AR096904A1 - DERIVATIVES OF PIPERIDINIL-INDOL AS INHIBITORS OF COMPLEMENT FACTOR B AND USES OF THE SAME - Google Patents
DERIVATIVES OF PIPERIDINIL-INDOL AS INHIBITORS OF COMPLEMENT FACTOR B AND USES OF THE SAMEInfo
- Publication number
- AR096904A1 AR096904A1 ARP140102589A ARP140102589A AR096904A1 AR 096904 A1 AR096904 A1 AR 096904A1 AR P140102589 A ARP140102589 A AR P140102589A AR P140102589 A ARP140102589 A AR P140102589A AR 096904 A1 AR096904 A1 AR 096904A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- alkoxy
- heteroaryl
- hydroxyl
- hydroxy
- Prior art date
Links
- 102000003712 Complement factor B Human genes 0.000 title 1
- 108090000056 Complement factor B Proteins 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 16
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 7
- 229910052736 halogen Inorganic materials 0.000 abstract 6
- 150000002367 halogens Chemical group 0.000 abstract 6
- 125000001072 heteroaryl group Chemical group 0.000 abstract 6
- 229910052760 oxygen Inorganic materials 0.000 abstract 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
- 229910052717 sulfur Inorganic materials 0.000 abstract 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000005842 heteroatom Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000004434 sulfur atom Chemical group 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 239000013543 active substance Substances 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- -1 cyano-methyl Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000006413 ring segment Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Un método para la elaboración de los compuestos de la presente y sus usos terapéuticos. La presente proporciona además una combinación de agentes farmacológicamente activos y una composición farmacéutica. Reivindicación 1: Un compuesto, o una sal o un tautómero del mismo, de acuerdo con la fórmula (1) en donde: n es 0, 1 ó 2; R es hidrógeno, alquilo C₁₋₄, o hidroxi-alquilo C₁₋₄; R¹ es halógeno, hidroxilo, alquilo C₁₋₆, alquenilo C₂₋₆, cicloalquilo C₃₋₆, alcoxilo C₁₋₆, halo-alquilo C₁₋₆, hidroxi-alquilo C₁₋₆, amino-alquilo C₁₋₆, alcoxilo C₁₋₆-alquilo C₁₋₆, alcoxilo C₁₋₆-alcoxilo C₁₋₆, cicloalquilo C₃₋₆-alcoxilo C₁₋₆, halo-alcoxilo C₁₋₆, -S(O)ₚ-alquilo C₁₋₆, -CH₂NHC(O)-alquilo C₁₋₄ u -OCH₂C(O)R⁷, p es 0, 1 ó 2; R² es alquilo C₁₋₆, alcoxilo C₁₋₆, hidroxi-alquilo C₁₋₆ o halógeno; R³ es hidrógeno, halógeno, ciano, alquilo C₁₋₄, halo-alquilo C₁₋₄, CH₂C(O)R⁷, fenilo o heteroarilo de 5 o 6 miembros que tiene 1, 2 ó 3 heteroátomos en el anillo independientemente seleccionados a partir de N, O ó S, en donde el fenilo o heteroarilo está opcionalmente sustituido con 0, 1 ó 2 grupos alquilo C₁₋₄, y en donde el alquilo y el halo-alquilo están opcionalmente sustituidos con 0 ó 1 hidroxilo; R⁴ es fenilo, naftilo o heteroarilo, en donde el heteroarilo es un heteroarilo de cinco o seis miembros que tiene 1, 2 ó 3 heteroátomos en el anillo independientemente seleccionados a partir de N, O ó S, y en donde el fenilo o heteroarilo está opcionalmente sustituido por R⁵ y está además sustituido por 0 ó 1 sustituyente seleccionado a partir de halógeno, alquilo C₁₋₄, alcoxilo C₁₋₄, hidroxi-alquilo C₁₋₄, hidroxilo, y ciano-metilo; R⁵ es -C(O)R⁸, -CH₂C(O)R⁸, R⁹, -C(O)NHSO₂-alquilo C₁₋₄, -SO₂NHC(O)-alquilo C₁₋₄, -SO₂N(H)ₘ(alquilo C₁₋₄)₂₋ₘ, -SO₂-alquilo C₁₋₄, ciano, halógeno, hidroxi-alquilo C₁₋₄ y heteroarilo de 5 miembros que tiene de 1 a 4 átomos de nitrógeno en el anillo y 0 ó 1 átomo de azufre o de oxígeno en el anillo; m es 0, 1 ó 2; W es O ó C(R⁶)₂; R⁶ se selecciona independientemente en cada presentación a partir del grupo que consiste en hidrógeno, hidroxilo, amino, mono- y di-alquilo C₁₋₄-amino, alquilo C₁₋₄, hidroxi-alquilo C₁₋₄, ciano-alquilo C₁₋₄ o alcoxilo C₁₋₄; o C(R⁶)₂, tomados en combinación, forman un carbociclo espirocíclico que tiene de 3 a 6 átomos en el anillo; R⁷ es hidroxilo, alcoxilo C₁₋₄, amino, o mono y di-alquilo C₁₋₄-amino; R⁸ es hidroxilo, alcoxilo C₁₋₄, amino, o un heterociclo saturado de 5 a 7 miembros que tiene 1, 2, ó 3 heteroátomos en el anillo independientemente seleccionados a partir de N, O ó S; o R⁸ es mono- y di-alquilo C₁₋₄-amino que está insustituido o sustituido con halógeno, hidroxilo, o alquilo C₁₋₄; y R⁹ es un heteroarilo de 5 miembros que tiene de 1 a 4 átomos de nitrógeno en el anillo y 0 ó 1 átomo de oxígeno o de azufre en el anillo, cuyo heterociclo está opcionalmente sustituido por 0 a 2 grupos alquilo C₁₋₄.A method for the elaboration of the compounds of the present and their therapeutic uses. The present further provides a combination of pharmacologically active agents and a pharmaceutical composition. Claim 1: A compound, or a salt or tautomer thereof, according to formula (1) wherein: n is 0, 1 or 2; R is hydrogen, C₁₋₄ alkyl, or hydroxy-C₁₋₄ alkyl; R¹ is halogen, hydroxyl, C₁₋₆ alkyl, C₂₋₆ alkenyl, C₃₋₆ cycloalkyl, C₁₋₆ alkoxy, halo₁₋₆C alquilo alkyl, hydroxyC₁₋₆ alkyl, aminoC₁₋₆ alkyl, C₁₋ alkoxy ₆-C₁₋₆ alkyl, C₁₋₆ alkoxy-C₁₋₆ alkoxy, C₃₋₆ cycloalkyl-C₁₋₆ alkoxy, -S (O) ₚ -C₁₋₆ alkyl, -CH₂NHC (O ) -C₁₋₄ or -OCH₂C (O) R⁷ alkyl, p is 0, 1 or 2; R² is C₁₋₆ alkyl, C₁₋₆ alkoxy, hydroxy-C₁₋₆ alkyl or halogen; R³ is hydrogen, halogen, cyano, C₁₋₄ alkyl, halo-C₁₋₄ alkyl, CH₂C (O) R⁷, 5 or 6 membered phenyl or heteroaryl having 1, 2 or 3 ring heteroatoms independently selected from N, O or S, wherein the phenyl or heteroaryl is optionally substituted with 0, 1 or 2 C₁₋₄ alkyl groups, and wherein the alkyl and halo-alkyl are optionally substituted with 0 or 1 hydroxyl; R⁴ is phenyl, naphthyl or heteroaryl, wherein the heteroaryl is a five or six membered heteroaryl having 1, 2 or 3 ring heteroatoms independently selected from N, O or S, and wherein the phenyl or heteroaryl is optionally substituted by R⁵ and is further substituted by 0 or 1 substituent selected from halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, hydroxy-C₁₋₄ alkyl, hydroxyl, and cyano-methyl; R⁵ is -C (O) R⁸, -CH₂C (O) R⁸, R⁹, -C (O) NHSO₂-C₁₋₄ alkyl, -SO₂NHC (O) -C₁₋₄ alkyl, -SO₂N (H) ₘ (C₁ alkyl ₋₄) ₂₋ₘ, -SO₂-C₁₋₄ alkyl, cyano, halogen, hydroxy-C₁₋₄ alkyl and 5-membered heteroaryl having 1 to 4 ring nitrogen atoms and 0 or 1 sulfur atom or of oxygen in the ring; m is 0, 1 or 2; W is O or C (R⁶) ₂; R⁶ is independently selected in each presentation from the group consisting of hydrogen, hydroxyl, amino, mono- and di-C₁₋₄-alkyl, C alquilo alkyl, hydroxy-C₁₋₄ alkyl, cyano-C₁₋₄ alkyl or C₁₋₄ alkoxy; or C (R⁶) ₂, taken in combination, form a spirocyclic carbocycle having 3 to 6 ring atoms; R⁷ is hydroxy, C₁₋₄ alkoxy, amino, or mono and di-C₁₋₄-amino alkyl; R⁸ is hydroxyl, C₁₋₄ alkoxy, amino, or a 5- to 7-membered saturated heterocycle having 1, 2, or 3 ring heteroatoms independently selected from N, O or S; or R⁸ is mono- and di-C₁₋₄-amino alkyl which is unsubstituted or substituted by halogen, hydroxyl, or C₁₋₄ alkyl; and R⁹ is a 5-membered heteroaryl having 1 to 4 ring nitrogen atoms and 0 or 1 ring oxygen or sulfur atom, whose heterocycle is optionally substituted by 0 to 2 C₁₋₄ alkyl groups.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361846355P | 2013-07-15 | 2013-07-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR096904A1 true AR096904A1 (en) | 2016-02-03 |
Family
ID=56125325
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP140102589A AR096904A1 (en) | 2013-07-15 | 2014-07-14 | DERIVATIVES OF PIPERIDINIL-INDOL AS INHIBITORS OF COMPLEMENT FACTOR B AND USES OF THE SAME |
Country Status (2)
| Country | Link |
|---|---|
| AR (1) | AR096904A1 (en) |
| MA (1) | MA38838B1 (en) |
-
2014
- 2014-07-14 AR ARP140102589A patent/AR096904A1/en active IP Right Grant
- 2014-07-14 MA MA38838A patent/MA38838B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MA38838B1 (en) | 2017-11-30 |
| MA38838A1 (en) | 2017-03-31 |
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