US20190119299A1 - Cyanoindoline derivatives as nik inhibitors - Google Patents
Cyanoindoline derivatives as nik inhibitors Download PDFInfo
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- US20190119299A1 US20190119299A1 US16/309,080 US201716309080A US2019119299A1 US 20190119299 A1 US20190119299 A1 US 20190119299A1 US 201716309080 A US201716309080 A US 201716309080A US 2019119299 A1 US2019119299 A1 US 2019119299A1
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- alkyl
- substituted
- het
- ring
- optionally
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Classifications
-
- 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
- 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
- A61K31/495—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
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/535—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
- A61K31/5365—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 ortho- or peri-condensed with heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K31/535—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—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 three or more hetero rings
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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
- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Definitions
- the present invention relates to pharmaceutical agents useful for therapy and/or prophylaxis in a mammal, and in particular to inhibitors of NF- ⁇ B-inducing kinase (NIK—also known as MAP3K14) useful for treating diseases such as cancer (in particular B-cell malignancies including leukemias, lymphomas and myeloma), inflammatory disorders, metabolic disorders including obesity and diabetes, and autoimmune disorders.
- NIK NF- ⁇ B-inducing kinase
- the invention is also directed to pharmaceutical compositions comprising such compounds, and to the use of such compounds or pharmaceutical compositions for the prevention or treatment of diseases such as cancer, inflammatory disorders, metabolic disorders including obesity and diabetes, and autoimmune disorders.
- the present invention relates to pharmaceutical agents useful for therapy and/or prophylaxis in a mammal, and in particular to inhibitors of NF- ⁇ B-inducing kinase (NIK—also known as MAP3K14) useful for treating diseases such as cancer and inflammatory disorders.
- NIK Nuclear factor-kappa B
- NF- ⁇ B nuclear factor-kappa B
- NF- ⁇ B dependent transcriptional activation is a tightly controlled signaling pathway, through sequential events including phosphorylation and protein degradation.
- NIK is a serine/threonine kinase which regulates NF- ⁇ B pathway activation.
- NIK NF- ⁇ B signaling pathway
- NIK is indispensable for the non-canonical signaling pathway where it phosphorylates IKK ⁇ , leading to the partial proteolysis of p100; liberating p52 which then heterodimerizes with RelB, translocates to the nucleus and mediates gene expression.
- the non-canonical pathway is activated by only a handful of ligands such as CD40 ligands, B-cell activating factor (BAFF), lymphotoxin ⁇ receptor ligands and TNF-related weak inducer of apoptosis (TWEAK) and NIK has been shown to be required for activation of the pathway by these ligands.
- BAFF B-cell activating factor
- TWEAK TNF-related weak inducer of apoptosis
- NIK expression is tightly regulated. Under normal non-stimulated conditions NIK protein levels are very low, this is due to its interaction with a range of TNF receptor associated factors (TRAF2 and TRAF3), which are ubiquitin ligases and result in degradation of NIK. It is believed that when the non-canonical pathway is stimulated by ligands, the activated receptors now compete for TRAFs, dissociating the TRAF-NIK complexes and thereby increasing the levels of NIK. (Thu and Richmond, Cytokine Growth F. R.
- the NF- ⁇ B pathway is dysregulated in multiple myeloma due to a range of diverse genetic abnormalities that lead to the engagement of the canonical and non-canonical pathways (Annuziata et al. Cancer Cell 2007, 12, 115-130; Keats et al. Cancer Cell 2007, 12, 131-144; Demchenko et al. Blood 2010, 115, 3541-3552).
- Myeloma patient samples frequently have increased levels of NIK activity. This can be due to chromosomal amplification, translocations (that result in NIK proteins that have lost TRAF binding domains), mutations (in the TRAF binding domain of NIK) or TRAF loss of function mutations.
- NIK levels are also enhanced in adult T cell leukemia (ATL) cells and targeting NIK with shRNA reduced ATL growth in vivo (Saitoh et al. Blood 2008, 111, 5118-5129).
- ATL adult T cell leukemia
- NIK NF- ⁇ B-inducing kinase
- BAFF B-cell activation factor
- B-S autochthonous B-lymphocyte stimulator
- TRAF3 loss-of-function mutations in TRAF3 have been characterized in human and canine DLBCL (Bushell et al., Blood 2015, 125, 999-1005).
- NIK protein levels are stabilised in some pancreatic cancer cell lines and as seen in blood cells proliferation of these pancreatic cancer lines are susceptible to NIK siRNA treatment (Nishina et al. Biochem. Bioph. Res. Co. 2009, 388, 96-101).
- Constitutive activation of NF- ⁇ B is preferentially involved in the proliferation of basal-like subtype breast cancer cell lines, including elevated NIK protein levels in specific lines (Yamamoto et al. Cancer Sci. 2010, 101, 2391-2397).
- tissue microarray analysis of NIK expression revealed that there was a statistically significant elevation in NIK expression when compared with benign tissue.
- shRNA techniques were used to knock-down NIK, the resultant NIK-depleted melanoma cell lines exhibited decreased proliferation, increased apoptosis, delayed cell cycle progression and reduced tumor growth in a mouse xenograft model (Thu et al. Oncogene 2012, 31(20), 2580-92).
- a wealth of evidence showed that NF- ⁇ B is often constitutively activated in non-small cell lung cancer tissue specimens and cell lines. Depletion of NIK by RNAi induced apoptosis and affected efficiency of anchorage-independent NSCLC cell growth.
- NF- ⁇ B controls the expression of many genes involved in inflammation and that NF- ⁇ B signalling is found to be chronically active in many inflammatory diseases, such as rheumatoid arthritis, inflammatory bowel disease, sepsis and others.
- pharmaceutical agents capable of inhibiting NIK and thereby reducing NF- ⁇ B signaling pathway can have a therapeutic benefit for the treatment of diseases and disorders for which over-activation of NF- ⁇ B signaling is observed.
- NLRP12 functions as a negative regulator of the NF- ⁇ B pathway through its interaction and regulation of NIK and TRAF3, and as a checkpoint of critical pathways associated with inflammation and inflammation-associated tumorigenesis (Allen et al. Immunity 2012, 36, 742-754).
- Tumor necrosis factor (TNF)- ⁇ is secreted in response to inflammatory stimuli in diseases such as rheumatoid arthritis and inflammatory bowel disease.
- TNF- ⁇ mediates both apoptosis and inflammation, stimulating an inflammatory cascade through the non-canonical pathway of NF- ⁇ B activation, leading to increased nuclear RelB and p52.
- TNF- ⁇ induced the ubiquitination of TRAFs, which interacts with NIK, leading to increased levels of phospho-NIK (Bhattacharyya et al. J Biol. Chem. 2011, 285, 39511-39522).
- NIK chronic obstructive pulmonary disease
- COPD chronic obstructive pulmonary disease
- CS cigarette smoke
- NIK oxidative stress induced cell death
- Diabetic individuals can be troubled by a range of additional manifestations associated with inflammation.
- One such complication is cardiovascular disease and it has been shown that there are elevated levels of p-NIK, p-IKK- ⁇ / ⁇ and p-I ⁇ B- ⁇ in diabetic aortic tissues (Bitar et al. Life Sci. 2010, 86, 844-853).
- NIK has been shown to regulate proinflammatory responses of renal proximal tubular epithelial cells via mechanisms involving TRAF3. This suggests a role for NF- ⁇ B noncanonical pathway activation in modulating diabetes-induced inflammation in renal tubular epithelium (Zhao et al. Exp. Diabetes Res. 2011, 1-9. doi:10.1155/2011/192564).
- NIK plays a critical role in noncanonical NF- ⁇ B pathway activation, induced skeletal muscle insulin resistance in vitro, suggesting that NIK could be an important therapeutic target for the treatment of insulin resistance associated with inflammation in obesity and type 2 diabetes (Choudhary et al. Endocrinology 2011, 152, 3622-3627).
- NF- ⁇ B is an important component of both autoimmunity and bone destruction in rheumatoid arthritis (RA).
- Mice lacking functional NIK have no peripheral lymph nodes, defective B and T cells, and impaired receptor activator of NF- ⁇ B ligand-stimulated osteoclastogenesis.
- Aya et al. J. Clin. Invest. 2005, 115, 1848-1854
- the serum transfer arthritis model was initiated by preformed antibodies and required only intact neutrophil and complement systems in recipients. While Nik ⁇ / ⁇ mice had inflammation equivalent to that of Nik+/+ controls, they showed significantly less periarticular osteoclastogenesis and less bone erosion.
- Nik ⁇ / ⁇ mice were completely resistant to antigen-induced arthritis (AIA), which requires intact antigen presentation and lymphocyte function but not lymph nodes. Additionally, transfer of Nik+/+ splenocytes or T cells to Rag2 ⁇ / ⁇ mice conferred susceptibility to AIA, while transfer of Nik ⁇ / ⁇ cells did not. Nik ⁇ / ⁇ mice were also resistant to a genetic, spontaneous form of arthritis, generated in mice expressing both the KRN T cell receptor and H-2g7.
- AIA antigen-induced arthritis
- NIK TRAF3 binding domain
- NIK neuropeptide kinase kinase
- T cells may have therapeutic value. Decreasing NIK activity in T cells might significantly ameliorate autoimmune responses and alloresponses, like GVHD (Graft Versus Host Disease) and transplant rejection, without crippling the immune system as severely as do inhibitors of canonical NF- ⁇ B activation.
- GVHD Gel Versus Host Disease
- WO2003030909 describes the preparation of 2- and 4-aminopyrimidines N-substituted by a bicyclic ring for use as kinase inhibitors in the treatment of cancer.
- WO2002079197 describes 4-aryl-substituted 2-pyrimidinamines and 2-pyridinamines, useful as inhibitors of c-Jun N-terminal kinases (JNK) and other protein kinases.
- WO2014174021, WO2015044267 and WO2015044269 describe NIK inhibitors for the treatment of cancer.
- WO2010042337 describes 6-azaindole aminopyrimidine derivatives having NIK inhibitory activity.
- the present invention concerns novel compounds of Formula (I):
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, C 1-6 alkyl substituted with one R 5 , or C 1-6 alkyl substituted with one, two or three fluoro atoms;
- Y represents CR 4 or N
- R 4 represents hydrogen or halo
- R 5 represents Het 3a , —NR 6a R 6b , or —OR 7 ;
- R 6a represents hydrogen or C 1-4 alkyl
- R 6b represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; —C( ⁇ O)—C 1-4 alkyl; —C( ⁇ O)-Het 4 ; —S( ⁇ O) 2 —C 1-4 alkyl; —C( ⁇ O)—C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —NR 16a R 16b ; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —S( ⁇ O) 2 —C 1-4 alkyl;
- R 7 represents hydrogen, C 1-4 alkyl, —C 1-4 alkyl-NR 8a R 8b , —C( ⁇ O)—R 9 , —S( ⁇ O) 2 —OH, —P( ⁇ O) 2 —OH, —(C ⁇ O)—CH(NH 2 )—C 1-4 alkyl-Ar 1 , or —C 1-4 alkyl-Het 3b ;
- R 8a represents hydrogen or C 1-4 alkyl
- R 8b represents hydrogen, C 1-4 alkyl, or C 3-6 cycloalkyl
- R 9 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one substituent selected from the group consisting of —NH 2 , —COOH, and Het 6 ;
- R 16a and R 16b each independently represents hydrogen, C 1-4 alkyl or C 3-6 cycloalkyl
- R 3 represents
- ring A1 represents phenyl or a 6-membered heteroaromatic ring containing 1 or 2 N-atoms
- ring A2 represents 2-oxo-1,2-dihydropyridin-3-yl
- ring B1 represents a 4- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- (1a-1) and (1a-2) may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo; cyano; oxo; —OH; C 1-6 alkyl; —O—C 1-4 alkyl; —C( ⁇ O)—R 10 ; —S( ⁇ O) 2 —C 1-4 alkyl; —S( ⁇ O)( ⁇ N—R 20a )—C 1-4 alkyl; —O—C 1-4 alkyl substituted with one, two or three halo atoms; —O—C 1-4 alkyl-R 12 ; C 3-6 cycloalkyl; —O—C 3-6 cycloalkyl; Het 1a ; —O-Het 1b ; R 18 ; —P( ⁇ O)—(C 1-4 alkyl) 2 ; —NH—C( ⁇ O)—C 1-4 alkyl; —NH
- ring A2 may optionally be substituted, where possible, on the N-atom with a substituent selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; Het 1a ; R 18 ; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; C 1-4 alkyl substituted with one R 18 ; C 2-6 alkenyl; and C 2-6 alkenyl substituted with one R 13 ; provided that when Het 1a or R 18 are directly attached to the N-atom of ring A2, said Het 1a or R 18 are attached to the N-atom via a ring carbon atom; and
- ring B1 may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; Het 1a ; R 18 ; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; C 1-4 alkyl substituted with one R 18 ; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)NR 14g R 14h ; —C( ⁇ O)—C 1-4 alkyl-NR 14i R 14j ; —C( ⁇ O)—C( ⁇ O)—NR 14k R 14l ; C 2-6 alkenyl; and C 2-6 alkenyl substituted with one R 13 ; provided that when Het 1a or R 18 are directly attached to the N-atom of
- ring A represents pyrazolyl optionally substituted with one substituent selected from the group consisting of C 1-4 alkyl, —C 1-4 alkyl-O—C 1-4 alkyl, and C 1-4 alkyl substituted with one, two or three halo atoms;
- ring B represents a C 5-7 cycloalkyl or a 5- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O and N;
- C 5-7 cycloalkyl or 5- to 7-membered saturated heterocyclyl may optionally be substituted on one or two ring carbon atoms with one or two substituents each independently selected from the group consisting of C 1-4 alkyl, —C 1-4 alkyl-O—C 1-4 alkyl and —C 1-4 alkyl-OH, or one ring carbon atom may optionally be substituted with oxo; and wherein said 5- to 7-membered saturated heterocyclyl may optionally be substituted on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)NR 14
- fused 6- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo; cyano; C 1-6 alkyl; —O—C 1-4 alkyl; —C( ⁇ O)—R 10 ; —S( ⁇ O) 2 —C 1-4 alkyl; —S( ⁇ O)( ⁇ N—R 20a )—C 1-4 alkyl; —O—C 1-4 alkyl substituted with one, two or three halo atoms; —O—C 1-4 alkyl-R 12 ; C 3-6 cycloalkyl; —O—C 3-6 cycloalkyl; Het 1a ; —O-Het 1b ; R 18 ; —P( ⁇ O)—(C 1-4 alkyl) 2 ; —NH—C( ⁇ O)—C 1-4 alkyl;
- fused 6- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted, where possible, on one ring N-atom with a substituent selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; Het 1a ; R 18 ; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; C 1-4 alkyl substituted with one R 18 ; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)NR 14g R 14h ; —C( ⁇ O)—C 1-4 alkyl-NR 14i R 14j ; —C( ⁇ O)—C( ⁇ O)—NR 14k R 14l ; C 2-6 alkenyl; and C 2-6 alkenyl substituted with one R 13 ; provided that when Het 1a or
- R 10 represents —OH, —O—C 1-4 alkyl, —NR 11a R 11b or Het 2 ;
- R 18 represents a 5-membered aromatic ring containing one, two or three N-atoms; wherein said 5-membered aromatic ring may optionally be substituted with one substituent selected from the group consisting of C 1-4 alkyl and C 3-6 cycloalkyl;
- Het 1a , Het 1c and Het 1d each independently represents a 4- to 7-membered monocyclic saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N; or a 6- to 11-membered bicyclic saturated heterocyclyl, including fused, spiro and bridged cycles, containing one, two or three heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- said 4- to 7-membered monocyclic saturated heterocyclyl or said 6- to 11-membered bicyclic saturated heterocyclyl may optionally be substituted, where possible, on one, two or three ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and
- said 4- to 7-membered monocyclic saturated heterocyclyl or said 6- to 11-membered bicyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, oxo, halo, C 1-4 alkyl, cyano, —C( ⁇ O)—C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), and —N(C 1-4 alkyl) 2 ;
- Het 1b , Het 1e , Het 1g and Het 4 each independently represents a 4- to 7-membered monocyclic saturated heterocyclyl, attached to the remainder of the molecule of Formula (I) through any available ring carbon atom, said Het 1b , Het 1e , Het 1g and Het 4 containing one or two heteroatoms each independently selected from O, S, S( ⁇
- said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl; and
- said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, halo, C 1-4 alkyl, cyano, —C( ⁇ O)—C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), and —N(C 1-4 alkyl) 2 ;
- Het 2 represents a heterocyclyl of formula (b-1):
- (b-1) represents a N-linked 4- to 7-membered monocyclic saturated heterocyclyl optionally containing one additional heteroatom selected from O, S, S( ⁇ O) p and N, or a N-linked 6- to 11-membered bicyclic saturated heterocyclyl, including fused, spiro and bridged cycles, optionally containing one or two additional heteroatoms each independently selected from O, S, S( ⁇ O), and N;
- (b-1) may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of halo, —OH, cyano, C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), —N(C 1-4 alkyl) 2 , and C 1-4 alkyl-OH;
- R 11b represents hydrogen; Het 1e ; C 1-4 alkyl; C 1-4 alkyl-Het 5 ; C 1-4 alkyl substituted with one, two or three substituents each independently selected from the group consisting of halo, —OH and —O—C 1-4 alkyl; C 3-6 cycloalkyl; or C 3-6 cycloalkyl substituted with one, two or three substituents each independently selected from the group consisting of halo, —OH and —O—C 1-4 alkyl;
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , —NR 19a R 19b , C 3-6 cycloalkyl, Het 1d , —S( ⁇ O) 2 —C 1-4 alkyl, —S( ⁇ O)( ⁇ N—R 20c )—C 1-4 alkyl, or —C( ⁇ O)-Het 1f ;
- R 12 represents —OH, —O—C 1-4 alkyl, —NR 14a R 14b , —C( ⁇ O)NR 14c R 14d , —S( ⁇ O) 2 —C 1-4 alkyl, —S( ⁇ O)( ⁇ N—R 20b )—C 1-4 alkyl, C 3-6 cycloalkyl, Ar 2 , or Het 1c ;
- Ar 1 represents phenyl optionally substituted with one hydroxy
- Ar 2 represents phenyl optionally substituted with one C 1-4 alkyl; or a 5- or 6-membered heteroaromatic ring containing one, two or three heteroatoms each independently selected from O, S, and N;
- Het 3a , Het 3b , Het 5 , Het 6 and Het 1f each independently represents a heterocyclyl of formula (c-1):
- (c-1) represents a N-linked 4- to 7-membered monocyclic saturated heterocyclyl optionally containing one additional heteroatom selected from O, S, S( ⁇ O) p and N;
- (c-1) may optionally be substituted on one or two ring C-atoms atoms with one or two substituents each independently selected from the group consisting of halo, C 1-4 alkyl, and C 3-6 cycloalkyl;
- R 11a , R 14a , R 14e , R 14g , R 14i , R 14k , R 15a , R 17a and R 19a each independently represents hydrogen or C 1-4 alkyl;
- R 14b , R 14d , R 14h , R 14j , R 14l , R 15b , R 17b and R 19b each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of halo, —OH and —O—C 1-4 alkyl;
- R 20a , R 20b and R 20c each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl;
- p 1 or 2;
- the present invention also relates to a pharmaceutical composition
- a pharmaceutical composition comprising a therapeutically effective amount of a compound of Formula (I), a pharmaceutically acceptable addition salt, or a solvate thereof, and a pharmaceutically acceptable carrier or excipient.
- the invention relates to a compound of Formula (I), a pharmaceutically acceptable addition salt, or a solvate thereof, for use as a medicament, and to a compound of Formula (I), a pharmaceutically acceptable addition salt, or a solvate thereof, for use in the treatment or in the prevention of cancer, inflammatory disorders, autoimmune disorders, and metabolic disorders such as diabetes and obesity.
- the invention relates to a compound of Formula (I), a pharmaceutically acceptable addition salt, or a solvate thereof, for use in the treatment or in the prevention of a haematological malignancy or solid tumour.
- said haematological malignancy is selected from the group consisting of multiple myeloma, Hodgkin lymphoma, T-cell leukaemia, mucosa-associated lymphoid tissue lymphoma, diffuse large B-cell lymphoma and mantle cell lymphoma.
- the solid tumour is selected from the group consisting of pancreatic cancer, breast cancer, melanoma and non-small cell lung cancer.
- the invention also relates to the use of a compound of Formula (I), a pharmaceutically acceptable addition salt, or a solvate thereof, in combination with an additional pharmaceutical agent for use in the treatment or prevention of cancer, inflammatory disorders, autoimmune disorders, and metabolic disorders such as diabetes and obesity.
- the invention relates to a process for preparing a pharmaceutical composition according to the invention, characterized in that a pharmaceutically acceptable carrier is intimately mixed with a therapeutically effective amount of a compound of Formula (I), a pharmaceutically acceptable addition salt, or a solvate thereof.
- the invention also relates to a product comprising a compound of Formula (I), a pharmaceutically acceptable addition salt, or a solvate thereof, and an additional pharmaceutical agent, as a combined preparation for simultaneous, separate or sequential use in the treatment or prevention of cancer, inflammatory disorders, autoimmune disorders, and metabolic disorders such as diabetes and obesity.
- the invention relates to a method of treating or preventing a cell proliferative disease in a warm-blooded animal which comprises administering to the said animal an effective amount of a compound of Formula (I), a pharmaceutically acceptable addition salt, or a solvate thereof, as defined herein, or a pharmaceutical composition or combination as defined herein.
- Some of the compounds of the present invention may undergo metabolism to a more active form in vivo (prodrugs).
- halo or ‘halogen’ as used herein represents fluoro, chloro, bromo and iodo.
- C x-y refers to the number of carbon atoms in a given group.
- a C 1-6 alkyl group contains from 1 to 6 carbon atoms
- a C 3-6 cycloalkyl group contains from 3 to 6 carbon atoms, and so on.
- C 1-4 alkyl as used herein as a group or part of a group represents a straight or branched chain saturated hydrocarbon radical having from 1 to 4 carbon atoms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, s-butyl, t-butyl and the like.
- C 1-6 alkyl as used herein as a group or part of a group represents a straight or branched chain saturated hydrocarbon radical having from 1 to 6 carbon atoms such as the groups defined for C 1-4 alkyl and n-pentyl, n-hexyl, 2-methylbutyl and the like.
- C 2-6 alkenyl as used herein as a group or part of a group represents a straight or branched chain hydrocarbon group containing from 2 to 6 carbon atoms and containing a carbon carbon double bond such as, but not limited to, ethenyl, propenyl, butenyl, pentenyl, 1-propen-2-yl, hexenyl and the like.
- C 3-6 cycloalkyl as used herein as a group or part of a group represents cyclic saturated hydrocarbon radicals having from 3 to 6 carbon atoms such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
- substituted in general, whenever the term “substituted” is used in the present invention, it is meant, unless otherwise is indicated or is clear from the context, to indicate that one or more hydrogens, in particular from 1 to 4 hydrogens, more in particular from 1 to 3 hydrogens, preferably 1 or 2 hydrogens, more preferably 1 hydrogen, on the atom or radical indicated in the expression using “substituted” are replaced with a selection from the indicated group, provided that the normal valency is not exceeded, and that the substitution results in a chemically stable compound, i.e. a compound that is sufficiently robust to survive isolation to a useful degree of purity from a reaction mixture, and formulation into a therapeutic agent.
- substituents When two or more substituents are present on a moiety they may, where possible and unless otherwise is indicated or is clear from the context, replace hydrogens on the same atom or they may replace hydrogen atoms on different atoms in the moiety.
- a substituent on a heterocyclyl group may replace any hydrogen atom on a ring carbon atom or on a ring heteroatom (e.g. a hydrogen on a nitrogen atom may be replaced by a substituent), for example in saturated heterocyclyl groups or 5-membered aromatic rings as used in the definition of R 18 .
- C(O) or C( ⁇ O) represents a carbonyl moiety.
- S( ⁇ O) 2 or SO 2 represents a sulfonyl moiety.
- oxo means ⁇ O; for example piperidine substituted with oxo in position 2 is represented by the following structure:
- saturated means ‘fully saturated’, if not otherwise specified.
- Het 1a , Het 1c and Het 1d may be attached to the remainder of the molecule of Formula (I) through any available ring carbon or nitrogen atom as appropriate, if not otherwise specified.
- the 5-membered aromatic ring containing one, two or three N-atoms as referred to in the definition of R 18 may be attached to the remainder of the molecule of Formula (I) through any available ring carbon or nitrogen atom as, if not otherwise specified.
- bicyclic saturated heterocyclyl groups include fused, spiro and bridged saturated heterocycles.
- Fused bicyclic groups are two cycles that share two atoms and the bond between these atoms.
- Spiro bicyclic groups are two cycles that are joined at a single atom.
- Bridged bicyclic groups are two cycles that share more than two atoms.
- N-linked 6- to 11-membered fused bicyclic saturated heterocyclyl groups include, but are not limited to
- N-linked 6- to 11-membered spiro bicyclic saturated heterocyclyl groups include, but are not limited to
- N-linked 6- to 11-membered bridged bicyclic saturated heterocyclyl groups include, but are not limited to
- Het 1a , Het 1c and Het 1d also includes C-linked bicycles (attached to the remainder of the molecule of Formula (I) through any available ring carbon atom).
- bicyclic saturated heterocyclyl groups referred to above may optionally be substituted, where possible, on carbon and/or nitrogen atoms according to any of the embodiments.
- Non-limiting examples of 4- to 7-membered monocyclic saturated heterocyclyl moieties containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N as in the definition oft Het 1a , Het 1c , and Het 1d ) are shown below:
- Non-limiting examples of 4- to 7-membered monocyclic saturated heterocyclyl moieties, attached to the remainder of the molecule of Formula (I) through any available ring carbon atom (C-linked), and containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N (as in the definition of Het 1b , Het 1e , Het 1g and Het 4 ) are shown below:
- N-linked 4- to 7-membered monocyclic saturated heterocyclyl moieties optionally containing one additional heteroatom selected from O, S, S( ⁇ O) p and N are shown below:
- Non-limiting examples of 5-membered aromatic ring containing one, two or three N-atoms as referred to in the definition of R 18 are shown below:
- R 3 represents a fused bicyclic ring system of formula (1a-1)
- (1a-1) is attached to the remainder of the molecule of Formula (I) (—NH-moiety) via ring A1.
- R 3 represents a fused bicyclic ring system of formula (1a-2), (1a-2) is attached to the remainder of the molecule of Formula (I) (—NH-moiety) via a ring carbon atom of ring A2.
- R 3 represents a fused bicyclic ring system of formula (2a-1), (2a-1) is attached to the remainder of the molecule of Formula (I) (—NH-moiety) via a ring carbon atom of ring A.
- Lines (such as “ ”) drawn into ring systems indicate that the bond may be attached to any of the suitable ring atoms.
- each definition is independent.
- subject refers to an animal, preferably a mammal (e.g. cat, dog, primate or human), more preferably a human, who is or has been the object of treatment, observation or experiment.
- a mammal e.g. cat, dog, primate or human
- terapéuticaally effective amount means that amount of active compound or pharmaceutical agent that elicits the biological or medicinal response in a tissue system, animal or human that is being sought by a researcher, veterinarian, medicinal doctor or other clinician, which includes alleviation or reversal of the symptoms of the disease or disorder being treated.
- composition is intended to encompass a product comprising the specified ingredients in the specified amounts, as well as any product which results, directly or indirectly, from combinations of the specified ingredients in the specified amounts.
- treatment is intended to refer to all processes wherein there may be a slowing, interrupting, arresting or stopping of the progression of a disease, but does not necessarily indicate a total elimination of all symptoms.
- compound(s) of the (present) invention or “compound(s) according to the (present) invention” as used herein, is meant to include the compounds of Formula (I) and the pharmaceutically acceptable addition salts, and the solvates thereof.
- stereoisomers “stereoisomeric forms” or “stereochemically isomeric forms” hereinbefore or hereinafter are used interchangeably.
- the invention includes all stereoisomers of the compounds of the invention either as a pure stereoisomer or as a mixture of two or more stereoisomers.
- Enantiomers are stereoisomers that are non-superimposable mirror images of each other.
- a 1:1 mixture of a pair of enantiomers is a racemate or racemic mixture.
- Atropisomers are stereoisomers which have a particular spatial configuration, resulting from a restricted rotation about a single bond, due to large steric hindrance. All atropisomeric forms of the compounds of Formula (I) are intended to be included within the scope of the present invention.
- Diastereomers are stereoisomers that are not enantiomers, i.e. they are not related as mirror images. If a compound contains a double bond, the substituents may be in the E or the Z configuration.
- Substituents on bivalent cyclic saturated or partially saturated radicals may have either the cis- or trans-configuration; for example if a compound contains a disubstituted cycloalkyl group, the substituents may be in the cis or trans configuration.
- the invention includes enantiomers, atropisomers, diastereomers, racemates, E isomers, Z isomers, cis isomers, trans isomers and mixtures thereof, whenever chemically possible.
- the absolute configuration is specified according to the Cahn-Ingold-Prelog system.
- the configuration at an asymmetric atom is specified by either R or S.
- Resolved stereoisomers whose absolute configuration is not known can be designated by (+) or ( ⁇ ) depending on the direction in which they rotate plane polarized light.
- resolved enantiomers whose absolute configuration is not known can be designated by (+) or ( ⁇ ) depending on the direction in which they rotate plane polarized light.
- stereoisomer is substantially free, i.e. associated with less than 50%, preferably less than 20%, more preferably less than 10%, even more preferably less than 5%, in particular less than 2% and most preferably less than 1%, of the other stereoisomers.
- a compound of Formula (I) is for instance specified as (R)
- a compound of Formula (I) is for instance specified as E
- Z Z isomer
- a compound of Formula (I) is for instance specified as cis, this means that the compound is substantially free of the trans isomer.
- Pharmaceutically-acceptable addition salts include acid addition salts and base addition salts. Such salts may be formed by conventional means, for example by reaction of a free acid or a free base form with one or more equivalents of an appropriate acid or base, optionally in a solvent, or in a medium in which the salt is insoluble, followed by removal of said solvent, or said medium, using standard techniques (e.g. in vacuo, by freeze-drying or by filtration). Salts may also be prepared by exchanging a counter-ion of a compound of the invention in the form of a salt with another counter-ion, for example using a suitable ion exchange resin.
- compositions of Formula (I) and solvates thereof are able to form.
- Appropriate acids comprise, for example, inorganic acids such as hydrohalic acids, e.g. hydrochloric or hydrobromic acid, sulfuric, nitric, phosphoric and the like acids; or organic acids such as, for example, acetic, propanoic, hydroxyacetic, lactic, pyruvic, oxalic (i.e. ethanedioic), malonic, succinic (i.e.
- salt forms can be converted by treatment with an appropriate base into the free base form.
- the compounds of Formula (I) and solvates thereof containing an acidic proton may also be converted into their non-toxic metal or amine addition salt forms by treatment with appropriate organic and inorganic bases.
- Appropriate base salt forms comprise, for example, the ammonium salts, the alkali and earth alkaline metal salts, e.g. the lithium, sodium, potassium, magnesium, calcium salts and the like, salts with organic bases, e.g.
- primary, secondary and tertiary aliphatic and aromatic amines such as methylamine, ethylamine, propylamine, isopropylamine, the four butylamine isomers, dimethylamine, diethylamine, diethanolamine, dipropylamine, diisopropylamine, di-n-butylamine, pyrrolidine, piperidine, morpholine, trimethylamine, triethylamine, tripropylamine, quinuclidine, pyridine, quinoline and isoquinoline; the benzathine, N-methyl-D-glucamine, hydrabamine salts, and salts with amino acids such as, for example, arginine, lysine and the like.
- the salt form can be converted by treatment with acid into the free acid form.
- solvate comprises the solvent addition forms as well as the salts thereof, which the compounds of Formula (I) are able to form.
- solvent addition forms are e.g. hydrates, alcoholates and the like.
- the compounds of the invention as prepared in the processes described below may be synthesized in the form of mixtures of enantiomers, in particular racemic mixtures of enantiomers, that can be separated from one another following art-known resolution procedures.
- a manner of separating the enantiomeric forms of the compounds of Formula (I), and pharmaceutically acceptable addition salts, and solvates thereof involves liquid chromatography using a chiral stationary phase.
- Said pure stereochemically isomeric forms may also be derived from the corresponding pure stereochemically isomeric forms of the appropriate starting materials, provided that the reaction occurs stereospecifically.
- the present invention also embraces isotopically-labeled compounds of the present invention which are identical to those recited herein, but for the fact that one or more atoms are replaced by an atom having an atomic mass or mass number different from the atomic mass or mass number usually found in nature (or the most abundant one found in nature).
- isotopes and isotopic mixtures of any particular atom or element as specified herein are contemplated within the scope of the compounds of the invention, either naturally occurring or synthetically produced, either with natural abundance or in an isotopically enriched form.
- Exemplary isotopes that can be incorporated into compounds of the invention include isotopes of hydrogen, carbon, nitrogen, oxygen, phosphorus, sulfur, fluorine, chlorine and iodine, such as 2 H, 3 H, 11 C, 13 C, 14 C, 13 N, 15 O, 17 O, 18 , 32 P, 33 P, 35 S, 18 F, 36 Cl, 122 I, 123 I, 125 I, 131 I, 75 Br, 76 Br, 77 Br and 82 Br.
- the radioactive isotope is selected from the group of 2 H, 3 H, 11 C and 18 F. More preferably, the radioactive isotope is 2 H.
- deuterated compounds are intended to be included within the scope of the present invention.
- Certain isotopically-labeled compounds of the present invention are useful in compound and for substrate tissue distribution assays. Tritiated ( 3 H) and carbon-14 ( 14 C) isotopes are useful for their ease of preparation and detectability.
- isotopes such as deuterium (i.e., 2 H may afford certain therapeutic advantages resulting from greater metabolic stability (e.g., increased in vivo half-life or reduced dosage requirements) and hence may be preferred in some circumstances.
- Positron emitting isotopes such as 15 O, 13 N, 11 C and 18 F are useful for positron emission tomography (PET) studies to examine substrate receptor occupancy.
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen or halo
- R 5 represents Het 3a , —NR 6a R 6b , or —OR 7 ;
- R 6a represents hydrogen or C 1-4 alkyl
- R 6b represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; —C( ⁇ O)—C 1-4 alkyl; —C( ⁇ O)-Het 4 ; —S( ⁇ O) 2 —C 1-4 alkyl; —C( ⁇ O)—C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —NR 16a R 16b ; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —S( ⁇ O) 2 —C 1-4 alkyl;
- R 7 represents hydrogen, C 1-4 alkyl, —C 1-4 alkyl-NR 8a R 8b , —C( ⁇ O)—R 9 , —S( ⁇ O) 2 —OH, —P( ⁇ O) 2 —OH, —(C ⁇ O)—CH(NH 2 )—C 1-4 alkyl-Ar 1 , or —C 1-4 alkyl-Het 3b ;
- R 8a represents hydrogen or C 1-4 alkyl
- R 8b represents hydrogen, C 1-4 alkyl, or C 3-6 cycloalkyl
- R 9 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one substituent selected from the group consisting of —NH 2 , —COOH, and Het 6 ;
- R 16a and R 16b each independently represents hydrogen, C 1-4 alkyl or C 3-6 cycloalkyl
- R 3 represents a fused bicyclic ring system of formula (1a-1):
- ring A1 represents phenyl or a 6-membered heteroaromatic ring containing 1 or 2 N-atoms
- ring B1 represents a 4- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- (1a-1) may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo; cyano; oxo; C 1-6 alkyl; —O—C 1-4 alkyl; —C( ⁇ O)—R 10 ; —S( ⁇ O) 2 —C 1-4 alkyl; —S( ⁇ O)( ⁇ N—R 20a )—C 1-4 alkyl; —O—C 1-4 alkyl substituted with one, two or three halo atoms; —O—C 1-4 alkyl-R 12 ; C 3-6 cycloalkyl; —O—C 3-6 cycloalkyl; Het 1a ; —O-Het 1b ; R 18 ; —P( ⁇ O)—(C 1-4 alkyl) 2 ; —NH—C( ⁇ O)—C 1-4 alkyl; —NH—C( ⁇ O)-Het
- ring B1 may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; Het 1a ; R 18 ; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; C 1-4 alkyl substituted with one R 18 ; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)NR 14g R 14h ; —C( ⁇ O)—C 1-4 alkyl-NR 14i R 14j ; —C( ⁇ O)—C( ⁇ O)—NR 14k R 14l ; C 2-6 alkenyl; and C 2-6 alkenyl substituted with one R 13 ; provided that when Het 1a or R 18 are directly attached to the N-atom of
- R 10 represents —OH, —O—C 1-4 alkyl, —NR 11a R 11b or Het 2 ;
- R 18 represents a 5-membered aromatic ring containing one, two or three N-atoms; wherein said 5-membered aromatic ring may optionally be substituted with one substituent selected from the group consisting of C 1-4 alkyl and C 3-6 cycloalkyl;
- Het 1a , Het 1c and Het 1d each independently represents a 4- to 7-membered monocyclic saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N; or a 6- to 11-membered bicyclic saturated heterocyclyl, including fused, spiro and bridged cycles, containing one, two or three heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- said 4- to 7-membered monocyclic saturated heterocyclyl or said 6- to 11-membered bicyclic saturated heterocyclyl may optionally be substituted, where possible, on one, two or three ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and
- said 4- to 7-membered monocyclic saturated heterocyclyl or said 6- to 11-membered bicyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, oxo, halo, C 1-4 alkyl, cyano, —C( ⁇ O)—C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), and —N(C 1-4 alkyl) 2 ;
- Het 1b , Het 1e , Het 1g and Het 4 each independently represents a 4- to 7-membered monocyclic saturated heterocyclyl, attached to the remainder of the molecule of Formula (I) through any available ring carbon atom, said Het 1b , Het 1e , Het 1g and Het 4 containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl; and
- said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, halo, C 1-4 alkyl, cyano, —C( ⁇ O)—C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), and —N(C 1-4 alkyl) 2 ;
- Het 2 represents a heterocyclyl of formula (b-1):
- (b-1) represents a N-linked 4- to 7-membered monocyclic saturated heterocyclyl optionally containing one additional heteroatom selected from O, S, S( ⁇ O) p and N, or a N-linked 6- to 11-membered bicyclic saturated heterocyclyl, including fused, spiro and bridged cycles, optionally containing one or two additional heteroatoms each independently selected from O, S, S( ⁇ O), and N;
- (b-1) may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of halo, —OH, cyano, C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), —N(C 1-4 alkyl) 2 , and C 1-4 alkyl-OH;
- R 11b represents hydrogen; Het 1e ; C 1-4 alkyl; C 1-4 alkyl-Het 5 ; C 1-4 alkyl substituted with one, two or three substituents each independently selected from the group consisting of halo, —OH and —O—C 1-4 alkyl; C 3-6 cycloalkyl; or C 3-6 cycloalkyl substituted with one, two or three substituents each independently selected from the group consisting of halo,
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , —NR 19a R 19b , C 3-6 cycloalkyl, Het 1d , —S( ⁇ O) 2 —C 1-4 alkyl, —S( ⁇ O)( ⁇ N—R 20c )—C 1-4 alkyl, or —C( ⁇ O)-Het 1f ;
- R 12 represents —OH, —O—C 1-4 alkyl, —NR 14a R 14b , —C( ⁇ O)NR 14c R 14d , —S( ⁇ O) 2 —C 1-4 alkyl, —S( ⁇ O)( ⁇ N—R 20b )—C 1-4 alkyl, C 3-6 cycloalkyl, Ar 2 , or Het 1c ;
- Ar 1 represents phenyl optionally substituted with one hydroxy
- Ar 2 represents phenyl optionally substituted with one C 1-4 alkyl
- Het 3a , Het 3b , Het 5 , Het 6 and Het 1f each independently represents a heterocyclyl of formula (c-1):
- (c-1) represents a N-linked 4- to 7-membered monocyclic saturated heterocyclyl optionally containing one additional heteroatom selected from O, S, S( ⁇ O) p and N;
- (c-1) may optionally be substituted on one or two ring C-atoms atoms with one or two substituents each independently selected from the group consisting of halo, C 1-4 alkyl, and C 3-6 cycloalkyl;
- R 11a , R 14a , R 14c , R 14g , R 14i , R 14k , R 15a , R 17a and R 19a each independently represents hydrogen or C 1-4 alkyl;
- R 14b , R 14d , R 14h , R 14j , R 14l , R 15b , R 17b and R 19b each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of halo, —OH and —O—C 1-4 alkyl;
- R 20a , R 20b and R 20c each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl;
- p 1 or 2;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, C 1-6 alkyl substituted with one R 5 , or C 1-6 alkyl substituted with one, two or three fluoro atoms;
- Y represents CR 4 or N
- R 4 represents hydrogen or halo
- R 5 represents Het 3a , —NR 6a R 6b , or —OR 7 ;
- R 6a represents hydrogen or C 1-4 alkyl
- R 6b represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; —C( ⁇ O)—C 1-4 alkyl; —C( ⁇ O)-Het 4 ; —S( ⁇ O) 2 —C 1-4 alkyl; —C( ⁇ O)—C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —NR 16a R 16b ; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —S( ⁇ O) 2 —C 1-4 alkyl;
- R 7 represents hydrogen, C 1-4 alkyl, —C 1-4 alkyl-NR 8a R 8b , —C( ⁇ O)—R 9 , —S( ⁇ O) 2 —OH, —P( ⁇ O) 2 —OH, —(C ⁇ O)—CH(NH 2 )—C 1-4 alkyl-Ar 1 , or —C 1-4 alkyl-Het 3b ;
- R 8a represents hydrogen or C 1-4 alkyl
- R 8b represents hydrogen, C 1-4 alkyl, or C 3-6 cycloalkyl
- R 9 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one substituent selected from the group consisting of —NH 2 , —COOH, and Het 6 ;
- R 16a and R 16b each independently represents hydrogen, C 1-4 alkyl or C 3-6 cycloalkyl
- R 3 represents
- ring A1 represents phenyl or a 6-membered heteroaromatic ring containing 1 or 2 N-atoms
- ring A2 represents 2-oxo-1,2-dihydropyridin-3-yl
- ring B1 represents a 4- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- (1a-1) and (1a-2) may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo; cyano; oxo; —OH; C 1-6 alkyl; —O—C 1-4 alkyl; —C( ⁇ O)—R 10 ; —S( ⁇ O) 2 —C 1-4 alkyl; —S( ⁇ O)( ⁇ N—R 20a )—C 1-4 alkyl; —O—C 1-4 alkyl substituted with one, two or three halo atoms; —O—C 1-4 alkyl-R 12 ; C 3-6 cycloalkyl; —O—C 3-6 cycloalkyl; Het 1a ; —O-Het 1b ; R 18 ; —P( ⁇ O)—(C 1-4 alkyl) 2 ; —NH—C( ⁇ O)—C 1-4 alkyl; —NH
- ring A2 may optionally be substituted, where possible, on the N-atom with a substituent selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; Het 1a ; R 18 ; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; C 1-4 alkyl substituted with one R 18 ; C 2-6 alkenyl; and C 2-6 alkenyl substituted with one R 13 ; provided that when Het 1a or R 18 are directly attached to the N-atom of ring A2, said Het 1a or R 18 are attached to the N-atom via a ring carbon atom; and
- ring B1 may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; Het 1a ; R 18 ; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; C 1-4 alkyl substituted with one R 18 ; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)NR 14g R 14h ; —C( ⁇ O)—C 1-4 alkyl-NR 14i R 14j ; —C( ⁇ O)—C( ⁇ O)—NR 14k R 14l ; C 2-6 alkenyl; and C 2-6 alkenyl substituted with one R 13 ; provided that when Het 1a or R 18 are directly attached to the N-atom of
- R 10 represents —OH, —O—C 1-4 alkyl, —NR 11a R 11b or Het 2 ;
- R 18 represents a 5-membered aromatic ring containing one, two or three N-atoms; wherein said 5-membered aromatic ring may optionally be substituted with one substituent selected from the group consisting of C 1-4 alkyl and C 3-6 cycloalkyl;
- Het 1a , Het 1c and Het 1d each independently represents a 4- to 7-membered monocyclic saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N; or a 6- to 11-membered bicyclic saturated heterocyclyl, including fused, spiro and bridged cycles, containing one, two or three heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- said 4- to 7-membered monocyclic saturated heterocyclyl or said 6- to 11-membered bicyclic saturated heterocyclyl may optionally be substituted, where possible, on one, two or three ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and
- said 4- to 7-membered monocyclic saturated heterocyclyl or said 6- to 11-membered bicyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, oxo, halo, C 1-4 alkyl, cyano, —C( ⁇ O)—C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), and —N(C 1-4 alkyl) 2 ;
- Het 1b , Het 1e , Het 1g and Het 4 each independently represents a 4- to 7-membered monocyclic saturated heterocyclyl, attached to the remainder of the molecule of Formula (I) through any available ring carbon atom, said Het 1b , Het 1e , Het 1g and Het 4 containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl; and
- said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, halo, C 1-4 alkyl, cyano, —C( ⁇ O)—C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), and —N(C 1-4 alkyl) 2 ;
- Het 2 represents a heterocyclyl of formula (b-1):
- (b-1) represents a N-linked 4- to 7-membered monocyclic saturated heterocyclyl optionally containing one additional heteroatom selected from O, S, S( ⁇ O) p and N, or a N-linked 6- to 11-membered bicyclic saturated heterocyclyl, including fused, spiro and bridged cycles, optionally containing one or two additional heteroatoms each independently selected from O, S, S( ⁇ O), and N;
- (b-1) may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of halo, —OH, cyano, C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), —N(C 1-4 alkyl) 2 , and C 1-4 alkyl-OH;
- R 11b represents hydrogen; Het 1e ; C 1-4 alkyl; C 1-4 alkyl-Het 5 ; C 1-4 alkyl substituted with one, two or three substituents each independently selected from the group consisting of halo, —OH and —O—C 1-4 alkyl; C 3-6 cycloalkyl; or C 3-6 cycloalkyl substituted with one, two or three substituents each independently selected from the group consisting of halo,
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , —NR 19a R 19b , C 3-6 cycloalkyl, Het 1d , —S( ⁇ O) 2 —C 1-4 alkyl, —S( ⁇ O)( ⁇ N—R 20c )—C 1-4 alkyl, or —C( ⁇ O)-Het 1f ;
- R 12 represents —OH, —O—C 1-4 alkyl, —NR 14a R 14b , —C( ⁇ O)NR 14c R 14d , —S( ⁇ O) 2 —C 1-4 alkyl, —S( ⁇ O)( ⁇ N—R 20b )—C 1-4 alkyl, C 3-6 cycloalkyl, Ar 2 , or Het 1c ;
- Ar 1 represents phenyl optionally substituted with one hydroxy
- Ar 2 represents phenyl optionally substituted with one C 1-4 alkyl; or a 5- or 6-membered heteroaromatic ring containing one, two or three heteroatoms each independently selected from O, S, and N;
- Het 3a , Het 3b , Het 5 , Het 6 and Het 1f each independently represents a heterocyclyl of formula (c-1):
- (c-1) represents a N-linked 4- to 7-membered monocyclic saturated heterocyclyl optionally containing one additional heteroatom selected from O, S, S( ⁇ O) p and N;
- (c-1) may optionally be substituted on one or two ring C-atoms atoms with one or two substituents each independently selected from the group consisting of halo, C 1-4 alkyl, and C 3-6 cycloalkyl;
- R 11a , R 14a , R 14c , R 14g , R 14i , R 14k , R 15a , R 17a and R 19a each independently represents hydrogen or C 1-4 alkyl;
- R 14b , R 14d , R 14h , R 14j , R 14l , R 15b , R 17b and R 19b each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of halo, —OH and —O—C 1-4 alkyl;
- R 20a , R 20b and R 20c each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl;
- p 1 or 2;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, C 1-6 alkyl substituted with one R 5 , or C 1-6 alkyl substituted with one, two or three fluoro atoms;
- Y represents CR 4 or N
- R 4 represents hydrogen or halo
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents
- ring A1 represents phenyl or a 6-membered heteroaromatic ring containing 1 or 2 N-atoms
- ring A2 represents 2-oxo-1,2-dihydropyridin-3-yl
- ring B1 represents a 4- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O and N;
- (1a-1) and (1a-2) may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo; oxo; —OH; C 1-6 alkyl; —O—C 1-4 alkyl; —C( ⁇ O)—R 10 ; —O—C 1-4 alkyl-R 12 ; —O—C 3-6 cycloalkyl;
- ring A2 may optionally be substituted, where possible, on the N-atom with a substituent selected from the group consisting of C 1-6 alkyl; and C 1-4 alkyl substituted with one R 13 ; and
- ring B1 may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)NR 14g R 14h ; —C( ⁇ O)—C 1-4 alkyl-NR 14i R 14j ; —C( ⁇ O)—C( ⁇ O)—NR 14k R 14l ; or
- ring A represents pyrazolyl optionally substituted with one substituent selected from the group consisting of C 1-4 alkyl, and —C 1-4 alkyl-O—C 1-4 alkyl;
- ring B represents a C 5-7 cycloalkyl or a 5- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O and N;
- C 5-7 cycloalkyl or 5- to 7-membered saturated heterocyclyl may optionally be substituted on one or two ring carbon atoms with one or two substituents each independently selected from the group consisting of C 1-4 alkyl, —C 1-4 alkyl-O—C 1-4 alkyl and —C 1-4 alkyl-OH, or one ring carbon atom may optionally be substituted with oxo; and
- said 5- to 7-membered saturated heterocyclyl may optionally be substituted on one or two ring N-atoms with C 1-6 alkyl;
- fused 7- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo; —O—C 1-4 alkyl; and —C( ⁇ O)—R 10 ; and
- fused 7- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted, where possible, on one ring N-atom with a substituent selected from the group consisting of C 1-4 alkyl substituted with one, two or three —OH substituents; and C 1-4 alkyl substituted with one R 13 ;
- R 10 represents —NR 11a R 11b ;
- Het 1d represents a 4- to 7-membered monocyclic saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- R 11b represents C 1-4 alkyl
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , C 3-6 cycloalkyl, or Het 1d ;
- R 12 represents C 3-6 cycloalkyl
- R 11a , R 14g , R 14i , R 14k , R 15a , and R 17a each independently represents hydrogen or C 1-4 alkyl
- R 14h , R 14j , R 14l , R 15b , and R 17b each independently represents hydrogen or C 1-4 alkyl
- p 1 or 2;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, C 1-6 alkyl substituted with one R 5 , or C 1-6 alkyl substituted with one, two or three fluoro atoms;
- Y represents CR 4 or N
- R 4 represents hydrogen or halo
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused bicyclic ring system of formula (1a-1) or (1a-2):
- ring A1 represents phenyl or a 6-membered heteroaromatic ring containing 1 or 2 N-atoms
- ring A2 represents 2-oxo-1,2-dihydropyridin-3-yl
- ring B1 represents a 4- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O and N;
- (1a-1) and (1a-2) may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo; oxo; —OH; C 1-6 alkyl; —O—C 1-4 alkyl; —C( ⁇ O)—R 10 ; —O—C 1-4 alkyl-R 12 ; —O—C 3-6 cycloalkyl;
- ring A2 may optionally be substituted, where possible, on the N-atom with a substituent selected from the group consisting of C 1-6 alkyl; and C 1-4 alkyl substituted with one R 13 ; and
- ring B1 may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)NR 14g R 14h ; —C( ⁇ O)—C 1-4 alkyl-NR 14i R 14j ; —C( ⁇ O)—C( ⁇ O)—NR 14k R 14l ;
- R 10 represents —NR 11a R 11b ;
- R 11b represents C 1-4 alkyl
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , or C 3-6 cycloalkyl;
- R 12 represents C 3-6 cycloalkyl
- R 11a , R 14g , R 14i , R 14k , R 15a , and R 17a each independently represents hydrogen or C 1-4 alkyl
- R 14h , R 14j , R 14l , R 15b , and R 17b each independently represents hydrogen or C 1-4 alkyl
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen or halo
- R 5 represents —OR 7 ;
- R 7 represents hydrogen, C 1-4 alkyl, —C 1-4 alkyl-NR 8a R 8b , —C( ⁇ O)—R 9 , —(C ⁇ O)—CH(NH 2 )— or C 1-4 alkyl-Ar 1 ;
- R 8a represents hydrogen or C 1-4 alkyl
- R 8b represents hydrogen, C 1-4 alkyl, or C 3-6 cycloalkyl
- R 9 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one substituent selected from the group consisting of —NH 2 , and —COOH;
- R 3 represents a fused bicyclic ring system of formula (1a-1):
- ring A1 represents phenyl or a 6-membered heteroaromatic ring containing 1 or 2 N-atoms
- ring B1 represents a 4- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- (1a-1) may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo; cyano; oxo; C 1-6 alkyl; —O—C 1-4 alkyl; —C( ⁇ O)—R 10 ; —S( ⁇ O) 2 —C 1-4 alkyl; —O—C 1-4 alkyl substituted with one, two or three halo atoms; —O—C 1-4 alkyl-R 12 ; C 3-6 cycloalkyl; —O—C 3-6 cycloalkyl; —NH—C( ⁇ O)—C 1-4 alkyl; —NR 17a R 17b ; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; C 2-6 alkenyl;
- ring B1 may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)NR 14g R 14h ; —C( ⁇ O)—C 1-4 alkyl-NR 14i R 14j ; C( ⁇ O)C( ⁇ O)—NR 14k R 14l ; C 2-6 alkenyl; and C 2-6 alkenyl substituted with one R 13 ;
- R 10 represents —OH, —O—C 1-4 alkyl, or —NR 11a R 11b ;
- R 11b represents hydrogen; C 1-4 alkyl; C 1-4 alkyl substituted with one, two or three substituents each independently selected from the group consisting of halo, —OH and —O—C 1-4 alkyl; C 3-6 cycloalkyl; or C 3-6 cycloalkyl substituted with one, two or three substituents each independently selected from the group consisting of halo, —OH and —O—C 1-4 alkyl;
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , —NR 19a R 19b , C 3-6 cycloalkyl, or —S( ⁇ O) 2 —C 1-4 alkyl;
- R 12 represents —OH, —O—C 1-4 alkyl, —NR 14a R 14b , —C( ⁇ O)NR 14 R 14d , —S( ⁇ O) 2 —C 1-4 alkyl, C 3-6 cycloalkyl, or Ar 2 ;
- Ar 1 represents phenyl optionally substituted with one hydroxy
- Ar 2 represents phenyl optionally substituted with one C 1-4 alkyl
- R 11a , R 14a , R 14c , R 14g , R 14i , R 14k , R 15a , R 17a and R 19a each independently represents hydrogen or C 1-4 alkyl;
- R 14b , R 14d , R 14h , R 14j , R 14l , R 15b , R 17b and R 19b each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of halo, —OH and —O—C 1-4 alkyl;
- R 20a , R 20b and R 20c each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl;
- p 1 or 2;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused bicyclic ring system of formula (1a-1):
- ring A1 represents phenyl or a 6-membered heteroaromatic ring containing 1 or 2 N-atoms
- ring B1 represents a 4- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O and N;
- (1a-1) may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo; C 1-6 alkyl; —O—C 1-4 alkyl; —C( ⁇ O)—R 10 ; —O—C 1-4 alkyl-R 12 ; —NR 17a R 17b ; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; C 2-6 alkenyl; and C 2-6 alkenyl substituted with one R 13 ; and
- ring B1 may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-6 alkyl; C 1-4 alkyl substituted with one R 13 ; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)—C 1-4 alkyl-NR 14i R 14j ; and —C( ⁇ O)—C( ⁇ O)—NR 14k R 14l ;
- R 10 represents —NR 11a R 11b ;
- R 11b represents C 1-4 alkyl
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , or C 3-6 cycloalkyl;
- R 12 represents C 3-6 cycloalkyl
- R 11a , R 14i , R 14k , R 15a , and R 17a each independently represents hydrogen or C 1-4 alkyl
- R 14j , R 14l , R 15b , and R 17b each independently represents hydrogen or C 1-4 alkyl
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused bicyclic ring system of formula (1a-1):
- ring A1 represents phenyl or a 6-membered heteroaromatic ring containing 1 N-atom
- ring B1 represents a 4- to 7-membered saturated heterocyclyl containing one heteroatom selected from O and N;
- (1a-1) may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of —O—C 1-4 alkyl; —O—C 1-4 alkyl-R 12 ; and C 1-4 alkyl substituted with one R 13 ; and
- ring B1 may optionally be substituted, where possible, on one N-atom with a C 1-6 alkyl substituent;
- R 13 represents C 3-6 cycloalkyl
- R 12 represents C 3-6 cycloalkyl
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents methyl
- R 2 represents methyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused bicyclic ring system selected from the following structures
- fused bicyclic ring system may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of —O—C 1-4 alkyl; —O—C 1-4 alkyl-R 12 ; and C 1-4 alkyl substituted with one R 13 ;
- R 13 represents C 3-6 cycloalkyl
- R 12 represents C 3-6 cycloalkyl
- Another embodiment of the present invention relates to those compounds of Formula (I) and the pharmaceutically acceptable addition salts, and the solvates thereof, or any subgroup thereof as mentioned in any of the other embodiments wherein one or more of the following restrictions apply:
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused bicyclic ring system of formula (1a-1):
- ring A1 represents phenyl or a 6-membered heteroaromatic ring containing 1 or 2 N-atoms
- ring B1 represents a 4- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O and N;
- (1a-1) may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo; C 1-6 alkyl; —O—C 1-4 alkyl; —C( ⁇ O)—R 10 ; —O—C 1-4 alkyl-R 12 ; —NR 17a R 17b ; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; C 2-6 alkenyl; and C 2-6 alkenyl substituted with one R 13 ; and
- ring B1 may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-6 alkyl; C 1-4 alkyl substituted with one R 13 ; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)—C 1-4 alkyl-NR 14i R 14j ; —C( ⁇ O)—C( ⁇ O)—NR 14k R 14l ;
- R 10 represents —NR 11a R 11b ;
- R 11b represents C 1-4 alkyl
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , or C 3-6 cycloalkyl;
- R 12 represents C 3-6 cycloalkyl
- R 11a , R 14i , R 14k , R 15a , and R 17a each independently represents hydrogen or C 1-4 alkyl;
- R 14j , R 14l , R 15b , and R 17b each independently represents hydrogen or C 1-4 alkyl.
- Another embodiment of the present invention relates to those compounds of Formula (I) and the pharmaceutically acceptable addition salts, and the solvates thereof, or any subgroup thereof as mentioned in any of the other embodiments wherein one or more of the following restrictions apply:
- R 1 represents methyl
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused bicyclic ring system selected from the following structures
- fused bicyclic ring system may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of —O—C 1-4 alkyl; —O—C 1-4 alkyl-R 12 ; and C 1-4 alkyl substituted with one R 13 ;
- R 13 represents C 3-6 cycloalkyl
- R 12 represents C 3-6 cycloalkyl.
- Another embodiment of the present invention relates to those compounds of Formula (I) and the pharmaceutically acceptable addition salts, and the solvates thereof, or any subgroup thereof as mentioned in any of the other embodiments wherein one or more of the following restrictions apply:
- R 1 represents methyl
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused bicyclic ring system selected from the following structures
- fused bicyclic ring system may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of —O—C 1-4 alkyl; —O—C 1-4 alkyl-R 12 ; and C 1-4 alkyl substituted with one R 13 ;
- R 13 represents C 3-6 cycloalkyl
- R 12 represents C 3-6 cycloalkyl.
- Another embodiment of the present invention relates to those compounds of Formula (I) and the pharmaceutically acceptable addition salts, and the solvates thereof, or any subgroup thereof as mentioned in any of the other embodiments wherein one or more of the following restrictions apply:
- R 1 represents methyl
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused bicyclic ring system selected from the following structures
- said fused bicyclic ring system may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo, oxo, C 1-6 alkyl, —O—C 1-4 alkyl; —O—C 1-4 alkyl-R 12 ; —NR 17a R 17b ; C 1-4 alkyl substituted with one, two or three —OH substituents; and C 1-4 alkyl substituted with one R 13 ; and wherein said fused bicyclic ring system may optionally be substituted on the ring N-atom with a substituent each independently selected from the group consisting of C 1-6 alkyl; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)—C 1-4 alkyl-NR 14i R 14j ; and —C( ⁇ O)—C( ⁇ O)—NR 14k R 14l ;
- R 14i , R 14k , R 14j , R 14l , R 17a , and R 17b each independently represents hydrogen or C 1-4 alkyl;
- R 13 represents C 3-6 cycloalkyl
- R 12 represents C 3-6 cycloalkyl.
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused bicyclic ring system of formula (1a-2):
- ring A2 represents 2-oxo-1,2-dihydropyridin-3-yl
- ring B1 represents a 4- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O and N;
- (1a-2) may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo; C 1-6 alkyl; —O—C 1-4 alkyl; —C( ⁇ O)—R 10 ; C 1-4 alkyl substituted with one, two or three —OH substituents; and C 1-4 alkyl substituted with one R 13 ;
- ring A2 may optionally be substituted, where possible, on the N-atom with a substituent selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; and C 1-4 alkyl substituted with one R 13 ; and
- ring B1 may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-6 alkyl; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)—C 1-4 alkyl-NR 14i R 14j ; and —C( ⁇ O)—C( ⁇ O)—NR 14k R 14l ;
- R 10 represents —NR 11a R 11b ;
- R 11b represents C 1-4 alkyl
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , or C 3-6 cycloalkyl;
- R 11a , R 14i , R 14k , and R 15a each independently represents hydrogen or C 1-4 alkyl
- R 14j , R 14l , and R 15b each independently represents hydrogen or C 1-4 alkyl
- the present invention also relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen or halo
- R 5 represents Het 3a , —NR 6a R 6b , or —OR 7 ;
- R 6a represents hydrogen or C 1-4 alkyl
- R 6b represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; —C( ⁇ O)—C 1-4 alkyl; —C( ⁇ O)-Het 4 ; —S( ⁇ O) 2 —C 1-4 alkyl; —C( ⁇ O)—C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —NR 16a R 16b ; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —S( ⁇ O) 2 —C 1-4 alkyl;
- R 7 represents hydrogen, C 1-4 alkyl, —C 1-4 alkyl-NR 8a R 8b , —C( ⁇ O)—R 9 , —S( ⁇ O) 2 —OH, —P( ⁇ O) 2 —OH, —(C ⁇ O)—CH(NH 2 )—C 1-4 alkyl-Ar 1 , or —C 1-4 alkyl-Het 3b ;
- R 8a represents hydrogen or C 1-4 alkyl
- R 8b represents hydrogen, C 1-4 alkyl, or C 3-6 cycloalkyl
- R 9 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one substituent selected from the group consisting of —NH 2 , —COOH, and Het 6 ;
- R 16a and R 16b each independently represents hydrogen, C 1-4 alkyl or C 3-6 cycloalkyl
- R 3 represents a fused bicyclic ring system of formula (2a-1):
- ring A represents pyrazolyl optionally substituted with one substituent selected from the group consisting of C 1-4 alkyl, —C 1-4 alkyl-O—C 1-4 alkyl, and C 1-4 alkyl substituted with one, two or three halo atoms;
- ring B represents a C 5-7 cycloalkyl or a 5- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O and N;
- C 5-7 cycloalkyl or 5- to 7-membered saturated heterocyclyl may optionally be substituted on one ring carbon atom with one or two C 1-4 alkyl substituents, or one ring carbon atom may optionally be substituted with oxo;
- said 5- to 7-membered saturated heterocyclyl may optionally be substituted on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)NR 14g R 14h ; —C( ⁇ O)—C 1-4 alkyl-NR 14i R 14j ;
- Het 4 represents a 4- to 7-membered monocyclic saturated heterocyclyl, attached to the remainder of the molecule of Formula (II) through any available ring carbon atom, said Het 4 containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl; and wherein said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, halo, C 1-4 alkyl, cyano, —C( ⁇ O)—C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), and —N(C 1-4 alkyl) 2 ;
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , —NR 19a R 19b , C 3-6 cycloalkyl, Het 1d , —S( ⁇ O) 2 —C 1-4 alkyl, —S( ⁇ O)( ⁇ N—R 20c )—C 1-4 alkyl, or —C( ⁇ O)-Het 1f ;
- Ar 1 represents phenyl optionally substituted with one hydroxy
- Het 3a , Het 3b , Het 6 and Het 1f each independently represents a heterocyclyl of formula (c-1):
- (c-1) represents a N-linked 4- to 7-membered monocyclic saturated heterocyclyl optionally containing one additional heteroatom selected from O, S, S( ⁇ O) p and N;
- (c-1) may optionally be substituted on one or two ring C-atoms atoms with one or two substituents each independently selected from the group consisting of halo, C 1-4 alkyl, and C 3-6 cycloalkyl;
- Het 1d represents a 4- to 7-membered monocyclic saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N; or a 6- to 11-membered bicyclic saturated heterocyclyl, including fused, spiro and bridged cycles, containing one, two or three heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- said 4- to 7-membered monocyclic saturated heterocyclyl or said 6- to 11-membered bicyclic saturated heterocyclyl may optionally be substituted, where possible, on one, two or three ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl; and wherein said 4- to 7-membered monocyclic saturated heterocyclyl or said 6- to 11-membered bicyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, oxo, halo, C 1-4 alkyl, cyano, —C( ⁇ O)—C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C —
- R 14g , R 14i , R 15a , and R 19a each independently represents hydrogen or C 1-4 alkyl
- R 14h , R 14j , R 15b , and R 19b each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of halo, —OH and —O—C 1-4 alkyl;
- R 20c represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl;
- p 1 or 2;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, C 1-6 alkyl substituted with one R 5 , or C 1-6 alkyl substituted with one, two or three fluoro atoms;
- Y represents CR 4 or N
- R 4 represents hydrogen or halo
- R 5 represents Het 3a , —NR 6a R 6b , or —OR 7 ;
- R 6a represents hydrogen or C 1-4 alkyl
- R 6b represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; —C( ⁇ O)—C 1-4 alkyl; —C( ⁇ O)-Het 4 ; —S( ⁇ O) 2 —C 1-4 alkyl; —C( ⁇ O)—C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —NR 16a R 16b ; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —S( ⁇ O) 2 —C 1-4 alkyl;
- R 7 represents hydrogen, C 1-4 alkyl, —C 1-4 alkyl-NR 8a R 8b , —C( ⁇ O)—R 9 , —S( ⁇ O) 2 —OH, —P( ⁇ O) 2 —OH, —(C ⁇ O)—CH(NH 2 )—C 1-4 alkyl-Ar 1 , or —C 1-4 alkyl-Het 3b ;
- R 8a represents hydrogen or C 1-4 alkyl
- R 8b represents hydrogen, C 1-4 alkyl, or C 3-6 cycloalkyl
- R 9 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one substituent selected from the group consisting of —NH 2 , —COOH, and Het 6 ;
- R 16a and R 16b each independently represents hydrogen, C 1-4 alkyl or C 3-6 cycloalkyl
- R 3 represents a fused bicyclic ring system of formula (2a-1):
- ring A represents pyrazolyl optionally substituted with one substituent selected from the group consisting of C 1-4 alkyl, —C 1-4 alkyl-O—C 1-4 alkyl, and C 1-4 alkyl substituted with one, two or three halo atoms;
- ring B represents a C 5-7 cycloalkyl or a 5- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O and N;
- C 5-7 cycloalkyl or 5- to 7-membered saturated heterocyclyl may optionally be substituted on one ring carbon atom with one or two substituents each independently selected from the group consisting of C 1-4 alkyl, —C 1-4 alkyl-O—C 1-4 alkyl and —C 1-4 alkyl-OH, or one ring carbon atom may optionally be substituted with oxo; and wherein said 5- to 7-membered saturated heterocyclyl may optionally be substituted on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)NR 14g R 14
- Het 4 represents a 4- to 7-membered monocyclic saturated heterocyclyl, attached to the remainder of the molecule of Formula (I) through any available ring carbon atom, said Het 4 containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl; and wherein said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, halo, C 1-4 alkyl, cyano, —C( ⁇ O)—C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), and —N(C 1-4 alkyl) 2 ;
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , —NR 19a R 19b , C 3-6 cycloalkyl, Het 1d , —S( ⁇ O) 2 —C 1-4 alkyl, —S( ⁇ O)( ⁇ N—R 20c )—C 1-4 alkyl, Ar 2 or —C( ⁇ O)-Het 1f ;
- Ar 1 represents phenyl optionally substituted with one hydroxy
- Ar 2 represents phenyl or a 5- or 6-membered heteroaromatic ring containing one, two or three heteroatoms each independently selected from O, S, and N;
- Het 3a , Het 3b , Het 6 and Het 1f each independently represents a heterocyclyl of formula (c-1):
- (c-1) represents a N-linked 4- to 7-membered monocyclic saturated heterocyclyl optionally containing one additional heteroatom selected from O, S, S( ⁇ O) p and N;
- (c-1) may optionally be substituted on one or two ring C-atoms atoms with one or two substituents each independently selected from the group consisting of halo, C 1-4 alkyl, and C 3-6 cycloalkyl;
- Het 1d represents a 4- to 7-membered monocyclic saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N; or a 6- to 11-membered bicyclic saturated heterocyclyl, including fused, spiro and bridged cycles, containing one, two or three heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- said 4- to 7-membered monocyclic saturated heterocyclyl or said 6- to 11-membered bicyclic saturated heterocyclyl may optionally be substituted, where possible, on one, two or three ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl; and wherein said 4- to 7-membered monocyclic saturated heterocyclyl or said 6- to 11-membered bicyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, oxo, halo, C 1-4 alkyl, cyano, —C( ⁇ O)—C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C —
- R 14g , R 14i , R 15a , and R 19a each independently represents hydrogen or C 1-4 alkyl
- R 14h , R 14j , R 15b , and R 19b each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of halo, —OH and —O—C 1-4 alkyl;
- R 20c represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl;
- p 1 or 2;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen or halo
- R 5 represents —OR 7 ;
- R 7 represents hydrogen, C 1-4 alkyl, —C 1-4 alkyl-NR 8a R 8b , —C( ⁇ O)—R 9 , —(C ⁇ O)—CH(NH 2 )— or C 1-4 alkyl-Ar 1 ;
- R 8a represents hydrogen or C 1-4 alkyl
- R 8b represents hydrogen, C 1-4 alkyl, or C 3-6 cycloalkyl
- R 9 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one substituent selected from the group consisting of —NH 2 , and —COOH;
- R 3 represents a fused bicyclic ring system of formula (2a-1):
- ring A represents pyrazolyl optionally substituted with one substituent selected from the group consisting of C 1-4 alkyl, —C 1-4 alkyl-O—C 1-4 alkyl, and C 1-4 alkyl substituted with one, two or three halo atoms;
- ring B represents a C 5-7 cycloalkyl or a 5- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O and N;
- C 5-7 cycloalkyl or 5- to 7-membered saturated heterocyclyl may optionally be substituted on one ring carbon atom with one or two C 1-4 alkyl substituents, or one ring carbon atom may optionally be substituted with oxo;
- said 5- to 7-membered saturated heterocyclyl may optionally be substituted on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)NR 14g R 14h ; —C( ⁇ O)—C 1-4 alkyl-NR 14i R 14j ;
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , —NR 19a R 19b , or C 3-6 cycloalkyl;
- Ar 1 represents phenyl optionally substituted with one hydroxy
- R 14g , R 14i , R 15a , and R 19a each independently represents hydrogen or C 1-4 alkyl
- R 14h , R 14j , R 15b , and R 19b each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of halo, —OH and —O—C 1-4 alkyl;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused bicyclic ring system of formula (2a-1):
- ring A represents pyrazolyl optionally substituted with one substituent selected from the group consisting of C 1-4 alkyl, and —C 1-4 alkyl-O—C 1-4 alkyl;
- ring B represents a C 5-7 cycloalkyl or a 5- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O and N;
- C 5-7 cycloalkyl or 5- to 7-membered saturated heterocyclyl may optionally be substituted on one or two ring carbon atoms with one or two substituents each independently selected from the group consisting of C 1-4 alkyl, —C 1-4 alkyl-O—C 1-4 alkyl and —C 1-4 alkyl-OH, or one ring carbon atom may optionally be substituted with oxo; and
- said 5- to 7-membered saturated heterocyclyl may optionally be substituted on one or two ring N-atoms with C 1-6 alkyl;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused bicyclic ring system of formula (2a-1):
- ring A represents pyrazolyl optionally substituted with one substituent selected from the group consisting of C 1-4 alkyl, and —C 1-4 alkyl-O—C 1-4 alkyl;
- ring B represents a C 5-7 cycloalkyl or a 5- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O and N;
- C 5-7 cycloalkyl or 5- to 7-membered saturated heterocyclyl may optionally be substituted on one ring carbon atom with one or two C 1-4 alkyl substituents, or one ring carbon atom may optionally be substituted with oxo;
- said 5- to 7-membered saturated heterocyclyl may optionally be substituted on one or two ring N-atoms with a C 1-6 alkyl substituent;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused bicyclic ring system of formula (2a-1):
- ring A represents pyrazolyl
- ring B represents a 6-membered saturated heterocyclyl containing one heteroatom selected from O and N;
- 6-membered saturated heterocyclyl may optionally be substituted on one ring carbon atom with one C 1-4 alkyl substituent, or one ring carbon atom may optionally be substituted with oxo;
- said 5- to 7-membered saturated heterocyclyl may optionally be substituted on one N-atom with a C 1-6 alkyl substituent;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused bicyclic ring system selected from the following structures:
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused bicyclic ring system of formula (2a-1):
- ring A represents pyrazolyl optionally substituted with one substituent selected from the group consisting of C 1-4 alkyl, and —C 1-4 alkyl-O—C 1-4 alkyl;
- ring B represents a C 5-7 cycloalkyl or a 5- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O and N;
- C 5-7 cycloalkyl or 5- to 7-membered saturated heterocyclyl may optionally be substituted on one or two ring carbon atoms with one or two substituents each independently selected from the group consisting of C 1-4 alkyl, —C 1-4 alkyl-O—C 1-4 alkyl and —C 1-4 alkyl-OH, or one ring carbon atom may optionally be substituted with oxo; and
- said 5- to 7-membered saturated heterocyclyl may optionally be substituted on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; and C 1-4 alkyl substituted with one R 13 ;
- R 13 represents Ar 2 ;
- Ar 2 represents phenyl
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused bicyclic ring system selected from the following structures:
- fused bicyclic ring may optionally be substituted on one or two ring carbon atoms with one or two substituents each independently selected from the group consisting of C 1-4 alkyl;
- Another embodiment of the present invention relates to those compounds of Formula (I) and the pharmaceutically acceptable addition salts, and the solvates thereof, or any subgroup thereof as mentioned in any of the other embodiments wherein one or more of the following restrictions apply:
- R 2 represents C 1-6 alkyl substituted with one R 5 ;
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused bicyclic ring system of formula (2a-1):
- ring A represents pyrazolyl optionally substituted with one substituent selected from the group consisting of C 1-4 alkyl, and —C 1-4 alkyl-O—C 1-4 alkyl;
- ring B represents a C 5-7 cycloalkyl or a 5- to 7-membered saturated heterocyclyl containing one or two heteroatoms each independently selected from O and N;
- C 5-7 cycloalkyl or 5- to 7-membered saturated heterocyclyl may optionally be substituted on one ring carbon atom with one or two C 1-4 alkyl substituents, or one ring carbon atom may optionally be substituted with oxo;
- said 5- to 7-membered saturated heterocyclyl may optionally be substituted on one or two ring N-atoms with a C 1-6 alkyl substituent.
- the present invention also relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen or halo
- R 5 represents Het 3a , —NR 6a R 6b , or —OR 7 ;
- R 6a represents hydrogen or C 1-4 alkyl
- R 6b represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; —C( ⁇ O)—C 1-4 alkyl; —C( ⁇ O)-Het 4 ; —S( ⁇ O) 2 —C 1-4 alkyl; —C( ⁇ O)—C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —NR 16a R 16b ; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —S( ⁇ O) 2 —C 1-4 alkyl;
- R 7 represents hydrogen, C 1-4 alkyl, —C 1-4 alkyl-NR 8a R 8b , —C( ⁇ O)—R 9 , —S( ⁇ O) 2 —OH, —P( ⁇ O) 2 —OH, —(C ⁇ O)—CH(NH 2 )—C 1-4 alkyl-Ar 1 , or —C 1-4 alkyl-Het 3b ;
- R 8a represents hydrogen or C 1-4 alkyl
- R 8b represents hydrogen, C 1-4 alkyl, or C 3-6 cycloalkyl
- R 9 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one substituent selected from the group consisting of —NH 2 , —COOH, and Het 6 ;
- R 16a and R 16b each independently represents hydrogen, C 1-4 alkyl or C 3-6 cycloalkyl
- R 3 represents a fused 6- to 11-membered bicyclic heteroaromatic ring system containing one or two heteroatoms each independently selected from O, S, and N;
- fused 6- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo; cyano; C 1-6 alkyl; —O—C 1-4 alkyl; —C( ⁇ O)—R 10 ; —S( ⁇ O) 2 —C 1-4 alkyl; —S( ⁇ O)( ⁇ N—R 20a )—C 1-4 alkyl; —O—C 1-4 alkyl substituted with one, two or three halo atoms; —O—C 1-4 alkyl-R 12 ; C 3-6 cycloalkyl; —O—C 3-6 cycloalkyl; Het 1a ; —O-Het 1b ; R 18 ; —P( ⁇ O)—(C 1-4 alkyl) 2 ; —NH—C( ⁇ O)—C 1-4 alkyl;
- fused 6- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted, where possible, on one ring N-atom with a substituent selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; Het 1a ; R 18 ; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; C 1-4 alkyl substituted with one R 18 ; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)NR 14g R 14h ; —C( ⁇ O)—C 1-4 alkyl-NR 14i R 14j ; —C( ⁇ O)—C( ⁇ O)—NR 14k R 14l ; C 2-6 alkenyl; and C 2-6 alkenyl substituted with one R 13 ; provided that when Het 1a or
- R 10 represents —OH, —O—C 1-4 alkyl, —NR 11a R 11b or Het 2 ;
- R 18 represents a 5-membered aromatic ring containing one, two or three N-atoms; wherein said 5-membered aromatic ring may optionally be substituted with one substituent selected from the group consisting of C 1-4 alkyl and C 3-6 cycloalkyl;
- Het 1a , Het 1c and Het 1d each independently represents a 4- to 7-membered monocyclic saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N; or a 6- to 11-membered bicyclic saturated heterocyclyl, including fused, spiro and bridged cycles, containing one, two or three heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- said 4- to 7-membered monocyclic saturated heterocyclyl or said 6- to 11-membered bicyclic saturated heterocyclyl may optionally be substituted, where possible, on one, two or three ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and
- said 4- to 7-membered monocyclic saturated heterocyclyl or said 6- to 11-membered bicyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, oxo, halo, C 1-4 alkyl, cyano, —C( ⁇ O)—C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), and —N(C 1-4 alkyl) 2 ;
- Het 1b , Het 1e , Het 1g and Het 4 each independently represents a 4- to 7-membered monocyclic saturated heterocyclyl, attached to the remainder of the molecule of Formula (I) through any available ring carbon atom, said Het 1b , Het 1e , Het 1g and Het 4 containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl; and
- said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, halo, C 1-4 alkyl, cyano, —C( ⁇ O)—C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), and —N(C 1-4 alkyl) 2 ;
- Het 2 represents a heterocyclyl of formula (b-1):
- (b-1) represents a N-linked 4- to 7-membered monocyclic saturated heterocyclyl optionally containing one additional heteroatom selected from O, S, S( ⁇ O) p and N, or a N-linked 6- to 11-membered bicyclic saturated heterocyclyl, including fused, spiro and bridged cycles, optionally containing one or two additional heteroatoms each independently selected from O, S, S( ⁇ O), and N;
- (b-1) may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of halo, —OH, cyano, C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), —N(C 1-4 alkyl) 2 , and C 1-4 alkyl-OH;
- R 11b represents hydrogen; Het 1e ; C 1-4 alkyl; C 1-4 alkyl-Het 5 ; C 1-4 alkyl substituted with one, two or three substituents each independently selected from the group consisting of halo, —OH and —O—C 1-4 alkyl; C 3-6 cycloalkyl; or C 3-6 cycloalkyl substituted with one, two or three substituents each independently selected from the group consisting of halo, —OH and —O—C 1-4 alkyl;
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , —NR 19a R 19b , C 3-6 cycloalkyl, Het 1d , —S( ⁇ O) 2 —C 1-4 alkyl, —S( ⁇ O)( ⁇ N—R 20c )—C 1-4 alkyl, or —C( ⁇ O)-Het 1f ;
- R 12 represents —OH, —O—C 1-4 alkyl, —NR 14a R 14b , —C( ⁇ O)NR 14c R 14d , —S( ⁇ O) 2 —C 1-4 alkyl, —S( ⁇ O)( ⁇ N—R 20b )—C 1-4 alkyl, C 3-6 cycloalkyl, Ar 2 , or Het 1c ;
- Ar 1 represents phenyl optionally substituted with one hydroxy
- Ar 2 represents phenyl optionally substituted with one C 1-4 alkyl
- Het 3a , Het 3b , Het 5 , Het 6 and Het 1f each independently represents a heterocyclyl of formula (c-1):
- (c-1) represents a N-linked 4- to 7-membered monocyclic saturated heterocyclyl optionally containing one additional heteroatom selected from O, S, S( ⁇ O) p and N;
- (c-1) may optionally be substituted on one or two ring C-atoms atoms with one or two substituents each independently selected from the group consisting of halo, C 1-4 alkyl, and C 3-6 cycloalkyl;
- R 11a , R 14a , R 14c , R 14g , R 14i , R 14k , R 15a , R 17a and R 19a each independently represents hydrogen or C 1-4 alkyl;
- R 14b , R 14d , R 14h , R 14j , R 14l , R 15b , R 17b and R 19b each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of halo, —OH and —O—C 1-4 alkyl;
- R 20a , R 20b and R 20c each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl;
- p 1 or 2;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, C 1-6 alkyl substituted with one R 5 , or C 1-6 alkyl substituted with one, two or three fluoro atoms;
- Y represents CR 4 or N
- R 4 represents hydrogen or halo
- R 5 represents Het 3a , —NR 6a R 6b , or —OR 7 ;
- R 6a represents hydrogen or C 1-4 alkyl
- R 6b represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; —C( ⁇ O)—C 1-4 alkyl; —C( ⁇ O)-Het 4 ; —S( ⁇ O) 2 —C 1-4 alkyl; —C( ⁇ O)—C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —NR 16a R 16b ; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —S( ⁇ O) 2 —C 1-4 alkyl;
- R 7 represents hydrogen, C 1-4 alkyl, —C 1-4 alkyl-NR 8a R 8b , —C( ⁇ O)—R 9 , —S( ⁇ O) 2 —OH, —P( ⁇ O) 2 —OH, —(C ⁇ O)—CH(NH 2 )—C 1-4 alkyl-Ar 1 , or —C 1-4 alkyl-Het 3b ;
- R 8a represents hydrogen or C 1-4 alkyl
- R 8b represents hydrogen, C 1-4 alkyl, or C 3-6 cycloalkyl
- R 9 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one substituent selected from the group consisting of —NH 2 , —COOH, and Het 6 ;
- R 16a and R 16b each independently represents hydrogen, C 1-4 alkyl or C 3-6 cycloalkyl
- R 3 represents a fused 6- to 11-membered bicyclic heteroaromatic ring system containing one or two heteroatoms each independently selected from O, S, and N;
- fused 6- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo; cyano; C 1-6 alkyl; —O—C 1-4 alkyl; —C( ⁇ O)—R 10 ; —S( ⁇ O) 2 —C 1-4 alkyl; —S( ⁇ O)( ⁇ N—R 20a )—C 1-4 alkyl; —O—C 1-4 alkyl substituted with one, two or three halo atoms; —O—C 1-4 alkyl-R 12 ; C 3-6 cycloalkyl; —O—C 3-6 cycloalkyl; Het 1a ; —O-Het 1b ; R 18 ; —P( ⁇ O)—(C 1-4 alkyl) 2 ; —NH—C( ⁇ O)—C 1-4 alkyl;
- fused 6- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted, where possible, on one ring N-atom with a substituent selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; Het 1a ; R 18 ; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; C 1-4 alkyl substituted with one R 18 ; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)NR 14g R 14h ; —C( ⁇ O)—C 1-4 alkyl-NR 14i R 14j ; —C( ⁇ O)—C( ⁇ O)—NR 14k R 14l ; C 2-6 alkenyl; and C 2-6 alkenyl substituted with one R 13 ; provided that when Het 1a or
- R 10 represents —OH, —O—C 1-4 alkyl, —NR 11a R 11b or Het 2 ;
- R 18 represents a 5-membered aromatic ring containing one, two or three N-atoms; wherein said 5-membered aromatic ring may optionally be substituted with one substituent selected from the group consisting of C 1-4 alkyl and C 3-6 cycloalkyl;
- Het 1a , Het 1c and Het 1d each independently represents a 4- to 7-membered monocyclic saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N; or a 6- to 11-membered bicyclic saturated heterocyclyl, including fused, spiro and bridged cycles, containing one, two or three heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- said 4- to 7-membered monocyclic saturated heterocyclyl or said 6- to 11-membered bicyclic saturated heterocyclyl may optionally be substituted, where possible, on one, two or three ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and
- said 4- to 7-membered monocyclic saturated heterocyclyl or said 6- to 11-membered bicyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, oxo, halo, C 1-4 alkyl, cyano, —C( ⁇ O)—C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), and —N(C 1-4 alkyl) 2 ;
- Het 1b , Het 1e , Het 1g and Het 4 each independently represents a 4- to 7-membered monocyclic saturated heterocyclyl, attached to the remainder of the molecule of Formula (I) through any available ring carbon atom, said Het 1b , Het 1e , Het 1g and Het 4 containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl; and
- said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, halo, C 1-4 alkyl, cyano, —C( ⁇ O)—C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), and —N(C 1-4 alkyl) 2 ;
- Het 2 represents a heterocyclyl of formula (b-1):
- (b-1) represents a N-linked 4- to 7-membered monocyclic saturated heterocyclyl optionally containing one additional heteroatom selected from O, S, S( ⁇ O) p and N, or a N-linked 6- to 11-membered bicyclic saturated heterocyclyl, including fused, spiro and bridged cycles, optionally containing one or two additional heteroatoms each independently selected from O, S, S( ⁇ O), and N;
- (b-1) may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of halo, —OH, cyano, C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), —N(C 1-4 alkyl) 2 , and C 1-4 alkyl-OH;
- R 11b represents hydrogen; Het 1e ; C 1-4 alkyl; C 1-4 alkyl-Het 5 ; C 1-4 alkyl substituted with one, two or three substituents each independently selected from the group consisting of halo, —OH and —O—C 1-4 alkyl; C 3-6 cycloalkyl; or C 3-6 cycloalkyl substituted with one, two or three substituents each independently selected from the group consisting of halo, —OH and —O—C 1-4 alkyl;
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , —NR 19a R 19b , C 3-6 cycloalkyl, Het 1d , —S( ⁇ O) 2 —C 1-4 alkyl, —S( ⁇ O)( ⁇ N—R 20c )—C 1-4 alkyl, or —C( ⁇ O)-Het 1f ;
- R 12 represents —OH, —O—C 1-4 alkyl, —NR 14a R 14b , —C( ⁇ O)NR 14 R 14d , —S( ⁇ O) 2 —C 1-4 alkyl, —S( ⁇ O)( ⁇ N—R 20b )—C 1-4 alkyl, C 3-6 cycloalkyl, Ar 2 , or Het 1c ;
- Ar 1 represents phenyl optionally substituted with one hydroxy
- Ar 2 represents phenyl optionally substituted with one C 1-4 alkyl
- Het 3a , Het 3b , Het 5 , Het 6 and Het 1f each independently represents a heterocyclyl of formula (c-1):
- (c-1) represents a N-linked 4- to 7-membered monocyclic saturated heterocyclyl optionally containing one additional heteroatom selected from O, S, S( ⁇ O) p and N;
- (c-1) may optionally be substituted on one or two ring C-atoms atoms with one or two substituents each independently selected from the group consisting of halo, C 1-4 alkyl, and C 3-6 cycloalkyl;
- R 11a , R 14a , R 14e , R 14g , R 14i , R 14k , R 15a , R 17a and R 19a each independently represents hydrogen or C 1-4 alkyl;
- R 14b , R 14d , R 14h , R 14j , R 14l , R 15b , R 17b and R 19b each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of halo, —OH and —O—C 1-4 alkyl;
- R 20a , R 20b and R 20c each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl;
- p 1 or 2;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, C 1-6 alkyl substituted with one R 5 , or C 1-6 alkyl substituted with one, two or three fluoro atoms;
- Y represents CR 4 or N
- R 4 represents hydrogen or halo
- R 5 represents Het 3a , —NR 6a R 6b , or —OR 7 ;
- R 6a represents hydrogen or C 1-4 alkyl
- R 6b represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; —C( ⁇ O)—C 1-4 alkyl; —C( ⁇ O)-Het 4 ; —S( ⁇ O) 2 —C 1-4 alkyl; —C( ⁇ O)—C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —NR 16a R 16b ; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —S( ⁇ O) 2 —C 1-4 alkyl;
- R 7 represents hydrogen, C 1-4 alkyl, —C 1-4 alkyl-NR 8a R 8b , —C( ⁇ O)—R 9 , —S( ⁇ O) 2 —OH, —P( ⁇ O) 2 —OH, —(C ⁇ O)—CH(NH 2 )—C 1-4 alkyl-Ar 1 , or —C 1-4 alkyl-Het 3b ;
- R 8a represents hydrogen or C 1-4 alkyl
- R 8b represents hydrogen, C 1-4 alkyl, or C 3-6 cycloalkyl
- R 9 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one substituent selected from the group consisting of —NH 2 , —COOH, and Het 6 ;
- R 16a and R 16b each independently represents hydrogen, C 1-4 alkyl or C 3-6 cycloalkyl
- R 3 represents a fused 7- to 11-membered bicyclic heteroaromatic ring system containing one or two heteroatoms each independently selected from O, S, and N;
- fused 7- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo; cyano; C 1-6 alkyl; —O—C 1-4 alkyl; —C( ⁇ O)—R 10 ; —S( ⁇ O) 2 —C 1-4 alkyl; —S( ⁇ O)( ⁇ N—R 20a )—C 1-4 alkyl; —O—C 1-4 alkyl substituted with one, two or three halo atoms; —O—C 1-4 alkyl-R 12 ; C 3-6 cycloalkyl; —O—C 3-6 cycloalkyl; Het 1a ; —O-Het 1b ; R 18 ; —P( ⁇ O)—(C 1-4 alkyl) 2 ; —NH—C( ⁇ O)—C 1-4 alkyl
- fused 7- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted, where possible, on one ring N-atom with a substituent selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; Het 1a ; R 18 ; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; C 1-4 alkyl substituted with one R 18 ; —(C ⁇ O)—C 1-4 alkyl; —C( ⁇ O)NR 14g R 14h ; —C( ⁇ O)—C 1-4 alkyl-NR 14i R 14j ; —C( ⁇ O)—C( ⁇ O)—NR 14k R 14l ; C 2-6 alkenyl; and C 2-6 alkenyl substituted with one R 13 ; provided that when Het 1a
- R 10 represents —OH, —O—C 1-4 alkyl, —NR 11a R 11b or Het 2 ;
- R 18 represents a 5-membered aromatic ring containing one, two or three N-atoms; wherein said 5-membered aromatic ring may optionally be substituted with one substituent selected from the group consisting of C 1-4 alkyl and C 3-6 cycloalkyl;
- Het 1a , Het 1c and Het 1d each independently represents a 4- to 7-membered monocyclic saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N; or a 6- to 11-membered bicyclic saturated heterocyclyl, including fused, spiro and bridged cycles, containing one, two or three heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- said 4- to 7-membered monocyclic saturated heterocyclyl or said 6- to 11-membered bicyclic saturated heterocyclyl may optionally be substituted, where possible, on one, two or three ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and
- said 4- to 7-membered monocyclic saturated heterocyclyl or said 6- to 11-membered bicyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, oxo, halo, C 1-4 alkyl, cyano, —C( ⁇ O)—C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), and —N(C 1-4 alkyl) 2 ;
- Het 1b , Het 1e , Het 1g and Het 4 each independently represents a 4- to 7-membered monocyclic saturated heterocyclyl, attached to the remainder of the molecule of Formula (I) through any available ring carbon atom, said Het 1b , Het 1e , Het 1g and Het 4 containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl; and
- said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, halo, C 1-4 alkyl, cyano, —C( ⁇ O)—C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), and —N(C 1-4 alkyl) 2 ;
- Het 2 represents a heterocyclyl of formula (b-1):
- (b-1) represents a N-linked 4- to 7-membered monocyclic saturated heterocyclyl optionally containing one additional heteroatom selected from O, S, S( ⁇ O) p and N, or a N-linked 6- to 11-membered bicyclic saturated heterocyclyl, including fused, spiro and bridged cycles, optionally containing one or two additional heteroatoms each independently selected from O, S, S( ⁇ O), and N;
- (b-1) may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of halo, —OH, cyano, C 1-4 alkyl, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), —N(C 1-4 alkyl) 2 , and C 1-4 alkyl-OH;
- R 11b represents hydrogen; Het 1e ; C 1-4 alkyl; C 1-4 alkyl-Het 5 ; C 1-4 alkyl substituted with one, two or three substituents each independently selected from the group consisting of halo, —OH and —O—C 1-4 alkyl; C 3-6 cycloalkyl; or C 3-6 cycloalkyl substituted with one, two or three substituents each independently selected from the group consisting of halo,
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , —NR 19a R 19b , C 3-6 cycloalkyl, Het 1d , —S( ⁇ O) 2 —C 1-4 alkyl, —S( ⁇ O)( ⁇ N—R 20c )—C 1-4 alkyl, or —C( ⁇ O)-Het 1f ;
- R 12 represents —OH, —O—C 1-4 alkyl, —NR 14a R 14b , —C( ⁇ O)NR 14c R 14d , —S( ⁇ O) 2 —C 1-4 alkyl, —S( ⁇ O)( ⁇ N—R 20b )—C 1-4 alkyl, C 3-6 cycloalkyl, Ar 2 , or Het c ;
- Ar 1 represents phenyl optionally substituted with one hydroxy
- Ar 2 represents phenyl optionally substituted with one C 1-4 alkyl
- Het 3a , Het 3b , Het 5 , Het 6 and Het 1f each independently represents a heterocyclyl of formula (c-1):
- (c-1) represents a N-linked 4- to 7-membered monocyclic saturated heterocyclyl optionally containing one additional heteroatom selected from O, S, S( ⁇ O) p and N;
- (c-1) may optionally be substituted on one or two ring C-atoms atoms with one or two substituents each independently selected from the group consisting of halo, C 1-4 alkyl, and C 3-6 cycloalkyl;
- R 11a , R 14a , R 14c , R 14g , R 14i , R 14k , R 15a , R 17a and R 19a each independently represents hydrogen or C 1-4 alkyl;
- R 14b , R 14d , R 14h , R 14j , R 14l , R 15b , R 17b and R 19b each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of halo, —OH and —O—C 1-4 alkyl;
- R 20a , R 20b and R 20c each independently represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and —O—C 1-4 alkyl;
- p 1 or 2;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen or halo
- R 5 represents —NR 6a R 6b , or —OR 7 ;
- R 6a represents hydrogen or C 1-4 alkyl
- R 6b represents hydrogen; C 1-4 alkyl; C 3-6 cycloalkyl; or —C( ⁇ O)—C 1-4 alkyl;
- R 7 represents hydrogen, C 1-4 alkyl, or —C 1-4 alkyl-NR 8a R 8b ;
- R 8a represents hydrogen or C 1-4 alkyl
- R 8b represents hydrogen, C 1-4 alkyl, or C 3-6 cycloalkyl
- R 3 represents a fused 6- to 11-membered bicyclic heteroaromatic ring system containing one or two heteroatoms each independently selected from O, S, and N;
- fused 6- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo; cyano; C 1-6 alkyl; —O—C 1-4 alkyl; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; C 2-6 alkenyl; and C 2-6 alkenyl substituted with one R 13 ; and
- fused 6- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted, where possible, on one ring N-atom with a substituent selected from the group consisting of C 1-6 alkyl; C 3-6 cycloalkyl; C 1-4 alkyl substituted with one, two or three halo atoms; C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ; C 1-4 alkyl substituted with one R 18 ; C 2-6 alkenyl; and C 2-6 alkenyl substituted with one R 13 ;
- Het 1d represents a 4- to 7-membered monocyclic saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted, where possible, on one or two ring N-atoms with a substituent each independently selected from the group consisting of C 1-4 alkyl, C 3-6 cycloalkyl, and C 1-4 alkyl substituted with one substituent selected from the group consisting of —OH and
- said 4- to 7-membered monocyclic saturated heterocyclyl may optionally be substituted on one, two or three ring C-atoms with one or two substituents each independently selected from the group consisting of —OH, halo, C 1-4 alkyl, cyano, —O—C 1-4 alkyl, —NH 2 , —NH(C 1-4 alkyl), and —N(C 1-4 alkyl) 2 ;
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , —NR 19a R 19b , C 3-6 cycloalkyl, or Het 1d ;
- R 15a , and R 19a each independently represents hydrogen or C 1-4 alkyl
- R 15b , and R 19b each independently represents hydrogen; C 1-4 alkyl;
- p 1 or 2;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused 6- to 11-membered bicyclic heteroaromatic ring system containing one or two heteroatoms each independently selected from O, S, and N;
- fused 6- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted on the ring carbon atoms with in total one, two or three halo substituents;
- fused 6- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted, where possible, on one ring N-atom with a substituent selected from the group consisting of C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ;
- Het 1d represents a 4- to 7-membered monocyclic saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , or Het 1d ;
- R 15a represents hydrogen or C 1-4 alkyl
- R 15b represents C 1-4 alkyl
- p 1 or 2;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused 7- to 11-membered bicyclic heteroaromatic ring system containing one or two heteroatoms each independently selected from O, S, and N;
- fused 7- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted on the ring carbon atoms with in total one, two or three halo substituents;
- fused 7- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted, where possible, on one ring N-atom with a substituent selected from the group consisting of C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ;
- Het 1d represents a 4- to 7-membered monocyclic saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , or Het 1d ;
- R 15a represents hydrogen or C 1-4 alkyl
- R 15b represents C 1-4 alkyl
- p 1 or 2;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused 7- to 11-membered bicyclic heteroaromatic ring system containing one or two heteroatoms each independently selected from O, S, and N;
- fused 7- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted on the ring carbon atoms with in total one, two or three substituents each independently selected from the group consisting of halo; —O—C 1-4 alkyl; and —C( ⁇ O)—R 10 ; and
- fused 7- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted, where possible, on one ring N-atom with a substituent selected from the group consisting of C 1-4 alkyl substituted with one, two or three —OH substituents; and C 1-4 alkyl substituted with one R 13 ;
- R 10 represents —NR 11a R 11b ;
- Het 1d represents a 4- to 7-membered monocyclic saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- R 11b represents C 1-4 alkyl
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , or Het 1d ;
- R 11a and R 15a each independently represents hydrogen or C 1-4 alkyl
- R 15b represents C 1-4 alkyl
- p 1 or 2;
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused 9-membered bicyclic heteroaromatic ring system containing one or two N-atoms
- fused 9-membered bicyclic heteroaromatic ring system may optionally be substituted on the ring carbon atoms with in total one, two or three halo substituents; and wherein said fused 9-membered bicyclic heteroaromatic ring system may optionally be substituted, where possible, on one ring N-atom with a substituent selected from the group consisting of C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ;
- Het 1d represents morpholinyl
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , or Het 1d ;
- R 15a represents hydrogen or C 1-4 alkyl
- R 15b represents C 1-4 alkyl
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused 9-membered bicyclic heteroaromatic ring system selected from the following structures
- the present invention relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused 9-membered bicyclic heteroaromatic ring system selected from the following structures
- the present invention also relates in particular to compounds of Formula (I) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl, or C 1-6 alkyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused 9-membered bicyclic heteroaromatic ring system containing one N-atom
- fused 9-membered bicyclic heteroaromatic ring system may optionally be substituted on the ring carbon atoms with in total one, two or three halo substituents; and wherein said fused 9-membered bicyclic heteroaromatic ring system may optionally be substituted, where possible, on one ring N-atom with a substituent selected from the group consisting of C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ;
- R 13 represents —O—C 1-4 alkyl, or —C( ⁇ O)NR 15a R 15b ;
- R 15a represents hydrogen or C 1-4 alkyl
- R 15b represents C 1-4 alkyl
- the present invention relates in particular to compounds of Formula (III) as defined herein, tautomers and stereoisomeric forms thereof, wherein
- R 1 represents methyl
- R 2 represents methyl substituted with one R 5 ;
- Y represents CR 4 ;
- R 4 represents hydrogen
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents
- R 13 represents —O—C 1-4 alkyl, or —C( ⁇ O)NR 15a R 15b ;
- R 15a represents hydrogen or C 1-4 alkyl
- R 15b represents C 1-4 alkyl
- Another embodiment of the present invention relates to those compounds of Formula (I) and the pharmaceutically acceptable addition salts, and the solvates thereof, or any subgroup thereof as mentioned in any of the other embodiments wherein one or more of the following restrictions apply:
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 3 represents a fused 6- to 11-membered bicyclic heteroaromatic ring system containing one or two heteroatoms each independently selected from O, S, and N;
- fused 6- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted on the ring carbon atoms with in total one, two or three halo substituents; and wherein said fused 6- to 11-membered bicyclic heteroaromatic ring system may optionally be substituted, where possible, on one ring N-atom with a substituent selected from the group consisting of C 1-4 alkyl substituted with one, two or three —OH substituents; C 1-4 alkyl substituted with one R 13 ;
- Het 1d represents a 4- to 7-membered monocyclic saturated heterocyclyl containing one or two heteroatoms each independently selected from O, S, S( ⁇ O) p and N;
- R 13 represents —O—C 1-4 alkyl, —C( ⁇ O)NR 15a R 15b , or Het 1d ;
- R 15a represents hydrogen or C 1-4 alkyl
- R 15b represents C 1-4 alkyl.
- Another embodiment of the present invention relates to those compounds of Formula (I) and the pharmaceutically acceptable addition salts, and the solvates thereof, or any subgroup thereof as mentioned in any of the other embodiments wherein one or more of the following restrictions apply:
- R 1 represents methyl
- R 2 represents methyl substituted with one R 5 ;
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- R 13 represents —O—C 1-4 alkyl, or —C( ⁇ O)NR 15a R 15b ;
- R 15a represents hydrogen or C 1-4 alkyl
- R 15b represents C 1-4 alkyl.
- the present invention relates to a subgroup of Formula (I), hereby named compounds of Formula (I′):
- the present invention relates to a subgroup of Formula (I), hereby named compounds of Formula (I′):
- R represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl substituted with one R 5 ;
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl substituted with one R 5 ;
- R 5 represents —OR 7 ;
- R 1 represents C 1-4 alkyl
- R 2 represents C 1-6 alkyl substituted with one R 5 ;
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- the present invention relates to those compounds of Formula (I) and the pharmaceutically acceptable addition salts, and the solvates thereof, or any subgroup thereof as mentioned in any of the other embodiments, wherein
- R 1 represents methyl
- R 2 represents methyl or —CH 2 —OH.
- the present invention relates to those compounds of Formula (I) and the pharmaceutically acceptable addition salts, and the solvates thereof, or any subgroup thereof as mentioned in any of the other embodiments, wherein
- R 1 represents methyl
- R 2 represents —CH 2 —OH.
- the present invention relates to those compounds of Formula (I) and the pharmaceutically acceptable addition salts, and the solvates thereof, or any subgroup thereof as mentioned in any of the other embodiments, wherein R 4 represents hydrogen or fluoro.
- the present invention relates to those compounds of Formula (I) and the pharmaceutically acceptable addition salts, and the solvates thereof, or any subgroup thereof as mentioned in any of the other embodiments, wherein R 4 represents hydrogen.
- the present invention relates to those compounds of Formula (I) and the pharmaceutically acceptable addition salts, and the solvates thereof, or any subgroup thereof as mentioned in any of the other embodiments, wherein
- R 7 represents hydrogen
- the present invention relates to those compounds of Formula (I) and the pharmaceutically acceptable addition salts, and the solvates thereof, or any subgroup thereof as mentioned in any of the other embodiments, wherein
- R 5 represents —OR 7 ;
- R 7 represents hydrogen
- the present invention relates to those compounds of Formula (I) and the pharmaceutically acceptable addition salts, and the solvates thereof, or any subgroup thereof as mentioned in any of the other embodiments, wherein
- R 9 represents C 1-4 alkyl, or C 1-4 alkyl substituted with one substituent selected from the group consisting of —NH 2 , —COOH, and Het 6 .
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Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
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EP16177131.6 | 2016-06-30 | ||
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US11136311B2 (en) | 2016-06-30 | 2021-10-05 | Janssen Pharmaceutica Nv | Heteroaromatic derivatives as NIK inhibitors |
US11180487B2 (en) | 2016-01-22 | 2021-11-23 | Janssen Pharmaceutica Nv | Substituted cyanoindoline derivatives as NIK inhibitors |
US11186589B2 (en) | 2016-06-30 | 2021-11-30 | Janssen Pharmaceutica Nv | Cyanoindoline derivatives as NIK inhibitors |
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US11001569B2 (en) | 2016-01-22 | 2021-05-11 | Janssen Pharmaceutica Nv | 6-membered heteroaromatic substituted cyanoindoline derivatives as NIK inhibitors |
US11180487B2 (en) | 2016-01-22 | 2021-11-23 | Janssen Pharmaceutica Nv | Substituted cyanoindoline derivatives as NIK inhibitors |
US11136311B2 (en) | 2016-06-30 | 2021-10-05 | Janssen Pharmaceutica Nv | Heteroaromatic derivatives as NIK inhibitors |
US11186589B2 (en) | 2016-06-30 | 2021-11-30 | Janssen Pharmaceutica Nv | Cyanoindoline derivatives as NIK inhibitors |
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CN109689645A (zh) | 2019-04-26 |
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US11186589B2 (en) | 2021-11-30 |
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AU2017289317B2 (en) | 2021-04-01 |
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WO2018002219A1 (en) | 2018-01-04 |
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JP6936814B2 (ja) | 2021-09-22 |
EP3478673A1 (en) | 2019-05-08 |
CA3027418A1 (en) | 2018-01-04 |
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