KR860008177A - 이미다조퀴놀린 항혈전성 강심제 - Google Patents
이미다조퀴놀린 항혈전성 강심제 Download PDFInfo
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- KR860008177A KR860008177A KR1019860003204A KR860003204A KR860008177A KR 860008177 A KR860008177 A KR 860008177A KR 1019860003204 A KR1019860003204 A KR 1019860003204A KR 860003204 A KR860003204 A KR 860003204A KR 860008177 A KR860008177 A KR 860008177A
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- compound
- quinolin
- imidazo
- dihydro
- lower alkyl
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- 230000002785 anti-thrombosis Effects 0.000 title 1
- 239000003146 anticoagulant agent Substances 0.000 title 1
- SQQXRXKYTKFFSM-UHFFFAOYSA-N chembl1992147 Chemical compound OC1=C(OC)C(OC)=CC=C1C1=C(C)C(C(O)=O)=NC(C=2N=C3C4=NC(C)(C)N=C4C(OC)=C(O)C3=CC=2)=C1N SQQXRXKYTKFFSM-UHFFFAOYSA-N 0.000 title 1
- 230000002526 effect on cardiovascular system Effects 0.000 title 1
- 229940124669 imidazoquinoline Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 48
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 150000003839 salts Chemical class 0.000 claims 20
- 229910052736 halogen Inorganic materials 0.000 claims 16
- 150000002367 halogens Chemical class 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 229910052739 hydrogen Inorganic materials 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 238000006243 chemical reaction Methods 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- 229940091173 hydantoin Drugs 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 2
- PBOWJMPDKAAEDU-UHFFFAOYSA-N 1,3,7,8-tetramethylimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2N(C)C(=O)N(C)C2=CC2=C(C)C(C)=CC=C21 PBOWJMPDKAAEDU-UHFFFAOYSA-N 0.000 claims 1
- OGGMUYJRABMJGV-UHFFFAOYSA-N 1,7-dimethyl-3h-imidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)N(C)C2=CC2=CC(C)=CC=C21 OGGMUYJRABMJGV-UHFFFAOYSA-N 0.000 claims 1
- YEZYOQWGSQOGIH-UHFFFAOYSA-N 1,8-dimethyl-3h-imidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C(C)=CC=CC2=NC2=C1N(C)C(=O)N2 YEZYOQWGSQOGIH-UHFFFAOYSA-N 0.000 claims 1
- SWFQYDVZFIVQHW-UHFFFAOYSA-N 1,8-dimethyl-9,9a-dihydro-4h-imidazo[4,5-b]quinolin-2-one Chemical compound C1C2=C(C)C=CC=C2N=C2C1N(C)C(=O)N2 SWFQYDVZFIVQHW-UHFFFAOYSA-N 0.000 claims 1
- AMQUYLNSYUJEKH-UHFFFAOYSA-N 6,7,8-trimethoxy-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C(OC)=C(OC)C(OC)=CC2=NC2=C1NC(=O)N2 AMQUYLNSYUJEKH-UHFFFAOYSA-N 0.000 claims 1
- CKJZPMFALWTSJS-UHFFFAOYSA-N 6,7-dimethoxy-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2C=C(OC)C(OC)=CC2=CC2=C1NC(=O)N2 CKJZPMFALWTSJS-UHFFFAOYSA-N 0.000 claims 1
- VBQVHGPNYUAGFI-UHFFFAOYSA-N 6,7-dimethyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2C=C(C)C(C)=CC2=CC2=C1NC(=O)N2 VBQVHGPNYUAGFI-UHFFFAOYSA-N 0.000 claims 1
- OIKKOZDXQORKSP-UHFFFAOYSA-N 6-(trifluoromethyl)-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2NC(=O)NC2=NC2=CC(C(F)(F)F)=CC=C21 OIKKOZDXQORKSP-UHFFFAOYSA-N 0.000 claims 1
- ODCKPUDNMNCWMR-UHFFFAOYSA-N 7,8-dimethyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=C(C)C(C)=CC=C21 ODCKPUDNMNCWMR-UHFFFAOYSA-N 0.000 claims 1
- YCKKLLYMMVHPIG-UHFFFAOYSA-N 7,8-dimethyl-1,4,9,9a-tetrahydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2CC2=C(C)C(C)=CC=C21 YCKKLLYMMVHPIG-UHFFFAOYSA-N 0.000 claims 1
- CTZIRIUSNWPEKZ-UHFFFAOYSA-N 7-bromo-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=CC(Br)=CC=C21 CTZIRIUSNWPEKZ-UHFFFAOYSA-N 0.000 claims 1
- YEBXOZQMALFMCP-UHFFFAOYSA-N 7-bromo-6,8-dimethyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C(C)=C(Br)C(C)=CC2=NC2=C1NC(=O)N2 YEBXOZQMALFMCP-UHFFFAOYSA-N 0.000 claims 1
- -1 7-chloro-1,3-dihydro-7,8-dimethyl-2H-imidazo [4,5-b] quinolin-2-one Chemical compound 0.000 claims 1
- OSBMKBWTTUTUMA-UHFFFAOYSA-N 7-chloro-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=CC(Cl)=CC=C21 OSBMKBWTTUTUMA-UHFFFAOYSA-N 0.000 claims 1
- KOPBXGWUOMDXIW-UHFFFAOYSA-N 7-chloro-6-methyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C=C(Cl)C(C)=CC2=NC2=C1NC(=O)N2 KOPBXGWUOMDXIW-UHFFFAOYSA-N 0.000 claims 1
- SBMFEGWRZYIWGG-UHFFFAOYSA-N 7-ethoxy-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=CC(OCC)=CC=C21 SBMFEGWRZYIWGG-UHFFFAOYSA-N 0.000 claims 1
- XTXHKKBSLRGOJD-UHFFFAOYSA-N 7-fluoro-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=CC(F)=CC=C21 XTXHKKBSLRGOJD-UHFFFAOYSA-N 0.000 claims 1
- WPNOABJRAVXWKU-UHFFFAOYSA-N 7-methoxy-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=CC(OC)=CC=C21 WPNOABJRAVXWKU-UHFFFAOYSA-N 0.000 claims 1
- BSAKVJKPJIQKNP-UHFFFAOYSA-N 7-methyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=CC(C)=CC=C21 BSAKVJKPJIQKNP-UHFFFAOYSA-N 0.000 claims 1
- FPYRERVDZQWRBO-UHFFFAOYSA-N 7-propan-2-yloxy-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=CC(OC(C)C)=CC=C21 FPYRERVDZQWRBO-UHFFFAOYSA-N 0.000 claims 1
- VZXBGYRONYENIL-UHFFFAOYSA-N 8-chloro-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C(Cl)=CC=CC2=NC2=C1NC(=O)N2 VZXBGYRONYENIL-UHFFFAOYSA-N 0.000 claims 1
- YRQWFYMTPBNERX-UHFFFAOYSA-N 8-chloro-7-methyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=C(Cl)C(C)=CC=C21 YRQWFYMTPBNERX-UHFFFAOYSA-N 0.000 claims 1
- GMKORAPPNLPTAX-UHFFFAOYSA-N 8-methoxy-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C(OC)=CC=CC2=NC2=C1NC(=O)N2 GMKORAPPNLPTAX-UHFFFAOYSA-N 0.000 claims 1
- NFWDGDAZJTYAHA-UHFFFAOYSA-N 8-methyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C(C)=CC=CC2=NC2=C1NC(=O)N2 NFWDGDAZJTYAHA-UHFFFAOYSA-N 0.000 claims 1
- VEOPPKJMCCZWDL-UHFFFAOYSA-N 8-methyl-1,4,9,9a-tetrahydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2CC2=C1C=CC=C2C VEOPPKJMCCZWDL-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- 108050008598 Phosphoesterases Proteins 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 238000006356 dehydrogenation reaction Methods 0.000 claims 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims 1
- 150000001469 hydantoins Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 230000002503 metabolic effect Effects 0.000 claims 1
- 239000007800 oxidant agent Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Chemical group 0.000 claims 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Cardiology (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
Claims (35)
- 다음 구조식의 화합물 또는 제약학적으로 바람직한 기의 염.여기서, R1는 할로겐, 저급알킬 저급알콜시, 트리플루오로메틸이고; R2는 수고, 할로겐, 저급알킬 저급알콕시이며; R5는 수소, 할로겐, 저급알킬, 저급알콕시이고; R4는 수고, 저급알킬 또는 제약학적으로 바람직한 그의 염이다.
- 다음 구조식의 청구범위 1의 화합물.여기서, R1는 할로겐, 저급알킬, 저급알콕시, 트리플루오로메틸이고; R2는 수소, 할로겐, 저급알킬, 거급알콕시이며; R3는 수소, 할로겐, 저급알킬, 저급알콕시 또는 제약학적으로 바람직한 그의 염이다.
- 8-클로로-1,3-디하이드로-2H-이미다조 [4,5-b]퀴놀린-2-온인 청구범위 1의 화합물 또는 제약학적으로 바람직한 그의염.
- 7-플루오로-1,3-디하이드로-2H-이미다조 [4,5-b]퀴놀린-2-온인 청구범위 1의 화합물 또는 제약학적으로 바람직한 그의염.
- 8-메틸-1,3-디하이드로-2H-이미다조 [4,5-b]퀴놀린-2-온인 청구범위 1의 화합물 또는 제약학적으로 바람직한 그의염.
- 7-메틸-1,3-디하이드로-2H-이미다조 [4,5-b]퀴놀린-2-온인 청구범위 1의 화합물 또는 제약학적으로 바람직한 그의염.
- 7-클로로-1,3-디하이드로-2H-이미다조 [4,5-b]퀴놀린-2-온인 청구범위 1의 화합물 또는 제약학적으로 바람직한 그의염.
- 1,3-디하이드로-6,7-디메틸-2H-이미다조 [4,5-b]퀴놀린-2-온인 청구범위 1의 화합물 또는 제약학적으로 바람직한 그의염.
- 1,3-디하이드로-7,8-디메틸-2H-이미다조 [4,5-b]퀴놀린-2-온인 청구범위 1의 화합물 또는 제약학적으로 바람직한 그의염.
- 1,3-디하이드로-7-클로로-6-메틸-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 1의 화합물 또는 제약학적으로 바람직한 그의염.
- 1,3-디하이드로-8-메톡시-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 1의 화합물 또는 제약학적으로 바람직한 그의염.
- 1,3-디하이드로-8-클로로-7-메틸-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 1의 화합물 또는 제약학적으로 바람직한 그의염.
- 7-클로로-1,3-디하이드로-7,8-디메틸-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 1의 화합물 또는 제약학적으로 바람직한 그의염.
- 7-메톡시-1,3-디하이드로-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 1의 화합물 또는 제약학적으로 바람직한 그의염.
- 1,3-디하이드로-6,7-디메톡시-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 1의 화합물.
- 7-브로모-1,3-디하이드로-6,8-디메틸-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 1의 화합물.
- 7-브로모-1,3-디하이드로-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 1의 화합물.
- 1,3-디하이드로-7-(1-메틸에톡시)-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 1의 화합물.
- 1,3-디하이드로-6,7,8-트리메톡시-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 1의 화합물.
- 1,3-디하이드로-6-(트리플루오로메틸)-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 1의 화합물.
- 1,3-디하이드로-1,8-디메틸-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 1의 화합물.
- 1,3-디하이드로-1,7-디메틸-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 2의 화합물.
- 1,3-하디이드로-7-메톡시-1-메틸-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 1의 화합물.
- 1,3-디하이드로-1,7,8-트릴메틸-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 1의 화합물.
- 1,3-디하이드로-7-에톡시-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 1의 화합물.
- 다음 구조식의 화합물.여기서, R1는 할로겐, 저급알킬, 저급알콕시, 트리플루오로메틸이고; R2는 수소, 할로겐, 저급알킬, 저급알콕시이며; R3는 수소, 할로겐, 저급알킬, 저급알콕시이고; R4는 수소, 저급알킬이다.
- 8-메틸-1,3,9,9a-테트라하이드로-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 26의 화합물.
- 7,8-디메틸-1,3,9,9a-테트라하이드로-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 26의 화합물.
- 1,3,9,9a-테트라하이드로-1,8-디메틸-2H-이미다조 [4,5-b] 퀴놀린-2-온인 청구범위 26의 화합물.
- 다음 구조식의 화합물 또는 제약학적으로 바람직한 그의염.여기서, R1는 할로겐, 저급알킬, 저급알콕시, 트리플루오로메틸이며; R2는 수소, 할로겐, 저급알킬, 저급알콕시이고; R3는 수소, 할로겐, 저급알킬 저급알콕시이고; R4는 수소, 저급알킬이다.
- 포유동물에서 포스포에스테라제 및 혈소판응집을 억제하기 위하여 치료학적으로 효과적인 양의 청구범위 1의 화합물 또는 제약학적으로 바람직한 그의 엄을 투여하는 방법.
- 심장 변력활동을 증진시키기 위하여 필요시 치료학적으로 효과적인 양의 청구범위 1의 화합물 또는 제약학적으로 바람직한 그의 염을 투여하는 방법.
- 치료학적으로 효과적인 양의 청구범위 1의 화합물 또는 제약학적으로 바람직한 그의 산부가염을 함유하는 제약학적 조성 및 그 수용기.
- 다음 구조식 XI의 화합물을 제조하는 방법.여기서, R1는 할로겐, 저급알킬 저급알콕시, 트리플루오로메틸; R2는 수소, 할로겐, 저급알킬, 저급알콕시; R3는 수고, 할로겐, 저급알킬, 저급알콕시; 및 R4는 수소, 저급알킬 또는 제약학적으로 바람직한 그의 염으로서 다음 반응을 포함한다; (a) a와 b가 수소 또는 코베일런트 결합을 이루고, R1,R2,R3및 R4는 위에서 정의된 바와 같은 다음구조식 XIII의 치환된 히단토인을 산화하는 반응.(b) 환원된 물질을 필요시 산화제로 처리하는 반응.(c) R1,R2,R3및 R4가 위에서 정의된 바와 같은 다음 구조식 XIIIB의 화합물의 탈수소반응.(d) R1,R2,R3및 R4가 위에서 정의된 바와 같은 다음 구조식 XV 화합물의 알킬화된 티오를 제조하기 위하여 다음 구조식 XIV의 티오화합물을 알킬화하는 반응.여기서 R1,R2,R3및 R4가 위에서 정의된 바와 같고 R5X에서 R5는 저급알킬이고, X는 메실레이트, 토실레이트, 포스페이트, 설페이트 및 할로겐같은 유리그룹을 나타낸다.(e) 구조식 XV화합물을 구조식 XI화합물로 전환시키는 반응.(f) 바람직한 경우에는 구조식 XI화합물을 제약학적으로 바람직한 염으로 전환시키는 반응.
- a와 b가 수소이고, R1,R2,R3,R4가 구조식 XIII에서 정의된 바와 같은 다음 구조식 XIIIA의화합물을 제조하기 위하여 구조식 XI의 히단토인을 환원시킨 다음 구조식 XIIIA의 화합물을 R1,R2,R3및R4가 정의된 바와 같은 다음 구조식 XIIIB의화합물로 환화시키는 반응을 포함하는 청구범위 1의 화합물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US72686985A | 1985-04-25 | 1985-04-25 | |
US726,869 | 1985-04-25 | ||
US726869 | 1985-04-25 | ||
US832,212 | 1986-02-26 | ||
US06/832,212 US4668686A (en) | 1985-04-25 | 1986-02-26 | Imidazoquinoline antithrombrogenic cardiotonic agents |
Publications (2)
Publication Number | Publication Date |
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KR860008177A true KR860008177A (ko) | 1986-11-12 |
KR940000828B1 KR940000828B1 (ko) | 1994-02-02 |
Family
ID=27111398
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019860003204A Expired - Lifetime KR940000828B1 (ko) | 1985-04-25 | 1986-04-25 | 항혈전성 강심제 이미다조 퀴놀린의 제조방법 |
Country Status (32)
Country | Link |
---|---|
US (1) | US4668686A (ko) |
KR (1) | KR940000828B1 (ko) |
CN (1) | CN1016175B (ko) |
AT (1) | AT390257B (ko) |
AU (1) | AU592983B2 (ko) |
BE (1) | BE904671A (ko) |
CA (1) | CA1298836C (ko) |
CH (1) | CH675722A5 (ko) |
CY (1) | CY1641A (ko) |
DE (1) | DE3614132A1 (ko) |
DK (3) | DK164868C (ko) |
EG (1) | EG18104A (ko) |
ES (3) | ES8708229A1 (ko) |
FI (1) | FI83316C (ko) |
FR (1) | FR2581065B1 (ko) |
GB (1) | GB2174987B (ko) |
GR (1) | GR861086B (ko) |
HK (1) | HK64492A (ko) |
HU (1) | HU195813B (ko) |
IL (1) | IL78581A0 (ko) |
IT (1) | IT1215651B (ko) |
LU (1) | LU86406A1 (ko) |
MY (1) | MY102086A (ko) |
NL (1) | NL8601053A (ko) |
NO (1) | NO163406C (ko) |
NZ (1) | NZ215885A (ko) |
OA (1) | OA08242A (ko) |
PT (1) | PT82460B (ko) |
SE (1) | SE461468B (ko) |
SG (1) | SG29092G (ko) |
SU (3) | SU1450746A3 (ko) |
YU (1) | YU46054B (ko) |
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US5552267A (en) * | 1992-04-03 | 1996-09-03 | The Trustees Of Columbia University In The City Of New York | Solution for prolonged organ preservation |
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MY145983A (en) | 2003-08-27 | 2012-05-31 | 3M Innovative Properties Co | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
JP2007504269A (ja) | 2003-09-05 | 2007-03-01 | スリーエム イノベイティブ プロパティズ カンパニー | Cd5+b細胞リンパ腫の治療方法 |
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EP1687307B1 (en) | 2003-11-25 | 2016-01-06 | 3M Innovative Properties Company | Substituted imidazo ring systems and methods |
US8802853B2 (en) | 2003-12-29 | 2014-08-12 | 3M Innovative Properties Company | Arylalkenyl and arylalkynyl substituted imidazoquinolines |
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US8017779B2 (en) | 2004-06-15 | 2011-09-13 | 3M Innovative Properties Company | Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
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US8026366B2 (en) | 2004-06-18 | 2011-09-27 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
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1986
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- 1986-04-21 AU AU56413/86A patent/AU592983B2/en not_active Ceased
- 1986-04-22 FI FI861684A patent/FI83316C/fi not_active IP Right Cessation
- 1986-04-22 IL IL78581A patent/IL78581A0/xx not_active IP Right Cessation
- 1986-04-23 EG EG237/86A patent/EG18104A/xx active
- 1986-04-23 CN CN86102747A patent/CN1016175B/zh not_active Expired
- 1986-04-24 CH CH1679/86A patent/CH675722A5/de not_active IP Right Cessation
- 1986-04-24 PT PT82460A patent/PT82460B/pt not_active IP Right Cessation
- 1986-04-24 GB GB8610037A patent/GB2174987B/en not_active Expired
- 1986-04-24 LU LU86406A patent/LU86406A1/fr unknown
- 1986-04-24 BE BE0/216585A patent/BE904671A/fr not_active IP Right Cessation
- 1986-04-24 IT IT8620206A patent/IT1215651B/it active
- 1986-04-24 NL NL8601053A patent/NL8601053A/xx not_active Application Discontinuation
- 1986-04-24 DK DK190986A patent/DK164868C/da not_active IP Right Cessation
- 1986-04-24 NO NO861617A patent/NO163406C/no unknown
- 1986-04-24 FR FR868605966A patent/FR2581065B1/fr not_active Expired - Fee Related
- 1986-04-24 SU SU864027355A patent/SU1450746A3/ru active
- 1986-04-24 GR GR861086A patent/GR861086B/el unknown
- 1986-04-24 ES ES554336A patent/ES8708229A1/es not_active Expired
- 1986-04-24 SE SE8601907A patent/SE461468B/sv not_active IP Right Cessation
- 1986-04-25 DE DE19863614132 patent/DE3614132A1/de not_active Ceased
- 1986-04-25 OA OA58845A patent/OA08242A/xx unknown
- 1986-04-25 AT AT0112186A patent/AT390257B/de not_active IP Right Cessation
- 1986-04-25 HU HU861723A patent/HU195813B/hu not_active IP Right Cessation
- 1986-04-25 KR KR1019860003204A patent/KR940000828B1/ko not_active Expired - Lifetime
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1987
- 1987-02-27 SU SU874202071A patent/SU1470192A3/ru active
- 1987-05-14 ES ES557551A patent/ES8801829A1/es not_active Expired
- 1987-05-14 ES ES557552A patent/ES8802521A1/es not_active Expired
- 1987-06-23 YU YU116787A patent/YU46054B/sh unknown
- 1987-09-25 SU SU874203391A patent/SU1560056A3/ru active
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1991
- 1991-04-30 DK DK080291A patent/DK165248C/da not_active IP Right Cessation
- 1991-05-01 DK DK081091A patent/DK165249C/da not_active IP Right Cessation
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1992
- 1992-03-10 SG SG290/92A patent/SG29092G/en unknown
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