AR107488A1 - Compuestos de benzopirazol y análogos de éstos - Google Patents
Compuestos de benzopirazol y análogos de éstosInfo
- Publication number
- AR107488A1 AR107488A1 ARP170100240A ARP170100240A AR107488A1 AR 107488 A1 AR107488 A1 AR 107488A1 AR P170100240 A ARP170100240 A AR P170100240A AR P170100240 A ARP170100240 A AR P170100240A AR 107488 A1 AR107488 A1 AR 107488A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- heterocycloalkyl
- cycloalkyl
- optionally substituted
- 6alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 8
- 125000000217 alkyl group Chemical group 0.000 abstract 24
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 17
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 15
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 8
- 125000004475 heteroaralkyl group Chemical group 0.000 abstract 8
- 125000003118 aryl group Chemical group 0.000 abstract 7
- 125000001072 heteroaryl group Chemical group 0.000 abstract 7
- 125000004429 atom Chemical group 0.000 abstract 6
- 125000001188 haloalkyl group Chemical group 0.000 abstract 6
- 125000003342 alkenyl group Chemical group 0.000 abstract 5
- 125000000304 alkynyl group Chemical group 0.000 abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 4
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000002837 carbocyclic group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 230000004154 complement system Effects 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- 230000002159 abnormal effect Effects 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 230000006806 disease prevention Effects 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 125000005549 heteroarylene group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000005017 substituted alkenyl group Chemical group 0.000 abstract 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
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- 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
- C07D209/12—Radicals substituted by oxygen atoms
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- 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
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- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- 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
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- 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
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
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- 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
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- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
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- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
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- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
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- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
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- 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
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- C07D401/14—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 three or more hetero rings
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- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
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- Vascular Medicine (AREA)
Abstract
Se describen compuestos y sales de estos aceptables desde el punto de vista farmacéutico. Los compuestos son inhibidores del sistema de complemento. También se proporcionan composiciones farmacéuticas que comprenden un compuesto, y métodos que incluyen el uso de compuestos y composiciones en el tratamiento y prevención de enfermedades y afecciones caracterizadas por la actividad anómala del sistema de complemento. Reivindicación 1: Un compuesto representado por la fórmula (1), o una sal de este aceptable desde el punto de vista farmacéutico, en donde, independientemente para cada caso: R¹ representa arilo, heteroarilo, cicloalquilo, heterocicloalquilo, alquilo, o alquenilo opcionalmente sustituidos; R² y R³ cada uno representa independientemente H, F, o alquilo, alquenilo, alquinilo, alcoxialquilo, haloalquilo, hidroxialquilo, (alquiltio)alquilo, aralquilo, heteroaralquilo, cicloalquilo, (cicloalquil)alquilo, heterocicloalquilo, o (heterocicloalquil)alquilo opcionalmente sustituidos; o R² y R³, junto con el átomo de carbono al que están unidos, forman un anillo de cicloalquilo o heterocicloalquilo opcionalmente sustituido; R⁴ representa H o alquilo, alquenilo, alquinilo, cicloalquilo, (cicloalquil)alquilo, heterocicloalquilo, (heterocicloalquil)alquilo, aralquilo, heteroaralquilo, hidroxialquilo, o haloalquilo opcionalmente sustituidos; X representa NH, CH₂, CHF, CF₂, CHC₁₋₆alquilo, o C(C₁₋₆alquilo)₂; Y está ausente o representa CH₂, C(O), CR¹⁵R¹⁶, S(O)₂, o C₃₋₇cicloalquileno, arileno o heteroarileno opcionalmente sustituidos; Rᵃ representa H o C₁₋₆alquilo, (heterocicloalquil)alquilo o C₃₋₇cicloalquilo opcionalmente sustituidos; m es un entero de 1 - 6; n es 0 ó 1; R¹⁵ y R¹⁶ se seleccionan independientemente del grupo que consiste en H, hidroxi, halógeno, -C(O)OR¹⁷, -OR¹⁷, -C(O)NR¹⁷R¹⁸, -NR¹⁷R¹⁸, alquilo, hidroxialquilo, haloalquilo, alcoxialquilo, arilo, aralquilo, heteroarilo, heteroaralquilo, cicloalquilo, (cicloalquil)alquilo, heterocicloalquilo, y (heterocicloalquil)alquilo, en donde alquilo, arilo, aralquilo, heteroarilo, heteroaralquilo, cicloalquilo, (cicloalquil)alquilo, heterocicloalquilo, y (heterocicloalquil)alquilo se sustituyen opcionalmente con uno o más sustituyentes seleccionados del grupo que consiste en -CN, -OR¹⁷, -NR¹⁷R¹⁸, halo, y alquilo; o R¹⁵ y R¹⁶, junto con el átomo interviniente, pueden formar un anillo carbocíclico o heterocíclico opcionalmente sustituido; R¹⁷ y R¹⁸ se seleccionan independientemente del grupo que consiste en H, alquilo, haloalquilo, hidroxialquilo, alcoxialquilo, arilo, aralquilo, heteroarilo, heteroaralquilo, cicloalquilo, (cicloalquil)alquilo, heterocicloalquilo, y (heterocicloalquil)alquilo; o R¹⁷ y R¹⁸, cuando están unidos al mismo átomo, pueden formar, junto con el átomo interviniente, un anillo heterocíclico opcionalmente sustituido; el Anillo B representa un compuesto de fórmula (2), (3), (4), (5) ó (6); Z¹ y Z³ cada uno representa independientemente C o N; Z² representa N, CH, o CF; Z⁴ representa N o CR⁸; Z⁵ representa N o CR⁵; Z⁶ representa N o CR⁶; Z⁷ representa N o CR⁹; Z⁸ y Z⁹ cada uno representa independientemente N o CR¹⁹; R⁵ y R⁶ cada uno representa independientemente H, halógeno, -CN, -NO₂, -OR¹³, -NR¹³R¹⁴, -C(O)R¹³, -C(O)OR¹³, -C(O)NR¹³R¹⁴, -OC(O)R¹³, -NR¹³C(O)R¹⁴, -OC(O)NR¹³R¹⁴, -OC(O)OR¹³, -NR¹³C(O)OR¹⁴, -NR¹³C(O)NR¹³R¹⁴, -OS(O)ₚ(R¹³), -NR¹³S(O)ₚ(R¹⁴), o alquilo, alquenilo, alquinilo, haloalquilo, aralquilo, heteroaralquilo, heteroarilo, arilo, cicloalquilo, (cicloalquil)alquilo, heterocicloalquilo, o (heterocicloalquil)alquilo opcionalmente sustituidos; L representa -H, -CN, -C(O)R⁷, -CH(OH)R⁷, o -S(O)ₚ(alquilo); R⁷, independientemente para cada caso, representa H, NH₂, CH₃, OH, CF₃, CH₂OH, C₁₋₆alquilo, hidroxi-C₁₋₆alquilo, C₁₋₆alcoxi-C₁₋₆alquilo, halo-C₁₋₆alquilo, NHC₁₋₆alquilo, N(C₁₋₆alquilo)₂; R⁸ y R⁹ cada uno representa independientemente H, halógeno, -OR¹³, -NR¹³R¹⁴, -C(O)R¹³, -C(O)OR¹³, -C(O)NR¹³R¹⁴, -OC(O)R¹³, -NR¹³C(O)R¹⁴, -OC(O)NR¹³R¹⁴, -OC(O)OR¹³, -NR¹³C(O)OR¹⁴, -NR¹³C(O)NR¹³R¹⁴, -OS(O)ₚ(R¹³), -NR¹³S(O)ₚ(R¹⁴), o alquilo, alquenilo, alquinilo, haloalquilo, aralquilo, heteroaralquilo, heteroarilo o arilo opcionalmente sustituidos; o R⁵ y R⁸ o R⁵ y R⁶, o R⁶ y R⁹, junto con los átomos intervinientes, pueden formar un anillo heterocíclico o carbocíclico opcionalmente sustituido; R¹³ y R¹⁴, independientemente para cada caso, representan H o alquilo, alquenilo, alquinilo, arilo, aralquilo, heteroarilo, heteroaralquilo, cicloalquilo, (cicloalquil)alquilo, heterocicloalquilo, o (heterocicloalquil)alquilo opcionalmente sustituidos; o cuando R¹³ y R¹⁴ están unidos al mismo átomo, R¹³ y R¹⁴, junto con el átomo, pueden formar un anillo heterocíclico opcionalmente sustituido; R¹⁹, independientemente para cada caso, representa H, F, CN, -C(O)R⁷, -CH(OH)R⁷, o -S(O)ₚ(alquilo); J representa H o NH₂; y p es 0, 1 ó 2; en donde, si Z¹ es N, o si el Anillo B representa el compuesto de fórmula (3), (4), (5) ó (6), entonces X representa CH₂.
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