IE46284B1 - Disubstituted piperazines,process for their preparation and pharmaceutical compositions containing them - Google Patents
Disubstituted piperazines,process for their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IE46284B1 IE46284B1 IE2597/77A IE259777A IE46284B1 IE 46284 B1 IE46284 B1 IE 46284B1 IE 2597/77 A IE2597/77 A IE 2597/77A IE 259777 A IE259777 A IE 259777A IE 46284 B1 IE46284 B1 IE 46284B1
- Authority
- IE
- Ireland
- Prior art keywords
- piperazine
- thiadiazol
- compound according
- general formula
- group
- Prior art date
Links
- 150000004885 piperazines Chemical class 0.000 title claims abstract description 4
- 238000000034 method Methods 0.000 title claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 230000008569 process Effects 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 benzo [b] furanyl Chemical group 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims abstract description 5
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims abstract description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 25
- 125000002619 bicyclic group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- FTYYFHAEHYSEOV-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-1,3,4-thiadiazole Chemical compound C=1C=C2OCOC2=CC=1CN(CC1)CCN1C1=NN=CS1 FTYYFHAEHYSEOV-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 230000009467 reduction Effects 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 229910052717 sulfur Chemical group 0.000 abstract description 3
- 206010020772 Hypertension Diseases 0.000 abstract description 2
- 208000018737 Parkinson disease Diseases 0.000 abstract description 2
- 208000018262 Peripheral vascular disease Diseases 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 150000002431 hydrogen Chemical group 0.000 abstract description 2
- 230000001225 therapeutic effect Effects 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 2
- 239000011593 sulfur Chemical group 0.000 abstract 2
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000005605 benzo group Chemical group 0.000 abstract 1
- 125000005059 halophenyl group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- VGAQTZHPPPUQOM-UHFFFAOYSA-N 2-piperazin-1-yl-1,3,4-thiadiazole Chemical compound C1CNCCN1C1=NN=CS1 VGAQTZHPPPUQOM-UHFFFAOYSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- AXYOQFCCRRADTR-UHFFFAOYSA-N 2-methyl-5-piperazin-1-yl-1,3,4-thiadiazole Chemical compound S1C(C)=NN=C1N1CCNCC1 AXYOQFCCRRADTR-UHFFFAOYSA-N 0.000 description 7
- DWSUJONSJJTODA-UHFFFAOYSA-N 5-(chloromethyl)-1,3-benzodioxole Chemical compound ClCC1=CC=C2OCOC2=C1 DWSUJONSJJTODA-UHFFFAOYSA-N 0.000 description 7
- CWKXDPPQCVWXAG-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxine-6-carbaldehyde Chemical compound O1CCOC2=CC(C=O)=CC=C21 CWKXDPPQCVWXAG-UHFFFAOYSA-N 0.000 description 6
- DQBCRVIBTFHJLM-UHFFFAOYSA-N 2-bromo-1,3,4-thiadiazole Chemical compound BrC1=NN=CS1 DQBCRVIBTFHJLM-UHFFFAOYSA-N 0.000 description 6
- HARUWJZORCBAAL-UHFFFAOYSA-N 6-(chloromethyl)-2,3-dihydro-1,4-benzodioxine Chemical compound O1CCOC2=CC(CCl)=CC=C21 HARUWJZORCBAAL-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- NBOOZXVYXHATOW-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-ylmethyl)piperazine Chemical compound C=1C=C2OCOC2=CC=1CN1CCNCC1 NBOOZXVYXHATOW-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- NSMKWTGDPQHTDH-UHFFFAOYSA-N 2-bromo-5-methyl-1,3,4-thiadiazole Chemical compound CC1=NN=C(Br)S1 NSMKWTGDPQHTDH-UHFFFAOYSA-N 0.000 description 4
- JOFZZOBYMBDDRM-UHFFFAOYSA-N 3-methyl-5-piperazin-1-yl-1,2,4-oxadiazole Chemical compound CC1=NOC(N2CCNCC2)=N1 JOFZZOBYMBDDRM-UHFFFAOYSA-N 0.000 description 4
- 229960005235 piperonyl butoxide Drugs 0.000 description 4
- AAWXOGAYHSEQKR-UHFFFAOYSA-N 1-(1h-1,2,4-triazol-5-yl)piperazine Chemical compound C1CNCCN1C1=NNC=N1 AAWXOGAYHSEQKR-UHFFFAOYSA-N 0.000 description 3
- YUQUNWNSQDULTI-UHFFFAOYSA-N 2-bromobenzenethiol Chemical compound SC1=CC=CC=C1Br YUQUNWNSQDULTI-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 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
- 239000000370 acceptor Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 description 2
- OEQQSRKLXHARQU-UHFFFAOYSA-N 1-(4-methyl-1,2,4-triazol-3-yl)piperazine Chemical compound CN1C=NN=C1N1CCNCC1 OEQQSRKLXHARQU-UHFFFAOYSA-N 0.000 description 2
- YILAROBYBHNHHI-UHFFFAOYSA-N 3-methyl-5-piperazin-1-yl-1,2,4-thiadiazole Chemical compound CC1=NSC(N2CCNCC2)=N1 YILAROBYBHNHHI-UHFFFAOYSA-N 0.000 description 2
- HHIZISRHAQPAMY-UHFFFAOYSA-N 5-bromo-1h-1,2,4-triazole Chemical compound BrC1=NC=NN1 HHIZISRHAQPAMY-UHFFFAOYSA-N 0.000 description 2
- QDBFRHGFMDYIIT-UHFFFAOYSA-N 5-chloro-3-methyl-1,2,4-oxadiazole Chemical compound CC1=NOC(Cl)=N1 QDBFRHGFMDYIIT-UHFFFAOYSA-N 0.000 description 2
- BLGDMQAEKJZPMD-UHFFFAOYSA-N 5-piperazin-1-yl-1,2,4-thiadiazole Chemical compound C1CNCCN1C1=NC=NS1 BLGDMQAEKJZPMD-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 206010042008 Stereotypy Diseases 0.000 description 2
- 241000906446 Theraps Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 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
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 230000004899 motility Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000001305 1,2,4-triazol-3-yl group Chemical group [H]N1N=C([*])N=C1[H] 0.000 description 1
- NHFDLXFENGGSLV-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)-4-(1h-1,2,4-triazol-5-yl)piperazine Chemical compound C=1C=C2OCCOC2=CC=1CN(CC1)CCN1C=1N=CNN=1 NHFDLXFENGGSLV-UHFFFAOYSA-N 0.000 description 1
- WVVYETFQVXIRRZ-UHFFFAOYSA-N 1-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazine Chemical compound C=1C=C2OCCC2=CC=1CN1CCNCC1 WVVYETFQVXIRRZ-UHFFFAOYSA-N 0.000 description 1
- FDVCUOJHWRHXMF-UHFFFAOYSA-N 1-(naphthalen-2-ylmethyl)piperazine Chemical compound C=1C=C2C=CC=CC2=CC=1CN1CCNCC1 FDVCUOJHWRHXMF-UHFFFAOYSA-N 0.000 description 1
- MSSDTZLYNMFTKN-UHFFFAOYSA-N 1-Piperazinecarboxaldehyde Chemical compound O=CN1CCNCC1 MSSDTZLYNMFTKN-UHFFFAOYSA-N 0.000 description 1
- YTQQIHUQLOZOJI-UHFFFAOYSA-N 2,3-dihydro-1,2-thiazole Chemical compound C1NSC=C1 YTQQIHUQLOZOJI-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- CMCPVQJDXRKXLC-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-5-methyl-1,3,4-thiadiazole Chemical compound S1C(C)=NN=C1N1CCN(CC=2C=C3OCOC3=CC=2)CC1 CMCPVQJDXRKXLC-UHFFFAOYSA-N 0.000 description 1
- YKADSCGHXGSZLP-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperazin-1-yl]-1,3,4-thiadiazole Chemical compound C=1C=C2OCCOC2=CC=1CN(CC1)CCN1C1=NN=CS1 YKADSCGHXGSZLP-UHFFFAOYSA-N 0.000 description 1
- DHRAYTFCHOLFFT-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperazin-1-yl]-1,3,4-thiadiazole;methanesulfonic acid Chemical compound CS(O)(=O)=O.C=1C=C2OCCOC2=CC=1CN(CC1)CCN1C1=NN=CS1 DHRAYTFCHOLFFT-UHFFFAOYSA-N 0.000 description 1
- QRVJACGGJYPKLO-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperazin-1-yl]-5-methyl-1,3,4-thiadiazole Chemical compound S1C(C)=NN=C1N1CCN(CC=2C=C3OCCOC3=CC=2)CC1 QRVJACGGJYPKLO-UHFFFAOYSA-N 0.000 description 1
- AJSZQSPOWZPAFL-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1-benzofuran-5-ylmethyl)piperazin-1-yl]-5-methyl-1,3,4-thiadiazole Chemical compound S1C(C)=NN=C1N1CCN(CC=2C=C3CCOC3=CC=2)CC1 AJSZQSPOWZPAFL-UHFFFAOYSA-N 0.000 description 1
- KEKZRSYHEMYUJM-UHFFFAOYSA-N 2-[4-(naphthalen-2-ylmethyl)piperazin-1-yl]-1,3,4-thiadiazole Chemical compound C=1C=C2C=CC=CC2=CC=1CN(CC1)CCN1C1=NN=CS1 KEKZRSYHEMYUJM-UHFFFAOYSA-N 0.000 description 1
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
- SFHSWEGYUAJRDI-UHFFFAOYSA-N 2-piperazin-1-yl-1,3,4-thiadiazole;dihydrochloride Chemical compound Cl.Cl.C1CNCCN1C1=NN=CS1 SFHSWEGYUAJRDI-UHFFFAOYSA-N 0.000 description 1
- PYMVKLCRJYMSGC-UHFFFAOYSA-N 3-bromo-4-methyl-1,2,4-triazole Chemical compound CN1C=NN=C1Br PYMVKLCRJYMSGC-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- SWPANFDAIKLKBD-UHFFFAOYSA-N 5-(chloromethyl)-2,3-dihydro-1-benzofuran Chemical compound ClCC1=CC=C2OCCC2=C1 SWPANFDAIKLKBD-UHFFFAOYSA-N 0.000 description 1
- LUMRVIWPWKNWKY-UHFFFAOYSA-N 5-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-1,2,4-thiadiazole Chemical compound C=1C=C2OCOC2=CC=1CN(CC1)CCN1C1=NC=NS1 LUMRVIWPWKNWKY-UHFFFAOYSA-N 0.000 description 1
- BUROIJFSDIAKGA-UHFFFAOYSA-N 5-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-3-methyl-1,2,4-oxadiazole Chemical compound CC1=NOC(N2CCN(CC=3C=C4OCOC4=CC=3)CC2)=N1 BUROIJFSDIAKGA-UHFFFAOYSA-N 0.000 description 1
- YZLBLASJNSIIGY-UHFFFAOYSA-N 5-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-3-methyl-1,2,4-thiadiazole Chemical compound CC1=NSC(N2CCN(CC=3C=C4OCOC4=CC=3)CC2)=N1 YZLBLASJNSIIGY-UHFFFAOYSA-N 0.000 description 1
- GDUXGRIGCARDMZ-UHFFFAOYSA-N 5-[4-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)piperazin-1-yl]-3-methyl-1,2,4-thiadiazole Chemical compound CC1=NSC(N2CCN(CC=3C=C4OCCOC4=CC=3)CC2)=N1 GDUXGRIGCARDMZ-UHFFFAOYSA-N 0.000 description 1
- UBUUGFLYVXDUPG-UHFFFAOYSA-N 5-bromo-1,2,4-thiadiazole Chemical compound BrC1=NC=NS1 UBUUGFLYVXDUPG-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- ILTLLMVRPBXCSX-UHFFFAOYSA-N 5-chloro-3-methyl-1,2,4-thiadiazole Chemical compound CC1=NSC(Cl)=N1 ILTLLMVRPBXCSX-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
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 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
- 229920000168 Microcrystalline cellulose Polymers 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000008431 aliphatic amides Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000000648 anti-parkinson Effects 0.000 description 1
- 239000000939 antiparkinson agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose 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
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 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
- 230000000926 neurological effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 description 1
- 229960002195 perazine Drugs 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical class [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- 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
-
- 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
-
- 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
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/14—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/08—1,2,4-Thiadiazoles; Hydrogenated 1,2,4-thiadiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB54398/76A GB1560084A (en) | 1976-12-31 | 1976-12-31 | Disubstituted piperazines processes for their preparation and pharmaceutical mompositions containing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE46284L IE46284L (en) | 1978-06-30 |
| IE46284B1 true IE46284B1 (en) | 1983-04-20 |
Family
ID=10470884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2597/77A IE46284B1 (en) | 1976-12-31 | 1977-12-21 | Disubstituted piperazines,process for their preparation and pharmaceutical compositions containing them |
Country Status (24)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2418798A1 (fr) * | 1978-03-03 | 1979-09-28 | Science Union & Cie | Nouvelles piperazines disubstituees, leurs procedes de preparation et les compositions pharmaceutiques les renfermant |
| US4421753A (en) * | 1982-01-15 | 1983-12-20 | American Cyanamid Company | 1-(5-Amino-4H-1,2,4-triazol-3-yl)-4-substituted-piperazines |
| FR2519986A1 (fr) * | 1982-01-21 | 1983-07-22 | Adir | Nouveaux derives de benzodioxine, leurs procedes de preparation et les compositions pharmaceutiques les renfermant |
| US5776963A (en) * | 1989-05-19 | 1998-07-07 | Hoechst Marion Roussel, Inc. | 3-(heteroaryl)-1- (2,3-dihydro-1h-isoindol-2-yl)alkyl!pyrrolidines and 3-(heteroaryl)-1- (2,3-dihydro-1h-indol-1-yl)alkyl!pyrrolidines and related compounds and their therapeutic untility |
| US5637592A (en) * | 1994-07-12 | 1997-06-10 | Janssen Pharmaceutica N.V. | Acyl derivatives of azolones |
| FR2799464B1 (fr) * | 1999-10-12 | 2001-12-28 | Norchim | Procede de fabrication de piperonyl piperazine par animation reductive |
| EP3119774A1 (en) | 2014-03-17 | 2017-01-25 | reMynd NV | Oxadiazole compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1595923A1 (de) * | 1965-02-20 | 1969-11-27 | Merck Ag E | 1-Aralkyl-4-(thiazolyl-2)-piperazine und Verfahren zu ihrer Herstellung |
| GB1307256A (en) * | 1970-09-15 | 1973-02-14 | Science Union & Cie | Piperazine derivatives and a process for their preparation |
| GB1369379A (en) * | 1972-04-07 | 1974-10-09 | Science Union & Cie | Benzodioxole derivatives and processes for preparing them |
| GB1407552A (en) * | 1973-04-02 | 1975-09-24 | Science Union & Cie | Disubstituted piperazines processes for their preparation and pharmaceutical compositions containing them |
-
1976
- 1976-12-31 GB GB54398/76A patent/GB1560084A/en not_active Expired
-
1977
- 1977-12-21 IE IE2597/77A patent/IE46284B1/en unknown
- 1977-12-22 CA CA293,755A patent/CA1100968A/fr not_active Expired
- 1977-12-22 YU YU03043/77A patent/YU304377A/xx unknown
- 1977-12-22 DK DK572977A patent/DK572977A/da not_active Application Discontinuation
- 1977-12-22 FR FR7738727A patent/FR2376148A1/fr active Granted
- 1977-12-23 AT AT927577A patent/AT358591B/de not_active IP Right Cessation
- 1977-12-24 OA OA56358A patent/OA05840A/xx unknown
- 1977-12-27 DE DE19772758314 patent/DE2758314A1/de not_active Ceased
- 1977-12-27 US US05/864,204 patent/US4177272A/en not_active Expired - Lifetime
- 1977-12-27 JP JP15854677A patent/JPS5384984A/ja active Granted
- 1977-12-27 SU SU772558955A patent/SU703021A3/ru active
- 1977-12-28 ZA ZA00777680A patent/ZA777680B/xx unknown
- 1977-12-29 SE SE7714884A patent/SE7714884L/xx unknown
- 1977-12-29 IL IL53714A patent/IL53714A/xx unknown
- 1977-12-29 AR AR270568A patent/AR216931A1/es active
- 1977-12-29 GR GR55066A patent/GR62407B/el unknown
- 1977-12-29 AU AU32045/77A patent/AU513087B2/en not_active Expired
- 1977-12-29 PH PH20605A patent/PH14321A/en unknown
- 1977-12-30 BE BE184051A patent/BE862568A/xx unknown
- 1977-12-30 PT PT67486A patent/PT67486B/pt unknown
- 1977-12-30 DD DD7700203032A patent/DD133802A5/xx unknown
- 1977-12-31 NL NL7714628A patent/NL7714628A/xx not_active Application Discontinuation
-
1978
- 1978-01-05 NZ NZ186158A patent/NZ186158A/xx unknown
- 1978-12-21 SU SU782699397A patent/SU793397A3/ru active
-
1979
- 1979-02-27 AR AR275635A patent/AR217144A1/es active
- 1979-02-27 AR AR275634A patent/AR217143A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| ZA777680B (en) | 1978-10-25 |
| SU703021A3 (ru) | 1979-12-05 |
| IE46284L (en) | 1978-06-30 |
| ATA927577A (de) | 1980-02-15 |
| GB1560084A (en) | 1980-01-30 |
| YU304377A (en) | 1983-01-21 |
| OA05840A (fr) | 1981-05-31 |
| GR62407B (en) | 1979-04-11 |
| AR217144A1 (es) | 1980-02-29 |
| AR216931A1 (es) | 1980-02-15 |
| FR2376148B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-05-29 |
| IL53714A (en) | 1981-07-31 |
| DK572977A (da) | 1978-07-01 |
| AU513087B2 (en) | 1980-11-13 |
| IL53714A0 (en) | 1978-03-10 |
| US4177272A (en) | 1979-12-04 |
| PH14321A (en) | 1981-05-27 |
| JPS5384984A (en) | 1978-07-26 |
| CA1100968A (fr) | 1981-05-12 |
| FR2376148A1 (fr) | 1978-07-28 |
| AR217143A1 (es) | 1980-02-29 |
| NL7714628A (nl) | 1978-07-04 |
| SU793397A3 (ru) | 1980-12-30 |
| DD133802A5 (de) | 1979-01-24 |
| JPS6149314B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1986-10-29 |
| AT358591B (de) | 1980-09-25 |
| PT67486A (fr) | 1978-01-01 |
| SE7714884L (sv) | 1978-07-02 |
| NZ186158A (en) | 1980-03-05 |
| BE862568A (fr) | 1978-06-30 |
| PT67486B (fr) | 1979-05-30 |
| AU3204577A (en) | 1979-07-05 |
| DE2758314A1 (de) | 1978-07-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4374248A (en) | 3,4-Disubstituted-1,2,5-thiadiazole-1-oxide compounds | |
| US3766180A (en) | 3-heterocyclicamino-4-chloro-1,2,5-thiadiazoles | |
| US4394508A (en) | Chemical compounds | |
| JP5443343B2 (ja) | ピペリジン／ピペラジン誘導体 | |
| HU211705A9 (en) | Piperidine compounds, their preparation and use | |
| EP2161266A1 (en) | Benzofuran derivatives as orexin receptor antagonists | |
| AU714701B2 (en) | Novel thiophene derivative and pharmaceutical composition thereof | |
| IE58084B1 (en) | Antidepressant 1,2,4-triazolone compounds | |
| IE46284B1 (en) | Disubstituted piperazines,process for their preparation and pharmaceutical compositions containing them | |
| SU1297729A3 (ru) | Способ получени 7-замещенных производных теофиллина или их кислотно-аддитивных фармацевтически приемлемых солей | |
| EP0359790B1 (en) | 1,4-benzoxazine and 1,4-benzothiazine derivatives and process for their preparation | |
| US4824833A (en) | Benzoxazine derivatives | |
| JPH0568451B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| IE54428B1 (en) | New benzodioxin derivatives, processes for their preparation and pharmaceutical compositions containing them | |
| US3954765A (en) | Piperazines derivatives | |
| JPS6136755B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| CA2111442A1 (en) | Aminoalkyl-substituted 2-amino-5-mercaptothiadiazoles the preparation and use thereof | |
| US4380639A (en) | Substituted 1,2,5-thiadiazole derivatives | |
| US4112092A (en) | 1-Naphthylmethyl-4-(thiazolyl-2)-piperazines | |
| US4436914A (en) | Benzodioxane-imidazoline compounds as antihypertensives | |
| GB2129426A (en) | Compounds of thiatriazines | |
| WO1982001874A1 (en) | 2-(1,4-benzodoioxan-2-ylalkyl)imidazoles useful as antidepressants | |
| US3538087A (en) | Oxadiazole derivatives | |
| GB2055043A (en) | Pharmaceutical compositions containing substituted biuret compounds | |
| JP2986184B2 (ja) | 二環性トリアゾール誘導体 |