SK1382001A3 - N-SUBSTITUTED AZABICYCLOHEPTANE DERIVATIVES, PRODUCTION AND USEì (54) THEREOF - Google Patents

N-SUBSTITUTED AZABICYCLOHEPTANE DERIVATIVES, PRODUCTION AND USEì (54) THEREOF Download PDF

Info

Publication number: SK1382001A3
Authority: SK; Slovakia
Prior art keywords: benzisothiazole; dihydro; dioxide; azabicyclo; exo
Prior art date: 1998-08-12

Application number

SK138-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Gerd Steiner

Thomas Hoger

Liliane Unger

Hans-Jurgen Teschendorf

Frieder Juchelka

Original Assignee

Basf Ag

Priority date (The priority date 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 date listed.)

1998-08-12

Filing date

1999-07-20

Publication date

2001-08-06

1999-07-20 Application filed by Basf Ag filed Critical Basf Ag

2001-08-06 Publication of SK1382001A3 publication Critical patent/SK1382001A3/sk

Links

UUAVYXKRUSVCDJ-UHFFFAOYSA-N 1-cycloheptylazepane Chemical class C1CCCCCC1N1CCCCCC1 UUAVYXKRUSVCDJ-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 18
201000010099 disease Diseases 0.000 claims abstract description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 4
239000002253 acid Substances 0.000 claims description 10
-1 N-substituted 3-azabicyclo [3.2.0] heptane Chemical class 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
150000007513 acids Chemical class 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 9
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
238000000034 method Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000000243 solution Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000003826 tablet Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 2
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 2
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 2
XHTPPQBDONGRAF-UHFFFAOYSA-N 3,3-dimethyl-2h-1,2-benzothiazole 1,1-dioxide Chemical compound C1=CC=C2C(C)(C)NS(=O)(=O)C2=C1 XHTPPQBDONGRAF-UHFFFAOYSA-N 0.000 description 2
NEOIOGUWEUTYIH-UHFFFAOYSA-N 3-azabicyclo[3.2.0]heptane Chemical class C1NCC2CCC21 NEOIOGUWEUTYIH-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000020477 pH reduction Effects 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
PXHFOKDZXZTWOB-UHFFFAOYSA-N 2-(2-chloroethyl)-3,3-dimethyl-1,2-benzothiazole 1,1-dioxide Chemical compound C1=CC=C2C(C)(C)N(CCCl)S(=O)(=O)C2=C1 PXHFOKDZXZTWOB-UHFFFAOYSA-N 0.000 description 1
PHXZTNABPCJOFZ-UHFFFAOYSA-N 2-(2-chloroethyl)-3,3-dimethyl-6-nitro-1,2-benzothiazole 1,1-dioxide Chemical compound [O-][N+](=O)C1=CC=C2C(C)(C)N(CCCl)S(=O)(=O)C2=C1 PHXZTNABPCJOFZ-UHFFFAOYSA-N 0.000 description 1
RSRBLCSRGDWLCA-UHFFFAOYSA-N 3,3-diethyl-2h-1,2-benzothiazole 1,1-dioxide Chemical compound C1=CC=C2C(CC)(CC)NS(=O)(=O)C2=C1 RSRBLCSRGDWLCA-UHFFFAOYSA-N 0.000 description 1
PHGXYLFVGTWXKR-UHFFFAOYSA-N 4-chloro-2-(2-chloroethyl)-3,3-dimethyl-1,2-benzothiazole 1,1-dioxide Chemical compound C1=CC(Cl)=C2C(C)(C)N(CCCl)S(=O)(=O)C2=C1 PHGXYLFVGTWXKR-UHFFFAOYSA-N 0.000 description 1
KARYKQNFDNURNN-UHFFFAOYSA-N 4-chloro-3,3-dimethyl-2h-1,2-benzothiazole 1,1-dioxide Chemical compound C1=CC(Cl)=C2C(C)(C)NS(=O)(=O)C2=C1 KARYKQNFDNURNN-UHFFFAOYSA-N 0.000 description 1
102000049773 5-HT2A Serotonin Receptor Human genes 0.000 description 1
108010072564 5-HT2A Serotonin Receptor Proteins 0.000 description 1
102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 description 1
101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 description 1
DICYEVYPNYYENN-UHFFFAOYSA-N 6-(4-chlorophenyl)-3-azabicyclo[3.2.0]heptane Chemical compound C1=CC(Cl)=CC=C1C1C2CNCC2C1 DICYEVYPNYYENN-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
208000022497 Cocaine-Related disease Diseases 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
102000003962 Dopamine D4 receptors Human genes 0.000 description 1
108090000357 Dopamine D4 receptors Proteins 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
201000006145 ***e dependence Diseases 0.000 description 1
239000012050 conventional carrier Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
206010013663 drug dependence Diseases 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000011554 guinea pig model Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
239000003326 hypnotic agent Substances 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
239000003176 neuroleptic agent Substances 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
210000003540 papillary muscle Anatomy 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003380 propellant Substances 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- 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

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Neurosurgery (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SK138-2001A 1998-08-12 1999-07-20 N-SUBSTITUTED AZABICYCLOHEPTANE DERIVATIVES, PRODUCTION AND USEì (54) THEREOF SK1382001A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19836406A DE19836406A1 (de)	1998-08-12	1998-08-12	N-Substituierte Azabicycloheptan-Derivate, ihre Herstellung und Verwendung
PCT/EP1999/005164 WO2000009501A1 (de)	1998-08-12	1999-07-20	N-substituierte azabicycloheptan-derivate, ihre herstellung und verwendung

Publications (1)

Publication Number	Publication Date
SK1382001A3 true SK1382001A3 (en)	2001-08-06

Family

ID=7877217

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK138-2001A SK1382001A3 (en)	1998-08-12	1999-07-20	N-SUBSTITUTED AZABICYCLOHEPTANE DERIVATIVES, PRODUCTION AND USEì (54) THEREOF

Country Status (29)

Country	Link
US (1)	US6300354B1 (pt)
EP (1)	EP1104419B1 (pt)
JP (1)	JP2002522539A (pt)
KR (1)	KR20010072408A (pt)
CN (1)	CN1312809A (pt)
AT (1)	ATE218138T1 (pt)
AU (1)	AU5285599A (pt)
BG (1)	BG105247A (pt)
BR (1)	BR9912885A (pt)
CA (1)	CA2339986A1 (pt)
CO (1)	CO5130024A1 (pt)
DE (2)	DE19836406A1 (pt)
DK (1)	DK1104419T3 (pt)
ES (1)	ES2178455T3 (pt)
HK (1)	HK1040399A1 (pt)
HR (1)	HRP20010180A2 (pt)
HU (1)	HUP0103358A3 (pt)
ID (1)	ID27656A (pt)
IL (1)	IL141009A0 (pt)
MY (1)	MY133140A (pt)
NO (1)	NO20010626L (pt)
NZ (1)	NZ510042A (pt)
PL (1)	PL345966A1 (pt)
PT (1)	PT1104419E (pt)
SK (1)	SK1382001A3 (pt)
TR (1)	TR200100475T2 (pt)
TW (1)	TW505644B (pt)
WO (1)	WO2000009501A1 (pt)
ZA (1)	ZA200101976B (pt)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20050119249A1 (en) *	2003-12-02	2005-06-02	Erik Buntinx	Method of treating neurodegenerative diseases using D4 and 5-HT2A antagonists, inverse agonists or partial agonists
US7884096B2 (en) *	2003-12-02	2011-02-08	Pharmaneuroboost N.V.	Method of treating mental disorders using of D4 and 5-HT2A antagonists, inverse agonists or partial agonists
EP1708790B1 (en) *	2003-12-02	2010-04-21	PharmaNeuroBoost N.V.	Use of pipamperone and a d2-receptor antagonist or a serotonin/dopamin antagonist for the treatment of psychotic disorders
US7855195B2 (en)	2003-12-02	2010-12-21	Pharmaneuroboost N.V.	Method of treating mental disorders using D4 and 5-HT2A antagonists, inverse agonists or partial agonists
US20050143349A1 (en) *	2003-12-17	2005-06-30	Quatrx Pharmaceuticals Co.	Phosphorus containing compounds useful for the regulation of LDL and Lp(a) levels

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4219973A1 (de)	1992-06-19	1993-12-23	Basf Ag	N-substituierte Azabicycloheptan-Derivate, ihre Herstellung und Verwendung
DE4243287A1 (de)	1992-06-19	1993-12-23	Basf Ag	N-Substituierte Azabicycloheptan-Derivate, ihre Herstellung und Verwendung
DE4427648A1 (de)	1994-08-04	1996-02-08	Basf Ag	N-Stubstituierte 3-Azabicyclo[3,2,0,]heptan-Derivate, ihre Herstellung und Verwendung
DE4341402A1 (de)	1993-12-04	1995-06-08	Basf Ag	N-substituierte Azabicycloheptan-Derivate, ihre Herstellung und Verwendung
DE4427647A1 (de)	1994-08-04	1996-02-08	Basf Ag	N-substituierte Azabicycloheptan-Derivate, ihre Herstellung und Verwendung

1998
- 1998-08-12 DE DE19836406A patent/DE19836406A1/de not_active Withdrawn
1999
- 1999-07-20 PT PT99938298T patent/PT1104419E/pt unknown
- 1999-07-20 AU AU52855/99A patent/AU5285599A/en not_active Abandoned
- 1999-07-20 PL PL99345966A patent/PL345966A1/xx not_active IP Right Cessation
- 1999-07-20 US US09/744,405 patent/US6300354B1/en not_active Expired - Fee Related
- 1999-07-20 HU HU0103358A patent/HUP0103358A3/hu unknown
- 1999-07-20 ES ES99938298T patent/ES2178455T3/es not_active Expired - Lifetime
- 1999-07-20 CA CA002339986A patent/CA2339986A1/en not_active Abandoned
- 1999-07-20 SK SK138-2001A patent/SK1382001A3/sk unknown
- 1999-07-20 ID IDW20010352A patent/ID27656A/id unknown
- 1999-07-20 KR KR1020017001781A patent/KR20010072408A/ko not_active Application Discontinuation
- 1999-07-20 JP JP2000564953A patent/JP2002522539A/ja active Pending
- 1999-07-20 EP EP99938298A patent/EP1104419B1/de not_active Expired - Lifetime
- 1999-07-20 NZ NZ510042A patent/NZ510042A/en unknown
- 1999-07-20 DK DK99938298T patent/DK1104419T3/da active
- 1999-07-20 AT AT99938298T patent/ATE218138T1/de not_active IP Right Cessation
- 1999-07-20 TR TR2001/00475T patent/TR200100475T2/xx unknown
- 1999-07-20 IL IL14100999A patent/IL141009A0/xx unknown
- 1999-07-20 WO PCT/EP1999/005164 patent/WO2000009501A1/de not_active Application Discontinuation
- 1999-07-20 CN CN99809588A patent/CN1312809A/zh active Pending
- 1999-07-20 DE DE59901563T patent/DE59901563D1/de not_active Expired - Fee Related
- 1999-07-20 BR BR9912885-3A patent/BR9912885A/pt not_active IP Right Cessation
- 1999-08-12 TW TW088114064A patent/TW505644B/zh active
- 1999-08-12 MY MYPI99003449A patent/MY133140A/en unknown
- 1999-08-12 CO CO99051370A patent/CO5130024A1/es unknown
2001
- 2001-02-06 NO NO20010626A patent/NO20010626L/no not_active Application Discontinuation
- 2001-02-13 BG BG105247A patent/BG105247A/xx unknown
- 2001-03-09 ZA ZA200101976A patent/ZA200101976B/en unknown
- 2001-03-12 HR HR20010180A patent/HRP20010180A2/hr not_active Application Discontinuation
2002
- 2002-03-08 HK HK02101798.0A patent/HK1040399A1/zh unknown

Also Published As

Publication number	Publication date
PL345966A1 (en)	2002-01-14
EP1104419A1 (de)	2001-06-06
HRP20010180A2 (en)	2002-04-30
DK1104419T3 (da)	2002-09-23
US6300354B1 (en)	2001-10-09
AU5285599A (en)	2000-03-06
TW505644B (en)	2002-10-11
MY133140A (en)	2007-10-31
TR200100475T2 (tr)	2001-06-21
EP1104419B1 (de)	2002-05-29
BG105247A (en)	2001-11-30
HUP0103358A2 (hu)	2002-05-29
DE19836406A1 (de)	2000-02-17
DE59901563D1 (de)	2002-07-04
ID27656A (id)	2001-04-19
ZA200101976B (en)	2002-03-11
ATE218138T1 (de)	2002-06-15
PT1104419E (pt)	2002-09-30
ES2178455T3 (es)	2002-12-16
CA2339986A1 (en)	2000-02-24
BR9912885A (pt)	2001-05-08
NZ510042A (en)	2003-08-29
HUP0103358A3 (en)	2002-10-28
NO20010626D0 (no)	2001-02-06
CN1312809A (zh)	2001-09-12
HK1040399A1 (zh)	2002-06-07
CO5130024A1 (es)	2002-02-27
IL141009A0 (en)	2002-02-10
JP2002522539A (ja)	2002-07-23
NO20010626L (no)	2001-02-06
KR20010072408A (ko)	2001-07-31
WO2000009501A1 (de)	2000-02-24

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