DE2639291C2 - - Google Patents
Info
- Publication number
- DE2639291C2 DE2639291C2 DE2639291A DE2639291A DE2639291C2 DE 2639291 C2 DE2639291 C2 DE 2639291C2 DE 2639291 A DE2639291 A DE 2639291A DE 2639291 A DE2639291 A DE 2639291A DE 2639291 C2 DE2639291 C2 DE 2639291C2
- Authority
- DE
- Germany
- Prior art keywords
- compound
- formula
- methyl
- dimethoxy
- ethyl
- 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
- 150000001875 compounds Chemical class 0.000 claims description 15
- -1 2- (3,4-dimethoxyphenyl) ethyl Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- BBLCECBCCPOOEX-UHFFFAOYSA-N 2-(3-chloropropyl)-6,7-dimethoxy-4-methylphthalazin-1-one Chemical compound CC1=NN(CCCCl)C(=O)C2=C1C=C(OC)C(OC)=C2 BBLCECBCCPOOEX-UHFFFAOYSA-N 0.000 description 3
- YFQJMKXVBQBYMC-UHFFFAOYSA-N 2-[3-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]propyl]-6,7-dimethoxy-4-methylphthalazin-1-one;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CCN(C)CCCN1C(=O)C2=CC(OC)=C(OC)C=C2C(C)=N1 YFQJMKXVBQBYMC-UHFFFAOYSA-N 0.000 description 3
- LZSMTBAWOWDVII-UHFFFAOYSA-N 6,7-dimethoxy-4-methyl-2h-phthalazin-1-one Chemical compound CC1=NNC(=O)C2=C1C=C(OC)C(OC)=C2 LZSMTBAWOWDVII-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 150000007530 organic bases Chemical group 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- UMSVPCYSAUKCAZ-UHFFFAOYSA-N propane;hydrochloride Chemical compound Cl.CCC UMSVPCYSAUKCAZ-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- SGEYIHMBOLZAFG-UHFFFAOYSA-N 2-[3-[benzyl-[2-(3,4-dimethoxyphenyl)ethyl]amino]propyl]-6,7-dimethoxy-4-methylphthalazin-1-one Chemical compound C1=C(OC)C(OC)=CC=C1CCN(CC=1C=CC=CC=1)CCCN1C(=O)C2=CC(OC)=C(OC)C=C2C(C)=N1 SGEYIHMBOLZAFG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DOQPXTMNIUCOSY-UHFFFAOYSA-N [4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexyl]-[2-(3,4-dimethoxyphenyl)ethyl]-methylazanium;chloride Chemical compound [H+].[Cl-].C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 DOQPXTMNIUCOSY-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HNJWKRMESUMDQE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-methylethanamine Chemical compound CNCCC1=CC=C(OC)C(OC)=C1 HNJWKRMESUMDQE-UHFFFAOYSA-N 0.000 description 1
- FDKHQZNETKRPQZ-UHFFFAOYSA-N 2-[3-[2-(3,4-dimethoxyphenyl)ethylamino]propyl]-7-methoxy-4,4-dimethylisoquinoline-1,3-dione;hydrochloride Chemical compound Cl.C=1C(OC)=CC=C(C(C2=O)(C)C)C=1C(=O)N2CCCNCCC1=CC=C(OC)C(OC)=C1 FDKHQZNETKRPQZ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 206010052895 Coronary artery insufficiency Diseases 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229940088024 isoptin Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- YKCAEQUWYQHAPP-UHFFFAOYSA-N n-benzyl-2-(3,4-dimethoxyphenyl)ethanamine Chemical compound C1=C(OC)C(OC)=CC=C1CCNCC1=CC=CC=C1 YKCAEQUWYQHAPP-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229960000881 verapamil hydrochloride Drugs 0.000 description 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
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- 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
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Electroluminescent Light Sources (AREA)
- Testing Or Measuring Of Semiconductors Or The Like (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Priority Applications (39)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762639291 DE2639291A1 (de) | 1976-09-01 | 1976-09-01 | Neue aryl-alkylamine |
| FI772261A FI63025C (fi) | 1976-09-01 | 1977-07-22 | Foerfarande foer framstaellning av blodtrycket och hjaertats slagfrekvens saenkande arylalkylaminer |
| DK367077A DK148684C (da) | 1976-09-01 | 1977-08-17 | Analogifremgangsmaade til fremstilling af aryl-alkylaminer |
| AT600577A AT350058B (de) | 1976-09-01 | 1977-08-19 | Verfahren zur herstellung neuer phthalazinon- und chinazolinonaralkylamine und deren salzen |
| US05/827,142 US4134980A (en) | 1976-09-01 | 1977-08-24 | Phenylalkylamino-alkyl derivatives of quinazolinone and phthalazinone |
| SU772513754A SU665802A3 (ru) | 1976-09-01 | 1977-08-25 | Способ получени арилалкиламинов или их солей |
| PH20176A PH13994A (en) | 1976-09-01 | 1977-08-29 | Phenylalkylamino-alxyl derivatives of quinazolinone and phthalazinone |
| BG037253A BG31378A3 (bg) | 1976-09-01 | 1977-08-29 | Метод за получаване на арилалкиламини |
| PT66975A PT66975B (de) | 1976-09-01 | 1977-08-30 | Neue aryl-alkylamine |
| DD77200803A DD133945A5 (de) | 1976-09-01 | 1977-08-30 | Verfahren zur herstellung neuer aryl-alkylamine |
| CS775663A CS197299B2 (en) | 1976-09-01 | 1977-08-30 | Method of producing the new 1-(quinazolinon-2-yl and phthalazinon-2-yl)alkylamines |
| LU78049A LU78049A1 (en:Method) | 1976-09-01 | 1977-08-30 | |
| IL52853A IL52853A (en) | 1976-09-01 | 1977-08-30 | Phenethylaminoalkyl phthalazinones and quinoxalinones,their preparation and pharmaceutical compositions containing them |
| ZA00775262A ZA775262B (en) | 1976-09-01 | 1977-08-31 | Aryl-alkylamines |
| RO7791508A RO73286A (ro) | 1976-09-01 | 1977-08-31 | Procedeu pentru prepararea unor noi aril-alchilamine |
| NO773010A NO147911C (no) | 1976-09-01 | 1977-08-31 | Analogifremgangsmaate for fremstilling av fysiologisk aktive kinazolinon- og ftalazinon-derivater som er substituert med en substituert n-fenylalkylaminoalkylrest |
| NZ185061A NZ185061A (en) | 1976-09-01 | 1977-08-31 | N-phenethyl-w (1-oxo-1,2-dihydrophthalazin-2-yl or 4-oxo-3,4-dihydroquinazolin-3-yl)-alkylamines |
| IE1816/77A IE45672B1 (en) | 1976-09-01 | 1977-08-31 | Substituted aminoalkyl phthalazinones and quinazolinones |
| NL7709577A NL7709577A (nl) | 1976-09-01 | 1977-08-31 | Werkwijze ter bereiding van nieuwe arylalkyl- aminen. |
| ES462005A ES462005A1 (es) | 1976-09-01 | 1977-08-31 | Procedimiento para la preparacion de nuevas aril-alcohilami-nas. |
| PL1977200570A PL103691B1 (pl) | 1976-09-01 | 1977-08-31 | Sposob wytwarzania nowych aryloalkiloamin |
| AU28424/77A AU513302B2 (en) | 1976-09-01 | 1977-08-31 | Substituted aminoalkyl phthalaziinones and quinazolinones |
| BE180604A BE858309A (fr) | 1976-09-01 | 1977-08-31 | Nouvelles aryl-alkylamines |
| PL1977207921A PL103564B1 (pl) | 1976-09-01 | 1977-08-31 | Sposob wytwarzania nowych aryloalkiloamin |
| JP10371277A JPS5331685A (en) | 1976-09-01 | 1977-08-31 | Production of novel aryll alkylamines |
| CA285,893A CA1085838A (en) | 1976-09-01 | 1977-08-31 | Aryl-alkylamines |
| HU77TO1059A HU175549B (en) | 1976-09-01 | 1977-08-31 | Process for producing new aryl-alkylamines containing substituents of heterocyclic rings with a nitrogen as hetero atom |
| GB36376/77A GB1544880A (en) | 1976-09-01 | 1977-08-31 | Substituted aminoalkyl phthalazinones and quinazolinones |
| SE7709816A SE442866B (sv) | 1976-09-01 | 1977-08-31 | Forfarande for framstellning av nya arylalkylaminer |
| FR7726565A FR2363564A1 (fr) | 1976-09-01 | 1977-09-01 | Nouvelles aryl-alkylamines, leur preparation et leur utilisation en tant que medicaments |
| GR54279A GR63624B (en) | 1976-09-01 | 1977-09-01 | Process for preparation of new aryl-alkylamine |
| ES465561A ES465561A1 (es) | 1976-09-01 | 1977-12-29 | Procedimiento para la preparacion de nuevas aril-alcohilami-nas. |
| ES465562A ES465562A1 (es) | 1976-09-01 | 1977-12-29 | Procedimiento para la preparacion de nuevas aril-alcohilami-nas. |
| ES465560A ES465560A1 (es) | 1976-09-01 | 1977-12-29 | Procedimiento para la preparacion de nuevas aril-alcohilami-nas. |
| AT429078A AT351039B (de) | 1976-09-01 | 1978-06-13 | Verfahren zur herstellung neuer phthalazinon- und chinazolinonaralkylamine und deren salzen |
| AT429178A AT351040B (de) | 1976-09-01 | 1978-06-13 | Verfahren zur herstellung neuer phtalazinon- und chinazolinonaralkylamine und deren salzen |
| SU782627806A SU837323A3 (ru) | 1976-09-01 | 1978-06-21 | Способ получени фталазинон- илиХиНАзОлиНОНАРАлКилАМиНОВ или иХ СОлЕй |
| HK335/82A HK33582A (en) | 1976-09-01 | 1982-07-22 | Substituted aminoakyl phthalazinones and quinazolinones |
| MY57/83A MY8300057A (en) | 1976-09-01 | 1983-12-30 | Substituted aminoazkyl phithalazinones and quinazolinones |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762639291 DE2639291A1 (de) | 1976-09-01 | 1976-09-01 | Neue aryl-alkylamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2639291A1 DE2639291A1 (de) | 1978-03-02 |
| DE2639291C2 true DE2639291C2 (en:Method) | 1987-05-27 |
Family
ID=5986872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762639291 Granted DE2639291A1 (de) | 1976-09-01 | 1976-09-01 | Neue aryl-alkylamine |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4134980A (en:Method) |
| JP (1) | JPS5331685A (en:Method) |
| AT (1) | AT350058B (en:Method) |
| AU (1) | AU513302B2 (en:Method) |
| BE (1) | BE858309A (en:Method) |
| BG (1) | BG31378A3 (en:Method) |
| CA (1) | CA1085838A (en:Method) |
| CS (1) | CS197299B2 (en:Method) |
| DD (1) | DD133945A5 (en:Method) |
| DE (1) | DE2639291A1 (en:Method) |
| DK (1) | DK148684C (en:Method) |
| ES (4) | ES462005A1 (en:Method) |
| FI (1) | FI63025C (en:Method) |
| FR (1) | FR2363564A1 (en:Method) |
| GB (1) | GB1544880A (en:Method) |
| GR (1) | GR63624B (en:Method) |
| HK (1) | HK33582A (en:Method) |
| HU (1) | HU175549B (en:Method) |
| IE (1) | IE45672B1 (en:Method) |
| IL (1) | IL52853A (en:Method) |
| LU (1) | LU78049A1 (en:Method) |
| MY (1) | MY8300057A (en:Method) |
| NL (1) | NL7709577A (en:Method) |
| NO (1) | NO147911C (en:Method) |
| NZ (1) | NZ185061A (en:Method) |
| PH (1) | PH13994A (en:Method) |
| PL (2) | PL103691B1 (en:Method) |
| PT (1) | PT66975B (en:Method) |
| RO (1) | RO73286A (en:Method) |
| SE (1) | SE442866B (en:Method) |
| SU (2) | SU665802A3 (en:Method) |
| ZA (1) | ZA775262B (en:Method) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8609331D0 (en) * | 1986-04-16 | 1986-05-21 | Pfizer Ltd | Anti-arrythmia agents |
| IT1222867B (it) * | 1987-10-12 | 1990-09-12 | Zambon Spa | Ftalazino derivati ad attivita' farmaceutica |
| IT1229118B (it) * | 1988-07-29 | 1991-07-22 | Simes | Composti attivi sul sistema cardiovascolare che presentano sia la struttura dei beta-bloccanti sia una porzione calcio-antagonista |
| JP6895002B1 (ja) | 2020-05-27 | 2021-06-30 | ウィンボンド エレクトロニクス コーポレーション | 半導体記憶装置および読出し方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2020234A1 (de) * | 1970-04-25 | 1971-11-18 | Cassella Farbwerke Mainkur Ag | Basisch substituierte Derivate des 4(3H)-Chinazolinons |
| US3829420A (en) * | 1970-07-13 | 1974-08-13 | Sumitomo Chemical Co | 3,4-dihydro-2(1h)-quinazolinones and preparation thereof |
| US3905976A (en) * | 1971-11-24 | 1975-09-16 | Sandoz Ag | Substituted tricyclic quinazolinones |
-
1976
- 1976-09-01 DE DE19762639291 patent/DE2639291A1/de active Granted
-
1977
- 1977-07-22 FI FI772261A patent/FI63025C/fi not_active IP Right Cessation
- 1977-08-17 DK DK367077A patent/DK148684C/da active
- 1977-08-19 AT AT600577A patent/AT350058B/de not_active IP Right Cessation
- 1977-08-24 US US05/827,142 patent/US4134980A/en not_active Expired - Lifetime
- 1977-08-25 SU SU772513754A patent/SU665802A3/ru active
- 1977-08-29 PH PH20176A patent/PH13994A/en unknown
- 1977-08-29 BG BG037253A patent/BG31378A3/bg unknown
- 1977-08-30 PT PT66975A patent/PT66975B/pt unknown
- 1977-08-30 DD DD77200803A patent/DD133945A5/xx unknown
- 1977-08-30 IL IL52853A patent/IL52853A/xx unknown
- 1977-08-30 CS CS775663A patent/CS197299B2/cs unknown
- 1977-08-30 LU LU78049A patent/LU78049A1/xx unknown
- 1977-08-31 JP JP10371277A patent/JPS5331685A/ja active Granted
- 1977-08-31 CA CA285,893A patent/CA1085838A/en not_active Expired
- 1977-08-31 PL PL1977200570A patent/PL103691B1/pl unknown
- 1977-08-31 IE IE1816/77A patent/IE45672B1/en unknown
- 1977-08-31 NL NL7709577A patent/NL7709577A/xx not_active Application Discontinuation
- 1977-08-31 ES ES462005A patent/ES462005A1/es not_active Expired
- 1977-08-31 HU HU77TO1059A patent/HU175549B/hu unknown
- 1977-08-31 BE BE180604A patent/BE858309A/xx not_active IP Right Cessation
- 1977-08-31 ZA ZA00775262A patent/ZA775262B/xx unknown
- 1977-08-31 AU AU28424/77A patent/AU513302B2/en not_active Expired
- 1977-08-31 RO RO7791508A patent/RO73286A/ro unknown
- 1977-08-31 NZ NZ185061A patent/NZ185061A/xx unknown
- 1977-08-31 SE SE7709816A patent/SE442866B/xx not_active IP Right Cessation
- 1977-08-31 GB GB36376/77A patent/GB1544880A/en not_active Expired
- 1977-08-31 NO NO773010A patent/NO147911C/no unknown
- 1977-08-31 PL PL1977207921A patent/PL103564B1/pl unknown
- 1977-09-01 GR GR54279A patent/GR63624B/el unknown
- 1977-09-01 FR FR7726565A patent/FR2363564A1/fr active Granted
- 1977-12-29 ES ES465560A patent/ES465560A1/es not_active Expired
- 1977-12-29 ES ES465561A patent/ES465561A1/es not_active Expired
- 1977-12-29 ES ES465562A patent/ES465562A1/es not_active Expired
-
1978
- 1978-06-21 SU SU782627806A patent/SU837323A3/ru active
-
1982
- 1982-07-22 HK HK335/82A patent/HK33582A/xx unknown
-
1983
- 1983-12-30 MY MY57/83A patent/MY8300057A/xx unknown
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| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |