE20030857A1 (es) 2003-10-25
US20030207861A1 (en) 2003-11-06
WO2003062228A1 (en) 2003-07-31

Similar Documents

Publication Publication Date Title
CN100352819C (zh) 作为ns3-丝氨酸蛋白酶抑制剂的脯氨酸化合物用于制备治疗丙型肝炎病毒感染的药物
US7485625B2 (en) Inhibitors of hepatitis C virus NS3/NS4a serine protease
US7253160B2 (en) Depeptidized inhibitors of hepatitis C virus NS3 protease
US8067379B2 (en) Sulfur compounds as inhibitors of hepatitis C virus NS3 serine protease
US7718691B2 (en) Compounds as inhibitors of hepatitis C virus NS3 serine protease
US7399749B2 (en) Substituted prolines as inhibitors of hepatitis C virus NS3 serine protease
US7423058B2 (en) Inhibitors of hepatitis C virus NS3 protease
US7425576B2 (en) Compounds as inhibitors of hepatitis C virus NS3 serine protease
JP4525982B2 (ja) C型肝炎ウイルスのns3セリンプロテアーゼの大環状インヒビター
JP4874227B2 (ja) C型肝炎ウイルスのns3セリンプロテアーゼインヒビターとしての環状p4’sを有する新規ケトアミド
JP4527722B2 (ja) C型肝炎ウイルスの新規のペプチド模倣性ns3−セリンプロテアーゼインヒビター
US20100104534A1 (en) Hydrazido-peptides as inhibitors of hcv ns3-protease
AU2003207625A1 (en) Proline compounds as NS3-serine protease inhibitors for use in treatment of hepatites C virus infection
JP2007525512A (ja) C型肝炎ウイルスns3セリンプロテアーゼのインヒビターとしての3,4−(シクロペンチル)−縮合プロリン化合物
CN101679240A (zh) Hcv ns3蛋白酶的p1-非可差向异构化酮酰胺抑制剂
CN101910195A (zh) 丙型肝炎病毒ns3丝氨酸蛋白酶的大环抑制剂
JP2007525521A (ja) C型肝炎ウイルスns3セリンプロテアーゼのインヒビターとしてのシクロブテンジオン基含有化合物

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
C14 Grant of patent or utility model
GR01 Patent grant
C17 Cessation of patent right
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20071205

Termination date: 20120121