BG107460A - Производни на бензимидазола, тяхното получаване иприложението им в терапията - Google Patents
Производни на бензимидазола, тяхното получаване иприложението им в терапията Download PDFInfo
- Publication number
- BG107460A BG107460A BG107460A BG10746003A BG107460A BG 107460 A BG107460 A BG 107460A BG 107460 A BG107460 A BG 107460A BG 10746003 A BG10746003 A BG 10746003A BG 107460 A BG107460 A BG 107460A
- Authority
- BG
- Bulgaria
- Prior art keywords
- group
- hydrogen atom
- alkyl group
- quinolein
- atom
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 14
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title abstract description 3
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title abstract 2
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 125
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 55
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 41
- -1 -(CH2)pCOOR Chemical group 0.000 claims abstract description 37
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 28
- 229910052799 carbon Chemical group 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract description 10
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 9
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims abstract description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 6
- 150000003512 tertiary amines Chemical class 0.000 claims abstract description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000005843 halogen group Chemical group 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 239000000543 intermediate Substances 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 10
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- 239000002585 base Substances 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 7
- 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 description 6
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
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- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 150000003335 secondary amines Chemical class 0.000 claims description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 208000035475 disorder Diseases 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- AVJKDKWRVSSJPK-UHFFFAOYSA-N 1-(4-fluorophenyl)piperazine Chemical compound C1=CC(F)=CC=C1N1CCNCC1 AVJKDKWRVSSJPK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
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- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 230000007170 pathology Effects 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 238000002054 transplantation Methods 0.000 claims description 3
- HDQZNKSAVGKPSC-UHFFFAOYSA-N 2-[4-(4-fluorophenyl)piperazin-1-yl]-5-methyl-1,3-diazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-9-one Chemical compound N=1C(=C23)C(C)=CC=C2C(=O)CCCN3C=1N(CC1)CCN1C1=CC=C(F)C=C1 HDQZNKSAVGKPSC-UHFFFAOYSA-N 0.000 claims description 2
- KKJUPNGICOCCDW-UHFFFAOYSA-N 7-N,N-Dimethylamino-1,2,3,4,5-pentathiocyclooctane Chemical compound CN(C)C1CSSSSSC1 KKJUPNGICOCCDW-UHFFFAOYSA-N 0.000 claims description 2
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- 208000033626 Renal failure acute Diseases 0.000 claims description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 2
- 206010040070 Septic Shock Diseases 0.000 claims description 2
- 206010052779 Transplant rejections Diseases 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- 206010047115 Vasculitis Diseases 0.000 claims description 2
- 201000011040 acute kidney failure Diseases 0.000 claims description 2
- 208000012998 acute renal failure Diseases 0.000 claims description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 206010008118 cerebral infarction Diseases 0.000 claims description 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 208000026278 immune system disease Diseases 0.000 claims description 2
- 230000002757 inflammatory effect Effects 0.000 claims description 2
- 208000028867 ischemia Diseases 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 206010028417 myasthenia gravis Diseases 0.000 claims description 2
- 208000010125 myocardial infarction Diseases 0.000 claims description 2
- 208000031225 myocardial ischemia Diseases 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- 230000036303 septic shock Effects 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- XNMYNYSCEJBRPZ-UHFFFAOYSA-N 2-[(3-butyl-1-isoquinolinyl)oxy]-N,N-dimethylethanamine Chemical compound C1=CC=C2C(OCCN(C)C)=NC(CCCC)=CC2=C1 XNMYNYSCEJBRPZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 208000005189 Embolism Diseases 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- 229910001508 alkali metal halide Inorganic materials 0.000 claims 1
- 150000008045 alkali metal halides Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
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- 230000000302 ischemic effect Effects 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 abstract description 5
- 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 abstract 1
- 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 238000005160 1H NMR spectroscopy Methods 0.000 description 27
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
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- 238000003760 magnetic stirring Methods 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- 229910052938 sodium sulfate Inorganic materials 0.000 description 15
- 235000011152 sodium sulphate Nutrition 0.000 description 15
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 14
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
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- 238000003756 stirring Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
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- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- RQCNHUCCQJMSRG-UHFFFAOYSA-N tert-butyl piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1 RQCNHUCCQJMSRG-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| FR0010419A FR2812878B1 (fr) | 2000-08-08 | 2000-08-08 | Derives de benzimidazole, leur preparation et leur application en therapeutique |
| FR0014696A FR2816619B1 (fr) | 2000-11-15 | 2000-11-15 | Derives de benzimidazole, leur preparation et leur application en therapeutique |
| PCT/FR2001/002556 WO2002012239A1 (fr) | 2000-08-08 | 2001-08-06 | Derives de benzimidazole, leur preparation et leur application en therapeutique |
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| BG107460A true BG107460A (bg) | 2003-09-30 |
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| US20050119251A1 (en) * | 2001-12-21 | 2005-06-02 | Jian-Min Fu | Nicotinamide derivatives and their use as therapeutic agents |
| US20040014744A1 (en) * | 2002-04-05 | 2004-01-22 | Fortuna Haviv | Substituted pyridines having antiangiogenic activity |
| AU2003236686A1 (en) * | 2002-06-07 | 2003-12-22 | Altana Pharma Ag | 4,5-dihydro-imidazo(4,5,1-j) quinolin-6-ones as parp inhibitors |
| WO2003104233A1 (en) * | 2002-06-07 | 2003-12-18 | Altana Pharma Ag | 4,5-dihydro-imidazo (4,5,1-ij) quinolin-6-ones derivatives and their use as poly (adp-ribosyl) transferase (parp) inhibitors |
| WO2004108723A1 (en) * | 2003-06-04 | 2004-12-16 | Altana Pharma Ag | 4,5-dihydro-imidazo[4,5,1-ii]quinolin-6-ones as parp inhibitors |
| GB0317466D0 (en) * | 2003-07-25 | 2003-08-27 | Univ Sheffield | Use |
| CN102107008B (zh) | 2003-12-01 | 2013-04-03 | 库多斯药物有限公司 | 用于治疗癌症的dna损伤修复抑制剂 |
| TW200626148A (en) * | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
| CN101084211A (zh) * | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为治疗剂的用途 |
| BRPI0515489A (pt) * | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | derivados heterocìclicos e sua utilização como inibidores de estearoil-coa desaturase |
| AR051091A1 (es) * | 2004-09-20 | 2006-12-20 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
| CN101090724A (zh) * | 2004-09-20 | 2007-12-19 | 泽农医药公司 | 用于抑制人硬脂酰CoA去饱和酶的吡啶衍生物 |
| CN101083994A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其用作硬脂酰CoA去饱和酶抑制剂的用途 |
| WO2006034315A2 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes |
| AU2005329423A1 (en) * | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| BRPI0515500A (pt) * | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | derivados piridazina para inibição de estearoil-coa-desaturase |
| WO2006074991A1 (en) * | 2005-01-11 | 2006-07-20 | Neurosearch A/S | Novel 2-amino benzimidazole derivatives and their use as modulators of small-conductance calcium-activated potassium channels |
| WO2007130075A1 (en) * | 2005-06-03 | 2007-11-15 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
| RU2008101923A (ru) * | 2005-08-05 | 2009-09-10 | Астразенека Аб (Se) | Трициклические бензимидазолы и их применение в качестве модуляторов метаботропного глутаматного рецептора |
| CA2654666A1 (en) * | 2006-07-03 | 2008-01-10 | Neurosearch A/S | Pharmaceutical compositions |
| GB0716532D0 (en) | 2007-08-24 | 2007-10-03 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| GB201220157D0 (en) | 2012-11-08 | 2012-12-26 | Selvita Sa | Substitute tricyclic benzimidazoles as kinase inhibitors |
| CN103923088B (zh) * | 2013-01-11 | 2016-09-07 | 上海汇伦生命科技有限公司 | 2,5-二氮杂双环[2.2.1]庚烷类化合物和制备方法、其药用组合物及其在医药上的应用 |
| SG11201506924YA (en) * | 2013-03-15 | 2015-09-29 | Incyte Corp | Tricyclic heterocycles as bet protein inhibitors |
| CN104230896A (zh) * | 2013-06-17 | 2014-12-24 | 上海汇伦生命科技有限公司 | 苯并咪唑-2-哌嗪杂环类化合物、其药物组合物及其制备方法和用途 |
| WO2015095492A1 (en) | 2013-12-19 | 2015-06-25 | Incyte Corporation | Tricyclic heterocycles as bet protein inhibitors |
| EP3674302B1 (en) | 2014-04-23 | 2023-03-01 | Incyte Holdings Corporation | 1h-pyrrolo[2,3-c]pyridin-7(6h)-ones and pyrazolo[3,4-c]pyridin-7(6h)-ones as inhibitors of bet proteins |
| CN107922423B (zh) * | 2015-05-29 | 2020-10-27 | 盐野义制药株式会社 | 具有hiv复制抑制作用的含氮三环性衍生物 |
| SI3472157T1 (sl) | 2016-06-20 | 2023-07-31 | Incyte Corporation | Kristalinične trdne oblike zaviralca BET |
| CN110661676B (zh) * | 2018-06-29 | 2022-06-28 | 大唐移动通信设备有限公司 | 一种带宽部分的测量方法、配置方法、终端及网络设备 |
| CN111349094B (zh) * | 2020-04-23 | 2021-02-02 | 杭州师范大学 | 一种6H-咪唑[4,5,1-ij]并喹诺酮及其合成方法和应用 |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
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| FR2710915B1 (fr) * | 1993-10-04 | 1995-11-24 | Synthelabo | Dérivés de pipéridine, leur préparation et leur utilisation en thérapeutique. |
| FR2731708B1 (fr) * | 1995-03-13 | 1997-04-30 | Synthelabo | Derives de piperidine, leur procede de preparation et leur application en therapeutique |
| UA61158C2 (uk) * | 1998-11-27 | 2003-11-17 | Басф Акціенгезелльшафт | Похідні бензимідазолу та лікарський засіб на їх основі |
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- 2001-08-06 SK SK158-2003A patent/SK1582003A3/sk unknown
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- 2001-08-06 DE DE60107859T patent/DE60107859T2/de not_active Expired - Lifetime
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