ZA200206664B - Substituted glutarimides and use thereof IL-12 production inhibitors. - Google Patents

Substituted glutarimides and use thereof IL-12 production inhibitors. Download PDF

Info

Publication number: ZA200206664B
Authority: ZA; South Africa
Prior art keywords: group; methyl; general formula; stands; formula
Prior art date: 2000-01-21

Application number

ZA200206664A

Other languages

English (en)

Inventor

Tieno Germann

Erik Wade

Oswald Zimmer

Stefanie Frosch

Helmut Buschmann

Original Assignee

Gruenenthal Gmbh

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-01-21

Filing date

2002-08-20

Publication date

2004-01-21

2002-08-20 Application filed by Gruenenthal Gmbh filed Critical Gruenenthal Gmbh

2004-01-21 Publication of ZA200206664B publication Critical patent/ZA200206664B/en

Links

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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- 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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- A61P11/06—Antiasthmatics
- 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- 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
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
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- C07D211/88—Oxygen atoms attached in positions 2 and 6, e.g. glutarimide
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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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ZA200206664A 2000-01-21 2002-08-20 Substituted glutarimides and use thereof IL-12 production inhibitors. ZA200206664B (en)

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Application Number	Priority Date	Filing Date	Title
DE10002509A DE10002509A1 (de)	2000-01-21	2000-01-21	Substituierte Glutarimide

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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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US (2)	US6656937B2 (es)
EP (1)	EP1252144B1 (es)
JP (1)	JP2003524641A (es)
KR (1)	KR20020067614A (es)
CN (1)	CN1185215C (es)
AR (1)	AR030185A1 (es)
AT (1)	ATE451355T1 (es)
AU (1)	AU780636B2 (es)
BR (1)	BR0108030A (es)
CA (1)	CA2398061A1 (es)
CO (1)	CO5261626A1 (es)
CY (1)	CY1109784T1 (es)
DE (2)	DE10002509A1 (es)
DK (1)	DK1252144T3 (es)
ES (1)	ES2337875T3 (es)
HU (1)	HUP0204235A3 (es)
IL (1)	IL150813A0 (es)
MX (1)	MXPA02007089A (es)
NO (1)	NO323395B1 (es)
NZ (1)	NZ520759A (es)
PE (1)	PE20011067A1 (es)
PL (1)	PL356986A1 (es)
PT (1)	PT1252144E (es)
RU (1)	RU2278857C2 (es)
SI (1)	SI1252144T1 (es)
SK (1)	SK287173B6 (es)
WO (1)	WO2001053261A1 (es)
ZA (1)	ZA200206664B (es)

Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
AU2003243272A1 (en)	2002-05-22	2003-12-12	Errant Gene Therapeutics, Llc	Histone deacetylase inhibitors based on alpha-ketoepoxide 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
AU2005223481A1 (en)	2004-03-17	2005-09-29	Pfizer Products 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
MX2020005738A (es) *	2013-04-12	2021-08-13	Valenta Intellekt Ltd	Derivados de glutarimida, uso de los mismos, composicion farmaceutica basada en los mismos y metodos para producir derivados de glutarimida.
WO2015103489A1 (en)	2014-01-03	2015-07-09	University Of Southern California	Heteroatom containing deoxyuridine triphosphatase inhibitors
US10544105B2 (en)	2015-07-08	2020-01-28	Cv6 Therapeutics (Ni) Limited	Deoxyuridine triphosphatase inhibitors containing cyclopropano linkage
AU2016290987C1 (en)	2015-07-08	2023-07-20	Cv6 Therapeutics (Ni) Limited	Hydantoin containing deoxyuridine triphosphatase inhibitors
WO2017006270A1 (en)	2015-07-08	2017-01-12	University Of Southern California	Deoxyuridine triphosphatase inhibitors
US10570100B2 (en)	2015-07-08	2020-02-25	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
KR102520814B1 (ko) *	2016-03-16	2023-04-11	에이치 리 모피트 캔서 센터 앤드 리서어치 인스티튜트 아이엔씨	작동자 t 세포 기능 개선을 위한 세레브론에 대한 소분자
US10858344B2 (en)	2016-11-23	2020-12-08	Cv6 Therapeutics (Ni) Limited	Hydantoin containing deoxyuridine triphosphatase inhibitors
WO2018098208A1 (en)	2016-11-23	2018-05-31	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
US11174271B2 (en)	2016-11-23	2021-11-16	Cv6 Therapeutics (Ni) Limited	6-membered uracil isosteres
WO2018098209A1 (en)	2016-11-23	2018-05-31	Cv6 Therapeutics (Ni) Limited	Amino sulfonyl compounds
US11247984B2 (en)	2017-01-05	2022-02-15	Cv6 Therapeutics (Ni) Limited	Uracil containing compounds
GEP20227354B (en)	2017-09-07	2022-02-25	Obschestvo S Ogranichennoi Otvetstvennostiyu Pharmenterprises	Use of a glutarimide derivative to treat diseases related to the aberrant activity of cytokines
IL273432B (en)	2017-09-22	2022-09-01	Kymera Therapeutics Inc	Protein compounds and their uses
WO2019060693A1 (en)	2017-09-22	2019-03-28	Kymera Therapeutics, Inc.	CRBN LIGANDS AND USES THEREOF
IL315310A (en)	2017-12-26	2024-10-01	Kymera Therapeutics Inc	IRAK joints and used in them
US11512080B2 (en)	2018-01-12	2022-11-29	Kymera Therapeutics, Inc.	CRBN ligands and uses thereof
US11485743B2 (en)	2018-01-12	2022-11-01	Kymera Therapeutics, Inc.	Protein degraders and uses thereof
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
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
WO2020010177A1 (en)	2018-07-06	2020-01-09	Kymera Therapeutics, Inc.	Tricyclic crbn ligands and uses thereof
BR112021000395A2 (pt)	2018-07-11	2021-04-06	H. Lee Moffitt Cancer Center And Research Institute, Inc.	Compostos imunomoduladores diméricos contra mecanismos baseados em cereblon
JP2022516401A (ja)	2018-11-30	2022-02-28	カイメラセラピューティクス，インコーポレイテッド	Ｉｒａｋ分解剤およびそれらの使用
JP2022527114A (ja)	2019-04-05	2022-05-30	カイメラセラピューティクス，インコーポレイテッド	分解剤およびそれらの使用
US11591332B2 (en)	2019-12-17	2023-02-28	Kymera Therapeutics, Inc.	IRAK degraders and uses thereof
TW202136251A (zh)	2019-12-17	2021-10-01	美商凱麥拉醫療公司	Irak降解劑及其用途
US11679109B2 (en)	2019-12-23	2023-06-20	Kymera Therapeutics, Inc.	SMARCA degraders and uses thereof
MX2022011602A (es)	2020-03-19	2023-01-04	Kymera Therapeutics Inc	Degradadores de la proteína de homólogo de ratón de minuto 2 (mdm2) y usos de los mismos.
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
AU2022271290A1 (en)	2021-05-07	2023-11-23	Kymera Therapeutics, Inc.	Cdk2 degraders and uses thereof
KR20240144266A (ko)	2022-01-31	2024-10-02	카이메라 쎄라퓨틱스 인코포레이티드	Irak 분해제 및 이의 용도

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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

2000
- 2000-01-21 DE DE10002509A patent/DE10002509A1/de not_active Ceased
2001
- 2001-01-09 RU RU2002121641/04A patent/RU2278857C2/ru not_active IP Right Cessation
- 2001-01-09 AU AU25140/01A patent/AU780636B2/en not_active Ceased
- 2001-01-09 HU HU0204235A patent/HUP0204235A3/hu unknown
- 2001-01-09 KR KR1020027009243A patent/KR20020067614A/ko not_active Application Discontinuation
- 2001-01-09 EP EP01900400A patent/EP1252144B1/de not_active Expired - Lifetime
- 2001-01-09 NZ NZ520759A patent/NZ520759A/en unknown
- 2001-01-09 SI SI200130961T patent/SI1252144T1/sl unknown
- 2001-01-09 SK SK1017-2002A patent/SK287173B6/sk not_active IP Right Cessation
- 2001-01-09 ES ES01900400T patent/ES2337875T3/es not_active Expired - Lifetime
- 2001-01-09 AT AT01900400T patent/ATE451355T1/de not_active IP Right Cessation
- 2001-01-09 CN CNB018038883A patent/CN1185215C/zh not_active Expired - Fee Related
- 2001-01-09 DK DK01900400.1T patent/DK1252144T3/da active
- 2001-01-09 PT PT01900400T patent/PT1252144E/pt unknown
- 2001-01-09 JP JP2001553265A patent/JP2003524641A/ja not_active Withdrawn
- 2001-01-09 MX MXPA02007089A patent/MXPA02007089A/es active IP Right Grant
- 2001-01-09 BR BR0108030-0A patent/BR0108030A/pt not_active IP Right Cessation
- 2001-01-09 PL PL01356986A patent/PL356986A1/xx not_active Application Discontinuation
- 2001-01-09 WO PCT/EP2001/000155 patent/WO2001053261A1/de active IP Right Grant
- 2001-01-09 CA CA002398061A patent/CA2398061A1/en not_active Abandoned
- 2001-01-09 DE DE50115252T patent/DE50115252D1/de not_active Expired - Lifetime
- 2001-01-09 IL IL15081301A patent/IL150813A0/xx unknown
- 2001-01-19 AR ARP010100251A patent/AR030185A1/es unknown
- 2001-01-19 PE PE2001000061A patent/PE20011067A1/es not_active Application Discontinuation
- 2001-01-19 CO CO01003816A patent/CO5261626A1/es not_active Application Discontinuation
2002
- 2002-07-09 NO NO20023319A patent/NO323395B1/no not_active IP Right Cessation
- 2002-07-19 US US10/198,073 patent/US6656937B2/en not_active Expired - Fee Related
- 2002-08-20 ZA ZA200206664A patent/ZA200206664B/en unknown
2003
- 2003-09-03 US US10/653,188 patent/US20040048859A1/en not_active Abandoned
2010
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Also Published As

Publication number	Publication date
US6656937B2 (en)	2003-12-02
DE10002509A1 (de)	2001-07-26
EP1252144A1 (de)	2002-10-30
NZ520759A (en)	2005-09-30
CO5261626A1 (es)	2003-03-31
DE50115252D1 (de)	2010-01-21
KR20020067614A (ko)	2002-08-22
WO2001053261A1 (de)	2001-07-26
AU2514001A (en)	2001-07-31
NO20023319D0 (no)	2002-07-09
EP1252144B1 (de)	2009-12-09
AR030185A1 (es)	2003-08-13
HUP0204235A3 (en)	2005-03-29
HUP0204235A2 (hu)	2003-03-28
IL150813A0 (en)	2003-02-12
SI1252144T1 (sl)	2010-04-30
NO323395B1 (no)	2007-04-23
US20040048859A1 (en)	2004-03-11
NO20023319L (no)	2002-09-03
ATE451355T1 (de)	2009-12-15
ES2337875T3 (es)	2010-04-30
RU2002121641A (ru)	2004-01-10
JP2003524641A (ja)	2003-08-19
CN1185215C (zh)	2005-01-19
PE20011067A1 (es)	2001-12-29
CN1394201A (zh)	2003-01-29
RU2278857C2 (ru)	2006-06-27
SK287173B6 (sk)	2010-02-08
PL356986A1 (en)	2004-07-12
CA2398061A1 (en)	2001-07-26
BR0108030A (pt)	2003-01-28
PT1252144E (pt)	2010-02-03
SK10172002A3 (sk)	2003-02-04
MXPA02007089A (es)	2002-12-13
US20030064987A1 (en)	2003-04-03
DK1252144T3 (da)	2010-04-19
CY1109784T1 (el)	2014-09-10
AU780636B2 (en)	2005-04-07

Publication	Publication Date	Title
ZA200206664B (en)	2004-01-21	Substituted glutarimides and use thereof IL-12 production inhibitors.
KR101231466B1 (ko)	2013-02-07	질소 함유 복소환 유도체 및 이들을 유효 성분으로 하는약제
US7790726B2 (en)	2010-09-07	Monocyclic and bicyclic compounds and methods of use
JP3710489B2 (ja)	2005-10-26	アリールスルホニルヒドロキサム酸誘導体
CA2434937C (en)	2010-11-09	Phenyl derivatives
EA200500342A1 (ru)	2005-08-25	Гетероциклические замещённые пиперазины для лечения шизофрении
US5296604A (en)	1994-03-22	Proline derivatives and compositions for their use as inhibitors of HIV protease
US7098212B2 (en)	2006-08-29	Piperazine derivatives
AP1860A (en)	2008-07-02	Aryl fused azapolycyclic compounds.
ES2137998T3 (es)	2000-01-01	Nuevos derivados de aminoacidos, procedimiento para su preparacion y composiciones farmaceuticas que contienen estos compuestos.
JP2013537533A (ja)	2013-10-03	マトリックスメタロプロテイナーゼ阻害剤
AU2003242941A1 (en)	2004-02-09	Piperidine derivatives and their use as selective inhibitors of mip-1alpha binding to its receptor ccr1
MXPA05004650A (es)	2005-06-08	Procedimientos de uso de derivados de piperazina.
HUP0003577A2 (hu)	2001-09-28	Tetrahidro-gamma-karbolinok, eljárás előállításukra, alkalmazásuk és az ezeket tartalmazó gyógyszerkészítmények
ATE141606T1 (de)	1996-09-15	Cephemverbindungen und verfahren zu ihrer herstellung
BR112012003255B1 (pt)	2018-10-23	processo de abertura de anel de lactonas e lactamas
CA2447687A1 (en)	2002-12-19	Substituted 1-benzazepines and derivatives thereof
PT732332E (pt)	2002-06-28	Benzotienilpiperazinas substituidas sua utilizacao como medicamentos e processos para a sua preparacao
EP1441726A1 (de)	2004-08-04	Derivate des phenoxy-n-'4-(isothiazolidin-1,1-dioxid-2yl)pheny!-valerian-säureamids und andere verbindungen als inhibitoren des koagulationsfaktors xa zur behandlung von thromboembolischen erkrankungen und tumoren
US4731369A (en)	1988-03-15	Amides and esters of 2-(N-(hydroxypiperidinoalkyl) and (hydroxypyrrolidinoalkyl)-aminosulfonyl)-6-nitrobenzoic acids useful as adjuncts to radiation therapy
TR200102639T2 (tr)	2002-02-21	Yeni morfolin türevleri, bunları hazırlamak için proses ve bunları içeren farmasötik kompozisyonlar.
MA27492A1 (fr)	2005-08-01	Nouveaux derives antagonistes du recepteur de la vitronectine, leur procede de preparation, leur application comme medicaments et les compositions pharmaceutiques les renfermant
ZA200300218B (en)	2004-06-25	Novel N-(2-phenyl-3-aminopropyl)naphtamides.
US3301862A (en)	1967-01-31	Nu-cyclopropyl, amides of 4-phenyl piperidino-alkanoic acids
ATE317380T1 (de)	2006-02-15	Bernsteinsäurederivate