JP2004502642A5 - - Google Patents
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- Publication number
- JP2004502642A5 JP2004502642A5 JP2001558420A JP2001558420A JP2004502642A5 JP 2004502642 A5 JP2004502642 A5 JP 2004502642A5 JP 2001558420 A JP2001558420 A JP 2001558420A JP 2001558420 A JP2001558420 A JP 2001558420A JP 2004502642 A5 JP2004502642 A5 JP 2004502642A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- methyl
- morpholinyl
- alkyl
- methoxy
- 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.)
- Pending
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- 229910052739 hydrogen Inorganic materials 0.000 description 62
- 239000001257 hydrogen Substances 0.000 description 62
- 125000000217 alkyl group Chemical group 0.000 description 60
- 150000001875 compounds Chemical class 0.000 description 53
- 150000002431 hydrogen Chemical class 0.000 description 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 46
- 125000003118 aryl group Chemical group 0.000 description 35
- 125000000753 cycloalkyl group Chemical group 0.000 description 32
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 description 29
- -1 alkylamide Chemical group 0.000 description 28
- 125000003545 alkoxy group Chemical group 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 26
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 25
- 125000000547 substituted alkyl group Chemical group 0.000 description 23
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 21
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 18
- 150000003839 salts Chemical class 0.000 description 17
- 125000003342 alkenyl group Chemical group 0.000 description 15
- 125000005017 substituted alkenyl group Chemical group 0.000 description 15
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 13
- 125000004103 aminoalkyl group Chemical group 0.000 description 12
- 125000004093 cyano group Chemical group *C#N 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 125000000304 alkynyl group Chemical group 0.000 description 11
- 125000004426 substituted alkynyl group Chemical group 0.000 description 11
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical class C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical class 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 239000008194 pharmaceutical composition Substances 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 125000005842 heteroatom Chemical group 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 208000023504 respiratory system disease Diseases 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 241000124008 Mammalia Species 0.000 description 5
- 230000004913 activation Effects 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 239000003520 cannabinoid receptor affecting agent Substances 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 0 CC(*)(C1N2*)[C@]1c([n](**)c1c3C=CC(*)(*)C=C1*)c3C2=O Chemical compound CC(*)(C1N2*)[C@]1c([n](**)c1c3C=CC(*)(*)C=C1*)c3C2=O 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 150000001602 bicycloalkyls Chemical group 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 210000000265 leukocyte Anatomy 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 230000008878 coupling Effects 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 230000008518 non respiratory effect Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- CTKINSOISVBQLD-GSVOUGTGSA-N (R)-Glycidol Chemical compound OC[C@@H]1CO1 CTKINSOISVBQLD-GSVOUGTGSA-N 0.000 description 1
- RKZCDADRRFKROG-KMGMCLHJSA-N 1-(2-cyclohexylethyl)-7-methoxy-2-methyl-n-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]indole-3-carboxamide Chemical compound C1=2C(OC)=CC=CC=2C(C(=O)N[C@@H]2C(C3CC[C@@]2(C)C3)(C)C)=C(C)N1CCC1CCCCC1 RKZCDADRRFKROG-KMGMCLHJSA-N 0.000 description 1
- NGBQGZULVBXWKI-MNIAQESNSA-N 1-(2-ethoxyethyl)-7-methoxy-2-methyl-n-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]indole-3-carboxamide Chemical compound C12=CC=CC(OC)=C2N(CCOCC)C(C)=C1C(=O)N[C@H]1[C@@](C2)(C)CCC2C1(C)C NGBQGZULVBXWKI-MNIAQESNSA-N 0.000 description 1
- UMSJZSKEUCVDDU-UCPOHXDKSA-N 1-(2-morpholin-4-ylethyl)-5-nitro-n-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]pyrazole-3-carboxamide Chemical compound N([C@@H]1C(C)(C)C2CC[C@]1(C2)C)C(=O)C(=N1)C=C([N+]([O-])=O)N1CCN1CCOCC1 UMSJZSKEUCVDDU-UCPOHXDKSA-N 0.000 description 1
- ZSBNYNLNQAALQY-XHYACHTCSA-N 1-(2-morpholin-4-ylethyl)-5-pentoxy-n-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]pyrazole-3-carboxamide Chemical compound CCCCCOC1=CC(C(=O)N[C@@H]2C(C3CC[C@@]2(C)C3)(C)C)=NN1CCN1CCOCC1 ZSBNYNLNQAALQY-XHYACHTCSA-N 0.000 description 1
- GOTMKWHLCZVWNF-MNIAQESNSA-N 1-[2-(dimethylamino)ethyl]-7-methoxy-2-methyl-n-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]indole-3-carboxamide Chemical compound COC1=CC=CC2=C1N(CCN(C)C)C(C)=C2C(=O)N[C@H]1[C@@](C2)(C)CCC2C1(C)C GOTMKWHLCZVWNF-MNIAQESNSA-N 0.000 description 1
- SAPSVILUXSCISL-KMGMCLHJSA-N 1-[2-[di(propan-2-yl)amino]ethyl]-7-methoxy-2-methyl-n-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]indole-3-carboxamide Chemical compound COC1=CC=CC2=C1N(CCN(C(C)C)C(C)C)C(C)=C2C(=O)N[C@@H]1C(C)(C)C2CC[C@@]1(C)C2 SAPSVILUXSCISL-KMGMCLHJSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- YECUDGCOHUBKEM-QGZVFWFLSA-N 2,5-dimethyl-1-(2-morpholin-4-ylethyl)-n-[(2r)-1-phenylpropan-2-yl]pyrrole-3-carboxamide Chemical compound C([C@@H](C)NC(=O)C1=C(N(CCN2CCOCC2)C(C)=C1)C)C1=CC=CC=C1 YECUDGCOHUBKEM-QGZVFWFLSA-N 0.000 description 1
- VARGLVSWMATKND-UCPOHXDKSA-N 2-(2-morpholin-4-ylethyl)-5-nitro-n-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]pyrazole-3-carboxamide Chemical compound N([C@@H]1C(C)(C)C2CC[C@]1(C2)C)C(=O)C1=CC([N+]([O-])=O)=NN1CCN1CCOCC1 VARGLVSWMATKND-UCPOHXDKSA-N 0.000 description 1
- NAFSGIMUDROETJ-UHFFFAOYSA-N 2-[(2,6-dimethylphenyl)methyl]-6-methoxy-5-(2-morpholin-4-ylethyl)pyrido[4,3-b]indol-1-one Chemical compound COC1=CC=CC(C=2C(=O)N(CC=3C(=CC=CC=3C)C)C=CC=22)=C1N2CCN1CCOCC1 NAFSGIMUDROETJ-UHFFFAOYSA-N 0.000 description 1
- UKWKFSKFWUTFRX-UHFFFAOYSA-N 2-[(2-fluorophenyl)methyl]-6-methoxy-5-(2-morpholin-4-ylethyl)pyrido[4,3-b]indol-1-one Chemical compound COC1=CC=CC(C=2C(=O)N(CC=3C(=CC=CC=3)F)C=CC=22)=C1N2CCN1CCOCC1 UKWKFSKFWUTFRX-UHFFFAOYSA-N 0.000 description 1
- UAAIPGIFCADKPE-UHFFFAOYSA-N 2-cyclopentyl-6-methoxy-5-(2-morpholin-4-ylethyl)pyrido[4,3-b]indol-1-one Chemical compound COC1=CC=CC(C=2C(=O)N(C3CCCC3)C=CC=22)=C1N2CCN1CCOCC1 UAAIPGIFCADKPE-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- JIXREYOBFPHPQG-UWJIBMLQSA-N 2-methyl-1-(2-morpholin-4-ylethyl)-4,5-diphenyl-n-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]pyrrole-3-carboxamide Chemical compound C1COCCN1CCN1C(C)=C(C(=O)N[C@@H]2C(C3CC[C@@]2(C)C3)(C)C)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JIXREYOBFPHPQG-UWJIBMLQSA-N 0.000 description 1
- JWPGFZBOKXSSAE-LFXFHBMYSA-N 2-methyl-1-(2-morpholin-4-ylethyl)-5-phenyl-n-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]pyrrole-3-carboxamide Chemical compound C1COCCN1CCN1C(C)=C(C(=O)N[C@@H]2C(C3CC[C@@]2(C)C3)(C)C)C=C1C1=CC=CC=C1 JWPGFZBOKXSSAE-LFXFHBMYSA-N 0.000 description 1
- STTXUMSIHQWORP-UHFFFAOYSA-N 2-methyl-1-(2-morpholin-4-ylethyl)-n-(2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl)pyrrole-3-carboxamide Chemical compound CC1=C(C(=O)NC2C(C3CCC2(C)C3)(C)C)C=CN1CCN1CCOCC1 STTXUMSIHQWORP-UHFFFAOYSA-N 0.000 description 1
- AMFCVKOCHWUBAG-NRFANRHFSA-N 2-methyl-n-[(1s)-1-(3-methyl-1,2,4-oxadiazol-5-yl)-2-phenylethyl]-1-(2-morpholin-4-ylethyl)pyrrole-3-carboxamide Chemical compound CC1=NOC([C@H](CC=2C=CC=CC=2)NC(=O)C2=C(N(CCN3CCOCC3)C=C2)C)=N1 AMFCVKOCHWUBAG-NRFANRHFSA-N 0.000 description 1
- WVKPYYLOFMTDHB-UHFFFAOYSA-N 2-norbornyl radical Chemical group C1CC2[CH]CC1C2 WVKPYYLOFMTDHB-UHFFFAOYSA-N 0.000 description 1
- OLWWQYROAWRRMR-UHFFFAOYSA-N 3,4-dihydro-2h-quinolin-1-yl-[5-fluoro-7-methoxy-2-methyl-1-(2-morpholin-4-ylethyl)indol-3-yl]methanone Chemical compound C1=2C(OC)=CC(F)=CC=2C(C(=O)N2C3=CC=CC=C3CCC2)=C(C)N1CCN1CCOCC1 OLWWQYROAWRRMR-UHFFFAOYSA-N 0.000 description 1
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 1
- BMYHCXBZNSSQFT-OGGJSMKJSA-N 5,7-dimethoxy-2-methyl-1-(2-morpholin-4-ylethyl)-n-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]indole-3-carboxamide Chemical compound CC1=C(C(=O)N[C@@H]2C(C3CC[C@@]2(C)C3)(C)C)C2=CC(OC)=CC(OC)=C2N1CCN1CCOCC1 BMYHCXBZNSSQFT-OGGJSMKJSA-N 0.000 description 1
- MXJVPIIMPVGSCK-DLOYZTDZSA-N 5-benzyl-6-methoxy-2-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]pyrido[4,3-b]indol-1-one Chemical compound COC1=CC=CC(C=2C(=O)N([C@H]3[C@@]4(C)CCC(C4)C3(C)C)C=CC=22)=C1N2CC1=CC=CC=C1 MXJVPIIMPVGSCK-DLOYZTDZSA-N 0.000 description 1
- BPCWSLRVZAOONI-XMWUBULVSA-N 5-butyl-6-methoxy-2-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]pyrido[4,3-b]indol-1-one Chemical compound C12=CC=CC(OC)=C2N(CCCC)C2=C1C(=O)N([C@H]1[C@@]3(C)CCC(C3)C1(C)C)C=C2 BPCWSLRVZAOONI-XMWUBULVSA-N 0.000 description 1
- FINTYTPBRFYBCW-QPBYVCLMSA-N 5-fluoro-7-methoxy-2-methyl-1-(2-morpholin-4-ylethyl)-n-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]indole-3-carboxamide Chemical compound C1=2C(OC)=CC(F)=CC=2C(C(=O)N[C@@H]2C(C3CC[C@@]2(C)C3)(C)C)=C(C)N1CCN1CCOCC1 FINTYTPBRFYBCW-QPBYVCLMSA-N 0.000 description 1
- YJBCXXBDTPUCPP-OGGJSMKJSA-N 5-fluoro-7-methoxy-2-methyl-1-(3-morpholin-4-ylpropyl)-n-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]indole-3-carboxamide Chemical compound C1=2C(OC)=CC(F)=CC=2C(C(=O)N[C@@H]2C(C3CC[C@@]2(C)C3)(C)C)=C(C)N1CCCN1CCOCC1 YJBCXXBDTPUCPP-OGGJSMKJSA-N 0.000 description 1
- LIJWNPZQIZRZFJ-UHFFFAOYSA-N 5-fluoro-7-methoxy-n-(2-methoxyphenyl)-2-methyl-1-(2-morpholin-4-ylethyl)indole-3-carboxamide Chemical compound COC1=CC=CC=C1NC(=O)C(C1=CC(F)=CC(OC)=C11)=C(C)N1CCN1CCOCC1 LIJWNPZQIZRZFJ-UHFFFAOYSA-N 0.000 description 1
- XXZCLKCFTHJCQG-LIRQYPNKSA-N 5-methoxy-1-(2-morpholin-4-ylethyl)-n-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]pyrazole-3-carboxamide Chemical compound COC1=CC(C(=O)N[C@@H]2C(C3CC[C@@]2(C)C3)(C)C)=NN1CCN1CCOCC1 XXZCLKCFTHJCQG-LIRQYPNKSA-N 0.000 description 1
- DHWXPOMVUUYBGK-UHFFFAOYSA-N 6-methoxy-2-(2-methoxyethyl)-5-(2-morpholin-4-ylethyl)pyrido[4,3-b]indol-1-one Chemical compound C12=C(OC)C=CC=C2C=2C(=O)N(CCOC)C=CC=2N1CCN1CCOCC1 DHWXPOMVUUYBGK-UHFFFAOYSA-N 0.000 description 1
- XIOBJOPZJWKCIV-UHFFFAOYSA-N 6-methoxy-2-(2-methoxyphenyl)-5-(2-morpholin-4-ylethyl)pyrido[4,3-b]indol-1-one Chemical compound COC1=CC=CC=C1N1C(=O)C(C2=CC=CC(OC)=C2N2CCN3CCOCC3)=C2C=C1 XIOBJOPZJWKCIV-UHFFFAOYSA-N 0.000 description 1
- JTHVKCNGXTTXIF-HXUWFJFHSA-N 6-methoxy-5-(2-morpholin-4-ylethyl)-2-[(2r)-1-phenylpropan-2-yl]pyrido[4,3-b]indol-1-one Chemical compound COC1=CC=CC(C=2C(=O)N([C@H](C)CC=3C=CC=CC=3)C=CC=22)=C1N2CCN1CCOCC1 JTHVKCNGXTTXIF-HXUWFJFHSA-N 0.000 description 1
- QYOXVDHZVYJTMY-IMIJRDQBSA-N 6-methoxy-5-(2-morpholin-4-ylethyl)-2-[(3r,4r)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]pyrido[4,3-b]indol-1-one Chemical compound COC1=CC=CC(C=2C(=O)N([C@H]3C(C4CC[C@]3(C)C4)(C)C)C=CC=22)=C1N2CCN1CCOCC1 QYOXVDHZVYJTMY-IMIJRDQBSA-N 0.000 description 1
- QYOXVDHZVYJTMY-OGGJSMKJSA-N 6-methoxy-5-(2-morpholin-4-ylethyl)-2-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]pyrido[4,3-b]indol-1-one Chemical compound COC1=CC=CC(C=2C(=O)N([C@@H]3C(C4CC[C@@]3(C)C4)(C)C)C=CC=22)=C1N2CCN1CCOCC1 QYOXVDHZVYJTMY-OGGJSMKJSA-N 0.000 description 1
- UFNLQUUMXCSEQA-UHFFFAOYSA-N 6-methoxy-5-(2-morpholin-4-ylethyl)-2-propylpyrido[4,3-b]indol-1-one Chemical compound C12=C(OC)C=CC=C2C=2C(=O)N(CCC)C=CC=2N1CCN1CCOCC1 UFNLQUUMXCSEQA-UHFFFAOYSA-N 0.000 description 1
- RGLUCTFRNHDAOB-KVVHPSQQSA-N 7-methoxy-1-(2-methoxyethyl)-2-methyl-n-[(3s,4s)-2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl]indole-3-carboxamide Chemical compound C12=CC=CC(OC)=C2N(CCOC)C(C)=C1C(=O)N[C@H]1[C@@](C2)(C)CCC2C1(C)C RGLUCTFRNHDAOB-KVVHPSQQSA-N 0.000 description 1
- CPTXZVAIZCMESQ-UHFFFAOYSA-N 7-methoxy-1-(2-morpholin-4-ylethyl)-n-(2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl)indazole-3-carboxamide Chemical compound C1=2C(OC)=CC=CC=2C(C(=O)NC2C(C3CCC2(C)C3)(C)C)=NN1CCN1CCOCC1 CPTXZVAIZCMESQ-UHFFFAOYSA-N 0.000 description 1
- VQGDMQICNRCQEH-UHFFFAOYSA-N 7-methoxy-1-(2-morpholin-4-ylethyl)-n-(2,2,4-trimethyl-3-bicyclo[2.2.1]heptanyl)indole-3-carboxamide Chemical compound C1=2C(OC)=CC=CC=2C(C(=O)NC2C(C3CCC2(C)C3)(C)C)=CN1CCN1CCOCC1 VQGDMQICNRCQEH-UHFFFAOYSA-N 0.000 description 1
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| US7897598B2 (en) * | 1998-06-09 | 2011-03-01 | Alexandros Makriyannis | Inhibitors of the anandamide transporter |
| US7161016B1 (en) | 1998-11-24 | 2007-01-09 | University Of Connecticut | Cannabimimetic lipid amides as useful medications |
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| US6943266B1 (en) | 1999-10-18 | 2005-09-13 | University Of Connecticut | Bicyclic cannabinoid agonists for the cannabinoid receptor |
| US7741365B2 (en) * | 1999-10-18 | 2010-06-22 | University Of Connecticut | Peripheral cannabinoid receptor (CB2) selective ligands |
| US8084467B2 (en) * | 1999-10-18 | 2011-12-27 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
| US6900236B1 (en) | 1999-10-18 | 2005-05-31 | University Of Connecticut | Cannabimimetic indole derivatives |
| US7393842B2 (en) | 2001-08-31 | 2008-07-01 | University Of Connecticut | Pyrazole analogs acting on cannabinoid receptors |
| US7119108B1 (en) * | 1999-10-18 | 2006-10-10 | University Of Connecticut | Pyrazole derivatives as cannabinoid receptor antagonists |
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| ATE478670T1 (de) | 2001-01-29 | 2010-09-15 | Univ Connecticut | Rezeptor-selektive cannabimimetische aminoalkylindole |
| CA2452881C (en) * | 2001-07-13 | 2012-03-06 | University Of Connecticut | Novel bicyclic and tricyclic cannabinoids |
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| AU2002331766A1 (en) * | 2001-08-31 | 2003-03-18 | University Of Connecticut | Novel pyrazole analogs acting on cannabinoid receptors |
| CA2464333C (en) * | 2001-10-26 | 2011-07-26 | University Of Connecticut | Heteroindanes: a new class of potent cannabimimetic ligands |
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2001
- 2001-02-08 WO PCT/US2001/004131 patent/WO2001058869A2/en not_active Ceased
- 2001-02-08 AU AU2001234958A patent/AU2001234958A1/en not_active Abandoned
- 2001-02-08 US US09/779,109 patent/US6653304B2/en not_active Expired - Lifetime
- 2001-02-08 EP EP01907144A patent/EP1254115A2/en not_active Withdrawn
- 2001-02-08 JP JP2001558420A patent/JP2004502642A/ja active Pending
- 2001-02-08 CA CA002399791A patent/CA2399791A1/en not_active Abandoned
- 2001-02-09 AR ARP010100611A patent/AR027406A1/es unknown
- 2001-02-09 PE PE2001000145A patent/PE20020746A1/es not_active Application Discontinuation
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