JPH029577B2 - - Google Patents

Info

Publication number: JPH029577B2
Authority: JP; Japan
Prior art keywords: acid; fluorophenacyl; dose; crl40854; crl40727
Prior art date: 1981-04-13
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

Application number

JP56055460A

Other languages

English (en)

Japanese (ja)

Other versions

JPS57169450A (en

Inventor

Rafuon Rui

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

RABO ERU RAFUON SA

Original Assignee

RABO ERU RAFUON SA

Priority date (The priority date 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 date listed.)

1981-04-13

Filing date

1981-04-13

Publication date

1990-03-02

1981-04-13 Application filed by RABO ERU RAFUON SA filed Critical RABO ERU RAFUON SA

1981-04-13 Priority to JP5546081A priority Critical patent/JPS57169450A/ja

1982-10-19 Publication of JPS57169450A publication Critical patent/JPS57169450A/ja

1990-03-02 Publication of JPH029577B2 publication Critical patent/JPH029577B2/ja

Status Granted legal-status Critical Current

Links

LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 15
150000003839 salts Chemical class 0.000 claims description 9
CHCHSONQFFZQBZ-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-(propan-2-ylamino)ethanone Chemical compound CC(C)NCC(=O)C1=CC=C(F)C=C1 CHCHSONQFFZQBZ-UHFFFAOYSA-N 0.000 claims description 2
LSCVUAJOMDAVBB-UHFFFAOYSA-N 2-(tert-butylamino)-1-(2-fluorophenyl)ethanone Chemical compound CC(C)(C)NCC(=O)C1=CC=CC=C1F LSCVUAJOMDAVBB-UHFFFAOYSA-N 0.000 claims description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
230000000694 effects Effects 0.000 description 17
241000699670 Mus sp. Species 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
241000282472 Canis lupus familiaris Species 0.000 description 8
239000000203 mixture Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 7
230000002631 hypothermal effect Effects 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
208000001953 Hypotension Diseases 0.000 description 5
239000002253 acid Substances 0.000 description 5
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 5
229960004046 apomorphine Drugs 0.000 description 5
230000008859 change Effects 0.000 description 5
230000036543 hypotension Effects 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
208000001871 Tachycardia Diseases 0.000 description 4
235000011054 acetic acid Nutrition 0.000 description 4
239000000935 antidepressant agent Substances 0.000 description 4
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210000000941 bile Anatomy 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
210000001105 femoral artery Anatomy 0.000 description 4
230000001939 inductive effect Effects 0.000 description 4
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230000008018 melting Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000006794 tachycardia Effects 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
206010021143 Hypoxia Diseases 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 3
206010042008 Stereotypy Diseases 0.000 description 3
230000016571 aggressive behavior Effects 0.000 description 3
229940025084 amphetamine Drugs 0.000 description 3
230000001430 anti-depressive effect Effects 0.000 description 3
230000004872 arterial blood pressure Effects 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229940079593 drug Drugs 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000012458 free base Substances 0.000 description 3
230000033001 locomotion Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000009467 reduction Effects 0.000 description 3
239000000932 sedative agent Substances 0.000 description 3
230000001624 sedative effect Effects 0.000 description 3
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 2
ZDPACSAHMZADFZ-UHFFFAOYSA-N 1-[3-(2,4,6-Trimethoxybenzoyl)propyl]pyrrolidinium chloride Chemical compound [Cl-].COC1=CC(OC)=CC(OC)=C1C(=O)CCC[NH+]1CCCC1 ZDPACSAHMZADFZ-UHFFFAOYSA-N 0.000 description 2
206010002660 Anoxia Diseases 0.000 description 2
241000976983 Anoxia Species 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
206010010904 Convulsion Diseases 0.000 description 2
208000020401 Depressive disease Diseases 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
241001465754 Metazoa Species 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 2
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
230000007953 anoxia Effects 0.000 description 2
239000002585 base Substances 0.000 description 2
230000006399 behavior Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
210000000748 cardiovascular system Anatomy 0.000 description 2
230000036461 convulsion Effects 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
150000002222 fluorine compounds Chemical class 0.000 description 2
230000001077 hypotensive effect Effects 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
229960001317 isoprenaline Drugs 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
238000000034 method Methods 0.000 description 2
230000004899 motility Effects 0.000 description 2
231100001160 nonlethal Toxicity 0.000 description 2
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 2
229960003147 reserpine Drugs 0.000 description 2
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 2
230000002269 spontaneous effect Effects 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
231100000419 toxicity Toxicity 0.000 description 2
230000001988 toxicity Effects 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
230000000304 vasodilatating effect Effects 0.000 description 2
GXFZCDMWGMFGFL-KKXMJGKMSA-N (+)-Tubocurarine chloride hydrochloride Chemical compound [Cl-].[Cl-].C([C@H]1[N+](C)(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CC[NH+]3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 GXFZCDMWGMFGFL-KKXMJGKMSA-N 0.000 description 1
-1 (2,4,6-trimethoxyphenyl)-3-pyrrolidinopropyl Chemical group 0.000 description 1
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
FPJVAOMRFGKZOS-UHFFFAOYSA-N 1-(2-fluorophenyl)-2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCC(O)C1=CC=CC=C1F FPJVAOMRFGKZOS-UHFFFAOYSA-N 0.000 description 1
IDAZVHMZFWXZDW-UHFFFAOYSA-N 1-(3-fluorophenyl)-2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCC(O)C1=CC=CC(F)=C1 IDAZVHMZFWXZDW-UHFFFAOYSA-N 0.000 description 1
ICFWAKHBPUVWHZ-UHFFFAOYSA-N 1-(4-fluorophenyl)-2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCC(O)C1=CC=C(F)C=C1 ICFWAKHBPUVWHZ-UHFFFAOYSA-N 0.000 description 1
ZDPAWHACYDRYIW-UHFFFAOYSA-N 1-(4-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(F)C=C1 ZDPAWHACYDRYIW-UHFFFAOYSA-N 0.000 description 1
YKXCHWSPIFUXMT-UHFFFAOYSA-N 2-(tert-butylamino)-1-(3-fluorophenyl)ethanol Chemical compound CC(C)(C)NCC(O)C1=CC=CC(F)=C1 YKXCHWSPIFUXMT-UHFFFAOYSA-N 0.000 description 1
KZZYTSLQLJTJQT-UHFFFAOYSA-N 2-(tert-butylamino)-1-(4-fluorophenyl)ethanol Chemical compound CC(C)(C)NCC(O)C1=CC=C(F)C=C1 KZZYTSLQLJTJQT-UHFFFAOYSA-N 0.000 description 1
YTWSXMSQRZJJCN-UHFFFAOYSA-N 2-(tert-butylamino)-1-(4-fluorophenyl)ethanol;hydrochloride Chemical compound Cl.CC(C)(C)NCC(O)C1=CC=C(F)C=C1 YTWSXMSQRZJJCN-UHFFFAOYSA-N 0.000 description 1
UJZWJOQRSMOFMA-UHFFFAOYSA-N 2-chloro-1-(4-fluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C=C1 UJZWJOQRSMOFMA-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
238000012935 Averaging Methods 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
241001111317 Chondrodendron tomentosum Species 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
239000008709 Curare Substances 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
229940116382 Diuretic inhibitor Drugs 0.000 description 1
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108010010803 Gelatin Proteins 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
206010039897 Sedation Diseases 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
241000906446 Theraps Species 0.000 description 1
206010044565 Tremor Diseases 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000003158 alcohol group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
230000002539 anti-aggressive effect Effects 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
230000036471 bradycardia Effects 0.000 description 1
208000006218 bradycardia Diseases 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
230000001713 cholinergic effect Effects 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000003205 diastolic effect Effects 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
230000002183 duodenal effect Effects 0.000 description 1
210000001198 duodenum Anatomy 0.000 description 1
XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
230000004927 fusion Effects 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
230000026781 habituation Effects 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000001146 hypoxic effect Effects 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
230000006872 improvement Effects 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
229940039009 isoproterenol Drugs 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000005192 partition Methods 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000003334 potential effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
201000003004 ptosis Diseases 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000036280 sedation Effects 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000003091 serenic agent Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000009295 sperm incapacitation Effects 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000005556 structure-activity relationship Methods 0.000 description 1
239000013589 supplement Substances 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Landscapes

Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP5546081A 1981-04-13 1981-04-13 Fluorophenacyl-amine derivative and application to remedy Granted JPS57169450A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP5546081A JPS57169450A (en)	1981-04-13	1981-04-13	Fluorophenacyl-amine derivative and application to remedy

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP5546081A JPS57169450A (en)	1981-04-13	1981-04-13	Fluorophenacyl-amine derivative and application to remedy

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP14852889A Division JPH0228110A (ja)	1989-06-13	1989-06-13	抗抑うつ剤

Publications (2)

Publication Number	Publication Date
JPS57169450A JPS57169450A (en)	1982-10-19
JPH029577B2 true JPH029577B2 (pl)	1990-03-02

Family

ID=12999208

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP5546081A Granted JPS57169450A (en)	1981-04-13	1981-04-13	Fluorophenacyl-amine derivative and application to remedy

Country Status (1)

Country	Link
JP (1)	JPS57169450A (pl)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2554811B2 (fr) *	1979-12-14	1987-02-13	Lafon Labor	(-)-1-(2-fluorophenyl)-2-tertiobutylamino-1-ethanol, utilisation en therapeutique
GB201714736D0 (en)	2017-09-13	2017-10-25	Atrogi Ab	New compounds and uses
GB201714734D0 (en)	2017-09-13	2017-10-25	Atrogi Ab	New compounds and uses

Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3819706A (en) *	1969-12-04	1974-06-25	Burroughs Wellcome Co	Meta chloro substituted-alpha-butylamino-propiophenones
JPS528818A (en) *	1975-07-11	1977-01-24	Kansai Paint Co Ltd	Resin formation to overalp light

1981
- 1981-04-13 JP JP5546081A patent/JPS57169450A/ja active Granted

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3819706A (en) *	1969-12-04	1974-06-25	Burroughs Wellcome Co	Meta chloro substituted-alpha-butylamino-propiophenones
JPS528818A (en) *	1975-07-11	1977-01-24	Kansai Paint Co Ltd	Resin formation to overalp light

Also Published As

Publication number	Publication date
JPS57169450A (en)	1982-10-19

Publication	Publication Date	Title
DE2813373C2 (pl)	1989-11-09
KR840001836B1 (ko)	1984-10-22	9-아미노알킬플루오렌의 제조방법
DD201305A5 (de)	1983-07-13	Verfahren zur herstellung von in 7-stellung substituierten benzopyranen
CH647519A5 (de)	1985-01-31	Bluthochdruck senkende amine.
EP0054872B1 (de)	1984-10-31	3,4-Bis-substituierte 1,2,5-Oxadiazol-2-oxide, Verfahren zu ihrer Herstellung, und sie enthaltende pharmazeutische Zubereitungen
US4046898A (en)	1977-09-06	6-Aryl-pyrrolo[1,2-a]Imidazole derivatives which possess anti-hypertensive activity
DE2839279A1 (de)	1979-03-29	Derivate des 1,2,3,3a,8,8a-hexahydropyrrolo eckige klammer auf 2,3-b eckige klammer zu indols, verfahren zu ihrer herstellung sowie diese enthaltende arzneimittel
JPH0378858B2 (pl)	1991-12-17
JPH029577B2 (pl)	1990-03-02
EP0063084B1 (fr)	1984-09-12	Dérivés de phénéthanolamine, leur préparation et leur application en thérapeutique
FR2467203A1 (fr)	1981-04-17	Derives de 1,2,4-oxadiazolin-5-one, procede pour leur preparation et compositions pharmaceutiques les contenant
JPS5943460B2 (ja)	1984-10-22	２−アミノ−６−ジアルキルアミノジヒドロピリジンの製造方法
FI61182B (fi)	1982-02-26	Foerfarande foer framstaellning av farmaceutiskt aktiva butylaminderivat
JPS60158190A (ja)	1985-08-19	ヒダントイン誘導体およびその製法ならびにそれを含有する医薬
DE1568929A1 (de)	1970-04-30	Aminosubstituierte Indane und Tetraline sowie Verfahren zu deren Herstellung
FR2465733A1 (fr)	1981-03-27	Nouveaux derives imidazolylethoxymethyliques de 1,3-dioxoloquinoleines utiles notamment comme medicaments antibacteriens et antifongiques, leur procede de preparation et compositions therapeutiques et formes pharmaceutiques les contenant
JPH0254831B2 (pl)	1990-11-22
JPS5935387B2 (ja)	1984-08-28	３−アミノ−２−ヒドロキシプロパンのジ−置換フエノ−ルエ−テル類、その製法ならびに医薬用途
JPH0522704B2 (pl)	1993-03-30
JPH0376287B2 (pl)	1991-12-05
EP0061406B1 (fr)	1984-06-13	Dérivés d'acide benzamido-alkyl-hydroxamique, procédé de préparation et composition thérapeutique
JPS6121234B2 (pl)	1986-05-26
DE3432985C2 (pl)	1993-09-16
EP0266336B1 (de)	1991-05-15	Neue 1-/ 3-(2-Dialkylaminoäthoxy)-2-thienyl/-3-phenyl-1-propanone und ihre Säureadditionssalze und Verfahren zu deren Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
JPS6317068B2 (pl)	1988-04-12