HU182667B - Process for preparing diphenyl-alkane ethers - Google Patents
Process for preparing diphenyl-alkane ethers Download PDFInfo
- Publication number
- HU182667B HU182667B HU73180A HU73180A HU182667B HU 182667 B HU182667 B HU 182667B HU 73180 A HU73180 A HU 73180A HU 73180 A HU73180 A HU 73180A HU 182667 B HU182667 B HU 182667B
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- phenyl
- formula
- group
- amino
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 pyrrolidino, piperidino Chemical group 0.000 claims abstract description 69
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 54
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 238000000034 method Methods 0.000 claims abstract description 17
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 9
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 150000002170 ethers Chemical class 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 231100000252 nontoxic Toxicity 0.000 claims description 5
- 230000003000 nontoxic effect Effects 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 125000005059 halophenyl group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 abstract description 5
- 210000004556 brain Anatomy 0.000 abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 3
- HQUIMAMPJJZHIU-UHFFFAOYSA-N 3-[1-(4-fluorophenyl)-4-phenylbutoxy]-n,n-dimethylpropan-1-amine Chemical compound C=1C=C(F)C=CC=1C(OCCCN(C)C)CCCC1=CC=CC=C1 HQUIMAMPJJZHIU-UHFFFAOYSA-N 0.000 abstract description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 2
- 230000000304 vasodilatating effect Effects 0.000 abstract description 2
- 241001354782 Nitor Species 0.000 abstract 1
- 230000003213 activating effect Effects 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 210000001772 blood platelet Anatomy 0.000 abstract 1
- 230000015271 coagulation Effects 0.000 abstract 1
- 238000005345 coagulation Methods 0.000 abstract 1
- 210000004351 coronary vessel Anatomy 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 230000004060 metabolic process Effects 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 230000002048 spasmolytic effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 11
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229910001626 barium chloride Inorganic materials 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000002490 cerebral effect Effects 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 229940124549 vasodilator Drugs 0.000 description 4
- 239000003071 vasodilator agent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- MFDDWGHYYPHEMG-UHFFFAOYSA-N [1-(3-chloropropoxy)-4-phenylbutyl]benzene Chemical compound C=1C=CC=CC=1C(OCCCCl)CCCC1=CC=CC=C1 MFDDWGHYYPHEMG-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 239000000739 antihistaminic agent Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- XLNKFHFRGQTHDH-UHFFFAOYSA-N ethyl n-[3-[1-(4-fluorophenyl)-4-phenylbutoxy]propyl]-n-methylcarbamate Chemical compound C=1C=C(F)C=CC=1C(OCCCN(C)C(=O)OCC)CCCC1=CC=CC=C1 XLNKFHFRGQTHDH-UHFFFAOYSA-N 0.000 description 2
- 210000003405 ileum Anatomy 0.000 description 2
- OCKPCBLVNKHBMX-UHFFFAOYSA-N n-butyl-benzene Natural products CCCCC1=CC=CC=C1 OCKPCBLVNKHBMX-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CAGIBUJGQRHYEW-UHFFFAOYSA-N 1,4-diphenylbutan-1-ol Chemical compound C=1C=CC=CC=1C(O)CCCC1=CC=CC=C1 CAGIBUJGQRHYEW-UHFFFAOYSA-N 0.000 description 1
- KADYLDVFYKZYSU-UHFFFAOYSA-N 1-[3-(1,4-diphenylbutoxy)propyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1CCCOC(C=1C=CC=CC=1)CCCC1=CC=CC=C1 KADYLDVFYKZYSU-UHFFFAOYSA-N 0.000 description 1
- MVSBULARNIHBOG-UHFFFAOYSA-N 1-[3-(1,4-diphenylbutoxy)propyl]-4-phenylpiperazine Chemical compound C1CN(C=2C=CC=CC=2)CCN1CCCOC(C=1C=CC=CC=1)CCCC1=CC=CC=C1 MVSBULARNIHBOG-UHFFFAOYSA-N 0.000 description 1
- BAKOFKMYBHXQOP-UHFFFAOYSA-N 1-[3-(1,4-diphenylbutoxy)propyl]piperidine Chemical compound C1CCCCN1CCCOC(C=1C=CC=CC=1)CCCC1=CC=CC=C1 BAKOFKMYBHXQOP-UHFFFAOYSA-N 0.000 description 1
- ZJYCNJIRGUCKPU-UHFFFAOYSA-N 1-[3-(1,4-diphenylbutoxy)propyl]pyrrolidine Chemical compound C1CCCN1CCCOC(C=1C=CC=CC=1)CCCC1=CC=CC=C1 ZJYCNJIRGUCKPU-UHFFFAOYSA-N 0.000 description 1
- JPWBVLOUAPVTOG-UHFFFAOYSA-N 1-[3-(1,5-diphenylpentoxy)propyl]piperidine Chemical compound C1CCCCN1CCCOC(C=1C=CC=CC=1)CCCCC1=CC=CC=C1 JPWBVLOUAPVTOG-UHFFFAOYSA-N 0.000 description 1
- HEIMWDTWMQGWGD-UHFFFAOYSA-N 1-[3-(1,5-diphenylpentoxy)propyl]pyrrolidine Chemical compound C1CCCN1CCCOC(C=1C=CC=CC=1)CCCCC1=CC=CC=C1 HEIMWDTWMQGWGD-UHFFFAOYSA-N 0.000 description 1
- VTIVQYUKBOVUIL-UHFFFAOYSA-N 2-(1,3-diphenylpropoxy)-n,n-dimethylethanamine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)CCC1=CC=CC=C1 VTIVQYUKBOVUIL-UHFFFAOYSA-N 0.000 description 1
- BLMKPBBIEHVCHY-UHFFFAOYSA-N 2-(1,5-diphenylpentoxy)-n,n-diethylethanamine Chemical compound C=1C=CC=CC=1C(OCCN(CC)CC)CCCCC1=CC=CC=C1 BLMKPBBIEHVCHY-UHFFFAOYSA-N 0.000 description 1
- VQVVSATZRAEKLV-UHFFFAOYSA-N 3-(1,3-diphenylpropoxy)-n,n-dimethylpropan-1-amine Chemical compound C=1C=CC=CC=1C(OCCCN(C)C)CCC1=CC=CC=C1 VQVVSATZRAEKLV-UHFFFAOYSA-N 0.000 description 1
- KXBOXHFHKSYVII-UHFFFAOYSA-N 3-(1,4-diphenylbutoxy)-n-methylpropan-1-amine Chemical compound C=1C=CC=CC=1C(OCCCNC)CCCC1=CC=CC=C1 KXBOXHFHKSYVII-UHFFFAOYSA-N 0.000 description 1
- DLGZTBZRSYMPJO-UHFFFAOYSA-N 3-(1,4-diphenylbutoxy)-n-propan-2-ylpropan-1-amine Chemical compound C=1C=CC=CC=1C(OCCCNC(C)C)CCCC1=CC=CC=C1 DLGZTBZRSYMPJO-UHFFFAOYSA-N 0.000 description 1
- MIKYHRNYKNXKLQ-UHFFFAOYSA-N 3-(1,4-diphenylbutoxy)propan-1-amine Chemical compound C=1C=CC=CC=1C(OCCCN)CCCC1=CC=CC=C1 MIKYHRNYKNXKLQ-UHFFFAOYSA-N 0.000 description 1
- RHOLDNKNSOTYJI-UHFFFAOYSA-N 3-[1-(4-fluorophenyl)-4-phenylbutoxy]-n-methylpropan-1-amine Chemical compound C=1C=C(F)C=CC=1C(OCCCNC)CCCC1=CC=CC=C1 RHOLDNKNSOTYJI-UHFFFAOYSA-N 0.000 description 1
- NCAOPUCWOQDRFT-UHFFFAOYSA-N 3-[1-(furan-2-yl)-4-phenylbutoxy]-n,n-dimethylpropan-1-amine Chemical compound C=1C=COC=1C(OCCCN(C)C)CCCC1=CC=CC=C1 NCAOPUCWOQDRFT-UHFFFAOYSA-N 0.000 description 1
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
- UZJBNJBIMRPVPY-UHFFFAOYSA-N 4-[1-[3-(dimethylamino)propoxy]-4-phenylbutyl]phenol Chemical compound C=1C=C(O)C=CC=1C(OCCCN(C)C)CCCC1=CC=CC=C1 UZJBNJBIMRPVPY-UHFFFAOYSA-N 0.000 description 1
- SCQLBZWHMHZMLY-UHFFFAOYSA-N 4-[3-(1,4-diphenylbutoxy)propyl]morpholine Chemical compound C1COCCN1CCCOC(C=1C=CC=CC=1)CCCC1=CC=CC=C1 SCQLBZWHMHZMLY-UHFFFAOYSA-N 0.000 description 1
- DWMMGPGNDBIGHT-UHFFFAOYSA-N 4-[3-(1,5-diphenylpentoxy)propyl]morpholine Chemical compound C1COCCN1CCCOC(C=1C=CC=CC=1)CCCCC1=CC=CC=C1 DWMMGPGNDBIGHT-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 206010003211 Arteriosclerosis coronary artery Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 206010066296 Cerebral calcification Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 206010049816 Muscle tightness Diseases 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 206010029897 Obsessive thoughts Diseases 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 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
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- WLZGVXRXIFIYJG-UHFFFAOYSA-N n,n-dimethyl-3-(4-phenyl-1-pyridin-2-ylbutoxy)propan-1-amine Chemical compound C=1C=CC=NC=1C(OCCCN(C)C)CCCC1=CC=CC=C1 WLZGVXRXIFIYJG-UHFFFAOYSA-N 0.000 description 1
- MITDJTWMHZTZLB-UHFFFAOYSA-N n,n-dimethyl-3-(4-phenyl-1-pyridin-4-ylbutoxy)propan-1-amine Chemical compound C=1C=NC=CC=1C(OCCCN(C)C)CCCC1=CC=CC=C1 MITDJTWMHZTZLB-UHFFFAOYSA-N 0.000 description 1
- NCXKBUXMXXGJIS-UHFFFAOYSA-N n,n-dimethyl-3-[1-(4-methylphenyl)-4-phenylbutoxy]propan-1-amine Chemical compound C=1C=C(C)C=CC=1C(OCCCN(C)C)CCCC1=CC=CC=C1 NCXKBUXMXXGJIS-UHFFFAOYSA-N 0.000 description 1
- ZZWGXMOVPSOJIQ-UHFFFAOYSA-N n,n-dimethyl-3-[4-phenyl-1-(4-phenylmethoxyphenyl)butoxy]propan-1-amine Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1C(OCCCN(C)C)CCCC1=CC=CC=C1 ZZWGXMOVPSOJIQ-UHFFFAOYSA-N 0.000 description 1
- IKXXRSJQMDOVFB-UHFFFAOYSA-N n,n-dimethyl-3-[4-phenyl-1-(4-propan-2-ylsulfanylphenyl)butoxy]propan-1-amine Chemical compound C1=CC(SC(C)C)=CC=C1C(OCCCN(C)C)CCCC1=CC=CC=C1 IKXXRSJQMDOVFB-UHFFFAOYSA-N 0.000 description 1
- WJPBYMBBHJYOQK-UHFFFAOYSA-N n,n-dimethyl-3-[4-phenyl-1-(4-propan-2-ylsulfinylphenyl)butoxy]propan-1-amine Chemical compound C1=CC(S(=O)C(C)C)=CC=C1C(OCCCN(C)C)CCCC1=CC=CC=C1 WJPBYMBBHJYOQK-UHFFFAOYSA-N 0.000 description 1
- NCXLYIWSXVGOEN-UHFFFAOYSA-N n-benzyl-3-(1,4-diphenylbutoxy)propan-1-amine Chemical compound C=1C=CC=CC=1CCCC(C=1C=CC=CC=1)OCCCNCC1=CC=CC=C1 NCXLYIWSXVGOEN-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 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 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4003279A JPS55133338A (en) | 1979-04-02 | 1979-04-02 | New aminoalkoxyalkane derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU182667B true HU182667B (en) | 1984-02-28 |
Family
ID=12569562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU73180A HU182667B (en) | 1979-04-02 | 1980-03-28 | Process for preparing diphenyl-alkane ethers |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS55133338A (enrdf_load_stackoverflow) |
| HU (1) | HU182667B (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63115260U (enrdf_load_stackoverflow) * | 1987-01-17 | 1988-07-25 |
-
1979
- 1979-04-02 JP JP4003279A patent/JPS55133338A/ja active Granted
-
1980
- 1980-03-28 HU HU73180A patent/HU182667B/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55133338A (en) | 1980-10-17 |
| JPS6249266B2 (enrdf_load_stackoverflow) | 1987-10-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |