KR100699514B1 - Hiv를 억제하는 피리미딘 유도체 - Google Patents
Hiv를 억제하는 피리미딘 유도체 Download PDFInfo
- Publication number
- KR100699514B1 KR100699514B1 KR1020067013365A KR20067013365A KR100699514B1 KR 100699514 B1 KR100699514 B1 KR 100699514B1 KR 1020067013365 A KR1020067013365 A KR 1020067013365A KR 20067013365 A KR20067013365 A KR 20067013365A KR 100699514 B1 KR100699514 B1 KR 100699514B1
- Authority
- KR
- South Korea
- Prior art keywords
- amino
- phenyl
- pyrimidinyl
- benzonitrile
- methyl
- Prior art date
Links
- 0 *c1cncnc1 Chemical compound *c1cncnc1 0.000 description 4
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic 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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
- C07D239/49—Two nitrogen atoms with an aralkyl radical, or substituted aralkyl radical, attached in position 5, e.g. trimethoprim
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/50—Three nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic 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
- C07D401/02—Heterocyclic 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
- C07D401/12—Heterocyclic 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 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)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
Claims (12)
- 하기 화학식 (I')의 화합물, 그의 N-옥사이드, 약제학적으로 허용되는 부가 염 또는 입체화학적 이성체 형태:상기 식에서,A 는 CH, CR4 또는 N 이고;Q 는 수소 또는 -NR1R2 이며;R1 및 R2 는 각각 독립적으로 수소, 하이드록시, C1-12알킬, C1-12알킬옥시, C1-12알킬카보닐, C1-12알킬옥시카보닐, 아릴, 아미노, 모노- 또는 디(C1-12알킬)아미노 및 모노- 또는 디(C1-12알킬)아미노카보닐로 구성된 군으로부터 선택되거나(여기에서, 상기 언급한 각각의 C1-12알킬기는 임의로 및 각각 개별적으로 하이드록시, C1-6알킬옥시, 하이드록시C1-6알킬옥시, 카복실, C1-6알킬옥시카보닐, 시아노, 아미노, 이미노, 아미노카보닐, 아미노카보닐아미노, 모노- 또는 디(C1-6알킬)아미노, 아릴 및 Het 로 구성된 군으로부터 각각 독립적으로 선택된 1 또는 2 개의 치환기로 치환될 수 있다);R1 및 R2 가 함께 피롤리디닐, 피페리디닐, 몰포리닐, 아지도 또는 모노- 또는 디(C1-12알킬)아미노C1-4알킬리덴을 형성할 수 있고;R3 은 수소, 아릴, C1-6알킬카보닐, C1-6알킬, C1-6알킬옥시카보닐 또는 C1-6알킬옥시카보닐로 치환된 C1-6알킬이며;R4 는 각각 독립적으로 하이드록시, 할로, C1-6알킬, C1-6알킬옥시, 시아노, 아미노카보닐, 니트로, 아미노, 트리할로메틸, 트리할로메틸옥시, 또는 시아노 또는 아미노카보닐로 치환된 C1-6알킬이고;R5 는 수소 또는 C1-4알킬이며;L 은 페닐로 치환된 C1-10알킬이거나(여기에서, 상기 페닐은 1 또는 2 개의 할로로 치환될 수 있다);L 은 -X1-R6 또는 -X2-Alk-R7 이고(여기에서,R6 및 R7 은 각각 독립적으로 페닐; 또는 할로, 하이드록시, C1-6알킬, C1-6알킬옥시, 시아노, 아미노카보닐, 트리할로메틸옥시 및 트리할로메틸로 구성된 군으로부터 각각 독립적으로 선택된 1, 2, 3, 4 또는 5 개의 치환기로 치환된 페닐이고;X1 및 X2 는 각각 독립적으로 -NR3-, -O- 또는 -S- 이며;Alk 는 C1-4알칸디일이다);아릴은 페닐 또는 할로, C1-6알킬, C1-6알킬옥시, 시아노, 니트로 및 트리플루오로메틸로 구성된 군으로부터 각각 독립적으로 선택된 1, 2, 3, 4 또는 5 개의 치환기로 치환된 페닐이고;Het 는 지방족 또는 방향족 헤테로사이클 라디칼이며;상기 지방족 헤테로사이클 라디칼은 피롤리디닐, 피페리디닐, 호모피페리디닐, 피페라지닐, 몰포리닐, 테트라하이드로퓨라닐 및 테트라하이드로티에닐로 구성된 군으로부터 선택되고(여기에서, 상기 지방족 헤테로사이클 라디칼은 각각 옥소기로 임의로 치환될 수 있다);상기 방향족 헤테로사이클 라디칼은 피롤릴, 퓨라닐, 티에닐, 피리딜, 피리미디닐, 피라지닐 및 피리다지닐로 구성된 군으로부터 선택되며(여기에서, 상기 방향족 헤테로사이클 라디칼은 각각 하이드록시로 임의로 치환될 수 있다);R4'는 시아노, 아미노카보닐, 또는 시아노 또는 아미노카보닐로 치환된 C1-6알킬이고;n'는 0, 1, 2 또는 3 이며;단, Q 및 L 은 아닐리노, 2,4,6-트리니트로-아닐리노, 3-메톡시아닐리노, 4-메톡시-아닐리노, 3,4-디메톡시-아닐리노, 3-클로로-4-플루오로-아닐리노, 4-시아노-아닐리노, 2-(C1-6알킬)-아닐리노, 4-(C1-6알킬)-아닐리노, 3-클로로-아닐리노, 4-브로모-아닐리노, 4-니트로-아닐리노 및 4-클로로-아닐리노가 아니다.
- 제1항 또는 제2항에 있어서, L 이 2,6-디클로로벤질이거나; L 이 -X1-R6 이거나(여기에서, X1 은 -NR3-, -S- 또는 -O- 이고, R6 은 2,4,6-트리클로로페닐, 2,4,6-트리메틸-페닐, 2,4-디브로모-3,5-디클로로-페닐, 2,4-디브로모-6-플루오로-페닐, 2,4-디클로로-6-메틸-페닐, 2,6-디브로모-4-이소프로필-페닐, 2,6-디브로모-4-메틸페닐, 2,6-디브로모-4-프로프-1-일-페닐, 2,6-디클로로-4-시아노-페닐, 2,6-디클로로-4-트리플루오로메톡시-페닐, 2,6-디클로로-4-트리플루오로메틸-페닐, 2,6-디클로로-페닐, 2,6-디메틸-4-(1,1-디메틸에틸)-페닐, 2,6-디메틸-페닐, 2-브로모-4-플루오로-6-메틸-페닐, 2-브로모-6-클로로-4-플루오로-페닐, 4-브로모-2,6-디메틸-페닐, 4-클로로-2,6-디메틸-페닐, 4-시아노-2,6-디메틸-페닐이다); L 은 -X2-Alk-R7 (여기에서, -X2-Alk- 는 -NH-CH2- 이고, R7 은 페닐이다)인 화합물.
- 제1항 또는 제2항에 있어서, Q 가 수소이고, L 이 -X1-R6 이며(여기에서, X1 은 -NH- 이고, R6 은 2,4,6-트리메틸-페닐 또는 4-시아노-2,6-디메틸페닐이다), NR3(페닐 또는 피리딜로 임의로 치환된) 부위가 p-시아노-아닐리노를 나타내고, 피리미딘 환의 2번 위치에 존재하는 화합물.
- 제1항 또는 제2항에 있어서, R4'는 시아노, 아미노카보닐 또는 시아노C1 - 6알킬이고; n'는 0이며; A 는 CH 이고; R3 는 수소이며; R5 는 수소 또는 메틸이고; Q 는 수소 또는 NHR1 이며; L 은 페닐, 2,4,6-트리클로로-페닐, 2,4,6-트리메틸-페닐, 2,4-디브로모-3,5-디클로로-페닐, 2,4-디브로모-6-플루오로-페닐, 2,4-디클로로-6-메틸-페닐, 2,6-디브로모-4-이소프로필-페닐, 2,6-디브로모-4-메틸-페닐, 2,6-디브로모-4-프로프-1-일-페닐, 2,6-디클로로-4-시아노-페닐, 2,6-디클로로-4-트리플루오로메톡시-페닐, 2,6-디클로로-4-트리플루오로메틸-페닐, 2,6-디클로로-페닐, 2,6-디메틸-4-(1,1-디메틸에틸)-페닐, 2,6-디메틸-페닐, 2-브로모-4-플루오로-6-메틸-페닐, 2-브로모-6-클로로-4-플루오로-페닐, 4-브로모-2,6-디메틸-페닐, 4-클로로-2,6-디메틸-페닐 또는 4-시아노-2,6-디메틸-페닐을 포함하는 화합물.
- 제1항에 있어서,4-[[4-아미노-6-[(2,6-디클로로페닐)메틸]-2-피리미디닐]아미노]벤조니트릴;6-[(2,6-디클로로페닐)메틸]-N2-(4-플루오로페닐)-2,4-피리미딘디아민;4-[[4-[(2,4-디클로로페닐)메틸]-6-[(4-하이드록시부틸)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디클로로페닐)메틸]-6-[(3-하이드록시프로필)아미노]-2-피리미디닐]아미노]벤조니트릴;N-[2-[(4-시아노페닐)아미노]-6-[(2,6-디클로로페닐)메틸]-4-피리미디닐]-아세트아미드;N-[2-[(4-시아노페닐)아미노]-6-[(2,6-디클로로페닐)메틸]-4-피리미디닐]-부탄아미드;4-[[2-아미노-6-(2,6-디클로로펜옥시)-4-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디클로로페닐)메틸]-6-[(2-하이드록시-2-페닐에틸)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디클로로페닐)메틸]-6-[(3-(2-옥소-1-피롤리디닐)프로필]아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디클로로페닐)메틸]-6-[[2-(2-하이드록시에톡시)에틸]아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디클로로페닐)메틸]-6-[(2,3-디하이드록시프로필)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디클로로페닐)메틸]-6-(하이드록시아미노)-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2-시아노에틸)아미노]-6-[(2,6-디클로로페닐)메틸]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디클로로페닐)메틸]-6-[[2-(1-피롤리디닐)에틸]아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-아미노-6-[(2,6-디클로로페닐)메틸]-5-메틸-2-피리미디닐]아미노]벤조 니트릴;N2-(4-브로모페닐)-6-[(2,6-디클로로페닐)메틸]-5-메틸-2,4-피리미딘디아민;4-[[4-[(2,4,6-트리메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[2-[(2,4,6-트리메틸페닐)아미노]-4-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-(2,4,6-트리메틸펜옥시)-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디클로로페닐)티오]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[[2,6-디브로모-4-(1-메틸에틸)페닐]아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[[2,6-디클로로-4-(트리플루오로메틸)페닐]아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,4-디클로로-6-메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[2-[(시아노페닐)아미노]-4-피리미디닐]아미노]-3,5-디메틸벤조니트릴;4-[[4-[(2,4-디브로모-6-플루오로페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-아미노-6-[(2,6-디클로로페닐)메틸]-5-메틸-2-피리미디닐]아미노]벤젠아세토니트릴;4-[[4-[메틸(2,4,6-트리메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,4,6-트리클로로페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,4,6-트리메틸페닐)티오]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,4,6-트리메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-아미노-6-(2,4,6-트리메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[2-아미노-6-(2,4,6-트리메틸페닐)아미노]-4-피리미디닐]아미노]벤조니트릴;4-[[4-(2-브로모-4-클로로-6-메틸펜옥시)-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(4-클로로-2,6-디메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;3,5-디클로로-4-[[2-[(4-시아노페닐)아미노]-4-피리미디닐]아미노]벤조니트릴;4-[[4-[[2,6-디클로로-4-(트리플루오로메톡시)페닐]아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,4-디브로모-3,6-디클로로페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디브로모-4-프로필페닐]아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,4,6-트리메틸페닐)아미노]-2-피리미디닐]아미노]벤즈아미드;4-[[4-[(4-(1,1-디메틸에틸)-2,6-디메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴;4-[[2-[(4-시아노페닐)아미노]-4-피리미디닐]옥시]-3,5-디메틸벤조니트릴;4-[[4-[(4-클로로-2,6-디메틸페닐)아미노]-5-메틸-2-피리미디닐]아미노]벤조 니트릴;4-[[2-[(4-시아노페닐)아미노]-5-메틸-4-피리미디닐]아미노]-3,5-디메틸벤조니트릴;4-[[4-[[4-(1,1-디메틸에틸)-2,6-디메틸페닐]아미노]-5-메틸-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(4-브로모-2,6-디메틸페닐)아미노]-5-메틸-2-피리미디닐]아미노]벤조니트릴;4-[[5-메틸-4-[(2,4,6-트리메틸페닐)티오]-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,6-디브로모-4-프로필페닐)아미노]-5-메틸-2-피리미디닐]아미노]벤조니트릴;4-[[4-[(2,4,6-트리메틸페닐)아미노]-2-피리미디닐]아미노]벤즈아미드, N3-옥사이드;N2-(4-클로로페닐)-N4-(2,4,6-트리메틸페닐)-2,4-피리미딘디아민;4-[[4-[[2,6-디브로모-4-(1-메틸에틸)페닐]아미노]-5-메틸-2-피리미디닐]아미노]벤조니트릴;4-[[2-[(4-시아노페닐)아미노]-5-메틸-4-피리미디닐]아미노]-3,5-디메틸벤조니트릴;4-[[4-[(페닐메틸)아미노]-2-피리미디닐]아미노]벤조니트릴;그의 N-옥사이드, 약제학적으로 허용되는 부가 염 또는 입체화학적 이성체 형태인 화합물.
- 제6항에 있어서, 4-[[2-[(시아노페닐)아미노]-4-피리미디닐]아미노]-3,5-디메틸벤조니트릴, 그의 N-옥사이드, 약제학적으로 허용되는 부가 염 또는 입체화학적 이성체 형태인 화합물.
- 제7항에 있어서, 4-[[2-[(시아노페닐)아미노]-4-피리미디닐]아미노]-3,5-디메틸벤조니트릴인 화합물.
- 제6항에 있어서, 4-[[4-[(2,4,6-트리메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴, 그의 N-옥사이드, 약제학적으로 허용되는 부가 염 또는 입체화학적 이성체 형태인 화합물.
- 제9항에 있어서, 4-[[4-[(2,4,6-트리메틸페닐)아미노]-2-피리미디닐]아미노]벤조니트릴인 화합물.
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US7963298P | 1998-03-27 | 1998-03-27 | |
US60/079632 | 1998-03-27 | ||
EP98201587.7 | 1998-05-14 | ||
EP98201587A EP0945442A1 (en) | 1998-03-27 | 1998-05-14 | Trisubstituted pyrimidine derivatives |
EP98203948 | 1998-11-25 | ||
EP98203948.9 | 1998-11-25 | ||
KR1020007007970A KR100643419B1 (ko) | 1998-03-27 | 1999-03-24 | Hiv를 억제하는 피리미딘 유도체 |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020007007970A Division KR100643419B1 (ko) | 1998-03-27 | 1999-03-24 | Hiv를 억제하는 피리미딘 유도체 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20060083440A KR20060083440A (ko) | 2006-07-20 |
KR100699514B1 true KR100699514B1 (ko) | 2007-03-26 |
Family
ID=27239326
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020067013365A KR100699514B1 (ko) | 1998-03-27 | 1999-03-24 | Hiv를 억제하는 피리미딘 유도체 |
Country Status (32)
Country | Link |
---|---|
EP (2) | EP0945443B9 (ko) |
JP (1) | JP3507917B2 (ko) |
KR (1) | KR100699514B1 (ko) |
CN (1) | CN1214014C (ko) |
AP (1) | AP1468A (ko) |
AT (1) | ATE232521T1 (ko) |
AU (1) | AU751573C (ko) |
BG (1) | BG64702B1 (ko) |
CA (1) | CA2324919C (ko) |
CZ (1) | CZ299380B6 (ko) |
DE (1) | DE69905306T2 (ko) |
DK (1) | DK0945443T3 (ko) |
EA (1) | EA002973B1 (ko) |
EE (1) | EE04850B1 (ko) |
ES (1) | ES2193660T3 (ko) |
HK (1) | HK1035901A1 (ko) |
HR (1) | HRP20000620B1 (ko) |
HU (1) | HU230522B1 (ko) |
ID (1) | ID26291A (ko) |
IL (1) | IL138669A0 (ko) |
MY (1) | MY126493A (ko) |
NO (1) | NO317424B1 (ko) |
NZ (1) | NZ506679A (ko) |
OA (1) | OA11492A (ko) |
PL (1) | PL202675B1 (ko) |
PT (1) | PT945443E (ko) |
SI (1) | SI0945443T1 (ko) |
SK (1) | SK287996B6 (ko) |
TR (1) | TR200002760T2 (ko) |
TW (1) | TW531534B (ko) |
UA (1) | UA72458C2 (ko) |
WO (1) | WO1999050250A1 (ko) |
Families Citing this family (118)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7772432B2 (en) | 1991-09-19 | 2010-08-10 | Astrazeneca Ab | Amidobenzamide derivatives which are useful as cytokine inhibitors |
EP0972770B1 (en) * | 1998-07-14 | 2001-09-19 | Basf Aktiengesellschaft | Acaricidal and insecticidal substituted pyrimidines and a process for the preparation thereof |
ES2270612T3 (es) | 1998-08-29 | 2007-04-01 | Astrazeneca Ab | Compuestos de pirimidina. |
ES2274634T3 (es) | 1998-08-29 | 2007-05-16 | Astrazeneca Ab | Compuestos de pirimidina. |
CN1158266C (zh) | 1998-10-01 | 2004-07-21 | 阿斯特拉曾尼卡有限公司 | 化合物 |
NZ511116A (en) | 1998-11-10 | 2003-08-29 | Janssen Pharmaceutica Nv | HIV replication inhibiting pyrimidines |
JP4535350B2 (ja) * | 1998-11-17 | 2010-09-01 | クミアイ化学工業株式会社 | ピリミジニルベンズイミダゾール誘導体及び農園芸用殺菌剤 |
AU755538B2 (en) | 1998-11-17 | 2002-12-12 | Ihara Chemical Industry Co. Ltd. | Pyrimidinylbenzimidazole and triazinylbenzimidazole derivatives and agricultural/horticultural fungicides |
GB9828511D0 (en) | 1998-12-24 | 1999-02-17 | Zeneca Ltd | Chemical compounds |
WO2000049001A2 (en) * | 1999-02-16 | 2000-08-24 | E.I. Du Pont De Nemours And Company | Phenoxy-, phenylthio-, phenylamino-, benzyloxy-, benzylthio- or benzylaminopyrimidine insectidices and acaricides |
GB9905075D0 (en) | 1999-03-06 | 1999-04-28 | Zeneca Ltd | Chemical compounds |
ES2219319T3 (es) | 1999-03-17 | 2004-12-01 | Astrazeneca Ab | Derivados de amida. |
GB9907658D0 (en) | 1999-04-06 | 1999-05-26 | Zeneca Ltd | Chemical compounds |
GB9919778D0 (en) | 1999-08-21 | 1999-10-27 | Zeneca Ltd | Chemical compounds |
DE19945982A1 (de) * | 1999-09-24 | 2001-03-29 | Knoll Ag | Geschwindigkeitsbestimmte Partikel |
IL148801A0 (en) | 1999-09-24 | 2002-09-12 | Janssen Pharmaceutica Nv | Antiviral compositions |
MXPA02003436A (es) | 1999-10-07 | 2002-08-20 | Amgen Inc | Inhibidores de triazina cinasa. |
GB9924092D0 (en) * | 1999-10-13 | 1999-12-15 | Zeneca Ltd | Pyrimidine derivatives |
CA2400447C (en) | 2000-02-17 | 2008-04-22 | Amgen Inc. | Kinase inhibitors |
GB0004887D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
GB0004888D0 (en) * | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
GB0004890D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
GB0004886D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
GB0007371D0 (en) | 2000-03-28 | 2000-05-17 | Astrazeneca Uk Ltd | Chemical compounds |
AU783981C (en) * | 2000-05-08 | 2007-05-03 | Janssen Pharmaceutica N.V. | HIV replication inhibitors |
US7034019B2 (en) | 2000-05-08 | 2006-04-25 | Janssen Pharmaceutica N.V. | Prodrugs of HIV replication inhibiting pyrimidines |
GB0016877D0 (en) | 2000-07-11 | 2000-08-30 | Astrazeneca Ab | Chemical compounds |
EP1313713B1 (en) * | 2000-08-08 | 2008-06-11 | Ortho-McNeil Pharmaceutical, Inc. | 4-pyrimidinamine derivatives, pharmaceutical compositions and related methods |
GB0021726D0 (en) | 2000-09-05 | 2000-10-18 | Astrazeneca Ab | Chemical compounds |
HU230574B1 (hu) | 2000-12-21 | 2023-11-28 | Novartis Ag | Pirimidinamin-származékok és ezeket tartalmazó gyógyászati készítmények, mint angiogenézis modulátorok |
US7081470B2 (en) | 2001-01-31 | 2006-07-25 | H. Lundbeck A/S | Use of GALR3 receptor antagonists for the treatment of depression and/or anxiety and compounds useful in such methods |
US20040127502A1 (en) | 2001-01-31 | 2004-07-01 | Synaptic Pharmaceutical Corporation | Use of GAL3 antagonist for treatment of depression |
US6555581B1 (en) | 2001-02-15 | 2003-04-29 | Jones Pharma, Inc. | Levothyroxine compositions and methods |
GB0103926D0 (en) | 2001-02-17 | 2001-04-04 | Astrazeneca Ab | Chemical compounds |
GB0113041D0 (en) | 2001-05-30 | 2001-07-18 | Astrazeneca Ab | Chemical compounds |
DK1433480T3 (da) | 2001-07-13 | 2011-04-11 | Btg Internat Ltd Company | Lægemiddel indeholdende pyrimidin-derivat |
US6958211B2 (en) | 2001-08-08 | 2005-10-25 | Tibotech Bvba | Methods of assessing HIV integrase inhibitor therapy |
US7638522B2 (en) | 2001-08-13 | 2009-12-29 | Janssen Pharmaceutica N.V. | Salt of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino] benzonitrile |
US8101629B2 (en) | 2001-08-13 | 2012-01-24 | Janssen Pharmaceutica N.V. | Salt of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile |
JO3429B1 (ar) * | 2001-08-13 | 2019-10-20 | Janssen Pharmaceutica Nv | مشتقات برميدينات مثبطة فيروس الايدز |
US7115617B2 (en) | 2001-08-22 | 2006-10-03 | Amgen Inc. | Amino-substituted pyrimidinyl derivatives and methods of use |
US6939874B2 (en) | 2001-08-22 | 2005-09-06 | Amgen Inc. | Substituted pyrimidinyl derivatives and methods of use |
WO2003032997A1 (de) | 2001-10-17 | 2003-04-24 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Pyrimidinderivate, arzneimittel enthaltend diese verbindungen, deren verwendung und verfahren zu ihrer herstellung |
EP1453516A2 (de) | 2001-10-17 | 2004-09-08 | Boehringer Ingelheim Pharma GmbH & Co.KG | 5-substituierte 4-amino-2-phenylamino-pyrimdinderivate und ihre verwendung als beta-amyloid modulatoren |
ATE389638T1 (de) * | 2001-11-01 | 2008-04-15 | Janssen Pharmaceutica Nv | Aminobenzamidderivate als inhibitoren der glycogensynthasekinase-3- |
BR0213792A (pt) | 2001-11-01 | 2004-12-07 | Janssen Pharmaceutica Nv | Heteroaril aminas como inibidores de glicogênio sintase cinase 3beta (inibidores de gsk3) |
JP2005507419A (ja) | 2001-11-01 | 2005-03-17 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | グリコーゲン合成酵素キナーゼ3ベータ阻害剤としてのアミド誘導体 |
AU2002367172A1 (en) * | 2001-12-21 | 2003-07-15 | Bayer Pharmaceuticals Corporation | 2,4-diamino-pyrimidine derivative compounds as inhibitors of prolylpeptidase, inducers of apoptosis and cancer treatment agents |
DE60305446T4 (de) | 2002-01-07 | 2009-07-09 | Eisai R&D Management Co., Ltd. | Desazapurine und deren verwendung |
TW200302728A (en) | 2002-02-01 | 2003-08-16 | Novartis Ag | Substituted amines as IgE inhibitors |
TWI329105B (en) * | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
GB0205693D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
GB0205688D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
GB0205690D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
JP2005524672A (ja) | 2002-03-09 | 2005-08-18 | アストラゼネカ アクチボラグ | Cdk阻害活性を有するイミダゾリル置換ピリミジン誘導体 |
PL213783B1 (pl) | 2002-03-13 | 2013-05-31 | Janssen Pharmaceutica Nv | Podstawiona pochodna piperydyny lub piperazyny, jej zastosowanie i sposób wytwarzania oraz kompozycja farmaceutyczna |
ATE396971T1 (de) | 2002-03-13 | 2008-06-15 | Janssen Pharmaceutica Nv | Sulfonylaminoderivate als neue inhibitoren von histondeacetylase |
GB0206215D0 (en) | 2002-03-15 | 2002-05-01 | Novartis Ag | Organic compounds |
AR039540A1 (es) * | 2002-05-13 | 2005-02-23 | Tibotec Pharm Ltd | Compuestos microbicidas con contenido de pirimidina o triazina |
SG176311A1 (en) | 2002-07-29 | 2011-12-29 | Rigel Pharmaceuticals | Methods of treating or preventing autoimmune diseases with 2,4-pyrimidinediamine compounds |
BR0313545B1 (pt) * | 2002-08-09 | 2021-07-27 | Janssen Pharmaceutica Nv | processos para a preparação de 4-[[4-[[4-(2-cianoetenil)-2,6-dimetilfenil]amino]-2-pirimidinil]amino]benzonitrila |
JP2006508997A (ja) * | 2002-11-28 | 2006-03-16 | シエーリング アクチエンゲゼルシャフト | Chk−、Pdk−およびAkt−阻害性ピリミジン、それらの製造および薬剤としての使用 |
WO2004050068A1 (en) * | 2002-11-29 | 2004-06-17 | Janssen Pharmaceutica N.V. | Pharmaceutical compositions comprising a basic respectively acidic drug compound, a surfactant and a physiologically tolerable water-soluble acid respectively base |
CA2513527C (en) * | 2003-02-07 | 2012-08-14 | Janssen Pharmaceutica N.V. | Pyrimidine derivatives for the prevention of hiv infection |
EA010379B1 (ru) * | 2003-02-07 | 2008-08-29 | Янссен Фармацевтика Н.В. | Ингибирующие вич 1,2,4-триазины |
US7514446B2 (en) | 2003-02-20 | 2009-04-07 | Smithkline Beecham Corporation | Pyrimidine compounds |
CL2004000303A1 (es) * | 2003-02-20 | 2005-04-08 | Tibotec Pharm Ltd | Compuestos derivados de pirimidinas y triazinas; proceso de preparacion; composicion farmaceutica; y su uso para inhibir la replicacion del vih. |
GB0305929D0 (en) | 2003-03-14 | 2003-04-23 | Novartis Ag | Organic compounds |
GB0311274D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
GB0311276D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
ES2667668T3 (es) | 2003-07-17 | 2018-05-14 | Janssen Sciences Ireland Uc | Procedimiento para preparar partículas que contienen un antiviral |
CN102358738A (zh) | 2003-07-30 | 2012-02-22 | 里格尔药品股份有限公司 | 2,4-嘧啶二胺化合物及其预防和治疗自体免疫疾病的用途 |
JP4607879B2 (ja) | 2003-08-15 | 2011-01-05 | ノバルティス アーゲー | 新生物疾患、炎症および免疫障害の処置に有用な2,4−ピリミジンジアミン |
EA009734B1 (ru) | 2003-09-25 | 2008-02-28 | Янссен Фармацевтика Н.В. | Производные пурина, ингибирующие репликацию вич |
GB0324790D0 (en) | 2003-10-24 | 2003-11-26 | Astrazeneca Ab | Amide derivatives |
TW200528101A (en) | 2004-02-03 | 2005-09-01 | Astrazeneca Ab | Chemical compounds |
WO2005086061A2 (en) | 2004-03-02 | 2005-09-15 | Virco Bvba | Estimation of clinical cut-offs |
EP1598343A1 (de) * | 2004-05-19 | 2005-11-23 | Boehringer Ingelheim International GmbH | 2-Arylaminopyrimidine als PLK Inhibitoren |
NZ552865A (en) | 2004-07-28 | 2009-09-25 | Janssen Pharmaceutica Nv | Substituted indolyl alkyl amino derivatives as novel inhibitors of histone deacetylase |
CA2575002C (en) | 2004-08-10 | 2015-01-20 | Janssen Pharmaceutica N.V. | Hiv inhibiting 1,2,4-triazin-6-one derivatives |
MX2007003796A (es) | 2004-09-30 | 2007-04-25 | Tibotec Pharm Ltd | Pirimidinas 5-sustituidas inhibidoras del virus de inmunodeficiencia humana. |
RU2405778C2 (ru) | 2004-09-30 | 2010-12-10 | Тиботек Фармасьютикалз Лтд. | 5-гетероциклилпиримидины, ингибирующие вич |
WO2006035068A2 (en) * | 2004-09-30 | 2006-04-06 | Tibotec Pharmaceuticals Ltd. | Hiv inhibiting 5-carbo- or heterocyclic substituted pyrimidines |
JP5118972B2 (ja) | 2004-10-29 | 2013-01-16 | テイボテク・フアーマシユーチカルズ | Hiv阻害性二環式ピリミジン誘導体 |
WO2006068770A1 (en) | 2004-11-24 | 2006-06-29 | Rigel Pharmaceuticals, Inc. | Spiro-2, 4-pyrimidinediamine compounds and their uses |
CA2591948C (en) | 2005-01-19 | 2013-11-12 | Rigel Pharmaceuticals, Inc. | Prodrugs of 2,4-pyrimidinediamine compounds and their uses |
DK1888537T3 (da) * | 2005-05-26 | 2013-12-09 | Janssen R & D Ireland | Fremgangsmåde til fremstilling af 4[(1,6-dihydro-6-oxo-2-pyrimidinyl)amino]benzonitril |
AU2006296386A1 (en) | 2005-09-30 | 2007-04-05 | Astrazeneca Ab | Imidazo [1,2-a] pyridine having anti-cell-proliferation activity |
CA2631232A1 (en) | 2005-12-01 | 2007-06-07 | F. Hoffmann-La Roche Ag | Novel vinylogous acids derivatives |
CA2630717C (en) | 2006-01-19 | 2015-02-24 | Janssen Pharmaceutica N.V. | Pyridine and pyrimidine derivatives as inhibitors of histone deacetylase |
CA2645958C (en) | 2006-03-30 | 2014-11-04 | Tibotec Pharmaceuticals Ltd. | Hiv inhibiting 5-amido substituted pyrimidines |
BRPI0709266B8 (pt) | 2006-03-30 | 2021-05-25 | Janssen R & D Ireland | 5-(hidroximetileno e aminometileno) pirimidinas substituídas e composição farmacêutica que as compreende |
US20070293494A1 (en) | 2006-06-15 | 2007-12-20 | Djung Jane F | 2-Anilino-4-(Heterocyclic) Amino-Pyrimidines |
KR20090023698A (ko) | 2006-06-15 | 2009-03-05 | 베링거 인겔하임 인터내셔날 게엠베하 | 2-아닐리노-4-아미노알킬렌아미노피리미딘 |
US7705034B2 (en) | 2006-10-13 | 2010-04-27 | Hoffmann-La Roche Inc. | Vinylogous acid derivatives |
WO2008051547A1 (en) * | 2006-10-23 | 2008-05-02 | Cephalon, Inc. | Fused bicyclic derivatives of 2,4-diaminopyrimidine as alk and c-met inhibitors |
UA100846C2 (uk) | 2006-12-08 | 2013-02-11 | Айерем Елелсі | Сполуки та композиція як інгібітори протеїнкінази |
CA2674178C (en) * | 2006-12-29 | 2015-11-10 | Tibotec Pharmaceuticals Ltd. | Hiv inhibiting 6-substituted pyrimidines |
AU2007341228B2 (en) | 2006-12-29 | 2013-04-18 | Janssen Sciences Ireland Uc | HIV inhibiting 5,6-substituted pyrimidines |
US7982036B2 (en) | 2007-10-19 | 2011-07-19 | Avila Therapeutics, Inc. | 4,6-disubstitued pyrimidines useful as kinase inhibitors |
US7989465B2 (en) | 2007-10-19 | 2011-08-02 | Avila Therapeutics, Inc. | 4,6-disubstituted pyrimidines useful as kinase inhibitors |
US8153790B2 (en) | 2009-07-27 | 2012-04-10 | Krizmanic Irena | Process for the preparation and purification of etravirine and intermediates thereof |
GR1007010B (el) | 2009-10-08 | 2010-10-07 | Χημικα Και Βιοφαρμακευτικα Εργαστηρια Πατρων Αε (Cbl-Patras), | Ινσουλινοειδη πεπτιδια |
CN101723904B (zh) * | 2009-11-26 | 2012-02-08 | 复旦大学 | 4-氰基二芳基嘧啶类衍生物及其制备方法和用途 |
CA2812109A1 (en) | 2010-09-20 | 2012-03-29 | Kareus Therapeutics, Sa | Methods and compositions for treatment of diabetes and dyslipidemia |
US8580294B2 (en) | 2010-10-19 | 2013-11-12 | International Partnership For Microbicides | Platinum-catalyzed intravaginal rings |
WO2012060847A1 (en) | 2010-11-07 | 2012-05-10 | Targegen, Inc. | Compositions and methods for treating myelofibrosis |
WO2013059572A1 (en) * | 2011-10-19 | 2013-04-25 | Assia Chemical Industries Ltd. | Process for the preparation of etravirine and intermediates in the synthesis thereof |
MX2014009933A (es) * | 2012-02-17 | 2015-12-16 | Abbvie Inc | Diaminopirimidinas utiles como inhibidores del virus sincitial respiratorio humano (rsv). |
WO2014072419A1 (en) | 2012-11-08 | 2014-05-15 | Universiteit Antwerpen | Novel anti-hiv compounds |
US9914709B2 (en) | 2013-06-21 | 2018-03-13 | Yale University | Compositions and methods of treating HIV-1 infections using same |
CN103483272B (zh) * | 2013-09-29 | 2015-10-21 | 山东大学 | 间二芳烃-多取代嘧啶类衍生物及其制备方法与应用 |
US9296727B2 (en) * | 2013-10-07 | 2016-03-29 | Vertex Pharmaceuticals Incorporated | Methods of regioselective synthesis of 2,4-disubstituted pyrimidines |
US10137031B2 (en) | 2013-11-14 | 2018-11-27 | International Partnership For Microbicides, Inc. | Combination therapy intravaginal rings |
CN106478521A (zh) * | 2016-10-11 | 2017-03-08 | 武汉工程大学 | 一种二芳基嘧啶类hiv‑1逆转录酶抑制剂及其制备方法 |
US10172856B2 (en) | 2017-04-06 | 2019-01-08 | Janssen Pharmaceutica Nv | 2,4-diaminopyrimidine derivatives as histamine H4 modulators |
EP4380613A1 (en) | 2021-08-03 | 2024-06-12 | The United States of America, as represented by the Secretary, Department of Health and Human Services | Hiv-1 vaccination and samt-247 microbicide to prevent hiv-1 infection |
WO2023220645A1 (en) | 2022-05-10 | 2023-11-16 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Vaccine for human t-lymphotropic virus-1 |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1477349A (en) | 1975-09-24 | 1977-06-22 | Ciba Geigy Ag | Azo pigments |
JPS57203072A (en) * | 1981-06-05 | 1982-12-13 | Sankyo Co Ltd | 4-anilinopyrimidine derivative, its preparation, antidepressant comprising it as active ingredient |
US4659363A (en) * | 1983-07-25 | 1987-04-21 | Ciba-Geigy Corporation | N-(2-nitrophenyl)-2-aminopyrimidine derivatives, the preparation and use thereof |
JPH0784445B2 (ja) * | 1986-12-03 | 1995-09-13 | クミアイ化学工業株式会社 | ピリミジン誘導体および農園芸用殺菌剤 |
JPH0252360A (ja) | 1988-08-15 | 1990-02-21 | Fujitsu Ltd | 電子写真感光体 |
JPH02300264A (ja) | 1989-05-16 | 1990-12-12 | Fuji Photo Film Co Ltd | アミノピリミジンアゾメチン色素とその製造方法 |
JPH02308248A (ja) | 1989-05-24 | 1990-12-21 | Fuji Photo Film Co Ltd | アミノピリミジン系色素形成カプラーおよび該カプラーを含有するハロゲン化銀カラー写真感光材料 |
GB9012592D0 (en) | 1990-06-06 | 1990-07-25 | Smithkline Beecham Intercredit | Compounds |
US5516775A (en) * | 1992-08-31 | 1996-05-14 | Ciba-Geigy Corporation | Further use of pyrimidine derivatives |
JP3398152B2 (ja) * | 1993-10-12 | 2003-04-21 | ブリストル‐マイヤーズ・スクイブ・ファーマ・カンパニー | 1n−アルキル−n−アリールピリミジンアミンおよびその誘導体 |
JP3691101B2 (ja) | 1995-01-24 | 2005-08-31 | 三洋電機株式会社 | 有機エレクトロルミネッセンス素子 |
JPH0968784A (ja) | 1995-08-31 | 1997-03-11 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料 |
JPH0980676A (ja) | 1995-09-13 | 1997-03-28 | Fuji Photo Film Co Ltd | ハロゲン化銀カラー写真感光材料およびその包装体 |
-
1999
- 1999-03-24 SI SI9930256T patent/SI0945443T1/xx unknown
- 1999-03-24 CA CA002324919A patent/CA2324919C/en not_active Expired - Lifetime
- 1999-03-24 UA UA2000105945A patent/UA72458C2/uk unknown
- 1999-03-24 AU AU35996/99A patent/AU751573C/en not_active Expired
- 1999-03-24 CN CNB998044490A patent/CN1214014C/zh not_active Expired - Lifetime
- 1999-03-24 IL IL13866999A patent/IL138669A0/xx not_active IP Right Cessation
- 1999-03-24 TR TR2000/02760T patent/TR200002760T2/xx unknown
- 1999-03-24 JP JP2000541155A patent/JP3507917B2/ja not_active Expired - Lifetime
- 1999-03-24 AT AT99200918T patent/ATE232521T1/de active
- 1999-03-24 HU HU0101204A patent/HU230522B1/hu unknown
- 1999-03-24 ID IDW20001897A patent/ID26291A/id unknown
- 1999-03-24 PL PL343196A patent/PL202675B1/pl unknown
- 1999-03-24 EA EA200000990A patent/EA002973B1/ru not_active IP Right Cessation
- 1999-03-24 PT PT99200918T patent/PT945443E/pt unknown
- 1999-03-24 NZ NZ506679A patent/NZ506679A/xx not_active IP Right Cessation
- 1999-03-24 ES ES99200918T patent/ES2193660T3/es not_active Expired - Lifetime
- 1999-03-24 DE DE69905306T patent/DE69905306T2/de not_active Expired - Lifetime
- 1999-03-24 WO PCT/EP1999/002043 patent/WO1999050250A1/en active IP Right Grant
- 1999-03-24 KR KR1020067013365A patent/KR100699514B1/ko not_active IP Right Cessation
- 1999-03-24 CZ CZ20003425A patent/CZ299380B6/cs not_active IP Right Cessation
- 1999-03-24 AP APAP/P/2000/001912A patent/AP1468A/en active
- 1999-03-24 EP EP99200918A patent/EP0945443B9/en not_active Expired - Lifetime
- 1999-03-24 SK SK1406-2000A patent/SK287996B6/sk not_active IP Right Cessation
- 1999-03-24 DK DK99200918T patent/DK0945443T3/da active
- 1999-03-24 EE EEP200000532A patent/EE04850B1/xx unknown
- 1999-03-24 EP EP02014566A patent/EP1245567B1/en not_active Expired - Lifetime
- 1999-03-25 MY MYPI99001133A patent/MY126493A/en unknown
- 1999-03-26 TW TW088104755A patent/TW531534B/zh not_active IP Right Cessation
-
2000
- 2000-08-30 BG BG104738A patent/BG64702B1/bg unknown
- 2000-09-19 HR HR20000620A patent/HRP20000620B1/xx not_active IP Right Cessation
- 2000-09-26 NO NO20004810A patent/NO317424B1/no not_active IP Right Cessation
- 2000-09-27 OA OA1200000265A patent/OA11492A/en unknown
-
2001
- 2001-09-14 HK HK01106524A patent/HK1035901A1/xx not_active IP Right Cessation
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR100699514B1 (ko) | Hiv를 억제하는 피리미딘 유도체 | |
KR100643419B1 (ko) | Hiv를 억제하는 피리미딘 유도체 | |
EP0834507B1 (en) | Substituted diamino-1,3,5-triazine derivatives | |
AU782948B2 (en) | Prodrugs of HIV replication inhibiting pyrimidines | |
EP0945447A1 (en) | Trisubstituted 1,3,5-triazine derivatives for treatment of HIV infections | |
EP0945442A1 (en) | Trisubstituted pyrimidine derivatives | |
MXPA00009435A (en) | Hiv inhibiting pyrimidine derivatives |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A107 | Divisional application of patent | ||
A201 | Request for examination | ||
E902 | Notification of reason for refusal | ||
E701 | Decision to grant or registration of patent right | ||
GRNT | Written decision to grant | ||
FPAY | Annual fee payment |
Payment date: 20130221 Year of fee payment: 7 |
|
FPAY | Annual fee payment |
Payment date: 20140220 Year of fee payment: 8 |
|
FPAY | Annual fee payment |
Payment date: 20150224 Year of fee payment: 9 |
|
FPAY | Annual fee payment |
Payment date: 20160218 Year of fee payment: 10 |
|
FPAY | Annual fee payment |
Payment date: 20170220 Year of fee payment: 11 |
|
FPAY | Annual fee payment |
Payment date: 20180219 Year of fee payment: 12 |
|
EXPY | Expiration of term |