KR20010080535A - 중추신경계 질환의 치료를 위한 n-치환 아자비시클로알칸유도체의 용도 - Google Patents
중추신경계 질환의 치료를 위한 n-치환 아자비시클로알칸유도체의 용도 Download PDFInfo
- Publication number
- KR20010080535A KR20010080535A KR1020017006445A KR20017006445A KR20010080535A KR 20010080535 A KR20010080535 A KR 20010080535A KR 1020017006445 A KR1020017006445 A KR 1020017006445A KR 20017006445 A KR20017006445 A KR 20017006445A KR 20010080535 A KR20010080535 A KR 20010080535A
- Authority
- KR
- South Korea
- Prior art keywords
- azabicyclo
- exo
- ethyl
- fluorophenyl
- heptan
- Prior art date
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 9
- 201000010099 disease Diseases 0.000 title claims abstract description 8
- 210000003169 central nervous system Anatomy 0.000 title abstract description 3
- -1 amino, monomethylamino, dimethylamino Chemical group 0.000 claims description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000001246 bromo group Chemical group Br* 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 3
- 229940025084 amphetamine Drugs 0.000 claims description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 206010012335 Dependence Diseases 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 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
- 150000001721 carbon Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910021386 carbon form Inorganic materials 0.000 claims description 2
- 229960003920 cocaine Drugs 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 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
- 230000002401 inhibitory effect Effects 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
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 1
- 208000015114 central nervous system disease 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
- 231100000572 poisoning Toxicity 0.000 claims 1
- 230000000607 poisoning effect Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 185
- 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 44
- 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 40
- 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 23
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 20
- RMHJJUOPOWPRBP-UHFFFAOYSA-N naphthalene-1-carboxamide Chemical class C1=CC=C2C(C(=O)N)=CC=CC2=C1 RMHJJUOPOWPRBP-UHFFFAOYSA-N 0.000 description 14
- 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
- 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
- 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
- CIGBERQUNYDMHH-UHFFFAOYSA-N 1H-indene-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CCC2=C1 CIGBERQUNYDMHH-UHFFFAOYSA-N 0.000 description 9
- 241000156724 Antirhea Species 0.000 description 9
- 206010041349 Somnolence Diseases 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 7
- CXUCKELNYMZTRT-UHFFFAOYSA-N 1-Ethyl-2-benzimidazolinone Chemical compound C1=CC=C2NC(=O)N(CC)C2=C1 CXUCKELNYMZTRT-UHFFFAOYSA-N 0.000 description 6
- 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 6
- SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 description 6
- DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 5
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 5
- 239000001273 butane Substances 0.000 description 5
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- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 4
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- 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 3
- HGSJSGJZOMBIAB-UHFFFAOYSA-N 2h-pyrimido[2,1-b][1,3]thiazin-6-one Chemical compound S1CC=CN2C(=O)C=CN=C21 HGSJSGJZOMBIAB-UHFFFAOYSA-N 0.000 description 3
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
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- BYXQNAWQFGHXDQ-UHFFFAOYSA-N 2-ethyl-7-methyl-2,3-dihydro-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C(C)C1CN2C(=NC(=CC2=O)C)S1 BYXQNAWQFGHXDQ-UHFFFAOYSA-N 0.000 description 2
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- YEMOSDIWPOFYPJ-UHFFFAOYSA-N 1-ethyl-3,6-dimethylpyrimidine-2,4-dione Chemical compound CCN1C(C)=CC(=O)N(C)C1=O YEMOSDIWPOFYPJ-UHFFFAOYSA-N 0.000 description 1
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- 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
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- AVSQGTAUBSVMBZ-UHFFFAOYSA-N 1-ethylthieno[3,4-d]pyrimidine-2,4-dione Chemical compound C(C)N1C(NC(C=2C1=CSC=2)=O)=O AVSQGTAUBSVMBZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- A—HUMAN NECESSITIES
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- 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
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- 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
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- 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
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- 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
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- 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)
Abstract
Description
Claims (4)
- 중추신경계 질환 치료용 약제의 제조를 위한, 하기 화학식 Ⅰ의 N-치환 3-아자비시클로알칸 유도체 및 이들 유도체와 생리학적으로 허용되는 산과의 염의 용도.<화학식 Ⅰ>상기 식에서,B는 이중 결합을 함유할 수 있는 4-, 5- 또는 6-원 고리이며,R1은 각각 할로겐 원자, C1-4알킬, 트리플루오로메틸, 히드록실, C1-4알콕시, 아미노, 모노메틸아미노, 디메틸아미노, 시아노 또는 니트로기에 의하여 단일치환 또는 이치환되거나, 치환되지 않은 페닐, 나프틸, 페난트릴 또는 티에닐기이고,n은 0, 1, 2, 3 또는 4의 수이며,R2는 1개 또는 2개의 할로겐 원자에 의하여 치환되거나, 치환되지 않은 나프틸기이거나, 또는 하기의 라디칼들 중 하나이다:(상기 식에서,R3은 수소 원자, 히드록실기이거나, 또는 불소, 염소 또는 브롬 원자에 의하여 치환되거나, 치환되지 않은 페닐 라디칼이고,R4는 수소 원자이거나, 또는R3및 R4는 함께 산소 원자이고,R5는 각각 불소, 염소 또는 브롬 원자에 의하여, 또는 히드록실, 니트로, 아미노, C1-4알카노일아미노, C1-4알킬아미노, C1-4알킬 또는 메톡시기에 의하여 단일치환 또는 이치환되거나, 치환되지 않은 페닐, 나프틸 또는 티에닐기이며,R6은 수소 원자 또는 메틸기이고,R7은 각각 불소, 염소 또는 브롬 원자에 의하여, 또는 C1-4알킬, 히드록실, 메톡시, 니트로, 시아노, 트리플루오로메틸, 아미노 또는 디-C1-4알킬아미노기에 의하여 단일치환 또는 이치환되거나, 치환되지 않은 페닐, 나프틸, 벤조푸릴, 벤조티에닐, 티에닐, 인돌릴, N-메틸인돌릴 또는 인데닐기이거나, 또는 C3-7시클로알킬기이고,R8은 수소 원자, 또는 불소 또는 염소 원자, 또는 C1-4알킬, 메톡시 또는 아미노기이며,R9는 수소 원자 또는 메틸기이며,R10은 수소 원자 또는 메틸기이거나, 또는R9와 R10은 고리 탄소 원자와 함께 스피로시클로프로판 고리를 형성하고,R11은 수소 원자, 히드록실, C1-C4알킬 또는 C1-C4알콕시기이거나, 인접한 탄소 원자와 함께 C=O- 또는 C=S기를 형성하고,X 및 Y는 탄소 원자, CH, CH2, NH 또는 C1-C4알킬-N기, 또는 질소 원자이고,Z는 직접 결합, CO기, CS기이거나, 또는 수소 원자가 히드록실, 아미노 또는 C1-C4알콕시기에 의하여 또는 할로겐 원자에 의하여 치환될 수 있는 CH 또는 CH2기이고,A는 수소 원자, 히드록실, 아미노, 메르캅토, C1-C4알킬아미노, 디-C1-C4알킬아미노, C1-C4알킬티오 또는 C1-C4알콕시기이거나, 인접한 탄소 원자와 함께 C=O기를 형성하거나, 또는A는 이중 결합을 비연속적으로 1개 또는 2개 함유할 수 있고 CH 또는 CH2기 중 하나가 질소 또는 황 원자에 의하여 또는 NH 또는 N-CH3기에 의하여 대체될 수 있는, Y에 결합된 C3-C4알킬렌기이고, 이와 같은 A 함유 고리는 불소 또는 염소 원자에 의하여, 또는 메틸, 메톡시, 니트로 또는 아미노기에 의하여 단일 치환되고, 상기 고리가 벤젠 고리인 경우, 이 고리는 불소 또는 염소 원자 또는 메틸, 트리플루오로메틸, 니트로, 히드록실, 메톡시, 아미노, 모노메틸 또는 디메틸아미노기에 의하여 단일치환, 이치환, 또는 삼치환될 수 있으며,X-, Y- 및 Z-함유 고리는 1번 질소 원자에서 C1-C4알킬, 알릴 또는 벤질기를가질 수 있으며, 이중 결합을 비연속적으로 1개 내지 3개 함유할 수 있다).
- 제1항에 있어서, 중독성 질환 치료용 약제의 제조를 위한 용도.
- 제1항 또는 제2항에 있어서, 코카인 중독 치료용 약제의 제조를 위한 용도.
- 제1항 또는 제2항에 있어서, 암페타민 및 암페타민계 물질에 대한 중독 억제용 약제의 제조를 위한 용도.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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DE19854147.3 | 1998-11-24 | ||
DE19854147A DE19854147A1 (de) | 1998-11-24 | 1998-11-24 | Verwendung von N-substituierten Azabicycloalkan-Derivaten zur Verwendung bei der Bekämpfung der Cocainsucht |
PCT/EP1999/008734 WO2000030639A1 (de) | 1998-11-24 | 1999-11-12 | Verwendung von n-substituierten azabicycloalkan-derivaten zur behandlung von erkrankungen des zentralen nervensystems |
Publications (1)
Publication Number | Publication Date |
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KR20010080535A true KR20010080535A (ko) | 2001-08-22 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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KR1020017006445A KR20010080535A (ko) | 1998-11-24 | 1999-11-12 | 중추신경계 질환의 치료를 위한 n-치환 아자비시클로알칸유도체의 용도 |
Country Status (21)
Country | Link |
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EP (1) | EP1133293A1 (ko) |
JP (1) | JP2002530333A (ko) |
KR (1) | KR20010080535A (ko) |
CN (1) | CN1328455A (ko) |
AR (1) | AR021502A1 (ko) |
AU (1) | AU1775300A (ko) |
BG (1) | BG105549A (ko) |
BR (1) | BR9915589A (ko) |
CA (1) | CA2352526A1 (ko) |
CZ (1) | CZ20011796A3 (ko) |
DE (1) | DE19854147A1 (ko) |
HK (1) | HK1040933A1 (ko) |
HR (1) | HRP20010472A2 (ko) |
HU (1) | HUP0104416A3 (ko) |
IL (1) | IL143181A0 (ko) |
NO (1) | NO20012538L (ko) |
PL (1) | PL348758A1 (ko) |
SK (1) | SK7112001A3 (ko) |
TR (1) | TR200101476T2 (ko) |
WO (1) | WO2000030639A1 (ko) |
ZA (1) | ZA200103976B (ko) |
Cited By (1)
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KR101879919B1 (ko) * | 2013-01-15 | 2018-07-18 | 노파르티스 아게 | 알파 7 니코틴성 아세틸콜린 수용체 작용물질의 용도 |
Families Citing this family (2)
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BRPI0519013A2 (pt) | 2004-12-13 | 2009-11-03 | Lilly Co Eli | composto ou esteroisÈmeros únicos, misturas de esteroisÈmeros, sais, tautÈmeros ou pró-drogas destes farmaceuticamente aceitáveis, composição farmacêutica, e, uso de um composto |
GB0812310D0 (en) | 2008-07-03 | 2008-08-13 | Syngenta Ltd | Novel herbicides |
Family Cites Families (4)
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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
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2002
- 2002-04-12 HK HK02102768.4A patent/HK1040933A1/zh unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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KR101879919B1 (ko) * | 2013-01-15 | 2018-07-18 | 노파르티스 아게 | 알파 7 니코틴성 아세틸콜린 수용체 작용물질의 용도 |
Also Published As
Publication number | Publication date |
---|---|
DE19854147A1 (de) | 2000-05-25 |
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 |
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