DE19854147A1 - Verwendung von N-substituierten Azabicycloalkan-Derivaten zur Verwendung bei der Bekämpfung der Cocainsucht - Google Patents
Verwendung von N-substituierten Azabicycloalkan-Derivaten zur Verwendung bei der Bekämpfung der CocainsuchtInfo
- Publication number
- DE19854147A1 DE19854147A1 DE19854147A DE19854147A DE19854147A1 DE 19854147 A1 DE19854147 A1 DE 19854147A1 DE 19854147 A DE19854147 A DE 19854147A DE 19854147 A DE19854147 A DE 19854147A DE 19854147 A1 DE19854147 A1 DE 19854147A1
- Authority
- DE
- Germany
- Prior art keywords
- azabicyclo
- exo
- ethyl
- fluorophenyl
- heptan
- 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.)
- Withdrawn
Links
- -1 NHCH3 Chemical group 0.000 abstract description 31
- 125000000217 alkyl group Chemical group 0.000 abstract description 14
- 229910052731 fluorine Inorganic materials 0.000 abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 9
- 125000001624 naphthyl group Chemical group 0.000 abstract description 8
- 229910052799 carbon Inorganic materials 0.000 abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 6
- 125000001544 thienyl group Chemical group 0.000 abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- 208000022497 Cocaine-Related disease Diseases 0.000 abstract description 4
- 201000006145 cocaine dependence Diseases 0.000 abstract description 4
- 206010013663 drug dependence Diseases 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 abstract description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract description 2
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 abstract description 2
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 abstract description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 2
- 125000001041 indolyl group Chemical group 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 125000005561 phenanthryl group Chemical group 0.000 abstract description 2
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 125000001475 halogen functional group Chemical group 0.000 abstract 3
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 96
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 60
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 45
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 29
- 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 28
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 28
- 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 24
- 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 24
- PCDHSSHKDZYLLI-UHFFFAOYSA-N butan-1-one Chemical compound CCC[C]=O PCDHSSHKDZYLLI-UHFFFAOYSA-N 0.000 description 24
- 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 11
- JRXCUTAHLPYHAY-UHFFFAOYSA-N 1-ethylquinolin-2-one Chemical compound C1=CC=C2C=CC(=O)N(CC)C2=C1 JRXCUTAHLPYHAY-UHFFFAOYSA-N 0.000 description 9
- CXUCKELNYMZTRT-UHFFFAOYSA-N 1-Ethyl-2-benzimidazolinone Chemical compound C1=CC=C2NC(=O)N(CC)C2=C1 CXUCKELNYMZTRT-UHFFFAOYSA-N 0.000 description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 239000001273 butane Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 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 4
- 150000001875 compounds Chemical class 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
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 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
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000005843 halogen group Chemical group 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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- 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 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
- BWNBLGQCCSCCHF-UHFFFAOYSA-N 2-ethyl-1h-indole Chemical compound C1=CC=C2NC(CC)=CC2=C1 BWNBLGQCCSCCHF-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
- AAIZLBJGGDQXFD-UHFFFAOYSA-N 3-ethyl-2,8-dimethylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(C)C=CN2C(=O)C(CC)=C(C)N=C21 AAIZLBJGGDQXFD-UHFFFAOYSA-N 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 description 2
- XRLDSWLMHUQECH-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1CCCC1 XRLDSWLMHUQECH-UHFFFAOYSA-N 0.000 description 2
- XBCXJKGHPABGSD-UHFFFAOYSA-N methyluracil Natural products CN1C=CC(=O)NC1=O XBCXJKGHPABGSD-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- QHKJIJXBJCOABP-UHFFFAOYSA-N 1-benzofuran-2-carboxamide Chemical compound C1=CC=C2OC(C(=O)N)=CC2=C1 QHKJIJXBJCOABP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- HWJSQHFEPQJHMG-UHFFFAOYSA-N 1-ethyl-6-methylpyrimidine-2,4-dione Chemical compound CCN1C(C)=CC(=O)NC1=O HWJSQHFEPQJHMG-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- VFHUJFBEFDVZPJ-UHFFFAOYSA-N 1h-indole-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=C1 VFHUJFBEFDVZPJ-UHFFFAOYSA-N 0.000 description 1
- CWWWTSHTBXXNEW-UHFFFAOYSA-N 2,7-dimethyl-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound S1C(C)=CN2C1=NC(C)=CC2=O CWWWTSHTBXXNEW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- DFNXHNBRQIABNY-UHFFFAOYSA-N 3-ethyl-2,6,8-trimethylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=C(C)C=C(C)N2C(=O)C(CC)=C(C)N=C21 DFNXHNBRQIABNY-UHFFFAOYSA-N 0.000 description 1
- RCSYPYSJSNRLSK-UHFFFAOYSA-N 3-ethyl-2,6-dimethylpyrido[1,2-a]pyrimidin-4-one Chemical compound C1=CC=C(C)N2C(=O)C(CC)=C(C)N=C21 RCSYPYSJSNRLSK-UHFFFAOYSA-N 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- UGCKJZOTEJEOMX-UHFFFAOYSA-N 4-[6-(4-chlorophenyl)-3-azabicyclo[3.2.0]heptan-3-yl]-1-thiophen-2-ylbutan-1-one Chemical compound C1=CC(Cl)=CC=C1C1C2CN(CCCC(=O)C=3SC=CC=3)CC2C1 UGCKJZOTEJEOMX-UHFFFAOYSA-N 0.000 description 1
- IEWMSXRYDTXBRF-UHFFFAOYSA-N 4-[6-(4-fluorophenyl)-3-azabicyclo[3.2.0]heptan-3-yl]-1-thiophen-2-ylbutan-1-one Chemical compound C1=CC(F)=CC=C1C1C2CN(CCCC(=O)C=3SC=CC=3)CC2C1 IEWMSXRYDTXBRF-UHFFFAOYSA-N 0.000 description 1
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- YCBSHDKATAPNIA-UHFFFAOYSA-N non-3-ene Chemical compound CCCCCC=CCC YCBSHDKATAPNIA-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 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 description 1
- 125000004430 oxygen atom Chemical group O* 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
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229960000581 salicylamide Drugs 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
- 239000007921 spray Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 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)
Priority Applications (21)
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 |
CN99813559A CN1328455A (zh) | 1998-11-24 | 1999-11-12 | N-取代的氮杂二环烷衍生物在治疗中枢神经系统疾病中的应用 |
SK711-2001A SK7112001A3 (en) | 1998-11-24 | 1999-11-12 | Use of n-substituted azabicycloalkane derivatives for treating diseases of the central nervous system |
AU17753/00A AU1775300A (en) | 1998-11-24 | 1999-11-12 | Use of n-substituted azabicycloalkane derivatives for treating diseases of the central nervous system |
BR9915589-3A BR9915589A (pt) | 1998-11-24 | 1999-11-12 | Uso de derivados de azabicicloalcano n-substituìdo |
CA002352526A CA2352526A1 (en) | 1998-11-24 | 1999-11-12 | Use of n-substituted azabicycloalkane derivatives for treating diseases of the central nervous system |
CZ20011796A CZ20011796A3 (cs) | 1998-11-24 | 1999-11-12 | Pouľití N-substituovaných azabicycloalkanových derivátů pro léčení poruch centrálního nervového systému |
PL99348758A PL348758A1 (en) | 1998-11-24 | 1999-11-12 | Use of n-substituted azabicycloalkane derivatives for treating diseases of the central nervous system |
TR2001/01476T TR200101476T2 (tr) | 1998-11-24 | 1999-11-12 | N-ikameli azabisikloaklan türevlerinin merkezi sinir sistemi bozukluklarının tedavisinde kullanılması |
HU0104416A HUP0104416A3 (en) | 1998-11-24 | 1999-11-12 | Use of n-substituted azabicycloalkane derivatives for treating diseases of the central nervous system and medicaments containing the compounds |
JP2000583522A JP2002530333A (ja) | 1998-11-24 | 1999-11-12 | 中枢神経系障害の治療用薬剤を製造するためのn−置換3−アザビシクロアルカン誘導体使用 |
EP99960974A EP1133293A1 (de) | 1998-11-24 | 1999-11-12 | Verwendung von n-substituierten azabicycloalkan-derivaten zur behandlung von erkrankungen des zentralen nervensystems |
KR1020017006445A KR20010080535A (ko) | 1998-11-24 | 1999-11-12 | 중추신경계 질환의 치료를 위한 n-치환 아자비시클로알칸유도체의 용도 |
IL14318199A IL143181A0 (en) | 1998-11-24 | 1999-11-12 | Use of n-substituted azabicycloalkane derivatives for treating diseases of the central nervous system |
PCT/EP1999/008734 WO2000030639A1 (de) | 1998-11-24 | 1999-11-12 | Verwendung von n-substituierten azabicycloalkan-derivaten zur behandlung von erkrankungen des zentralen nervensystems |
ARP990105979A AR021502A1 (es) | 1998-11-24 | 1999-11-24 | Uso de derivados de azabicicloalcanos n-sustituidos para el tratamiento de enfermedades del sistema central nervioso |
ZA200103976A ZA200103976B (en) | 1998-11-24 | 2001-05-16 | Use of N-substituted azabicycloalkane derivatives for treating diseases of the central nervous system. |
NO20012538A NO20012538L (no) | 1998-11-24 | 2001-05-23 | Anvendelse av N-substituerte azabicycloalkanderivater for behandling av forstyrrelser i sentralnervesystemet |
BG105549A BG105549A (en) | 1998-11-24 | 2001-05-30 | Use of n-substituted azabicycloalkane derivatives for treating diseases of the central nervous system |
HR20010472A HRP20010472A2 (en) | 1998-11-24 | 2001-06-21 | Use of n-substituted azabicycloalkane derivatives for treating diseases of the central nervous system |
HK02102768.4A HK1040933A1 (zh) | 1998-11-24 | 2002-04-12 | N-取代的氮雜二環烷衍生物在治療中樞神經系統疾病中的應用 |
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 |
---|---|
DE19854147A1 true DE19854147A1 (de) | 2000-05-25 |
Family
ID=7888824
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19854147A Withdrawn DE19854147A1 (de) | 1998-11-24 | 1998-11-24 | Verwendung von N-substituierten Azabicycloalkan-Derivaten zur Verwendung bei der Bekämpfung der Cocainsucht |
Country Status (21)
Country | Link |
---|---|
EP (1) | EP1133293A1 (zh) |
JP (1) | JP2002530333A (zh) |
KR (1) | KR20010080535A (zh) |
CN (1) | CN1328455A (zh) |
AR (1) | AR021502A1 (zh) |
AU (1) | AU1775300A (zh) |
BG (1) | BG105549A (zh) |
BR (1) | BR9915589A (zh) |
CA (1) | CA2352526A1 (zh) |
CZ (1) | CZ20011796A3 (zh) |
DE (1) | DE19854147A1 (zh) |
HK (1) | HK1040933A1 (zh) |
HR (1) | HRP20010472A2 (zh) |
HU (1) | HUP0104416A3 (zh) |
IL (1) | IL143181A0 (zh) |
NO (1) | NO20012538L (zh) |
PL (1) | PL348758A1 (zh) |
SK (1) | SK7112001A3 (zh) |
TR (1) | TR200101476T2 (zh) |
WO (1) | WO2000030639A1 (zh) |
ZA (1) | ZA200103976B (zh) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7576094B2 (en) | 2004-12-13 | 2009-08-18 | Eli Lilly And Company | Spiro derivatives as lipoxygenase inhibitors |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0812310D0 (en) | 2008-07-03 | 2008-08-13 | Syngenta Ltd | Novel herbicides |
MX379289B (es) * | 2013-01-15 | 2025-03-10 | Novartis Ag | Uso de agonistas del receptor nicotinico de acetilcolina alfa 7. |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2717288A (en) * | 1987-11-12 | 1989-06-01 | 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 IL IL14318199A patent/IL143181A0/xx unknown
- 1999-11-12 HU HU0104416A patent/HUP0104416A3/hu unknown
- 1999-11-12 AU AU17753/00A patent/AU1775300A/en not_active Abandoned
- 1999-11-12 BR BR9915589-3A patent/BR9915589A/pt not_active IP Right Cessation
- 1999-11-12 EP EP99960974A patent/EP1133293A1/de not_active Withdrawn
- 1999-11-12 WO PCT/EP1999/008734 patent/WO2000030639A1/de not_active Application Discontinuation
- 1999-11-12 KR KR1020017006445A patent/KR20010080535A/ko not_active Application Discontinuation
- 1999-11-12 SK SK711-2001A patent/SK7112001A3/sk unknown
- 1999-11-12 TR TR2001/01476T patent/TR200101476T2/xx unknown
- 1999-11-12 JP JP2000583522A patent/JP2002530333A/ja active Pending
- 1999-11-12 CZ CZ20011796A patent/CZ20011796A3/cs unknown
- 1999-11-12 PL PL99348758A patent/PL348758A1/xx not_active Application Discontinuation
- 1999-11-12 CN CN99813559A patent/CN1328455A/zh active Pending
- 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
- 2001-06-21 HR HR20010472A patent/HRP20010472A2/hr not_active Application Discontinuation
-
2002
- 2002-04-12 HK HK02102768.4A patent/HK1040933A1/zh unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7576094B2 (en) | 2004-12-13 | 2009-08-18 | Eli Lilly And Company | Spiro derivatives as lipoxygenase inhibitors |
Also Published As
Publication number | Publication date |
---|---|
HUP0104416A3 (en) | 2002-11-28 |
BG105549A (en) | 2001-12-29 |
IL143181A0 (en) | 2002-04-21 |
CA2352526A1 (en) | 2000-06-02 |
CZ20011796A3 (cs) | 2002-05-15 |
WO2000030639A1 (de) | 2000-06-02 |
HRP20010472A2 (en) | 2003-04-30 |
EP1133293A1 (de) | 2001-09-19 |
AR021502A1 (es) | 2002-07-24 |
NO20012538D0 (no) | 2001-05-23 |
BR9915589A (pt) | 2001-08-07 |
CN1328455A (zh) | 2001-12-26 |
ZA200103976B (en) | 2002-05-16 |
JP2002530333A (ja) | 2002-09-17 |
NO20012538L (no) | 2001-07-04 |
TR200101476T2 (tr) | 2001-10-22 |
PL348758A1 (en) | 2002-06-03 |
SK7112001A3 (en) | 2001-12-03 |
HUP0104416A2 (hu) | 2002-04-29 |
HK1040933A1 (zh) | 2002-06-28 |
AU1775300A (en) | 2000-06-13 |
KR20010080535A (ko) | 2001-08-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
KR102427777B1 (ko) | 디안하이드로갈락티톨, 디아세틸디안하이드로갈락티톨, 디브로모둘시톨, 또는 그의 유사체 또는 유도체를 이용하여 유전학적 다형성이 있는 환자에 있어서 티로신-키나아제-억제제 내성 악성종양, ahi1 조절곤란 또는 돌연변이를 치료하는 방법 | |
EP2021006B1 (en) | Use of flibanserin for the treatment of post-menopausal sexual desire disorders | |
DE60200492T2 (de) | Kombination eines Inhibitoren der Serotoninwiederaufnahme und eines atypischen Antipsychotikums zur Behandlung von Depression, Zwangsneurosen und Psychosen | |
KR20160005341A (ko) | Ampk 활성인자 및 세로토닌성 제제를 포함하는 약학 조성물 및 이의 사용 방법 | |
US20110312978A1 (en) | Pde1 inhibitors for ophthalmic disorders | |
SK286864B6 (sk) | Použitie opticky čistého (S,S) reboxetínu alebo jeho farmaceuticky prijateľnej soli na výrobu lieku na liečenie alebo prevenciu fibromyalgie alebo iných somatoformných porúch | |
JP2024522736A (ja) | がん治療のためのparp阻害剤と組み合わせたatr阻害剤の使用 | |
KR20130045379A (ko) | 글리신 수송 억제제 화합물과 항정신병약의 조합물 | |
JP2004504376A (ja) | 医薬製剤としてのセロトニンアゴニスト(5ht2)とアンタゴニスト(5ht6)の新規組み合わせ | |
AU2021320957B2 (en) | Pharmaceutical composition for preventing, suppressing, or treating symptom associated with allergic reaction | |
JPH10507777A (ja) | ドパミン系の障害を治療するためのフェノキシピペラジン誘導体 | |
US20030235631A1 (en) | Combination treatment for depression and anxiety | |
US20020094986A1 (en) | Combination treatment for depression, anxiety and psychosis | |
US20020049211A1 (en) | Combination treatment for depression and anxiety | |
AU600852B2 (en) | Treatment of alcoholism using 2-pyrimidinyl-1-piperazine derivative | |
US4208417A (en) | Indole derivatives and their use as anxiolytics | |
WO2018148737A1 (en) | 5-ht2a serotonin receptor serotonin receptor inverse agonists useful for the prophylaxis and treatment of parkinsonian symptoms associated with a neurodegenerative disease | |
DE19854147A1 (de) | Verwendung von N-substituierten Azabicycloalkan-Derivaten zur Verwendung bei der Bekämpfung der Cocainsucht | |
ZA200209272B (en) | Aromatic polyurethane polyol. | |
GB2303303A (en) | 5HT-1A and 5HT-2 antagonists for treating side-effects of serotonin re-uptake inhibitors | |
MXPA01005104A (en) | Use of n-substituted azabicycloalkane derivatives for treating diseases of the central nervous system | |
HU205855B (en) | Process for producing anxciety-solving pharmaceutical composition | |
Land et al. | Risperidone: a novel antipsychotic medication | |
Micheletto et al. | Antipsychotics 17 | |
CA2489791A1 (en) | Combinations of pde-v inhibitors and nk1 antagonists for the treatment of anxiety or depression |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
8130 | Withdrawal |