PL193802B1 - Zastosowanie pochodnych arylo (lub heteroarylo) azolilokarbinoli do wytwarzania leku do leczenia zaburzeń wywoływanych nadmiarem substancji P - Google Patents
Zastosowanie pochodnych arylo (lub heteroarylo) azolilokarbinoli do wytwarzania leku do leczenia zaburzeń wywoływanych nadmiarem substancji PInfo
- Publication number
- PL193802B1 PL193802B1 PL99346221A PL34622199A PL193802B1 PL 193802 B1 PL193802 B1 PL 193802B1 PL 99346221 A PL99346221 A PL 99346221A PL 34622199 A PL34622199 A PL 34622199A PL 193802 B1 PL193802 B1 PL 193802B1
- Authority
- PL
- Poland
- Prior art keywords
- methyl
- imidazole
- dimethylamino
- pyrazole
- chloro
- Prior art date
Links
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 5
- 125000001072 heteroaryl group Chemical group 0.000 title claims abstract description 5
- 239000003814 drug Substances 0.000 title claims description 7
- 230000001404 mediated effect Effects 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title description 4
- ADNPLDHMAVUMIW-CUZNLEPHSA-N substance P Chemical compound C([C@@H](C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(N)=O)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CCCN=C(N)N)C1=CC=CC=C1 ADNPLDHMAVUMIW-CUZNLEPHSA-N 0.000 title 1
- -1 N-methylpiperidyl group Chemical group 0.000 claims abstract description 65
- 208000019901 Anxiety disease Diseases 0.000 claims abstract description 7
- 230000036506 anxiety Effects 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 201000001880 Sexual dysfunction Diseases 0.000 claims abstract description 6
- 206010013663 drug dependence Diseases 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 6
- 231100000872 sexual dysfunction Toxicity 0.000 claims abstract description 6
- 208000011117 substance-related disease Diseases 0.000 claims abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- 241000124008 Mammalia Species 0.000 claims abstract description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 99
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 24
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 claims description 21
- 102100024304 Protachykinin-1 Human genes 0.000 claims description 21
- 101800003906 Substance P Proteins 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 12
- 150000003254 radicals Chemical class 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 208000020925 Bipolar disease Diseases 0.000 claims description 5
- 208000028683 bipolar I disease Diseases 0.000 claims description 5
- 208000010877 cognitive disease Diseases 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 208000028698 Cognitive impairment Diseases 0.000 claims description 4
- 201000003152 motion sickness Diseases 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- KORIJXKQGMTQTO-UHFFFAOYSA-N 1h-pyrrol-2-ylmethanol Chemical class OCC1=CC=CN1 KORIJXKQGMTQTO-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 82
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 72
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 55
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 32
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 8
- DZDYNIMYBBETIC-UHFFFAOYSA-N (1-butylimidazol-2-yl)-(4-chlorophenyl)methanol Chemical compound CCCCN1C=CN=C1C(O)C1=CC=C(Cl)C=C1 DZDYNIMYBBETIC-UHFFFAOYSA-N 0.000 claims 2
- DOEYYTQISIVAMY-UHFFFAOYSA-N 1-(1-methylimidazol-2-yl)-1-[3-(trifluoromethyl)phenyl]pentan-1-ol Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(O)(CCCC)C1=NC=CN1C DOEYYTQISIVAMY-UHFFFAOYSA-N 0.000 claims 2
- POXWDTQUDZUOGP-UHFFFAOYSA-N 1h-1,4-diazepine Chemical compound N1C=CC=NC=C1 POXWDTQUDZUOGP-UHFFFAOYSA-N 0.000 claims 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 125000006178 methyl benzyl group Chemical group 0.000 claims 2
- 229940095064 tartrate Drugs 0.000 claims 2
- GKFJUJCWQUQWCK-UHFFFAOYSA-N (1-butylimidazol-2-yl)-(3,4,5-trimethoxyphenyl)methanol Chemical compound CCCCN1C=CN=C1C(O)C1=CC(OC)=C(OC)C(OC)=C1 GKFJUJCWQUQWCK-UHFFFAOYSA-N 0.000 claims 1
- ADWWKGSHHTZDGW-UHFFFAOYSA-N (1-butylimidazol-2-yl)-(3,4-dichlorophenyl)methanol Chemical compound CCCCN1C=CN=C1C(O)C1=CC=C(Cl)C(Cl)=C1 ADWWKGSHHTZDGW-UHFFFAOYSA-N 0.000 claims 1
- PLTSXNZBXQRFSL-UHFFFAOYSA-N (1-butylimidazol-2-yl)-(4-chlorophenyl)-(1-methylpiperidin-4-yl)methanol Chemical compound CCCCN1C=CN=C1C(O)(C=1C=CC(Cl)=CC=1)C1CCN(C)CC1 PLTSXNZBXQRFSL-UHFFFAOYSA-N 0.000 claims 1
- IMFOYQOQIODGQW-UHFFFAOYSA-N (1-butylimidazol-2-yl)-[4-(trifluoromethyl)phenyl]methanol Chemical compound CCCCN1C=CN=C1C(O)C1=CC=C(C(F)(F)F)C=C1 IMFOYQOQIODGQW-UHFFFAOYSA-N 0.000 claims 1
- DVHHTIGJNVCFDE-UHFFFAOYSA-N (1-dodecylimidazol-2-yl)-(3,4,5-trimethoxyphenyl)methanol Chemical compound CCCCCCCCCCCCN1C=CN=C1C(O)C1=CC(OC)=C(OC)C(OC)=C1 DVHHTIGJNVCFDE-UHFFFAOYSA-N 0.000 claims 1
- YJQRNWFHOPZNKJ-UHFFFAOYSA-N (1-methylimidazol-2-yl)-(3,4,5-trimethoxyphenyl)methanol Chemical compound COC1=C(OC)C(OC)=CC(C(O)C=2N(C=CN=2)C)=C1 YJQRNWFHOPZNKJ-UHFFFAOYSA-N 0.000 claims 1
- IVWSNLPIJWOKEL-UHFFFAOYSA-N (1-methylimidazol-2-yl)-[3-(trifluoromethyl)phenyl]methanol Chemical compound CN1C=CN=C1C(O)C1=CC=CC(C(F)(F)F)=C1 IVWSNLPIJWOKEL-UHFFFAOYSA-N 0.000 claims 1
- DGBUCHZPKPTBTF-UHFFFAOYSA-N (1-methylimidazol-2-yl)-[4-(trifluoromethyl)phenyl]methanol Chemical compound CN1C=CN=C1C(O)C1=CC=C(C(F)(F)F)C=C1 DGBUCHZPKPTBTF-UHFFFAOYSA-N 0.000 claims 1
- GOVKUSQTCDGAMA-UHFFFAOYSA-N (2-butylpyrazol-3-yl)-(3,4,5-trimethoxyphenyl)methanol Chemical compound CCCCN1N=CC=C1C(O)C1=CC(OC)=C(OC)C(OC)=C1 GOVKUSQTCDGAMA-UHFFFAOYSA-N 0.000 claims 1
- VRNGWCCYQAXTAY-UHFFFAOYSA-N (2-butylpyrazol-3-yl)-phenylmethanol Chemical compound CCCCN1N=CC=C1C(O)C1=CC=CC=C1 VRNGWCCYQAXTAY-UHFFFAOYSA-N 0.000 claims 1
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- CEJLGKWTVRUHIP-UHFFFAOYSA-N (4-chloro-2-methylpyrazol-3-yl)-phenylmethanol Chemical compound CN1N=CC(Cl)=C1C(O)C1=CC=CC=C1 CEJLGKWTVRUHIP-UHFFFAOYSA-N 0.000 claims 1
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- CGBHLJFEXGOGFF-UHFFFAOYSA-N 1-(1-butylimidazol-2-yl)-1-(3,4,5-trimethoxyphenyl)pentan-1-ol Chemical compound CCCCN1C=CN=C1C(O)(CCCC)C1=CC(OC)=C(OC)C(OC)=C1 CGBHLJFEXGOGFF-UHFFFAOYSA-N 0.000 claims 1
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- NYQSCMIJHPKRSK-UHFFFAOYSA-N 1-(1-dodecylimidazol-2-yl)-1-(3,4,5-trimethoxyphenyl)pentan-1-ol Chemical compound CCCCCCCCCCCCN1C=CN=C1C(O)(CCCC)C1=CC(OC)=C(OC)C(OC)=C1 NYQSCMIJHPKRSK-UHFFFAOYSA-N 0.000 claims 1
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- PGZIXIJCMBPHCS-UHFFFAOYSA-N 1-[2-[1-(1-methylimidazol-2-yl)-1-[3-(trifluoromethyl)phenyl]ethoxy]ethyl]piperidine Chemical compound CN1C=CN=C1C(C)(C=1C=C(C=CC=1)C(F)(F)F)OCCN1CCCCC1 PGZIXIJCMBPHCS-UHFFFAOYSA-N 0.000 claims 1
- APKDHLMIBHYURQ-UHFFFAOYSA-N 1h-imidazol-2-yl(phenyl)methanol Chemical compound C=1C=CC=CC=1C(O)C1=NC=CN1 APKDHLMIBHYURQ-UHFFFAOYSA-N 0.000 claims 1
- IUHGHUIFWRTGTR-UHFFFAOYSA-N 2-[(2,5-dimethylpyrazol-3-yl)-phenylmethoxy]-n,n-dimethylethanamine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC(C)=NN1C IUHGHUIFWRTGTR-UHFFFAOYSA-N 0.000 claims 1
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
- A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
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- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
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- Pain & Pain Management (AREA)
- Addiction (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES009801708A ES2150378B1 (es) | 1998-08-07 | 1998-08-07 | Empleo de derivados de aril(o heteroaril)azolilcarbinoles en la elaboracion de un medicamento para el tratamiento de los trastornos mediados por un exceso de substancia p. |
| PCT/ES1999/000255 WO2000007542A2 (es) | 1998-08-07 | 1999-08-05 | Empleo de derivados de aril(o heteroaril)azolilcarbinoles en la elaboracion de un medicamento para el tratamiento de los trastornos mediados por un exceso de substancia p |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL346221A1 PL346221A1 (en) | 2002-01-28 |
| PL193802B1 true PL193802B1 (pl) | 2007-03-30 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL99346221A PL193802B1 (pl) | 1998-08-07 | 1999-08-05 | Zastosowanie pochodnych arylo (lub heteroarylo) azolilokarbinoli do wytwarzania leku do leczenia zaburzeń wywoływanych nadmiarem substancji P |
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|---|---|
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| EP (1) | EP1103243B1 (enExample) |
| JP (1) | JP2002522359A (enExample) |
| KR (1) | KR100558506B1 (enExample) |
| CN (1) | CN1151789C (enExample) |
| AR (1) | AR019999A1 (enExample) |
| AT (1) | ATE257379T1 (enExample) |
| AU (1) | AU754124B2 (enExample) |
| BR (1) | BR9912807A (enExample) |
| CA (1) | CA2339661C (enExample) |
| CO (1) | CO5080747A1 (enExample) |
| CZ (1) | CZ292065B6 (enExample) |
| DE (1) | DE69914085T8 (enExample) |
| DK (1) | DK1103243T3 (enExample) |
| ES (2) | ES2150378B1 (enExample) |
| HU (1) | HUP0105428A3 (enExample) |
| IL (1) | IL141295A0 (enExample) |
| NO (1) | NO20010634L (enExample) |
| NZ (1) | NZ509645A (enExample) |
| PL (1) | PL193802B1 (enExample) |
| PT (1) | PT1103243E (enExample) |
| RU (1) | RU2223116C2 (enExample) |
| TR (1) | TR200100378T2 (enExample) |
| TW (1) | TW445259B (enExample) |
| WO (1) | WO2000007542A2 (enExample) |
| ZA (1) | ZA200100867B (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
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| ES2174756B2 (es) * | 2001-04-06 | 2003-11-16 | Esteve Labor Dr | Derivados de aril (o heteroaril) azolilcarbinoles para el tratamiento de enfermedades respiratorias. |
| ES2180449B1 (es) * | 2001-07-06 | 2004-01-16 | Esteve Labor Dr | Derivados de aril (o heteroaril) azolilcarbinoles para el tratamiento de la incontinencia urinaria. |
| US20040142929A1 (en) * | 2001-07-06 | 2004-07-22 | Ramon Merce-Vidal | Derivatives of aryl (or heteroaryl) azolylcarbinoles for the treatment of urinary incontinence |
| DE10335566A1 (de) * | 2003-07-31 | 2005-02-24 | Grünenthal GmbH | Arzneimittel enthaltend Derivate von Aryl( oder Heteroaryl)azolylcarbinolen |
| ES2244326B1 (es) * | 2004-04-05 | 2007-02-16 | Laboratorios Del Dr. Esteve, S.A. | Combinacion de substancias activas. |
| EP1584335A3 (en) * | 2004-04-05 | 2006-02-22 | Laboratorios Del Dr. Esteve, S.A. | Active substance combination comprising a carbinol composition and an opioid |
| EP1784178A1 (en) * | 2004-07-30 | 2007-05-16 | Laboratorios Del Dr. Esteve, S.A. | Aryl (or heteroaryl) azolylcarbinols |
| AU2005286733B2 (en) * | 2004-09-23 | 2009-11-05 | Alexander Michalow | Methods for regulating neurotransmitter systems by inducing counteradaptations |
| US20080045610A1 (en) * | 2004-09-23 | 2008-02-21 | Alexander Michalow | Methods for regulating neurotransmitter systems by inducing counteradaptations |
| EP1690537A1 (en) * | 2005-02-15 | 2006-08-16 | Laboratorios Del Dr. Esteve, S.A. | Derivatives of aryl(or heteroaryl) azolycarbinols for the treatment of fibromyalgia |
| ES2286920B1 (es) * | 2005-02-15 | 2008-08-16 | Laboratorios Del Dr. Esteve, S.A. | Derivados de aril (o heteroaril)azolilcarbinoles para el tratamiento de la fibromialgia. |
| EP1695704A1 (en) * | 2005-02-28 | 2006-08-30 | Laboratorios Del Dr. Esteve, S.A. | Derivatives of aryl (or heteroaryl) azolylcarbinols for the treatment of fibromyalgia |
| WO2006087147A2 (en) * | 2005-02-15 | 2006-08-24 | Laboratorios Del Dr. Esteve, S.A. | Derivatives of aryl (or heteroaryl) azolylcarbinols for the treatment of fibromyalgia |
| JP2009524617A (ja) | 2006-01-27 | 2009-07-02 | エフ．ホフマン−ラ ロシュ アーゲー | 置換２−イミダゾール又はイミダゾリン誘導体の使用 |
| EP1820502A1 (en) * | 2006-02-10 | 2007-08-22 | Laboratorios Del Dr. Esteve, S.A. | Active substance combination comprising azolylcarbinol compounds |
| RU2009112496A (ru) | 2006-10-19 | 2010-11-27 | Ф. Хоффманн-Ля Рош Аг (Ch) | Аминометил-4-имидазолы |
| KR101176700B1 (ko) | 2006-11-02 | 2012-08-23 | 에프. 호프만-라 로슈 아게 | 미량 아민 결합된 수용체의 조절자로서 치환된 2-이미다졸 |
| CN101535298A (zh) | 2006-11-16 | 2009-09-16 | 弗·哈夫曼-拉罗切有限公司 | 取代的4-咪唑类化合物 |
| CN101190330A (zh) | 2006-11-30 | 2008-06-04 | 深圳市鼎兴生物医药技术开发有限公司 | 胆碱酯酶在拮抗速激肽药物中的应用 |
| WO2008071574A1 (en) | 2006-12-13 | 2008-06-19 | F. Hoffmann-La Roche Ag | Novel 2 -imidazoles as ligands for trace amine associated receptors (taar) |
| UA98951C2 (ru) | 2007-02-02 | 2012-07-10 | Ф. Хоффманн-Ля Рош Аг | 2-аминооксазолины и лекарственное средство, которое их содержит |
| KR101335845B1 (ko) | 2007-02-15 | 2013-12-02 | 에프. 호프만-라 로슈 아게 | Ｔａａｒ1 리간드로서의 2-아미노옥사졸린 |
| CA2691082A1 (en) | 2007-07-02 | 2009-01-08 | F. Hoffmann-La Roche Ag | 2 -imidazolines having a good affinity to the trace amine associated receptors (taars) |
| CN101687811A (zh) | 2007-07-03 | 2010-03-31 | 弗·哈夫曼-拉罗切有限公司 | 4-咪唑啉类及其作为抗抑郁剂的应用 |
| EP2183216A1 (en) | 2007-07-27 | 2010-05-12 | F. Hoffmann-Roche AG | 2-azetidinemethaneamines and 2-pyrrolidinemethaneamines as taar-ligands |
| JP5341084B2 (ja) | 2007-08-03 | 2013-11-13 | エフ．ホフマン−ラ ロシュ アーゲー | Ｔａａｒ１リガンドとしてのピリジンカルボキシアミド及びベンズアミド誘導体 |
| US8242153B2 (en) | 2008-07-24 | 2012-08-14 | Hoffmann-La Roche Inc. | 4,5-dihydro-oxazol-2YL derivatives |
| WO2010123999A2 (en) * | 2009-04-21 | 2010-10-28 | Auspex Pharmaceuticals, Inc. | 1-methylpyrazole modulators of substance p, calcitonin gene-related peptide, adrenergic receptor, and/or 5-ht receptor |
| US8354441B2 (en) | 2009-11-11 | 2013-01-15 | Hoffmann-La Roche Inc. | Oxazoline derivatives |
| US9452980B2 (en) | 2009-12-22 | 2016-09-27 | Hoffmann-La Roche Inc. | Substituted benzamides |
| CA3013696C (en) | 2016-03-17 | 2024-04-16 | F. Hoffmann-La Roche Ag | 5-ethyl-4-methyl-pyrazole-3-carboxamide derivative having activity as agonist of taar |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2613720B1 (fr) * | 1987-04-10 | 1990-01-19 | Esteve Labor Dr | Derives d'aryl-heteroaryl carbinols avec activite analgesique |
| FR2681322B1 (fr) * | 1991-09-12 | 1993-12-17 | Laboratorios Dr Esteve Sa | Derives d'aryl-heteroaryl-{n-[2-(3,4-dimethoxyphenyl)-ethyl]-n-methyl-3-aminopropoxy}-methane leur preparation et leur application en tant que medicaments . |
| CA2154116A1 (en) * | 1994-07-22 | 1996-01-23 | Philip Arthur Hipskind | 1-aryl-2-acetamidopentanone derivatives for use as tachykinin receptor antagonists |
| FR2742147B1 (fr) * | 1995-12-06 | 1998-02-27 | Esteve Labor Dr | Procede de separation de carbinols |
| JP2001508412A (ja) * | 1996-12-02 | 2001-06-26 | メルク シヤープ エンド ドーム リミテツド | 認識障害の治療のためのｎｋ−１受容体拮抗薬の使用 |
| ATE285776T1 (de) * | 1996-12-02 | 2005-01-15 | Merck Sharp & Dohme | Verfahren und vorrichtung zur kompensation von durch chrominanzsignalverarbeitung verursachten luminanzstörungen |
| EP0942734A1 (en) * | 1996-12-02 | 1999-09-22 | MERCK SHARP & DOHME LTD. | Use of nk-1 receptor antagonists for treating severe anxiety disorders |
| CA2273807A1 (en) * | 1996-12-02 | 1998-06-11 | Merck Sharp & Dohme Limited | Use of nk-1 receptor antagonists for treating schizophrenic disorders |
| ES2150353B1 (es) * | 1998-04-15 | 2001-07-01 | Esteve Labor Dr | Tienilazolilalcoxietanaminas, su preparacion y su aplicacion como medicamentos. |
-
1998
- 1998-08-07 ES ES009801708A patent/ES2150378B1/es not_active Expired - Fee Related
-
1999
- 1999-08-04 AR ARP990103870A patent/AR019999A1/es unknown
- 1999-08-04 CO CO99049291A patent/CO5080747A1/es unknown
- 1999-08-05 DE DE69914085T patent/DE69914085T8/de not_active Expired - Fee Related
- 1999-08-05 ES ES99940199T patent/ES2213380T3/es not_active Expired - Lifetime
- 1999-08-05 PL PL99346221A patent/PL193802B1/pl not_active IP Right Cessation
- 1999-08-05 CZ CZ2001412A patent/CZ292065B6/cs not_active IP Right Cessation
- 1999-08-05 WO PCT/ES1999/000255 patent/WO2000007542A2/es not_active Ceased
- 1999-08-05 JP JP2000563228A patent/JP2002522359A/ja active Pending
- 1999-08-05 PT PT99940199T patent/PT1103243E/pt unknown
- 1999-08-05 HU HU0105428A patent/HUP0105428A3/hu unknown
- 1999-08-05 AT AT99940199T patent/ATE257379T1/de not_active IP Right Cessation
- 1999-08-05 CA CA002339661A patent/CA2339661C/en not_active Expired - Fee Related
- 1999-08-05 DK DK99940199T patent/DK1103243T3/da active
- 1999-08-05 US US09/762,079 patent/US6518295B1/en not_active Expired - Fee Related
- 1999-08-05 EP EP99940199A patent/EP1103243B1/en not_active Expired - Lifetime
- 1999-08-05 KR KR1020017001560A patent/KR100558506B1/ko not_active Expired - Fee Related
- 1999-08-05 NZ NZ509645A patent/NZ509645A/xx unknown
- 1999-08-05 TR TR2001/00378T patent/TR200100378T2/xx unknown
- 1999-08-05 RU RU2001106644/15A patent/RU2223116C2/ru not_active IP Right Cessation
- 1999-08-05 AU AU54229/99A patent/AU754124B2/en not_active Ceased
- 1999-08-05 TW TW088113353A patent/TW445259B/zh not_active IP Right Cessation
- 1999-08-05 BR BR9912807-1A patent/BR9912807A/pt not_active Application Discontinuation
- 1999-08-05 CN CNB998109150A patent/CN1151789C/zh not_active Expired - Fee Related
-
2001
- 2001-01-31 ZA ZA200100867A patent/ZA200100867B/en unknown
- 2001-02-06 NO NO20010634A patent/NO20010634L/no not_active Application Discontinuation
- 2001-02-07 IL IL14129501A patent/IL141295A0/xx unknown
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