NO312243B1 - N-substituerte 3-azabicyklo[3.2.0]heptanderivater egnet som neuroleptika - Google Patents

N-substituerte 3-azabicyklo[3.2.0]heptanderivater egnet som neuroleptika Download PDF

Info

Publication number: NO312243B1
Authority: NO; Norway
Prior art keywords: formula; azabicyclo; acid; substituted; compound
Prior art date: 1994-08-04

Application number

NO19970473A

Other languages

English (en)

Norwegian (no)

Other versions

NO970473L (no

NO970473D0 (no

Inventor

Gerd Steiner

Rainer Munschauer

Thomas Hoeger

Liliane Unger

Hans-Juergen Teschendorf

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.)

1994-08-04

Filing date

1997-02-03

Publication date

2002-04-15

1997-02-03 Application filed by Basf Ag filed Critical Basf Ag

1997-02-03 Publication of NO970473D0 publication Critical patent/NO970473D0/no

1997-04-01 Publication of NO970473L publication Critical patent/NO970473L/no

2002-04-15 Publication of NO312243B1 publication Critical patent/NO312243B1/no

Links

-1 N-substituted 3-azabicyclo [3.2.0] heptane Chemical class 0.000 title claims description 8
NEOIOGUWEUTYIH-UHFFFAOYSA-N 3-azabicyclo[3.2.0]heptane Chemical class C1NCC2CCC21 NEOIOGUWEUTYIH-UHFFFAOYSA-N 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 13
238000004519 manufacturing process Methods 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
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 claims description 2
239000003176 neuroleptic agent Substances 0.000 claims 1
230000000701 neuroleptic effect Effects 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
238000000034 method Methods 0.000 abstract description 5
239000002831 pharmacologic agent Substances 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
241001465754 Metazoa Species 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000000243 solution Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 6
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 6
229960001252 methamphetamine Drugs 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
241000699670 Mus sp. Species 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000037023 motor activity Effects 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
230000008485 antagonism Effects 0.000 description 3
VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 description 3
229960004046 apomorphine Drugs 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
238000013421 nuclear magnetic resonance imaging Methods 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
239000000902 placebo Substances 0.000 description 3
229940068196 placebo Drugs 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
238000010992 reflux Methods 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
WOSAIZGZGABYOJ-UHFFFAOYSA-N 1-(3-chloroprop-1-enyl)naphthalene Chemical compound C1=CC=C2C(C=CCCl)=CC=CC2=C1 WOSAIZGZGABYOJ-UHFFFAOYSA-N 0.000 description 2
UUAVYXKRUSVCDJ-UHFFFAOYSA-N 1-cycloheptylazepane Chemical class C1CCCCCC1N1CCCCCC1 UUAVYXKRUSVCDJ-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-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
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
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 2
239000000164 antipsychotic agent Substances 0.000 description 2
229940005529 antipsychotics Drugs 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
238000012512 characterization method Methods 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
230000009194 climbing Effects 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
IJMWREDHKRHWQI-UHFFFAOYSA-M magnesium;ethene;chloride Chemical compound [Mg+2].[Cl-].[CH-]=C IJMWREDHKRHWQI-UHFFFAOYSA-M 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000010453 quartz Substances 0.000 description 2
102000005962 receptors Human genes 0.000 description 2
108020003175 receptors Proteins 0.000 description 2
230000007017 scission Effects 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
208000011580 syndromic disease Diseases 0.000 description 2
239000003826 tablet Substances 0.000 description 2
150000003892 tartrate salts Chemical class 0.000 description 2
239000008096 xylene Substances 0.000 description 2
KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SQAINHDHICKHLX-UHFFFAOYSA-N 1-naphthaldehyde Chemical compound C1=CC=C2C(C=O)=CC=CC2=C1 SQAINHDHICKHLX-UHFFFAOYSA-N 0.000 description 1
PMGYJTHQBWJRDY-UHFFFAOYSA-N 5-(2-chloroethyl)-3,6-dimethyl-2-(methylamino)pyrimidin-4-one Chemical compound CNC1=NC(C)=C(CCCl)C(=O)N1C PMGYJTHQBWJRDY-UHFFFAOYSA-N 0.000 description 1
102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-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
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
102000015554 Dopamine receptor Human genes 0.000 description 1
108050004812 Dopamine receptor Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
208000028017 Psychotic disease Diseases 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
206010044565 Tremor Diseases 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000004913 activation Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000000561 anti-psychotic effect Effects 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000037007 arousal Effects 0.000 description 1
239000003693 atypical antipsychotic agent Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
230000006399 behavior Effects 0.000 description 1
125000002619 bicyclic group Chemical group 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
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229940117916 cinnamic aldehyde Drugs 0.000 description 1
KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
230000002493 climbing effect Effects 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000006352 cycloaddition reaction Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 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
239000000706 filtrate Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000012458 free base Substances 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
125000005843 halogen group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000003326 hypnotic agent Substances 0.000 description 1
230000000147 hypnotic effect Effects 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229940035363 muscle relaxants Drugs 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 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
238000007911 parenteral administration Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
239000003380 propellant Substances 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000013223 sprague-dawley female rat Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000007885 tablet disintegrant Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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
- A61P25/20—Hypnotics; Sedatives
- 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
- A61P25/22—Anxiolytics
- 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
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

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

NO19970473A 1994-08-04 1997-02-03 N-substituerte 3-azabicyklo[3.2.0]heptanderivater egnet som neuroleptika NO312243B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE4427648A DE4427648A1 (de)	1994-08-04	1994-08-04	N-Stubstituierte 3-Azabicyclo[3,2,0,]heptan-Derivate, ihre Herstellung und Verwendung
PCT/EP1995/002893 WO1996004272A1 (de)	1994-08-04	1995-07-21	N-substituierte 3-azabicyclo(3.2.0)heptan-derivate als neuroleptika

Publications (3)

Publication Number	Publication Date
NO970473D0 NO970473D0 (no)	1997-02-03
NO970473L NO970473L (no)	1997-04-01
NO312243B1 true NO312243B1 (no)	2002-04-15

Family

ID=6524944

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO19970473A NO312243B1 (no)	1994-08-04	1997-02-03	N-substituerte 3-azabicyklo[3.2.0]heptanderivater egnet som neuroleptika

Country Status (25)

Country	Link
US (1)	US6028073A (ru)
EP (1)	EP0775135B1 (ru)
JP (1)	JPH10503503A (ru)
CN (1)	CN1066145C (ru)
AT (1)	ATE242236T1 (ru)
AU (1)	AU696230B2 (ru)
BG (1)	BG63633B1 (ru)
CA (1)	CA2196809A1 (ru)
CZ (1)	CZ287862B6 (ru)
DE (2)	DE4427648A1 (ru)
DK (1)	DK0775135T3 (ru)
ES (1)	ES2201111T3 (ru)
FI (1)	FI970448A (ru)
HR (1)	HRP950438A2 (ru)
HU (1)	HUT77772A (ru)
MX (1)	MX9700807A (ru)
NO (1)	NO312243B1 (ru)
NZ (1)	NZ290426A (ru)
PL (1)	PL183526B1 (ru)
PT (1)	PT775135E (ru)
RU (1)	RU2163604C2 (ru)
SI (1)	SI9520094B (ru)
UA (1)	UA44903C2 (ru)
WO (1)	WO1996004272A1 (ru)
ZA (1)	ZA956477B (ru)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19836404A1 (de) *	1998-08-12	2000-02-17	Basf Ag	N-Substituierte Azabicycloheptan-Derivate, ihre Herstellung und Verwendung
US6458821B1 (en)	1998-08-12	2002-10-01	Abbott Laboratories	N-substituted azabicycloheptane derivatives, production and use thereof
DE19836406A1 (de)	1998-08-12	2000-02-17	Basf Ag	N-Substituierte Azabicycloheptan-Derivate, ihre Herstellung und Verwendung
DE19848521A1 (de) *	1998-10-21	2000-04-27	Basf Ag	Verfahren zur Herstellung von (+)-exo-6-Phenyl-3-azabicyclo-[3.2.0]heptanen
DE19854147A1 (de) *	1998-11-24	2000-05-25	Basf Ag	Verwendung von N-substituierten Azabicycloalkan-Derivaten zur Verwendung bei der Bekämpfung der Cocainsucht
CA2583333C (en) *	2004-10-14	2013-05-14	Abbott Gmbh & Co. Kg	Azabicycloheptyl compounds suitable for treating disorders that respond to modulation of the dopamine d3 receptor
KR102306951B1 (ko)	2013-07-10	2021-10-01	버텍스 파마슈티칼스 인코포레이티드	이온 채널의 조절제로서의 융합된 피페리딘 아미드
EA033420B1 (ru) *	2014-06-26	2019-10-31	Hoffmann La Roche	Производные индолин-2-она или пирролопиридин-2-она, обладающие антипсихотической активностью
EP3371168B1 (en)	2015-11-06	2020-05-27	H. Hoffnabb-La Roche Ag	Indolin-2-one derivatives
CN108137555B (zh)	2015-11-06	2021-02-19	豪夫迈·罗氏有限公司	可用于治疗cns疾病的二氢吲哚-2-酮衍生物
CN108349942B (zh)	2015-11-06	2021-03-30	豪夫迈·罗氏有限公司	用于治疗cns和相关疾病的二氢吲哚-2-酮衍生物
EP3371174B1 (en)	2015-11-06	2021-03-17	H. Hoffnabb-La Roche Ag	Indolin-2-one derivatives
US20220227773A1 (en) *	2019-05-30	2022-07-21	Shanghai Institute Of Materia Medica, Chinese Academy Of Sciences	Fused ring compound, preparation method therefor and use thereof

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4243287A1 (de) *	1992-06-19	1993-12-23	Basf Ag	N-Substituierte Azabicycloheptan-Derivate, ihre Herstellung und Verwendung
DE4341402A1 (de) *	1993-12-04	1995-06-08	Basf Ag	N-substituierte Azabicycloheptan-Derivate, ihre Herstellung und Verwendung

1994
- 1994-08-04 DE DE4427648A patent/DE4427648A1/de not_active Withdrawn
1995
- 1995-07-21 DE DE59510713T patent/DE59510713D1/de not_active Expired - Fee Related
- 1995-07-21 EP EP95926970A patent/EP0775135B1/de not_active Expired - Lifetime
- 1995-07-21 PL PL95318460A patent/PL183526B1/pl unknown
- 1995-07-21 PT PT95926970T patent/PT775135E/pt unknown
- 1995-07-21 CN CN95194835A patent/CN1066145C/zh not_active Expired - Fee Related
- 1995-07-21 RU RU97103198/04A patent/RU2163604C2/ru not_active IP Right Cessation
- 1995-07-21 MX MX9700807A patent/MX9700807A/es unknown
- 1995-07-21 SI SI9520094A patent/SI9520094B/sl unknown
- 1995-07-21 HU HU9700329A patent/HUT77772A/hu unknown
- 1995-07-21 UA UA97030904A patent/UA44903C2/uk unknown
- 1995-07-21 JP JP8506146A patent/JPH10503503A/ja not_active Ceased
- 1995-07-21 US US08/776,577 patent/US6028073A/en not_active Expired - Lifetime
- 1995-07-21 CZ CZ1997310A patent/CZ287862B6/cs not_active IP Right Cessation
- 1995-07-21 DK DK95926970T patent/DK0775135T3/da active
- 1995-07-21 CA CA002196809A patent/CA2196809A1/en not_active Abandoned
- 1995-07-21 AT AT95926970T patent/ATE242236T1/de not_active IP Right Cessation
- 1995-07-21 ES ES95926970T patent/ES2201111T3/es not_active Expired - Lifetime
- 1995-07-21 WO PCT/EP1995/002893 patent/WO1996004272A1/de active IP Right Grant
- 1995-07-21 AU AU31162/95A patent/AU696230B2/en not_active Ceased
- 1995-07-21 NZ NZ290426A patent/NZ290426A/en unknown
- 1995-08-03 ZA ZA9506477A patent/ZA956477B/xx unknown
- 1995-08-04 HR HRP4427648.6A patent/HRP950438A2/hr not_active Application Discontinuation
1997
- 1997-02-03 FI FI970448A patent/FI970448A/fi unknown
- 1997-02-03 NO NO19970473A patent/NO312243B1/no not_active IP Right Cessation
- 1997-02-12 BG BG101220A patent/BG63633B1/bg unknown

Also Published As

Publication number	Publication date
DE59510713D1 (de)	2003-07-10
ES2201111T3 (es)	2004-03-16
SI9520094A (en)	1997-08-31
RU2163604C2 (ru)	2001-02-27
UA44903C2 (uk)	2002-03-15
PT775135E (pt)	2003-10-31
CZ287862B6 (en)	2001-02-14
ATE242236T1 (de)	2003-06-15
CA2196809A1 (en)	1996-02-15
NO970473L (no)	1997-04-01
US6028073A (en)	2000-02-22
CZ31097A3 (en)	1997-10-15
ZA956477B (en)	1997-02-03
BG63633B1 (bg)	2002-07-31
NZ290426A (en)	1998-02-26
AU696230B2 (en)	1998-09-03
PL183526B1 (pl)	2002-06-28
FI970448A0 (fi)	1997-02-03
EP0775135B1 (de)	2003-06-04
MX9700807A (es)	1997-05-31
BG101220A (en)	1997-08-29
NO970473D0 (no)	1997-02-03
DE4427648A1 (de)	1996-02-08
AU3116295A (en)	1996-03-04
PL318460A1 (en)	1997-06-09
HRP950438A2 (en)	1997-10-31
CN1156454A (zh)	1997-08-06
JPH10503503A (ja)	1998-03-31
WO1996004272A1 (de)	1996-02-15
EP0775135A1 (de)	1997-05-28
DK0775135T3 (da)	2003-09-29
HUT77772A (hu)	1998-08-28
SI9520094B (sl)	2002-02-28
FI970448A (fi)	1997-04-03
CN1066145C (zh)	2001-05-23

Legal Events

Date	Code	Title	Description
2003-03-10	MM1K	Lapsed by not paying the annual fees	Free format text: LAPSED IN JANUARY 2003

Publication	Publication Date	Title
NZ231855A (en)	1992-02-25	Heterocyclylalkyl - substituted piperazine derivatives and pharmaceutical compositions
NO302522B1 (no)	1998-03-16	4-pyrimidinyl- og pyridinylderivater av indolyl-3-yl-alkylpiperazin og farmasöytisk preparat som inneholder en slik forbindelse
MX2008010645A (es)	2008-10-14	Derivado de amida o sal del mismo.
SK15852000A3 (sk)	2001-06-11	Derivát 1-[(1-substituovaného-4-piperidinyl)metyl]-4-piperidínu, spôsob jeho prípravy, farmaceutický prípravok obsahujúci tento derivát a medziprodukt tohto derivátu
NO312243B1 (no)	2002-04-15	N-substituerte 3-azabicyklo[3.2.0]heptanderivater egnet som neuroleptika
FR2667068A1 (fr)	1992-03-27	Nouvelles amines alkyl heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
AU1594988A (en)	1988-11-02	Psychotropic bicyclic imides
HU220070B (hu)	2001-10-28	N-szubsztituált aza-biciklo[3.2.0]heptán-származékok és ezeket a vegyületeket tartalmazó gyógyszerkészítmények
US5753690A (en)	1998-05-19	N-substituted azobicycloheptane derivatives, the preparation and use thereof
CS233746B2 (en)	1985-03-14	Processing of amidazolin derivatives
US6458821B1 (en)	2002-10-01	N-substituted azabicycloheptane derivatives, production and use thereof
TW393482B (en)	2000-06-11	N-substituted 3-azabicyclo[3.2.0]heptane derivatives, the preparation and use thereof
JP2004131497A (ja)	2004-04-30	シスシクロプロパン誘導体
ES2198947T3 (es)	2004-02-01	Derivados de azabicicloheptano n-substituidos, su obtencion y empleo.
NO180192B (no)	1996-11-25	N-substituerte azabicykloheptanderivater og anvendelse derav
HU182717B (en)	1984-03-28	Process for preparing 2-/4-hydroxy-alkyl-1-piperazinyl/-2,4,6-cycloheptatrien-1-one derivatives and pharmaceutical compositions containing such compounds as active substances