UA73518C2 - N-(indolecarbonyl)piperazine derivatives - Google Patents
N-(indolecarbonyl)piperazine derivatives Download PDFInfo
- Publication number
- UA73518C2 UA73518C2 UA2002021354A UA2002021354A UA73518C2 UA 73518 C2 UA73518 C2 UA 73518C2 UA 2002021354 A UA2002021354 A UA 2002021354A UA 2002021354 A UA2002021354 A UA 2002021354A UA 73518 C2 UA73518 C2 UA 73518C2
- Authority
- UA
- Ukraine
- Prior art keywords
- formula
- indol
- compounds
- group
- methanone
- Prior art date
Links
- 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 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 7
- 208000018737 Parkinson disease Diseases 0.000 claims abstract description 7
- 201000000980 schizophrenia Diseases 0.000 claims abstract description 7
- 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
- 208000028017 Psychotic disease Diseases 0.000 claims abstract description 6
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims abstract description 6
- 235000014632 disordered eating Nutrition 0.000 claims abstract description 6
- 208000023105 Huntington disease Diseases 0.000 claims abstract description 5
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 5
- 206010036618 Premenstrual syndrome Diseases 0.000 claims abstract description 5
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 4
- 208000025966 Neurological disease Diseases 0.000 claims abstract description 4
- -1 of M-(indolecarbonyl)piperazine Chemical class 0.000 claims description 100
- 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 32
- 150000003839 salts Chemical class 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 230000003042 antagnostic effect Effects 0.000 claims description 11
- 102000005962 receptors Human genes 0.000 claims description 11
- 108020003175 receptors Proteins 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical group C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 206010026749 Mania Diseases 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 230000004596 appetite loss Effects 0.000 claims description 6
- 206010008118 cerebral infarction Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 208000019017 loss of appetite Diseases 0.000 claims description 6
- 235000021266 loss of appetite Nutrition 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 208000035475 disorder Diseases 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 235000003642 hunger Nutrition 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 102000014630 G protein-coupled serotonin receptor activity proteins Human genes 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 230000000694 effects Effects 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 201000006474 Brain Ischemia Diseases 0.000 claims description 3
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 3
- 206010033664 Panic attack Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 208000019906 panic disease Diseases 0.000 claims description 3
- 201000002859 sleep apnea Diseases 0.000 claims description 3
- 208000019116 sleep disease Diseases 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 210000005056 cell body Anatomy 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 6
- 208000026106 cerebrovascular disease Diseases 0.000 claims 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 2
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 2
- WSPOMRSOLSGNFJ-VGOFMYFVSA-N (E)-chlorprothixene Chemical compound C1=C(Cl)C=C2C(=C/CCN(C)C)/C3=CC=CC=C3SC2=C1 WSPOMRSOLSGNFJ-VGOFMYFVSA-N 0.000 claims 1
- BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 claims 1
- PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 claims 1
- KLPWJLBORRMFGK-UHFFFAOYSA-N Molindone Chemical compound O=C1C=2C(CC)=C(C)NC=2CCC1CN1CCOCC1 KLPWJLBORRMFGK-UHFFFAOYSA-N 0.000 claims 1
- RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-UHFFFAOYSA-N 0.000 claims 1
- KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 claims 1
- GFBKORZTTCHDGY-UWVJOHFNSA-N Thiothixene Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2\C1=C\CCN1CCN(C)CC1 GFBKORZTTCHDGY-UWVJOHFNSA-N 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- WNTYBHLDCKXEOT-UHFFFAOYSA-N acetophenazine Chemical compound C12=CC(C(=O)C)=CC=C2SC2=CC=CC=C2N1CCCN1CCN(CCO)CC1 WNTYBHLDCKXEOT-UHFFFAOYSA-N 0.000 claims 1
- 229960000276 acetophenazine Drugs 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 claims 1
- 229960001076 chlorpromazine Drugs 0.000 claims 1
- 229960004170 clozapine Drugs 0.000 claims 1
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 claims 1
- 229960002690 fluphenazine Drugs 0.000 claims 1
- 229960003878 haloperidol Drugs 0.000 claims 1
- 229960000423 loxapine Drugs 0.000 claims 1
- XJGVXQDUIWGIRW-UHFFFAOYSA-N loxapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2OC2=CC=C(Cl)C=C12 XJGVXQDUIWGIRW-UHFFFAOYSA-N 0.000 claims 1
- SLVMESMUVMCQIY-UHFFFAOYSA-N mesoridazine Chemical compound CN1CCCCC1CCN1C2=CC(S(C)=O)=CC=C2SC2=CC=CC=C21 SLVMESMUVMCQIY-UHFFFAOYSA-N 0.000 claims 1
- 229960000300 mesoridazine Drugs 0.000 claims 1
- 229960004938 molindone Drugs 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 229960005017 olanzapine Drugs 0.000 claims 1
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims 1
- 229960000762 perphenazine Drugs 0.000 claims 1
- YVUQSNJEYSNKRX-UHFFFAOYSA-N pimozide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC(N2C(NC3=CC=CC=C32)=O)CC1 YVUQSNJEYSNKRX-UHFFFAOYSA-N 0.000 claims 1
- 229960003634 pimozide Drugs 0.000 claims 1
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims 1
- 229960001534 risperidone Drugs 0.000 claims 1
- 229960004940 sulpiride Drugs 0.000 claims 1
- 229960002784 thioridazine Drugs 0.000 claims 1
- 229960005013 tiotixene Drugs 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- ZEWQUBUPAILYHI-UHFFFAOYSA-N trifluoperazine Chemical compound C1CN(C)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 ZEWQUBUPAILYHI-UHFFFAOYSA-N 0.000 claims 1
- 229960002324 trifluoperazine Drugs 0.000 claims 1
- JOLJIIDDOBNFHW-UHFFFAOYSA-N xanomeline Chemical compound CCCCCCOC1=NSN=C1C1=CCCN(C)C1 JOLJIIDDOBNFHW-UHFFFAOYSA-N 0.000 claims 1
- 229950006755 xanomeline Drugs 0.000 claims 1
- 229960000607 ziprasidone Drugs 0.000 claims 1
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 claims 1
- 239000005557 antagonist Substances 0.000 abstract description 2
- 208000032841 Bulimia Diseases 0.000 abstract 1
- 206010006550 Bulimia nervosa Diseases 0.000 abstract 1
- 208000022531 anorexia Diseases 0.000 abstract 1
- 230000006399 behavior Effects 0.000 abstract 1
- 206010061428 decreased appetite Diseases 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 24
- BKXVVCILCIUCLG-UHFFFAOYSA-N raloxifene hydrochloride Chemical compound [H+].[Cl-].C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 BKXVVCILCIUCLG-UHFFFAOYSA-N 0.000 description 21
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 17
- 239000011734 sodium Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 13
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- 229910052708 sodium Inorganic materials 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000872 buffer Substances 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
- 239000002585 base Substances 0.000 description 5
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 5
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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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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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Classifications
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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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- 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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- Endocrinology (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 (1)
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| UA73518C2 true UA73518C2 (en) | 2005-08-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2002021354A UA73518C2 (en) | 1999-07-22 | 2000-07-07 | N-(indolecarbonyl)piperazine derivatives |
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| Country | Link |
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| US (2) | US6838461B1 (pl) |
| EP (1) | EP1198453B9 (pl) |
| JP (2) | JP5242871B2 (pl) |
| KR (1) | KR100779207B1 (pl) |
| CN (1) | CN1229345C (pl) |
| AR (1) | AR024819A1 (pl) |
| AT (1) | ATE236877T1 (pl) |
| AU (1) | AU770411B2 (pl) |
| BR (1) | BR0012607A (pl) |
| CA (1) | CA2383779C (pl) |
| CZ (1) | CZ300510B6 (pl) |
| DE (2) | DE19934433A1 (pl) |
| DK (1) | DK1198453T5 (pl) |
| ES (1) | ES2192535T3 (pl) |
| HK (1) | HK1048636B (pl) |
| HU (1) | HUP0201988A3 (pl) |
| MX (1) | MXPA02000730A (pl) |
| MY (1) | MY122531A (pl) |
| NO (1) | NO322154B1 (pl) |
| PL (1) | PL201893B1 (pl) |
| PT (1) | PT1198453E (pl) |
| RU (1) | RU2251548C2 (pl) |
| SK (1) | SK286066B6 (pl) |
| UA (1) | UA73518C2 (pl) |
| WO (1) | WO2001007435A2 (pl) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2549963C1 (ru) * | 2014-04-08 | 2015-05-10 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Дальневосточный государственный медицинский университет" Министерства здравоохранения Российской Федерации (ГБОУ ВПО "ДВГМУ" Минздрава России) | Способ прогнозирования развития критической печеночной недостаточности на основании сывороточного уровня селена |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| 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 |
| 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 |
| US20020156453A1 (en) * | 1999-10-14 | 2002-10-24 | Pettis Ronald J. | Method and device for reducing therapeutic dosage |
| DE10102053A1 (de) * | 2001-01-17 | 2002-07-18 | Merck Patent Gmbh | Piperazinylcarbonylchinoline und -isochinoline |
| EP1401812B1 (en) * | 2001-06-15 | 2006-06-28 | F. Hoffmann-La Roche Ag | 4-piperazinylindole derivatives with 5-ht6 receptor affinity |
| JP2004531578A (ja) * | 2001-06-29 | 2004-10-14 | ベクトン・ディキンソン・アンド・カンパニー | ワクチンおよび遺伝子治療剤のマイクロカニューレによる皮内送達 |
| 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 |
| BR0313890A (pt) * | 2002-08-30 | 2005-07-26 | Becton Dickinson Co | Método de controle da farmacocinética de compostos imunomoduladores |
| DE10246357A1 (de) * | 2002-10-04 | 2004-04-15 | Merck Patent Gmbh | Verwendung von 5-HT2Rezeptorantagonisten |
| EP1635876A4 (en) * | 2003-06-13 | 2009-05-06 | Becton Dickinson Co | IMPROVED INTRADERMAL ADMINISTRATION OF BIOACTIVE AGENTS |
| US20050180952A1 (en) * | 2003-08-26 | 2005-08-18 | Pettis Ronald J. | Methods for intradermal delivery of therapeutics agents |
| US20050256499A1 (en) * | 2004-03-03 | 2005-11-17 | Pettis Ronald J | Methods and devices for improving delivery of a substance to skin |
| EP1755605A2 (en) * | 2004-04-15 | 2007-02-28 | Samaritan Pharmaceuticals, Inc. | 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 |
| PT1831159E (pt) * | 2004-12-21 | 2010-03-03 | Hoffmann La Roche | Derivados de tetralina e de indano e as suas utilizações |
| GT200600042A (es) * | 2005-02-10 | 2006-09-27 | Aventis Pharma Inc | Compuestos de bis arilo y heteroarilo sustituido como antagonistas selectivos de 5ht2a |
| WO2007130814A1 (en) * | 2006-05-05 | 2007-11-15 | Merck Patent Gmbh | Crystalline (3-cyano-1h-indol-7-yl)-[4-(4-fluorophenethyl)piperazin-1-yl]methanone phosphate |
| US7514433B2 (en) * | 2006-08-03 | 2009-04-07 | Hoffmann-La Roche Inc. | 1H-indole-6-yl-piperazin-1-yl-methanone derivatives |
| AU2008251259B2 (en) * | 2007-05-14 | 2013-02-14 | Sk Biopharmaceuticals Co., Ltd. | Novel carbamoyloxy arylalkanoyl arylpiperazine compound, pharmaceutical compositions comprising the compound and method for treating pain, anxiety and depression by administering the compound |
| EP2008656A1 (en) * | 2007-06-28 | 2008-12-31 | Bergen Teknologioverforing AS | Compositions for the treatment of hyperphenylalaninemia |
| US9567327B2 (en) * | 2007-08-15 | 2017-02-14 | Arena Pharmaceuticals, Inc. | Imidazo[1,2-a]pyridine derivatives as modulators of the 5-HT2A serotonin receptor useful for the treatment of disorders related thereto |
| KR101062376B1 (ko) | 2008-04-10 | 2011-09-06 | 한국화학연구원 | 신규 인돌 카르복실산 비스피리딜 카르복사마이드 유도체,이의 제조방법 및 이를 유효성분으로 함유하는 조성물 |
| US9308323B2 (en) | 2011-11-15 | 2016-04-12 | Smiths Medical Asd, Inc. | Systems and methods for illuminated medical tubing detection and management indicating a characteristic of at least one infusion pump |
| EP3419976B1 (en) | 2016-02-25 | 2021-04-07 | Asceneuron SA | Acid addition salts of piperazine derivatives |
| GB2554371B (en) * | 2016-09-22 | 2019-10-09 | Resolute Energy Solutions Ltd | Well apparatus and associated methods |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU214598B (hu) | 1987-09-24 | 1998-04-28 | Jencap Research Ltd | Eljárás fogamzásgátló és hormonterápiához alkalmazható, ösztrogént és progesztint tartalmazó gyógyszerkészítmények előállítására |
| US5093341A (en) * | 1987-12-17 | 1992-03-03 | Merrell Dow Pharmaceuticals Inc. | N-aralkyl piperidine derivatives useful as antithrombolytic agents |
| US5032598A (en) | 1989-12-08 | 1991-07-16 | Merck & Co., Inc. | Nitrogens containing heterocyclic compounds as class III antiarrhythmic agents |
| US5032604A (en) * | 1989-12-08 | 1991-07-16 | Merck & Co., Inc. | Class III antiarrhythmic agents |
| US5330986A (en) * | 1992-11-24 | 1994-07-19 | Hoechst-Roussel Pharmaceuticals Inc. | Indole-7-carboxamide derivatives |
| IL114026A (en) | 1994-06-08 | 1999-06-20 | Lundbeck & Co As H | 4-aryl-1-(indanmethyl dihydrobenzofuranmethyl or dihydrobenzo thiophenemethyl) piperidines tetrahydropyridines or piperazines and pharmaceutical compositions containing them |
| JP2001506230A (ja) | 1996-08-09 | 2001-05-15 | スミスクライン・ビーチャム・コーポレイション | 新規ピペラジン含有化合物 |
| GB9718712D0 (en) | 1997-09-03 | 1997-11-12 | Merck Sharp & Dohme | Theraputic Agents |
| 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 |
| JPWO2005099240A1 (ja) * | 2004-04-07 | 2008-03-06 | 松下電器産業株式会社 | 情報交換支援装置、情報交換支援方法、及び情報交換支援プログラム |
-
1999
- 1999-07-22 DE DE19934433A patent/DE19934433A1/de not_active Withdrawn
-
2000
- 2000-07-07 SK SK51-2002A patent/SK286066B6/sk not_active IP Right Cessation
- 2000-07-07 WO PCT/EP2000/006464 patent/WO2001007435A2/de not_active Ceased
- 2000-07-07 HK HK03100811.4A patent/HK1048636B/zh not_active IP Right Cessation
- 2000-07-07 CN CNB00810719XA patent/CN1229345C/zh not_active Expired - Fee Related
- 2000-07-07 PT PT00949288T patent/PT1198453E/pt unknown
- 2000-07-07 BR BR0012607-1A patent/BR0012607A/pt active Search and Examination
- 2000-07-07 DK DK00949288T patent/DK1198453T5/da active
- 2000-07-07 PL PL353446A patent/PL201893B1/pl not_active IP Right Cessation
- 2000-07-07 HU HU0201988A patent/HUP0201988A3/hu unknown
- 2000-07-07 AT AT00949288T patent/ATE236877T1/de not_active IP Right Cessation
- 2000-07-07 KR KR1020027000315A patent/KR100779207B1/ko not_active Expired - Fee Related
- 2000-07-07 UA UA2002021354A patent/UA73518C2/uk unknown
- 2000-07-07 EP EP00949288A patent/EP1198453B9/de not_active Expired - Lifetime
- 2000-07-07 US US10/031,367 patent/US6838461B1/en not_active Expired - Lifetime
- 2000-07-07 DE DE50001729T patent/DE50001729D1/de not_active Expired - Lifetime
- 2000-07-07 CZ CZ20020068A patent/CZ300510B6/cs not_active IP Right Cessation
- 2000-07-07 RU RU2002103302/04A patent/RU2251548C2/ru not_active IP Right Cessation
- 2000-07-07 MX MXPA02000730A patent/MXPA02000730A/es active IP Right Grant
- 2000-07-07 AU AU62704/00A patent/AU770411B2/en not_active Ceased
- 2000-07-07 ES ES00949288T patent/ES2192535T3/es not_active Expired - Lifetime
- 2000-07-07 JP JP2001512519A patent/JP5242871B2/ja not_active Expired - Fee Related
- 2000-07-07 CA CA2383779A patent/CA2383779C/en not_active Expired - Fee Related
- 2000-07-20 MY MYPI20003320A patent/MY122531A/en unknown
- 2000-07-21 AR ARP000103775A patent/AR024819A1/es active IP Right Grant
-
2002
- 2002-01-21 NO NO20020307A patent/NO322154B1/no not_active IP Right Cessation
- 2002-02-21 ZA ZA200201486A patent/ZA200201486B/en unknown
-
2004
- 2004-12-17 US US11/013,908 patent/US7084143B2/en not_active Expired - Fee Related
-
2011
- 2011-07-29 JP JP2011166851A patent/JP2012006940A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2549963C1 (ru) * | 2014-04-08 | 2015-05-10 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Дальневосточный государственный медицинский университет" Министерства здравоохранения Российской Федерации (ГБОУ ВПО "ДВГМУ" Минздрава России) | Способ прогнозирования развития критической печеночной недостаточности на основании сывороточного уровня селена |
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