BG62169B1 - 3-(5-тетразолил-бензил)амино-пиперидинови производни, методи за получаването им и фармацевтични състави с тях, използвани κακτο при метод за лечение, така и за производство на лекарства с приложе- ние при лечение на състояния, в които тахикинините са посредници - Google Patents
3-(5-тетразолил-бензил)амино-пиперидинови производни, методи за получаването им и фармацевтични състави с тях, използвани κακτο при метод за лечение, така и за производство на лекарства с приложе- ние при лечение на състояния, в които тахикинините са посредници Download PDFInfo
- Publication number
- BG62169B1 BG62169B1 BG100487A BG10048796A BG62169B1 BG 62169 B1 BG62169 B1 BG 62169B1 BG 100487 A BG100487 A BG 100487A BG 10048796 A BG10048796 A BG 10048796A BG 62169 B1 BG62169 B1 BG 62169B1
- Authority
- BG
- Bulgaria
- Prior art keywords
- methoxy
- tetrazol
- phenyl
- formula
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 26
- 238000011282 treatment Methods 0.000 title claims description 22
- 239000003814 drug Substances 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 13
- 102000003141 Tachykinin Human genes 0.000 title claims description 10
- 108060008037 tachykinin Proteins 0.000 title claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 230000001404 mediated effect Effects 0.000 title claims description 6
- 229940079593 drug Drugs 0.000 title description 6
- JEZOFBZBNQWWKG-UHFFFAOYSA-N n-[[3-(2h-tetrazol-5-yl)phenyl]methyl]piperidin-3-amine Chemical class C=1C=CC(C2=NNN=N2)=CC=1CNC1CCCNC1 JEZOFBZBNQWWKG-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 352
- -1 2-methoxy-5-tetrazole- 1-yl-benzyl Chemical group 0.000 claims description 90
- 150000003839 salts Chemical class 0.000 claims description 41
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 239000012453 solvate Substances 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
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- 101800003906 Substance P Proteins 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- QDZOEBFLNHCSSF-PFFBOGFISA-N (2S)-2-[[(2R)-2-[[(2S)-1-[(2S)-6-amino-2-[[(2S)-1-[(2R)-2-amino-5-carbamimidamidopentanoyl]pyrrolidine-2-carbonyl]amino]hexanoyl]pyrrolidine-2-carbonyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-N-[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]pentanediamide Chemical compound C([C@@H](C(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CCCNC(N)=N)C1=CC=CC=C1 QDZOEBFLNHCSSF-PFFBOGFISA-N 0.000 claims description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 235000019270 ammonium chloride Nutrition 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
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- 239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 claims description 3
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- 125000002252 acyl group Chemical group 0.000 claims description 2
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- 229960003727 granisetron Drugs 0.000 claims description 2
- 229960004503 metoclopramide Drugs 0.000 claims description 2
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 claims description 2
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- 239000002904 solvent Substances 0.000 description 36
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 30
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- 229910052757 nitrogen Inorganic materials 0.000 description 26
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 25
- 239000012044 organic layer Substances 0.000 description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- 238000003756 stirring Methods 0.000 description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 20
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- 239000002253 acid Substances 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
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- 235000019341 magnesium sulphate Nutrition 0.000 description 19
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 17
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- ZGEOYRPBZDERPR-UHFFFAOYSA-N 1-[3-(1,3-dioxolan-2-yl)-4-methoxyphenyl]tetrazole Chemical compound COC1=CC=C(N2N=NN=C2)C=C1C1OCCO1 ZGEOYRPBZDERPR-UHFFFAOYSA-N 0.000 description 4
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
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- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939319606A GB9319606D0 (en) | 1993-09-22 | 1993-09-22 | Chemical compounds |
| GB9326583A GB9326583D0 (en) | 1993-12-31 | 1993-12-31 | Chemical compounds |
| PCT/EP1994/003129 WO1995008549A1 (en) | 1993-09-22 | 1994-09-20 | 3-(5-tetrazolyl-benzyl)amino-piperidine derivatives and antagonists of tachykinins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG100487A BG100487A (bg) | 1996-12-31 |
| BG62169B1 true BG62169B1 (bg) | 1999-04-30 |
Family
ID=26303560
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG100487A BG62169B1 (bg) | 1993-09-22 | 1996-04-09 | 3-(5-тетразолил-бензил)амино-пиперидинови производни, методи за получаването им и фармацевтични състави с тях, използвани κακτο при метод за лечение, така и за производство на лекарства с приложе- ние при лечение на състояния, в които тахикинините са посредници |
Country Status (29)
| Country | Link |
|---|---|
| US (2) | US5703240A (cs) |
| EP (1) | EP0720609B1 (cs) |
| JP (2) | JP2865872B2 (cs) |
| CN (1) | CN1061041C (cs) |
| AP (1) | AP495A (cs) |
| AT (1) | ATE173255T1 (cs) |
| AU (1) | AU681190B2 (cs) |
| BG (1) | BG62169B1 (cs) |
| CA (1) | CA2172529A1 (cs) |
| CO (1) | CO4290298A1 (cs) |
| CZ (1) | CZ285479B6 (cs) |
| DE (1) | DE69414590T2 (cs) |
| DK (1) | DK0720609T3 (cs) |
| ES (1) | ES2123829T3 (cs) |
| FI (1) | FI961270A7 (cs) |
| GR (1) | GR3029354T3 (cs) |
| HR (1) | HRP940575B1 (cs) |
| HU (1) | HU217428B (cs) |
| IL (1) | IL111002A (cs) |
| IS (1) | IS4208A (cs) |
| NO (1) | NO307830B1 (cs) |
| NZ (1) | NZ273614A (cs) |
| OA (1) | OA10576A (cs) |
| PE (1) | PE18295A1 (cs) |
| PL (1) | PL179585B1 (cs) |
| SI (1) | SI0720609T1 (cs) |
| SK (1) | SK280901B6 (cs) |
| UA (1) | UA44711C2 (cs) |
| WO (1) | WO1995008549A1 (cs) |
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| GB9317987D0 (en) * | 1993-08-26 | 1993-10-13 | Glaxo Group Ltd | Chemical compounds |
| IS4208A (is) * | 1993-09-22 | 1995-03-23 | Glaxo Group Limited | 3-(tetrazólýl-benzyl)amínó-piperadidín afleiður |
| WO1996021661A1 (en) * | 1995-01-12 | 1996-07-18 | Glaxo Group Limited | Piperidine derivatives having tachykinin antagonist activity |
| GB9505692D0 (en) * | 1995-03-21 | 1995-05-10 | Glaxo Group Ltd | Chemical compounds |
| GB9513117D0 (en) * | 1995-06-28 | 1995-08-30 | Merck Sharp & Dohme | Therapeutic agents |
| TW458774B (en) | 1995-10-20 | 2001-10-11 | Pfizer | Antiemetic pharmaceutical compositions |
| US6211199B1 (en) | 1995-11-17 | 2001-04-03 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl-amino)piperidines useful for the treatment of allergic diseases |
| GB9525296D0 (en) * | 1995-12-11 | 1996-02-07 | Merck Sharp & Dohme | Therapeutic agents |
| US5998439A (en) | 1996-02-21 | 1999-12-07 | Hoescht Marion Roussel, Inc. | Substituted N-methyl-N-(4-(piperidin-1-yl)-2-(aryl)butyl)benzamides useful for the treatment of allergic diseases |
| US5932571A (en) * | 1996-02-21 | 1999-08-03 | Hoechst Marion Roussel, Inc. | Substituted N-methyl-N-(4-(4-(1H-benzimidazol-2-yl) {1,4}diazepan-1-yl)-2-(aryl) butyl) benzamides useful for the treatment of allergic diseases |
| US5922737A (en) * | 1996-02-21 | 1999-07-13 | Hoechst Marion Roussel, Inc. | Substituted N-methyl-N-(4-(4-(1H-Benzimidazol-2-YL-amino) piperidin-1-YL)-2-(arlyl) butyl) benzamides useful for the treatment of allergic diseases |
| JP2000514047A (ja) * | 1996-06-26 | 2000-10-24 | ワーナー―ランバート・コンパニー | 催吐の処置用医薬の製造のためのタキキニンアンタゴニストの使用 |
| MX9706196A (es) * | 1996-08-14 | 1998-02-28 | Pfizer | Compuestos triciclicos de piperidinilamino como antagonistas de la sustancia p. |
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| EP0942731B1 (en) * | 1996-12-02 | 2004-11-17 | MERCK SHARP & DOHME LTD. | Use of nk-1 receptor antagonists for treating substance use disorders |
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| DE69732492T2 (de) * | 1996-12-02 | 2006-03-30 | Merck Sharp & Dohme Ltd., Hoddesdon | Verwendung von nk-1 rezeptorantagonisten zur behandlung von schweren depressionen, die von angstzuständen begleitet werden |
| US5977104A (en) * | 1996-12-02 | 1999-11-02 | Merck Sharp & Dohme Ltd. | Use of NK-1 receptor antagonists for treating bipolar disorders |
| ATE282417T1 (de) * | 1996-12-02 | 2004-12-15 | Merck Sharp & Dohme | Die verwendung von nk-1 rezeptor antagonisten für die behandlung von bewegungsstörungen |
| CA2273807A1 (en) * | 1996-12-02 | 1998-06-11 | Merck Sharp & Dohme Limited | Use of nk-1 receptor antagonists for treating schizophrenic disorders |
| ATE274908T1 (de) * | 1996-12-02 | 2004-09-15 | Merck Sharp & Dohme | Die verwendung von nk-1 rezeptor antagonisten für die behandlungen von stress störungen |
| JP2001504848A (ja) * | 1996-12-02 | 2001-04-10 | メルク シヤープ エンド ドーム リミテツド | 重症不安障害の治療のためのｎｋ−１受容体拮抗薬の使用 |
| JP2001504851A (ja) * | 1996-12-02 | 2001-04-10 | メルク シヤープ エンド ドーム リミテツド | 性的機能不全の治療のためのｎｋ−１受容体拮抗薬の使用 |
| US6613765B1 (en) | 1996-12-02 | 2003-09-02 | Merck Sharp & Dohme Limited | Use of NK-1 receptor antagonists for treating major depressive disorders |
| US6100256A (en) * | 1996-12-02 | 2000-08-08 | Merck Sharp & Dohme Ltd. | Use of NK-1 receptors antagonists for treating schizophrenic disorders |
| US6114315A (en) * | 1996-12-02 | 2000-09-05 | Merck Sharp & Dohme Ltd. | Use of NK-1 receptor antagonists for treating major depressive disorders with anxiety |
| CA2273856A1 (en) * | 1996-12-02 | 1998-06-11 | Merck Sharp & Dohme Limited | Use of nk-1 receptor antagonists for treating bipolar disorders |
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| JP2002506459A (ja) | 1997-06-27 | 2002-02-26 | メルク シヤープ エンド ドーム リミテツド | 置換された３−（ベンジルアミノ）ピペリジン誘導体およびその治療薬としての使用 |
| CA2298779A1 (en) * | 1997-08-04 | 1999-02-18 | Merck Sharp & Dohme Limited | Use of nk-1 receptor antagonists for treating aggressive behaviour disorders |
| GB9716457D0 (en) * | 1997-08-04 | 1997-10-08 | Merck Sharp & Dohme | Therapeutic agents |
| GB9716463D0 (en) * | 1997-08-04 | 1997-10-08 | Merck Sharp & Dohme | Therapeutic agents |
| WO1999007376A1 (en) * | 1997-08-04 | 1999-02-18 | Merck Sharp & Dohme Limited | Use of nk-1 receptor antagonists for treating mania |
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| US6087348A (en) * | 1997-12-01 | 2000-07-11 | Merck Sharp & Dohme Ltd. | Use of NK-1 receptor antagonists for treating stress disorders |
| US6271230B1 (en) | 1997-12-01 | 2001-08-07 | Merck Sharp & Dohme Limited | Use of NK-1 receptor antagonists for treating cognitive disorders |
| US6156749A (en) * | 1997-12-01 | 2000-12-05 | Merck Sharp & Dohme Limited | Use of NK-1 receptor antagonists for treating movement disorders |
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| US20040142929A1 (en) * | 2001-07-06 | 2004-07-22 | Ramon Merce-Vidal | Derivatives of aryl (or heteroaryl) azolylcarbinoles for the treatment of urinary incontinence |
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| US5332817A (en) * | 1990-01-04 | 1994-07-26 | Pfizer Inc. | 3-aminopiperidine derivatives and related nitrogen containing heterocycles |
| UA41251C2 (uk) * | 1990-01-04 | 2001-09-17 | Пфайзер, Інк. | Гідровані азотвмісні гетероциклічні сполуки, похідні піперидину, фармацевтична композиція та спосіб пригнічення активності речовини р в організмі |
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| CA2109613C (en) * | 1991-06-20 | 1996-11-19 | John Adams Lowe Iii | Fluoroalkoxybenzylamino derivatives of nitrogen containing heterocycles |
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1994
- 1994-09-19 IS IS4208A patent/IS4208A/is unknown
- 1994-09-19 IL IL11100294A patent/IL111002A/en not_active IP Right Cessation
- 1994-09-20 ES ES94927627T patent/ES2123829T3/es not_active Expired - Lifetime
- 1994-09-20 CO CO94042544A patent/CO4290298A1/es unknown
- 1994-09-20 PE PE1994251007A patent/PE18295A1/es not_active Application Discontinuation
- 1994-09-20 US US08/612,843 patent/US5703240A/en not_active Expired - Lifetime
- 1994-09-20 NZ NZ273614A patent/NZ273614A/en unknown
- 1994-09-20 DE DE69414590T patent/DE69414590T2/de not_active Expired - Lifetime
- 1994-09-20 SI SI9430208T patent/SI0720609T1/xx unknown
- 1994-09-20 AT AT94927627T patent/ATE173255T1/de not_active IP Right Cessation
- 1994-09-20 UA UA96031099A patent/UA44711C2/uk unknown
- 1994-09-20 JP JP7509554A patent/JP2865872B2/ja not_active Expired - Lifetime
- 1994-09-20 WO PCT/EP1994/003129 patent/WO1995008549A1/en active IP Right Grant
- 1994-09-20 DK DK94927627T patent/DK0720609T3/da active
- 1994-09-20 AU AU76974/94A patent/AU681190B2/en not_active Ceased
- 1994-09-20 PL PL94313619A patent/PL179585B1/pl unknown
- 1994-09-20 CZ CZ96830A patent/CZ285479B6/cs not_active IP Right Cessation
- 1994-09-20 CA CA002172529A patent/CA2172529A1/en not_active Abandoned
- 1994-09-20 HR HR940575A patent/HRP940575B1/xx not_active IP Right Cessation
- 1994-09-20 SK SK383-96A patent/SK280901B6/sk unknown
- 1994-09-20 EP EP94927627A patent/EP0720609B1/en not_active Expired - Lifetime
- 1994-09-20 HU HU9600722A patent/HU217428B/hu not_active IP Right Cessation
- 1994-09-20 CN CN94194145A patent/CN1061041C/zh not_active Expired - Fee Related
- 1994-09-21 AP APAP/P/1994/000671A patent/AP495A/en active
-
1996
- 1996-03-19 FI FI961270A patent/FI961270A7/fi unknown
- 1996-03-21 NO NO961156A patent/NO307830B1/no not_active IP Right Cessation
- 1996-03-21 OA OA60801A patent/OA10576A/en unknown
- 1996-04-09 BG BG100487A patent/BG62169B1/bg unknown
-
1997
- 1997-07-23 US US08/899,190 patent/US5843966A/en not_active Expired - Lifetime
-
1998
- 1998-08-07 JP JP10224991A patent/JPH11106341A/ja active Pending
-
1999
- 1999-02-10 GR GR990400441T patent/GR3029354T3/el unknown
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