MX2007015084A - Derivados de ergolina y su uso como ligandos del receptor de quimiocina. - Google Patents
Derivados de ergolina y su uso como ligandos del receptor de quimiocina.Info
- Publication number
- MX2007015084A MX2007015084A MX2007015084A MX2007015084A MX2007015084A MX 2007015084 A MX2007015084 A MX 2007015084A MX 2007015084 A MX2007015084 A MX 2007015084A MX 2007015084 A MX2007015084 A MX 2007015084A MX 2007015084 A MX2007015084 A MX 2007015084A
- Authority
- MX
- Mexico
- Prior art keywords
- formula
- compound
- heteroaryl
- optionally substituted
- mmol
- Prior art date
Links
- 239000003446 ligand Substances 0.000 title claims abstract description 15
- 102000009410 Chemokine receptor Human genes 0.000 title claims abstract description 6
- 108050000299 Chemokine receptor Proteins 0.000 title claims abstract description 6
- AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical class O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 title abstract description 3
- -1 heteroaryl N-oxide Chemical class 0.000 claims abstract description 32
- 150000003839 salts Chemical group 0.000 claims abstract description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 208000035475 disorder Diseases 0.000 claims abstract description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 6
- 201000010099 disease Diseases 0.000 claims abstract description 6
- 230000001404 mediated effect Effects 0.000 claims abstract description 6
- 230000003993 interaction Effects 0.000 claims abstract description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical class 0.000 claims abstract description 4
- 125000004648 C2-C8 alkenyl group Chemical class 0.000 claims abstract description 3
- 125000004649 C2-C8 alkynyl group Chemical class 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
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- 238000011282 treatment Methods 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 3
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- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
- 101100134929 Gallus gallus COR9 gene Proteins 0.000 claims description 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 2
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 2
- 229940059260 amidate Drugs 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 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 2
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000000565 sulfonamide group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 101100448208 Human herpesvirus 6B (strain Z29) U69 gene Proteins 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical class 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
- 239000011541 reaction mixture Substances 0.000 description 42
- 239000002253 acid Substances 0.000 description 35
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 23
- 101000916050 Homo sapiens C-X-C chemokine receptor type 3 Proteins 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- 102100028990 C-X-C chemokine receptor type 3 Human genes 0.000 description 20
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000002994 raw material Substances 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- WXXVQWSDMOAHHV-UHFFFAOYSA-N quinoline-7-carboxylic acid Chemical compound C1=CC=NC2=CC(C(=O)O)=CC=C21 WXXVQWSDMOAHHV-UHFFFAOYSA-N 0.000 description 10
- 238000004809 thin layer chromatography Methods 0.000 description 10
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 9
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- 239000012071 phase Substances 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 7
- 239000005557 antagonist Substances 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000002519 immonomodulatory effect Effects 0.000 description 6
- 230000002757 inflammatory effect Effects 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 102100025279 C-X-C motif chemokine 11 Human genes 0.000 description 5
- 101710098272 C-X-C motif chemokine 11 Proteins 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- 239000007832 Na2SO4 Substances 0.000 description 4
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- 102100039498 Cytotoxic T-lymphocyte protein 4 Human genes 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 101000889276 Homo sapiens Cytotoxic T-lymphocyte protein 4 Proteins 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/04—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid 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 8
- C07D457/06—Lysergic acid amides
- C07D457/08—Lysergic acid amides in which the amide nitrogen is a member of a heterocyclic ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Physical Education & Sports Medicine (AREA)
- Endocrinology (AREA)
- Oncology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Communicable Diseases (AREA)
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- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Gastroenterology & Hepatology (AREA)
- Emergency Medicine (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0511060.6A GB0511060D0 (en) | 2005-05-31 | 2005-05-31 | Organic compounds |
| PCT/EP2006/005106 WO2006128658A1 (en) | 2005-05-31 | 2006-05-29 | Ergoline derivatives and their use as chemokine receptor ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2007015084A true MX2007015084A (es) | 2008-01-17 |
Family
ID=34834898
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2007015084A MX2007015084A (es) | 2005-05-31 | 2006-05-29 | Derivados de ergolina y su uso como ligandos del receptor de quimiocina. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7666877B2 (enExample) |
| EP (1) | EP1893611A1 (enExample) |
| JP (1) | JP5121703B2 (enExample) |
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Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG181896A1 (en) * | 2009-12-23 | 2012-07-30 | Map Pharmaceuticals Inc | Novel ergoline analogs |
| JP5874124B2 (ja) | 2010-06-28 | 2016-03-02 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | 緑内障の処置に使用するための薬学的組成物 |
| CA2838991A1 (en) | 2011-06-23 | 2012-12-27 | Map Pharmaceuticals, Inc. | Novel fluoroergoline analogs |
| CA2859173A1 (en) | 2011-12-19 | 2013-06-27 | Map Pharmaceuticals, Inc. | Novel iso-ergoline derivatives |
| WO2013095708A1 (en) | 2011-12-21 | 2013-06-27 | Map Pharmaceuticals, Inc. | Novel neuromodulatory compounds |
| AU2012382929A1 (en) * | 2012-06-22 | 2015-02-05 | Map Pharmaceuticals, Inc. | Novel cabergoline derivatives |
| US9012640B2 (en) | 2012-06-22 | 2015-04-21 | Map Pharmaceuticals, Inc. | Cabergoline derivatives |
| CN113149982A (zh) | 2015-01-20 | 2021-07-23 | Xoc制药股份有限公司 | 麦角灵化合物及其用途 |
| AU2016209490B2 (en) | 2015-01-20 | 2020-09-03 | Xoc Pharmaceuticals, Inc. | Isoergoline compounds and uses thereof |
| EP3630758A1 (en) | 2017-06-01 | 2020-04-08 | Xoc Pharmaceuticals, Inc | Ergoline derivatives for use in medicine |
| US12459965B2 (en) | 2017-10-09 | 2025-11-04 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| GB2571696B (en) | 2017-10-09 | 2020-05-27 | Compass Pathways Ltd | Large scale method for the preparation of Psilocybin and formulations of Psilocybin so produced |
| WO2020212951A1 (en) | 2019-04-17 | 2020-10-22 | Compass Pathfinder Limited | Methods for treating anxiety disorders, headache disorders, and eating disorders with psilocybin |
| WO2022232093A1 (en) | 2021-04-30 | 2022-11-03 | Mind Medicine, Inc. | Lsd salt crystal forms |
| AU2022331317B2 (en) | 2021-08-19 | 2025-09-11 | Definium Therapeutics US, Inc. | IMMEDIATE RELEASE FORMULATIONS OF d-LYSERGIC ACID DIETHYLAMIDE FOR THERAPEUTIC APPLICATIONS |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000042071A2 (en) * | 1999-01-12 | 2000-07-20 | Cambridge University Technical Services Ltd. | Compounds and methods to inhibit or augment an inflammatory response |
| RU2329263C2 (ru) | 2000-11-07 | 2008-07-20 | Новартис Аг | Производные имида индолилмалеиновой кислоты как ингибиторы протеинкиназы с |
| AR039209A1 (es) | 2002-04-03 | 2005-02-09 | Novartis Ag | Derivados de indolilmaleimida |
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2005
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2006
- 2006-05-29 US US11/914,570 patent/US7666877B2/en not_active Expired - Fee Related
- 2006-05-29 JP JP2008513997A patent/JP5121703B2/ja not_active Expired - Fee Related
- 2006-05-29 CA CA2608702A patent/CA2608702C/en not_active Expired - Fee Related
- 2006-05-29 KR KR1020077027902A patent/KR20080013971A/ko not_active Withdrawn
- 2006-05-29 RU RU2007147597/04A patent/RU2416613C2/ru not_active IP Right Cessation
- 2006-05-29 EP EP06753946A patent/EP1893611A1/en not_active Withdrawn
- 2006-05-29 CN CN2006800186451A patent/CN101184754B/zh not_active Expired - Fee Related
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- 2006-05-29 WO PCT/EP2006/005106 patent/WO2006128658A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| RU2007147597A (ru) | 2009-07-20 |
| CA2608702A1 (en) | 2006-12-07 |
| EP1893611A1 (en) | 2008-03-05 |
| BRPI0611489A2 (pt) | 2010-11-23 |
| JP5121703B2 (ja) | 2013-01-16 |
| RU2416613C2 (ru) | 2011-04-20 |
| WO2006128658A1 (en) | 2006-12-07 |
| CA2608702C (en) | 2013-10-15 |
| KR20080013971A (ko) | 2008-02-13 |
| GB0511060D0 (en) | 2005-07-06 |
| JP2008545725A (ja) | 2008-12-18 |
| CN101184754B (zh) | 2010-12-22 |
| US20090018127A1 (en) | 2009-01-15 |
| AU2006254395B2 (en) | 2010-09-09 |
| US7666877B2 (en) | 2010-02-23 |
| CN101184754A (zh) | 2008-05-21 |
| AU2006254395A1 (en) | 2006-12-07 |
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