NO309378B1 - Kondenserte pyridazinforbindelser og anvendelser derav ved fremstilling av medikamenter - Google Patents
Kondenserte pyridazinforbindelser og anvendelser derav ved fremstilling av medikamenter Download PDFInfo
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- NO309378B1 NO309378B1 NO19961397A NO961397A NO309378B1 NO 309378 B1 NO309378 B1 NO 309378B1 NO 19961397 A NO19961397 A NO 19961397A NO 961397 A NO961397 A NO 961397A NO 309378 B1 NO309378 B1 NO 309378B1
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- chloro
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- 238000004519 manufacturing process Methods 0.000 title description 23
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- HJFQNCKHSWFYEF-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-4,6-dichlorophthalazin-1-amine Chemical compound C1=C2OCOC2=CC(CNC=2C3=CC=C(C=C3C(Cl)=NN=2)Cl)=C1 HJFQNCKHSWFYEF-UHFFFAOYSA-N 0.000 description 1
- NXFKRDZHUDGELZ-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-4,7-dichlorophthalazin-1-amine Chemical compound C1=C2OCOC2=CC(CNC2=NN=C(Cl)C3=CC=C(C=C32)Cl)=C1 NXFKRDZHUDGELZ-UHFFFAOYSA-N 0.000 description 1
- RUWRDTSQEVSUNK-UHFFFAOYSA-N n-(1,3-benzodioxol-5-ylmethyl)-4-chloro-6-nitrophthalazin-1-amine Chemical compound C1=C2OCOC2=CC(CNC=2C3=CC=C(C=C3C(Cl)=NN=2)[N+](=O)[O-])=C1 RUWRDTSQEVSUNK-UHFFFAOYSA-N 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- WTYSCLHDMXBMKM-UHFFFAOYSA-N phthalazin-1-amine Chemical compound C1=CC=C2C(N)=NN=CC2=C1 WTYSCLHDMXBMKM-UHFFFAOYSA-N 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
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- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical class C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 206010040560 shock Diseases 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
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- 239000005720 sucrose Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YJESYFAMYFNOGE-UHFFFAOYSA-N tert-butyl 2-[4-[(3-chloro-4-methoxyphenyl)methylamino]-6-cyano-1-oxophthalazin-2-yl]acetate Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NN(CC(=O)OC(C)(C)C)C(=O)C2=CC=C(C#N)C=C12 YJESYFAMYFNOGE-UHFFFAOYSA-N 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- FUYBPBOHNIHCHM-UHFFFAOYSA-N tert-butyl piperidine-4-carboxylate Chemical compound CC(C)(C)OC(=O)C1CCNCC1 FUYBPBOHNIHCHM-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 239000012929 tonicity agent Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/34—Phthalazines with nitrogen atoms directly attached to carbon atoms of the nitrogen-containing ring, e.g. hydrazine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- 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
- C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D401/14—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 three or more hetero rings
-
- 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
- C07D403/02—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 two hetero rings
- C07D403/04—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 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
- C07D403/02—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 two hetero rings
- C07D403/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP18712894 | 1994-08-09 | ||
JP31633794 | 1994-12-20 | ||
PCT/JP1995/001575 WO1996005176A1 (fr) | 1994-08-09 | 1995-08-08 | Compose de pyridazine condense |
Publications (3)
Publication Number | Publication Date |
---|---|
NO961397D0 NO961397D0 (no) | 1996-04-09 |
NO961397L NO961397L (no) | 1996-06-06 |
NO309378B1 true NO309378B1 (no) | 2001-01-22 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO19961397A NO309378B1 (no) | 1994-08-09 | 1996-04-09 | Kondenserte pyridazinforbindelser og anvendelser derav ved fremstilling av medikamenter |
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Country | Link |
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US (2) | US5849741A (zh) |
EP (1) | EP0722936B1 (zh) |
KR (1) | KR100189865B1 (zh) |
CN (1) | CN1151136C (zh) |
AT (1) | ATE267174T1 (zh) |
AU (1) | AU705229B2 (zh) |
CA (1) | CA2173493C (zh) |
DE (1) | DE69533057T2 (zh) |
ES (1) | ES2224130T3 (zh) |
FI (1) | FI111841B (zh) |
HU (1) | HU219864B (zh) |
MX (1) | MX9601310A (zh) |
NO (1) | NO309378B1 (zh) |
NZ (1) | NZ290952A (zh) |
WO (1) | WO1996005176A1 (zh) |
Families Citing this family (48)
Publication number | Priority date | Publication date | Assignee | Title |
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WO1998007430A1 (fr) * | 1996-08-20 | 1998-02-26 | Eisai Co., Ltd. | Medicament contre les defaillances de l'erection, renfermant un compose a base de pyridazine fondue |
US6331543B1 (en) | 1996-11-01 | 2001-12-18 | Nitromed, Inc. | Nitrosated and nitrosylated phosphodiesterase inhibitors, compositions and methods of use |
BR9806752A (pt) * | 1997-01-15 | 2000-03-14 | Byk Gulden Lomberg Chem Fab | Ftalazinonas. |
CO4950519A1 (es) * | 1997-02-13 | 2000-09-01 | Novartis Ag | Ftalazinas, preparaciones farmaceuticas que las comprenden y proceso para su preparacion |
ZA9810766B (en) | 1997-11-28 | 1999-05-25 | Mochida Pharm Co Ltd | Novel compounds having cgmp-pde inhibitory activity |
US6380196B1 (en) | 1997-12-15 | 2002-04-30 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Dihydrobenzofurans |
PL339836A1 (en) | 1998-02-19 | 2001-01-02 | Eisai Co Ltd | Phtalazine compounds and therapeutic agents suitable to treat erection disorders |
ITMI981670A1 (it) | 1998-07-21 | 2000-01-21 | Zambon Spa | Derivati ftalazinici inibitori della fosfodiesterasi 4 |
IT1302677B1 (it) | 1998-10-15 | 2000-09-29 | Zambon Spa | Derivati benzazinici inibitori della fosfodiesterasi 4 |
IT1303272B1 (it) | 1998-10-29 | 2000-11-06 | Zambon Spa | Derivati triciclici inibitori della fosfodiesterasi 4 |
CN1161341C (zh) * | 1999-03-22 | 2004-08-11 | 布里斯托尔-迈尔斯斯奎布公司 | cGMP磷酸二酯酶的稠合吡啶并哒嗪抑制剂 |
ES2265929T3 (es) * | 1999-03-30 | 2007-03-01 | Novartis Ag | Derivados de ftalazina para el tratamiento de enfermedades inflamatorias. |
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-
1995
- 1995-08-08 NZ NZ290952A patent/NZ290952A/en not_active IP Right Cessation
- 1995-08-08 AT AT95927990T patent/ATE267174T1/de active
- 1995-08-08 CN CNB951908626A patent/CN1151136C/zh not_active Expired - Fee Related
- 1995-08-08 ES ES95927990T patent/ES2224130T3/es not_active Expired - Lifetime
- 1995-08-08 US US08/619,621 patent/US5849741A/en not_active Expired - Lifetime
- 1995-08-08 EP EP95927990A patent/EP0722936B1/en not_active Expired - Lifetime
- 1995-08-08 CA CA002173493A patent/CA2173493C/en not_active Expired - Fee Related
- 1995-08-08 WO PCT/JP1995/001575 patent/WO1996005176A1/ja active IP Right Grant
- 1995-08-08 HU HU9600933A patent/HU219864B/hu not_active IP Right Cessation
- 1995-08-08 AU AU31919/95A patent/AU705229B2/en not_active Ceased
- 1995-08-08 DE DE69533057T patent/DE69533057T2/de not_active Expired - Lifetime
- 1995-08-08 KR KR1019960701845A patent/KR100189865B1/ko not_active IP Right Cessation
-
1996
- 1996-04-03 FI FI961510A patent/FI111841B/fi not_active IP Right Cessation
- 1996-04-08 MX MX9601310A patent/MX9601310A/es unknown
- 1996-04-09 NO NO19961397A patent/NO309378B1/no not_active IP Right Cessation
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1998
- 1998-09-29 US US09/161,946 patent/US6218392B1/en not_active Expired - Fee Related
Also Published As
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US6218392B1 (en) | 2001-04-17 |
AU3191995A (en) | 1996-03-07 |
DE69533057T2 (de) | 2005-06-16 |
EP0722936B1 (en) | 2004-05-19 |
NZ290952A (en) | 1998-05-27 |
EP0722936A4 (en) | 1996-12-11 |
NO961397D0 (no) | 1996-04-09 |
DE69533057D1 (de) | 2004-06-24 |
AU705229B2 (en) | 1999-05-20 |
ATE267174T1 (de) | 2004-06-15 |
WO1996005176A1 (fr) | 1996-02-22 |
FI961510A0 (fi) | 1996-04-03 |
KR100189865B1 (ko) | 1999-06-01 |
CA2173493A1 (en) | 1996-02-22 |
EP0722936A1 (en) | 1996-07-24 |
FI111841B (fi) | 2003-09-30 |
CN1135210A (zh) | 1996-11-06 |
HUT76067A (en) | 1997-06-30 |
FI961510A (fi) | 1996-05-29 |
KR960704854A (ko) | 1996-10-09 |
HU219864B (hu) | 2001-08-28 |
NO961397L (no) | 1996-06-06 |
CN1151136C (zh) | 2004-05-26 |
ES2224130T3 (es) | 2005-03-01 |
MX9601310A (es) | 1998-11-30 |
US5849741A (en) | 1998-12-15 |
HU9600933D0 (en) | 1996-07-29 |
CA2173493C (en) | 2008-03-25 |
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