IL101102A - Phar aceut cal p epara ion f r the treatment of cognitive disorders containing 3-piperidyl-indole derivatives - Google Patents
Phar aceut cal p epara ion f r the treatment of cognitive disorders containing 3-piperidyl-indole derivativesInfo
- Publication number
- IL101102A IL101102A IL10110292A IL10110292A IL101102A IL 101102 A IL101102 A IL 101102A IL 10110292 A IL10110292 A IL 10110292A IL 10110292 A IL10110292 A IL 10110292A IL 101102 A IL101102 A IL 101102A
- Authority
- IL
- Israel
- Prior art keywords
- piperidyl
- indole
- fluorophenyl
- ethyl
- lower alkyl
- Prior art date
Links
- 208000010877 cognitive disease Diseases 0.000 title claims description 9
- XKJJOWGAKBYIQV-UHFFFAOYSA-N 2-piperidin-3-yl-1h-indole Chemical class C1CCNCC1C1=CC2=CC=CC=C2N1 XKJJOWGAKBYIQV-UHFFFAOYSA-N 0.000 title description 2
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 8
- 239000000651 prodrug Substances 0.000 claims abstract description 7
- 229940002612 prodrug Drugs 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- -1 lower alkylsulionyl Chemical group 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Chemical group 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- 229910052799 carbon Chemical group 0.000 claims description 2
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 47
- 238000000034 method Methods 0.000 abstract description 12
- 206010027175 memory impairment Diseases 0.000 abstract description 2
- 238000012360 testing method Methods 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 241000699670 Mus sp. Species 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- GZKLJWGUPQBVJQ-UHFFFAOYSA-N sertindole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(Cl)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 GZKLJWGUPQBVJQ-UHFFFAOYSA-N 0.000 description 11
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 229960000652 sertindole Drugs 0.000 description 9
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 230000002903 catalepsic effect Effects 0.000 description 7
- 150000002431 hydrogen Chemical group 0.000 description 7
- 229930000680 A04AD01 - Scopolamine Natural products 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
- 208000009132 Catalepsy Diseases 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- STECJAGHUSJQJN-GAUPFVANSA-N Hyoscine Natural products C1([C@H](CO)C(=O)OC2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-GAUPFVANSA-N 0.000 description 6
- STECJAGHUSJQJN-UHFFFAOYSA-N N-Methyl-scopolamin Natural products C1C(C2C3O2)N(C)C3CC1OC(=O)C(CO)C1=CC=CC=C1 STECJAGHUSJQJN-UHFFFAOYSA-N 0.000 description 6
- 206010047853 Waxy flexibility Diseases 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 229960002646 scopolamine Drugs 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- STECJAGHUSJQJN-FWXGHANASA-N scopolamine Chemical compound C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3N([C@H](C2)[C@@H]2[C@H]3O2)C)=CC=CC=C1 STECJAGHUSJQJN-FWXGHANASA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000019771 cognition Effects 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
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- 239000003826 tablet Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000001828 Gelatine Substances 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- 230000001149 cognitive effect Effects 0.000 description 3
- 230000003920 cognitive function Effects 0.000 description 3
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
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- HZAXFHJVJLSVMW-UHFFFAOYSA-N monoethanolamine hydrochloride Natural products NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
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- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
- KTOKSMAKXHBMJM-UHFFFAOYSA-N 1-[2-[4-[1-(4-fluorophenyl)-5-methoxyindol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-one Chemical compound C12=CC(OC)=CC=C2N(C=2C=CC(F)=CC=2)C=C1C(CC1)CCN1CCN1CCNC1=O KTOKSMAKXHBMJM-UHFFFAOYSA-N 0.000 description 2
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
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- 108091005477 5-HT3 receptors Proteins 0.000 description 2
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- 230000000996 additive effect Effects 0.000 description 2
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- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
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- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
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- RHASQCTWMNDBBX-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-[1-[2-(2-oxoimidazolidin-1-yl)ethyl]piperidin-4-yl]indole-5-carbonitrile Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(C#N)C=C2C(C2CCN(CCN3C(NCC3)=O)CC2)=C1 RHASQCTWMNDBBX-UHFFFAOYSA-N 0.000 description 1
- ULBTYVNUCUDTOB-UHFFFAOYSA-N 1-(4-fluorophenyl)-3-piperidin-4-yl-5-(trifluoromethyl)indole Chemical compound C1=CC(F)=CC=C1N1C2=CC=C(C(F)(F)F)C=C2C(C2CCNCC2)=C1 ULBTYVNUCUDTOB-UHFFFAOYSA-N 0.000 description 1
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- ACSPDVQPRFWYKW-UHFFFAOYSA-N 1-[2-[4-[1-(4-fluorophenyl)-5-hydroxyindol-3-yl]piperidin-1-yl]ethyl]imidazolidin-2-one Chemical compound C12=CC(O)=CC=C2N(C=2C=CC(F)=CC=2)C=C1C(CC1)CCN1CCN1CCNC1=O ACSPDVQPRFWYKW-UHFFFAOYSA-N 0.000 description 1
- SPTZXCADEBYXHP-UHFFFAOYSA-N 1-[2-[4-[1-(4-fluorophenyl)-5-methylindol-3-yl]piperidin-1-yl]ethyl]-3-propan-2-ylimidazolidin-2-one Chemical compound O=C1N(C(C)C)CCN1CCN1CCC(C=2C3=CC(C)=CC=C3N(C=3C=CC(F)=CC=3)C=2)CC1 SPTZXCADEBYXHP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Processing Of Meat And Fish (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK036291A DK36291D0 (da) | 1991-03-01 | 1991-03-01 | Anvendelse af piperidylsubstituerede indolderivater til behandling af kognitive lidelser |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL101102A0 IL101102A0 (en) | 1992-11-15 |
| IL101102A true IL101102A (en) | 1996-03-31 |
Family
ID=8092662
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10110292A IL101102A (en) | 1991-03-01 | 1992-02-28 | Phar aceut cal p epara ion f r the treatment of cognitive disorders containing 3-piperidyl-indole derivatives |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US5444073A (da) |
| EP (1) | EP0575429B1 (da) |
| JP (1) | JP3108434B2 (da) |
| KR (1) | KR0183424B1 (da) |
| AT (1) | ATE131055T1 (da) |
| AU (1) | AU663699B2 (da) |
| CA (1) | CA2105385C (da) |
| CY (1) | CY2083B1 (da) |
| DE (1) | DE69206607T2 (da) |
| DK (2) | DK36291D0 (da) |
| HK (1) | HK1003560A1 (da) |
| IE (1) | IE70600B1 (da) |
| IL (1) | IL101102A (da) |
| NO (1) | NO307406B1 (da) |
| NZ (1) | NZ241800A (da) |
| WO (1) | WO1992015303A1 (da) |
| ZA (1) | ZA921462B (da) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5468768A (en) * | 1994-01-06 | 1995-11-21 | Bristol-Myers Squibb Company | Antimigraine derivatives of indolylcycloalkanylamines |
| US6489341B1 (en) | 1999-06-02 | 2002-12-03 | Sepracor Inc. | Methods for the treatment of neuroleptic and related disorders using sertindole derivatives |
| EP1535616B1 (en) | 2002-08-22 | 2009-05-13 | Dainippon Sumitomo Pharma Co., Ltd. | Remedy for integration dysfunction syndrome |
| KR101113630B1 (ko) * | 2003-06-23 | 2012-02-13 | 다이닛본 스미토모 세이야꾸 가부시끼가이샤 | 노인성 치매 치료제 |
| US20070160537A1 (en) | 2004-02-20 | 2007-07-12 | Takeo Ishiyama | In vivo screening method of therapeutic agent for memory/learning dysfunctions by schizophrenia |
| US20070212412A1 (en) * | 2005-09-08 | 2007-09-13 | H. Lundbeck A/S | Stable solid formulation of sertindole |
| TW200821296A (en) * | 2006-06-01 | 2008-05-16 | Lundbeck & Co As H | Use of sertindole for the preventive treatment of suicidal behaviour |
| US8258139B2 (en) | 2010-11-08 | 2012-09-04 | Dainippon Sumitomo Pharma Co., Ltd. | Method of treatment for mental disorders |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL48508A (en) * | 1974-12-09 | 1979-10-31 | Roussel Uclaf | Pharmaceutical compositions comprising piperidylindole derivatives |
| FR2362628A1 (fr) * | 1976-08-26 | 1978-03-24 | Roussel Uclaf | Nouveaux derives du piperidyl-indole et leurs sels, procede de preparation et application a titre de medicaments |
| SE8004129L (sv) * | 1979-07-13 | 1981-01-14 | Roussel Uclaf | Nya tetrahydropyridin-4-yl-indolderivat samt salter derav, framstellning och anvendning derav sasom lekemedel samt kompositioner innehallande dessa foreningar |
| IE58370B1 (en) * | 1985-04-10 | 1993-09-08 | Lundbeck & Co As H | Indole derivatives |
| GB8704572D0 (en) * | 1987-02-26 | 1987-04-01 | Lundbeck & Co As H | Organic compounds |
| DK158590D0 (da) * | 1990-07-02 | 1990-07-02 | Lundbeck & Co As H | Indolderivater |
-
1991
- 1991-03-01 DK DK036291A patent/DK36291D0/da not_active Application Discontinuation
-
1992
- 1992-02-24 IE IE920572A patent/IE70600B1/en not_active IP Right Cessation
- 1992-02-27 ZA ZA921462A patent/ZA921462B/xx unknown
- 1992-02-28 AT AT92906578T patent/ATE131055T1/de not_active IP Right Cessation
- 1992-02-28 DE DE69206607T patent/DE69206607T2/de not_active Expired - Fee Related
- 1992-02-28 JP JP04505932A patent/JP3108434B2/ja not_active Expired - Fee Related
- 1992-02-28 DK DK92906578.7T patent/DK0575429T3/da active
- 1992-02-28 AU AU13707/92A patent/AU663699B2/en not_active Ceased
- 1992-02-28 KR KR1019930702618A patent/KR0183424B1/ko not_active Expired - Fee Related
- 1992-02-28 CA CA002105385A patent/CA2105385C/en not_active Expired - Fee Related
- 1992-02-28 WO PCT/DK1992/000063 patent/WO1992015303A1/en not_active Ceased
- 1992-02-28 IL IL10110292A patent/IL101102A/en not_active IP Right Cessation
- 1992-02-28 HK HK98102377A patent/HK1003560A1/en not_active IP Right Cessation
- 1992-02-28 EP EP92906578A patent/EP0575429B1/en not_active Expired - Lifetime
- 1992-03-02 NZ NZ241800A patent/NZ241800A/en not_active IP Right Cessation
-
1993
- 1993-08-31 NO NO933091A patent/NO307406B1/no not_active IP Right Cessation
- 1993-09-01 US US08/115,449 patent/US5444073A/en not_active Expired - Lifetime
-
1998
- 1998-10-16 CY CY9802083A patent/CY2083B1/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK36291D0 (da) | 1991-03-01 |
| KR0183424B1 (ko) | 1999-05-01 |
| IE70600B1 (en) | 1996-12-11 |
| CY2083B1 (en) | 1998-10-16 |
| CA2105385C (en) | 2000-08-15 |
| HK1003560A1 (en) | 1998-10-30 |
| WO1992015303A1 (en) | 1992-09-17 |
| JP3108434B2 (ja) | 2000-11-13 |
| ATE131055T1 (de) | 1995-12-15 |
| DE69206607D1 (de) | 1996-01-18 |
| ZA921462B (en) | 1992-11-25 |
| NO933091D0 (no) | 1993-08-31 |
| IE920572A1 (en) | 1992-09-09 |
| DK0575429T3 (da) | 1996-04-22 |
| NO307406B1 (no) | 2000-04-03 |
| AU1370792A (en) | 1992-10-06 |
| AU663699B2 (en) | 1995-10-19 |
| JPH06504787A (ja) | 1994-06-02 |
| KR930702978A (ko) | 1993-11-29 |
| IL101102A0 (en) | 1992-11-15 |
| CA2105385A1 (en) | 1992-09-02 |
| NZ241800A (en) | 1997-03-24 |
| NO933091L (no) | 1993-11-01 |
| EP0575429A1 (en) | 1993-12-29 |
| EP0575429B1 (en) | 1995-12-06 |
| DE69206607T2 (de) | 1996-05-15 |
| US5444073A (en) | 1995-08-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FF | Patent granted | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| KB | Patent renewed | ||
| MM9K | Patent not in force due to non-payment of renewal fees |