JPS6312871B2 - - Google Patents
Info
- Publication number
- JPS6312871B2 JPS6312871B2 JP59123892A JP12389284A JPS6312871B2 JP S6312871 B2 JPS6312871 B2 JP S6312871B2 JP 59123892 A JP59123892 A JP 59123892A JP 12389284 A JP12389284 A JP 12389284A JP S6312871 B2 JPS6312871 B2 JP S6312871B2
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- methoxy
- hydrogen
- substd
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 14
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 7
- 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 description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- -1 ethylenedioxy Chemical group 0.000 abstract description 17
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
- 125000002252 acyl group Chemical group 0.000 abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 3
- 125000004983 dialkoxyalkyl group Chemical group 0.000 abstract description 3
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract description 2
- 230000001077 hypotensive effect Effects 0.000 abstract description 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 230000000172 allergic effect Effects 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 208000010668 atopic eczema Diseases 0.000 abstract 1
- 229940124630 bronchodilator Drugs 0.000 abstract 1
- 239000000168 bronchodilator agent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RUUDFUZVWHZDGD-UHFFFAOYSA-N 2-(6,7-dimethoxy-3,4-dihydro-2h-isoquinolin-1-ylidene)acetamide Chemical compound C1CNC(=CC(N)=O)C2=C1C=C(OC)C(OC)=C2 RUUDFUZVWHZDGD-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- INHWRYCGDHWSFQ-UHFFFAOYSA-N 9,10-dimethoxy-3-propan-2-yl-6,7-dihydropyrimido[6,1-a]isoquinoline-2,4-dione Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN2C1=CC(=O)N(C(C)C)C2=O INHWRYCGDHWSFQ-UHFFFAOYSA-N 0.000 description 1
- HLTDPZGESWXQLF-UHFFFAOYSA-N 9,10-dimethoxy-6,7-dihydropyrimido[6,1-a]isoquinoline-2,4-dione Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN2C1=CC(=O)NC2=O HLTDPZGESWXQLF-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910001502 inorganic halide Inorganic materials 0.000 description 1
- 229910052945 inorganic sulfide Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- A61P37/08—Antiallergic agents
-
- 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
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- 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
- C07D491/12—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 three hetero rings
- C07D491/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650905—Six-membered rings having the nitrogen atoms in the positions 1 and 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772720085 DE2720085A1 (de) | 1977-05-05 | 1977-05-05 | Pyrimido(6,1-a)isochinolin-2-on- derivate |
| DE2720085.7 | 1977-05-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6041677A JPS6041677A (ja) | 1985-03-05 |
| JPS6312871B2 true JPS6312871B2 (en, 2012) | 1988-03-23 |
Family
ID=6008073
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13845577A Granted JPS53137997A (en) | 1977-05-05 | 1977-11-19 | Pyrimido*6*11a*isoquinolinee22one derivative |
| JP59123892A Granted JPS6041677A (ja) | 1977-05-05 | 1984-06-18 | ピリミド（６，１−ａ）イソキノリン−２，４−ジオン誘導体およびその製法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13845577A Granted JPS53137997A (en) | 1977-05-05 | 1977-11-19 | Pyrimido*6*11a*isoquinolinee22one derivative |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US4482556A (en, 2012) |
| JP (2) | JPS53137997A (en, 2012) |
| AT (1) | AT372383B (en, 2012) |
| BE (1) | BE862785A (en, 2012) |
| CH (2) | CH640854A5 (en, 2012) |
| DK (2) | DK158789C (en, 2012) |
| EG (1) | EG12982A (en, 2012) |
| ES (3) | ES464776A1 (en, 2012) |
| FI (1) | FI64370C (en, 2012) |
| FR (1) | FR2389623B1 (en, 2012) |
| GR (1) | GR72114B (en, 2012) |
| IL (1) | IL53336A (en, 2012) |
| IT (1) | IT1192252B (en, 2012) |
| NL (1) | NL185078C (en, 2012) |
| NO (2) | NO148032C (en, 2012) |
| PT (1) | PT67265B (en, 2012) |
| SE (2) | SE436357B (en, 2012) |
| ZA (1) | ZA776706B (en, 2012) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2847693A1 (de) * | 1978-11-03 | 1980-05-22 | Hoechst Ag | Verfahren zur herstellung von pyrimido-(6,1-a)-isochinolin-2-onen |
| FR2470130A2 (fr) * | 1979-11-21 | 1981-05-29 | Hoechst Ag | Derives de pyrimido (6,1-a) isoquinoleine-4-one, leur procede de preparation et leur application en therapeutique |
| DE3135831A1 (de) * | 1981-09-10 | 1983-04-28 | Hoechst Ag, 6230 Frankfurt | 9,10-substituierte 2-mesitylimino-3-alkyl-3,4,6,7-tetrahydro-2h-pyrimido(6,1-a)isochinolin-4-one, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| CA1237429A (en) * | 1983-05-05 | 1988-05-31 | Frank Kienzle | Pyrimidone derivatives |
| DE3816995A1 (de) * | 1988-05-19 | 1989-11-23 | Hoechst Ag | Verwendung von pyrimido-(6,1-a)-isochinolin-4-on-derivaten und medizinische zubereitungen auf basis dieser verbindungen |
| DE68902811D1 (de) * | 1988-11-19 | 1992-10-15 | Hoechst Ag | Pharmazeutische zusammensetzungen mit einem gehalt an labdan-di-terpenoid-derivaten und pyrimido(6,1-a)isochinolin-4-on-derivaten und ihre anwendung. |
| BRPI0009446B8 (pt) * | 1999-03-31 | 2021-05-25 | Rhinopharma Ltd | composto derivado de pirimido [6,1-a] isoquinolin-4-ona, processo para preparar p mesmo, composição, e, uso de um composto |
| JP2007525475A (ja) * | 2003-07-08 | 2007-09-06 | スミスクライン・ビーチャム・コーポレイション | 新規化学化合物 |
| CN101671336B (zh) | 2009-09-23 | 2013-11-13 | 辽宁利锋科技开发有限公司 | 芳杂环并嘧啶衍生物和类似物及其制备方法和用途 |
| GB201613054D0 (en) | 2016-07-28 | 2016-09-14 | Verona Pharma Plc | New compound and process |
| US11993596B2 (en) * | 2018-07-13 | 2024-05-28 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Fused tri-cyclic compound as PDE3/PDE4 dual inhibitor |
| WO2021143841A1 (zh) * | 2020-01-15 | 2021-07-22 | 正大天晴药业集团股份有限公司 | 三并环类pde3/pde4双重抑制剂化合物的药物组合物 |
| EP4092022A4 (en) * | 2020-01-15 | 2024-01-24 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | DOUBLE PDE3/PDE4 INHIBITOR CRYSTAL AND USE THEREOF |
| CA3211820A1 (en) * | 2021-04-29 | 2022-11-03 | Zhiya LI | Isoquinolone compound and use thereof |
| GB202202297D0 (en) | 2022-02-21 | 2022-04-06 | Verona Pharma Plc | Formulation production process |
| KR20250095708A (ko) * | 2022-10-28 | 2025-06-26 | 지앙수 헨그루이 파마슈티컬스 컴퍼니 리미티드 | 이소퀴놀리논계 화합물의 결정형 및 이의 제조 방법 |
| TW202506117A (zh) | 2023-06-26 | 2025-02-16 | 英商維羅納製藥Ｐｌｃ公司 | 顆粒組成物 |
| CN118955496A (zh) * | 2023-06-28 | 2024-11-15 | 郑州德迈药业有限公司 | 一种化合物及其应用 |
| CN120136868A (zh) * | 2023-12-13 | 2025-06-13 | 石家庄以岭药业股份有限公司 | 三环稠杂环类pde3/4双重抑制剂及其制备方法与应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3021331A (en) * | 1959-07-20 | 1962-02-13 | Pfizer & Co C | Azabenzopyridocolines |
| US3081306A (en) * | 1959-11-04 | 1963-03-12 | Pfizer & Co C | 2, 4-dioxo-3-aralkylaza-9, 10-di(lower alkoxy)-1, 2, 3, 4, 6, 7-hexahydro-11b-h-benzopyridocolines |
| US3297696A (en) * | 1965-05-28 | 1967-01-10 | Sandoz Ag | 6-amino-8, 9-dihydro-13bh-isoquinolo-[2, 1-c] quinazolines and intermediates therefor |
| DE2126148A1 (en) * | 1971-05-26 | 1972-12-07 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Prepn of uracil derivs - useful as plant - protection agents and their inters |
| DE2847693A1 (de) * | 1978-11-03 | 1980-05-22 | Hoechst Ag | Verfahren zur herstellung von pyrimido-(6,1-a)-isochinolin-2-onen |
| US5740368A (en) * | 1995-06-30 | 1998-04-14 | Canon Kabushiki Kaisha | Method and apparatus for providing information on a managed peripheral device to plural agents |
-
1977
- 1977-11-02 FI FI773286A patent/FI64370C/fi not_active IP Right Cessation
- 1977-11-03 AT AT0784477A patent/AT372383B/de active
- 1977-11-03 DK DK489477A patent/DK158789C/da active
- 1977-11-04 SE SE7712513A patent/SE436357B/sv not_active IP Right Cessation
- 1977-11-08 IL IL53336A patent/IL53336A/xx unknown
- 1977-11-09 ZA ZA00776706A patent/ZA776706B/xx unknown
- 1977-11-11 PT PT67265A patent/PT67265B/pt unknown
- 1977-11-19 JP JP13845577A patent/JPS53137997A/ja active Granted
- 1977-12-02 NO NO774131A patent/NO148032C/no unknown
- 1977-12-06 ES ES464776A patent/ES464776A1/es not_active Expired
- 1977-12-10 EG EG680/77A patent/EG12982A/xx active
-
1978
- 1978-01-01 CH CH1331977A patent/CH640854A5/de not_active IP Right Cessation
- 1978-01-05 NL NLAANVRAGE7800149,A patent/NL185078C/xx not_active IP Right Cessation
- 1978-01-10 BE BE184225A patent/BE862785A/xx not_active IP Right Cessation
- 1978-02-02 FR FR7802935A patent/FR2389623B1/fr not_active Expired
- 1978-03-14 GR GR55702A patent/GR72114B/el unknown
- 1978-04-21 IT IT22619/78A patent/IT1192252B/it active
- 1978-08-16 ES ES472606A patent/ES472606A1/es not_active Expired
- 1978-10-19 CH CH1084178A patent/CH642949A5/de not_active IP Right Cessation
- 1978-11-13 ES ES475027A patent/ES475027A1/es not_active Expired
-
1980
- 1980-03-26 US US06/134,080 patent/US4482556A/en not_active Expired - Lifetime
-
1982
- 1982-04-19 NO NO821266A patent/NO821266L/no unknown
- 1982-11-19 SE SE8206619A patent/SE439307B/sv not_active IP Right Cessation
-
1984
- 1984-06-18 JP JP59123892A patent/JPS6041677A/ja active Granted
- 1984-09-19 US US06/652,005 patent/US4598148A/en not_active Expired - Lifetime
-
1989
- 1989-06-01 DK DK267089A patent/DK267089D0/da not_active Application Discontinuation
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