KR950017971A - 신규한 항바이러스성 2, 4-피리미딘디온 유도체 및 그의 제조방법 - Google Patents
신규한 항바이러스성 2, 4-피리미딘디온 유도체 및 그의 제조방법 Download PDFInfo
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- KR950017971A KR950017971A KR1019940029388A KR19940029388A KR950017971A KR 950017971 A KR950017971 A KR 950017971A KR 1019940029388 A KR1019940029388 A KR 1019940029388A KR 19940029388 A KR19940029388 A KR 19940029388A KR 950017971 A KR950017971 A KR 950017971A
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- 230000000840 anti-viral effect Effects 0.000 title claims abstract 3
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title 1
- 125000005843 halogen group Chemical group 0.000 claims abstract 10
- 125000003277 amino group Chemical group 0.000 claims abstract 6
- 150000003839 salts Chemical class 0.000 claims abstract 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 6
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract 3
- -1 carbonyloxy, hydroxy Chemical group 0.000 claims abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims abstract 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims abstract 2
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 2
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract 2
- 125000004185 ester group Chemical group 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 125000005499 phosphonyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000012299 nitrogen atmosphere Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- NBFQYHKHPBMJJV-UHFFFAOYSA-N risocaine Chemical group CCCOC(=O)C1=CC=C(N)C=C1 NBFQYHKHPBMJJV-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
Classifications
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- 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
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- 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
-
- 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
- C07D239/60—Three or more oxygen or sulfur atoms
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Description
Claims (8)
- 하기 일반식(Ⅰ)의 화합물 또는 그의 약제학적으로 허용가능한 염;상기식에서 R1은 C3-C15의 식 CH2CH=CR5R6의 치환된 알릴기 또는 식 CH2C=CR7의 치환된 프로파질기를 나타내며, 여기서 R5, R6및 R7은 각각 독립적으로 수소원자; C1-C10의 카르보닐옥시기, 히드록시기, 아지도기, 시아노기, 할로겐 원자, 치환되거나 치환되지 않은 아미노기, 치환되거나 치환되지 않은 포스포닐기, 치환되거나 치환되지 않은 페닐기, C3-C10의 헤테로아릴기, C1-C3의 알콕시기 또는 벤질옥시기로 치환되거나 치환되지 않은 메틸기; C2-C10의 알킬기 또는 알케닐기; 시클로프로필기; 치환되거나 치환되지 않은 페닐기; C3-C10의 헤테로아릴기; C1-C10의 에스테르기; 또는 치환되거나 치환되지 않은 C1-C10의 알킬아미드기를 나타내며, R2는 할로겐원자, 치환되거나 치환되지 않은 C1-C5의 알킬기, 치환되거나 치환되지 않은 C3-C6의 시클로알킬기, 치환되거나 치환되지 않은 C2-C8의 알케닐기, 치환되거나 치환되지 않은 C2-C8의 알키닐기 또는 벤질기를 나타내며, R3및 R4는 각각 독립적으로 수소원자, 할로겐원자, 히드록시기, C1-C3의 알킬기, 불소화메틸기, C1-C3의 알콕시기, 아미노기, C2-C6의 알킬에스테르기 또는 C2-C7의 알킬아미드기를 나타내며, A는 산소원자 또는 황원자를 나타내며, Z는 산소원자; 황원자; 카르보닐기; 아미노기; 할로겐원자, 시아노기, 히드록시기, 아지도기, 아미노기, C1-C3의 아미드기, C1-C4의 에스테르기 및 니트로기중에서 선택된 하나 또는 그 이상의 치환기로 치환되거나 치환되지 않은 메틸렌기를 나타낸다.
- 제1항에 있어서, 상기 일반식(Ⅰ)에서 A가 산소원자이고, Z가 산소원자, 황원자, 카르보닐기 또는 메틸렌기인 일반식(Ⅰ)의 화합물 또는 그의 약제학적으로 허용가능한 염.
- 제3항에 있어서, 상기 일반식(Ⅰ)에서 R2가 치환되거나 치환되지 않은 C1-C3의 알킬기인 일반식(Ⅰ)의 화합물 또는 그의 약제학적으로 허용가능한 염.
- 제3항에 있어서, 상기 일반식(Ⅰ)에서 R2가 에틸기 또는 이소프로필기이고, R3및 R4가 각각 독립적으로 수소원자, 할로겐원자, 히드록시기, C1-C3의 알킬기, 불소화메틸기 또는 C1-C3의 알콕시기인 일반식(Ⅰ)의 화합물 또는 그의 약제학적으로 허용가능한 염.
- 하기 일반식(Ⅱ)의 화합물과 하기 일반식(Ⅲ)의 화합물을 반응시킴을 포함하는, 하기 일반식(Ⅰ)의 제조 방법;상기식에서, A,R1,R2,R3,R4,R5및 Z는 제1항에서 정의한 바와 같고, X는 할로겐원자 또는 술포닐옥시기를 나타낸다.
- 제5항에 있어서, 상기 일반식(Ⅱ)의 화합물과 상기 일반식(Ⅲ)의 화합물을 염기 및 극성 용매중에서 0 내지 100℃에서 질소분위기하에 1:0.8 내지 1:1.2의 몰비로 반응시키는 방법.
- 하기 일반식(Ⅱ)의 화합물;상기식에서, R2는 에틸기 또는 이소프로필기를 나타내고, R3및 R4는 메틸기를 나타내고, Z는 산소원자, 황원자, 카르보닐기 또는 메틸렌기를 나타낸다.
- 제1항 내지 제4항중 어느 한 항의 화합물 또는 그의 약제학적으로 허용가능한 염의 항 바이러스 효과량 및 그의 약제학적으로 허용 가능한 담체를 포함하는 약학 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR1019940029388A KR0151811B1 (ko) | 1993-12-21 | 1994-11-10 | 신규한 항바이러스성 2,4-피리미딘디온 유도체 및 그의 제조방법 |
AU12502/95A AU1250295A (en) | 1993-12-21 | 1994-12-20 | Novel antiviral 2,4-pyrimidinedione derivatives and processes for the preparation thereof |
DE69426836T DE69426836D1 (de) | 1993-12-21 | 1994-12-20 | Antivirale 2,4-pyrimidindion-derivate und verfahren zu ihrer herstellung |
EP95903455A EP0736015B1 (en) | 1993-12-21 | 1994-12-20 | Antiviral 2,4-pyrimidindione derivatives and processes for the preparation thereof |
PCT/KR1994/000178 WO1995018109A1 (en) | 1993-12-21 | 1994-12-20 | Novel antiviral 2,4-pyrimidinedione derivatives and processes for the preparation thereof |
JP7517935A JP2935573B2 (ja) | 1993-12-21 | 1994-12-20 | 新規な抗ウイルス性2,4−ピリミジンジオン誘導体及びその製造方法 |
AT95903455T ATE199549T1 (de) | 1993-12-21 | 1994-12-20 | Antivirale 2,4-pyrimidindion-derivate und verfahren zu ihrer herstellung |
US08/656,354 US5747500A (en) | 1993-12-21 | 1994-12-20 | Antiviral 2, 4-pyrimidinedione derivatives |
Applications Claiming Priority (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR2019930028909U KR950017498U (ko) | 1993-12-21 | 1993-12-21 | 자동차의 스태빌라이저 장착구조 |
KR93-20909 | 1993-12-21 | ||
KR2019930028908U KR0132614Y1 (ko) | 1993-12-21 | 1993-12-21 | 자동차의 좌석 틸트장치 |
KR93-28908 | 1993-12-21 | ||
KR93-28909 | 1993-12-21 | ||
KR19940010263 | 1994-05-11 | ||
KR19940010264 | 1994-05-11 | ||
KR94-10262 | 1994-05-11 | ||
KR19940010262 | 1994-05-11 | ||
KR94-10263 | 1994-05-11 | ||
KR94-10264 | 1994-05-11 | ||
KR1019940029388A KR0151811B1 (ko) | 1993-12-21 | 1994-11-10 | 신규한 항바이러스성 2,4-피리미딘디온 유도체 및 그의 제조방법 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR950017971A true KR950017971A (ko) | 1995-07-22 |
KR0151811B1 KR0151811B1 (ko) | 1998-10-15 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019940029388A KR0151811B1 (ko) | 1993-12-21 | 1994-11-10 | 신규한 항바이러스성 2,4-피리미딘디온 유도체 및 그의 제조방법 |
Country Status (8)
Country | Link |
---|---|
US (1) | US5747500A (ko) |
EP (1) | EP0736015B1 (ko) |
JP (1) | JP2935573B2 (ko) |
KR (1) | KR0151811B1 (ko) |
AT (1) | ATE199549T1 (ko) |
AU (1) | AU1250295A (ko) |
DE (1) | DE69426836D1 (ko) |
WO (1) | WO1995018109A1 (ko) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100311949B1 (ko) * | 1999-03-10 | 2001-11-02 | 최승주 | 1-[(사이클로펜트-3-엔-1-일)메틸]-5-에틸-6-(3,5-다이메틸벤조일)-2,4-피리미딘다이온의제조방법 |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
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US5476855A (en) * | 1993-11-02 | 1995-12-19 | Mahmoud H. el Kouni | Enzyme inhibitors, their synthesis and methods for use |
RU2138487C1 (ru) * | 1996-02-22 | 1999-09-27 | Самдзин Фармасьютикал Ко., Лтд. | Новые противовирусные гомокарбоциклические нуклеозидные производные замещенных пиримидиндионов, способ их получения и композиция, содержащая их в качестве активных ингредиентов |
KR100219922B1 (ko) * | 1996-05-16 | 1999-09-01 | 이서봉 | 신규한 항바이러스성 6-아릴옥시 및 6-아릴카르보닐 2,4-피리미딘디온 유도체 및 그의 제조 방법 |
ES2182420T3 (es) * | 1998-06-26 | 2003-03-01 | Crompton Vinyl Additives Gmbh | 6-aminouracilos sustituidos en posicion 5 como estabilizadores para polimeros halogenados. |
IT1305313B1 (it) * | 1998-07-17 | 2001-05-04 | Colla Paolo | 3,4 - diidro- 6- benzil-4-oxopirimidine sostituite e relativo processodi produzione e impiego nella terapia delle infezioni da hiv-1. |
US6713486B1 (en) * | 1999-03-04 | 2004-03-30 | Korea Research Institute Of Chemical Technology | Antiviral 2,4-pyrimidinedione derivatives and process for the preparation thereof |
KR100368891B1 (ko) * | 1999-03-04 | 2003-01-24 | 한국화학연구원 | 신규한 항바이러스성 2,4-피리미딘디온 유도체 |
KR20000065885A (ko) * | 1999-04-10 | 2000-11-15 | 최승주 | 항바이러스성 피리미딘다이온 유도체 및 그 제조방법 |
AU2002248910A1 (en) | 2000-11-17 | 2002-05-27 | Idenix (Cayman) Limited | Methods for inhibiting the transmission of HIV using topically applied substituted 6-benzyl-4-oxopyrmidines |
KR20020074683A (ko) * | 2001-03-21 | 2002-10-04 | 주식회사 엘지씨아이 | 항바이러스성 2,4-피리미딘디온 유도체 및 그의 제조방법 |
KR101257378B1 (ko) * | 2006-04-19 | 2013-04-23 | 삼진제약주식회사 | 항바이러스성 피리미딘디온 유도체 및 이의 제조 방법 |
US8334295B2 (en) * | 2007-06-29 | 2012-12-18 | Korea Research Institute Of Chemical Technology | Pyrimidine derivatives as HIV reverse transcriptase inhibitors |
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KR20170132326A (ko) | 2015-05-05 | 2017-12-01 | 화이자 인코포레이티드 | 2-티오피리미딘온 |
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---|---|---|---|---|
US4730001A (en) * | 1986-01-22 | 1988-03-08 | Southern Research Institute | Carbocyclic analogues of amino and azido thymidines |
HU205917B (en) * | 1989-09-29 | 1992-07-28 | Mitsubishi Chem Ind | Process for producing 6-substituted pyrimidine derivatives and antiviral pharmaceutical compositions containing them as active components |
CA2036304C (en) * | 1990-02-15 | 2001-04-17 | Takehiko Naka | Pyrimidinedione derivatives, their production and use |
CA2039039C (en) * | 1990-03-29 | 2001-05-15 | Tadashi Miyasaka | Pyrimidine nucleoside derivative and antiviral agent containing the derivative as active ingredient |
USH1142H (en) * | 1990-11-05 | 1993-02-02 | Optically active cyclobutyl pyrimidine |
-
1994
- 1994-11-10 KR KR1019940029388A patent/KR0151811B1/ko not_active IP Right Cessation
- 1994-12-20 EP EP95903455A patent/EP0736015B1/en not_active Expired - Lifetime
- 1994-12-20 WO PCT/KR1994/000178 patent/WO1995018109A1/en active IP Right Grant
- 1994-12-20 DE DE69426836T patent/DE69426836D1/de not_active Expired - Lifetime
- 1994-12-20 JP JP7517935A patent/JP2935573B2/ja not_active Expired - Fee Related
- 1994-12-20 AU AU12502/95A patent/AU1250295A/en not_active Abandoned
- 1994-12-20 US US08/656,354 patent/US5747500A/en not_active Expired - Lifetime
- 1994-12-20 AT AT95903455T patent/ATE199549T1/de not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100311949B1 (ko) * | 1999-03-10 | 2001-11-02 | 최승주 | 1-[(사이클로펜트-3-엔-1-일)메틸]-5-에틸-6-(3,5-다이메틸벤조일)-2,4-피리미딘다이온의제조방법 |
Also Published As
Publication number | Publication date |
---|---|
WO1995018109A1 (en) | 1995-07-06 |
EP0736015A1 (en) | 1996-10-09 |
ATE199549T1 (de) | 2001-03-15 |
US5747500A (en) | 1998-05-05 |
AU1250295A (en) | 1995-07-17 |
JPH09509405A (ja) | 1997-09-22 |
EP0736015B1 (en) | 2001-03-07 |
KR0151811B1 (ko) | 1998-10-15 |
DE69426836D1 (de) | 2001-04-12 |
JP2935573B2 (ja) | 1999-08-16 |
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