ZA200607133B - Novel benzyl(idene)-lactam derivatives - Google Patents
Novel benzyl(idene)-lactam derivatives Download PDFInfo
- Publication number
- ZA200607133B ZA200607133B ZA200607133A ZA200607133A ZA200607133B ZA 200607133 B ZA200607133 B ZA 200607133B ZA 200607133 A ZA200607133 A ZA 200607133A ZA 200607133 A ZA200607133 A ZA 200607133A ZA 200607133 B ZA200607133 B ZA 200607133B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- benzyl
- piperazin
- phenyl
- hydroxy
- Prior art date
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 title claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 110
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 100
- -1 chloro, fluoro, bromo, iodo Chemical group 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 57
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 49
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 48
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims description 43
- HNJBEVLQSNELDL-UHFFFAOYSA-N gamma-butyrolactam Natural products O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 41
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 125000001624 naphthyl group Chemical group 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 27
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 208000019901 Anxiety disease Diseases 0.000 claims description 23
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 22
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 230000036506 anxiety Effects 0.000 claims description 19
- 230000003287 optical effect Effects 0.000 claims description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 239000012442 inert solvent Substances 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 229910052760 oxygen Chemical group 0.000 claims description 15
- 239000001301 oxygen Chemical group 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 150000003951 lactams Chemical group 0.000 claims description 14
- 208000019906 panic disease Diseases 0.000 claims description 14
- 239000011593 sulfur Chemical group 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 125000003386 piperidinyl group Chemical group 0.000 claims description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 13
- 125000003107 substituted aryl group Chemical group 0.000 claims description 13
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 11
- 208000018737 Parkinson disease Diseases 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 150000002431 hydrogen Chemical group 0.000 claims description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 11
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 10
- 229910000510 noble metal Inorganic materials 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 239000011995 wilkinson's catalyst Substances 0.000 claims description 9
- UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 8
- 208000028017 Psychotic disease Diseases 0.000 claims description 8
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims description 8
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 8
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 8
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 8
- 206010061428 decreased appetite Diseases 0.000 claims description 8
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 8
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 claims description 8
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 claims description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 8
- 208000024891 symptom Diseases 0.000 claims description 8
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 8
- 208000023105 Huntington disease Diseases 0.000 claims description 7
- 208000022531 anorexia Diseases 0.000 claims description 7
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- 208000024732 dysthymic disease Diseases 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 125000004434 sulfur atom Chemical group 0.000 claims description 7
- 206010010904 Convulsion Diseases 0.000 claims description 6
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 6
- 206010012335 Dependence Diseases 0.000 claims description 6
- 206010036618 Premenstrual syndrome Diseases 0.000 claims description 6
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 6
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- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 206010015037 epilepsy Diseases 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 6
- 208000019116 sleep disease Diseases 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
- 208000020925 Bipolar disease Diseases 0.000 claims description 5
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 5
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 5
- 229960003920 cocaine Drugs 0.000 claims description 5
- 150000004678 hydrides Chemical class 0.000 claims description 5
- 208000014674 injury Diseases 0.000 claims description 5
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- 238000009901 transfer hydrogenation reaction Methods 0.000 claims description 5
- 230000009529 traumatic brain injury Effects 0.000 claims description 5
- SSJXIUAHEKJCMH-OLQVQODUSA-N (1s,2r)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-OLQVQODUSA-N 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 4
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 4
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 4
- 206010020772 Hypertension Diseases 0.000 claims description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
- 208000019022 Mood disease Diseases 0.000 claims description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims description 4
- 201000004810 Vascular dementia Diseases 0.000 claims description 4
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 4
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 4
- 229940045803 cuprous chloride Drugs 0.000 claims description 4
- 150000004985 diamines Chemical class 0.000 claims description 4
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- 150000002596 lactones Chemical class 0.000 claims description 4
- 229940005483 opioid analgesics Drugs 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
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- 229910000160 potassium phosphate Inorganic materials 0.000 claims description 4
- 235000011009 potassium phosphates Nutrition 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- DASUJKKKKGHFBF-UHFFFAOYSA-L thallium(i) carbonate Chemical compound [Tl+].[Tl+].[O-]C([O-])=O DASUJKKKKGHFBF-UHFFFAOYSA-L 0.000 claims description 4
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 3
- GRFOHUBBUMAJMM-UHFFFAOYSA-N 3-(2-aminoquinolin-3-yl)-n-cyclohexyl-n-methylpropanamide Chemical compound C=1C2=CC=CC=C2N=C(N)C=1CCC(=O)N(C)C1CCCCC1 GRFOHUBBUMAJMM-UHFFFAOYSA-N 0.000 claims description 3
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- 229910052684 Cerium Inorganic materials 0.000 claims description 3
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
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- 125000002393 azetidinyl group Chemical group 0.000 claims description 3
- 229940125717 barbiturate Drugs 0.000 claims description 3
- 229940049706 benzodiazepine Drugs 0.000 claims description 3
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims description 3
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- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims description 3
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 claims description 3
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- MTDZAVXORNLAMB-OAQYLSRUSA-N (3s)-3-[[2-(4-methylpiperazin-1-yl)phenyl]methyl]-1-(6-morpholin-4-ylpyridin-3-yl)pyrrolidin-2-one Chemical compound C1CN(C)CCN1C1=CC=CC=C1C[C@@H]1C(=O)N(C=2C=NC(=CC=2)N2CCOCC2)CC1 MTDZAVXORNLAMB-OAQYLSRUSA-N 0.000 claims description 2
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Psychology (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55380804P | 2004-03-17 | 2004-03-17 |
Publications (1)
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|---|---|
| ZA200607133B true ZA200607133B (en) | 2007-12-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| ZA200607133A ZA200607133B (en) | 2004-03-17 | 2006-08-25 | Novel benzyl(idene)-lactam derivatives |
Country Status (29)
| Country | Link |
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| US (1) | US7479559B2 (es) |
| EP (1) | EP1727794B1 (es) |
| JP (1) | JP4880583B2 (es) |
| KR (1) | KR20060124770A (es) |
| CN (1) | CN1934081A (es) |
| AP (1) | AP2006003726A0 (es) |
| AR (1) | AR050403A1 (es) |
| AT (1) | ATE533745T1 (es) |
| AU (1) | AU2005223481A1 (es) |
| BR (1) | BRPI0508825A (es) |
| CA (1) | CA2559530C (es) |
| CR (1) | CR8618A (es) |
| DO (1) | DOP2005000035A (es) |
| EA (1) | EA200601461A1 (es) |
| EC (1) | ECSP066853A (es) |
| ES (1) | ES2374629T3 (es) |
| GT (1) | GT200500051A (es) |
| IL (1) | IL178105A0 (es) |
| MA (1) | MA28474B1 (es) |
| NL (1) | NL1028558C2 (es) |
| NO (1) | NO20063602L (es) |
| PA (1) | PA8626501A1 (es) |
| PE (1) | PE20051153A1 (es) |
| SV (1) | SV2005002051A (es) |
| TN (1) | TNSN06287A1 (es) |
| TW (1) | TW200604165A (es) |
| UY (1) | UY28811A1 (es) |
| WO (1) | WO2005090300A1 (es) |
| ZA (1) | ZA200607133B (es) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE521591T1 (de) * | 2005-01-13 | 2011-09-15 | Ge Healthcare Ltd | 11c-markierte benzyl-lactam-verbindungen und deren verwendung als bildgebungsmittel |
| US20090286804A1 (en) * | 2005-06-17 | 2009-11-19 | Pfizer Inc | Metabolites of 1-[6-(1-ethyl-1-hydroxy-propyl)-pyridin-3-yl]-3-[2-(4-methyl-piperazin-1-yl)-benzyl]-pyrrolidin-2-one as seratonin receptor antagonists |
| WO2007026219A2 (en) * | 2005-08-31 | 2007-03-08 | Pfizer Products Inc. | Combinations of a 5-ht1b antagonist with a noradrenalin re-uptake inhibitor or a serotonin noradrenalin reutake inhibitor for treating cns conditions |
| WO2008068614A2 (en) * | 2006-12-06 | 2008-06-12 | Pfizer Products Inc. | Stereoselective synthesis of 1-[6-ethyl-1,2-dihydroxy-propyl)-pyridin-3-yl]-3-[2-(4-methyl-piperazin-1-yl)-benzyl]-pyrrolidin-2-one |
| FR2948660B1 (fr) * | 2009-07-30 | 2011-08-19 | Oroxcell | Derives de 2-amino-2-phenyl-alkanol, leur preparation et les compositions pharmaceutiques qui les contiennent |
| EP2338873A1 (en) | 2009-12-22 | 2011-06-29 | Gmeiner, Peter | New aminotetraline derivatives |
| EP2515903A4 (en) * | 2009-12-23 | 2013-07-10 | Peter Maccallum Cancer Inst | COMPOUNDS, PREPARATION AND USES THEREOF |
| ES2750640T3 (es) * | 2012-08-16 | 2020-03-26 | Scripps Research Inst | Ligandos opioides kappa novedosos |
| EP3610890A1 (en) | 2012-11-14 | 2020-02-19 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| CN106061964B (zh) * | 2014-01-20 | 2019-10-25 | 豪夫迈·罗氏有限公司 | 能够刺激神经发生的n-苯基-内酰胺衍生物及其在神经性病症的治疗中的用途 |
| EP3268360B1 (en) | 2015-03-09 | 2019-04-24 | Bristol-Myers Squibb Company | Lactams as inhibitors of rock |
| WO2020183011A1 (en) | 2019-03-14 | 2020-09-17 | Institut Curie | Htr1d inhibitors and uses thereof in the treatment of cancer |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58189163A (ja) * | 1982-04-02 | 1983-11-04 | Takeda Chem Ind Ltd | 縮合ピロリノン誘導体 |
| IL106142A (en) | 1992-06-29 | 1997-03-18 | Merck & Co Inc | Morpholine and thiomorpholine tachykinin receptor antagonists, their preparation and pharmaceutical compositions containing them |
| DE69427289T2 (de) | 1993-03-16 | 2001-09-06 | Pfizer Inc., New York | Naphtalinderivate |
| JP3786983B2 (ja) * | 1994-01-27 | 2006-06-21 | シエーリング アクチエンゲゼルシャフト | ピロリジノン誘導体 |
| GB9410512D0 (en) | 1994-05-25 | 1994-07-13 | Smithkline Beecham Plc | Novel treatment |
| AU692862B2 (en) | 1994-06-29 | 1998-06-18 | Pfizer Inc. | Aryl and heteroaryl alkoxynaphthalene derivatives |
| ES2246058T3 (es) * | 1996-03-29 | 2006-02-01 | Pfizer Inc. | Derivados bencil(iden)-lactama, su preparacion y su uso como (ant)agonistas selectivos de receptores 5-ht1a y/o 5-ht1d. |
| US6423708B1 (en) * | 1996-09-30 | 2002-07-23 | Pfizer Inc | Aralkyl and aralkylidene heterocyclic lactams and imides |
| UA56185C2 (uk) * | 1996-09-30 | 2003-05-15 | Пфайзер Інк. | Аралкіл- та аралкіліденгетероциклічні лактами та іміди, фармацевтична композиція та спосіб лікування |
| DE10002509A1 (de) * | 2000-01-21 | 2001-07-26 | Gruenenthal Gmbh | Substituierte Glutarimide |
| US20020049211A1 (en) * | 2000-09-06 | 2002-04-25 | Sobolov-Jaynes Susan Beth | Combination treatment for depression and anxiety |
| TWI263640B (en) * | 2001-12-19 | 2006-10-11 | Bristol Myers Squibb Co | Fused heterocyclic succinimide compounds and analogs thereof, modulators of nuclear hormone receptor function |
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2005
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- 2005-03-07 AP AP2006003726A patent/AP2006003726A0/xx unknown
- 2005-03-07 EP EP05708687A patent/EP1727794B1/en active Active
- 2005-03-07 EA EA200601461A patent/EA200601461A1/ru unknown
- 2005-03-07 JP JP2007503427A patent/JP4880583B2/ja not_active Expired - Fee Related
- 2005-03-07 AT AT05708687T patent/ATE533745T1/de active
- 2005-03-07 CN CNA2005800085634A patent/CN1934081A/zh active Pending
- 2005-03-07 CA CA2559530A patent/CA2559530C/en not_active Expired - Fee Related
- 2005-03-07 BR BRPI0508825-9A patent/BRPI0508825A/pt not_active IP Right Cessation
- 2005-03-07 AU AU2005223481A patent/AU2005223481A1/en not_active Abandoned
- 2005-03-07 KR KR1020067019078A patent/KR20060124770A/ko not_active Application Discontinuation
- 2005-03-07 ES ES05708687T patent/ES2374629T3/es active Active
- 2005-03-10 DO DO2005000035A patent/DOP2005000035A/es unknown
- 2005-03-15 GT GT200500051A patent/GT200500051A/es unknown
- 2005-03-15 TW TW094107893A patent/TW200604165A/zh unknown
- 2005-03-15 PE PE2005000296A patent/PE20051153A1/es not_active Application Discontinuation
- 2005-03-15 UY UY28811A patent/UY28811A1/es not_active Application Discontinuation
- 2005-03-16 SV SV2005002051A patent/SV2005002051A/es not_active Application Discontinuation
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- 2006-09-15 EC EC2006006853A patent/ECSP066853A/es unknown
- 2006-09-15 MA MA29327A patent/MA28474B1/fr unknown
- 2006-09-15 TN TNP2006000287A patent/TNSN06287A1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2559530A1 (en) | 2005-09-29 |
| JP2007529495A (ja) | 2007-10-25 |
| CR8618A (es) | 2006-11-15 |
| DOP2005000035A (es) | 2005-10-31 |
| NL1028558C2 (nl) | 2006-06-27 |
| AP2006003726A0 (en) | 2006-10-31 |
| EP1727794B1 (en) | 2011-11-16 |
| JP4880583B2 (ja) | 2012-02-22 |
| BRPI0508825A (pt) | 2007-08-14 |
| CN1934081A (zh) | 2007-03-21 |
| TW200604165A (en) | 2006-02-01 |
| EP1727794A1 (en) | 2006-12-06 |
| ES2374629T3 (es) | 2012-02-20 |
| TNSN06287A1 (fr) | 2007-12-03 |
| MA28474B1 (fr) | 2007-03-01 |
| AU2005223481A1 (en) | 2005-09-29 |
| GT200500051A (es) | 2005-10-24 |
| NO20063602L (no) | 2006-09-08 |
| NL1028558A1 (nl) | 2005-09-20 |
| PE20051153A1 (es) | 2006-01-28 |
| US7479559B2 (en) | 2009-01-20 |
| IL178105A0 (en) | 2006-12-31 |
| CA2559530C (en) | 2012-04-24 |
| PA8626501A1 (es) | 2005-11-25 |
| SV2005002051A (es) | 2005-12-13 |
| WO2005090300A1 (en) | 2005-09-29 |
| ECSP066853A (es) | 2006-11-24 |
| ATE533745T1 (de) | 2011-12-15 |
| US20050245521A1 (en) | 2005-11-03 |
| KR20060124770A (ko) | 2006-12-05 |
| AR050403A1 (es) | 2006-10-25 |
| EA200601461A1 (ru) | 2007-02-27 |
| UY28811A1 (es) | 2005-10-31 |
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