DE2623314C2 - 1-Aryloxy-2-Hydroxy-3-aminopropane, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel - Google Patents
1-Aryloxy-2-Hydroxy-3-aminopropane, Verfahren zu ihrer Herstellung und diese enthaltende ArzneimittelInfo
- Publication number
- DE2623314C2 DE2623314C2 DE2623314A DE2623314A DE2623314C2 DE 2623314 C2 DE2623314 C2 DE 2623314C2 DE 2623314 A DE2623314 A DE 2623314A DE 2623314 A DE2623314 A DE 2623314A DE 2623314 C2 DE2623314 C2 DE 2623314C2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- acid
- meaning given
- hydroxy
- compound
- 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
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000003814 drug Substances 0.000 title description 2
- 239000002253 acid Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 17
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- -1 alkali metal salt Chemical class 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 75
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000012458 free base Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003849 aromatic solvent Substances 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000002917 oxazolidines Chemical class 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 150000008379 phenol ethers Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
- YONLFQNRGZXBBF-KBPBESRZSA-N (2s,3s)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@H](C(=O)O)[C@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-KBPBESRZSA-N 0.000 description 1
- DIVNUTGTTIRPQA-UHFFFAOYSA-N (3,4-dimethoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1OC DIVNUTGTTIRPQA-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- AFDBKKUOCNDDSN-UHFFFAOYSA-N 1-amino-1-phenoxypropan-2-ol Chemical class CC(O)C(N)OC1=CC=CC=C1 AFDBKKUOCNDDSN-UHFFFAOYSA-N 0.000 description 1
- YDTQAPOROITHCN-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)ethanamine Chemical compound COC1=CC=C(CCN)C(OC)=C1 YDTQAPOROITHCN-UHFFFAOYSA-N 0.000 description 1
- FPWLTKFZPJGKSX-UHFFFAOYSA-N 2-methoxy-2-(3-methoxyphenyl)ethanamine Chemical compound COC(CN)C1=CC=CC(OC)=C1 FPWLTKFZPJGKSX-UHFFFAOYSA-N 0.000 description 1
- IIVWHGMLFGNMOW-UHFFFAOYSA-N 2-methylpropane Chemical compound C[C](C)C IIVWHGMLFGNMOW-UHFFFAOYSA-N 0.000 description 1
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical class O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-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
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 description 1
- LTPVSOCPYWDIFU-UHFFFAOYSA-N 4-methoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1 LTPVSOCPYWDIFU-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
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- 241000416162 Astragalus gummifer Species 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 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
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyridine Compounds (AREA)
Priority Applications (27)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2623314A DE2623314C2 (de) | 1976-05-25 | 1976-05-25 | 1-Aryloxy-2-Hydroxy-3-aminopropane, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| ES458957A ES458957A1 (es) | 1976-05-25 | 1977-05-19 | Procedimiento para la preparacion de nuevos 1-ariloxi-2-hi- droxi-3-aminopropanos. |
| CH624077A CH637105A5 (en) | 1976-05-25 | 1977-05-20 | Process for preparing novel 1-aryloxy-2-hydroxy-3-aminopropanes |
| NL7705587A NL7705587A (nl) | 1976-05-25 | 1977-05-20 | Werkwijze voor het bereiden van 1-aryloxy-2-hy- droxy-3-aminopropanen. |
| IT23892/77A IT1077193B (it) | 1976-05-25 | 1977-05-23 | 1-arilossi-2-idrossi-3-aminopropani e processo per la loro preparazione |
| FI771630A FI67698C (fi) | 1976-05-25 | 1977-05-23 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 1-aryloxi-2-hydroxi-3-aminopropaner |
| CA278,974A CA1108633A (en) | 1976-05-25 | 1977-05-24 | 1-aryloxy-2-hydroxy-3-aminopropanes and process for preparing same |
| AT370177A AT354421B (de) | 1976-05-25 | 1977-05-24 | Verfahren zur herstellung von neuen substituierten 3-(3'-amino-2'-hydroxy- propoxyphenyl)-acrylsaeurederivaten |
| ZA00773120A ZA773120B (en) | 1976-05-25 | 1977-05-24 | Novel 1-aryloxy-2-hydroxy-3-aminopropanes and process for preparing same |
| DK227177A DK227177A (da) | 1976-05-25 | 1977-05-24 | 1-aryloxy-2-hydroxy-3-aminopropaner samt deres fremstilling og anvendelse |
| HU77HO1987A HU179198B (en) | 1976-05-25 | 1977-05-24 | Process for producing new 1-aryloxy-2-hydroxy-3-amino-propane derivatives |
| SE7706059A SE440903B (sv) | 1976-05-25 | 1977-05-24 | Forfarande for framstellning av nya 1-aryloxi-2-hydroxi-3-aminopropaner |
| AU25434/77A AU511704B2 (en) | 1976-05-25 | 1977-05-24 | 1-aryloxy-2-hydroxy-3-aminopropanes |
| IL52148A IL52148A (en) | 1976-05-25 | 1977-05-24 | Substituted 1-phenoxy-2-hydroxy-3-aminopropanes,process for preparing same and pharmaceutical compositions containing them |
| GB22051/77A GB1577670A (en) | 1976-05-25 | 1977-05-25 | 1-aryloxy-2 - hydroxy - 3 - aminopropanes and process for their preparation |
| FR7715881A FR2353520A1 (fr) | 1976-05-25 | 1977-05-25 | 1-aryloxy-2-hydroxy-3-aminopropanes, leur procede de preparation et leurs applications therapeutiques |
| BE177909A BE855041A (fr) | 1976-05-25 | 1977-05-25 | 1-aryloxy-2-hydroxy-3-aminopropanes, leur procede de preparation et leurs applications |
| JP6000477A JPS5312827A (en) | 1976-05-25 | 1977-05-25 | Novell11aryloxyy22hydroxyy33 aminopropane compound and producing the same |
| US05/932,504 US4191765A (en) | 1976-05-25 | 1978-08-10 | 1-Aryloxy-2-hydroxy-3-aminopropanes |
| AT520079A AT368484B (de) | 1976-05-25 | 1979-07-27 | Verfahren zur herstellung von neuen substituierten 3-(3'-amino-2'-hydroxypropoxyphenyl)acryls[urederivaten |
| AT519879A AT367742B (de) | 1976-05-25 | 1979-07-27 | Verfahren zur herstellung von neuen substituierten 3-(3'-amino-2'-hydroxypropoxyphenyl)-acrylsaeure derivaten sowie deren saeureadditionssalzen |
| AT519779A AT367757B (de) | 1976-05-25 | 1979-07-27 | Verfahren zur herstellung von neuen substituierten 3-(3'-amino-2'-hydroxypropoxyphenyl)-acrylsaeure derivaten sowie deren saeureadditionssalzen |
| AT519979A AT367743B (de) | 1976-05-25 | 1979-07-27 | Verfahren zur herstellung von neuen substituierten 3-(3'-amino-2'-hydroxypropoxyphenyl)-acrylsaeure derivaten sowie deren saeureadditionssalzen |
| CH655681A CH637109A5 (en) | 1976-05-25 | 1981-10-13 | Process for preparing novel 1-aryloxy-2-hydroxy-3-aminopropanes |
| CH655781A CH640507A5 (en) | 1976-05-25 | 1981-10-13 | Process for preparing novel 1-aryloxy-2-hydroxy-3-aminopropanes |
| CH655481A CH637107A5 (en) | 1976-05-25 | 1981-10-13 | Process for preparing novel 1-aryloxy-2-hydroxy-3-aminopropanes |
| CH655581A CH637108A5 (en) | 1976-05-25 | 1981-10-13 | Process for preparing novel 1-aryloxy-2-hydroxy-3-aminopropanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2623314A DE2623314C2 (de) | 1976-05-25 | 1976-05-25 | 1-Aryloxy-2-Hydroxy-3-aminopropane, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2623314A1 DE2623314A1 (de) | 1977-12-08 |
| DE2623314C2 true DE2623314C2 (de) | 1984-08-02 |
Family
ID=5978907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2623314A Expired DE2623314C2 (de) | 1976-05-25 | 1976-05-25 | 1-Aryloxy-2-Hydroxy-3-aminopropane, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5312827A (forum.php) |
| AT (1) | AT354421B (forum.php) |
| AU (1) | AU511704B2 (forum.php) |
| BE (1) | BE855041A (forum.php) |
| CA (1) | CA1108633A (forum.php) |
| CH (5) | CH637105A5 (forum.php) |
| DE (1) | DE2623314C2 (forum.php) |
| DK (1) | DK227177A (forum.php) |
| ES (1) | ES458957A1 (forum.php) |
| FI (1) | FI67698C (forum.php) |
| FR (1) | FR2353520A1 (forum.php) |
| GB (1) | GB1577670A (forum.php) |
| HU (1) | HU179198B (forum.php) |
| IL (1) | IL52148A (forum.php) |
| IT (1) | IT1077193B (forum.php) |
| NL (1) | NL7705587A (forum.php) |
| SE (1) | SE440903B (forum.php) |
| ZA (1) | ZA773120B (forum.php) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2415622A1 (fr) * | 1978-01-25 | 1979-08-24 | Lipha | Amino alcools derives de l'ortho-hydroxy cinnamate de methyle applicables notamment comme medicaments |
| DE2824764A1 (de) * | 1978-06-06 | 1979-12-20 | Hoechst Ag | Neue pyridylpiperazinderivate und verfahren zu ihrer herstellung |
| IT1118835B (it) * | 1978-08-15 | 1986-03-03 | Smithkline Corp | Procedimento per introdurre catene laterali di bloccaggio in nuclei aromatici contenenti un gruppo fenolico |
| FR2459235A1 (fr) * | 1979-06-14 | 1981-01-09 | Sanofi Sa | Nouveaux derives de sulfonyl-aniline, leur procede de preparation et leur application therapeutique |
| JPH0629833B2 (ja) * | 1984-06-15 | 1994-04-20 | 株式会社島津製作所 | 疲労試験機 |
| GB8603120D0 (en) * | 1986-02-07 | 1986-03-12 | Pfizer Ltd | Anti-dysrhythmia agents |
| IL146564A0 (en) | 1999-05-24 | 2002-07-25 | Mitsubishi Pharma Corp | Phenoxypropylamine derivatives and pharmaceutical compositions containing the same |
| DE19941657A1 (de) * | 1999-09-01 | 2001-03-08 | Schwabe Willmar Gmbh & Co | Zimtsäurenitrile, Verfahren zu ihrer Herstellung und Verwendung |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA945172A (en) * | 1969-02-21 | 1974-04-09 | Imperial Chemical Industries Limited | Alkanolamine derivatives |
| FR2132570B1 (forum.php) * | 1971-04-09 | 1974-08-02 | Lipha | |
| BE791650R (fr) * | 1971-11-18 | 1973-05-21 | Ici Ltd | Derives d'alkanolamines. |
| ES411826A1 (es) * | 1973-02-20 | 1976-01-01 | Liade Sa Lab | Procedimiento de obtencion de 1-ariloxi - 2 - propanolami- nas farmacologicamente activos. |
-
1976
- 1976-05-25 DE DE2623314A patent/DE2623314C2/de not_active Expired
-
1977
- 1977-05-19 ES ES458957A patent/ES458957A1/es not_active Expired
- 1977-05-20 NL NL7705587A patent/NL7705587A/xx not_active Application Discontinuation
- 1977-05-20 CH CH624077A patent/CH637105A5/de not_active IP Right Cessation
- 1977-05-23 IT IT23892/77A patent/IT1077193B/it active
- 1977-05-23 FI FI771630A patent/FI67698C/fi not_active IP Right Cessation
- 1977-05-24 AU AU25434/77A patent/AU511704B2/en not_active Expired
- 1977-05-24 AT AT370177A patent/AT354421B/de not_active IP Right Cessation
- 1977-05-24 SE SE7706059A patent/SE440903B/xx unknown
- 1977-05-24 DK DK227177A patent/DK227177A/da not_active Application Discontinuation
- 1977-05-24 HU HU77HO1987A patent/HU179198B/hu unknown
- 1977-05-24 CA CA278,974A patent/CA1108633A/en not_active Expired
- 1977-05-24 IL IL52148A patent/IL52148A/xx unknown
- 1977-05-24 ZA ZA00773120A patent/ZA773120B/xx unknown
- 1977-05-25 JP JP6000477A patent/JPS5312827A/ja active Granted
- 1977-05-25 FR FR7715881A patent/FR2353520A1/fr active Granted
- 1977-05-25 BE BE177909A patent/BE855041A/xx unknown
- 1977-05-25 GB GB22051/77A patent/GB1577670A/en not_active Expired
-
1981
- 1981-10-13 CH CH655581A patent/CH637108A5/de not_active IP Right Cessation
- 1981-10-13 CH CH655781A patent/CH640507A5/de not_active IP Right Cessation
- 1981-10-13 CH CH655681A patent/CH637109A5/de not_active IP Right Cessation
- 1981-10-13 CH CH655481A patent/CH637107A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HU179198B (en) | 1982-09-28 |
| AT354421B (de) | 1979-01-10 |
| JPS5312827A (en) | 1978-02-04 |
| JPS6214545B2 (forum.php) | 1987-04-02 |
| SE7706059L (sv) | 1977-11-26 |
| IL52148A0 (en) | 1977-07-31 |
| SE440903B (sv) | 1985-08-26 |
| ZA773120B (en) | 1978-04-26 |
| AU511704B2 (en) | 1980-09-04 |
| FI67698C (fi) | 1985-05-10 |
| GB1577670A (en) | 1980-10-29 |
| DK227177A (da) | 1977-11-26 |
| AU2543477A (en) | 1978-11-30 |
| BE855041A (fr) | 1977-11-25 |
| NL7705587A (nl) | 1977-11-29 |
| CH637107A5 (en) | 1983-07-15 |
| FI67698B (fi) | 1985-01-31 |
| CH637109A5 (en) | 1983-07-15 |
| IL52148A (en) | 1982-07-30 |
| FR2353520A1 (fr) | 1977-12-30 |
| IT1077193B (it) | 1985-05-04 |
| ES458957A1 (es) | 1978-07-16 |
| FI771630A7 (forum.php) | 1977-11-26 |
| CH637108A5 (en) | 1983-07-15 |
| ATA370177A (de) | 1979-06-15 |
| FR2353520B1 (forum.php) | 1980-07-25 |
| CH640507A5 (en) | 1984-01-13 |
| CA1108633A (en) | 1981-09-08 |
| DE2623314A1 (de) | 1977-12-08 |
| CH637105A5 (en) | 1983-07-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8125 | Change of the main classification |
Ipc: C07C121/70 |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8320 | Willingness to grant licences declared (paragraph 23) | ||
| 8339 | Ceased/non-payment of the annual fee |