RU2014153672A - NEW CABBERGOLINE DERIVATIVES - Google Patents
NEW CABBERGOLINE DERIVATIVES Download PDFInfo
- Publication number
- RU2014153672A RU2014153672A RU2014153672A RU2014153672A RU2014153672A RU 2014153672 A RU2014153672 A RU 2014153672A RU 2014153672 A RU2014153672 A RU 2014153672A RU 2014153672 A RU2014153672 A RU 2014153672A RU 2014153672 A RU2014153672 A RU 2014153672A
- Authority
- RU
- Russia
- Prior art keywords
- alkyl
- substituted
- hydrogen
- compound
- fluorine atoms
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract 38
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 38
- 239000001257 hydrogen Substances 0.000 claims abstract 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract 20
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 20
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 15
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract 12
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract 12
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 9
- 125000002252 acyl group Chemical group 0.000 claims abstract 8
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 8
- 150000002431 hydrogen Chemical group 0.000 claims abstract 6
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract 4
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 150000004677 hydrates Chemical class 0.000 claims abstract 2
- 239000002207 metabolite Substances 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 239000012453 solvate Substances 0.000 claims abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 35
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- -1 3-dimethylaminopropyl Chemical group 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
1. Соединение формулы (I) или формулы (II)или его ионные пары, соли, гидраты, сольваты или метаболиты,где R- водород, (С-С)алкил, замещенный (С-С)алкил или (С-С)алкил, замещенный одним или несколькими атомами фтора;R- алкил, замещенный алкил, ацил, замещенный ацил, галоген, гетероалкил, замещенный гетероалкил, -NO, -N, -ОН, -S(O)R, -OR, -NRR, -CONRR, -CORили -OCR;R- водород, (С-С)алкил, (С-С) замещенный алкил, (С-С)алкил, замещенный одним или несколькими атомами фтора, арилалкил или замещенный арилалкил;R- водород, (С-С)алкил, (C-C) замещенный алкил, (С-С)алкил, замещенный одним или несколькими атомами фтора, арилалкил или замещенный арилалкил;Rи Rнезависимо - водород, (С-С)алкил, замещенный (С-С)алкил, (С-С)алкил, замещенный одним или несколькими атомами фтора, гетероалкил, замещенный гетероалкил, арилалкил, замещенный арилалкил, гетероарил, замещенный гетероарил или Rи Rвместе с атомом азота, к которому они присоединены, образуют циклогетероалкильное или замещенное циклогетероалкильное кольцо;R- водород, (С-С)алкил или (С-С)алкил, замещенный одним или несколькими атомами фтора;R-Rнезависимо - водород, алкил, замещенный алкил, ацил, замещенный ацил, арил, замещенный арил, арилалкил, замещенный арилалкил, гетероалкил, замещенный гетероалкил, гетероарил, замещенный гетероарил, гетероарилалкил или замещенный гетероарилалкил;k равно 0,1 или 2 иn равно 0, 1, 2 или 3.2. Соединение по п. 1 формулы (III) или (IV)3. Соединение по п. 2, где R- водород, (С-С)алкил или (С-С)алкил, замещенный одним или несколькими атомами фтора.4. Соединение по п. 2, где R- водород, -СНили -CF.5. Соединение по п. 2, где R- -СНили -CF.6. Соединение по п. 2, где R- водород или (C-C)алкил.7. Соединение по п. 2, где R- водород, метил или аллил.8. Соединение по п. 2, где R- метил или аллил.9. Соединение по п. 2, где R- водород, (С-С)алкил, (С-С) замещенный алкил или (С-С)алкил,1. The compound of formula (I) or formula (II) or its ionic pairs, salts, hydrates, solvates or metabolites, where R is hydrogen, (C-C) alkyl, substituted (C-C) alkyl or (C-C) alkyl substituted with one or more fluorine atoms; R- alkyl, substituted alkyl, acyl, substituted acyl, halogen, heteroalkyl, substituted heteroalkyl, —NO, —N, —OH, —S (O) R, —OR, —NRR, -CONRR, -COR or -OCR; R- hydrogen, (C — C) alkyl, (C — C) substituted alkyl, (C — C) alkyl substituted with one or more fluorine atoms, arylalkyl or substituted arylalkyl; R is hydrogen, (C — C) alkyl, (CC) substituted alkyl, (C — C) alkyl substituted with one or not how many fluorine, arylalkyl or substituted arylalkyl atoms; R and R are independently hydrogen, (C — C) alkyl, substituted (C — C) alkyl, (C — C) alkyl substituted by one or more fluorine atoms, heteroalkyl, substituted heteroalkyl, arylalkyl, substituted arylalkyl, heteroaryl, substituted heteroaryl or R and R together with the nitrogen atom to which they are attached form a cycloheteroalkyl or substituted cycloheteroalkyl ring; R is hydrogen, (C-C) alkyl or (C-C) alkyl substituted with one or more fluorine atoms ; R-R is independently hydrogen, alkyl, substituted alkyl, acyl, substituted acyl, aryl, substituted aryl, arylalkyl, substituted arylalkyl, heteroalkyl, substituted heteroalkyl, heteroaryl, substituted heteroaryl, heteroarylalkyl or substituted heteroarylalkyl; k is 0.1 or 2 and n is 0, 1, 2 or 3.2. The compound of claim 1 of formula (III) or (IV) 3. A compound according to claim 2, wherein R is hydrogen, (C — C) alkyl or (C — C) alkyl substituted with one or more fluorine atoms. A compound according to claim 2, wherein R is hydrogen, —CN or —CF. 5. A compound according to claim 2, wherein R is —CN or —CF. 6. A compound according to claim 2, wherein R is hydrogen or (C-C) alkyl. A compound according to claim 2, wherein R is hydrogen, methyl or allyl. A compound according to claim 2, wherein R is methyl or allyl. The compound of claim 2, wherein R is hydrogen, (C — C) alkyl, (C — C) substituted alkyl or (C — C) alkyl,
Claims (30)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2012/043687 WO2013191704A1 (en) | 2012-06-22 | 2012-06-22 | Novel cabergoline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2014153672A true RU2014153672A (en) | 2016-08-10 |
Family
ID=49769156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2014153672A RU2014153672A (en) | 2012-06-22 | 2012-06-22 | NEW CABBERGOLINE DERIVATIVES |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP2863747A4 (en) |
| JP (1) | JP2015525239A (en) |
| CN (1) | CN104822264A (en) |
| AU (1) | AU2012382929A1 (en) |
| BR (1) | BR112014031945A2 (en) |
| CA (1) | CA2876321A1 (en) |
| HK (1) | HK1208997A1 (en) |
| IL (1) | IL236310A0 (en) |
| RU (1) | RU2014153672A (en) |
| SG (1) | SG11201408567PA (en) |
| WO (1) | WO2013191704A1 (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107428745A (en) * | 2015-01-20 | 2017-12-01 | Xoc制药股份有限公司 | Ergoline compounds and their uses |
| CN106866656A (en) * | 2017-02-28 | 2017-06-20 | 西南交通大学 | One class ergoline derivatives and its purposes in prevention and treatment mental illness |
| EP3530651A1 (en) * | 2018-02-21 | 2019-08-28 | Adamed sp. z o.o. | Indole and benzimidazole derivatives as dual 5-ht2a and 5-ht6 receptor antagonists |
| EP4155306A1 (en) | 2021-01-15 | 2023-03-29 | Beckley Psytech Limited | Neuroactive ergoline analogue |
| US12264131B2 (en) | 2022-08-19 | 2025-04-01 | Beckley Psytech Limited | Pharmaceutically acceptable salts and compositions thereof |
| US12246005B2 (en) | 2023-06-13 | 2025-03-11 | Beckley Psytech Limited | 5-methoxy-n,n-dimethyltryptamine (5-MeO-DMT) formulations |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4526892A (en) * | 1981-03-03 | 1985-07-02 | Farmitalia Carlo Erba, S.P.A. | Dimethylaminoalkyl-3-(ergoline-8'βcarbonyl)-ureas |
| DK338789A (en) * | 1988-07-15 | 1990-01-16 | Schering Ag | 2-SUBSTITUTED ERGOLINYLURINE DERIVATIVES AND PROCEDURES FOR THE PRODUCTION THEREOF, THEIR USE AS MEDICINES AND INTERMEDIATES FOR THE PRODUCTION THEREOF |
| DE3913756A1 (en) * | 1989-04-21 | 1990-10-25 | Schering Ag | 8 (BETA) SUBSTITUTED ERGOLINE, METHOD FOR THE PRODUCTION AND USE THEREOF |
| WO1995005176A1 (en) * | 1993-08-18 | 1995-02-23 | Alcon Laboratories, Inc. | Use of ergoline derivatives for the treatment of glaucoma |
| CZ287176B6 (en) * | 1997-10-03 | 2000-10-11 | Galena A. S. | Process for preparing ergoline derivatives |
| JP2006516596A (en) * | 2003-02-05 | 2006-07-06 | ファルマシア イタリア ソチエタ ペル アツィオニ | Cabergoline for the prevention and treatment of migraine |
| GB0307377D0 (en) * | 2003-03-31 | 2003-05-07 | Merad Pharmaceuticals Ltd | Ergoline derivatives |
| HUP0400517A3 (en) * | 2004-03-04 | 2006-05-29 | Richter Gedeon Vegyeszet | Process for producing cabergoline |
| WO2006097345A1 (en) * | 2005-03-17 | 2006-09-21 | Synthon Argentina S.A. | Improved process for making cabergoline |
| GB0511060D0 (en) * | 2005-05-31 | 2005-07-06 | Novartis Ag | Organic compounds |
| EP2083008A1 (en) * | 2007-12-07 | 2009-07-29 | Axxonis Pharma AG | Ergoline derivatives as selective radical scavengers for neurons |
| AU2010203461A1 (en) * | 2009-01-09 | 2011-07-28 | President And Fellows Of Harvard College | Fluorine containing compounds and methods of use thereof |
| EP2419425A4 (en) * | 2009-04-15 | 2012-08-29 | Astrazeneca Ab | Imidazole substituted pyrimidines useful in the treatment of glycogen synthase kinase 3 related disorders such as alzheimer's disease |
| EP2793583A4 (en) * | 2011-12-21 | 2015-08-12 | Map Pharmaceuticals Inc | Novel neuromodulatory compounds |
-
2012
- 2012-06-22 RU RU2014153672A patent/RU2014153672A/en unknown
- 2012-06-22 CA CA2876321A patent/CA2876321A1/en not_active Abandoned
- 2012-06-22 AU AU2012382929A patent/AU2012382929A1/en not_active Abandoned
- 2012-06-22 CN CN201280075321.7A patent/CN104822264A/en active Pending
- 2012-06-22 BR BR112014031945A patent/BR112014031945A2/en not_active IP Right Cessation
- 2012-06-22 EP EP12879191.0A patent/EP2863747A4/en not_active Withdrawn
- 2012-06-22 SG SG11201408567PA patent/SG11201408567PA/en unknown
- 2012-06-22 JP JP2015518385A patent/JP2015525239A/en active Pending
- 2012-06-22 HK HK15109927.2A patent/HK1208997A1/en unknown
- 2012-06-22 WO PCT/US2012/043687 patent/WO2013191704A1/en not_active Ceased
-
2014
- 2014-12-17 IL IL236310A patent/IL236310A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK1208997A1 (en) | 2016-03-24 |
| EP2863747A4 (en) | 2015-12-23 |
| JP2015525239A (en) | 2015-09-03 |
| BR112014031945A2 (en) | 2017-06-27 |
| SG11201408567PA (en) | 2015-02-27 |
| AU2012382929A1 (en) | 2015-02-05 |
| IL236310A0 (en) | 2015-02-26 |
| CA2876321A1 (en) | 2013-12-27 |
| CN104822264A (en) | 2015-08-05 |
| WO2013191704A1 (en) | 2013-12-27 |
| EP2863747A1 (en) | 2015-04-29 |
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