AR034396A1 - Compuestos 4-(1r-4-piperidilen)-4h-benzo[4,5]ciclohepta[1,2]-tiofeno-1-a y sus isomeros opticamente activos, un metodo para su sintesis y el uso de dichos compuestos para la manufactura de un medicamento - Google Patents
Compuestos 4-(1r-4-piperidilen)-4h-benzo[4,5]ciclohepta[1,2]-tiofeno-1-a y sus isomeros opticamente activos, un metodo para su sintesis y el uso de dichos compuestos para la manufactura de un medicamentoInfo
- Publication number
- AR034396A1 AR034396A1 ARP000104790A ARP000104790A AR034396A1 AR 034396 A1 AR034396 A1 AR 034396A1 AR P000104790 A ARP000104790 A AR P000104790A AR P000104790 A ARP000104790 A AR P000104790A AR 034396 A1 AR034396 A1 AR 034396A1
- Authority
- AR
- Argentina
- Prior art keywords
- compounds
- ketotifen
- norketotifen
- hydroxy
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 7
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 229940126601 medicinal product Drugs 0.000 title 1
- 229960004958 ketotifen Drugs 0.000 abstract 4
- ZCVMWBYGMWKGHF-UHFFFAOYSA-N Ketotifene Chemical class C1CN(C)CCC1=C1C2=CC=CC=C2CC(=O)C2=C1C=CS2 ZCVMWBYGMWKGHF-UHFFFAOYSA-N 0.000 abstract 2
- IYSYPCSSDZBWHN-UHFFFAOYSA-N Nor-ketotifen Chemical compound C1=2C=CSC=2C(=O)CC2=CC=CC=C2C1=C1CCNCC1 IYSYPCSSDZBWHN-UHFFFAOYSA-N 0.000 abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 2
- 208000018522 Gastrointestinal disease Diseases 0.000 abstract 1
- 230000000172 allergic effect Effects 0.000 abstract 1
- 230000003266 anti-allergic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 208000010668 atopic eczema Diseases 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 208000030533 eye disease Diseases 0.000 abstract 1
- 208000023504 respiratory system disease Diseases 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 208000017520 skin disease Diseases 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Nutrition Science (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Un compuesto 4-(1R-4-piperidilen)-4H-benzo[4,5]ciclohepta[1,2]-tiofeno-1-A, que comprende la estructura (1) en la cual A es -CO- o -CHPH- y R es CH3 o H y las formas estereoquímicamente isoméricas y diastereómeros del mismo, con las siguientes condiciones: que A no sea -CO- cuando R es CH3; que A no sea -CO- cuando R es H si el compuesto es un racemato, que A no sea -CHOH- cuando R es CH3 si el compuesto es un racemato; que A no sea -CHOH- cuando R es H si el compuesto es un racemato; y sales y solvatos farmacéuticamente aceptables del mismo. Se encontró que el norketotifeno racémico, el 10-hidroxi-ketotifeno racémico, el 10-hidroxi-norketotifeno racémico y los isómeros ópticamente activos del ketotifeno, norketotifeno, 10-hidroxi-ketotifeno y 10-hidroxi-norketotifeno tenía efectos antialérgicos y antiinflamatorios careciendo, sin embargo, de los serios efectos colaterales limitantes de la dosis del ketotifeno. Además se describe un método para la síntesis de dichos compuestos y el uso de los mismos para la manufactura de un medicamento para prevenir o tratar una enfermedad seleccionada entre el grupo que consiste en trastornos respiratorios, trastornos alérgicos, trastornos cutáneos, trastornos gastrointestinales y trastornos oculares.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15356699P | 1999-09-13 | 1999-09-13 | |
| US19736300P | 2000-04-15 | 2000-04-15 | |
| US19790500P | 2000-04-15 | 2000-04-15 | |
| US19798500P | 2000-04-15 | 2000-04-15 | |
| US19790600P | 2000-04-15 | 2000-04-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR034396A1 true AR034396A1 (es) | 2004-02-25 |
Family
ID=27538454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP000104790A AR034396A1 (es) | 1999-09-13 | 2000-09-13 | Compuestos 4-(1r-4-piperidilen)-4h-benzo[4,5]ciclohepta[1,2]-tiofeno-1-a y sus isomeros opticamente activos, un metodo para su sintesis y el uso de dichos compuestos para la manufactura de un medicamento |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US7226934B1 (es) |
| EP (1) | EP1218007B1 (es) |
| JP (1) | JP5116928B2 (es) |
| CN (1) | CN1391475A (es) |
| AR (1) | AR034396A1 (es) |
| AT (1) | ATE516804T1 (es) |
| AU (1) | AU782816B2 (es) |
| BR (1) | BR0013935A (es) |
| CA (1) | CA2383222C (es) |
| CY (1) | CY1112605T1 (es) |
| DK (1) | DK1218007T3 (es) |
| HU (1) | HUP0202671A3 (es) |
| IL (2) | IL148368A0 (es) |
| MX (1) | MXPA02002658A (es) |
| MY (1) | MY134888A (es) |
| PL (1) | PL353586A1 (es) |
| PT (1) | PT1218007E (es) |
| WO (1) | WO2001019367A1 (es) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1218007T3 (da) * | 1999-09-13 | 2011-11-07 | Bridge Pharma Inc | Optisk aktive isomerer af ketotifen og terapeutiske aktive metaboliter deraf |
| WO2008153761A1 (en) * | 2007-05-23 | 2008-12-18 | Mastcell Pharmaceuticals, Inc. | Methods |
| WO2009142772A2 (en) * | 2008-05-23 | 2009-11-26 | Mastcell Pharmaceuticals, Inc. | Methods and treatment for allergies and inflammation associated with gastrointestinal diseases |
| US9006210B2 (en) | 2008-06-13 | 2015-04-14 | Case Western Reserve University | Compositions and methods for treating corneal inflammation |
| US8741930B2 (en) * | 2008-10-24 | 2014-06-03 | Bridge Pharma, Inc. | Treating xerophthalmia with norketotifen |
| US8765787B2 (en) * | 2008-11-21 | 2014-07-01 | Bridge Pharma, Inc. | Methods of treatment of xerophthalmia with self-preserving ocular formulations of norketotifen |
| JP2012520880A (ja) * | 2009-03-17 | 2012-09-10 | アーシエックス セラピューティックス， インコーポレイテッド | ケトチフェンの眼科用製剤および使用方法 |
| EP2727919B1 (en) * | 2011-06-28 | 2019-05-08 | Fujian Mindong Rejuvenation Pharmaceutical Co., Ltd. | Benzocycloheptanethiophene derivatives for anti-allergic reactions |
| US8778971B2 (en) * | 2012-10-23 | 2014-07-15 | Bridge Pharma, Inc. | Medicinal treatment of dermal diseases in companion animals |
| US8557846B1 (en) * | 2012-10-23 | 2013-10-15 | Bridge Pharma, Inc. | Medicinal treatment of dermal diseases in dogs |
| US20150272941A1 (en) * | 2012-10-30 | 2015-10-01 | Bridge Pharma, Inc. | Medicinal treatment of chronic pulmonary inflammatory diseases with norketotifen |
| US20140120121A1 (en) * | 2012-10-30 | 2014-05-01 | Bridge Pharma, Inc. | Medicinal treatment of atopic inflammatory diseases |
| US9439895B2 (en) | 2013-08-06 | 2016-09-13 | Bridge Pharma, Inc. | Methods of treating pruritic conditions mediated through non-histaminergic mechanisms in diabetic patients |
| US9345697B2 (en) | 2013-08-06 | 2016-05-24 | Bridge Pharma, Inc. | Methods of treatment of non-histaminic pruritus |
| US9138431B2 (en) * | 2013-08-06 | 2015-09-22 | Bridge Pharma, Inc. | Methods of treatment of histamine H-4 receptor-related pruritus |
| CN104059056B (zh) * | 2014-06-26 | 2017-08-25 | 福建省闽东力捷迅药业有限公司 | 一种富马酸卢帕替芬晶型b及其制备方法 |
| ES2703693T3 (es) * | 2015-06-11 | 2019-03-12 | Bridge Pharma Inc | Métodos de tratamiento del prurito no histamínico en mamíferos |
| US9694003B2 (en) | 2015-10-15 | 2017-07-04 | Bridge Pharma, Inc. | Formulations and methods for treating high intraocular pressure |
| CN106243096B (zh) * | 2016-07-29 | 2019-11-29 | 上海璃道医药科技有限公司 | 三环类药物的新用途 |
| WO2018048989A1 (en) * | 2016-09-08 | 2018-03-15 | Emergo Therapeutics, Inc. | Mast cell stabilizers for treatment of hypercytokinemia and viral infection |
| WO2018075574A1 (en) | 2016-10-18 | 2018-04-26 | Emergo Therapeutics, Inc. | Mast cell stabilizers for treatment of chronic inflammatory conditions |
| US10959992B2 (en) | 2019-02-22 | 2021-03-30 | Bridge Pharma Inc. | Methods of treatment of asthma and COPD |
| US20200268734A1 (en) * | 2019-02-22 | 2020-08-27 | Bridge Pharma, Inc. | Methods of treatment of respiratory disorders |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1089483A (en) | 1964-02-04 | 1967-11-01 | Sandoz Ltd | Improvements in or relating to 4h-benzo(4,5)cyclohepta (1,2-b) thiophene derivatives |
| FR1447527A (fr) | 1964-08-11 | 1966-07-29 | Sandoz Sa | Nouveaux benzo-cyclohepta-thiophènes et leur préparation |
| CH531000A (de) | 1970-03-11 | 1972-11-30 | Sandoz Ag | Verfahren zur Herstellung neuer Benzocycloheptathiophene |
| BE794377A (fr) * | 1972-01-24 | 1973-07-23 | Sandoz Sa | Nouveaux derives du benzo-cyclohepta-thiophene |
| US3994974A (en) | 1972-02-05 | 1976-11-30 | Yamanouchi Pharmaceutical Co., Ltd. | α-Aminomethylbenzyl alcohol derivatives |
| US4073915A (en) | 1975-05-20 | 1978-02-14 | Sandoz Ltd. | Treating asthma |
| US4128549A (en) | 1976-02-27 | 1978-12-05 | Sandoz Ltd. | Precursors of 4-(1-alkyl-4-piperidylidene-4H-benzo[4,5]cyclohepta-[1,2-b]thiophen-10(9H)-ones |
| CS263993B1 (cs) * | 1988-03-11 | 1989-05-12 | Polivka Zdenek | Způsob přípravy čistých enantiomerů 4- (l-meíhyl-4-piperidyliden) -4,9-dihydrobenzo [ 4,5) cyklohepta [ 1,2-b ] - thiofen-lQ-onu |
| JP2511550B2 (ja) | 1988-04-28 | 1996-06-26 | シェリング・コーポレーション | 融合多環式化合物、組成物、製造方法およびｐａｆ拮抗、抗ヒスタミンおよび／または抗炎症剤としてのその使用 |
| GB9012926D0 (en) * | 1990-06-09 | 1990-08-01 | Scras | Pyrrolo-pyridine derivatives |
| CA2093646A1 (en) * | 1990-10-10 | 1992-04-11 | Jesse K. Wong | Bis-benzo cyclohepta piperidylidene, piperidine and piperazine compounds, compositions and methods of use |
| DK0616524T3 (da) * | 1991-12-12 | 1999-06-21 | Glaxo Group Ltd | Lægemidler |
| DK0613371T3 (da) | 1991-12-18 | 2002-05-13 | Astrazeneca Ab | Ny kombination af formoterol og budesonid |
| US6040344A (en) | 1996-11-11 | 2000-03-21 | Sepracor Inc. | Formoterol process |
| ID24487A (id) * | 1997-04-03 | 2000-07-20 | Bridge Pharma Inc | Senyawa-senyawa benzosikloheptatiofen |
| WO1998056381A1 (en) * | 1997-06-09 | 1998-12-17 | Bridge Pharma, Inc. | Compounds with combined antihistaminic and mast cell stabilizing activities, intended for ophthalmic use |
| DK1218007T3 (da) | 1999-09-13 | 2011-11-07 | Bridge Pharma Inc | Optisk aktive isomerer af ketotifen og terapeutiske aktive metaboliter deraf |
-
2000
- 2000-09-12 DK DK00966709.8T patent/DK1218007T3/da active
- 2000-09-12 MX MXPA02002658A patent/MXPA02002658A/es active IP Right Grant
- 2000-09-12 WO PCT/US2000/024892 patent/WO2001019367A1/en not_active Ceased
- 2000-09-12 CA CA002383222A patent/CA2383222C/en not_active Expired - Fee Related
- 2000-09-12 AT AT00966709T patent/ATE516804T1/de active
- 2000-09-12 IL IL14836800A patent/IL148368A0/xx active IP Right Grant
- 2000-09-12 CN CN00815422A patent/CN1391475A/zh active Pending
- 2000-09-12 US US10/069,663 patent/US7226934B1/en not_active Expired - Fee Related
- 2000-09-12 AU AU77014/00A patent/AU782816B2/en not_active Ceased
- 2000-09-12 HU HU0202671A patent/HUP0202671A3/hu unknown
- 2000-09-12 PT PT00966709T patent/PT1218007E/pt unknown
- 2000-09-12 PL PL00353586A patent/PL353586A1/xx not_active Application Discontinuation
- 2000-09-12 BR BR0013935-1A patent/BR0013935A/pt not_active Application Discontinuation
- 2000-09-12 JP JP2001523001A patent/JP5116928B2/ja not_active Expired - Fee Related
- 2000-09-12 EP EP00966709A patent/EP1218007B1/en not_active Expired - Lifetime
- 2000-09-13 AR ARP000104790A patent/AR034396A1/es not_active Application Discontinuation
- 2000-09-13 MY MYPI20004252A patent/MY134888A/en unknown
-
2002
- 2002-02-25 IL IL148368A patent/IL148368A/en not_active IP Right Cessation
-
2007
- 2007-04-30 US US11/796,998 patent/US7557128B2/en not_active Expired - Fee Related
-
2009
- 2009-02-12 US US12/378,231 patent/US7872025B2/en not_active Expired - Fee Related
-
2011
- 2011-10-17 CY CY20111100984T patent/CY1112605T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003509369A (ja) | 2003-03-11 |
| PL353586A1 (en) | 2003-12-01 |
| HUP0202671A2 (hu) | 2002-11-28 |
| IL148368A0 (en) | 2002-09-12 |
| EP1218007B1 (en) | 2011-07-20 |
| US7872025B2 (en) | 2011-01-18 |
| PT1218007E (pt) | 2011-10-27 |
| EP1218007A4 (en) | 2003-04-09 |
| CA2383222C (en) | 2008-11-18 |
| AU782816B2 (en) | 2005-09-01 |
| US20090149502A1 (en) | 2009-06-11 |
| BR0013935A (pt) | 2002-05-14 |
| CY1112605T1 (el) | 2016-02-10 |
| WO2001019367A1 (en) | 2001-03-22 |
| CA2383222A1 (en) | 2001-03-22 |
| JP5116928B2 (ja) | 2013-01-09 |
| US7557128B2 (en) | 2009-07-07 |
| US7226934B1 (en) | 2007-06-05 |
| HUP0202671A3 (en) | 2005-01-28 |
| IL148368A (en) | 2007-10-31 |
| MXPA02002658A (es) | 2002-10-23 |
| AU7701400A (en) | 2001-04-17 |
| CN1391475A (zh) | 2003-01-15 |
| US20080287498A1 (en) | 2008-11-20 |
| DK1218007T3 (da) | 2011-11-07 |
| EP1218007A1 (en) | 2002-07-03 |
| MY134888A (en) | 2007-12-31 |
| ATE516804T1 (de) | 2011-08-15 |
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