TW200520756A - Lta4h modulators - Google Patents
Lta4h modulators Download PDFInfo
- Publication number
- TW200520756A TW200520756A TW093122566A TW93122566A TW200520756A TW 200520756 A TW200520756 A TW 200520756A TW 093122566 A TW093122566 A TW 093122566A TW 93122566 A TW93122566 A TW 93122566A TW 200520756 A TW200520756 A TW 200520756A
- Authority
- TW
- Taiwan
- Prior art keywords
- yloxy
- group
- alkyl
- benzyl
- benzothiazol
- Prior art date
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- 101150099556 LTA4H gene Proteins 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 206
- 102100022118 Leukotriene A-4 hydrolase Human genes 0.000 claims abstract description 42
- 206010061218 Inflammation Diseases 0.000 claims abstract description 32
- 230000004054 inflammatory process Effects 0.000 claims abstract description 32
- 230000000694 effects Effects 0.000 claims abstract description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 571
- 125000000217 alkyl group Chemical group 0.000 claims description 402
- -1 alkyl hydrazine Chemical compound 0.000 claims description 388
- 150000001875 compounds Chemical class 0.000 claims description 262
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 261
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 194
- 229910052757 nitrogen Inorganic materials 0.000 claims description 157
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Natural products CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 139
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 122
- 229910052799 carbon Inorganic materials 0.000 claims description 117
- 125000005842 heteroatom Chemical group 0.000 claims description 115
- 125000000623 heterocyclic group Chemical group 0.000 claims description 115
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 111
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 93
- 125000001424 substituent group Chemical group 0.000 claims description 92
- 239000002253 acid Substances 0.000 claims description 57
- 239000007789 gas Substances 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
- 101000619898 Homo sapiens Leukotriene A-4 hydrolase Proteins 0.000 claims description 46
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 44
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 150000001412 amines Chemical class 0.000 claims description 40
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 39
- 229960000583 acetic acid Drugs 0.000 claims description 38
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 32
- 239000008194 pharmaceutical composition Substances 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 30
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 235000021419 vinegar Nutrition 0.000 claims description 26
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Substances OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 25
- 229920006395 saturated elastomer Polymers 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 24
- 239000000052 vinegar Substances 0.000 claims description 24
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 23
- 241000700159 Rattus Species 0.000 claims description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 22
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 claims description 17
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 150000002923 oximes Chemical class 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 229910052740 iodine Inorganic materials 0.000 claims description 14
- 229910052707 ruthenium Inorganic materials 0.000 claims description 14
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
- 239000011159 matrix material Substances 0.000 claims description 13
- 238000006467 substitution reaction Methods 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 12
- 208000006673 asthma Diseases 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 230000002757 inflammatory effect Effects 0.000 claims description 12
- 239000011347 resin Substances 0.000 claims description 12
- 229920005989 resin Polymers 0.000 claims description 12
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 201000001320 Atherosclerosis Diseases 0.000 claims description 11
- 201000004681 Psoriasis Diseases 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- 230000002401 inhibitory effect Effects 0.000 claims description 11
- 150000002576 ketones Chemical class 0.000 claims description 11
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 10
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 10
- 125000005605 benzo group Chemical group 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- 206010036790 Productive cough Diseases 0.000 claims description 9
- 201000006417 multiple sclerosis Diseases 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- 208000024794 sputum Diseases 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 9
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000001041 indolyl group Chemical group 0.000 claims description 8
- 125000006308 propyl amino group Chemical group 0.000 claims description 8
- 125000006531 (C2-C5) alkyl group Chemical group 0.000 claims description 7
- ZGSQQPIVBRWTEB-UHFFFAOYSA-N 3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methylamino]propanoic acid Chemical compound C1=CC(CNCCC(=O)O)=CC=C1OC1=NC2=CC=CC=C2S1 ZGSQQPIVBRWTEB-UHFFFAOYSA-N 0.000 claims description 7
- 241000699670 Mus sp. Species 0.000 claims description 7
- 150000002430 hydrocarbons Chemical group 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 150000003335 secondary amines Chemical group 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 6
- 108090000790 Enzymes Proteins 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 241000699666 Mus <mouse, genus> Species 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 229910052802 copper Inorganic materials 0.000 claims description 6
- 125000004494 ethyl ester group Chemical group 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 210000003802 sputum Anatomy 0.000 claims description 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
- CFTXJKKITUELKJ-UHFFFAOYSA-N 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-ol Chemical compound C1CC(O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 CFTXJKKITUELKJ-UHFFFAOYSA-N 0.000 claims description 5
- BUZBVOKDNAZIIM-UHFFFAOYSA-N 1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidine-4-carboxylic acid Chemical compound C1CC(C(=O)O)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 BUZBVOKDNAZIIM-UHFFFAOYSA-N 0.000 claims description 5
- NSQMWZLLTGEDQU-UHFFFAOYSA-N 2-aminocyclobutane-1-carboxylic acid Chemical compound NC1CCC1C(O)=O NSQMWZLLTGEDQU-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 5
- 238000003324 Six Sigma (6σ) Methods 0.000 claims description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 229910052805 deuterium Inorganic materials 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 150000004702 methyl esters Chemical class 0.000 claims description 5
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 241000555745 Sciuridae Species 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 235000006408 oxalic acid Nutrition 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- BPBIGNTWIBJUFE-UHFFFAOYSA-N 1-[1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCN(CC=2C=CC(OC=3SC4=CC=CC=C4N=3)=CC=2)CC1 BPBIGNTWIBJUFE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 3
- AVRWIZZEDUWJDM-UHFFFAOYSA-N 2-[4-[(4,4-difluoropiperidin-1-yl)methyl]phenoxy]-1,3-benzothiazole Chemical compound C1CC(F)(F)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 AVRWIZZEDUWJDM-UHFFFAOYSA-N 0.000 claims description 3
- MOOTXNIBLHHYFC-UHFFFAOYSA-N 6-methoxy-2-[4-(piperidin-1-ylmethyl)phenoxy]-1,3-benzothiazole Chemical compound S1C2=CC(OC)=CC=C2N=C1OC(C=C1)=CC=C1CN1CCCCC1 MOOTXNIBLHHYFC-UHFFFAOYSA-N 0.000 claims description 3
- 241000237858 Gastropoda Species 0.000 claims description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical class C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 230000002950 deficient Effects 0.000 claims description 3
- 230000006735 deficit Effects 0.000 claims description 3
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims description 3
- 239000008267 milk Substances 0.000 claims description 3
- IEPGXTISLYYPRB-UHFFFAOYSA-N n-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]cyclopropanamine Chemical compound C=1C=C(OC=2SC3=CC=CC=C3N=2)C=CC=1CNC1CC1 IEPGXTISLYYPRB-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- HNDXKIMMSFCCFW-UHFFFAOYSA-N propane-2-sulphonic acid Chemical compound CC(C)S(O)(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-N 0.000 claims description 3
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 claims description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- RVBPILVVAOIPAV-UHFFFAOYSA-N 1-[4-(1,3-benzothiazol-2-yloxy)phenyl]-n-methylmethanamine Chemical compound C1=CC(CNC)=CC=C1OC1=NC2=CC=CC=C2S1 RVBPILVVAOIPAV-UHFFFAOYSA-N 0.000 claims description 2
- YMVQIDAYXZCGJI-UHFFFAOYSA-N 1-cyclopropylpropane-1,3-diamine Chemical compound NCCC(N)C1CC1 YMVQIDAYXZCGJI-UHFFFAOYSA-N 0.000 claims description 2
- IQTADKJWOJRVNV-UHFFFAOYSA-N 2-(4-ethylphenoxy)-1,3-benzothiazole Chemical compound C1=CC(CC)=CC=C1OC1=NC2=CC=CC=C2S1 IQTADKJWOJRVNV-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- GBRPJSNUBUWYIA-UHFFFAOYSA-N S1C(=NC2=C1C=CC=C2)OC2=CC=C(CN1CCC(CC1)NCCCCCCCCCC)C=C2 Chemical compound S1C(=NC2=C1C=CC=C2)OC2=CC=C(CN1CCC(CC1)NCCCCCCCCCC)C=C2 GBRPJSNUBUWYIA-UHFFFAOYSA-N 0.000 claims description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
- QSXCOQDPUUXGCR-UHFFFAOYSA-N [1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-2-yl]methanol Chemical compound OCC1CCCCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 QSXCOQDPUUXGCR-UHFFFAOYSA-N 0.000 claims description 2
- NOSINBBPECBLQO-UHFFFAOYSA-N [1-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl]piperidin-4-yl]thiourea Chemical compound C1CC(NC(=S)N)CCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 NOSINBBPECBLQO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
- 229960001541 benzthiazide Drugs 0.000 claims description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- QVVWRAAMUPSWRE-UHFFFAOYSA-N ethyl 3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methylamino]propanoate Chemical compound C1=CC(CNCCC(=O)OCC)=CC=C1OC1=NC2=CC=CC=C2S1 QVVWRAAMUPSWRE-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000000593 indol-1-yl group Chemical group [H]C1=C([H])C([H])=C2N([*])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 235000013336 milk Nutrition 0.000 claims description 2
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- GASFVSRUEBGMDI-UHFFFAOYSA-N n-aminohydroxylamine Chemical compound NNO GASFVSRUEBGMDI-UHFFFAOYSA-N 0.000 claims description 2
- PJMKKSGLJJBQMY-UHFFFAOYSA-N nonan-1-one Chemical compound CCCCCCCC[C]=O PJMKKSGLJJBQMY-UHFFFAOYSA-N 0.000 claims description 2
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- 150000007949 saponins Chemical class 0.000 claims description 2
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 4
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 108090000623 proteins and genes Proteins 0.000 claims 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims 4
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- WKVZMKDXJFCMMD-UVWUDEKDSA-L (5ar,8ar,9r)-5-[[(2r,4ar,6r,7r,8r,8as)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one;azanide;n,3-bis(2-chloroethyl)-2-ox Chemical compound [NH2-].[NH2-].Cl[Pt+2]Cl.ClCCNP1(=O)OCCCN1CCCl.COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3C(O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 WKVZMKDXJFCMMD-UVWUDEKDSA-L 0.000 claims 2
- 229940057054 1,3-dimethylurea Drugs 0.000 claims 2
- ZMIBIIAWFMCVFD-UHFFFAOYSA-N 2,2-difluoroacetamide Chemical compound NC(=O)C(F)F ZMIBIIAWFMCVFD-UHFFFAOYSA-N 0.000 claims 2
- LDQLMAQAGHYNDZ-UHFFFAOYSA-N 2-[4-[(3-methylpiperidin-1-yl)methyl]phenoxy]-1,3-benzothiazole Chemical compound C1C(C)CCCN1CC(C=C1)=CC=C1OC1=NC2=CC=CC=C2S1 LDQLMAQAGHYNDZ-UHFFFAOYSA-N 0.000 claims 2
- WHQQJWGYHZAHDC-UHFFFAOYSA-N 3-[[4-(1,3-benzothiazol-2-yloxy)phenyl]methyl-methylamino]propanenitrile Chemical compound C1=CC(CN(CCC#N)C)=CC=C1OC1=NC2=CC=CC=C2S1 WHQQJWGYHZAHDC-UHFFFAOYSA-N 0.000 claims 2
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- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
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Classifications
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- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
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- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
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- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
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| CN100591679C (zh) * | 2003-07-28 | 2010-02-24 | 詹森药业有限公司 | 苯并咪唑、苯并噻唑和苯并唑衍生物及其作为lta4h调节剂的应用 |
| CN101189012A (zh) * | 2005-03-31 | 2008-05-28 | 詹森药业有限公司 | 苯基和吡啶基lta4h调节剂 |
| ES2523565T3 (es) | 2005-04-13 | 2014-11-27 | Astex Therapeutics Limited | Derivados de hidroxibenzamida y sus usos como inhibidores de la hsp90 |
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| UA101943C2 (ru) * | 2005-09-21 | 2013-05-27 | Декод Дженетикс Ехф | Биарилзамещенные гетероциклические ингибиторы lta4h для лечения воспаления |
| AU2006333522A1 (en) * | 2005-12-21 | 2007-07-12 | Decode Genetics, Ehf. | Biaryl nitrogen heterocycle inhibitors of LTA4H for treating inflammation |
| WO2007073405A1 (en) * | 2005-12-21 | 2007-06-28 | Decode Genetics Ehf | N-linked aryl heteroaryl inhibitors of lta4h for treating inflammation |
| CA2634701C (en) | 2005-12-21 | 2014-07-29 | Decode Genetics Ehf | Biaryl substituted nitrogen containing heterocycle inhibitors of lta4h for treating inflammation |
| HUE031972T2 (en) * | 2005-12-29 | 2017-08-28 | Celtaxsys Inc | Diamine derivatives as inhibitors of leukotriene a4 hydrolase |
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| US7951829B2 (en) * | 2006-05-03 | 2011-05-31 | Janssen Pharmaceutica Nv | Benzimidazole modulators of VR1 |
| US8299095B2 (en) * | 2006-06-16 | 2012-10-30 | H. Lundbeck A/S | Crystalline forms of 4-[2-(4-methylphenylsulfanyl)-phenyl] piperidine with combined serotonin and norepinephrine reuptake inhibition and uses thereof |
| US7728032B2 (en) * | 2006-08-04 | 2010-06-01 | Decode Genetics Ehf | Phenoxymethylalkyne inhibitors of LTA4H for treating inflammation |
| WO2008019302A1 (en) * | 2006-08-04 | 2008-02-14 | Decode Genetics Ehf | Pyrazolylphenyl and pyrrolylphenyl inhibitors of lta4h for treating inflammation |
| EP2066800A2 (en) * | 2006-08-04 | 2009-06-10 | Decode Genetics EHF | Aryl amino acid derivatives as inhibitors of lta4h (leukotriene a4 hydrolase) for treating inflammation |
| US8916552B2 (en) | 2006-10-12 | 2014-12-23 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US8883790B2 (en) | 2006-10-12 | 2014-11-11 | Astex Therapeutics Limited | Pharmaceutical combinations |
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| WO2008044029A1 (en) | 2006-10-12 | 2008-04-17 | Astex Therapeutics Limited | Pharmaceutical combinations |
| GB0620259D0 (en) | 2006-10-12 | 2006-11-22 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| TW200906396A (en) * | 2007-02-14 | 2009-02-16 | Janssen Pharmaceutica Nv | LTA4H modulators and uses thereof |
| US20100120807A1 (en) * | 2007-03-08 | 2010-05-13 | Irm Llc | Compounds and compositions as modulators of gpr119 activity |
| WO2008120710A1 (ja) * | 2007-03-30 | 2008-10-09 | Panasonic Electric Works Co., Ltd. | 活動強度計 |
| UY31443A1 (es) * | 2007-10-31 | 2009-04-30 | Diaminas en puente o fusionadas sustituidas con arilo como moduladores de leucotrieno a4 hidrolasa | |
| US20090176785A1 (en) * | 2007-11-16 | 2009-07-09 | Abbott Laboratories | Method of treating arthritis |
| GB0806527D0 (en) | 2008-04-11 | 2008-05-14 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| MX2010011154A (es) * | 2008-04-11 | 2010-12-21 | Janssen Pharmaceutica Nv | Tiazolopiridin-2-iloxi-fenilo y tiazolopirazin-2-iloxifenilaminas como moduladores de la leucotrieno a4 hidrolasa. |
| PT2294066E (pt) | 2008-04-28 | 2014-11-21 | Janssen Pharmaceutica Nv | Benzoimidazoles como inibidores da prolil-hidroxilase |
| AU2010249041B2 (en) | 2009-05-14 | 2014-11-13 | Janssen Pharmaceutica Nv | Compounds with two fused bicyclic heteroaryl moieties as modulators of leukotriene A4 hydrolase |
| CN102442962A (zh) * | 2010-11-10 | 2012-05-09 | 江苏德峰药业有限公司 | 1-烷基四氮唑的生产方法 |
| CN102442961A (zh) * | 2010-11-10 | 2012-05-09 | 江苏德峰药业有限公司 | 1-甲基四氮唑的生产方法 |
| EP2776023B1 (en) | 2011-10-25 | 2016-03-09 | Janssen Pharmaceutica, N.V. | Meglumine salt formulations of 1-(5,6-dichloro-1h-benzo[d]imidazol-2-yl)-1h-pyrazole-4-carboxylic acid |
| CA2905340C (en) | 2013-03-12 | 2022-05-31 | Celtaxsys, Inc. | Low dose oral formulations of acebilustat |
| BR112015022226A2 (pt) | 2013-03-14 | 2017-07-18 | Celtaxsys Inc | inibidores de leucotrieno a4 hidrolase |
| KR20150131211A (ko) * | 2013-03-14 | 2015-11-24 | 켈탁시스, 인코퍼레이티드 | 류코트라이엔 a4 가수분해효소의 저해제 |
| BR112015022864A8 (pt) | 2013-03-14 | 2019-11-26 | Celtaxsys Inc | composto, composição farmacêutica e uso dos mesmos |
| WO2015094902A1 (en) * | 2013-12-17 | 2015-06-25 | Eli Lilly And Company | Phenoxyethyl cyclic amine derivatives and their activity as ep4 receptor modulators |
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| EP3233799B1 (en) | 2014-12-19 | 2021-05-19 | The Broad Institute, Inc. | Dopamine d2 receptor ligands |
| RU2715897C2 (ru) | 2015-06-09 | 2020-03-04 | Эббви Инк. | Модуляторы ядерных рецепторов |
| IL267352B2 (en) | 2016-12-21 | 2023-10-01 | Hoffmann La Roche | Method for in vitro glycoengineering of antibodies |
| WO2018114878A1 (en) | 2016-12-21 | 2018-06-28 | F. Hoffmann-La Roche Ag | Re-use of enzymes in in vitro glycoengineering of antibodies |
| CN107663192B (zh) * | 2017-11-03 | 2019-05-10 | 梯尔希（南京）药物研发有限公司 | 一种雷贝拉唑杂质的制备方法 |
| JP7386815B2 (ja) | 2018-05-31 | 2023-11-27 | セルタクシー、エルエルシー | 呼吸器疾患患者の肺増悪を軽減する方法 |
| WO2020087031A1 (en) | 2018-10-26 | 2020-04-30 | The Research Foundation For The State University Of New York | Combination serotonin specific reuptake inhibitor and serotonin 1a receptor partial agonist for reducing l-dopa-induced dyskinesia |
| CN113784713A (zh) * | 2019-01-11 | 2021-12-10 | 纳吉斯制药股份有限公司 | 白三烯合成抑制剂 |
| CN110026557B (zh) * | 2019-05-28 | 2021-08-27 | 南方科技大学 | 一种混合固体颗粒重熔的直写装置及成型方法 |
| TW202235071A (zh) * | 2020-11-19 | 2022-09-16 | 美商特洛治療公司 | 小分子化合物及組成物 |
| US11932630B2 (en) * | 2021-04-16 | 2024-03-19 | Novartis Ag | Heteroaryl aminopropanol derivatives |
| CN113683491A (zh) * | 2021-09-01 | 2021-11-23 | 王传良 | 一种4-(2-溴乙基)苯酚的制备方法 |
| CN113735798B (zh) * | 2021-09-27 | 2022-07-12 | 安徽美致诚药业有限公司 | 一种盐酸罗沙替丁醋酸酯的制备方法 |
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| IL90337A0 (en) * | 1988-05-24 | 1989-12-15 | Pfizer | Aromatic and heterocyclic carboxamide derivatives as antineoplastic agents |
| IT1240598B (it) * | 1990-03-13 | 1993-12-17 | Mini Ricerca Scient Tecnolog | Derivati amminici ad azione antifungina |
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| US5925654A (en) * | 1997-03-12 | 1999-07-20 | G.D. Searle & Co. | LTA4 , hydrolase inhibitors |
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| US20040110757A1 (en) * | 2002-03-21 | 2004-06-10 | Thomas Arrhenius | Flt-1 ligands and their uses in the treatment of diseases regulatable by angiogenesis |
| CN100591679C (zh) * | 2003-07-28 | 2010-02-24 | 詹森药业有限公司 | 苯并咪唑、苯并噻唑和苯并唑衍生物及其作为lta4h调节剂的应用 |
| US7541466B2 (en) * | 2003-12-23 | 2009-06-02 | Genzyme Corporation | Tetrahydroisoquinoline derivatives for treating protein trafficking diseases |
| HRP20160373T1 (hr) * | 2005-03-16 | 2016-05-06 | Meda Pharma Gmbh & Co. Kg | Kombinacija antikolinergika i antagonista leukotrien receptora za liječenje bolesti dišnog sustava |
| TW200906396A (en) * | 2007-02-14 | 2009-02-16 | Janssen Pharmaceutica Nv | LTA4H modulators and uses thereof |
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