KR880008987A - 헤테로아릴 3-옥소-프로판니트릴 유도체 및 그의 제조방법 - Google Patents
헤테로아릴 3-옥소-프로판니트릴 유도체 및 그의 제조방법 Download PDFInfo
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- KR880008987A KR880008987A KR1019880000056A KR880000056A KR880008987A KR 880008987 A KR880008987 A KR 880008987A KR 1019880000056 A KR1019880000056 A KR 1019880000056A KR 880000056 A KR880000056 A KR 880000056A KR 880008987 A KR880008987 A KR 880008987A
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- Prior art keywords
- phenyl
- cyano
- oxo
- dihydro
- pyrazol
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- -1 Heteroaryl 3-oxo-propanenitrile derivatives Chemical class 0.000 title claims 12
- 238000002360 preparation method Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 10
- 150000002367 halogens Chemical class 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims 5
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000001301 oxygen Substances 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims 1
- KLYRLYNXBRHFBU-UHFFFAOYSA-N 2-cyano-3-(4-methyl-1-phenyl-4h-chromeno[4,3-c]pyrazol-3-yl)-3-oxo-n-phenylpropanamide Chemical compound CC1OC2=CC=CC=C2C2=C1C(C(=O)C(C#N)C(=O)NC=1C=CC=CC=1)=NN2C1=CC=CC=C1 KLYRLYNXBRHFBU-UHFFFAOYSA-N 0.000 claims 1
- JHFROWUCDDTNHM-UHFFFAOYSA-N 2-cyano-3-(8-methyl-1-phenyl-4h-thiochromeno[4,3-c]pyrazol-3-yl)-3-oxo-n-phenylpropanamide Chemical compound C1=2C3=CC(C)=CC=C3SCC=2C(C(=O)C(C#N)C(=O)NC=2C=CC=CC=2)=NN1C1=CC=CC=C1 JHFROWUCDDTNHM-UHFFFAOYSA-N 0.000 claims 1
- SHJJYJJGAAEISB-UHFFFAOYSA-N 2-cyano-3-[1-(3,5-dichlorophenyl)-4h-thiochromeno[4,3-c]pyrazol-3-yl]-3-oxo-n-phenylpropanamide Chemical compound ClC1=CC(Cl)=CC(N2C=3C4=CC=CC=C4SCC=3C(C(=O)C(C#N)C(=O)NC=3C=CC=CC=3)=N2)=C1 SHJJYJJGAAEISB-UHFFFAOYSA-N 0.000 claims 1
- STOQDQKQPUUXKF-UHFFFAOYSA-N 2-cyano-3-oxo-3-(1-phenyl-4h-thiochromeno[4,3-c]pyrazol-3-yl)-n-[3-(trifluoromethyl)phenyl]propanamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)C(C#N)C(=O)C=2C3=C(C4=CC=CC=C4SC3)N(N=2)C=2C=CC=CC=2)=C1 STOQDQKQPUUXKF-UHFFFAOYSA-N 0.000 claims 1
- SDQBABUTAKURPS-UHFFFAOYSA-N 2-cyano-3-oxopropanamide Chemical compound NC(=O)C(C=O)C#N SDQBABUTAKURPS-UHFFFAOYSA-N 0.000 claims 1
- UKAYDQDCVIKPBU-UHFFFAOYSA-N 2-cyano-n-(3-fluorophenyl)-3-oxo-3-(1-phenyl-4h-thiochromeno[4,3-c]pyrazol-3-yl)propanamide Chemical compound FC1=CC=CC(NC(=O)C(C#N)C(=O)C=2C3=C(C4=CC=CC=C4SC3)N(N=2)C=2C=CC=CC=2)=C1 UKAYDQDCVIKPBU-UHFFFAOYSA-N 0.000 claims 1
- RLKIZXFGDAHRML-UHFFFAOYSA-N 2-cyano-n-(4-fluorophenyl)-3-[1-(4-fluorophenyl)-4h-thiochromeno[4,3-c]pyrazol-3-yl]-3-oxopropanamide Chemical compound C1=CC(F)=CC=C1NC(=O)C(C#N)C(=O)C1=NN(C=2C=CC(F)=CC=2)C2=C1CSC1=CC=CC=C21 RLKIZXFGDAHRML-UHFFFAOYSA-N 0.000 claims 1
- YDOYHGBBIIFRJR-UHFFFAOYSA-N 2-cyano-n-(4-fluorophenyl)-3-oxo-3-(1-phenyl-4h-thiochromeno[4,3-c]pyrazol-3-yl)propanamide Chemical compound C1=CC(F)=CC=C1NC(=O)C(C#N)C(=O)C1=NN(C=2C=CC=CC=2)C2=C1CSC1=CC=CC=C21 YDOYHGBBIIFRJR-UHFFFAOYSA-N 0.000 claims 1
- VDYNPNAPWQIFTQ-UHFFFAOYSA-N 3-(8-chloro-1-phenyl-4h-chromeno[4,3-c]pyrazol-3-yl)-2-cyano-3-oxo-n-phenylpropanamide Chemical compound C1=2C3=CC(Cl)=CC=C3OCC=2C(C(=O)C(C#N)C(=O)NC=2C=CC=CC=2)=NN1C1=CC=CC=C1 VDYNPNAPWQIFTQ-UHFFFAOYSA-N 0.000 claims 1
- JTMBOTUURXATFK-UHFFFAOYSA-N 3-(8-chloro-1-phenyl-4h-chromeno[4,3-c]pyrazol-3-yl)-2-cyano-n-(4-fluorophenyl)-3-oxopropanamide Chemical compound C1=CC(F)=CC=C1NC(=O)C(C#N)C(=O)C1=NN(C=2C=CC=CC=2)C2=C1COC1=CC=C(Cl)C=C21 JTMBOTUURXATFK-UHFFFAOYSA-N 0.000 claims 1
- ZLFJSXAYMVBZBM-UHFFFAOYSA-N 3-(8-chloro-1-phenyl-4h-thiochromeno[4,3-c]pyrazol-3-yl)-2-cyano-n-(3-fluorophenyl)-3-oxopropanamide Chemical compound FC1=CC=CC(NC(=O)C(C#N)C(=O)C=2C3=C(C4=CC(Cl)=CC=C4SC3)N(N=2)C=2C=CC=CC=2)=C1 ZLFJSXAYMVBZBM-UHFFFAOYSA-N 0.000 claims 1
- LOYKAQUQXXZDBA-UHFFFAOYSA-N 3-(8-chloro-1-phenyl-4h-thiochromeno[4,3-c]pyrazol-3-yl)-2-cyano-n-(4-fluorophenyl)-3-oxopropanamide Chemical compound C1=CC(F)=CC=C1NC(=O)C(C#N)C(=O)C1=NN(C=2C=CC=CC=2)C2=C1CSC1=CC=C(Cl)C=C21 LOYKAQUQXXZDBA-UHFFFAOYSA-N 0.000 claims 1
- IFADRJRXYOQRLL-UHFFFAOYSA-N 3-[1-(3-chlorophenyl)-4h-chromeno[4,3-c]pyrazol-3-yl]-2-cyano-3-oxo-n-phenylpropanamide Chemical compound ClC1=CC=CC(N2C=3C4=CC=CC=C4OCC=3C(C(=O)C(C#N)C(=O)NC=3C=CC=CC=3)=N2)=C1 IFADRJRXYOQRLL-UHFFFAOYSA-N 0.000 claims 1
- QVSQGWSKWOHOHF-UHFFFAOYSA-N 3-[8-chloro-1-(4-fluorophenyl)-4h-thiochromeno[4,3-c]pyrazol-3-yl]-2-cyano-3-oxo-n-phenylpropanamide Chemical compound C1=CC(F)=CC=C1N1C(C2=CC(Cl)=CC=C2SC2)=C2C(C(=O)C(C#N)C(=O)NC=2C=CC=CC=2)=N1 QVSQGWSKWOHOHF-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004423 acyloxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- SXNSMTFYBKURQX-UHFFFAOYSA-N n-(3-chlorophenyl)-2-cyano-3-oxo-3-(1-phenyl-4h-thiochromeno[4,3-c]pyrazol-3-yl)propanamide Chemical compound ClC1=CC=CC(NC(=O)C(C#N)C(=O)C=2C3=C(C4=CC=CC=C4SC3)N(N=2)C=2C=CC=CC=2)=C1 SXNSMTFYBKURQX-UHFFFAOYSA-N 0.000 claims 1
- BDMBPUGREPXOAP-UHFFFAOYSA-N n-benzyl-2-cyano-3-(4-methyl-1-phenyl-4h-chromeno[4,3-c]pyrazol-3-yl)-3-oxopropanamide Chemical compound CC1OC2=CC=CC=C2C2=C1C(C(=O)C(C#N)C(=O)NCC=1C=CC=CC=1)=NN2C1=CC=CC=C1 BDMBPUGREPXOAP-UHFFFAOYSA-N 0.000 claims 1
- XNIVYFYVBVRXDQ-UHFFFAOYSA-N n-benzyl-2-cyano-3-(8-methoxy-1-phenyl-4h-thiochromeno[4,3-c]pyrazol-3-yl)-3-oxopropanamide Chemical compound C1=2C3=CC(OC)=CC=C3SCC=2C(C(=O)C(C#N)C(=O)NCC=2C=CC=CC=2)=NN1C1=CC=CC=C1 XNIVYFYVBVRXDQ-UHFFFAOYSA-N 0.000 claims 1
- QKERGXQCKGMOGB-UHFFFAOYSA-N n-benzyl-2-cyano-3-(8-methyl-1-phenyl-4h-thiochromeno[4,3-c]pyrazol-3-yl)-3-oxopropanamide Chemical compound C1=2C3=CC(C)=CC=C3SCC=2C(C(=O)C(C#N)C(=O)NCC=2C=CC=CC=2)=NN1C1=CC=CC=C1 QKERGXQCKGMOGB-UHFFFAOYSA-N 0.000 claims 1
- KLHCCTWPKBXJSJ-UHFFFAOYSA-N n-benzyl-2-cyano-3-[1-(3,5-dichlorophenyl)-4h-thiochromeno[4,3-c]pyrazol-3-yl]-3-oxopropanamide Chemical compound ClC1=CC(Cl)=CC(N2C=3C4=CC=CC=C4SCC=3C(C(=O)C(C#N)C(=O)NCC=3C=CC=CC=3)=N2)=C1 KLHCCTWPKBXJSJ-UHFFFAOYSA-N 0.000 claims 1
- NRJNDQSMLXLKBY-UHFFFAOYSA-N n-benzyl-2-cyano-3-[1-(4-fluorophenyl)-4h-chromeno[4,3-c]pyrazol-3-yl]-3-oxopropanamide Chemical compound C1=CC(F)=CC=C1N1C(C2=CC=CC=C2OC2)=C2C(C(=O)C(C#N)C(=O)NCC=2C=CC=CC=2)=N1 NRJNDQSMLXLKBY-UHFFFAOYSA-N 0.000 claims 1
- ACHCVNZWYGDXIZ-UHFFFAOYSA-N n-benzyl-2-cyano-3-oxo-3-(1-phenyl-4h-thiochromeno[4,3-c]pyrazol-3-yl)propanamide Chemical compound N=1N(C=2C=CC=CC=2)C(C2=CC=CC=C2SC2)=C2C=1C(=O)C(C#N)C(=O)NCC1=CC=CC=C1 ACHCVNZWYGDXIZ-UHFFFAOYSA-N 0.000 claims 1
- STIDVQXSAHAXSP-UHFFFAOYSA-N n-benzyl-3-(8-chloro-1-phenyl-4h-chromeno[4,3-c]pyrazol-3-yl)-2-cyano-3-oxopropanamide Chemical compound C1=2C3=CC(Cl)=CC=C3OCC=2C(C(=O)C(C#N)C(=O)NCC=2C=CC=CC=2)=NN1C1=CC=CC=C1 STIDVQXSAHAXSP-UHFFFAOYSA-N 0.000 claims 1
- GMIXCSQUZDNSOH-UHFFFAOYSA-N n-benzyl-3-(8-chloro-1-phenyl-4h-thiochromeno[4,3-c]pyrazol-3-yl)-2-cyano-3-oxopropanamide Chemical compound C1=2C3=CC(Cl)=CC=C3SCC=2C(C(=O)C(C#N)C(=O)NCC=2C=CC=CC=2)=NN1C1=CC=CC=C1 GMIXCSQUZDNSOH-UHFFFAOYSA-N 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 159000000000 sodium salts Chemical group 0.000 claims 1
- 229910052717 sulfur Chemical group 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
-
- 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
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyridine Compounds (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (7)
- 일반식 (I)의 화합물 및 그의 약제학적으로 허용되는 염.상기식에서, X는 산소원자 또는 -S(O)n- 그룹(여기에서, n은 0,1 또는 2이다)이고, R1은 C1-C6알킬, 벤질, 피리딜 ; 또는 할로겐, 트리플루오로메틸, C1-C6알킬, C1-C6-알콕시, 니트로, 아미노, 프로밀아미노 및 C2-C8알카노일아미노중에서 독립적으로 선택된 하나 또는 두개의 치환체에 의해 치환되거나 비치환된 페닐이며 ; R2및 R3는 각기 독립적으로, a) 수소, 할로겐 또는 C1-C6알킬이거나 ; b) 하이드록시, C1-C6알콕시 또는 C3-C4알케닐옥시이거나 ; 또는 c) 니트로, 아미노, 포르밀아미노 또는 C2-C8알카노일아미노이고 ; R4는 수소 또는 C1-C6알킬이며 ; Q는 수소, 카복시, CONH2, C2-c7알콕시카보닐 또는또는그룹 [여기에서, Ra는 수소 또는 C1-C20알킬이고, Rb는 C1-C20알킬 또는 -(CH2)m-R5그룹(여기에서, m은 0,1 또는 2이고, R5는 a′C5-C8시클로알킬이거나 ; b′) 할로겐, C1-C6알킬 및 C1-C6알콕시중에서 독립적으로 선택된 하나 또는 두개의 치환체에 의해 치환되거나 비치환된 피리딜이거나 ; 또는 C′) 할로겐, CF3, C1-C6알킬, C1-C6알콕시, 아미노, 니트로, 포르밀아미노, C2-C8알카노일아미노, 디(C1-C6알킬)아미노, 하이드록시, 포르밀옥시 및 C2-C8알카노일옥시 중에서 독립적으로 선택된 하나 또는 두개의 치환체에 의해 치환되거나 비치환된 페닐이다)]이다.
- 제1항에 있어서, X가 산소 또는 -S(O)P- 그룹 (여기에서, P는 0 또는 1이다)이고 ; R1은 C1-C6알킬 ; 비치환된 피리딜 ; 또는 할로겐, 트리플루오로메틸, C1-C6알킬, C1-C6알콕시, 니트로, 아미노 및 C2-C8알카노일아미노중에서 독립적으로 선택된 하나 또는 두개의 치환체로 치환되거나 비치환된 페닐이며 ; R2및 R3는 각각 독립적으로 수소, 할로겐, C1-C4알킬 또는 C1-C4알콕시이고 ; R4는 수소 또는 C1-C4알킬이며 ; Q는 수소, -CONH2, C2-C5알콕시카보닐 또는 -CONR′aR′b또는 -CSNHR′b그룹 [여기에서, R′a는 수소 또는 C1-C6알킬이고, R′b는 C1-C6알킬 또는 -(CH2)m-R5′ 그룹(여기서, m은 0,1 또는 2이고, R5′는 C5-C8시클로알킬,비치환된 피리딜 ; 또는 할로겐, CF3,C1-C4알킬, C1-C4알콕시, 하이드록시, 니트로 및 디-(C1-C4알킬) 아미노중에서 독립적으로 선택된 하나 또는 두개의 치환체에 의해 치환되거나 비치환된 페닐이다)이다]인 일반식 (1)의 화합물 및 그의 약제학적으로 허용되는 염.
- 제1항에 있어서, X가 산소 또는 황이고 ; R1이 C1-C4알킬 ; 또는 니트로, 할로겐, CF3, C1-C4알킬 및 C1-C4알콕시중에서 독립적으로 선택된 하나 또는 두개의 치환체에 의해 치환되거나 비치환된 페닐 이며; R2및 R3가 각각 독립적으로 수소, 할로겐, C1-C4알킬 또는 C1-C4알콕시이고 ; R4가 수소 또는 C1-C4알킬이고 ; Q가 수소, C1-C3알콕시카보닐 또는 -CONRa″Rb″ 또는 -CSNRb″ 그룹(여기에서, Ra″는 수소 또는 C1-C4알킬이고, Rb″는 C1-C4알킬 또는 -(CH2)m-R5″ 그룹(여기서, m은 0,1 또는 2이고, R5″는 C5-C6시클로알킬, 또는 니트로, 할로겐, CF3, C1-C4알킬 및 C1-C4알콕시중에서, 독립적으로 선택된 하나 또는 두개의 치환체에 의해 치환되거나 비치환된 페닐이다)이다)인 일반식 (I)의 화합물 및 그의 약제학적으로 허용되는 염.
- 2-시아노-3-(1,4-디하이드로-1-페닐)-[1]벤조티오피라노[4,3-C] 피라졸-3-일)-3-옥소-N-페닐-프로판아미드 ; N-(3-클로로-페닐)-2-시아노-3-(1,4-디하이드로-1-페닐-[1]-벤조티오피라노[4,3-C] 피라졸-3-일)-3-옥소-프로판아미드 ; 2-시아노-3-(1,4-디하이드로-1-페닐-[1]-벤조티오피라노[4, 3-C] 피라졸-3-일)-3-옥소-N-(3-트리플루오로메틸-페닐)-프로판아미드 ; 2-시아노-3-(1,4-디하이드로-1-페닐-[1]-벤조티오피라노[4,3-C] 피라졸-3-일)-N-(4-플루오로-페닐)-3-옥소-프로판아미드 ; 3-(8-클로로-1,4-디하이드로-1-페닐-[1]-벤조피라노[4,3-C] 피라졸-3-일)-2-시아노-N-(4-플루오로 -페닐)-3-옥소프로판아미드 ; N-(3,5-디클로로-페닐)]-2-시아노-3-(1,4-디하이드로-1-페닐-[1]-벤조티오피라노[4,3-C] 피라졸-3-일)-3-옥소-프로판아미드 ; N-벤질-2-시아노-3-(1,4-디하이드로-1-페닐-[1]-벤조티오피라노[4 ,3-C] 피라졸-3-일)-3-옥소-프로판아미드 ; 3-(8-클로로-1,4-디하이드로-1-페닐-[1]-벤조티오피라노-[4,3-C] 파라졸-3-일)-2-시아노-3-옥소-N-페닐-프로판아미드 ; 2-시아노-3-(1,4-디하이드로-8-메틸-1-페닐-[1]-벤조티오피라노[4,3-C] 피라졸-3-일)-3-옥소-N-페닐-프로판아미드 ; N-벤질-3-(8-클로로-1,4-디하이드로-1-페닐-[1]-벤조티오피라노[4,3-C] 피라졸-3-일)-2-시아노-3-옥소-프로판아미드 ; N-벤질-2-시아노-3-(1,4-디하이드로-8-메틸-1-페닐-[1]-벤조티오피라노[4,3-C] 피라졸-3-일)-3-옥소-프로판아미드 ; 2-시아노-3-(1,4-디하이드로-8-메톡시-1-피닐-[1]-벤조티오피라노[4 ,3-C] 피라졸-3-일)-3-옥소-N-페닐-프로판아미드 ; N-(3-클로로-페닐)-3-(8-클로로-1,4-디하이드로-1-페닐-[1]-벤조티오피라노[4,4-C] 피라졸-3-일)-2-시아노-3-옥소-프로판아미드 ; N-벤질-2-시아노-3-(1,4-디하이드로-8-메톡시-1-페닐[1]-벤조티오피라노[4,3-C] 피라졸-3-일)-3-옥소-프로판아미드 ; 3-(8-클로로-1,4-디하이드로-1-페닐-[1]-벤조티오피라노[4,3-C] 피라졸-3-일)-2-시아노-N-(4-플루오로-페닐)-3-옥소-프로판아미드 ; 3-[1-(4-플루오로-페닐)-1,4-디하이드로-[1]-벤조티오피라노[4,3-C] 피라졸-3-일]-2-시아노-N-(4-플루오로-페닐)-3-옥소-프로판아미드 ; 3-[1-(3,5-디클로로-페닐)-1,4-디하이드로-[1]-벤조티오피라노[4,3-C] 피라졸-3-일]-2-시아노-3-옥소-N-페닐-프로판아미드 ; 2-시아노-3-[1,4-디하이드로-1-(4-플루오로-페닐)-[1]-벤조티오리라노[4,3-C] 피라졸-3-일]-3-옥소-N-페닐-프로파아미드 ; N-벤질-3-[1-(3-클로로-페닐)-1,4-디하이드로-[1]-벤조피라노 [4,3-C] 피라졸-3-일]-2-시아노-3-옥소 프로판아미드 ; N-벤질-3-[1-(3,5-디클로로-페닐)-1,4-디하이드로-[1]-벤조티오피라노[4,3-C] 피라졸-3-일]-2-시아노-3-옥소-프로판아미드 ; N-벤질2-시아노-2-시아노-3-[1-(4-플루오로-페닐)-1,4-디하이드로-[1]-벤조티오피라노[4,3-C]피라졸-3-일]-3-옥소-프로판아미드 ; N-벤질-3-[8-클로로-1-(4-플루오로-페닐)-1,4-디하이드로-[1]-벤조티오피라노[4,3-C] 피라졸-3-일)-2-시아노-3-옥소-프로판아미드 ; 3-[8-클로로-1-(4-플루오로-페닐)-1,4-디하이드로-[1]-벤조티오피라노[4,3-C] 피라졸-3-일]-2-시아노-3-옥소-N-페닐-프로판아미드 ; 2-시아노-3-(1,4-디하이드로-1-페닐-[1]-벤조피라노[4,3-C] 피라졸-3-일)-3-옥소-N-페닐-프로판아미드 ; N-(3-클로로-페닐)-2-시아노-3-(1,4-디하이드로-1-페닐-[1]-벤조피라노[4,3-C] 피라졸-3-일)-3-옥소-프로판아미드 ; 2-시아노-3-(1,4-디하이드로-1-페닐-[1]벤조피라노[4,3-C] 피라졸-3-일)-N-(4-플루오로-페닐)-3-옥소-프로판아미드 ; N-벤질-2-시아노-3-(1,4-디하이드로-1-페닐-[1]-벤조피라노[4,3-C] 피라졸-3-일)-3-옥소-프로판아미드 ; 2-시아노-3-(1,4-디하이드로-1-페닐-[1]-벤조티오피라노[4,3-C] 피라졸-3-일)-N-(3-플루오로-페닐)-3-옥소-프로판아미드 ; 3-[1-(3-클로로-페닐)-1,4-디하이드로-[1]-벤조피라노[4,3-C] 피라졸-3-일]-2-시아노-3-옥소-N-페닐-프로판아미드 ; 2-시아노-3-[1,4-디하이드로-1-(4-플루오로-페닐)-[1]-벤조피라노[4,3-C] 피라졸-3-일]-3-옥소-N-페닐-프로판아미드 ; N-벤질-3-[1-(3-클로로-페닐)-1,4-디하이드로-[1]-벤조피라노[4,3-C] 피라졸-3-일]-2-시아노-3-옥소-프로판아미드 ; N-벤질-2-시아노-3-[1-(4-플루오로-페닐)-1,4-디하이드로-[1]-벤조피라노[4,3-C] 피라졸-3-일]-3-옥소-프로판아미드 ; 2-시아노-3-(1,4-디하이드로-4-메틸-1-페닐-[1]-벤조피라노[4,3-C] 피라 졸-3-일)-3-옥소-N-페닐-프로판아미드 ; N-벤질-2-시아노-3-(1,4-디하이드로-4-메틸-1-페닐-[1]-벤조피라노[4,3-C] 피라졸-3-일)-3-옥소-프로판아미드 ; 3-(8-클로로-1,4-디하이드로-1-페닐-[1]-벤조피라노[4,3-C] 피라졸-3-일)-2-시아노-3-옥소-N-페닐-프로판아미드 ; N-벤질-3-(8-클로로-1,4-디하이드로-1-페닐-[1]-벤조피라노[4,3-C] 피라졸-3-일)-2-시아노-3-옥소 -프로판아미드 ; 3-(8-클로로-1,4-디하이드로-1-페닐-[1]-벤조티오피라노 [4,3-C] 피라졸-3-일)-2-시아노-N-(3-플루오로-페닐)-3-옥소-프로판아미드 ; 3-(8-클로로-1,4-디하이드로-1-페닐-[1]-벤조피라노[4,3-C] 피라졸-3-일)-2-시아노-N-(3-플루오로-페닐)-3-옥소-프로판아미드로 구성되어 있는 그룹으로 부터 선택된 화합물 및 그의 약제학적으로 허용되는 염.
- 제4항에 있어서, 염이 나트륨염 또는 칼륨염인 약제학적으로 허용되는 염.
- a) 일반식 (II)의 화합물과 일반식 (III)의 화합물을 반응시켜 Q가 카복시가 아닌 일반식 (I)의 화합물을 수득하거나 ; b) 일반식 (IV)의 화합물과 일반식 (V) 또는 (Va)의 화합물을 반응시켜 각각 Q가 -CONHRb또는 -CSNHRb그룹인 일반식 (I)의 화합물을 수득하거나 ; c) 일반식 (VI)의 화합물과 일반식 (VII)의 화합물을 반응시켜 Q가그룹인 일반식 (I)의 화합물을 수득하거나 ; 또는 d) Q가 C2-C7알콕시카보닐 그룹인 일반식 (I)의 화합물을 Q가 유리 카복시 그룹인 상응하는 일반식 (I)의 화합물을 일반식 (I)의 다른 화합물로 전환시키고/거나 경우에 따라, 일반식 (I)의 화합물을 약제학적으로 허용되는 염으로 전환시키고/거나 경우에 따라 염을 유리 화합물로 전환시킴을 특징으로 하여 제1항에 정의된 일반식 (I)의 화합물 또는 그의 약제학적으로 허용되는 염을 제조하는 방법.상기식에서, X,R1,R2,R3,R4,Ra및 Rb는 제1항에서 정의한 바와 같고 ; Y는 카복시 그룹 또는 카복시 그룹의 반응성 유도체이며 ; Q′는 제1항에서 정의한 Q와 같으나, 단 카복시는 제외하며 ; Z는 카복시 그룹의 반응성 유도체이다.
- 적당한 담체 및/또는 희석제 및, 활성성분으로서 제1항에 따른 일반식 (I)의 화합물 또는 그의 약제학적으로 허용되는 염을 함유하는 약제학적 조성물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878700477A GB8700477D0 (en) | 1987-01-09 | 1987-01-09 | Heteroaryl 2-cyano-3-oxo-propanamide derivatives |
| IT8700477 | 1987-01-09 | ||
| GB8700477 | 1987-01-09 | ||
| GB878717282A GB8717282D0 (en) | 1987-07-22 | 1987-07-22 | Heteroaryl 3-oxo-propanenitrile derivatives |
| IT8717282 | 1987-07-22 | ||
| GB8717282 | 1987-07-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR880008987A true KR880008987A (ko) | 1988-09-13 |
| KR960002852B1 KR960002852B1 (ko) | 1996-02-27 |
Family
ID=26291768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019880000056A KR960002852B1 (ko) | 1987-01-09 | 1988-01-08 | 헤테로아릴 3-옥소-프로판니트릴 유도체, 이의 제조방법 및 이를 함유하는 약제학적 조성물 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4816467A (ko) |
| EP (1) | EP0274443B1 (ko) |
| JP (1) | JP2672312B2 (ko) |
| KR (1) | KR960002852B1 (ko) |
| CN (1) | CN1025500C (ko) |
| AU (1) | AU598893B2 (ko) |
| CA (1) | CA1310647C (ko) |
| CZ (1) | CZ277972B6 (ko) |
| DE (1) | DE3862937D1 (ko) |
| DK (1) | DK8088A (ko) |
| ES (1) | ES2029003T3 (ko) |
| FI (1) | FI89489C (ko) |
| GR (1) | GR3002032T3 (ko) |
| HU (1) | HU198722B (ko) |
| IE (1) | IE60620B1 (ko) |
| IL (1) | IL85004A (ko) |
| MY (1) | MY103348A (ko) |
| NO (1) | NO165841C (ko) |
| NZ (1) | NZ223113A (ko) |
| PH (1) | PH27000A (ko) |
| PT (1) | PT86516B (ko) |
| SU (1) | SU1695826A3 (ko) |
| YU (2) | YU46787B (ko) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0286346B1 (en) * | 1987-04-09 | 1994-04-06 | E.I. Du Pont De Nemours And Company | Insecticidal substituted indazoles |
| GB8814586D0 (en) * | 1988-06-20 | 1988-07-27 | Erba Carlo Spa | Tricyclic 3-oxo-propanenitrile derivatives & process for their preparation |
| GB8814587D0 (en) * | 1988-06-20 | 1988-07-27 | Erba Carlo Spa | Condensed pyrazole 3-oxo-propanenitrile derivatives & process for their preparation |
| GB2227741B (en) * | 1989-02-06 | 1992-08-05 | Erba Carlo Spa | Condensed 3-oxo-propanenitrile derivatives and process for their preparation |
| GB8907799D0 (en) * | 1989-04-06 | 1989-05-17 | Erba Carlo Spa | Heteroaryl-3-oxo-propanenitrile derivatives useful in the treatment of rheumatoid arthritis and other autoimmune diseases |
| US5260328A (en) * | 1989-04-06 | 1993-11-09 | Farmitalia Carlo Erba Srl | Phenyl-indenopurazol 3-oxo-propanamide derivatives useful in the treatment of rheumatoid arthritis |
| GB8916290D0 (en) * | 1989-07-17 | 1989-08-31 | Erba Carlo Spa | Heteroaryl-3-oxo-propanenitrile derivatives useful in stimulating myelopoiesis |
| DK0527736T3 (da) * | 1990-05-18 | 1997-10-20 | Hoechst Ag | Isoxazol-4-carboxylsyreamider og hydroxyalkyliden-cyanoacetamider, lægemidler indeholdende disse forbindelser og anvendelsen af disse lægemidler. |
| US5547975A (en) * | 1994-09-20 | 1996-08-20 | Talley; John J. | Benzopyranopyrazolyl derivatives for the treatment of inflammation |
| US5886016A (en) * | 1995-09-15 | 1999-03-23 | G.D. Searle & Co. | Benzopyranopyrazolyl derivatives for the treatment of inflammation |
| GB9720899D0 (en) * | 1997-10-01 | 1997-12-03 | Pharmacia & Upjohn Spa | Condensed heterocyclic compounds |
| DK2857516T3 (en) * | 2000-04-11 | 2017-08-07 | Genentech Inc | Multivalent antibodies and uses thereof |
| ES2286275T3 (es) * | 2001-09-19 | 2007-12-01 | Pharmacia Corporation | Compuestos de pirazolo sustituidos para el tratamiento de la inflamacion. |
| CA2534426A1 (en) * | 2003-08-08 | 2005-02-17 | Barnes-Jewish Hospital | Emulsion particles for imaging and therapy and methods of use thereof |
| US20060035242A1 (en) | 2004-08-13 | 2006-02-16 | Michelitsch Melissa D | Prion-specific peptide reagents |
| CA2650574A1 (en) * | 2006-04-27 | 2007-11-08 | Barnes-Jewish Hospital | Detection and imaging of target tissue |
| CA2778174C (en) * | 2009-11-13 | 2018-02-20 | Merck Serono S.A. | Tricyclic pyrazol amine derivatives as pi3k inhibitors |
| CN102086212B (zh) * | 2009-12-03 | 2013-06-12 | 沈阳药科大学 | 抗真菌剂-2，3，4，5-四氢-4H-苯并[b]噻喃并[4，3-c]吡唑-2-甲酰胺衍生物 |
| WO2018075564A1 (en) | 2016-10-17 | 2018-04-26 | University Of Maryland, College Park | Multispecific antibodies targeting human immunodeficiency virus and methods of using the same |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4268516A (en) * | 1978-10-11 | 1981-05-19 | Pfizer Inc. | [1]Benzothiopyrano[4,3-c]pyrazoles as immunoregulatory agents |
| EP0022446A1 (de) * | 1979-04-06 | 1981-01-21 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Verfahren zur Herstellung von Biotinestern und von Biotin |
| EP0057932A1 (en) * | 1981-02-11 | 1982-08-18 | E.I. Du Pont De Nemours And Company | Antiinflammatory and/or analgesic 3,4-dihydro(or 1,4-dihydro)-2-((substituted)thiol)-(1)-benzopyrano(3,4-d)imidazoles and their corresponding sulfoxides and sulfones |
| PH21213A (en) * | 1984-10-26 | 1987-08-21 | Fujisawa Pharmaceutical Co | Benzene- and pyrazole- fused heterocyclic compound and pharmaceutical composition comprising the same |
-
1987
- 1987-12-31 US US07/140,221 patent/US4816467A/en not_active Expired - Fee Related
-
1988
- 1988-01-01 IL IL85004A patent/IL85004A/xx not_active IP Right Cessation
- 1988-01-04 PH PH36319A patent/PH27000A/en unknown
- 1988-01-04 IE IE288A patent/IE60620B1/en not_active IP Right Cessation
- 1988-01-05 AU AU10037/88A patent/AU598893B2/en not_active Ceased
- 1988-01-06 YU YU1088A patent/YU46787B/sh unknown
- 1988-01-07 NZ NZ223113A patent/NZ223113A/xx unknown
- 1988-01-07 CN CN88100153A patent/CN1025500C/zh not_active Expired - Fee Related
- 1988-01-07 CA CA000556010A patent/CA1310647C/en not_active Expired - Fee Related
- 1988-01-07 CZ CS88179A patent/CZ277972B6/cs not_active IP Right Cessation
- 1988-01-08 PT PT86516A patent/PT86516B/pt not_active IP Right Cessation
- 1988-01-08 DK DK008088A patent/DK8088A/da not_active Application Discontinuation
- 1988-01-08 EP EP88300115A patent/EP0274443B1/en not_active Expired - Lifetime
- 1988-01-08 HU HU8858A patent/HU198722B/hu not_active IP Right Cessation
- 1988-01-08 DE DE8888300115T patent/DE3862937D1/de not_active Expired - Fee Related
- 1988-01-08 NO NO880068A patent/NO165841C/no unknown
- 1988-01-08 SU SU884355070A patent/SU1695826A3/ru active
- 1988-01-08 ES ES198888300115T patent/ES2029003T3/es not_active Expired - Lifetime
- 1988-01-08 JP JP63002374A patent/JP2672312B2/ja not_active Expired - Lifetime
- 1988-01-08 MY MYPI88000014A patent/MY103348A/en unknown
- 1988-01-08 FI FI880078A patent/FI89489C/fi not_active IP Right Cessation
- 1988-01-08 KR KR1019880000056A patent/KR960002852B1/ko active IP Right Grant
-
1989
- 1989-04-18 YU YU00794/89A patent/YU79489A/xx unknown
-
1991
- 1991-05-30 GR GR91400684T patent/GR3002032T3/el unknown
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