HRP20110721T1 - Supstituirani spirociklički derivati cikloheksana - Google Patents
Supstituirani spirociklički derivati cikloheksana Download PDFInfo
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- HRP20110721T1 HRP20110721T1 HR20110721T HRP20110721T HRP20110721T1 HR P20110721 T1 HRP20110721 T1 HR P20110721T1 HR 20110721 T HR20110721 T HR 20110721T HR P20110721 T HRP20110721 T HR P20110721T HR P20110721 T1 HRP20110721 T1 HR P20110721T1
- Authority
- HR
- Croatia
- Prior art keywords
- cyclohexane
- indole
- phenyl
- amine
- dimethyl
- Prior art date
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- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 15
- 125000003118 aryl group Chemical group 0.000 claims 9
- RERZNCLIYCABFS-UHFFFAOYSA-N harmaline Chemical compound C1CN=C(C)C2=C1C1=CC=C(OC)C=C1N2 RERZNCLIYCABFS-UHFFFAOYSA-N 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 5
- CGLYBEYFUQIRIS-UHFFFAOYSA-N 3'-benzyl-n,n-dimethyl-1'-phenylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(N(C)C)(C=2C=CC=CC=2)CCC2(C3=C(C4=CC=CC=C4N3)CCN2)C1CC1=CC=CC=C1 CGLYBEYFUQIRIS-UHFFFAOYSA-N 0.000 claims 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- RGRFHXRVKJVFOG-UHFFFAOYSA-N 3',6-difluoro-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)C(F)CC1(N(C)C)C1=CC=CC=C1 RGRFHXRVKJVFOG-UHFFFAOYSA-N 0.000 claims 3
- ZRVFZCWVNBOHAP-UHFFFAOYSA-N 3'-[(3-fluorophenyl)methyl]-n,n-dimethyl-1'-phenylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(N(C)C)(C=2C=CC=CC=2)CCC2(C3=C(C4=CC=CC=C4N3)CCN2)C1CC1=CC=CC(F)=C1 ZRVFZCWVNBOHAP-UHFFFAOYSA-N 0.000 claims 3
- XLEGHKKTFZALDA-UHFFFAOYSA-N 3'-fluoro-n,n-dimethyl-1'-phenylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCN2)C(F)CC1(N(C)C)C1=CC=CC=C1 XLEGHKKTFZALDA-UHFFFAOYSA-N 0.000 claims 3
- 229910006069 SO3H Inorganic materials 0.000 claims 3
- 125000001931 aliphatic group Chemical group 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- -1 -OR13 Chemical group 0.000 claims 2
- YJTZWNKGTJGABL-UHFFFAOYSA-N 3'-benzyl-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(N(C)C)(C=2C=CC=CC=2)CCC2(C3=C(C4=CC=CC=C4N3)CCO2)C1CC1=CC=CC=C1 YJTZWNKGTJGABL-UHFFFAOYSA-N 0.000 claims 2
- ILNCEOIGYRKHIT-UHFFFAOYSA-N 3'-fluoro-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCO2)C(F)CC1(N(C)C)C1=CC=CC=C1 ILNCEOIGYRKHIT-UHFFFAOYSA-N 0.000 claims 2
- YRDMRECBXVVXCE-UHFFFAOYSA-N 6-fluoro-3'-[(3-fluorophenyl)methyl]-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(N(C)C)(C=2C=CC=CC=2)CCC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)C1CC1=CC=CC(F)=C1 YRDMRECBXVVXCE-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 206010012335 Dependence Diseases 0.000 claims 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 2
- 230000003444 anaesthetic effect Effects 0.000 claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- JQXWFTNKMVVFSJ-SDNWHVSQSA-N (e)-1-[1'-(dimethylamino)-2',2',6-trifluoro-1'-(3-fluorophenyl)spiro[4,9-dihydro-3h-pyrido[3,4-b]indole-1,4'-cyclohexane]-2-yl]-3-phenylprop-2-en-1-one Chemical compound C1C(F)(F)C(N(C)C)(C=2C=C(F)C=CC=2)CCC1(C1=C(C2=CC(F)=CC=C2N1)CC1)N1C(=O)\C=C\C1=CC=CC=C1 JQXWFTNKMVVFSJ-SDNWHVSQSA-N 0.000 claims 1
- XDUIXKLBEZFBMU-FOCLMDBBSA-N (e)-1-[1'-(dimethylamino)-2',2'-difluoro-1'-(3-fluorophenyl)spiro[4,9-dihydro-3h-pyrido[3,4-b]indole-1,4'-cyclohexane]-2-yl]-3-phenylprop-2-en-1-one Chemical compound C1C(F)(F)C(N(C)C)(C=2C=C(F)C=CC=2)CCC1(C1=C(C2=CC=CC=C2N1)CC1)N1C(=O)\C=C\C1=CC=CC=C1 XDUIXKLBEZFBMU-FOCLMDBBSA-N 0.000 claims 1
- AUEWUQZCOOYAKM-SDNWHVSQSA-N (e)-1-[1'-(dimethylamino)-2',6-difluoro-1'-(3-fluorophenyl)spiro[4,9-dihydro-3h-pyrido[3,4-b]indole-1,4'-cyclohexane]-2-yl]-3-phenylprop-2-en-1-one Chemical compound C1C(F)C(N(C)C)(C=2C=C(F)C=CC=2)CCC1(C1=C(C2=CC(F)=CC=C2N1)CC1)N1C(=O)\C=C\C1=CC=CC=C1 AUEWUQZCOOYAKM-SDNWHVSQSA-N 0.000 claims 1
- NWNVIDLCAYEQJL-FOCLMDBBSA-N (e)-1-[1'-(dimethylamino)-2'-fluoro-1'-(3-fluorophenyl)spiro[4,9-dihydro-3h-pyrido[3,4-b]indole-1,4'-cyclohexane]-2-yl]-3-phenylprop-2-en-1-one Chemical compound C1C(F)C(N(C)C)(C=2C=C(F)C=CC=2)CCC1(C1=C(C2=CC=CC=C2N1)CC1)N1C(=O)\C=C\C1=CC=CC=C1 NWNVIDLCAYEQJL-FOCLMDBBSA-N 0.000 claims 1
- QYAKJKQHHRPYMN-SDNWHVSQSA-N (e)-1-[4'-(dimethylamino)-2',2',6-trifluoro-4'-(3-fluorophenyl)spiro[4,9-dihydro-3h-pyrido[3,4-b]indole-1,1'-cyclohexane]-2-yl]-3-phenylprop-2-en-1-one Chemical compound FC1(F)CC(N(C)C)(C=2C=C(F)C=CC=2)CCC1(C1=C(C2=CC(F)=CC=C2N1)CC1)N1C(=O)\C=C\C1=CC=CC=C1 QYAKJKQHHRPYMN-SDNWHVSQSA-N 0.000 claims 1
- WKWVMYRSWNLYBP-FOCLMDBBSA-N (e)-1-[4'-(dimethylamino)-2',2'-difluoro-4'-(3-fluorophenyl)spiro[4,9-dihydro-3h-pyrido[3,4-b]indole-1,1'-cyclohexane]-2-yl]-3-phenylprop-2-en-1-one Chemical compound FC1(F)CC(N(C)C)(C=2C=C(F)C=CC=2)CCC1(C1=C(C2=CC=CC=C2N1)CC1)N1C(=O)\C=C\C1=CC=CC=C1 WKWVMYRSWNLYBP-FOCLMDBBSA-N 0.000 claims 1
- RFTGSCXHGGPDDA-FOCLMDBBSA-N (e)-1-[4'-(dimethylamino)-2',6'-difluoro-4'-(3-fluorophenyl)spiro[4,9-dihydro-3h-pyrido[3,4-b]indole-1,1'-cyclohexane]-2-yl]-3-phenylprop-2-en-1-one Chemical compound FC1CC(N(C)C)(C=2C=C(F)C=CC=2)CC(F)C1(C1=C(C2=CC=CC=C2N1)CC1)N1C(=O)\C=C\C1=CC=CC=C1 RFTGSCXHGGPDDA-FOCLMDBBSA-N 0.000 claims 1
- BSVSFYLZURLGTN-SDNWHVSQSA-N (e)-1-[4'-(dimethylamino)-2',6,6'-trifluoro-4'-(3-fluorophenyl)spiro[4,9-dihydro-3h-pyrido[3,4-b]indole-1,1'-cyclohexane]-2-yl]-3-phenylprop-2-en-1-one Chemical compound FC1CC(N(C)C)(C=2C=C(F)C=CC=2)CC(F)C1(C1=C(C2=CC(F)=CC=C2N1)CC1)N1C(=O)\C=C\C1=CC=CC=C1 BSVSFYLZURLGTN-SDNWHVSQSA-N 0.000 claims 1
- COWSYUCZXXZURJ-SDNWHVSQSA-N (e)-1-[4'-(dimethylamino)-2',6-difluoro-4'-(3-fluorophenyl)spiro[4,9-dihydro-3h-pyrido[3,4-b]indole-1,1'-cyclohexane]-2-yl]-3-phenylprop-2-en-1-one Chemical compound FC1CC(N(C)C)(C=2C=C(F)C=CC=2)CCC1(C1=C(C2=CC(F)=CC=C2N1)CC1)N1C(=O)\C=C\C1=CC=CC=C1 COWSYUCZXXZURJ-SDNWHVSQSA-N 0.000 claims 1
- QSIWIUOGISVJRD-FOCLMDBBSA-N (e)-1-[4'-(dimethylamino)-2'-fluoro-4'-(3-fluorophenyl)spiro[4,9-dihydro-3h-pyrido[3,4-b]indole-1,1'-cyclohexane]-2-yl]-3-phenylprop-2-en-1-one Chemical compound FC1CC(N(C)C)(C=2C=C(F)C=CC=2)CCC1(C1=C(C2=CC=CC=C2N1)CC1)N1C(=O)\C=C\C1=CC=CC=C1 QSIWIUOGISVJRD-FOCLMDBBSA-N 0.000 claims 1
- NDBLPZORFSBNFP-UHFFFAOYSA-N 1'-butyl-2',6-difluoro-n,n-dimethylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(F)C(CCCC)(N(C)C)CCC21C(NC=1C3=CC(F)=CC=1)=C3CCO2 NDBLPZORFSBNFP-UHFFFAOYSA-N 0.000 claims 1
- XWZRWYMJXBMBEJ-UHFFFAOYSA-N 1'-butyl-3',3',6-trifluoro-n,n-dimethylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound FC1(F)CC(CCCC)(N(C)C)CCC11C(NC=2C3=CC(F)=CC=2)=C3CCO1 XWZRWYMJXBMBEJ-UHFFFAOYSA-N 0.000 claims 1
- GUWAEAUYDRHBRM-UHFFFAOYSA-N 1'-butyl-3',5',6-trifluoro-n,n-dimethylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound FC1CC(CCCC)(N(C)C)CC(F)C11C(NC=2C3=CC(F)=CC=2)=C3CCO1 GUWAEAUYDRHBRM-UHFFFAOYSA-N 0.000 claims 1
- JLSORPCRDLLDLD-UHFFFAOYSA-N 1'-butyl-3',6-difluoro-n,n-dimethylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound FC1CC(CCCC)(N(C)C)CCC11C(NC=2C3=CC(F)=CC=2)=C3CCO1 JLSORPCRDLLDLD-UHFFFAOYSA-N 0.000 claims 1
- QERFEDFJCNNUNU-UHFFFAOYSA-N 2',2',6-trifluoro-1'-(3-fluorophenyl)-n,n-dimethylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCN2)CC(F)(F)C1(N(C)C)C1=CC=CC(F)=C1 QERFEDFJCNNUNU-UHFFFAOYSA-N 0.000 claims 1
- LZFDDVHXABBJPX-UHFFFAOYSA-N 2',2',6-trifluoro-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)CC(F)(F)C1(N(C)C)C1=CC=CC=C1 LZFDDVHXABBJPX-UHFFFAOYSA-N 0.000 claims 1
- KROQWYPFFGMGID-UHFFFAOYSA-N 2',2',6-trifluoro-n,n-dimethyl-1'-thiophen-2-ylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)CC(F)(F)C1(N(C)C)C1=CC=CS1 KROQWYPFFGMGID-UHFFFAOYSA-N 0.000 claims 1
- PRYJGPVLQGEIHP-UHFFFAOYSA-N 2',6-difluoro-1'-(3-fluorophenyl)-n,n-dimethylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCN2)CC(F)C1(N(C)C)C1=CC=CC(F)=C1 PRYJGPVLQGEIHP-UHFFFAOYSA-N 0.000 claims 1
- WALZLZQINUMROW-UHFFFAOYSA-N 2',6-difluoro-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)CC(F)C1(N(C)C)C1=CC=CC=C1 WALZLZQINUMROW-UHFFFAOYSA-N 0.000 claims 1
- HCMDJQWNYPVKDP-UHFFFAOYSA-N 2',6-difluoro-n,n-dimethyl-1'-thiophen-2-ylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)CC(F)C1(N(C)C)C1=CC=CS1 HCMDJQWNYPVKDP-UHFFFAOYSA-N 0.000 claims 1
- KRSPNUVHHWJPBX-UHFFFAOYSA-N 2'-[(dimethylamino)methyl]-n,n-dimethyl-1'-phenylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound CN(C)CC1CC2(C3=C(C4=CC=CC=C4N3)CCN2)CCC1(N(C)C)C1=CC=CC=C1 KRSPNUVHHWJPBX-UHFFFAOYSA-N 0.000 claims 1
- ZTOKBWFOPCUIQE-UHFFFAOYSA-N 2'-[(dimethylamino)methyl]-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound CN(C)CC1CC2(C3=C(C4=CC=CC=C4N3)CCO2)CCC1(N(C)C)C1=CC=CC=C1 ZTOKBWFOPCUIQE-UHFFFAOYSA-N 0.000 claims 1
- VMWCVNRWKYXQMS-UHFFFAOYSA-N 2'-fluoro-1'-(3-fluorophenyl)-n,n-dimethylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCN2)CC(F)C1(N(C)C)C1=CC=CC(F)=C1 VMWCVNRWKYXQMS-UHFFFAOYSA-N 0.000 claims 1
- JBGGXKNSLOKVFU-UHFFFAOYSA-N 2'-fluoro-n,n-dimethyl-1'-phenylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCN2)CC(F)C1(N(C)C)C1=CC=CC=C1 JBGGXKNSLOKVFU-UHFFFAOYSA-N 0.000 claims 1
- GCNWPMUGPBWWBO-UHFFFAOYSA-N 2'-fluoro-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCO2)CC(F)C1(N(C)C)C1=CC=CC=C1 GCNWPMUGPBWWBO-UHFFFAOYSA-N 0.000 claims 1
- RJLKEYGXHXIEMB-UHFFFAOYSA-N 2-[5'-(dimethylamino)-5'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,2'-cyclohexane]-1'-yl]acetonitrile Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCO2)C(CC#N)CC1(N(C)C)C1=CC=CC=C1 RJLKEYGXHXIEMB-UHFFFAOYSA-N 0.000 claims 1
- MHEHAGBCOANASI-UHFFFAOYSA-N 2-[5'-(dimethylamino)-5'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,2'-cyclohexane]-1'-yl]ethanol Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCO2)C(CCO)CC1(N(C)C)C1=CC=CC=C1 MHEHAGBCOANASI-UHFFFAOYSA-N 0.000 claims 1
- DBWJRYDBOSDJPY-UHFFFAOYSA-N 3',3',6-trifluoro-1'-(3-fluorophenyl)-n,n-dimethylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCN2)C(F)(F)CC1(N(C)C)C1=CC=CC(F)=C1 DBWJRYDBOSDJPY-UHFFFAOYSA-N 0.000 claims 1
- KQXNLJGHKFCLBB-UHFFFAOYSA-N 3',3',6-trifluoro-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)C(F)(F)CC1(N(C)C)C1=CC=CC=C1 KQXNLJGHKFCLBB-UHFFFAOYSA-N 0.000 claims 1
- BWWFSITUFBMPKV-UHFFFAOYSA-N 3',3',6-trifluoro-n,n-dimethyl-1'-thiophen-2-ylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)C(F)(F)CC1(N(C)C)C1=CC=CS1 BWWFSITUFBMPKV-UHFFFAOYSA-N 0.000 claims 1
- YTPXABNEHGWOPC-UHFFFAOYSA-N 3',3',6-trifluoro-n-methyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCO2)C(F)(F)CC1(NC)C1=CC=CC=C1 YTPXABNEHGWOPC-UHFFFAOYSA-N 0.000 claims 1
- YZTKCOYZTZVEIJ-UHFFFAOYSA-N 3',3'-difluoro-1'-(3-fluorophenyl)-n,n-dimethylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC=CC=C4N3)CCN2)C(F)(F)CC1(N(C)C)C1=CC=CC(F)=C1 YZTKCOYZTZVEIJ-UHFFFAOYSA-N 0.000 claims 1
- KJRIQDNHVYBMSO-UHFFFAOYSA-N 3',5',6-trifluoro-1'-(3-fluorophenyl)-n,n-dimethylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(F)C2(C3=C(C4=CC(F)=CC=C4N3)CCN2)C(F)CC1(N(C)C)C1=CC=CC(F)=C1 KJRIQDNHVYBMSO-UHFFFAOYSA-N 0.000 claims 1
- DOJIZTTWBZQIBI-UHFFFAOYSA-N 3',5',6-trifluoro-n,n-dimethyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(F)C2(C3=C(C4=CC(F)=CC=C4N3)CCO2)C(F)CC1(N(C)C)C1=CC=CC=C1 DOJIZTTWBZQIBI-UHFFFAOYSA-N 0.000 claims 1
- MOBXNOCYCQCRPT-UHFFFAOYSA-N 3',5',6-trifluoro-n,n-dimethyl-1'-thiophen-2-ylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(F)C2(C3=C(C4=CC(F)=CC=C4N3)CCO2)C(F)CC1(N(C)C)C1=CC=CS1 MOBXNOCYCQCRPT-UHFFFAOYSA-N 0.000 claims 1
- WQHFHTXNLFEAHV-UHFFFAOYSA-N 3',5',6-trifluoro-n-methyl-1'-phenylspiro[4,9-dihydro-3h-pyrano[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1C(F)C2(C3=C(C4=CC(F)=CC=C4N3)CCO2)C(F)CC1(NC)C1=CC=CC=C1 WQHFHTXNLFEAHV-UHFFFAOYSA-N 0.000 claims 1
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- MPELBLISKJKROZ-UHFFFAOYSA-N 3',6-difluoro-1'-(3-fluorophenyl)-n,n-dimethylspiro[2,3,4,9-tetrahydropyrido[3,4-b]indole-1,4'-cyclohexane]-1'-amine Chemical compound C1CC2(C3=C(C4=CC(F)=CC=C4N3)CCN2)C(F)CC1(N(C)C)C1=CC=CC(F)=C1 MPELBLISKJKROZ-UHFFFAOYSA-N 0.000 claims 1
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08005808 | 2008-03-27 | ||
| PCT/EP2009/002186 WO2009118173A1 (de) | 2008-03-27 | 2009-03-25 | Substituierte spirocyclische cyclohexan-derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20110721T1 true HRP20110721T1 (hr) | 2011-11-30 |
Family
ID=39506563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20110721T HRP20110721T1 (hr) | 2008-03-27 | 2011-10-06 | Supstituirani spirociklički derivati cikloheksana |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US8293758B2 (pt) |
| EP (1) | EP2260042B1 (pt) |
| JP (1) | JP5597188B2 (pt) |
| KR (1) | KR101615505B1 (pt) |
| CN (1) | CN102046633B (pt) |
| AR (1) | AR071068A1 (pt) |
| AT (1) | ATE525379T1 (pt) |
| AU (1) | AU2009228647B2 (pt) |
| BR (1) | BRPI0910607A2 (pt) |
| CA (1) | CA2719742C (pt) |
| CL (1) | CL2009000731A1 (pt) |
| CO (1) | CO6251244A2 (pt) |
| CY (1) | CY1112095T1 (pt) |
| DK (1) | DK2260042T3 (pt) |
| EC (1) | ECSP11010529A (pt) |
| ES (1) | ES2371230T3 (pt) |
| HK (1) | HK1149759A1 (pt) |
| HR (1) | HRP20110721T1 (pt) |
| IL (1) | IL208278A (pt) |
| MX (1) | MX2010009955A (pt) |
| NZ (1) | NZ587831A (pt) |
| PE (1) | PE20091650A1 (pt) |
| PL (1) | PL2260042T3 (pt) |
| PT (1) | PT2260042E (pt) |
| RU (1) | RU2497824C2 (pt) |
| SI (1) | SI2260042T1 (pt) |
| TW (1) | TWI450899B (pt) |
| WO (1) | WO2009118173A1 (pt) |
| ZA (1) | ZA201007645B (pt) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006033114A1 (de) * | 2006-07-18 | 2008-01-24 | Grünenthal GmbH | Spirocyclische Azaindol-Derivate |
| BRPI0906244A2 (pt) | 2008-03-24 | 2015-06-30 | Medivation Technologies Inc | Composto, composição farmacêutica, método para tratar um distúrbio cognitivo, psicótico, mediado por neurotransmissores ou um distúrbio neuronal em um indivíduo, uso de um composto e kit |
| CN102046625B (zh) | 2008-03-24 | 2015-04-08 | 梅迪维新技术公司 | 桥连杂环化合物及其使用方法 |
| DK2260042T3 (da) | 2008-03-27 | 2011-10-31 | Gruenenthal Gmbh | Substituerede spirocykliske cyklohexan-derivater |
| ES2663398T3 (es) | 2008-03-27 | 2018-04-12 | Grünenthal GmbH | Derivados de 4-aminociclohexano sustituidos |
| WO2009118174A1 (de) * | 2008-03-27 | 2009-10-01 | Grünenthal GmbH | Substituierte cyclohexyldiamine |
| MX2010010337A (es) | 2008-03-27 | 2010-10-07 | Gruenenthal Gmbh | Derivados de espiro(5.5)undecano. |
| AR071066A1 (es) | 2008-03-27 | 2010-05-26 | Gruenenthal Chemie | Derivados de (hetero) aril-ciclohexano |
| CL2009000732A1 (es) | 2008-03-27 | 2009-05-15 | Gruenethal Gmbh | Compuestos derivados de hidroximetil ciclohexilaminas sustituidos; composicion farmaceutica que contiene a dicho compuesto y sus uso como moduladores del receptor de opiodes u y el receptor orl-1 para tratar el dolor, ansiedad, depresion, epilepsia, alzheimer, abuso del alcohol, hipertension, anorexia, obesidad y diarrea. |
| EP2480081A4 (en) | 2009-09-23 | 2013-03-06 | Medivation Technologies Inc | Bridged heterocyclic compounds and methods for their use |
| EP2480078A4 (en) | 2009-09-23 | 2013-03-06 | Medivation Technologies Inc | PYRIDO- [4,3-B] INDOLE AND USE METHOD THEREFOR |
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| TWI582092B (zh) * | 2010-07-28 | 2017-05-11 | 歌林達股份有限公司 | 順式－四氫－螺旋（環己烷－１,１’－吡啶［３,４－b］吲哚）－４－胺－衍生物 |
| NZ605887A (en) * | 2010-08-04 | 2014-08-29 | Gruenenthal Gmbh | Pharmaceutical dosage form comprising 6’-fluoro-(n-methyl- or n,n-dimethyl-)-4-phenyl-4’,9’-dihydro-3’h-spiro[cyclohexane-1,1’-pyrano[3,4,b]indol]-4-amine for the treatment of neuropathic pain |
| SI2649044T1 (en) * | 2010-12-08 | 2018-01-31 | Gruenenthal Gmbh | A process for the synthesis of substituted aminocyclohexanone derivatives |
| AU2012254158B2 (en) | 2011-02-18 | 2016-02-04 | Medivation Technologies, Inc. | Compounds and methods of treating diabetes |
| EA025456B1 (ru) | 2011-03-23 | 2016-12-30 | Тревена, Инк. | Лиганды опиоидных рецепторов и способы их применения и получения |
| HUE029406T2 (hu) * | 2011-12-12 | 2017-03-28 | Gruenenthal Gmbh | (1R,4R)-6'-fluor-N,N-dimetil-4-fenil-4',9'-dihidro-3'H-spiro-[ciklohexán-1,1'- pirano[3,4,B]indol]-4-amin-hidroklorid szilárd formái |
| CA2955071A1 (en) | 2014-07-15 | 2016-01-21 | Grunenthal Gmbh | Substituted azaspiro(4.5)decane derivatives |
| TW201607923A (zh) | 2014-07-15 | 2016-03-01 | 歌林達有限公司 | 被取代之氮螺環（４．５）癸烷衍生物 |
| JP6991993B2 (ja) | 2015-12-14 | 2022-01-13 | トレベナ・インコーポレイテッド | 痛覚過敏を治療する方法 |
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| WO2009118174A1 (de) | 2008-03-27 | 2009-10-01 | Grünenthal GmbH | Substituierte cyclohexyldiamine |
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| DK2260042T3 (da) | 2008-03-27 | 2011-10-31 | Gruenenthal Gmbh | Substituerede spirocykliske cyklohexan-derivater |
| ES2663398T3 (es) | 2008-03-27 | 2018-04-12 | Grünenthal GmbH | Derivados de 4-aminociclohexano sustituidos |
| MX2010010337A (es) | 2008-03-27 | 2010-10-07 | Gruenenthal Gmbh | Derivados de espiro(5.5)undecano. |
-
2009
- 2009-03-25 DK DK09724314.1T patent/DK2260042T3/da active
- 2009-03-25 JP JP2011501144A patent/JP5597188B2/ja not_active Expired - Fee Related
- 2009-03-25 PL PL09724314T patent/PL2260042T3/pl unknown
- 2009-03-25 SI SI200930079T patent/SI2260042T1/sl unknown
- 2009-03-25 RU RU2010143437/04A patent/RU2497824C2/ru not_active IP Right Cessation
- 2009-03-25 BR BRPI0910607A patent/BRPI0910607A2/pt not_active IP Right Cessation
- 2009-03-25 PE PE2009000443A patent/PE20091650A1/es not_active Application Discontinuation
- 2009-03-25 PT PT09724314T patent/PT2260042E/pt unknown
- 2009-03-25 WO PCT/EP2009/002186 patent/WO2009118173A1/de active Application Filing
- 2009-03-25 KR KR1020107024134A patent/KR101615505B1/ko not_active IP Right Cessation
- 2009-03-25 EP EP09724314A patent/EP2260042B1/de not_active Not-in-force
- 2009-03-25 TW TW098109648A patent/TWI450899B/zh not_active IP Right Cessation
- 2009-03-25 ES ES09724314T patent/ES2371230T3/es active Active
- 2009-03-25 AR ARP090101058A patent/AR071068A1/es unknown
- 2009-03-25 CA CA2719742A patent/CA2719742C/en not_active Expired - Fee Related
- 2009-03-25 AT AT09724314T patent/ATE525379T1/de active
- 2009-03-25 CL CL2009000731A patent/CL2009000731A1/es unknown
- 2009-03-25 US US12/410,544 patent/US8293758B2/en not_active Expired - Fee Related
- 2009-03-25 NZ NZ587831A patent/NZ587831A/en not_active IP Right Cessation
- 2009-03-25 CN CN200980119293.2A patent/CN102046633B/zh not_active Expired - Fee Related
- 2009-03-25 AU AU2009228647A patent/AU2009228647B2/en not_active Ceased
- 2009-03-25 MX MX2010009955A patent/MX2010009955A/es active IP Right Grant
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2010
- 2010-09-09 CO CO10111547A patent/CO6251244A2/es active IP Right Grant
- 2010-09-21 IL IL208278A patent/IL208278A/en not_active IP Right Cessation
- 2010-10-06 EC EC2011010529A patent/ECSP11010529A/es unknown
- 2010-10-26 ZA ZA2010/07645A patent/ZA201007645B/en unknown
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- 2011-04-21 HK HK11104056.0A patent/HK1149759A1/xx not_active IP Right Cessation
- 2011-10-06 HR HR20110721T patent/HRP20110721T1/hr unknown
- 2011-11-28 CY CY20111101169T patent/CY1112095T1/el unknown
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