JPS6118553B2 - - Google Patents

Info

Publication number: JPS6118553B2
Authority: JP; Japan
Prior art keywords: group; formula; complex; malonylurea; represent
Prior art date: 1978-04-24
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

Application number

JP4920878A

Other languages

English (en)

Japanese (ja)

Other versions

JPS54144384A (en

Inventor

Goorudo Oobaato Fuiritsupu

Merukonian Deiran

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.)

SAHOSU SA

Original Assignee

SAHOSU 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.)

1978-04-24

Filing date

1978-04-24

Publication date

1986-05-13

1978-04-24 Application filed by SAHOSU SA filed Critical SAHOSU SA

1978-04-24 Priority to JP4920878A priority Critical patent/JPS54144384A/ja

1979-11-10 Publication of JPS54144384A publication Critical patent/JPS54144384A/ja

1986-05-13 Publication of JPS6118553B2 publication Critical patent/JPS6118553B2/ja

Status Granted legal-status Critical Current

Links

239000000203 mixture Substances 0.000 claims description 41
HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical class O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 16
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
125000003118 aryl group Chemical group 0.000 claims description 5
125000001931 aliphatic group Chemical group 0.000 claims description 4
-1 carbamoyloxy group Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
238000002844 melting Methods 0.000 claims description 4
230000008018 melting Effects 0.000 claims description 4
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
239000008024 pharmaceutical diluent Substances 0.000 claims description 2
238000010298 pulverizing process Methods 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
238000012360 testing method Methods 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
239000000243 solution Substances 0.000 description 18
241001465754 Metazoa Species 0.000 description 15
239000000047 product Substances 0.000 description 13
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 12
239000000843 powder Substances 0.000 description 12
230000000694 effects Effects 0.000 description 11
238000004519 manufacturing process Methods 0.000 description 11
229960002695 phenobarbital Drugs 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 10
239000003208 petroleum Substances 0.000 description 8
241000699670 Mus sp. Species 0.000 description 7
230000009471 action Effects 0.000 description 7
239000003814 drug Substances 0.000 description 7
238000001556 precipitation Methods 0.000 description 7
235000011121 sodium hydroxide Nutrition 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
229940079593 drug Drugs 0.000 description 6
238000003756 stirring Methods 0.000 description 6
QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 6
239000000126 substance Substances 0.000 description 6
239000000463 material Substances 0.000 description 5
FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
206010039897 Sedation Diseases 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
206010044565 Tremor Diseases 0.000 description 4
239000000470 constituent Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
230000036280 sedation Effects 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 3
241001279009 Strychnos toxifera Species 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
WRLGYAWRGXKSKG-UHFFFAOYSA-M phenobarbital sodium Chemical compound [Na+].C=1C=CC=CC=1C1(CC)C(=O)NC([O-])=NC1=O WRLGYAWRGXKSKG-UHFFFAOYSA-M 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000000932 sedative agent Substances 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
229960005453 strychnine Drugs 0.000 description 3
239000003826 tablet Substances 0.000 description 3
230000002936 tranquilizing effect Effects 0.000 description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
206010010071 Coma Diseases 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
208000029808 Psychomotor disease Diseases 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
229960002319 barbital Drugs 0.000 description 2
229940125717 barbiturate Drugs 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000003518 caustics Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000000147 hypnotic effect Effects 0.000 description 2
239000007924 injection Substances 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000005259 measurement Methods 0.000 description 2
239000004570 mortar (masonry) Substances 0.000 description 2
210000003205 muscle Anatomy 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
230000004044 response Effects 0.000 description 2
229940125723 sedative agent Drugs 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
241000894007 species Species 0.000 description 2
239000007858 starting material Substances 0.000 description 2
230000002195 synergetic effect Effects 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
230000001256 tonic effect Effects 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
239000003204 tranquilizing agent Substances 0.000 description 2
238000005303 weighing Methods 0.000 description 2
ADNICYRGSLSGRT-UHFFFAOYSA-N (1-butoxy-3-chloropropyl) carbamate Chemical compound CCCCOC(CCCl)OC(N)=O ADNICYRGSLSGRT-UHFFFAOYSA-N 0.000 description 1
AZFJNYUXIJHNJH-UHFFFAOYSA-N (3-chloro-1-propoxypropyl) carbamate Chemical compound CCCOC(CCCl)OC(N)=O AZFJNYUXIJHNJH-UHFFFAOYSA-N 0.000 description 1
GOOCRIHPADOQAS-ZNUXJMJHSA-N (4ar,5as,8ar,13as,15as,15br)-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2h-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-14-one;sulfuric acid Chemical compound OS(O)(=O)=O.O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1.O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 GOOCRIHPADOQAS-ZNUXJMJHSA-N 0.000 description 1
SCUGNFZOHVZCJZ-UHFFFAOYSA-N 1-(4-chlorobutoxy)propan-1-ol Chemical compound CCC(O)OCCCCCl SCUGNFZOHVZCJZ-UHFFFAOYSA-N 0.000 description 1
206010001605 Alcohol poisoning Diseases 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000700198 Cavia Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
206010053398 Clonic convulsion Diseases 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
206010012335 Dependence Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
208000012902 Nervous system disease Diseases 0.000 description 1
208000025966 Neurological disease Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
208000003443 Unconsciousness Diseases 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
231100000460 acute oral toxicity Toxicity 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
230000001410 anti-tremor Effects 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
229960003965 antiepileptics Drugs 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
230000008901 benefit Effects 0.000 description 1
238000009835 boiling Methods 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
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 description 1
229960001076 chlorpromazine Drugs 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000009918 complex formation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000009795 derivation Methods 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000002996 emotional effect Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000030214 innervation Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
206010022437 insomnia Diseases 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001012 protector Effects 0.000 description 1
229940001470 psychoactive drug Drugs 0.000 description 1
239000004089 psychotropic agent Substances 0.000 description 1
230000000506 psychotropic effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000012264 purified product Substances 0.000 description 1
230000011514 reflex Effects 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
239000012262 resinous product Substances 0.000 description 1
239000012261 resinous substance Substances 0.000 description 1
238000005185 salting out Methods 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
RGHFKWPGWBFQLN-UHFFFAOYSA-M sodium;5,5-diethylpyrimidin-3-ide-2,4,6-trione Chemical compound [Na+].CCC1(CC)C([O-])=NC(=O)NC1=O RGHFKWPGWBFQLN-UHFFFAOYSA-M 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000010972 statistical evaluation Methods 0.000 description 1
229960000412 strychnine sulfate Drugs 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000002889 sympathetic effect Effects 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
230000008719 thickening Effects 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
231100000563 toxic property Toxicity 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
229940125725 tranquilizer Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP4920878A 1978-04-24 1978-04-24 Complex compound for tranquilization Granted JPS54144384A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP4920878A JPS54144384A (en)	1978-04-24	1978-04-24	Complex compound for tranquilization

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP4920878A JPS54144384A (en)	1978-04-24	1978-04-24	Complex compound for tranquilization

Publications (2)

Publication Number	Publication Date
JPS54144384A JPS54144384A (en)	1979-11-10
JPS6118553B2 true JPS6118553B2 (ko)	1986-05-13

Family

ID=12824554

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP4920878A Granted JPS54144384A (en)	1978-04-24	1978-04-24	Complex compound for tranquilization

Country Status (1)

Country	Link
JP (1)	JPS54144384A (ko)

1978
- 1978-04-24 JP JP4920878A patent/JPS54144384A/ja active Granted

Also Published As

Publication number	Publication date
JPS54144384A (en)	1979-11-10

Publication	Publication Date	Title
JPS6049192B2 (ja)	1985-10-31	新規置換ベンズアミド、その製造方法及びこれを有効成分とする向精神薬
BG61367B2 (bg)	1997-06-30	Циклоалкилтриазоли
WO1990012574A1 (en)	1990-11-01	Dopamine agonist compounds
JPH0723365B2 (ja)	1995-03-15	フエノキシアルキルまたはチオフエノキシアルキル側鎖を有する新規ピペラジンカルボキシアミド化合物
DE3854981T2 (de)	1996-09-05	1-Pyrrolidinacetamid-Derivate und ihre Verwendung
JPS6043348B2 (ja)	1985-09-27	新規化合物またはその生理的に許容可能な塩及びこれらの製造法
JPH03866B2 (ko)	1991-01-09
Drake et al.	1949	Some N1-(6-methoxy-8-quinolylaminoalkyl)-guanidines
US3210247A (en)	1965-10-05	Anti-epileptic i-cyclohexyl-z-methyl- aiviino propane salt of phenyl ethyl barbituric acid
JPS63203691A (ja)	1988-08-23	ピペラジンカルボン酸、その製造方法およびそれを含有する医薬組成物
KR900003301B1 (ko)	1990-05-14	2-피페라지닐-4-페닐 퀴나졸린 유도체 및 그의 산염의 제조 방법
JPS5888369A (ja)	1983-05-26	新規な４−フエニルキナゾリン誘導体、その製法及びその医薬品としての利用
DE69210229T2 (de)	1996-11-14	Dihydrochinolin NMDA Antagonisten
DE69625226T2 (de)	2004-01-22	Neue n-acetylierte 4-hydroxyphenylaminen derivate mit analgetischen eigenschaften sowie diese enthaltende arzneimittel
JPS6118553B2 (ko)	1986-05-13
WO1998043638A1 (fr)	1998-10-08	Agent therapeutique pour maladies auto-immunes
JPH10507446A (ja)	1998-07-21	ビス−２−アミノピリジン類、その製造方法及び寄生虫感染を制御するためのその用途
US3629418A (en)	1971-12-21	Process for producing an anti-depressant effect with piperazine quinolines
US4755601A (en)	1988-07-05	Nonyl prenyl-N heterocyclics
US4185104A (en)	1980-01-22	Tranquillizing complexes
US3553267A (en)	1971-01-05	3-dimethylamino-1,2,3,4-tetrahydrofluorene
US3635971A (en)	1972-01-18	3 (3 4-dihydro-3-oxo-2-quinoxalinyl) propionamides
US3128278A (en)	1964-04-07	Substituted l
FR2544313A1 (fr)	1984-10-19	Les n-cycloalcoyl methyl-2 oxo-3 diaryl 5-6 as triazines, leur procede de fabrication et leur utilisation en tant que medicament
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