IL44301A - 1-Aryloxy-2-Hydroxy-3-Alkylenylamino-propanes and their salts, their manufacture and pharmaceutical preparations containing them - Google Patents
1-Aryloxy-2-Hydroxy-3-Alkylenylamino-propanes and their salts, their manufacture and pharmaceutical preparations containing themInfo
- Publication number
- IL44301A IL44301A IL44301A IL4430174A IL44301A IL 44301 A IL44301 A IL 44301A IL 44301 A IL44301 A IL 44301A IL 4430174 A IL4430174 A IL 4430174A IL 44301 A IL44301 A IL 44301A
- Authority
- IL
- Israel
- Prior art keywords
- group
- formula
- compound
- compounds
- amino
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 40
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims description 140
- 238000000034 method Methods 0.000 claims description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 47
- 239000002253 acid Substances 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 239000004480 active ingredient Substances 0.000 claims description 30
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 24
- -1 cyano, amino Chemical group 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 239000003826 tablet Substances 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 6
- 239000002775 capsule Substances 0.000 claims description 6
- 125000001589 carboacyl group Chemical group 0.000 claims description 6
- 125000001475 halogen functional group Chemical group 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 239000008187 granular material Substances 0.000 claims description 4
- 230000026030 halogenation Effects 0.000 claims description 4
- 238000005658 halogenation reaction Methods 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 238000002347 injection Methods 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 239000000829 suppository Substances 0.000 claims description 3
- 125000004036 acetal group Chemical group 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229940097217 cardiac glycoside Drugs 0.000 claims description 2
- 239000002368 cardiac glycoside Substances 0.000 claims description 2
- 239000003218 coronary vasodilator agent Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 229930002534 steroid glycoside Natural products 0.000 claims description 2
- 239000006188 syrup Substances 0.000 claims description 2
- 235000020357 syrup Nutrition 0.000 claims description 2
- 239000003204 tranquilizing agent Substances 0.000 claims description 2
- 230000002936 tranquilizing effect Effects 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 2
- 230000002140 halogenating effect Effects 0.000 claims 2
- WZIKOBGAODPFQN-UHFFFAOYSA-N 5-amino-1-[2-(hydroxymethyl)phenoxy]-5-methylhept-6-yn-2-ol Chemical compound OCC1=C(OCC(CCC(C#C)(C)N)O)C=CC=C1 WZIKOBGAODPFQN-UHFFFAOYSA-N 0.000 claims 1
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 239000006196 drop Substances 0.000 claims 1
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 claims 1
- 239000006187 pill Substances 0.000 claims 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical group [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 229940125725 tranquilizer Drugs 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- 239000002585 base Substances 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 229960004592 isopropanol Drugs 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- 230000001376 precipitating effect Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000012730 sustained-release form Substances 0.000 description 5
- VUGCBIWQHSRQBZ-UHFFFAOYSA-N 2-methylbut-3-yn-2-amine Chemical compound CC(C)(N)C#C VUGCBIWQHSRQBZ-UHFFFAOYSA-N 0.000 description 4
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 150000002118 epoxides Chemical class 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000013268 sustained release Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
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- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- ILMYGNALXZMVHB-UHFFFAOYSA-N 2-(5-amino-2-hydroxy-5-methylhept-6-ynoxy)-5-chlorobenzonitrile Chemical compound C(#N)C1=C(OCC(CCC(C#C)(C)N)O)C=CC(=C1)Cl ILMYGNALXZMVHB-UHFFFAOYSA-N 0.000 description 2
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- 239000001506 calcium phosphate Substances 0.000 description 2
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- 238000002844 melting Methods 0.000 description 2
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
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- 238000000926 separation method Methods 0.000 description 2
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- 238000005303 weighing Methods 0.000 description 2
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- 235000010489 acacia gum Nutrition 0.000 description 1
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- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
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- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
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- 229960005150 glycerol Drugs 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- QYRFJLLXPINATB-UHFFFAOYSA-N hydron;2,4,5,6-tetrafluorobenzene-1,3-diamine;dichloride Chemical compound Cl.Cl.NC1=C(F)C(N)=C(F)C(F)=C1F QYRFJLLXPINATB-UHFFFAOYSA-N 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
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000013849 propane Nutrition 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
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- 238000007127 saponification reaction Methods 0.000 description 1
- 230000036280 sedation Effects 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000008143 steroidal glycosides Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 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
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/32—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms
- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (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)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2309887A DE2309887C2 (de) | 1973-02-28 | 1973-02-28 | 1-Aryloxy-2-hydroxy-3-alkinylaminopropan-Derivate und deren physiologisch verträgliche Säureadditionssalze, pharmazeutische Präparate und Herstellungsverfahren für die Verbindungen |
| DE19742403809 DE2403809C2 (de) | 1974-01-26 | 1974-01-26 | 1-Aryloxy-2-hydroxy-3-alkinylaminopropane und Verfahren zu ihrer Herstellung und pharmazeutische Präparate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44301A0 IL44301A0 (en) | 1974-06-30 |
| IL44301A true IL44301A (en) | 1977-03-31 |
Family
ID=25764753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44301A IL44301A (en) | 1973-02-28 | 1974-02-27 | 1-Aryloxy-2-Hydroxy-3-Alkylenylamino-propanes and their salts, their manufacture and pharmaceutical preparations containing them |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3925446A (en, 2012) |
| JP (1) | JPS594417B2 (en, 2012) |
| AT (1) | AT330150B (en, 2012) |
| BG (7) | BG20565A3 (en, 2012) |
| CA (1) | CA1062717A (en, 2012) |
| CH (7) | CH605689A5 (en, 2012) |
| CS (1) | CS186263B2 (en, 2012) |
| DD (1) | DD110652A5 (en, 2012) |
| DK (1) | DK143128C (en, 2012) |
| ES (7) | ES423466A1 (en, 2012) |
| FI (1) | FI62054C (en, 2012) |
| FR (1) | FR2218900B1 (en, 2012) |
| GB (1) | GB1450287A (en, 2012) |
| HU (1) | HU168598B (en, 2012) |
| IE (1) | IE39482B1 (en, 2012) |
| IL (1) | IL44301A (en, 2012) |
| MX (2) | MX4592E (en, 2012) |
| NL (1) | NL169733C (en, 2012) |
| NO (1) | NO138062C (en, 2012) |
| PH (1) | PH9722A (en, 2012) |
| PL (2) | PL91560B1 (en, 2012) |
| SE (1) | SE411897B (en, 2012) |
| SU (1) | SU793381A3 (en, 2012) |
| YU (2) | YU50074A (en, 2012) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4038313A (en) * | 1970-01-08 | 1977-07-26 | Ciba-Geigy Corporation | Cycloalkylureido phenoxy propanolamines |
| US4035420A (en) * | 1972-07-06 | 1977-07-12 | Aktiebolaget Hassle | Substituted ureido alkylene phenoxy propanolamines |
| US4078146A (en) * | 1972-07-06 | 1978-03-07 | Aktiebolaget Hassle | Phenoxy propanolamines |
| GB1374366A (en) * | 1972-07-21 | 1974-11-20 | Science Union & Cie | Propanol derivatives and a process for their preparation |
| AT334385B (de) * | 1973-12-20 | 1976-01-10 | Chemie Linz Ag | Verfahren zur herstellung von neuen phenoxypropylaminderivaten und deren salzen |
| US4243681A (en) * | 1977-10-11 | 1981-01-06 | Mead Johnson & Company | Alkylthiophenoxypropanolamines and pharmaceutical compositions and uses thereof |
| DE2805404A1 (de) * | 1978-02-09 | 1979-08-16 | Merck Patent Gmbh | 1-aryloxy-3-nitratoalkylamino-2-propanole und verfahren zu ihrer herstellung |
| DE3009047A1 (de) * | 1980-03-08 | 1981-09-24 | C.H. Boehringer Sohn, 6507 Ingelheim | Neue l-(acylamino-aryloxy-)2-hydroxy-3-alkinylaminopropane und verfahren zu ihrer herstellung |
| DE3009036A1 (de) * | 1980-03-08 | 1981-09-24 | C.H. Boehringer Sohn, 6507 Ingelheim | Neue l-(acylamino-aryloxy-)2-hydroxy-3-alkinylaminopropane und verfahren zu ihrer herstellung |
| US4387103A (en) * | 1980-11-28 | 1983-06-07 | American Hospital Supply Corporation | Method for treatment or prophylaxis of cardiac disorders |
| US4454154A (en) * | 1981-06-23 | 1984-06-12 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| DE3248835A1 (de) * | 1981-06-23 | 1983-06-30 | American Hospital Supply Corp | Zusammensetzungen fuer die behandlung von glaukom |
| US4559359A (en) * | 1981-06-23 | 1985-12-17 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| US4455317A (en) * | 1981-06-23 | 1984-06-19 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| US4578403A (en) * | 1981-06-23 | 1986-03-25 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| DE3133719A1 (de) * | 1981-08-26 | 1983-03-10 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue 1-aryloxy-3-alkinylamino-2-propanole und verfahren zu ihrer herstellung |
| JPH02130007U (en, 2012) * | 1989-03-31 | 1990-10-26 | ||
| BRPI0507670A (pt) * | 2004-02-13 | 2007-07-17 | Warner Lambert Co | moduladores do receptor de androgênio |
| JP5838114B2 (ja) | 2012-04-02 | 2015-12-24 | 株式会社リガク | Ｘ線トポグラフィ装置 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3459782A (en) * | 1963-08-26 | 1969-08-05 | Boehringer Sohn Ingelheim | 1-substituted phenoxy-2-hydroxy-3-isopropylamino-propanes |
| GB1199037A (en) * | 1967-09-27 | 1970-07-15 | Ici Ltd | Alkanolamine Derivatives |
| US3541130A (en) * | 1967-02-06 | 1970-11-17 | Boehringer Sohn Ingelheim | 1-(cyanophenoxy)-2-hydroxy-3-tert.-butylamine propanes |
-
1974
- 1974-02-11 AT AT104774A patent/AT330150B/de not_active IP Right Cessation
- 1974-02-21 ES ES423466A patent/ES423466A1/es not_active Expired
- 1974-02-22 US US444713A patent/US3925446A/en not_active Expired - Lifetime
- 1974-02-25 CS CS7400001369A patent/CS186263B2/cs unknown
- 1974-02-25 FI FI544/74A patent/FI62054C/fi active
- 1974-02-26 DD DD176809A patent/DD110652A5/xx unknown
- 1974-02-26 BG BG026942A patent/BG20565A3/xx unknown
- 1974-02-26 BG BG026943A patent/BG20566A3/xx unknown
- 1974-02-26 HU HUBO1487A patent/HU168598B/hu unknown
- 1974-02-26 BG BG026941A patent/BG20335A3/xx unknown
- 1974-02-26 BG BG026939A patent/BG21208A3/xx unknown
- 1974-02-26 BG BG026940A patent/BG21394A3/xx unknown
- 1974-02-26 BG BG025901A patent/BG20564A3/xx unknown
- 1974-02-26 BG BG026938A patent/BG20334A3/xx unknown
- 1974-02-27 CH CH1485677A patent/CH605689A5/xx not_active IP Right Cessation
- 1974-02-27 YU YU00500/74A patent/YU50074A/xx unknown
- 1974-02-27 CH CH1485577A patent/CH605638A5/xx not_active IP Right Cessation
- 1974-02-27 NO NO740670A patent/NO138062C/no unknown
- 1974-02-27 MX MX745493U patent/MX4592E/es unknown
- 1974-02-27 PL PL1974169115A patent/PL91560B1/pl unknown
- 1974-02-27 CH CH1486077A patent/CH605691A5/xx not_active IP Right Cessation
- 1974-02-27 MX MX745489U patent/MX4588E/es unknown
- 1974-02-27 DK DK105174A patent/DK143128C/da not_active IP Right Cessation
- 1974-02-27 CH CH278074A patent/CH605636A5/xx not_active IP Right Cessation
- 1974-02-27 CH CH1485477A patent/CH605637A5/xx not_active IP Right Cessation
- 1974-02-27 CA CA193,683A patent/CA1062717A/en not_active Expired
- 1974-02-27 SE SE7402622A patent/SE411897B/sv not_active IP Right Cessation
- 1974-02-27 PL PL1974183356A patent/PL93591B1/pl unknown
- 1974-02-27 GB GB894974A patent/GB1450287A/en not_active Expired
- 1974-02-27 PH PH15555*UA patent/PH9722A/en unknown
- 1974-02-27 JP JP49023221A patent/JPS594417B2/ja not_active Expired
- 1974-02-27 CH CH1485977A patent/CH605690A5/xx not_active IP Right Cessation
- 1974-02-27 IL IL44301A patent/IL44301A/en unknown
- 1974-02-28 IE IE428/74A patent/IE39482B1/xx unknown
- 1974-02-28 FR FR7406835A patent/FR2218900B1/fr not_active Expired
- 1974-02-28 NL NLAANVRAGE7402704,A patent/NL169733C/xx not_active IP Right Cessation
- 1974-08-27 CH CH1485877A patent/CH605639A5/xx not_active IP Right Cessation
-
1975
- 1975-01-29 SU SU752100046A patent/SU793381A3/ru active
- 1975-04-04 ES ES436316A patent/ES436316A1/es not_active Expired
- 1975-04-04 ES ES436311A patent/ES436311A1/es not_active Expired
- 1975-04-04 ES ES436315A patent/ES436315A1/es not_active Expired
- 1975-04-04 ES ES436313A patent/ES436313A1/es not_active Expired
- 1975-04-04 ES ES436314A patent/ES436314A1/es not_active Expired
- 1975-04-04 ES ES436312A patent/ES436312A1/es not_active Expired
-
1980
- 1980-04-22 YU YU01095/80A patent/YU109580A/xx unknown
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