JP2011513367A5 - - Google Patents
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- JP2011513367A5 JP2011513367A5 JP2010549146A JP2010549146A JP2011513367A5 JP 2011513367 A5 JP2011513367 A5 JP 2011513367A5 JP 2010549146 A JP2010549146 A JP 2010549146A JP 2010549146 A JP2010549146 A JP 2010549146A JP 2011513367 A5 JP2011513367 A5 JP 2011513367A5
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- JP
- Japan
- Prior art keywords
- carbon atoms
- group
- hydrogen
- alkyl group
- different
- 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.)
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 135
- 125000000217 alkyl group Chemical group 0.000 claims description 83
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 53
- 125000003545 alkoxy group Chemical group 0.000 claims description 44
- 150000002431 hydrogen Chemical class 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 102100021943 C-C motif chemokine 2 Human genes 0.000 claims description 4
- 101710155857 C-C motif chemokine 2 Proteins 0.000 claims description 4
- 108090000835 CX3C Chemokine Receptor 1 Proteins 0.000 claims description 4
- 102100039196 CX3C chemokine receptor 1 Human genes 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims 2
- 206010002383 Angina Pectoris Diseases 0.000 claims 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 208000005777 Lupus Nephritis Diseases 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 2
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 208000029078 coronary artery disease Diseases 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000033679 diabetic kidney disease Diseases 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- -1 glucamine Chemical compound 0.000 claims 2
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 208000010125 myocardial infarction Diseases 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 208000037803 restenosis Diseases 0.000 claims 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims 2
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 claims 1
- KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 claims 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 claims 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 claims 1
- 206010065040 AIDS dementia complex Diseases 0.000 claims 1
- 208000003200 Adenoma Diseases 0.000 claims 1
- 206010001233 Adenoma benign Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical group [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 239000004475 Arginine Substances 0.000 claims 1
- 208000036487 Arthropathies Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- 208000024172 Cardiovascular disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- 239000001263 FEMA 3042 Substances 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 208000029523 Interstitial Lung disease Diseases 0.000 claims 1
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 claims 1
- 208000012659 Joint disease Diseases 0.000 claims 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 1
- 239000004472 Lysine Substances 0.000 claims 1
- 208000001145 Metabolic Syndrome Diseases 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 claims 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010047115 Vasculitis Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims 1
- 239000002250 absorbent Substances 0.000 claims 1
- 230000002745 absorbent Effects 0.000 claims 1
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- 229960005070 ascorbic acid Drugs 0.000 claims 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims 1
- 229940092714 benzenesulfonic acid Drugs 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 229960004365 benzoic acid Drugs 0.000 claims 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 claims 1
- 229960003237 betaine Drugs 0.000 claims 1
- 239000011230 binding agent Substances 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 229960001948 caffeine Drugs 0.000 claims 1
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 0.000 claims 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 1
- 239000000920 calcium hydroxide Substances 0.000 claims 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims 1
- 229960001231 choline Drugs 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 229960004106 citric acid Drugs 0.000 claims 1
- 235000015165 citric acid Nutrition 0.000 claims 1
- 239000003086 colorant Substances 0.000 claims 1
- 230000003412 degenerative effect Effects 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- 239000007884 disintegrant Substances 0.000 claims 1
- XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 235000003599 food sweetener Nutrition 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 229960002598 fumaric acid Drugs 0.000 claims 1
- 235000011087 fumaric acid Nutrition 0.000 claims 1
- LRBQNJMCXXYXIU-QWKBTXIPSA-N gallotannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@H]2[C@@H]([C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-QWKBTXIPSA-N 0.000 claims 1
- 229960002442 glucosamine Drugs 0.000 claims 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 1
- 230000009610 hypersensitivity Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims 1
- 208000017169 kidney disease Diseases 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- 229960000448 lactic acid Drugs 0.000 claims 1
- 239000000314 lubricant Substances 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims 1
- 239000001095 magnesium carbonate Substances 0.000 claims 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 229940098895 maleic acid Drugs 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- ACTNHJDHMQSOGL-UHFFFAOYSA-N n',n'-dibenzylethane-1,2-diamine Chemical compound C=1C=CC=CC=1CN(CCN)CC1=CC=CC=C1 ACTNHJDHMQSOGL-UHFFFAOYSA-N 0.000 claims 1
- 201000008383 nephritis Diseases 0.000 claims 1
- 229940074355 nitric acid Drugs 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 229940116315 oxalic acid Drugs 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 229960004838 phosphoric acid Drugs 0.000 claims 1
- 208000030761 polycystic kidney disease Diseases 0.000 claims 1
- 239000011736 potassium bicarbonate Substances 0.000 claims 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims 1
- 235000015497 potassium bicarbonate Nutrition 0.000 claims 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims 1
- 239000003755 preservative agent Substances 0.000 claims 1
- 229940032330 sulfuric acid Drugs 0.000 claims 1
- 239000003765 sweetening agent Substances 0.000 claims 1
- 229940033123 tannic acid Drugs 0.000 claims 1
- 235000015523 tannic acid Nutrition 0.000 claims 1
- 229920002258 tannic acid Polymers 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 229960001367 tartaric acid Drugs 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 229960004559 theobromine Drugs 0.000 claims 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 1
- 229960000281 trometamol Drugs 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- 239000000080 wetting agent Substances 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08425139 | 2008-03-07 | ||
| EP08425139.6 | 2008-03-07 | ||
| PCT/EP2009/052590 WO2009109618A2 (en) | 2008-03-07 | 2009-03-05 | Novel 1-benzyl-3-hydroxymethylindazole derivatives and use thereof in the treatment of diseases based on the expression of mcp-1, cx3cr1 and p40 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011513367A JP2011513367A (ja) | 2011-04-28 |
| JP2011513367A5 true JP2011513367A5 (https=) | 2014-03-20 |
| JP5509101B2 JP5509101B2 (ja) | 2014-06-04 |
Family
ID=39671487
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010549146A Active JP5509101B2 (ja) | 2008-03-07 | 2009-03-05 | 新規な１−ベンジル−３−ヒドロキシメチルインダゾール誘導体、ならびにそのＭＣＰ−１、ＣＸ３ＣＲ１およびｐ４０の発現に基づく疾患の治療への使用 |
| JP2010549143A Active JP5509099B2 (ja) | 2008-03-07 | 2009-03-05 | 新規な１−ベンジル−３−ヒドロキシメチルインダゾール誘導体並びにそのＭＣＰ−１、ＣＸ３ＣＲ１およびｐ４０の発現に基づく疾患の治療への使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010549143A Active JP5509099B2 (ja) | 2008-03-07 | 2009-03-05 | 新規な１−ベンジル−３−ヒドロキシメチルインダゾール誘導体並びにそのＭＣＰ−１、ＣＸ３ＣＲ１およびｐ４０の発現に基づく疾患の治療への使用 |
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| EP (3) | EP2254869B1 (https=) |
| JP (2) | JP5509101B2 (https=) |
| KR (2) | KR101581828B1 (https=) |
| CN (2) | CN101952256B (https=) |
| AR (2) | AR070810A1 (https=) |
| AU (2) | AU2009221083B2 (https=) |
| BR (2) | BRPI0907976A2 (https=) |
| CA (2) | CA2712403C (https=) |
| CY (2) | CY1117584T1 (https=) |
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| EA (2) | EA019711B1 (https=) |
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| GE (2) | GEP20135912B (https=) |
| HR (2) | HRP20160462T1 (https=) |
| HU (1) | HUE027098T2 (https=) |
| IL (3) | IL206893A0 (https=) |
| LT (1) | LT2254869T (https=) |
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| PL (2) | PL2254869T3 (https=) |
| PT (1) | PT2254869T (https=) |
| SG (1) | SG188177A1 (https=) |
| SI (2) | SI2254870T1 (https=) |
| UA (2) | UA103605C2 (https=) |
| WO (2) | WO2009109618A2 (https=) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2009221063B2 (en) | 2008-03-07 | 2013-03-21 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | 1-benzyl-3-hydroxymethylindazole derivatives and use thereof in the treatment of diseases based on the expression of MCP-1, and CX3CR1 |
| JP5509100B2 (ja) * | 2008-03-07 | 2014-06-04 | アジェンデ・キミケ・リウニテ・アンジェリニ・フランチェスコ・ア・チ・エレ・ア・エフェ・ソシエタ・ペル・アチオニ | 新規な１−ベンジル−３−ヒドロキシメチルインダゾール誘導体及びそのＭＣＰ−１，ＣＸ３ＣＲ１及びｐ４０の発現に基づく疾病の治療への使用 |
| EA019711B1 (ru) * | 2008-03-07 | 2014-05-30 | Ацьенде Кимике Рьюните Анджелини Франческо A.K.P.A.Ф. С.П.А. | ПРОИЗВОДНЫЕ 1-БЕНЗИЛ-3-ГИДРОКСИМЕТИЛИНДАЗОЛА, СОДЕРЖАЩАЯ ИХ ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ И ИХ ПРИМЕНЕНИЕ ПРИ ЛЕЧЕНИИ ЗАБОЛЕВАНИЙ, ОБУСЛОВЛЕННЫХ ЭКСПРЕССИЕЙ МСР-1, СХ3CR1 ИЛИ р40 |
| GEP20135879B (en) * | 2009-08-03 | 2013-07-10 | Aziende Chimiche Riunite Angelini Francesco A C R A F S P A It | Method of 1-benzyl-3-hydroxymethyl-1h-indazole preparation, derivatives thereof, and required magnesium intermediates |
| UA108742C2 (uk) * | 2009-09-23 | 2015-06-10 | Фармацевтична композиція для лікування запальних захворювань, опосередкованих mcp-1 | |
| ES2656292T3 (es) * | 2012-05-01 | 2018-02-26 | Translatum Medicus Inc. | Métodos de tratamiento y diagnóstico de enfermedades oculares que causan ceguera |
| US8999292B2 (en) | 2012-05-01 | 2015-04-07 | Translatum Medicus Inc. | Methods for treating and diagnosing blinding eye diseases |
| EP2850062B1 (en) | 2012-05-18 | 2017-07-19 | Sanofi | Pyridine derivatives and their use in the treatment of conditions associated with pathological thrombus formation |
| US9346762B2 (en) | 2012-05-18 | 2016-05-24 | Sanofi | Pyrazole derivatives and their use as LPAR5 antagonists |
| US10918588B2 (en) | 2012-11-09 | 2021-02-16 | Colgate-Palmolive Company | Block copolymers for tooth enamel protection |
| WO2015173786A1 (en) * | 2014-05-15 | 2015-11-19 | Boyd Shelley Romayne | Compositions and methods for treating and diagnosing ocular disorders |
| BR112017026535B1 (pt) | 2015-06-12 | 2023-12-19 | Vettore, LLC | Composto e composição farmacêutica |
| US20180221339A1 (en) * | 2015-06-16 | 2018-08-09 | Translatum Medicus, Inc. | Compositions and methods for treating and diagnosing ocular disorders |
| WO2018111904A1 (en) | 2016-12-12 | 2018-06-21 | Vettore, LLC | Heterocyclic inhibitors of mct4 |
| GB201811169D0 (en) | 2018-07-06 | 2018-08-29 | Kancera Ab | New compounds |
| JP6612004B1 (ja) * | 2018-07-31 | 2019-11-27 | 株式会社親広産業 | グルコース消費促進剤および解糖系促進剤 |
| WO2020026471A1 (ja) * | 2018-07-31 | 2020-02-06 | 株式会社親広産業 | グルコース消費促進剤および解糖系促進剤 |
| EP3990433A4 (en) * | 2019-06-25 | 2023-07-26 | Translatum Medicus Inc. | METHODS FOR THE MANUFACTURE OF 2-((1-BENZYL-1H-INDAZOL-3-YL)METHOXY)-2-METHYLPROPANOIC ACID AND ITS DERIVATIVES |
| CN113929627A (zh) * | 2021-10-19 | 2022-01-14 | 吕梁学院 | 一种宾达利的合成方法 |
| WO2024108386A1 (zh) * | 2022-11-22 | 2024-05-30 | 中国科学院深圳先进技术研究院 | 抗mcp1中和抗体在制备治疗神经退行性疾病引起的系统性炎症药物中的应用 |
| WO2024165925A1 (en) * | 2023-02-10 | 2024-08-15 | Translatum Medicus Inc. | Bindarit conjugates, compositions and methods for treating ocular diseases or disorders |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US416359A (en) * | 1889-12-03 | Sash-fastener | ||
| US364371A (en) * | 1887-06-07 | peice | ||
| IT1230441B (it) * | 1989-02-07 | 1991-10-23 | Acraf | Eteri della serie dell'indazolo |
| IT1253703B (it) * | 1991-04-22 | 1995-08-23 | Angelini Francesco Ist Ricerca | Uso di acidi metossi alcanoici dell'indazolo per preparare un farmaco attivo nel trattamento di malattie autoimmunitarie |
| IT1293795B1 (it) | 1997-07-28 | 1999-03-10 | Angelini Ricerche Spa | Farmaco attivo nel ridurre la produzione di proteina mcp-1 |
| WO2000078757A1 (en) | 1999-06-17 | 2000-12-28 | Shionogi Bioresearch Corp. | Inhibitors of il-12 production |
| EP1188438A1 (en) | 2000-09-15 | 2002-03-20 | Warner-Lambert Company | Pharmaceutical composition for preventing or treating a disease associated with an excess of Il-12 production |
| EP1199074A1 (en) | 2000-09-15 | 2002-04-24 | Warner-Lambert Company | Pharmaceutical composition for preventing or treating a disease associated with an excess of il-12 production |
| JP4234439B2 (ja) | 2001-03-15 | 2009-03-04 | 生化学工業株式会社 | Ｉｌ−１２発現調節剤 |
| CA2468349A1 (en) | 2001-11-30 | 2003-06-12 | Synta Pharmaceuticals Corporation | Pyrimidine compounds |
| CA2541533A1 (en) | 2003-10-07 | 2005-04-14 | Astrazeneca Ab | New 2-substituted, 4-amino-thiazolo[4,5-d] pyrimidines, useful as chemokine receptor antagonists, esp. cx3cr1 |
| ES2641815T3 (es) * | 2004-10-29 | 2017-11-14 | Eisai R&D Management Co., Ltd. | Tratamiento para enfermedades inflamatorias |
| EP1819341A4 (en) | 2004-11-10 | 2011-06-29 | Synta Pharmaceuticals Corp | IL-12 MODULATORY CONNECTIONS |
| US7851466B2 (en) | 2004-11-19 | 2010-12-14 | Synta Pharmaceuticals Corp. | Pyrimidine compounds and uses thereof |
| UA90707C2 (en) | 2005-04-06 | 2010-05-25 | Астразенека Аб | Novel 5-substituted 7-amino-[1,3]thiazolo[4,5-d]pyrimidine derivatives |
| AR053347A1 (es) | 2005-04-06 | 2007-05-02 | Astrazeneca Ab | Derivados de [1,3]tiazolo[4,5-d]pirimidin-2(3h)-ona 5,7-sustituidos |
| EA019711B1 (ru) | 2008-03-07 | 2014-05-30 | Ацьенде Кимике Рьюните Анджелини Франческо A.K.P.A.Ф. С.П.А. | ПРОИЗВОДНЫЕ 1-БЕНЗИЛ-3-ГИДРОКСИМЕТИЛИНДАЗОЛА, СОДЕРЖАЩАЯ ИХ ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ И ИХ ПРИМЕНЕНИЕ ПРИ ЛЕЧЕНИИ ЗАБОЛЕВАНИЙ, ОБУСЛОВЛЕННЫХ ЭКСПРЕССИЕЙ МСР-1, СХ3CR1 ИЛИ р40 |
| JP5509100B2 (ja) | 2008-03-07 | 2014-06-04 | アジェンデ・キミケ・リウニテ・アンジェリニ・フランチェスコ・ア・チ・エレ・ア・エフェ・ソシエタ・ペル・アチオニ | 新規な１−ベンジル−３−ヒドロキシメチルインダゾール誘導体及びそのＭＣＰ−１，ＣＸ３ＣＲ１及びｐ４０の発現に基づく疾病の治療への使用 |
| AU2009221063B2 (en) | 2008-03-07 | 2013-03-21 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | 1-benzyl-3-hydroxymethylindazole derivatives and use thereof in the treatment of diseases based on the expression of MCP-1, and CX3CR1 |
-
2009
- 2009-03-05 EA EA201071040A patent/EA019711B1/ru not_active IP Right Cessation
- 2009-03-05 CN CN200980105556.4A patent/CN101952256B/zh not_active Expired - Fee Related
- 2009-03-05 US US12/865,923 patent/US8835481B2/en not_active Expired - Fee Related
- 2009-03-05 BR BRPI0907976-9A patent/BRPI0907976A2/pt not_active IP Right Cessation
- 2009-03-05 HR HRP20160462TT patent/HRP20160462T1/hr unknown
- 2009-03-05 ES ES09718467.5T patent/ES2569330T3/es active Active
- 2009-03-05 JP JP2010549146A patent/JP5509101B2/ja active Active
- 2009-03-05 DK DK09717638.2T patent/DK2254869T3/en active
- 2009-03-05 KR KR1020107017806A patent/KR101581828B1/ko not_active Expired - Fee Related
- 2009-03-05 WO PCT/EP2009/052590 patent/WO2009109618A2/en not_active Ceased
- 2009-03-05 CN CN200980105073.4A patent/CN101945855B/zh not_active Expired - Fee Related
- 2009-03-05 EA EA201071038A patent/EA018241B1/ru not_active IP Right Cessation
- 2009-03-05 EP EP09717638.2A patent/EP2254869B1/en active Active
- 2009-03-05 HU HUE09718467A patent/HUE027098T2/en unknown
- 2009-03-05 AU AU2009221083A patent/AU2009221083B2/en not_active Ceased
- 2009-03-05 WO PCT/EP2009/052585 patent/WO2009109613A2/en not_active Ceased
- 2009-03-05 CA CA2712403A patent/CA2712403C/en not_active Expired - Fee Related
- 2009-03-05 PL PL09717638T patent/PL2254869T3/pl unknown
- 2009-03-05 BR BRPI0907977-7A patent/BRPI0907977A2/pt not_active IP Right Cessation
- 2009-03-05 MX MX2010009626A patent/MX2010009626A/es active IP Right Grant
- 2009-03-05 DK DK09718467.5T patent/DK2254870T3/en active
- 2009-03-05 CA CA2712703A patent/CA2712703C/en not_active Expired - Fee Related
- 2009-03-05 SI SI200931404A patent/SI2254870T1/sl unknown
- 2009-03-05 LT LTEP09717638.2T patent/LT2254869T/lt unknown
- 2009-03-05 PT PT97176382T patent/PT2254869T/pt unknown
- 2009-03-05 GE GEAP200911965A patent/GEP20135912B/en unknown
- 2009-03-05 ES ES09717638.2T patent/ES2637009T3/es active Active
- 2009-03-05 PL PL09718467T patent/PL2254870T3/pl unknown
- 2009-03-05 MX MX2010009623A patent/MX2010009623A/es active IP Right Grant
- 2009-03-05 KR KR1020107017445A patent/KR101599867B1/ko not_active Expired - Fee Related
- 2009-03-05 EP EP09718467.5A patent/EP2254870B1/en active Active
- 2009-03-05 SI SI200931705T patent/SI2254869T1/sl unknown
- 2009-03-05 AU AU2009221089A patent/AU2009221089B2/en not_active Ceased
- 2009-03-05 US US12/864,767 patent/US7919518B2/en not_active Expired - Fee Related
- 2009-03-05 SG SG2013013123A patent/SG188177A1/en unknown
- 2009-03-05 HR HRP20171208TT patent/HRP20171208T1/hr unknown
- 2009-03-05 EP EP17153930.7A patent/EP3181551A1/en not_active Withdrawn
- 2009-03-05 JP JP2010549143A patent/JP5509099B2/ja active Active
- 2009-03-05 GE GEAP200911963A patent/GEP20135983B/en unknown
- 2009-03-06 AR ARP090100800A patent/AR070810A1/es unknown
- 2009-03-06 AR ARP090100801A patent/AR070811A1/es unknown
- 2009-05-03 UA UAA201008883A patent/UA103605C2/uk unknown
- 2009-05-03 UA UAA201008570A patent/UA105170C2/uk unknown
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2010
- 2010-07-08 IL IL206893A patent/IL206893A0/en not_active IP Right Cessation
- 2010-07-21 IL IL207131A patent/IL207131A/en not_active IP Right Cessation
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2011
- 2011-03-07 US US13/041,557 patent/US8283348B2/en not_active Expired - Fee Related
- 2011-10-06 IL IL215579A patent/IL215579A/en not_active IP Right Cessation
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2016
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