ZA200305623B - Aniline derivatives useful as phosphodiesterase 4 inhibitors - Google Patents
Aniline derivatives useful as phosphodiesterase 4 inhibitors Download PDFInfo
- Publication number
- ZA200305623B ZA200305623B ZA2003/05623A ZA200305623A ZA200305623B ZA 200305623 B ZA200305623 B ZA 200305623B ZA 2003/05623 A ZA2003/05623 A ZA 2003/05623A ZA 200305623 A ZA200305623 A ZA 200305623A ZA 200305623 B ZA200305623 B ZA 200305623B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyridylmethyl
- diphenylamine
- methoxy
- cyclopentyloxy
- substituted
- Prior art date
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- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title description 6
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title 1
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 371
- -1 cyano, hydroxy Chemical group 0.000 claims description 201
- 125000000217 alkyl group Chemical group 0.000 claims description 193
- 125000004432 carbon atom Chemical group C* 0.000 claims description 160
- 229910052736 halogen Inorganic materials 0.000 claims description 148
- 150000002367 halogens Chemical class 0.000 claims description 136
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 112
- 150000001875 compounds Chemical class 0.000 claims description 111
- 125000003545 alkoxy group Chemical group 0.000 claims description 86
- 125000006413 ring segment Chemical group 0.000 claims description 73
- 125000004043 oxo group Chemical group O=* 0.000 claims description 71
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 54
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 48
- 239000000203 mixture Substances 0.000 claims description 44
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 33
- 125000003282 alkyl amino group Chemical group 0.000 claims description 32
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 229920006395 saturated elastomer Polymers 0.000 claims description 31
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 22
- 125000002837 carbocyclic group Chemical group 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 22
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- 125000002252 acyl group Chemical group 0.000 claims description 20
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 20
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 16
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 16
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 16
- 230000000694 effects Effects 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 125000004434 sulfur atom Chemical group 0.000 claims description 15
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 206010027175 memory impairment Diseases 0.000 claims description 12
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 11
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 102000004190 Enzymes Human genes 0.000 claims description 8
- 108090000790 Enzymes Proteins 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- YUCFVHQCAFKDQG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH] YUCFVHQCAFKDQG-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000019771 cognition Effects 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 5
- 125000005389 trialkylsiloxy group Chemical group 0.000 claims description 5
- 230000003247 decreasing effect Effects 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 230000002708 enhancing effect Effects 0.000 claims description 4
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 31
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 16
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 8
- 229920000728 polyester Polymers 0.000 claims 7
- 230000002265 prevention Effects 0.000 claims 7
- VTFYMSNCTVOXOQ-UHFFFAOYSA-N 3-[4-methoxy-3-(oxolan-3-yloxy)-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)C=C1OC1CCOC1 VTFYMSNCTVOXOQ-UHFFFAOYSA-N 0.000 claims 6
- PNIUJOQYAGLPHM-UHFFFAOYSA-N 3-[3-cyclopentyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)C=C1OC1CCCC1 PNIUJOQYAGLPHM-UHFFFAOYSA-N 0.000 claims 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 150000001412 amines Chemical class 0.000 claims 5
- 230000037396 body weight Effects 0.000 claims 5
- FDJBPHLXAYPMRF-UHFFFAOYSA-N 3-(3-cyclopentyloxy-4-methoxyanilino)benzoic acid Chemical compound C1=C(OC2CCCC2)C(OC)=CC=C1NC1=CC=CC(C(O)=O)=C1 FDJBPHLXAYPMRF-UHFFFAOYSA-N 0.000 claims 4
- RULLGLRZJAUWJC-UHFFFAOYSA-N 3-[3-(2,3-dihydro-1h-inden-2-yloxy)-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound C1=C(OC2CC3=CC=CC=C3C2)C(OC)=CC=C1N(C=1C=C(C=CC=1)C(O)=O)CC1=CC=CN=C1 RULLGLRZJAUWJC-UHFFFAOYSA-N 0.000 claims 4
- UGWWTKUPDVMIAT-UHFFFAOYSA-N 3-[3-(cyclopropylmethoxy)-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)C=C1OCC1CC1 UGWWTKUPDVMIAT-UHFFFAOYSA-N 0.000 claims 4
- XQVMANRSBUNGSR-UHFFFAOYSA-N 4-[3-(cyclopropylmethoxy)-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=CC(=CC=2)C(O)=O)C=C1OCC1CC1 XQVMANRSBUNGSR-UHFFFAOYSA-N 0.000 claims 4
- PFNVGWKABOYUIG-UHFFFAOYSA-N 4-[3-cyclopentyloxy-4-methoxy-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=CC(=CC=2)C(O)=O)C=C1OC1CCCC1 PFNVGWKABOYUIG-UHFFFAOYSA-N 0.000 claims 4
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 4
- LKEMHOKFBVYBFR-VQCQRNETSA-N N-[2-[(3R)-4-(difluoromethoxy)oxolan-3-yl]oxyphenyl]-N-(pyridin-3-ylmethyl)pyridin-3-amine Chemical compound FC(OC1[C@@H](COC1)OC1=C(C=CC=C1)N(CC=1C=NC=CC=1)C=1C=NC=CC=1)F LKEMHOKFBVYBFR-VQCQRNETSA-N 0.000 claims 4
- WZWGSXNVMJZJQG-UHFFFAOYSA-N n-(3-cyclopentyloxy-4-methoxyphenyl)-n-(pyridin-3-ylmethyl)pyridin-3-amine Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=NC=CC=2)C=C1OC1CCCC1 WZWGSXNVMJZJQG-UHFFFAOYSA-N 0.000 claims 4
- NHUAZXDSSJLSSR-UHFFFAOYSA-N n-[[3,4-bis(difluoromethoxy)-2h-pyridin-3-yl]methyl]-n-phenylaniline Chemical compound FC(F)OC1=CC=NCC1(OC(F)F)CN(C=1C=CC=CC=1)C1=CC=CC=C1 NHUAZXDSSJLSSR-UHFFFAOYSA-N 0.000 claims 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 4
- WNAODSRZKOTLRD-UHFFFAOYSA-N 3-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound OC(=O)C1=CC=CC(N(CC=2C=NC=CC=2)C=2C=C(OCC3CC3)C(OC(F)F)=CC=2)=C1 WNAODSRZKOTLRD-UHFFFAOYSA-N 0.000 claims 3
- YQCXOTXOYZMSGT-UHFFFAOYSA-N 3-[4-methoxy-3-(2-methoxyethoxy)-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound C1=C(OC)C(OCCOC)=CC(N(CC=2C=NC=CC=2)C=2C=C(C=CC=2)C(O)=O)=C1 YQCXOTXOYZMSGT-UHFFFAOYSA-N 0.000 claims 3
- LLJRXVHJOJRCSM-UHFFFAOYSA-N 3-pyridin-4-yl-1H-indole Chemical group C=1NC2=CC=CC=C2C=1C1=CC=NC=C1 LLJRXVHJOJRCSM-UHFFFAOYSA-N 0.000 claims 3
- 102000009346 Adenosine receptors Human genes 0.000 claims 3
- 108050000203 Adenosine receptors Proteins 0.000 claims 3
- 229940127291 Calcium channel antagonist Drugs 0.000 claims 3
- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 claims 3
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 claims 3
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- 101100082610 Plasmodium falciparum (isolate 3D7) PDEdelta gene Proteins 0.000 claims 3
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- KMMWYQNGITYSFV-UHFFFAOYSA-N n-[3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl]-n-(pyridin-3-ylmethyl)pyridin-3-amine Chemical compound FC(F)OC1=CC=C(N(CC=2C=NC=CC=2)C=2C=NC=CC=2)C=C1OCC1CC1 KMMWYQNGITYSFV-UHFFFAOYSA-N 0.000 claims 3
- DCWIRBQULCICSN-UHFFFAOYSA-N n-[3-cyclopentyloxy-4-(difluoromethoxy)phenyl]-n-(pyridin-3-ylmethyl)pyridin-3-amine Chemical compound FC(F)OC1=CC=C(N(CC=2C=NC=CC=2)C=2C=NC=CC=2)C=C1OC1CCCC1 DCWIRBQULCICSN-UHFFFAOYSA-N 0.000 claims 3
- OUMUNOWUXDBYMX-UHFFFAOYSA-N n-[[3-(cyclopropylmethoxy)-4-(difluoromethoxy)-2h-pyridin-3-yl]methyl]-n-phenylaniline Chemical compound FC(F)OC1=CC=NCC1(OCC1CC1)CN(C=1C=CC=CC=1)C1=CC=CC=C1 OUMUNOWUXDBYMX-UHFFFAOYSA-N 0.000 claims 3
- BOIVZFFQBGEXFX-UHFFFAOYSA-N n-[[4-methoxy-3-(2-pyridin-2-ylethoxy)-2h-pyridin-3-yl]methyl]-n-phenylaniline Chemical compound COC1=CC=NCC1(OCCC=1N=CC=CC=1)CN(C=1C=CC=CC=1)C1=CC=CC=C1 BOIVZFFQBGEXFX-UHFFFAOYSA-N 0.000 claims 3
- 239000008177 pharmaceutical agent Substances 0.000 claims 3
- QDAUEZSAGQJRSN-UHFFFAOYSA-N 3-[3-cyclopentyloxy-4-(difluoromethoxy)-n-(pyridin-3-ylmethyl)anilino]benzoic acid Chemical compound OC(=O)C1=CC=CC(N(CC=2C=NC=CC=2)C=2C=C(OC3CCCC3)C(OC(F)F)=CC=2)=C1 QDAUEZSAGQJRSN-UHFFFAOYSA-N 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
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- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 2
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- VGTXHUFPGAREKA-UHFFFAOYSA-N n-(3-cyclopentyloxy-4-methoxyphenyl)-n-(pyridin-3-ylmethyl)pyridin-2-amine Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2N=CC=CC=2)C=C1OC1CCCC1 VGTXHUFPGAREKA-UHFFFAOYSA-N 0.000 claims 2
- OSNHRDBNKUEDPF-UHFFFAOYSA-N n-(3-cyclopentyloxy-4-methoxyphenyl)-n-(pyridin-3-ylmethyl)pyrimidin-5-amine Chemical compound COC1=CC=C(N(CC=2C=NC=CC=2)C=2C=NC=NC=2)C=C1OC1CCCC1 OSNHRDBNKUEDPF-UHFFFAOYSA-N 0.000 claims 2
- MYSNBAJHBYMBNT-UHFFFAOYSA-N n-[(3-cyclopentyloxy-4-methoxy-2h-pyridin-3-yl)methyl]-n-phenylaniline Chemical compound COC1=CC=NCC1(OC1CCCC1)CN(C=1C=CC=CC=1)C1=CC=CC=C1 MYSNBAJHBYMBNT-UHFFFAOYSA-N 0.000 claims 2
- QVHODOMCMPUSNN-UHFFFAOYSA-N n-[[3-(2,3-dihydro-1h-inden-1-yloxy)-4-methoxy-2h-pyridin-3-yl]methyl]-n-phenylaniline Chemical compound COC1=CC=NCC1(OC1C2=CC=CC=C2CC1)CN(C=1C=CC=CC=1)C1=CC=CC=C1 QVHODOMCMPUSNN-UHFFFAOYSA-N 0.000 claims 2
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- AWSQSUXLWVZOFC-UHFFFAOYSA-N n-[[3-[2-(4-chlorophenyl)ethenoxy]-4-methoxy-2h-pyridin-3-yl]methyl]-n-phenylaniline Chemical compound COC1=CC=NCC1(OC=CC=1C=CC(Cl)=CC=1)CN(C=1C=CC=CC=1)C1=CC=CC=C1 AWSQSUXLWVZOFC-UHFFFAOYSA-N 0.000 claims 2
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 2
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- 125000003870 2-(1-piperidinyl)ethoxy group Chemical group [*]OC([H])([H])C([H])([H])N1C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
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- JZGBKXVQWKAUBX-UHFFFAOYSA-N 4-chloro-n-[2-[[4-methoxy-3-[(n-phenylanilino)methyl]-2h-pyridin-3-yl]oxy]ethyl]aniline Chemical compound COC1=CC=NCC1(OCCNC=1C=CC(Cl)=CC=1)CN(C=1C=CC=CC=1)C1=CC=CC=C1 JZGBKXVQWKAUBX-UHFFFAOYSA-N 0.000 claims 1
- JRJOWCAFOMTANO-UHFFFAOYSA-N 4-methoxy-3-[(n-phenylanilino)methyl]-2h-pyridin-3-ol Chemical compound COC1=CC=NCC1(O)CN(C=1C=CC=CC=1)C1=CC=CC=C1 JRJOWCAFOMTANO-UHFFFAOYSA-N 0.000 claims 1
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon 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
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen 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
- C07D333/26—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Virology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Oncology (AREA)
- AIDS & HIV (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US26265101P | 2001-01-22 | 2001-01-22 | |
US26719601P | 2001-02-08 | 2001-02-08 | |
US30614001P | 2001-07-19 | 2001-07-19 | |
PCT/US2002/001508 WO2002074726A2 (en) | 2001-01-22 | 2002-01-22 | Aniline derivatives useful as phosphodiesterase 4 inhibitors |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200305623B true ZA200305623B (en) | 2005-01-26 |
Family
ID=27401532
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA2003/05623A ZA200305623B (en) | 2001-01-22 | 2003-07-21 | Aniline derivatives useful as phosphodiesterase 4 inhibitors |
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Country | Link |
---|---|
EP (1) | EP1353907A2 (no) |
JP (1) | JP4223287B2 (no) |
KR (1) | KR100856622B1 (no) |
CN (1) | CN100378075C (no) |
AU (1) | AU2002303078B2 (no) |
BG (1) | BG108003A (no) |
BR (1) | BR0206943A (no) |
CA (1) | CA2435847A1 (no) |
CL (1) | CL2004001165A1 (no) |
CZ (1) | CZ20031986A3 (no) |
EE (1) | EE05362B1 (no) |
HK (1) | HK1066215A1 (no) |
HR (1) | HRP20030662A2 (no) |
HU (1) | HUP0302793A3 (no) |
IL (1) | IL156958A0 (no) |
MA (1) | MA25996A1 (no) |
MX (1) | MXPA03006519A (no) |
NO (1) | NO329548B1 (no) |
NZ (1) | NZ527081A (no) |
PL (1) | PL373301A1 (no) |
SK (1) | SK9152003A3 (no) |
WO (1) | WO2002074726A2 (no) |
YU (1) | YU57603A (no) |
ZA (1) | ZA200305623B (no) |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
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US7153871B2 (en) | 2001-01-22 | 2006-12-26 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors, including aminoindazole and aminobenzofuran analogs |
DE60233111D1 (de) * | 2001-02-14 | 2009-09-10 | Karobio Ab | Glucocorticoid-rezeptoren-modulatoren |
WO2004009552A1 (en) | 2002-07-19 | 2004-01-29 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors, including n-substituted aniline and diphenylamine analogs |
CN101423497A (zh) | 2002-07-19 | 2009-05-06 | 记忆药物公司 | 作为磷酸二酯酶4抑制剂的6-氨基-1h-吲唑和4-氨基苯并呋喃化合物 |
US7087625B2 (en) * | 2002-11-19 | 2006-08-08 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors |
AU2003286024A1 (en) * | 2002-11-22 | 2004-06-18 | Daniel Dube | Use of phosphodiesterase-4 inhibitors as enhancers of cognition |
CA2511502A1 (en) * | 2002-12-27 | 2004-07-15 | H. Lundbeck A/S | 1,2,4-triaminobenzene derivatives,useful for treating disorders of the central nervous system |
FR2856595B1 (fr) * | 2003-06-27 | 2008-05-30 | Exonhit Therapeutics Sa | Methodes et compositions pour le traitement de deficits cognitifs. |
US7776893B2 (en) | 2003-09-05 | 2010-08-17 | Nycomed Gmbh | Use of PDE4 inhibitors for the treatment of diabetes mellitus |
MY141255A (en) | 2003-12-11 | 2010-03-31 | Memory Pharm Corp | Phosphodiesterase 4 inhibitors, including n-substituted diarylamine analogs |
BRPI0513286A (pt) | 2004-07-15 | 2008-05-06 | Japan Tobacco Inc | compostos de benzamida condensada e inibidores de atividade de receptor vanilóide subtipo (vr1), suas composições farmacêuticas, pacote comercial, fármaco e respectivos usos |
US20070287716A1 (en) * | 2004-10-28 | 2007-12-13 | Hu Essa H | Pyrimidine and Quinoline Potentiators of Metabotropic Glutamate Receptors |
WO2006094933A1 (en) | 2005-03-08 | 2006-09-14 | Nycomed Gmbh | Roflumilast for the treatment of diabetes mellitus |
EP1888528A2 (en) * | 2005-06-10 | 2008-02-20 | Memory Pharmaceuticals Corporation | Phosphodiesterase 4 inhibitors |
AR057455A1 (es) * | 2005-07-22 | 2007-12-05 | Merck & Co Inc | Inhibidores de la transcriptasa reversa de vih y composicion farmaceutica |
US7906508B2 (en) | 2005-12-28 | 2011-03-15 | Japan Tobacco Inc. | 3,4-dihydrobenzoxazine compounds and inhibitors of vanilloid receptor subtype 1 (VRI) activity |
JP2010518064A (ja) | 2007-02-12 | 2010-05-27 | メルク・シャープ・エンド・ドーム・コーポレイション | Adおよび関連状態の治療のためのピペラジン誘導体 |
EP2110375A1 (en) * | 2008-04-14 | 2009-10-21 | CHIESI FARMACEUTICI S.p.A. | Phosphodiesterase-4 inhibitors belonging to the tertiary amine class |
US8461389B2 (en) | 2008-04-18 | 2013-06-11 | University College Dublin, National University Of Ireland, Dublin | Psycho-pharmaceuticals |
JP5542059B2 (ja) * | 2008-10-09 | 2014-07-09 | 国立大学法人 岡山大学 | Rxr作動性物質を有効成分とする抗アレルギー剤 |
US10253020B2 (en) | 2009-06-12 | 2019-04-09 | Abivax | Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging |
MX2019008390A (es) * | 2009-06-12 | 2019-09-09 | Abivax | Compuestos utiles para tratar cancer. |
WO2010143169A2 (en) | 2009-06-12 | 2010-12-16 | Société Splicos | Compounds useful for treating aids |
RU2569733C2 (ru) | 2010-02-12 | 2015-11-27 | Раквалиа Фарма Инк. | Агонисты 5-нт4-рецепторов для лечения деменции |
WO2013118855A1 (ja) | 2012-02-09 | 2013-08-15 | 塩野義製薬株式会社 | 複素環および炭素環誘導体 |
CN102603676B (zh) * | 2012-02-20 | 2014-02-12 | 徐江平 | 一种能避免呕吐反应的磷酸二酯酶4抑制剂 |
EP2826474B1 (en) * | 2012-03-14 | 2021-05-26 | Sinochem Corporation | Use of substituted diphenylamine compounds in preparing anti-tumour drugs |
EP2757161A1 (en) | 2013-01-17 | 2014-07-23 | Splicos | miRNA-124 as a biomarker of viral infection |
AU2014285733B2 (en) | 2013-07-05 | 2019-05-16 | Abivax | Bicyclic compounds useful for treating diseases caused by retroviruses |
US10357486B2 (en) | 2013-08-16 | 2019-07-23 | Universiteit Maastricht | Treatment of cognitive impairment with PDE4 inhibitor |
EP2974729A1 (en) | 2014-07-17 | 2016-01-20 | Abivax | Quinoline derivatives for use in the treatment of inflammatory diseases |
EP3669873A1 (en) | 2018-12-20 | 2020-06-24 | Abivax | Quinoline derivatives for use ine the traeatment of inflammation diseases |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH09501405A (ja) * | 1993-05-27 | 1997-02-10 | スミスクライン・ビーチャム・ラボラトワール・ファルマソーティク | 抗不整脈用n−置換3−ベンズアゼピンまたはイソキノリン |
JPH07206789A (ja) * | 1993-09-01 | 1995-08-08 | Taisho Pharmaceut Co Ltd | コンブレタスタチン類縁化合物 |
US5591776A (en) | 1994-06-24 | 1997-01-07 | Euro-Celtique, S.A. | Pheynl or benzyl-substituted rolipram-based compounds for and method of inhibiting phosphodiesterase IV |
FR2729142A1 (fr) * | 1995-01-06 | 1996-07-12 | Smithkline Beecham Lab | Nouvelles amines heterocycliques, leur procede de preparation et leur utilisation en tant que medicaments et notamment en tant qu'agents anti-arythmiques |
US6235736B1 (en) * | 1997-06-24 | 2001-05-22 | Nikken Chemicals Co., Ltd. | 3-anilino-2-cycloalkenone derivatives |
WO2000071129A1 (en) * | 1999-05-21 | 2000-11-30 | Bristol-Myers Squibb Company | Pyrrolotriazine inhibitors of kinases |
EP1116711B1 (de) * | 1999-12-18 | 2005-12-14 | Wella Aktiengesellschaft | 2-Aminoalkyl-1,4-diaminobenzol-Derivate und diese Verbindungen enthaltende Färbemittel |
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2002
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- 2002-01-22 EP EP02731078A patent/EP1353907A2/en not_active Withdrawn
- 2002-01-22 YU YU57603A patent/YU57603A/sh unknown
- 2002-01-22 KR KR1020037009624A patent/KR100856622B1/ko not_active IP Right Cessation
- 2002-01-22 JP JP2002573735A patent/JP4223287B2/ja not_active Expired - Fee Related
- 2002-01-22 MX MXPA03006519A patent/MXPA03006519A/es active IP Right Grant
- 2002-01-22 HU HU0302793A patent/HUP0302793A3/hu unknown
- 2002-01-22 CZ CZ20031986A patent/CZ20031986A3/cs unknown
- 2002-01-22 IL IL15695802A patent/IL156958A0/xx unknown
- 2002-01-22 BR BR0206943-1A patent/BR0206943A/pt not_active Application Discontinuation
- 2002-01-22 WO PCT/US2002/001508 patent/WO2002074726A2/en active Application Filing
- 2002-01-22 NZ NZ527081A patent/NZ527081A/xx unknown
- 2002-01-22 CA CA002435847A patent/CA2435847A1/en not_active Abandoned
- 2002-01-22 PL PL02373301A patent/PL373301A1/xx not_active Application Discontinuation
- 2002-01-22 EE EEP200300347A patent/EE05362B1/xx not_active IP Right Cessation
- 2002-01-22 CN CNB028070100A patent/CN100378075C/zh not_active Expired - Fee Related
- 2002-01-22 SK SK915-2003A patent/SK9152003A3/sk unknown
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2003
- 2003-07-18 BG BG108003A patent/BG108003A/bg unknown
- 2003-07-21 ZA ZA2003/05623A patent/ZA200305623B/en unknown
- 2003-07-21 NO NO20033288A patent/NO329548B1/no not_active IP Right Cessation
- 2003-07-22 MA MA27246A patent/MA25996A1/fr unknown
- 2003-08-20 HR HR20030662A patent/HRP20030662A2/hr not_active Application Discontinuation
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2004
- 2004-05-20 CL CL200401165A patent/CL2004001165A1/es unknown
- 2004-11-17 HK HK04109061A patent/HK1066215A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
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IL156958A0 (en) | 2004-02-08 |
BR0206943A (pt) | 2006-01-24 |
YU57603A (sh) | 2006-08-17 |
KR100856622B1 (ko) | 2008-09-03 |
CA2435847A1 (en) | 2002-09-26 |
BG108003A (bg) | 2004-09-30 |
HRP20030662A2 (en) | 2005-06-30 |
SK9152003A3 (en) | 2004-04-06 |
NO20033288D0 (no) | 2003-07-21 |
CN100378075C (zh) | 2008-04-02 |
MXPA03006519A (es) | 2004-10-15 |
NZ527081A (en) | 2006-03-31 |
JP4223287B2 (ja) | 2009-02-12 |
EP1353907A2 (en) | 2003-10-22 |
WO2002074726A2 (en) | 2002-09-26 |
NO20033288L (no) | 2003-09-22 |
CL2004001165A1 (es) | 2005-04-15 |
EE05362B1 (et) | 2010-12-15 |
NO329548B1 (no) | 2010-11-08 |
WO2002074726A3 (en) | 2003-03-13 |
JP2005507365A (ja) | 2005-03-17 |
KR20040064606A (ko) | 2004-07-19 |
MA25996A1 (fr) | 2003-12-31 |
EE200300347A (et) | 2003-12-15 |
HK1066215A1 (en) | 2005-03-18 |
CZ20031986A3 (cs) | 2003-12-17 |
HUP0302793A3 (en) | 2006-01-30 |
PL373301A1 (en) | 2005-08-22 |
CN1498211A (zh) | 2004-05-19 |
HUP0302793A2 (hu) | 2003-11-28 |
AU2002303078B2 (en) | 2007-08-30 |
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