KR960041166A - 4-(아릴아미노 메틸렌)-2,4-디하이드로-3-피라졸론 - Google Patents
4-(아릴아미노 메틸렌)-2,4-디하이드로-3-피라졸론 Download PDFInfo
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- KR960041166A KR960041166A KR1019960016421A KR19960016421A KR960041166A KR 960041166 A KR960041166 A KR 960041166A KR 1019960016421 A KR1019960016421 A KR 1019960016421A KR 19960016421 A KR19960016421 A KR 19960016421A KR 960041166 A KR960041166 A KR 960041166A
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- alkyl
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- ethylanilinomethylene
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- -1 phospho Phenyl Chemical group 0.000 claims abstract 55
- 229910005965 SO 2 Inorganic materials 0.000 claims abstract 37
- 125000000217 alkyl group Chemical group 0.000 claims abstract 36
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 36
- 150000001875 compounds Chemical class 0.000 claims abstract 18
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 14
- 125000005842 heteroatom Chemical group 0.000 claims abstract 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 10
- 150000003839 salts Chemical class 0.000 claims abstract 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 7
- 125000006307 alkoxy benzyl group Chemical group 0.000 claims abstract 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 6
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 6
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 5
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims abstract 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 4
- ZOOGRGPOEVQQDX-UUOKFMHZSA-N 3',5'-cyclic GMP Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-UUOKFMHZSA-N 0.000 claims abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract 3
- 150000002367 halogens Chemical class 0.000 claims abstract 3
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims abstract 2
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims abstract 2
- 229940124639 Selective inhibitor Drugs 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 17
- 239000003814 drug Substances 0.000 claims 5
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 3
- 239000005711 Benzoic acid Substances 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- IEMGWBMVQLVHEY-UHFFFAOYSA-N ethyl 2-(3-amino-6,7-dihydro-5h-cyclopenta[b]pyridin-7-yl)acetate Chemical compound NC1=CN=C2C(CC(=O)OCC)CCC2=C1 IEMGWBMVQLVHEY-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims 1
- ZXBMKIRZCNXQPT-UHFFFAOYSA-N 4-(3,4-dihydropyrazol-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1N1N=CCC1 ZXBMKIRZCNXQPT-UHFFFAOYSA-N 0.000 claims 1
- DANLZOIRUUHIIX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DANLZOIRUUHIIX-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical group CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 150000001448 anilines Chemical class 0.000 claims 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000002552 dosage form Substances 0.000 claims 1
- MSTVQHUDEPGSNO-UHFFFAOYSA-N ethyl 2-[4-[(2-ethylanilino)methylidene]-1-[4-(methanesulfonamido)phenyl]-5-oxopyrazol-3-yl]acetate Chemical compound CCOC(=O)CC1=NN(C=2C=CC(NS(C)(=O)=O)=CC=2)C(=O)C1=CNC1=CC=CC=C1CC MSTVQHUDEPGSNO-UHFFFAOYSA-N 0.000 claims 1
- GFAUNYMRSKVDJL-UHFFFAOYSA-N formyl chloride Chemical compound ClC=O GFAUNYMRSKVDJL-UHFFFAOYSA-N 0.000 claims 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 1
- 239000010931 gold Substances 0.000 claims 1
- 229910052737 gold Inorganic materials 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical class COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims 1
- ZRHUHDUEXWHZMA-UHFFFAOYSA-N 1,4-dihydropyrazol-5-one Chemical class O=C1CC=NN1 ZRHUHDUEXWHZMA-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
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- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
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Abstract
본 발명은 하기 일반식(Ⅰ)의 5-피라졸리논 유도체 및 그의 생리학적으로 허용가능한 염에 관한 것이다.
상기 식에서, R1은 벤질; 탄소수 1 내지 3의 알킬 잔기를 갖는 알콕시벤질; 페닐; 아미노, 할로겐, NO2, CN, 아실, AO-, HSO3-, CO2H, A-CO-, A-O-CO-NH-, -A-CO-NA-, 카바모일, N-알킬카바모일, N,N-디알킬카바모일(알킬 잔기의 탄소수는 1 내지 6이다), A-O-CO-NH-, A-O-CO-NA-, SO2NR4R5(이때 R4및 R5는 H 또는 탄소수 1 내지 6의 알킬이거나, 똔느 NR4R5는 임의로 다른 헤테로원자, 예를들어 N, S, O를 갖고 A로 치환될수도 있는 5- 또는 6원 고리이다), A-CO-NH-SO2-, A-O-NA-SO2, A-SO2-NH-, A-SO2-NA-, (A-SO2-)2N-, 테트라졸릴 또는 포스포에 의해 일 내지 삼치환된 페닐; 또는 피리딜이고; R2는 탄소수 1 내지 5의 알킬, 알콕시카보닐알킬, 하이드록시알킬, 하이드록시카보닐알킬이고; R3는 H, 탄소수 1 내지 5의 직쇄 또는 분지된 알킬, 탄소수 1 내지 5의 직쇄 또는 분지된 알콕시, 불소- 또는 염소-치환된 알킬, 아미노알카노일, 아미노알킬, 카바모일, SO2NR4R5(이때 R4및 R5는 H 또는 탄소수 1 내지 6의 알킬이거나, 또는 NR4R5는 임의로 다른 헤테로원자, 예를들어 N, S, O를 갖고 A로 치환될 수도 있는 5- 또는 6원 고리이다)이고; A는 탄소수 1 내지 6의 직쇄 또는 분지된 알킬, 또는 탄소수 1 내지 6의 직쇄 또는 분지된 불소- 또는 염소-치환된 알킬이다.
본 발명은 또한 상기 화합물의 제조 방법, 및 특히 cGMP-특이적인 포스포디에스테라제(cGMP PDE)의 선택적인 억제제 및 따라서 약학적으로 활성인 화합물로서의 상기 화합물의 용도를 포함한다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (12)
- 하기 일반식(Ⅰ)의 화합물 또는 그의 염;상기 식에서, R1은 벤질; 탄소수 1 내지 3의 알킬 잔기를 갖는 알콕시벤질; 페닐; 아미노, 시아노, 할로겐, 니트로, A-CO-, 카복시, AO-, 카바모일, N-알킬카바모일, N,N-디알킬카바모일(알킬 잔기의 탄소수는 1 내지 6이다), A-O-CO-, A-O-CO-NH-, -A-O-CO-NA-, A-CO-NH-, A-CO-NA-, HSO3-, A-SO2-, SO2NR4R5(이때 R4및 R5는 H 또는 탄소수 1 내지 6의 알킬이거나, 또는 NR4R5는 임의로 다른 헤테로원자, 예를들어 N, S, O를 갖고 A로 치환될수도 있는 5- 또는 6원 고리이다), A-CO-NH-SO2-, A-O-NA-SO2, A-SO2-NH-, A-SO2-NA-, (A-SO2-)2N-, 테트라졸릴 또는 포스포에 의해 일 내지 삼치환된 페닐; 또는 피리딜이고; R2는 탄소수 1 내지 5의 알킬, 알콕시카보닐알킬, 하이드록시알킬, 하이드록시카보닐알킬이고; R3는 H, 탄소수 1 내지 5의 직쇄 또는 분지된 알킬, 탄소수 1 내지 5의 직쇄 또는 분지된 알콕시, 불소- 또는 염소-치환된 알킬, 아미노알카노일, 아미노알킬, 설파모일(상기는 SO2NR4R5를 가지며, 이때 R4및 R5는 H 또는 탄소수 1 내지 6의 알킬이거나 또는 NR4R5는 임의로 다른 헤테로원자, 예를들어 N, S, O를 갖고 A로 치환될수도 있는 5- 또는 6원 고리이다)이고; A는 탄소수 1 내지 6의 직쇄 또는 분지된 알킬, 또는 탄소수 1 내지 6의 직쇄 또는 분지된 불소- 또는 염소-치환된 알킬이다.
- 제1항에 있어서, R1는 벤질; 탄소수 1 내지 3의 알킬 잔기를 갖는 알콕시벤질; 페닐; 아미노, 할로겐, 니트로, 시아노, HSO3-, 카복실, A-O-CO-, A-CO-NH-, A-CO-NA-, 카바모일, N-알킬카바모일, N,N-디알킬카바모일(알킬 잔기의 탄소수는 1 내지 6이다), SO2NR4R5(이때 R4및 R5는 H 또는 탄소수 1 내지 6의 알킬이거나, 또는 NR4R5는 임의로 다른 헤테로원자, 예를들어 N, S, O를 갖고 A로 치환될 수도 있는 5- 또는 6원 고리이다), A-CO-NH-SO2-, A-CO-NA-SO2-, A-SO2-NH-, A-SO2-NA-, 아실설폰아미도, 테트라졸릴 또는 포스포에 의해 일 내지 삼치환된 페닐; 또는 피리딜이고; R2가 하이드록시알킬이고; R3가 H, 탄소수 1 내지 5의 직쇄 또는 분지된 알킬, 탄소수 1 내지 5의 직쇄 또는 분지된 알콕시, 불소- 또는 염소-치환된 알킬이고; A가 제1항에서 정의된 바와 같은 화합물 또는 그의 염.
- 제1항에 있어서, R1이 벤질; 탄소수 1 내지 3의 알킬 잔기를 갖는 알콕시벤질; 페닐; HSO3-, A-CO-NH-, A-CO-NA-, N-알킬카바모일, N,N-디알킬카바모일(알킬 잔기의 탄소수는 1 내지 6이다), SO2NR4R5(이때 R4및 R5는 H 또는 탄소수 1 내지 6의 알킬이거나, 또는 NR4R5는 임의로 다른 헤테로원자, 예를들어 N, S, O를 갖고 A로 치환될 수도 있는 5- 또는 6원 고리이다), A-CO-NH-SO2-, A-CO-NA-SO2-, 테트라졸릴 또는 포스포에 의해 일 내지 삼치환된 페닐; 또는 피리딜이고; R2가 H3C-O-CO-CH2-이고; R3가 아미노알킬, 아미노알카노일, SO2NR4R5(이때 R4및 R5는 H 또는 탄소수 1 내지 6의 알킬이거나, 또는 NR4R5는 임의로 다른 헤테로원자, 예를들어 N, S, O를 갖고 A로 치환될수도 있는 5- 또는 6원 고리이다)이고; A가 제1항에서 정의한 바와 같은 화합물 또는 그의 염.
- 제1항 내지 3항중 어느 한 항에 있어서, 메틸 N-(3-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-3-메틸-5-옥소-1H-피라졸-1-일)페닐)카바메이트,4-((2-에톡시아닐리노메틸렌)-4,5-디히이드로-3-메틸-5-옥소-1H-피라졸-1-일)-N-에틸벤젠설폰아미드, 에틸 2-(1-(4-N,N-디에틸설파모일)페닐)-4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-1H-피라졸-3-일)-아세테이트 에틸2-(1-(4-아세트아미도페닐)-4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-1H-피라졸-3-일)-아세테이트, 에틸 2-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-1-(4-트리플루오로아세트아미도페닐)-1H-피라졸-3-일)-아세테이트, 에틸 2-(1-(4-에톡시카보닐아미노페닐)-4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-1H-피라졸-3-일)-아세테이트, 에틸 2-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-1-(4-메탄설폰아미도페닐)-5-옥소-1H-피라졸-3-일)-아세테이트, N-(3-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-3-메틸-5-옥소-5H-피라졸-1-일)페닐)아세트아미드, N,N-디에틸-4-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-3-메틸-5-옥소-1H-피라졸-1-일)벤젠설폰아미드, N-에틸-4-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-3-메틸-5-옥소-1H-피라졸-1-일)벤젠설폰아미드, 4-(2-에톡시아닐리노메틸렌)-2,4-디하이드로-5-메틸-2-(4-(4-모르폴리닐설포닐)페닐)-3H-피라졸-3-온, 4-(2-에틸아닐리노메틸렌)-2,4-디하이드로-5-메틸-2-(4-(4-메틸-1-피페라지닐설포닐)페닐)-3H-피라졸-3-온, N-(3-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-3-메틸-5-옥소-1H-피라졸-1-일)페닐)메틴설폰아미드, N-(3-(4-(2-에틸아닐리노메틸렌)4,5-디하이드로-3-메틸-5-옥소-1H-피라졸-5-일)페닐)트리플루오로아세트아미드, N-(4-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-3-메틸-5-옥소-1H-피라졸-1-일)페닐)-N-메틸설포닐메탄설폰아미드, N,N-디에틸-4-(4,5-디하이드로-4-(2-에톡시아닐리노메틸렌)-3-메틸-5-옥소-1H-피라졸-1-일)벤젠설폰아미드, N,N-디에틸-4-(4,5-디하이드로-4-(2-메톡시아닐리메틸렌)-3-메틸-5-옥소-1H-피라졸-1-일)벤젠설폰아미드, 3-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-3-프로필-1H-피라졸-1일)벤젠설폰산, 4-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-3-프로필-1H-피라졸-1-일)벤젠설폰산, 에틸 2-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-1-(4-니트로페닐)-5-옥소-1H-피라졸-3-일)아세테이트, 4-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-3-프로필-1H-피라졸-1-일)벤조산, 4-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-3-메틸-5-옥소-1H-피라졸-1-일)-N-헥실벤즈아미드, 4-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-3-메틸-5-옥소-1H-피라졸-1-일)벤즈아미드, N,N-디에틸-4-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-3-메틸-5-옥소-1H-피라졸-1-일)벤즈아미드, 4-(2-에틸아닐리노메틸렌)-2,4-디하이드로-5-프로필-2-(4-피리딜)-3H-피라졸-3-온, N,N-디에틸-4-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-3-프로필-1H-피라졸-1-일)벤즈아미드, 4-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-3-프로필-1H-피라졸-1-일)-N-헥실벤즈아미드, 4-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-3-프로필-1H-피라졸-1-일)벤즈아미드, 4-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-3-프로필-1H-피라졸-1-일)벤조산, 4-(2-에틸아닐리노메틸렌)-2,4-디하이드로-5-프로필-(2-(4-(1H-테트라졸-5-일)페닐)-3H-피라졸-3-온, 4-(2-에틸아닐리노메틸렌)-2,4-디하이드로-5-메틸-(2-(3-(1H-테트라졸-5-일)페닐)-3H-피라졸-3-온,4-(4,5-디하이드로-3-메틸-5-옥소-4-(2-트리플루오로메틸아닐리노메틸렌)-1H-피라졸-1-일)벤조산, 4-(4-2에틸아닐리노메틸렌)-3-에톡시카보닐메틸-4,5-디하이드로-5-옥소-1H-피라졸-1-일)벤조산, 4-(4,5-디하이드로-3-메틸-5-옥소-4-(2-(2-프로피닐옥시)아닐리노메틸렌)-1H-피라졸-1-일)벤조산, 4-(4,5-디하이드로-3-메틸-5-옥소-4-(2-프로폭시아닐리노메틸렌)-1H-피라졸-1-일)벤조산, 4-(4,5-디하이드로-4-(2-이소프로필아닐리노메틸렌)-3-메틸-5-옥소-1H-피라졸-1-일)벤조산, 3-(4-(2-에틸아닐리노메틸렌아미노메틸렌)-4,5-디하이드로-3-메틸-5-옥소-1H-피라졸-1--일)벤젠설폰아미드, 에틸2-(1-(4-아세트아미도페닐)-4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-1H-피라졸-3-일)아세테이트, 에틸 2-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-1-(4-트리플루오로아세트아미도페닐)-5-옥소-1H-피라졸-3-일)아세테이트, 에틸 2-(1-(4-메톡시카보닐아미노페닐)-4-(2-에틸아닐라노메틸렌)-4,5-디하이드로-5-옥소-1H-피라졸-3-일)아세테이트, 에틸 2-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-1-(4-메탄설폰아미도페닐)-5-옥소-1H-피라졸-3-일)아세테이트, 에틸 2-(1-(4-(N,N-디에틸설파모닐)페닐)-4-(2-에톡시아닐리노메틸렌)-4,5-디하이드로-5-옥소-1H-피라졸-3-일)아세테이트, 에틸 2-(1-(4-(N,N-디에틸설파모닐)페닐)-4-(2-에톡시아닐리노메틸렌)-4,5-디하이드로-5-옥소-1H-피라졸-3-일)아세테이트, 에틸 2-(1-(4-(아세트아미도페닐)-4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-1H-피라졸-3-일)아세테이트, 에틸 2-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-1-(4-트리플루오로아세트아미도페닐)-1H-피라졸-3-일)아세테이트, 에틸 2-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-1-(4-메톡시카보니라미노페닐)-5-옥소-1H-피라졸-3-일)아세테이트, 에틸 2-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-1-(4-메탄설폰아미도페닐)-5-옥소-1H-피라졸-3-일)아세테이트, 에틸 2-(1-(4-아세트아미도페닐)-4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-1H-피라졸-3-일)아세테이트, 2-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-1-(4-메톡시카보닐아미노페닐)-5-옥소-1H-피라졸-3-일)아세트산, N-(3-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-3-프로필-1H-피라졸-1-일)페닐)메탄설폰아미드, N-(3-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-3-프로필-1H-피라졸-1-일)페닐)아세트아미드, 메틸 N-(3-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-3-프로필-1H-피라졸-1-일)페닐)카바메이트, 에틸 2-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-5-옥소-1-(3-트리플루오로아세트아미도페닐)-1H-피라졸-1-일)아세테이트, 및 에틸 2-(4-(2-에틸아닐리노메틸렌)-4,5-디하이드로-1-(3-메탄설폰아미도페닐)-5-옥소-1H-피라졸-3-일)아세테이트로 이루어진 그룹중에서 선택된 화합물.
- R1이 벤질; 탄소수 1 내지 3의 알킬 잔기를 갖는 알콕시벤질; 페닐; 아미노, 할로겐, 니트로, 시아노, 카복실, HSO3-, A-O-CO-, A-CO-NH-, A-CO-NA-, 카바모일, N-알킬카바모일, N,N-디알킬카바모일(알킬 잔기의 탄소수는 1 내지 6이다), SO2NR4R5(이때 R4및 R5는 H 또는 탄소수 1 내지 6의 알킬이거나, 또는 NR4R5는 임의로 다른 헤테로원자, 예를들어 N, S, O를 갖고 A로 치환될 수도 있는 5- 또는 6원고리이다0, A-CO-NH-SO2, A-CO-NH-SO2, A-SO2-NH-, A-SO2-NA-, 아실설폰아미도, 테트라졸릴 또는 포스포에 의해 일 내지 삼치환된 페닐; 또는 피리딜이고; R2가 탄소수 1 내지 5의 알킬, 알콕시카보닐알킬, 하이드록시알킬, 하아드록시카보닐알킬이고; R3가 H, 탄소수 1 내지 5의 직쇄 또는 분지된 알킬, 탄소수 1 내지 5의 직쇄 또는 분지된 알콕시, 불소- 또는 염소-치환된 알킬, 아미노알카노일, 아미노알킬, SO2NR4R5(이때 R4및 R5는 H 또는 탄소수 1 내지 6의 알킬이거나, 또는 NR4R5는 임의로 다른 헤테로원자, 예를들어 N, S, O를 갖는 5- 또는 6원 고리이다)인 제1항에 따른 일반식(Ⅰ)의 약제 또는 그의 생리학적으로 허용가능한 염.
- cGMP-특이적인 포스포디에스테라제의 선택적인 억제제로서 제5항에 따른 약제의 용도.
- 약제 제형의 제조를 위한 제5항에 따른 화합물 또는 그의 생리학적으로 허용가능한 염의 용도.
- 질병의 치료를 위한 제5항에 따른 약제의 용도.
- 심혈관계 질환 및 심부전증의 치료를 위한 약제 제형의 제조를 위한 제5항에 따른 약제의 용도.
- 하나이상의 제1항 내지 4항 중 어느 한 항의 화합물 및/또는 하나 이상의 그의 생리학적 염 또는 제5항에 따른 약제를 함유함을 특징으로 하는 약학 제제.
- 하나이상의 제5항에 따른 약제를 함유하고 하나이상의 고체, 액체, 또는 반액체 비히클 또는 보조제와 함께 적합한 투여형을 형성함을 특징으로 하는 약학 제제.
- 하기 일반식(Ⅱ)의 화합물을 트리아진, 디메틸포름아미드, 디메틸-포름아미드 디메틸 아세탈, 골드(Gold) 시약, 포르밀 클로라이드, 포름 아미드 및 탄소수 1 내지 6의 알킬 잔기를 갖는 포름아미드의 알킬 유도체의 그룹중에서 선택된 포름알데히드-공여 화합물, 또는 트리알킬 오르토포르메이트, 바람직하게 트리메틸 오르토포르메이트의 그룹중에서 선택된 포름알데히드-공여 화합물과 반응시켜 하기 일반식(Ⅱa)의 화합물을 수득하고, 이를, 경우에 따라 동일반응계내에서, 하기 일반식(Ⅲ)의 적합한 아닐린 유도체 또는 그의 염과 반응시켜 일반식(Ⅰ)의 화합물을 수득하고/하고나 상기 일반식(Ⅰ) 화합물의 하나이상의 라디칼(들)을 하나이상의 다른 라디칼(들)로 전환시키거나, 또는 일반식(Ⅱ)의 화합물을 부틸- 및 메틸리튬 그룹중에서 선택된 염기의 존재하에서 아릴 이소시아네이트와 반응시킴을 특징으로 하는, 제1항 내지 4항 중 어느 한 항에 따른 화합물 또는 제5항에 따른 약제의 제조 방법.상기 식들에서, R1은 벤질; 탄소수 1 내지 3의 알킬 잔기를 갖는 알콕시벤질; 페닐; 아미노, 시아노, 할로겐, 니트로, A-CO-, 카복시, AO-, 카바모일, N-알킬카바모일, N,N-디알킬카바모일(알킬 잔기의 탄소수는 1 내지 6이다), A-O-CO-, A-O-CO-NH-, A-O-CO-NA-, A-CO-NH-, A-CO-NA-, HSO3-, A-SO2-, SO2NR4R5(이때 R4및 R5는 H 또는 탄소수 1 내지 6의 알킬이거나, 또는 NR4R5는 임의로 다른 헤테로원자, 예를들어 N, S, O를 갖고 A로 치환될 수도 있는 5- 또는 6원 고리이다), A-CO-NH-SO2-, A-CO-NA-SO2, A-SO2-NH-, A-SO2-NA-, (A-SO2-)2N-, 테트라졸릴 또는 포스포에 의해 일 내지 삼치환된 페닐; 또는 피리딜이고; R2가 탄소수 1 내지 5의 알킬, 알콕시카보닐알킬, 하이드록시알킬, 하이드록시카보닐알킬이고; R3가 H, 탄소수 1 내지 5의 직쇄 또는 분지된 알킬, 탄소수 1 내지 5의 직쇄 또는 분지된 알콕시, 불소- 또는 염소-치환된 알킬, 아미노알카노일, 아미노알킬, 설파모일(상기는 SXO2NR4R5를 가지며, 이때 R4및 R5는 H 또는 탄소수 1 내지 6의 알킬이거나, 또는 NR4R5는 임의로 다른 헤테로원자, 예를 들어 N, S, O를 갖고 A로 치환될수도 있는 5- 또는 6원 고리이다)이고; X는 아미노 또는 -O-알킬 그룹(이때 알킬 잔기는 탄소수 1 내지 6을 갖는다)이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19518082.8 | 1995-05-17 | ||
| DE19518082A DE19518082A1 (de) | 1995-05-17 | 1995-05-17 | 4(-Arylaminomethylen)-2,4-dihydropyrazol-3-one |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR960041166A true KR960041166A (ko) | 1996-12-19 |
| KR100413154B1 KR100413154B1 (ko) | 2004-05-12 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019960016421A KR100413154B1 (ko) | 1995-05-17 | 1996-05-16 | 4-(아릴아미노메틸렌)-2,4-디하이드로-3-피라졸론 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US5869516A (ko) |
| EP (1) | EP0743304B1 (ko) |
| JP (1) | JP3996656B2 (ko) |
| KR (1) | KR100413154B1 (ko) |
| CN (1) | CN1066138C (ko) |
| AT (1) | ATE235469T1 (ko) |
| AU (1) | AU713042B2 (ko) |
| CA (1) | CA2176649C (ko) |
| CZ (1) | CZ291572B6 (ko) |
| DE (2) | DE19518082A1 (ko) |
| DK (1) | DK0743304T3 (ko) |
| ES (1) | ES2192588T3 (ko) |
| HU (1) | HUP9601328A3 (ko) |
| NO (1) | NO306777B1 (ko) |
| PL (1) | PL186049B1 (ko) |
| PT (1) | PT743304E (ko) |
| RU (1) | RU2180659C2 (ko) |
| SI (1) | SI0743304T1 (ko) |
| SK (1) | SK284295B6 (ko) |
| TW (1) | TW349093B (ko) |
| UA (1) | UA59330C2 (ko) |
| ZA (1) | ZA963918B (ko) |
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-
1995
- 1995-05-17 DE DE19518082A patent/DE19518082A1/de not_active Withdrawn
-
1996
- 1996-03-18 TW TW085103221A patent/TW349093B/zh active
- 1996-05-09 SK SK589-96A patent/SK284295B6/sk unknown
- 1996-05-10 ES ES96107518T patent/ES2192588T3/es not_active Expired - Lifetime
- 1996-05-10 DK DK96107518T patent/DK0743304T3/da active
- 1996-05-10 PT PT96107518T patent/PT743304E/pt unknown
- 1996-05-10 AT AT96107518T patent/ATE235469T1/de not_active IP Right Cessation
- 1996-05-10 DE DE59610254T patent/DE59610254D1/de not_active Expired - Lifetime
- 1996-05-10 EP EP96107518A patent/EP0743304B1/de not_active Expired - Lifetime
- 1996-05-10 SI SI9630609T patent/SI0743304T1/xx unknown
- 1996-05-13 UA UA96051861A patent/UA59330C2/uk unknown
- 1996-05-13 AU AU52253/96A patent/AU713042B2/en not_active Ceased
- 1996-05-15 NO NO961996A patent/NO306777B1/no not_active IP Right Cessation
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- 1996-05-16 RU RU96109192/04A patent/RU2180659C2/ru not_active IP Right Cessation
- 1996-05-16 ZA ZA963918A patent/ZA963918B/xx unknown
- 1996-05-16 HU HU9601328A patent/HUP9601328A3/hu unknown
- 1996-05-16 KR KR1019960016421A patent/KR100413154B1/ko not_active IP Right Cessation
- 1996-05-16 US US08/648,951 patent/US5869516A/en not_active Expired - Lifetime
- 1996-05-16 PL PL96314286A patent/PL186049B1/pl not_active IP Right Cessation
- 1996-05-16 CZ CZ19961421A patent/CZ291572B6/cs not_active IP Right Cessation
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Also Published As
| Publication number | Publication date |
|---|---|
| CZ291572B6 (cs) | 2003-04-16 |
| NO961996D0 (no) | 1996-05-15 |
| NO306777B1 (no) | 1999-12-20 |
| EP0743304B1 (de) | 2003-03-26 |
| HU9601328D0 (en) | 1996-07-29 |
| CN1141291A (zh) | 1997-01-29 |
| EP0743304A1 (de) | 1996-11-20 |
| CN1066138C (zh) | 2001-05-23 |
| ZA963918B (en) | 1996-11-25 |
| ES2192588T3 (es) | 2003-10-16 |
| HUP9601328A2 (en) | 1997-02-28 |
| CA2176649C (en) | 2008-08-05 |
| US5869516A (en) | 1999-02-09 |
| TW349093B (en) | 1999-01-01 |
| SK58996A3 (en) | 1996-12-04 |
| SI0743304T1 (en) | 2003-10-31 |
| AU713042B2 (en) | 1999-11-25 |
| DE19518082A1 (de) | 1996-11-21 |
| JPH08311035A (ja) | 1996-11-26 |
| AU5225396A (en) | 1996-11-28 |
| DK0743304T3 (da) | 2003-07-14 |
| NO961996L (no) | 1996-11-18 |
| DE59610254D1 (de) | 2003-04-30 |
| PL186049B1 (pl) | 2003-09-30 |
| CA2176649A1 (en) | 1996-11-18 |
| CZ142196A3 (en) | 1997-01-15 |
| SK284295B6 (sk) | 2005-01-03 |
| ATE235469T1 (de) | 2003-04-15 |
| KR100413154B1 (ko) | 2004-05-12 |
| PL314286A1 (en) | 1996-11-25 |
| JP3996656B2 (ja) | 2007-10-24 |
| HUP9601328A3 (en) | 1999-04-28 |
| RU2180659C2 (ru) | 2002-03-20 |
| PT743304E (pt) | 2003-08-29 |
| UA59330C2 (uk) | 2003-09-15 |
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