KR920006347A - 헤테로사이클릭 유도체 - Google Patents
헤테로사이클릭 유도체 Download PDFInfo
- Publication number
- KR920006347A KR920006347A KR1019910016597A KR910016597A KR920006347A KR 920006347 A KR920006347 A KR 920006347A KR 1019910016597 A KR1019910016597 A KR 1019910016597A KR 910016597 A KR910016597 A KR 910016597A KR 920006347 A KR920006347 A KR 920006347A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- imidazo
- methyl
- pyridine
- tetrazol
- Prior art date
Links
- 125000000623 heterocyclic group Chemical group 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 32
- 150000001875 compounds Chemical class 0.000 claims 22
- 229910052736 halogen Inorganic materials 0.000 claims 17
- 150000002367 halogens Chemical class 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- 150000003839 salts Chemical class 0.000 claims 14
- -1 3H-imidazo [4,5-b] pyridin-2-yl Chemical group 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000004414 alkyl thio group Chemical group 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 102000005862 Angiotensin II Human genes 0.000 claims 2
- 101800000733 Angiotensin-2 Proteins 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 229950006323 angiotensin ii Drugs 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 231100000252 nontoxic Toxicity 0.000 claims 2
- 230000003000 nontoxic effect Effects 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims 1
- SUCACHBVGZPQIJ-UHFFFAOYSA-N 2-butyl-3-[[4-[4-chloro-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-7-methylimidazo[4,5-b]pyridine Chemical compound CCCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C=C(Cl)C=C1C1=NN=NN1 SUCACHBVGZPQIJ-UHFFFAOYSA-N 0.000 claims 1
- GMVKOARZIHFHES-UHFFFAOYSA-N 2-ethyl-5,7-dimethyl-3-[[4-[2-methyl-5-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]imidazo[4,5-b]pyridine Chemical compound CCC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1N1C(C)=CC=C1C1=NN=NN1 GMVKOARZIHFHES-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- JYWTUQYDJWROBU-UHFFFAOYSA-N 3-[[4-[1-ethyl-3-(2h-tetrazol-5-yl)pyrrol-2-yl]phenyl]methyl]-5,7-dimethyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1C(N(C=C1)CC)=C1C1=NN=NN1 JYWTUQYDJWROBU-UHFFFAOYSA-N 0.000 claims 1
- HFFUHKSOQSITLY-UHFFFAOYSA-N 3-[[4-[1-ethyl-3-(2h-tetrazol-5-yl)pyrrol-2-yl]phenyl]methyl]-7-methyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1C(N(C=C1)CC)=C1C1=NN=NN1 HFFUHKSOQSITLY-UHFFFAOYSA-N 0.000 claims 1
- AUBCPJWAFNWFQY-UHFFFAOYSA-N 3-[[4-[2,3-dimethyl-5-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-7-methyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C(C)=C(C)C=C1C=1N=NNN=1 AUBCPJWAFNWFQY-UHFFFAOYSA-N 0.000 claims 1
- RJFKLCPHPHROKU-UHFFFAOYSA-N 3-[[4-[2-bromo-5-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-2-butyl-7-methylimidazo[4,5-b]pyridine Chemical compound CCCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C(Br)=CC=C1C1=NN=NN1 RJFKLCPHPHROKU-UHFFFAOYSA-N 0.000 claims 1
- PRHFIICWZSMSCL-UHFFFAOYSA-N 3-[[4-[2-chloro-1-methyl-4-(2h-tetrazol-5-yl)pyrrol-3-yl]phenyl]methyl]-2-ethyl-5,7-dimethylimidazo[4,5-b]pyridine Chemical compound CCC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1C1=C(Cl)N(C)C=C1C=1N=NNN=1 PRHFIICWZSMSCL-UHFFFAOYSA-N 0.000 claims 1
- SJCSWWIDVDGUBZ-UHFFFAOYSA-N 3-[[4-[2-chloro-1-methyl-4-(2h-tetrazol-5-yl)pyrrol-3-yl]phenyl]methyl]-5,7-dimethyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1C1=C(Cl)N(C)C=C1C1=NN=NN1 SJCSWWIDVDGUBZ-UHFFFAOYSA-N 0.000 claims 1
- IJZDRCUFOIPZGG-UHFFFAOYSA-N 3-[[4-[2-chloro-3-methyl-5-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-7-methyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C(Cl)=C(C)C=C1C1=NN=NN1 IJZDRCUFOIPZGG-UHFFFAOYSA-N 0.000 claims 1
- CEGGCVVNQNGFPT-UHFFFAOYSA-N 3-[[4-[4-bromo-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-2-butyl-7-methylimidazo[4,5-b]pyridine Chemical compound CCCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C=C(Br)C=C1C1=NN=NN1 CEGGCVVNQNGFPT-UHFFFAOYSA-N 0.000 claims 1
- PWJMOOCJXTXGQF-UHFFFAOYSA-N 3-[[4-[4-bromo-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-7-methyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C=C(Br)C=C1C1=NN=NN1 PWJMOOCJXTXGQF-UHFFFAOYSA-N 0.000 claims 1
- OSSWQSCMABLHNH-UHFFFAOYSA-N 3-[[4-[4-chloro-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-2-ethyl-5,7-dimethylimidazo[4,5-b]pyridine Chemical compound CCC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1N1C=C(Cl)C=C1C1=NN=NN1 OSSWQSCMABLHNH-UHFFFAOYSA-N 0.000 claims 1
- BVJDHGHXBOUCST-UHFFFAOYSA-N 3-[[4-[4-chloro-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-2-ethyl-7-methylimidazo[4,5-b]pyridine Chemical compound CCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C=C(Cl)C=C1C1=NN=NN1 BVJDHGHXBOUCST-UHFFFAOYSA-N 0.000 claims 1
- NQAOQSVAXWRKDL-UHFFFAOYSA-N 3-[[4-[4-chloro-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-5,7-dimethyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1N1C=C(Cl)C=C1C=1N=NNN=1 NQAOQSVAXWRKDL-UHFFFAOYSA-N 0.000 claims 1
- BNGSXGHVQZHPPV-UHFFFAOYSA-N 3-[[4-[4-chloro-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-7-methyl-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C=C(Cl)C=C1C1=NN=NN1 BNGSXGHVQZHPPV-UHFFFAOYSA-N 0.000 claims 1
- WERCGTGECUZPKN-UHFFFAOYSA-N 5,7-dimethyl-3-[[4-[2-methyl-5-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=C(C)N=C2N1CC(C=C1)=CC=C1N1C(C)=CC=C1C=1N=NNN=1 WERCGTGECUZPKN-UHFFFAOYSA-N 0.000 claims 1
- ABHIOFVVJQEBHY-UHFFFAOYSA-N 7-methyl-3-[[4-[4-methyl-2-(2h-tetrazol-5-yl)pyrrol-1-yl]phenyl]methyl]-2-propylimidazo[4,5-b]pyridine Chemical compound CCCC1=NC2=C(C)C=CN=C2N1CC(C=C1)=CC=C1N1C=C(C)C=C1C1=NN=NN1 ABHIOFVVJQEBHY-UHFFFAOYSA-N 0.000 claims 1
- 229940123413 Angiotensin II antagonist Drugs 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000005189 alkyl hydroxy group Chemical group 0.000 claims 1
- 239000002333 angiotensin II receptor antagonist Substances 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 238000005755 formation reaction Methods 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 150000003536 tetrazoles Chemical group 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 238000011282 treatment Methods 0.000 claims 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- 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
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- 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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (16)
- 하기 일반식(Ⅰ)의 화합물 및 그의 약제학적으로 허용가능한 염.상기 식에서 R1은 수소, 할로겐, 니트로, 저급 알킬, 저급 알콕시, 아미노 또는 아실아미노이고, R2, R3및 R4는 각각 수소, 할로겐, 니트로, 시아노, 저급알킬, 저급 알케닐, 저급 알킬티오, 모노 또는 디 또는 트리할로(저급)알킬, 옥소(저급)알킬 하이드록시(저급)알킬 또는 임의로 에스테르화된 카르복시이거나, R2및 R3는 함께 결합하여 1,3-부타디에닐렌을 형성하기도 하며, R5는 수소 또는 아미노-보호기이며, A는 저급 알킬렌이고, Q는 CH 또는 N이며, X는 N또는 CH이며, Y는 NH, O또는 S이며,는 적합한 치환기(들)을 가질수 있는 축합 또는 비축합된 이미다졸릴이다.
- 제1항에 있어서,가 방향족 또는 헤테로사이클릭환과 축합될수 있으며, 저급알킬, 할로겐, 저급 알콕시, 하이드록시(저급)알킬 또는 임의로 에스테르화된 카르복시를 함유할수 있는 1H-이미다졸-1-일인 화합물.
- 제2항에 있어서,가 벤젠, 나프탈렌, 피롤, 이미다졸릴, 피라졸, 피리딘, 푸란, 또는 티오펜과 축합될수 있으며, 저급알킬, 할로겐, 저급 알콕시, 하이드록시(저급)알킬, 카르복시 또는 저급알콕시카르보닐을 함유할수 있는 1H-이미다졸-1-일인 화합물.
- 제3항에 있어서, R1은 수소, 할로겐, 니트로, 저급 알킬, 저급 알콕시, 아미노 또는 저급알카노일아미노이고, R2, R3및 R4는 각각 수소, 할로겐, 니트로, 시아노, 저급알킬, 저급 알케닐, 저급 알킬티오, 모노 또는 디 또는 트리할로(저급)알킬, 옥소(저급)알킬, 하이드록시(저급)알킬, 카르복시 또는 저급 알콕시카르보닐이며, R5가 수소 또는 모노 또는 디 또는 트리페닐(저급)알킬이고,각각 저급알킬, 할로겐, 저급알콕시, 하이드록시(저급)알킬 또는 저급 알콕시카르보닐을 함유할수 있는 3H-이미다조[4,5-b]피리딘-2-일, 1H-벤즈이미다졸-1-일, 3H-이미다조[4,5-b]피리미딘-3-일, 1H-티에노[3,4-d]이미다졸-1-일 또는 1H-이미다졸-1-일인 화합물.
- 제4항에 있어서, R1및 R4각 각각 수소이며, Q 및 X가 각각 CH인 화합물.
- 제5항에 있어서, 하기 일반식(1-7)로 표시된 화합물.
- 제6항에 있어서,가 2-저급알킬-3H-이미다조[4,5-b]피리딘-3-일, 2,7-디(저급)알킬-3H-이미다조-[4,5-b]피리딘-3-일, 2,5,7-트리(저급)알킬-3H-이미다조-[4,5-b]피리딘-2-일, 5-할로-2-저급알킬-3H-이미다조-[4,5-b]피리딘-3-일, 5-저급알콕시-2-저급 알킬-3H-이미다조[4,5-b]피리딘-3-일 6-저급 알콕시카르보닐-2-저급알킬-1H-벤즈이미다졸-1-일, 2-저급알킬-3H-이미다조-[4,5-b]피리미딘-3-일, 2-저급알킬-1H-티에노-[3,4-d]이미다졸-1-일-2-저급알킬-4-할로-5-하이드록시(저급)알킬-H-이미다졸-1-일이고,가 하기 일반식(1) 내지 (6)의 그룹중 어느 하나인 화합물.(상기 식에서, Ra 2는 수소, 할로겐, 시아노, 저급 알킬 또는 저급 알킬티오이며, Ra 3는 수소, 할로겐, 니트로, 저급알킬, 저급 알케닐, 트리할로(저급)알킬, 옥소(저급)알킬, 하이드록시(저급)알킬 또는 저급 알콕시카르보닐이다);(상기 식에서, Rb 2및 Rb 3는 각각 할로겐이다);(상기 식에서, Rc 2는 수소, 할로겐 또는 저급 알킬이고, Rc 3은 저급알킬이며; Rc 4은 수소 또는 할로겐이다);(상기 식에서, Rd 2는 수소, 및 할로겐 또는 저급 알킬이고, Rd 3은 저급 알킬이다);(상기 식에서, Re 2는 수소 또는 할로겐이다); 또는
- 제7항에 있어서, (1)3-[4-[4-브로모-2-(1H-테트라졸-5-일)-1-피롤릴]벤질]-2-부틸-7-메틸-3H-이미다조[4,5-b]피리딘, (2)2-부틸-3-[4-[3,4-디클로로-2-(1H-테트라졸-5-일)-1-피롤릴]벤조일-7-메틸-3H-이미다조[4,5-b]피리딘, (3)3-[4-[2-브로모-5-(1H-테트라졸-5-일)-1-피롤릴]벤질]-2-부틸-7-메틸-3H-이미다조[4,5-b]피리딘, 4)3-[4-[4-브로모-2-(1H-테트라졸-5-일)-1-피롤릴]벤질]-7-메틸-2-프로필-3H-이미다조[4,5-b]피리딘, (5)2-부틸-3-[4-[4-클로로-2-(1H-테트라졸-5-일)-1-피롤릴]벤질]-7-메틸-3H-이미다조[4,5-b]피리딘, (6)3-[4-[4-클로로-2-(1H-테트라졸-5-일)-1-피롤릴]벤질]-7-메틸-2-프로필-3H-이미다조[4,5-b]피리딘, (7)7-메틸-3-[4-[4-메틸-2-(1H-테트라졸-5-일)-1-피롤릴]벤질]-2-프로필-3H-이미다조[4,5-b]피리딘, (8)7-메틸-3-[4-[2-메틸-5-(1H-테트라졸-5-일)-1-피롤릴]벤질]-프로필-메틸-3H-이미다조[4,5-b]피리딘, (9)3-[4-[3-클로로-2-메틸-5-(1H-테트라졸-5-일)-1-피롤릴]벤질]-7-메틸-2-프로필-3H-이미다조[4,5-b]피리딘, (10))3-[4-[4-클로로-2-(1H-테트라졸-5-일)-1-피롤릴]벤질]-2-에틸-5,7-디메틸-3H-이미다조[4,5-b]피리딘, (11)5,7-디메틸-3-[4-[2-메틸-5-(1H-테트라졸-5-일)-1-피롤릴]벤질]-2프로필-3H-이미다조[4,5-b]피리딘, (12)3-[4-[2,3-디메틸-5-(1H-테트라졸-5-일)-1-피롤릴]벤질]-7-메틸-2-프로필-3H-이미다조[4,5-b]피리딘, (13)3-[4-[2-클로로-3-메틸-5-(1H-테트라졸-5-일)-1-피롤릴]벤질]-7-메틸-2-프로필-3H-이미다조[4,5-b]피리딘, (14)2-에틸-5,7-디메틸-3-[4-[2-메틸-5-(1H-테트라졸-5-일)-1-피롤릴]벤질]--3H-이미다조[4,5-b]피리딘, (15)3-[4-[4-클로로-2-(1H-테트라졸-5-일)-1-피롤릴]벤질]-2-에틸-7-메틸-3H-이미다조[4,5-b]피리딘, (16)3-[4-[4-클로로-2-(1H-테트라졸-5-일)-1-피롤릴]벤질]-5,7-디메틸-2-프로필-3H-이미다조[4,5-b]피리딘, (17)3-[4-[2-클로로-1-메틸-4-(1H-테트라졸-5-일)-1-피롤릴]벤질]-7-메틸-2-프로필-3H-이미다조[4,5-b]피리딘, (18)3-[4-[5-브로모-1-에틸-3-(1H-테트라졸-5-일)-1-피롤릴]벤질]-7-메틸-2-프로필-3H-이미다조[4,5-b]피리딘, (19)3-[4-[1-에틸-3-(1H-테트라졸-5-일)-2-피롤릴]벤질]-7-메틸-2-프로필-3H-이미다조[4,5-b]피리딘,(20)3-[4-[2-클로로-1-메틸-4-(1H-테트라졸-5-일)-3-피롤릴]벤질]-5,7-디메틸-2-에틸-3H-이미다조[4,5-b]피리딘, (21)5,7-디메틸-2-에틸-3-[4-[1-에틸-3-(1H-테트라졸-5-일)-2-피롤릴]벤질]-이미다조[4,5-b]피리딘, (22)5,7-디메틸-3-[4-[1-에틸-3-(1H-테트라졸-5-일)-2-피롤릴]벤질]-2-프로필-3H-이미다조[4,5-b]피리딘 및 (23)3-[4-[2클로로-1-메틸-4-(1H-테트라졸-5-일)-3-피롤릴]벤질]-5,7-디메틸-2-프로필-3H-이미다조[4,5-b]피리딘, 및 그들의 나트륨염 및 하이드로쿨로라이드로 이루어진 그룹 중에서 선택된 화합물.
- 하기 일반식(Ⅲ)의 화합물을 테트라졸기 형성 반응시켜 하기 일반식(Ⅰ)의 화합물 또는 그의 염을 수득하거나; 하기 일반식(Ⅰ-a)의 화합물 또는 그의 염을 환원시켜 하기 일반식(Ⅰ-b)의 화합물 또는 그의 염을 수득하거나, 하기 일반식(Ⅲ)의 화합물 또는 그의 염을 하기 일반식(Ⅳ)의 화합물 또는 그의 염과 반응시켜 하기 일반식(Ⅰ)의 화합물 또는 그의 염을 수득하거나, 하기 일반식(Ⅰ-c)의 화합물 또는 그의 염으로부터 아미노-보호기를 제거하여 하기 일반식(Ⅰ-d)의 화합물 또는 그의 염을 수득함을 특징으로 하여, 하기 일반식(Ⅰ)의 화합물 또는 그의 염을 제조하는 방법.상기 식에서 R1은 수소, 할로겐, 니트로, 저급 알킬, 저급 알콕시, 아미노 또는 아실아미노이고, R2, R3및 R4는 각각 수소, 할로겐, 니트로, 시아노, 저급알킬, 저급 알케닐, 저급' 알킬티오, 모노 또는 디 또는 트리할로(저급)알킬, 옥소(저급)알킬, 하이드록시(저급)알킬 또는 임의로 에스테르화된 카르복시이거나, R2와 R3는 함께 결합하여 1,3-부타디에닐렌을 형성하기도 하며, R5는 수소 또는 이미노-보호기이고, A는 저급 알킬렌이며, Q는 CH 또는 N이고, X는 N 또는 CH이고, Y는 NH, O또는 S이고,는 적합한 치환기(들)을 가질수 있는 축합 또는 비축합된 이미다졸릴이며, Ra 4는 옥소(저급)알킬또는 할로겐이고, Rb 4는 하이드록시(저급)알킬 또는 수소이며, R6은 산 잔기이고, Ra 5이미노-보호기이다.
- 약제학적으로 허용되며, 본질적으로 무독성인 담체 또는 부형제와 함께 제1항에 따른 화합물 또는 그의 약제학적으로 허용되는 염을 함유하는 약제학적 조성물.
- 사람 또는 동물에게 제1항에 따른 화합물 또는 그의 약제학적으로 허용되는 염을 투여함을 특징으로 하여 안지오텐신 Ⅱ-개재된 질환을 치료 또는 예방하는 방법.
- 사람 또는 동물에게 제1항에 따른 화합물 또는 그의 약제학적으로 허용되는 염을 투여함을 특징으로 하여 고혈압 또는 심부전증을 치료 또는 예방하는 방법.
- 약제로서 사용하기 위한 제1항에 따른 화합물 또는 그의 약제학적으로 허용되는 염.
- 안지오텐신 Ⅱ길항제로서 사용하기 위한 제1항에 따른 화합물 또는 그의 약제학적으로 허용되는 염.
- 안지오텐신 Ⅱ-개재된 질환의 치료 또는 예방용 약제를 제조하기 위한 제1항에 따른 화합물의 용도.
- 제1항에 따른 화합물을 약제학적으로 허용되는 본질적으로 무독성인 담체 또는 부형제와 혼합함을 특징으로 하여 약제학적 조성물을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9020838.0 | 1990-09-25 | ||
| GB909020838A GB9020838D0 (en) | 1990-09-25 | 1990-09-25 | Condensed imidazole derivatives and process for preparation thereof |
| GB909023467A GB9023467D0 (en) | 1990-10-29 | 1990-10-29 | Condensed imidazole derivatives and process for preparation thereof |
| GB9023467.5 | 1990-10-29 | ||
| GB9028216.1 | 1990-12-31 | ||
| GB909028216A GB9028216D0 (en) | 1990-12-31 | 1990-12-31 | Condensed imidazole derivatives and process for preparation thereof |
| GB919103874A GB9103874D0 (en) | 1991-02-25 | 1991-02-25 | Heterocyclic derivatives |
| GB9103874.5 | 1991-02-25 | ||
| GB919106956A GB9106956D0 (en) | 1991-04-03 | 1991-04-03 | Heterocyclic derivatives |
| GB9106956.7 | 1991-04-03 | ||
| GB9107231.4 | 1991-04-05 | ||
| GB919107231A GB9107231D0 (en) | 1991-04-05 | 1991-04-05 | Heterocyclic derivatives |
| GB919112803A GB9112803D0 (en) | 1991-06-14 | 1991-06-14 | Heterocyclic derivatives |
| GB9112803.3 | 1991-06-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR920006347A true KR920006347A (ko) | 1992-04-27 |
Family
ID=27562836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019910016597A KR920006347A (ko) | 1990-09-25 | 1991-09-24 | 헤테로사이클릭 유도체 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5210092A (ko) |
| EP (1) | EP0480204B1 (ko) |
| JP (1) | JPH04288075A (ko) |
| KR (1) | KR920006347A (ko) |
| CN (1) | CN1059723A (ko) |
| AT (1) | ATE135701T1 (ko) |
| AU (1) | AU650473B2 (ko) |
| CA (1) | CA2052125A1 (ko) |
| DE (1) | DE69118082T2 (ko) |
| FI (1) | FI914163A (ko) |
| HU (1) | HUT59404A (ko) |
| IE (1) | IE913164A1 (ko) |
| IL (1) | IL99443A0 (ko) |
| NO (1) | NO913750L (ko) |
| PT (1) | PT99038A (ko) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5177074A (en) * | 1991-03-26 | 1993-01-05 | Merck & Co., Inc. | Angiotensin ii antagonists incorporating a substituted thiophene or furan |
| TW274551B (ko) * | 1991-04-16 | 1996-04-21 | Takeda Pharm Industry Co Ltd | |
| US5252574A (en) * | 1991-04-26 | 1993-10-12 | Merck & Co., Inc. | Angiotensin II antagonists incorporating a substituted thiophene or furan |
| US5198438A (en) * | 1991-05-07 | 1993-03-30 | Merck & Co., Inc. | Angiotensin ii antagonists incorporating a substituted thiophene or furan |
| WO1993019067A1 (en) * | 1991-09-12 | 1993-09-30 | Fujisawa Pharmaceutical Co., Ltd. | Imidazopyridine derivatives as angiotensin ii antagonists |
| GB9201789D0 (en) * | 1992-01-28 | 1992-03-11 | Fujisawa Pharmaceutical Co | Heterocyclic derivatives |
| US5354759A (en) * | 1991-09-12 | 1994-10-11 | Fujisawa Pharmaceutical Co., Ltd. | Angiotenin II antagonizing heterocyclic compounds |
| US5283242A (en) * | 1991-10-24 | 1994-02-01 | American Home Products Corporation | Substituted benzimidazoles and quinazolines as antihypertensives |
| WO1993018030A1 (en) * | 1992-03-03 | 1993-09-16 | Fujisawa Pharmaceutical Co., Ltd. | Benzimidazole derivatives as angiotensin ii antagonists |
| US5364869A (en) * | 1992-03-09 | 1994-11-15 | Abbott Laboratories | Heterocycle-substituted benzyaminopyridine angiotensin II receptor antagonists |
| US5583229A (en) * | 1992-12-07 | 1996-12-10 | Eisai Co., Ltd. | Process for the preparation of imidazopyridine derivatives |
| EP0577025A3 (de) * | 1992-07-01 | 1998-02-04 | Hoechst Aktiengesellschaft | Angiotensin-II-Rezeptorantagonisten zur Behandlung und Prophylaxe von koronaren Herzerkrankungen |
| EP0577023A3 (en) * | 1992-07-01 | 1996-12-18 | Hoechst Ag | Angiotensin-ii receptor-antagonists for the treatment of arrhythmices |
| GB9218449D0 (en) | 1992-08-29 | 1992-10-14 | Boots Co Plc | Therapeutic agents |
| WO1994005633A1 (en) * | 1992-09-01 | 1994-03-17 | Ciba-Geigy Ag | 3-cyano-4-halogeno-2-(subst.phenyl)-pyrroles as pesticides and fungicides |
| DK0664802T3 (da) * | 1992-10-13 | 2000-06-05 | Searle & Co | N-Arylheteroarylalkyl-1-phenyl-imidazol-2-on-forbindelser til behandling af kredsløbssygdomme |
| DE4236026A1 (de) * | 1992-10-24 | 1994-04-28 | Merck Patent Gmbh | Imidazopyridine |
| US5376666A (en) * | 1992-11-30 | 1994-12-27 | The Du Pont Merck Pharmaceutical Company | Angiotension-II receptor blocking, azacycloalkyl or azacycloalkenyl |
| US5455260A (en) * | 1993-05-21 | 1995-10-03 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Aliphatic amino bis-aryl squalene synthase inhibitors |
| US5338740A (en) * | 1993-07-13 | 1994-08-16 | Pfizer Inc. | Angiotensin II receptor antagonists |
| DE69635857T2 (de) * | 1995-06-07 | 2006-10-19 | Nippon Shinyaku Co., Ltd. | Pyrrolderivate und medizinische zusammensetzung |
| EP0994877A1 (en) | 1997-07-03 | 2000-04-26 | Du Pont Pharmaceuticals Company | Imidazopyrimidines and imidazopyridines for the treatment of neurological disorders |
| US6365589B1 (en) | 1998-07-02 | 2002-04-02 | Bristol-Myers Squibb Pharma Company | Imidazo-pyridines, -pyridazines, and -triazines as corticotropin releasing factor antagonists |
| US6124463A (en) * | 1998-07-02 | 2000-09-26 | Dupont Pharmaceuticals | Benzimidazoles as corticotropin release factor antagonists |
| SE9903028D0 (sv) | 1999-08-27 | 1999-08-27 | Astra Ab | New use |
| US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7868037B2 (en) | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US7772271B2 (en) | 2004-07-14 | 2010-08-10 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| US8013006B2 (en) | 2004-07-14 | 2011-09-06 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
| EP1781289A1 (en) | 2004-07-22 | 2007-05-09 | PTC Therapeutics, Inc. | Thienopyridines for treating hepatitis c |
| US7531560B2 (en) * | 2004-11-10 | 2009-05-12 | Boehringer Ingelheim Pharmaceuticals, Inc. | Anti-cytokine heterocyclic compounds |
| PE20070341A1 (es) * | 2005-07-29 | 2007-04-13 | Wyeth Corp | Derivados de pirrol como moduladores del receptor de progesterona |
| PE20070182A1 (es) * | 2005-07-29 | 2007-03-06 | Wyeth Corp | Derivados cianopirrol-fenil amida como moduladores del receptor de progesterona |
| US20100120694A1 (en) | 2008-06-04 | 2010-05-13 | Synergy Pharmaceuticals, Inc. | Agonists of Guanylate Cyclase Useful for the Treatment of Gastrointestinal Disorders, Inflammation, Cancer and Other Disorders |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| EP2527360B1 (en) | 2007-06-04 | 2015-10-28 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
| AR072297A1 (es) | 2008-06-27 | 2010-08-18 | Novartis Ag | Derivados de indol-2-il-piridin-3-ilo, composicion farmaceutica que los comprende y su uso en medicamentos para el tratamiento de enfermedades mediadas por la sintasa aldosterona. |
| ES2624828T3 (es) | 2008-07-16 | 2017-07-17 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| US8703776B2 (en) | 2011-06-15 | 2014-04-22 | Cymabay Therapeutics, Inc. | Agonists of GPR131 and uses thereof |
| WO2013032939A1 (en) * | 2011-08-26 | 2013-03-07 | Metabolex, Inc. | Bicyclic agonists of gpr131 and uses thereof |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| WO2014151206A1 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonists of guanylate cyclase and their uses |
| CA2905242C (en) | 2013-03-15 | 2016-11-29 | Pfizer Inc. | Indole compounds that activate ampk |
| WO2014151200A2 (en) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Compositions useful for the treatment of gastrointestinal disorders |
| US10011637B2 (en) | 2013-06-05 | 2018-07-03 | Synergy Pharmaceuticals, Inc. | Ultra-pure agonists of guanylate cyclase C, method of making and using same |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3130251A1 (de) * | 1981-07-31 | 1983-02-17 | A. Nattermann & Cie GmbH, 5000 Köln | 6-(4-((omega)-(1-imidazolyl)-alkyl)-phenyl)-3-oxo -2,3,4,5-tetrahydro-pyridazine und deren saeureadditionssalze, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| CA1338238C (en) * | 1988-01-07 | 1996-04-09 | David John Carini | Angiotensin ii receptor blocking imidazoles and combinations thereof with diuretics and nsaids |
| US4916129A (en) * | 1989-01-19 | 1990-04-10 | E. I. Du Pont De Nemours And Company | Combination β-blocking/angiotensin II blocking antihypertensives |
| IE64514B1 (en) * | 1989-05-23 | 1995-08-09 | Zeneca Ltd | Azaindenes |
| IL94390A (en) * | 1989-05-30 | 1996-03-31 | Merck & Co Inc | The 6-membered trans-nitrogen-containing heterocycles are compressed with imidazo and pharmaceutical preparations containing them |
| IL96019A0 (en) * | 1989-10-31 | 1991-07-18 | Fujisawa Pharmaceutical Co | Imidazole derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same |
| TW300219B (ko) * | 1991-09-14 | 1997-03-11 | Hoechst Ag |
-
1991
- 1991-08-23 US US07/748,954 patent/US5210092A/en not_active Expired - Fee Related
- 1991-08-30 AU AU83454/91A patent/AU650473B2/en not_active Ceased
- 1991-09-04 FI FI914163A patent/FI914163A/fi not_active Application Discontinuation
- 1991-09-08 IL IL99443A patent/IL99443A0/xx unknown
- 1991-09-09 IE IE316491A patent/IE913164A1/en unknown
- 1991-09-14 EP EP91115644A patent/EP0480204B1/en not_active Expired - Lifetime
- 1991-09-14 DE DE69118082T patent/DE69118082T2/de not_active Expired - Fee Related
- 1991-09-14 AT AT91115644T patent/ATE135701T1/de not_active IP Right Cessation
- 1991-09-24 PT PT99038A patent/PT99038A/pt not_active Application Discontinuation
- 1991-09-24 KR KR1019910016597A patent/KR920006347A/ko not_active Application Discontinuation
- 1991-09-24 CN CN91109182A patent/CN1059723A/zh active Pending
- 1991-09-24 JP JP3317589A patent/JPH04288075A/ja active Pending
- 1991-09-24 NO NO91913750A patent/NO913750L/no unknown
- 1991-09-24 HU HU913052A patent/HUT59404A/hu unknown
- 1991-09-24 CA CA002052125A patent/CA2052125A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| IL99443A0 (en) | 1992-08-18 |
| EP0480204B1 (en) | 1996-03-20 |
| CA2052125A1 (en) | 1992-03-26 |
| IE913164A1 (en) | 1992-02-25 |
| AU650473B2 (en) | 1994-06-23 |
| FI914163A (fi) | 1992-03-26 |
| DE69118082T2 (de) | 1996-10-17 |
| EP0480204A1 (en) | 1992-04-15 |
| US5210092A (en) | 1993-05-11 |
| ATE135701T1 (de) | 1996-04-15 |
| PT99038A (pt) | 1992-08-31 |
| NO913750D0 (no) | 1991-09-24 |
| CN1059723A (zh) | 1992-03-25 |
| NO913750L (no) | 1992-03-26 |
| JPH04288075A (ja) | 1992-10-13 |
| FI914163A0 (fi) | 1991-09-04 |
| DE69118082D1 (de) | 1996-04-25 |
| AU8345491A (en) | 1992-04-02 |
| HU913052D0 (en) | 1992-01-28 |
| HUT59404A (en) | 1992-05-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR920006347A (ko) | 헤테로사이클릭 유도체 | |
| US6143746A (en) | Tetracyclic cyclic GMP-specific phosphodiesterase inhibitors, process of preparation and use | |
| US6143757A (en) | Chemical compounds | |
| US6462047B1 (en) | Carboline derivatives as cGMP phosphodiesterase inhibitors | |
| AU704955B2 (en) | Use of CGMP-phosphodiesterase inhibitors to treat impotence | |
| AU2002253357B2 (en) | Fused pyrimidines as antagonists of the corticotropin releasing factor (crf) | |
| JP6785384B2 (ja) | 新規なヘテロ環化合物、その製造方法およびこれを含む薬学的組成物 | |
| JP2006514980A5 (ko) | ||
| RU95118439A (ru) | Имидазопиридины и способ их получения, фармацевтическая композиция на их основе и способ ее получения | |
| AU775993B2 (en) | Imidazopyridine derivatives as phosphodiesterase VII inhibitors | |
| HRP950023A2 (en) | Tetracyclic derivatives, process of preparation and use | |
| SI9620103A (sl) | Pirolopirimidini in postopki za njihovo pripravo | |
| CN101835776A (zh) | 用于癌症治疗的稠合的咪唑 | |
| JPH05502872A (ja) | 医薬 | |
| WO2000043392A2 (de) | Verwendung von imidazo[1,5-a]-pyrido[3,2-e]-pyrazinonen als arzneimittel | |
| US4457932A (en) | Anti-ulcer agents | |
| US6878711B2 (en) | Indole derivatives as PDE5-inhibitors | |
| PT85455A (de) | Neue substituierte pyrido ]2,3-b" ]1,4" benzodiazepin-6-one verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel | |
| JP4339679B2 (ja) | Ｐｄｅ５阻害剤としてのカルボリン誘導体 | |
| JPH08500587A (ja) | 高脂血症の治療のためのアンジオテンシン▲ｉｉ▼拮抗剤の使用 | |
| DE4131579A1 (de) | Thiadiazolo(4,3-a)pyridinderivate, verfahren zu ihrer herstellung und diese enthaltenden arzneimittel | |
| HUT60500A (en) | Process for producing 3h,6h-1,4,5a,8a-tetraaza-acenaphthylene-3,5-(4h)-diones and 4,5-dihydro-5-mercapto or thioxo-3h,6h-1,4,5a,8a-tetraaza-acenapthylen-3-one derivatives | |
| AU713804B2 (en) | Pyrazolopyrimidines having CRF antagonist activity | |
| DE19961302A1 (de) | Verwendung von Imidazo(1,5-a)-pyrido(3,2-e)-pyrazinonen als duale Inhibitoren der Phosphodiesterase 5 und der Phosphodiesterase 3 zur Therapie der Herzinsuffizienz, von pulmonaler Hypertonie und Gefäßerkrankungen, die mit einer Minderdurchblutung einhergehen | |
| MXPA01007380A (en) | Use of imidazo[1,5-a]-pyrido[3,2-e]-pyrazinones as medicaments |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WITN | Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid |