CS209918B2 - Method of preparation of the (omega-aminoalcoxy) bibenzyles - Google Patents
Method of preparation of the (omega-aminoalcoxy) bibenzyles Download PDFInfo
- Publication number
- CS209918B2 CS209918B2 CS786561A CS656178A CS209918B2 CS 209918 B2 CS209918 B2 CS 209918B2 CS 786561 A CS786561 A CS 786561A CS 656178 A CS656178 A CS 656178A CS 209918 B2 CS209918 B2 CS 209918B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- bibenzyl
- butoxy
- carbon atoms
- alkyl
- integer
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- -1 monosubstituted methylene Chemical group 0.000 claims description 117
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims description 79
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 abstract description 10
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 49
- 239000000243 solution Substances 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 5
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229920001436 collagen Polymers 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- DMAXMXPDVWTIRV-UHFFFAOYSA-N 2-(2-phenylethyl)phenol Chemical group OC1=CC=CC=C1CCC1=CC=CC=C1 DMAXMXPDVWTIRV-UHFFFAOYSA-N 0.000 description 3
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-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
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002504 physiological saline solution Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- GIHWWIZPDNRZQG-UHFFFAOYSA-N 1-[4-[2-(2-phenylethyl)phenoxy]butyl]piperidine-4-carboxylic acid;hydrochloride Chemical compound Cl.C1CC(C(=O)O)CCN1CCCCOC1=CC=CC=C1CCC1=CC=CC=C1 GIHWWIZPDNRZQG-UHFFFAOYSA-N 0.000 description 2
- JZRUBIXRQUVQPG-UHFFFAOYSA-N 1-[4-[2-[2-(2-chlorophenyl)ethyl]phenoxy]butyl]piperidine Chemical group ClC1=CC=CC=C1CCC1=CC=CC=C1OCCCCN1CCCCC1 JZRUBIXRQUVQPG-UHFFFAOYSA-N 0.000 description 2
- RMYYIPXOTYIUTI-UHFFFAOYSA-N 3-[2-[2-(3-chlorophenyl)ethyl]phenoxy]-n,n-dimethylpropan-1-amine Chemical group CN(C)CCCOC1=CC=CC=C1CCC1=CC=CC(Cl)=C1 RMYYIPXOTYIUTI-UHFFFAOYSA-N 0.000 description 2
- YHIAICIUPYBMOD-UHFFFAOYSA-N 4-[2-[2-(3-methoxyphenyl)ethyl]phenoxy]-n,n-dimethylbutan-1-amine Chemical group COC1=CC=CC(CCC=2C(=CC=CC=2)OCCCCN(C)C)=C1 YHIAICIUPYBMOD-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
- 241001465754 Metazoa Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 230000000702 anti-platelet effect Effects 0.000 description 2
- 239000003146 anticoagulant agent Substances 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000012057 packaged powder Substances 0.000 description 2
- 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 description 2
- 210000004623 platelet-rich plasma Anatomy 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RSVXRLUSSUZVDL-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-(2-phenylethyl)benzene Chemical group BrCCOC1=CC=CC=C1CCC1=CC=CC=C1 RSVXRLUSSUZVDL-UHFFFAOYSA-N 0.000 description 1
- REECUKAZRVHFMG-UHFFFAOYSA-N 1-(4-bromobutoxy)-2-[2-(2-chlorophenyl)ethyl]benzene Chemical group ClC1=CC=CC=C1CCC1=CC=CC=C1OCCCCBr REECUKAZRVHFMG-UHFFFAOYSA-N 0.000 description 1
- KKUHZIPSFPCXAA-UHFFFAOYSA-N 1-[2-[2-(2-phenylethyl)phenoxy]ethyl]piperidine-4-carboxamide Chemical group C1CC(C(=O)N)CCN1CCOC1=CC=CC=C1CCC1=CC=CC=C1 KKUHZIPSFPCXAA-UHFFFAOYSA-N 0.000 description 1
- COWRQWLTZAMMKG-UHFFFAOYSA-N 1-[4-[2-(2-phenylethyl)phenoxy]butyl]piperidine-3-carboxamide Chemical group C1C(C(=O)N)CCCN1CCCCOC1=CC=CC=C1CCC1=CC=CC=C1 COWRQWLTZAMMKG-UHFFFAOYSA-N 0.000 description 1
- JEWRDYBYCQIRKS-UHFFFAOYSA-N 1-[4-[2-(2-phenylethyl)phenoxy]butyl]piperidine-4-carbonyl chloride;hydrochloride Chemical compound Cl.C1CC(C(=O)Cl)CCN1CCCCOC1=CC=CC=C1CCC1=CC=CC=C1 JEWRDYBYCQIRKS-UHFFFAOYSA-N 0.000 description 1
- ROWPAXNVXWTPHF-UHFFFAOYSA-N 1-[4-[2-(2-phenylethyl)phenoxy]butyl]piperidine-4-carboxamide Chemical group C1CC(C(=O)N)CCN1CCCCOC1=CC=CC=C1CCC1=CC=CC=C1 ROWPAXNVXWTPHF-UHFFFAOYSA-N 0.000 description 1
- STGQBIHSCXPHJG-UHFFFAOYSA-N 1-[4-[2-[2-(2-chlorophenyl)ethyl]phenoxy]butyl]piperidine-4-carboxamide Chemical group C1CC(C(=O)N)CCN1CCCCOC1=CC=CC=C1CCC1=CC=CC=C1Cl STGQBIHSCXPHJG-UHFFFAOYSA-N 0.000 description 1
- FUCULELBHCXSBR-UHFFFAOYSA-N 1-[4-[2-[2-(2-chlorophenyl)ethyl]phenoxy]butyl]piperidine-4-carboxylic acid Chemical group C1CC(C(=O)O)CCN1CCCCOC1=CC=CC=C1CCC1=CC=CC=C1Cl FUCULELBHCXSBR-UHFFFAOYSA-N 0.000 description 1
- NYCLKNRRVNBLBB-UHFFFAOYSA-N 1-[4-[2-[2-(2-fluorophenyl)ethyl]phenoxy]butyl]piperidine-4-carboxylic acid Chemical group C1CC(C(=O)O)CCN1CCCCOC1=CC=CC=C1CCC1=CC=CC=C1F NYCLKNRRVNBLBB-UHFFFAOYSA-N 0.000 description 1
- MLGKTJYZIMASMA-UHFFFAOYSA-N 1-[4-[2-[2-(2-methoxyphenyl)ethyl]phenoxy]butyl]piperidine Chemical group COC1=CC=CC=C1CCC1=CC=CC=C1OCCCCN1CCCCC1 MLGKTJYZIMASMA-UHFFFAOYSA-N 0.000 description 1
- RXKZJIWFGYOHRD-UHFFFAOYSA-N 1-[4-[2-[2-(2-methylphenyl)ethyl]phenoxy]butyl]piperidine Chemical group CC1=CC=CC=C1CCC1=CC=CC=C1OCCCCN1CCCCC1 RXKZJIWFGYOHRD-UHFFFAOYSA-N 0.000 description 1
- IZAZESLENZVUSP-UHFFFAOYSA-N 1-[4-[2-[2-(3-chlorophenyl)ethyl]phenoxy]butyl]piperidine-4-carboxamide Chemical group C1CC(C(=O)N)CCN1CCCCOC1=CC=CC=C1CCC1=CC=CC(Cl)=C1 IZAZESLENZVUSP-UHFFFAOYSA-N 0.000 description 1
- YTVUOXHPHLFBOE-UHFFFAOYSA-N 1-[4-[2-[2-(3-chlorophenyl)ethyl]phenoxy]butyl]pyrrolidine Chemical group ClC1=CC=CC(CCC=2C(=CC=CC=2)OCCCCN2CCCC2)=C1 YTVUOXHPHLFBOE-UHFFFAOYSA-N 0.000 description 1
- MOUXANLNSVCLDL-UHFFFAOYSA-N 1-[4-[2-[2-(4-chlorophenyl)ethyl]phenoxy]butyl]-4-methylpiperidine Chemical group C1CC(C)CCN1CCCCOC1=CC=CC=C1CCC1=CC=C(Cl)C=C1 MOUXANLNSVCLDL-UHFFFAOYSA-N 0.000 description 1
- UXTDDUARMOSRSD-UHFFFAOYSA-N 1-[4-[2-[2-(4-chlorophenyl)ethyl]phenoxy]butyl]piperidine Chemical group C1=CC(Cl)=CC=C1CCC1=CC=CC=C1OCCCCN1CCCCC1 UXTDDUARMOSRSD-UHFFFAOYSA-N 0.000 description 1
- FUEPWYLHOVYBBQ-UHFFFAOYSA-N 1-[4-[2-[2-(4-chlorophenyl)ethyl]phenoxy]butyl]piperidine-4-carboxamide Chemical group C1CC(C(=O)N)CCN1CCCCOC1=CC=CC=C1CCC1=CC=C(Cl)C=C1 FUEPWYLHOVYBBQ-UHFFFAOYSA-N 0.000 description 1
- IVZOLBOGVQMCOT-UHFFFAOYSA-N 1-[4-[2-[2-(4-chlorophenyl)ethyl]phenoxy]butyl]piperidine-4-carboxylic acid Chemical group C1CC(C(=O)O)CCN1CCCCOC1=CC=CC=C1CCC1=CC=C(Cl)C=C1 IVZOLBOGVQMCOT-UHFFFAOYSA-N 0.000 description 1
- UNKNMTIYVLVORN-UHFFFAOYSA-N 1-[4-[2-[2-(4-fluorophenyl)ethyl]phenoxy]butyl]-4-methylpiperidine Chemical group C1CC(C)CCN1CCCCOC1=CC=CC=C1CCC1=CC=C(F)C=C1 UNKNMTIYVLVORN-UHFFFAOYSA-N 0.000 description 1
- XZNIWJUJJDKRSU-UHFFFAOYSA-N 1-[4-[2-[2-(4-fluorophenyl)ethyl]phenoxy]butyl]piperidin-4-ol Chemical group C1CC(O)CCN1CCCCOC1=CC=CC=C1CCC1=CC=C(F)C=C1 XZNIWJUJJDKRSU-UHFFFAOYSA-N 0.000 description 1
- SWBPIEZZPBIEKR-UHFFFAOYSA-N 1-[4-[2-[2-(4-fluorophenyl)ethyl]phenoxy]butyl]piperidine Chemical group C1=CC(F)=CC=C1CCC1=CC=CC=C1OCCCCN1CCCCC1 SWBPIEZZPBIEKR-UHFFFAOYSA-N 0.000 description 1
- XXFHFQAEDHCKFO-UHFFFAOYSA-N 1-[4-[2-[2-(4-fluorophenyl)ethyl]phenoxy]butyl]piperidine-4-carboxamide Chemical group C1CC(C(=O)N)CCN1CCCCOC1=CC=CC=C1CCC1=CC=C(F)C=C1 XXFHFQAEDHCKFO-UHFFFAOYSA-N 0.000 description 1
- APVCOJFGLQVZIM-UHFFFAOYSA-N 1-[4-[2-[2-(4-fluorophenyl)ethyl]phenoxy]butyl]piperidine-4-carboxylic acid Chemical group C1CC(C(=O)O)CCN1CCCCOC1=CC=CC=C1CCC1=CC=C(F)C=C1 APVCOJFGLQVZIM-UHFFFAOYSA-N 0.000 description 1
- VVGLSGCKKMJPEA-UHFFFAOYSA-N 1-[4-[4-chloro-2-(2-phenylethyl)phenoxy]butyl]piperidine Chemical group C=1C=CC=CC=1CCC1=CC(Cl)=CC=C1OCCCCN1CCCCC1 VVGLSGCKKMJPEA-UHFFFAOYSA-N 0.000 description 1
- CAFFJBSQMBCVIH-UHFFFAOYSA-N 2-[2-[2-(2-chlorophenyl)ethyl]phenoxy]-n,n-dimethylethanamine Chemical group CN(C)CCOC1=CC=CC=C1CCC1=CC=CC=C1Cl CAFFJBSQMBCVIH-UHFFFAOYSA-N 0.000 description 1
- YIXJANDXELPTRP-UHFFFAOYSA-N 2-[2-[2-(2-methoxyphenyl)ethyl]phenoxy]-n,n-dimethylethanamine Chemical group COC1=CC=CC=C1CCC1=CC=CC=C1OCCN(C)C YIXJANDXELPTRP-UHFFFAOYSA-N 0.000 description 1
- TWRZZCZOZLLXSL-UHFFFAOYSA-N 2-[2-[2-(4-chlorophenyl)ethyl]phenoxy]-n,n-dimethylethanamine Chemical group CN(C)CCOC1=CC=CC=C1CCC1=CC=C(Cl)C=C1 TWRZZCZOZLLXSL-UHFFFAOYSA-N 0.000 description 1
- IUVCPDNXVSWPAU-UHFFFAOYSA-N 2-[2-[2-[2-(dimethylamino)ethoxy]phenyl]ethyl]benzoic acid Chemical group CN(C)CCOC1=CC=CC=C1CCC1=CC=CC=C1C(O)=O IUVCPDNXVSWPAU-UHFFFAOYSA-N 0.000 description 1
- UHLNFCJUFRPKNV-UHFFFAOYSA-N 2-[2-[2-[2-(dimethylamino)ethoxy]phenyl]ethyl]phenol Chemical group CN(C)CCOC1=CC=CC=C1CCC1=CC=CC=C1O UHLNFCJUFRPKNV-UHFFFAOYSA-N 0.000 description 1
- FRVYZCDFKVSULE-UHFFFAOYSA-N 2-[2-[2-[4-(dimethylamino)butoxy]phenyl]ethyl]benzoic acid Chemical group CN(C)CCCCOC1=CC=CC=C1CCC1=CC=CC=C1C(O)=O FRVYZCDFKVSULE-UHFFFAOYSA-N 0.000 description 1
- CTXASSGAJBUUJD-UHFFFAOYSA-N 2-[2-[2-[4-(dimethylamino)butoxy]phenyl]ethyl]phenol Chemical group CN(C)CCCCOC1=CC=CC=C1CCC1=CC=CC=C1O CTXASSGAJBUUJD-UHFFFAOYSA-N 0.000 description 1
- JLDKSDPRXHZLOY-UHFFFAOYSA-N 2-[2-hydroxyethyl-[4-[2-methoxy-6-(2-phenylethyl)phenoxy]butyl]amino]ethanol Chemical group COC1=CC=CC(CCC=2C=CC=CC=2)=C1OCCCCN(CCO)CCO JLDKSDPRXHZLOY-UHFFFAOYSA-N 0.000 description 1
- ACUUSXFBXQOKQT-UHFFFAOYSA-N 2-[4-[4-[2-[2-(4-chlorophenyl)ethyl]phenoxy]butyl]piperazin-1-yl]ethanol Chemical group C1CN(CCO)CCN1CCCCOC1=CC=CC=C1CCC1=CC=C(Cl)C=C1 ACUUSXFBXQOKQT-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 125000000872 2-diethylaminoethoxy group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
- VZDOXBQTOSYOOE-UHFFFAOYSA-N 3-[2-[2-(2-ethoxyphenyl)ethyl]phenoxy]-n,n-dimethylpropan-1-amine Chemical group CCOC1=CC=CC=C1CCC1=CC=CC=C1OCCCN(C)C VZDOXBQTOSYOOE-UHFFFAOYSA-N 0.000 description 1
- PTIRWSHHONMJNK-UHFFFAOYSA-N 3-[2-[2-(3-fluorophenyl)ethyl]phenoxy]-n,n-dimethylpropan-1-amine Chemical group CN(C)CCCOC1=CC=CC=C1CCC1=CC=CC(F)=C1 PTIRWSHHONMJNK-UHFFFAOYSA-N 0.000 description 1
- GUSXIZATDPZDPU-UHFFFAOYSA-N 3-[2-[2-(4-fluorophenyl)ethyl]phenoxy]-n,n-dimethylpropan-1-amine Chemical group CN(C)CCCOC1=CC=CC=C1CCC1=CC=C(F)C=C1 GUSXIZATDPZDPU-UHFFFAOYSA-N 0.000 description 1
- BKYDTTIUDFXGTH-UHFFFAOYSA-N 3-[2-[2-[3-(dimethylamino)propoxy]phenyl]ethyl]benzoic acid Chemical group CN(C)CCCOC1=CC=CC=C1CCC1=CC=CC(C(O)=O)=C1 BKYDTTIUDFXGTH-UHFFFAOYSA-N 0.000 description 1
- VXWPCBXNAWJLST-UHFFFAOYSA-N 3-[4-fluoro-2-(2-phenylethyl)phenoxy]-n,n-dimethylpropan-1-amine Chemical group CN(C)CCCOC1=CC=C(F)C=C1CCC1=CC=CC=C1 VXWPCBXNAWJLST-UHFFFAOYSA-N 0.000 description 1
- JXIMJKXKBNIAAG-UHFFFAOYSA-N 4-[2-[2-(2-chlorophenyl)ethyl]phenoxy]-n,n-dimethylbutan-1-amine Chemical group CN(C)CCCCOC1=CC=CC=C1CCC1=CC=CC=C1Cl JXIMJKXKBNIAAG-UHFFFAOYSA-N 0.000 description 1
- FWDGSOAYZKZCGJ-UHFFFAOYSA-N 4-[2-[2-(2-ethoxyphenyl)ethyl]phenoxy]-n,n-diethylbutan-1-amine Chemical group CCOC1=CC=CC=C1CCC1=CC=CC=C1OCCCCN(CC)CC FWDGSOAYZKZCGJ-UHFFFAOYSA-N 0.000 description 1
- TXKSDVCQALVEBZ-UHFFFAOYSA-N 4-[2-[2-(2-fluorophenyl)ethyl]phenoxy]-n,n-dimethylbutan-1-amine Chemical group CN(C)CCCCOC1=CC=CC=C1CCC1=CC=CC=C1F TXKSDVCQALVEBZ-UHFFFAOYSA-N 0.000 description 1
- NLXSPIRRSDAKPD-UHFFFAOYSA-N 4-[2-[2-(2-fluorophenyl)ethyl]phenoxy]-n,n-dipropylbutan-1-amine Chemical group CCCN(CCC)CCCCOC1=CC=CC=C1CCC1=CC=CC=C1F NLXSPIRRSDAKPD-UHFFFAOYSA-N 0.000 description 1
- VPTMVMRUXHXVOL-UHFFFAOYSA-N 4-[2-[2-(2-methoxyphenyl)ethyl]phenoxy]-n,n-dimethylbutan-1-amine Chemical group COC1=CC=CC=C1CCC1=CC=CC=C1OCCCCN(C)C VPTMVMRUXHXVOL-UHFFFAOYSA-N 0.000 description 1
- VZLQGJHLJDPDQX-UHFFFAOYSA-N 4-[2-[2-(4-chlorophenyl)ethyl]phenoxy]-n,n-diethylbutan-1-amine Chemical group CCN(CC)CCCCOC1=CC=CC=C1CCC1=CC=C(Cl)C=C1 VZLQGJHLJDPDQX-UHFFFAOYSA-N 0.000 description 1
- CPURTRRUMVYGSX-UHFFFAOYSA-N 4-[2-[2-(4-fluorophenyl)ethyl]phenoxy]-n,n-dimethylbutan-1-amine Chemical group CN(C)CCCCOC1=CC=CC=C1CCC1=CC=C(F)C=C1 CPURTRRUMVYGSX-UHFFFAOYSA-N 0.000 description 1
- NVNSRYWWQXPXQA-UHFFFAOYSA-N 4-[2-[2-[4-(dimethylamino)butoxy]phenyl]ethyl]benzoic acid Chemical group CN(C)CCCCOC1=CC=CC=C1CCC1=CC=C(C(O)=O)C=C1 NVNSRYWWQXPXQA-UHFFFAOYSA-N 0.000 description 1
- YGHQJQAYNOLWGD-UHFFFAOYSA-N 4-[2-ethoxy-6-(2-phenylethyl)phenoxy]-n,n-diethylbutan-1-amine Chemical group CCOC1=CC=CC(CCC=2C=CC=CC=2)=C1OCCCCN(CC)CC YGHQJQAYNOLWGD-UHFFFAOYSA-N 0.000 description 1
- AWIGQTBMHMBKNF-UHFFFAOYSA-N 4-[2-methoxy-6-(2-phenylethyl)phenoxy]-n,n-dimethylbutan-1-amine Chemical group COC1=CC=CC(CCC=2C=CC=CC=2)=C1OCCCCN(C)C AWIGQTBMHMBKNF-UHFFFAOYSA-N 0.000 description 1
- QEBBEAIMJGRZTK-UHFFFAOYSA-N 4-[4-methoxy-2-(2-phenylethyl)phenoxy]-n,n-dimethylbutan-1-amine Chemical group COC1=CC=C(OCCCCN(C)C)C(CCC=2C=CC=CC=2)=C1 QEBBEAIMJGRZTK-UHFFFAOYSA-N 0.000 description 1
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 1
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 1
- QPTLTKHFSWBEPI-UHFFFAOYSA-N 6-[2-[2-(4-chlorophenyl)ethyl]phenoxy]-n,n-dimethylhexan-1-amine Chemical group CN(C)CCCCCCOC1=CC=CC=C1CCC1=CC=C(Cl)C=C1 QPTLTKHFSWBEPI-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YPALQOWQMZJVKI-UHFFFAOYSA-N CCCCOC1=CC=CC=C1CCC2=CC(=CC=C2)F Chemical group CCCCOC1=CC=CC=C1CCC2=CC(=CC=C2)F YPALQOWQMZJVKI-UHFFFAOYSA-N 0.000 description 1
- DPLDYONFIMWWMZ-UHFFFAOYSA-N CCCCOC1=CC=CC=C1CCC2=CC=C(C=C2)N(C)C Chemical group CCCCOC1=CC=CC=C1CCC2=CC=C(C=C2)N(C)C DPLDYONFIMWWMZ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 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
- 238000003747 Grignard reaction Methods 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000019483 Peanut oil Nutrition 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
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
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- 229940073608 benzyl chloride Drugs 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000037396 body weight Effects 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
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- CUGLIEVTLNHSIZ-UHFFFAOYSA-N ethyl 1-[4-[2-[2-(4-fluorophenyl)ethyl]phenoxy]butyl]piperidine-4-carboxylate Chemical group C1CC(C(=O)OCC)CCN1CCCCOC1=CC=CC=C1CCC1=CC=C(F)C=C1 CUGLIEVTLNHSIZ-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- SDWQTGMYDHPJSJ-UHFFFAOYSA-N methyl 2-[2-[2-[2-(dimethylamino)ethoxy]phenyl]ethyl]benzoate Chemical group COC(=O)C1=CC=CC=C1CCC1=CC=CC=C1OCCN(C)C SDWQTGMYDHPJSJ-UHFFFAOYSA-N 0.000 description 1
- OUKLLLDERDLXFQ-UHFFFAOYSA-N methyl 3-[2-[2-[4-(dimethylamino)butoxy]phenyl]ethyl]benzoate Chemical group COC(=O)C1=CC=CC(CCC=2C(=CC=CC=2)OCCCCN(C)C)=C1 OUKLLLDERDLXFQ-UHFFFAOYSA-N 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 1
- LINAUBRQQHFPSC-UHFFFAOYSA-N n,n-diethyl-4-[2-[2-(4-fluorophenyl)ethyl]phenoxy]butan-1-amine Chemical group CCN(CC)CCCCOC1=CC=CC=C1CCC1=CC=C(F)C=C1 LINAUBRQQHFPSC-UHFFFAOYSA-N 0.000 description 1
- SLCKFQMUDLILDQ-UHFFFAOYSA-N n,n-dimethyl-3-[2-[2-(3-methylphenyl)ethyl]phenoxy]propan-1-amine Chemical group CN(C)CCCOC1=CC=CC=C1CCC1=CC=CC(C)=C1 SLCKFQMUDLILDQ-UHFFFAOYSA-N 0.000 description 1
- SRHHZLPHXPSXPK-UHFFFAOYSA-N n,n-dimethyl-4-[2-[2-(2-methylphenyl)ethyl]phenoxy]butan-1-amine Chemical group CN(C)CCCCOC1=CC=CC=C1CCC1=CC=CC=C1C SRHHZLPHXPSXPK-UHFFFAOYSA-N 0.000 description 1
- 230000014508 negative regulation of coagulation Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011533 pre-incubation Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class 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
- 241000894007 species Species 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 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
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 235000013311 vegetables Nutrition 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- 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
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/25—Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles
- Y10T428/258—Alkali metal or alkaline earth metal or compound thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS794084A CS209917B2 (cs) | 1977-10-07 | 1979-06-13 | Způsob přípravy (omega-aminoalkoxy) bibanzylů |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52120710A JPS6021578B2 (ja) | 1977-10-07 | 1977-10-07 | （オメガ−アミノアルコキシ）ビベンジル類 |
| JP8583378A JPS5513222A (en) | 1978-07-14 | 1978-07-14 | Aminoalkoxybibenzyl and its acid addition salt |
| JP9404478A JPS5520740A (en) | 1978-08-01 | 1978-08-01 | Aminoalkoxybibenzyl and its acid addition salt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS209918B2 true CS209918B2 (en) | 1981-12-31 |
Family
ID=27304972
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS786561A CS209918B2 (en) | 1977-10-07 | 1978-10-09 | Method of preparation of the (omega-aminoalcoxy) bibenzyles |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US4220603A (fi) |
| EP (1) | EP0001759B1 (fi) |
| CA (1) | CA1105931A (fi) |
| CS (1) | CS209918B2 (fi) |
| DD (1) | DD139255A5 (fi) |
| DE (1) | DE2861477D1 (fi) |
| DK (1) | DK152040C (fi) |
| ES (2) | ES474575A1 (fi) |
| FI (1) | FI69840C (fi) |
| HU (1) | HU178306B (fi) |
| IT (1) | IT1099778B (fi) |
| NO (1) | NO146744C (fi) |
| SU (1) | SU786883A3 (fi) |
Families Citing this family (5)
| 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 |
| 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 |
| AU713236B2 (en) | 1996-02-15 | 1999-11-25 | Sankyo Company Limited | Diarly alkane derivatives containing an alicyclic group, their preparation and their theraputic and prophylactic uses |
| KR101653816B1 (ko) | 2014-06-25 | 2016-09-06 | 주식회사 대희화학 | 결정형 사포그릴레이트 옥살산염 일수화물 또는 이의 무수물 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3164607A (en) * | 1961-01-10 | 1965-01-05 | Upjohn Co | 2-phenyl-3-(tertiary amino alkoxy) phenyl-indenes |
| US3077472A (en) * | 1961-03-21 | 1963-02-12 | Univ Kansas Res Foundation | 3-[4-(aminoalkoxy)-phenyl]-4-(4-oxyphenyl)-alkanes and alkenes |
| GB945864A (en) * | 1961-08-18 | 1964-01-08 | Richardson Merrell Inc | Substituted triphenylethane |
| GB1063744A (en) * | 1964-05-25 | 1967-03-30 | American Cyanamid Co | 4-substituted-4'-tertiary aminoalkoxy biphenyls |
| US3476767A (en) * | 1965-10-11 | 1969-11-04 | Ciba Geigy Corp | 1,2-diaryl - 6 - tertiary amino lower-alkoxy-3,4-dihydro naphthalenes |
| BE754405A (fr) * | 1969-08-05 | 1971-02-04 | Thomae Gmbh Dr K | Nouveaux beta-aryl-2-aminoalcoxystyrenes |
| JPS598265B2 (ja) * | 1975-06-19 | 1984-02-23 | 三菱化学株式会社 | オメガ − アミノアルコキシビフエニルルイ マタハ ソノサンフカエンノセイゾウホウ |
| NL188944C (nl) * | 1975-06-19 | 1992-11-16 | Mitsubishi Chem Ind | Werkwijze voor het bereiden van omega-aminoalkoxybenzeenderivaten alsmede werkwijze voor het bereiden van farmaceutische preparaten met toepassing daarvan, als werkzame verbinding. |
| US4024282A (en) * | 1975-11-25 | 1977-05-17 | Mitsubishi Chemical Industries Ltd. | Pharmaceutically active 2-(3-alkylaminopropoxy)diphenylmethanes |
| US4001216A (en) * | 1975-10-30 | 1977-01-04 | American Home Products Corporation | Aminoalkyl ethers of 2,2'- and 3,3'-dihydroxydesoxybenzoin |
-
1978
- 1978-09-19 US US05/943,621 patent/US4220603A/en not_active Expired - Lifetime
- 1978-09-22 CA CA311,866A patent/CA1105931A/en not_active Expired
- 1978-10-03 HU HU78MI636A patent/HU178306B/hu not_active IP Right Cessation
- 1978-10-04 DK DK441878A patent/DK152040C/da not_active IP Right Cessation
- 1978-10-05 DD DD78208291A patent/DD139255A5/xx not_active IP Right Cessation
- 1978-10-06 ES ES474575A patent/ES474575A1/es not_active Expired
- 1978-10-06 DE DE7878101092T patent/DE2861477D1/de not_active Expired
- 1978-10-06 EP EP78101092A patent/EP0001759B1/en not_active Expired
- 1978-10-06 SU SU782668855A patent/SU786883A3/ru active
- 1978-10-06 NO NO78783399A patent/NO146744C/no unknown
- 1978-10-06 IT IT28531/78A patent/IT1099778B/it active
- 1978-10-06 FI FI783049A patent/FI69840C/fi not_active IP Right Cessation
- 1978-10-09 CS CS786561A patent/CS209918B2/cs unknown
-
1979
- 1979-04-30 ES ES480091A patent/ES480091A1/es not_active Expired
- 1979-12-06 US US06/100,741 patent/US4323568A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SU786883A3 (ru) | 1980-12-07 |
| HU178306B (en) | 1982-04-28 |
| NO783399L (no) | 1979-04-10 |
| CA1105931A (en) | 1981-07-28 |
| FI69840C (fi) | 1986-05-26 |
| IT7828531A0 (it) | 1978-10-06 |
| EP0001759B1 (en) | 1981-12-30 |
| DK152040B (da) | 1988-01-25 |
| ES474575A1 (es) | 1980-01-16 |
| IT1099778B (it) | 1985-09-28 |
| DD139255A5 (de) | 1979-12-19 |
| DK441878A (da) | 1979-04-08 |
| ES480091A1 (es) | 1980-04-01 |
| NO146744B (no) | 1982-08-23 |
| FI783049A7 (fi) | 1979-04-08 |
| EP0001759A1 (en) | 1979-05-16 |
| DK152040C (da) | 1988-07-11 |
| DE2861477D1 (en) | 1982-02-18 |
| NO146744C (no) | 1982-12-01 |
| US4220603A (en) | 1980-09-02 |
| US4323568A (en) | 1982-04-06 |
| FI69840B (fi) | 1985-12-31 |
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