CA2521199A1 - Pyrazole compounds - Google Patents
Pyrazole compounds Download PDFInfo
- Publication number
- CA2521199A1 CA2521199A1 CA002521199A CA2521199A CA2521199A1 CA 2521199 A1 CA2521199 A1 CA 2521199A1 CA 002521199 A CA002521199 A CA 002521199A CA 2521199 A CA2521199 A CA 2521199A CA 2521199 A1 CA2521199 A1 CA 2521199A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compounds
- denotes
- solvates
- salts
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
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- 150000003217 pyrazoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 92
- 150000003839 salts Chemical class 0.000 claims abstract description 42
- 239000012453 solvate Substances 0.000 claims abstract description 28
- -1 ethyl- Chemical group 0.000 claims description 42
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 238000011282 treatment Methods 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 238000011321 prophylaxis Methods 0.000 claims description 8
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 102000005962 receptors Human genes 0.000 claims description 6
- 108020003175 receptors Proteins 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 150000007514 bases Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 3
- 208000032841 Bulimia Diseases 0.000 claims description 3
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 3
- 208000030814 Eating disease Diseases 0.000 claims description 3
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 235000014632 disordered eating Nutrition 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
- 125000004944 pyrazin-3-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 2
- 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 claims description 2
- 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 claims description 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 2
- 208000012902 Nervous system disease Diseases 0.000 claims description 2
- 208000025966 Neurological disease Diseases 0.000 claims description 2
- 206010036618 Premenstrual syndrome Diseases 0.000 claims description 2
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 abstract description 4
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 abstract description 4
- 239000003446 ligand Substances 0.000 abstract description 4
- 235000013350 formula milk Nutrition 0.000 description 60
- 239000004480 active ingredient Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 8
- 238000010626 work up procedure Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 230000000875 corresponding effect Effects 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 229940093499 ethyl acetate Drugs 0.000 description 5
- 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 101150104779 HTR2A gene Proteins 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 208000002193 Pain Diseases 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
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- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- 239000007858 starting material Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- OUZHKZDOXDCQDE-UHFFFAOYSA-N 1-[1-[2-fluoro-4-(4-fluorophenyl)phenyl]-5-(furan-2-yl)pyrazol-4-yl]-n,n-dimethylmethanamine Chemical compound CN(C)CC=1C=NN(C=2C(=CC(=CC=2)C=2C=CC(F)=CC=2)F)C=1C1=CC=CO1 OUZHKZDOXDCQDE-UHFFFAOYSA-N 0.000 description 2
- ZWCQQFCJXASWDD-UHFFFAOYSA-N 1-[[1-[2-fluoro-4-(4-fluorophenyl)phenyl]-5-(furan-2-yl)pyrazol-4-yl]methyl]piperazine Chemical compound C1=CC(F)=CC=C1C1=CC=C(N2C(=C(CN3CCNCC3)C=N2)C=2OC=CC=2)C(F)=C1 ZWCQQFCJXASWDD-UHFFFAOYSA-N 0.000 description 2
- ZIPLULAYKVIJID-UHFFFAOYSA-N 1-[[1-[3,5-difluoro-4-(4-fluorophenyl)phenyl]-5-(furan-2-yl)pyrazol-4-yl]methyl]-4-ethylpiperazine Chemical compound C1CN(CC)CCN1CC1=C(C=2OC=CC=2)N(C=2C=C(F)C(=C(F)C=2)C=2C=CC(F)=CC=2)N=C1 ZIPLULAYKVIJID-UHFFFAOYSA-N 0.000 description 2
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- FPCCSQOGAWCVBH-UHFFFAOYSA-N ketanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1 FPCCSQOGAWCVBH-UHFFFAOYSA-N 0.000 description 2
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- 235000019359 magnesium stearate Nutrition 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
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Landscapes
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- Public Health (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10315571.6 | 2003-04-05 | ||
| DE2003115571 DE10315571A1 (de) | 2003-04-05 | 2003-04-05 | Pyrazolverbindungen |
| PCT/EP2004/002352 WO2004089888A1 (de) | 2003-04-05 | 2004-03-08 | Pyrazolverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2521199A1 true CA2521199A1 (en) | 2004-10-21 |
Family
ID=32981072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002521199A Abandoned CA2521199A1 (en) | 2003-04-05 | 2004-03-08 | Pyrazole compounds |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7960413B2 (https=) |
| EP (1) | EP1611094B1 (https=) |
| JP (1) | JP4833832B2 (https=) |
| KR (1) | KR20050119195A (https=) |
| CN (1) | CN1768053A (https=) |
| AR (1) | AR043836A1 (https=) |
| AT (1) | ATE365161T1 (https=) |
| AU (1) | AU2004228119B2 (https=) |
| BR (1) | BRPI0409160A (https=) |
| CA (1) | CA2521199A1 (https=) |
| DE (2) | DE10315571A1 (https=) |
| ES (1) | ES2287707T3 (https=) |
| MX (1) | MXPA05010651A (https=) |
| PL (1) | PL377685A1 (https=) |
| RU (1) | RU2005133985A (https=) |
| WO (1) | WO2004089888A1 (https=) |
| ZA (1) | ZA200508946B (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7919626B2 (en) * | 2006-02-28 | 2011-04-05 | Helicon Therapeutics, Inc. | Pyrazole compounds and uses thereof |
| US8501745B2 (en) | 2006-02-28 | 2013-08-06 | Dart Neuroscience (Cayman) Ltd. | Piperazine PDE4 inhibitors and uses thereof |
| US9650349B2 (en) | 2007-08-27 | 2017-05-16 | Dart Neuroscience (Cayman) Ltd. | Therapeutic isoxazole compounds |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10315571A1 (de) | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Pyrazolverbindungen |
| DE10315573A1 (de) | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazole |
| DE10315572A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazole |
| DE10315569A1 (de) * | 2003-04-05 | 2004-10-14 | Merck Patent Gmbh | Substituierte Pyrazolverbindungen |
| BRPI0612287A8 (pt) | 2005-06-27 | 2019-01-22 | Exelixis Inc | composição para uso farmacêutico no tratamento de doenças através da medicina nuclear e métodos de uso e para modulação de atividade de receptor nuclear |
| JP2008169191A (ja) * | 2006-02-20 | 2008-07-24 | Eisai R & D Management Co Ltd | 運動ニューロン疾患治療剤 |
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- 2004-03-08 US US10/551,905 patent/US7960413B2/en not_active Expired - Fee Related
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- 2004-03-08 PL PL377685A patent/PL377685A1/pl unknown
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7919626B2 (en) * | 2006-02-28 | 2011-04-05 | Helicon Therapeutics, Inc. | Pyrazole compounds and uses thereof |
| US8399487B2 (en) | 2006-02-28 | 2013-03-19 | Dart Neuroscience (Cayman) Ltd. | Pyrazole compounds and uses thereof |
| US8501745B2 (en) | 2006-02-28 | 2013-08-06 | Dart Neuroscience (Cayman) Ltd. | Piperazine PDE4 inhibitors and uses thereof |
| US8791137B2 (en) | 2006-02-28 | 2014-07-29 | Dart Neuroscience (Cayman) Ltd. | Therapeutic compounds |
| US9650349B2 (en) | 2007-08-27 | 2017-05-16 | Dart Neuroscience (Cayman) Ltd. | Therapeutic isoxazole compounds |
| US10053467B2 (en) | 2007-08-27 | 2018-08-21 | Dart Neuroscience (Cayman) Ltd. | Therapeutic isoxazole compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006523626A (ja) | 2006-10-19 |
| EP1611094B1 (de) | 2007-06-20 |
| ZA200508946B (en) | 2007-02-28 |
| BRPI0409160A (pt) | 2006-05-02 |
| AR043836A1 (es) | 2005-08-17 |
| RU2005133985A (ru) | 2006-03-27 |
| DE10315571A1 (de) | 2004-10-14 |
| MXPA05010651A (es) | 2005-12-12 |
| CN1768053A (zh) | 2006-05-03 |
| US20060276650A1 (en) | 2006-12-07 |
| AU2004228119A1 (en) | 2004-10-21 |
| US7960413B2 (en) | 2011-06-14 |
| PL377685A1 (pl) | 2006-02-06 |
| AU2004228119B2 (en) | 2010-09-02 |
| EP1611094A1 (de) | 2006-01-04 |
| ES2287707T3 (es) | 2007-12-16 |
| ATE365161T1 (de) | 2007-07-15 |
| DE502004004146D1 (en) | 2007-08-02 |
| JP4833832B2 (ja) | 2011-12-07 |
| WO2004089888A1 (de) | 2004-10-21 |
| KR20050119195A (ko) | 2005-12-20 |
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