ZA200405780B - Piperidine-2,6-diones that are heterocyclically substituted in position 3. - Google Patents
Piperidine-2,6-diones that are heterocyclically substituted in position 3. Download PDFInfo
- Publication number
- ZA200405780B ZA200405780B ZA200405780A ZA200405780A ZA200405780B ZA 200405780 B ZA200405780 B ZA 200405780B ZA 200405780 A ZA200405780 A ZA 200405780A ZA 200405780 A ZA200405780 A ZA 200405780A ZA 200405780 B ZA200405780 B ZA 200405780B
- Authority
- ZA
- South Africa
- Prior art keywords
- piperidine
- dione
- general formula
- quinazolin
- compounds
- Prior art date
Links
- 150000005459 piperidine-2,6-diones Chemical class 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 17
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 14
- -1 hydrochloride 3-(7-fluoro-4H-quinazolin-3-yl)piperidine-2,6-dione Chemical compound 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 208000023275 Autoimmune disease Diseases 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 230000002757 inflammatory effect Effects 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 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 5
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 claims description 5
- 230000000771 oncological effect Effects 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 230000002489 hematologic effect Effects 0.000 claims description 4
- 230000002519 immonomodulatory effect Effects 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 238000011321 prophylaxis 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
- 125000001424 substituent group Chemical group 0.000 claims description 4
- GOAYEVLXZBMEJI-UHFFFAOYSA-N 3-(7-chloro-4h-quinazolin-3-yl)piperidine-2,6-dione Chemical compound C1=NC2=CC(Cl)=CC=C2CN1C1CCC(=O)NC1=O GOAYEVLXZBMEJI-UHFFFAOYSA-N 0.000 claims description 3
- 238000006268 reductive amination reaction Methods 0.000 claims description 3
- UZUYAWODKGEDNP-UHFFFAOYSA-N 3-(2-hydroxy-2,4-dihydro-1H-quinazolin-3-yl)piperidine-2,6-dione 3-(6-methoxy-4H-quinazolin-3-yl)piperidine-2,6-dione hydrochloride Chemical compound COC=1C=C2CN(C=NC2=CC1)C1C(NC(CC1)=O)=O.OC1NC2=CC=CC=C2CN1C1C(NC(CC1)=O)=O.Cl UZUYAWODKGEDNP-UHFFFAOYSA-N 0.000 claims description 2
- GDOIZNGKHQRCCX-UHFFFAOYSA-N 3-(4h-quinazolin-3-yl)piperidine-2,6-dione Chemical compound O=C1NC(=O)CCC1N1C=NC2=CC=CC=C2C1 GDOIZNGKHQRCCX-UHFFFAOYSA-N 0.000 claims description 2
- NBFCFQNQDZAMGR-UHFFFAOYSA-N 3-(6-chloro-4h-quinazolin-3-yl)piperidine-2,6-dione;hydrobromide Chemical compound Br.C1C2=CC(Cl)=CC=C2N=CN1C1CCC(=O)NC1=O NBFCFQNQDZAMGR-UHFFFAOYSA-N 0.000 claims description 2
- MSOWBXJQQSEVIY-UHFFFAOYSA-N 3-(8-methoxy-4h-quinazolin-3-yl)piperidine-2,6-dione Chemical compound C1=NC=2C(OC)=CC=CC=2CN1C1CCC(=O)NC1=O MSOWBXJQQSEVIY-UHFFFAOYSA-N 0.000 claims description 2
- CJFHQJDFNSXAOC-UHFFFAOYSA-N 3-bromopiperidin-2-one Chemical class BrC1CCCNC1=O CJFHQJDFNSXAOC-UHFFFAOYSA-N 0.000 claims description 2
- RYSICGXZRVMXDP-UHFFFAOYSA-N 3-bromopiperidine-2,6-dione Chemical class BrC1CCC(=O)NC1=O RYSICGXZRVMXDP-UHFFFAOYSA-N 0.000 claims description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- 238000007171 acid catalysis Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 238000006344 deformylation reaction Methods 0.000 claims description 2
- 150000003948 formamides Chemical class 0.000 claims description 2
- 238000006170 formylation reaction Methods 0.000 claims description 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims description 2
- 238000005658 halogenation reaction Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 239000003586 protic polar solvent Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 2
- FGZKRRBIHMYDDA-UHFFFAOYSA-N 3-(5-chloro-4H-quinazolin-3-yl)piperidine-2,6-dione 3-(8-chloro-4H-quinazolin-3-yl)piperidine-2,6-dione 3-(6-fluoro-4H-quinazolin-3-yl)piperidine-2,6-dione hydrochloride Chemical compound FC=1C=C2CN(C=NC2=CC1)C1C(NC(CC1)=O)=O.ClC=1C=CC=C2CN(C=NC12)C1C(NC(CC1)=O)=O.ClC1=C2CN(C=NC2=CC=C1)C1C(NC(CC1)=O)=O.Cl FGZKRRBIHMYDDA-UHFFFAOYSA-N 0.000 claims 1
- XRGCSNBWPPSDIW-UHFFFAOYSA-N 3-(5-methyl-4h-quinazolin-3-yl)piperidine-2,6-dione Chemical compound C1C=2C(C)=CC=CC=2N=CN1C1CCC(=O)NC1=O XRGCSNBWPPSDIW-UHFFFAOYSA-N 0.000 claims 1
- VKASXHUGFZYSIY-UHFFFAOYSA-N N1=CN(CCC2=C1C=CC=C2)C2C(NC(CC2)=O)=O.CC2(C(NC(CC2)=O)=O)N2C=NC1=CC=CC=C1C2 Chemical compound N1=CN(CCC2=C1C=CC=C2)C2C(NC(CC2)=O)=O.CC2(C(NC(CC2)=O)=O)N2C=NC1=CC=CC=C1C2 VKASXHUGFZYSIY-UHFFFAOYSA-N 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 230000006198 deformylation Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 102000013462 Interleukin-12 Human genes 0.000 description 19
- 108010065805 Interleukin-12 Proteins 0.000 description 19
- 229940117681 interleukin-12 Drugs 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- 206010061218 Inflammation Diseases 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 10
- 210000001616 monocyte Anatomy 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 210000001744 T-lymphocyte Anatomy 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 210000002540 macrophage Anatomy 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 230000004054 inflammatory process Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 description 4
- UDRDQLILQHGDOE-UHFFFAOYSA-N 3-(4h-quinazolin-3-yl)piperidine-2,6-dione;hydrobromide Chemical compound Br.O=C1NC(=O)CCC1N1C=NC2=CC=CC=C2C1 UDRDQLILQHGDOE-UHFFFAOYSA-N 0.000 description 4
- 102000004127 Cytokines Human genes 0.000 description 4
- 108090000695 Cytokines Proteins 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000002158 endotoxin Substances 0.000 description 4
- 229920006008 lipopolysaccharide Polymers 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 229960003433 thalidomide Drugs 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 208000028774 intestinal disease Diseases 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 201000004624 Dermatitis Diseases 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 208000034578 Multiple myelomas Diseases 0.000 description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 206010070517 Type 2 lepra reaction Diseases 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 210000000612 antigen-presenting cell Anatomy 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 206010012601 diabetes mellitus Diseases 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000006196 drop Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 2
- 239000002955 immunomodulating agent Substances 0.000 description 2
- 229940121354 immunomodulator Drugs 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000019734 interleukin-12 production Effects 0.000 description 2
- 201000006417 multiple sclerosis Diseases 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 230000008506 pathogenesis Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 208000017520 skin disease Diseases 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- MUDGPJDWJIFUDB-UHFFFAOYSA-N (2-amino-4-chlorophenyl)methanol Chemical compound NC1=CC(Cl)=CC=C1CO MUDGPJDWJIFUDB-UHFFFAOYSA-N 0.000 description 1
- PSJDKILTGSOUQU-UHFFFAOYSA-N 3-(2-hydroxy-2,4-dihydro-1h-quinazolin-3-yl)piperidine-2,6-dione Chemical compound OC1NC2=CC=CC=C2CN1C1CCC(=O)NC1=O PSJDKILTGSOUQU-UHFFFAOYSA-N 0.000 description 1
- MGKRQXJZZBQPAT-UHFFFAOYSA-N 3-(4h-benzo[g]quinazolin-3-yl)piperidine-2,6-dione Chemical compound O=C1NC(=O)CCC1N1C=NC2=CC3=CC=CC=C3C=C2C1 MGKRQXJZZBQPAT-UHFFFAOYSA-N 0.000 description 1
- WNFZKWLFKQICMB-UHFFFAOYSA-N 3-(5-amino-4h-quinazolin-3-yl)piperidine-2,6-dione Chemical compound C1C=2C(N)=CC=CC=2N=CN1C1CCC(=O)NC1=O WNFZKWLFKQICMB-UHFFFAOYSA-N 0.000 description 1
- MGJAIEVMDMPLQC-UHFFFAOYSA-N 3-(5-chloro-4H-quinazolin-3-yl)piperidine-2,6-dione 3-(7-fluoro-4H-quinazolin-3-yl)piperidine-2,6-dione hydrobromide Chemical compound FC1=CC=C2CN(C=NC2=C1)C1C(NC(CC1)=O)=O.ClC1=C2CN(C=NC2=CC=C1)C1C(NC(CC1)=O)=O.Br MGJAIEVMDMPLQC-UHFFFAOYSA-N 0.000 description 1
- WKKHPSWWNPEOGD-UHFFFAOYSA-N 3-(5-fluoro-4H-quinazolin-3-yl)piperidine-2,6-dione hydrochloride Chemical compound FC1=C2CN(C=NC2=CC=C1)C1C(NC(CC1)=O)=O.Cl WKKHPSWWNPEOGD-UHFFFAOYSA-N 0.000 description 1
- KSXXBXVPMHJCPG-UHFFFAOYSA-N 3-(5-nitro-4h-quinazolin-3-yl)piperidine-2,6-dione Chemical compound C1C=2C([N+](=O)[O-])=CC=CC=2N=CN1C1CCC(=O)NC1=O KSXXBXVPMHJCPG-UHFFFAOYSA-N 0.000 description 1
- FHRANXHBVVQNKM-UHFFFAOYSA-N 3-(6-fluoro-4h-quinazolin-3-yl)piperidine-2,6-dione Chemical compound C1C2=CC(F)=CC=C2N=CN1C1CCC(=O)NC1=O FHRANXHBVVQNKM-UHFFFAOYSA-N 0.000 description 1
- YBOJWAGOEBFPEJ-UHFFFAOYSA-N 3-(7-amino-4h-quinazolin-3-yl)piperidine-2,6-dione Chemical compound C1=NC2=CC(N)=CC=C2CN1C1CCC(=O)NC1=O YBOJWAGOEBFPEJ-UHFFFAOYSA-N 0.000 description 1
- CKDFWWVMYYARAH-UHFFFAOYSA-N 3-methyl-3-(4h-quinazolin-3-yl)piperidine-2,6-dione Chemical compound C1C2=CC=CC=C2N=CN1C1(C)CCC(=O)NC1=O CKDFWWVMYYARAH-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
- 206010003011 Appendicitis Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 108020000946 Bacterial DNA Proteins 0.000 description 1
- 101100273064 Brassica oleracea var. botrytis CAL-B gene Proteins 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
- 206010007558 Cardiac failure chronic Diseases 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 206010009944 Colon cancer Diseases 0.000 description 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 1
- 208000013586 Complex regional pain syndrome type 1 Diseases 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 208000001640 Fibromyalgia Diseases 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 1
- 102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 1
- 102000012153 HLA-B27 Antigen Human genes 0.000 description 1
- 108010061486 HLA-B27 Antigen Proteins 0.000 description 1
- 208000023661 Haematological disease Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 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
- 102000000589 Interleukin-1 Human genes 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- 102000004889 Interleukin-6 Human genes 0.000 description 1
- 108090001005 Interleukin-6 Proteins 0.000 description 1
- 102000004890 Interleukin-8 Human genes 0.000 description 1
- 108090001007 Interleukin-8 Proteins 0.000 description 1
- 208000007766 Kaposi sarcoma Diseases 0.000 description 1
- 108010028921 Lipopeptides Proteins 0.000 description 1
- 206010027202 Meningitis bacterial Diseases 0.000 description 1
- 208000034493 Mucous membrane disease Diseases 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 206010062207 Mycobacterial infection Diseases 0.000 description 1
- 208000001388 Opportunistic Infections Diseases 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 201000001947 Reflex Sympathetic Dystrophy Diseases 0.000 description 1
- 208000006265 Renal cell carcinoma Diseases 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- 201000010001 Silicosis Diseases 0.000 description 1
- 108700012920 TNF Proteins 0.000 description 1
- 206010043275 Teratogenicity Diseases 0.000 description 1
- 208000024770 Thyroid neoplasm Diseases 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000002424 anti-apoptotic effect Effects 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 238000003782 apoptosis assay Methods 0.000 description 1
- 230000006907 apoptotic process Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 210000003719 b-lymphocyte Anatomy 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 201000009904 bacterial meningitis Diseases 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- YLNWQVNIGOAHJP-UHFFFAOYSA-N benzyl n-(2,6-dioxopiperidin-3-yl)-n-[(2-formamidophenyl)methyl]carbamate Chemical compound O=CNC1=CC=CC=C1CN(C(=O)OCC=1C=CC=CC=1)C1C(=O)NC(=O)CC1 YLNWQVNIGOAHJP-UHFFFAOYSA-N 0.000 description 1
- ZXSULZJBOZFWNR-UHFFFAOYSA-N benzyl n-[(4-chloro-2-formamidophenyl)methyl]-n-(2,6-dioxopiperidin-3-yl)carbamate Chemical compound O=CNC1=CC(Cl)=CC=C1CN(C(=O)OCC=1C=CC=CC=1)C1C(=O)NC(=O)CC1 ZXSULZJBOZFWNR-UHFFFAOYSA-N 0.000 description 1
- FHRRJZZGSJXPRQ-UHFFFAOYSA-N benzyl phenylmethoxycarbonyl carbonate Chemical compound C=1C=CC=CC=1COC(=O)OC(=O)OCC1=CC=CC=C1 FHRRJZZGSJXPRQ-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000009134 cell regulation Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007910 chewable tablet Substances 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- ZFLAEHBSVFWEHW-UHFFFAOYSA-N cyanomethyl formate Chemical compound O=COCC#N ZFLAEHBSVFWEHW-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 229960003957 dexamethasone Drugs 0.000 description 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 231100000029 gastro-duodenal ulcer Toxicity 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 208000005017 glioblastoma Diseases 0.000 description 1
- 208000024908 graft versus host disease Diseases 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 201000010536 head and neck cancer Diseases 0.000 description 1
- 208000014829 head and neck neoplasm Diseases 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 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
- 230000004957 immunoregulator effect Effects 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000031261 interleukin-10 production Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 206010023332 keratitis Diseases 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 210000004698 lymphocyte Anatomy 0.000 description 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 239000013586 microbial product Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 208000027531 mycobacterial infectious disease Diseases 0.000 description 1
- IUBZZHIYWSOFKE-UHFFFAOYSA-N n-(5-chloro-2-formylphenyl)formamide Chemical compound ClC1=CC=C(C=O)C(NC=O)=C1 IUBZZHIYWSOFKE-UHFFFAOYSA-N 0.000 description 1
- MVJKSYGXALJDFB-UHFFFAOYSA-N n-[2-[[(2,6-dioxopiperidin-3-yl)amino]methyl]phenyl]formamide Chemical compound O=CNC1=CC=CC=C1CNC1C(=O)NC(=O)CC1 MVJKSYGXALJDFB-UHFFFAOYSA-N 0.000 description 1
- ZHCISTXXKPDTLU-UHFFFAOYSA-N n-[5-chloro-2-[[(2,6-dioxopiperidin-3-yl)amino]methyl]phenyl]formamide Chemical compound O=CNC1=CC(Cl)=CC=C1CNC1C(=O)NC(=O)CC1 ZHCISTXXKPDTLU-UHFFFAOYSA-N 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 201000001119 neuropathy Diseases 0.000 description 1
- 230000007823 neuropathy Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000012261 overproduction Methods 0.000 description 1
- 201000002528 pancreatic cancer Diseases 0.000 description 1
- 208000008443 pancreatic carcinoma Diseases 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 206010034674 peritonitis Diseases 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000005522 programmed cell death Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000010410 reperfusion Effects 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100000211 teratogenicity Toxicity 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 230000000699 topical effect Effects 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10163595A DE10163595A1 (de) | 2001-12-21 | 2001-12-21 | In 3-Position heterocyclisch substituierte Piperidin-2,6-dione |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200405780B true ZA200405780B (en) | 2005-07-26 |
Family
ID=7710600
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200405780A ZA200405780B (en) | 2001-12-21 | 2004-07-20 | Piperidine-2,6-diones that are heterocyclically substituted in position 3. |
Country Status (27)
Country | Link |
---|---|
US (1) | US7183274B2 (sl) |
EP (1) | EP1456197B1 (sl) |
JP (1) | JP2005516953A (sl) |
KR (1) | KR20040068325A (sl) |
CN (1) | CN1620448A (sl) |
AR (1) | AR037963A1 (sl) |
AT (1) | ATE355285T1 (sl) |
AU (1) | AU2002364286A1 (sl) |
BR (1) | BR0215337A (sl) |
CA (1) | CA2471079A1 (sl) |
CY (1) | CY1106540T1 (sl) |
DE (2) | DE10163595A1 (sl) |
DK (1) | DK1456197T3 (sl) |
EC (1) | ECSP045161A (sl) |
ES (1) | ES2282514T3 (sl) |
HU (1) | HUP0402477A2 (sl) |
IL (1) | IL162619A0 (sl) |
MX (1) | MXPA04006120A (sl) |
NO (1) | NO20042946L (sl) |
NZ (1) | NZ533995A (sl) |
PE (1) | PE20030745A1 (sl) |
PL (1) | PL371028A1 (sl) |
PT (1) | PT1456197E (sl) |
RU (1) | RU2004122633A (sl) |
SI (1) | SI1456197T1 (sl) |
WO (1) | WO2003053956A1 (sl) |
ZA (1) | ZA200405780B (sl) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102004026703A1 (de) * | 2004-05-28 | 2005-12-29 | Grünenthal GmbH | Verfahren zur Herstellung von in 3-Position heterocyclisch substituierten Piperidin-2,6-dionen |
DE102005057912A1 (de) | 2005-12-02 | 2007-07-19 | Grünenthal GmbH | In 3-Position heterocyclisch substituierte Pyrrolidin(thi)one |
KR200484781Y1 (ko) | 2017-07-04 | 2017-10-25 | 김정래 | 지퍼손잡이 보호장치 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2163410T3 (es) * | 1992-07-29 | 2002-02-01 | Merck Sharp & Dohme | Derivados de benzodiazepina. |
JPH09500134A (ja) * | 1993-07-16 | 1997-01-07 | メルク エンド カンパニー インコーポレーテッド | ベンゾオキサジノンおよびベンゾピリミジノンピペリジニル早産防止オキシトシン受容体拮抗剤 |
DE19843793C2 (de) * | 1998-09-24 | 2000-08-03 | Gruenenthal Gmbh | Substituierte Benzamide |
WO2000072836A2 (en) | 1999-05-27 | 2000-12-07 | The Rockefeller University | Methods of promoting or enhancing interleukin-12 production through administration of thalidomide |
US6767926B1 (en) * | 1999-10-12 | 2004-07-27 | Temple University - Of The Commonwealth System Of Higher Education | Method for protecting normal cells from cytotoxicity of chemotherapeutic agents |
DE19957342A1 (de) | 1999-11-29 | 2001-05-31 | Gruenenthal Gmbh | Verfahren zur Behandlung und/oder Prophylaxe von IL-12-bedingten Erkrankungen |
DE10002509A1 (de) * | 2000-01-21 | 2001-07-26 | Gruenenthal Gmbh | Substituierte Glutarimide |
DE10250082A1 (de) * | 2002-10-25 | 2004-05-13 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Ausgewählte CGRP-Antagonisten, Verfahren zu deren Herstellung sowie deren Verwendung als Arzneimittel |
-
2001
- 2001-12-21 DE DE10163595A patent/DE10163595A1/de not_active Withdrawn
-
2002
- 2002-12-18 DK DK02799058T patent/DK1456197T3/da active
- 2002-12-18 AT AT02799058T patent/ATE355285T1/de active
- 2002-12-18 HU HU0402477A patent/HUP0402477A2/hu unknown
- 2002-12-18 DE DE50209613T patent/DE50209613D1/de not_active Expired - Lifetime
- 2002-12-18 CN CNA028281519A patent/CN1620448A/zh active Pending
- 2002-12-18 MX MXPA04006120A patent/MXPA04006120A/es active IP Right Grant
- 2002-12-18 WO PCT/EP2002/014447 patent/WO2003053956A1/de active IP Right Grant
- 2002-12-18 SI SI200230543T patent/SI1456197T1/sl unknown
- 2002-12-18 AU AU2002364286A patent/AU2002364286A1/en not_active Abandoned
- 2002-12-18 RU RU2004122633/04A patent/RU2004122633A/ru not_active Application Discontinuation
- 2002-12-18 CA CA002471079A patent/CA2471079A1/en not_active Abandoned
- 2002-12-18 JP JP2003554672A patent/JP2005516953A/ja not_active Withdrawn
- 2002-12-18 NZ NZ533995A patent/NZ533995A/en unknown
- 2002-12-18 ES ES02799058T patent/ES2282514T3/es not_active Expired - Lifetime
- 2002-12-18 IL IL16261902A patent/IL162619A0/xx unknown
- 2002-12-18 EP EP02799058A patent/EP1456197B1/de not_active Expired - Lifetime
- 2002-12-18 PT PT02799058T patent/PT1456197E/pt unknown
- 2002-12-18 BR BR0215337-8A patent/BR0215337A/pt not_active IP Right Cessation
- 2002-12-18 KR KR10-2004-7009844A patent/KR20040068325A/ko not_active Application Discontinuation
- 2002-12-18 PL PL02371028A patent/PL371028A1/xx not_active Application Discontinuation
- 2002-12-20 AR ARP020105052A patent/AR037963A1/es not_active Application Discontinuation
-
2003
- 2003-01-06 PE PE2003000023A patent/PE20030745A1/es not_active Application Discontinuation
-
2004
- 2004-06-17 EC EC2004005161A patent/ECSP045161A/es unknown
- 2004-06-21 US US10/871,522 patent/US7183274B2/en not_active Expired - Fee Related
- 2004-07-12 NO NO20042946A patent/NO20042946L/no not_active Application Discontinuation
- 2004-07-20 ZA ZA200405780A patent/ZA200405780B/en unknown
-
2007
- 2007-04-26 CY CY20071100555T patent/CY1106540T1/el unknown
Also Published As
Publication number | Publication date |
---|---|
SI1456197T1 (sl) | 2007-08-31 |
JP2005516953A (ja) | 2005-06-09 |
PL371028A1 (en) | 2005-06-13 |
NZ533995A (en) | 2006-11-30 |
WO2003053956A1 (de) | 2003-07-03 |
US20050020581A1 (en) | 2005-01-27 |
PT1456197E (pt) | 2007-03-30 |
EP1456197A1 (de) | 2004-09-15 |
AU2002364286A1 (en) | 2003-07-09 |
DK1456197T3 (da) | 2007-06-11 |
ATE355285T1 (de) | 2006-03-15 |
CY1106540T1 (el) | 2012-01-25 |
ES2282514T3 (es) | 2007-10-16 |
BR0215337A (pt) | 2004-11-16 |
CA2471079A1 (en) | 2003-07-03 |
DE10163595A1 (de) | 2003-08-07 |
CN1620448A (zh) | 2005-05-25 |
NO20042946L (no) | 2004-09-20 |
AR037963A1 (es) | 2004-12-22 |
KR20040068325A (ko) | 2004-07-30 |
EP1456197B1 (de) | 2007-02-28 |
IL162619A0 (en) | 2005-11-20 |
RU2004122633A (ru) | 2005-06-10 |
DE50209613D1 (de) | 2007-04-12 |
US7183274B2 (en) | 2007-02-27 |
MXPA04006120A (es) | 2004-11-01 |
PE20030745A1 (es) | 2003-09-05 |
ECSP045161A (es) | 2004-08-27 |
HUP0402477A2 (hu) | 2005-05-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP3464245B1 (en) | Benzazepine dicarboxamide compounds with tertiary amide function | |
EP2964223B1 (en) | Compounds inhibiting leucine-rich repeat kinase enzyme activity | |
US5834493A (en) | Indole derivatives as 5-HT1A and/or 5-HT2 ligands | |
JP3449611B2 (ja) | 掻痒症の治療のための新規な4−アリールピペリジン誘導体 | |
AU688120B2 (en) | New piperidine compounds, process for their preparation and the pharmaceutical compositions which contain them | |
EP2176250B1 (en) | Substituted heteroarylpiperidine derivatives as melanocortin-4 receptor modulators | |
JP2002509148A (ja) | Orl1−レセプターアゴニストとしての4−(2−ケト−1−ベンズイミダゾリニル)ピペリジン化合物 | |
JPH03169860A (ja) | 置換n―ベンジルピペリジンアミド | |
EP1436283B1 (en) | Method for preparing pyrimidinone compound and pharmaceutically acceptable salts thereof | |
JP3889623B2 (ja) | 置換ジアゼパン類 | |
KR20040002386A (ko) | 아편양 수용체 친화성을 갖는3-아자비사이클로(3.1.0)헥산 유도체 | |
EP1960387B1 (fr) | Derives de isoquinoline et benzo[h]isoquinoline, leur preparation et leur utilisation en therapeutique en tant qu antagonistes du recepteur de l histamine h3 | |
ZA200405780B (en) | Piperidine-2,6-diones that are heterocyclically substituted in position 3. | |
JPH08501287A (ja) | アミド誘導体 | |
NZ248776A (en) | Imidazole-substituted piperidine derivatives; pharmaceutical compositions and preparatory methods | |
EP1539738B1 (fr) | Nouveaux derives d'aryl-4-halogeno-4- heteroarylmethylamino)-methyl -piperidin-1-yl-methanone,leur procede de preparation et leur utilisation a titre de medicaments | |
US5508400A (en) | Preparation of cyclic urea compounds | |
IL103595A (en) | 2-pyrazinyl ethyl amine derivatives, process for their preparation and pharmaceutical compositions containing them | |
JPH037280A (ja) | 新規ベンゾチオピラニルアミン | |
EP1318983B1 (en) | Substituted imidazoles as histamine h1 and h3 agonists or antagonists | |
KR20010031724A (ko) | 페닐-알킬-이미다졸 유형의 h₃ 수용체 리간드 | |
JP2005516953A6 (ja) | 3−位がヘテロ環によって置換されたピペリジン−2,6−ジオン | |
EP2519507A1 (en) | Amino alcohol derivatives and their therapeutic activities | |
JPWO2005030722A1 (ja) | N−置換−n−(4−ピペリジニル)アミド誘導体 | |
ZA200407381B (en) | 1-phenyl-2-heteroaryl-substituted benzimidazole derivatives the use thereof for producing drugs used in the treatment of immunological diseases |