SK286066B6 - Derivát N-(indolkarbonyl)piperazínu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje - Google Patents
Derivát N-(indolkarbonyl)piperazínu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje Download PDFInfo
- Publication number
- SK286066B6 SK286066B6 SK51-2002A SK512002A SK286066B6 SK 286066 B6 SK286066 B6 SK 286066B6 SK 512002 A SK512002 A SK 512002A SK 286066 B6 SK286066 B6 SK 286066B6
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- SK
- Slovakia
- Prior art keywords
- indol
- formula
- disorders
- methanone
- disease
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 11
- FIVCRRVYLAXYFC-UHFFFAOYSA-N 1h-indol-2-yl(piperazin-1-yl)methanone Chemical class C=1C2=CC=CC=C2NC=1C(=O)N1CCNCC1 FIVCRRVYLAXYFC-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 230000008569 process Effects 0.000 title claims abstract description 5
- 239000000825 pharmaceutical preparation Substances 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 238000011282 treatment Methods 0.000 claims abstract description 24
- 239000003814 drug Substances 0.000 claims abstract description 16
- 239000012453 solvate Substances 0.000 claims abstract description 13
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical group C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 7
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- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
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- 206010006550 Bulimia nervosa Diseases 0.000 claims abstract description 6
- 208000030814 Eating disease Diseases 0.000 claims abstract description 6
- 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 6
- 208000026139 Memory disease Diseases 0.000 claims abstract description 6
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 6
- 206010036618 Premenstrual syndrome Diseases 0.000 claims abstract description 6
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 6
- 235000014632 disordered eating Nutrition 0.000 claims abstract description 6
- 125000001041 indolyl group Chemical group 0.000 claims abstract description 6
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- 208000025966 Neurological disease Diseases 0.000 claims abstract description 5
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- 206010008120 Cerebral ischaemia Diseases 0.000 claims abstract description 4
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- 208000026106 cerebrovascular disease Diseases 0.000 claims abstract description 4
- -1 indol-7-yl Chemical group 0.000 claims description 128
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 5
- 239000003215 serotonin 5-HT2 receptor antagonist Substances 0.000 claims description 5
- WOSOETCNFILDMJ-UHFFFAOYSA-N 1h-indol-5-yl-[4-(2-phenylethyl)piperazin-1-yl]methanone Chemical compound C=1C=C2NC=CC2=CC=1C(=O)N(CC1)CCN1CCC1=CC=CC=C1 WOSOETCNFILDMJ-UHFFFAOYSA-N 0.000 claims description 4
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 231100000867 compulsive behavior Toxicity 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
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- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Chemical group 0.000 claims description 4
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 201000006474 Brain Ischemia Diseases 0.000 claims description 3
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- SOONQGBOUDZOIC-UHFFFAOYSA-N 7-[4-[2-(4-fluorophenyl)ethyl]piperazine-1-carbonyl]-1h-indole-3-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNC2=C1C(=O)N(CC1)CCN1CCC1=CC=C(F)C=C1 SOONQGBOUDZOIC-UHFFFAOYSA-N 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- AQRLDDAFYYAIJP-UHFFFAOYSA-N Pruvanserin Chemical compound C1=CC(F)=CC=C1CCN1CCN(C(=O)C=2C=3NC=C(C=3C=CC=2)C#N)CC1 AQRLDDAFYYAIJP-UHFFFAOYSA-N 0.000 claims description 2
- 230000003042 antagnostic effect Effects 0.000 claims description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- BJLPQVTZQXCBTI-UHFFFAOYSA-N (5-methoxy-1h-indol-7-yl)-[4-(2-phenylethyl)piperazin-1-yl]methanone Chemical compound C=12NC=CC2=CC(OC)=CC=1C(=O)N(CC1)CCN1CCC1=CC=CC=C1 BJLPQVTZQXCBTI-UHFFFAOYSA-N 0.000 claims 2
- 208000000103 Anorexia Nervosa Diseases 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 abstract description 6
- 208000022531 anorexia Diseases 0.000 abstract description 6
- 206010061428 decreased appetite Diseases 0.000 abstract description 6
- 102000049773 5-HT2A Serotonin Receptor Human genes 0.000 abstract 1
- 108010072564 5-HT2A Serotonin Receptor Proteins 0.000 abstract 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 abstract 1
- 201000002859 sleep apnea Diseases 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 description 10
- 150000002367 halogens Chemical group 0.000 description 10
- 102000005962 receptors Human genes 0.000 description 10
- 108020003175 receptors Proteins 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 239000002585 base Substances 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 239000002400 serotonin 2A antagonist Substances 0.000 description 6
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- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 3
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- 125000001544 thienyl group Chemical group 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- 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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- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Public Health (AREA)
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- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Endocrinology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19934433A DE19934433A1 (de) | 1999-07-22 | 1999-07-22 | N-(Indolcarbonyl-)piperazinderivate |
| PCT/EP2000/006464 WO2001007435A2 (de) | 1999-07-22 | 2000-07-07 | N-(indolcarbonyl-)piperazinderivate als 5-ht2a-rezeptor liganden |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK512002A3 SK512002A3 (en) | 2002-05-09 |
| SK286066B6 true SK286066B6 (sk) | 2008-02-05 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK51-2002A SK286066B6 (sk) | 1999-07-22 | 2000-07-07 | Derivát N-(indolkarbonyl)piperazínu, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US6838461B1 (cs) |
| EP (1) | EP1198453B9 (cs) |
| JP (2) | JP5242871B2 (cs) |
| KR (1) | KR100779207B1 (cs) |
| CN (1) | CN1229345C (cs) |
| AR (1) | AR024819A1 (cs) |
| AT (1) | ATE236877T1 (cs) |
| AU (1) | AU770411B2 (cs) |
| BR (1) | BR0012607A (cs) |
| CA (1) | CA2383779C (cs) |
| CZ (1) | CZ300510B6 (cs) |
| DE (2) | DE19934433A1 (cs) |
| DK (1) | DK1198453T5 (cs) |
| ES (1) | ES2192535T3 (cs) |
| HK (1) | HK1048636B (cs) |
| HU (1) | HUP0201988A3 (cs) |
| MX (1) | MXPA02000730A (cs) |
| MY (1) | MY122531A (cs) |
| NO (1) | NO322154B1 (cs) |
| PL (1) | PL201893B1 (cs) |
| PT (1) | PT1198453E (cs) |
| RU (1) | RU2251548C2 (cs) |
| SK (1) | SK286066B6 (cs) |
| UA (1) | UA73518C2 (cs) |
| WO (1) | WO2001007435A2 (cs) |
| ZA (1) | ZA200201486B (cs) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6589954B1 (en) * | 1998-05-22 | 2003-07-08 | Scios, Inc. | Compounds and methods to treat cardiac failure and other disorders |
| IL146309A (en) | 1999-05-21 | 2008-03-20 | Scios Inc | Derivatives of the indole type and pharmaceutical preparations containing them as inhibitors of kinase p38 |
| DE19934432A1 (de) * | 1999-07-22 | 2001-02-01 | Merck Patent Gmbh | Indolderivate |
| DE19934433A1 (de) * | 1999-07-22 | 2001-01-25 | Merck Patent Gmbh | N-(Indolcarbonyl-)piperazinderivate |
| US20020156453A1 (en) * | 1999-10-14 | 2002-10-24 | Pettis Ronald J. | Method and device for reducing therapeutic dosage |
| US20020095134A1 (en) * | 1999-10-14 | 2002-07-18 | Pettis Ronald J. | Method for altering drug pharmacokinetics based on medical delivery platform |
| US8465468B1 (en) | 2000-06-29 | 2013-06-18 | Becton, Dickinson And Company | Intradermal delivery of substances |
| DE10102053A1 (de) * | 2001-01-17 | 2002-07-18 | Merck Patent Gmbh | Piperazinylcarbonylchinoline und -isochinoline |
| DE60212841T2 (de) | 2001-06-15 | 2007-06-21 | F. Hoffmann-La Roche Ag | 4 piperazinylindolderivate mit affinität zum 5-ht6-rezeptor |
| CN1253220C (zh) * | 2001-06-29 | 2006-04-26 | 贝克顿迪肯森公司 | 通过微管在真皮内输入疫苗和基因治疗剂 |
| DE10157673A1 (de) * | 2001-11-24 | 2003-06-05 | Merck Patent Gmbh | Verwendung von N-(Indolcarbonyl-)piperazinderivaten |
| GB0203811D0 (en) * | 2002-02-18 | 2002-04-03 | Glaxo Group Ltd | Compounds |
| DE10212564B4 (de) * | 2002-03-12 | 2007-04-19 | Neurobiotec Gmbh | 1-Allyl-ergotalkaloid-Derivate und ihre Verwendung zur Prophylaxe und Therapie von Migräne |
| DE10217006A1 (de) * | 2002-04-16 | 2003-11-06 | Merck Patent Gmbh | Substituierte Indole |
| CA2497086A1 (en) * | 2002-08-30 | 2004-03-11 | Becton, Dickinson And Company | Method of controlling pharmacokinetics of immunomodulatory compounds |
| DE10246357A1 (de) * | 2002-10-04 | 2004-04-15 | Merck Patent Gmbh | Verwendung von 5-HT2Rezeptorantagonisten |
| JP2007500251A (ja) * | 2003-06-13 | 2007-01-11 | ベクトン・ディキンソン・アンド・カンパニー | 生物学的に活性な作用物質の改良型皮内送達 |
| JP2007503435A (ja) * | 2003-08-26 | 2007-02-22 | ベクトン・ディキンソン・アンド・カンパニー | 治療薬の皮内送達法 |
| WO2005091922A2 (en) * | 2004-03-03 | 2005-10-06 | Becton, Dickinson And Company | Methods and devices for improving delivery of a substance to skin |
| AU2005240991A1 (en) * | 2004-04-15 | 2005-11-17 | Georgetown University | Use of (4-alkylpiperazinyl) (phenyl) methanones in the treatment of Alzheimer's disease |
| EP1744784A2 (en) * | 2004-05-11 | 2007-01-24 | Becton, Dickinson and Company | Formulations of anti-pain agents and methods of using the same |
| DE102004047517A1 (de) * | 2004-09-28 | 2006-03-30 | Merck Patent Gmbh | Neuartige Kristallform von (3-Cyan-1H-indol-7-yl)-[4-(4-fluorphenethyl)-piperazin-1-yl]-methanon, Hydrochlorid |
| WO2006066790A1 (en) * | 2004-12-21 | 2006-06-29 | F. Hoffmann-La Roche Ag | Tetralin and indane derivatives and uses thereof |
| GT200600042A (es) * | 2005-02-10 | 2006-09-27 | Aventis Pharma Inc | Compuestos de bis arilo y heteroarilo sustituido como antagonistas selectivos de 5ht2a |
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| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20110707 |