NO301974B1 - Analogifremgangsmåte for fremstilling av terapeutisk aktive arylalkylaminer og -amider - Google Patents
Analogifremgangsmåte for fremstilling av terapeutisk aktive arylalkylaminer og -amider Download PDFInfo
- Publication number
- NO301974B1 NO301974B1 NO923006A NO923006A NO301974B1 NO 301974 B1 NO301974 B1 NO 301974B1 NO 923006 A NO923006 A NO 923006A NO 923006 A NO923006 A NO 923006A NO 301974 B1 NO301974 B1 NO 301974B1
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- amino
- propylamine
- acetamide
- methylethyl
- Prior art date
Links
- 150000001408 amides Chemical class 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 66
- 238000002360 preparation method Methods 0.000 title claims description 65
- 150000003975 aryl alkyl amines Chemical class 0.000 title claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- -1 4-pyridinyl Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 117
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- ISQJWLCMXCZKHQ-UHFFFAOYSA-N 1-(3-nitrophenyl)-2-phenylpropan-2-amine Chemical compound C=1C=CC=CC=1C(N)(C)CC1=CC=CC([N+]([O-])=O)=C1 ISQJWLCMXCZKHQ-UHFFFAOYSA-N 0.000 claims description 3
- MDDJBCCCTQYLLC-UHFFFAOYSA-N 2-(2-methylphenyl)-1-phenylpropan-2-amine Chemical compound CC1=CC=CC=C1C(C)(N)CC1=CC=CC=C1 MDDJBCCCTQYLLC-UHFFFAOYSA-N 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 238000005576 amination reaction Methods 0.000 claims description 3
- 125000006242 amine protecting group Chemical group 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- HAUFLNPHNKNKRR-UHFFFAOYSA-N 1-(3-bromophenyl)-2-phenylpropan-2-amine Chemical compound C=1C=CC=CC=1C(N)(C)CC1=CC=CC(Br)=C1 HAUFLNPHNKNKRR-UHFFFAOYSA-N 0.000 claims description 2
- CDXUJGDOKDICLE-UHFFFAOYSA-N 1-(3-chlorophenyl)-2-phenylpropan-2-amine Chemical compound C=1C=CC=CC=1C(N)(C)CC1=CC=CC(Cl)=C1 CDXUJGDOKDICLE-UHFFFAOYSA-N 0.000 claims description 2
- SZNKIJVBDJSGHS-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-phenylpropan-2-amine Chemical compound C=1C=CC=CC=1C(N)(C)CC1=CC=C(Cl)C=C1 SZNKIJVBDJSGHS-UHFFFAOYSA-N 0.000 claims description 2
- SFSKKDZMTAWTCK-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-1-phenylpropan-2-amine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(N)(C)CC1=CC=CC=C1 SFSKKDZMTAWTCK-UHFFFAOYSA-N 0.000 claims description 2
- NEAASNGBOSCWFU-UHFFFAOYSA-N 2-(3-chlorophenyl)-1-phenylpropan-2-amine Chemical compound C=1C=CC(Cl)=CC=1C(N)(C)CC1=CC=CC=C1 NEAASNGBOSCWFU-UHFFFAOYSA-N 0.000 claims description 2
- COCYZODYARYYFB-UHFFFAOYSA-N 3-(2-amino-2-phenylpropyl)benzonitrile Chemical compound C=1C=CC=CC=1C(N)(C)CC1=CC=CC(C#N)=C1 COCYZODYARYYFB-UHFFFAOYSA-N 0.000 claims description 2
- XNIHOBICEHULLC-UHFFFAOYSA-N 4-(2-amino-1-phenylpropan-2-yl)phenol Chemical compound C=1C=C(O)C=CC=1C(N)(C)CC1=CC=CC=C1 XNIHOBICEHULLC-UHFFFAOYSA-N 0.000 claims description 2
- CORRGLWUEOPYBY-UHFFFAOYSA-N 4-(2-amino-2-phenylpropyl)phenol Chemical compound C=1C=CC=CC=1C(N)(C)CC1=CC=C(O)C=C1 CORRGLWUEOPYBY-UHFFFAOYSA-N 0.000 claims description 2
- DAXXADQGCDWPAI-UHFFFAOYSA-N 4-[2-amino-2-(4-hydroxyphenyl)propyl]phenol Chemical compound C=1C=C(O)C=CC=1C(N)(C)CC1=CC=C(O)C=C1 DAXXADQGCDWPAI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- RVAUFHAJSOMPOZ-UHFFFAOYSA-N NCl[N+]([O-])=O Chemical compound NCl[N+]([O-])=O RVAUFHAJSOMPOZ-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 238000005878 carbamate elimination reaction Methods 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- WIOJVEBKSTTWMH-UHFFFAOYSA-N 2-(3-nitrophenyl)-1-phenylpropan-2-amine Chemical compound C=1C=CC([N+]([O-])=O)=CC=1C(N)(C)CC1=CC=CC=C1 WIOJVEBKSTTWMH-UHFFFAOYSA-N 0.000 claims 1
- KDRZEPKNVIKGSN-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-phenylpropan-2-amine Chemical compound C=1C=C(Cl)C=CC=1C(N)(C)CC1=CC=CC=C1 KDRZEPKNVIKGSN-UHFFFAOYSA-N 0.000 claims 1
- JPHLFZYORRRMFO-UHFFFAOYSA-N 2-(4-methylphenyl)-1-phenylpropan-2-amine Chemical compound C1=CC(C)=CC=C1C(C)(N)CC1=CC=CC=C1 JPHLFZYORRRMFO-UHFFFAOYSA-N 0.000 claims 1
- TZLCPMQQJPNLGF-UHFFFAOYSA-N 2-amino-n-[1-(3,4-dichlorophenyl)-2-phenylpropan-2-yl]acetamide Chemical compound C=1C=CC=CC=1C(C)(NC(=O)CN)CC1=CC=C(Cl)C(Cl)=C1 TZLCPMQQJPNLGF-UHFFFAOYSA-N 0.000 claims 1
- JSHKGVUCSWHYEP-UHFFFAOYSA-N 2-amino-n-[1-(3-nitrophenyl)-2-phenylpropan-2-yl]acetamide Chemical compound C=1C=CC=CC=1C(C)(NC(=O)CN)CC1=CC=CC([N+]([O-])=O)=C1 JSHKGVUCSWHYEP-UHFFFAOYSA-N 0.000 claims 1
- TVYNMIHHCHCCIT-UHFFFAOYSA-N 2-amino-n-[1-(4-methoxyphenyl)-2-phenylpropan-2-yl]acetamide Chemical compound C1=CC(OC)=CC=C1CC(C)(NC(=O)CN)C1=CC=CC=C1 TVYNMIHHCHCCIT-UHFFFAOYSA-N 0.000 claims 1
- KMUAKMCZBRQLDH-UHFFFAOYSA-N 2-amino-n-[2-(2-chlorophenyl)-1-phenylpropan-2-yl]acetamide Chemical compound C=1C=CC=C(Cl)C=1C(C)(NC(=O)CN)CC1=CC=CC=C1 KMUAKMCZBRQLDH-UHFFFAOYSA-N 0.000 claims 1
- DDHGICMEAWDQNW-UHFFFAOYSA-N 2-amino-n-[2-(4-hydroxyphenyl)-1-phenylethyl]acetamide Chemical compound C=1C=CC=CC=1C(NC(=O)CN)CC1=CC=C(O)C=C1 DDHGICMEAWDQNW-UHFFFAOYSA-N 0.000 claims 1
- ILDUKVXLQQXAIV-UHFFFAOYSA-N 2-amino-n-[2-(4-hydroxyphenyl)-1-phenylpropan-2-yl]acetamide Chemical compound C=1C=C(O)C=CC=1C(C)(NC(=O)CN)CC1=CC=CC=C1 ILDUKVXLQQXAIV-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- 239000000243 solution Substances 0.000 description 51
- 239000007787 solid Substances 0.000 description 49
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- 239000002904 solvent Substances 0.000 description 41
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- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
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- 229940093915 gynecological organic acid Drugs 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000000971 hippocampal effect Effects 0.000 description 1
- 210000004295 hippocampal neuron Anatomy 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- YPGCWEMNNLXISK-UHFFFAOYSA-N hydratropic acid Chemical compound OC(=O)C(C)C1=CC=CC=C1 YPGCWEMNNLXISK-UHFFFAOYSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002527 isonitriles Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
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- 230000002045 lasting effect Effects 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 230000028161 membrane depolarization Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- GNMNPHPUCWQGJK-UHFFFAOYSA-N n-methyl-1,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(NC)CC1=CC=CC=C1 GNMNPHPUCWQGJK-UHFFFAOYSA-N 0.000 description 1
- WYRZZAHJLNGUTG-UHFFFAOYSA-N n-methyl-1,2-diphenylpropan-2-amine Chemical compound C=1C=CC=CC=1C(C)(NC)CC1=CC=CC=C1 WYRZZAHJLNGUTG-UHFFFAOYSA-N 0.000 description 1
- LDOJWMZOFZPNHJ-UHFFFAOYSA-N n-methyl-2-phenyl-1-pyridin-3-ylethanamine Chemical compound C=1C=CN=CC=1C(NC)CC1=CC=CC=C1 LDOJWMZOFZPNHJ-UHFFFAOYSA-N 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 208000031237 olivopontocerebellar atrophy Diseases 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 208000033300 perinatal asphyxia Diseases 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229960002695 phenobarbital Drugs 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ISYORFGKSZLPNW-UHFFFAOYSA-N propan-2-ylazanium;chloride Chemical compound [Cl-].CC(C)[NH3+] ISYORFGKSZLPNW-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006894 reductive elimination reaction Methods 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
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- 229920005989 resin Polymers 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
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- 239000012258 stirred mixture Substances 0.000 description 1
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- 230000009782 synaptic response Effects 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- 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
- C07C211/27—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 saturated carbon chains
-
- 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
- C07C211/29—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 the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- 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
- C07C215/52—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 two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified 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
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified 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 singly-bound oxygen atoms
- C07C217/60—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified 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 singly-bound oxygen atoms linked by carbon chains having two carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/10—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (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)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pyridine Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Fats And Perfumes (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US23256688A | 1988-08-12 | 1988-08-12 | |
PCT/GB1990/000184 WO1991011995A1 (en) | 1988-08-12 | 1990-02-07 | Arylalkyl-amines and -amides having anticonvulsant and neuroprotective properties |
Publications (3)
Publication Number | Publication Date |
---|---|
NO923006L NO923006L (no) | 1992-07-30 |
NO923006D0 NO923006D0 (no) | 1992-07-30 |
NO301974B1 true NO301974B1 (no) | 1998-01-05 |
Family
ID=22873660
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO923006A NO301974B1 (no) | 1988-08-12 | 1992-07-30 | Analogifremgangsmåte for fremstilling av terapeutisk aktive arylalkylaminer og -amider |
Country Status (19)
Country | Link |
---|---|
EP (3) | EP0648489A1 (pt) |
JP (2) | JP2846895B2 (pt) |
KR (1) | KR0169998B1 (pt) |
AT (1) | ATE135206T1 (pt) |
AU (1) | AU654802B2 (pt) |
CA (1) | CA1341136C (pt) |
DE (1) | DE68925933T2 (pt) |
DK (2) | DK175755B1 (pt) |
ES (1) | ES2083972T3 (pt) |
FI (1) | FI111712B (pt) |
GR (1) | GR3020407T3 (pt) |
HU (1) | HU211467A9 (pt) |
IE (3) | IE960775L (pt) |
LV (1) | LV11817B (pt) |
NO (1) | NO301974B1 (pt) |
PT (1) | PT91435B (pt) |
SG (1) | SG52662A1 (pt) |
WO (1) | WO1991011995A1 (pt) |
ZA (1) | ZA90878B (pt) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9320273D0 (en) * | 1993-04-01 | 1993-11-17 | Fisons Corp | Compound useful in therapy |
US5455259A (en) * | 1987-02-06 | 1995-10-03 | Fisons Corporation | Compounds for the treatment of neurodegenerative disorders |
ZA908490B (en) * | 1989-10-27 | 1991-07-31 | Fisons Corp | Use of arylalkylamides in the treatment of neurodegenerative diseases |
AU668682B2 (en) * | 1991-02-22 | 1996-05-16 | Howard K. Shapiro | Use of pharmaceutical compounds in the treatment of symptoms of disorders related to neurological diseases and etiologically related symptomology |
US5607935A (en) * | 1991-10-30 | 1997-03-04 | Fisons Corporation | 2-heterocyclicethylamine derivatives and their use as pharmaceuticals |
PL180014B1 (pl) * | 1992-04-03 | 2000-11-30 | Astra Ab | (S)- a-fenylo-2-pirydoetanoamina i kompozycja farmaceutyczna zawierajaca (S)- a-fenylo-2-pirydoetanoamine PL PL PL PL PL PL |
ZA942140B (en) * | 1993-04-01 | 1994-10-03 | Fisons Corp | Salt of (S)-alpha-phenyl-2-pyridineethanamine useful in therapy |
GB9410320D0 (en) * | 1994-05-24 | 1994-07-13 | Fisons Corp | Novel therapeutic method |
SE9901237D0 (sv) * | 1999-04-06 | 1999-04-06 | Astra Ab | Novel use |
US7659241B2 (en) | 2002-07-31 | 2010-02-09 | Seattle Genetics, Inc. | Drug conjugates and their use for treating cancer, an autoimmune disease or an infectious disease |
WO2007017652A2 (en) * | 2005-08-10 | 2007-02-15 | Astrazeneca Ab | Arylakylamines for the treatment of cancer |
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PT3066091T (pt) * | 2013-11-05 | 2019-07-11 | Astrazeneca Ab | Pro-farmacos de antagonista de nmda |
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US2503285A (en) * | 1945-10-18 | 1950-04-11 | Winthrop Stearns Inc | Beta-substituted alpha, beta-diphenylethylamines and the preparation thereof |
US2691680A (en) * | 1951-06-16 | 1954-10-12 | George A Breon And Company | N-methyl-1-(3-hydroxyphenyl)-2-phenylethylamine and addition salts thereof |
CH343388A (de) * | 1956-03-09 | 1959-12-31 | Cilag Chemie Aktiengesellschaf | Verfahren zur Herstellung neuer Amide |
NL128079C (pt) * | 1958-04-02 | |||
NL6512616A (pt) * | 1964-09-30 | 1966-03-31 | ||
ES484553A1 (es) * | 1978-10-05 | 1980-05-16 | Hoechst Ag | Un metodo para preparar 4-fenil-1,3-benzodiazepinas |
US4757076A (en) * | 1984-06-18 | 1988-07-12 | Eli Lilly And Company | Method of inhibiting aromatase |
HU207280B (en) * | 1986-09-25 | 1993-03-29 | Chinoin Gyogyszer Es Vegyeszet | Process for producing new phenyl-alkyl-amines and pharmaceutical compositions containing them |
GB9320273D0 (en) * | 1993-04-01 | 1993-11-17 | Fisons Corp | Compound useful in therapy |
US4798687A (en) * | 1987-02-06 | 1989-01-17 | Pennwalt Corporation | 2-Amino-N-[1,2-Diphenyl-1-(thifluoromethyl)ethyl]acetamide derivatives |
US4769466A (en) * | 1987-02-06 | 1988-09-06 | Pennwalt Corporation | 2-aminoacetamide pyridinyl derivatives |
IL84305A (en) * | 1987-02-06 | 1992-01-15 | Fisons Corp | 2-aminoacetamide derivatives |
EP0322582A3 (en) * | 1987-12-07 | 1989-09-13 | Hoechst-Roussel Pharmaceuticals Incorporated | 4-heteroaryl-1,3-benzodiazepines and 2-substituted-alpha-(heteroaryl)benzeneethanamines, a process for their preparation and their use us medicaments |
EP0401253A1 (en) * | 1988-01-20 | 1990-12-12 | Fisons Corporation | 2-amino acetamide derivatives |
GB8801883D0 (en) * | 1988-01-28 | 1988-02-24 | Oldham Crompton Batteries Ltd | Improvements in/relating to clamp reflectors |
ZA908490B (en) * | 1989-10-27 | 1991-07-31 | Fisons Corp | Use of arylalkylamides in the treatment of neurodegenerative diseases |
PL180014B1 (pl) * | 1992-04-03 | 2000-11-30 | Astra Ab | (S)- a-fenylo-2-pirydoetanoamina i kompozycja farmaceutyczna zawierajaca (S)- a-fenylo-2-pirydoetanoamine PL PL PL PL PL PL |
-
1989
- 1989-08-01 EP EP94119941A patent/EP0648489A1/en not_active Withdrawn
- 1989-08-01 EP EP89307815A patent/EP0356035B1/en not_active Expired - Lifetime
- 1989-08-01 ES ES89307815T patent/ES2083972T3/es not_active Expired - Lifetime
- 1989-08-01 EP EP94119942A patent/EP0648745A1/en not_active Withdrawn
- 1989-08-01 SG SG1996007517A patent/SG52662A1/en unknown
- 1989-08-01 AT AT89307815T patent/ATE135206T1/de not_active IP Right Cessation
- 1989-08-01 DE DE68925933T patent/DE68925933T2/de not_active Expired - Fee Related
- 1989-08-11 IE IE960775A patent/IE960775L/xx unknown
- 1989-08-11 JP JP1207062A patent/JP2846895B2/ja not_active Expired - Fee Related
- 1989-08-11 IE IE960774A patent/IE960774L/xx unknown
- 1989-08-11 CA CA000608107A patent/CA1341136C/en not_active Expired - Fee Related
- 1989-08-11 DK DK198903941A patent/DK175755B1/da not_active IP Right Cessation
- 1989-08-11 PT PT91435A patent/PT91435B/pt not_active IP Right Cessation
- 1989-08-11 IE IE259689A patent/IE74216B1/en not_active IP Right Cessation
-
1990
- 1990-02-06 ZA ZA90878A patent/ZA90878B/xx unknown
- 1990-02-07 AU AU50927/90A patent/AU654802B2/en not_active Ceased
- 1990-02-07 KR KR1019920701879A patent/KR0169998B1/ko not_active IP Right Cessation
- 1990-02-07 WO PCT/GB1990/000184 patent/WO1991011995A1/en active IP Right Grant
-
1992
- 1992-07-30 NO NO923006A patent/NO301974B1/no unknown
- 1992-08-06 FI FI923540A patent/FI111712B/fi active
-
1995
- 1995-06-12 HU HU95P/P00188P patent/HU211467A9/hu unknown
- 1995-07-05 DK DK078995A patent/DK78995A/da not_active Application Discontinuation
-
1996
- 1996-03-26 JP JP8069758A patent/JPH08291112A/ja active Pending
- 1996-06-12 GR GR960401582T patent/GR3020407T3/el unknown
-
1997
- 1997-03-13 LV LVP-97-40A patent/LV11817B/en unknown
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