CZ300510B6 - Derivát N-(indolkarbonyl)piperazinu, zpusob jeho prípravy a farmaceutický prostredek s jeho obsahem - Google Patents
Derivát N-(indolkarbonyl)piperazinu, zpusob jeho prípravy a farmaceutický prostredek s jeho obsahem Download PDFInfo
- Publication number
- CZ300510B6 CZ300510B6 CZ20020068A CZ200268A CZ300510B6 CZ 300510 B6 CZ300510 B6 CZ 300510B6 CZ 20020068 A CZ20020068 A CZ 20020068A CZ 200268 A CZ200268 A CZ 200268A CZ 300510 B6 CZ300510 B6 CZ 300510B6
- Authority
- CZ
- Czechia
- Prior art keywords
- indol
- methanone
- formula
- piperazine
- indolecarbonyl
- Prior art date
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- 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 16
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims abstract description 11
- 230000008569 process Effects 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 239000012453 solvate Substances 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 125000001041 indolyl group Chemical group 0.000 claims abstract description 9
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical group C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000002252 acyl group Chemical group 0.000 claims abstract description 8
- 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 abstract description 7
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 4
- 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 abstract description 3
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims abstract 2
- -1 3-Aminocarbonyl-1H-indol-7-yl Chemical group 0.000 claims description 122
- 150000001875 compounds Chemical class 0.000 claims description 55
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 36
- 238000011282 treatment Methods 0.000 claims description 26
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- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 8
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- 230000003042 antagnostic effect Effects 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
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- 231100000867 compulsive behavior Toxicity 0.000 claims description 6
- 235000014632 disordered eating Nutrition 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
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- 239000011737 fluorine Substances 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004169 (C1-C6) alkyl group Chemical group 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
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- 125000004429 atom Chemical group 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 abstract description 9
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
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- C—CHEMISTRY; METALLURGY
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- 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)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19934433A DE19934433A1 (de) | 1999-07-22 | 1999-07-22 | N-(Indolcarbonyl-)piperazinderivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ200268A3 CZ200268A3 (cs) | 2002-04-17 |
| CZ300510B6 true CZ300510B6 (cs) | 2009-06-03 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20020068A CZ300510B6 (cs) | 1999-07-22 | 2000-07-07 | Derivát N-(indolkarbonyl)piperazinu, zpusob jeho prípravy a farmaceutický prostredek s jeho obsahem |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US6838461B1 (https=) |
| EP (1) | EP1198453B9 (https=) |
| JP (2) | JP5242871B2 (https=) |
| KR (1) | KR100779207B1 (https=) |
| CN (1) | CN1229345C (https=) |
| AR (1) | AR024819A1 (https=) |
| AT (1) | ATE236877T1 (https=) |
| AU (1) | AU770411B2 (https=) |
| BR (1) | BR0012607A (https=) |
| CA (1) | CA2383779C (https=) |
| CZ (1) | CZ300510B6 (https=) |
| DE (2) | DE19934433A1 (https=) |
| DK (1) | DK1198453T5 (https=) |
| ES (1) | ES2192535T3 (https=) |
| HK (1) | HK1048636B (https=) |
| HU (1) | HUP0201988A3 (https=) |
| MX (1) | MXPA02000730A (https=) |
| MY (1) | MY122531A (https=) |
| NO (1) | NO322154B1 (https=) |
| PL (1) | PL201893B1 (https=) |
| PT (1) | PT1198453E (https=) |
| RU (1) | RU2251548C2 (https=) |
| SK (1) | SK286066B6 (https=) |
| UA (1) | UA73518C2 (https=) |
| WO (1) | WO2001007435A2 (https=) |
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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 |
| WO2003002069A2 (en) * | 2001-06-29 | 2003-01-09 | Becton, Dickinson And Company | Intradermal delivery of vaccines and gene therapeutic agents via microcannula |
| 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 |
| AU2003262888A1 (en) * | 2002-08-30 | 2004-03-19 | 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 |
| AU2004264839B2 (en) * | 2003-06-13 | 2009-06-04 | Becton, Dickinson And Company | Improved intra-dermal delivery of biologically active agents |
| AU2004270113A1 (en) * | 2003-08-26 | 2005-03-17 | Becton, Dickinson And Company | Methods for intradermal delivery of therapeutics agents |
| WO2005091922A2 (en) * | 2004-03-03 | 2005-10-06 | Becton, Dickinson And Company | Methods and devices for improving delivery of a substance to skin |
| CN101022806A (zh) * | 2004-04-15 | 2007-08-22 | 萨马里坦药品公司 | （4－烷基哌嗪基）（苯基）甲酮在治疗阿尔茨海默病中的应用 |
| WO2005115360A2 (en) * | 2004-05-11 | 2005-12-08 | 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 |
| MX2007007558A (es) * | 2004-12-21 | 2007-07-24 | Hoffmann La Roche | Derivados de tetralina y de indano y usos de los mismos. |
| 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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| Date | Code | Title | Description |
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| MM4A | Patent lapsed due to non-payment of fee |
Effective date: 20110707 |