EP0419604A1 - 2-stufen-zubereitung mit cumarin oder dobesilat-calcium zur behandlung von osteoarthrose - Google Patents
2-stufen-zubereitung mit cumarin oder dobesilat-calcium zur behandlung von osteoarthroseInfo
- Publication number
- EP0419604A1 EP0419604A1 EP19900903746 EP90903746A EP0419604A1 EP 0419604 A1 EP0419604 A1 EP 0419604A1 EP 19900903746 EP19900903746 EP 19900903746 EP 90903746 A EP90903746 A EP 90903746A EP 0419604 A1 EP0419604 A1 EP 0419604A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- benzopyrone
- stage
- portions
- preparation
- coumarin
- 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.)
- Withdrawn
Links
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 229960000956 coumarin Drugs 0.000 title claims abstract description 30
- 201000008482 osteoarthritis Diseases 0.000 title claims abstract description 18
- 238000011282 treatment Methods 0.000 title claims abstract description 11
- QGNBTYAQAPLTMX-UHFFFAOYSA-L calcium dobesilate Chemical compound [Ca+2].OC1=CC=C(O)C(S([O-])(=O)=O)=C1.OC1=CC=C(O)C(S([O-])(=O)=O)=C1 QGNBTYAQAPLTMX-UHFFFAOYSA-L 0.000 title claims abstract description 9
- 235000001671 coumarin Nutrition 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title claims description 19
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 229960005489 paracetamol Drugs 0.000 claims abstract description 4
- 229960002895 phenylbutazone Drugs 0.000 claims abstract description 4
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000004480 active ingredient Substances 0.000 claims description 12
- IKQCSJBQLWJEPU-UHFFFAOYSA-N 2,5-dihydroxybenzenesulfonic acid Chemical compound OC1=CC=C(O)C(S(O)(=O)=O)=C1 IKQCSJBQLWJEPU-UHFFFAOYSA-N 0.000 claims description 7
- 239000011575 calcium Substances 0.000 claims description 7
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 6
- 229960001138 acetylsalicylic acid Drugs 0.000 claims description 6
- 230000001364 causal effect Effects 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 230000000144 pharmacologic effect Effects 0.000 claims description 3
- 230000000069 prophylactic effect Effects 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 2
- 210000002751 lymph Anatomy 0.000 abstract description 7
- 230000006872 improvement Effects 0.000 abstract description 6
- 210000000988 bone and bone Anatomy 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 abstract description 2
- 238000009825 accumulation Methods 0.000 abstract 2
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical class CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 abstract 1
- 206010003246 arthritis Diseases 0.000 abstract 1
- 229960005438 calcium dobesilate Drugs 0.000 abstract 1
- 230000002045 lasting effect Effects 0.000 abstract 1
- 230000037396 body weight Effects 0.000 description 10
- 241000700159 Rattus Species 0.000 description 7
- 230000000202 analgesic effect Effects 0.000 description 5
- 230000001684 chronic effect Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- 230000000711 cancerogenic effect Effects 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- 231100000357 carcinogen Toxicity 0.000 description 3
- 239000003183 carcinogenic agent Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 230000001926 lymphatic effect Effects 0.000 description 3
- 210000001365 lymphatic vessel Anatomy 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- 210000000629 knee joint Anatomy 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 230000004089 microcirculation Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 230000008728 vascular permeability Effects 0.000 description 2
- VZYDKJOUEPFKMW-UHFFFAOYSA-N 2,3-dihydroxybenzenesulfonic acid Chemical compound OC1=CC=CC(S(O)(=O)=O)=C1O VZYDKJOUEPFKMW-UHFFFAOYSA-N 0.000 description 1
- 208000010444 Acidosis Diseases 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 208000032170 Congenital Abnormalities Diseases 0.000 description 1
- 206010020565 Hyperaemia Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 241001504519 Papio ursinus Species 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- 102000007562 Serum Albumin Human genes 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- 206010043275 Teratogenicity Diseases 0.000 description 1
- VWNJNGUJNHKZMC-UHFFFAOYSA-N [Ca].C1(O)=C(O)C(=CC=C1)S(=O)(=O)O Chemical compound [Ca].C1(O)=C(O)C(=CC=C1)S(=O)(=O)O VWNJNGUJNHKZMC-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000007950 acidosis Effects 0.000 description 1
- 208000026545 acidosis disease Diseases 0.000 description 1
- 210000003423 ankle Anatomy 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- FXRDPPFLWGSMQT-UHFFFAOYSA-N benzo[f]chromen-3-one Chemical compound C1=CC=C2C(C=CC(O3)=O)=C3C=CC2=C1 FXRDPPFLWGSMQT-UHFFFAOYSA-N 0.000 description 1
- -1 benzopyronyl Chemical group 0.000 description 1
- 210000003445 biliary tract Anatomy 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 206010010121 compartment syndrome Diseases 0.000 description 1
- 150000004775 coumarins Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 230000001700 effect on tissue Effects 0.000 description 1
- 210000002310 elbow joint Anatomy 0.000 description 1
- 210000003722 extracellular fluid Anatomy 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 231100000304 hepatotoxicity Toxicity 0.000 description 1
- 210000004394 hip joint Anatomy 0.000 description 1
- 210000000003 hoof Anatomy 0.000 description 1
- 230000004941 influx Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 210000000281 joint capsule Anatomy 0.000 description 1
- 210000003041 ligament Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 230000007056 liver toxicity Effects 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 231100000243 mutagenic effect Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 235000019645 odor Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000003128 rodenticide Substances 0.000 description 1
- IKGXIBQEEMLURG-NVPNHPEKSA-N rutin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=C(O)C(O)=CC=2)=O)O1 IKGXIBQEEMLURG-NVPNHPEKSA-N 0.000 description 1
- 229960004555 rutoside Drugs 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 210000001137 tarsal bone Anatomy 0.000 description 1
- 231100000211 teratogenicity Toxicity 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229960003232 troxerutin Drugs 0.000 description 1
- 230000009724 venous congestion Effects 0.000 description 1
- 239000011800 void material 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
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
- A61K31/37—Coumarins, e.g. psoralen
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
Definitions
- This invention relates to human or veterinary pharmacological
- 1,2-benzopyrone (or 5,6-benzocoumarin) is a well-known and extensively described, naturally occurring organic compound:
- 1,2-benzopyrone is used as a flavoring agent in the essence industry and perfumery, among other things to flavor tobacco, to mask unpleasant odors and as a fluorescence indicator.
- Coumarin derivatives serve as rodenticides.
- 1,2-benzopyrone entry 2543 to: Pharmaceutical auxiliary agent (flavor, smell).
- auxiliary agent flavor, smell
- Dobesilate calcium is listed in THE MERCK INDEX, 10th edition, 1983 (entry 3406); above all, the compound is said to have a vasotropic effect.
- Paracetamol (acetaminophen) is also known as an analgesic; see THE MERCK INDEX, 10th edition, entry 39. Phenylbutazone is described in THE MERCK INDEX, 7th edition, pages 800/801; it shows analgesic properties.
- Bones, ligaments and joint capsules form a limiting shell for the structures embedded in them.
- the "edema” cannot expand, resulting in an interstitial pressure increase.
- Lymphatic vessels are closed. Hemodynamically and lymph dynamically disused areas arise in which the circulatory disorder is maintained in the sense of a vicious circle. The delayed microcirculation reduces the oxygen supply. The oxygen deficit leads to anaerobic glucolysis and
- the vascular permeability is increased, i.e. there is an increased influx of fluid into the interstitium.
- 1,2-benzoparone causes histological liver damage in the rat and in the dog with high-dose long-term administration, it does not cause harm to the baboon (67.5 mg / kg daily for two years).
- the diagnosis of "biliary tract carcinoma" after feeding 5000 and 6000 ppm diets for two years must be questioned from today's perspective, given the lack of metastases and the negative results of other experiments with rats.
- 1,2-benzopyrone has no mutagenic properties and does not act as a carcinogen on the mouse skin. Repeated subcutaneous administration in rats showed no evidence of carcinogenic activity. In view of the different metabolism processes of primates and rats, rat experiments as a basis for liver toxicity tests must be assessed with caution. A sensitization study on 25 volunteers showed no occurrence of hypersensitivity reactions. Teratogenicity studies in rats with 1,2-benzopyrone and a 1,2-benzopyrone-rutin combination showed negative results with regard to absorption rate, fetal mortality and occurrence of fetal malformations, both after oral and intravenous administration. As already mentioned, it is known to influence the vessel walls in the Meaning of a pre-capillary angiospasmolytic effect
- 1,2-benzopyrone and its effect on tissue change 1,2-benzopyrone is rapidly absorbed after oral administration and bound to serum albumin. Together with these proteins, coumarin is produced by the monocytes e.g. of damaged tissue and the macrophages present there. This results in proteolysis of the proteins present in the edema area. The proteins are broken down into small fragments and transported away. This and the spasmolytic effect on the vessel wall leads to effective lymphatic drainage.
- the inventive human or veterinary pharmacological 2-step preparation for the prophylactic and therapeutic treatment of osteoarthritis contains, as active ingredient, 1,2-benzopyrone (coumarin) or 2,5-dihydroxybenzenesulfonic acid
- the active ingredient being present in the portions of the first stage in concentrations ⁇ 4% by weight and in the portions of the second stage in a concentration of> 1% by weight in addition to excipients.
- the preferred, new 2-stage preparation has, as active ingredients, in the first stage 1, 2-benzopyrone or 2,5-dihydroxybenzenesulfonic acid Ca as a causal component, in addition to one of the following pain-relieving active ingredients: acetylsalicylic acid plus salts, Paracetamol and phenylbutazone, and in the second stage 1,2-benzopyrone (coumarin) or 2,5-dihydroxybenzenesulfonic acid Ca (dobesilate calcium), the active compounds in the form of solutions to be administered parenterally in packs containing those separated according to the two stages and labeled individual preparation portions or in the form of solid preparations in packs with the individual preparation portions separated and written according to the two stages.
- active ingredients in the first stage 1, 2-benzopyrone or 2,5-dihydroxybenzenesulfonic acid Ca as a causal component, in addition to one of the following pain-relieving active ingredients: acetylsalicylic acid plus salts, Paracetamol and
- Special forms of the new 2-stage preparations are characterized by the fact that the individual active ingredients - besides Excipients - contain the active ingredient to 0.1 to 100 wt .-%, and that the weight ratio between the active ingredients, ie 1,2-benzo ⁇ yron or 2,5-dihydroxybenzenesulfonic acid Ca and the pain reliever, in the combine portions between Can vary 20: 1 and 0.05: 1.
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH131289A CH679372A5 (da) | 1989-04-07 | 1989-04-07 | |
| CH1312/89 | 1989-04-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0419604A1 true EP0419604A1 (de) | 1991-04-03 |
Family
ID=4207501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19900903746 Withdrawn EP0419604A1 (de) | 1989-04-07 | 1990-03-15 | 2-stufen-zubereitung mit cumarin oder dobesilat-calcium zur behandlung von osteoarthrose |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0419604A1 (da) |
| CH (1) | CH679372A5 (da) |
| WO (1) | WO1990011759A1 (da) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5645081A (en) * | 1991-11-14 | 1997-07-08 | Wake Forest University | Method of treating tissue damage and apparatus for same |
| RU2250769C2 (ru) * | 2003-06-05 | 2005-04-27 | Главный клинический госпиталь Министерства внутренних дел Российской Федерации (ГКГ МВД РФ) | Способ лечения остеоартроза |
| EP2056805B1 (en) * | 2006-08-16 | 2011-05-25 | Action Medicines, S.L. | Use of 2, 5-dihydroxybenzene derivatives for the treatment of tissue reactive diseases |
| EP1970059B1 (de) * | 2007-03-12 | 2009-11-25 | DOBAVET GmbH | Arzneimittel mit Dobesilat-Calcium zur Behandlung und Prophylaxe von Sehnenerkrankungen |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5096887A (en) * | 1984-03-01 | 1992-03-17 | Lamorna Investments Proprietary Limited | Treatment of high protein oedemas |
| AU581885B2 (en) * | 1984-03-01 | 1989-03-09 | Lamorna Investments Proprietary Limited | Treatment of high protein oedemas by direct application of benzo-pyrones |
-
1989
- 1989-04-07 CH CH131289A patent/CH679372A5/de not_active IP Right Cessation
-
1990
- 1990-03-15 WO PCT/CH1990/000072 patent/WO1990011759A1/de not_active Ceased
- 1990-03-15 EP EP19900903746 patent/EP0419604A1/de not_active Withdrawn
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9011759A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1990011759A1 (de) | 1990-10-18 |
| CH679372A5 (da) | 1992-02-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 19901105 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB IT LI LU NL SE |
|
| 17Q | First examination report despatched |
Effective date: 19920730 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 19921210 |