AR107795A1 - Indazoles 2-sustituidos, procedimientos para su preparación, y su uso para la preparación de medicamentos - Google Patents
Indazoles 2-sustituidos, procedimientos para su preparación, y su uso para la preparación de medicamentosInfo
- Publication number
- AR107795A1 AR107795A1 ARP170100533A ARP170100533A AR107795A1 AR 107795 A1 AR107795 A1 AR 107795A1 AR P170100533 A ARP170100533 A AR P170100533A AR P170100533 A ARP170100533 A AR P170100533A AR 107795 A1 AR107795 A1 AR 107795A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- cyano
- hydroxy
- alkoxy
- fluorine
- Prior art date
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- 239000003814 drug Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 20
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 17
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 16
- 229910052739 hydrogen Inorganic materials 0.000 abstract 13
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 12
- 229910052731 fluorine Inorganic materials 0.000 abstract 12
- 239000011737 fluorine Substances 0.000 abstract 12
- 239000001257 hydrogen Substances 0.000 abstract 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 11
- 125000000217 alkyl group Chemical group 0.000 abstract 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 11
- 229910017711 NHRa Inorganic materials 0.000 abstract 10
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 9
- 150000002431 hydrogen Chemical group 0.000 abstract 9
- 125000001153 fluoro group Chemical group F* 0.000 abstract 8
- 229910052799 carbon Inorganic materials 0.000 abstract 7
- 229910052717 sulfur Inorganic materials 0.000 abstract 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 6
- 229910052794 bromium Inorganic materials 0.000 abstract 6
- 229910052736 halogen Inorganic materials 0.000 abstract 6
- 150000002367 halogens Chemical group 0.000 abstract 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 5
- -1 2-substituted indazoles Chemical class 0.000 abstract 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 4
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- 239000000460 chlorine Chemical group 0.000 abstract 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 4
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 abstract 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 abstract 3
- 201000009273 Endometriosis Diseases 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 abstract 3
- 201000010099 disease Diseases 0.000 abstract 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 3
- 125000001072 heteroaryl group Chemical group 0.000 abstract 3
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 238000011321 prophylaxis Methods 0.000 abstract 3
- 238000011282 treatment Methods 0.000 abstract 3
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 201000005671 spondyloarthropathy Diseases 0.000 abstract 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000006163 5-membered heteroaryl group Chemical group 0.000 abstract 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 abstract 1
- 208000005171 Dysmenorrhea Diseases 0.000 abstract 1
- 206010013935 Dysmenorrhoea Diseases 0.000 abstract 1
- 208000004483 Dyspareunia Diseases 0.000 abstract 1
- 201000005569 Gout Diseases 0.000 abstract 1
- 206010022489 Insulin Resistance Diseases 0.000 abstract 1
- 206010025323 Lymphomas Diseases 0.000 abstract 1
- 229910003204 NH2 Inorganic materials 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- JDTPCYGRCOGGAB-UHFFFAOYSA-N O[Br]Cl Chemical compound O[Br]Cl JDTPCYGRCOGGAB-UHFFFAOYSA-N 0.000 abstract 1
- 208000002193 Pain Diseases 0.000 abstract 1
- 201000004681 Psoriasis Diseases 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
- 206010013990 dysuria Diseases 0.000 abstract 1
- 208000010706 fatty liver disease Diseases 0.000 abstract 1
- 150000002222 fluorine compounds Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 abstract 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 abstract 1
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 abstract 1
- 208000002780 macular degeneration Diseases 0.000 abstract 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 201000006417 multiple sclerosis Diseases 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 230000036407 pain Effects 0.000 abstract 1
- 230000001185 psoriatic effect Effects 0.000 abstract 1
- 206010039073 rheumatoid arthritis Diseases 0.000 abstract 1
- 125000005415 substituted alkoxy group Chemical group 0.000 abstract 1
- 208000024891 symptom Diseases 0.000 abstract 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 abstract 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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Abstract
La presente solicitud se refiere a indazoles 2-sustituidos, a procedimientos para su preparación, el uso de los indazoles sustituidos para el tratamiento y/o la profilaxis de enfermedades, así como su uso para la preparación de medicamentos para el tratamiento y/o la profilaxis de enfermedades, en particular para el tratamiento y/o la profilaxis de endometriosis así dolores asociados a la endometriosis y otros síntomas de endometriosis como dismenorrea, dispareunia, disuria y disquecia, de linfomas, artritis reumatoidea, espondiloartritis (en particular espondiloartritis psoriásica y enfermedad de Bechterew), lupus eritematoso sistémico, esclerosis múltiple, degeneración macular, EPOC, gota, afecciones por hígado graso, resistencia a la insulina, enfermedades tumorales y psoriasis. Reivindicación 1: Compuestos de la fórmula general (1), en la que R¹ representa halógeno, ciano, C(=O)OH, C(=O)ORᵃ, C(=O)NH₂, C(=O)N(H)Rᵃ, C(=O)N(Rᵃ)Rᵇ, C(=O)Rᵈ, hidroxi o alquilo C₁₋₆, donde el resto alquilo C₁₋₆ dado el caso puede estar mono- o polisustituido de modo igual o diferente con hidroxi, halógeno, ciano, C(=O)OH, C(=O)ORᵃ, S(=O)₂-alquilo C₁₋₆, NH₂, NHRᵃ, N(Rᵃ)Rᵇ, un alcoxi C₁₋₆ o cicloalcoxi C₃₋₇ sustituido dado el caso una o seis veces con flúor, un heterocicloalquilo de 4 a 7 miembros sustituido dado el caso una a tres veces, de modo igual o diferente con Rᶜ, o representa alcoxi C₁₋₆, donde el resto alcoxi C₁₋₆ dado el caso puede estar mono- o polisustituido de modo igual o diferente con hidroxi, halógeno, ciano, C(=O)OH, C(=O)ORᵃ, S(=O)₂-alquilo C₁₋₆, NH₂, NHRᵃ, N(Rᵃ)Rᵇ, un cicloalquilo C₃₋₇ sustituido dado el caso una a cuatro veces con flúor, alcoxi C₁₋₆ sustituido dado el caso una a cinco veces con flúor, un cicloalcoxi C₃₋₇ sustituido dado el caso una a cuatro veces con flúor, un heterocicloalquilo de 4 a 7 miembros dado el caso mono o polisustituido de manera igual o diferente con Rᶜ, o representa cicloalquiloxi C₃₋₇ o heterocicloalquiloxi de 4 a 7 miembros, donde cicloalquiloxi C₃₋₇ y heterocicloalquiloxi de 4 a 7 miembros dado el caso pueden estar mono o polisustituidos de manera igual o diferente con hidroxi, flúor, ciano, alquilo C₁₋₆ o alcoxi C₁₋₆; Rᵃ representa alquilo C₁₋₆, cicloalquilo C₃₋₇, heterocicloalquilo de 4 a 7 miembros, donde alquilo C₁₋₆, cicloalquilo C₃₋₇ y heterocicloalquilo de 4 a 7 miembros dado el caso pueden estar mono o polisustituidos de manera igual o diferente con flúor, hidroxi, ciano, alquilo C₁₋₄, alcoxi C₁₋₄ o cicloalquilo C₃₋₇; Rᵇ representa alquilo C₁₋₆ o cicloalquilo C₃₋₇; o Rᵃ y Rᵇ junto con el átomo de nitrógeno forman un heterociclo de 5 ó 6 miembros, el que dado el caso puede estar mono- o disustituido de modo igual o diferente con hidroxi, halógeno, ciano o alquilo C₁₋₆; Rᶜ representa hidroxi, flúor, cloro, ciano, alquilo C₁₋₄ o alcoxi C₁₋₄; Rᵈ representa hidrógeno, cicloalquilo C₃₋₇ o representa alquilo C₁₋₆, que dado el caso puede estar sustituido con un grupo hidroxi; R² representa un heteroarilo de 5 miembros, que está monosustituido con R⁴ y está monosustituido con R⁵ o R² representa un heteroarilo de 6 miembros, que está monosustituido con R⁴ y está mono- o disustituido, de manera igual o diferente con R⁵; R³ representa un grupo, seleccionado de los compuestos de fórmula (2), (3) ó (4), donde * representa el lugar de unión del grupo con el resto de la molécula; R⁴ representa hidrógeno, halógeno, hidroxi, C(=O)OH, ciano, NH₂, NHRᵃ, N(Rᵃ)Rᵇ, C(=O)Rᵃ, N(H)C(=O)Rᵃ, C(=O)NH₂, C(=O)N(H)Rᵃ, C(=O)N(Rᵃ)Rᵇ, S(=O)Rᵃ, S(=O)₂Rᵃ, S(=O)₂NH₂, S(=O)₂NHRᵃ o S(=O)₂N(Rᵃ)Rᵇ, o representa alquilo C₁₋₆, donde alquilo C₁₋₆ puede estar sustituido dado el caso con uno a cinco átomos de flúor y dado el caso puede estar mono- o disustituido de modo igual o diferente con hidroxi, bromo, cloro, ciano, C(=O)OH, S(=O)₂-alquilo C₁₋₆, NH₂, NHRᵃ, N(Rᵃ)Rᵇ, cicloalquilo C₃₋₇, alcoxi C₁₋₄, cicloalcoxi C₃₋₇, trifluorometoxi, o representa alcoxi C₁₋₆, donde alcoxi C₁₋₆ puede estar sustituido dado el caso con uno a cinco átomos de flúor y dado el caso puede estar mono- o disustituido de modo igual o diferente con hidroxi, cloro, bromo, ciano, C(=O)OH, S(=O)₂-alquilo C₁₋₆, NH₂, NHRᵃ, N(Rᵃ)Rᵇ, cicloalquilo C₃₋₇, alcoxi C₁₋₄, cicloalcoxi C₃₋₇, trifluorometoxi, o representa cicloalquilo C₃₋₇ o representa cicloalquiloxi C₃₋₇, donde cicloalquilo C₃₋₇ y cicloalquiloxi C₃₋₇ dado el caso pueden estar sustituidos con uno a cuatro átomos de flúor y dado el caso pueden estar mono- o disustituidos de modo igual o diferente con hidroxi, cloro, bromo, ciano, C(=O)Rᵈ, C(=O)OH, alquilo C₁₋₆ o alcoxi C₁₋₄, o representa un heterocicloalquilo de 4 a 7 miembros, que dado el caso puede estar sustituidos con uno a cuatro átomos del flúor y dado el caso puede estar mono- o disustituido de modo igual o diferente con hidroxi, cloro, bromo, ciano, NH₂, NHRᵃ, N(Rᵃ)Rᵇ, C(=O)Rᵈ, C(=O)OH, alquilo C₁₋₆, trifluorometilo, 2,2,2-trifluoroetilo, ciclopropilo, ciclopropilmetilo o alcoxi C₁₋₄, bromo, ciano, NH₂, NHRᵃ, N(Rᵃ)Rᵇ, C(=O)Rᵈ, C(=O)OH, alquilo C₁₋₆, trifluorometilo, 2,2,2-trifluoroetilo, ciclopropilo, ciclopropilmetilo o alcoxi C₁₋₄, o representa fenilo o heteroarilo de 5 ó 6 miembros, donde fenilo y heteroarilo de 5 ó 6 miembros dado el caso pueden estar mono- o disustituidos de manera igual o diferente con flúor, cloro, bromo, hidroxi, ciano, C(=O)OH, S(=O)₂-alquilo C₁₋₄, NH₂, NHRᵃ, N(Rᵃ)Rᵇ, N(H)C(=O)Rᵃ, alcoxi C₁₋₄, trifluorometoxi o alquilo C₁₋₄, donde alquilo C₁₋₄ dado el caso puede estar mono- a trisustituido con flúor; R⁵ representa hidrógeno, halógeno, hidroxi, ciano, alcoxi C₁₋₄, trifluorometoxi o alquilo C₁₋₆, donde alquilo C₁₋₆ puede estar sustituido dado el caso con uno a cinco átomos de flúor; R⁶ᶠ representa hidrógeno, flúor, C(=O)OH, C(=O)NH₂, trifluorometilo, hidroximetilo, metoximetilo, ciano o alquilo C₁₋₆; R⁶ᵍ representa hidrógeno, flúor o alquilo C₁₋₆ o R⁶ᶠ y R⁶ᵍ forman junto con el átomo de carbono al que están unidos, un cicloalquilo C₃₋₇, o R⁶ᶠ y R⁶ᵍ representan juntos un grupo oxo; R⁶ʰ representa hidrógeno, trifluorometilo o alquilo C₁₋₆; R⁶ⁱ representa hidrógeno o alquilo C₁₋₆, o R⁶ʰ y R⁶ⁱ representan juntos un grupo oxo; R⁶ʲ representa hidrógeno, flúor, NH₂, N(H)Rᵃ, N(Rᵃ)Rᵇ, alquilo C₁₋₆, hidroxi, ciano, alcoxi C₁₋₄, C₍₌O₎OH, C₍₌O₎NH₂, C(=O)N(H)Rᵃ, C(=O)N(Rᵃ)Rᵇ, hidroximetilo, dimetilaminometilo, trifluorometilo; R⁶ᵏ representa hidrógeno, flúor o alquilo C₁₋₆ o R⁶ʲ y R⁶ᵏ forman junto con el átomo de carbono un cicloalquilo C₃₋₇; R⁶ˡ representa hidrógeno o metilo; R⁶ᵐ representa hidrógeno o metilo; G representa -CH₂- o -CH₂CH₂-; n en la fórmula (2) representa 0, 1 ó 2; n en la fórmula (3) representa 1 ó 2; n en la fórmula (4) representa 0 ó 1; z representa un grupo seleccionado de NR⁷, O, S, S(=O), S(=O)₂, S(=O)(=NH); R⁷ representa hidrógeno, C(=O)Rᵉ, C(=O)ORᵃ, C(=O)NH₂, C(=O)N(H)Rᵃ, C(=O)N(Rᵃ)Rᵇ, S(=O)₂Rᵃ, S(=O)₂NH₂, S(=O)₂N(Rᵃ)H, S(=O)₂N(Rᵃ)Rᵇ, S(=O)₂NHC(=O)CH₃, S(=O)₂NHC(=O)CH₂CH₃ o alquilo C₁₋₆, donde alquilo C₁₋₆, dado el caso puede estar mono- a pentasustituido con átomos de flúor y puede estar mono- a disustituido de manera igual o diferente con hidroxi, cloro, bromo, ciano, C(=O)Rᵃ, C(=O)OH, C(=O)NH₂, C(=O)N(H)Rᵃ, C(=O)N(Rᵃ)Rᵇ, S(=O)₂-alquilo C₁₋₆, NH₂, NHRᵃ, N(Rᵃ)Rᵇ, morfolin-4-ilo, 4-metilpiperazin-1-ilo, cicloalquilo C₃₋₇, alcoxi C₁₋₄ o cicloalcoxi C₃₋₇; o representa cicloalquilo C₃₋₇, que dado el caso puede estar mono- a tetrasustituido con átomos de flúor y dado el caso puede estar mono- a disustituido de manera igual o diferente con hidroxi, metilo, etilo, trifluorometilo o ciano; o representa un heterocicloalquilo de 4 - 7 miembros unido con el resto de la molécula mediante un átomo de carbono o representa heterocicloalquil-alquilo C₁₋₄ de 4 - 7 miembros, los cuales dado el caso pueden estar sustituidos uno a seis veces con átomos de flúor y pueden estar sustituidos una a tres veces, de manera igual o diferente, con hidroxi, cloro, bromo, ciano, alquilo C₁₋₆, alcoxi C₁₋₆, trifluorometilo, 2,2,2-trifluoroetilo, trifluorometoxi, ciclopropilo, ciclopropilmetilo; Rᵉ representa alquilo C₁₋₆, donde alquilo C₁₋₆ dado el caso puede estar sustituido una a tres veces, de manera igual o diferente, con hidroxi, flúor, cloro, ciano, C(=O)Rᵃ, C(=O)OH, NH₂, NHRᵃ, N(Rᵃ)Rᵇ, cicloalquilo C₃₋₇, alcoxi C₁₋₄, trifluorometoxi o cicloalcoxi C₃₋₇ o Rᵉ representa cicloalquilo C₃₋₇, donde cicloalquilo C₃₋₇ dado el caso puede estar mono- a tetrasustituido con flúor y dado el caso está monosustituido con hidroxi.
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| US10501417B2 (en) | 2016-04-29 | 2019-12-10 | Bayer Pharma Aktiengesellschaft | Synthesis of indazoles |
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| CN112513027B (zh) * | 2018-08-17 | 2024-03-29 | 浙江海正药业股份有限公司 | 吲唑胺类衍生物及其制备方法和其在医药上的用途 |
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| US10435396B2 (en) | 2019-10-08 |
| JP6947743B2 (ja) | 2021-10-13 |
| CN109153665A (zh) | 2019-01-04 |
| UY37142A (es) | 2017-10-31 |
| TW201734004A (zh) | 2017-10-01 |
| US20190071432A1 (en) | 2019-03-07 |
| CN109153665B (zh) | 2021-10-15 |
| EP3423446A1 (de) | 2019-01-09 |
| CA3016364A1 (en) | 2017-09-08 |
| EP3423446B1 (de) | 2020-09-16 |
| WO2017148902A1 (de) | 2017-09-08 |
| JP2019507168A (ja) | 2019-03-14 |
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