JPS6353162B2 - - Google Patents

Info

Publication number: JPS6353162B2
Authority: JP; Japan
Prior art keywords: formula; compound; hydrogen; hydroxy; mol
Prior art date: 1978-06-06
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

JP54071796A

Other languages

English (en)

Japanese (ja)

Other versions

JPS54160389A (en

Inventor

Ratsutoreru Rudorufu

Barutoman Uiruherumu

Geruharutsu Heruman

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.)

Hoechst AG

Original Assignee

Hoechst AG

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.)

1978-06-06

Filing date

1979-06-05

Publication date

1988-10-21

1979-06-05 Application filed by Hoechst AG filed Critical Hoechst AG

1979-12-19 Publication of JPS54160389A publication Critical patent/JPS54160389A/ja

1988-10-21 Publication of JPS6353162B2 publication Critical patent/JPS6353162B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 46
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
230000037396 body weight Effects 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 5
241001465754 Metazoa Species 0.000 claims description 4
239000003176 neuroleptic agent Substances 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
238000000034 method Methods 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
241000699670 Mus sp. Species 0.000 description 16
-1 n- butyl Chemical group 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 13
239000002904 solvent Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
238000004519 manufacturing process Methods 0.000 description 11
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
229910000027 potassium carbonate Inorganic materials 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
229960000632 dexamfetamine Drugs 0.000 description 5
229940079593 drug Drugs 0.000 description 5
239000003814 drug Substances 0.000 description 5
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
239000000155 melt Substances 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 3
AVJKDKWRVSSJPK-UHFFFAOYSA-N 1-(4-fluorophenyl)piperazine Chemical compound C1=CC(F)=CC=C1N1CCNCC1 AVJKDKWRVSSJPK-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
229940025084 amphetamine Drugs 0.000 description 3
238000004458 analytical method Methods 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
238000000354 decomposition reaction Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
230000006742 locomotor activity Effects 0.000 description 3
UNEIHNMKASENIG-UHFFFAOYSA-N para-chlorophenylpiperazine Chemical compound C1=CC(Cl)=CC=C1N1CCNCC1 UNEIHNMKASENIG-UHFFFAOYSA-N 0.000 description 3
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
229920000053 polysorbate 80 Polymers 0.000 description 3
239000000126 substance Substances 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
239000003981 vehicle Substances 0.000 description 3
238000005303 weighing Methods 0.000 description 3
YVSXZYNMCGXGND-UHFFFAOYSA-N 5-(3-bromopropoxy)-1-methyl-3h-indol-2-one Chemical compound BrCCCOC1=CC=C2N(C)C(=O)CC2=C1 YVSXZYNMCGXGND-UHFFFAOYSA-N 0.000 description 2
241000251468 Actinopterygii Species 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
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 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
241000699666 Mus <mouse, genus> Species 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
241000700159 Rattus Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 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
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000004899 motility Effects 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000000243 solution Substances 0.000 description 2
229950001675 spiperone Drugs 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 2
230000001256 tonic effect 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
JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
MHJCONKUOOYWLN-UHFFFAOYSA-N (4-ethoxy-4-methoxy-4-propan-2-yloxybutyl) hypofluorite Chemical compound COC(CCCOF)(OC(C)C)OCC MHJCONKUOOYWLN-UHFFFAOYSA-N 0.000 description 1
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
WLXGQMVCYPUOLM-UHFFFAOYSA-N 1-hydroxyethanesulfonic acid Chemical group CC(O)S(O)(=O)=O WLXGQMVCYPUOLM-UHFFFAOYSA-N 0.000 description 1
RSQUAQMIGSMNNE-UHFFFAOYSA-N 1-methyl-3h-indol-2-one Chemical compound C1=CC=C2N(C)C(=O)CC2=C1 RSQUAQMIGSMNNE-UHFFFAOYSA-N 0.000 description 1
PGZVFRAEAAXREB-UHFFFAOYSA-N 2,2-dimethylpropanoyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC(=O)C(C)(C)C PGZVFRAEAAXREB-UHFFFAOYSA-N 0.000 description 1
AOYDKMRAVTUTFE-UHFFFAOYSA-N 5-(2-hydroxy-3-piperazin-1-ylpropoxy)-1-methyl-3h-indol-2-one Chemical compound C=1C=C2N(C)C(=O)CC2=CC=1OCC(O)CN1CCNCC1 AOYDKMRAVTUTFE-UHFFFAOYSA-N 0.000 description 1
WNXHCNSQQOOOND-UHFFFAOYSA-N 5-(3-amino-2-hydroxypropoxy)-1-methyl-3h-indol-2-one Chemical compound NCC(O)COC1=CC=C2N(C)C(=O)CC2=C1 WNXHCNSQQOOOND-UHFFFAOYSA-N 0.000 description 1
XELGSFSJVFZDNQ-UHFFFAOYSA-N 5-[3-[bis(2-chloroethyl)amino]-2-hydroxypropoxy]-1-methyl-3h-indol-2-one Chemical compound ClCCN(CCCl)CC(O)COC1=CC=C2N(C)C(=O)CC2=C1 XELGSFSJVFZDNQ-UHFFFAOYSA-N 0.000 description 1
JUPNUOIZFNVFOB-UHFFFAOYSA-N 5-hydroxy-1-methyl-3h-indol-2-one Chemical compound OC1=CC=C2N(C)C(=O)CC2=C1 JUPNUOIZFNVFOB-UHFFFAOYSA-N 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
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical group OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 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
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 description 1
229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 description 1
206010061216 Infarction Diseases 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
241000124008 Mammalia Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-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
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
235000019486 Sunflower oil Nutrition 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
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
239000010775 animal oil Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N beta-hydroxyethanesulfonic acid Chemical group OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
230000004531 blood pressure lowering effect Effects 0.000 description 1
210000004556 brain Anatomy 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
238000004364 calculation method Methods 0.000 description 1
244000309466 calf Species 0.000 description 1
239000002775 capsule Substances 0.000 description 1
210000000170 cell membrane Anatomy 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 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
239000003026 cod liver oil Substances 0.000 description 1
235000012716 cod liver oil Nutrition 0.000 description 1
238000004590 computer program Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
230000007574 infarction Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000019359 magnesium stearate 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
239000000463 material Substances 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
JMABIVFAGAEUEG-UHFFFAOYSA-N n-(2-chloroethyl)-2-methoxyaniline Chemical compound COC1=CC=CC=C1NCCCl JMABIVFAGAEUEG-UHFFFAOYSA-N 0.000 description 1
210000001577 neostriatum Anatomy 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
150000004885 piperazines Chemical class 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
239000004033 plastic Substances 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
DKGZKTPJOSAWFA-UHFFFAOYSA-N spiperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCC2(C(NCN2C=2C=CC=CC=2)=O)CC1 DKGZKTPJOSAWFA-UHFFFAOYSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000002600 sunflower oil Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Cardiology (AREA)
Anesthesiology (AREA)
Heart & Thoracic Surgery (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Quinoline Compounds (AREA)
Indole Compounds (AREA)

JP7179679A 1978-06-06 1979-06-05 Novel substituted phenylpiperazine derivative and its manufacture Granted JPS54160389A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782824677 DE2824677A1 (de)	1978-06-06	1978-06-06	Neue substituierte phenylpiperazinderivate und verfahren zu deren herstellung

Publications (2)

Publication Number	Publication Date
JPS54160389A JPS54160389A (en)	1979-12-19
JPS6353162B2 true JPS6353162B2 (ru)	1988-10-21

Family

ID=6041107

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7179679A Granted JPS54160389A (en)	1978-06-06	1979-06-05	Novel substituted phenylpiperazine derivative and its manufacture

Country Status (3)

Country	Link
JP (1)	JPS54160389A (ru)
DE (1)	DE2824677A1 (ru)
ZA (1)	ZA792783B (ru)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS56122351A (en) *	1980-02-29	1981-09-25	Otsuka Pharmaceut Co Ltd	Oxyindole derivative
JPS56140970A (en) *	1980-04-04	1981-11-04	Ronza Chem:Kk	Preparation of indole derivative
DE3026331A1 (de) *	1980-07-11	1982-02-18	Basf Ag, 6700 Ludwigshafen	Indanon-oxyalkyl-piperazinderivate, ihre herstellung und diese enthaltende pharmazeutische zubereitung
DE3101502A1 (de) *	1981-01-19	1982-08-26	Basf Ag, 6700 Ludwigshafen	Phenylpiperazinderivate von hetarylphenolen und hetarylanilinen, ihre hersttellung und diese enthaltendetherapeutische mittel
DE3424685A1 (de) *	1984-07-05	1986-02-06	Beiersdorf Ag, 2000 Hamburg	Neue substituierte phenylpiperazinyl-propanole, verfahren zu ihrer herstellung und ihre verwendung sowie diese verbindungen enthaltende zubereitungen
JPS62135423A (ja) *	1985-12-09	1987-06-18	Otsuka Pharmaceut Co Ltd	低酸素症改善剤
JPS63290821A (ja) *	1987-05-25	1988-11-28	Otsuka Pharmaceut Co Ltd	抗不整脈剤
DE3721260A1 (de) *	1987-06-27	1989-01-12	Beiersdorf Ag	Neue indolylpropanole, verfahren zu ihrer herstellung und ihre verwendung sowie die verbindungen enthaltende zubereitungen
JPH07285940A (ja) *	1988-08-10	1995-10-31	Otsuka Pharmaceut Co Ltd	カルボスチリル誘導体
JP2608813B2 (ja) *	1991-05-31	1997-05-14	大塚製薬株式会社	アカシジア治療剤
JPH07252153A (ja) *	1995-01-25	1995-10-03	Otsuka Pharmaceut Co Ltd	抗不整脈剤
JP2987484B2 (ja) *	1995-03-16	1999-12-06	大塚製薬株式会社	カルボスチリル誘導体の製造方法
WO2009137843A2 (en) *	2008-05-09	2009-11-12	Emory University	Nmda receptor antagonists for the treatment of neuropsychiatric disorders

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1424571A (en) *	1921-10-19	1922-08-01	Kaufmann Siegfried Henry	Manicure case

1978
- 1978-06-06 DE DE19782824677 patent/DE2824677A1/de not_active Withdrawn
1979
- 1979-06-05 ZA ZA792783A patent/ZA792783B/xx unknown
- 1979-06-05 JP JP7179679A patent/JPS54160389A/ja active Granted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1424571A (en) *	1921-10-19	1922-08-01	Kaufmann Siegfried Henry	Manicure case

Also Published As

Publication number	Publication date
DE2824677A1 (de)	1979-12-20
JPS54160389A (en)	1979-12-19
ZA792783B (en)	1980-06-25

Publication	Publication Date	Title
RU2075478C1 (ru)	1997-03-20	2-(4-этил-1-пиперазинил)-4-(4-фторфенил)-5,6,7,8,9,10-гексагидроциклоокта (в) пиридин или его кислотно-аддитивная соль
SU1367857A3 (ru)	1988-01-15	Способ получени карбостирильных производных
US3780040A (en)	1973-12-18	2-substituted-3,4-dihydroquinazolines
US3669968A (en)	1972-06-13	Trialkoxy quinazolines
SU1340589A3 (ru)	1987-09-23	Способ получени 2-(4-замещенных пиперазино-4-амино-6,7-диметокси)хинолинов или их гидрохлоридов
KR880002232B1 (ko)	1988-10-20	퀴놀린 유도체와 그 염의 제조방법
US4059621A (en)	1977-11-22	Substituted benzamido propanolamines
US4234584A (en)	1980-11-18	Substituted phenylpiperazine derivatives
JPS6353162B2 (ru)	1988-10-21
JPS6331465B2 (ru)	1988-06-23
JPH04982B2 (ru)	1992-01-09
JPH0440347B2 (ru)	1992-07-02
HU193258B (en)	1987-08-28	Process for preparing piperazine derivatives and acid addition salts thereof
EP0133244A2 (en)	1985-02-20	Phenylquinolinecarboxylic acids and derivatives as antitumor agents
JPS6230780A (ja)	1987-02-09	１，７−ナフチリジン誘導体及びこれを含有する薬剤
JPH1171351A (ja)	1999-03-16	置換キノロン誘導体及びこれを含有する医薬
EP0111226B1 (en)	1987-09-16	Carboximide derivatives, process for their production and medicines containing same
US5084456A (en)	1992-01-28	Oxazolopyridine compounds
CA1207774A (en)	1986-07-15	1-phenylindazol-3-one compounds, a method of preparing them and pharmaceutical compositions containing these compounds
US4716161A (en)	1987-12-29	Phenylpiperazine derivatives and their acid addition salts
RU2140919C1 (ru)	1999-11-10	Производные 8-трифторметилхинолинкарбоновой кислоты, фармацевтическая композиция и способ ингибирования вируса иммунодефицита
US4983606A (en)	1991-01-08	Pharmaceutically-active phthalazine compounds
US4746661A (en)	1988-05-24	Phenylpiperazine propyloxyquinolinones and methods for sedating and inhibiting aggression in livestock therewith
JPS6130588A (ja)	1986-02-12	ベンゾ〔ｃ〕〔１，８〕ナフチリジン、その製造方法及びその使用、並びにこれらの化合物を含有する調製剤
US3562280A (en)	1971-02-09	Substituted 1,2,3,4-tetrahydroisoquinolines