AR115228A1 - DERIVADOS DE (AZA)INDOL SUSTITUIDOS, UN MÉTODO PARA SU PREPARACIÓN, INTERMEDIARIOS PARA SU SÍNTESIS, COMPOSICIÓN Y COMBINACIÓN FARMACÉUTICA QUE LOS COMPRENDEN Y EL USO DE LOS MISMOS EN EL TRATAMIENTO DE ENFERMEDADES ASOCIADAS AL RECEPTOR NICOTÍNICO DE ACETILCOLINA a7 - Google Patents
DERIVADOS DE (AZA)INDOL SUSTITUIDOS, UN MÉTODO PARA SU PREPARACIÓN, INTERMEDIARIOS PARA SU SÍNTESIS, COMPOSICIÓN Y COMBINACIÓN FARMACÉUTICA QUE LOS COMPRENDEN Y EL USO DE LOS MISMOS EN EL TRATAMIENTO DE ENFERMEDADES ASOCIADAS AL RECEPTOR NICOTÍNICO DE ACETILCOLINA a7Info
- Publication number
- AR115228A1 AR115228A1 ARP190101993A ARP190101993A AR115228A1 AR 115228 A1 AR115228 A1 AR 115228A1 AR P190101993 A ARP190101993 A AR P190101993A AR P190101993 A ARP190101993 A AR P190101993A AR 115228 A1 AR115228 A1 AR 115228A1
- Authority
- AR
- Argentina
- Prior art keywords
- 6alkyl
- responds
- compound characterized
- hydrogen
- pyrrolo
- Prior art date
Links
- 229940054051 antipsychotic indole derivative Drugs 0.000 title abstract 2
- 201000010099 disease Diseases 0.000 title abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- JJQQOTDMHDOYTF-UHFFFAOYSA-N (1,2-dimethylpyrrolo[2,3-b]pyridin-5-yl)methanamine Chemical compound CN1C(=CC=2C1=NC=C(C=2)CN)C JJQQOTDMHDOYTF-UHFFFAOYSA-N 0.000 abstract 1
- BESDAEWBKZKOOE-UHFFFAOYSA-N (3-bromo-1-methylpyrrolo[2,3-b]pyridin-5-yl)methanamine Chemical compound BrC1=CN(C2=NC=C(C=C21)CN)C BESDAEWBKZKOOE-UHFFFAOYSA-N 0.000 abstract 1
- UNOXCWIALZCQIP-UHFFFAOYSA-N (3-chloro-1-methylpyrrolo[2,3-b]pyridin-5-yl)methanamine Chemical compound Cn1cc(Cl)c2cc(CN)cnc12 UNOXCWIALZCQIP-UHFFFAOYSA-N 0.000 abstract 1
- ALJBMDSNNOXPJL-UHFFFAOYSA-N 2-(azetidin-3-yloxymethyl)-5-(trifluoromethyl)pyridine Chemical compound N1CC(C1)OCC1=NC=C(C=C1)C(F)(F)F ALJBMDSNNOXPJL-UHFFFAOYSA-N 0.000 abstract 1
- IBLGHVMLQMHMSQ-UHFFFAOYSA-N 7-fluoro-1h-indol-5-amine Chemical compound NC1=CC(F)=C2NC=CC2=C1 IBLGHVMLQMHMSQ-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- WWHWKVMZIPGKAD-UHFFFAOYSA-N CC1=CN(C)C2=NC=C(CN)C=C12 Chemical compound CC1=CN(C)C2=NC=C(CN)C=C12 WWHWKVMZIPGKAD-UHFFFAOYSA-N 0.000 abstract 1
- GQZIPIMBOMUQTL-UHFFFAOYSA-N FC1=CN(C2=NC=C(C=C21)N)C Chemical compound FC1=CN(C2=NC=C(C=C21)N)C GQZIPIMBOMUQTL-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 102000047725 alpha7 Nicotinic Acetylcholine Receptor Human genes 0.000 abstract 1
- 108700006085 alpha7 Nicotinic Acetylcholine Receptor Proteins 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- 150000002475 indoles Chemical class 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000002207 metabolite Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
Classifications
-
- 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
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Derivados de (aza)indol sustituidos, un método de obtención de los mismos, intermediarios para su preparación y composiciones farmacéuticas que lo comprenden como principio activo. Dichos compuestos se emplean para el tratamiento de enfermedades asociadas a la actividad del receptor nicotínico de acetilcolina a7. Reivindicación 1: Un compuesto caracterizado porque es de fórmula (1), donde R¹ es hidrógeno o C₁₋₆alquilo; R² es hidrógeno o C₁₋₆alquilo, o R² se encuentra ausente cuando n es 0; R³ es hidrógeno ó O; o R³ se encuentra ausente cuando m es 0; R⁴ y R⁵ son en forma independiente hidrógeno, C₁₋₆alquilo, halógeno, haloC₁₋₆alquilo, C₁₋₆alcoxi, o CN; n y m son en forma independiente 0 ó 1, con la condición de que n y m no pueden ser 0 al mismo tiempo; k y l son en forma independiente 1, 2 ó 3; Y es N o C(R⁶); R⁶ es hidrógeno, C₁₋₆alquilo, halógeno, o haloC₁₋₆alquilo; R⁷ es hidrógeno, C₁₋₆alquilo, o halógeno; W es CH o N; Z es CH, C-C₁₋₃alquilo o N; L es un conector opcionalmente sustituido que consiste en 1, 2 ó 3 átomos, representado por T-U-V, donde T es CH₂, C(O), NH, SO₂ ó O; U es CH₂, C(O), O ó se encuentra ausente; y V es CH₂, O ó se encuentra ausente; A es un carbociclilo saturado, insaturado, o aromático, o un heterociclilo saturado, insaturado, o aromático, donde los heteroátomos se seleccionan entre el grupo de nitrógeno, oxígeno y azufre; opcionalmente sustituido en forma independiente con uno o más átomos de halógeno, C₁₋₆alquilo, C₁₋₆alcoxi, haloC₁₋₆alquilo, haloC₁₋₆alcoxi, CN, o bencilo; o sales farmacéuticamente aceptables, metabolitos biológicamente activos, profármacos, racematos, enantiómeros, diasterómeros, solvatos e hidratos del mismo. Reivindicación 20: El compuesto caracterizado porque responde a 7-fluoro-1H-indol-5-amina. Reivindicación 21: El compuesto caracterizado porque responde a 3-fluoro-1-metil-1H-pirrolo[2,3-b]piridin-5-amina. Reivindicación 22: El compuesto caracterizado porque responde a 2-[(azetidin-3-iloxi)metil]-5-(trifluorometil)piridina. Reivindicación 23: El compuesto caracterizado porque responde a {1,2-dimetil-1H-pirrolo[2,3-b]piridin-5-il}metanamina. Reivindicación 24: El compuesto caracterizado porque responde a {1,3-dimetil-1H-pirrolo[2,3-b]piridin-5-il}metanamina. Reivindicación 25: El compuesto caracterizado porque responde a {3-cloro-1-metil-1H-pirrolo[2,3-b]piridin-5-il}metanamina. Reivindicación 26: El compuesto caracterizado porque responde a {3-bromo-1-metil-1H-pirrolo[2,3-b]piridin-5-il}metanamina.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUP1800250A HU231478B1 (hu) | 2018-07-13 | 2018-07-13 | Szubsztituált (aza)indol származékok |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR115228A1 true AR115228A1 (es) | 2020-12-09 |
Family
ID=89985025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP190101993A AR115228A1 (es) | 2018-07-13 | 2019-07-12 | DERIVADOS DE (AZA)INDOL SUSTITUIDOS, UN MÉTODO PARA SU PREPARACIÓN, INTERMEDIARIOS PARA SU SÍNTESIS, COMPOSICIÓN Y COMBINACIÓN FARMACÉUTICA QUE LOS COMPRENDEN Y EL USO DE LOS MISMOS EN EL TRATAMIENTO DE ENFERMEDADES ASOCIADAS AL RECEPTOR NICOTÍNICO DE ACETILCOLINA a7 |
Country Status (4)
| Country | Link |
|---|---|
| AR (1) | AR115228A1 (es) |
| HU (1) | HU231478B1 (es) |
| TW (1) | TW202017904A (es) |
| WO (1) | WO2020012424A1 (es) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW202202495A (zh) | 2020-03-26 | 2022-01-16 | 匈牙利商羅特格登公司 | 作為ｇａｍｍａ－胺基丁酸Ａ受體次單元ａｌｐｈａ ５受體調節劑之㖠啶及吡啶并〔３，４－ｃ〕嗒𠯤衍生物 |
| HUP2100338A1 (hu) | 2021-09-29 | 2023-04-28 | Richter Gedeon Nyrt | GABAA ALFA5 receptor modulátor hatású biciklusos aminszármazékok |
| AR127972A1 (es) | 2021-12-17 | 2024-03-13 | Pi Industries Ltd | Novedosos compuestos de piridina carboxamida bicíclica sustituida fusionada para combatir hongos fitopatogénicos |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1782811A4 (en) | 2004-08-09 | 2010-09-01 | Eisai R&D Man Co Ltd | INNOVATIVE ANTIPALUDITIC AGENT CONTAINING A HETEROCYCLIC COMPOUND |
| JP5341516B2 (ja) | 2005-09-13 | 2013-11-13 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ２−アニリン−４−アリール置換チアゾール誘導体 |
| ES2460897T3 (es) | 2007-10-04 | 2014-05-14 | F. Hoffmann-La Roche Ag | Derivados de ciclopropil aril amida y usos de los mismos |
| KR101186704B1 (ko) | 2007-10-04 | 2012-09-27 | 에프. 호프만-라 로슈 아게 | 테트라졸-치환된 아릴 아마이드 유도체 및 이의 용도 |
| US8536221B2 (en) | 2008-02-07 | 2013-09-17 | Abbvie Inc. | Amide derivatives as positive allosteric modulators and methods of use thereof |
| CN102066343B (zh) | 2008-03-19 | 2013-12-04 | 詹森药业有限公司 | 作为烟碱乙酰胆碱受体调节剂的三取代1，2，4-三唑类 |
| ES2392795T3 (es) | 2008-04-17 | 2012-12-13 | Proximagen Limited | Indoles como moduladores del receptor nicotínico de acetilcolina de subtipo alfa-7 |
| WO2009135944A1 (en) | 2008-05-09 | 2009-11-12 | Janssen Pharmaceutica Nv | Trisubstituted pyrazoles as acetylcholine receptor modulators |
| JP2011524864A (ja) | 2008-05-30 | 2011-09-08 | メルク・シャープ・エンド・ドーム・コーポレイション | 新規な置換されたアザベンゾオキサゾール |
| US8829026B2 (en) | 2010-10-01 | 2014-09-09 | Raqualia Pharma Inc. | Sulfamoyl benzoic acid heterobicyclic derivatives as TRPM8 antagonists |
| US20120252853A1 (en) | 2011-04-01 | 2012-10-04 | H. Lundbeck A/S | Positive allosteric modulators of nicotinic acetylcholine receptor |
| WO2014049133A1 (en) * | 2012-09-28 | 2014-04-03 | H. Lundbeck A/S | New positive allosteric modulators of nicotinic acetylcholine receptor |
| JP2016512225A (ja) | 2013-03-13 | 2016-04-25 | ルピン・リミテッドＬｕｐｉｎ Ｌｉｍｉｔｅｄ | アルファー７ｎａｃｈｒモジュレータとしてのピロール誘導体 |
| GB201421088D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | New enzyme inhibitors |
| GEP20207149B (en) | 2016-03-22 | 2020-09-10 | Merck Sharp & Dohme | Allosteric modulators of nicotinic acetylcholine receptors |
| EP3534888B1 (en) | 2016-11-01 | 2022-04-06 | Merck Sharp & Dohme Corp. | Substituted bicyclic heteroaryl allosteric modulators of nicotinic acetylcholine receptors |
-
2018
- 2018-07-13 HU HUP1800250A patent/HU231478B1/hu unknown
-
2019
- 2019-06-27 TW TW108122551A patent/TW202017904A/zh unknown
- 2019-07-12 AR ARP190101993A patent/AR115228A1/es unknown
- 2019-07-12 WO PCT/IB2019/055950 patent/WO2020012424A1/en active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| HU231478B1 (hu) | 2024-02-28 |
| WO2020012424A1 (en) | 2020-01-16 |
| HUP1800250A2 (en) | 2020-01-28 |
| TW202017904A (zh) | 2020-05-16 |
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