HUP0500920A2 - Oxadiazole derivatives, process for their preparation and their use - Google Patents

Oxadiazole derivatives, process for their preparation and their use Download PDF

Info

Publication number: HUP0500920A2
Authority: HU; Hungary
Prior art keywords: oxadiazol; alkyl; group; chlorophenyl; piperidin
Prior art date: 2005-10-05

Application number

HU0500920A

Other languages

English (en)

Hungarian (hu)

Inventor

Krisztina Dr Gal

Csaba Weber

Gabor Andras Wagner

Attila Dr Horvath

Gyoergyne Dr Nyeki

Monika Dr Vastag

Gyoergy Dr Keserue

Original Assignee

Richter Gedeon Nyrt

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.)

2005-10-05

Filing date

2005-10-05

Publication date

2007-07-30

2005-10-05 Application filed by Richter Gedeon Nyrt filed Critical Richter Gedeon Nyrt

2005-10-05 Priority to HU0500920A priority Critical patent/HUP0500920A2/hu

2005-12-28 Publication of HU0500920D0 publication Critical patent/HU0500920D0/hu

2006-10-05 Priority to PCT/HU2006/000087 priority patent/WO2007039781A2/fr

2007-07-30 Publication of HUP0500920A2 publication Critical patent/HUP0500920A2/hu

Links

238000000034 method Methods 0.000 title claims description 44
238000002360 preparation method Methods 0.000 title claims description 23
230000008569 process Effects 0.000 title claims description 7
150000004866 oxadiazoles Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 152
-1 (R) {2- [3-(3-chlorophenyl)- [1,2,4] oxadiazol-5-yl] -pyrrolidin-1-yl} -(furan-2-yl)-methanone Chemical compound 0.000 claims description 60
125000000217 alkyl group Chemical group 0.000 claims description 43
150000003839 salts Chemical class 0.000 claims description 37
108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims description 36
102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims description 36
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
208000035475 disorder Diseases 0.000 claims description 31
239000002253 acid Substances 0.000 claims description 27
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 24
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 23
230000001404 mediated effect Effects 0.000 claims description 23
239000004480 active ingredient Substances 0.000 claims description 20
230000002265 prevention Effects 0.000 claims description 19
208000002193 Pain Diseases 0.000 claims description 18
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 18
125000000304 alkynyl group Chemical group 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
125000001072 heteroaryl group Chemical group 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 13
229910052717 sulfur Inorganic materials 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 11
150000007513 acids Chemical class 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
125000004430 oxygen atom Chemical group O* 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 9
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 9
125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 9
208000012902 Nervous system disease Diseases 0.000 claims description 9
125000001589 carboacyl group Chemical group 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
125000004966 cyanoalkyl group Chemical group 0.000 claims description 9
125000004043 oxo group Chemical group O=* 0.000 claims description 9
125000004434 sulfur atom Chemical group 0.000 claims description 9
125000003545 alkoxy group Chemical group 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
208000020016 psychiatric disease Diseases 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
208000000094 Chronic Pain Diseases 0.000 claims description 7
208000005298 acute pain Diseases 0.000 claims description 7
208000018360 neuromuscular disease Diseases 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
210000001635 urinary tract Anatomy 0.000 claims description 7
230000001684 chronic effect Effects 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
230000001225 therapeutic effect Effects 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 5
125000000335 thiazolyl group Chemical group 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 4
239000000969 carrier Substances 0.000 claims description 4
125000000168 pyrrolyl group Chemical group 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
125000000842 isoxazolyl group Chemical group 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Chemical group 0.000 claims description 3
125000003373 pyrazinyl group Chemical group 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 3
125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
XOCWVXGWDNXBHY-UHFFFAOYSA-N 1-[2-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-2-methoxyethanone Chemical compound COCC(=O)N1CCCC1C1=NC(C=2C=C(Cl)C=CC=2)=NO1 XOCWVXGWDNXBHY-UHFFFAOYSA-N 0.000 claims description 2
HURZIDKLDWMXQO-UHFFFAOYSA-N 1-[3-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-2-methylpropan-1-one Chemical compound C1N(C(=O)C(C)C)CCCC1C1=NC(C=2C=C(Cl)C=CC=2)=NO1 HURZIDKLDWMXQO-UHFFFAOYSA-N 0.000 claims description 2
JZLUAPQUEFOVBU-UHFFFAOYSA-N 2-methoxy-1-[2-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]ethanone Chemical compound COCC(=O)N1CCCC1C1=NC(C=2C=C(C)C=CC=2)=NO1 JZLUAPQUEFOVBU-UHFFFAOYSA-N 0.000 claims description 2
OOINIBJVKPDFHK-UHFFFAOYSA-N 2-methyl-1-[2-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]propan-1-one Chemical compound CC(C)C(=O)N1CCCCC1C1=NC(C=2C=C(C)C=CC=2)=NO1 OOINIBJVKPDFHK-UHFFFAOYSA-N 0.000 claims description 2
UMKYTYRPUAXZHB-UHFFFAOYSA-N [2-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-(furan-2-yl)methanone Chemical compound ClC1=CC=CC(C=2N=C(ON=2)C2N(CCC2)C(=O)C=2OC=CC=2)=C1 UMKYTYRPUAXZHB-UHFFFAOYSA-N 0.000 claims description 2
PFVHJRXWVNVUQZ-UHFFFAOYSA-N [2-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-thiophen-2-ylmethanone Chemical compound ClC1=CC=CC(C=2N=C(ON=2)C2N(CCC2)C(=O)C=2SC=CC=2)=C1 PFVHJRXWVNVUQZ-UHFFFAOYSA-N 0.000 claims description 2
GWDIGLOPVOMWHT-UHFFFAOYSA-N [2-[3-(3-methoxyphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-thiophen-2-ylmethanone Chemical compound COC1=CC=CC(C=2N=C(ON=2)C2N(CCCC2)C(=O)C=2SC=CC=2)=C1 GWDIGLOPVOMWHT-UHFFFAOYSA-N 0.000 claims description 2
SVDUTEHSNVPABA-UHFFFAOYSA-N [3-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-cyclobutylmethanone Chemical compound ClC1=CC=CC(C=2N=C(ON=2)C2CN(CCC2)C(=O)C2CCC2)=C1 SVDUTEHSNVPABA-UHFFFAOYSA-N 0.000 claims description 2
MBAGGIFLYQBGOQ-UHFFFAOYSA-N cyclobutyl-[2-[3-(3-methoxyphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound COC1=CC=CC(C=2N=C(ON=2)C2N(CCCC2)C(=O)C2CCC2)=C1 MBAGGIFLYQBGOQ-UHFFFAOYSA-N 0.000 claims description 2
LGGQAFOBZFUFIL-UHFFFAOYSA-N cyclobutyl-[2-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=CC=CC(C=2N=C(ON=2)C2N(CCCC2)C(=O)C2CCC2)=C1 LGGQAFOBZFUFIL-UHFFFAOYSA-N 0.000 claims description 2
DAPUEJFIPORGIT-UHFFFAOYSA-N cyclopentyl-[2-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=CC=CC(C=2N=C(ON=2)C2N(CCCC2)C(=O)C2CCCC2)=C1 DAPUEJFIPORGIT-UHFFFAOYSA-N 0.000 claims description 2
WWHUAHHBOXKYNY-UHFFFAOYSA-N cyclopropyl-[2-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=CC=CC(C=2N=C(ON=2)C2N(CCCC2)C(=O)C2CC2)=C1 WWHUAHHBOXKYNY-UHFFFAOYSA-N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
ODWBGWGUAJZGNJ-UHFFFAOYSA-N furan-2-yl-[2-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=CC=CC(C=2N=C(ON=2)C2N(CCCC2)C(=O)C=2OC=CC=2)=C1 ODWBGWGUAJZGNJ-UHFFFAOYSA-N 0.000 claims description 2
WQHXSRFESPDMBW-UHFFFAOYSA-N furan-3-yl-[2-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=CC=CC(C=2N=C(ON=2)C2N(CCCC2)C(=O)C2=COC=C2)=C1 WQHXSRFESPDMBW-UHFFFAOYSA-N 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
INTBVGDNRFKKFQ-UHFFFAOYSA-N [2-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-cyclobutylmethanone Chemical compound ClC1=CC=CC(C=2N=C(ON=2)C2N(CCCC2)C(=O)C2CCC2)=C1 INTBVGDNRFKKFQ-UHFFFAOYSA-N 0.000 claims 1
ABWONHBWGCZVOP-UHFFFAOYSA-N [2-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-(5-methylthiophen-2-yl)methanone Chemical compound S1C(C)=CC=C1C(=O)N1C(C=2ON=C(N=2)C=2C=C(Cl)C=CC=2)CCC1 ABWONHBWGCZVOP-UHFFFAOYSA-N 0.000 claims 1
BKCDBAMVMCCPAF-UHFFFAOYSA-N [2-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]pyrrolidin-1-yl]-cycloheptylmethanone Chemical compound ClC1=CC=CC(C=2N=C(ON=2)C2N(CCC2)C(=O)C2CCCCCC2)=C1 BKCDBAMVMCCPAF-UHFFFAOYSA-N 0.000 claims 1
AUSNSOZGIUAIGQ-UHFFFAOYSA-N [4-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]-1,3-thiazolidin-3-yl]-(5-methylthiophen-2-yl)methanone Chemical compound S1C(C)=CC=C1C(=O)N1C(C=2ON=C(N=2)C=2C=C(Cl)C=CC=2)CSC1 AUSNSOZGIUAIGQ-UHFFFAOYSA-N 0.000 claims 1
BDHPBNDYZSJFEG-UHFFFAOYSA-N [4-[3-(3-chlorophenyl)-1,2,4-oxadiazol-5-yl]-1,3-thiazolidin-3-yl]-(furan-2-yl)methanone Chemical compound ClC1=CC=CC(C=2N=C(ON=2)C2N(CSC2)C(=O)C=2OC=CC=2)=C1 BDHPBNDYZSJFEG-UHFFFAOYSA-N 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 87
239000000243 solution Substances 0.000 description 58
239000000543 intermediate Substances 0.000 description 51
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 46
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
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239000011541 reaction mixture Substances 0.000 description 27
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 26
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125000004432 carbon atom Chemical group C* 0.000 description 13
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DBABZHXKTCFAPX-UHFFFAOYSA-N probenecid Chemical compound CCCN(CCC)S(=O)(=O)C1=CC=C(C(O)=O)C=C1 DBABZHXKTCFAPX-UHFFFAOYSA-N 0.000 description 1
229960003081 probenecid Drugs 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
229950010131 puromycin Drugs 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
239000002287 radioligand Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000002594 sorbent Substances 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000010186 staining Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
230000026676 system process Effects 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
APFUDGDIIFSTSD-UHFFFAOYSA-N tert-butyl 3-carbamoylpiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC(C(N)=O)C1 APFUDGDIIFSTSD-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
231100000886 tinnitus Toxicity 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
206010044652 trigeminal neuralgia Diseases 0.000 description 1
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239000001993 wax Substances 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

HU0500920A 2005-10-05 2005-10-05 Oxadiazole derivatives, process for their preparation and their use HUP0500920A2 (en)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
HU0500920A HUP0500920A2 (en)	2005-10-05	2005-10-05	Oxadiazole derivatives, process for their preparation and their use
PCT/HU2006/000087 WO2007039781A2 (fr)	2005-10-05	2006-10-05	Nouveaux composes

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU0500920A HUP0500920A2 (en)	2005-10-05	2005-10-05	Oxadiazole derivatives, process for their preparation and their use

Publications (2)

Publication Number	Publication Date
HU0500920D0 HU0500920D0 (en)	2005-12-28
HUP0500920A2 true HUP0500920A2 (en)	2007-07-30

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ID=89986317

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU0500920A HUP0500920A2 (en)	2005-10-05	2005-10-05	Oxadiazole derivatives, process for their preparation and their use

Country Status (2)

Country	Link
HU (1)	HUP0500920A2 (fr)
WO (1)	WO2007039781A2 (fr)

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US8349852B2 (en)	2009-01-13	2013-01-08	Novartis Ag	Quinazolinone derivatives useful as vanilloid antagonists
WO2010124055A1 (fr) *	2009-04-23	2010-10-28	Merck Sharp & Dohme Corp.	Modulateurs du récepteur mglur5 fourrés de 2-alkyl pipéridines
CA2808582A1 (fr)	2009-08-14	2011-02-17	University Of Virginia Patent Foundation	Imidamides inhibiteurs de sphingosine kinase
US8592590B2 (en)	2009-12-29	2013-11-26	Eli Lilly And Company	Tetrahydrotriazolopyridine compounds as selective MGLU5 receptor potentiators useful for the treatment of schizophrenia
WO2011092293A2 (fr)	2010-02-01	2011-08-04	Novartis Ag	Dérivés de cyclohexylamide utilisés en tant qu'antagonistes du récepteur du crf
EP2531510B1 (fr)	2010-02-01	2014-07-23	Novartis AG	Dérivés de pyrazolo[5,1-b]utilisés en tant qu'antagonistes du récepteur de crf-1
US8835444B2 (en)	2010-02-02	2014-09-16	Novartis Ag	Cyclohexyl amide derivatives as CRF receptor antagonists
EP2630135B1 (fr)	2010-10-21	2020-03-04	Bayer Intellectual Property GmbH	1-(carbonyl hétérocyclique)pipéridines
KR101689093B1 (ko)	2012-06-04	2016-12-22	액테리온 파마슈티칼 리미티드	벤즈이미다졸-프롤린 유도체
JP6244365B2 (ja)	2012-10-10	2017-12-06	アクテリオンファーマシューティカルズリミテッドＡｃｔｅｌｉｏｎＰｈａｒｍａｃｅｕｔｉｃａｌｓＬｔｄ	［オルトビ−（ヘテロ−）アリール］−［２−（メタビ−（ヘテロ−）アリール）−ピロリジン−１−イル］−メタノン誘導体であるオレキシン受容体アンタゴニスト
CN105051040A (zh)	2013-03-12	2015-11-11	埃科特莱茵药品有限公司	作为食欲素受体拮抗剂的氮杂环丁烷酰胺衍生物
MX366642B (es)	2013-12-04	2019-07-17	Idorsia Pharmaceuticals Ltd	Uso de derivados de bencimidazol-prolina.
EP3914592A1 (fr) *	2019-01-25	2021-12-01	University of Virginia Patent Foundation	Inhibiteurs de l'homologue 2 de spinster (spns2) destinés à être utilisés en thérapie
MX2022003494A (es) *	2019-10-17	2022-04-25	Givaudan Sa	Azacilos sustituidos como moduladores del miembro 8 de melastatina de potencial receptor transitorio (trmp8).
GB202012170D0 (en) *	2020-08-05	2020-09-16	Givaudan Sa	Organic compounds
US20230373937A1 (en) *	2020-09-09	2023-11-23	University Of Virginia Patent Foundation	Inhibitors of spinster homolog 2 (spns2) for use in therapy
KR20250022023A (ko)	2022-06-13	2025-02-14	알리벡시스 가부시키가이샤	아자사이클로알킬카보닐 환상 아민 화합물

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DE19643037A1 (de) *	1996-10-18	1998-04-23	Boehringer Ingelheim Kg	Neue Oxadiazole, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel
US7217714B1 (en) *	1998-12-23	2007-05-15	Agouron Pharmaceuticals, Inc.	CCR5 modulators
US6596731B2 (en) *	2001-03-27	2003-07-22	Hoffmann-La Roche Inc.	Substituted imidazo[1,2-A] pyridine derivatives
US7074809B2 (en) *	2002-08-09	2006-07-11	Astrazeneca Ab	Compounds
GB0325956D0 (en) *	2003-11-06	2003-12-10	Addex Pharmaceuticals Sa	Novel compounds

2005
- 2005-10-05 HU HU0500920A patent/HUP0500920A2/hu unknown
2006
- 2006-10-05 WO PCT/HU2006/000087 patent/WO2007039781A2/fr not_active Ceased

Also Published As

Publication number	Publication date
WO2007039781A3 (fr)	2010-08-26
WO2007039781A2 (fr)	2007-04-12
HU0500920D0 (en)	2005-12-28

Publication	Publication Date	Title
HUP0500920A2 (en)	2007-07-30	Oxadiazole derivatives, process for their preparation and their use
US7074809B2 (en)	2006-07-11	Compounds
JP4958560B2 (ja)	2012-06-20	Ｇｐｃｒ受容体作動薬としてのヘテロ環誘導体
US10538498B2 (en)	2020-01-21	1,3,4-oxadiazole sulfonamide derivative compounds as histone deacetylase 6 inhibitor, and the pharmaceutical composition comprising the same
US8415379B2 (en)	2013-04-09	Pyridines
CN101903372B (zh)	2014-06-18	作为食欲肽受体拮抗剂的杂芳基衍生物
US20090325924A1 (en)	2009-12-31	GPCR Agonists
US20060025414A1 (en)	2006-02-02	Poly-heterocyclic compounds and their use as metabotropic glutamate receptor antagonists
US20090203676A1 (en)	2009-08-13	G-protein Coupled Receptor Agonists
CN101511802A (zh)	2009-08-19	螺唑烷酮化合物及其作为代谢型谷氨酸受体增效剂的用途
JP2009509921A (ja)	2009-03-12	置換イソインドロン類及び代謝調節型グルタミン酸受容体増強剤としてのその使用
US20110166155A1 (en)	2011-07-07	Substituted Isoindolones and Their Use as Metabotropic Glutamate Receptor Potentiators
WO2008050200A1 (fr)	2008-05-02	Composés d'oxadiazole comme antagonistes des canaux calciques
US20130197011A1 (en)	2013-08-01	Phenyl-3-aza-bicyclo[3.1.0]hex-3-yl-methanones and the use thereof as medicament
EP1558598A1 (fr)	2005-08-03	Composes triazole pour le traitement de la dysmenorrhee
CA2760746A1 (fr)	2010-11-11	Derives d'isoxazole-pyrazole
US7084145B2 (en)	2006-08-01	Triazole compounds useful in therapy
TW201249830A (en)	2012-12-16	Heteroaromatic ring derivatives
WO2007039782A1 (fr)	2007-04-12	Derives de tetrazole utilises comme modulateurs de recepteurs metabotropiques du glutamate
JP2008524325A (ja)	2008-07-10	複素環式ＭＣＨｒ１アンタゴニストと療法におけるその使用
US11623919B2 (en)	2023-04-11	Heterocyclic P2X7 antagonists
US7763732B2 (en)	2010-07-27	Indole derivatives
HUP0501170A2 (en)	2007-09-28	2-heteroaryl-3-phenyl-thieno[2,3-b]pyridines, process for their preparation, their use and pharmaceutical compositions containing them
BR112018001720B1 (pt)	2024-05-07	Compostos de derivado de 1,3,4-oxadiazol sulfonamida como inibidor de histona desacetilase 6 e a composição farmacêutica que compreende os mesmos
HK1084666A (en)	2006-08-04	Triazole compounds useful in therapy

Legal Events

Date	Code	Title	Description
2008-03-28	FD9A	Lapse of provisional protection due to non-payment of fees