JP2008516982A5 - - Google Patents
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- Publication number
- JP2008516982A5 JP2008516982A5 JP2007537010A JP2007537010A JP2008516982A5 JP 2008516982 A5 JP2008516982 A5 JP 2008516982A5 JP 2007537010 A JP2007537010 A JP 2007537010A JP 2007537010 A JP2007537010 A JP 2007537010A JP 2008516982 A5 JP2008516982 A5 JP 2008516982A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- aminopropyl
- difluorophenyl
- thiadiazol
- fluorophenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 44
- 125000000217 alkyl group Chemical group 0.000 claims 41
- 125000003118 aryl group Chemical group 0.000 claims 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims 36
- 125000001072 heteroaryl group Chemical group 0.000 claims 32
- 125000003342 alkenyl group Chemical group 0.000 claims 26
- 125000000304 alkynyl group Chemical group 0.000 claims 26
- -1 cycloalkynyl Chemical group 0.000 claims 26
- 229920006395 saturated elastomer Polymers 0.000 claims 26
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 23
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 17
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 16
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 16
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 14
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 14
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 13
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 13
- 125000004043 oxo group Chemical group O=* 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- BPXYEYJNCXITEY-UHFFFAOYSA-N diazonio(trifluoromethoxy)azanide Chemical compound FC(F)(F)ON=[N+]=[N-] BPXYEYJNCXITEY-UHFFFAOYSA-N 0.000 claims 9
- 208000035475 disorder Diseases 0.000 claims 8
- 125000005842 heteroatom Chemical group 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 229910052717 sulfur Inorganic materials 0.000 claims 6
- 201000010099 disease Diseases 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 4
- 230000002159 abnormal effect Effects 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 241001465754 Metazoa Species 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 150000001413 amino acids Chemical class 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 230000010261 cell growth Effects 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 230000011278 mitosis Effects 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000001544 thienyl group Chemical group 0.000 claims 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 3
- LLXISKGBWFTGEI-UHFFFAOYSA-N 2-(3-aminopropyl)-5-(2,5-difluorophenyl)-n-methoxy-n-methyl-2-phenyl-1,3,4-thiadiazole-3-carboxamide Chemical compound CON(C)C(=O)N1N=C(C=2C(=CC=C(F)C=2)F)SC1(CCCN)C1=CC=CC=C1 LLXISKGBWFTGEI-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
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000004419 alkynylene group Chemical group 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 150000001540 azides Chemical class 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 125000002837 carbocyclic group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000002538 fungal effect Effects 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 230000003463 hyperproliferative effect Effects 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 239000000651 prodrug Substances 0.000 claims 2
- 229940002612 prodrug Drugs 0.000 claims 2
- 230000035755 proliferation Effects 0.000 claims 2
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 2
- FRNUVXGMPOTVLK-SPLOXXLWSA-N (2r)-1-[(2r)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-methoxypropan-1-one Chemical compound C1([C@@]2(CCCN)SC(=NN2C(=O)[C@@H](C)OC)C=2C(=CC=C(F)C=2)F)=CC=CC=C1 FRNUVXGMPOTVLK-SPLOXXLWSA-N 0.000 claims 1
- FRNUVXGMPOTVLK-SZNDQCEHSA-N (2r)-1-[(2s)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-methoxypropan-1-one Chemical compound C1([C@]2(CCCN)SC(=NN2C(=O)[C@@H](C)OC)C=2C(=CC=C(F)C=2)F)=CC=CC=C1 FRNUVXGMPOTVLK-SZNDQCEHSA-N 0.000 claims 1
- XIWYDLDSTPLOKM-QMRFKDRMSA-N (2r)-1-[2-(3-aminopropyl)-5-(3-fluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-hydroxypropan-1-one Chemical compound C[C@@H](O)C(=O)N1N=C(C=2C=C(F)C=CC=2)SC1(CCCN)C1=CC=CC=C1 XIWYDLDSTPLOKM-QMRFKDRMSA-N 0.000 claims 1
- CIWTVTAHSWFCGR-RBFZIWAESA-N (2r)-1-[2-(3-aminopropyl)-5-(3-fluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-methoxypropan-1-one Chemical compound CO[C@H](C)C(=O)N1N=C(C=2C=C(F)C=CC=2)SC1(CCCN)C1=CC=CC=C1 CIWTVTAHSWFCGR-RBFZIWAESA-N 0.000 claims 1
- AEWGLQSXTHRVBI-SIKLNZKXSA-N (2s)-1-[(2r)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-hydroxy-3-methylbutan-1-one Chemical compound C1([C@@]2(CCCN)SC(=NN2C(=O)[C@@H](O)C(C)C)C=2C(=CC=C(F)C=2)F)=CC=CC=C1 AEWGLQSXTHRVBI-SIKLNZKXSA-N 0.000 claims 1
- XBWDDRWBRPHXMA-GHTZIAJQSA-N (2s)-1-[(2r)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-hydroxybutan-1-one Chemical compound C1([C@@]2(CCCN)SC(=NN2C(=O)[C@@H](O)CC)C=2C(=CC=C(F)C=2)F)=CC=CC=C1 XBWDDRWBRPHXMA-GHTZIAJQSA-N 0.000 claims 1
- VONBTAYFUNQJER-NZQKXSOJSA-N (2s)-1-[(2r)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-methoxy-3-methylbutan-1-one Chemical compound C1([C@@]2(CCCN)SC(=NN2C(=O)[C@H](C(C)C)OC)C=2C(=CC=C(F)C=2)F)=CC=CC=C1 VONBTAYFUNQJER-NZQKXSOJSA-N 0.000 claims 1
- HYKHLUYANVECQN-SIKLNZKXSA-N (2s)-1-[(2r)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-methoxybutan-1-one Chemical compound C1([C@@]2(CCCN)SC(=NN2C(=O)[C@@H](OC)CC)C=2C(=CC=C(F)C=2)F)=CC=CC=C1 HYKHLUYANVECQN-SIKLNZKXSA-N 0.000 claims 1
- FRNUVXGMPOTVLK-LHSJRXKWSA-N (2s)-1-[(2r)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-methoxypropan-1-one Chemical compound C1([C@@]2(CCCN)SC(=NN2C(=O)[C@H](C)OC)C=2C(=CC=C(F)C=2)F)=CC=CC=C1 FRNUVXGMPOTVLK-LHSJRXKWSA-N 0.000 claims 1
- KNSRALLOUBTTQK-BUXKBTBVSA-N (2s)-1-[(2r)-5-(2,5-difluorophenyl)-2-(hydroxymethyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-methoxypropan-1-one Chemical compound C1([C@]2(CO)SC(=NN2C(=O)[C@H](C)OC)C=2C(=CC=C(F)C=2)F)=CC=CC=C1 KNSRALLOUBTTQK-BUXKBTBVSA-N 0.000 claims 1
- DYBVBGCOGRBTLZ-QKKBWIMNSA-N (2s)-1-[(2r)-5-(2,5-difluorophenyl)-2-(methoxymethoxymethyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-methoxypropan-1-one Chemical compound S([C@@](N(N=1)C(=O)[C@H](C)OC)(COCOC)C=2C=CC=CC=2)C=1C1=CC(F)=CC=C1F DYBVBGCOGRBTLZ-QKKBWIMNSA-N 0.000 claims 1
- AEWGLQSXTHRVBI-UGKGYDQZSA-N (2s)-1-[(2s)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-hydroxy-3-methylbutan-1-one Chemical compound C1([C@]2(CCCN)SC(=NN2C(=O)[C@@H](O)C(C)C)C=2C(=CC=C(F)C=2)F)=CC=CC=C1 AEWGLQSXTHRVBI-UGKGYDQZSA-N 0.000 claims 1
- XPIJDDVTGGBUNR-RBZFPXEDSA-N (2s)-1-[(2s)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-hydroxypropan-1-one Chemical compound C1([C@]2(CCCN)SC(=NN2C(=O)[C@@H](O)C)C=2C(=CC=C(F)C=2)F)=CC=CC=C1 XPIJDDVTGGBUNR-RBZFPXEDSA-N 0.000 claims 1
- VONBTAYFUNQJER-REWPJTCUSA-N (2s)-1-[(2s)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-methoxy-3-methylbutan-1-one Chemical compound C1([C@]2(CCCN)SC(=NN2C(=O)[C@H](C(C)C)OC)C=2C(=CC=C(F)C=2)F)=CC=CC=C1 VONBTAYFUNQJER-REWPJTCUSA-N 0.000 claims 1
- CIWTVTAHSWFCGR-BTYIYWSLSA-N (2s)-1-[(2s)-2-(3-aminopropyl)-5-(3-fluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-methoxypropan-1-one Chemical compound C1([C@]2(CCCN)SC(=NN2C(=O)[C@H](C)OC)C=2C=C(F)C=CC=2)=CC=CC=C1 CIWTVTAHSWFCGR-BTYIYWSLSA-N 0.000 claims 1
- DYBVBGCOGRBTLZ-LHSJRXKWSA-N (2s)-1-[(2s)-5-(2,5-difluorophenyl)-2-(methoxymethoxymethyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-methoxypropan-1-one Chemical compound S([C@](N(N=1)C(=O)[C@H](C)OC)(COCOC)C=2C=CC=CC=2)C=1C1=CC(F)=CC=C1F DYBVBGCOGRBTLZ-LHSJRXKWSA-N 0.000 claims 1
- VFQYYEDDJRNXNQ-JRTLGTJJSA-N (2s)-1-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-(3-fluorophenyl)-1,3,4-thiadiazol-3-yl]-2-methoxypropan-1-one Chemical compound CO[C@@H](C)C(=O)N1N=C(C=2C(=CC=C(F)C=2)F)SC1(CCCN)C1=CC=CC(F)=C1 VFQYYEDDJRNXNQ-JRTLGTJJSA-N 0.000 claims 1
- HHEIQZQTZYSSIL-SVZXGPMESA-N (2s)-1-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-(3-hydroxyphenyl)-1,3,4-thiadiazol-3-yl]-2-hydroxypropan-1-one Chemical compound C[C@H](O)C(=O)N1N=C(C=2C(=CC=C(F)C=2)F)SC1(CCCN)C1=CC=CC(O)=C1 HHEIQZQTZYSSIL-SVZXGPMESA-N 0.000 claims 1
- HPRIHYIELCEOTQ-YXWRBFHGSA-N (2s)-1-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-oxadiazol-3-yl]-2-methoxypropan-1-one Chemical compound CO[C@@H](C)C(=O)N1N=C(C=2C(=CC=C(F)C=2)F)OC1(CCCN)C1=CC=CC=C1 HPRIHYIELCEOTQ-YXWRBFHGSA-N 0.000 claims 1
- FRNUVXGMPOTVLK-YXWRBFHGSA-N (2s)-1-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-methoxypropan-1-one Chemical compound CO[C@@H](C)C(=O)N1N=C(C=2C(=CC=C(F)C=2)F)SC1(CCCN)C1=CC=CC=C1 FRNUVXGMPOTVLK-YXWRBFHGSA-N 0.000 claims 1
- SYIRUFUVCJSTPC-UEDXYCIISA-N (2s)-1-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-methylbutan-1-one Chemical compound CC[C@H](C)C(=O)N1N=C(C=2C(=CC=C(F)C=2)F)SC1(CCCN)C1=CC=CC=C1 SYIRUFUVCJSTPC-UEDXYCIISA-N 0.000 claims 1
- HAXWEAUTCXQZFB-ZDGMYTEDSA-N (2s)-1-[2-(3-aminopropyl)-5-(3-chlorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-methoxypropan-1-one Chemical compound CO[C@@H](C)C(=O)N1N=C(C=2C=C(Cl)C=CC=2)SC1(CCCN)C1=CC=CC=C1 HAXWEAUTCXQZFB-ZDGMYTEDSA-N 0.000 claims 1
- CIWTVTAHSWFCGR-ZDGMYTEDSA-N (2s)-1-[2-(3-aminopropyl)-5-(3-fluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-methoxypropan-1-one Chemical compound CO[C@@H](C)C(=O)N1N=C(C=2C=C(F)C=CC=2)SC1(CCCN)C1=CC=CC=C1 CIWTVTAHSWFCGR-ZDGMYTEDSA-N 0.000 claims 1
- ABFQWYWPCAIFHQ-NAEPXGHHSA-N (2s)-2-amino-n-[(2s)-1-[3-[(2s)-5-(2,5-difluorophenyl)-3-[(2s)-2-methoxypropanoyl]-2-phenyl-1,3,4-thiadiazol-2-yl]propylamino]-1-oxopropan-2-yl]propanamide Chemical compound C1([C@]2(CCCNC(=O)[C@H](C)NC(=O)[C@H](C)N)SC(=NN2C(=O)[C@H](C)OC)C=2C(=CC=C(F)C=2)F)=CC=CC=C1 ABFQWYWPCAIFHQ-NAEPXGHHSA-N 0.000 claims 1
- AHMGNDVKKUVOSC-UHFFFAOYSA-N 1-[2-(3-aminopropyl)-2-(4-bromophenyl)-5-(2,5-difluorophenyl)-1,3,4-oxadiazol-3-yl]-2,2-dimethylpropan-1-one;dihydrochloride Chemical compound Cl.Cl.CC(C)(C)C(=O)N1N=C(C=2C(=CC=C(F)C=2)F)OC1(CCCN)C1=CC=C(Br)C=C1 AHMGNDVKKUVOSC-UHFFFAOYSA-N 0.000 claims 1
- UBJILDGKKBSMRP-UHFFFAOYSA-N 1-[2-(3-aminopropyl)-2-(4-chlorophenyl)-5-(2,5-difluorophenyl)-1,3,4-oxadiazol-3-yl]-2,2-dimethylpropan-1-one;dihydrochloride Chemical compound Cl.Cl.CC(C)(C)C(=O)N1N=C(C=2C(=CC=C(F)C=2)F)OC1(CCCN)C1=CC=C(Cl)C=C1 UBJILDGKKBSMRP-UHFFFAOYSA-N 0.000 claims 1
- YKYBCQQJFUKWSZ-UHFFFAOYSA-N 1-[2-(3-aminopropyl)-2-(4-tert-butylphenyl)-5-(2,5-difluorophenyl)-1,3,4-oxadiazol-3-yl]-2,2-dimethylpropan-1-one Chemical compound CC(C)(C)C(=O)N1N=C(C=2C(=CC=C(F)C=2)F)OC1(CCCN)C1=CC=C(C(C)(C)C)C=C1 YKYBCQQJFUKWSZ-UHFFFAOYSA-N 0.000 claims 1
- LPBLLPBVCFITEK-UHFFFAOYSA-N 1-[2-(3-aminopropyl)-2-phenyl-5-thiophen-2-yl-1,3,4-oxadiazol-3-yl]-2,2-dimethylpropan-1-one;dihydrochloride Chemical compound Cl.Cl.CC(C)(C)C(=O)N1N=C(C=2SC=CC=2)OC1(CCCN)C1=CC=CC=C1 LPBLLPBVCFITEK-UHFFFAOYSA-N 0.000 claims 1
- PNFOPYHPIWUQPF-UHFFFAOYSA-N 1-[2-(3-aminopropyl)-5-(2,5-dichlorophenyl)-2-phenyl-1,3,4-oxadiazol-3-yl]-2,2-dimethylpropan-1-one;dihydrochloride Chemical compound Cl.Cl.CC(C)(C)C(=O)N1N=C(C=2C(=CC=C(Cl)C=2)Cl)OC1(CCCN)C1=CC=CC=C1 PNFOPYHPIWUQPF-UHFFFAOYSA-N 0.000 claims 1
- RGPFVDYFBVGQLP-UHFFFAOYSA-N 1-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-(3-fluorophenyl)-1,3,4-thiadiazol-3-yl]-2-methylpropan-1-one Chemical compound CC(C)C(=O)N1N=C(C=2C(=CC=C(F)C=2)F)SC1(CCCN)C1=CC=CC(F)=C1 RGPFVDYFBVGQLP-UHFFFAOYSA-N 0.000 claims 1
- UVTWRKCKEQPAQV-UHFFFAOYSA-N 1-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-(3-fluorophenyl)-1,3,4-thiadiazol-3-yl]ethanone Chemical compound CC(=O)N1N=C(C=2C(=CC=C(F)C=2)F)SC1(CCCN)C1=CC=CC(F)=C1 UVTWRKCKEQPAQV-UHFFFAOYSA-N 0.000 claims 1
- JTAXCDZFPFOGGA-UHFFFAOYSA-N 1-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-(3-methylphenyl)-1,3,4-oxadiazol-3-yl]-2,2-dimethylpropan-1-one;dihydrochloride Chemical compound Cl.Cl.CC1=CC=CC(C2(CCCN)N(N=C(O2)C=2C(=CC=C(F)C=2)F)C(=O)C(C)(C)C)=C1 JTAXCDZFPFOGGA-UHFFFAOYSA-N 0.000 claims 1
- SAWPHAVUWBUYTG-UHFFFAOYSA-N 1-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-(4-fluorophenyl)-1,3,4-oxadiazol-3-yl]-2,2-dimethylpropan-1-one;dihydrochloride Chemical compound Cl.Cl.CC(C)(C)C(=O)N1N=C(C=2C(=CC=C(F)C=2)F)OC1(CCCN)C1=CC=C(F)C=C1 SAWPHAVUWBUYTG-UHFFFAOYSA-N 0.000 claims 1
- VCWHNFFJUVQCHR-UHFFFAOYSA-N 1-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-(4-methylphenyl)-1,3,4-oxadiazol-3-yl]-2,2-dimethylpropan-1-one;dihydrochloride Chemical compound Cl.Cl.C1=CC(C)=CC=C1C1(CCCN)N(C(=O)C(C)(C)C)N=C(C=2C(=CC=C(F)C=2)F)O1 VCWHNFFJUVQCHR-UHFFFAOYSA-N 0.000 claims 1
- CRTFLZQBXHYNTP-UHFFFAOYSA-N 1-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-oxadiazol-3-yl]-2,2-dimethylpropan-1-one;dihydrochloride Chemical compound Cl.Cl.CC(C)(C)C(=O)N1N=C(C=2C(=CC=C(F)C=2)F)OC1(CCCN)C1=CC=CC=C1 CRTFLZQBXHYNTP-UHFFFAOYSA-N 0.000 claims 1
- ICZTUWDFSCRZLJ-UHFFFAOYSA-N 1-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-oxadiazol-3-yl]-3-methylbutan-1-one;dihydrochloride Chemical compound Cl.Cl.CC(C)CC(=O)N1N=C(C=2C(=CC=C(F)C=2)F)OC1(CCCN)C1=CC=CC=C1 ICZTUWDFSCRZLJ-UHFFFAOYSA-N 0.000 claims 1
- RNKYKNXABSXTEZ-UHFFFAOYSA-N 1-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2,2-dimethylpropan-1-one Chemical compound CC(C)(C)C(=O)N1N=C(C=2C(=CC=C(F)C=2)F)SC1(CCCN)C1=CC=CC=C1 RNKYKNXABSXTEZ-UHFFFAOYSA-N 0.000 claims 1
- MFLLBNSVCLJXHZ-UHFFFAOYSA-N 1-[2-(3-aminopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3-yl]-2-methoxyethanone Chemical compound COCC(=O)N1N=C(C=2C(=CC=C(F)C=2)F)SC1(CCCN)C1=CC=CC=C1 MFLLBNSVCLJXHZ-UHFFFAOYSA-N 0.000 claims 1
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| KR101713453B1 (ko) * | 2010-03-12 | 2017-03-07 | 오메로스 코포레이션 | Pde10 억제제 및 관련 조성물 및 방법 |
| FR2991199B1 (fr) * | 2012-05-30 | 2015-05-15 | IFP Energies Nouvelles | Procede de preparation d'un catalyseur mettant en oeuvre une etape de sechage rapide et son utilisation pour la synthese fischer-tropsch |
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- 2005-10-18 CA CA2952920A patent/CA2952920A1/en not_active Abandoned
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