AU2023213736A1

AU2023213736A1 - Compounds and methods of use

Compounds and methods of use Download PDF

Info

Publication number: AU2023213736A1
Authority: AU; Australia
Prior art keywords: group; alkyl; compound; pharmaceutically acceptable; acceptable salt
Prior art date: 2022-01-26
Legal status : Pending

Application number

AU2023213736A

Other languages

English (en)

Inventor

Kevin M. Cottrell

Current Assignee

Tango Therapeutics Inc

Original Assignee

Tango Therapeutics Inc

Priority date

2022-01-26

Filing date

2023-01-26

Publication date

2024-08-01

2023-01-26 Application filed by Tango Therapeutics Inc filed Critical Tango Therapeutics Inc

2024-08-01 Publication of AU2023213736A1 publication Critical patent/AU2023213736A1/en

Status Pending legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 242
238000000034 method Methods 0.000 title abstract description 20
150000003839 salts Chemical class 0.000 claims abstract description 117
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
-1 –C1–C6 heteroalkyl Chemical group 0.000 claims description 1084
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 217
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 182
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 169
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 166
125000000623 heterocyclic group Chemical group 0.000 claims description 164
125000000217 alkyl group Chemical group 0.000 claims description 147
125000003710 aryl alkyl group Chemical group 0.000 claims description 138
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 135
125000005843 halogen group Chemical group 0.000 claims description 133
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 132
229910052739 hydrogen Inorganic materials 0.000 claims description 132
125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims description 127
125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 127
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 126
125000003118 aryl group Chemical group 0.000 claims description 112
125000004093 cyano group Chemical group *C#N 0.000 claims description 109
125000004452 carbocyclyl group Chemical group 0.000 claims description 106
125000001072 heteroaryl group Chemical group 0.000 claims description 105
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 94
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 92
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 91
125000000753 cycloalkyl group Chemical group 0.000 claims description 76
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 75
201000010099 disease Diseases 0.000 claims description 70
229910052757 nitrogen Inorganic materials 0.000 claims description 68
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 65
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 64
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 59
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 57
102100034187 S-methyl-5'-thioadenosine phosphorylase Human genes 0.000 claims description 55
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 54
125000001424 substituent group Chemical group 0.000 claims description 53
125000004404 heteroalkyl group Chemical group 0.000 claims description 51
125000004076 pyridyl group Chemical group 0.000 claims description 47
125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 claims description 45
206010028980 Neoplasm Diseases 0.000 claims description 41
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 40
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 39
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 36
239000000203 mixture Substances 0.000 claims description 36
201000011510 cancer Diseases 0.000 claims description 34
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 33
230000002950 deficient Effects 0.000 claims description 32
229910052805 deuterium Inorganic materials 0.000 claims description 29
125000003566 oxetanyl group Chemical group 0.000 claims description 27
125000000714 pyrimidinyl group Chemical group 0.000 claims description 27
125000001188 haloalkyl group Chemical group 0.000 claims description 24
125000004193 piperazinyl group Chemical group 0.000 claims description 24
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 23
125000003386 piperidinyl group Chemical group 0.000 claims description 23
125000004917 3-methyl-2-butyl group Chemical group CC(C(C)*)C 0.000 claims description 22
125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 22
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 21
125000004433 nitrogen atom Chemical group N* 0.000 claims description 21
125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims description 21
239000003814 drug Substances 0.000 claims description 20
125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 19
125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims description 18
125000003226 pyrazolyl group Chemical group 0.000 claims description 18
229910052705 radium Inorganic materials 0.000 claims description 18
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 17
125000000335 thiazolyl group Chemical group 0.000 claims description 17
125000001544 thienyl group Chemical group 0.000 claims description 17
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 16
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 claims description 16
125000004289 pyrazol-3-yl group Chemical group [H]N1N=C(*)C([H])=C1[H] 0.000 claims description 16
229910052794 bromium Inorganic materials 0.000 claims description 15
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 15
125000000168 pyrrolyl group Chemical group 0.000 claims description 15
230000002062 proliferating effect Effects 0.000 claims description 14
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 14
125000002883 imidazolyl group Chemical group 0.000 claims description 13
125000002971 oxazolyl group Chemical group 0.000 claims description 13
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 12
208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims description 12
125000005873 benzo[d]thiazolyl group Chemical group 0.000 claims description 12
206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims description 12
125000002541 furyl group Chemical group 0.000 claims description 12
125000001041 indolyl group Chemical group 0.000 claims description 12
125000001786 isothiazolyl group Chemical group 0.000 claims description 12
125000000842 isoxazolyl group Chemical group 0.000 claims description 12
125000001624 naphthyl group Chemical group 0.000 claims description 12
208000029974 neurofibrosarcoma Diseases 0.000 claims description 12
208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 12
125000001425 triazolyl group Chemical group 0.000 claims description 12
206010039491 Sarcoma Diseases 0.000 claims description 11
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 11
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 11
229940124597 therapeutic agent Drugs 0.000 claims description 11
125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 11
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
125000003373 pyrazinyl group Chemical group 0.000 claims description 10
125000002098 pyridazinyl group Chemical group 0.000 claims description 10
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 10
125000006716 (C1-C6) heteroalkyl group Chemical group 0.000 claims description 9
125000005955 1H-indazolyl group Chemical group 0.000 claims description 9
229910006074 SO2NH2 Inorganic materials 0.000 claims description 9
208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 6
208000036764 Adenocarcinoma of the esophagus Diseases 0.000 claims description 6
206010052747 Adenocarcinoma pancreas Diseases 0.000 claims description 6
206010003571 Astrocytoma Diseases 0.000 claims description 6
206010005003 Bladder cancer Diseases 0.000 claims description 6
208000003174 Brain Neoplasms Diseases 0.000 claims description 6
208000000461 Esophageal Neoplasms Diseases 0.000 claims description 6
208000032612 Glial tumor Diseases 0.000 claims description 6
206010018338 Glioma Diseases 0.000 claims description 6
206010027406 Mesothelioma Diseases 0.000 claims description 6
206010066948 Myxofibrosarcoma Diseases 0.000 claims description 6
206010030137 Oesophageal adenocarcinoma Diseases 0.000 claims description 6
206010030155 Oesophageal carcinoma Diseases 0.000 claims description 6
206010061534 Oesophageal squamous cell carcinoma Diseases 0.000 claims description 6
206010061902 Pancreatic neoplasm Diseases 0.000 claims description 6
208000036765 Squamous cell carcinoma of the esophagus Diseases 0.000 claims description 6
208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 6
206010005084 bladder transitional cell carcinoma Diseases 0.000 claims description 6
201000001528 bladder urothelial carcinoma Diseases 0.000 claims description 6
210000000481 breast Anatomy 0.000 claims description 6
208000006990 cholangiocarcinoma Diseases 0.000 claims description 6
210000004696 endometrium Anatomy 0.000 claims description 6
208000028653 esophageal adenocarcinoma Diseases 0.000 claims description 6
201000004101 esophageal cancer Diseases 0.000 claims description 6
208000007276 esophageal squamous cell carcinoma Diseases 0.000 claims description 6
201000006585 gastric adenocarcinoma Diseases 0.000 claims description 6
208000005017 glioblastoma Diseases 0.000 claims description 6
201000010536 head and neck cancer Diseases 0.000 claims description 6
208000014829 head and neck neoplasm Diseases 0.000 claims description 6
210000003734 kidney Anatomy 0.000 claims description 6
208000032839 leukemia Diseases 0.000 claims description 6
210000004185 liver Anatomy 0.000 claims description 6
210000004072 lung Anatomy 0.000 claims description 6
201000005249 lung adenocarcinoma Diseases 0.000 claims description 6
208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 6
201000001441 melanoma Diseases 0.000 claims description 6
201000002094 pancreatic adenocarcinoma Diseases 0.000 claims description 6
201000002528 pancreatic cancer Diseases 0.000 claims description 6
208000008443 pancreatic carcinoma Diseases 0.000 claims description 6
210000004872 soft tissue Anatomy 0.000 claims description 6
210000002784 stomach Anatomy 0.000 claims description 6
208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 6
201000005112 urinary bladder cancer Diseases 0.000 claims description 6
210000001635 urinary tract Anatomy 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 5
210000002429 large intestine Anatomy 0.000 claims description 5
VMWJCFLUSKZZDX-UHFFFAOYSA-N n,n-dimethylmethanamine Chemical compound [CH2]N(C)C VMWJCFLUSKZZDX-UHFFFAOYSA-N 0.000 claims description 5
210000004224 pleura Anatomy 0.000 claims description 5
101710136206 S-methyl-5'-thioadenosine phosphorylase Proteins 0.000 claims 3
230000008569 process Effects 0.000 abstract description 2
125000005842 heteroatom Chemical group 0.000 description 106
125000004432 carbon atom Chemical group C* 0.000 description 90
210000004027 cell Anatomy 0.000 description 64
125000000304 alkynyl group Chemical group 0.000 description 61
125000001309 chloro group Chemical group Cl* 0.000 description 59
229910052760 oxygen Inorganic materials 0.000 description 52
WUUGFSXJNOTRMR-IOSLPCCCSA-N 5'-S-methyl-5'-thioadenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](CSC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 WUUGFSXJNOTRMR-IOSLPCCCSA-N 0.000 description 49
125000003342 alkenyl group Chemical group 0.000 description 49
229910052717 sulfur Inorganic materials 0.000 description 49
102100034607 Protein arginine N-methyltransferase 5 Human genes 0.000 description 45
101000924530 Homo sapiens Protein arginine N-methyltransferase 5 Proteins 0.000 description 43
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 43
235000002639 sodium chloride Nutrition 0.000 description 42
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 26
125000002887 hydroxy group Chemical group [H]O* 0.000 description 26
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 26
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 25
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 23
208000035475 disorder Diseases 0.000 description 22
239000001301 oxygen Substances 0.000 description 22
125000001412 tetrahydropyranyl group Chemical group 0.000 description 22
125000006708 (C5-C14) heteroaryl group Chemical group 0.000 description 21
125000002950 monocyclic group Chemical group 0.000 description 21
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 21
125000003725 azepanyl group Chemical group 0.000 description 20
125000002393 azetidinyl group Chemical group 0.000 description 20
125000002757 morpholinyl group Chemical group 0.000 description 20
125000000719 pyrrolidinyl group Chemical group 0.000 description 20
239000011593 sulfur Substances 0.000 description 19
125000002619 bicyclic group Chemical group 0.000 description 18
239000001257 hydrogen Substances 0.000 description 18
150000003254 radicals Chemical class 0.000 description 16
238000009825 accumulation Methods 0.000 description 15
125000004122 cyclic group Chemical group 0.000 description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 description 15
229920006395 saturated elastomer Polymers 0.000 description 15
229940125897 PRMT5 inhibitor Drugs 0.000 description 14
125000001246 bromo group Chemical group Br* 0.000 description 13
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 13
230000001225 therapeutic effect Effects 0.000 description 13
238000011282 treatment Methods 0.000 description 13
125000005915 C6-C14 aryl group Chemical group 0.000 description 12
MEFKEPWMEQBLKI-AIRLBKTGSA-N S-adenosyl-L-methioninate Chemical compound O[C@@H]1[C@H](O)[C@@H](C[S+](CC[C@H](N)C([O-])=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MEFKEPWMEQBLKI-AIRLBKTGSA-N 0.000 description 12
239000003112 inhibitor Substances 0.000 description 12
108090000623 proteins and genes Proteins 0.000 description 12
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 description 12
102100037373 DNA-(apurinic or apyrimidinic site) endonuclease Human genes 0.000 description 11
101710088570 Flagellar hook-associated protein 1 Proteins 0.000 description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
239000011203 carbon fibre reinforced carbon Substances 0.000 description 11
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 11
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 11
125000006513 pyridinyl methyl group Chemical group 0.000 description 11
229960001570 ademetionine Drugs 0.000 description 10
125000003545 alkoxy group Chemical group 0.000 description 10
230000027455 binding Effects 0.000 description 10
229910052799 carbon Inorganic materials 0.000 description 10
125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 10
125000006622 cycloheptylmethyl group Chemical group 0.000 description 10
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 10
125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 10
125000001153 fluoro group Chemical group F* 0.000 description 10
229910052736 halogen Inorganic materials 0.000 description 10
125000006173 tetrahydropyranylmethyl group Chemical group 0.000 description 10
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 9
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 9
125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 9
230000000694 effects Effects 0.000 description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 description 9
230000036967 uncompetitive effect Effects 0.000 description 9
125000000008 (C1-C10) alkyl group Chemical group 0.000 description 8
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 8
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 8
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 8
150000002367 halogens Chemical class 0.000 description 8
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 8
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 8
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 8
239000000758 substrate Substances 0.000 description 8
210000001519 tissue Anatomy 0.000 description 8
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 7
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 7
125000006374 C2-C10 alkenyl group Chemical group 0.000 description 7
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
230000007812 deficiency Effects 0.000 description 7
230000005764 inhibitory process Effects 0.000 description 7
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 6
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 6
108010009392 Cyclin-Dependent Kinase Inhibitor p16 Proteins 0.000 description 6
102100024458 Cyclin-dependent kinase inhibitor 2A Human genes 0.000 description 6
229910002651 NO3 Inorganic materials 0.000 description 6
229910019142 PO4 Inorganic materials 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
125000002252 acyl group Chemical group 0.000 description 6
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125000002947 alkylene group Chemical group 0.000 description 6
125000001183 hydrocarbyl group Chemical group 0.000 description 6
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
125000006574 non-aromatic ring group Chemical group 0.000 description 6
125000001715 oxadiazolyl group Chemical group 0.000 description 6
125000004304 oxazol-5-yl group Chemical group O1C=NC=C1* 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
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125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
125000001113 thiadiazolyl group Chemical group 0.000 description 6
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 description 5
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 5
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
229910006069 SO3H Inorganic materials 0.000 description 5
125000004104 aryloxy group Chemical group 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
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230000014509 gene expression Effects 0.000 description 5
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230000000670 limiting effect Effects 0.000 description 5
XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 description 5
235000021317 phosphate Nutrition 0.000 description 5
125000003367 polycyclic group Chemical group 0.000 description 5
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125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
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101000582546 Homo sapiens Methylosome protein 50 Proteins 0.000 description 4
102100030528 Methylosome protein 50 Human genes 0.000 description 4
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
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QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
230000009471 action Effects 0.000 description 4
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230000008901 benefit Effects 0.000 description 4
125000005605 benzo group Chemical group 0.000 description 4
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WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 4
125000002618 bicyclic heterocycle group Chemical group 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
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