NO312958B1 - Akridinderivater, fremgangsmåte for fremstilling av disse og anvendelse av derivatene - Google Patents
Akridinderivater, fremgangsmåte for fremstilling av disse og anvendelse av derivatene Download PDFInfo
- Publication number
- NO312958B1 NO312958B1 NO19993320A NO993320A NO312958B1 NO 312958 B1 NO312958 B1 NO 312958B1 NO 19993320 A NO19993320 A NO 19993320A NO 993320 A NO993320 A NO 993320A NO 312958 B1 NO312958 B1 NO 312958B1
- Authority
- NO
- Norway
- Prior art keywords
- hydrochloride
- phenyl
- acridin
- dimethylaminomethyl
- methoxy
- Prior art date
Links
- 229940027998 antiseptic and disinfectant acridine derivative Drugs 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 6
- 125000000641 acridinyl group Chemical class C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 title claims 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 72
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000002253 acid Substances 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- -1 hydrochloride Chemical compound 0.000 claims description 10
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
- 238000003776 cleavage reaction Methods 0.000 claims description 8
- 230000007017 scission Effects 0.000 claims description 8
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- FXWFZIRWWNPPOV-UHFFFAOYSA-N 2-aminobenzaldehyde Chemical class NC1=CC=CC=C1C=O FXWFZIRWWNPPOV-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- STPUBFLBPKBADP-UHFFFAOYSA-N 1-[3-(3-methoxyphenyl)-1,2-dihydroacridin-2-yl]-n,n-dimethylmethanamine Chemical compound COC1=CC=CC(C=2C(CC3=CC4=CC=CC=C4N=C3C=2)CN(C)C)=C1 STPUBFLBPKBADP-UHFFFAOYSA-N 0.000 claims description 5
- 230000000202 analgesic effect Effects 0.000 claims description 5
- LUQMICHJIDWOFM-UHFFFAOYSA-N 1-[1-(3-methoxyphenyl)-3,4-dihydroacridin-2-yl]-n,n-dimethylmethanamine Chemical compound COC1=CC=CC(C=2C3=CC4=CC=CC=C4N=C3CCC=2CN(C)C)=C1 LUQMICHJIDWOFM-UHFFFAOYSA-N 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 4
- 238000003379 elimination reaction Methods 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- PGWYYTNYQQDNLB-UHFFFAOYSA-N 3-[2-[(dimethylamino)methyl]-3,4-dihydroacridin-1-yl]phenol Chemical compound C12=CC3=CC=CC=C3N=C2CCC(CN(C)C)=C1C1=CC=CC(O)=C1 PGWYYTNYQQDNLB-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 19
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 13
- 239000013078 crystal Substances 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
- 239000005051 trimethylchlorosilane Substances 0.000 description 13
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 229940098779 methanesulfonic acid Drugs 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 229930182817 methionine Natural products 0.000 description 8
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 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 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000001251 acridines Chemical class 0.000 description 6
- 235000019253 formic acid Nutrition 0.000 description 6
- 229940127240 opiate Drugs 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 150000001934 cyclohexanes Chemical class 0.000 description 5
- 239000003480 eluent Substances 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000011835 investigation Methods 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- 229960005181 morphine Drugs 0.000 description 4
- 150000002900 organolithium compounds Chemical class 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- NQARLSJORZEBHF-FPOVZHCZSA-N COC1=CC=CC([C@H]2[C@@H](CC3=CC4=CC=CC=C4N=C3C2)CN(C)C)=C1 Chemical compound COC1=CC=CC([C@H]2[C@@H](CC3=CC4=CC=CC=C4N=C3C2)CN(C)C)=C1 NQARLSJORZEBHF-FPOVZHCZSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 230000027455 binding Effects 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003054 catalyst Substances 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
- 230000000694 effects Effects 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229940005483 opioid analgesics Drugs 0.000 description 3
- 150000002902 organometallic compounds Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- OUYMIVVXCKWKBY-MBSDFSHPSA-N 1-[(1r,2r)-1-(3-methoxyphenyl)-1,2,3,4-tetrahydroacridin-2-yl]-n,n-dimethylmethanamine Chemical compound COC1=CC=CC([C@@H]2C3=CC4=CC=CC=C4N=C3CC[C@H]2CN(C)C)=C1 OUYMIVVXCKWKBY-MBSDFSHPSA-N 0.000 description 2
- OUYMIVVXCKWKBY-JPYJTQIMSA-N 1-[(1r,2s)-1-(3-methoxyphenyl)-1,2,3,4-tetrahydroacridin-2-yl]-n,n-dimethylmethanamine Chemical compound COC1=CC=CC([C@@H]2C3=CC4=CC=CC=C4N=C3CC[C@@H]2CN(C)C)=C1 OUYMIVVXCKWKBY-JPYJTQIMSA-N 0.000 description 2
- PLDWAJLZAAHOGG-UHFFFAOYSA-N 1-bromo-3-methoxybenzene Chemical compound COC1=CC=CC(Br)=C1 PLDWAJLZAAHOGG-UHFFFAOYSA-N 0.000 description 2
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical group CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- 102100025841 Cholecystokinin Human genes 0.000 description 2
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- 150000007513 acids Chemical class 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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- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
- VKRKCBWIVLSRBJ-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decan-8-one Chemical compound C1CC(=O)CCC21OCCO2 VKRKCBWIVLSRBJ-UHFFFAOYSA-N 0.000 description 1
- IQYLDEDKTKNMFE-UHFFFAOYSA-N 1-[1-(3-methoxyphenyl)-3,4-dihydroacridin-2-yl]-n,n-dimethylmethanamine;hydrochloride Chemical compound Cl.COC1=CC=CC(C=2C3=CC4=CC=CC=C4N=C3CCC=2CN(C)C)=C1 IQYLDEDKTKNMFE-UHFFFAOYSA-N 0.000 description 1
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- NHFVEBWIBVLQKP-UHFFFAOYSA-N 3,3-dimethyl-1,5-dioxaspiro[5.5]undecan-10-one Chemical compound O1CC(C)(C)COC11CC(=O)CCC1 NHFVEBWIBVLQKP-UHFFFAOYSA-N 0.000 description 1
- NGIJYZXCLGHEKG-UHFFFAOYSA-N 3,3-dimethyl-2,4-dihydroacridin-1-one Chemical compound C1=CC=C2N=C(CC(C)(C)CC3=O)C3=CC2=C1 NGIJYZXCLGHEKG-UHFFFAOYSA-N 0.000 description 1
- AHYRKKMYONDWBQ-UHFFFAOYSA-N 3-[2-[(dimethylamino)methyl]-3,3-dimethyl-4h-acridin-1-yl]phenol Chemical compound C12=CC3=CC=CC=C3N=C2CC(C)(C)C(CN(C)C)=C1C1=CC=CC(O)=C1 AHYRKKMYONDWBQ-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/06—Oxygen atoms
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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
-
- 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]
-
- 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]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Press Drives And Press Lines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19830105A DE19830105C1 (de) | 1998-07-06 | 1998-07-06 | Acridinderivate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO993320D0 NO993320D0 (no) | 1999-07-05 |
| NO993320L NO993320L (no) | 2000-01-07 |
| NO312958B1 true NO312958B1 (no) | 2002-07-22 |
Family
ID=7873106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19993320A NO312958B1 (no) | 1998-07-06 | 1999-07-05 | Akridinderivater, fremgangsmåte for fremstilling av disse og anvendelse av derivatene |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US6077845A (ko) |
| EP (2) | EP1369417A1 (ko) |
| JP (1) | JP2000026426A (ko) |
| KR (1) | KR100601742B1 (ko) |
| CN (1) | CN1206221C (ko) |
| AR (1) | AR019219A1 (ko) |
| AT (1) | ATE247643T1 (ko) |
| AU (1) | AU749935B2 (ko) |
| BR (1) | BR9903115A (ko) |
| CA (1) | CA2276764C (ko) |
| CO (1) | CO5080790A1 (ko) |
| CZ (1) | CZ296559B6 (ko) |
| DE (2) | DE19830105C1 (ko) |
| DK (1) | DK0970949T3 (ko) |
| ES (1) | ES2205642T3 (ko) |
| HK (1) | HK1024699A1 (ko) |
| HU (1) | HU226039B1 (ko) |
| IL (1) | IL130801A (ko) |
| MY (1) | MY124404A (ko) |
| NO (1) | NO312958B1 (ko) |
| NZ (1) | NZ336122A (ko) |
| PE (1) | PE20000733A1 (ko) |
| PL (1) | PL193386B1 (ko) |
| PT (1) | PT970949E (ko) |
| RU (1) | RU2225399C2 (ko) |
| SI (1) | SI0970949T1 (ko) |
| SK (1) | SK284234B6 (ko) |
| UY (1) | UY25592A1 (ko) |
| ZA (1) | ZA994369B (ko) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10000311A1 (de) * | 2000-01-05 | 2001-07-12 | Gruenenthal Gmbh | Aminomethyl-Phonyl-Cyclohexanonderivate |
| KR100381716B1 (ko) * | 2000-10-09 | 2003-04-26 | 한국화학연구원 | 항암활성을 가지는 아크리딘 유도체 |
| HUE026184T2 (en) * | 2008-03-27 | 2016-05-30 | Gruenenthal Gmbh | (Hetero-) aryl-cyclohexane derivatives |
| CN105315205B (zh) * | 2015-01-19 | 2018-03-23 | 威海惠安康生物科技有限公司 | 一种以邻硝基苯甲醛和环己醇为原料制备吖啶的方法 |
| RU2616247C1 (ru) * | 2016-03-28 | 2017-04-13 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Северо-Осетинский государственный университет имени Коста Левановича Хетагурова" (СОГУ) | Твердая лекарственная форма, обладающая холинопозитивным действием, на основе 9-бутиламино-3,3-диметил-1,2,4-тригидроакридина |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3652589A (en) * | 1967-07-27 | 1972-03-28 | Gruenenthal Chemie | 1-(m-substituted phenyl)-2-aminomethyl cyclohexanols |
| US4851536A (en) * | 1987-05-07 | 1989-07-25 | American Home Products Corporation | Cyclohexylquinolines as inhibitors of interleukin 1 |
| DE19525137C2 (de) * | 1995-07-11 | 2003-02-27 | Gruenenthal Gmbh | 6-Dimethylaminomethyl-1-phenyl-cyclohexanverbin -dungen als Zwischenprodukte zur Herstellung pharmazeutischer Wirkstoffe |
| DE19547766A1 (de) * | 1995-12-20 | 1997-06-26 | Gruenenthal Gmbh | 1-Phenyl-2-dimethylaminomethyl-cyclohexan-1-ol-verbindungen als pharmazeutische Wirkstoffe |
| DE19609847A1 (de) * | 1996-03-13 | 1997-09-18 | Gruenenthal Gmbh | Dimethyl-(3-aryl-but-3-enyl)-aminverbindungen als pharmazeutische Wirkstoffe |
| DE19805370A1 (de) * | 1997-03-14 | 1998-09-17 | Gruenenthal Gmbh | Substituierte Aminoverbindungen und ihre Verwendung als analgetisch wirksame Substanzen |
| DE19755480A1 (de) * | 1997-12-13 | 1999-06-24 | Gruenenthal Gmbh | Substituierte heterocyclische Benzocycloalkene und ihre Verwendung als analgetisch wirksame Substanzen |
-
1998
- 1998-07-06 DE DE19830105A patent/DE19830105C1/de not_active Expired - Fee Related
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1999
- 1999-06-03 NZ NZ336122A patent/NZ336122A/en unknown
- 1999-06-04 MY MYPI99002260A patent/MY124404A/en unknown
- 1999-06-15 ES ES99111564T patent/ES2205642T3/es not_active Expired - Lifetime
- 1999-06-15 AT AT99111564T patent/ATE247643T1/de not_active IP Right Cessation
- 1999-06-15 EP EP03013144A patent/EP1369417A1/de not_active Withdrawn
- 1999-06-15 DE DE59906645T patent/DE59906645D1/de not_active Expired - Lifetime
- 1999-06-15 SI SI9930393T patent/SI0970949T1/xx unknown
- 1999-06-15 PT PT99111564T patent/PT970949E/pt unknown
- 1999-06-15 EP EP99111564A patent/EP0970949B1/de not_active Expired - Lifetime
- 1999-06-15 DK DK99111564T patent/DK0970949T3/da active
- 1999-06-24 PE PE1999000565A patent/PE20000733A1/es not_active Application Discontinuation
- 1999-06-29 US US09/340,729 patent/US6077845A/en not_active Expired - Fee Related
- 1999-06-30 UY UY25592A patent/UY25592A1/es not_active Application Discontinuation
- 1999-07-02 CA CA002276764A patent/CA2276764C/en not_active Expired - Fee Related
- 1999-07-02 CO CO99041630A patent/CO5080790A1/es unknown
- 1999-07-02 AR ARP990103231A patent/AR019219A1/es active IP Right Grant
- 1999-07-02 SK SK908-99A patent/SK284234B6/sk not_active IP Right Cessation
- 1999-07-02 CZ CZ0240799A patent/CZ296559B6/cs not_active IP Right Cessation
- 1999-07-05 JP JP11190920A patent/JP2000026426A/ja active Pending
- 1999-07-05 PL PL334180A patent/PL193386B1/pl not_active IP Right Cessation
- 1999-07-05 AU AU37983/99A patent/AU749935B2/en not_active Ceased
- 1999-07-05 RU RU99114454/04A patent/RU2225399C2/ru not_active IP Right Cessation
- 1999-07-05 HU HU9902270A patent/HU226039B1/hu not_active IP Right Cessation
- 1999-07-05 ZA ZA9904369A patent/ZA994369B/xx unknown
- 1999-07-05 NO NO19993320A patent/NO312958B1/no not_active IP Right Cessation
- 1999-07-05 IL IL130801A patent/IL130801A/en not_active IP Right Cessation
- 1999-07-05 CN CNB991101618A patent/CN1206221C/zh not_active Expired - Fee Related
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