TW201240661A - Ester pro-drugs of [3-(1-(1H-imidazol-4-yl)ethyl)-2-methylphenyl] methanol for lowering intraocular pressure - Google Patents
Ester pro-drugs of [3-(1-(1H-imidazol-4-yl)ethyl)-2-methylphenyl] methanol for lowering intraocular pressure Download PDFInfo
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- TW201240661A TW201240661A TW100133488A TW100133488A TW201240661A TW 201240661 A TW201240661 A TW 201240661A TW 100133488 A TW100133488 A TW 100133488A TW 100133488 A TW100133488 A TW 100133488A TW 201240661 A TW201240661 A TW 201240661A
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- Prior art keywords
- methyl
- ethyl
- ester
- acid
- imidazol
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- 230000004410 intraocular pressure Effects 0.000 title claims abstract description 50
- 150000002148 esters Chemical class 0.000 title claims abstract description 19
- 239000000651 prodrug Substances 0.000 title abstract description 36
- 229940002612 prodrug Drugs 0.000 title abstract description 36
- HTQCEFAVROSRIW-UHFFFAOYSA-N [3-[1-(1h-imidazol-5-yl)ethyl]-2-methylphenyl]methanol Chemical compound C=1C=CC(CO)=C(C)C=1C(C)C1=CNC=N1 HTQCEFAVROSRIW-UHFFFAOYSA-N 0.000 title abstract description 3
- 238000000034 method Methods 0.000 claims abstract description 61
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- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 19
- 238000011282 treatment Methods 0.000 claims abstract description 19
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract description 4
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- -1 hydrazine compound Chemical class 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 31
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
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- SZXBQTSZISFIAO-UHFFFAOYSA-N 3-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoic acid Chemical compound CC(C)C(C(O)=O)NC(=O)OC(C)(C)C SZXBQTSZISFIAO-UHFFFAOYSA-N 0.000 claims 2
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- 125000001544 thienyl group Chemical group 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 208000009935 visceral pain Diseases 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4174—Arylalkylimidazoles, e.g. oxymetazolin, naphazoline, miconazole
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
-
- 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
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- 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
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38337010P | 2010-09-16 | 2010-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW201240661A true TW201240661A (en) | 2012-10-16 |
Family
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| TW100133488A TW201240661A (en) | 2010-09-16 | 2011-09-16 | Ester pro-drugs of [3-(1-(1H-imidazol-4-yl)ethyl)-2-methylphenyl] methanol for lowering intraocular pressure |
| TW100133498A TW201240662A (en) | 2010-09-16 | 2011-09-16 | Ester pro-drugs of [3-(1-(1H-imidazol-4-yl)ethyl)-2-methylphenyl] methanol for treating retinal diseases |
| TW100133491A TWI591058B (zh) | 2010-09-16 | 2011-09-16 | ［３－（１－（１ｈ－咪唑－４－基）乙基）－２－甲基苯基］甲醇之酯類前藥 |
| TW100133487A TW201305116A (zh) | 2010-09-16 | 2011-09-16 | 用於治療皮膚疾病及病況之［３－（１－（１ｈ－咪唑－４－基）乙基）－２－甲基苯基］甲醇之酯類前藥 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW100133498A TW201240662A (en) | 2010-09-16 | 2011-09-16 | Ester pro-drugs of [3-(1-(1H-imidazol-4-yl)ethyl)-2-methylphenyl] methanol for treating retinal diseases |
| TW100133491A TWI591058B (zh) | 2010-09-16 | 2011-09-16 | ［３－（１－（１ｈ－咪唑－４－基）乙基）－２－甲基苯基］甲醇之酯類前藥 |
| TW100133487A TW201305116A (zh) | 2010-09-16 | 2011-09-16 | 用於治療皮膚疾病及病況之［３－（１－（１ｈ－咪唑－４－基）乙基）－２－甲基苯基］甲醇之酯類前藥 |
Country Status (28)
| Country | Link |
|---|---|
| US (9) | US8492557B2 (https=) |
| EP (13) | EP3050564B1 (https=) |
| JP (4) | JP2013541527A (https=) |
| KR (7) | KR101952457B1 (https=) |
| CN (5) | CN103209694A (https=) |
| AR (4) | AR083018A1 (https=) |
| AU (4) | AU2011301932C1 (https=) |
| BR (4) | BR112013006362A2 (https=) |
| CA (8) | CA2812191C (https=) |
| CL (4) | CL2013000735A1 (https=) |
| CY (3) | CY1121024T1 (https=) |
| DK (9) | DK2616068T3 (https=) |
| ES (10) | ES2607084T3 (https=) |
| HU (5) | HUE047476T2 (https=) |
| IL (4) | IL225280A0 (https=) |
| MX (4) | MX2013003004A (https=) |
| MY (4) | MY161607A (https=) |
| NZ (1) | NZ608751A (https=) |
| PL (7) | PL3348264T3 (https=) |
| PT (7) | PT2616069T (https=) |
| RU (4) | RU2013116405A (https=) |
| SG (4) | SG188571A1 (https=) |
| SI (5) | SI3348264T1 (https=) |
| TR (1) | TR201909249T4 (https=) |
| TW (4) | TW201240661A (https=) |
| UA (1) | UA112973C2 (https=) |
| WO (4) | WO2012037453A1 (https=) |
| ZA (4) | ZA201302193B (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3241553B1 (en) * | 2009-02-13 | 2019-04-10 | Allergan, Inc. | Pharmaceutical compositions comprising (3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl)methanol |
| MX344303B (es) | 2010-01-11 | 2016-12-13 | Orexigen Therapeutics Inc | Metodos para proveer terapia de perdida de peso en pacientes con depresion mayor. |
| US8492557B2 (en) * | 2010-09-16 | 2013-07-23 | Allergan, Inc. | Ester pro-drugs of [3-(1-(1H-imidazol-4-yl)ethyl)-2-methylphenyl] methanol |
| CA2842866A1 (en) * | 2011-07-22 | 2013-01-31 | Allergan, Inc. | Alpha-2 adrenergic modulators for treating visual disorders mediated by central visual projections from the eye |
| EP2782569A1 (en) | 2011-11-21 | 2014-10-01 | Allergan, Inc. | Pharmaceutical compositions comprising 4-[1-(2,3-dimethylphenyl)ethyl]-3h-imidazole derivatives for treating retinal diseases |
| USD794650S1 (en) | 2014-11-28 | 2017-08-15 | Samsung Electronics Co., Ltd. | Display screen or portion thereof with a graphical user interface |
| CN108310442B (zh) * | 2017-01-17 | 2021-08-27 | 台北科技大学 | 眼科用组合物 |
| KR102050506B1 (ko) | 2017-06-20 | 2019-11-29 | 한국식품연구원 | 망막 질환 예방, 개선, 완화 또는 치료용 조성물 |
| CN108872431B (zh) * | 2018-07-09 | 2021-03-23 | 成都倍特药业股份有限公司 | 一种检测4-(1-(2,5-二甲基苯基)乙基)-1h-咪唑或/和其盐酸盐的方法 |
| JP7584802B2 (ja) * | 2018-08-24 | 2024-11-18 | アドライ・ノーティ・バイオファーマ・カンパニー・リミテッド | 高活性ｓｔｉｎｇタンパク質アゴニスト |
| WO2022221071A1 (en) * | 2021-04-16 | 2022-10-20 | Ads Therapeutics Llc | Alpha2 adrenergic agonist codrugs conjugated with muscarinic agonist drugs |
| AU2024217271A1 (en) * | 2023-02-08 | 2025-09-18 | Bausch + Lomb Ireland Limited | Alpha-2-adrenergic agonists for improving vision |
| WO2025179071A1 (en) * | 2024-02-20 | 2025-08-28 | Bausch + Lomb Ireland Limited | Sustained-release drug delivery compositions for treating ocular diseases |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE69307505T2 (de) | 1992-05-13 | 1997-07-24 | Sandoz-Patent-Gmbh, 79539 Loerrach | Opthalmische zusammensetzungen enthaltend ein cyclosporin |
| US5459133A (en) * | 1992-06-05 | 1995-10-17 | Telor Ophthalmic Pharmaceuticals, Inc. | Methods and products for treating presbyopia |
| ATE234290T1 (de) | 1993-11-15 | 2003-03-15 | Schering Corp | Phenylalkyl-imidazole als h3-rezeptor- antagonisten |
| US5474979A (en) | 1994-05-17 | 1995-12-12 | Allergan, Inc. | Nonirritating emulsions for sensitive tissue |
| EP0957073A1 (en) * | 1998-05-12 | 1999-11-17 | Schwarz Pharma Ag | Novel derivatives of 3,3-diphenylpropylamines |
| US20040214829A1 (en) * | 2000-07-14 | 2004-10-28 | Allergan, Inc. | Compositions containing alpha-2-adrenergic agonist components |
| US20020198209A1 (en) | 2001-05-03 | 2002-12-26 | Allergan Sales Inc. | Compositions having enhanced pharmacokinetic characteristics |
| MXPA05012679A (es) * | 2003-05-27 | 2006-02-08 | Sod Conseils Rech Applic | Nuevos derivados de imidazoles, su preparacion y su uso como medicamento. |
| US7439241B2 (en) * | 2003-05-27 | 2008-10-21 | Galderma Laboratories, Inc. | Compounds, formulations, and methods for treating or preventing rosacea |
| US20060209374A1 (en) * | 2003-07-14 | 2006-09-21 | Koninklijke Philips Electronics N.V. | Projection device |
| MXPA06002716A (es) * | 2003-09-12 | 2006-06-06 | Allergan Inc | Metodos y composiciones para el tratamiento de dolor y otras condiciones mediadas por adrenergicos de alfa-2. |
| US20050059583A1 (en) | 2003-09-15 | 2005-03-17 | Allergan, Inc. | Methods of providing therapeutic effects using cyclosporin components |
| US20050244463A1 (en) * | 2004-04-30 | 2005-11-03 | Allergan, Inc. | Sustained release intraocular implants and methods for treating ocular vasculopathies |
| JP4955543B2 (ja) | 2004-05-25 | 2012-06-20 | サンズローザ ファーマシューティカル ディヴェロップメント インコーポレイテッド | 炎症性皮膚疾患を治療又は予防するための化合物、製剤及び方法 |
| US20050277584A1 (en) | 2004-06-09 | 2005-12-15 | Allergan, Inc. | Pharmaceutical compositions comprising cyclosporins |
| NZ553341A (en) | 2004-09-24 | 2010-11-26 | Allergan Inc | 4-(phenylmethyl and substituted phenylmethyl)-imidazole-2-thiones acting as specific alpha2 adrenergic agonists |
| US7931909B2 (en) | 2005-05-10 | 2011-04-26 | Allergan, Inc. | Ocular therapy using alpha-2 adrenergic receptor compounds having enhanced anterior clearance rates |
| US7297679B2 (en) | 2005-07-13 | 2007-11-20 | Allergan, Inc. | Cyclosporin compositions |
| US20070015691A1 (en) | 2005-07-13 | 2007-01-18 | Allergan, Inc. | Cyclosporin compositions |
| US20070082070A1 (en) * | 2005-10-11 | 2007-04-12 | Stookey Evangeline L | Treating skin disorders |
| US7902247B2 (en) | 2008-01-09 | 2011-03-08 | Allergan, Inc. | Substituted-aryl-2-phenylethyl-1H-imidazole compounds as subtype selective modulators of alpha 2B and/or alpha 2C adrenergic receptors |
| JP2012517433A (ja) | 2009-02-06 | 2012-08-02 | アラーガン インコーポレイテッド | アルファ２ｂおよび／またはアルファ２ｃアドレナリンレセプターのサブタイプ選択的モジュレーターとしてのピリジン化合物 |
| EP3241553B1 (en) * | 2009-02-13 | 2019-04-10 | Allergan, Inc. | Pharmaceutical compositions comprising (3-(1-(1h-imidazol-4-yl)ethyl)-2-methylphenyl)methanol |
| US8394800B2 (en) * | 2009-11-19 | 2013-03-12 | Galderma Laboratories, L.P. | Method for treating psoriasis |
| US8492557B2 (en) * | 2010-09-16 | 2013-07-23 | Allergan, Inc. | Ester pro-drugs of [3-(1-(1H-imidazol-4-yl)ethyl)-2-methylphenyl] methanol |
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2011
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