UA73749C2 - Diarylenines - Google Patents
Diarylenines Download PDFInfo
- Publication number
- UA73749C2 UA73749C2 UA2002043703A UA2002043703A UA73749C2 UA 73749 C2 UA73749 C2 UA 73749C2 UA 2002043703 A UA2002043703 A UA 2002043703A UA 2002043703 A UA2002043703 A UA 2002043703A UA 73749 C2 UA73749 C2 UA 73749C2
- Authority
- UA
- Ukraine
- Prior art keywords
- phenyl
- penten
- sarcosine
- group
- usarcosine
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 125
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 58
- -1 heterocycloalkyloxy Chemical group 0.000 claims abstract description 39
- 125000001424 substituent group Chemical group 0.000 claims abstract description 29
- 125000003118 aryl group Chemical group 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000005000 thioaryl group Chemical group 0.000 claims abstract description 5
- 125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 4
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims abstract description 4
- 239000012453 solvate Substances 0.000 claims abstract description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 4
- 229940043230 sarcosine Drugs 0.000 claims description 168
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 74
- 238000000034 method Methods 0.000 claims description 48
- 239000004471 Glycine Substances 0.000 claims description 41
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 229910052700 potassium Inorganic materials 0.000 claims description 26
- 108010077895 Sarcosine Proteins 0.000 claims description 18
- 150000004820 halides Chemical class 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 230000003920 cognitive function Effects 0.000 claims description 5
- 201000010099 disease Diseases 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 229910052731 fluorine Chemical group 0.000 claims description 3
- 239000011737 fluorine Chemical group 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 229910052796 boron Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical group [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 1
- YNWDKZIIWCEDEE-UHFFFAOYSA-N pantoprazole sodium Chemical compound [Na+].COC1=CC=NC(CS(=O)C=2[N-]C3=CC=C(OC(F)F)C=C3N=2)=C1OC YNWDKZIIWCEDEE-UHFFFAOYSA-N 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract description 10
- 125000003710 aryl alkyl group Chemical group 0.000 abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 8
- 125000004001 thioalkyl group Chemical group 0.000 abstract description 7
- 125000005160 aryl oxy alkyl group Chemical group 0.000 abstract description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract description 4
- 125000001589 carboacyl group Chemical group 0.000 abstract description 4
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 description 89
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 78
- 239000003921 oil Substances 0.000 description 75
- 235000019198 oils Nutrition 0.000 description 75
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 108020003175 receptors Proteins 0.000 description 32
- 102000005962 receptors Human genes 0.000 description 32
- 239000007787 solid Substances 0.000 description 32
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 28
- 238000005481 NMR spectroscopy Methods 0.000 description 24
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 22
- 239000013067 intermediate product Substances 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 17
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- 238000012360 testing method Methods 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000012230 colorless oil Substances 0.000 description 15
- 239000003446 ligand Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 13
- 239000006260 foam Substances 0.000 description 13
- 230000027455 binding Effects 0.000 description 12
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- 238000004440 column chromatography Methods 0.000 description 12
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- 230000000694 effects Effects 0.000 description 10
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- PQJOSEVTIKYWLH-UHFFFAOYSA-N 1-iodo-4-propan-2-ylbenzene Chemical compound CC(C)C1=CC=C(I)C=C1 PQJOSEVTIKYWLH-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 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 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
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- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 230000001404 mediated effect Effects 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 108010032595 Antibody Binding Sites Proteins 0.000 description 6
- 108010078791 Carrier Proteins Proteins 0.000 description 6
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- 150000007513 acids Chemical class 0.000 description 6
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- 239000002858 neurotransmitter agent Substances 0.000 description 6
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- 102000011714 Glycine Receptors Human genes 0.000 description 5
- 108010076533 Glycine Receptors Proteins 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001503 aryl iodides Chemical class 0.000 description 5
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- 239000012528 membrane Substances 0.000 description 5
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
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- 239000011734 sodium Substances 0.000 description 5
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- WQVIVQDHNKQWTM-UHFFFAOYSA-N 1-tert-butyl-4-iodobenzene Chemical compound CC(C)(C)C1=CC=C(I)C=C1 WQVIVQDHNKQWTM-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
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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 4
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- JFGWPXKGINUNDH-UHFFFAOYSA-N methyl 3-phenylprop-2-ynoate Chemical compound COC(=O)C#CC1=CC=CC=C1 JFGWPXKGINUNDH-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
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- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
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- 238000011269 treatment regimen Methods 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
-
- 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
- A61P25/18—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/39—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton at least one of the nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom
- C07C323/40—Y being a hydrogen or a carbon atom
- C07C323/41—Y being a hydrogen or an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Confectionery (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline Compounds (AREA)
- Furan Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43102299A | 1999-11-01 | 1999-11-01 | |
| PCT/US2000/030074 WO2001032602A1 (en) | 1999-11-01 | 2000-11-01 | Diaryl-enynes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA73749C2 true UA73749C2 (en) | 2005-09-15 |
Family
ID=23710104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2002043703A UA73749C2 (en) | 1999-11-01 | 2000-01-11 | Diarylenines |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP1226108A4 (xx) |
| JP (1) | JP2003513063A (xx) |
| KR (1) | KR100702717B1 (xx) |
| CN (1) | CN100357274C (xx) |
| AU (1) | AU780922C (xx) |
| BG (1) | BG65275B1 (xx) |
| BR (1) | BR0015199A (xx) |
| CA (1) | CA2387660A1 (xx) |
| CZ (1) | CZ20021545A3 (xx) |
| EA (1) | EA004602B1 (xx) |
| EE (1) | EE05031B1 (xx) |
| HR (1) | HRP20020376A2 (xx) |
| HU (1) | HUP0203182A3 (xx) |
| IL (1) | IL149347A0 (xx) |
| MX (1) | MXPA02004354A (xx) |
| NO (1) | NO20021936L (xx) |
| NZ (1) | NZ529245A (xx) |
| PL (1) | PL355425A1 (xx) |
| SK (1) | SK6202002A3 (xx) |
| UA (1) | UA73749C2 (xx) |
| WO (1) | WO2001032602A1 (xx) |
| ZA (1) | ZA200203458B (xx) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04225953A (ja) * | 1990-05-07 | 1992-08-14 | Shionogi & Co Ltd | スピロ ジベンゾスベラン誘導体 |
| ATE136461T1 (de) * | 1990-08-13 | 1996-04-15 | Searle & Co | Verwendung von heterozyklischen aminoalkoholverbindungen zur herstellung eines medikaments für die behandlung von erkrankungen des zns |
| ATE320804T1 (de) * | 1995-12-07 | 2006-04-15 | Daniel C Javitt | Behandlung negativer und kognitiver symptome der schizophrenie mit antagonisten der glycinaufnahme |
| UA52698C2 (uk) * | 1996-10-04 | 2003-01-15 | Х. Луннбек А/С | Похідні (3-алкоксіізоксазол-4-іл)заміщеної 2-амінокарбонової кислоти та їх сірковмісні аналоги, фармацевтична композиція на їх основі |
| BR9907951A (pt) * | 1998-03-06 | 2001-01-30 | Janssen Pharmaceutica Nv | Inibidores de transporte de glicina |
| CA2322136A1 (en) * | 1998-03-06 | 1999-09-10 | Ludo Edmond Josephine Kennis | Glycine transport inhibitors |
| PE20000728A1 (es) * | 1998-06-26 | 2000-08-21 | Cocensys Inc | Heterociclos 4-bencil piperidina alquilsulfoxido y su uso como antagonistas receptores subtipo-selectivo nmda |
| US6103743A (en) * | 1999-08-06 | 2000-08-15 | Allelix Neuroscience, Inc. | Unsaturated amino acid derivatives |
-
2000
- 2000-01-11 UA UA2002043703A patent/UA73749C2/uk unknown
- 2000-11-01 CA CA002387660A patent/CA2387660A1/en not_active Abandoned
- 2000-11-01 AU AU14507/01A patent/AU780922C/en not_active Ceased
- 2000-11-01 HU HU0203182A patent/HUP0203182A3/hu unknown
- 2000-11-01 BR BR0015199-8A patent/BR0015199A/pt not_active Application Discontinuation
- 2000-11-01 JP JP2001534756A patent/JP2003513063A/ja active Pending
- 2000-11-01 SK SK620-2002A patent/SK6202002A3/sk unknown
- 2000-11-01 WO PCT/US2000/030074 patent/WO2001032602A1/en active IP Right Grant
- 2000-11-01 EP EP00976775A patent/EP1226108A4/en not_active Withdrawn
- 2000-11-01 MX MXPA02004354A patent/MXPA02004354A/es active IP Right Grant
- 2000-11-01 KR KR1020027005593A patent/KR100702717B1/ko not_active IP Right Cessation
- 2000-11-01 CZ CZ20021545A patent/CZ20021545A3/cs unknown
- 2000-11-01 EA EA200200521A patent/EA004602B1/ru not_active IP Right Cessation
- 2000-11-01 NZ NZ529245A patent/NZ529245A/en active Application Filing
- 2000-11-01 EE EEP200200229A patent/EE05031B1/xx not_active IP Right Cessation
- 2000-11-01 PL PL00355425A patent/PL355425A1/xx not_active IP Right Cessation
- 2000-11-01 CN CNB008151970A patent/CN100357274C/zh not_active Expired - Fee Related
- 2000-11-01 IL IL14934700A patent/IL149347A0/xx unknown
-
2002
- 2002-04-24 NO NO20021936A patent/NO20021936L/no not_active Application Discontinuation
- 2002-04-29 HR HR20020376A patent/HRP20020376A2/hr not_active Application Discontinuation
- 2002-04-30 ZA ZA200203458A patent/ZA200203458B/xx unknown
- 2002-04-30 BG BG106671A patent/BG65275B1/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU780922C (en) | 2005-10-20 |
| HUP0203182A2 (hu) | 2003-01-28 |
| KR100702717B1 (ko) | 2007-04-03 |
| HUP0203182A3 (en) | 2003-04-28 |
| IL149347A0 (en) | 2002-11-10 |
| MXPA02004354A (es) | 2003-10-06 |
| ZA200203458B (en) | 2003-10-29 |
| NO20021936L (no) | 2002-07-01 |
| EP1226108A4 (en) | 2004-06-16 |
| HRP20020376A2 (en) | 2004-02-29 |
| CA2387660A1 (en) | 2001-05-10 |
| WO2001032602A1 (en) | 2001-05-10 |
| PL355425A1 (en) | 2004-04-19 |
| NO20021936D0 (no) | 2002-04-24 |
| EA200200521A1 (ru) | 2002-10-31 |
| EA004602B1 (ru) | 2004-06-24 |
| EP1226108A1 (en) | 2002-07-31 |
| JP2003513063A (ja) | 2003-04-08 |
| BR0015199A (pt) | 2002-07-09 |
| SK6202002A3 (en) | 2002-10-08 |
| NZ529245A (en) | 2005-09-30 |
| EE05031B1 (et) | 2008-06-16 |
| CN100357274C (zh) | 2007-12-26 |
| AU1450701A (en) | 2001-05-14 |
| AU780922B2 (en) | 2005-04-28 |
| CZ20021545A3 (cs) | 2002-10-16 |
| BG65275B1 (bg) | 2007-11-30 |
| EE200200229A (et) | 2003-06-16 |
| KR20020060961A (ko) | 2002-07-19 |
| CN1387507A (zh) | 2002-12-25 |
| BG106671A (en) | 2003-02-28 |
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