CZ20011796A3 - Pouľití N-substituovaných azabicycloalkanových derivátů pro léčení poruch centrálního nervového systému - Google Patents
Pouľití N-substituovaných azabicycloalkanových derivátů pro léčení poruch centrálního nervového systému Download PDFInfo
- Publication number
- CZ20011796A3 CZ20011796A3 CZ20011796A CZ20011796A CZ20011796A3 CZ 20011796 A3 CZ20011796 A3 CZ 20011796A3 CZ 20011796 A CZ20011796 A CZ 20011796A CZ 20011796 A CZ20011796 A CZ 20011796A CZ 20011796 A3 CZ20011796 A3 CZ 20011796A3
- Authority
- CZ
- Czechia
- Prior art keywords
- azabicyclo
- exo
- ethyl
- fluorophenyl
- heptyl
- Prior art date
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- 208000015114 central nervous system disease Diseases 0.000 title description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- 206010012335 Dependence Diseases 0.000 claims abstract description 4
- -1 C 1 -C 4 alkyl Chemical group 0.000 claims description 453
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 229940025084 amphetamine Drugs 0.000 claims description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000005561 phenanthryl group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 208000022497 Cocaine-Related disease Diseases 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 201000006145 cocaine dependence Diseases 0.000 claims 1
- 230000001955 cumulated effect Effects 0.000 claims 1
- 206010013663 drug dependence Diseases 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims 1
- 201000010099 disease Diseases 0.000 abstract 2
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 183
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 62
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 47
- CVIBKISSHDMEKJ-UHFFFAOYSA-N 1-ethylquinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)N(CC)C2=C1 CVIBKISSHDMEKJ-UHFFFAOYSA-N 0.000 description 43
- YJJOJBNUDCBRTM-UHFFFAOYSA-N 5-ethyl-3,6-dimethyl-2-(methylamino)pyrimidin-4-one Chemical compound CCC1=C(C)N=C(NC)N(C)C1=O YJJOJBNUDCBRTM-UHFFFAOYSA-N 0.000 description 28
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 28
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 26
- PCDHSSHKDZYLLI-UHFFFAOYSA-N butan-1-one Chemical compound CCC[C]=O PCDHSSHKDZYLLI-UHFFFAOYSA-N 0.000 description 26
- LETMUHYAZQNEQL-UHFFFAOYSA-N 2-ethyl-7-methyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound S1C(CC)=CN2C1=NC(C)=CC2=O LETMUHYAZQNEQL-UHFFFAOYSA-N 0.000 description 22
- IICQZTQZQSBHBY-UHFFFAOYSA-N non-2-ene Chemical compound CCCCCCC=CC IICQZTQZQSBHBY-UHFFFAOYSA-N 0.000 description 21
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 17
- YCBSHDKATAPNIA-UHFFFAOYSA-N non-3-ene Chemical compound CCCCCC=CCC YCBSHDKATAPNIA-UHFFFAOYSA-N 0.000 description 17
- RMHJJUOPOWPRBP-UHFFFAOYSA-N naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=C1 RMHJJUOPOWPRBP-UHFFFAOYSA-N 0.000 description 16
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 14
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 14
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 13
- VSMXLKGFTKFOSB-UHFFFAOYSA-N 1-ethyl-3h-indol-2-one Chemical compound C1=CC=C2N(CC)C(=O)CC2=C1 VSMXLKGFTKFOSB-UHFFFAOYSA-N 0.000 description 10
- CIGBERQUNYDMHH-UHFFFAOYSA-N 1H-indene-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CCC2=C1 CIGBERQUNYDMHH-UHFFFAOYSA-N 0.000 description 10
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- CXUCKELNYMZTRT-UHFFFAOYSA-N 1-Ethyl-2-benzimidazolinone Chemical compound C1=CC=C2NC(=O)N(CC)C2=C1 CXUCKELNYMZTRT-UHFFFAOYSA-N 0.000 description 8
- JRXCUTAHLPYHAY-UHFFFAOYSA-N 1-ethylquinolin-2-one Chemical compound C1=CC=C2C=CC(=O)N(CC)C2=C1 JRXCUTAHLPYHAY-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000001273 butane Substances 0.000 description 7
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- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 7
- DKKRVLCXVRLMMU-UHFFFAOYSA-N 3-ethyl-2-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC=CN2C(=O)C(CC)=C(C)N=C21 DKKRVLCXVRLMMU-UHFFFAOYSA-N 0.000 description 6
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 6
- GJDPKSPCTDQLKP-UHFFFAOYSA-N C(C)C1C=CN2C(S1)=NC(=CC2=O)C Chemical compound C(C)C1C=CN2C(S1)=NC(=CC2=O)C GJDPKSPCTDQLKP-UHFFFAOYSA-N 0.000 description 5
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- BWNBLGQCCSCCHF-UHFFFAOYSA-N 2-ethyl-1h-indole Chemical compound C1=CC=C2NC(CC)=CC2=C1 BWNBLGQCCSCCHF-UHFFFAOYSA-N 0.000 description 4
- FIEYHAAMDAPVCH-UHFFFAOYSA-N 2-methyl-1h-quinazolin-4-one Chemical compound C1=CC=C2NC(C)=NC(=O)C2=C1 FIEYHAAMDAPVCH-UHFFFAOYSA-N 0.000 description 4
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 description 4
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 description 4
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 3
- NYWQHWCJDBQSBY-UHFFFAOYSA-N 1-ethyl-3-octan-3-ylquinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)N(C(CC)CCCCC)C(=O)N(CC)C2=C1 NYWQHWCJDBQSBY-UHFFFAOYSA-N 0.000 description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 3
- XFYIIXTWGSQBFN-UHFFFAOYSA-N 3-ethyl-2,7-dimethylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC(C)=CN2C(=O)C(CC)=C(C)N=C21 XFYIIXTWGSQBFN-UHFFFAOYSA-N 0.000 description 3
- ZKTPNFVIILANHV-UHFFFAOYSA-N 3-ethyl-2-methyl-6,7,8,9-tetrahydropyrido[1,2-a]pyrimidin-4-one Chemical compound C1CCCN2C(=O)C(CC)=C(C)N=C21 ZKTPNFVIILANHV-UHFFFAOYSA-N 0.000 description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 3
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- QNPCLOIFWORBJP-UHFFFAOYSA-N 1-ethyl-6-fluoroquinazoline-2,4-dione Chemical compound C(C)N1C(NC(C2=CC(=CC=C12)F)=O)=O QNPCLOIFWORBJP-UHFFFAOYSA-N 0.000 description 2
- HKDKELZTBPEWSU-UHFFFAOYSA-N 1-ethyl-6-methylquinazoline-2,4-dione Chemical compound C(C)N1C(NC(C2=CC(=CC=C12)C)=O)=O HKDKELZTBPEWSU-UHFFFAOYSA-N 0.000 description 2
- LSGKMZLPZFPAIN-UHFFFAOYSA-N 1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=C1 LSGKMZLPZFPAIN-UHFFFAOYSA-N 0.000 description 2
- OFPWIXYGAJDWPC-UHFFFAOYSA-N 2-ethyl-1h-pyrimidin-6-one Chemical compound CCC1=NC=CC(=O)N1 OFPWIXYGAJDWPC-UHFFFAOYSA-N 0.000 description 2
- CJCVPBLPKUXYKO-UHFFFAOYSA-N 2-ethyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound S1C(CC)=CN2C1=NC=CC2=O CJCVPBLPKUXYKO-UHFFFAOYSA-N 0.000 description 2
- LDZYRENCLPUXAX-UHFFFAOYSA-N 2-methyl-1h-benzimidazole Chemical compound C1=CC=C2NC(C)=NC2=C1 LDZYRENCLPUXAX-UHFFFAOYSA-N 0.000 description 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 2
- KIYKJTIONPRZJR-UHFFFAOYSA-N 3-ethyl-2,9-dimethylpyrido[1,2-a]pyrimidin-4-one Chemical compound CC1=CC=CN2C(=O)C(CC)=C(C)N=C21 KIYKJTIONPRZJR-UHFFFAOYSA-N 0.000 description 2
- QAZLESDATKIWGZ-UHFFFAOYSA-N 5-chloro-1-ethylquinazoline-2,4-dione Chemical compound C(C)N1C(NC(C2=C(C=CC=C12)Cl)=O)=O QAZLESDATKIWGZ-UHFFFAOYSA-N 0.000 description 2
- KWNQIIMVPSMYEM-UHFFFAOYSA-N 6,7-dimethoxy-1h-quinazoline-2,4-dione Chemical compound N1C(=O)NC(=O)C2=C1C=C(OC)C(OC)=C2 KWNQIIMVPSMYEM-UHFFFAOYSA-N 0.000 description 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 description 2
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- 230000037396 body weight Effects 0.000 description 2
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- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 description 2
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- 239000003826 tablet Substances 0.000 description 2
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
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- ZMXIYERNXPIYFR-UHFFFAOYSA-N 1-ethylnaphthalene Chemical compound C1=CC=C2C(CC)=CC=CC2=C1 ZMXIYERNXPIYFR-UHFFFAOYSA-N 0.000 description 1
- ASMIAPCOQULGEO-UHFFFAOYSA-N 1-ethylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)N(CC)C2=C1C=CS2 ASMIAPCOQULGEO-UHFFFAOYSA-N 0.000 description 1
- PKVLOXUKWNLUNA-UHFFFAOYSA-N 1-ethylthieno[3,2-d]pyrimidine-2,4-dione Chemical compound C(C)N1C(NC(C2=C1C=CS2)=O)=O PKVLOXUKWNLUNA-UHFFFAOYSA-N 0.000 description 1
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- GVYVHZKTSVDMNT-UHFFFAOYSA-N 2,3-dihydro-1,2-benzothiazole 1,1-dioxide Chemical compound C1=CC=C2S(=O)(=O)NCC2=C1 GVYVHZKTSVDMNT-UHFFFAOYSA-N 0.000 description 1
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- QZFJPVDLQICTAW-UHFFFAOYSA-N 3-ethyl-2-methylpyrimido[1,2-a]pyrimidin-4-one Chemical compound C(C)C1=C(N=C2N(C1=O)C=CC=N2)C QZFJPVDLQICTAW-UHFFFAOYSA-N 0.000 description 1
- UMQKDYHNDQNEBD-UHFFFAOYSA-N 3-ethyl-2-methylquinazolin-4-one Chemical compound C1=CC=C2C(=O)N(CC)C(C)=NC2=C1 UMQKDYHNDQNEBD-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- AYESCWWMKKCHKO-UHFFFAOYSA-N 5-ethyl-1,3,6-trimethylpyrimidine-2,4-dione Chemical compound CCC1=C(C)N(C)C(=O)N(C)C1=O AYESCWWMKKCHKO-UHFFFAOYSA-N 0.000 description 1
- JCSPMARRNGTFMN-UHFFFAOYSA-N 5-ethyl-4-methoxy-N,6-dimethylpyrimidin-2-amine Chemical compound C(C)C=1C(=NC(=NC=1C)NC)OC JCSPMARRNGTFMN-UHFFFAOYSA-N 0.000 description 1
- POHMUYGBYJQDCN-UHFFFAOYSA-N 5-heptan-3-yl-2,4-dimethyl-1H-pyrimidin-6-one Chemical compound CCC(CCCC)C=1C(=NC(=NC=1C)C)O POHMUYGBYJQDCN-UHFFFAOYSA-N 0.000 description 1
- ORGZMSYMWCSDIZ-UHFFFAOYSA-N 6,8-dichloro-1-ethylquinazoline-2,4-dione Chemical compound C1=C(Cl)C=C2C(=O)NC(=O)N(CC)C2=C1Cl ORGZMSYMWCSDIZ-UHFFFAOYSA-N 0.000 description 1
- OSRPAHRCPIGTJZ-UHFFFAOYSA-N 6-amino-1-ethylquinazoline-2,4-dione Chemical compound C1=C(N)C=C2C(=O)NC(=O)N(CC)C2=C1 OSRPAHRCPIGTJZ-UHFFFAOYSA-N 0.000 description 1
- ZXGAVIXWLAXEGE-UHFFFAOYSA-N 6-amino-3-ethyl-1-methylpyrimidine-2,4-dione Chemical compound CCN1C(=O)C=C(N)N(C)C1=O ZXGAVIXWLAXEGE-UHFFFAOYSA-N 0.000 description 1
- KOJIUFIJUGTHDB-UHFFFAOYSA-N 7-amino-1-ethylquinazoline-2,4-dione Chemical compound C(C)N1C(NC(C2=CC=C(C=C12)N)=O)=O KOJIUFIJUGTHDB-UHFFFAOYSA-N 0.000 description 1
- UELASANXXMJSKG-UHFFFAOYSA-N 7-chloro-1-ethylquinazoline-2,4-dione Chemical compound ClC1=CC=C2C(=O)NC(=O)N(CC)C2=C1 UELASANXXMJSKG-UHFFFAOYSA-N 0.000 description 1
- NYBDRQJPWDONJD-UHFFFAOYSA-N 7-chloro-3-ethyl-2-methylpyrimido[1,2-a]pyrimidin-4-one Chemical compound C(C)C1=C(N=C2N(C1=O)C=C(C=N2)Cl)C NYBDRQJPWDONJD-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- YCIPQJTZJGUXND-UHFFFAOYSA-N Aglaia odorata Alkaloid Natural products C1=CC(OC)=CC=C1C1(C(C=2C(=O)N3CCCC3=NC=22)C=3C=CC=CC=3)C2(O)C2=C(OC)C=C(OC)C=C2O1 YCIPQJTZJGUXND-UHFFFAOYSA-N 0.000 description 1
- GOEQLTJCLUKOFD-UHFFFAOYSA-N CCC1=C(C)N=C(N)N(C)C1=O Chemical compound CCC1=C(C)N=C(N)N(C)C1=O GOEQLTJCLUKOFD-UHFFFAOYSA-N 0.000 description 1
- IJXWKONOCIMIDP-UHFFFAOYSA-N Cl.Cl.C(C)C1=C(N=C2N(C1=O)C=CC=C2)C Chemical compound Cl.Cl.C(C)C1=C(N=C2N(C1=O)C=CC=C2)C IJXWKONOCIMIDP-UHFFFAOYSA-N 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 102000004300 GABA-A Receptors Human genes 0.000 description 1
- 108090000839 GABA-A Receptors Proteins 0.000 description 1
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 1
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- RJTJVVYSTUQWNI-UHFFFAOYSA-N beta-ethyl naphthalene Natural products C1=CC=CC2=CC(CC)=CC=C21 RJTJVVYSTUQWNI-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 description 1
- 229960002069 diamorphine Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XBCXJKGHPABGSD-UHFFFAOYSA-N methyluracil Natural products CN1C=CC(=O)NC1=O XBCXJKGHPABGSD-UHFFFAOYSA-N 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 125000005187 nonenyl group Chemical group C(=CCCCCCCC)* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229960000581 salicylamide Drugs 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000007885 tablet disintegrant Substances 0.000 description 1
- IOHCGRJBQIIEOU-UHFFFAOYSA-N thiazin-6-one Chemical compound O=C1C=CC=NS1 IOHCGRJBQIIEOU-UHFFFAOYSA-N 0.000 description 1
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19854147A DE19854147A1 (de) | 1998-11-24 | 1998-11-24 | Verwendung von N-substituierten Azabicycloalkan-Derivaten zur Verwendung bei der Bekämpfung der Cocainsucht |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ20011796A3 true CZ20011796A3 (cs) | 2002-05-15 |
Family
ID=7888824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20011796A CZ20011796A3 (cs) | 1998-11-24 | 1999-11-12 | Pouľití N-substituovaných azabicycloalkanových derivátů pro léčení poruch centrálního nervového systému |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP1133293A1 (pt) |
| JP (1) | JP2002530333A (pt) |
| KR (1) | KR20010080535A (pt) |
| CN (1) | CN1328455A (pt) |
| AR (1) | AR021502A1 (pt) |
| AU (1) | AU1775300A (pt) |
| BG (1) | BG105549A (pt) |
| BR (1) | BR9915589A (pt) |
| CA (1) | CA2352526A1 (pt) |
| CZ (1) | CZ20011796A3 (pt) |
| DE (1) | DE19854147A1 (pt) |
| HK (1) | HK1040933A1 (pt) |
| HR (1) | HRP20010472A2 (pt) |
| HU (1) | HUP0104416A3 (pt) |
| IL (1) | IL143181A0 (pt) |
| NO (1) | NO20012538L (pt) |
| PL (1) | PL348758A1 (pt) |
| SK (1) | SK7112001A3 (pt) |
| TR (1) | TR200101476T2 (pt) |
| WO (1) | WO2000030639A1 (pt) |
| ZA (1) | ZA200103976B (pt) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2005316739A1 (en) | 2004-12-13 | 2006-06-22 | Galileo Pharmaceuticals, Inc. | Spiro derivatives as lipoxygenase inhibitors |
| GB0812310D0 (en) | 2008-07-03 | 2008-08-13 | Syngenta Ltd | Novel herbicides |
| JP2016508159A (ja) * | 2013-01-15 | 2016-03-17 | ノバルティス アーゲー | アルファ７ニコチン性アセチルコリン受容体アゴニストの使用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1989004311A1 (en) * | 1987-11-12 | 1989-05-18 | American Home Products Corporation | Polycyclicamines with psychotropic activity |
| DE4427648A1 (de) * | 1994-08-04 | 1996-02-08 | Basf Ag | N-Stubstituierte 3-Azabicyclo[3,2,0,]heptan-Derivate, ihre Herstellung und Verwendung |
| DE4341403A1 (de) * | 1993-12-04 | 1995-06-08 | Basf Ag | N-substituierte 3-Azabicycloalkan-Derivate, ihre Herstellung und Verwendung |
| DE4427647A1 (de) * | 1994-08-04 | 1996-02-08 | Basf Ag | N-substituierte Azabicycloheptan-Derivate, ihre Herstellung und Verwendung |
-
1998
- 1998-11-24 DE DE19854147A patent/DE19854147A1/de not_active Withdrawn
-
1999
- 1999-11-12 CA CA002352526A patent/CA2352526A1/en not_active Abandoned
- 1999-11-12 EP EP99960974A patent/EP1133293A1/de not_active Withdrawn
- 1999-11-12 AU AU17753/00A patent/AU1775300A/en not_active Abandoned
- 1999-11-12 HK HK02102768.4A patent/HK1040933A1/zh unknown
- 1999-11-12 IL IL14318199A patent/IL143181A0/xx unknown
- 1999-11-12 KR KR1020017006445A patent/KR20010080535A/ko not_active Ceased
- 1999-11-12 HU HU0104416A patent/HUP0104416A3/hu unknown
- 1999-11-12 JP JP2000583522A patent/JP2002530333A/ja active Pending
- 1999-11-12 CN CN99813559A patent/CN1328455A/zh active Pending
- 1999-11-12 HR HR20010472A patent/HRP20010472A2/hr not_active Application Discontinuation
- 1999-11-12 BR BR9915589-3A patent/BR9915589A/pt not_active IP Right Cessation
- 1999-11-12 PL PL99348758A patent/PL348758A1/xx not_active Application Discontinuation
- 1999-11-12 CZ CZ20011796A patent/CZ20011796A3/cs unknown
- 1999-11-12 SK SK711-2001A patent/SK7112001A3/sk unknown
- 1999-11-12 WO PCT/EP1999/008734 patent/WO2000030639A1/de not_active Ceased
- 1999-11-12 TR TR2001/01476T patent/TR200101476T2/xx unknown
- 1999-11-24 AR ARP990105979A patent/AR021502A1/es unknown
-
2001
- 2001-05-16 ZA ZA200103976A patent/ZA200103976B/en unknown
- 2001-05-23 NO NO20012538A patent/NO20012538L/no not_active Application Discontinuation
- 2001-05-30 BG BG105549A patent/BG105549A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0104416A3 (en) | 2002-11-28 |
| NO20012538L (no) | 2001-07-04 |
| BG105549A (en) | 2001-12-29 |
| HUP0104416A2 (hu) | 2002-04-29 |
| WO2000030639A1 (de) | 2000-06-02 |
| KR20010080535A (ko) | 2001-08-22 |
| NO20012538D0 (no) | 2001-05-23 |
| AR021502A1 (es) | 2002-07-24 |
| DE19854147A1 (de) | 2000-05-25 |
| CA2352526A1 (en) | 2000-06-02 |
| CN1328455A (zh) | 2001-12-26 |
| PL348758A1 (en) | 2002-06-03 |
| IL143181A0 (en) | 2002-04-21 |
| HRP20010472A2 (en) | 2003-04-30 |
| BR9915589A (pt) | 2001-08-07 |
| EP1133293A1 (de) | 2001-09-19 |
| SK7112001A3 (en) | 2001-12-03 |
| AU1775300A (en) | 2000-06-13 |
| ZA200103976B (en) | 2002-05-16 |
| JP2002530333A (ja) | 2002-09-17 |
| TR200101476T2 (tr) | 2001-10-22 |
| HK1040933A1 (zh) | 2002-06-28 |
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