ZA200206664B - Substituted glutarimides and use thereof IL-12 production inhibitors. - Google Patents
Substituted glutarimides and use thereof IL-12 production inhibitors. Download PDFInfo
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- ZA200206664B ZA200206664B ZA200206664A ZA200206664A ZA200206664B ZA 200206664 B ZA200206664 B ZA 200206664B ZA 200206664 A ZA200206664 A ZA 200206664A ZA 200206664 A ZA200206664 A ZA 200206664A ZA 200206664 B ZA200206664 B ZA 200206664B
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- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical class O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 title claims description 26
- 239000003112 inhibitor Substances 0.000 title description 3
- 230000019734 interleukin-12 production Effects 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 20
- -1 trifluoromethoxy, nitro, amino Chemical group 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000003254 radicals Chemical class 0.000 claims description 14
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000004185 ester group Chemical group 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 230000009467 reduction Effects 0.000 claims description 5
- 238000006722 reduction reaction Methods 0.000 claims description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003368 amide group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 230000002519 immonomodulatory effect Effects 0.000 claims description 4
- 229940095102 methyl benzoate Drugs 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 claims description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- SESFRYSPDFLNCH-UHFFFAOYSA-N Benzyl benzoate Natural products C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 2
- KRTGJZMJJVEKRX-UHFFFAOYSA-N 2-phenylethan-1-yl Chemical compound [CH2]CC1=CC=CC=C1 KRTGJZMJJVEKRX-UHFFFAOYSA-N 0.000 claims description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- FPEIKJDVIJSMOH-UHFFFAOYSA-N 4-methylidenepiperidine-2,6-dione Chemical compound C=C1CC(=O)NC(=O)C1 FPEIKJDVIJSMOH-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 2
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 230000003213 activating effect Effects 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 229960002903 benzyl benzoate Drugs 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 claims description 2
- NNTOJPXOCKCMKR-UHFFFAOYSA-N boron;pyridine Chemical compound [B].C1=CC=NC=C1 NNTOJPXOCKCMKR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- OAOPDYUHWPBJCW-UHFFFAOYSA-N cyanoboron;sodium Chemical compound [Na].[B]C#N OAOPDYUHWPBJCW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 238000006911 enzymatic reaction Methods 0.000 claims description 2
- 239000008098 formaldehyde solution Substances 0.000 claims description 2
- 150000002310 glutaric acid derivatives Chemical class 0.000 claims description 2
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 150000003951 lactams Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229920002866 paraformaldehyde Polymers 0.000 claims description 2
- 238000006268 reductive amination reaction Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 4
- 206010059245 Angiopathy Diseases 0.000 claims 3
- 230000002489 hematologic effect Effects 0.000 claims 3
- 230000000771 oncological effect Effects 0.000 claims 3
- 239000005711 Benzoic acid Substances 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 5
- 210000002540 macrophage Anatomy 0.000 description 5
- 210000001616 monocyte Anatomy 0.000 description 5
- 208000023275 Autoimmune disease Diseases 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002158 endotoxin Substances 0.000 description 3
- 229920006008 lipopolysaccharide Polymers 0.000 description 3
- 230000000770 proinflammatory effect Effects 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 208000027866 inflammatory disease Diseases 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- 108020000946 Bacterial DNA Proteins 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 102100023999 Heterogeneous nuclear ribonucleoprotein R Human genes 0.000 description 1
- 101001047853 Homo sapiens Heterogeneous nuclear ribonucleoprotein R Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 108010028921 Lipopeptides Proteins 0.000 description 1
- ILHJYNCSCJALMP-PPHPATTJSA-N O=C1NC(CC[C@@H]1NCC1=C(C(=O)NN)C=CC=C1)=O.N1C(CCCC1=O)=O Chemical compound O=C1NC(CC[C@@H]1NCC1=C(C(=O)NN)C=CC=C1)=O.N1C(CCCC1=O)=O ILHJYNCSCJALMP-PPHPATTJSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000002424 anti-apoptotic effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 210000000612 antigen-presenting cell Anatomy 0.000 description 1
- 238000003782 apoptosis assay Methods 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 150000003936 benzamides Chemical class 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 210000004443 dendritic cell Anatomy 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000008105 immune reaction Effects 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 230000004957 immunoregulator effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000013586 microbial product Substances 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000005522 programmed cell death Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
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| DE10002509A DE10002509A1 (de) | 2000-01-21 | 2000-01-21 | Substituierte Glutarimide |
Publications (1)
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| ZA200206664B true ZA200206664B (en) | 2004-01-21 |
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| ZA200206664A ZA200206664B (en) | 2000-01-21 | 2002-08-20 | Substituted glutarimides and use thereof IL-12 production inhibitors. |
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| EP (1) | EP1252144B1 (da) |
| JP (1) | JP2003524641A (da) |
| KR (1) | KR20020067614A (da) |
| CN (1) | CN1185215C (da) |
| AR (1) | AR030185A1 (da) |
| AT (1) | ATE451355T1 (da) |
| AU (1) | AU780636B2 (da) |
| BR (1) | BR0108030A (da) |
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| NO (1) | NO323395B1 (da) |
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| WO (1) | WO2001053261A1 (da) |
| ZA (1) | ZA200206664B (da) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE10002509A1 (de) * | 2000-01-21 | 2001-07-26 | Gruenenthal Gmbh | Substituierte Glutarimide |
| US7842727B2 (en) | 2001-03-27 | 2010-11-30 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors |
| US7193105B2 (en) * | 2002-05-22 | 2007-03-20 | Errant Gene Therapeutics, Llc | Histone deacetylase inhibitors based on trihalomethylcarbonyl compounds |
| DE10163595A1 (de) | 2001-12-21 | 2003-08-07 | Gruenenthal Gmbh | In 3-Position heterocyclisch substituierte Piperidin-2,6-dione |
| EP1511477A4 (en) | 2002-05-22 | 2008-04-09 | Errant Gene Therapeutics Llc | HISTONE DEACETYLASE INHIBITORS BASED ON ALPHA-KETO-EPOXYDE COMPOUNDS |
| US20040192738A1 (en) * | 2003-03-18 | 2004-09-30 | Aventis Pharma Deutschland Gmbh | 2-(Butyl-1-sulfonylamino)-N-[1(R)-(6-methoxypyridin-3-yl)propyl] benzamide, its use as a medicament, and pharmaceutical preparations comprising it |
| AP2006003726A0 (en) | 2004-03-17 | 2006-10-31 | Pfizer Prod Inc | Novel benzyl(idene)-lactam derivatives |
| DE102004026703A1 (de) * | 2004-05-28 | 2005-12-29 | Grünenthal GmbH | Verfahren zur Herstellung von in 3-Position heterocyclisch substituierten Piperidin-2,6-dionen |
| CA2914178C (en) | 2013-01-07 | 2023-06-13 | University Of Southern California | Deoxyuridine triphosphatase inhibitors |
| CN110128406B (zh) | 2013-04-12 | 2021-08-27 | 制药有限责任公司 | 戊二酰亚胺衍生物、其用途、基于所述衍生物的药物组合物及戊二酰亚胺衍生物的制备方法 |
| CA2935717C (en) | 2014-01-03 | 2022-06-21 | University Of Southern California | Uracil isostere and pharmaceutical compositions thereof useful as deoxyuridine triphosphatase inhibitors |
| JP6836589B2 (ja) | 2015-07-08 | 2021-03-03 | シーブイ６ セラピューティクス （エヌアイ） リミテッド | ヒダントインを含むデオキシウリジントリホスファターゼ阻害剤 |
| WO2017006270A1 (en) | 2015-07-08 | 2017-01-12 | University Of Southern California | Deoxyuridine triphosphatase inhibitors |
| WO2017006283A1 (en) | 2015-07-08 | 2017-01-12 | Cv6 Therapeutics (Ni) Limited | Deoxyuridine triphosphatase inhibitors containing cyclopropano linkage |
| WO2017006271A1 (en) | 2015-07-08 | 2017-01-12 | University Of Southern California | Deoxyuridine triphosphatase inhibitors containing amino sulfonyl linkage |
| RU2610275C2 (ru) * | 2015-07-30 | 2017-02-08 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Производное глутаримидов, его применение, фармацевтическая композиция на его основе, способ его получения |
| US11395820B2 (en) * | 2016-03-16 | 2022-07-26 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Small molecules against cereblon to enhance effector t cell function |
| WO2018098209A1 (en) | 2016-11-23 | 2018-05-31 | Cv6 Therapeutics (Ni) Limited | Amino sulfonyl compounds |
| WO2018098206A1 (en) | 2016-11-23 | 2018-05-31 | Cv6 Therapeutics (Ni) Limited | Hydantoin containing deoxyuridine triphosphatase inhibitors |
| US10829457B2 (en) | 2016-11-23 | 2020-11-10 | Cv6 Therapeutics (Ni) Limited | Nitrogen ring linked deoxyuridine triphosphatase inhibitors |
| WO2018098207A1 (en) | 2016-11-23 | 2018-05-31 | Cv6 Therapeutics (Ni) Limited | Hydantoin containing deoxyuridine triphosphatase inhibitors |
| WO2018098204A1 (en) | 2016-11-23 | 2018-05-31 | Cv6 Therapeutics (Ni) Limited | 6-membered uracil isosteres |
| US11247984B2 (en) | 2017-01-05 | 2022-02-15 | Cv6 Therapeutics (Ni) Limited | Uracil containing compounds |
| MY197850A (en) * | 2017-09-07 | 2023-07-20 | Chemimmune Therapeutics Llc | Use of a glutarimide derivative to treat diseases related to the aberrant activity of cytokines |
| IL295603B2 (en) | 2017-09-22 | 2024-03-01 | Kymera Therapeutics Inc | Protein compounds and their uses |
| WO2019060693A1 (en) | 2017-09-22 | 2019-03-28 | Kymera Therapeutics, Inc. | CRBN LIGANDS AND USES THEREOF |
| MX2020006812A (es) | 2017-12-26 | 2020-11-06 | Kymera Therapeutics Inc | Degradadores de cinasas asociadas al receptor de interleucina-1 (irak) y usos de los mismos. |
| US11512080B2 (en) | 2018-01-12 | 2022-11-29 | Kymera Therapeutics, Inc. | CRBN ligands and uses thereof |
| EP3737666A4 (en) | 2018-01-12 | 2022-01-05 | Kymera Therapeutics, Inc. | PROTEIN DEGRADANTS AND USES THEREOF |
| CN107857754B (zh) * | 2018-01-15 | 2018-11-09 | 泰山医学院 | 一种化合物及其在制备预防/治疗类风湿性关节炎药物中的应用 |
| CN107903245B (zh) * | 2018-01-15 | 2018-11-13 | 青岛大学附属医院 | 一种化合物及其在制备治疗类风湿性关节炎药物中的应用 |
| WO2020010177A1 (en) | 2018-07-06 | 2020-01-09 | Kymera Therapeutics, Inc. | Tricyclic crbn ligands and uses thereof |
| EA202190248A1 (ru) | 2018-07-11 | 2021-06-16 | Х. Ли Моффитт Кэнсер Сентер Энд Рисерч Инститьют, Инк. | Димерные иммуномодулирующие соединения против механизмов на основе цереблона |
| AU2019389174A1 (en) | 2018-11-30 | 2021-07-01 | Kymera Therapeutics, Inc. | Irak degraders and uses thereof |
| MA55565A (fr) | 2019-04-05 | 2022-02-09 | Kymera Therapeutics Inc | Agents de dégradation de stat et leurs utilisations |
| KR20220145325A (ko) | 2019-12-17 | 2022-10-28 | 카이메라 쎄라퓨틱스 인코포레이티드 | Irak 분해제 및 이의 용도 |
| US11591332B2 (en) | 2019-12-17 | 2023-02-28 | Kymera Therapeutics, Inc. | IRAK degraders and uses thereof |
| CA3162502A1 (en) | 2019-12-23 | 2021-07-01 | Yi Zhang | Smarca degraders and uses thereof |
| IL296451A (en) | 2020-03-19 | 2022-11-01 | Kymera Therapeutics Inc | mdm2 joints and their uses |
| TW202210483A (zh) | 2020-06-03 | 2022-03-16 | 美商凱麥拉醫療公司 | Irak降解劑之結晶型 |
| BR112022026356A2 (pt) * | 2020-06-26 | 2023-01-17 | Valenta Intellekt Ltd | Uso de um derivado de glutarimida para tratar doenças associadas à atividade aberrante da interleucina-6 |
Family Cites Families (9)
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|---|---|---|---|---|
| US2673205A (en) * | 1951-02-13 | 1954-03-23 | Ciba Pharm Prod Inc | 3-disubstituted dioxopiperidines and the manufacture thereof |
| US3214431A (en) * | 1958-08-04 | 1965-10-26 | Pfizer & Co C | Novel glutarimides |
| US5114937A (en) * | 1989-11-28 | 1992-05-19 | Warner-Lambert Company | Renin inhibiting nonpeptides |
| GB8928043D0 (en) * | 1989-12-12 | 1990-02-14 | Pfizer Ltd | Muscarinic receptor antagonists |
| FR2745811B1 (fr) * | 1996-03-07 | 1998-05-22 | Sanofi Sa | Glutarimide disubstitue procede pour sa preparation, et son utilisation |
| US6281230B1 (en) * | 1996-07-24 | 2001-08-28 | Celgene Corporation | Isoindolines, method of use, and pharmaceutical compositions |
| DE19703763C1 (de) * | 1997-02-01 | 1998-10-01 | Gruenenthal Gmbh | Thalidomidanaloge Verbindungen aus der Klasse der Piperidin-2,6-Dione |
| DE19843793C2 (de) * | 1998-09-24 | 2000-08-03 | Gruenenthal Gmbh | Substituierte Benzamide |
| DE10002509A1 (de) * | 2000-01-21 | 2001-07-26 | Gruenenthal Gmbh | Substituierte Glutarimide |
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- 2001-01-09 CN CNB018038883A patent/CN1185215C/zh not_active Expired - Fee Related
- 2001-01-09 RU RU2002121641/04A patent/RU2278857C2/ru not_active IP Right Cessation
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- 2001-01-09 DE DE50115252T patent/DE50115252D1/de not_active Expired - Lifetime
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- 2001-01-09 AT AT01900400T patent/ATE451355T1/de not_active IP Right Cessation
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- 2001-01-09 WO PCT/EP2001/000155 patent/WO2001053261A1/de active IP Right Grant
- 2001-01-09 PT PT01900400T patent/PT1252144E/pt unknown
- 2001-01-09 BR BR0108030-0A patent/BR0108030A/pt not_active IP Right Cessation
- 2001-01-09 ES ES01900400T patent/ES2337875T3/es not_active Expired - Lifetime
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