EA004602B1 - Диариленины - Google Patents
Диариленины Download PDFInfo
- Publication number
- EA004602B1 EA004602B1 EA200200521A EA200200521A EA004602B1 EA 004602 B1 EA004602 B1 EA 004602B1 EA 200200521 A EA200200521 A EA 200200521A EA 200200521 A EA200200521 A EA 200200521A EA 004602 B1 EA004602 B1 EA 004602B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- phenyl
- sarcosine
- penten
- compound according
- alkyl
- Prior art date
Links
- 229940043230 sarcosine Drugs 0.000 claims abstract description 229
- -1 heterocycloalkyloxy Chemical group 0.000 claims abstract description 164
- 150000001875 compounds Chemical class 0.000 claims abstract description 135
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims abstract description 82
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 77
- 125000003118 aryl group Chemical group 0.000 claims abstract description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 44
- 239000004471 Glycine Substances 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 38
- 125000001424 substituent group Chemical group 0.000 claims abstract description 33
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 15
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 12
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 9
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
- 125000004001 thioalkyl group Chemical group 0.000 claims abstract description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 7
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 7
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims abstract description 6
- 125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 125000005000 thioaryl group Chemical group 0.000 claims abstract description 6
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims abstract description 5
- 239000004305 biphenyl Substances 0.000 claims abstract description 5
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 4
- 239000003937 drug carrier Substances 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
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims abstract 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 443
- 108010077895 Sarcosine Proteins 0.000 claims description 224
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 31
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 15
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 13
- 229910052700 potassium Inorganic materials 0.000 claims description 11
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 9
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 9
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 125000004864 4-thiomethylphenyl group Chemical group 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 229910052731 fluorine Chemical group 0.000 claims description 4
- 230000003920 cognitive function Effects 0.000 claims description 3
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
- 125000005338 substituted cycloalkoxy group Chemical group 0.000 claims 2
- 102000010410 Nogo Proteins Human genes 0.000 claims 1
- 108010077641 Nogo Proteins Proteins 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 abstract description 6
- 239000003112 inhibitor Substances 0.000 abstract description 4
- 125000005160 aryl oxy alkyl group Chemical group 0.000 abstract description 3
- 208000010877 cognitive disease Diseases 0.000 abstract description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract description 2
- KIGCTKNPXSPYMQ-XKZIYDEJSA-N 2-[[(e)-5-[4-(furan-3-yl)phenyl]-3-phenylpent-2-en-4-ynyl]-methylamino]acetic acid Chemical compound C=1C=CC=CC=1C(=C/CN(C)CC(O)=O)\C#CC(C=C1)=CC=C1C=1C=COC=1 KIGCTKNPXSPYMQ-XKZIYDEJSA-N 0.000 abstract 2
- VMUNXBUEOYOOAR-UHFFFAOYSA-N 2-[[3-(2-chlorophenyl)-5-(4-ethylphenyl)pent-2-en-4-ynyl]-methylamino]acetic acid Chemical compound C1=CC(CC)=CC=C1C#CC(=CCN(C)CC(O)=O)C1=CC=CC=C1Cl VMUNXBUEOYOOAR-UHFFFAOYSA-N 0.000 abstract 1
- UJACLHZGYAYKTK-UHFFFAOYSA-N 2-[[3-(2-chlorophenyl)-5-(4-propylphenyl)pent-2-en-4-ynyl]-methylamino]acetic acid Chemical compound C1=CC(CCC)=CC=C1C#CC(=CCN(C)CC(O)=O)C1=CC=CC=C1Cl UJACLHZGYAYKTK-UHFFFAOYSA-N 0.000 abstract 1
- ZDUHEAHMELDYHK-UHFFFAOYSA-N 2-[[3-(4-fluorophenyl)-5-(4-propan-2-ylphenyl)pent-2-en-4-ynyl]-methylamino]acetic acid 2-[methyl-[5-(4-propan-2-ylphenyl)-3-[4-(trifluoromethyl)phenyl]pent-2-en-4-ynyl]amino]acetic acid Chemical compound C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=C(C=C1)F.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=C(C=C1)C(F)(F)F ZDUHEAHMELDYHK-UHFFFAOYSA-N 0.000 abstract 1
- ZBUNUPLXGZUREY-UHFFFAOYSA-N 2-[[5-(1,3-benzodioxol-5-yl)-3-(3-fluorophenyl)pent-2-en-4-ynyl]-methylamino]acetic acid 2-[[3-(4-methoxyphenyl)-5-(4-propan-2-ylphenyl)pent-2-en-4-ynyl]-methylamino]acetic acid Chemical compound CN(CC=C(C#Cc1ccc2OCOc2c1)c1cccc(F)c1)CC(O)=O.COc1ccc(cc1)C(=CCN(C)CC(O)=O)C#Cc1ccc(cc1)C(C)C ZBUNUPLXGZUREY-UHFFFAOYSA-N 0.000 abstract 1
- AUSKEXIWZLFQBZ-UHFFFAOYSA-N 2-[[5-(4-benzylphenyl)-3-phenylpent-2-en-4-ynyl]-methylamino]acetic acid 2-[[5-(4-ethylphenyl)-3-phenylpent-2-en-4-ynyl]-methylamino]acetic acid 2-[methyl-[3-phenyl-5-[4-(trifluoromethyl)phenyl]pent-2-en-4-ynyl]amino]acetic acid Chemical compound C(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C(C1=CC=CC=C1)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.FC(C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1)(F)F AUSKEXIWZLFQBZ-UHFFFAOYSA-N 0.000 abstract 1
- LTGNCFCEPVIRRQ-UHFFFAOYSA-N 2-[[5-(4-chlorophenyl)-3-phenylpent-2-en-4-ynyl]-methylamino]acetic acid 2-[methyl-[3-phenyl-5-(4-propan-2-ylphenyl)pent-2-en-4-ynyl]amino]acetic acid Chemical compound C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.ClC1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 LTGNCFCEPVIRRQ-UHFFFAOYSA-N 0.000 abstract 1
- VKSQEFQZQGQCCF-UHFFFAOYSA-N 2-[methyl-[5-(4-methylphenyl)-3-phenylpent-2-en-4-ynyl]amino]acetic acid Chemical compound C=1C=CC=CC=1C(=CCN(C)CC(O)=O)C#CC1=CC=C(C)C=C1 VKSQEFQZQGQCCF-UHFFFAOYSA-N 0.000 abstract 1
- BORJBSBRKQHWRL-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=C(C=CC=C1)Cl.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=C(C=CC=C1)Cl Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=C(C=CC=C1)Cl.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=C(C=CC=C1)Cl BORJBSBRKQHWRL-UHFFFAOYSA-N 0.000 abstract 1
- FWLUAHUEIQLNKL-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=C(C=CC=C1)F.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=C(C=CC=C1)F Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=C(C=CC=C1)F.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=C(C=CC=C1)F FWLUAHUEIQLNKL-UHFFFAOYSA-N 0.000 abstract 1
- WGMDIMQMNPJQHF-UHFFFAOYSA-N C(C)(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=C(C=C1)Cl.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=C(C=C1)Cl Chemical compound C(C)(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=C(C=C1)Cl.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=C(C=C1)Cl WGMDIMQMNPJQHF-UHFFFAOYSA-N 0.000 abstract 1
- KZBRSMDVMITLTO-UHFFFAOYSA-N C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CSC=C1.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC(=CC=C1)F Chemical compound C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CSC=C1.C(C)(C)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC(=CC=C1)F KZBRSMDVMITLTO-UHFFFAOYSA-N 0.000 abstract 1
- AGMRWXNYRXGTON-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.O(C1=CC=CC=C1)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 Chemical compound C1(=CC=CC2=CC=CC=C12)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.O(C1=CC=CC=C1)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 AGMRWXNYRXGTON-UHFFFAOYSA-N 0.000 abstract 1
- YGTRJOGPGUOVHV-UHFFFAOYSA-N C1(=CC=CC=C1)C(=CCN(C)CC(=O)O)C#CC1=CC=CC=C1.FC(C=1C=C(C=C(C1)C(F)(F)F)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1)(F)F Chemical compound C1(=CC=CC=C1)C(=CCN(C)CC(=O)O)C#CC1=CC=CC=C1.FC(C=1C=C(C=C(C1)C(F)(F)F)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1)(F)F YGTRJOGPGUOVHV-UHFFFAOYSA-N 0.000 abstract 1
- MRAGRIYHJYUMQZ-UHFFFAOYSA-N CC=1C=C(C=CC1C)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C1=C(C=CC2=CC=CC=C12)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C(C)(C)C=1C=C(C=CC1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 Chemical compound CC=1C=C(C=CC1C)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C1=C(C=CC2=CC=CC=C12)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C(C)(C)C=1C=C(C=CC1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 MRAGRIYHJYUMQZ-UHFFFAOYSA-N 0.000 abstract 1
- QGCVRYRLRVVMSF-UHFFFAOYSA-N COC=1C=C(C=CC1OC)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.FC(OC1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1)(F)F Chemical compound COC=1C=C(C=CC1OC)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.FC(OC1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1)(F)F QGCVRYRLRVVMSF-UHFFFAOYSA-N 0.000 abstract 1
- XRFPOAAGUBVQEP-UHFFFAOYSA-N FC1=C(C=CC(=C1)F)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.FC1=C(C=CC=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.FC1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 Chemical compound FC1=C(C=CC(=C1)F)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.FC1=C(C=CC=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.FC1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 XRFPOAAGUBVQEP-UHFFFAOYSA-N 0.000 abstract 1
- SYBRNLPEAJXMNU-UHFFFAOYSA-N N1C(=CC=C1)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C1OC=2C=C(C=CC2O1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C(C)(C)C1=C(C=CC=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 Chemical compound N1C(=CC=C1)C1=CC=C(C=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C1OC=2C=C(C=CC2O1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1.C(C)(C)C1=C(C=CC=C1)C#CC(=CCN(C)CC(=O)O)C1=CC=CC=C1 SYBRNLPEAJXMNU-UHFFFAOYSA-N 0.000 abstract 1
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 71
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
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- 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
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- 108010078791 Carrier Proteins Proteins 0.000 description 7
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- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 7
- 102100030413 Spermidine synthase Human genes 0.000 description 7
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
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- 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
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- 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
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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
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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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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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
- A61P25/28—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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- 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
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- 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
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- 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
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- 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
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- 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
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- 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)
- Furan Compounds (AREA)
- Pyrrole Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Quinoline 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 (2)
| Publication Number | Publication Date |
|---|---|
| EA200200521A1 EA200200521A1 (ru) | 2002-10-31 |
| EA004602B1 true EA004602B1 (ru) | 2004-06-24 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200200521A EA004602B1 (ru) | 1999-11-01 | 2000-11-01 | Диариленины |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP1226108A4 (cs) |
| JP (1) | JP2003513063A (cs) |
| KR (1) | KR100702717B1 (cs) |
| CN (1) | CN100357274C (cs) |
| AU (1) | AU780922C (cs) |
| BG (1) | BG65275B1 (cs) |
| BR (1) | BR0015199A (cs) |
| CA (1) | CA2387660A1 (cs) |
| CZ (1) | CZ20021545A3 (cs) |
| EA (1) | EA004602B1 (cs) |
| EE (1) | EE05031B1 (cs) |
| HR (1) | HRP20020376A2 (cs) |
| HU (1) | HUP0203182A3 (cs) |
| IL (1) | IL149347A0 (cs) |
| MX (1) | MXPA02004354A (cs) |
| NO (1) | NO20021936L (cs) |
| NZ (1) | NZ529245A (cs) |
| PL (1) | PL355425A1 (cs) |
| SK (1) | SK6202002A3 (cs) |
| UA (1) | UA73749C2 (cs) |
| WO (1) | WO2001032602A1 (cs) |
| ZA (1) | ZA200203458B (cs) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| CA2087449A1 (en) * | 1990-08-13 | 1992-02-14 | Joseph L. Roba | Use of heterocyclic amino-alcohol compounds for treatment of cns diseases |
| EP0871440B1 (en) * | 1995-12-07 | 2006-03-22 | Daniel C. Javitt | Treatment of negative and cognitive symptoms of schizophrenia with glycine uptake antagonists |
| 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 |
| AU3254499A (en) * | 1998-03-06 | 1999-09-20 | Janssen Pharmaceutica N.V. | Glycine transport inhibitors |
| HRP20000523A2 (en) * | 1998-03-06 | 2001-02-28 | Janssen Pharmaceutica Nv | 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 |
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2000
- 2000-01-11 UA UA2002043703A patent/UA73749C2/uk unknown
- 2000-11-01 JP JP2001534756A patent/JP2003513063A/ja active Pending
- 2000-11-01 SK SK620-2002A patent/SK6202002A3/sk unknown
- 2000-11-01 BR BR0015199-8A patent/BR0015199A/pt not_active Application Discontinuation
- 2000-11-01 HR HR20020376A patent/HRP20020376A2/hr not_active Application Discontinuation
- 2000-11-01 EP EP00976775A patent/EP1226108A4/en not_active Withdrawn
- 2000-11-01 EA EA200200521A patent/EA004602B1/ru not_active IP Right Cessation
- 2000-11-01 CA CA002387660A patent/CA2387660A1/en not_active Abandoned
- 2000-11-01 EE EEP200200229A patent/EE05031B1/xx not_active IP Right Cessation
- 2000-11-01 AU AU14507/01A patent/AU780922C/en not_active Ceased
- 2000-11-01 IL IL14934700A patent/IL149347A0/xx unknown
- 2000-11-01 CZ CZ20021545A patent/CZ20021545A3/cs unknown
- 2000-11-01 WO PCT/US2000/030074 patent/WO2001032602A1/en not_active Ceased
- 2000-11-01 PL PL00355425A patent/PL355425A1/xx not_active IP Right Cessation
- 2000-11-01 NZ NZ529245A patent/NZ529245A/en active Application Filing
- 2000-11-01 CN CNB008151970A patent/CN100357274C/zh not_active Expired - Fee Related
- 2000-11-01 KR KR1020027005593A patent/KR100702717B1/ko not_active Expired - Fee Related
- 2000-11-01 MX MXPA02004354A patent/MXPA02004354A/es active IP Right Grant
- 2000-11-01 HU HU0203182A patent/HUP0203182A3/hu unknown
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2002
- 2002-04-24 NO NO20021936A patent/NO20021936L/no not_active Application Discontinuation
- 2002-04-30 BG BG106671A patent/BG65275B1/bg unknown
- 2002-04-30 ZA ZA200203458A patent/ZA200203458B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1226108A4 (en) | 2004-06-16 |
| NO20021936D0 (no) | 2002-04-24 |
| BG106671A (en) | 2003-02-28 |
| HUP0203182A2 (hu) | 2003-01-28 |
| CN100357274C (zh) | 2007-12-26 |
| CZ20021545A3 (cs) | 2002-10-16 |
| AU780922C (en) | 2005-10-20 |
| EE05031B1 (et) | 2008-06-16 |
| SK6202002A3 (en) | 2002-10-08 |
| NO20021936L (no) | 2002-07-01 |
| JP2003513063A (ja) | 2003-04-08 |
| KR20020060961A (ko) | 2002-07-19 |
| AU1450701A (en) | 2001-05-14 |
| CA2387660A1 (en) | 2001-05-10 |
| IL149347A0 (en) | 2002-11-10 |
| NZ529245A (en) | 2005-09-30 |
| HRP20020376A2 (en) | 2004-02-29 |
| HUP0203182A3 (en) | 2003-04-28 |
| MXPA02004354A (es) | 2003-10-06 |
| WO2001032602A1 (en) | 2001-05-10 |
| PL355425A1 (en) | 2004-04-19 |
| BG65275B1 (bg) | 2007-11-30 |
| CN1387507A (zh) | 2002-12-25 |
| EP1226108A1 (en) | 2002-07-31 |
| UA73749C2 (en) | 2005-09-15 |
| BR0015199A (pt) | 2002-07-09 |
| KR100702717B1 (ko) | 2007-04-03 |
| EA200200521A1 (ru) | 2002-10-31 |
| EE200200229A (et) | 2003-06-16 |
| ZA200203458B (en) | 2003-10-29 |
| AU780922B2 (en) | 2005-04-28 |
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| Date | Code | Title | Description |
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| PC4A | Registration of transfer of a eurasian patent by assignment | ||
| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |