AR048597A1 - BETA-CARBOLIN COMPOUNDS, PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND USES IN INFLAMMATORY AND CANCER PROCESSES - Google Patents
BETA-CARBOLIN COMPOUNDS, PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND USES IN INFLAMMATORY AND CANCER PROCESSESInfo
- Publication number
- AR048597A1 AR048597A1 ARP050101405A AR048597A1 AR 048597 A1 AR048597 A1 AR 048597A1 AR P050101405 A ARP050101405 A AR P050101405A AR 048597 A1 AR048597 A1 AR 048597A1
- Authority
- AR
- Argentina
- Prior art keywords
- aliphatic
- heterocyclyl
- heteroaryl
- ring
- optionally substituted
- Prior art date
Links
- 206010028980 Neoplasm Diseases 0.000 title 1
- 201000011510 cancer Diseases 0.000 title 1
- 230000002757 inflammatory effect Effects 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical class N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 title 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 16
- 125000000623 heterocyclic group Chemical group 0.000 abstract 12
- 125000001072 heteroaryl group Chemical group 0.000 abstract 11
- 125000003118 aryl group Chemical group 0.000 abstract 9
- 229910052739 hydrogen Inorganic materials 0.000 abstract 9
- 239000001257 hydrogen Substances 0.000 abstract 9
- 125000004452 carbocyclyl group Chemical group 0.000 abstract 7
- 125000005843 halogen group Chemical group 0.000 abstract 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 4
- 150000002431 hydrogen Chemical group 0.000 abstract 4
- -1 hydroxy, amino Chemical group 0.000 abstract 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 3
- 125000004043 oxo group Chemical group O=* 0.000 abstract 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 2
- 125000002950 monocyclic group Chemical group 0.000 abstract 2
- 125000002757 morpholinyl group Chemical group 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000004193 piperazinyl group Chemical group 0.000 abstract 2
- 125000003386 piperidinyl group Chemical group 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 abstract 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000003275 alpha amino acid group Chemical group 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 abstract 1
- 125000004001 thioalkyl group Chemical group 0.000 abstract 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 abstract 1
- 229910052721 tungsten Inorganic materials 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Reivindicacion 1: Un compuesto de formula (1) o una sal farmacéuticamente aceptable de los mismos, donde: El anillo A se selecciona entre el grupo compuesto por (a) un anillo de piridinilo o pirimidinilo que está sustituido con (i) CH2C(O)-G y 0-1 R6a o (ii) 1-2 R6a y (b) un anillo de morfolinilo, piperidinilo, piperazinilo, pirrolidinilo, piranilo, tetrahidrofuranilo, ciclohexilo, ciclopentilo o tiomorfolinilo que está sustituido con (i) -C(R9)3, -W-G o -G, (ii) 0-4 R6b y (iii) 0-1 grupos oxo sobre un carbono del anillo o 0-2 grupos oxo sobre un azufre del anillo; cada R6a se selecciona independientemente entre alifático C1-6, halo, alcoxi C1-6 o amino; cada R6b se selecciona independientemente entre alifático C1-3 o N(R7)2 y dos R6b sobre el mismo o un carbono adyacente opcionalmente se toman junto con el/los carbono(s) que intervienen para formar un anillo de 5-6 miembros que tiene 1-2 heteroátomos en el anillo seleccionados entre N, O o S, W es -Q-, -Q-C(O)-, -C(R9)2- C(R9)(R12)- o -C(R9)2-[C(R9)(R12)]2-; Q es -C(R9)2- o -C(R9)2C(R9)2-; G es -OH, -NR4R5, -N(R9)CONR4R5, -N(R9)SO2(alifático C1-3), -N(R9)COCF3, -N(R9)CO(alifático C1-6), -N(R9)CO(heterociclilo), -N(R9)CO(heteroarilo), -N(R9)CO(arilo), un anillo de heterociclilo monocíclico o bicíclico de 3-10 miembros o un anillo de heteroarilo de 5-6 miembros, donde cada uno de los restos heteroarilo, arilo y heterociclilo de G está opcionalmente sustituido con 1-4 R10; R1 es hidrogeno, halo, alifático C1-3, amino, ciano (alquil C1-3)1-2-amino, alcoxi C1-3, -CONH2, -NHCOCF3 o -CH2NH2; R2 es hidrogeno, halo, alifático C1-4, alcoxi C1-2 o haloalquilo C1-2; R3 es hidrogeno, halo, haloalquilo C1-6, hidroxi, amino, ciano o un grupo opcionalmente sustituido seleccionado entre alifático C1-6, alcoxi C1-6, (alquil C1-6)1-2-amino, tioalquilo C1-6, morfolinilo, piperazinilo, piperidinilo o pirrolidinilo; R4 es hidrogeno, heterociclilo de 3-7 miembros o alifático C1-6; R5 es a) hidrogeno; b) un grupo opcionalmente sustituido seleccionado entre arilo, heteroarilo, heterociclilo o carbociclilo, o c) un grupo alifático C1-6 que está opcionalmente sustituido con: halo, -OR7, -CN, -SR8, -S(O)2R8, -C(O)R7, CO2R7, -N(R7)2, -C(O)N(R7)2, -N(R7)C(O)R7, - N(R7)CO2R8, -SO2N(R7)2, -NR7SO2R7, -N(R7)C(O)N(R7)2 o un grupo arilo, heteroarilo, heterociclilo o carbociclilo que está opcionalmente sustituido con alifático C1-6, -CF3, halo, -OR7, -CN, -SR8, -S(O)2R8, -C(O)R7, -CO2R7, -N(R7)2, -C(O)N(R7)2, - N(R7)C(O)R7, -N(R7)CO2R8, -SO2N(R7)2, -NR7SO2R7, -N(R7)C(O)N(R7)2; cada R7 se selecciona independientemente entre hidrogeno o un grupo opcionalmente sustituido seleccionado entre alifático C1-4, arilo, heteroarilo, heterociclilo o carbociclilo, o dos R7 sobre el mismo átomo de nitrogeno se toman junto con el nitrogeno para formar un anillo de heteroarilo o heterociclilo de 3-6 miembros; cada R7a se selecciona independientemente entre hidrogeno o un grupo opcionalmente sustituido seleccionado entre alifático C1-4, arilo, heteroarilo, heterociclilo o carbociclilo, o dos R7a sobre el mismo átomo de nitrogeno se toman junto con el nitrogeno para formar un anillo de heteroarilo o heterociclilo de 3-6 miembros; cada R8 es independientemente un alifático C1-4 opcionalmente sustituido; cada R8a es independientemente un grupo opcionalmente sustituido seleccionado entre alifático C1-4, arilo, heteroarilo, heterociclilo o carbociclilo; cada R9 se selecciona independientemente entre hidrogeno o alifático C1-3; cada R10 se selecciona independientemente entre oxo, -R11, -T-R11 o -V-T-R11, o dos apariciones de R10, tomadas junto con el/los átomo(s) de carbono a los que están unidos, forman un anillo arilo monocíclico o bicíclico de 3-8 miembros opcionalmente sustituido, heteroarilo, heterociclilo o carbociclilo; cada R11 se selecciona independientemente entre -CF3, halo, OR7a, -CN, -SR8a, -S(O)2R8a, -C(O)R7a, -CO2R7a, -N(R7a)2, -C(O)N(R7a)2, -N(R7)C(O)R7a, -N(R7)CO2R7a, - SO2N(R7a), -N(R7)SO2R7a, -N(R7)C(O)N(R7a)2 o un grupo opcionalmente sustituido seleccionado entre alifático C1-6, arilo, heteroarilo, heterociclilo o carbociclilo; T es una cadena de alquileno C1-4 lineal o ramificada; V es -O-, -N(R7)-, -S-, -S(O)- , -S(O)2-, -C(O)- o -CO2-; y R12 es hidrogeno o una cadena lateral de aminoácidosClaim 1: A compound of formula (1) or a pharmaceutically acceptable salt thereof, wherein: Ring A is selected from the group consisting of (a) a pyridinyl or pyrimidinyl ring that is substituted with (i) CH2C (O ) -G and 0-1 R6a or (ii) 1-2 R6a and (b) a morpholinyl, piperidinyl, piperazinyl, pyrrolidinyl, pyranyl, tetrahydrofuranyl, cyclohexyl, cyclopentyl or thiomorpholinyl ring which is substituted with (i) -C ( R9) 3, -WG or -G, (ii) 0-4 R6b and (iii) 0-1 oxo groups on a ring carbon or 0-2 oxo groups on a ring sulfur; each R6a is independently selected from C1-6 aliphatic, halo, C1-6 alkoxy or amino; each R6b is independently selected from C1-3 or N (R7) 2 aliphatic and two R6b on it or an adjacent carbon are optionally taken together with the carbon (s) involved to form a 5-6 member ring that It has 1-2 ring heteroatoms selected from N, O or S, W is -Q-, -QC (O) -, -C (R9) 2- C (R9) (R12) - or -C (R9) 2- [C (R9) (R12)] 2-; Q is -C (R9) 2- or -C (R9) 2C (R9) 2-; G is -OH, -NR4R5, -N (R9) CONR4R5, -N (R9) SO2 (C1-3 aliphatic), -N (R9) COCF3, -N (R9) CO (C1-6 aliphatic), -N (R9) CO (heterocyclyl), -N (R9) CO (heteroaryl), -N (R9) CO (aryl), a 3-10 membered monocyclic or bicyclic heterocyclyl ring or a 5-6 membered heteroaryl ring , where each of the heteroaryl, aryl and heterocyclyl moieties of G is optionally substituted with 1-4 R10; R1 is hydrogen, halo, C1-3 aliphatic, amino, cyano (C1-3 alkyl) 1-2-amino, C1-3 alkoxy, -CONH2, -NHCOCF3 or -CH2NH2; R2 is hydrogen, halo, C1-4 aliphatic, C1-2 alkoxy or C1-2 haloalkyl; R3 is hydrogen, halo, C1-6 haloalkyl, hydroxy, amino, cyano or an optionally substituted group selected from C1-6 aliphatic, C1-6 alkoxy, (C1-6 alkyl) 1-2-amino, C1-6 thioalkyl, morpholinyl, piperazinyl, piperidinyl or pyrrolidinyl; R4 is hydrogen, 3-7 membered heterocyclyl or C1-6 aliphatic; R5 is a) hydrogen; b) an optionally substituted group selected from aryl, heteroaryl, heterocyclyl or carbocyclyl, or c) a C1-6 aliphatic group that is optionally substituted with: halo, -OR7, -CN, -SR8, -S (O) 2R8, -C (O) R7, CO2R7, -N (R7) 2, -C (O) N (R7) 2, -N (R7) C (O) R7, - N (R7) CO2R8, -SO2N (R7) 2, -NR7SO2R7, -N (R7) C (O) N (R7) 2 or an aryl, heteroaryl, heterocyclyl or carbocyclyl group which is optionally substituted with C1-6 aliphatic, -CF3, halo, -OR7, -CN, -SR8 , -S (O) 2R8, -C (O) R7, -CO2R7, -N (R7) 2, -C (O) N (R7) 2, - N (R7) C (O) R7, -N ( R7) CO2R8, -SO2N (R7) 2, -NR7SO2R7, -N (R7) C (O) N (R7) 2; each R7 is independently selected from hydrogen or an optionally substituted group selected from C1-4 aliphatic, aryl, heteroaryl, heterocyclyl or carbocyclyl, or two R7 on the same nitrogen atom are taken together with the nitrogen to form a heteroaryl or heterocyclyl ring 3-6 members; each R7a is independently selected from hydrogen or an optionally substituted group selected from C1-4 aliphatic, aryl, heteroaryl, heterocyclyl or carbocyclyl, or two R7a on the same nitrogen atom are taken together with the nitrogen to form a heteroaryl or heterocyclyl ring 3-6 members; each R8 is independently an optionally substituted C1-4 aliphatic; each R8a is independently an optionally substituted group selected from C1-4 aliphatic, aryl, heteroaryl, heterocyclyl or carbocyclyl; each R9 is independently selected from hydrogen or C1-3 aliphatic; each R10 is independently selected from oxo, -R11, -T-R11 or -VT-R11, or two occurrences of R10, taken together with the carbon atom (s) to which they are attached, form a monocyclic aryl ring or optionally substituted 3-8 bicyclic, heteroaryl, heterocyclyl or carbocyclyl; Each R11 is independently selected from -CF3, halo, OR7a, -CN, -SR8a, -S (O) 2R8a, -C (O) R7a, -CO2R7a, -N (R7a) 2, -C (O) N ( R7a) 2, -N (R7) C (O) R7a, -N (R7) CO2R7a, - SO2N (R7a), -N (R7) SO2R7a, -N (R7) C (O) N (R7a) 2 or an optionally substituted group selected from C1-6 aliphatic, aryl, heteroaryl, heterocyclyl or carbocyclyl; T is a linear or branched C1-4 alkylene chain; V is -O-, -N (R7) -, -S-, -S (O) -, -S (O) 2-, -C (O) - or -CO2-; and R12 is hydrogen or an amino acid side chain
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US56089204P | 2004-04-09 | 2004-04-09 | |
| US10/821,545 US7727985B2 (en) | 2003-04-09 | 2004-04-09 | Beta-carbolines useful for treating inflammatory disease |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR048597A1 true AR048597A1 (en) | 2006-05-10 |
Family
ID=36608959
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP050101405 AR048597A1 (en) | 2004-04-09 | 2005-04-11 | BETA-CARBOLIN COMPOUNDS, PHARMACEUTICAL COMPOSITIONS THAT CONTAIN THEM AND USES IN INFLAMMATORY AND CANCER PROCESSES |
Country Status (1)
| Country | Link |
|---|---|
| AR (1) | AR048597A1 (en) |
-
2005
- 2005-04-11 AR ARP050101405 patent/AR048597A1/en unknown
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