ZA200504338B - Combination for the treatment of ADHD - Google Patents
Combination for the treatment of ADHD Download PDFInfo
- Publication number
- ZA200504338B ZA200504338B ZA200504338A ZA200504338A ZA200504338B ZA 200504338 B ZA200504338 B ZA 200504338B ZA 200504338 A ZA200504338 A ZA 200504338A ZA 200504338 A ZA200504338 A ZA 200504338A ZA 200504338 B ZA200504338 B ZA 200504338B
- Authority
- ZA
- South Africa
- Prior art keywords
- substituted
- azabicyclo
- carboxamide
- alkyl
- oct
- Prior art date
Links
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 title claims description 20
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 title claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 80
- -1 haloheterocycloalkyl Chemical group 0.000 claims description 63
- 125000001188 haloalkyl group Chemical group 0.000 claims description 60
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 59
- 150000001875 compounds Chemical class 0.000 claims description 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- 125000001424 substituent group Chemical group 0.000 claims description 50
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 50
- 239000000556 agonist Substances 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 22
- 239000003368 psychostimulant agent Substances 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 229910052799 carbon Inorganic materials 0.000 claims description 19
- 102000015296 acetylcholine-gated cation-selective channel activity proteins Human genes 0.000 claims description 18
- 108040006409 acetylcholine-gated cation-selective channel activity proteins Proteins 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 229940126403 monoamine reuptake inhibitor Drugs 0.000 claims description 17
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 11
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 10
- VHGCDTVCOLNTBX-QGZVFWFLSA-N atomoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=CC=C1C VHGCDTVCOLNTBX-QGZVFWFLSA-N 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 8
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical group C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 claims description 7
- 229960002430 atomoxetine Drugs 0.000 claims description 7
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 6
- YFGHCGITMMYXAQ-UHFFFAOYSA-N 2-[(diphenylmethyl)sulfinyl]acetamide Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)N)C1=CC=CC=C1 YFGHCGITMMYXAQ-UHFFFAOYSA-N 0.000 claims description 6
- SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 claims description 6
- 235000005152 nicotinamide Nutrition 0.000 claims description 5
- 239000011570 nicotinamide Substances 0.000 claims description 5
- NRNCYVBFPDDJNE-UHFFFAOYSA-N pemoline Chemical compound O1C(N)=NC(=O)C1C1=CC=CC=C1 NRNCYVBFPDDJNE-UHFFFAOYSA-N 0.000 claims description 5
- RZTBCSXEUILDSF-UHFFFAOYSA-N pyrrolo[1,2-a]pyrazine-3-carboxamide Chemical compound C1=NC(C(=O)N)=CN2C=CC=C21 RZTBCSXEUILDSF-UHFFFAOYSA-N 0.000 claims description 5
- VFGUCKRRIWUMQR-UHFFFAOYSA-N [1,3]dioxolo[4,5-c]pyridine-6-carboxamide Chemical compound O1COC=2C=NC(=CC=21)C(=O)N VFGUCKRRIWUMQR-UHFFFAOYSA-N 0.000 claims description 4
- 229940025084 amphetamine Drugs 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229960000761 pemoline Drugs 0.000 claims description 4
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims description 3
- PYHRZPFZZDCOPH-QXGOIDDHSA-N (S)-amphetamine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C[C@H](N)CC1=CC=CC=C1.C[C@H](N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-QXGOIDDHSA-N 0.000 claims description 3
- RTHCYVBBDHJXIQ-UHFFFAOYSA-N N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)OC1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-UHFFFAOYSA-N 0.000 claims description 3
- PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 claims description 3
- 229940047812 adderall Drugs 0.000 claims description 3
- 229960001058 bupropion Drugs 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229960003914 desipramine Drugs 0.000 claims description 3
- 229960000632 dexamfetamine Drugs 0.000 claims description 3
- 229940099242 dexedrine Drugs 0.000 claims description 3
- 229960002464 fluoxetine Drugs 0.000 claims description 3
- JUMYIBMBTDDLNG-UHFFFAOYSA-N methylphenidate hydrochloride Chemical group [Cl-].C=1C=CC=CC=1C(C(=O)OC)C1CCCC[NH2+]1 JUMYIBMBTDDLNG-UHFFFAOYSA-N 0.000 claims description 3
- 229960001165 modafinil Drugs 0.000 claims description 3
- AMRWFRQVCKJNSX-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC=C2 AMRWFRQVCKJNSX-BONVTDFDSA-N 0.000 claims description 3
- ILPMCCHSJHBDDW-LOACHALJSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-ethyl-2,3-dihydro-1,4-benzodioxine-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2OCC(CC)OC2=C1 ILPMCCHSJHBDDW-LOACHALJSA-N 0.000 claims description 3
- PTGWFYYEAUFEAS-ZYHUDNBSSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2 PTGWFYYEAUFEAS-ZYHUDNBSSA-N 0.000 claims description 3
- 229940087480 norpramin Drugs 0.000 claims description 3
- 229960001158 nortriptyline Drugs 0.000 claims description 3
- 229940117394 provigil Drugs 0.000 claims description 3
- 229940035613 prozac Drugs 0.000 claims description 3
- CBQGYUDMJHNJBX-RTBURBONSA-N reboxetine Chemical compound CCOC1=CC=CC=C1O[C@H](C=1C=CC=CC=1)[C@@H]1OCCNC1 CBQGYUDMJHNJBX-RTBURBONSA-N 0.000 claims description 3
- 229960003770 reboxetine Drugs 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 229940012488 strattera Drugs 0.000 claims description 3
- TUPZWIXDHKKDRH-UHFFFAOYSA-N thieno[3,2-c]pyridine-6-carboxamide Chemical compound C1=NC(C(=O)N)=CC2=C1C=CS2 TUPZWIXDHKKDRH-UHFFFAOYSA-N 0.000 claims description 3
- VEPNWVXJDUROKQ-UHFFFAOYSA-N thieno[3,4-c]pyridine-6-carboxamide Chemical compound C=1SC=C2C=NC(=CC21)C(=O)N VEPNWVXJDUROKQ-UHFFFAOYSA-N 0.000 claims description 3
- 229940009065 wellbutrin Drugs 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- SCPISZABYCFAAT-UHFFFAOYSA-N 3-ethylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C(C)C1=COC2=CN=C(C=C21)C(=O)N SCPISZABYCFAAT-UHFFFAOYSA-N 0.000 claims description 2
- IPKZCLGGYKRDES-ZDUSSCGKSA-N Pha-543613 Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1OC=C2 IPKZCLGGYKRDES-ZDUSSCGKSA-N 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 claims description 2
- JMDKTKWBOZYREH-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)-[1]benzothiolo[3,2-c]pyridine-3-carboxamide Chemical compound S1C2=CC=CC=C2C(C=N2)=C1C=C2C(=O)NC1C(CC2)CCN2C1 JMDKTKWBOZYREH-UHFFFAOYSA-N 0.000 claims description 2
- IPKZCLGGYKRDES-UHFFFAOYSA-N n-(1-azabicyclo[2.2.2]octan-3-yl)furo[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2C1NC(=O)C(N=C1)=CC2=C1OC=C2 IPKZCLGGYKRDES-UHFFFAOYSA-N 0.000 claims description 2
- WZTHKRMSZTXOAZ-ZBEGNZNMSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]-1-benzothiophene-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC=C(SC=C2)C2=C1 WZTHKRMSZTXOAZ-ZBEGNZNMSA-N 0.000 claims description 2
- ZKKGMKJDVSZXBI-UGSOOPFHSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]naphthalene-2-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC=C(C=CC=C2)C2=C1 ZKKGMKJDVSZXBI-UGSOOPFHSA-N 0.000 claims description 2
- OHRZCDCIGLVBCG-BONVTDFDSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,2-c]pyridine-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1C=CS2 OHRZCDCIGLVBCG-BONVTDFDSA-N 0.000 claims description 2
- CXDMUUBLDHSHNL-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=CC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 CXDMUUBLDHSHNL-AWEZNQCLSA-N 0.000 claims description 2
- AFLJKKMTBWNZFE-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=CSC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 AFLJKKMTBWNZFE-AWEZNQCLSA-N 0.000 claims description 2
- DPSFSXMSAJMDPZ-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1-methylindole-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2C=CN(C)C2=C1 DPSFSXMSAJMDPZ-HNNXBMFYSA-N 0.000 claims description 2
- GTDDJGZNXMIDBO-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-methyl-1,3-benzoxazole-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C(OC(C)=N2)C2=C1 GTDDJGZNXMIDBO-AWEZNQCLSA-N 0.000 claims description 2
- KBQZRHKFXMWELS-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-methyl-1-benzofuran-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C(OC(C)=C2)C2=C1 KBQZRHKFXMWELS-HNNXBMFYSA-N 0.000 claims description 2
- GAMVBVIWDSSMAL-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2-methyl-1-benzofuran-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2C=C(C)OC2=C1 GAMVBVIWDSSMAL-HNNXBMFYSA-N 0.000 claims description 2
- LIPFPTTWJOEZMN-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2h-chromene-6-carboxamide Chemical compound O1CC=CC2=CC(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC=C21 LIPFPTTWJOEZMN-HNNXBMFYSA-N 0.000 claims description 2
- NEEBQXWTTPJPPJ-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-bromo-1-benzofuran-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2OC=C(Br)C2=C1 NEEBQXWTTPJPPJ-AWEZNQCLSA-N 0.000 claims description 2
- HVUMNDIDTVKZBY-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-bromofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(Br)C2=C1 HVUMNDIDTVKZBY-ZDUSSCGKSA-N 0.000 claims description 2
- JZLHKFBLZXCFNR-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-bromothieno[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2SC=C(Br)C2=C1 JZLHKFBLZXCFNR-ZDUSSCGKSA-N 0.000 claims description 2
- CPYLAMFWQOHAQI-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-cyano-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(C#N)C2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 CPYLAMFWQOHAQI-HNNXBMFYSA-N 0.000 claims description 2
- SXPBPHDGAXTQLO-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-cyanofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1OC=C2C#N SXPBPHDGAXTQLO-AWEZNQCLSA-N 0.000 claims description 2
- NIKKRPJTQPOEOO-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-ethylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(CC)C2=C1 NIKKRPJTQPOEOO-HNNXBMFYSA-N 0.000 claims description 2
- MWRVGLIHPSVYPS-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-ethynyl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(C#C)C2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 MWRVGLIHPSVYPS-INIZCTEOSA-N 0.000 claims description 2
- FIKWYHHRAFNLSF-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-methyl-1-benzofuran-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2OC=C(C)C2=C1 FIKWYHHRAFNLSF-HNNXBMFYSA-N 0.000 claims description 2
- JJEYDHWWUYPKDW-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-prop-1-ynyl-1-benzofuran-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2OC=C(C#CC)C2=C1 JJEYDHWWUYPKDW-KRWDZBQOSA-N 0.000 claims description 2
- XGRQNDGMEYPKIB-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-prop-1-ynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(C#CC)C2=C1 XGRQNDGMEYPKIB-INIZCTEOSA-N 0.000 claims description 2
- HYRFDAUWCLPERX-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-propan-2-yl-1-benzofuran-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2OC=C(C(C)C)C2=C1 HYRFDAUWCLPERX-KRWDZBQOSA-N 0.000 claims description 2
- VHWVJYZANUDUMS-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-propan-2-ylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(C(C)C)C2=C1 VHWVJYZANUDUMS-INIZCTEOSA-N 0.000 claims description 2
- MLQQWDWROFCCOB-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-methylisoquinoline-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC2=CC(C)=CC=C2C=N1 MLQQWDWROFCCOB-KRWDZBQOSA-N 0.000 claims description 2
- HABGTPPBMNXFLE-SFHVURJKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-7-methoxynaphthalene-2-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC2=CC(OC)=CC=C2C=C1 HABGTPPBMNXFLE-SFHVURJKSA-N 0.000 claims description 2
- JHRRADCVOUYBLD-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]dibenzothiophene-2-carboxamide Chemical compound C1=CC=C2C3=CC(C(N[C@@H]4C5CCN(CC5)C4)=O)=CC=C3SC2=C1 JHRRADCVOUYBLD-KRWDZBQOSA-N 0.000 claims description 2
- YMZFSPQBWIIQLA-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]furo[3,2-c]pyridine-6-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1C=CO2 YMZFSPQBWIIQLA-ZDUSSCGKSA-N 0.000 claims description 2
- SJUAXKQQDBQMMM-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]indolizine-6-carboxamide Chemical compound C1=CC2=CC=CN2C=C1C(=O)N[C@@H]1C(CC2)CCN2C1 SJUAXKQQDBQMMM-HNNXBMFYSA-N 0.000 claims description 2
- CAAYBIHYHYDTMB-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]isoquinoline-3-carboxamide Chemical compound C1=CC=C2C=NC(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC2=C1 CAAYBIHYHYDTMB-INIZCTEOSA-N 0.000 claims description 2
- OHJHVDISSKRTPI-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]naphthalene-2-carboxamide Chemical compound C1=CC=CC2=CC(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC=C21 OHJHVDISSKRTPI-KRWDZBQOSA-N 0.000 claims description 2
- VHNOLIUQHIUIRU-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]pyrrolo[1,2-c]pyrimidine-3-carboxamide Chemical compound C=1C2=CC=CN2C=NC=1C(=O)N[C@@H]1C(CC2)CCN2C1 VHNOLIUQHIUIRU-AWEZNQCLSA-N 0.000 claims description 2
- NJNIZJCRCANYGV-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1SC=C2 NJNIZJCRCANYGV-ZDUSSCGKSA-N 0.000 claims description 2
- CKZPWHBWHVGFPO-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,2-c]pyridine-6-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1C=CS2 CKZPWHBWHVGFPO-ZDUSSCGKSA-N 0.000 claims description 2
- YFKLRJAXZCUFEL-STQMWFEESA-N n-[(3r,4s)-1-azabicyclo[2.2.1]heptan-3-yl]-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=CC2=CC(C(=O)N[C@H]2CN3CC[C@]2(C3)[H])=C1 YFKLRJAXZCUFEL-STQMWFEESA-N 0.000 claims description 2
- FAANZPHMLANWAQ-STQMWFEESA-N n-[(3r,4s)-1-azabicyclo[2.2.1]heptan-3-yl]-1-benzothiophene-6-carboxamide Chemical compound C1=C2C=CSC2=CC(C(=O)N[C@H]2CN3CC[C@]2(C3)[H])=C1 FAANZPHMLANWAQ-STQMWFEESA-N 0.000 claims description 2
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- ZLYNXTYFPVYJKB-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzothiazole-6-carboxamide Chemical compound C1=C2N=CSC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 ZLYNXTYFPVYJKB-ZDUSSCGKSA-N 0.000 description 1
- FDHHAJRIMDJGMH-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzoxazole-5-carboxamide Chemical compound C1=C2OC=NC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 FDHHAJRIMDJGMH-ZDUSSCGKSA-N 0.000 description 1
- VHAJPVHGNQXFSO-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1-benzothiophene-5-carboxamide Chemical compound C1=C2SC=CC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 VHAJPVHGNQXFSO-AWEZNQCLSA-N 0.000 description 1
- YGTNJCNUBHRGNM-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2,3-dihydro-1-benzofuran-5-carboxamide Chemical compound C1=C2OCCC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 YGTNJCNUBHRGNM-AWEZNQCLSA-N 0.000 description 1
- YCSBGDZYEYEBHT-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(Cl)C2=C1 YCSBGDZYEYEBHT-ZDUSSCGKSA-N 0.000 description 1
- BRKZBUICSDLTJB-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-ethynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1OC=C2C#C BRKZBUICSDLTJB-HNNXBMFYSA-N 0.000 description 1
- VSFFJFOPGAUTNI-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(C)C2=C1 VSFFJFOPGAUTNI-AWEZNQCLSA-N 0.000 description 1
- SDQLBZDKIXQSDJ-LBPRGKRZSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-bromopyrrolo[1,2-a]pyrazine-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CN2C(Br)=CC=C2C=N1 SDQLBZDKIXQSDJ-LBPRGKRZSA-N 0.000 description 1
- VLQHCUFLQYLUIY-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-8-methoxynaphthalene-2-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2C=CC=C(OC)C2=C1 VLQHCUFLQYLUIY-KRWDZBQOSA-N 0.000 description 1
- MZQSJUPWLIOLPC-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-[1]benzofuro[2,3-c]pyridine-3-carboxamide Chemical compound O1C2=CC=CC=C2C2=C1C=NC(C(N[C@@H]1C3CCN(CC3)C1)=O)=C2 MZQSJUPWLIOLPC-INIZCTEOSA-N 0.000 description 1
- GVWLRDPBVKRAIS-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]pyrazino[1,2-a]indole-3-carboxamide Chemical compound N1=CC2=CC3=CC=CC=C3N2C=C1C(=O)N[C@@H]1C(CC2)CCN2C1 GVWLRDPBVKRAIS-INIZCTEOSA-N 0.000 description 1
- FSWJILNACZEMQN-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,4-c]pyridine-6-carboxamide Chemical compound C=1C2=CSC=C2C=NC=1C(=O)N[C@@H]1C(CC2)CCN2C1 FSWJILNACZEMQN-AWEZNQCLSA-N 0.000 description 1
- WCDJHBXMVYUZLN-UFBFGSQYSA-N n-[(3r,4s)-1-azabicyclo[2.2.1]heptan-3-yl]-3-bromofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@]1(C2)[H])C(=O)C(N=C1)=CC2=C1OC=C2Br WCDJHBXMVYUZLN-UFBFGSQYSA-N 0.000 description 1
- CDQRPYYOVWJPET-UFBFGSQYSA-N n-[(3r,4s)-1-azabicyclo[2.2.1]heptan-3-yl]-3-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@]1(C2)[H])C(=O)C(N=C1)=CC2=C1OC=C2Cl CDQRPYYOVWJPET-UFBFGSQYSA-N 0.000 description 1
- XGRYNRMGVCZDEI-JQWIXIFHSA-N n-[(3r,4s)-1-azabicyclo[2.2.1]heptan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@]1(C2)[H])C(=O)C(N=C1)=CC2=C1OC=C2 XGRYNRMGVCZDEI-JQWIXIFHSA-N 0.000 description 1
- ZCHLHQVYHFPHIF-VXGBXAGGSA-N n-[(3r,5r)-1-azabicyclo[3.2.1]octan-3-yl]-3-methylfuro[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1CN2CC[C@@](C2)(C1)[H])C(=O)C(N=C1)=CC2=C1OC=C2C ZCHLHQVYHFPHIF-VXGBXAGGSA-N 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical group C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 150000008584 quinuclidines Chemical class 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Developing Agents For Electrophotography (AREA)
- Liquid Crystal Substances (AREA)
- Mechanical Treatment Of Semiconductor (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43258602P | 2002-12-11 | 2002-12-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200504338B true ZA200504338B (en) | 2006-07-26 |
Family
ID=32507968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200504338A ZA200504338B (en) | 2002-12-11 | 2005-05-27 | Combination for the treatment of ADHD |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US20050107425A1 (pl) |
| EP (1) | EP1572300A1 (pl) |
| JP (1) | JP2006510663A (pl) |
| KR (1) | KR20050085538A (pl) |
| CN (1) | CN1735441A (pl) |
| AP (1) | AP2005003336A0 (pl) |
| AU (1) | AU2003283656A1 (pl) |
| BR (1) | BR0317229A (pl) |
| CA (1) | CA2509142A1 (pl) |
| CO (1) | CO5700801A2 (pl) |
| CR (1) | CR7868A (pl) |
| EA (1) | EA200500783A1 (pl) |
| EC (1) | ECSP055852A (pl) |
| HR (1) | HRP20050522A2 (pl) |
| IS (1) | IS7858A (pl) |
| MA (1) | MA27606A1 (pl) |
| MX (1) | MXPA05006336A (pl) |
| NO (1) | NO20053185L (pl) |
| OA (1) | OA12969A (pl) |
| PL (1) | PL377552A1 (pl) |
| TN (1) | TNSN05158A1 (pl) |
| WO (1) | WO2004052461A1 (pl) |
| ZA (1) | ZA200504338B (pl) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| GB0310867D0 (en) * | 2003-05-12 | 2003-06-18 | Novartis Ag | Organic compounds |
| US20050234095A1 (en) | 2004-03-25 | 2005-10-20 | Wenge Xie | Indazoles, benzothiazoles, benzoisothiazoles, benzisoxazoles, and preparation and uses thereof |
| GB0424564D0 (en) * | 2004-11-05 | 2004-12-08 | Novartis Ag | Organic compounds |
| WO2008083442A1 (en) * | 2007-01-10 | 2008-07-17 | Brc Operations Pty Limited | Method for formulating combination medications for adhd |
| WO2008119017A1 (en) * | 2007-03-28 | 2008-10-02 | High Point Pharmaceuticals, Llc | 11beta-hsd1 active compounds |
| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| NZ594937A (en) * | 2008-02-19 | 2013-03-28 | Adolor Corp | Beloxepin, its enantiomers, and analogs thereof for the treatment of pain |
| US8927549B2 (en) | 2008-11-21 | 2015-01-06 | High Point Pharmaceuticals, Llc | Adamantyl benzamide derivatives |
| TW201031664A (en) | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| BR112012029237A2 (pt) | 2010-05-17 | 2016-11-29 | Envivo Pharmaceuticals Inc | forma cristalina de cloridrato de (r)-7-cloro-n-(quinuclidin-3-il) benzo[b] tiofeno-2-carboxamida monohidratado |
| US8513430B2 (en) | 2010-07-27 | 2013-08-20 | High Point Pharmaceuticals, Llc | Substituted thiazol-2-ylamine derivatives, pharmaceutical compositions, and methods of use as 11-beta HSD1 modulators |
| RU2635522C2 (ru) | 2012-05-08 | 2017-11-13 | Форум Фармасьютикалз, Инк. | Способы поддержания, лечения или улучшения когнитивной функции |
| EP2919788A4 (en) | 2012-11-14 | 2016-05-25 | Univ Johns Hopkins | METHODS AND COMPOSITIONS FOR THE TREATMENT OF SCHIZOPHRENIA |
| CA3123215C (en) | 2018-12-19 | 2024-04-02 | Disarm Therapeutics, Inc. | Inhibitors of sarm1 in combination with neuroprotective agents |
| WO2023022256A1 (ko) | 2021-08-19 | 2023-02-23 | 단국대학교 천안캠퍼스 산학협력단 | Kds2010을 유효성분으로 포함하는 주의력결핍 과잉행동장애의 예방 또는 치료용 약학적 조성물 |
| WO2023022269A1 (ko) | 2021-08-20 | 2023-02-23 | 단국대학교 천안캠퍼스 산학협력단 | 주의력결핍 과잉행동장애의 예방 또는 치료용 약학적 조성물 |
| KR102684933B1 (ko) | 2021-08-20 | 2024-07-16 | 단국대학교 천안캠퍼스 산학협력단 | 주의력결핍 과잉행동장애의 진단을 위한 gat-3의 용도 |
| KR102597711B1 (ko) | 2021-08-20 | 2023-11-06 | 단국대학교 천안캠퍼스 산학협력단 | Snap5114을 유효성분으로 포함하는 주의력결핍 과잉행동장애의 예방 또는 치료용 약학적 조성물 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020016334A1 (en) * | 2000-07-31 | 2002-02-07 | Coe Jotham Wadsworth | Pharmaceutical composition for the treatment of attention deficit hyperactivity disorder (ADHD) |
| US20030236287A1 (en) * | 2002-05-03 | 2003-12-25 | Piotrowski David W. | Positive allosteric modulators of the nicotinic acetylcholine receptor |
-
2003
- 2003-11-28 CA CA002509142A patent/CA2509142A1/en not_active Abandoned
- 2003-11-28 CN CNA2003801084894A patent/CN1735441A/zh active Pending
- 2003-11-28 BR BR0317229-5A patent/BR0317229A/pt not_active IP Right Cessation
- 2003-11-28 WO PCT/IB2003/005542 patent/WO2004052461A1/en not_active Application Discontinuation
- 2003-11-28 EA EA200500783A patent/EA200500783A1/ru unknown
- 2003-11-28 PL PL377552A patent/PL377552A1/pl not_active Application Discontinuation
- 2003-11-28 JP JP2004558921A patent/JP2006510663A/ja active Pending
- 2003-11-28 OA OA1200500174A patent/OA12969A/en unknown
- 2003-11-28 AU AU2003283656A patent/AU2003283656A1/en not_active Abandoned
- 2003-11-28 AP AP2005003336A patent/AP2005003336A0/xx unknown
- 2003-11-28 KR KR1020057010591A patent/KR20050085538A/ko not_active Application Discontinuation
- 2003-11-28 MX MXPA05006336A patent/MXPA05006336A/es not_active Application Discontinuation
- 2003-11-28 EP EP03775637A patent/EP1572300A1/en not_active Withdrawn
-
2004
- 2004-10-12 US US10/963,922 patent/US20050107425A1/en not_active Abandoned
-
2005
- 2005-05-23 IS IS7858A patent/IS7858A/is unknown
- 2005-05-27 ZA ZA200504338A patent/ZA200504338B/en unknown
- 2005-06-09 HR HR20050522A patent/HRP20050522A2/hr not_active Application Discontinuation
- 2005-06-10 CO CO05056569A patent/CO5700801A2/es not_active Application Discontinuation
- 2005-06-10 CR CR7868A patent/CR7868A/es not_active Application Discontinuation
- 2005-06-10 TN TNP2005000158A patent/TNSN05158A1/fr unknown
- 2005-06-10 EC EC2005005852A patent/ECSP055852A/es unknown
- 2005-06-10 MA MA28325A patent/MA27606A1/fr unknown
- 2005-06-29 NO NO20053185A patent/NO20053185L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2509142A1 (en) | 2004-06-24 |
| CN1735441A (zh) | 2006-02-15 |
| ECSP055852A (es) | 2005-09-20 |
| WO2004052461A1 (en) | 2004-06-24 |
| IS7858A (is) | 2005-05-23 |
| MA27606A1 (fr) | 2005-11-01 |
| OA12969A (en) | 2006-10-13 |
| CO5700801A2 (es) | 2006-11-30 |
| NO20053185D0 (no) | 2005-06-29 |
| NO20053185L (no) | 2005-08-17 |
| AU2003283656A1 (en) | 2004-06-30 |
| BR0317229A (pt) | 2005-11-01 |
| AP2005003336A0 (en) | 2005-06-30 |
| HRP20050522A2 (en) | 2005-12-31 |
| EP1572300A1 (en) | 2005-09-14 |
| US20050107425A1 (en) | 2005-05-19 |
| EA200500783A1 (ru) | 2005-12-29 |
| KR20050085538A (ko) | 2005-08-29 |
| JP2006510663A (ja) | 2006-03-30 |
| PL377552A1 (pl) | 2006-02-06 |
| CR7868A (es) | 2005-07-08 |
| TNSN05158A1 (fr) | 2007-05-14 |
| MXPA05006336A (es) | 2005-08-26 |
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