AR094982A1 - Derivados de triazolo[4,5-d]pirimidina - Google Patents
Derivados de triazolo[4,5-d]pirimidinaInfo
- Publication number
- AR094982A1 AR094982A1 ARP140100697A ARP140100697A AR094982A1 AR 094982 A1 AR094982 A1 AR 094982A1 AR P140100697 A ARP140100697 A AR P140100697A AR P140100697 A ARP140100697 A AR P140100697A AR 094982 A1 AR094982 A1 AR 094982A1
- Authority
- AR
- Argentina
- Prior art keywords
- phet1
- mono
- denotes
- oconh
- nhcoo
- Prior art date
Links
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical class C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 title 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title 1
- -1 4,5,6,7-tetrahydro-1H-indazol-5-yl Chemical group 0.000 abstract 14
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 4
- 125000004076 pyridyl group Chemical group 0.000 abstract 4
- 125000002393 azetidinyl group Chemical group 0.000 abstract 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 3
- 125000001715 oxadiazolyl group Chemical group 0.000 abstract 3
- 125000003386 piperidinyl group Chemical group 0.000 abstract 3
- 125000003373 pyrazinyl group Chemical group 0.000 abstract 3
- 125000002098 pyridazinyl 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
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 2
- 125000001041 indolyl group Chemical group 0.000 abstract 2
- 125000000842 isoxazolyl group Chemical group 0.000 abstract 2
- 125000002757 morpholinyl group Chemical group 0.000 abstract 2
- 125000002971 oxazolyl group Chemical group 0.000 abstract 2
- 125000003566 oxetanyl group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 2
- 125000003831 tetrazolyl group Chemical group 0.000 abstract 2
- 125000001425 triazolyl group Chemical group 0.000 abstract 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 abstract 1
- 240000000543 Pentas lanceolata Species 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003828 azulenyl group Chemical group 0.000 abstract 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 abstract 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 abstract 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 abstract 1
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 abstract 1
- 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 abstract 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 abstract 1
- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 abstract 1
- 125000005879 dioxolanyl group Chemical group 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 125000005945 imidazopyridyl group Chemical group 0.000 abstract 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 abstract 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 abstract 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 abstract 1
- 125000005956 isoquinolyl group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000004193 piperazinyl group Chemical group 0.000 abstract 1
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 abstract 1
- 125000005493 quinolyl group Chemical group 0.000 abstract 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 125000005942 tetrahydropyridyl group Chemical group 0.000 abstract 1
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 abstract 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 abstract 1
- 125000000335 thiazolyl group Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 125000001166 thiolanyl group Chemical group 0.000 abstract 1
Classifications
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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
-
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- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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Abstract
Reivindicación 1: Compuestos de la fórmula (1), en donde R¹ denota Ar o Het; R² denota alquilo no ramificado o ramificado C₁₋₇, en donde dos átomos de carbono adyacentes pueden formar un enlace doble o triple y que puede estar mono-, di-, tri-, tetra- o pentasustituido con Hal y/o que puede estar mono- o disustituido con OR³, N(R³)₂, Het¹, CN, COOR³, OCOOR³, CONH₂, CONHA, CONA₂, NR³COA, NR³SO₂A, SO₂N(R³)₂, S(O)ₙA, COHet¹, O[C(R³)₂]ₘN(R³)₂, O[C(R³)₂]ₚHet¹, NHCOOA, NHCON(R³)₂, NHCOO[C(R³)₂]ₘN(R³)₂, NHCOO[C(R³)₂]ₚHet¹, NHCONH[C(R³)₂]ₘN(R³)₂, NHCONH[C(R³)₂]ₚHet¹, OCONH[C(R³)₂]ₘN(R³)₂, OCONH[C(R³)₂]ₚHet¹, y/o COA, o denota cicloalquilo C₃₋₇ o ciclopentenilo, cada uno de los cuales puede estar mono-, di-, tri-, tetra- o pentasustituido con A y/o Hal y/o que puede estar mono- o disustituido con [C(R³)₂]ₚOR³, O[C(R³)₂]ₚOR³, [C(R³)₂]ₚN(R³)₂, O[C(R³)₂]ₚN(R³)₂, [C(R³)₂]ₚAr, [C(R³)₂]ₚHet¹, O[C(R³)₂]ₚHet¹, CN, [C(R³)₂]ₚCOOR³, O[C(R³)₂]ₚCOOR³, CONH₂, CONHA, CONA₂, [C(R³)₂]ₚNR³COA, CONR³SO₂A, NR³SO₂A, SO₂N(R³)₂, S(O)ₙA, COHet¹, O[C(R³)₂]ₘN(R³)₂, [C(R³)₂]ₚNR³COOA, [C(R³)₂]ₚNR³COOCH₂Ph, NR³CON(R³)₂, NHCOO[C(R³)₂]ₘN(R³)₂, NHCOO[C(R³)₂]ₚHet¹, NHCONH[C(R³)₂]ₘ N(R³)₂, NHCONH[C(R³)₂]ₚHet¹, OCONH[C(R³)₂]ₘN(R³)₂, OCONH[C(R³)₂]ₚHet¹, CONH(CH₂)ₚHet², CONR³NR³COA, CONR³N(R³)₂, CONHCyc, COA, S, =NR³ y/u =O, o denota piperidinilo, tetrahidropiranilo, pirrolidinilo, azetidinilo, tiolanilo, oxetanilo, 3-aza-biciclo[3,1,0]hexilo, tetrahidrotiofenilo, tetrahidrotiopiranilo, 4,5,6,7-tetrahidro-1H-indazol-5-ilo, 4,5,6,7-tetrahidro-1H-indazol-6-ilo, tetrahidropirazolilo, tetrahidrofuranilo o hexahidropiridazinilo, cada uno de los cuales puede estar mono-, di-, tri-, tetra- o pentasustituido con A y/o Hal y/o que puede estar mono- o disustituido con [C(R³)₂]ₚOR³, O[C(R³)₂]ₚOR³, [C(R³)₂]ₚN(R³)₂, [C(R³)₂]ₚAr, [C(R³)₂]ₚHet¹, [C(R³)₂]ₚHet3, CN, [C(R³)₂]COOR³, CO[C(R³)₂]ₚN(R³)₂, CO[C(R³)₂]ₚHet¹, CO[C(R³)₂]ₚHet3, NR³COA, NR³SO₂A, SO₂N(R³)₂, S(O)ₙA, COHet¹, O[C(R³)₂]ₘN(R³)₂, O[C(R³)₂]ₚHet¹, NHCOOA, NHCON(R³)₂, NHCOO[C(R³)₂]ₘN(R³)₂, NHCOO[C(R³)₂]ₚHet¹, NHCONH[C(R³)₂]ₘN(R³)₂, NHCONH[C(R³)₂]ₚHet¹, OCONH[C(R³)₂]ₘN(R³)₂, OCONH[C(R³)₂]ₚHet¹, C(O)R³, =S, =NR³ y/u =O; R³ denota H o alquilo no ramificado o ramificado C₁₋₆; Ar denota fenilo o naftilo, cada uno de los cuales no está sustituido o está mono-, di- o trisustituido con Hal, A, [C(R³)₂]ₚOR³, O[C(R³)₂]ₚOR³, [C(R³)₂]ₚN(R³)₂, O[C(R³)₂]ₚN(R³)₂, [C(R³)₂]ₚHet¹, [C(R³)₂]ₚHet3, NO₂, CN, [C(R³)₂]ₚCOOR³, O[C(R³)₂]ₚCOOR³, CON(R³)₂, NR³COA, NR³SO₂A, SO₂N(R³)₂, S(O)ₙA, COHet¹, O[C(R³)₂]ₚHet¹, NHCOOA, NHCON(R³)₂, NHCOO[C(R³)₂]ₘN(R³)₂, NHCOO[C(R³)₂]ₚHet¹, NHCONH[C(R³)₂]ₘN(R³)₂, NHCONH[C(R³)₂]ₚHet¹, OCONH[C(R³)₂]ₘN(R³)₂, OCONH[C(R³)₂]ₚHet¹, S(O)ₙHet¹, CHO y/o COA, o denota azulenilo; Het denota furilo, tienilo, pirrolilo, imidazolilo, pirazolilo, oxazolilo, isoxazolilo, oxadiazolilo, tiazolilo, triazolilo, tetrazolilo, piridilo, pirimidilo, piridazinilo, pirazinilo, indolilo, isoindolilo, bencimidazolilo, indazolilo, indolizinilo, cinnolinilo, quinolilo, isoquinolilo, benzoxazolilo, 1,3-benzodioxolilo, benzotiofenilo, benzofuranilo, imidazopiridilo, dihidroindolilo, quinoxalinilo, imidazo[1,2-a]piridinilo, benzo[1,2,5]tiadiazolilo, naftiridinilo, 2,3-dihidro-benzo[1,4]dioxinilo, quinazolinilo, benzotiazolilo o furo[3,2-b]piridilo, cada uno de los cuales no está sustituido o está mono- o disustituido con Hal, A, [C(R³)₂]ₚOR³, O[C(R³)₂]ₚOR³, [C(R³)₂]ₚ N(R³)₂, O[C(R³)₂]ₚN(R³)₂, [C(R³)₂]ₚHet¹, NO₂, [C(R³)₂]ₚ CN, [C(R³)₂]ₚCOOR³, O[C(R³)₂]ₚCOOR³, [C(R³)₂]ₚCON(R³)₂, NR³COA, NR³SO₂A, SO₂N(R³)₂, S(O)ₙA, COHet², O[C(R³)₂]ₚHet², NHCOOA, NHCON(R³)₂, NHCOO[C(R³)₂]ₘN(R³)₂, NHCOO[C(R³)₂]ₚHet², NHCONH[C(R³)₂]ₘN(R³)₂, NHCONH[C(R³)₂]ₚHet², OCONH[C(R³)₂]ₘN(R³)₂, OCONH[C(R³)₂]ₚHet², S(O)ₙHet², CHO, COA, =S y/u =O; Het¹ denota pirazolilo, piridazinilo, piridinilo, oxazolilo, isoxazolilo, oxadiazolilo, pirazinilo, indolilo, dihidropirrolilo, pirrolidinilo, azetidinilo, oxetanilo, tetrahidroimidazolilo, dihidropirazolilo, tetrahidropirazolilo, tetrahidrofuranilo, dihidropiridilo, tetrahidropiridilo, piperidinilo, morfolinilo, hexahidropiridazinilo, hexahidropirimidinilo, [1,3]dioxolanilo, tetrahidropiranilo o piperazinilo, cada uno de los cuales no está sustituido o está mono- o disustituido con Hal, A, [C(R³)₂]ₚOR³, O[C(R³)₂]ₚOR³, [C(R³)₂]ₚN(R³)₂, [C(R³)₂]ₚHet², NO₂, [C(R³)₂]ₚCN, [C(R³)₂]ₚCOOR³, O[C(R³)₂]ₚCOOR³, [C(R³)₂]ₚCON(R³)₂, NR³COA, NR³SO₂A, SO₂N(R³)₂, S(O)ₙA, COHet², O[C(R³)₂]ₘN(R³)₂, O[C(R³)₂]ₚHet², NHCOOA, NHCON(R³)₂, NHCOO[C(R³)₂]ₘN(R³)₂, NHCOO[C(R³)₂]ₚ Het², NHCONH[C(R³)₂]ₘN(R³)₂, NHCONH[C(R³)₂]ₚHet², OCONH[C(R³)₂]ₘN(R³)₂, OCONH[C(R³)₂]ₚHet², S(O)ₙHet², CHO, COA, =S y/u =O; Het² denota pirazolilo, oxadiazolilo, piridinilo, triazolilo, tetrazolilo, piridazinilo, pirrolidinilo, azetidinilo, azoxetanilo, tetrahidroimidazolilo, tetrahidropirazolilo, tetrahidrofuranilo, piperidinilo, morfolinilo, tetrahidropiranilo o piperazinilo, cada uno de los cuales no está sustituido o está mono- o disustituido con Hal, A, OA, CN, COOA, CONH₂, S(O)ₙA, S(O)ₙAr, COA y/u =O; Het³ denota pirazolilo, piridinilo, pirimidinilo o pirazinilo, cada uno de los cuales no está sustituido o está mono- o disustituido con Hal, A, [C(R³)₂]ₚOR³, O[C(R³)₂]ₚOR³, [C(R³)₂]ₚN(R³)₂, [C(R³)₂]ₚHet², NO₂, CN, [C(R³)₂]ₚCOOR³, O[C(R³)₂]ₚCOOR³, CON(R³)₂, NR³COA, NR³SO₂A, SO₂N(R³)₂, S(O)ₙA, COHet², O[C(R³)₂]ₘN(R³)₂, O[C(R³)₂]ₚHet², NHCOOA, NHCON(R³)₂, NHCOO[C(R³)₂]ₘN(R³)₂, NHCOO[C(R³)₂]ₚHet², NHCONH[C(R³)₂]ₘN(R³)₂, NHCONH[C(R³)₂]ₚHet², OCONH[C(R³)₂]ₘN(R³)₂, OCONH[C(R³)₂]ₚHet², S(O)ₙHet², CHO, COA, =S y/u =O; Cyc es cicloalquilo C₃₋₇, que puede estar mono- o disustituido con OH; Ph denota fenilo; A denota alquilo no ramificado o ramificado C₁₋₁₀, en donde uno, dos o tres grupos CH y/o CH₂ no adyacentes pueden estar reemplazados por átomos de N, O y/o S y en donde 1 - 7 átomos de H pueden estar reemplazados por OH, F y/o Cl; Hal denota F, Cl, Br o I; n denota 0, 1 ó 2; m denota 1, 2 ó 3; p denota 0, 1, 2, 3 ó 4; y sus solvatos, sales, tautómeros y estereoisómeros farmacéuticamente aceptables, incluyendo su mezclas en todas las proporciones.
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| EA034440B1 (ru) * | 2015-10-29 | 2020-02-07 | Эффектор Терапьютикс, Инк. | СОЕДИНЕНИЯ ПИРРОЛО-, ПИРАЗОЛО-, ИМИДАЗОПИРИМИДИНА И ПИРИДИНА, КОТОРЫЕ ИНГИБИРУЮТ Mnk1 И Mnk2 |
| US10874672B2 (en) | 2015-12-10 | 2020-12-29 | Ptc Therapeutics, Inc. | Methods for treating Huntington's disease |
| TWI794171B (zh) | 2016-05-11 | 2023-03-01 | 美商滬亞生物國際有限公司 | Ｈｄａｃ抑制劑與ｐｄ-ｌ１抑制劑之組合治療 |
| TWI808055B (zh) | 2016-05-11 | 2023-07-11 | 美商滬亞生物國際有限公司 | Hdac 抑制劑與 pd-1 抑制劑之組合治療 |
| CN109790122B (zh) | 2016-08-10 | 2022-06-24 | 武田药品工业株式会社 | 杂环化合物 |
| PT3559009T (pt) | 2016-12-22 | 2021-05-04 | Calithera Biosciences Inc | Composições e métodos para inibir a atividade da arginase |
| KR20200033249A (ko) | 2017-06-05 | 2020-03-27 | 피티씨 테라퓨틱스, 인크. | 헌팅턴병 치료 화합물 |
| CN111182898B (zh) | 2017-06-28 | 2024-04-16 | Ptc医疗公司 | 用于治疗亨廷顿氏病的方法 |
| CA3067592A1 (en) | 2017-06-28 | 2019-01-03 | Ptc Therapeutics, Inc. | Methods for treating huntington's disease |
| CA3090130A1 (en) * | 2018-02-02 | 2019-08-08 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| CA3094703A1 (en) | 2018-03-27 | 2019-10-03 | Ptc Therapeutics, Inc. | Compounds for treating huntington's disease |
| JP2021527051A (ja) * | 2018-06-05 | 2021-10-11 | ラプト・セラピューティクス・インコーポレイテッド | ピラゾロ−ピリミジン−アミノ−シクロアルキル化合物及びその治療的使用 |
| KR20210038845A (ko) | 2018-06-27 | 2021-04-08 | 피티씨 테라퓨틱스, 인크. | 헌팅턴병 치료를 위한 헤테로아릴 화합물 |
| WO2020005882A1 (en) | 2018-06-27 | 2020-01-02 | Ptc Therapeutics, Inc. | Heteroaryl compounds for treating huntington's disease |
| SG11202012674PA (en) | 2018-06-27 | 2021-01-28 | Ptc Therapeutics Inc | Heterocyclic and heteroaryl compounds for treating huntington's disease |
| US20210299233A1 (en) * | 2018-07-12 | 2021-09-30 | The Children's Medical Center Corporation | Method for treating cancer |
| KR102328423B1 (ko) * | 2018-09-11 | 2021-11-18 | 재단법인 대구경북첨단의료산업진흥재단 | 신규 트리아졸로-피리미딘 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 단백질 키나아제 관련 질환의 예방 또는 치료용 약학적 조성물 |
| GB202008749D0 (en) | 2020-06-09 | 2020-07-22 | Ip2Ipo Innovations Ltd | Novel compounds |
| US20230279006A1 (en) * | 2020-07-08 | 2023-09-07 | Klotho Therapeutics, Inc. | Novel compounds and methods for increasing klotho gene expression |
| WO2023107705A1 (en) | 2021-12-10 | 2023-06-15 | Incyte Corporation | Bicyclic amines as cdk12 inhibitors |
| CN114487157A (zh) * | 2021-12-23 | 2022-05-13 | 苏州华测生物技术有限公司 | 一种分离生物基质中游离态和脂质体态艾立布林的方法 |
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| CN100404536C (zh) * | 2003-07-16 | 2008-07-23 | 詹森药业有限公司 | 作为糖原合酶激酶3抑制剂的三唑并嘧啶衍生物 |
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| CA2809331C (en) * | 2010-08-27 | 2018-09-25 | Merck Patent Gmbh | Triazolopyrazine derivatives |
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| Publication number | Publication date |
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| EP2964649B1 (en) | 2017-05-10 |
| CN105026398A (zh) | 2015-11-04 |
| US20160015712A1 (en) | 2016-01-21 |
| JP6427115B2 (ja) | 2018-11-21 |
| EP2964649A1 (en) | 2016-01-13 |
| AU2014224975B2 (en) | 2017-09-14 |
| ES2636936T3 (es) | 2017-10-10 |
| CA2903903C (en) | 2021-05-04 |
| CA2903903A1 (en) | 2014-09-12 |
| WO2014135244A1 (en) | 2014-09-12 |
| US9855268B2 (en) | 2018-01-02 |
| IL240877A0 (en) | 2015-10-29 |
| AU2014224975A1 (en) | 2015-10-22 |
| JP2016510044A (ja) | 2016-04-04 |
| CN105026398B (zh) | 2018-05-18 |
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