AR098991A1 - Compuestos de nicotinamida sustituida con heteroarilo - Google Patents
Compuestos de nicotinamida sustituida con heteroariloInfo
- Publication number
- AR098991A1 AR098991A1 ARP140104949A ARP140104949A AR098991A1 AR 098991 A1 AR098991 A1 AR 098991A1 AR P140104949 A ARP140104949 A AR P140104949A AR P140104949 A ARP140104949 A AR P140104949A AR 098991 A1 AR098991 A1 AR 098991A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- fluoroalkyl
- nhc
- ch2nhc
- fluoroalkylene
- Prior art date
Links
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical class NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 title 1
- -1 pyrrolo [2,3-b] pyridinyl Chemical group 0.000 abstract 29
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 28
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 16
- 125000003709 fluoroalkyl group Chemical group 0.000 abstract 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 10
- 125000005466 alkylenyl group Chemical group 0.000 abstract 9
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 8
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 abstract 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 7
- 125000001424 substituent group Chemical group 0.000 abstract 7
- 125000003566 oxetanyl group Chemical group 0.000 abstract 6
- 125000002757 morpholinyl group Chemical group 0.000 abstract 5
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 5
- 125000004076 pyridyl group Chemical group 0.000 abstract 5
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000002883 imidazolyl group Chemical group 0.000 abstract 4
- 125000003386 piperidinyl group Chemical group 0.000 abstract 4
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 abstract 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 2
- 125000004122 cyclic group Chemical group 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000004193 piperazinyl group Chemical group 0.000 abstract 2
- 125000000335 thiazolyl group Chemical group 0.000 abstract 2
- 125000006712 (C1-C4) deuteroalkyl group Chemical group 0.000 abstract 1
- 125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 abstract 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- IGVGARQHWLUJIO-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1,3-benzothiazol-2-amine Chemical compound C1C=CC=C2SC(N)NC21 IGVGARQHWLUJIO-UHFFFAOYSA-N 0.000 abstract 1
- 125000005899 2,3-dihydro-1H-pyrrolo[2,3-b]pyridinyl group Chemical group 0.000 abstract 1
- 208000023275 Autoimmune disease Diseases 0.000 abstract 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 1
- 101000977771 Homo sapiens Interleukin-1 receptor-associated kinase 4 Proteins 0.000 abstract 1
- 102100023533 Interleukin-1 receptor-associated kinase 4 Human genes 0.000 abstract 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 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
- NIZFPIBTGJOVRT-UHFFFAOYSA-N bicyclo[2.2.1]heptan-4-ol Chemical compound C1CC2CCC1(O)C2 NIZFPIBTGJOVRT-UHFFFAOYSA-N 0.000 abstract 1
- 125000006390 chloropyrimidinyl group Chemical group 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000005345 deuteroalkyl group Chemical group 0.000 abstract 1
- 125000004212 difluorophenyl group Chemical group 0.000 abstract 1
- 125000001207 fluorophenyl group Chemical group 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 abstract 1
- 125000001041 indolyl group Chemical group 0.000 abstract 1
- 208000027866 inflammatory disease Diseases 0.000 abstract 1
- 230000002757 inflammatory effect Effects 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 abstract 1
- 125000001715 oxadiazolyl group Chemical group 0.000 abstract 1
- 125000002971 oxazolyl group Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 abstract 1
- 125000002098 pyridazinyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000003831 tetrazolyl group Chemical group 0.000 abstract 1
- 125000001113 thiadiazolyl group Chemical group 0.000 abstract 1
- 125000004306 triazinyl group Chemical group 0.000 abstract 1
- 125000001425 triazolyl group Chemical group 0.000 abstract 1
Classifications
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- 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
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- 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
- A61K31/435—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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—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
- A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- 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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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
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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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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
También se describen el uso de tales compuestos como moduladores de IRAK4, y composiciones farmacéuticas que comprenden tales compuestos. Estos compuestos son útiles para tratar, prevenir o ralentizar enfermedades inflamatorias y autoinmunitarias. Reivindicación 1: Un compuesto caracterizado por la fórmula (1) o una sal de aquel, en donde: HET es un heteroarilo seleccionado de pirazolilo, indolilo, pirrolo[2,3-b]piridinilo, pirrolo[2,3-d]pirimidinilo, pirazolo[3,4-b]piridinilo, pirazolo[3,4-d]pirimidinilo, 2,3-dihidro-1H-pirrolo[2,3-b]piridinilo, imidazo[4,5-b]piridinilo y purinilo, en donde el heteroarilo se sustituye con Rᵃ y Rᵇ; Rᵃ es H, F, Cl, Br, -CN, -OH, C₁₋₄ alquilo, C₁₋₄ fluoroalquilo, C₁₋₄ hidroxialquilo, C₁₋₄ alcoxi, -NH₂, -NH(C₁₋₄ alquilo), -N(C₁₋₄ alquilo)₂, -NH(C₁₋₄ hidroxialquilo), -NH(C₁₋₄ fluoroalquilo), -NH(C₁₋₆ hidroxi-fluoroalquilo), -C(O)NH₂, -CH₂NHC(O)(C₁₋₆ alquilo), -CH₂NHC(O)(C₁₋₆ hidroxialquilo), -CH₂NHC(O)NH(C₁₋₆ alquilo), -CH₂NHC(O)NHCH₂(fenilo), -CH₂NHC(O)N(C₁₋₄ alquilo)₂, -CH₂NHC(O)O(C₁₋₄ alquilo), -CH₂NHC(O)(C₃₋₈ cicloalquilo), -CH₂NHC(O)(tetrahidrofuranilo), -CH₂NHC(O)CH₂(C₃₋₆ cicloalquilo), -CH₂NHC(O)CH₂(tetrahidropiranilo), -CH₂NHC(O)CH₂(fenilo), -NHC(O)(C₁₋₄ alquilo), pirrolidinilo, hidroxipirrolidinilo o piridazinilo; Rᵇ es H o -NH₂; R¹ es: (i) C₁₋₆ alquilo, C₁₋₆ fluoroalquilo, C₁₋₆ hidroxialquilo, C₁₋₈ hidroxi-fluoroalquilo,-(C₁₋₆ alquilenil)O(C₁₋₄ alquilo), -(C₁₋₆ alquilenil)O(C₁₋₄ fluoroalquilo), -(C₁₋₆ fluoroalquilenil)O(C₁₋₄ alquilo), -(C₁₋₆ fluoroalquilenil)O(C₁₋₄ deuteroalquilo), -(C₁₋₆ fluoroalquilenil)O(C₁₋₄ fluoroalquilo), -(C₁₋₄ fluoroalquilenil)C(C₃₋₆ cicloalquil)₂(OH), -(C₁₋₄ alquilenil)NHC(O)(C₁₋₄ alquilenil)OC(O)(C₁₋₃ alquilo), -(C₁₋₆ alquilenil)NHS(O)₂(C₁₋₄ alquilo), -(C₁₋₆ alquilenil)P(O)(C₁₋₄ alcoxi)₂, -(C₁₋₆ fluoroalquilenil)NH(C₁₋₄ alquilo), -(C₁₋₆ alquilenil)C(O)NH(C₁₋₄ alquilo), -(C₁₋₆ fluoroalquilenil)C(O)NH(C₁₋₄ alquilo), -(C₁₋₆ fluoroalquilenil)C(O)NH(C₁₋₄ hidroxialquilo) o -(C₁₋₆ fluoroalquilenil)OP(O)(OH)₂; (ii) -(C₁₋₃, alquilenil)Rˣ, -(C₁₋₃ fluoroalquilenil)Rˣ, -(C₁₋₃ alquilenil)C(O)Rˣ, -(C₁₋₃ alquilenil)C(O)NHRˣ, -(C₁₋₃, fluoroalquilenil)C(O)Rˣ o CH₂CF=(tetrahidropiranilo), en donde Rˣ es un grupo cíclico seleccionado de C₃₋₆ cicloalquilo, tetrazolilo, 1,1-dioxidotetrahidrotiofenilo, 1,1-dioxidotiomorfolinilo, oxadiazolilo, piperidinilo, piperazinilo, pirrolidinilo, oxetanilo, tetrahidrofuranilo, tetrahidropiranilo, piridinilo, imidazolilo, morfolinilo, fenilo y triazinilo, en donde cada grupo cíclico se sustituye con 0 a 3 sustituyentes seleccionados independientemente de F, -OH, -CH₃, -C(CH₂)₂OH, -OCH₃, -C(O)CH₂CN, -S(O)₂CH₃, -S(O)₂NH₂, -NHC(O)CH₃, -N(S(O)₂CH₃)₂, -CH₂CH₂(acetamidofenilo), -CH₂CH₂(metoxifenilo), -CH₂CH₂(sulfamoilfenilo), oxetanilo, bencilo y morfolinilo; (iii) C₃₋₆ cicloalquilo o C₄₋₆ cicloalquenilo, cada uno sustituido con 0 a 3 sustituyentes seleccionados independientemente de F, -OH, -CN, C₁₋₃ alquilo, C₁₋₃ alcoxi, -S(C₁₋₃ alquilo), -NO₂, -S(O)₂(C₁₋₃ alquilo), C₁₋₄ hidroxialquilo, -C(C₁₋₃ alquil)(OH)(C₃₋₆ cicloalquilo), -CH₂C(O)NH(C₁₋₃ alquilo), -NHC(O)(C₁₋₃ alquilo), -NHC(O)(C₁₋₄ hidroxialquilo), -C(O)NH(C₁₋₃ alquilo), -C(O)NH(C₁₋₃ deuteroalquilo), -C(O)NH(C₃₋₆ cicloalquilo), -NHC(O)O(C₁₋₃ alquilo), -NHS(O)₂(C₁₋₃ alquilo), piridinilo, imidazolilo, pirazolilo, metilimidazolilo, metilpirazolilo y tiazolilo; (iv) tetrahidropiranilo, piperidinilo, pirazolilo, fenilo, piridinilo o pirimidinilo, cada uno sustituido con 0 a 1 sustituyente seleccionado de -OH, C₁₋₃ alquilo, C₁₋₃ fluoroalquilo, C₁₋₄ hidroxialquilo, C₁₋₃ alcoxi, -C(O)(C₁₋₄ alquilo), -S(O)₂(C₁₋₄ alquilo), -S(O)₂NH(C₁₋₄ alquilo), -NH(C₁₋₃ alquilo), -N(C₁₋₃ alquilo)₂, -O(C₁₋₃ alquilenil)N(C₁₋₃ alquilo)₂, -CH₂(morfolinilo), acetidinilo, oxetanilo, tetrahidropiranilo, morfolinilo, piperazinilo, piperidinilo, metilpiperazinilo, metoxipiperidinilo, piridinilo, pirimidinilo, metilsulfonilo acetidinilo y -C(O)(acetidinilo de metilsulfonilo); o (v) pirrolo[2,3-c]piridinilo, biciclo[2.2.1]heptan-1-ol, tetrahidrobenzo[d]tiazol-2-amina o 1,3-diazaspiro[4.5]decan-2,4-diona; y R² es (i) C₁₋₇ alquilo o C₂₋₆ alquenilo, cada uno sustituido con 0 a 3 sustituyentes seleccionados independientemente de F, -OH y -CN; -(C₁₋₄ alquilenil)O(C₁₋₄ alquilo), -(C₁₋₄ alquilenil)O(C₁₋₄ fluoroalquilo), -(C₁₋₆ alquilenil)NH₂, -(C₁₋₆ alquilenil)S(O)₂(C₁₋₃ alquilo), -(C₁₋₆ fluoroalquilenil)NH(C₁₋₃ alquilo) o -(C₁₋₆ alquilenil)NHC(O)(C₁₋₄ fluoroalquilo); (ii) -(C₁₋₄ alquilenil)Rʸ, en donde Rʸ es C₃₋₆ cicloalquilo, acetidinilo, oxetanilo, oxazolilo, piridinilo, tetrahidropiranilo o morfolinilo, cada uno sustituido con o a 2 sustituyentes seleccionados independientemente de F, OH y C₁₋₃ alquilo; (iii) C₃₋₆ cicloalquilo, acetidinilo, oxetanilo, furanilo, tetrahidrofuranilo, pirrolidinilo, piperidinilo o tetrahidropiranilo, cada uno sustituido con 0 a 3 sustituyentes seleccionados independientemente de F, -OH, C₁₋₃ alquilo, C₁₋₃, hidroxialquilo, -C(O)(C₁₋₃ alquilo), -C(O)(C₁₋₃ fluoroalquilo), -C(O)(C₁₋₃ cianoalquilo), -C(O)O(C₁₋₃ alquilo), -C(O)NH₂, -C(O)NH(C₁₋₃ alquilo), -C(O)(difluorofenilo), -NH₂, -NH(C₁₋₃ alquilo), -NH(C₁₋₃ fluoroalquilo), -NH(oxetanilo), -NHC(O)(C₁₋₃ alquilo), -NHC(O)(C₁₋₃ fluoroalquilo), -NHC(O)(C₃₋₆ cicloalquilo), -NHC(O)(fluorofenilo), -S(O)₂(C₁₋₃ alquilo), imidazolilo, fenilo, pirimidinilo, fluoropirimidinilo, cloropirimidinilo y metoxipirimidinilo; (iv) adamantanilo, hidroxiadamantanilo, benzo[d]imidazolilo, benzo[d]oxazolilo, benzo[d]triazolilo, benzotiazolilo, biciclo[1.1.1]pentanilo o hidroxibiciclo[2.2.1]heptanilo; o (v) fenilo, pirazolilo, tiazolilo, tiadiazolilo o indazolilo, cada uno sustituido con 0 a 2 sustituyentes seleccionados independientemente de F, Cl, -OH, -CN, C₁₋₄ alquilo, C₁₋₄ hidroxialquilo, C₁₋₄ fluoroalquilo, C₁₋₄ cianoalquilo, C₁₋₃ alcoxi, C₃₋₆ cicloalquilo, -(C₁₋₃ alquilenil)O(C₁₋₃ alquilo), -(C₁₋₃ alquilenil)O(C₁₋₃ fluoroalquilo), -C(O)NH₂, -C(O)NH(C₁₋₃ alquilo), -NHC(O)(C₁₋₃ alquilo), -NHC(O)S(O)₂(C₁₋₃ alquilo), -S(O)₂NH₂, -S(O)₂(C₁₋₃ alquilo), pirazolilo, metilpirazolilo, imidazolilo, triazolilo, metiltetrazolilo, etiltetrazolilo, fenilo, pirimidinilo, fluoropirimidinilo y tetrahidropiranilo.
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TW201609693A (zh) | 2016-03-16 |
EP3089973B1 (en) | 2020-04-29 |
WO2015103453A1 (en) | 2015-07-09 |
EA201691343A1 (ru) | 2016-11-30 |
PE20161292A1 (es) | 2016-11-23 |
MX2016008723A (es) | 2016-09-07 |
TN2016000271A1 (en) | 2017-10-06 |
ES2804707T3 (es) | 2021-02-09 |
JP2017501202A (ja) | 2017-01-12 |
US9169252B2 (en) | 2015-10-27 |
CA2935329A1 (en) | 2015-07-09 |
UY35935A (es) | 2015-06-30 |
AU2015204045A1 (en) | 2016-08-18 |
CL2016001706A1 (es) | 2017-02-10 |
US20150191464A1 (en) | 2015-07-09 |
KR20160101191A (ko) | 2016-08-24 |
EP3089973A1 (en) | 2016-11-09 |
JP6475252B2 (ja) | 2019-02-27 |
MA39162A1 (fr) | 2017-12-29 |
CN106061967A (zh) | 2016-10-26 |
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