HRP20120215T1 - Derivati sulfonil-pirazolinil-1-karboksamidina kao 5-ht6-antagonista - Google Patents
Derivati sulfonil-pirazolinil-1-karboksamidina kao 5-ht6-antagonista Download PDFInfo
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- HRP20120215T1 HRP20120215T1 HR20120215T HRP20120215T HRP20120215T1 HR P20120215 T1 HRP20120215 T1 HR P20120215T1 HR 20120215 T HR20120215 T HR 20120215T HR P20120215 T HRP20120215 T HR P20120215T HR P20120215 T1 HRP20120215 T1 HR P20120215T1
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- OFTZXXRHJIXHMP-UHFFFAOYSA-N 3-sulfonyl-1H-pyrazole-2-carboximidamide Chemical class NC(=N)N1NC=CC1=S(=O)=O OFTZXXRHJIXHMP-UHFFFAOYSA-N 0.000 title 1
- 229940124801 5-HT6 antagonist Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 23
- 150000001875 compounds Chemical class 0.000 claims abstract 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 18
- 239000001257 hydrogen Substances 0.000 claims abstract 18
- 125000001424 substituent group Chemical group 0.000 claims abstract 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 14
- 125000005843 halogen group Chemical group 0.000 claims abstract 9
- 150000001204 N-oxides Chemical class 0.000 claims abstract 8
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 8
- 125000002950 monocyclic group Chemical group 0.000 claims abstract 8
- 150000003839 salts Chemical class 0.000 claims abstract 8
- 239000012453 solvate Substances 0.000 claims abstract 7
- 229910052799 carbon Inorganic materials 0.000 claims abstract 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract 5
- -1 bromo, hydroxyl Chemical group 0.000 claims abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 4
- 125000003118 aryl group Chemical group 0.000 claims abstract 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract 2
- 125000004122 cyclic group Chemical group 0.000 claims abstract 2
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract 2
- ACYSDPAUYCFDPT-UHFFFAOYSA-N n-(4,6-dimethylpyrimidin-2-yl)-n'-(4-methylphenyl)sulfonyl-3-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N=C(N1C(CC=N1)C=1C=CC=CC=1)NC1=NC(C)=CC(C)=N1 ACYSDPAUYCFDPT-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 9
- 150000002431 hydrogen Chemical group 0.000 claims 9
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 6
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 6
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 6
- 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 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 208000035475 disorder Diseases 0.000 claims 6
- 208000010877 cognitive disease Diseases 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- 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 4
- 229940079593 drug Drugs 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 3
- 206010001540 Akathisia Diseases 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 3
- 208000020925 Bipolar disease Diseases 0.000 claims 3
- 208000032841 Bulimia Diseases 0.000 claims 3
- 206010006550 Bulimia nervosa Diseases 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 208000030814 Eating disease Diseases 0.000 claims 3
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 3
- 206010019196 Head injury Diseases 0.000 claims 3
- 208000023105 Huntington disease Diseases 0.000 claims 3
- 208000019695 Migraine disease Diseases 0.000 claims 3
- 208000019022 Mood disease Diseases 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 3
- 208000002193 Pain Diseases 0.000 claims 3
- 206010033664 Panic attack Diseases 0.000 claims 3
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- 208000001431 Psychomotor Agitation Diseases 0.000 claims 3
- 208000028017 Psychotic disease Diseases 0.000 claims 3
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 3
- 208000022531 anorexia Diseases 0.000 claims 3
- 230000036506 anxiety Effects 0.000 claims 3
- 229940049706 benzodiazepine Drugs 0.000 claims 3
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 3
- 208000014679 binge eating disease Diseases 0.000 claims 3
- 208000028683 bipolar I disease Diseases 0.000 claims 3
- 229960003920 cocaine Drugs 0.000 claims 3
- 206010061428 decreased appetite Diseases 0.000 claims 3
- 235000014632 disordered eating Nutrition 0.000 claims 3
- 206010015037 epilepsy Diseases 0.000 claims 3
- 229960004756 ethanol Drugs 0.000 claims 3
- 208000003906 hydrocephalus Diseases 0.000 claims 3
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 3
- 206010027599 migraine Diseases 0.000 claims 3
- 208000027061 mild cognitive impairment Diseases 0.000 claims 3
- 229960002715 nicotine Drugs 0.000 claims 3
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 208000019906 panic disease Diseases 0.000 claims 3
- 201000000980 schizophrenia Diseases 0.000 claims 3
- 208000019116 sleep disease Diseases 0.000 claims 3
- 238000011282 treatment Methods 0.000 claims 3
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 2
- 208000020339 Spinal injury Diseases 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 230000006999 cognitive decline Effects 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 150000004677 hydrates Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 238000003786 synthesis reaction Methods 0.000 claims 2
- 230000007000 age related cognitive decline Effects 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 210000000936 intestine Anatomy 0.000 claims 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 208000020431 spinal cord injury Diseases 0.000 claims 1
- 150000003461 sulfonyl halides Chemical class 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 1
Classifications
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- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
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- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/02—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 two hetero rings
- C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
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- C07D491/10—Spiro-condensed systems
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- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
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| US846406A | 2006-09-22 | 2006-09-22 | |
| EP06121087 | 2006-09-22 | ||
| US90286507P | 2007-02-23 | 2007-02-23 | |
| EP07102965 | 2007-02-23 | ||
| PCT/EP2007/059944 WO2008034863A2 (en) | 2006-09-22 | 2007-09-20 | Sulfonylpyrazoline carboxamidine derivatives as 5-ht6 antagonists |
Publications (1)
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| HRP20120215T1 true HRP20120215T1 (hr) | 2012-04-30 |
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| HR20120215T HRP20120215T1 (hr) | 2006-09-22 | 2012-03-06 | Derivati sulfonil-pirazolinil-1-karboksamidina kao 5-ht6-antagonista |
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| NO (1) | NO20091485L (da) |
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| US7786144B2 (en) * | 2006-05-31 | 2010-08-31 | Solvay Pharmaceuticals B.V. | Sulphur containing pyrazole derivatives as selective cannabinoid CB1 receptor antagonists |
| SA07280510B1 (ar) | 2006-09-22 | 2012-02-07 | سولفاي فارماسوتيكالز بي . في | سلفونيل بيرازول ومشتقات سلفونيل كربوكساميدين كمضادات ht6-5 |
| AR070898A1 (es) | 2008-03-18 | 2010-05-12 | Solvay Pharm Bv | Derivados de arilsulfonil pirazolin carboxamidina como antagonistas de 5-ht6 |
| AR079935A1 (es) * | 2010-01-29 | 2012-02-29 | Abbott Healthcare Products Bv | Sintesis de derivados de pirazolin carboxamidina sustituida |
| WO2013055386A2 (en) * | 2011-10-03 | 2013-04-18 | The University Of Utah Research Foundation | Application of 5-ht6 receptor antagonists for the alleviation of cognitive deficits of down syndrome |
| FR2999574B1 (fr) * | 2012-12-18 | 2014-12-05 | Isochem Sa | Procede de synthese des hydrazines endocycliques |
| TR201808781T4 (tr) | 2013-07-25 | 2018-07-23 | Centre Nat Rech Scient | 5-ht6 antagonistleri olarak pirolokinolin türevleri, hazırlama yöntemi ve bunların kullanımı. |
| EP3109237A1 (en) * | 2015-06-22 | 2016-12-28 | AnaMar AB | Novel 5-ht2 antagonists |
| EP3112334A1 (en) * | 2015-06-29 | 2017-01-04 | DPx Fine Chemicals Austria GmbH & CoKG | Process for manufacturing 1-cyclopropyl-naphthalenes |
| CN111133086B (zh) * | 2017-08-08 | 2023-09-05 | 丝趣科尔卡有限公司 | 包含气味剂的组合物 |
| WO2019180176A1 (en) | 2018-03-21 | 2019-09-26 | Spherium Biomed, S.L. | Composition for the treatment of schizophrenia and/or psychosis |
| EP4178982A1 (en) | 2020-07-13 | 2023-05-17 | Precirix N.V. | Antibody fragment against folr1 |
| WO2023203135A1 (en) | 2022-04-22 | 2023-10-26 | Precirix N.V. | Improved radiolabelled antibody |
| WO2023213801A1 (en) | 2022-05-02 | 2023-11-09 | Precirix N.V. | Pre-targeting |
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| UA74367C2 (uk) * | 2000-03-23 | 2005-12-15 | Сольве Фармас'Ютікалз Б.В. | ПОХІДНІ 4,5-ДИГІДРО-1Н-ПІРАЗОЛУ, ЩО ВИЯВЛЯЮТЬ АНТАГОНІСТИЧНУ АКТИВНІСТЬ ЩОДО СВ<sub>1</sub>, СПОСІБ ЇХ ОДЕРЖАННЯ, ФАРМАЦЕВТИЧНА КОМПОЗИЦІЯ ТА СПОСІБ ЇЇ ВИГОТОВЛЕННЯ, СПОСІБ ЛІКУВАННЯ ЗАХВОРЮВАНЬ (ВАРІАНТИ) |
| PE20021046A1 (es) | 2000-09-30 | 2002-12-14 | Gruenenthal Chemie | Sulfonilguanidina que tiene afinidad al punto de fijacion de gabapentina |
| UA78523C2 (en) * | 2001-09-21 | 2007-04-10 | Solvay Pharm Bv | 4,5-dihydro-1h-pyrazoie derivatives as cb1 antagonists |
| PL367814A1 (en) | 2001-09-21 | 2005-03-07 | Solvay Pharmaceuticals B.V. | 4,5-dihydro-1h-pyrazole derivatives having potent cb1-antagonistic activity |
| CA2619480A1 (en) * | 2005-08-17 | 2007-02-22 | Solvay Pharmaceuticals Gmbh | Method of using potassium channel inhibiting compounds |
| SA07280510B1 (ar) | 2006-09-22 | 2012-02-07 | سولفاي فارماسوتيكالز بي . في | سلفونيل بيرازول ومشتقات سلفونيل كربوكساميدين كمضادات ht6-5 |
| US20080171779A1 (en) * | 2007-01-16 | 2008-07-17 | Solvay Pharmaceuticals B.V. | Use of 5-ht6 antagonists to prevent relapse into addiction |
| WO2008087123A2 (en) * | 2007-01-16 | 2008-07-24 | Solvay Pharmaceuticals B.V. | Use of 5-ht6 antagonists to prevent relapse into addiction |
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2007
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2010
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- 2012-02-28 CY CY20121100208T patent/CY1112418T1/el unknown
- 2012-03-06 HR HR20120215T patent/HRP20120215T1/hr unknown
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