JPH0318607B2 - - Google Patents
Info
- Publication number
- JPH0318607B2 JPH0318607B2 JP56105726A JP10572681A JPH0318607B2 JP H0318607 B2 JPH0318607 B2 JP H0318607B2 JP 56105726 A JP56105726 A JP 56105726A JP 10572681 A JP10572681 A JP 10572681A JP H0318607 B2 JPH0318607 B2 JP H0318607B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- alkyl
- oxygen
- bond
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 86
- 125000004432 carbon atom Chemical group C* 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 239000001301 oxygen Substances 0.000 claims description 20
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 125000002947 alkylene group Chemical group 0.000 claims description 5
- 102000012740 beta Adrenergic Receptors Human genes 0.000 claims description 5
- 108010079452 beta Adrenergic Receptors Proteins 0.000 claims description 5
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 208000029078 coronary artery disease Diseases 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 210000002820 sympathetic nervous system Anatomy 0.000 claims description 3
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
- 206010002383 Angina Pectoris Diseases 0.000 claims description 2
- 206010019280 Heart failures Diseases 0.000 claims description 2
- 206010020850 Hyperthyroidism Diseases 0.000 claims description 2
- 208000019695 Migraine disease Diseases 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 206010027599 migraine Diseases 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 239000008024 pharmaceutical diluent Substances 0.000 claims description 2
- 208000005057 thyrotoxicosis Diseases 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
- 239000003087 receptor blocking agent Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 description 24
- 238000002474 experimental method Methods 0.000 description 15
- 210000002216 heart Anatomy 0.000 description 15
- 241000700159 Rattus Species 0.000 description 14
- 239000003814 drug Substances 0.000 description 13
- 230000000747 cardiac effect Effects 0.000 description 12
- 229940079593 drug Drugs 0.000 description 12
- -1 3-aminopropoxyphenyl Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 241000700198 Cavia Species 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 230000000144 pharmacologic effect Effects 0.000 description 7
- 230000002861 ventricular Effects 0.000 description 7
- METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 6
- 241000700199 Cavia porcellus Species 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 229960002274 atenolol Drugs 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- 210000002837 heart atrium Anatomy 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 239000004031 partial agonist Substances 0.000 description 6
- 230000004044 response Effects 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 4
- TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 230000001746 atrial effect Effects 0.000 description 4
- 239000002876 beta blocker Substances 0.000 description 4
- 230000036772 blood pressure Effects 0.000 description 4
- 231100000673 dose–response relationship Toxicity 0.000 description 4
- 230000000004 hemodynamic effect Effects 0.000 description 4
- 229960001340 histamine Drugs 0.000 description 4
- 230000004410 intraocular pressure Effects 0.000 description 4
- 210000005246 left atrium Anatomy 0.000 description 4
- 210000004072 lung Anatomy 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 229960003712 propranolol Drugs 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 229960004605 timolol Drugs 0.000 description 4
- 210000001519 tissue Anatomy 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 229940097320 beta blocking agent Drugs 0.000 description 3
- 229960004324 betaxolol Drugs 0.000 description 3
- CHDPSNLJFOQTRK-UHFFFAOYSA-N betaxolol hydrochloride Chemical compound [Cl-].C1=CC(OCC(O)C[NH2+]C(C)C)=CC=C1CCOCC1CC1 CHDPSNLJFOQTRK-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 210000001715 carotid artery Anatomy 0.000 description 3
- 230000001186 cumulative effect Effects 0.000 description 3
- 239000012954 diazonium Substances 0.000 description 3
- 150000001989 diazonium salts Chemical class 0.000 description 3
- 208000028867 ischemia Diseases 0.000 description 3
- 229940039009 isoproterenol Drugs 0.000 description 3
- 210000004731 jugular vein Anatomy 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 230000010410 reperfusion Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 238000011200 topical administration Methods 0.000 description 3
- 210000003437 trachea Anatomy 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000005821 Claisen rearrangement reaction Methods 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 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 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000003302 alkenyloxy group Chemical group 0.000 description 2
- 230000008485 antagonism Effects 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000010009 beating Methods 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000036471 bradycardia Effects 0.000 description 2
- 208000006218 bradycardia Diseases 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 2
- 210000004351 coronary vessel Anatomy 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 231100000956 nontoxicity Toxicity 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 230000010412 perfusion Effects 0.000 description 2
- 230000036581 peripheral resistance Effects 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000033764 rhythmic process Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 230000001975 sympathomimetic effect Effects 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- 239000003981 vehicle Substances 0.000 description 2
- 206010047302 ventricular tachycardia Diseases 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JQJNXOLXNCKAIH-UHFFFAOYSA-N 1-(2-methoxyethoxy)-4-phenylmethoxybenzene Chemical compound C1=CC(OCCOC)=CC=C1OCC1=CC=CC=C1 JQJNXOLXNCKAIH-UHFFFAOYSA-N 0.000 description 1
- XTIGGAHUZJWQMD-UHFFFAOYSA-N 1-chloro-2-methoxyethane Chemical compound COCCCl XTIGGAHUZJWQMD-UHFFFAOYSA-N 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- KXZIBRUIJDEWKY-UHFFFAOYSA-N 2,5-dimethoxyfuran Chemical compound COC1=CC=C(OC)O1 KXZIBRUIJDEWKY-UHFFFAOYSA-N 0.000 description 1
- YXRCDWIZAGWUBL-UHFFFAOYSA-N 2-(4-methoxyphenoxy)ethanamine Chemical compound COC1=CC=C(OCCN)C=C1 YXRCDWIZAGWUBL-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- LDVJBHPIVXEDTI-UHFFFAOYSA-N 2-bromo-4-(2-methoxyethoxy)-1-phenylmethoxybenzene Chemical compound BrC1=CC(OCCOC)=CC=C1OCC1=CC=CC=C1 LDVJBHPIVXEDTI-UHFFFAOYSA-N 0.000 description 1
- DAQDBWKQGYANFW-UHFFFAOYSA-N 2-bromo-4-(2-methoxyethoxy)phenol Chemical compound COCCOC1=CC=C(O)C(Br)=C1 DAQDBWKQGYANFW-UHFFFAOYSA-N 0.000 description 1
- YGLYIKXNOAGEKB-UHFFFAOYSA-N 2-hydroxy-5-(2-methoxyethoxy)benzonitrile Chemical compound COCCOC1=CC=C(O)C(C#N)=C1 YGLYIKXNOAGEKB-UHFFFAOYSA-N 0.000 description 1
- JHXDCKWLPYBHJY-UHFFFAOYSA-N 3-cyclopent-2-en-1-yloxycyclopentene Chemical compound C1=CCCC1OC1C=CCC1 JHXDCKWLPYBHJY-UHFFFAOYSA-N 0.000 description 1
- NIGIGWPNXVNZRK-UHFFFAOYSA-N 4-(2-methoxyethoxy)phenol Chemical compound COCCOC1=CC=C(O)C=C1 NIGIGWPNXVNZRK-UHFFFAOYSA-N 0.000 description 1
- LUYOOYUMAAXCQV-UHFFFAOYSA-N 5-(2-methoxyethoxy)-2-(oxiran-2-ylmethoxy)benzonitrile Chemical compound N#CC1=CC(OCCOC)=CC=C1OCC1OC1 LUYOOYUMAAXCQV-UHFFFAOYSA-N 0.000 description 1
- XFFJZBPNJPASCD-UHFFFAOYSA-N 5-(2-methoxyethoxy)-2-phenylmethoxybenzonitrile Chemical compound N#CC1=CC(OCCOC)=CC=C1OCC1=CC=CC=C1 XFFJZBPNJPASCD-UHFFFAOYSA-N 0.000 description 1
- 108060003345 Adrenergic Receptor Proteins 0.000 description 1
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- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 208000021642 Muscular disease Diseases 0.000 description 1
- 201000009623 Myopathy Diseases 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 238000010934 O-alkylation reaction Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 241000700157 Rattus norvegicus Species 0.000 description 1
- 206010058156 Reperfusion arrhythmia Diseases 0.000 description 1
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- 206010047289 Ventricular extrasystoles Diseases 0.000 description 1
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- DXPOSRCHIDYWHW-UHFFFAOYSA-N Xamoterol Chemical compound C=1C=C(O)C=CC=1OCC(O)CNCCNC(=O)N1CCOCC1 DXPOSRCHIDYWHW-UHFFFAOYSA-N 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
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- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical group [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 230000000138 effect on histamine Effects 0.000 description 1
- 230000004406 elevated intraocular pressure Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 1
- 229960003132 halothane Drugs 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
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- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
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- 230000002083 iodinating effect Effects 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000008722 morphological abnormality Effects 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 231100000299 mutagenicity Toxicity 0.000 description 1
- 230000007886 mutagenicity Effects 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- PHUTUTUABXHXLW-UHFFFAOYSA-N pindolol Chemical compound CC(C)NCC(O)COC1=CC=CC2=NC=C[C]12 PHUTUTUABXHXLW-UHFFFAOYSA-N 0.000 description 1
- 229960002508 pindolol Drugs 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000000284 resting effect Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000035488 systolic blood pressure Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 210000005062 tracheal ring Anatomy 0.000 description 1
- 210000005092 tracheal tissue Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 208000003663 ventricular fibrillation Diseases 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229960004928 xamoterol Drugs 0.000 description 1
Landscapes
- 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)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8022412 | 1980-07-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5746946A JPS5746946A (en) | 1982-03-17 |
| JPH0318607B2 true JPH0318607B2 (el) | 1991-03-13 |
Family
ID=10514633
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56105726A Granted JPS5746946A (en) | 1980-07-09 | 1981-07-08 | 3-aminopropoxyphenyl derivative, manufacture and medicine containing same |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5746946A (el) |
| ZA (1) | ZA814677B (el) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993024121A1 (en) * | 1992-05-22 | 1993-12-09 | Senju Pharmaceutical Co., Ltd. | Remedy for glaucoma |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009040769A (ja) * | 2008-07-09 | 2009-02-26 | William John Louis | ３−アミノ−プロポキシフェニル誘導体（ｉ） |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49101343A (el) * | 1973-01-17 | 1974-09-25 | ||
| JPS53149937A (en) * | 1977-06-02 | 1978-12-27 | Yoshitomi Pharmaceut Ind Ltd | Phenoxyaminopropanol derivatives and their preparation |
| JPS559084A (en) * | 1978-06-30 | 1980-01-22 | Haessle Ab | Membrane stabilizing compound having betaaacceptor interrupting activity |
-
1981
- 1981-07-08 JP JP56105726A patent/JPS5746946A/ja active Granted
- 1981-07-09 ZA ZA814677A patent/ZA814677B/xx unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS49101343A (el) * | 1973-01-17 | 1974-09-25 | ||
| JPS53149937A (en) * | 1977-06-02 | 1978-12-27 | Yoshitomi Pharmaceut Ind Ltd | Phenoxyaminopropanol derivatives and their preparation |
| JPS559084A (en) * | 1978-06-30 | 1980-01-22 | Haessle Ab | Membrane stabilizing compound having betaaacceptor interrupting activity |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993024121A1 (en) * | 1992-05-22 | 1993-12-09 | Senju Pharmaceutical Co., Ltd. | Remedy for glaucoma |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA814677B (en) | 1983-02-23 |
| JPS5746946A (en) | 1982-03-17 |
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