TW200829563A - Organic compounds - Google Patents
Organic compounds Download PDFInfo
- Publication number
- TW200829563A TW200829563A TW096138922A TW96138922A TW200829563A TW 200829563 A TW200829563 A TW 200829563A TW 096138922 A TW096138922 A TW 096138922A TW 96138922 A TW96138922 A TW 96138922A TW 200829563 A TW200829563 A TW 200829563A
- Authority
- TW
- Taiwan
- Prior art keywords
- phenyl
- group
- benzimidazole
- carboxylic acid
- acid
- Prior art date
Links
- 150000002894 organic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 145
- 102100036869 Diacylglycerol O-acyltransferase 1 Human genes 0.000 claims abstract description 35
- 101000927974 Homo sapiens Diacylglycerol O-acyltransferase 1 Proteins 0.000 claims abstract description 18
- -1 Amidino, carboxyl Chemical group 0.000 claims description 491
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 355
- 239000002253 acid Substances 0.000 claims description 224
- 125000000217 alkyl group Chemical group 0.000 claims description 214
- 229910052739 hydrogen Inorganic materials 0.000 claims description 150
- 239000001257 hydrogen Substances 0.000 claims description 150
- 150000001412 amines Chemical class 0.000 claims description 114
- 125000000623 heterocyclic group Chemical group 0.000 claims description 102
- 125000003545 alkoxy group Chemical group 0.000 claims description 97
- 125000003118 aryl group Chemical group 0.000 claims description 89
- 125000001072 heteroaryl group Chemical group 0.000 claims description 89
- 150000002431 hydrogen Chemical class 0.000 claims description 89
- 239000004305 biphenyl Substances 0.000 claims description 84
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 80
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 78
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
- 229910052799 carbon Inorganic materials 0.000 claims description 77
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 73
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 70
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 64
- 229910052736 halogen Inorganic materials 0.000 claims description 61
- 150000002367 halogens Chemical class 0.000 claims description 60
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 56
- 125000001424 substituent group Chemical group 0.000 claims description 56
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 54
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 54
- COYPLDIXZODDDL-UHFFFAOYSA-N 3h-benzimidazole-5-carboxylic acid Chemical compound OC(=O)C1=CC=C2N=CNC2=C1 COYPLDIXZODDDL-UHFFFAOYSA-N 0.000 claims description 53
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 53
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 48
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 47
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 45
- 125000003277 amino group Chemical group 0.000 claims description 44
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 42
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 41
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 40
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 40
- MYXFJJLPJSMHEA-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-3h-benzimidazole-5-carboxylic acid Chemical compound N1C2=CC(C(=O)O)=CC=C2N=C1C1=C(Cl)C=CC=C1Cl MYXFJJLPJSMHEA-UHFFFAOYSA-N 0.000 claims description 37
- 125000004104 aryloxy group Chemical group 0.000 claims description 35
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 33
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 30
- 239000007789 gas Substances 0.000 claims description 30
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
- 239000000126 substance Substances 0.000 claims description 29
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 28
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 26
- SPXLGJUKLZVPKV-UHFFFAOYSA-N N-decyl-3,4-dimethylaniline Chemical compound CCCCCCCCCCNC1=CC=C(C)C(C)=C1 SPXLGJUKLZVPKV-UHFFFAOYSA-N 0.000 claims description 25
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 22
- 125000003282 alkyl amino group Chemical group 0.000 claims description 22
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 22
- 229940002612 prodrug Drugs 0.000 claims description 21
- 239000000651 prodrug Substances 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- DOLQYFPDPKPQSS-UHFFFAOYSA-N 4-amino-o-xylene Natural products CC1=CC=C(N)C=C1C DOLQYFPDPKPQSS-UHFFFAOYSA-N 0.000 claims description 18
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 16
- 125000002950 monocyclic group Chemical group 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 16
- 125000004494 ethyl ester group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 14
- 125000005110 aryl thio group Chemical group 0.000 claims description 14
- 125000002619 bicyclic group Chemical group 0.000 claims description 14
- MYFOECRTRRMVFM-UHFFFAOYSA-N 3-chloro-N-decylaniline Chemical compound CCCCCCCCCCNC1=CC=CC(Cl)=C1 MYFOECRTRRMVFM-UHFFFAOYSA-N 0.000 claims description 13
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 12
- 239000000796 flavoring agent Substances 0.000 claims description 12
- NKWCGTOZTHZDHB-UHFFFAOYSA-N 1h-imidazol-1-ium-4-carboxylate Chemical compound OC(=O)C1=CNC=N1 NKWCGTOZTHZDHB-UHFFFAOYSA-N 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 150000002923 oximes Chemical class 0.000 claims description 11
- 125000003003 spiro group Chemical group 0.000 claims description 11
- 229960005286 carbaryl Drugs 0.000 claims description 10
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims description 10
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 10
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 10
- 239000000052 vinegar Substances 0.000 claims description 10
- 235000021419 vinegar Nutrition 0.000 claims description 10
- RHXSYTACTOMVLJ-UHFFFAOYSA-N 1H-benzimidazole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=NC2=C1 RHXSYTACTOMVLJ-UHFFFAOYSA-N 0.000 claims description 9
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 9
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 8
- 206010036790 Productive cough Diseases 0.000 claims description 8
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 8
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 8
- 208000024794 sputum Diseases 0.000 claims description 8
- 229940124530 sulfonamide Drugs 0.000 claims description 8
- MLNAJQMKSWRXHR-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-1h-benzimidazole Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC=CC=C2N1 MLNAJQMKSWRXHR-UHFFFAOYSA-N 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 125000005265 dialkylamine group Chemical group 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 7
- 150000003456 sulfonamides Chemical class 0.000 claims description 7
- 125000003944 tolyl group Chemical group 0.000 claims description 7
- 150000003973 alkyl amines Chemical class 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 6
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 6
- 210000003296 saliva Anatomy 0.000 claims description 6
- 239000004575 stone Substances 0.000 claims description 6
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 5
- XYCXHEJYSCYZOD-UHFFFAOYSA-N C1(=CC=CC=C1)C=1C=C(C=CC1)NCCCCCCCCCC Chemical compound C1(=CC=CC=C1)C=1C=C(C=CC1)NCCCCCCCCCC XYCXHEJYSCYZOD-UHFFFAOYSA-N 0.000 claims description 5
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000005055 alkyl alkoxy group Chemical group 0.000 claims description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-dimethylbenzene Natural products CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 5
- 150000003573 thiols Chemical class 0.000 claims description 5
- MGEISDILQNFVEX-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-1,3-benzoxazole Chemical compound ClC1=CC=CC(Cl)=C1C1=NC2=CC=CC=C2O1 MGEISDILQNFVEX-UHFFFAOYSA-N 0.000 claims description 4
- OAZHXZJUWHKFMP-UHFFFAOYSA-N 2-methylindazole Chemical compound C1=CC=CC2=NN(C)C=C21 OAZHXZJUWHKFMP-UHFFFAOYSA-N 0.000 claims description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 claims description 4
- JATXJNNOTHVDIQ-UHFFFAOYSA-N CCCCCCCCCCNC1=CC(=C(C=C1)S)S Chemical compound CCCCCCCCCCNC1=CC(=C(C=C1)S)S JATXJNNOTHVDIQ-UHFFFAOYSA-N 0.000 claims description 4
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims description 4
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 125000004188 dichlorophenyl group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000000286 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 4
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims description 4
- 230000002441 reversible effect Effects 0.000 claims description 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 235000019640 taste Nutrition 0.000 claims description 4
- VVZRKVYGKNFTRR-UHFFFAOYSA-N 12h-benzo[a]xanthene Chemical class C1=CC=CC2=C3CC4=CC=CC=C4OC3=CC=C21 VVZRKVYGKNFTRR-UHFFFAOYSA-N 0.000 claims description 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 3
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 3
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 2
- VTTCWUHZUXWTPP-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)-1,3-benzoxazole-5-carboxylic acid Chemical compound N=1C2=CC(C(=O)O)=CC=C2OC=1C1=C(Cl)C=CC=C1Cl VTTCWUHZUXWTPP-UHFFFAOYSA-N 0.000 claims description 2
- BMTCKKNGHJATLU-UHFFFAOYSA-N 2-(2,6-dimethylphenyl)-3h-benzimidazole-5-carboxylic acid Chemical compound CC1=CC=CC(C)=C1C1=NC2=CC=C(C(O)=O)C=C2N1 BMTCKKNGHJATLU-UHFFFAOYSA-N 0.000 claims description 2
- 125000000301 2-(3-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 2
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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- 150000002460 imidazoles Chemical class 0.000 claims description 2
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- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 2
- FEZJHUREPLIWQD-UHFFFAOYSA-N n-decyl-2-methylaniline Chemical compound CCCCCCCCCCNC1=CC=CC=C1C FEZJHUREPLIWQD-UHFFFAOYSA-N 0.000 claims description 2
- VTHOTOFWYDBNID-UHFFFAOYSA-N n-decylaniline Chemical compound CCCCCCCCCCNC1=CC=CC=C1 VTHOTOFWYDBNID-UHFFFAOYSA-N 0.000 claims description 2
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- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 claims 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
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| TWI826525B (zh) * | 2018-09-18 | 2023-12-21 | 美商拓臻股份有限公司 | 用於治療特定白血病之化合物 |
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| ATE492541T1 (de) | 2006-05-30 | 2011-01-15 | Astrazeneca Ab | Substituierte 5-phenylamino-1,3,4-oxadiazol-2- ylcarbonylamino-4-phenoxycyclohexancarbonsäuren als inhibitoren von acetylcoenzym-a- diacylglycerolacyltransferase |
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| WO2010039668A2 (en) * | 2008-10-01 | 2010-04-08 | The Regents Of The University Of California | Inhibitors of cyclin kinase inhibitor p21 |
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| US8637507B2 (en) * | 2009-03-18 | 2014-01-28 | Merck Sharp & Dohme Corp. | Bicyclic compounds as inhibitors of diacylglycerol acyltransferase |
| AU2010261499A1 (en) | 2009-06-19 | 2012-01-12 | Astrazeneca Ab | Pyrazine carboxamides as inhibitors of DGAT1 |
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- 2007-10-16 AR ARP070104573A patent/AR063311A1/es not_active Application Discontinuation
- 2007-10-16 PE PE2007001396A patent/PE20080888A1/es not_active Application Discontinuation
- 2007-10-17 BR BRPI0718478-6A2A patent/BRPI0718478A2/pt not_active IP Right Cessation
- 2007-10-17 ES ES07854118.2T patent/ES2440253T3/es active Active
- 2007-10-17 CA CA002666880A patent/CA2666880A1/en not_active Abandoned
- 2007-10-17 EP EP07854118.2A patent/EP2074089B1/en not_active Not-in-force
- 2007-10-17 US US12/446,088 patent/US8222248B2/en not_active Expired - Fee Related
- 2007-10-17 MX MX2009004047A patent/MX2009004047A/es not_active Application Discontinuation
- 2007-10-17 TW TW096138922A patent/TW200829563A/zh unknown
- 2007-10-17 RU RU2009118489/04A patent/RU2009118489A/ru not_active Application Discontinuation
- 2007-10-17 JP JP2009533499A patent/JP5298022B2/ja not_active Expired - Fee Related
- 2007-10-17 WO PCT/US2007/081607 patent/WO2008048991A2/en not_active Ceased
- 2007-10-17 KR KR1020097010003A patent/KR20090071642A/ko not_active Withdrawn
- 2007-10-17 AU AU2007311087A patent/AU2007311087B2/en not_active Ceased
- 2007-10-17 CL CL200702974A patent/CL2007002974A1/es unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI826525B (zh) * | 2018-09-18 | 2023-12-21 | 美商拓臻股份有限公司 | 用於治療特定白血病之化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| MX2009004047A (es) | 2009-07-21 |
| RU2009118489A (ru) | 2010-11-27 |
| CL2007002974A1 (es) | 2008-05-23 |
| BRPI0718478A2 (pt) | 2013-11-26 |
| US8222248B2 (en) | 2012-07-17 |
| WO2008048991A3 (en) | 2008-07-10 |
| CA2666880A1 (en) | 2008-04-28 |
| AU2007311087B2 (en) | 2012-03-01 |
| KR20090071642A (ko) | 2009-07-01 |
| WO2008048991A2 (en) | 2008-04-24 |
| AU2007311087A1 (en) | 2008-04-24 |
| AR063311A1 (es) | 2009-01-21 |
| JP2010506950A (ja) | 2010-03-04 |
| ES2440253T3 (es) | 2014-01-28 |
| PE20080888A1 (es) | 2008-08-26 |
| EP2074089A2 (en) | 2009-07-01 |
| US20110046133A1 (en) | 2011-02-24 |
| JP5298022B2 (ja) | 2013-09-25 |
| EP2074089B1 (en) | 2013-09-18 |
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