NO317054B1 - Aminometyl-2,3,8,9-tetrahydro-7H-1,4-dioksono [2,3-e]-indol-8-oner og derivater, samt anvendelse av dem - Google Patents
Aminometyl-2,3,8,9-tetrahydro-7H-1,4-dioksono [2,3-e]-indol-8-oner og derivater, samt anvendelse av dem Download PDFInfo
- Publication number
- NO317054B1 NO317054B1 NO19964686A NO964686A NO317054B1 NO 317054 B1 NO317054 B1 NO 317054B1 NO 19964686 A NO19964686 A NO 19964686A NO 964686 A NO964686 A NO 964686A NO 317054 B1 NO317054 B1 NO 317054B1
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- tetrahydro
- dioxino
- acceptable salt
- indol
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 158
- 150000003839 salts Chemical class 0.000 claims description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- -1 4-methyl-benzylamino Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 229960003638 dopamine Drugs 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 5
- 208000028017 Psychotic disease Diseases 0.000 claims description 5
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 3
- 208000016620 Tourette disease Diseases 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 208000031424 hyperprolactinemia Diseases 0.000 claims description 3
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- AXTMJYJTMSEHLD-UHFFFAOYSA-N 2-(aminomethyl)-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical compound C1=C2NC(=O)CC2=C2OC(CN)COC2=C1 AXTMJYJTMSEHLD-UHFFFAOYSA-N 0.000 claims description 2
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- AACXXTPYXFYWHE-UHFFFAOYSA-N 2-[(2-pyridin-3-ylethylamino)methyl]-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical compound N1C(=O)CC(C=2O3)=C1C=CC=2OCC3CNCCC1=CC=CN=C1 AACXXTPYXFYWHE-UHFFFAOYSA-N 0.000 claims 1
- OTVMHFYWQHFJFA-UHFFFAOYSA-N 2-[(3-hydroxypropylamino)methyl]-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical group C1=C2NC(=O)CC2=C2OC(CNCCCO)COC2=C1 OTVMHFYWQHFJFA-UHFFFAOYSA-N 0.000 claims 1
- AEYWZMUJOOUVRU-UHFFFAOYSA-N 2-[(benzylamino)methyl]-3,7,9,10-tetrahydro-2h-[1,4]dioxino[2,3-f]quinolin-8-one Chemical compound N1C(=O)CCC(C=2O3)=C1C=CC=2OCC3CNCC1=CC=CC=C1 AEYWZMUJOOUVRU-UHFFFAOYSA-N 0.000 claims 1
- ALQQHTNLZHNFSE-UHFFFAOYSA-N 2-[(benzylamino)methyl]-3,7-dihydro-2h-[1,4]dioxino[2,3-e]indole-8,9-dione Chemical group O1C2=C3C(=O)C(=O)NC3=CC=C2OCC1CNCC1=CC=CC=C1 ALQQHTNLZHNFSE-UHFFFAOYSA-N 0.000 claims 1
- VAQQLHYBNQUUPH-UHFFFAOYSA-N 2-[(benzylamino)methyl]-6-fluoro-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical group O1C=2C=3CC(=O)NC=3C(F)=CC=2OCC1CNCC1=CC=CC=C1 VAQQLHYBNQUUPH-UHFFFAOYSA-N 0.000 claims 1
- KNTNJFBWDVWWMP-UHFFFAOYSA-N 2-[(benzylamino)methyl]-6-methyl-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical group O1C=2C=3CC(=O)NC=3C(C)=CC=2OCC1CNCC1=CC=CC=C1 KNTNJFBWDVWWMP-UHFFFAOYSA-N 0.000 claims 1
- GOBBXNXZHFSGPA-UHFFFAOYSA-N 2-[(prop-2-ynylamino)methyl]-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical compound O1CC(CNCC#C)OC2=C1C=CC1=C2CC(=O)N1 GOBBXNXZHFSGPA-UHFFFAOYSA-N 0.000 claims 1
- JZCKVNNAWKXIGV-UHFFFAOYSA-N 2-[[(4-fluorophenyl)methylamino]methyl]-6-methyl-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical group O1C=2C=3CC(=O)NC=3C(C)=CC=2OCC1CNCC1=CC=C(F)C=C1 JZCKVNNAWKXIGV-UHFFFAOYSA-N 0.000 claims 1
- ANAAYHRMPZCDKR-UHFFFAOYSA-N 2-[[2-(1h-indol-3-yl)ethylamino]methyl]-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical group C1=CC=C2C(CCNCC3COC=4C=CC5=C(C=4O3)CC(N5)=O)=CNC2=C1 ANAAYHRMPZCDKR-UHFFFAOYSA-N 0.000 claims 1
- GFOREZIOZJPIAR-UHFFFAOYSA-N 2-[[3-[3-(dimethylamino)phenoxy]propylamino]methyl]-6-fluoro-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical group CN(C)C1=CC=CC(OCCCNCC2OC3=C4CC(=O)NC4=C(F)C=C3OC2)=C1 GFOREZIOZJPIAR-UHFFFAOYSA-N 0.000 claims 1
- TYUCHIVJZCDWSW-UHFFFAOYSA-N 2-methyl-2-(4-phenylbutylamino)-7,9-dihydro-3h-[1,4]dioxino[2,3-e]indol-8-one Chemical group C1OC2=CC=C3NC(=O)CC3=C2OC1(C)NCCCCC1=CC=CC=C1 TYUCHIVJZCDWSW-UHFFFAOYSA-N 0.000 claims 1
- FCFNGBSIDWXXBE-UHFFFAOYSA-N 6-chloro-2-[[(4-fluorophenyl)methylamino]methyl]-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical group C1=CC(F)=CC=C1CNCC1OC2=C3CC(=O)NC3=C(Cl)C=C2OC1 FCFNGBSIDWXXBE-UHFFFAOYSA-N 0.000 claims 1
- VLXAEQSAFIRGAM-UHFFFAOYSA-N 6-chloro-2-[[(4-methylphenyl)methylamino]methyl]-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical group C1=CC(C)=CC=C1CNCC1OC2=C3CC(=O)NC3=C(Cl)C=C2OC1 VLXAEQSAFIRGAM-UHFFFAOYSA-N 0.000 claims 1
- JYFOEWHPNZOURL-UHFFFAOYSA-N 6-fluoro-2-[[(4-fluorophenyl)methylamino]methyl]-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical group C1=CC(F)=CC=C1CNCC1OC2=C3CC(=O)NC3=C(F)C=C2OC1 JYFOEWHPNZOURL-UHFFFAOYSA-N 0.000 claims 1
- FNFZVRFWNDRQNP-UHFFFAOYSA-N 6-fluoro-2-[[(4-methylphenyl)methylamino]methyl]-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical group C1=CC(C)=CC=C1CNCC1OC2=C3CC(=O)NC3=C(F)C=C2OC1 FNFZVRFWNDRQNP-UHFFFAOYSA-N 0.000 claims 1
- PSDXGHNGCKKPMX-UHFFFAOYSA-N 6-fluoro-2-[[3-(1h-indol-3-yl)propylamino]methyl]-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical group C1=CC=C2C(CCCNCC3COC=4C=C(C=5NC(=O)CC=5C=4O3)F)=CNC2=C1 PSDXGHNGCKKPMX-UHFFFAOYSA-N 0.000 claims 1
- QTVXKIIOWBOLHK-UHFFFAOYSA-N 6-methyl-2-[(thiophen-2-ylmethylamino)methyl]-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-8-one Chemical compound O1C=2C=3CC(=O)NC=3C(C)=CC=2OCC1CNCC1=CC=CS1 QTVXKIIOWBOLHK-UHFFFAOYSA-N 0.000 claims 1
- BBZLRMNIIKHTRE-UHFFFAOYSA-N 9-[2-(4-fluorophenyl)ethylidene]-2-[[(4-fluorophenyl)methylamino]methyl]-3,7-dihydro-2h-[1,4]dioxino[2,3-e]indol-8-one Chemical compound C1=CC(F)=CC=C1CNCC(COC1=CC=C2NC3=O)OC1=C2C3=CCC1=CC=C(F)C=C1 BBZLRMNIIKHTRE-UHFFFAOYSA-N 0.000 claims 1
- MMLMAJDRUIBMDG-UHFFFAOYSA-N CNC(C1COC2=C(O1)C3=C(C=C2)NC(=O)C3)C4=CC=CC5=CC=CC=C54 Chemical group CNC(C1COC2=C(O1)C3=C(C=C2)NC(=O)C3)C4=CC=CC5=CC=CC=C54 MMLMAJDRUIBMDG-UHFFFAOYSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- DYJIKHYBKVODAC-UHFFFAOYSA-N aplindore Chemical group N1C(=O)CC(C=2O3)=C1C=CC=2OCC3CNCC1=CC=CC=C1 DYJIKHYBKVODAC-UHFFFAOYSA-N 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 125000005606 carbostyryl group Chemical group 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- RDVGCSBXTULVHB-UHFFFAOYSA-N n-[3-[3-[(8-oxo-2,3,7,9-tetrahydro-[1,4]dioxino[2,3-e]indol-2-yl)methylamino]propoxy]phenyl]acetamide Chemical group CC(=O)NC1=CC=CC(OCCCNCC2OC3=C4CC(=O)NC4=CC=C3OC2)=C1 RDVGCSBXTULVHB-UHFFFAOYSA-N 0.000 claims 1
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- 239000002904 solvent Substances 0.000 description 19
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (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)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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US728395P | 1995-11-06 | 1995-11-06 | |
US08/730,267 US5756532A (en) | 1995-11-06 | 1996-10-15 | Aminomethyl-2 3 8 9-tetrahydro-7H-1 4-dioxino 2 3-E!-indol-8-ones and derivatives |
Publications (3)
Publication Number | Publication Date |
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NO964686D0 NO964686D0 (no) | 1996-11-05 |
NO964686L NO964686L (no) | 1997-05-07 |
NO317054B1 true NO317054B1 (no) | 2004-08-02 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO19964686A NO317054B1 (no) | 1995-11-06 | 1996-11-05 | Aminometyl-2,3,8,9-tetrahydro-7H-1,4-dioksono [2,3-e]-indol-8-oner og derivater, samt anvendelse av dem |
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US (2) | US5756532A (pt) |
EP (3) | EP1375503B1 (pt) |
JP (1) | JP4311770B2 (pt) |
KR (1) | KR100566678B1 (pt) |
CN (1) | CN1084748C (pt) |
AR (2) | AR004284A1 (pt) |
AT (1) | ATE349450T1 (pt) |
AU (1) | AU701624B2 (pt) |
CA (1) | CA2189524C (pt) |
CZ (1) | CZ291731B6 (pt) |
DE (1) | DE69636801T2 (pt) |
DK (1) | DK1375503T3 (pt) |
ES (1) | ES2277014T3 (pt) |
HU (1) | HU224841B1 (pt) |
IL (1) | IL119565A (pt) |
MX (1) | MX9605367A (pt) |
NO (1) | NO317054B1 (pt) |
NZ (1) | NZ299693A (pt) |
PT (1) | PT1375503E (pt) |
RU (1) | RU2178416C2 (pt) |
SK (1) | SK282168B6 (pt) |
Families Citing this family (40)
Publication number | Priority date | Publication date | Assignee | Title |
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GB9627005D0 (en) * | 1996-12-27 | 1997-02-12 | Knoll Ag | Therapeutic agents |
GB9704948D0 (en) | 1997-03-11 | 1997-04-30 | Knoll Ag | Therapeutic agents |
US6362009B1 (en) | 1997-11-21 | 2002-03-26 | Merck & Co., Inc. | Solid phase synthesis of heterocycles |
US6350773B1 (en) * | 1999-12-10 | 2002-02-26 | American Home Products Corporation | Therapeutic combinations of (S)-2-(benzylamino-methyl)-2,3,8,9,-tetrahydro 7H-1,4-dioxino{2,3-e}indol-8-one and neuroleptics for the treatment or prevention of psychotic disorders |
JP5557409B2 (ja) * | 1999-12-10 | 2014-07-23 | ワイス・エルエルシー | (s)−2−(ベンジルアミノメチル)−2,3,8,9−テトラヒドロ−7h−1,4−ジオキシノ(2,3)eインドール−8−オンと神経遮断薬との組合せ |
US20060287335A1 (en) * | 2000-11-28 | 2006-12-21 | Wyeth | Serotonergic agents for treating sexual dysfunction |
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AU639536B2 (en) * | 1990-03-15 | 1993-07-29 | Pharmacia & Upjohn Company | Therapeutically useful heterocyclic indole compounds |
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-
1996
- 1996-10-15 US US08/730,267 patent/US5756532A/en not_active Expired - Lifetime
- 1996-10-22 ES ES03021780T patent/ES2277014T3/es not_active Expired - Lifetime
- 1996-10-22 EP EP03021780A patent/EP1375503B1/en not_active Expired - Lifetime
- 1996-10-22 EP EP06015712A patent/EP1726592A1/en not_active Withdrawn
- 1996-10-22 PT PT03021780T patent/PT1375503E/pt unknown
- 1996-10-22 EP EP96307616A patent/EP0771800A3/en not_active Ceased
- 1996-10-22 AT AT03021780T patent/ATE349450T1/de active
- 1996-10-22 DK DK03021780T patent/DK1375503T3/da active
- 1996-10-22 DE DE69636801T patent/DE69636801T2/de not_active Expired - Lifetime
- 1996-10-31 SK SK1414-96A patent/SK282168B6/sk not_active IP Right Cessation
- 1996-11-01 AU AU70553/96A patent/AU701624B2/en not_active Ceased
- 1996-11-04 CA CA002189524A patent/CA2189524C/en not_active Expired - Fee Related
- 1996-11-04 NZ NZ299693A patent/NZ299693A/xx not_active IP Right Cessation
- 1996-11-04 RU RU96121824/04A patent/RU2178416C2/ru not_active IP Right Cessation
- 1996-11-05 IL IL11956596A patent/IL119565A/en not_active IP Right Cessation
- 1996-11-05 CN CN96121650A patent/CN1084748C/zh not_active Expired - Fee Related
- 1996-11-05 HU HU9603057A patent/HU224841B1/hu not_active IP Right Cessation
- 1996-11-05 KR KR1019960051969A patent/KR100566678B1/ko not_active IP Right Cessation
- 1996-11-05 NO NO19964686A patent/NO317054B1/no not_active IP Right Cessation
- 1996-11-05 JP JP29247996A patent/JP4311770B2/ja not_active Expired - Fee Related
- 1996-11-05 AR ARP960105059A patent/AR004284A1/es active IP Right Grant
- 1996-11-05 CZ CZ19963241A patent/CZ291731B6/cs not_active IP Right Cessation
- 1996-11-05 MX MX9605367A patent/MX9605367A/es unknown
-
1998
- 1998-01-29 US US09/015,149 patent/US5962465A/en not_active Expired - Lifetime
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2000
- 2000-09-15 AR ARP000104875A patent/AR025698A1/es unknown
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