NO310597B1 - Anvendelse av oksadiazol- og tiadiazolforbindelser til fremstilling av farmasöytiske preparater for behandling avschizofreni eller schizofreniforme sykdommer - Google Patents

Info

Publication number

NO310597B1

NO310597B1 NO19960620A NO960620A NO310597B1 NO 310597 B1 NO310597 B1 NO 310597B1 NO 19960620 A NO19960620 A NO 19960620A NO 960620 A NO960620 A NO 960620A NO 310597 B1 NO310597 B1 NO 310597B1

Authority

NO

Norway

Prior art keywords

thiadiazol

azabicyclo

octane

exo

endo

Prior art date

1993-08-19

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• 238000011282 treatment Methods 0.000 title claims description 20
• 201000000980 schizophrenia Diseases 0.000 title claims description 17
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 title claims description 6
• 239000000825 pharmaceutical preparation Substances 0.000 title claims description 6
• 208000020186 Schizophreniform disease Diseases 0.000 title claims description 5
• 238000002360 preparation method Methods 0.000 title description 8
• 150000004867 thiadiazoles Chemical class 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims description 260
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 80
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 37
• 229910052739 hydrogen Inorganic materials 0.000 claims description 15
• -1 -CHO Chemical group 0.000 claims description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
• 150000003839 salts Chemical class 0.000 claims description 14
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 12
• 239000001257 hydrogen Substances 0.000 claims description 12
• 229910052736 halogen Inorganic materials 0.000 claims description 10
• 150000002367 halogens Chemical group 0.000 claims description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims description 9
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 9
• CTYXSVWHVHZAFK-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-chloro-1,2,5-thiadiazole Chemical compound ClC1=NSN=C1C1C(CC2)CCN2C1 CTYXSVWHVHZAFK-UHFFFAOYSA-N 0.000 claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• 150000002431 hydrogen Chemical group 0.000 claims description 8
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• KPKPATRJMXVDFB-UHFFFAOYSA-N 3-chloro-4-(3-chloro-1-azabicyclo[2.2.2]octan-3-yl)-1,2,5-thiadiazole Chemical compound ClC1=NSN=C1C1(Cl)C(CC2)CCN2C1 KPKPATRJMXVDFB-UHFFFAOYSA-N 0.000 claims description 5
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• 229910052717 sulfur Chemical group 0.000 claims description 5
• AAEGLEOFPNYRSB-UHFFFAOYSA-N 3-chloro-4-(4-chloro-1-azabicyclo[3.3.1]non-3-en-3-yl)-1,2,5-thiadiazole Chemical compound ClC1=NSN=C1C(C1)=C(Cl)C2CN1CCC2 AAEGLEOFPNYRSB-UHFFFAOYSA-N 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 125000003118 aryl group Chemical group 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 150000001721 carbon Chemical group 0.000 claims description 4
• 239000001301 oxygen Substances 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• 239000011593 sulfur Chemical group 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• WZZPXVURFDJHGI-UHFFFAOYSA-N vedaclidine Chemical compound CCCCSC1=NSN=C1C1C(CC2)CCN2C1 WZZPXVURFDJHGI-UHFFFAOYSA-N 0.000 claims description 4
• GCJYAANOIMVFFK-UHFFFAOYSA-N 3-(4-chloro-1-azabicyclo[3.3.1]non-3-en-3-yl)-4-propoxy-1,2,5-thiadiazole Chemical compound CCCOC1=NSN=C1C(C1)=C(Cl)C2CN1CCC2 GCJYAANOIMVFFK-UHFFFAOYSA-N 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• YCBSHDKATAPNIA-UHFFFAOYSA-N non-3-ene Chemical compound CCCCCC=CCC YCBSHDKATAPNIA-UHFFFAOYSA-N 0.000 claims description 3
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
• ZLAUVFSNIFHZKD-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-(4-chlorobutylsulfanyl)-1,2,5-thiadiazole Chemical compound ClCCCCSC1=NSN=C1C1C(CC2)CCN2C1 ZLAUVFSNIFHZKD-UHFFFAOYSA-N 0.000 claims description 2
• BBEFXLQIFQWHHD-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-butylsulfonyl-1,2,5-thiadiazole Chemical compound CCCCS(=O)(=O)C1=NSN=C1C1C(CC2)CCN2C1 BBEFXLQIFQWHHD-UHFFFAOYSA-N 0.000 claims description 2
• IWUNBZVYYZUQMC-UHFFFAOYSA-N 3-(1-azabicyclo[3.2.1]octan-5-yl)-4-chloro-1,2,5-thiadiazole Chemical compound ClC1=NSN=C1C1(CCC2)CN2CC1 IWUNBZVYYZUQMC-UHFFFAOYSA-N 0.000 claims description 2
• CIISKBGWJOIJOL-UHFFFAOYSA-N 3-(1-azabicyclo[3.3.1]non-3-en-3-yl)-4-methoxy-1,2,5-thiadiazole Chemical compound COC1=NSN=C1C(C1)=CC2CN1CCC2 CIISKBGWJOIJOL-UHFFFAOYSA-N 0.000 claims description 2
• ZUBBXJQRWCNGSG-UHFFFAOYSA-N 3-butoxy-4-(4-chloro-1-azabicyclo[3.3.1]non-3-en-3-yl)-1,2,5-thiadiazole Chemical compound CCCCOC1=NSN=C1C(C1)=C(Cl)C2CN1CCC2 ZUBBXJQRWCNGSG-UHFFFAOYSA-N 0.000 claims description 2
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims description 2
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
• 238000004519 manufacturing process Methods 0.000 claims description 2
• 125000001624 naphthyl group Chemical group 0.000 claims description 2
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
• ZUGCUOYDOMJOIN-UHFFFAOYSA-N 1-[[4-(1-azabicyclo[2.2.2]octan-3-yl)-1,2,5-thiadiazol-3-yl]sulfanyl]butan-2-ol Chemical compound CCC(O)CSC1=NSN=C1C1C(CC2)CCN2C1 ZUGCUOYDOMJOIN-UHFFFAOYSA-N 0.000 claims 1
• SLUZSJOQQYWWSX-UHFFFAOYSA-N 1-[[4-(1-azabicyclo[2.2.2]octan-3-yl)-1,2,5-thiadiazol-3-yl]sulfanyl]butan-2-one Chemical compound CCC(=O)CSC1=NSN=C1C1C(CC2)CCN2C1 SLUZSJOQQYWWSX-UHFFFAOYSA-N 0.000 claims 1
• ORSNGBROJOASLE-UHFFFAOYSA-N 2-[[4-(1-azabicyclo[2.2.2]octan-3-yl)-1,2,5-thiadiazol-3-yl]sulfanyl]acetonitrile Chemical compound N#CCSC1=NSN=C1C1C(CC2)CCN2C1 ORSNGBROJOASLE-UHFFFAOYSA-N 0.000 claims 1
• ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 claims 1
• OMMVENYKIUNJOR-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]oct-2-en-3-yl)-4-hexoxy-1,2,5-thiadiazole Chemical compound CCCCCCOC1=NSN=C1C1=CN2CCC1CC2 OMMVENYKIUNJOR-UHFFFAOYSA-N 0.000 claims 1
• XBXKQDRKUIAAIL-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]oct-2-en-3-yl)-4-methoxy-1,2,5-thiadiazole Chemical compound COC1=NSN=C1C1=CN2CCC1CC2 XBXKQDRKUIAAIL-UHFFFAOYSA-N 0.000 claims 1
• SUIIVXPBOGTCLJ-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-1,2,5-thiadiazole Chemical compound C1CN(C2)CCC1C2C=1C=NSN=1 SUIIVXPBOGTCLJ-UHFFFAOYSA-N 0.000 claims 1
• AFPOWWZKNCEBKY-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-(2-methoxyethylsulfanyl)-1,2,5-thiadiazole Chemical compound COCCSC1=NSN=C1C1C(CC2)CCN2C1 AFPOWWZKNCEBKY-UHFFFAOYSA-N 0.000 claims 1
• RKSYRMFBSVLYIS-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-(2-methylpropylsulfanyl)-1,2,5-thiadiazole Chemical compound CC(C)CSC1=NSN=C1C1C(CC2)CCN2C1 RKSYRMFBSVLYIS-UHFFFAOYSA-N 0.000 claims 1
• ADDANRIXDNPMJE-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-(2-phenoxyethylsulfanyl)-1,2,5-thiadiazole Chemical compound N=1SN=C(C2C3CCN(CC3)C2)C=1SCCOC1=CC=CC=C1 ADDANRIXDNPMJE-UHFFFAOYSA-N 0.000 claims 1
• CSQZGLBQPMPLJG-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-(3-methylbutoxy)-1,2,5-thiadiazole Chemical compound CC(C)CCOC1=NSN=C1C1C(CC2)CCN2C1 CSQZGLBQPMPLJG-UHFFFAOYSA-N 0.000 claims 1
• JHQNNOUISOQMFV-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-(3-methylbutylsulfanyl)-1,2,5-thiadiazole Chemical compound CC(C)CCSC1=NSN=C1C1C(CC2)CCN2C1 JHQNNOUISOQMFV-UHFFFAOYSA-N 0.000 claims 1
• SVAVYRNWONVTRG-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-(3-phenylpropylsulfanyl)-1,2,5-thiadiazole Chemical compound N=1SN=C(C2C3CCN(CC3)C2)C=1SCCCC1=CC=CC=C1 SVAVYRNWONVTRG-UHFFFAOYSA-N 0.000 claims 1
• CDPOEVJIADYBDO-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-(3-thiophen-2-ylpropoxy)-1,2,5-thiadiazole Chemical compound N=1SN=C(C2C3CCN(CC3)C2)C=1OCCCC1=CC=CS1 CDPOEVJIADYBDO-UHFFFAOYSA-N 0.000 claims 1
• XXLAHLWLBSZYCG-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-(3-thiophen-2-ylpropylsulfanyl)-1,2,5-thiadiazole Chemical compound N=1SN=C(C2C3CCN(CC3)C2)C=1SCCCC1=CC=CS1 XXLAHLWLBSZYCG-UHFFFAOYSA-N 0.000 claims 1
• PNUHPRXOKICIPB-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-(cyclopropylmethylsulfanyl)-1,2,5-thiadiazole Chemical compound N=1SN=C(C2C3CCN(CC3)C2)C=1SCC1CC1 PNUHPRXOKICIPB-UHFFFAOYSA-N 0.000 claims 1
• ZOUYLBLUUMJTED-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-(pyridin-4-ylmethylsulfanyl)-1,2,5-thiadiazole Chemical compound N=1SN=C(C2C3CCN(CC3)C2)C=1SCC1=CC=NC=C1 ZOUYLBLUUMJTED-UHFFFAOYSA-N 0.000 claims 1
• UGYHELGVXXXIRC-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-[(3-phenoxyphenyl)methoxy]-1,2,5-thiadiazole Chemical compound N=1SN=C(C2C3CCN(CC3)C2)C=1OCC(C=1)=CC=CC=1OC1=CC=CC=C1 UGYHELGVXXXIRC-UHFFFAOYSA-N 0.000 claims 1
• QPYQPZBDWBQMGL-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-[(4-ethylphenyl)methoxy]-1,2,5-thiadiazole Chemical compound C1=CC(CC)=CC=C1COC1=NSN=C1C1C(CC2)CCN2C1 QPYQPZBDWBQMGL-UHFFFAOYSA-N 0.000 claims 1
• UJXWWHIVPSILDS-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-[(4-fluorophenyl)methylsulfanyl]-1,2,5-thiadiazole Chemical compound C1=CC(F)=CC=C1CSC1=NSN=C1C1C(CC2)CCN2C1 UJXWWHIVPSILDS-UHFFFAOYSA-N 0.000 claims 1
• JSHMHTPKMSXMIK-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-[3-(1-methyltetrazol-5-yl)sulfanylbutylsulfanyl]-1,2,5-thiadiazole Chemical compound N=1SN=C(C2C3CCN(CC3)C2)C=1SCCC(C)SC1=NN=NN1C JSHMHTPKMSXMIK-UHFFFAOYSA-N 0.000 claims 1
• CKHYDSUIUPRVGR-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-butan-2-ylsulfanyl-1,2,5-thiadiazole Chemical compound CCC(C)SC1=NSN=C1C1C(CC2)CCN2C1 CKHYDSUIUPRVGR-UHFFFAOYSA-N 0.000 claims 1
• YDQPNPWAZMGKGZ-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-butoxy-1,2,5-thiadiazole Chemical compound CCCCOC1=NSN=C1C1C(CC2)CCN2C1 YDQPNPWAZMGKGZ-UHFFFAOYSA-N 0.000 claims 1
• YPKJBZLHKQPDGL-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-ethoxy-1,2,5-thiadiazole Chemical compound CCOC1=NSN=C1C1C(CC2)CCN2C1 YPKJBZLHKQPDGL-UHFFFAOYSA-N 0.000 claims 1
• LHKIDBKDCVOYCD-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-ethylsulfanyl-1,2,5-thiadiazole Chemical compound CCSC1=NSN=C1C1C(CC2)CCN2C1 LHKIDBKDCVOYCD-UHFFFAOYSA-N 0.000 claims 1
• FKZXBPDCOICVIW-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-heptylsulfanyl-1,2,5-thiadiazole Chemical compound CCCCCCCSC1=NSN=C1C1C(CC2)CCN2C1 FKZXBPDCOICVIW-UHFFFAOYSA-N 0.000 claims 1
• RABAVFRLCCSEQJ-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-hex-3-enoxy-1,2,5-thiadiazole Chemical compound CCC=CCCOC1=NSN=C1C1C(CC2)CCN2C1 RABAVFRLCCSEQJ-UHFFFAOYSA-N 0.000 claims 1
• HPSLIXDSEYRXTI-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-hexoxy-1,2,5-thiadiazole Chemical compound CCCCCCOC1=NSN=C1C1C(CC2)CCN2C1 HPSLIXDSEYRXTI-UHFFFAOYSA-N 0.000 claims 1
• GWMZXCMXHFDDJT-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-hexylsulfanyl-1,2,5-thiadiazole Chemical compound CCCCCCSC1=NSN=C1C1C(CC2)CCN2C1 GWMZXCMXHFDDJT-UHFFFAOYSA-N 0.000 claims 1
• LESMWVRPUVIAAY-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-pentoxy-1,2,5-thiadiazole Chemical compound CCCCCOC1=NSN=C1C1C(CC2)CCN2C1 LESMWVRPUVIAAY-UHFFFAOYSA-N 0.000 claims 1
• CDHAUECRXULZKZ-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-propoxy-1,2,5-thiadiazole Chemical compound CCCOC1=NSN=C1C1C(CC2)CCN2C1 CDHAUECRXULZKZ-UHFFFAOYSA-N 0.000 claims 1
• ZXPLIMFCWLLUFG-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-4-propylsulfanyl-1,2,5-thiadiazole Chemical compound CCCSC1=NSN=C1C1C(CC2)CCN2C1 ZXPLIMFCWLLUFG-UHFFFAOYSA-N 0.000 claims 1
• IIXWIEBXGQZOAR-UHFFFAOYSA-N 3-(1-azabicyclo[3.2.1]octan-5-yl)-4-hexylsulfanyl-1,2,5-thiadiazole Chemical compound CCCCCCSC1=NSN=C1C1(CCC2)CN2CC1 IIXWIEBXGQZOAR-UHFFFAOYSA-N 0.000 claims 1
• DRAMZVWPNLACOI-UHFFFAOYSA-N 3-(1-azabicyclo[3.3.1]non-3-en-3-yl)-4-butoxy-1,2,5-thiadiazole Chemical compound CCCCOC1=NSN=C1C(C1)=CC2CN1CCC2 DRAMZVWPNLACOI-UHFFFAOYSA-N 0.000 claims 1
• QTLFMNIUHKNXQU-UHFFFAOYSA-N 3-(1-azabicyclo[3.3.1]non-3-en-3-yl)-4-hexoxy-1,2,5-thiadiazole Chemical compound CCCCCCOC1=NSN=C1C(C1)=CC2CN1CCC2 QTLFMNIUHKNXQU-UHFFFAOYSA-N 0.000 claims 1
• CIBOJGMIGPKLMI-UHFFFAOYSA-N 3-(1-azabicyclo[3.3.1]non-3-en-3-yl)-4-propoxy-1,2,5-thiadiazole Chemical compound CCCOC1=NSN=C1C(C1)=CC2CN1CCC2 CIBOJGMIGPKLMI-UHFFFAOYSA-N 0.000 claims 1
• IXMLNNNSHOBKKY-UHFFFAOYSA-N 3-(4-chloro-1,2,5-thiadiazol-3-yl)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound C1N(CC2)CCC2C1(O)C1=NSN=C1Cl IXMLNNNSHOBKKY-UHFFFAOYSA-N 0.000 claims 1
• MFRGCWSSXLWRTK-UHFFFAOYSA-N 3-(4-chloro-1-azabicyclo[3.3.1]non-3-en-3-yl)-1,2,5-thiadiazole Chemical compound C1N(C2)CCCC2C(Cl)=C1C=1C=NSN=1 MFRGCWSSXLWRTK-UHFFFAOYSA-N 0.000 claims 1
• JNKJAHXFGKGAJZ-UHFFFAOYSA-N 3-(4-chloro-1-azabicyclo[3.3.1]non-3-en-3-yl)-4-pentoxy-1,2,5-thiadiazole Chemical compound CCCCCOC1=NSN=C1C(C1)=C(Cl)C2CN1CCC2 JNKJAHXFGKGAJZ-UHFFFAOYSA-N 0.000 claims 1
• GWLPEJQHNYRWGA-UHFFFAOYSA-N 3-(4-hexoxy-1,2,5-thiadiazol-3-yl)-1-azabicyclo[2.2.2]octan-3-ol Chemical compound CCCCCCOC1=NSN=C1C1(O)C(CC2)CCN2C1 GWLPEJQHNYRWGA-UHFFFAOYSA-N 0.000 claims 1
• MQXOQDKWYLMKBH-UHFFFAOYSA-N 3-chloro-4-(3-chloro-1-azabicyclo[2.2.1]heptan-3-yl)-1,2,5-thiadiazole Chemical compound ClC1=NSN=C1C1(Cl)C(C2)CCN2C1 MQXOQDKWYLMKBH-UHFFFAOYSA-N 0.000 claims 1
• SDZLOUZCGASTBE-UHFFFAOYSA-N 3-chloro-4-(3-chloro-8-azabicyclo[3.2.1]oct-3-en-4-yl)-1,2,5-thiadiazole Chemical compound ClC1=NSN=C1C1=C(Cl)CC2NC1CC2 SDZLOUZCGASTBE-UHFFFAOYSA-N 0.000 claims 1
• QCQVHEXCGGZMLV-UHFFFAOYSA-N 3-chloro-4-(6-chloro-2-methyl-1-azabicyclo[3.2.1]octan-6-yl)-1,2,5-thiadiazole Chemical compound CC1CCC2CN1CC2(Cl)C1=NSN=C1Cl QCQVHEXCGGZMLV-UHFFFAOYSA-N 0.000 claims 1
• KPQLCXWABVQWHK-UHFFFAOYSA-N 3-hexoxy-4-(3-hexoxy-1-azabicyclo[2.2.2]octan-3-yl)-1,2,5-thiadiazole Chemical compound CCCCCCOC1=NSN=C1C1(OCCCCCC)C(CC2)CCN2C1 KPQLCXWABVQWHK-UHFFFAOYSA-N 0.000 claims 1
• YUYUPTUPVNJDHY-UHFFFAOYSA-N 3-methoxy-4-(3-methoxy-1-azabicyclo[2.2.2]octan-3-yl)-1,2,5-thiadiazole Chemical compound COC1=NSN=C1C1(OC)C(CC2)CCN2C1 YUYUPTUPVNJDHY-UHFFFAOYSA-N 0.000 claims 1
• FRDZYWNOMHNYQI-UHFFFAOYSA-N 4-(1-azabicyclo[2.2.2]octan-3-yl)-1,2,5-oxadiazol-3-amine Chemical compound NC1=NON=C1C1C(CC2)CCN2C1 FRDZYWNOMHNYQI-UHFFFAOYSA-N 0.000 claims 1
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