HU186560B - Process for producing pharmaceutically active new bracket-3-amino-propoxy-bracket closed-biaenzyl derivatives - Google Patents
Process for producing pharmaceutically active new bracket-3-amino-propoxy-bracket closed-biaenzyl derivatives Download PDFInfo
- Publication number
- HU186560B HU186560B HU822634A HU263482A HU186560B HU 186560 B HU186560 B HU 186560B HU 822634 A HU822634 A HU 822634A HU 263482 A HU263482 A HU 263482A HU 186560 B HU186560 B HU 186560B
- Authority
- HU
- Hungary
- Prior art keywords
- formula
- propoxy
- carboxy
- bibenzyl
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- 230000008569 process Effects 0.000 title claims description 7
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims abstract description 12
- -1 3-aminopropoxyl Chemical group 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 35
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims description 31
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 229910052736 halogen Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical group 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000004593 Epoxy Substances 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 230000023555 blood coagulation Effects 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- VUSWCWPCANWBFG-UHFFFAOYSA-N cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CCC=CC1 VUSWCWPCANWBFG-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- ANGFQVCFIHRMQD-UHFFFAOYSA-N 3-[2-(2-phenylethyl)phenoxy]propan-1-amine Chemical group NCCCOC1=CC=CC=C1CCC1=CC=CC=C1 ANGFQVCFIHRMQD-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000008177 pharmaceutical agent Substances 0.000 abstract 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- DPBWFNDFMCCGGJ-UHFFFAOYSA-N 4-Piperidine carboxamide Chemical compound NC(=O)C1CCNCC1 DPBWFNDFMCCGGJ-UHFFFAOYSA-N 0.000 description 4
- 102000008186 Collagen Human genes 0.000 description 4
- 108010035532 Collagen Proteins 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 239000003146 anticoagulant agent Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 229920001436 collagen Polymers 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000002265 prevention Effects 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 2
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 230000000702 anti-platelet effect Effects 0.000 description 2
- 229940127219 anticoagulant drug Drugs 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003180 prostaglandins Chemical class 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- KUYMVWXKHQSIAS-UHFFFAOYSA-N tert-butyl 2-chloroacetate Chemical compound CC(C)(C)OC(=O)CCl KUYMVWXKHQSIAS-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- OHYRLFBEYGJLLH-UHFFFAOYSA-N 1-(dimethylamino)-3-[2-(2-phenylethyl)phenoxy]propan-2-ol;hydrochloride Chemical compound Cl.CN(C)CC(O)COC1=CC=CC=C1CCC1=CC=CC=C1 OHYRLFBEYGJLLH-UHFFFAOYSA-N 0.000 description 1
- SVFWNMQJBMSRRW-UHFFFAOYSA-N 1-[2-(2-phenylethyl)phenoxy]-3-piperidin-1-ylpropan-2-ol Chemical group C1CCCCN1CC(O)COC1=CC=CC=C1CCC1=CC=CC=C1 SVFWNMQJBMSRRW-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- DMAXMXPDVWTIRV-UHFFFAOYSA-N 2-(2-phenylethyl)phenol Chemical group OC1=CC=CC=C1CCC1=CC=CC=C1 DMAXMXPDVWTIRV-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- 125000006290 2-hydroxybenzyl group Chemical group [H]OC1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 1
- UHAMZAWRNXQEKY-UHFFFAOYSA-N 4-[1-(4-carbamoylpiperidin-1-yl)-3-[2-(2-phenylethyl)phenoxy]propan-2-yl]oxy-4-oxobutanoic acid Chemical group C1CC(C(=O)N)CCN1CC(OC(=O)CCC(O)=O)COC1=CC=CC=C1CCC1=CC=CC=C1 UHAMZAWRNXQEKY-UHFFFAOYSA-N 0.000 description 1
- BSIZCJOHLSKIIK-UHFFFAOYSA-N 6-[1-(dimethylamino)-3-[2-(2-phenylethyl)phenoxy]propan-2-yl]oxycarbonylcyclohex-3-ene-1-carboxylic acid Chemical group C1C=CCC(C(O)=O)C1C(=O)OC(CN(C)C)COC1=CC=CC=C1CCC1=CC=CC=C1 BSIZCJOHLSKIIK-UHFFFAOYSA-N 0.000 description 1
- 240000002470 Amphicarpaea bracteata Species 0.000 description 1
- 206010003178 Arterial thrombosis Diseases 0.000 description 1
- 235000016068 Berberis vulgaris Nutrition 0.000 description 1
- 241000335053 Beta vulgaris Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 101000972485 Homo sapiens Lupus La protein Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 102100022742 Lupus La protein Human genes 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- POQBIDFFYCYHOB-UHFFFAOYSA-N Sarpogrelate hydrochloride Chemical compound Cl.COC1=CC=CC(CCC=2C(=CC=CC=2)OCC(CN(C)C)OC(=O)CCC(O)=O)=C1 POQBIDFFYCYHOB-UHFFFAOYSA-N 0.000 description 1
- 206010047141 Vasodilatation Diseases 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 239000008365 aqueous carrier Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000007883 bronchodilation Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000003177 cardiotonic effect Effects 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 210000002464 muscle smooth vascular Anatomy 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000003208 petroleum 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
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 108091006082 receptor inhibitors Proteins 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 210000003019 respiratory muscle Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 230000001732 thrombotic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229940124629 β-receptor antagonist Drugs 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56130704A JPS5832847A (ja) | 1981-08-20 | 1981-08-20 | （３−アミノプロポキシ）ビベンジル類 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU186560B true HU186560B (en) | 1985-08-28 |
Family
ID=15040620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU822634A HU186560B (en) | 1981-08-20 | 1982-08-17 | Process for producing pharmaceutically active new bracket-3-amino-propoxy-bracket closed-biaenzyl derivatives |
Country Status (9)
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5832847A (ja) * | 1981-08-20 | 1983-02-25 | Mitsubishi Chem Ind Ltd | （３−アミノプロポキシ）ビベンジル類 |
| US4616017A (en) * | 1984-06-04 | 1986-10-07 | Merck & Co., Inc. | Aminohydroxypropoxy substituted aryl compounds |
| JPH02304022A (ja) * | 1989-05-18 | 1990-12-17 | Mitsubishi Kasei Corp | セロトニン拮抗剤 |
| CA2110251A1 (en) * | 1992-11-30 | 1994-05-31 | Koichi Fujimoto | Alpha, omega-diarylalkane derivatives, their preparation and their use in the treatment and prevention of circulatory diseases and psychosis |
| JP4063341B2 (ja) * | 1994-07-06 | 2008-03-19 | メイ株式会社 | 緑内障治療剤及び眼圧降下剤 |
| DE69710258T2 (de) * | 1996-06-17 | 2002-08-22 | Mitsubishi Chemical Corp., Tokio/Tokyo | Mittel zur Beschleunigung des Tränenflusses enthaltend einen Serotonin-Liganden, insbesondere Aminoalkoxybibenzyle |
| US6468998B1 (en) | 1998-11-02 | 2002-10-22 | Mitsubishi Pharma Corporation | Pyrrolidine compounds and medicinal utilization thereof |
| WO2003026636A1 (fr) * | 2001-09-26 | 2003-04-03 | Mitsubishi Pharma Corporation | Inhibiteurs de thrombus/thrombogenese |
| JP2006160764A (ja) * | 2005-02-22 | 2006-06-22 | Mitsubishi Pharma Corp | （±）２−（ジメチルアミノ）−１−｛〔Ｏ−（ｍ−メトキシフェネチル）フェノキシ〕メチル｝エチル水素サクシナート塩酸塩の結晶 |
| KR101393178B1 (ko) * | 2005-02-22 | 2014-05-08 | 미쓰비시 타나베 파마 코퍼레이션 | (±)2-(디메틸아미노)-1-｛[Ｏ-(ｍ-메톡시페네틸)페녹시]메틸｝에틸 수소 숙시네이트 염산염의 결정 |
| CN1824647B (zh) * | 2005-02-22 | 2011-04-20 | 田边三菱制药株式会社 | (±)2-(二甲基氨基)-1-{[O-(m-甲氧基苯乙基)苯氧基]甲基}乙基氢琥珀酸酯盐酸盐的晶体 |
| US8123513B2 (en) | 2005-06-03 | 2012-02-28 | Rheon Automatic Machinery Co., Ltd. | Apparatus for rolling food dough |
| CN101239920B (zh) * | 2007-02-05 | 2013-05-22 | 南京康然医药科技有限公司 | 一种盐酸沙格雷酯的制备方法 |
| JP5090770B2 (ja) * | 2007-04-06 | 2012-12-05 | ダイト株式会社 | 塩酸サルポグレラートの工業的製造方法 |
| KR100881890B1 (ko) | 2007-05-03 | 2009-02-04 | 주식회사 엔지켐 | 사포그렐레이트 염산염의 제조방법 |
| JP5479909B2 (ja) * | 2007-11-09 | 2014-04-23 | 田辺三菱製薬株式会社 | 新規製剤 |
| JP5116025B2 (ja) | 2008-01-21 | 2013-01-09 | レオン自動機株式会社 | 食品生地延展成形装置および食品生地延展成形方法 |
| KR20100050371A (ko) * | 2008-11-10 | 2010-05-13 | 주식회사 참조아 | 염산((±)-２-(디메칠아미노)-１-[[ｏ-(ｍ-메톡시펜에틸)페녹시]메틸]에틸하이드로겐 숙시네이트의 신규 결정 및 이 신규결정을 유효성분으로 함유하는 의약조성물 |
| KR100911720B1 (ko) | 2009-04-10 | 2009-08-10 | 주식회사 한서켐 | 결정형 염산 사포그릴레이트의 제조방법 |
| KR101653816B1 (ko) | 2014-06-25 | 2016-09-06 | 주식회사 대희화학 | 결정형 사포그릴레이트 옥살산염 일수화물 또는 이의 무수물 |
| CN104356012B (zh) * | 2014-09-23 | 2016-06-15 | 山东齐都药业有限公司 | 盐酸沙格雷酯光降解杂质的制备方法 |
| WO2018039642A1 (en) | 2016-08-26 | 2018-03-01 | Exciva Ug (Haftungsbeschränkt) | Compositions and methods thereof |
| KR101905865B1 (ko) | 2017-04-11 | 2018-10-08 | 아주대학교산학협력단 | 사포그릴레이트를 유효성분으로 포함하는 감각신경성 난청의 예방 또는 치료용 조성물 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL301580A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1962-12-11 | |||
| DE2001431C3 (de) * | 1970-01-06 | 1974-12-12 | Helopharm W. Petrik & Co Kg, 1000 Berlin | 2-(2'-Hydroxy-3'-alkylaminopropoxy)-Omega-phenyl-propiophenone und Verfahren zur Herstellung derselben |
| SE386892B (sv) * | 1972-07-06 | 1976-08-23 | Haessle Ab | Forfarande for framstellning av oxaminoforeningar |
| GB1486001A (en) * | 1974-07-30 | 1977-09-14 | Beecham Group Ltd | 7-aminoalkoxy substituted benzopyrans benzo thiopyrans and naphthalenes |
| GB1493998A (en) * | 1975-06-03 | 1977-12-07 | Beecham Group Ltd | Propanolamine derivatives |
| US4071552A (en) * | 1976-05-19 | 1978-01-31 | Ayerst Mckenna And Harrison Ltd. | Aryloxy aminobutanols, their preparation and use thereof |
| JPS5365836A (en) * | 1976-11-26 | 1978-06-12 | Teijin Ltd | Preparation of aminopropanol derivs. or their salts |
| US4220603A (en) * | 1977-10-07 | 1980-09-02 | Mitsubishi Chemical Industries, Limited | Pharmaceutically active (omega-aminoalkoxy)bibenzyls |
| JPS6045632B2 (ja) * | 1978-03-09 | 1985-10-11 | 三菱化学株式会社 | ω−アミノアルコキシスチルベン類及びその酸付加塩 |
| JPS5531136A (en) * | 1978-08-25 | 1980-03-05 | Hitachi Metals Ltd | Fe-cr-co type magnet alloy |
| JPS5629549A (en) * | 1979-08-18 | 1981-03-24 | Tsutomu Kunishige | Preparation of 1-aryloxy-3-isopropylaminopropan-2-ol |
| JPS5629550A (en) * | 1979-08-18 | 1981-03-24 | Tsutomu Kunishige | Novel preparation of 1-aryloxy-3-isopropylaminopropan-2-ol |
| JPS56123954A (en) * | 1980-03-05 | 1981-09-29 | Sagami Chem Res Center | Preparation of aminoalcohol derivative |
| JPS5770844A (en) * | 1980-10-20 | 1982-05-01 | Paamakemu Asia:Kk | Preparation of aminopropanol derivative |
| JPS5832847A (ja) * | 1981-08-20 | 1983-02-25 | Mitsubishi Chem Ind Ltd | （３−アミノプロポキシ）ビベンジル類 |
| JPS6123954A (ja) * | 1984-07-12 | 1986-02-01 | Hitachi Ltd | Ｎｍｒイメ−ジング装置 |
-
1981
- 1981-08-20 JP JP56130704A patent/JPS5832847A/ja active Granted
-
1982
- 1982-07-29 US US06/403,119 patent/US4485258A/en not_active Expired - Lifetime
- 1982-08-04 EP EP82107067A patent/EP0072942B1/en not_active Expired
- 1982-08-04 DE DE8282107067T patent/DE3275540D1/de not_active Expired
- 1982-08-10 CA CA000409074A patent/CA1193264A/en not_active Expired
- 1982-08-13 DK DK365682A patent/DK166381C/da active
- 1982-08-17 HU HU822634A patent/HU186560B/hu unknown
- 1982-08-18 DD DD82242600A patent/DD202531A5/de not_active IP Right Cessation
- 1982-08-19 NO NO822833A patent/NO156525C/no not_active IP Right Cessation
-
1984
- 1984-07-09 US US06/629,061 patent/US4599419A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0072942A2 (en) | 1983-03-02 |
| JPS5832847A (ja) | 1983-02-25 |
| US4599419A (en) | 1986-07-08 |
| NO156525C (no) | 1987-10-07 |
| DD202531A5 (de) | 1983-09-21 |
| EP0072942A3 (en) | 1984-06-06 |
| NO156525B (no) | 1987-06-29 |
| DE3275540D1 (en) | 1987-04-09 |
| DK365682A (da) | 1983-02-21 |
| JPS6313427B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-03-25 |
| NO822833L (no) | 1983-02-21 |
| DK166381B (da) | 1993-05-10 |
| CA1193264A (en) | 1985-09-10 |
| DK166381C (da) | 1993-09-27 |
| EP0072942B1 (en) | 1987-03-04 |
| US4485258A (en) | 1984-11-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |