JP2017510611A5 - - Google Patents
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- JP2017510611A5 JP2017510611A5 JP2016561780A JP2016561780A JP2017510611A5 JP 2017510611 A5 JP2017510611 A5 JP 2017510611A5 JP 2016561780 A JP2016561780 A JP 2016561780A JP 2016561780 A JP2016561780 A JP 2016561780A JP 2017510611 A5 JP2017510611 A5 JP 2017510611A5
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- Prior art keywords
- compound
- aryl
- pharmaceutical composition
- alkyl
- cry
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 64
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 64
- 125000000623 heterocyclic group Chemical group 0.000 claims description 46
- 201000010099 disease Diseases 0.000 claims description 32
- 208000035475 disorder Diseases 0.000 claims description 32
- 230000001404 mediated effect Effects 0.000 claims description 32
- 239000008194 pharmaceutical composition Substances 0.000 claims description 28
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 26
- 108010037139 Cryptochromes Proteins 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 21
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 20
- 101150078024 CRY2 gene Proteins 0.000 claims description 18
- 101150102464 Cry1 gene Proteins 0.000 claims description 18
- 125000002619 bicyclic group Chemical group 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 16
- 229940124597 therapeutic agent Drugs 0.000 claims description 16
- KCYOZNARADAZIZ-CWBQGUJCSA-N 2-[(2e,4e,6e,8e,10e,12e,14e)-15-(4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl)-6,11-dimethylhexadeca-2,4,6,8,10,12,14-heptaen-2-yl]-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol Chemical compound O1C2(C)CC(O)CC(C)(C)C2=CC1C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)C1C=C2C(C)(C)CCCC2(C)O1 KCYOZNARADAZIZ-CWBQGUJCSA-N 0.000 claims description 14
- KCYOZNARADAZIZ-PPBBKLJYSA-N Cryptochrome Natural products O[C@@H]1CC(C)(C)C=2[C@@](C)(O[C@H](/C(=C\C=C\C(=C/C=C/C=C(\C=C\C=C(\C)/[C@H]3O[C@@]4(C)C(C(C)(C)CCC4)=C3)/C)\C)/C)C=2)C1 KCYOZNARADAZIZ-PPBBKLJYSA-N 0.000 claims description 14
- KCYOZNARADAZIZ-XZOHMNSDSA-N beta-cryptochrome Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C1OC2(C)CC(O)CC(C)(C)C2=C1)C=CC=C(/C)C3OC4(C)CCCC(C)(C)C4=C3 KCYOZNARADAZIZ-XZOHMNSDSA-N 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 239000003112 inhibitor Substances 0.000 claims description 12
- 125000002950 monocyclic group Chemical group 0.000 claims description 12
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- 208000010412 Glaucoma Diseases 0.000 claims description 8
- 102000003676 Glucocorticoid Receptors Human genes 0.000 claims description 8
- 108090000079 Glucocorticoid Receptors Proteins 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 238000012544 monitoring process Methods 0.000 claims description 8
- 230000003247 decreasing effect Effects 0.000 claims description 7
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000217 alkyl group Chemical group 0.000 claims description 6
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- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 101150008094 per1 gene Proteins 0.000 claims description 6
- 108700005075 Regulator Genes Proteins 0.000 claims description 5
- 230000001105 regulatory effect Effects 0.000 claims description 5
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 claims description 4
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- USUZGMWDZDXMDG-CYBMUJFWSA-N 4-[(5r)-6,7-dihydro-5h-pyrrolo[1,2-c]imidazol-5-yl]-3-fluorobenzonitrile Chemical compound FC1=CC(C#N)=CC=C1[C@@H]1N2C=NC=C2CC1 USUZGMWDZDXMDG-CYBMUJFWSA-N 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 208000002177 Cataract Diseases 0.000 claims description 4
- JWBOIMRXGHLCPP-UHFFFAOYSA-N Chloditan Chemical compound C=1C=CC=C(Cl)C=1C(C(Cl)Cl)C1=CC=C(Cl)C=C1 JWBOIMRXGHLCPP-UHFFFAOYSA-N 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
- 108010009911 Cytochrome P-450 CYP11B2 Proteins 0.000 claims description 4
- 102100024329 Cytochrome P450 11B2, mitochondrial Human genes 0.000 claims description 4
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- 108010067722 Dipeptidyl Peptidase 4 Proteins 0.000 claims description 4
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- 108010049356 Steroid 11-beta-Hydroxylase Proteins 0.000 claims description 4
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- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 4
- 150000001408 amides Chemical group 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 210000001175 cerebrospinal fluid Anatomy 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 201000009101 diabetic angiopathy Diseases 0.000 claims description 4
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 4
- 201000002249 diabetic peripheral angiopathy Diseases 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 claims description 4
- 229960001690 etomidate Drugs 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229960004125 ketoconazole Drugs 0.000 claims description 4
- 229940038098 korlym Drugs 0.000 claims description 4
- 208000002780 macular degeneration Diseases 0.000 claims description 4
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 4
- 229960003105 metformin Drugs 0.000 claims description 4
- FJLBFSROUSIWMA-UHFFFAOYSA-N metyrapone Chemical compound C=1C=CN=CC=1C(C)(C)C(=O)C1=CC=CN=C1 FJLBFSROUSIWMA-UHFFFAOYSA-N 0.000 claims description 4
- 229960004465 metyrapone Drugs 0.000 claims description 4
- VKHAHZOOUSRJNA-GCNJZUOMSA-N mifepristone Chemical compound C1([C@@H]2C3=C4CCC(=O)C=C4CC[C@H]3[C@@H]3CC[C@@]([C@]3(C2)C)(O)C#CC)=CC=C(N(C)C)C=C1 VKHAHZOOUSRJNA-GCNJZUOMSA-N 0.000 claims description 4
- 229960000350 mitotane Drugs 0.000 claims description 4
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- NEEFMPSSNFRRNC-HQUONIRXSA-N pasireotide aspartate Chemical compound OC(=O)[C@@H](N)CC(O)=O.OC(=O)[C@@H](N)CC(O)=O.C([C@H]1C(=O)N2C[C@@H](C[C@H]2C(=O)N[C@H](C(=O)N[C@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@H](C(N[C@@H](CC=2C=CC(OCC=3C=CC=CC=3)=CC=2)C(=O)N1)=O)CCCCN)C=1C=CC=CC=1)OC(=O)NCCN)C1=CC=CC=C1 NEEFMPSSNFRRNC-HQUONIRXSA-N 0.000 claims description 4
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- 125000001424 substituent group Chemical group 0.000 claims description 4
- 238000011477 surgical intervention Methods 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- FJVWQOQSMAKEAY-OXJNMPFZSA-N C1=CC=CC=2C3=CC=CC=C3N(C12)C[C@](CN1C([C@H](CC1)F)=O)(C)O Chemical compound C1=CC=CC=2C3=CC=CC=C3N(C12)C[C@](CN1C([C@H](CC1)F)=O)(C)O FJVWQOQSMAKEAY-OXJNMPFZSA-N 0.000 claims description 3
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- CTLHGLZELHMPOK-UHFFFAOYSA-N FC=1C=CC=2N(C3=CC=C(C=C3C2C1)F)CC(CN1C(C(CC1)F)=O)O Chemical compound FC=1C=CC=2N(C3=CC=C(C=C3C2C1)F)CC(CN1C(C(CC1)F)=O)O CTLHGLZELHMPOK-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- -1 azido, hydroxyl Chemical group 0.000 claims description 3
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 3
- 201000009395 primary hyperaldosteronism Diseases 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- MUVYYQQLOKRDQS-UHFFFAOYSA-N 1-[3-(3,6-difluorocarbazol-9-yl)-2-hydroxypropyl]imidazolidin-2-one Chemical compound FC=1C=CC=2N(C3=CC=C(C=C3C2C1)F)CC(CN1C(NCC1)=O)O MUVYYQQLOKRDQS-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
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- 150000001924 cycloalkanes Chemical class 0.000 claims description 2
- BPXYEYJNCXITEY-UHFFFAOYSA-N diazonio(trifluoromethoxy)azanide Chemical compound FC(F)(F)ON=[N+]=[N-] BPXYEYJNCXITEY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical group O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical group O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 2
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- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical group OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
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- WIBSYPXJJKRRRB-UHFFFAOYSA-N 3,6-difluoro-9h-carbazole Chemical compound C1=C(F)C=C2C3=CC(F)=CC=C3NC2=C1 WIBSYPXJJKRRRB-UHFFFAOYSA-N 0.000 claims 1
- 208000004930 Fatty Liver Diseases 0.000 claims 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N ethyl-n-butyl-ketone Natural products CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 claims 1
- VLYOSQYVOMGGDB-MRTQMZDGSA-N (3S)-1-[(2S)-3-carbazol-9-yl-2-hydroxy-2-methylpropyl]-3-fluoropyrrolidin-2-one (4R)-1-[(2R)-3-carbazol-9-yl-2-hydroxypropyl]-4-methylimidazolidin-2-one Chemical compound C1=CC=CC=2C3=CC=CC=C3N(C12)C[C@H](CN1C(N[C@@H](C1)C)=O)O.C1=CC=CC=2C3=CC=CC=C3N(C12)C[C@](CN1C([C@H](CC1)F)=O)(C)O VLYOSQYVOMGGDB-MRTQMZDGSA-N 0.000 description 1
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461976350P | 2014-04-07 | 2014-04-07 | |
| US61/976,350 | 2014-04-07 | ||
| PCT/US2015/024537 WO2015157182A1 (en) | 2014-04-07 | 2015-04-06 | Carbazole-containing amides, carbamates, and ureas as cryptochrome modulators |
Related Child Applications (1)
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Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ728724A (en) | 2012-05-11 | 2018-03-23 | Reset Therapeutics Inc | Carbazole-containing sulfonamides as cryptochrome modulators |
| TWI690521B (zh) | 2014-04-07 | 2020-04-11 | 美商同步製藥公司 | 作為隱花色素調節劑之含有咔唑之醯胺類、胺基甲酸酯類及脲類 |
| WO2018013546A1 (en) * | 2016-07-11 | 2018-01-18 | The Regents Of The University Of California | Bic inhibitor of cry-cry and cry-cib oligomerization/clustering |
| CN108779115B (zh) | 2016-10-14 | 2021-02-26 | 江苏恒瑞医药股份有限公司 | 五元杂芳环并桥环类衍生物、其制备方法及其在医药上的应用 |
| JP6835308B2 (ja) * | 2016-10-19 | 2021-02-24 | 国立研究開発法人理化学研究所 | クリプトクロムの機能を抑制するための組成物 |
| US12385914B2 (en) * | 2017-01-10 | 2025-08-12 | The Regents Of The University Of California | CRY1-clock-BMAL1 complex-disrupting agents and methods of identifying and using same |
| US11713470B2 (en) * | 2017-03-20 | 2023-08-01 | University of Pittsburgh—of the Commonwealth System of Higher Education | Targeted gene therapies for pain and other neuro-related disorders |
| US11542275B2 (en) * | 2018-03-22 | 2023-01-03 | Aurigene Discovery Technologies Limited | Substituted imidazolidin-2-one derivatives as PRMT5 inhibitors |
| US20210267939A1 (en) * | 2018-06-18 | 2021-09-02 | Duke University | Compositions and methods for treating nafld/nash and related disease phenotypes |
| US20210393621A1 (en) | 2018-10-26 | 2021-12-23 | 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 |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| MA56226A (fr) | 2018-12-07 | 2022-04-20 | Neurocrine Biosciences Inc | Antagoniste du récepteur crf1, formulations pharmaceutiques et ses formes solides pour le traitement de l'hyperplasie surrénale congénitale |
| CN111217741B (zh) * | 2019-03-01 | 2022-03-15 | 广东省中医院（广州中医药大学第二附属医院、广州中医药大学第二临床医学院、广东省中医药科学院） | 氟取代单咔唑类衍生物、其制备方法及应用 |
| CN111285793B (zh) * | 2019-03-01 | 2022-04-22 | 广州中医药大学(广州中医药研究院) | 氟取代双分子咔唑衍生物、其制备方法及应用 |
| EP3934649A4 (en) | 2019-03-04 | 2022-11-23 | Strongbridge Dublin Limited | METHODS OF TREATING A DISEASE WITH LEVOKETOCONAZOLE |
| US20220296604A1 (en) * | 2019-08-08 | 2022-09-22 | New York University | Indole compounds as modulators of rage activity and uses thereof |
| CN118252829A (zh) | 2019-09-27 | 2024-06-28 | 纽罗克里生物科学有限公司 | Crf受体拮抗剂及使用方法 |
| CN112162028A (zh) * | 2020-09-29 | 2021-01-01 | 中国农业科学院农业质量标准与检测技术研究所 | 一种用于草莓组织中维生素c的质谱成像方法 |
| GB202106143D0 (en) * | 2021-04-29 | 2021-06-16 | Adaptive Diagnostics Ltd | Determination of the presence of a target species |
| CN112986451B (zh) * | 2021-05-06 | 2022-05-17 | 湖南师范大学 | 一种基于风味特征的杂交鱼类肉品质评价方法 |
| CN113461674B (zh) * | 2021-08-09 | 2022-05-13 | 山东农业大学 | 一种促进植物根系生长的酰胺类化合物及其制备方法和应用 |
| EP4382529A1 (en) | 2022-12-07 | 2024-06-12 | Bayer Consumer Care AG | A process for preparing pure (3s)-pyrrolidin-3-ol and pure (3s)-pyrrolidin-3-ol hydrochloride |
| CN115974763B (zh) * | 2022-12-26 | 2025-03-11 | 常州大学 | 一种咔唑衍生物及其应用 |
| CN117567396A (zh) * | 2023-11-27 | 2024-02-20 | 宁夏坤正生物科技有限公司 | R型3-氯-1,2-丙二醇制s型缩水甘油甲磺酸酯的工艺 |
Family Cites Families (106)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4302386A (en) | 1978-08-25 | 1981-11-24 | The Ohio State University | Antigenic modification of polypeptides |
| US4105776A (en) | 1976-06-21 | 1978-08-08 | E. R. Squibb & Sons, Inc. | Proline derivatives and related compounds |
| CA1178414A (en) | 1978-02-08 | 1984-11-27 | Toyo Boseki Kabushiki Kaisha (Trading Under The Name Of Toyobo Co., Ltd.) | Packaging material having excellent seal packaging property |
| US4275149A (en) | 1978-11-24 | 1981-06-23 | Syva Company | Macromolecular environment control in specific receptor assays |
| US4233402A (en) | 1978-04-05 | 1980-11-11 | Syva Company | Reagents and method employing channeling |
| US4325952A (en) | 1978-04-18 | 1982-04-20 | Aziende Chimiche Riunite Angelini Francesco | Method of treating abstinence syndrome with cycloaklyltriazoles |
| US4316906A (en) | 1978-08-11 | 1982-02-23 | E. R. Squibb & Sons, Inc. | Mercaptoacyl derivatives of substituted prolines |
| IL58849A (en) | 1978-12-11 | 1983-03-31 | Merck & Co Inc | Carboxyalkyl dipeptides and derivatives thereof,their preparation and pharmaceutical compositions containing them |
| US4276890A (en) | 1979-04-11 | 1981-07-07 | Fichera Anthony T | Tobacco smoking inhibitor |
| US4231938A (en) | 1979-06-15 | 1980-11-04 | Merck & Co., Inc. | Hypocholesteremic fermentation products and process of preparation |
| US4508729A (en) | 1979-12-07 | 1985-04-02 | Adir | Substituted iminodiacids, their preparation and pharmaceutical compositions containing them |
| US4444784A (en) | 1980-08-05 | 1984-04-24 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| DK149080C (da) | 1980-06-06 | 1986-07-28 | Sankyo Co | Fremgangsmaade til fremstilling af derivater af ml-236b-carboxylsyre |
| US4376110A (en) | 1980-08-04 | 1983-03-08 | Hybritech, Incorporated | Immunometric assays using monoclonal antibodies |
| US4344949A (en) | 1980-10-03 | 1982-08-17 | Warner-Lambert Company | Substituted acyl derivatives of 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids |
| ZA817261B (en) | 1980-10-23 | 1982-09-29 | Schering Corp | Carboxyalkyl dipeptides,processes for their production and pharmaceutical compositions containing them |
| US4337201A (en) | 1980-12-04 | 1982-06-29 | E. R. Squibb & Sons, Inc. | Phosphinylalkanoyl substituted prolines |
| US4410520A (en) | 1981-11-09 | 1983-10-18 | Ciba-Geigy Corporation | 3-Amino-[1]-benzazepin-2-one-1-alkanoic acids |
| GB2128984B (en) | 1982-05-12 | 1985-05-22 | Hoffmann La Roche | Diaza-bicyclic compounds |
| US4659678A (en) | 1982-09-29 | 1987-04-21 | Serono Diagnostics Limited | Immunoassay of antigens |
| US4739073A (en) | 1983-11-04 | 1988-04-19 | Sandoz Pharmaceuticals Corp. | Intermediates in the synthesis of indole analogs of mevalonolactone and derivatives thereof |
| US4727022A (en) | 1984-03-14 | 1988-02-23 | Syntex (U.S.A.) Inc. | Methods for modulating ligand-receptor interactions and their application |
| US4780401A (en) | 1984-04-09 | 1988-10-25 | Ciba-Geigy Corporation | Novel monoclonal antibodies to human renin and hybridoma cells, processes for their preparation and their applications |
| US4845079A (en) | 1985-01-23 | 1989-07-04 | Luly Jay R | Peptidylaminodiols |
| US5066643A (en) | 1985-02-19 | 1991-11-19 | Sandoz Ltd. | Fluorine and chlorine statine or statone containing peptides and method of use |
| US4894437A (en) | 1985-11-15 | 1990-01-16 | The Upjohn Company | Novel renin inhibiting polypeptide analogs containing S-aryl-D- or L- or DL-cysteinyl, 3-(arylthio)lactic acid or 3-(arylthio)alkyl moieties |
| US4885292A (en) | 1986-02-03 | 1989-12-05 | E. R. Squibb & Sons, Inc. | N-heterocyclic alcohol renin inhibitors |
| US4816463A (en) | 1986-04-01 | 1989-03-28 | Warner-Lambert Company | Substituted diimidazo [1,5-a: 4',5'-d]pyridines having antihypertensive activity |
| CA1334092C (en) | 1986-07-11 | 1995-01-24 | David John Carini | Angiotensin ii receptor blocking imidazoles |
| US4772684A (en) | 1987-01-20 | 1988-09-20 | Triton Biosciences, Inc. | Peptides affecting blood pressure regulation |
| US4786653A (en) | 1987-08-24 | 1988-11-22 | Golwyn Daniel H | Treatment of neurotransmitter-linked drug abuse |
| US4980283A (en) | 1987-10-01 | 1990-12-25 | Merck & Co., Inc. | Renin-inhibitory pepstatin phenyl derivatives |
| US5089471A (en) | 1987-10-01 | 1992-02-18 | G. D. Searle & Co. | Peptidyl beta-aminoacyl aminodiol carbamates as anti-hypertensive agents |
| US5034512A (en) | 1987-10-22 | 1991-07-23 | Warner-Lambert Company | Branched backbone renin inhibitors |
| US5063207A (en) | 1987-10-26 | 1991-11-05 | Warner-Lambert Company | Renin inhibitors, method for using them, and compositions containing them |
| US5055466A (en) | 1987-11-23 | 1991-10-08 | E. R. Squibb & Sons, Inc. | N-morpholino derivatives and their use as anti-hypertensive agents |
| US5081127A (en) | 1988-01-07 | 1992-01-14 | E. I. Du Pont De Nemours And Company | Substituted 1,2,3-triazole angiotensin II antagonists |
| US5036054A (en) | 1988-02-11 | 1991-07-30 | Warner-Lambert Company | Renin inhibitors containing alpha-heteroatom amino acids |
| US4788189A (en) | 1988-02-29 | 1988-11-29 | Glazer Howard I | Method to treat smoking withdrawal symptoms by potentiated central noradrenergic blocking |
| US5036053A (en) | 1988-05-27 | 1991-07-30 | Warner-Lambert Company | Diol-containing renin inhibitors |
| DE3841520A1 (de) | 1988-12-09 | 1990-06-13 | Hoechst Ag | Enzymhemmende harnstoffderivate von dipeptiden, verfahren zu ihrer herstellung, diese enthaltende mittel und ihre verwendung |
| US5106835A (en) | 1988-12-27 | 1992-04-21 | American Cyanamid Company | Renin inhibitors |
| DE4004820A1 (de) | 1989-08-05 | 1991-04-25 | Bayer Ag | Renininhibitoren, verfahren zur herstellung und ihre verwendung in arzneimitteln |
| US5064825A (en) | 1989-06-01 | 1991-11-12 | Merck & Co., Inc. | Angiotensin ii antagonists |
| US5744101A (en) | 1989-06-07 | 1998-04-28 | Affymax Technologies N.V. | Photolabile nucleoside protecting groups |
| FI94339C (fi) | 1989-07-21 | 1995-08-25 | Warner Lambert Co | Menetelmä farmaseuttisesti käyttökelpoisen /R-(R*,R*)/-2-(4-fluorifenyyli)- , -dihydroksi-5-(1-metyylietyyli)-3-fenyyli-4-/(fenyyliamino)karbonyyli/-1H-pyrroli-1-heptaanihapon ja sen farmaseuttisesti hyväksyttävien suolojen valmistamiseksi |
| US5063208A (en) | 1989-07-26 | 1991-11-05 | Abbott Laboratories | Peptidyl aminodiol renin inhibitors |
| US5098924A (en) | 1989-09-15 | 1992-03-24 | E. R. Squibb & Sons, Inc. | Diol sulfonamide and sulfinyl renin inhibitors |
| US5104869A (en) | 1989-10-11 | 1992-04-14 | American Cyanamid Company | Renin inhibitors |
| US5114937A (en) | 1989-11-28 | 1992-05-19 | Warner-Lambert Company | Renin inhibiting nonpeptides |
| US5073566A (en) | 1989-11-30 | 1991-12-17 | Eli Lilly And Company | Angiotensin ii antagonist 1,3-imidazoles and use thereas |
| US5750015A (en) | 1990-02-28 | 1998-05-12 | Soane Biosciences | Method and device for moving molecules by the application of a plurality of electrical fields |
| US5075451A (en) | 1990-03-08 | 1991-12-24 | American Home Products Corporation | Pyrrolimidazolones useful as renin inhibitors |
| US5064965A (en) | 1990-03-08 | 1991-11-12 | American Home Products Corporation | Renin inhibitors |
| US5095119A (en) | 1990-03-08 | 1992-03-10 | American Home Products Corporation | Renin inhibitors |
| US5085992A (en) | 1990-07-19 | 1992-02-04 | Merck & Co., Inc. | Microbial transformation process for antihypertensive products |
| US5087634A (en) | 1990-10-31 | 1992-02-11 | G. D. Searle & Co. | N-substituted imidazol-2-one compounds for treatment of circulatory disorders |
| US5071837A (en) | 1990-11-28 | 1991-12-10 | Warner-Lambert Company | Novel renin inhibiting peptides |
| US5604260A (en) | 1992-12-11 | 1997-02-18 | Merck Frosst Canada Inc. | 5-methanesulfonamido-1-indanones as an inhibitor of cyclooxygenase-2 |
| US5474995A (en) | 1993-06-24 | 1995-12-12 | Merck Frosst Canada, Inc. | Phenyl heterocycles as cox-2 inhibitors |
| GB9602877D0 (en) | 1996-02-13 | 1996-04-10 | Merck Frosst Canada Inc | 3,4-Diaryl-2-hydroxy-2,5- dihydrofurans as prodrugs to cox-2 inhibitors |
| US5538848A (en) | 1994-11-16 | 1996-07-23 | Applied Biosystems Division, Perkin-Elmer Corp. | Method for detecting nucleic acid amplification using self-quenching fluorescence probe |
| WO1995018799A1 (en) | 1994-01-10 | 1995-07-13 | Merck Frosst Canada Inc. | Phenyl heterocycles as cox-2 inhibitors |
| US5521213A (en) | 1994-08-29 | 1996-05-28 | Merck Frosst Canada, Inc. | Diaryl bicyclic heterocycles as inhibitors of cyclooxygenase-2 |
| JPH10507765A (ja) | 1994-10-27 | 1998-07-28 | メルク フロスト カナダ インコーポレーテツド | シクロオキシゲナーゼ−２阻害剤として有用なスチルベン誘導体 |
| US5552422A (en) | 1995-01-11 | 1996-09-03 | Merck Frosst Canada, Inc. | Aryl substituted 5,5 fused aromatic nitrogen compounds as anti-inflammatory agents |
| US5801155A (en) | 1995-04-03 | 1998-09-01 | Epoch Pharmaceuticals, Inc. | Covalently linked oligonucleotide minor grove binder conjugates |
| US5691374A (en) | 1995-05-18 | 1997-11-25 | Merck Frosst Canada Inc. | Diaryl-5-oxygenated-2-(5H) -furanones as COX-2 inhibitors |
| US5604253A (en) | 1995-05-22 | 1997-02-18 | Merck Frosst Canada, Inc. | N-benzylindol-3-yl propanoic acid derivatives as cyclooxygenase inhibitors |
| US5639780A (en) | 1995-05-22 | 1997-06-17 | Merck Frosst Canada, Inc. | N-benzyl indol-3-yl butanoic acid derivatives as cyclooxygenase inhibitors |
| US5643933A (en) | 1995-06-02 | 1997-07-01 | G. D. Searle & Co. | Substituted sulfonylphenylheterocycles as cyclooxygenase-2 and 5-lipoxygenase inhibitors |
| US5733909A (en) | 1996-02-01 | 1998-03-31 | Merck Frosst Canada, Inc. | Diphenyl stilbenes as prodrugs to COX-2 inhibitors |
| US5789413A (en) | 1996-02-01 | 1998-08-04 | Merck Frosst Canada, Inc. | Alkylated styrenes as prodrugs to COX-2 inhibitors |
| GB9607503D0 (en) | 1996-04-11 | 1996-06-12 | Merck Frosst Canada Inc | Bisaryl cyclobutenes derivatives as cyclooxygenase inhibitors |
| US5922742A (en) | 1996-04-23 | 1999-07-13 | Merck Frosst Canada | Pyridinyl-2-cyclopenten-1-ones as selective cyclooxygenase-2 inhibitors |
| US5677318A (en) | 1996-07-11 | 1997-10-14 | Merck Frosst Canada, Inc. | Diphenyl-1,2-3-thiadiazoles as anti-inflammatory agents |
| US5861419A (en) | 1996-07-18 | 1999-01-19 | Merck Frosst Canad, Inc. | Substituted pyridines as selective cyclooxygenase-2 inhibitors |
| AR008331A1 (es) | 1997-01-23 | 1999-12-29 | Smithkline Beecham Corp | Compuestos antagonistas de un receptor de il-8, uso de los mismos para la fabricacion de medicamentos, procedimiento para su obtencion, composicionesfarmaceuticas que los contienen |
| US6475744B1 (en) | 1999-07-22 | 2002-11-05 | The General Hospital Corporation | Methods for identifying compounds which modulate circadian rhythm |
| US6399631B1 (en) | 1999-07-23 | 2002-06-04 | Pfizer Inc. | Carbazole neuropeptide Y5 antagonists |
| EP1236173A2 (en) | 1999-10-27 | 2002-09-04 | Biowulf Technologies, LLC | Methods and devices for identifying patterns in biological systems |
| KR101054732B1 (ko) | 2000-07-18 | 2011-08-05 | 더 유나이티드 스테이츠 오브 아메리카 애즈 리프리젠티드 바이 더 세크레터리 오브 더 디파트먼트 오브 헬쓰 앤드 휴먼 써비시즈 | 생물학적 데이터의 숨겨진 패턴에 근거한 생물학적 상태의 식별 방법 |
| CA2429633A1 (en) | 2000-11-16 | 2002-05-30 | Ciphergen Biosystems, Inc. | Method for analyzing mass spectra |
| US7113896B2 (en) | 2001-05-11 | 2006-09-26 | Zhen Zhang | System and methods for processing biological expression data |
| US20020193950A1 (en) | 2002-02-25 | 2002-12-19 | Gavin Edward J. | Method for analyzing mass spectra |
| WO2003105759A2 (en) * | 2002-06-12 | 2003-12-24 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Pharmacologic inhibition of myc function |
| US20040121305A1 (en) | 2002-12-18 | 2004-06-24 | Wiegand Roger Charles | Generation of efficacy, toxicity and disease signatures and methods of use thereof |
| WO2004088309A2 (en) | 2003-03-28 | 2004-10-14 | Cantata Laboratories, Inc. | Methods for diagnosing urinary tract and prostatic disorders |
| PL1732892T3 (pl) | 2004-03-26 | 2009-03-31 | Hoffmann La Roche | Tetrahydrokarbazole i pochodne |
| DE602005017162D1 (de) | 2004-08-19 | 2009-11-26 | Aventis Pharma Inc | 3-arylthioindol-2-carbonsäureamidderivate und ihre analoge als hemmer von caseinkinase i |
| ES2882684T3 (es) | 2006-04-07 | 2021-12-02 | Vertex Pharma | Preparación de moduladores de transportadores del casete de unión a ATP |
| CL2007003591A1 (es) | 2006-12-12 | 2008-02-29 | Wyeth Corp | Compuestos derivados de sulfonamida ciclicos, inhibidores de retoma de monoamina; procedimiento de preparacion; composicion farmaceutica; y uso para el tratamiento o prevencion de disfuncion sexual, trastorno gastrointestinal, trastorno genitourinari |
| CA2709784A1 (en) * | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| UA107652C2 (en) * | 2008-10-06 | 2015-02-10 | Incuron Llc | Carbazole compounds and therapeutic uses of the compounds |
| WO2010081115A1 (en) * | 2009-01-09 | 2010-07-15 | University Of Texas Southwestern Medical Center | Pro-neurogenic compounds |
| US8362277B2 (en) | 2009-01-09 | 2013-01-29 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| US9962368B2 (en) | 2009-01-09 | 2018-05-08 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| US9162980B2 (en) * | 2009-01-09 | 2015-10-20 | Board Of Regents Of The University Of Texas System | Anti-depression compounds |
| CN103415289B (zh) * | 2010-07-07 | 2017-04-12 | 得克萨斯州大学系统董事会 | 前神经原性化合物 |
| US20130116445A1 (en) | 2010-07-12 | 2013-05-09 | Colorado State University Research Foundation | Triazolium carbene catalysts and processes for asymmetric carbon-carbon bond formation |
| NZ728724A (en) * | 2012-05-11 | 2018-03-23 | Reset Therapeutics Inc | Carbazole-containing sulfonamides as cryptochrome modulators |
| WO2014031125A1 (en) * | 2012-08-24 | 2014-02-27 | Board Of Regents Of The University Of Texas System | Pro-neurogenic compounds |
| WO2014039515A2 (en) * | 2012-09-04 | 2014-03-13 | University Of Massachusetts | Antifungal agents and uses thereof |
| WO2014179785A1 (en) * | 2013-05-03 | 2014-11-06 | Inscent, Inc. | Improved honeybee repellents and uses thereof |
| US9353078B2 (en) | 2013-10-01 | 2016-05-31 | New York University | Amino, amido and heterocyclic compounds as modulators of rage activity and uses thereof |
| TWI690521B (zh) | 2014-04-07 | 2020-04-11 | 美商同步製藥公司 | 作為隱花色素調節劑之含有咔唑之醯胺類、胺基甲酸酯類及脲類 |
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