GB1043141A - Substituted-4-oxo-1, 3, 8-triazaspiro (4, 5) decanes and their therapeutically active non-toxic acid addition salts and the preparation thereof - Google Patents
Substituted-4-oxo-1, 3, 8-triazaspiro (4, 5) decanes and their therapeutically active non-toxic acid addition salts and the preparation thereofInfo
- Publication number
- GB1043141A GB1043141A GB24824/63A GB2482463A GB1043141A GB 1043141 A GB1043141 A GB 1043141A GB 24824/63 A GB24824/63 A GB 24824/63A GB 2482463 A GB2482463 A GB 2482463A GB 1043141 A GB1043141 A GB 1043141A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chloro
- fluorophenyl
- phenyl
- cyclopropyl
- prepared
- Prior art date
- 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
Links
- -1 Substituted-4-oxo-1, 3, 8-triazaspiro (4, 5) decanes Chemical class 0.000 title abstract 18
- 239000002253 acid Substances 0.000 title abstract 2
- 231100000252 nontoxic Toxicity 0.000 title abstract 2
- 230000003000 nontoxic effect Effects 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 9
- 125000003118 aryl group Chemical group 0.000 abstract 7
- 238000006243 chemical reaction Methods 0.000 abstract 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 abstract 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 abstract 3
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
- 150000003857 carboxamides Chemical class 0.000 abstract 3
- CCPNPBRERVEAFH-UHFFFAOYSA-N cyclopropyl-(4-fluorophenyl)-thiophen-2-ylmethanol Chemical compound C=1C=CSC=1C(C=1C=CC(F)=CC=1)(O)C1CC1 CCPNPBRERVEAFH-UHFFFAOYSA-N 0.000 abstract 3
- 238000006264 debenzylation reaction Methods 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 238000007363 ring formation reaction Methods 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- OSFCGPVNQAPOHW-UHFFFAOYSA-N 1-(4-chlorophenyl)-1-cyclopropylethanol Chemical compound C=1C=C(Cl)C=CC=1C(O)(C)C1CC1 OSFCGPVNQAPOHW-UHFFFAOYSA-N 0.000 abstract 2
- PRSPZMCGRMNHGL-UHFFFAOYSA-N 1-(5-chloropent-2-en-2-yl)-4-methylbenzene Chemical compound ClCCC=C(C)C1=CC=C(C)C=C1 PRSPZMCGRMNHGL-UHFFFAOYSA-N 0.000 abstract 2
- FWKSXVPFRPLQPN-UHFFFAOYSA-N 2-(4-fluorophenyl)sulfanylethanol Chemical compound OCCSC1=CC=C(F)C=C1 FWKSXVPFRPLQPN-UHFFFAOYSA-N 0.000 abstract 2
- NZPXXZOZIHHFQI-UHFFFAOYSA-N 5-chloro-1,1-diphenylpentan-1-ol Chemical compound ClCCCCC(O)(C1=CC=CC=C1)C1=CC=CC=C1 NZPXXZOZIHHFQI-UHFFFAOYSA-N 0.000 abstract 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 235000019270 ammonium chloride Nutrition 0.000 abstract 2
- 150000008064 anhydrides Chemical class 0.000 abstract 2
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 2
- YKNMBTZOEVIJCM-UHFFFAOYSA-N dec-2-ene Chemical compound CCCCCCCC=CC YKNMBTZOEVIJCM-UHFFFAOYSA-N 0.000 abstract 2
- 125000001207 fluorophenyl group Chemical group 0.000 abstract 2
- 125000005059 halophenyl group Chemical group 0.000 abstract 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 150000002825 nitriles Chemical group 0.000 abstract 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 abstract 2
- JLNYNSOPLYOWFA-UHFFFAOYSA-N (4-chloro-1-phenylbutyl)benzene Chemical compound C=1C=CC=CC=1C(CCCCl)C1=CC=CC=C1 JLNYNSOPLYOWFA-UHFFFAOYSA-N 0.000 abstract 1
- LYVVLLJWGCJWGB-UHFFFAOYSA-N (4-chlorophenyl)-cyclopropyl-(4-fluorophenyl)methanol Chemical compound ClC1=CC=C(C=C1)C(O)(C1=CC=C(C=C1)F)C1CC1 LYVVLLJWGCJWGB-UHFFFAOYSA-N 0.000 abstract 1
- YKDWEGVCSVEYLW-UHFFFAOYSA-N (5-chloro-1-phenylpent-1-enyl)benzene Chemical compound ClCCCC=C(C1=CC=CC=C1)C1=CC=CC=C1 YKDWEGVCSVEYLW-UHFFFAOYSA-N 0.000 abstract 1
- ZIBQXKPVDDAHKW-UHFFFAOYSA-N (5-chloro-1-phenylpentyl)benzene Chemical compound ClCCCCC(C1=CC=CC=C1)C1=CC=CC=C1 ZIBQXKPVDDAHKW-UHFFFAOYSA-N 0.000 abstract 1
- 125000005877 1,4-benzodioxanyl group Chemical group 0.000 abstract 1
- ZLXNKUOEVVKAIQ-UHFFFAOYSA-N 1-(1-bromobutan-2-yl)-4-fluorobenzene Chemical compound CCC(CBr)C1=CC=C(F)C=C1 ZLXNKUOEVVKAIQ-UHFFFAOYSA-N 0.000 abstract 1
- PHGMUOJCQCLPBD-UHFFFAOYSA-N 1-(1-bromoethyl)-4-fluorobenzene Chemical compound CC(Br)C1=CC=C(F)C=C1 PHGMUOJCQCLPBD-UHFFFAOYSA-N 0.000 abstract 1
- KCCIVVCMLFKSPS-UHFFFAOYSA-N 1-(1-bromopropan-2-yl)-4-fluorobenzene Chemical compound BrCC(C)C1=CC=C(F)C=C1 KCCIVVCMLFKSPS-UHFFFAOYSA-N 0.000 abstract 1
- OYKWFHPKDHJXFS-UHFFFAOYSA-N 1-(1-bromopropyl)-4-chlorobenzene Chemical compound CCC(Br)C1=CC=C(Cl)C=C1 OYKWFHPKDHJXFS-UHFFFAOYSA-N 0.000 abstract 1
- MCKGKQQNRIJNPX-UHFFFAOYSA-N 1-(1-bromopropyl)-4-fluorobenzene Chemical compound CCC(Br)C1=CC=C(F)C=C1 MCKGKQQNRIJNPX-UHFFFAOYSA-N 0.000 abstract 1
- FVPJPTJNQRLTJO-UHFFFAOYSA-N 1-(2-chloroethylsulfanyl)-4-fluorobenzene Chemical compound FC1=CC=C(SCCCl)C=C1 FVPJPTJNQRLTJO-UHFFFAOYSA-N 0.000 abstract 1
- ZJYXLKFSPOMOHG-UHFFFAOYSA-N 1-(3-chloropropylsulfanyl)-4-methylbenzene Chemical compound CC1=CC=C(SCCCCl)C=C1 ZJYXLKFSPOMOHG-UHFFFAOYSA-N 0.000 abstract 1
- VCHMYYCVCLAKFC-UHFFFAOYSA-N 1-(4-chloro-1-phenylbut-1-enyl)-3-(trifluoromethyl)benzene Chemical compound ClCCC=C(C1=CC(=CC=C1)C(F)(F)F)C1=CC=CC=C1 VCHMYYCVCLAKFC-UHFFFAOYSA-N 0.000 abstract 1
- WWNMMLUHAHKRAV-UHFFFAOYSA-N 1-(4-chloro-1-phenylbut-1-enyl)-4-fluorobenzene Chemical compound ClCCC=C(C1=CC=CC=C1)C1=CC=C(C=C1)F WWNMMLUHAHKRAV-UHFFFAOYSA-N 0.000 abstract 1
- QQSFOCCCJLHEKI-UHFFFAOYSA-N 1-(4-chloro-1-phenylbut-1-enyl)-4-methoxybenzene Chemical compound ClCCC=C(C1=CC=CC=C1)C1=CC=C(C=C1)OC QQSFOCCCJLHEKI-UHFFFAOYSA-N 0.000 abstract 1
- DSOWFZVMZINIRG-UHFFFAOYSA-N 1-(4-chloro-1-phenylbut-1-enyl)-4-methylbenzene Chemical compound C1=CC(C)=CC=C1C(=CCCCl)C1=CC=CC=C1 DSOWFZVMZINIRG-UHFFFAOYSA-N 0.000 abstract 1
- LJSMZTZPLOWAHK-UHFFFAOYSA-N 1-(4-chloro-1-phenylbutyl)-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1C(CCCCl)C1=CC=CC=C1 LJSMZTZPLOWAHK-UHFFFAOYSA-N 0.000 abstract 1
- QETQVPZDEUZESP-UHFFFAOYSA-N 1-(4-chloro-1-phenylbutyl)-4-methoxybenzene Chemical compound COC1=CC=C(C=C1)C(CCCCl)C1=CC=CC=C1 QETQVPZDEUZESP-UHFFFAOYSA-N 0.000 abstract 1
- RQNSFQNDECZWCA-UHFFFAOYSA-N 1-(4-chlorobut-1-enyl)-4-fluorobenzene Chemical compound FC1=CC=C(C=CCCCl)C=C1 RQNSFQNDECZWCA-UHFFFAOYSA-N 0.000 abstract 1
- TXAWBKBMGZKBNN-UHFFFAOYSA-N 1-(4-chlorophenyl)propan-1-ol Chemical compound CCC(O)C1=CC=C(Cl)C=C1 TXAWBKBMGZKBNN-UHFFFAOYSA-N 0.000 abstract 1
- PSDSORRYQPTKSV-UHFFFAOYSA-N 1-(4-fluorophenyl)ethanol Chemical compound CC(O)C1=CC=C(F)C=C1 PSDSORRYQPTKSV-UHFFFAOYSA-N 0.000 abstract 1
- WLGMTOZJYHEVDO-UHFFFAOYSA-N 1-(5-bromopent-2-en-2-yl)-4-fluorobenzene Chemical compound BrCCC=C(C)C1=CC=C(F)C=C1 WLGMTOZJYHEVDO-UHFFFAOYSA-N 0.000 abstract 1
- HPPNHKSPHXCLRE-UHFFFAOYSA-N 1-(5-bromopentan-2-yl)-4-fluorobenzene Chemical compound BrCCCC(C)C1=CC=C(F)C=C1 HPPNHKSPHXCLRE-UHFFFAOYSA-N 0.000 abstract 1
- HQPIFWRVICLQHU-UHFFFAOYSA-N 1-(5-chloro-1-phenylpent-1-enyl)-4-fluorobenzene Chemical compound ClCCCC=C(C1=CC=CC=C1)C1=CC=C(C=C1)F HQPIFWRVICLQHU-UHFFFAOYSA-N 0.000 abstract 1
- FZQNRUYEMJXVPV-UHFFFAOYSA-N 1-(5-chloro-1-phenylpentyl)-4-fluorobenzene Chemical compound ClCCCCC(C1=CC=CC=C1)C1=CC=C(C=C1)F FZQNRUYEMJXVPV-UHFFFAOYSA-N 0.000 abstract 1
- YDOMFXIDLRDYDR-UHFFFAOYSA-N 1-(5-chloro-2-phenylpentyl)-4-fluorobenzene Chemical compound FC1=CC=C(CC(CCCCl)C2=CC=CC=C2)C=C1 YDOMFXIDLRDYDR-UHFFFAOYSA-N 0.000 abstract 1
- NBEBTHGWVGRUEA-UHFFFAOYSA-N 1-(5-chloropent-2-en-2-yl)-4-methoxybenzene Chemical compound COC1=CC=C(C(C)=CCCCl)C=C1 NBEBTHGWVGRUEA-UHFFFAOYSA-N 0.000 abstract 1
- VSCYASCPMKCALE-UHFFFAOYSA-N 1-(5-chloropentan-2-yl)-4-methoxybenzene Chemical compound COC1=CC=C(C=C1)C(C)CCCCl VSCYASCPMKCALE-UHFFFAOYSA-N 0.000 abstract 1
- HBBIUOKGGUTJFD-UHFFFAOYSA-N 1-(5-chloropentan-2-yl)-4-methylbenzene Chemical compound CC(CCCCl)C1=CC=C(C)C=C1 HBBIUOKGGUTJFD-UHFFFAOYSA-N 0.000 abstract 1
- KQWIPOLVTZIASH-UHFFFAOYSA-N 1-[4-bromo-1-[3-(trifluoromethyl)phenyl]but-1-enyl]-3-(trifluoromethyl)benzene Chemical compound BrCCC=C(C1=CC(=CC=C1)C(F)(F)F)C1=CC(=CC=C1)C(F)(F)F KQWIPOLVTZIASH-UHFFFAOYSA-N 0.000 abstract 1
- XJNUVXUBAMUIJB-UHFFFAOYSA-N 1-[4-bromo-1-[3-(trifluoromethyl)phenyl]butyl]-3-(trifluoromethyl)benzene Chemical compound BrCCCC(C1=CC(=CC=C1)C(F)(F)F)C1=CC(=CC=C1)C(F)(F)F XJNUVXUBAMUIJB-UHFFFAOYSA-N 0.000 abstract 1
- QXEBDPWKTAJFHA-UHFFFAOYSA-N 1-[4-chloro-1-(4-fluorophenyl)but-1-enyl]-3-(trifluoromethyl)benzene Chemical compound ClCCC=C(C1=CC(=CC=C1)C(F)(F)F)C1=CC=C(C=C1)F QXEBDPWKTAJFHA-UHFFFAOYSA-N 0.000 abstract 1
- SGZXIWYCGSJFEF-UHFFFAOYSA-N 1-[4-chloro-1-(4-fluorophenyl)but-1-enyl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1C(=CCCCl)C1=CC=C(F)C=C1 SGZXIWYCGSJFEF-UHFFFAOYSA-N 0.000 abstract 1
- UUWQMFIMUGNTIL-UHFFFAOYSA-N 1-[4-chloro-1-(4-fluorophenyl)but-1-enyl]-4-methylbenzene Chemical compound ClCCC=C(C1=CC=C(C=C1)C)C1=CC=C(C=C1)F UUWQMFIMUGNTIL-UHFFFAOYSA-N 0.000 abstract 1
- HZGVJBHUJRODNW-UHFFFAOYSA-N 1-[4-chloro-1-(4-fluorophenyl)butyl]-3-(trifluoromethyl)benzene Chemical compound FC1=CC=C(C=C1)C(CCCCl)C1=CC(=CC=C1)C(F)(F)F HZGVJBHUJRODNW-UHFFFAOYSA-N 0.000 abstract 1
- UXXLTPGCINZEFM-UHFFFAOYSA-N 1-[4-chloro-1-(4-fluorophenyl)butyl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1C(CCCCl)C1=CC=C(F)C=C1 UXXLTPGCINZEFM-UHFFFAOYSA-N 0.000 abstract 1
- JLJKPFDAALNNTQ-UHFFFAOYSA-N 1-[4-chloro-1-(4-fluorophenyl)butyl]-4-methylbenzene Chemical compound CC1=CC=C(C=C1)C(CCCCl)C1=CC=C(F)C=C1 JLJKPFDAALNNTQ-UHFFFAOYSA-N 0.000 abstract 1
- FWRPLUWJXAXJQA-UHFFFAOYSA-N 1-[4-chloro-1-(4-methoxyphenyl)but-1-enyl]-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1C(=CCCCl)C1=CC=C(OC)C=C1 FWRPLUWJXAXJQA-UHFFFAOYSA-N 0.000 abstract 1
- FDAQUIDJFSCFQG-UHFFFAOYSA-N 1-[4-chloro-1-(4-methylphenyl)but-1-enyl]-4-methylbenzene Chemical compound C1=CC(C)=CC=C1C(=CCCCl)C1=CC=C(C)C=C1 FDAQUIDJFSCFQG-UHFFFAOYSA-N 0.000 abstract 1
- AMVQUWCIPSIQBA-UHFFFAOYSA-N 1-[5-chloro-1-(4-fluorophenyl)pent-1-enyl]-4-fluorobenzene Chemical compound ClCCCC=C(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F AMVQUWCIPSIQBA-UHFFFAOYSA-N 0.000 abstract 1
- XVUUECUGEKMKLP-UHFFFAOYSA-N 1-[5-chloro-1-(4-fluorophenyl)pent-2-en-2-yl]-4-fluorobenzene Chemical compound ClCCC=C(CC1=CC=C(C=C1)F)C1=CC=C(C=C1)F XVUUECUGEKMKLP-UHFFFAOYSA-N 0.000 abstract 1
- PEHRTLWBRXDXPV-UHFFFAOYSA-N 1-[5-chloro-1-(4-fluorophenyl)pentan-2-yl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1CC(CCCCl)C1=CC=C(F)C=C1 PEHRTLWBRXDXPV-UHFFFAOYSA-N 0.000 abstract 1
- AIZKHKIKQBOULC-UHFFFAOYSA-N 1-[5-chloro-1-(4-fluorophenyl)pentyl]-4-fluorobenzene Chemical compound C1=CC(F)=CC=C1C(CCCCCl)C1=CC=C(F)C=C1 AIZKHKIKQBOULC-UHFFFAOYSA-N 0.000 abstract 1
- VMURKBLKZQMOFG-UHFFFAOYSA-N 1-chloro-4-(5-chloropent-2-en-2-yl)benzene Chemical compound ClCCC=C(C)C1=CC=C(Cl)C=C1 VMURKBLKZQMOFG-UHFFFAOYSA-N 0.000 abstract 1
- JZVHMIFJAWBZNL-UHFFFAOYSA-N 1-chloro-4-(5-chloropentan-2-yl)benzene Chemical compound CC(CCCCl)C1=CC=C(Cl)C=C1 JZVHMIFJAWBZNL-UHFFFAOYSA-N 0.000 abstract 1
- KGGHMPJQVZWWES-UHFFFAOYSA-N 1-chloro-4-[4-chloro-1-(4-fluorophenyl)but-1-enyl]benzene Chemical compound C1=CC(F)=CC=C1C(=CCCCl)C1=CC=C(Cl)C=C1 KGGHMPJQVZWWES-UHFFFAOYSA-N 0.000 abstract 1
- YRAOZGUESBQEMM-UHFFFAOYSA-N 1-cyclopropyl-1,2-bis(4-fluorophenyl)ethanol Chemical compound C1CC1C(C=1C=CC(F)=CC=1)(O)CC1=CC=C(F)C=C1 YRAOZGUESBQEMM-UHFFFAOYSA-N 0.000 abstract 1
- YJOUFYGLJJLZDH-UHFFFAOYSA-N 1-cyclopropyl-1-(4-methoxyphenyl)ethanol Chemical compound C1=CC(OC)=CC=C1C(C)(O)C1CC1 YJOUFYGLJJLZDH-UHFFFAOYSA-N 0.000 abstract 1
- ODESSVLMCLJHHD-UHFFFAOYSA-N 1-cyclopropyl-1-phenylethanol Chemical compound C=1C=CC=CC=1C(O)(C)C1CC1 ODESSVLMCLJHHD-UHFFFAOYSA-N 0.000 abstract 1
- PIXKYCSBCNDSQC-UHFFFAOYSA-N 1-cyclopropyl-2-(4-fluorophenyl)-1-phenylethanol Chemical compound OC(CC1=CC=C(F)C=C1)(C1CC1)C1=CC=CC=C1 PIXKYCSBCNDSQC-UHFFFAOYSA-N 0.000 abstract 1
- PMXAYOWZQGLJBI-UHFFFAOYSA-N 2-[4-chloro-1-(4-fluorophenyl)but-1-enyl]thiophene Chemical compound ClCCC=C(C=1SC=CC1)C1=CC=C(C=C1)F PMXAYOWZQGLJBI-UHFFFAOYSA-N 0.000 abstract 1
- DHLPOPOQJVUCIL-UHFFFAOYSA-N 2-[4-chloro-1-(4-fluorophenyl)butyl]thiophene Chemical compound FC1=CC=C(C=C1)C(CCCCl)C1=CC=CS1 DHLPOPOQJVUCIL-UHFFFAOYSA-N 0.000 abstract 1
- BMNVIMUWMCISBT-UHFFFAOYSA-N 2-cyclopropyl-1-(4-methylphenyl)ethanol Chemical compound C1=CC(C)=CC=C1C(O)CC1CC1 BMNVIMUWMCISBT-UHFFFAOYSA-N 0.000 abstract 1
- TVRAIYLSBBAZTK-UHFFFAOYSA-N 4-(4-fluorophenyl)-4-thiophen-2-ylbut-3-en-1-ol Chemical compound FC1=CC=C(C=C1)C(=CCCO)C=1SC=CC1 TVRAIYLSBBAZTK-UHFFFAOYSA-N 0.000 abstract 1
- VMQDMVIGMCDOMQ-UHFFFAOYSA-N 4-(4-fluorophenyl)-4-thiophen-2-ylbutan-1-ol Chemical compound FC1=CC=C(C=C1)C(CCCO)C=1SC=CC1 VMQDMVIGMCDOMQ-UHFFFAOYSA-N 0.000 abstract 1
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 abstract 1
- QXCDKFHIJUHTFG-UHFFFAOYSA-N 5-bromopent-2-en-2-ylbenzene Chemical compound BrCCC=C(C)C1=CC=CC=C1 QXCDKFHIJUHTFG-UHFFFAOYSA-N 0.000 abstract 1
- QMMKBUPYOMZGSU-UHFFFAOYSA-N 5-chloro-1,1-bis(4-fluorophenyl)pentan-1-ol Chemical compound ClCCCCC(O)(C1=CC=C(C=C1)F)C1=CC=C(C=C1)F QMMKBUPYOMZGSU-UHFFFAOYSA-N 0.000 abstract 1
- GQMXNKCGCRHTFN-UHFFFAOYSA-N 5-chloro-1-(4-fluorophenyl)-1-phenylpentan-1-ol Chemical compound ClCCCCC(O)(C1=CC=CC=C1)C1=CC=C(C=C1)F GQMXNKCGCRHTFN-UHFFFAOYSA-N 0.000 abstract 1
- DIHWBAOGLBRSHJ-UHFFFAOYSA-N C1(=CC=CC=C1)C(CCCCl)C1=CC=C(C=C1)C Chemical compound C1(=CC=CC=C1)C(CCCCl)C1=CC=C(C=C1)C DIHWBAOGLBRSHJ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 abstract 1
- 229910010084 LiAlH4 Inorganic materials 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 abstract 1
- 229910020828 NaAlH4 Inorganic materials 0.000 abstract 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 1
- QYDBZVRKADDLFQ-UHFFFAOYSA-N [2-(bromomethyl)cyclopropyl]benzene Chemical compound BrCC1CC1C1=CC=CC=C1 QYDBZVRKADDLFQ-UHFFFAOYSA-N 0.000 abstract 1
- AYLIEDQYYJIGDP-UHFFFAOYSA-N [C]1=CC=CS1 Chemical compound [C]1=CC=CS1 AYLIEDQYYJIGDP-UHFFFAOYSA-N 0.000 abstract 1
- DDSZWBCJXDRQDU-UHFFFAOYSA-N [N].C1CCNCC1 Chemical group [N].C1CCNCC1 DDSZWBCJXDRQDU-UHFFFAOYSA-N 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000007933 aliphatic carboxylic acids Chemical group 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 abstract 1
- 125000004849 alkoxymethyl group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 125000005110 aryl thio group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 1
- JPBIBQAYXLZJBV-UHFFFAOYSA-N bis[1-(4-chlorophenyl)cyclopropyl]methanone Chemical compound C1=CC(Cl)=CC=C1C1(C(=O)C2(CC2)C=2C=CC(Cl)=CC=2)CC1 JPBIBQAYXLZJBV-UHFFFAOYSA-N 0.000 abstract 1
- 239000001273 butane Substances 0.000 abstract 1
- 125000005242 carbamoyl alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- GHYGLJGTZQZVJE-UHFFFAOYSA-N cyclopropyl-(4-fluorophenyl)-(4-methoxyphenyl)methanol Chemical compound C1(CC1)C(O)(C1=CC=C(C=C1)OC)C1=CC=C(C=C1)F GHYGLJGTZQZVJE-UHFFFAOYSA-N 0.000 abstract 1
- BTWVBVWGRFLFBK-UHFFFAOYSA-N cyclopropyl-(4-fluorophenyl)-(4-methylphenyl)methanol Chemical compound CC1=CC=C(C=C1)C(O)(C1CC1)C1=CC=C(F)C=C1 BTWVBVWGRFLFBK-UHFFFAOYSA-N 0.000 abstract 1
- MCVXFAHNMZSNDU-UHFFFAOYSA-N cyclopropyl-(4-fluorophenyl)-[3-(trifluoromethyl)phenyl]methanol Chemical compound OC(C1CC1)(C1=CC=C(F)C=C1)C1=CC(=CC=C1)C(F)(F)F MCVXFAHNMZSNDU-UHFFFAOYSA-N 0.000 abstract 1
- XEPUHHNAKZHVCG-UHFFFAOYSA-N cyclopropyl-(4-fluorophenyl)-phenylmethanol Chemical compound OC(C1CC1)(C1=CC=CC=C1)C1=CC=C(F)C=C1 XEPUHHNAKZHVCG-UHFFFAOYSA-N 0.000 abstract 1
- SIRULVGQLZGELT-UHFFFAOYSA-N cyclopropyl-(4-methoxyphenyl)-phenylmethanol Chemical compound C1=CC(OC)=CC=C1C(O)(C=1C=CC=CC=1)C1CC1 SIRULVGQLZGELT-UHFFFAOYSA-N 0.000 abstract 1
- KGPYJDJMUJWJDQ-UHFFFAOYSA-N cyclopropyl-(4-methylphenyl)-phenylmethanol Chemical compound C1=CC(C)=CC=C1C(O)(C=1C=CC=CC=1)C1CC1 KGPYJDJMUJWJDQ-UHFFFAOYSA-N 0.000 abstract 1
- NOGAUXVBQHVJRH-UHFFFAOYSA-N cyclopropyl-bis(4-methylphenyl)methanol Chemical compound C1=CC(C)=CC=C1C(O)(C=1C=CC(C)=CC=1)C1CC1 NOGAUXVBQHVJRH-UHFFFAOYSA-N 0.000 abstract 1
- OEJVVCMOEPNMRT-UHFFFAOYSA-N cyclopropyl-phenyl-[3-(trifluoromethyl)phenyl]methanol Chemical compound OC(C1CC1)(C1=CC=CC=C1)C1=CC(=CC=C1)C(F)(F)F OEJVVCMOEPNMRT-UHFFFAOYSA-N 0.000 abstract 1
- 238000005695 dehalogenation reaction Methods 0.000 abstract 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 125000006331 halo benzoyl group Chemical group 0.000 abstract 1
- 125000003106 haloaryl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229960000443 hydrochloric acid Drugs 0.000 abstract 1
- 235000011167 hydrochloric acid Nutrition 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 abstract 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 abstract 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 abstract 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 238000007086 side reaction Methods 0.000 abstract 1
- 150000003413 spiro compounds Chemical class 0.000 abstract 1
- CTDQAGUNKPRERK-UHFFFAOYSA-N spirodecane Chemical compound C1CCCC21CCCCC2 CTDQAGUNKPRERK-UHFFFAOYSA-N 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 abstract 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 abstract 1
- 229940070710 valerate Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Wire Processing (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20462362A | 1962-06-22 | 1962-06-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1043141A true GB1043141A (en) | 1966-09-21 |
Family
ID=22758700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24824/63A Expired GB1043141A (en) | 1962-06-22 | 1963-06-21 | Substituted-4-oxo-1, 3, 8-triazaspiro (4, 5) decanes and their therapeutically active non-toxic acid addition salts and the preparation thereof |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE633914A (enrdf_load_stackoverflow) |
| CH (1) | CH462835A (enrdf_load_stackoverflow) |
| DE (1) | DE1470125C3 (enrdf_load_stackoverflow) |
| DK (1) | DK119880B (enrdf_load_stackoverflow) |
| FI (1) | FI46967C (enrdf_load_stackoverflow) |
| FR (6) | FR1573808A (enrdf_load_stackoverflow) |
| GB (1) | GB1043141A (enrdf_load_stackoverflow) |
| NO (1) | NO117368B (enrdf_load_stackoverflow) |
| SE (1) | SE311019B (enrdf_load_stackoverflow) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2361889A1 (fr) * | 1975-07-21 | 1978-03-17 | Janssen Pharmaceutica Nv | Nouveaux derives de 1-(benzazolyalcoyl)piperidine |
| US4080328A (en) * | 1971-07-13 | 1978-03-21 | Sumitomo Chemical Company, Limited | N-substituted heterocyclic derivatives and preparation thereof |
| WO1999059997A1 (en) * | 1998-05-18 | 1999-11-25 | Novo Nordisk A/S | Novel 1,3,8-triazaspiro[4.5]decanones with high affinity for opioid receptor subtypes |
| EP0997464A1 (en) * | 1998-10-23 | 2000-05-03 | Pfizer Inc. | 1,3,8-Triazaspiro[4,5] decanone compounds as orl1-receptor agonists |
| US6277991B1 (en) | 1998-05-18 | 2001-08-21 | Novo Nordisk A/S | 1,3,8-triazaspiro[4.5]decanones with high affinity for opioid receptor subtypes |
| US6716846B2 (en) * | 1998-07-27 | 2004-04-06 | Schering Corporation | High affinity ligands for nociceptin receptor ORL-1 |
| US8394804B2 (en) | 2001-10-19 | 2013-03-12 | Janssen Pharmaceutica N.V. | Phosphonic acid compounds as inhibitors of serine proteases |
| EP3138841A1 (en) * | 2010-06-18 | 2017-03-08 | Altos Therapeutics, LLC | D2 antagonists, methods of synthesis and methods of use |
| IT201800007580A1 (it) * | 2018-07-27 | 2020-01-27 | Maria Cecilia Hospital Spa | Composti 1,3,8-triazaspiro e loro uso come medicamenti |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE792187A (fr) * | 1971-12-03 | 1973-03-30 | Sumitomo Chemical Co | Nouveaux derives d'alkylamines |
| NZ181256A (en) * | 1975-07-21 | 1978-04-28 | Janssen Pharmaceutica Nv | 1-(w-benzazol-11-ylalkyl)-piperidine derivatives and pharmaceutical compositions containing certain of these derivatives |
| DK139684A (da) * | 1983-04-11 | 1984-10-12 | Janssen Pharmaceutica Nv | N-aryl-alpha-amino-carboxamider |
| US5244902A (en) * | 1989-08-21 | 1993-09-14 | Beth Israel Hospital Association | Topical application of spiperone or derivatives thereof for treatment of pathological conditions associated with immune responses |
| US5703088A (en) * | 1989-08-21 | 1997-12-30 | Beth Israel Deaconess Medical Center, Inc. | Topical application of spiperone or derivatives thereof for treatment of pathological conditions associated with immune responses |
| US5574041A (en) * | 1990-03-16 | 1996-11-12 | Beth Israel Hospital Association | Use of spiperone derivatives as immunosuppressant agents |
| US5693645A (en) * | 1992-12-23 | 1997-12-02 | Beth Israel Deaconess Medical Center, Inc. | Use of spiperone or spiperone derivatives as immunosuppressant agents |
| DE19610397A1 (de) * | 1996-03-16 | 1997-09-18 | Krewel Meuselbach Gmbh | Gewinnung von Fluspirilen-Suspensionen |
| DE102005038141A1 (de) * | 2005-08-12 | 2007-02-15 | Grünenthal GmbH | Substituierte 8-(3-Aminopropyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-on-Derivate |
-
0
- BE BE633914D patent/BE633914A/xx unknown
-
1963
- 1963-06-19 SE SE6834/63A patent/SE311019B/xx unknown
- 1963-06-21 CH CH776363A patent/CH462835A/de unknown
- 1963-06-21 GB GB24824/63A patent/GB1043141A/en not_active Expired
- 1963-06-21 NO NO149114A patent/NO117368B/no unknown
- 1963-06-21 FI FI631267A patent/FI46967C/fi active
- 1963-06-21 DE DE1470125A patent/DE1470125C3/de not_active Expired
- 1963-06-22 FR FR1573808D patent/FR1573808A/fr not_active Expired
- 1963-06-22 DK DK297763AA patent/DK119880B/da unknown
- 1963-09-20 FR FR948241A patent/FR2986M/fr active Active
- 1963-09-20 FR FR948242A patent/FR2987M/fr active Active
- 1963-09-20 FR FR948240A patent/FR3043M/fr active Active
- 1963-09-20 FR FR948243A patent/FR2988M/fr active Active
- 1963-09-20 FR FR948244A patent/FR3059M/fr active Active
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4080328A (en) * | 1971-07-13 | 1978-03-21 | Sumitomo Chemical Company, Limited | N-substituted heterocyclic derivatives and preparation thereof |
| FR2361889A1 (fr) * | 1975-07-21 | 1978-03-17 | Janssen Pharmaceutica Nv | Nouveaux derives de 1-(benzazolyalcoyl)piperidine |
| WO1999059997A1 (en) * | 1998-05-18 | 1999-11-25 | Novo Nordisk A/S | Novel 1,3,8-triazaspiro[4.5]decanones with high affinity for opioid receptor subtypes |
| US6277991B1 (en) | 1998-05-18 | 2001-08-21 | Novo Nordisk A/S | 1,3,8-triazaspiro[4.5]decanones with high affinity for opioid receptor subtypes |
| US6716846B2 (en) * | 1998-07-27 | 2004-04-06 | Schering Corporation | High affinity ligands for nociceptin receptor ORL-1 |
| US7094784B2 (en) | 1998-07-27 | 2006-08-22 | Schering Corporation | High affinity ligands for nociceptin receptor ORL-1 |
| EP0997464A1 (en) * | 1998-10-23 | 2000-05-03 | Pfizer Inc. | 1,3,8-Triazaspiro[4,5] decanone compounds as orl1-receptor agonists |
| US8394804B2 (en) | 2001-10-19 | 2013-03-12 | Janssen Pharmaceutica N.V. | Phosphonic acid compounds as inhibitors of serine proteases |
| EP3138841A1 (en) * | 2010-06-18 | 2017-03-08 | Altos Therapeutics, LLC | D2 antagonists, methods of synthesis and methods of use |
| IT201800007580A1 (it) * | 2018-07-27 | 2020-01-27 | Maria Cecilia Hospital Spa | Composti 1,3,8-triazaspiro e loro uso come medicamenti |
| WO2020021378A1 (en) * | 2018-07-27 | 2020-01-30 | Maria Cecilia Hospital S.P.A. | 1,3,8-triazaspiro compounds and their use as medicaments for the treatment of reperfusion injury |
Also Published As
| Publication number | Publication date |
|---|---|
| CH462835A (de) | 1968-09-30 |
| DK119880B (da) | 1971-03-08 |
| FI46967C (fi) | 1973-08-10 |
| SE311019B (enrdf_load_stackoverflow) | 1969-05-27 |
| FR3043M (fr) | 1965-01-04 |
| FR2986M (fr) | 1964-12-07 |
| FR1573808A (enrdf_load_stackoverflow) | 1969-07-11 |
| NO117368B (enrdf_load_stackoverflow) | 1969-08-04 |
| FR2987M (fr) | 1964-12-07 |
| FR2988M (fr) | 1964-12-07 |
| FI46967B (enrdf_load_stackoverflow) | 1973-05-02 |
| FR3059M (fr) | 1965-01-11 |
| DE1470125C3 (de) | 1980-07-10 |
| BE633914A (enrdf_load_stackoverflow) | |
| DE1470125B2 (enrdf_load_stackoverflow) | 1979-10-31 |
| DE1470125A1 (de) | 1969-05-08 |
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