CA2612364A1 - Substituted phenylphosphates as mutual prodrugs of steroids and .beta.-agonists the treatment of pulmonary inflammation and bronchoconstriction - Google Patents
Substituted phenylphosphates as mutual prodrugs of steroids and .beta.-agonists the treatment of pulmonary inflammation and bronchoconstriction Download PDFInfo
- Publication number
- CA2612364A1 CA2612364A1 CA002612364A CA2612364A CA2612364A1 CA 2612364 A1 CA2612364 A1 CA 2612364A1 CA 002612364 A CA002612364 A CA 002612364A CA 2612364 A CA2612364 A CA 2612364A CA 2612364 A1 CA2612364 A1 CA 2612364A1
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- Canada
- Prior art keywords
- diene
- bis
- oxy
- dione
- fluoro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 229940002612 prodrug Drugs 0.000 title claims abstract description 89
- 239000000651 prodrug Substances 0.000 title claims abstract description 87
- 239000000556 agonist Substances 0.000 title claims abstract description 41
- 238000011282 treatment Methods 0.000 title claims abstract description 24
- 206010006482 Bronchospasm Diseases 0.000 title claims abstract description 16
- 230000007885 bronchoconstriction Effects 0.000 title claims abstract description 16
- CMPQUABWPXYYSH-UHFFFAOYSA-N phenyl phosphate Chemical class OP(O)(=O)OC1=CC=CC=C1 CMPQUABWPXYYSH-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 206010035664 Pneumonia Diseases 0.000 title claims abstract description 13
- 150000003431 steroids Chemical class 0.000 title claims description 95
- 239000000203 mixture Substances 0.000 claims abstract description 53
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- 238000012387 aerosolization Methods 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 144
- 238000000034 method Methods 0.000 claims description 82
- -1 Cyclohexylmethylene Chemical group 0.000 claims description 55
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 28
- 229910019142 PO4 Inorganic materials 0.000 claims description 21
- 239000010452 phosphate Substances 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 230000015572 biosynthetic process Effects 0.000 claims description 18
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- LQCLVBQBTUVCEQ-QTFUVMRISA-N troleandomycin Chemical compound O1[C@@H](C)[C@H](OC(C)=O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](OC(C)=O)[C@@H](C)C(=O)[C@@]2(OC2)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)OC(C)=O)[C@H]1C LQCLVBQBTUVCEQ-QTFUVMRISA-N 0.000 description 1
- 229960005041 troleandomycin Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000006886 vinylation reaction Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/0075—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Otolaryngology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69054505P | 2005-06-14 | 2005-06-14 | |
| US60/690,545 | 2005-06-14 | ||
| PCT/US2006/022790 WO2006138212A1 (en) | 2005-06-14 | 2006-06-12 | SUBSTITUTED PHENYLPHOSPHATES AS MUTUAL PRODRUGS OF STEROIDS AND β -AGONISTS FOR THE TREATMENT OF PULMONARY INFLAMMATION AND BRONCHOCONSTRICTION |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2612364A1 true CA2612364A1 (en) | 2006-12-28 |
Family
ID=37570763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002612364A Abandoned CA2612364A1 (en) | 2005-06-14 | 2006-06-12 | Substituted phenylphosphates as mutual prodrugs of steroids and .beta.-agonists the treatment of pulmonary inflammation and bronchoconstriction |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20100209508A1 (https=) |
| EP (1) | EP1893220A4 (https=) |
| JP (1) | JP2008546694A (https=) |
| KR (1) | KR20060130515A (https=) |
| CN (1) | CN101227912A (https=) |
| AR (1) | AR054475A1 (https=) |
| AU (1) | AU2006259604A1 (https=) |
| BR (1) | BRPI0611567A2 (https=) |
| CA (1) | CA2612364A1 (https=) |
| IL (1) | IL187816A0 (https=) |
| NO (1) | NO20080182L (https=) |
| RU (1) | RU2008100237A (https=) |
| TW (1) | TW200718707A (https=) |
| WO (1) | WO2006138212A1 (https=) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20090078329A (ko) * | 2006-09-19 | 2009-07-17 | 씨아이피엘에이 엘티디. | 시클레소니드의 제조방법 및 그의 결정형 |
| US20100112061A1 (en) * | 2006-12-13 | 2010-05-06 | William Baker | Monophosphates as Mutual Prodrugs of Muscarinic Receptor Antagonists and Beta-Agonists for the Treatment of COPD And Chronic Bronchitis |
| US20100098641A1 (en) * | 2006-12-13 | 2010-04-22 | William Baker | Monophosphates as Mutual Prodrugs of Anti-Inflammatory Signal Transduction Modulators (AISTM's) and Beta-Agonists for the Treatment of Pulmonary Inflammation and Bronchoconstriction |
| CA2710149A1 (en) * | 2007-12-21 | 2009-07-09 | John C. Anthes | C20-c21 substituted glucocorticoid receptor agonists |
| EP2235035A2 (en) * | 2007-12-21 | 2010-10-06 | Schering Corporation | C-21 thioethers as glucocorticoid receptor agonists |
| US20090318396A1 (en) * | 2008-06-10 | 2009-12-24 | Gilead Sciences, Inc. | Corticosteroid linked beta-agonist compounds for use in therapy |
| WO2010126953A1 (en) * | 2009-04-29 | 2010-11-04 | Gilead Sciences, Inc. | Corticosteroid linked beta-agonist compounds for use in therapy |
| WO2010132743A1 (en) * | 2009-05-15 | 2010-11-18 | Gilead Sciences, Inc. | Corticosteroid beta-agonist compounds for use in therapy |
| JP2012530140A (ja) * | 2009-06-16 | 2012-11-29 | メルク・シャープ・アンド・ドーム・コーポレーション | グルココルチコイド受容体アゴニストとしての新規［３，２−ｃ］ヘテロアリールステロイド、組成物およびこの使用 |
| WO2011029547A2 (en) * | 2009-09-11 | 2011-03-17 | Chiesi Farmaceutici S.P.A. | Pregnane derivatives condensed in the 16, 17 position with an n-substituted isoxazolidine ring as anti-inflammatory agents |
| WO2011081937A1 (en) | 2009-12-15 | 2011-07-07 | Gilead Sciences, Inc. | Corticosteroid-beta-agonist-muscarinic antagonist compounds for use in therapy |
| JP6124176B2 (ja) * | 2013-03-26 | 2017-05-10 | 株式会社伏見製薬所 | 樹脂成形体用組成物 |
| CN104510726A (zh) * | 2013-09-27 | 2015-04-15 | 张金华 | 一种用于清洁呼吸道系统的食盐干粉吸入剂 |
| PT107567B (pt) * | 2014-03-31 | 2019-02-13 | Hovione Farm S A | Secador por atomização com atomizador múltiplo, método para o aumento de escala de pós para inalação secos por dispositivo de atomização múltiplo e uso de vários atomizadores num secador por atomização |
| MY194619A (en) | 2016-06-02 | 2022-12-07 | Abbvie Inc | Glucocorticoid receptor agonist and immunoconjugates thereof |
| KR20250114431A (ko) * | 2016-11-08 | 2025-07-29 | 리제너론 파마슈티칼스 인코포레이티드 | 스테로이드 및 이의 단백질-접합체 |
| KR20250008984A (ko) | 2017-05-18 | 2025-01-16 | 리제너론 파마슈티칼스 인코포레이티드 | 사이클로덱스트린 단백질 약물 접합체 |
| MX2020004691A (es) | 2017-11-07 | 2020-08-20 | Regeneron Pharma | Enlazadores hidrofilicos para conjugados anticuerpo-farmaco. |
| AU2018374634A1 (en) | 2017-12-01 | 2020-05-28 | Abbvie Inc. | Glucocorticoid receptor agonist and immunoconjugates thereof |
| CN112004557B (zh) | 2018-01-08 | 2024-07-30 | 里珍纳龙药品有限公司 | 类固醇类化合物及其抗体偶联物 |
| CN112533951A (zh) | 2018-05-09 | 2021-03-19 | 里珍纳龙药品有限公司 | 抗msr1抗体及其使用方法 |
| IT201900014178A1 (it) * | 2019-08-06 | 2021-02-06 | Genetic S P A | Esteri del montelukast e loro formulazioni farmaceutiche |
| JP7656784B2 (ja) * | 2020-11-26 | 2025-04-04 | 国立医薬品食品衛生研究所長 | 新規化合物及び抗コロナウイルス剤 |
| CN112592280B (zh) * | 2020-12-09 | 2023-05-23 | 青岛职业技术学院 | 一种消旋沙丁胺醇的制备方法 |
| AR125079A1 (es) | 2021-03-23 | 2023-06-07 | Lilly Co Eli | Agonistas de receptores de glucocorticoides sustituidos con carboxi |
| TWI899455B (zh) | 2021-03-23 | 2025-10-01 | 美商美國禮來大藥廠 | 糖皮質素受體激動劑 |
| AR125084A1 (es) | 2021-03-23 | 2023-06-07 | Lilly Co Eli | Agonistas del receptor de glucocorticoides novedosos |
| JP2024523545A (ja) * | 2021-06-24 | 2024-06-28 | 江蘇先声薬業有限公司 | ステロイド系化合物、その医薬組成物及びその応用 |
| WO2023040793A1 (zh) * | 2021-09-14 | 2023-03-23 | 映恩生物制药（苏州）有限公司 | 一种抗炎症的化合物及其用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB933868A (en) * | 1958-12-08 | 1963-08-14 | American Cyanamid Co | Process for fluorinating steroids |
| US4757079A (en) * | 1986-06-24 | 1988-07-12 | Dynamac Corporaton | Anti-hypertensive piperidine compounds |
| GR1001529B (el) * | 1990-09-07 | 1994-03-31 | Elmuquimica Farm Sl | Μέ?οδος για την λήψη νέων 21-εστέρων της 16-17-ακετάλης της πρ να-1,4-διενο-3,20-διόνης. |
| UA45311C2 (uk) * | 1993-04-02 | 2002-04-15 | Бік Гульден Ломберг Хеміше Фабрік Гмбх | 16<font face="Symbol">a</font>,17-ЦИКЛОГЕКСИЛМЕТИЛЕНДІОКСИ-11<font face="Symbol">b</font>,21-ДИГІДРОКСИПРЕГНА-1,4-ДІЄН-3,20-ДІОН, СПОСІБ ЙОГО ОДЕРЖАННЯ, ЛІКАРСЬКИЙ ЗАСІБ |
| US6300326B1 (en) * | 1994-11-02 | 2001-10-09 | Michael R. Dobbs | Composition and method for control and treatment of cutaneous inflammation |
| IT1303671B1 (it) * | 1998-07-28 | 2001-02-23 | Nicox Sa | Sali dell'acido nitrico con farmaci attivi nel trattamento dipatologie del sistema respiratorio |
| US20060293293A1 (en) * | 2003-05-22 | 2006-12-28 | Altana Pharma Ag | Salmeterol and ciclesonide combination |
| WO2005028495A1 (en) * | 2003-09-24 | 2005-03-31 | Glaxo Group Limited | Anti-inflammatory glucocorticoids |
| WO2005063777A1 (en) * | 2003-12-23 | 2005-07-14 | Corus Pharma | Benzylphosphate and substituted benzylphosphate prodrugs for the treatment of pulmonary inflammation |
-
2006
- 2006-06-12 EP EP06784777A patent/EP1893220A4/en not_active Withdrawn
- 2006-06-12 BR BRPI0611567A patent/BRPI0611567A2/pt not_active IP Right Cessation
- 2006-06-12 RU RU2008100237/04A patent/RU2008100237A/ru not_active Application Discontinuation
- 2006-06-12 WO PCT/US2006/022790 patent/WO2006138212A1/en not_active Ceased
- 2006-06-12 US US11/922,258 patent/US20100209508A1/en not_active Abandoned
- 2006-06-12 AU AU2006259604A patent/AU2006259604A1/en not_active Abandoned
- 2006-06-12 CN CNA2006800213783A patent/CN101227912A/zh active Pending
- 2006-06-12 JP JP2008516976A patent/JP2008546694A/ja active Pending
- 2006-06-12 CA CA002612364A patent/CA2612364A1/en not_active Abandoned
- 2006-06-14 TW TW095121230A patent/TW200718707A/zh unknown
- 2006-06-14 KR KR1020060053519A patent/KR20060130515A/ko not_active Withdrawn
- 2006-06-14 AR ARP060102527A patent/AR054475A1/es unknown
-
2007
- 2007-12-02 IL IL187816A patent/IL187816A0/en unknown
-
2008
- 2008-01-11 NO NO20080182A patent/NO20080182L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20080182L (no) | 2008-02-21 |
| RU2008100237A (ru) | 2009-07-20 |
| BRPI0611567A2 (pt) | 2016-11-16 |
| JP2008546694A (ja) | 2008-12-25 |
| IL187816A0 (en) | 2008-08-07 |
| TW200718707A (en) | 2007-05-16 |
| EP1893220A1 (en) | 2008-03-05 |
| AR054475A1 (es) | 2007-06-27 |
| KR20060130515A (ko) | 2006-12-19 |
| WO2006138212A1 (en) | 2006-12-28 |
| EP1893220A4 (en) | 2011-06-15 |
| CN101227912A (zh) | 2008-07-23 |
| US20100209508A1 (en) | 2010-08-19 |
| AU2006259604A1 (en) | 2006-12-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |