CA2351463C - Antiviral formulations comprising propylene glycol and an isopropyl alkanoic acid ester - Google Patents
Antiviral formulations comprising propylene glycol and an isopropyl alkanoic acid ester Download PDFInfo
- Publication number
- CA2351463C CA2351463C CA002351463A CA2351463A CA2351463C CA 2351463 C CA2351463 C CA 2351463C CA 002351463 A CA002351463 A CA 002351463A CA 2351463 A CA2351463 A CA 2351463A CA 2351463 C CA2351463 C CA 2351463C
- Authority
- CA
- Canada
- Prior art keywords
- composition
- propylene glycol
- isopropyl
- acid ester
- alkanoic acid
- 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.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 124
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 title claims abstract description 92
- 150000002148 esters Chemical class 0.000 title claims abstract description 23
- 230000000840 anti-viral effect Effects 0.000 title claims abstract description 21
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 title claims abstract description 18
- 239000002253 acid Substances 0.000 title claims description 17
- 238000009472 formulation Methods 0.000 title description 40
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- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 claims description 42
- 229960000890 hydrocortisone Drugs 0.000 claims description 21
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- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 claims description 14
- JNTOCHDNEULJHD-UHFFFAOYSA-N Penciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(CCC(CO)CO)C=N2 JNTOCHDNEULJHD-UHFFFAOYSA-N 0.000 claims description 12
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- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical class CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
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- DALKLAYLIPSCQL-YPYQNWSCSA-N methylprednisolone aceponate Chemical compound C1([C@@H](C)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@@](C(=O)COC(C)=O)(OC(=O)CC)[C@@]2(C)C[C@@H]1O DALKLAYLIPSCQL-YPYQNWSCSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 229960001664 mometasone Drugs 0.000 description 1
- QLIIKPVHVRXHRI-CXSFZGCWSA-N mometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O QLIIKPVHVRXHRI-CXSFZGCWSA-N 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 229950007703 pendecamaine Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920001992 poloxamer 407 Polymers 0.000 description 1
- 229940044476 poloxamer 407 Drugs 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- IXTCZMJQGGONPY-XJAYAHQCSA-N rofleponide Chemical compound C1([C@@H](F)C2)=CC(=O)CC[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H]3O[C@@H](CCC)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O IXTCZMJQGGONPY-XJAYAHQCSA-N 0.000 description 1
- 229950004432 rofleponide Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 235000019615 sensations Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229940080350 sodium stearate Drugs 0.000 description 1
- 229940045902 sodium stearyl fumarate Drugs 0.000 description 1
- FVEFRICMTUKAML-UHFFFAOYSA-M sodium tetradecyl sulfate Chemical compound [Na+].CCCCC(CC)CCC(CC(C)C)OS([O-])(=O)=O FVEFRICMTUKAML-UHFFFAOYSA-M 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE9803929-0 | 1998-11-18 | ||
| SE9803929A SE9803929D0 (sv) | 1998-11-18 | 1998-11-18 | Antiviral formulation |
| PCT/SE1999/002043 WO2000029027A1 (en) | 1998-11-18 | 1999-11-12 | Antiviral formulations comprising propylene glycol and an isopropyl alkanoic acid ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2351463A1 CA2351463A1 (en) | 2000-05-25 |
| CA2351463C true CA2351463C (en) | 2009-10-13 |
Family
ID=20413320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002351463A Expired - Lifetime CA2351463C (en) | 1998-11-18 | 1999-11-12 | Antiviral formulations comprising propylene glycol and an isopropyl alkanoic acid ester |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP1131104B1 (enExample) |
| JP (2) | JP2002529520A (enExample) |
| KR (1) | KR100608963B1 (enExample) |
| CN (1) | CN1160128C (enExample) |
| AR (1) | AR023705A1 (enExample) |
| AT (1) | ATE288283T1 (enExample) |
| AU (1) | AU772435B2 (enExample) |
| CA (1) | CA2351463C (enExample) |
| DE (1) | DE69923584T2 (enExample) |
| DK (1) | DK1131104T3 (enExample) |
| EG (1) | EG23853A (enExample) |
| ES (1) | ES2233104T3 (enExample) |
| HK (1) | HK1042440B (enExample) |
| IL (2) | IL142702A0 (enExample) |
| MY (1) | MY122397A (enExample) |
| NZ (1) | NZ511832A (enExample) |
| PT (1) | PT1131104E (enExample) |
| SE (1) | SE9803929D0 (enExample) |
| TW (1) | TW589191B (enExample) |
| WO (1) | WO2000029027A1 (enExample) |
| ZA (1) | ZA200103335B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100956369B1 (ko) * | 2001-11-19 | 2010-05-10 | 메디진 아게 | 바이러스성 피부 질환 및 종양 질환 치료용 약제 |
| ZA200602544B (en) | 2003-10-09 | 2007-06-27 | Medigene Ag | The use of a polyphenol for the treatment of a cancerous or pre-cancerous lesion of the skin |
| JP4972062B2 (ja) * | 2008-03-17 | 2012-07-11 | メディヴィル・アクチエボラーグ | 抗ウイルス製剤 |
| ES2955089T3 (es) * | 2018-08-17 | 2023-11-28 | Ilko Ilac Sanayi Ve Ticaret Anonim Sirketi | Composición tópica estable en fase que comprende aciclovir e hidrocortisona |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW438585B (en) * | 1995-02-06 | 2001-06-07 | Astra Ab | Pharmaceutical compositions for topical administration for prophylaxis and/or treatment of herpesvirus infections |
| US5760096A (en) * | 1996-10-18 | 1998-06-02 | Thornfeldt; Carl R. | Potent penetration enhancers |
-
1998
- 1998-11-18 SE SE9803929A patent/SE9803929D0/xx unknown
-
1999
- 1999-11-12 AU AU14364/00A patent/AU772435B2/en not_active Expired
- 1999-11-12 NZ NZ511832A patent/NZ511832A/en not_active IP Right Cessation
- 1999-11-12 EP EP99972109A patent/EP1131104B1/en not_active Expired - Lifetime
- 1999-11-12 DE DE69923584T patent/DE69923584T2/de not_active Expired - Lifetime
- 1999-11-12 HK HK02104279.2A patent/HK1042440B/zh not_active IP Right Cessation
- 1999-11-12 PT PT99972109T patent/PT1131104E/pt unknown
- 1999-11-12 CN CNB998133825A patent/CN1160128C/zh not_active Expired - Lifetime
- 1999-11-12 CA CA002351463A patent/CA2351463C/en not_active Expired - Lifetime
- 1999-11-12 ES ES99972109T patent/ES2233104T3/es not_active Expired - Lifetime
- 1999-11-12 JP JP2000582073A patent/JP2002529520A/ja active Pending
- 1999-11-12 IL IL14270299A patent/IL142702A0/xx active IP Right Grant
- 1999-11-12 KR KR1020017006232A patent/KR100608963B1/ko not_active Expired - Fee Related
- 1999-11-12 DK DK99972109T patent/DK1131104T3/da active
- 1999-11-12 AT AT99972109T patent/ATE288283T1/de active
- 1999-11-12 WO PCT/SE1999/002043 patent/WO2000029027A1/en not_active Ceased
- 1999-11-15 TW TW088119865A patent/TW589191B/zh not_active IP Right Cessation
- 1999-11-16 MY MYPI99004979A patent/MY122397A/en unknown
- 1999-11-16 EG EG146899A patent/EG23853A/xx active
- 1999-11-17 AR ARP990105846A patent/AR023705A1/es active IP Right Grant
-
2001
- 2001-04-19 IL IL142702A patent/IL142702A/en not_active IP Right Cessation
- 2001-04-24 ZA ZA200103335A patent/ZA200103335B/en unknown
-
2011
- 2011-04-11 JP JP2011087438A patent/JP5420583B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| HK1042440A1 (en) | 2002-08-16 |
| EG23853A (en) | 2007-11-06 |
| AU1436400A (en) | 2000-06-05 |
| AU772435B2 (en) | 2004-04-29 |
| TW589191B (en) | 2004-06-01 |
| CN1326364A (zh) | 2001-12-12 |
| DK1131104T3 (da) | 2005-03-14 |
| ES2233104T3 (es) | 2005-06-01 |
| IL142702A (en) | 2006-07-05 |
| HK1042440B (zh) | 2005-04-29 |
| EP1131104B1 (en) | 2005-02-02 |
| ZA200103335B (en) | 2002-07-24 |
| MY122397A (en) | 2006-04-29 |
| NZ511832A (en) | 2003-09-26 |
| ATE288283T1 (de) | 2005-02-15 |
| CN1160128C (zh) | 2004-08-04 |
| DE69923584T2 (de) | 2006-03-23 |
| JP2002529520A (ja) | 2002-09-10 |
| IL142702A0 (en) | 2002-03-10 |
| KR20010075720A (ko) | 2001-08-09 |
| PT1131104E (pt) | 2005-03-31 |
| EP1131104A1 (en) | 2001-09-12 |
| WO2000029027A1 (en) | 2000-05-25 |
| JP5420583B2 (ja) | 2014-02-19 |
| SE9803929D0 (sv) | 1998-11-18 |
| CA2351463A1 (en) | 2000-05-25 |
| AR023705A1 (es) | 2002-09-04 |
| JP2011157392A (ja) | 2011-08-18 |
| KR100608963B1 (ko) | 2006-08-09 |
| DE69923584D1 (de) | 2005-03-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20191112 |