BG65847B1 - Приложение на производни на бигуанидина за получаване на лекарствено средство с цикатризиращ ефект - Google Patents
Приложение на производни на бигуанидина за получаване на лекарствено средство с цикатризиращ ефект Download PDFInfo
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- BG65847B1 BG65847B1 BG107304A BG10730402A BG65847B1 BG 65847 B1 BG65847 B1 BG 65847B1 BG 107304 A BG107304 A BG 107304A BG 10730402 A BG10730402 A BG 10730402A BG 65847 B1 BG65847 B1 BG 65847B1
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- 201000002282 venous insufficiency Diseases 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 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
- A61K31/13—Amines
- A61K31/155—Amidines (), e.g. guanidine (H2N—C(=NH)—NH2), isourea (N=C(OH)—NH2), isothiourea (—N=C(SH)—NH2)
-
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0006798A FR2809310B1 (fr) | 2000-05-26 | 2000-05-26 | Utilisation de derives de biguanide pour fabriquer un medicament ayant un effet cicatrisant |
| PCT/FR2001/001598 WO2001091696A2 (fr) | 2000-05-26 | 2001-05-23 | Utilisation de derives de biguanide pour fabriquer un medicament ayant un effet cicatrisant |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BG107304A BG107304A (bg) | 2003-06-30 |
| BG65847B1 true BG65847B1 (bg) | 2010-03-31 |
Family
ID=8850685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG107304A BG65847B1 (bg) | 2000-05-26 | 2002-11-21 | Приложение на производни на бигуанидина за получаване на лекарствено средство с цикатризиращ ефект |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7199159B2 (enExample) |
| EP (1) | EP1283708B1 (enExample) |
| JP (1) | JP4987209B2 (enExample) |
| KR (1) | KR20030029050A (enExample) |
| CN (1) | CN100420439C (enExample) |
| AR (1) | AR032617A1 (enExample) |
| AT (1) | ATE300942T1 (enExample) |
| AU (2) | AU6401101A (enExample) |
| BG (1) | BG65847B1 (enExample) |
| BR (1) | BRPI0111142C1 (enExample) |
| CA (1) | CA2410025C (enExample) |
| DE (1) | DE60112431T2 (enExample) |
| DK (1) | DK1283708T3 (enExample) |
| EC (1) | ECSP024359A (enExample) |
| EE (1) | EE05393B1 (enExample) |
| ES (1) | ES2244625T3 (enExample) |
| FR (1) | FR2809310B1 (enExample) |
| HU (1) | HU229205B1 (enExample) |
| MX (1) | MXPA02011622A (enExample) |
| MY (1) | MY137468A (enExample) |
| NO (1) | NO20025635L (enExample) |
| PT (1) | PT1283708E (enExample) |
| SK (1) | SK287249B6 (enExample) |
| UA (1) | UA76415C2 (enExample) |
| WO (1) | WO2001091696A2 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2858232B1 (fr) * | 2003-07-29 | 2006-03-03 | Pierre Potier | Utilisation d'un derive de biguanide pour proteger la peau des radiations uvb |
| DE102004022645A1 (de) * | 2004-05-07 | 2005-12-15 | Resorba Wundversorgung Gmbh & Co. Kg | Bioresorbierbares Material auf Kollagen-Basis |
| JP4877456B2 (ja) * | 2005-04-14 | 2012-02-15 | 株式会社 メドレックス | ビグアナイド系薬剤を含有するゼリー製剤 |
| EP2109447B1 (en) | 2007-01-29 | 2015-06-10 | HanAll Biopharma Co., Ltd. | N, n- dimethyl imidodicarbonimidic diamide acetate, method for producing the same and pharmaceutical compositions comprising the same |
| WO2010025227A1 (en) * | 2008-08-28 | 2010-03-04 | Tyco Healthcare Group Lp | Carrier neutralization/modification in antimicrobial compositions, articles and methods |
| KR101274981B1 (ko) * | 2010-01-06 | 2013-06-18 | 한올바이오파마주식회사 | 바이구아나이드 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 약학 조성물 |
| US10279007B2 (en) | 2010-11-15 | 2019-05-07 | Oxygenetix Institute, Inc. | Topical treatment method for healing wounds, disinfecting, covering and concealing the wound until healing occurs |
| GB2510712A (en) | 2011-07-22 | 2014-08-13 | Karel Paul Bouter | Nutritional product comprising a biguanide |
| KR101424667B1 (ko) * | 2011-08-08 | 2014-08-04 | 한올바이오파마주식회사 | Ｎ1-고리아민-ｎ2-치환된 바이구아나이드 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 약학 조성물 |
| WO2013022279A2 (en) * | 2011-08-08 | 2013-02-14 | Hanall Biopharma Co., Ltd. | N1-cyclic amine-n5-substituted biguanide derivatives, methods of preparing the same and pharmaceutical composition comprising the same |
| WO2013022278A2 (en) * | 2011-08-08 | 2013-02-14 | Hanall Biopharma Co., Ltd. | N1-cyclic amine-n5-substituted phenyl biguanide derivatives, methods of preparing the same and pharmaceutical composition comprising the same |
| JP6487031B2 (ja) | 2014-04-17 | 2019-03-20 | イミューノメット セラピューティクス インコーポレイテッド | グアニジン化合物、及びその用途 |
| CN104262205B (zh) * | 2014-09-02 | 2017-04-12 | 浙江工业大学 | N‑芳基双胍氢碘酸盐类化合物及其制备方法和应用 |
| KR102216701B1 (ko) | 2014-11-20 | 2021-02-18 | 이뮤노메트테라퓨틱스 인코포레이티드 | 바이구아나이드 화합물 및 이의 용도 |
| FR3035787B1 (fr) | 2015-05-07 | 2018-08-24 | L'oreal | Procede de traitement des matieres keratiniques a partir de derives de c-glycosides amides, acides ou ester, et la composition cosmetique les contenant |
| FR3053892A1 (fr) | 2016-07-12 | 2018-01-19 | Urgo Recherche Innovation Et Developpement | Pansement permettant la liberation controlee et prolongee de la metformine |
| CN106822075A (zh) * | 2017-03-31 | 2017-06-13 | 浙江萧山医院 | 二甲双胍在促进伤口愈合中的应用 |
| FR3068974B1 (fr) | 2017-07-12 | 2019-08-02 | Urgo Recherche Innovation Et Developpement | Pansement permettant la liberation controlee et prolongee d'actif |
| FR3088542B1 (fr) | 2018-11-21 | 2021-03-19 | Waterdiam France Sas | Composition cicatrisante comprenant une eau électrolysée |
| CN110179776B (zh) * | 2019-05-31 | 2022-09-06 | 宁夏医科大学 | 二甲双胍的新用途与二甲双胍组合物及组合物的制备方法和应用 |
| CN112494469A (zh) * | 2020-07-30 | 2021-03-16 | 吴学雷 | 二甲双胍在制备预防和/或治疗瘢痕的药物中的应用 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2213778A1 (en) * | 1973-01-16 | 1974-08-09 | Voorhees John | Adrenergics or hypoglycaemics for relieving skin disorders - e.g. psoriasis, dermatitis, skin carcinoma and acne in human beings |
Family Cites Families (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB852584A (en) | 1956-05-31 | 1960-10-26 | Us Vitamin Corp | Biguanide compositions |
| US2961377A (en) | 1957-08-05 | 1960-11-22 | Us Vitamin Pharm Corp | Oral anti-diabetic compositions and methods |
| US3098008A (en) * | 1960-10-05 | 1963-07-16 | Us Vitamin Pharm Corp | Method for treatment of dermatological disorders |
| US3174901A (en) | 1963-01-31 | 1965-03-23 | Jan Marcel Didier Aron Samuel | Process for the oral treatment of diabetes |
| US3468898A (en) | 1966-05-26 | 1969-09-23 | Sterling Drug Inc | Bridged bis-biguanides and bis-guanidines |
| US3996232A (en) * | 1970-11-23 | 1976-12-07 | William H. Rorer, Inc. | 1,5-Disubstituted biguanides |
| GB1351025A (en) | 1971-08-20 | 1974-04-24 | Aron Md Samuel J | Oxadiazol-5-yl biguanide derivatives method for their preparation and pharmaceutical compositions containing them |
| US3929999A (en) | 1972-12-12 | 1975-12-30 | Clifford John Heaphy | Oral hypoglycemic method |
| US3852353A (en) | 1972-12-12 | 1974-12-03 | C Heaphy | Oral hypoglycemic aminophenylsulfonyl-hydrocarbylbiguanides |
| US4211770A (en) * | 1973-01-16 | 1980-07-08 | The Upjohn Company | Treatment of psoriasis intralesionally with N6 -2'-O-dibutyryl cyclic AMP |
| CH602612A5 (enExample) | 1974-10-11 | 1978-07-31 | Hoffmann La Roche | |
| FR2320735A1 (fr) * | 1975-08-12 | 1977-03-11 | Dabis Georges | Composition anti-cellulite |
| US4163800A (en) * | 1977-08-17 | 1979-08-07 | The Procter & Gamble Company | Topical composition and treatment of skin lesions therewith |
| NZ207147A (en) | 1983-02-28 | 1987-08-31 | Johnson & Johnson Prod Inc | Adhesive bandage containing medicinal substance: pad and base prepared from bulky, non-woven material |
| FR2552305B1 (fr) * | 1983-09-22 | 1985-12-20 | Salkin Andre | Composition a pouvoir bactericide eleve contenant un biguanide et une pyrimidine |
| FR2585572B3 (fr) | 1985-07-31 | 1987-12-31 | Hugelin Andre | Nouvelles compositions pharmaceutiques a base d'un sel de l'acide p. chlorophenoxyacetique destinees au traitement des neuropathies et assurant la regeneration nerveuse |
| FR2611500B1 (fr) * | 1987-03-06 | 1990-05-04 | Lipha | Emploi de derives du biguanide dans la preparation de medicaments |
| AU1834188A (en) | 1987-06-29 | 1989-01-05 | Kendall Company, The | Novel medicated dressings |
| US5246708A (en) | 1987-10-28 | 1993-09-21 | Pro-Neuron, Inc. | Methods for promoting wound healing with deoxyribonucleosides |
| SU1560212A1 (ru) * | 1988-11-10 | 1990-04-30 | Киевский Медицинский Институт Им.Акад.А.А.Богомольца | Способ лечени сифилиса |
| IT1241994B (it) | 1990-08-30 | 1994-02-02 | Idi Farmaceutici | Composizione farmaceutica ad effetto cicatrizzante. |
| IL97771A (en) * | 1991-04-04 | 1996-12-05 | Sion Narrow Weaving | Dry polymeric material having antimicrobial activity |
| IT1249711B (it) * | 1991-09-30 | 1995-03-09 | Boniscontro E Gazzone S R L | Composizioni farmaceutiche, per uso topico, contenenti "scavengers" di radicali liberi dell'ossigeno e antibatterici,indicate nella terapia dei tessuti superficiali. |
| IT1256111B (it) * | 1992-11-23 | 1995-11-28 | Lifegroup Spa | Sali dell'acido traumatico ad attivita' cicatrizzante ed antibatterica |
| JP3493692B2 (ja) | 1993-09-09 | 2004-02-03 | 三菱マテリアル株式会社 | ビスビグアナイド系化合物およびそれを含む殺菌剤 |
| DE19503336C2 (de) * | 1995-02-02 | 1998-07-30 | Lohmann Therapie Syst Lts | Arzneiform zur Abgabe von Wirkstoffen an Wunden, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US5747527A (en) * | 1995-06-06 | 1998-05-05 | Shaman Pharmaceuticals, Inc. | Furanoeremophilane and eremophilanolide sesquiterpenes for treatment of diabetes |
| US5668084A (en) | 1995-08-01 | 1997-09-16 | Zeneca Inc. | Polyhexamethylene biguanide and surfactant composition and method for preventing waterline residue |
| US5872145A (en) * | 1996-08-16 | 1999-02-16 | Pozen, Inc. | Formulation of 5-HT agonist and NSAID for treatment of migraine |
| US5827898A (en) * | 1996-10-07 | 1998-10-27 | Shaman Pharmaceuticals, Inc. | Use of bisphenolic compounds to treat type II diabetes |
| US5837255A (en) * | 1996-12-10 | 1998-11-17 | Shaman Pharmaceuticals, Inc. | Method of reducing blood glucose by administering Harunganin or Vismin |
| US5741926A (en) * | 1997-02-12 | 1998-04-21 | Shaman Pharmaceuticals, Inc. | Aniline derivatives having antihyperglycemic activity |
| US5811078A (en) * | 1997-03-14 | 1998-09-22 | Adolor Corporation | Spray formulations of antihyperalgesic opiates and method of treating topical hyperalgesic conditions therewith |
| JP3054758B2 (ja) * | 1997-03-27 | 2000-06-19 | 小林製薬株式会社 | 外傷用組成物 |
| CN1197643A (zh) * | 1997-04-30 | 1998-11-04 | 谢瑞钢 | 一种创伤油膏 |
| WO1999029314A1 (en) * | 1997-12-08 | 1999-06-17 | Bristol-Myers Squibb Company | Novel salts of metformin and method |
| WO1999032120A1 (en) * | 1997-12-22 | 1999-07-01 | Euro-Celtique, S.A. | A method of preventing abuse of opioid dosage forms |
| WO2000004875A2 (en) * | 1998-07-24 | 2000-02-03 | Seo Hong Yoo | Preparation of aqueous clear solution dosage forms with bile acids |
| WO2000033829A1 (de) | 1998-12-05 | 2000-06-15 | Fresenius Kabi Deutschland Gmbh | Verwendung von poly (hexamethylen) biguanid zur herstellung eines mittels zur förderung der heilung von infektionsfreien wunden |
| US6248363B1 (en) * | 1999-11-23 | 2001-06-19 | Lipocine, Inc. | Solid carriers for improved delivery of active ingredients in pharmaceutical compositions |
| AR028299A1 (es) * | 1999-09-17 | 2003-05-07 | Novartis Ag | Una composicion farmaceutica que comprende nateglinida, un proceso para su preparacion y el uso de dicha composicion para la preparacion de un medicamento para el tratamiento de desordenes metabolicos, especialmente diabetes, o de una enfermedad o condicion asociada con diabetes. |
| PH12000002657B1 (en) * | 1999-10-12 | 2006-02-21 | Bristol Myers Squibb Co | C-aryl glucoside SGLT2 inhibitors |
| US6515117B2 (en) * | 1999-10-12 | 2003-02-04 | Bristol-Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| AU2001239826B2 (en) * | 2000-02-23 | 2006-06-15 | Orentreich Foundation For The Advancement Of Science, Inc. | Methods and compositions for the treatment of alopecia and other disorders of the pilosebaceous apparatus |
| DK1145717T3 (da) * | 2000-04-13 | 2004-08-02 | Pfizer Prod Inc | Synergistisk virkning af glyburid og milrinon |
-
2000
- 2000-05-26 FR FR0006798A patent/FR2809310B1/fr not_active Expired - Lifetime
-
2001
- 2001-05-23 DK DK01938318T patent/DK1283708T3/da active
- 2001-05-23 BR BRPI0111142A patent/BRPI0111142C1/pt not_active IP Right Cessation
- 2001-05-23 AU AU6401101A patent/AU6401101A/xx active Pending
- 2001-05-23 KR KR1020027016052A patent/KR20030029050A/ko not_active Ceased
- 2001-05-23 SK SK1658-2002A patent/SK287249B6/sk not_active IP Right Cessation
- 2001-05-23 WO PCT/FR2001/001598 patent/WO2001091696A2/fr not_active Ceased
- 2001-05-23 US US10/297,003 patent/US7199159B2/en not_active Expired - Lifetime
- 2001-05-23 AT AT01938318T patent/ATE300942T1/de active
- 2001-05-23 JP JP2001587712A patent/JP4987209B2/ja not_active Expired - Lifetime
- 2001-05-23 HU HU0302038A patent/HU229205B1/hu not_active IP Right Cessation
- 2001-05-23 UA UA2002097477A patent/UA76415C2/uk unknown
- 2001-05-23 PT PT01938318T patent/PT1283708E/pt unknown
- 2001-05-23 EP EP01938318A patent/EP1283708B1/fr not_active Expired - Lifetime
- 2001-05-23 AU AU2001264011A patent/AU2001264011B2/en not_active Expired
- 2001-05-23 ES ES01938318T patent/ES2244625T3/es not_active Expired - Lifetime
- 2001-05-23 CA CA2410025A patent/CA2410025C/fr not_active Expired - Lifetime
- 2001-05-23 CN CNB018114032A patent/CN100420439C/zh not_active Expired - Lifetime
- 2001-05-23 MX MXPA02011622A patent/MXPA02011622A/es active IP Right Grant
- 2001-05-23 DE DE60112431T patent/DE60112431T2/de not_active Expired - Lifetime
- 2001-05-23 EE EEP200200657A patent/EE05393B1/xx not_active IP Right Cessation
- 2001-05-24 AR ARP010102484A patent/AR032617A1/es unknown
- 2001-05-24 MY MYPI20012487A patent/MY137468A/en unknown
-
2002
- 2002-11-21 BG BG107304A patent/BG65847B1/bg unknown
- 2002-11-22 NO NO20025635A patent/NO20025635L/no not_active Application Discontinuation
- 2002-11-22 EC EC2002004359A patent/ECSP024359A/es unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2213778A1 (en) * | 1973-01-16 | 1974-08-09 | Voorhees John | Adrenergics or hypoglycaemics for relieving skin disorders - e.g. psoriasis, dermatitis, skin carcinoma and acne in human beings |
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