US20150099730A1 - Imidazolin-5-one derivative useful as fasn inhibitors for the treatment of cancer - Google Patents
Imidazolin-5-one derivative useful as fasn inhibitors for the treatment of cancer Download PDFInfo
- Publication number
- US20150099730A1 US20150099730A1 US14/020,122 US201314020122A US2015099730A1 US 20150099730 A1 US20150099730 A1 US 20150099730A1 US 201314020122 A US201314020122 A US 201314020122A US 2015099730 A1 US2015099730 A1 US 2015099730A1
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- United States
- Prior art keywords
- methyl
- group
- cyclopropyl
- alkyl
- phenyl
- Prior art date
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- Abandoned
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
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- 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
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- 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
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- C07D498/04—Ortho-condensed systems
Definitions
- the present invention is directed to imidazolin-5-one derivatives, pharmaceutical compositions containing them, and their use as FASN inhibitors, in for example, the treatment of cancer, obesity related disorders, and liver related disorders.
- Fatty acid synthase is a key enzyme for the synthesis of long-chain fatty acids from acetyl-coenzyme A (CoA) and malonyl-CoA that uses reduced nicotinamide adenine dinucleotidephosphate as a cofactor.
- the final step in the de novo synthesis of fatty acids in mammalians is carried out by FASN, a 250 kDa protein containing 7 functional domains.
- FASN produces palmitate starting from the substrates acetylCoA and malonylCo, using NADPH (as defined below) as a cofactor (See, MAIER, T., et al., “Architecture of mammalian fatty acid synthase at 4.5 ⁇ resolution”, Science, 2006, pp 1258-1262, Vol. 311).
- FASN is minimally expressed in most normal human tissues except the liver and adipose tissue, where it is expressed at high levels. Except for these lipogenic tissues (such as liver, lactating breast, fetal lung, and adipose tissue), FASN has a low expression in normal cells which use fatty acids from the diet, while tumor cells largely depend on de novo fatty acid synthesis. FASN expression is highly up-regulated in various tumors, e.g. prostate, breast, colon, and lung cancer (See, SWINNEN, J. V., et al., “Stimulation of tumor-associated fatty acid synthase expression by growth factor activation of the sterol regulatory element-binding protein pathway”.
- FASN overexpression leads to growth and survival advantage to the tumors achieved through multiple mechanisms. Firstly, it provides lipids for membrane synthesis. Moreover, the more saturated lipid composition of the membranes increases resistance to chemotherapy. FASN also contributes to improved growth factor receptor expression in lipid rafts (See, SWINNEN, J. V., et al., “Fatty acid synthase drives the synthesis of phospholipids partitioning into detergent resistant membrane microdomains”, Biochem. Biophys. Res. Commun., 2000, pp 898-903, Vol. 302; MENENDEZ, J.
- FASN is also over expressed in androgen-independent prostate cancers most likely through activation of the PI3K/Akt pathway (See, BANDYOPADHYAY, S., et al., “FAS expression inversely correlates with PTEN level in prostate cancer and a PI-3 kinase inhibitor synergizes with FAS siRNA to induce apoptosis”, Oncogene, 2005, pp 5389-5395, Vol.
- FASN inhibitors are viewed as potential therapeutics for the treatment of cancer.
- pharmaceutical agents for the treatment of a variety of cancers including breast, prostate, head, neck, skin, lung, ovary, endometrium, thyroid, colon, rectum, esophagus, stomach, kidney, liver, bladder, pancreas, brain, blood, bone, and others.
- FASN inhibitors have also shown promise in the treatment of other FASN-mediated diseases, disorders or conditions, such as, obesity, lack of appetite control, and inflammatory conditions. Additionally, FASN has been implicated in diabetes and/or regulation of the general wellness of the liver, and therefore has potential in the treatment of obesity, Type II diabetes mellitus, Syndrome X, and disorders of the liver; the treatment of which there remains a need for pharmaceutical agents.
- the present invention is directed to compounds of formula (I)
- R 1 and R 2 are taken together with the carbon atom to which they are bound to form an optionally substituted ring structure selected from the group consisting of
- R 10 is selected from the group consisting of hydrogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, —CH 2 -(hydroxy substituted C 1-4 alkyl), —(C 2-4 alkyl)-O—(C 1-4 alkyl), —(C 2-4 alkenyl), —(C 1-4 alkyl)-phenyl, —C(O)—NR A R B , —C(O)—(C 1-3 alkyl)-NR A R B , —C(O)—(C 1-4 alkyl), —C(O)-(fluorinated C 1-2 alkyl), —C(O)—(C 3-6 cycloalkyl), —C(O)-phenyl, —C(O)-(5 to 6-membered heteroaryl),
- phenyl or 5 to 6-membered heteroaryl whether alone or as part of a substituent group is further optionally substituted with one to two substituents independently selected from the group consisting of halogen, hydroxy, cyano, NR A R B , C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy and fluorinated C 1-4 alkoxy;
- each R 11 is independently selected from the group consisting of hydroxy, oxo, halogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, hydroxy substituted C 1-4 alkyl, —(C 1-4 alkyl)-O—(C 1-4 alkyl), —(C 1-4 alkyl)-phenyl, -cyano, —NR D R E , —C(O)—NR D R E , —C(O)—(C 1-4 alkyl), —C(O)-phenyl, —C(O)-(5 to 6-membered heteroaryl),
- Z 2 is selected from the group consisting of —CH 2 —, —O—, —N(R C )—, —S—, —S(O)— and —SO 2 —; wherein R D , R E and R F are each independently selected from the group consisting of hydrogen and C 1-4 alkyl;
- phenyl or 5 to 6-membered heteroaryl is further optionally substituted with one to two substituents independently selected from the group consisting of halogen, hydroxy, cyano, NR D R E , C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy and fluorinated C 1-4 alkoxy;
- R 12 is selected from the group consisting of hydroxy, oxo, halogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy and hydroxy substituted C 1-4 alkyl;
- n is an integer from 0 to 2; provided that when n is 2, then m is 1;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl, pyrrolidin-3-yl, pyrrolidin-3R-yl, pyrrolidin-3S-yl, piperidin-3-yl, piperidin-3R-yl, piperidin-2S-yl, and piperidin-4-yl;
- a is an integer from 0 to 1;
- L 1 is selected from the group consisting of —C(O)—, —C(O)O—, —C(O)—NR L —, —C(S)—, —SO 2 —, —SO 2 —NR L —; wherein R L is selected from the group consisting of hydrogen and C 1-4 alkyl;
- R 3 is selected from the group consisting of C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, C 2-4 alkenyl, C 3-6 cycloalkyl, —(C 1-4 alkyl)-(C 3-6 cycloalkyl), 4 to 6-membered, saturated heterocyclyl, —(C 1-4 alkyl)-(4 to 6-membered, saturated heterocyclyl), —(C 2-4 alkenyl)-(5 to 6-membered, saturated heterocyclyl), 5 to 6-membered heteroaryl, —(C 1-4 alkyl)-(5 to 6-membered heteroaryl), —(C 2-4 alkenyl)-(5 to 6-membered heteroaryl), and NR V R W ; wherein R V and R W are each independently selected from the group consisting of hydrogen and C 1-4 alkyl;
- C 3-6 cycloalkyl, 4 to 6-membered saturated heterocyclyl or 5 to 6-membered heteroaryl, whether alone or as part of a substituent group, is optionally substituted with one to two substituents independently selected from the group consisting of halogen, hydroxy, cyano, C 1-4 alkyl, fluorinated C 1-4 alkyl, —(C 1-4 alkyl)-OH, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, and NR G R H ; wherein R G and R H are each independently selected from the group consisting of hydrogen and C 1-4 alkyl;
- b is an integer from 0 to 2;
- each R 4 is independently selected from the group consisting of hydroxy, halogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, cyano, and NR J R K ; wherein R J and R K are each independently selected from the group consisting of hydrogen and C 1-4 alkyl; provided that each R 4 group is bound to a carbon atom;
- b is an integer from 0 to 1;
- R 5 is selected from the group consisting of
- aryl selected from the group consisting of aryl, heteroaryl and partially unsaturated heterocyclyl
- c is an integer from 0 to 2;
- each R 6 is independently selected from the group consisting of hydroxy, oxo, halogen, cyano, nitro, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, —(C 1-4 alkyl)-CN, —(C 1-4 alkyl)-O—(C 1-4 alkyl), C 1-4 alkoxy, fluorinated C 1-4 alkoxy, —SO 2 —(C 1-4 alkyl), —NR M R N , —(C 1-4 alkyl)-NR P R Q , —C(O)—(C 1-4 alkyl), —C(O)-(fluorinated C 1-2 alkyl), —C(O)—NR M R N , —C(O)OH, —C(O)O—(C 1-4 alkyl), —NR M —C(O)H, —NR M —C(O)—(C 1-4 alkyl),
- R M and R N are each independently selected from the group consisting of hydrogen and C 1-4 alkyl
- R P and R Q are each independently selected from the group consisting of hydrogen and C 1-4 alkyl; alternatively R P and R Q are taken together with the nitrogen atom to which they are bound to form a 5 to 6-membered saturated heterocyclyl; such 5 to 6-membered saturated heterocyclyl is optionally substituted with a substituent selected from the group consisting of halogen, C 1-4 alkyl and fluorinated C 1-4 alkyl;
- d is an integer from 0 to 1;
- R 7 is selected from the group consisting of hydroxy, halogen, cyano, nitro, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, —NR R R S , —C(O)—NR R R S , —C(O)OH and —C(O)O—(C 1-4 alkyl); wherein R R and R S are each independently selected from the group consisting of hydrogen and C 1-4 alkyl;
- phenyl is selected from the group consisting of phenyl, 5 to 6-membered saturated heterocyclyl and 5 to 6-membered heteroaryl;
- e is an integer from 0 to 2;
- each R 8 is independently selected from the group consisting of hydroxy, halogen, cyano, nitro, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, —NR T R U , —C(O)—NR T R U , —C(O)OH, —C(O)O—(C 1-4 alkyl), —(C 1-4 alkyl)-NR T R U , C 3-5 cycloalkyl, —(C 1-2 alkyl)-(C 3-5 cycloalkyl), oxetanyl, —(C 1-2 alkyl)-oxetanyl, tetrahydofuranyl, —(C 1-2 alkyl)-tetrahydro-furanyl, tetrahydro-pyranyl and —(C 1-2 alkyl)-tetrahydro-
- R 1 and R 2 are taken together with the carbon atom to which they are bound to form 1-(methoxycarbonyl)-azetidin-3-yl, m is 1 and n is 0 or m is 0 and n is 1;
- -(L 1 ) a -R 3 is selected from the group consisting of —C(O)—CF 3 , —C(O)-cyclopropyl, —C(O)-(thiazol-2-yl), —C(O)OCH 3 or —SO 2 —CH 3 ,
- R 5 is other than quinolin-7-yl, benzofuran-5-yl, 1-methyl-indazol-5-yl, 1-methyl-pyrazol-4-yl, 4-(1-methyl-pyrazol-4-yl)-phenyl, 1,2,3,4,4a,8a-hexahydro-2-methyl-carbonyl-isoquinolin-6-yl) and 1,2,3,4-trihydro-2-methylcarbonyl-isoquinolin-2-yl;
- R 1 and R 2 are taken together with the carbon atom to which they are bound to form cyclopentyl; m is 1 and n is 0 or m is 0 and m is 1;
- pyrrolidin-3R-yl is pyrrolidin-3R-yl; -(L 1 ) a -R 3 is —C(O)-cyclopropyl;
- R 1 and R 2 are taken together with the carbon atom to which they are bound to form cyclopentyl; m is 1 and n is 0 or m is 0 and m is 1;
- pyrrolidin-3R-yl is pyrrolidin-3R-yl; -(L 1 ) a -R 3 is —SO 2 -pyrrolidin-1-yl;
- -(L 1 ) a -R 3 is selected from the group consisting of —C(O)-cyclopropyl, —C(O)-(1-methyl-cyclopropyl) and —C(O)-(1-hydroxy-cyclopropyl);
- R 4 b 0 or (R 4 ) b is selected from the group consisting of 2-fluoro and 2-methyl; then R 5 is other than 1-isopropylsulfonyl-phenyl, 1-methyl-indazol-5-yl, 1-isopropyl-indazol-5-yl, 1-oxetan-3-yl, indazol-5-yl, 1-methyl-pyrazol-4-yl, 4-methyl-7-bromo-quinolin-2-yl, 5-(2-hydroxy-2-methyl-propyl)-pyridin-2-yl, 6-isopropyl-pyridin-3-yl, 6-(1-cyanomethyl)-pyridin-3-yl, 6-(2-hydroxy-2-methyl-propyl)-pyridin-3-yl, 1,5-naphthyridin-3-yl, 3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl, 4-(1-isobutyl-pyra
- R 4 is 2-methyl; then R 5 is other 1-methyl-indazol-5-yl;
- -(L 1 ) a -R 3 is —C(O)-pyridin-3-yl
- (R 4 ) b is 2-methyl; then R 5 is other than 1-methyl-indazol-5-yl;
- R 5 is other than indazol-5-yl, benzofuran-5-yl, benzothien-5-yl, 1-methyl-indazol-5-yl, 4-(4-methylphenyl)phenyl or 4-(3-chlorophenyl)-phenyl;
- R 5 is other than 4-trifluoromethyl-phenyl, 1-methyl-pyrazol-4-yl, benzoxazol-5-yl, pyridin-4-yl or 4-(1-methyl-pyrazol-4-yl)-phenyl;
- R 1 and R 2 are taken together with the carbon atom to which they are bound to form cyclopropyl; m is 0 and n is 1 or m is 1 and n is 0;
- pyrrolidin-3R-yl is pyrrolidin-3R-yl; -(L 1 ) a -R 3 is —C(O)-cyclopropyl;
- R 5 is other than 5-chloro-pyridin-3-yl, 2-oxo-3,4-dihydro-quinolin-7-yl or 6-(4-methyl-piperazin-1-yl)-pyridin-3-yl;
- R 1 and R 2 are taken together with the carbon atom to which they are bound to form tetrahydrofuran-3,3-diyl or tetrahydropyran-4,4-diyl; m is an integer from 0 to 1 and n is 0 or m is 0 and n is an integer from 0 to 1;
- -(L 1 ) a -R 3 is selected from the group consisting of —C(O)-thiazol-2-yl, —C(O)—CF 3 , —C(O)OCH 3 and —SO 2 —CH 3 ;
- R 5 is other than quinolin-7-yl, 1-methyl-indazol-5-yl, benzofuran-5-yl or 4-(1-methyl-pyrazol-4-yl)-phenyl;
- the present invention is further directed to processes for the preparation of the compounds of formula (I), as described in more detail in the general synthesis schemes and examples below.
- the present invention is further directed to a product prepared according to any of the processes as described in the general synthesis schemes and examples below.
- the present invention is further directed to intermediates in the synthesis of the compounds of formula (I), including, but not limited to, compounds of formula (XVIII), compounds of formula (XXI), compounds of formula (XXIII), compounds of formula (XXV) and compounds of formula (XXVII), as described in more detail below.
- Illustrative of the invention is a pharmaceutical composition comprising, consisting of and/or consisting essentially of a pharmaceutically acceptable carrier and the product prepared according to the process described herein.
- An illustration of the invention is a pharmaceutical composition made by mixing the product prepared according to the process described herein and a pharmaceutically acceptable carrier.
- Illustrating the invention is a process for making a pharmaceutical composition comprising, consisting of, and/or consisting essentially of mixing the product prepared according to the process described herein and a pharmaceutically acceptable carrier.
- Exemplifying the invention are methods of treating a disorder mediated by inhibition of fatty acid synthase (FASN) enzyme (selected from the group consisting of cancer, obesity and related disorders, and liver related disorders, as defined below) comprising, consisting of, and/or consisting essentially of administering to a subject in need thereof a therapeutically effective amount of any of the compounds or pharmaceutical compositions described above.
- FASN fatty acid synthase
- the present invention is directed to a compound of formula (I) for use as a medicament.
- the present invention is directed to a compound of formula (I) for use in the treatment of a disorder mediated by inhibition of fatty acid synthase (FASN) enzyme (selected from the group consisting of cancer, obesity and related disorders, and liver related disorders, as defined below).
- the present invention is directed to a composition comprising a compound of formula (I) for the treatment of a disorder mediated by inhibition of fatty acid synthase (FASN) enzyme (selected from the group consisting of cancer, obesity and related disorders and liver related disorders, as herein below).
- Another example of the invention is the use of any of the compounds described herein in the preparation of a medicament for treating: (a) cancer, as defined below, (b) obesity or related disorder, (c) liver related disorder, in a subject in need thereof.
- the present invention is directed to a compound as described herein for use in a methods for treating a disorder selected from the group consisting of cancer, obesity and related disorders, and liver related disorders, as herein defined, in a subject in need thereof.
- the present invention is directed to compounds of formula (I)
- the compounds of the present invention are FASN inhibitors useful in the treatment of, for example, cancer. More particularly, the compounds of formula (I) of the present invention are useful in the treatment of FASN-mediated disorders including, but not limited to, (a) cancer, as herein defined, (b) obesity and related disorders and (c) liver related disorders, as herein defined.
- the present invention is directed to methods for the treatment of cancer comprising, consisting of, and/or consisting essentially of administering to a subjected in need thereof, a therapeutically effective amount of a compound of formula (I); wherein the cancer is selected from the group consisting of cancer of the breast, prostate, head, neck, skin, lung, ovary, endometrium, thyroid, colon, rectum, esophagus, stomach, kidney, liver, bladder, pancreas, brain, spinal cord, blood, and bone.
- the cancer is selected from the group consisting of breast, prostate, colon, lung, brain, spinal cord, ovary, endometrium, thyroid, kidney, and stomach.
- the cancer is selected from the group consisting of glioma, glioblastoma, leukemia, Bannayan-Zonana syndrome, Cowden disease, Lhermitte-Duclos disease, breast cancer, inflammatory breast cancer, Wilm's tumor, Ewing's sarcoma, Rhabdomyosarcoma, ependymoma, medulloblastoma, sarcoma, osteosarcoma, melanoma, giant cell tumor of bone, and giant cell tumor of thyroid.
- the present invention is directed to methods for the treatment of obesity or a related disorder comprising, consisting of, and/or consisting essentially of administering to a subjected in need thereof, a therapeutically effective amount of a compound of formula (I); wherein the obesity or related disorder is selected from the group consisting of obesity, overweight, weight gain, Type II diabetes mellitus, Syndrome X, appetite and/or satiety modulation.
- the obesity or related disorders is selected from the group consisting of obesity, Type II diabetes mellitus, Syndrome X, and appetite and/or satiety modulation, more preferably obesity or Type II diabetes mellitus.
- the present invention is directed to methods for the treatment of an liver related disorder comprising, consisting of, and/or consisting essentially of administering to a subjected in need thereof, a therapeutically effective amount of a compound of formula (I); wherein the liver related disorder is selected from the group consisting of dyslipidemia, elevated cholesterol levels, elevated LDL, decreased HDL, elevated triglicerides, fatty libver, non-alcoholic steatohepatitis (NASH), fatty liver, and/or non-alcoholic fatty liver disease (NAFLD).
- the liver related disorder is selected from dylipidemia or elevated cholestrol levels.
- the present invention is directed to a pharmaceutical composition comprising, consisting of, and/or consisting essentially of a pharmaceutically acceptable carrier and a compound of formula (I).
- the present invention is directed to a pharmaceutical composition made by mixing a compound of formula (I) and a pharmaceutically acceptable carrier.
- the present invention is directed to a process for making a pharmaceutical composition comprising mixing a compound of formula (I) and a pharmaceutically acceptable carrier.
- the present invention is directed to a method of treating a disorder mediated by inhibition of fatty acid synthase (FASN) enzyme, comprising, consisting of, and/or consisting essentially of administering to a subject in need thereof a therapeutically effective amount of the compound of formula (I).
- FASN fatty acid synthase
- the present invention is directed to a method of treating a disorder mediated by inhibition of fatty acid synthase (FASN) enzyme, wherein the disorder mediated by inhibition of fatty acid synthase (FASN) enzyme is a cancer selected from the group consisting of the breast, prostate, head, neck, skin, lung, ovary, endometrium, thyroid, colon, rectum, esophagus, stomach, kidney, liver, bladder, pancreas, brain, spinal cord, blood, and bone.
- FASN fatty acid synthase
- the present invention is directed to a method of treating a disorder mediated by inhibition of fatty acid synthase (FASN) enzyme, wherein the disorder mediated by inhibition of fatty acid synthase (FASN) enzyme is selected from the group consisting of obesity, overweight, weight gain, Type II diabetes mellitus, Syndrome X, and appetite or satiety modulation.
- FASN fatty acid synthase
- the present invention is directed to a method of treating a disorder mediated by inhibition of fatty acid synthase (FASN) enzyme, wherein the disorder mediated by inhibition of fatty acid synthase (FASN) enzyme is selected from the group consisting of dyslipidemia, elevated cholesterol levels, elevated LDL, decreased HDL, elevated triglicerides, fatty liver, non-alcoholic steatohepatitis (NASH), fatty liver and non-alcoholic fatty liver disease (NAFLD).
- FASN fatty acid synthase
- the present invention is directed to a method of treating (a) cancer of the breast, prostate, head, neck, skin, lung, ovary, endometrium, thyroid, colon, rectum, esophagus, stomach, kidney, liver, bladder, pancreas, brain, spinal cord, blood or bone; (b) obesity or a related disorder selected from the group consisting of obesity, overweight, weight gain, Type II diabetes mellitus, Syndrome X, and appetite or satiety modulation; or (c) a liver related disorders selected from the group consisting of dyslipidemia, elevated cholesterol levels, elevated LDL, decreased HDL, elevated triglicerides, fatty liver, non-alcoholic steatohepatitis (NASH), fatty liver and non-alcoholic fatty liver disease (NAFLD); comprising, consisting of, and/or consisting essentially of administering to a subject in need thereof, a therapeutically effective amount of the compound of formula (I).
- a method of treating (a) cancer of the breast, prostate, head, neck, skin
- the present invention is directed to a method of treating (a) cancer of the breast, prostate, head, neck, skin, lung, ovary, endometrium, thyroid, colon, rectum, esophagus, stomach, kidney, liver, bladder, pancreas, brain, spinal cord, blood or bone; (b) obesity or a related disorder selected from the group consisting of obesity, overweight, weight gain, Type II diabetes mellitus, Syndrome X, and appetite or satiety modulation; or (c) a liver related disorders selected from the group consisting of dyslipidemia, elevated cholesterol levels, elevated LDL, decreased HDL, elevated triglicerides, fatty liver, non-alcoholic steatohepatitis (NASH), fatty liver and non-alcoholic fatty liver disease (NAFLD); comprising, consisting of, and/or consisting essentially of administering to a subject in need thereof a therapeutically effective amount of a pharmaceutical composition comprising a compound of formula (I).
- a pharmaceutical composition comprising a compound of formula (I).
- the present invention is directed to the use of a compound formula (I) for the preparation of a medicament for treating: (a) cancer of the breast, prostate, head, neck, skin, lung, ovary, endometrium, thyroid, colon, rectum, esophagus, stomach, kidney, liver, bladder, pancreas, brain, spinal cord, blood or bone; (b) obesity or a related disorder selected from the group consisting of obesity, overweight, weight gain, Type II diabetes mellitus, Syndrome X, and appetite or satiety modulation; or (c) a liver related disorders selected from the group consisting of dyslipidemia, elevated cholesterol levels, elevated LDL, decreased HDL, elevated triglicerides, fatty liver, non-alcoholic steatohepatitis (NASH), fatty liver and non-alcoholic fatty liver disease (NAFLD); in a subject in need thereof.
- NASH non-alcoholic steatohepatitis
- NAFLD non-alcoholic fatty liver disease
- the present invention is directed to the use of a compound of formula (I), for use in a method for treating a disorder selected from the group consisting of (a) cancer of the breast, prostate, head, neck, skin, lung, ovary, endometrium, thyroid, colon, rectum, esophagus, stomach, kidney, liver, bladder, pancreas, brain, spinal cord, blood or bone; (b) obesity or a related disorder selected from the group consisting of obesity, overweight, weight gain, Type II diabetes mellitus, Syndrome X, and appetite or satiety modulation; or (c) a liver related disorders selected from the group consisting of dyslipidemia, elevated cholesterol levels, elevated LDL, decreased HDL, elevated triglicerides, fatty liver, non-alcoholic steatohepatitis (NASH), fatty liver and non-alcoholic fatty liver disease (NAFLD); in a subject in need thereof.
- a disorder selected from the group consisting of selected from the group consisting of (a) cancer of the breast, prostate,
- the present invention is directed to a compound of formula (I) for use as a medicament.
- the present invention is directed to a compound of formula (I) (as in claim 1 ) for use in the treatment of a disorder mediated by inhibition of fatty acid synthase (FASN) enzyme.
- the present invention is directed to a compound of formula (I), for use in the treatment of a disorder mediated by inhibition of fatty acid synthase (FASN) enzyme, selected from the group consisting of cancer of the breast, prostate, head, neck, skin, lung, ovary, endometrium, thyroid, colon, rectum, esophagus, stomach, kidney, liver, bladder, pancreas, brain, spinal cord, blood or bone.
- the present invention is directed to a compound of formula (I), for use in the treatment of a disorder mediated by inhibition of fatty acid synthase (FASN) enzyme, selected from (a) obesity and related disorders or (b) liver related disorders.
- the present invention is directed to a composition comprising, consisting of, and/or consisting essentially of a compound of formula (I) for use in the treatment of a disorder mediated by inhibition of fatty acid synthase (FASN) enzyme.
- a composition comprising, consisting of, and/or consisting essentially of a compound of formula (I) for use in the treatment of a disorder mediated by inhibition of fatty acid synthase (FASN) enzyme.
- FASN fatty acid synthase
- the present invention is directed to a composition
- a composition comprising, consisting of, and/or consisting essentially of compound of formula (I) for use in the treatment of a disorder mediated by inhibition of fatty acid synthase (FASN) enzyme selected from the group consisting of (a) cancer of the breast, prostate, head, neck, skin, lung, ovary, endometrium, thyroid, colon, rectum, esophagus, stomach, kidney, liver, bladder, pancreas, brain, spinal cord, blood or bone; (b) obesity or a related disorder selected from the group consisting of obesity, overweight, weight gain, Type II diabetes mellitus, Syndrome X, and appetite or satiety modulation; and (c) a liver related disorders selected from the group consisting of dyslipidemia, elevated cholesterol levels, elevated LDL, decreased HDL, elevated triglicerides, fatty liver, non-alcoholic steatohepatitis (NASH), fatty liver and non-alcoholic fatty liver disease (NAFLD).
- FASN
- the present invention is directed to compounds of formula (I)
- R 1 and R 2 are taken together with the carbon atom to which they are bound to form an optionally substituted ring structure selected from the group consisting of
- R 10 is selected from the group consisting of hydrogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, —CH 2 -(hydroxy substituted C 1-4 alkyl), —(C 2-4 alkyl)-O—(C 1-4 alkyl), —(C 1-4 alkyl)-phenyl, —C(O)—NR A R B , —C(O)—(C 1-3 alkyl)-NR A R B , —C(O)—(C 1-4 alkyl), —C(O)—(C 3-6 cycloalkyl), —C(O)-phenyl, —C(O)-(5 to 6-membered heteroaryl),
- Z 1 is selected from the group consisting of —CH 2 —, —O—, —N(R C )—, —S—, —S(O)— and —SO 2 —; wherein R A , R B and R C are each independently selected from the group consisting of hydrogen and C 1-4 alkyl;
- phenyl or 5 to 6-membered heteroaryl whether alone or as part of a substituent group is further optionally substituted with one to two substituents independently selected from the group consisting of halogen, hydroxy, cyano, NR A R B , C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy and fluorinated C 1-4 alkoxy;
- each R 11 is independently selected from the group consisting of hydroxy, oxo, halogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, hydroxy substituted C 1-4 alkyl, —(C 1-4 alkyl)-O—(C 1-4 alkyl), —(C 1-4 alkyl)-phenyl, -cyano, —NR D R E , —C(O)—NR D R E , —C(O)—(C 1-4 alkyl), —C(O)-phenyl, —C(O)-(5 to 6-membered heteroaryl),
- Z 2 is selected from the group consisting of —CH 2 —, —O—, —N(R C )—, —S—, —S(O)— and —SO 2 —; wherein R D , R E and R F are each independently selected from the group consisting of hydrogen and C 1-4 alkyl;
- phenyl or 5 to 6-membered heteroaryl whether alone or as part of a substituent group is further optionally substituted with one to two substituents independently selected from the group consisting of halogen, hydroxy, cyano, NR D R E , C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, and fluorinated C 1-4 alkoxy;
- R 12 is selected from the group consisting of hydroxy, oxo, halogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, and hydroxy substituted C 1-4 alkyl;
- n is an integer from 0 to 1;
- n is an integer from 0 to 1;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl, pyrrolidin-3-yl, pyrrolidin-3R-yl, pyrrolidin-3S-yl, and piperidin-4-yl;
- a is an integer from 0 to 1;
- L 1 is selected from the group consisting of —C(O)—, —C(O)—NR L —, —C(S)—, —SO 2 —, and —SO 2 —NR L —; wherein R L is selected from the group consisting of hydrogen and C 1-4 alkyl;
- R 3 is selected from the group consisting of C 1-4 alkyl, fluorinated C 1-4 alkyl, C 2-4 alkenyl, C 3-6 cycloalkyl, —(C 1-4 alkyl)-(C 3-6 cycloalkyl), 5 to 6-membered, saturated heterocyclyl, —(C 1-4 alkyl)-(5 to 6-membered, saturated heterocyclyl), —(C 2-4 alkenyl)-(5 to 6-membered, saturated heterocyclyl), 5 to 6-membered heteroaryl, —(C 1-4 alkyl)-(5 to 6-membered heteroaryl), and —(C 2-4 alkenyl)-(5 to 6-membered heteroaryl);
- C 3-6 cycloalkyl, 5 to 6-membered, saturated heterocyclyl or 5 to 6-membered heteroaryl, whether alone or as part of a substituent group, is optionally substituted with one to two substituents independently selected from the group consisting of halogen, hydroxy, cyano, C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, and NR G R H ; wherein R G and R H are each independently selected from the group consisting of hydrogen and C 1-4 alkyl;
- b is an integer from 0 to 2;
- each R 4 is independently selected from the group consisting of hydroxy, halogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, cyano, and NR J R K ; wherein R J and R K are each independently selected from the group consisting of hydrogen and C 1-4 alkyl; provided that each R 4 group is bound to a carbon atom;
- b is an integer from 0 to 1;
- R 5 is selected from
- aryl selected from the group consisting of aryl, heteroaryl, and partially unsaturated heterocyclyl
- c is an integer from 0 to 2;
- each R 6 is independently selected from the group consisting of hydroxy, halogen, cyano, nitro, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, —NR M R N , —(C 1-4 alkyl)-NR P R Q , —C(O)—(C 1-4 alkyl), —C(O)—NR M R N , —C(O)OH, —C(O)O—(C 1-4 alkyl), —NR M —C(O)H, —NR M —C(O)—(C 1-4 alkyl), and —NR M —SO 2 —(C 1-4 alkyl);
- R M and R N are each independently selected from the group consisting of hydrogen and C 1-4 alkyl
- R P and R Q are each independently selected from hydrogen or C 1-4 alkyl; alternatively R P and R Q are taken together with the nitrogen atom to which they are bound to form a 5 to 6-membered saturated heterocyclyl; such 5 to 6-membered saturated heterocyclyl is optionally substituted with a substituent selected from the group consisting of halogen, C 1-4 alkyl, and fluorinated C 1-4 alkyl;
- d is an integer from 0 to 1;
- R 7 is selected from the group consisting of hydroxy, halogen, cyano, nitro, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, —NR R R S , —C(O)—NR R R S , —C(O)OH and —C(O)O—(C 1-4 alkyl); wherein R R and R S are each independently selected from the group consisting of hydrogen and C 1-4 alkyl;
- e is an integer from 0 to 2;
- each R 8 is independently selected from the group consisting of hydroxy, halogen, cyano, nitro, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, —NR T R U , —C(O)—NR T R U , —C(O)OH, —C(O)O—(C 1-4 alkyl) and —(C 1-4 alkyl)-NR T R U ; wherein R T and R U are each independently selected from the group consisting of hydrogen and C 1-4 alkyl;
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form an optionally substituted ring structure selected from the group consisting of
- R 10 is selected from the group consisting of hydrogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, —CH 2 -(hydroxy substituted C 1-4 alkyl), —(C 2-4 alkenyl), —(C 1-4 alkyl)-phenyl, —(C 2 alkyl)-O—(C 1-4 alkyl), —C(O)O—(C 1-4 alkyl), —C(O)—(C 1-4 alkyl), —C(O)-(fluorinated C 1-2 alkyl), —C(O)—(C 3-6 cycloalkyl),
- R 11 is independently selected from the group consisting of hydroxy, oxo, halogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, hydroxy substituted C 1-4 alkyl, —(C 1-4 alkyl)-phenyl, -cyano, —NR D R E , —C(O)—NR D R E , —C(O)—(C 1-4 alkyl), —C(O)OH and —C(O)O—(C 1-4 alkyl);
- R 12 is selected from the group consisting of hydroxy, oxo, halogen, C 1-2 alkyl, CF 3 , C 1-2 alkoxy, —OCF 3 and hydroxy substituted C 1-2 alkyl;
- n is an integer from 0 to 2; provided that when n is 2, then m is 0;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl, pyrrolidin-3-yl, pyrrolidin-3R-yl, pyrrolidin-3S-yl, piperidin-3-yl, piperidin-3S-yl, piperidin-3R-yl and piperidin-4-yl;
- a 1;
- L 1 is selected from the group consisting of —C(O)—, —C(O)O—, —C(O)—NR L - and —SO 2 —; wherein R L is selected from the group consisting of hydrogen and methyl;
- R 3 is selected from the group consisting of C 1-4 alkyl, fluorinated C 1-2 alkyl, hydroxy substituted C 1-4 alkyl, C 2-4 alkenyl, C 3-6 cycloalkyl, 4 to 6-membered, saturated heterocyclyl, 5 to 6-membered heteroaryl and NR V R W ; wherein R V and R W are each independently selected from the group consisting of hydrogen and C 1-2 alkyl;
- C 3-6 cycloalkyl, 4 to 6-membered, saturated heterocyclyl or 5 to 6-membered heteroaryl is optionally substituted with one to two substituents independently selected from the group consisting of halogen, hydroxy, cyano, C 1-4 alkyl, fluorinated C 1-4 alkyl, —(C 1-2 alkyl)-OH, C 1-4 alkoxy, fluorinated C 1-4 alkoxy and NR G R H ; wherein R G and R H are each independently selected from the group consisting of hydrogen and C 1-4 alkyl;
- b is an integer from 0 to 1;
- R 4 is selected from the group consisting of, halogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy and NR J R K ; wherein R J and R K are each independently selected from the group consisting of hydrogen and C 1-2 alkyl; provided that the R 4 group is bound to a carbon atom;
- R 5 is selected from the group consisting of
- aryl selected from the group consisting of aryl, heteroaryl and partially unsaturated heterocyclyl
- c is an integer from 0 to 2;
- each R 6 is independently selected from the group consisting of hydroxy, oxo, halogen, cyano, nitro, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, cyano substituted (C 1-4 alkyl), —(C 1-2 alkyl)-O—(C 1-4 alkyl), C 1-4 alkoxy, fluorinated C 1-4 alkoxy, —SO 2 —(C 1-4 alkyl), —C(O)—(C 1-4 alkyl), —C(O)-(fluorinated C 1-2 alkyl), —C(O)OH, —C(O)O—(C 1-4 alkyl), —C(O)—NR M R N , —NR M R N , —NR M —C(O)H, —NR M —SO 2 —(C 1-4 alkyl), C 3-5 cycloalkyl, 1-cyano-(C 3-5
- R M and R N are each independently selected from the group consisting of hydrogen and C 1-4 alkyl;
- d is an integer from 0 to 1;
- R 7 is selected from the group consisting of hydroxy, halogen, cyano, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, C 1-4 alkoxy and fluorinated C 1-4 alkoxy;
- phenyl is selected from the group consisting of phenyl, 5 to 6-membered saturated heterocyclyl and 5 to 6-membered heteroaryl;
- e is an integer from 0 to 2;
- each R 8 is independently selected from the group consisting of hydroxy, halogen, cyano, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, —NR T R U , —C(O)—NR T R U , —C(O)OH, —C(O)O—(C 1-4 alkyl), —(C 1-4 alkyl)-NR T R U , C 3-5 cycloalkyl, —(C 1-2 alkyl)-(C 3-5 cycloalkyl), oxetanyl, and tetrahydro-furanyl; wherein R T and R U are each independently selected from the group consisting of hydrogen and C 1-4 alkyl;
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form an optionally substituted ring structure selected from the group consisting of
- R 10 is selected from the group consisting of hydrogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, —CH 2 -(hydroxy substituted C 1-4 alkyl), —(C 1-4 alkyl)-phenyl, —C(O)—NR A R B , —C(O)—(C 1-4 alkyl), —C(O)—(C 3-6 cycloalkyl),
- Z 1 is selected from the group consisting of —CH 2 —, —O— and —N(R C )—; and wherein R A , R B and R D are each independently selected from the group consisting of hydrogen and C 1-4 alkyl;
- R 11 is independently selected from the group consisting of hydroxy, oxo, halogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, hydroxy substituted C 1-4 alkyl, —(C 1-4 alkyl)-phenyl, -cyano, —NR D R E , —C(O)—NR D R E , —C(O)—(C 1-4 alkyl), —C(O)OH and —C(O)O—(C 1-4 alkyl);
- R 12 is selected from the group consisting of hydroxy, oxo, halogen, C 1-2 alkyl, CF 3 , C 1-2 alkoxy, —OCF 3 and hydroxy substituted C 1-2 alkyl;
- n is an integer from 0 to 1;
- n is an integer from 0 to 1;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl, pyrrolidin-3-yl, pyrrolidin-3R-yl, pyrrolidin-3S-yl and piperidin-4-yl;
- a 1;
- L 1 is selected from the group consisting of —C(O)—, —C(O)—NR L — and —SO 2 —; wherein R L is selected from the group consisting of hydrogen and methyl;
- R 3 is selected from the group consisting of C 2-4 alkenyl, C 3-6 cycloalkyl, 5 to 6-membered, saturated heterocyclyl and 5 to 6-membered heteroaryl;
- C 3-6 cycloalkyl, 5 to 6-membered, saturated heterocyclyl or 5 to 6-membered heteroaryl is optionally substituted with one to two substituents independently selected from the group consisting of halogen, hydroxy, cyano, C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy and NR G R H ; wherein R G and R H are each independently selected from the group consisting of hydrogen and C 1-4 alkyl;
- b is an integer from 0 to 1;
- R 4 is selected from the group consisting of, halogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy and NR J R K ; wherein R J and R K are each independently selected from the group consisting of hydrogen and C 1-2 alkyl; provided that the R 4 group is bound to a carbon atom;
- R 5 is selected from the group consisting of
- aryl selected from the group consisting of aryl, heteroaryl and partially unsaturated heterocyclyl
- c is an integer from 0 to 2;
- each R 6 is independently selected from the group consisting of hydroxy, halogen, cyano, nitro, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, —NR M R N , —C(O)—(C 1-4 alkyl), —C(O)—NR M R N , —C(O)OH, —C(O)O—(C 1-4 alkyl), —NR M —C(O)H and —NR M —SO 2 —(C 1-4 alkyl);
- R M and R N are each independently selected from the group consisting of hydrogen and C 1-4 alkyl
- d is an integer from 0 to 1;
- R 7 is selected from the group consisting of hydroxy, halogen, cyano, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, C 1-4 alkoxy and fluorinated C 1-4 alkoxy;
- e is an integer from 0 to 2;
- each R 8 is independently selected from the group consisting of hydroxy, halogen, cyano, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, —NR T R U , —C(O)—NR T R U , —C(O)OH, —C(O)O—(C 1-4 alkyl) and —(C 1-4 alkyl)-NR T R U ; wherein R T and R U are each independently selected from the group consisting of hydrogen and C 1-4 alkyl;
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form an optionally substituted ring structure selected from the group consisting of
- R 10 is selected from the group consisting of hydrogen, C 1-4 alkyl, C 2-4 alkenyl, —CH 2 -(hydroxy substituted C 1-2 alkyl), —CH 2 -(phenyl), —(C 2 alkyl)-O—(C 1-2 alkyl), —C(O)—(C 1-4 alkyl), —C(O)-(fluorinated C 1-2 alkyl), —C(O)-(cyclopropyl), —C(O)O—(C 1-4 alkyl), —C(O)—NR A R B , —SO 2 —(C 1-2 alkyl), wherein R A and R B are each independently selected from the group consisting of hydrogen and methyl;
- n is an integer from 0 to 2 provide that when n is 2, then m is 0
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl, pyrrolidin-3-yl, pyrrolidin-3R-yl, pyrrolidin-3S-yl, piperidin-3-yl, piperidin-3R-yl, piperidin-3S-yl, and piperidin-4-yl;
- a 1;
- L 1 is selected from the group consisting of —C(O)—, —C(O)O— and —SO 2 —;
- R 3 is selected from the group consisting of C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, fluorinated C 1-2 alkyl, C 2-4 alkenyl, C 3-5 cycloalkyl, 4 to 5-membered, saturated heterocyclyl, 5 to 6-membered heteroaryl and NR V R W ; wherein the C 3-5 cycloalkyl, 4 to 5-membered, saturated heterocyclyl or 5 to 6-membered heteroaryl is optionally substituted with a substituent selected from the group consisting of halogen, hydroxy, C 1-2 alkyl, (C 1-2 alkyl)-OH, fluorinated C 1-2 alkyl, cyano and NH 2 ; and wherein R V and R W are each independently selected from the group consisting of hydrogen and methyl;
- b is an integer from 0 to 1;
- R 4 is selected from the group consisting of halogen, C 1-2 alkyl and C 1-2 alkoxy;
- R 5 is selected from the group consisting of
- phenyl selected from the group consisting of phenyl, naphthyl, 5 to 6-membered heteroaryl, 9 to 10-membered heteroaryl and partially unsaturated 9 to 10-membered heterocyclyl;
- c is an integer from 0 to 2;
- each R 6 is independently selected from the group consisting of hydroxy, oxo, halogen, cyano, C 1-4 alkyl, fluorinated C 1-2 alkyl, hydroxy substituted C 1-4 alkyl, cyano-substituted C 1-2 alkyl, —(C 1-2 alkyl)-O—(C 1-2 alkyl), C 1-4 alkoxy, fluorinated C 1-2 alkoxy, —SO 2 —(C 1-4 alkyl), —CO 2 H, —C(O)O—(C 1-2 alkyl), —C(O)—(C 1-2 alkyl), —C(O)-(fluorinated C 1-2 alkyl), —C(O)—NR M R N , —NR M R N , —NR M —C(O)H, —NR M —SO 2 —(C 1-2 alkyl), C 3-5 cycloalkyl, 1-cyano-cyclopropyl,
- phenyl is selected from the group consisting of phenyl, 5 to 6-membered, saturated, nitrogen containing heterocylyl and 5 to 6-membered, nitrogen containing heteroaryl;
- e is an integer from 0 to 1;
- R 8 is selected from the group consisting of halogen, C 1-4 alkyl, C 3-5 cycloalkyl, —(C 1-2 alkyl)-(C 3-5 cycloalkyl) and oxetanyl;
- the present invention is directed to compounds of formula (I) wherein,
- R 1 and R 2 are taken together to form an optionally substituted ring structure selected from the group consisting of
- R 10 is selected from the group consisting of hydrogen, C 1-4 alkyl, —CH 2 -(hydroxy substituted C 1-2 alkyl), —CH 2 -(phenyl), —C(O)—(C 1-4 alkyl), —C(O)-(cyclopropyl) and —C(O)—NR A R B ; wherein R A and R B are each independently selected from the group consisting of hydrogen and methyl;
- n is an integer from 0 to 1;
- n is an integer from 0 to 1;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl, pyrrolidin-3R-yl, pyrrolidin-3S-yl and piperidin-4-yl;
- a 1;
- L 1 is selected from the group consisting of —C(O)— and —SO 2 —;
- R 3 is selected from the group consisting of C 2 alkenyl, C 3 cycloalkyl, 5-membered, saturated heterocyclyl and 5-membered heteroaryl; wherein the C 3 cycloalkyl, 5-membered, saturated heterocyclyl or 5-membered heteroaryl is optionally substituted with a substituent selected from the group consisting of halogen, C 1-2 alkyl, fluorinated C 1-2 alkyl and cyano;
- b is an integer from 0 to 1;
- R 4 is selected from the group consisting of halogen, C 1-2 alkyl and C 1-2 alkoxy;
- R 5 is selected from the group consisting of
- c is an integer from 0 to 2;
- each R 6 is independently selected from the group consisting of hydroxy, halogen, cyano, C 1-2 alkyl, fluorinated C 1-2 alkyl, C 1-2 alkoxy, fluorinated C 1-2 alkoxy, —NR M R N , —C(O)—(C 1-2 alkyl), —NR M —C(O)H and —NR M —SO 2 —(C 1-2 alkyl); and wherein R M and R N are each independently selected from the group consisting of hydrogen and C 1-2 alkyl;
- phenyl is selected from the group consisting of phenyl and 5 to 6-membered, nitrogen containing heteroaryl;
- e is an integer from 0 to 1;
- R 8 is selected from the group consisting of halogen and C 1-2 alkyl
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, piperidin-4,4-diyl, 1-(methyl)-piperidin-4,4-diyl, 1-(isopropyl)piperidin-4,4-diyl, 1-(ethenyl)piperidin-4,4-diyl, 1-(2-hydroxy-ethyl)-piperidin-4,4-diyl, 1-(methoxy-carbonyl)piperidin-4,4-diyl, 1-(benzyl)-piperidin-4,4-diyl, 1-(methyl-carbonyl)piperidin-4,4-diyl, 1-(isopropyl-carbonyl)-piperidin-4,4-diyl, 1-(trifluoromethyl-carbonyl)piperidin-4,4-diyl, 1-(cyclopropyl-carbonyl)-piperidin
- n is an integer from 0 to 2; provided that when n is 2 then m is 1;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl, pyrrolidin-3-yl, pyrrolidin-3R-yl, pyrrolidin-3S-yl, piperidin-3R-yl, piperidin-3S-yl and piperidin-4-yl;
- a 1;
- L 1 is selected from the group consisting of —C(O)—, —C(O)O— and —SO 2 —;
- R 3 is selected from the group consisting of methyl, ethyl, isopropyl, 1-hydroxyethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2-hydroxy-propan-2-yl. 3-hydroxy-2-methyl-propan-2-yl, ethenyl, cyclopropyl, 1-fluoro-cyclopropyl, 1-hydroxy-cyclopropyl, 1-hydroxymethyl-cyclopropyl, 1-methyl-cyclopropyl, 1-cyano-cyclopropyl, 1-amino-cyclopropyl, cyclobutyl, 1-methyl-cyclobutyl, amino, dimethylamino, pyrrolidin-1-yl, 1-methyl-pyrazol-3-yl, thiazol-2-yl, tetrahydro-furan-2-yl, tetrahydro-furan-2R-yl, oxetan-2-yl, oxetan-3-yl, 3-methyl
- b is an integer from 0 to 1;
- R 4 is selected from the group consisting of 2-fluoro, 3-fluoro, 2-chloro, 3-chloro, 2-methyl, 3-methyl and 2-methoxy;
- R 5 is selected from the group consisting of
- phenyl is selected from the group consisting of phenyl, pyridin-3-yl and pyridin-4-yl;
- the present invention is directed to compounds of formula (I) wherein,
- R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, piperidin-4,4-diyl, 1-(methyl)-piperidin-4,4-diyl, 1-(isopropyl)piperidin-4,4-diyl, 1-(2-hydroxy-ethyl)-piperidin-4,4-diyl, 1-(methoxy-carbonyl)piperidin-4,4-diyl, 1-(benzyl)piperidin-4,4-diyl, 1-(methyl-carbonyl)-piperidin-4,4-diyl, 1-(isopropyl-carbonyl)-piperidin-4,4-diyl, 1-(cyclopropyl-carbonyl)-piperidin-4,4-diyl and 1-(dimethylamino-carbonyl)-piperidin-4,4-diyl;
- n is an integer from 0 to 1;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl, pyrrolidin-3R-yl, pyrrolidin-3S-yl and piperidin-4-yl; a is 1; L 1 is selected from the group consisting of —C(O)— and —SO 2 —; R 3 is selected from the group consisting of 2,2,2-trifluoroethyl, ethenyl, cyclopropyl, 1-fluoro-cyclopropyl, 1-methyl-cyclopropyl, 1-cyano-cyclopropyl, pyrrolidin-1-yl, 1-methyl-pyrazol-3-yl and tetrahydro-furan-2-yl;
- R 4 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy
- R 5 is selected from the group consisting of
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, piperidin-4,4-diyl, 1-(methyl)-piperidin-4,4-diyl, 1-(isopropyl)-piperidin-4,4-diyl, 1-(2-hydroxy-ethyl)-piperidin-4,4-diyl, 1-(ethenylcarbonyl)-piperidin-4,4-diyl, 1-(trifluoromethyl-carbonyl)piperidin-4,4-diyl, 1-(methoxy-carbonyl)piperidin-4,4-diyl, 1-(2-methoxyethyl)-piperidin-4,4-diyl, 1-(benzyl)piperidin-4,4-diyl, 1-(methyl-carbonyl)-piperidin-4,4-diyl, 1-(isopropyl-carbonyl)
- n is an integer from 0 to 1;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl, pyrrolidin-3R-yl, pyrrolidin-3S-yl and piperidin-4-yl;
- a 1;
- L 1 is —C(O)—
- R 3 is selected from the group consisting of ethyl, 1-hydroxy-ethyl, isopropyl, 2-hydroxy-propan-2-yl, 3-hydroxy-2-methyl-propan-2-yl, 2,2,2-trifluoroethyl, ethenyl, cyclopropyl, 1-fluoro-cyclopropyl, 1-methyl-cyclopropyl, 1-hydroxy-cyclopropyl, 1-hydroxymethyl-cyclopropyl, 1-amino-cyclopropyl, cyclobutyl, 1-methyl-cyclobutyl, pyrrolidin-1-yl, 1-methyl-pyrazol-3-yl, oxetan-2-yl, oxetan-3yl, 3-methyl-oxetan-3-yl, tetrahydro-furan-2yl, tetrahydro-furan-2R-yl, tetrahydro-furan-2S-yl and dimethylamino;
- b is an integer from 0 to 1;
- R 4 is selected from the group consisting of 2-fluoro, 2-chloro, 2-methyl, 2-methoxy, 3-fluoro and 3-methyl;
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, piperidin-4,4-diyl, 1-(methyl)-piperidin-4,4-diyl, 1-(isopropyl)-piperidin-4,4-diyl, 1-(2-hydroxy-ethyl)-piperidin-4,4-diyl, 1-(methoxy-carbonyl)piperidin-4,4-diyl, 1-(benzyl)piperidin-4,4-diyl, 1-(methyl-carbonyl)-piperidin-4,4-diyl, 1-(isopropyl-carbonyl)-piperidin-4,4-diyl, 1-(cyclopropyl-carbonyl)-piperidin-4,4-diyl and 1-(dimethylamino-carbonyl)-piperidin-4,4-diyl;
- n is an integer from 0 to 1;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl, pyrrolidin-3R-yl, pyrrolidin-3S-yl and piperidin-4-yl; a is 1; L 1 is —C(O)—; R 3 is selected from the group consisting of 2,2,2-trifluoroethyl, ethenyl, cyclopropyl, 1-methyl-cyclopropyl, pyrrolidin-1-yl and 1-methyl-pyrazol-3-yl;
- b is an integer from 0 to 1;
- R 4 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, piperidin-4,4-diyl, 1-(methyl)-piperidin-4,4-diyl, 1-(isopropyl)piperidin-4,4-diyl, 1-(2-hydroxy-ethyl)-piperidin-4,4-diyl, 1-(methoxy-carbonyl)piperidin-4,4-diyl, 1-(benzyl)piperidin-4,4-diyl, 1-(methyl-carbonyl)-piperidin-4,4-diyl, 1-(isopropyl-carbonyl)-piperidin-4,4-diyl, 1-(cyclopropyl-carbonyl)-piperidin-4,4-diyl, 1-(dimethylamino-carbonyl)-piperidin-4,4-diyl, 1-(trifluoromethyl-carbon
- n is an integer from 0 to 1;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl, pyrrolidin-3R-yl and piperidin-4-yl;
- a 1;
- L 1 is —C(O)—
- R 3 is selected from the group consisting of ethyl, cyclopropyl, 1-hydroxy-cyclopropyl, 1-fluoro-cyclopropyl, 1-methyl-cyclopropyl, 1-hydroxymethyl-cyclopropyl, cyclobutyl, tetrahydro-furan-2-yl, tetrahydro-furan-2R-yl, tetrahydro-furan-2S-yl, and oxetan-2-yl;
- b is an integer from 0 to 1;
- R 4 is selected from the group consisting of 2-fluoro, 2-chloro, 2-methyl, 2-methoxy, 3-fluoro and 3-methyl;
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, piperidin-4,4-diyl, 1-(methyl)-piperidin-4,4-diyl, 1-(2-hydroxy-ethyl)-piperidin-4,4-diyl, 1-(methoxy-carbonyl)-piperidin-4,4-diyl, 1-(benzyl)-piperidin-4,4-diyl, 1-(methyl-carbonyl)-piperidin-4,4-diyl, 1-(isopropyl-carbonyl)piperidin-4,4-diyl, 1-(cyclopropyl-carbonyl)-piperidin-4,4-diyl and 1-(dimethylamino-carbonyl)-piperidin-4,4-diyl;
- n is an integer from 0 to 1;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl, pyrrolidin-3R-yl and piperidin-4-yl; a is 1; L 1 is —C(O)—; R 3 is selected from the group consisting of cyclopropyl and 1-methyl-cyclopropyl;
- b is an integer from 0 to 1;
- R 4 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy; R 5 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, 1-(methoxy-carbonyl)-piperidin-4,4-diyl, 1-(isopropyl-carbonyl)-piperidin-4,4-diyl, and 1-(dimethylamino-carbonyl)-piperidin-4,4-diyl;
- n is 0;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl and pyrrolidin-3R-yl;
- a 1;
- L 1 is —C(O)—
- R 3 is selected from the group consisting of cyclopropyl, 1-fluoro-cyclopropyl, 1-hydroxy-cyclopropyl, 1-methyl-cyclopropyl, tetrahydrfuran-2S-yl and oxetan-2-yl;
- b is an integer from 0 to 1;
- R 4 is selected from the group consisting of 2-fluoro, 2-chloro and 2-methyl
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, 1-(methoxy-carbonyl)-piperidin-4,4-diyl, 1-(isopropyl-carbonyl)-piperidin-4,4-diyl, and 1-(dimethylamino-carbonyl)-piperidin-4,4-diyl;
- m is an integer from 0 to 1;
- n is 0;
- R 3 is selected from the group consisting of cyclopropyl and 1-methyl-cyclopropyl;
- R 4 is selected from the group consisting of 2-fluoro and 2-methyl;
- R 5 is
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl and cyclopentyl;
- n is 0;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl and pyrrolidin-3R-yl;
- a 1;
- L 1 is —C(O)—
- R 3 is selected from the group consisting of cyclopropyl, 1-hydroxy-cyclopropyl, 1-methyl-cyclopropyl and oxetan-2-yl;
- b is an integer from 0 to 1;
- R 4 is selected from the group consisting of 2-fluoro and 2-methyl
- R 5 is selected from the group consisting of
- naphtha-2-yl is selected from the group consisting of naphtha-2-yl, 6-chloro-naphth-2-yl, 6-fluoro-naphth-2-yl, 6-methyl-naphth-2-yl, 6-methoxy-naphth-2-yl, 6-cyano-naphth-2-yl, indol-5-yl, indol-6-yl, 1-methyl-indol-5-yl, 2-methyl-indol-5-yl, 2-hydroxymethyl-indol-5-yl, 3-(2-hydroxyethyl)-indol-5-yl, 3-cyanomethyl-indol-5-yl, indazol-5-yl, indazol-6-yl, 1-methyl-indazol-5-yl, quinolin-7-yl, 3-chloro-quinolin-7-yl, 6-fluoro-quinolin-2-yl, 8-fluoro
- pyridin-4-yl is selected from the group consisting of pyridin-4-yl and 1-methyl-pyrazol-4-yl;
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, 1-(methyl)-piperidin-4,4-diyl, 1-(methoxy-carbonyl)-piperidin-4,4-diyl and 1-(benzyl)piperidin-4,4-diyl;
- m is an integer from 0 to 1;
- n is 0;
- azetidin-3-yl and pyrrolidin-3R-yl is selected from the group consisting of azetidin-3-yl and pyrrolidin-3R-yl; a is 1; L 1 is —C(O)—; R 3 is cyclopropyl;
- b is an integer from 0 to 1; R 4 is 2-methyl; R 5 is
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl and cyclopentyl; m is an integer from 0 to 1; n is 0;
- azetidin-3-yl and pyrrolidin-3R-yl is selected from the group consisting of azetidin-3-yl and pyrrolidin-3R-yl; a is 1; L 1 is —C(O)—; R 3 is cyclopropyl;
- R 5 is phenyl
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl and tetrahydropyran-4,4-diyl;
- n is 0;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl and pyrrolidin-3R-yl;
- a 1;
- L 1 is —C(O)—
- R 3 is selected from the group consisting of cyclopropyl, 1-fluoro-cyclopropyl, 1-hydroxy-cyclopropyl, 1-methyl-cyclopropyl, tetrahydrofuran-2-yl, tetrahydrofuran-2S-yl and oxetan-2-yl;
- b is an integer from 0 to 1;
- R 4 is selected from the group consisting of 2-fluoro and 2-methyl
- R 5 is selected from the group consisting of
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl and cyclopentyl; m is an integer from 0 to 1; and n is 0;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl and pyrrolidin-3R-yl;
- a 1;
- L 1 is —C(O)—
- R 3 is selected from the group consisting of cyclopropyl, 1-fluoro-cyclopropyl, 1-hydroxy-cyclopropyl, 1-methyl-cyclopropyl, 1-methyl-cyclobutyl, tetrahydrofuran-2-yl, tetrahydrofuran-2S-yl and oxetan-2-yl;
- b is an integer from 0 to 1;
- R 4 is selected from the group consisting of 2-fluoro, 2-chloro and 2-methyl
- R 5 is selected from the group consisting of
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form cyclopropyl
- n is 0;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl and pyrrolidin-3R-yl;
- a 1;
- L 1 is —C(O)—
- R 3 is cyclopropyl
- indol-5-yl is selected from the group consisting of indol-5-yl, indol-6-yl, indazol-4-yl, indazol-5-yl, 1-methyl-indazol-5-yl, benzthiazol-5-yl, benzofuran-5-yl, benzothien-5-yl and 6-cyano-naphth-2-yl;
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, tetrahydro-furan-3,3-diyl, tetrahydro-pyran-4,4-diyl, 1-(methoxycarbonyl)-azetidin-3,3-diyl, piperidin-4,4-diyl, 1-(isopropylcarbonyl)-piperidin-4,4-diyl, 1-(2-hydroxyethyl)-piperidin-4,4-diyl, 1-(dimethylamino-methylcarbonyl)-piperidin-4,4-diyl, 1-(methylsulfonyl)piperidin-4,4-diyl and 1-(cyclopropylcarbonyl)-piperidin-4,4-diyl; m is an integer from 0 to 2; and n is an integer from 0 to 1; provided that when
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl, pyrrolidin-3R-yl, pyrrolidin-3R-yl, piperidin-3R-yl, and piperidin-4-yl;
- a 1;
- L 1 is selected from the group consisting of —C(O)—, —C(O)O— and —SO 2 —;
- R 3 is selected from the group consisting of methyl, 1-hydroxyethyl, trifluoromethyl, cyclopropyl, 1-methyl-cyclopropyl, 1-hydroxy-cyclopropyl, tetrahydro-furan-2R-yl, pyrrolidin-1-yl and thiazol-2-yl;
- b is an integer from 0 to 1;
- R 4 is selected from the group consisting of 2-fluoro and 2-methyl
- phenyl is selected from the group consisting of phenyl, pyridin-3-yl, pyridin-4-yl and pyrazol-4-yl;
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl and cyclopentyl; n is an integer from 0 to 1; m is an integer from 0 to 1;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl, pyrrolidin-3R-yl and piperidin-4-yl; a is 1; L 1 is —C(O)—; R 3 is cyclopropyl;
- R 5 is phenyl
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl and cyclopentyl;
- n is 0;
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl and pyrrolidin-3R-yl;
- a 1;
- L 1 is —C(O)—
- R 3 is selected from the group consisting of cyclopropyl, 1-hydroxy-cyclopropyl and 1-methyl-cyclopropyl;
- b is an integer from 0 to 1;
- R 4 is selected from the group consisting of 2-fluoro and 2-methyl
- the present invention is directed to compounds of formula (I) wherein
- R 1 and R 2 are taken together to form cyclopropyl; m is an integer from 0 to 1; n is 0;
- azetidin-3-yl and pyrrolidin-3R-yl is selected from the group consisting of azetidin-3-yl and pyrrolidin-3R-yl; a is 1; L 1 is —C(O)—; R 3 is cyclopropyl;
- R 5 is phenyl
- the present invention is directed to compounds of formula (I) wherein R 1 and R 2 are taken together to form an optionally substituted ring structure selected from the group consisting of (a) C 3-6 cycloalkyl; wherein the C 3-8 cycloalkyl is optionally substituted with one R 11 group; (b) benzo-fused C 5-6 cycloalkyl; wherein the benzo-fused C 5-6 cycloalkyl is bound through a carbon atom of the C 5-6 cycloalkyl portion of the ring structure; and wherein the benzo-fused C 5-6 cycloalkyl is optionally substituted with one R 11 group; and (c) 4 to 8-membered, saturated heterocyclyl; wherein the 4 to 8-membered, saturated heterocyclyl contains O or NR 10 ; provided that the O or NR 10 is not present at the 2-position relative to the carbon atom of the imidazolin-5-one; and wherein the 4 to 8-membere
- the present invention is directed to compounds of formula (I) wherein R 1 and R 2 are taken together to form an optionally substituted ring structure selected from the group consisting of (a) C 3-6 cycloalkyl; and (c) 4 to 6-membered, saturated heterocyclyl; wherein the 4 to 6-membered saturated heterocyclyl contains NR 10 ; provided that the NR 10 is not present at the 2-position relative to the carbon atom of the imidazolidin-5-one.
- the present invention is directed to compounds of formula (I) wherein R 1 and R 2 are taken together to form an optionally substituted ring structure selected from the group consisting of (a) C 3-6 cycloalkyl; wherein the C 3-8 cycloalkyl is optionally substituted with one R 11 group; (b) benzo-fused C 5-6 cycloalkyl; wherein the benzo-fused C 5-6 cycloalkyl is bound through a carbon atom of the C 5-6 cycloalkyl portion of the ring structure; and wherein the benzo-fused C 5-6 cycloalkyl is optionally substituted with one R 11 group; and (c) 4 to 6-membered, saturated heterocyclyl; wherein the 4 to 6-membered, saturated heterocyclyl contains O or NR 10 ; provided that the O or NR 10 is not present at the 2-position relative to the carbon atom of the imidazolin-5-one; and wherein the 4 to 6-membered, saturated hetero
- the present invention is directed to compounds of formula (I) wherein R 1 and R 2 are taken together to form an optionally substituted ring structure selected from the group consisting of (a) C 3-6 cycloalkyl; and (c) 4 to 6-membered, saturated heterocyclyl; wherein the 4 to 6-membered saturated heterocyclyl contains NR 10 ; provided that the NR 10 is not present at the 2-position relative to the carbon atom of the imidazolidin-5-one.
- the present invention is directed to compounds of formula (I) wherein R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, piperidin-4,4-diyl, 1-(methyl)piperidin-4,4-diyl, 1-(isopropyl)piperidin-4,4-diyl, 1-(ethenyl)piperidin-4,4-diyl, 1-(2-hydroxy-ethyl)-piperidin-4,4-diyl, 1-(methoxy-carbonyl)-piperidin-4,4-diyl, 1-(benzyl)piperidin-4,4-diyl, 1-(methyl-carbonyl)-piperidin-4,4-diyl, 1-(isopropyl-carbonyl)-piperidin-4,4-diyl, 1-(trifluoromethyl-carbonyl)-piperidin-4,4-di
- the present invention is directed to compounds of formula (I) wherein R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, piperidin-4,4-diyl, 1-(methyl)piperidin-4,4-diyl, 1-(isopropyl)-piperidin-4,4-diyl, 1-(2-hydroxy-ethyl)-piperidin-4,4-diyl, 1-(ethenylcarbonyl)-piperidin-4,4-diyl, 1-(trifluoromethyl-carbonyl)piperidin-4,4-diyl, 1-(methoxy-carbonyl)-piperidin-4,4-diyl, 1-(2-methoxyethyl)-piperidin-4,4-diyl, 1-(benzyl)piperidin-4,4-diyl, 1-(methyl-carbonyl)-piperidin-4,4-diy
- the present invention is directed to compounds of formula (I) wherein R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, piperidin-4,4-diyl, 1-(methyl)piperidin-4,4-diyl, 1-(isopropyl)-piperidin-4,4-diyl, 1-(2-hydroxy-ethyl)-piperidin-4,4-diyl, 1-(methoxy-carbonyl)piperidin-4,4-diyl, 1-(benzyl)-piperidin-4,4-diyl, 1-(methyl-carbonyl)piperidin-4,4-diyl, 1-(isopropyl-carbonyl)-piperidin-4,4-diyl, 1-(cyclopropyl-carbonyl)-piperidin-4,4-diyl, 1-(dimethylamino-carbonyl)-piperidin
- the present invention is directed to compounds of formula (I) wherein R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, tetrahydro-furan-3,3-diyl, tetrahydro-pyran-4,4-diyl, 1-(methoxycarbonyl)-azetidin-3,3-diyl, piperidin-4,4-diyl, 1-(isopropylcarbonyl)-piperidin-4,4-diyl, 1-(2-hydroxyethyl)-piperidin-4,4-diyl, 1-(dimethylamino-methylcarbonyl)-piperidin-4,4-diyl, 1-(methylsulfonyl)piperidin-4,4-diyl, and 1-(cyclopropylcarbonyl)-piperidin-4,4-diyl.
- R 1 and R 2 are taken together to form
- the present invention is directed to compounds of formula (I) wherein R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, piperidin-4,4-diyl, 1-(methyl)piperidin-4,4-diyl, 1-(isopropyl)piperidin-4,4-diyl, 1-(2-hydroxy-ethyl)-piperidin-4,4-diyl, 1-(methoxy-carbonyl)piperidin-4,4-diyl, 1-(benzyl)-piperidin-4,4-diyl, 1-(methyl-carbonyl)piperidin-4,4-diyl, 1-(isopropyl-carbonyl)-piperidin-4,4-diyl, 1-(cyclopropyl-carbonyl)-piperidin-4,4-diyl, and 1-(dimethylamino-carbonyl)-piperidin
- the present invention is directed to compounds of formula (I) wherein R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, piperidin-4,4-diyl, 1-(methyl)piperidin-4,4-diyl, 1-(2-hydroxy-ethyl)-piperidin-4,4-diyl, 1-(methoxy-carbonyl)piperidin-4,4-diyl, 1-(benzyl)piperidin-4,4-diyl, 1-(methyl-carbonyl)-piperidin-4,4-diyl, 1-(isopropyl-carbonyl)-piperidin-4,4-diyl, 1-(cyclopropyl-carbonyl)-piperidin-4,4-diyl, and 1-(dimethylamino-carbonyl)-piperidin-4,4-diyl.
- R 1 and R 2 are taken together to form a
- the present invention is directed to compounds of formula (I) wherein R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, 1-(methoxy-carbonyl)-piperidin-4,4-diyl, 1-(isopropyl-carbonyl)piperidin-4,4-diyl, and 1-(dimethylamino-carbonyl)piperidin-4,4-diyl.
- the present invention is directed to compounds of formula (I) wherein R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, 1-(methyl)-piperidin-4,4-diyl, 1-(methoxy-carbonyl)piperidin-4,4-diyl, and 1-(benzyl)-piperidin-4,4-diyl.
- the present invention is directed to compounds of formula (I) wherein R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl, cyclopentyl, and tetrahydropyran-4,4-diyl.
- the present invention is directed to compounds of formula (I) wherein R 1 and R 2 are taken together to form a ring structure selected from the group consisting of cyclopropyl and cyclopentyl. In another preferred embodiment, the present invention is directed to compounds of formula (I) wherein R 1 and R 2 are taken together to form cyclopropyl.
- the present invention is directed to compounds of formula (I) wherein R 1 ° is selected from the group consisting of hydrogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, —CH 2 -(hydroxy substituted C 1-4 alkyl), —(C 1-4 alkyl)-phenyl, —C(O)—NR A R B , —C(O)—(C 1-4 alkyl), —C(O)—(C 3-6 cycloalkyl),
- Z 1 is selected from the group consisting of —CH 2 —, —O— and —N(R C )—; and wherein R A , R B and R C are each independently selected from the group consisting of hydrogen and C 1-4 alkyl.
- the present invention is directed to compounds of formula (I) wherein R 1 ° is selected from the group consisting of hydrogen, C 1-4 alkyl, —CH 2 -(hydroxy substituted C 1-2 alkyl), —CH 2 -(phenyl), —C(O)—(C 1-4 alkyl), —C(O)-(cyclopropyl) and —C(O)—NR A R B ; wherein R A and R B are each independently selected from the group consisting of hydrogen and methyl.
- the present invention is directed to compounds of formula (I) wherein R 10 is selected from the group consisting of hydrogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, —CH 2 -(hydroxy substituted C 1-4 alkyl), —(C 2-4 alkenyl), —(C 1-4 alkyl)-phenyl, —(C 2 alkyl)-O—(C 1-4 alkyl), —C(O)O—(C 1-4 alkyl), —C(O)—(C 1-4 alkyl), —C(O)—(C 1-4 alkyl), —C(O)-(fluorinated C 1-2 alkyl), —C(O)—(C 3-6 cycloalkyl),
- the present invention is directed to compounds of formula (I) wherein wherein R 10 is selected from the group consisting of hydrogen, C 1-4 alkyl, C 2-4 alkenyl, —CH 2 -(hydroxy substituted C 1-2 alkyl), —CH 2 -(phenyl), —(C 2 alkyl)-O—(C 1-2 alkyl), —C(O)—(C 1-4 alkyl), —C(O)-(fluorinated C 1-2 alkyl), —C(O)-(cyclopropyl), —C(O)O—(C 1-4 alkyl), —C(O)—NR A R B , —SO 2 —(C 1-2 alkyl), wherein R A and R B are each independently selected from the group consisting of hydrogen and methyl.
- the present invention is directed to compounds of formula (I) wherein R 11 is independently selected from the group consisting of hydroxy, oxo, halogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, hydroxy substituted C 1-4 alkyl, —(C 1-4 alkyl)-phenyl, -cyano, —NR D R E , —C(O)—NR D R E , —C(O)—(C 1-4 alkyl), —C(O)OH and —C(O)O—(C 1-4 alkyl); wherein R 12 is selected from the group consisting of hydroxy, oxo, halogen, C 1-2 alkyl, CF 3 , C 1-2 alkoxy, —OCF 3 and hydroxy substituted C 1-2 alkyl.
- the present invention is directed to compounds of formula (I) wherein R 11 is independently selected from the group consisting of hydroxy, oxo, halogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, hydroxy substituted C 1-4 alkyl, —(C 1-4 alkyl)-phenyl, -cyano, —NR D R E , —C(O)—NR D R E , —C(O)—(C 1-4 alkyl), —C(O)OH and —C(O)O—(C 1-4 alkyl).
- the present invention is directed to compounds of formula (I) wherein R 12 is selected from the group consisting of hydroxy, oxo, halogen, C 1-2 alkyl, CF 3 , C 1-2 alkoxy, —OCF 3 and hydroxy substituted C 1-2 alkyl.
- R 12 is selected from the group consisting of —OH, oxo, —Cl, —F, —CH 3 , CF 3 , —OCH 3 , —OCF 3 , —CH 2 —OH and —CH 2 CH 2 —OH.
- the present invention is directed to compounds of formula (I) wherein m is an integer from 0 to 1; and n is an integer from 0 to 2; provided that when n is 2, then m is 0.
- the present invention is directed to compounds of formula (I) wherein m is 0. In another preferred embodiment, the present invention is directed to compounds of formula (I) wherein m is 1.
- the present invention is directed to compounds of formula (I) wherein n is 0. In another preferred embodiment, the present invention is directed to compounds of formula (I) wherein n is 1. In another preferred embodiment, the present invention is directed to compounds of formula (I) wherein n is 2.
- the present invention is directed to compounds of formula (I) wherein m is 0 and n is 0. In a preferred embodiment, the present invention is directed to compounds of formula (I) wherein m is 1 and n is 1. In a preferred embodiment, the present invention is directed to compounds of formula (I) wherein m is 1 and n is 0 or alternatively, m is 0 and n is 1. In another preferred embodiment, the present invention is directed to compounds of formula (I) wherein m is 0 and n is 2.
- the present invention is directed to compounds of formula (I) wherein is
- azetidin-3-yl selected from the group consisting of azetidin-3-yl, pyrrolidin-3-yl, pyrrolidin-3R-yl, pyrrolidin-3S-yl, piperidin-3-yl, piperidin-3S-yl, piperidin-3R-yl and piperidin-4-yl.
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- azetidin-3-yl is selected from the group consisting of azetidin-3-yl and pyrrolidin-3R-yl.
- the present invention is directed to compounds of formula (I) wherein a is 1. In another preferred embodiment, the present invention is directed to compounds of formula (I) wherein a is O.
- the present invention is directed to compounds of formula (I) wherein L 1 is selected from the group consisting of —C(O)—, —C(O)O—, —C(O)—NR L — and —SO 2 —; wherein R L is selected from the group consisting of hydrogen and methyl.
- the present invention is directed to compounds of formula (I) wherein L 1 is selected from the group consisting of —C(O)—, —C(O)O— and —SO 2 —.
- the present invention is directed to compounds of formula (I) wherein L 1 is selected from the group consisting of —C(O)—, —C(O)—NR L — and —SO 2 —; wherein R L is selected from the group consisting of hydrogen and methyl.
- the present invention is directed to compounds of formula (I) wherein L 1 is selected from the group consisting of —C(O)— and —SO 2 —.
- the present invention is directed to compounds of formula (I) wherein L 1 is —C(O)—.
- the present invention is directed to compounds of formula (I) wherein R 3 is selected from the group consisting of C 1-4 alkyl, fluorinated C 1-2 alkyl, hydroxy substituted C 1-4 alkyl, C 2-4 alkenyl, C 3-6 cycloalkyl, 4 to 6-membered, saturated heterocyclyl, 5 to 6-membered heteroaryl and NR V R W ; wherein R V and R W are each independently selected from the group consisting of hydrogen and C 1-2 alkyl; wherein the C 3-6 cycloalkyl, 4 to 6-membered, saturated heterocyclyl or 5 to 6-membered heteroaryl, is optionally substituted with one to two substituents independently selected from the group consisting of halogen, hydroxy, cyano, C 1-4 alkyl, fluorinated C 1-4 alkyl, —(C 1-2 alkyl)-OH, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, and NR G R H
- the present invention is directed to compounds of formula (I) wherein R 3 is selected from the group consisting of C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, fluorinated C 1-2 alkyl, C 2-4 alkenyl, C 3-5 cycloalkyl, 4 to 5-membered, saturated heterocyclyl, 5 to 6-membered heteroaryl and NR V R W ; wherein the C 3-5 cycloalkyl, 4 to 5-membered, saturated heterocyclyl or 5 to 6-membered heteroaryl is optionally substituted with a substituent selected from the group consisting of halogen, hydroxy, C 1-2 alkyl, (C 1-2 alkyl)-OH, fluorinated C 1-2 alkyl, cyano and NH 2 ; and wherein R V and R W are each independently selected from the group consisting of hydrogen and methyl.
- the present invention is directed to compounds of formula (I) wherein R 3 is selected from the group consisting of C 2-4 alkenyl, C 3-6 cycloalkyl, 5 to 6-membered, saturated heterocyclyl and 5 to 6-membered heteroaryl; wherein the C 3-6 cycloalkyl, 5 to 6-membered, saturated heterocyclyl or 5 to 6-membered heteroaryl, is optionally substituted with one to two substituents independently selected from the group consisting of halogen, hydroxy, cyano, C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy and NR G R H ; wherein R G and R H are each independently selected from the group consisting of hydrogen and C 1-4 alkyl.
- the present invention is directed to compounds of formula (I) wherein R 3 is selected from the group consisting of C 2 alkenyl, C 3 cycloalkyl, 5-membered, saturated heterocyclyl and 5-membered heteroaryl; wherein the C 3 cycloalkyl, 5-membered, saturated heterocyclyl or 5-membered heteroaryl is optionally substituted with a substituent selected from the group consisting of halogen, C 1-2 alkyl, fluorinated C 1-2 alkyl and cyano.
- the present invention is directed to compounds of formula (I) wherein R 3 is selected from the group consisting of methyl, ethyl, isopropyl, 1-hydroxyethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2-hydroxy-propan-2-yl.
- the present invention is directed to compounds of formula (I) wherein R 3 is selected from the group consisting of ethyl, 1-hydroxy-ethyl, isopropyl, 2-hydroxy-propan-2-yl, 3-hydroxy-2-methyl-propan-2-yl, 2,2,2-trifluoroethyl, ethenyl, cyclopropyl, 1-fluoro-cyclopropyl, 1-methyl-cyclopropyl, 1-hydroxy-cyclopropyl, 1-hydroxymethyl-cyclopropyl, 1-amino-cyclopropyl, cyclobutyl, 1-methyl-cyclobutyl, pyrrolidin-1-yl, 1-methyl-pyrazol-3-yl, oxetan-2-yl, oxetan-3yl, 3-methyl-oxetan-3-yl, tetrahydro-furan-2yl, tetrahydro-furan-2R-yl, tetrahydro-fur
- the present invention is directed to compounds of formula (I) wherein R 3 is selected from the group consisting of 2,2,2-trifluoroethyl, ethenyl, cyclopropyl, 1-fluoro-cyclopropyl, 1-methyl-cyclopropyl, 1-cyano-cyclopropyl, pyrrolidin-1-yl, 1-methyl-pyrazol-3-yl and tetrahydro-furan-2-yl.
- the present invention is directed to compounds of formula (I) wherein R 3 is selected from the group consisting of 2,2,2-trifluoroethyl, ethenyl, cyclopropyl, 1-methyl-cyclopropyl, pyrrolidin-1-yl and 1-methyl-pyrazol-3-yl.
- the present invention is directed to compounds of formula (I) wherein R 3 is selected from the group consisting of ethyl, cyclopropyl, 1-hydroxy-cyclopropyl, 1-fluoro-cyclopropyl, 1-methyl-cyclopropyl, 1-hydroxymethyl-cyclopropyl, cyclobutyl, tetrahydro-furan-2-yl, tetrahydro-furan-2R-yl, tetrahydro-furan-2S-yl, and oxetan-2-yl.
- the present invention is directed to compounds of formula (I) wherein R 3 is selected from the group consisting of cyclopropyl, 1-fluoro-cyclopropyl, 1-hydroxy-cyclopropyl, 1-methyl-cyclopropyl, tetrahydrfuran-2S-yl and oxetan-2-yl.
- R 3 is selected from the group consisting of cyclopropyl, 1-fluoro-cyclopropyl, 1-hydroxy-cyclopropyl, 1-methyl-cyclopropyl, tetrahydrofuran-2-yl, tetrahydrofuran-2S-yl and oxetan-2-yl.
- the present invention is directed to compounds of formula (I) wherein R 3 is selected from the group consisting of methyl, 1-hydroxyethyl, trifluoromethyl, cyclopropyl, 1-methyl-cyclopropyl, 1-hydroxy-cyclopropyl, tetrahydro-furan-2R-yl, pyrrolidin-1-yl and thiazol-2-yl.
- the present invention is directed to compounds of formula (I) wherein R 3 is selected from the group consisting of cyclopropyl, 1-hydroxy-cyclopropyl, 1-methyl-cyclopropyl and oxetan-2-yl. In another preferred embodiment, the present invention is directed to compounds of formula (I) wherein R 3 is selected from the group consisting of cyclopropyl, 1-hydroxy-cyclopropyl and 1-methyl-cyclopropyl. In another preferred embodiment, the present invention is directed to compounds of formula (I) wherein R 3 is selected from the group consisting of cyclopropyl and 1-methyl-cyclopropyl. In another preferred embodiment, the present invention is directed to compounds of formula (I) wherein R 3 is cyclopropyl.
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- substituent group is further substituted with —(R 4 ) b , as herein defined.
- the present invention is directed to compounds of formula (I) wherein b is an integer from 0 to 1. In another preferred embodiment, the present invention is directed to compounds of formula (I) wherein b is 1. In another preferred embodiment, the present invention is directed to compounds of formula (I) wherein b is 1
- the present invention is directed to compounds of formula (I) wherein R 4 is selected from the group consisting of, halogen, C 1-4 alkyl, fluorinated C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy and NR J R K ; wherein R J and R K are each independently selected from the group consisting of hydrogen and C 1-2 alkyl; provided that the R 4 group is bound to a carbon atom.
- the present invention is directed to compounds of formula (I) wherein R 4 is selected from the group consisting of halogen, C 1-2 alkyl and C 1-2 alkoxy.
- the present invention is directed to compounds of formula (I) wherein R 4 is selected from the group consisting of halogen, C 1-2 alkyl and C 1-2 alkoxy.
- the present invention is directed to compounds of formula (I) wherein R 4 is selected from the group consisting of 2-fluoro, 3-fluoro, 2-chloro, 3-chloro, 2-methyl, 3-methyl and 2-methoxy.
- the present invention is directed to compounds of formula (I) wherein R 4 is selected from the group consisting of 2-fluoro, 2-chloro, 2-methyl, 2-methoxy, 3-fluoro and 3-methyl.
- the present invention is directed to compounds of formula (I) wherein R 4 is selected from the group consisting of 2-fluoro, 2-chloro, and 2-methyl.
- the present invention is directed to compounds of formula (I) wherein R 4 is selected from the group consisting of 2-fluoro, 2-methyl, 3-methyl and 2-methoxy. In another preferred embodiment, the present invention is directed to compounds of formula (I) wherein R 4 is selected from the group consisting of 2-fluoro and 2-methyl. In another preferred embodiment, the present invention is directed to compounds of formula (I) wherein R 4 is 2-methyl.
- the present invention is directed to compounds of formula (I) wherein R 5 is
- the present invention is directed to compounds of formula (I) wherein R 5 is
- the present invention is directed to compounds of formula (I) wherein R 5 is
- the present invention is directed to compounds of formula (I) wherein R 5 is
- the present invention is directed to compounds of formula (I) wherein R 5 is
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- phenyl selected from the group consisting of phenyl, heteroaryl and partially unsaturated heterocyclyl.
- the present invention is directed to compounds of formula (I) wherein
- phenyl selected from the group consisting of phenyl, naphthyl, 5 to 6-membered heteroaryl, 9 to 10-membered heteroaryl and partially unsaturated 9 to 10-membered heterocyclyl.
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- 3-cyano-phenyl is selected from the group consisting of 3-cyano-phenyl, 4-cyano-phenyl, 3-hydroxy-phenyl, 4-hydroxy-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl, 3-chloro-phenyl, 4-chloro-phenyl, 2,4-dichloro-phenyl, 3-methyl-phenyl, 4-methyl-phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 3-dimethylamino-phenyl, 4-dimethylamino-phenyl, 3-methylsulfonyl-amino-phenyl, 3-amino-4-hydroxy-phenyl, 3-formamido-4-hydroxy-phenyl, pyridin-2-yl
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- naphtha-2-yl is selected from the group consisting of naphtha-2-yl, 6-chloro-naphth-2-yl, 6-fluoro-naphth-2-yl, 6-methyl-naphth-2-yl, 6-methoxy-naphth-2-yl, 6-cyano-naphth-2-yl, indol-5-yl, indol-6-yl, 1-methyl-indol-5-yl, 2-methyl-indol-5-yl, 2-hydroxymethyl-indol-5-yl, 3-(2-hydroxyethyl)-indol-5-yl, 3-cyanomethyl-indol-5-yl, indazol-5-yl, indazol-6-yl, 1-methyl-indazol-5-yl, quinolin-7-yl, 3-chloro-quinolin-7-yl, 6-fluoro-quinolin-2-yl, 8-fluoro
- the present invention is directed to compounds of formula (I) wherein
- naphth-2-yl is selected from the group consisting of naphth-2-yl, 6-chloro-naphth-2-yl, 6-fluoro-naphth-2-yl, 7-fluoro-naphth-2-yl, 8-fluoro-naphth-2-yl, 6-methyl-naphth-2-yl, 6-methoxy-naphth-2-yl, 6-cyano-naphth-2-yl, indol-3-yl, indol-5-yl, indol-6-yl, 1-methyl-indol-5-yl, 2-methyl-indol-6-yl, 3-(2-hydroxyethyl)indol-5-yl, 3-cyanomethyl-indol-5-yl, 1,3-dimethyl-indol-5-yl, 1-methyl-3-(2-hydroxyethyl)indol-5-yl, quinolin-7-yl
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein wherein
- indol-5-yl is selected from the group consisting of indol-5-yl, indol-6-yl, indazol-4-yl, indazol-5-yl, 1-methyl-indazol-5-yl, benzthiazol-5-yl, benzofuran-5-yl, benzothien-5-yl, and 6-cyano-naphth-2-yl.
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I wherein
- indol-5-yl is selected from the group consisting of indol-5-yl, indol-6-yl, isoquinolin-6-yl, and benzofuran-5-yl.
- the present invention is directed to compounds of formula (I) wherein c is an integer from 0 to 2.
- the present invention is directed to compounds of formula (I) wherein each R 6 is independently selected from the group consisting of hydroxy, oxo, halogen, cyano, nitro, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, cyano substituted (C 1-4 alkyl), —(C 1-2 alkyl)-O—(C 1-4 alkyl), C 1-4 alkoxy, fluorinated C 1-4 alkoxy, —SO 2 —(C 1-4 alkyl), —C(O)—(C 1-4 alkyl), —C(O)-(fluorinated C 1-2 alkyl), —C(O)OH, —C(O)O—(C 1-4 alkyl), —C(O)—NR M R N , —NR M R N , —NR M —C(O)H, —NR M —SO 2 —(C 1-4 alkyl),
- the present invention is directed to compounds of formula (I) wherein each R 6 is independently selected from the group consisting of hydroxy, oxo, halogen, cyano, C 1-4 alkyl, fluorinated C 1-2 alkyl, hydroxy substituted C 1-4 alkyl, cyano-substituted C 1-2 alkyl, —(C 1-2 alkyl)-O—(C 1-2 alkyl), C 1-4 alkoxy, fluorinated C 1-2 alkoxy, —SO 2 —(C 1-4 alkyl), —CO 2 H, —C(O)O—(C 1-2 alkyl), —C(O)—(C 1-2 alkyl), —C(O)-(fluorinated C 1-2 alkyl), —C(O)—NR M R N , —NR M R N , —NR M —C(O)H, —NR M —SO 2 —(C 1-2 alkyl), C 3-5
- the present invention is directed to compounds of formula (I) wherein each R 6 is independently selected from the group consisting of hydroxy, halogen, cyano, nitro, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, —NR M R N , —C(O)—(C 1-4 alkyl), —C(O)—NR M R N , —C(O)OH, —C(O)O—(C 1-4 alkyl), —NR M —C(O)H, and —NR M —SO 2 —(C 1-4 alkyl); wherein R M and R N are each independently selected from the group consisting of hydrogen and C 1-4 alkyl.
- the present invention is directed to compounds of formula (I) wherein each R 6 is independently selected from the group consisting of hydroxy, halogen, cyano, C 1-2 alkyl, fluorinated C 1-2 alkyl, C 1-2 alkoxy, fluorinated C 1-2 alkoxy, —NR M R N , —C(O)—(C 1-2 alkyl), —NR M —C(O)H and —NR M —SO 2 —(C 1-2 alkyl); and wherein R M and R N are each independently selected from the group consisting of hydrogen and C 1-2 alkyl.
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein wherein
- the present invention is directed to compounds of formula (I) wherein wherein
- the present invention is directed to compounds of formula (I) wherein
- phenyl is selected from the group consisting of phenyl, pyridin-3-yl and pyridin-4-yl.
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein d is an integer from 0 to 1.
- the present invention is directed to compounds of formula (I) wherein R 7 is selected from the group consisting of hydroxy, halogen, cyano, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, C 1-4 alkoxy and fluorinated C 1-4 alkoxy.
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- phenyl is selected from the group consisting of phenyl, 5 to 6-membered, saturated, nitrogen containing heterocylyl and 5 to 6-membered, nitrogen containing heteroaryl.
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- phenyl is selected from the group consisting of phenyl and 5 to 6-membered, nitrogen containing heteroaryl.
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein and wherein
- the present invention is directed to compounds of formula (I) wherein
- pyridin-3-yl is selected from the group consisting of pyridin-3-yl, pyridin-4-yl, 1-methyl-pyrazol-4-yl, 1-isopropyl-pyrazol-4-yl, 1-cyclopropyl-pyrazol-4-yl, 1-cyclobutyl-pyrazol-4-yl, 1-methyl-pyrazol-5-yl, and 5-methyl-oxadiazol-2-yl.
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- the present invention is directed to compounds of formula (I) wherein
- pyridin-3-yl is selected from the group consisting of pyridin-3-yl and 1-methyl-pyrazol-4-yl.
- the present invention is directed to compounds of formula (I) wherein e is an integer from 0 to 2. In another preferred embodiment, the present invention is directed to compounds of formula (I) wherein e is an integer from 0 to 1.
- the present invention is directed to compounds of formula (I) wherein each R 8 is independently selected from the group consisting of hydroxy, halogen, cyano, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, —NR T R U , —C(O)—NR T R U , —C(O)OH, —C(O)O—(C 1-4 alkyl), —(C 1-4 alkyl)-NR T R U , C 3-5 cycloalkyl, —(C 1-2 alkyl)-(C 3-5 cycloalkyl), oxetanyl, and tetrahydro-furanyl; wherein R T and R U are each independently selected from the group consisting of hydrogen and C 1-4 alkyl.
- the present invention is directed to compounds of formula (I) wherein R 8 is selected from the group consisting of halogen, C 1-4 alkyl, C 3-5 cycloalkyl, —(C 1-2 alkyl)-(C 3-5 cycloalkyl), and oxetanyl.
- the present invention is directed to compounds of formula (I) wherein each R 8 is independently selected from the group consisting of hydroxy, halogen, cyano, C 1-4 alkyl, fluorinated C 1-4 alkyl, hydroxy substituted C 1-4 alkyl, C 1-4 alkoxy, fluorinated C 1-4 alkoxy, —NR T R U , —C(O)—NR T R U , —C(O)OH, —C(O)O—(C 1-4 alkyl) and —(C 1-4 alkyl)-NR T R U ; wherein R T and R U are each independently selected from the group consisting of hydrogen and C 1-4 alkyl.
- the present invention is directed to compounds of formula (I) wherein R 8 is selected from the group consisting of halogen and C 1-2 alkyl.
- the present invention is directed to compounds of formula (I) selected from the group consisting of 5-[4-(1-Benzofuran-5-yl)phenyl]-6- ⁇ [1-(cyclopropylcarbonyl)azetidin-3-yl]methyl ⁇ -4,6-diazaspiro[2.4]hept-4-en-7-one; 6- ⁇ [1-(Cyclopropylcarbonyl)azetidin-3-yl]methyl ⁇ -5-[4′-(1-methyl-1H-pyrazol-4-yl)biphenyl-4-yl]-4,6-diazaspiro[2.4]hept-4-en-7-one; (R)-6-((1-(Cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-5-(4′-(1-methyl-1H-pyrazol-4-yl)-[1,1′-biphenyl]-4-yl)-4,6-diazaspiro[2.4]hept
- the present invention is directed to compounds of formula (I) selected from the group consisting of 6- ⁇ [1-(Cyclopropylcarbonyl)azetidin-3-yl]methyl ⁇ -5-[4′-(1-methyl-1H-pyrazol-4-yl)biphenyl-4-yl]-4,6-diazaspiro[2.4]hept-4-en-7-one; (R)-6-((1-(Cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-5-(4′-(1-methyl-1H-pyrazol-4-yl)-[1,1′-biphenyl]-4-yl)-4,6-diazaspiro[2.4]hept-4-en-7-one; (R)-6-((1-(cyclopropanecarbonyl)pyrrolidin-3-yl)methyl)-5-(2-fluoro-4-(1-methyl-1H-indazol-5-yl)phenyl)
- the present invention is directed to compounds of formula (I) wherein R 1 and R 2 are taken together with the carbon atom to which they are bound to form a ring structure other than tetrahydrofuran-3,3-diyl or tetrahydropyran-4,4-diyl.
- the present invention is directed to compounds of formula (I) wherein (L 1 ) a is other than —SO 2 -pyrrolidin-1-yl or —SO 2 -pyridin-3-yl. In another embodiment, the present invention is directed to compounds of formula (I) wherein (L 1 ) a is other than C(O)-thiazol-2-yl, —C(O)—CF 3 , —C(O)OCH 3 or —SO 2 —CH 3 .
- the present invention is directed to compounds of formula (I) wherein R 5 is other than 1,2,3,4,4a,8a-hexahydro-2-methyl-carbonyl-isoquinolin-6-yl), 1,2,3,4-trihydro-2-methylcarbonyl-isoquinolin-2-yl, 4-methyl-3,4-dihydro-pyrido[2,3-b]oxazon-7-yl, 2-oxo-3,4-dihydro-quinolin-7-yl, 5-chloro-pyridin-3-yl, 5-(2-hydroxy-2-methyl-propyl)-pyridin-2-yl, 6-isopropyl-pyridin-3-yl, 6-(1-cyanomethyl)-pyridin-3-yl, 6-(2-hydroxy-2-methyl-propyl)-pyridin-3-yl, 2-(piperazin-1-yl)-pyridin-4-yl, 2-(4-methyl-piperazin-1-yl)-pyridin-pyr
- the present invention is directed to compounds of formula (I) as herein described, provided that when R 1 and R 2 are taken together with the carbon atom to which they are bound to form 1-(methoxycarbonyl)-azetidin-3-yl, m is 1 and n is 0 or m is 0 and n is 1;
- -(L 1 ) a -R 3 is selected from the group consisting of —C(O)—CF 3 , —C(O)-cyclopropyl, —C(O)-(thiazol-2-yl), —C(O)OCH 3 , and —SO 2 —CH 3 ,
- R 5 is other than quinolin-7-yl, benzofuran-5-yl, 1-methyl-indazol-5-yl, 1-methyl-pyrazol-4-yl, 4-(1-methyl-pyrazol-4-yl)phenyl, 1,2,3,4,4a,8a-hexahydro-2-methyl-carbonyl-isoquinolin-6-yl), or 1,2,3,4-trihydro-2-methylcarbonyl-isoquinolin-2-yl.
- the present invention is directed to compounds of formula (I) as herein described, provided that when R 1 and R 2 are taken together with the carbon atom to which they are bound to form cyclopentyl; m is 1 and n is 0 or m is 0 and m is 1;
- pyrrolidin-3R-yl is pyrrolidin-3R-yl; -(L 1 ) a -R 3 is —C(O)-cyclopropyl;
- the present invention is directed to compounds of formula (I) as herein described, provided that when R 1 and R 2 are taken together with the carbon atom to which they are bound to form cyclopentyl; m is 1 and n is 0 or m is 0 and m is 1;
- pyrrolidin-3R-yl is pyrrolidin-3R-yl; -(L 1 ) a -R 3 is —SO 2 -pyrrolidin-1-yl;
- the present invention is directed to compounds of formula (I) as herein described, provided that when R 1 and R 2 are taken together with the carbon atom to which they are bound to form cyclopropyl; m is 0, n is 0,
- -(L 1 ) a -R 3 is selected from the group consisting of —C(O)-cyclopropyl, —C(O)-(1-methyl-cyclopropyl) and —C(O)-(1-hydroxy-cyclopropyl);
- R 4 b 0 or (R 4 ) b is selected from the group consisting of 2-fluoro and 2-methyl; then R 5 is other than 1-isopropylsulfonyl-phenyl, 1-methyl-indazol-5-yl, 1-isopropyl-indazol-5-yl, 1-oxetan-3-yl, indazol-5-yl, 1-methyl-pyrazol-4-yl, 4-methyl-7-bromo-quinolin-2-yl, 5-(2-hydroxy-2-methyl-propyl)-pyridin-2-yl, 6-isopropyl-pyridin-3-yl, 6-(1-cyanomethyl)-pyridin-3-yl, 6-(2-hydroxy-2-methyl-propyl)-pyridin-3-yl, 1,5-naphthyridin-3-yl, 3-methyl-[1,2,4]triazolo[4,3-a]pyridin-6-yl, 4-(1-isobutyl-pyra
- the present invention is directed to compounds of formula (I) as herein described, provided that when R 1 and R 2 are taken together with the carbon atom to which they are bound to form cyclopropyl; m is 0, n is 0,
- R 4 is 2-methyl; then R 5 is other 1-methyl-indazol-5-yl.
- the present invention is directed to compounds of formula (I) as herein described, provided that when R 1 and R 2 are taken together with the carbon atom to which they are bound to form cyclopropyl; m is 0, n is 0,
- -(L 1 ) a -R 3 is —C(O)-pyridin-3-yl
- (R 4 ) b is 2-methyl; then R 5 is other than 1-methyl-indazol-5-yl.
- the present invention is directed to compounds of formula (I) as herein described, provided that when R 1 and R 2 are taken together with the carbon atom to which they are bound to form cyclopropyl; m is 0, n is 2,
- R 5 is other than indazol-5-yl, benzofuran-5-yl, benzothien-5-yl, 1-methyl-indazol-5-yl, 4-(4-methylphenyl)phenyl, or 4-(3-chlorophenyl)-phenyl.
- the present invention is directed to compounds of formula (I) as herein described, provided that when R 1 and R 2 are taken together with the carbon atom to which they are bound to form cyclopropyl; m is 1, n is 1,
- R 5 is other 4-trifluoromethyl-phenyl, 1-methyl-pyrazol-4-yl, benzoxazol-5-yl, pyridin-4-yl, or 4-(1-methyl-pyrazol-4-yl)-phenyl.
- the present invention is directed to compounds of formula (I) as herein described, provided that when R 1 and R 2 are taken together with the carbon atom to which they are bound to form cyclopropyl; m is 0 and n is 1 or m is 1 and n is 0;
- pyrrolidin-3R-yl is pyrrolidin-3R-yl; -(L 1 ) a -R 3 is —C(O)-cyclopropyl;
- R 5 is other than 5-chloro-pyridin-3-yl, 2-oxo-3,4-dihydro-quinolin-7-yl, or 6-(4-methyl-piperazin-1-yl)-pyridin-3-yl.
- the present invention is directed to compounds of formula (I) as herein described, provided that when R 1 and R 2 are taken together with the carbon atom to which they are bound to form tetrahydrofuran-3,3-diyl or tetrahydropyran-4,4-diyl; m is an integer from 0 to 1 and n is 0 or m is 0 and n is an integer from 0 to 1;
- -(L 1 ) a -R 3 is selected from the group consisting of —C(O)-thiazol-2-yl, —C(O)—CF 3 , —C(O)OCH 3 and —SO 2 —CH 3 ;
- R 5 is other than quinolin-7-yl, 1-methyl-indazol-5-yl, benzofuran-5-yl, or 4-(1-methyl-pyrazol-4-yl)-phenyl.
- the present invention is directed to compounds of formula (I) as herein described, provided that when R 1 and R 2 are taken together with the carbon atom to which they are bound to form 1-(methoxycarbonyl)-azetidin-3-yl; m is 1 and n is 0 or m is 0 and m is 1;
- pyrrolidin-3R-yl is pyrrolidin-3R-yl; -(L 1 ) a -R 3 is —C(O)-cyclopropyl;
- R 5 is other than quinolin-7-yl, benzofuran-5-yl, or 1-methyl-indazol-5-yl.
- the present invention is directed to compounds of formula (I) as herein described, provided that when R al and R 2 are taken together with the carbon atom to which they are bound to form cyclopropyl; m is 0, n is 0,
- -(L 1 ) a -R 3 is selected from the group consisting of —C(O)-cyclopropyl, —C(O)-(1-methyl-cyclopropyl) and —C(O)-(1-hydroxy-cyclopropyl);
- R 4 b 0 or (R 4 ) b is selected from the group consisting of 2-fluoro and 2-methyl; then R 5 is other than 1-methyl-indazol-5-yl or indazol-5-yl.
- the present invention is directed to compounds of formula (I) as herein described, provided that when R 1 and R 2 are taken together with the carbon atom to which they are bound to form cyclopropyl; m is 1, n is 1,
- R 5 is other than benzoxazol-5-yl.
- the present invention is directed to compounds of formula (I) as herein described, provided that when R 1 and R 2 are taken together with the carbon atom to which they are bound to form cyclopropyl; m is 0 and n is 1 or m is 1 and n is 0;
- pyrrolidin-3R-yl is pyrrolidin-3R-yl; -(L 1 ) a -R 3 is —C(O)-cyclopropyl;
- R 5 is other than 2-oxo-3,4-dihydro-quinolin-7-yl.
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Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US14/020,122 US20150099730A1 (en) | 2012-09-07 | 2013-09-06 | Imidazolin-5-one derivative useful as fasn inhibitors for the treatment of cancer |
US14/851,738 US10077261B2 (en) | 2012-09-07 | 2015-09-11 | Imidazolin-5-one derivative useful as FASN inhibitors for the treatment of cancer |
US16/040,004 US20180327401A1 (en) | 2012-09-07 | 2018-07-19 | Imidazolin-5-one derivative useful as fasn inhibitors for the treatment of cancer |
Applications Claiming Priority (2)
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US201261698125P | 2012-09-07 | 2012-09-07 | |
US14/020,122 US20150099730A1 (en) | 2012-09-07 | 2013-09-06 | Imidazolin-5-one derivative useful as fasn inhibitors for the treatment of cancer |
Related Child Applications (1)
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US14/851,738 Continuation US10077261B2 (en) | 2012-09-07 | 2015-09-11 | Imidazolin-5-one derivative useful as FASN inhibitors for the treatment of cancer |
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US20150099730A1 true US20150099730A1 (en) | 2015-04-09 |
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US14/020,122 Abandoned US20150099730A1 (en) | 2012-09-07 | 2013-09-06 | Imidazolin-5-one derivative useful as fasn inhibitors for the treatment of cancer |
US14/851,738 Active US10077261B2 (en) | 2012-09-07 | 2015-09-11 | Imidazolin-5-one derivative useful as FASN inhibitors for the treatment of cancer |
US16/040,004 Abandoned US20180327401A1 (en) | 2012-09-07 | 2018-07-19 | Imidazolin-5-one derivative useful as fasn inhibitors for the treatment of cancer |
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US14/851,738 Active US10077261B2 (en) | 2012-09-07 | 2015-09-11 | Imidazolin-5-one derivative useful as FASN inhibitors for the treatment of cancer |
US16/040,004 Abandoned US20180327401A1 (en) | 2012-09-07 | 2018-07-19 | Imidazolin-5-one derivative useful as fasn inhibitors for the treatment of cancer |
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US (3) | US20150099730A1 (es) |
EP (1) | EP2892892B1 (es) |
JP (1) | JP6285442B2 (es) |
AR (1) | AR092491A1 (es) |
CA (1) | CA2884355C (es) |
WO (1) | WO2014039769A1 (es) |
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CN116139138A (zh) * | 2016-11-11 | 2023-05-23 | 3-V生物科学股份有限公司 | 脂质合成的杂环调节剂 |
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US20170119786A1 (en) | 2011-03-08 | 2017-05-04 | 3-V Biosciences, Inc. | Heterocyclic modulators of lipid synthesis |
WO2014039769A1 (en) * | 2012-09-07 | 2014-03-13 | Janssen Pharmaceutica Nv | Imidazolin-5-one derivatives useful as fatty acid snthase (fasn) inhibitors for|the treatment of cancer |
JP6617106B2 (ja) * | 2013-12-17 | 2019-12-04 | ヤンセン ファーマシューティカ エヌ.ベー. | 癌の治療用のfasn阻害剤として有用なイミダゾリン−5−オン誘導体 |
EP3220901B1 (en) | 2014-11-20 | 2020-02-19 | VIB vzw | Means and methods for treatment of early-onset parkinson's disease |
ES2849951T3 (es) | 2015-06-18 | 2021-08-24 | 89Bio Ltd | Derivados de piperidina 4-bencil y 4-benzoil sustituidos |
PE20180572A1 (es) | 2015-06-18 | 2018-04-04 | Cephalon Inc | Derivados de piperidina 1,4-sustituidos |
TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
US10902613B2 (en) | 2019-03-20 | 2021-01-26 | Bi Incorporated | Systems and methods for textural zone identification |
US10692345B1 (en) | 2019-03-20 | 2020-06-23 | Bi Incorporated | Systems and methods for textural zone monitoring |
US10893383B2 (en) | 2019-05-06 | 2021-01-12 | Bi Incorporated | Systems and methods for monitoring system equipment diagnosis |
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WO2004058727A1 (en) * | 2002-12-20 | 2004-07-15 | Bayer Pharmaceuticals Corporation | Substituted 3,5-dihydro-4h-imidazol-4-ones for the treatment of obesity |
US20130172384A1 (en) * | 2010-09-17 | 2013-07-04 | Glaxosmithkline Intellectual Property Development Limited | Fatty acid synthase inhibitors |
WO2014039769A1 (en) * | 2012-09-07 | 2014-03-13 | Janssen Pharmaceutica Nv | Imidazolin-5-one derivatives useful as fatty acid snthase (fasn) inhibitors for|the treatment of cancer |
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KR20050072670A (ko) * | 2002-07-01 | 2005-07-12 | 파스젠, 엘엘씨. | 신규 화합물, 이를 함유하는 약제학적 조성물 및 이의사용방법 |
EP2386551A1 (en) * | 2002-07-09 | 2011-11-16 | Fasgen Inc. | Novel compounds, pharmaceutical compositions containing same, and methods of use for same |
ZA200700024B (en) * | 2004-05-26 | 2008-06-25 | Fasgen Llc | Novel compounds, pharmaceutical compositions containing same, and methods of use for same |
-
2013
- 2013-09-06 WO PCT/US2013/058416 patent/WO2014039769A1/en active Application Filing
- 2013-09-06 EP EP13762696.6A patent/EP2892892B1/en active Active
- 2013-09-06 CA CA2884355A patent/CA2884355C/en not_active Expired - Fee Related
- 2013-09-06 US US14/020,122 patent/US20150099730A1/en not_active Abandoned
- 2013-09-06 JP JP2015531220A patent/JP6285442B2/ja not_active Expired - Fee Related
- 2013-09-09 AR ARP130103205A patent/AR092491A1/es unknown
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2015
- 2015-09-11 US US14/851,738 patent/US10077261B2/en active Active
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2018
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US20130172384A1 (en) * | 2010-09-17 | 2013-07-04 | Glaxosmithkline Intellectual Property Development Limited | Fatty acid synthase inhibitors |
WO2014039769A1 (en) * | 2012-09-07 | 2014-03-13 | Janssen Pharmaceutica Nv | Imidazolin-5-one derivatives useful as fatty acid snthase (fasn) inhibitors for|the treatment of cancer |
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Cited By (1)
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CN116139138A (zh) * | 2016-11-11 | 2023-05-23 | 3-V生物科学股份有限公司 | 脂质合成的杂环调节剂 |
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JP6285442B2 (ja) | 2018-02-28 |
US20180327401A1 (en) | 2018-11-15 |
AR092491A1 (es) | 2015-04-22 |
US10077261B2 (en) | 2018-09-18 |
EP2892892A1 (en) | 2015-07-15 |
US20160002219A1 (en) | 2016-01-07 |
CA2884355C (en) | 2022-05-17 |
CA2884355A1 (en) | 2014-03-13 |
EP2892892B1 (en) | 2017-05-31 |
WO2014039769A1 (en) | 2014-03-13 |
JP2015527397A (ja) | 2015-09-17 |
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