NO311128B1 - Substituerte aminoforbindelser, fremgangsmåte for fremstilling derav samt anvendelse av forbindelsene - Google Patents
Substituerte aminoforbindelser, fremgangsmåte for fremstilling derav samt anvendelse av forbindelsene Download PDFInfo
- Publication number
- NO311128B1 NO311128B1 NO19981121A NO981121A NO311128B1 NO 311128 B1 NO311128 B1 NO 311128B1 NO 19981121 A NO19981121 A NO 19981121A NO 981121 A NO981121 A NO 981121A NO 311128 B1 NO311128 B1 NO 311128B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- formula
- phenyl
- dihydro
- substituted amino
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 239000003814 drug Substances 0.000 claims abstract description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])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
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 4
- -1 amino compound Chemical class 0.000 claims description 4
- 230000000202 analgesic effect Effects 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000003509 tertiary alcohols Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 150000002902 organometallic compounds Chemical class 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 74
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
- 238000002844 melting Methods 0.000 description 47
- 230000008018 melting Effects 0.000 description 47
- 239000000243 solution Substances 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- 239000000047 product Substances 0.000 description 15
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 14
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 14
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
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- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
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- 238000010992 reflux Methods 0.000 description 6
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- 239000008346 aqueous phase Substances 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
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- XHLHPRDBBAGVEG-UHFFFAOYSA-N 1-tetralone Chemical compound C1=CC=C2C(=O)CCCC2=C1 XHLHPRDBBAGVEG-UHFFFAOYSA-N 0.000 description 4
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229960005181 morphine Drugs 0.000 description 4
- 239000012071 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
- 238000012360 testing method Methods 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
- 238000010626 work up procedure Methods 0.000 description 4
- PLDWAJLZAAHOGG-UHFFFAOYSA-N 1-bromo-3-methoxybenzene Chemical compound COC1=CC=CC(Br)=C1 PLDWAJLZAAHOGG-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 210000004556 brain Anatomy 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
- 230000008020 evaporation Effects 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- IOXXVNYDGIXMIP-UHFFFAOYSA-N n-methylprop-2-en-1-amine Chemical compound CNCC=C IOXXVNYDGIXMIP-UHFFFAOYSA-N 0.000 description 3
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- ZHUJMSMQIPIPTF-IBURTVSXSA-N (2r)-2-[[(2s)-2-[[2-[[(2r)-2-[[(2s)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]acetyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoic acid Chemical compound C([C@@H](C(=O)N[C@H](CC(C)C)C(O)=O)NC(=O)CNC(=O)[C@@H](C)NC(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=CC=C1 ZHUJMSMQIPIPTF-IBURTVSXSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- KWHUHTFXMNQHAA-UHFFFAOYSA-N 6,7,8,9-tetrahydrobenzo[7]annulen-5-one Chemical compound O=C1CCCCC2=CC=CC=C12 KWHUHTFXMNQHAA-UHFFFAOYSA-N 0.000 description 2
- XXAQLPZLFNKVJJ-UHFFFAOYSA-N 6-[(dimethylamino)methyl]-2-methoxy-6,7,8,9-tetrahydrobenzo[7]annulen-5-one Chemical compound C1CCC(CN(C)C)C(=O)C=2C1=CC(OC)=CC=2 XXAQLPZLFNKVJJ-UHFFFAOYSA-N 0.000 description 2
- ZFOLQUQHELUVNU-UHFFFAOYSA-N 7-phenoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1=C2C(=O)CCCC2=CC=C1OC1=CC=CC=C1 ZFOLQUQHELUVNU-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 101800001982 Cholecystokinin Proteins 0.000 description 2
- 102100025841 Cholecystokinin Human genes 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
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- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- 230000000144 pharmacologic effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
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- IZTQOLKUZKXIRV-YRVFCXMDSA-N sincalide Chemical compound C([C@@H](C(=O)N[C@@H](CCSC)C(=O)NCC(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](N)CC(O)=O)C1=CC=C(OS(O)(=O)=O)C=C1 IZTQOLKUZKXIRV-YRVFCXMDSA-N 0.000 description 2
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- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
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- LPXCKPMAYAOICR-UHFFFAOYSA-N 1-[3-[tert-butyl(diphenyl)silyl]oxyphenyl]-2-[(dimethylamino)methyl]-7-phenoxy-3,4-dihydro-2H-naphthalen-1-ol Chemical compound C(C)(C)(C)[Si](OC=1C=C(C=CC=1)C1(C(CCC2=CC=C(C=C12)OC1=CC=CC=C1)CN(C)C)O)(C1=CC=CC=C1)C1=CC=CC=C1 LPXCKPMAYAOICR-UHFFFAOYSA-N 0.000 description 1
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- IEOQNDAIYGDKSP-UHFFFAOYSA-N 2-phenoxy-6,7,8,9-tetrahydrobenzo[7]annulen-5-one Chemical compound C=1C=C2C(=O)CCCCC2=CC=1OC1=CC=CC=C1 IEOQNDAIYGDKSP-UHFFFAOYSA-N 0.000 description 1
- MEOJHRLKWUNOAO-UHFFFAOYSA-N 3,4-dihydro-2h-anthracen-1-one Chemical compound C1=CC=C2C=C3C(=O)CCCC3=CC2=C1 MEOJHRLKWUNOAO-UHFFFAOYSA-N 0.000 description 1
- KBARGPSSEIXDQU-UHFFFAOYSA-N 3,4-dihydro-2h-phenanthren-1-one Chemical compound C1=CC2=CC=CC=C2C2=C1C(=O)CCC2 KBARGPSSEIXDQU-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/28—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by unsaturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/64—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/12—One of the condensed rings being a six-membered aromatic ring the other ring being at least seven-membered
Landscapes
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
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- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19710628 | 1997-03-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO981121D0 NO981121D0 (no) | 1998-03-13 |
| NO981121L NO981121L (no) | 1998-09-15 |
| NO311128B1 true NO311128B1 (no) | 2001-10-15 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19981121A NO311128B1 (no) | 1997-03-14 | 1998-03-13 | Substituerte aminoforbindelser, fremgangsmåte for fremstilling derav samt anvendelse av forbindelsene |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US6022895A (ru) |
| EP (1) | EP0864559B1 (ru) |
| JP (1) | JP4132189B2 (ru) |
| KR (1) | KR100579428B1 (ru) |
| CN (1) | CN1243721C (ru) |
| AR (1) | AR010129A1 (ru) |
| AT (1) | ATE218534T1 (ru) |
| AU (1) | AU728501B2 (ru) |
| CA (1) | CA2231975C (ru) |
| CO (1) | CO4940510A1 (ru) |
| CZ (1) | CZ295522B6 (ru) |
| DE (2) | DE19805370A1 (ru) |
| DK (1) | DK0864559T3 (ru) |
| ES (1) | ES2178055T3 (ru) |
| HK (1) | HK1015351A1 (ru) |
| HU (1) | HU226060B1 (ru) |
| IL (1) | IL123647A (ru) |
| MY (1) | MY118828A (ru) |
| NO (1) | NO311128B1 (ru) |
| NZ (1) | NZ329951A (ru) |
| PE (1) | PE59899A1 (ru) |
| PL (1) | PL191727B1 (ru) |
| PT (1) | PT864559E (ru) |
| RU (1) | RU2197474C2 (ru) |
| SI (1) | SI0864559T1 (ru) |
| SK (1) | SK284279B6 (ru) |
| UA (1) | UA56997C2 (ru) |
| UY (1) | UY24919A1 (ru) |
| ZA (1) | ZA982157B (ru) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19830105C1 (de) * | 1998-07-06 | 2000-02-17 | Gruenenthal Gmbh | Acridinderivate |
| DE19963179B4 (de) | 1999-12-27 | 2009-02-05 | Grünenthal GmbH | Substituierte 1- und 2-Naphthol-Mannichbasen |
| DE10033459A1 (de) * | 2000-07-10 | 2002-01-24 | Gruenenthal Gmbh | Cyclische substituierte Aminomethylverbindungen und diese Verbindungen enthaltende Arzeimittel |
| UA76224C2 (en) | 2001-10-15 | 2006-07-17 | Janssen Pharmaceutica Nv | Substituted 4-phenyl 4-[1h-imidazol-2-yl]-piperidine derivatives and use thereof as selective non-peptide delta-opioid agonists |
| DE10206405A1 (de) * | 2002-02-14 | 2003-08-28 | Gruenenthal Gmbh | Synthese von substituierten Carbamidestern |
| DE10206403A1 (de) * | 2002-02-14 | 2003-08-28 | Gruenenthal Gmbh | Synthese von Beta-Aminoketonen |
| AR044010A1 (es) * | 2003-04-11 | 2005-08-24 | Janssen Pharmaceutica Nv | Uso de derivados de 4-fenil-4- [1h-imidazol-2-il]- piperidina sustituidos como agonistas delta opioideos no peptidos selectivos, con actividad antidepresiva y ansiolitica |
| DE10341534A1 (de) * | 2003-09-09 | 2005-03-31 | Bayer Chemicals Ag | Difluoralkylaromaten |
| NZ546834A (en) | 2003-10-01 | 2010-03-26 | Adolor Corp | Spirocyclic heterocyclic derivatives and methods of their use |
| DE102004030099A1 (de) * | 2004-06-22 | 2006-01-12 | Grünenthal GmbH | Gesättigte und ungesättigte 3-Pyridyl-benzocycloalkylmethyl-amine als Serotonin- und/oder Noradrenalin-Reuptake-Hemmer und/oder µ-Opioidrezeptor-Modulatoren |
| WO2006023757A2 (en) * | 2004-08-19 | 2006-03-02 | University Of Virginia Patent Foundation | Novel tricyclic, bicyclic, monocyclic, and acyclic amines as potent sodium channel blocking agents |
| US7598261B2 (en) * | 2005-03-31 | 2009-10-06 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
| JP5090639B2 (ja) * | 2005-11-18 | 2012-12-05 | 出光興産株式会社 | 芳香族アミン誘導体及びそれを用いた有機エレクトロルミネッセンス素子 |
| US7576207B2 (en) * | 2006-04-06 | 2009-08-18 | Adolor Corporation | Spirocyclic heterocyclic derivatives and methods of their use |
| TWI401237B (zh) * | 2006-07-24 | 2013-07-11 | ３-〔（１ｒ，２ｒ）-３-（二甲基氨基）-１-乙基-２-甲基丙基〕酚之製備 | |
| AU2007294968A1 (en) | 2006-09-12 | 2008-03-20 | Adolor Corporation | Use of N-containing spirocompounds for the enhancement of cognitive function |
| AU2008219115A1 (en) | 2007-02-16 | 2008-08-28 | Synta Pharmaceuticals Corp. | Substituted fused-ring compounds for inflammation and immune-related uses |
| WO2012100423A1 (en) * | 2011-01-27 | 2012-08-02 | Eli Lilly And Company | Analgesic compounds, methods, and formulations |
| RU2538727C1 (ru) * | 2013-11-15 | 2015-01-10 | Закрытое акционерное общество "Институт экспериментальной фармакологии" | Анальгетическое средство пептидной структуры на основе тридекапептида, содержащего d-октааргининовый вектор |
| CN104844471B (zh) * | 2015-04-21 | 2017-05-03 | 苏州远智医药科技有限公司 | 一种作为dor受体拮抗剂的化合物 |
| CN109896991B (zh) * | 2017-12-08 | 2020-11-20 | 苏州远智医药科技有限公司 | 一种δ阿片受体拮抗剂及其用途和药物组合物 |
| JP7413048B2 (ja) | 2020-01-30 | 2024-01-15 | 三和シヤッター工業株式会社 | シャッターカーテン及びシャッターカーテンの梱包方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE623394A (ru) * | ||||
| DE1203247B (de) * | 1961-10-10 | 1965-10-21 | Koninklijke Pharma Fab Nv | Verfahren zur Herstellung von Diphenylalkenyl-aminen sowie deren nicht-toxischen Salzen |
| FR1578702A (ru) * | 1961-10-10 | 1969-08-22 | ||
| DE1149002B (de) * | 1961-10-19 | 1963-05-22 | Giulini Gmbh Geb | Verfahren zur Herstellung von blutdrucksteigernden Salzen von N, N-Dialkyl-2-aethyl-3, 3-diphenyl-propen-(2)-yl-aminen |
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1998
- 1998-02-11 DE DE19805370A patent/DE19805370A1/de not_active Withdrawn
- 1998-02-19 AT AT98102853T patent/ATE218534T1/de active
- 1998-02-19 EP EP98102853A patent/EP0864559B1/de not_active Expired - Lifetime
- 1998-02-19 PT PT98102853T patent/PT864559E/pt unknown
- 1998-02-19 SI SI9830137T patent/SI0864559T1/xx unknown
- 1998-02-19 DE DE59804276T patent/DE59804276D1/de not_active Expired - Lifetime
- 1998-02-19 ES ES98102853T patent/ES2178055T3/es not_active Expired - Lifetime
- 1998-02-19 DK DK98102853T patent/DK0864559T3/da active
- 1998-03-09 MY MYPI98001021A patent/MY118828A/en unknown
- 1998-03-09 UY UY24919A patent/UY24919A1/es not_active Application Discontinuation
- 1998-03-11 AR ARP980101094A patent/AR010129A1/es unknown
- 1998-03-11 US US09/038,033 patent/US6022895A/en not_active Expired - Lifetime
- 1998-03-11 CO CO98013443A patent/CO4940510A1/es unknown
- 1998-03-12 SK SK333-98A patent/SK284279B6/sk not_active IP Right Cessation
- 1998-03-12 CA CA002231975A patent/CA2231975C/en not_active Expired - Fee Related
- 1998-03-12 CZ CZ1998755A patent/CZ295522B6/cs not_active IP Right Cessation
- 1998-03-12 CN CNB981078680A patent/CN1243721C/zh not_active Expired - Fee Related
- 1998-03-12 IL IL12364798A patent/IL123647A/en not_active IP Right Cessation
- 1998-03-12 RU RU98105507/04A patent/RU2197474C2/ru active
- 1998-03-12 UA UA98031284A patent/UA56997C2/ru unknown
- 1998-03-12 NZ NZ329951A patent/NZ329951A/en unknown
- 1998-03-12 PE PE1998000170A patent/PE59899A1/es not_active Application Discontinuation
- 1998-03-13 KR KR1019980008435A patent/KR100579428B1/ko not_active IP Right Cessation
- 1998-03-13 AU AU58408/98A patent/AU728501B2/en not_active Ceased
- 1998-03-13 NO NO19981121A patent/NO311128B1/no unknown
- 1998-03-13 PL PL325322A patent/PL191727B1/pl not_active IP Right Cessation
- 1998-03-13 JP JP06350098A patent/JP4132189B2/ja not_active Expired - Fee Related
- 1998-03-13 HU HU9800555A patent/HU226060B1/hu not_active IP Right Cessation
- 1998-03-13 ZA ZA982157A patent/ZA982157B/xx unknown
-
1999
- 1999-01-21 HK HK99100283A patent/HK1015351A1/xx not_active IP Right Cessation
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