DE2221281C3 - Pharmazeutische Zubereitungen mit entzündungshemmender und analgetischer Wirkung - Google Patents
Pharmazeutische Zubereitungen mit entzündungshemmender und analgetischer WirkungInfo
- Publication number
- DE2221281C3 DE2221281C3 DE2221281A DE2221281A DE2221281C3 DE 2221281 C3 DE2221281 C3 DE 2221281C3 DE 2221281 A DE2221281 A DE 2221281A DE 2221281 A DE2221281 A DE 2221281A DE 2221281 C3 DE2221281 C3 DE 2221281C3
- Authority
- DE
- Germany
- Prior art keywords
- phenylbutazone
- inflammatory
- preparations
- hydrogen atom
- pharmaceutical preparations
- 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
Links
- 230000003110 anti-inflammatory effect Effects 0.000 title claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
- 230000001760 anti-analgesic effect Effects 0.000 title claims description 4
- 229960002895 phenylbutazone Drugs 0.000 claims description 16
- 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 description 16
- 238000012360 testing method Methods 0.000 claims description 13
- 230000000694 effects Effects 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 claims description 3
- 229960001067 hydrocortisone acetate Drugs 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 230000007059 acute toxicity Effects 0.000 claims description 2
- 231100000403 acute toxicity Toxicity 0.000 claims description 2
- 230000000052 comparative effect Effects 0.000 claims description 2
- 230000000144 pharmacologic effect Effects 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 2
- 239000003470 adrenal cortex hormone Substances 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- RKHQGWMMUURILY-UHRZLXHJSA-N cortivazol Chemical compound C([C@H]1[C@@H]2C[C@H]([C@]([C@@]2(C)C[C@H](O)[C@@H]1[C@@]1(C)C2)(O)C(=O)COC(C)=O)C)=C(C)C1=CC1=C2C=NN1C1=CC=CC=C1 RKHQGWMMUURILY-UHRZLXHJSA-N 0.000 claims 1
- UCQFSGCWHRTMGG-UHFFFAOYSA-N pyrazole-1-carboximidamide Chemical compound NC(=N)N1C=CC=N1 UCQFSGCWHRTMGG-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010018691 Granuloma Diseases 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 208000002193 Pain Diseases 0.000 description 3
- 235000010418 carrageenan Nutrition 0.000 description 3
- 229920001525 carrageenan Polymers 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000036407 pain Effects 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 2
- 206010028813 Nausea Diseases 0.000 description 2
- 206010037660 Pyrexia Diseases 0.000 description 2
- 206010041349 Somnolence Diseases 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000008693 nausea Effects 0.000 description 2
- 210000004798 organs belonging to the digestive system Anatomy 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- KVJHGPAAOUGYJX-UHFFFAOYSA-N 1,1,3,3-tetraethoxypropane Chemical compound CCOC(OCC)CC(OCC)OCC KVJHGPAAOUGYJX-UHFFFAOYSA-N 0.000 description 1
- 201000010000 Agranulocytosis Diseases 0.000 description 1
- 208000009137 Behcet syndrome Diseases 0.000 description 1
- 201000006390 Brachial Plexus Neuritis Diseases 0.000 description 1
- 241001517013 Calidris pugnax Species 0.000 description 1
- 206010007882 Cellulitis Diseases 0.000 description 1
- 201000011275 Epicondylitis Diseases 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- 206010063560 Excessive granulation tissue Diseases 0.000 description 1
- 201000005569 Gout Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 206010034464 Periarthritis Diseases 0.000 description 1
- 206010057267 Periphlebitis Diseases 0.000 description 1
- 206010036030 Polyarthritis Diseases 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 208000008765 Sciatica Diseases 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 208000000491 Tendinopathy Diseases 0.000 description 1
- 206010043255 Tendonitis Diseases 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
- 230000001195 anabolic effect Effects 0.000 description 1
- 230000036592 analgesia Effects 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 208000002849 chondrocalcinosis Diseases 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 210000001126 granulation tissue Anatomy 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 230000007803 itching Effects 0.000 description 1
- 229960000991 ketoprofen Drugs 0.000 description 1
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 description 1
- 201000002364 leukopenia Diseases 0.000 description 1
- 231100001022 leukopenia Toxicity 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 208000001297 phlebitis Diseases 0.000 description 1
- 208000030428 polyarticular arthritis Diseases 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000001185 psoriatic effect Effects 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 201000004415 tendinitis Diseases 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7115592A FR2134293A1 (en) | 1971-04-30 | 1971-04-30 | Pyrazole carboxamidines - as analgesics and anti inflammatory agents |
| FR7207995A FR2174710A1 (en) | 1972-03-08 | 1972-03-08 | Pyrazole carboxamidines - as analgesics and anti inflammatory agents |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2221281A1 DE2221281A1 (de) | 1972-11-16 |
| DE2221281B2 DE2221281B2 (de) | 1979-01-18 |
| DE2221281C3 true DE2221281C3 (de) | 1979-11-22 |
Family
ID=26216363
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2221281A Expired DE2221281C3 (de) | 1971-04-30 | 1972-04-29 | Pharmazeutische Zubereitungen mit entzündungshemmender und analgetischer Wirkung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3833605A (enExample) |
| BE (1) | BE782220A (enExample) |
| CA (1) | CA978971A (enExample) |
| CH (1) | CH545292A (enExample) |
| DE (1) | DE2221281C3 (enExample) |
| ES (1) | ES402179A1 (enExample) |
| GB (1) | GB1369888A (enExample) |
| NL (1) | NL7205584A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3887548A (en) * | 1971-10-22 | 1975-06-03 | Hoffmann La Roche | Pyrazole derivatives |
| US4073636A (en) * | 1973-04-27 | 1978-02-14 | Bayer Aktiengesellschaft | Azolylamidine compounds and herbicidal compositions |
| EP1607381A4 (en) * | 2003-03-26 | 2006-09-13 | Nippon Carbide Kogyo Kk | PROCESS FOR THE PREPARATION OF TETRAALKOXYPROPAN AND DERIVATIVES THEREOF |
-
1972
- 1972-04-17 BE BE782220A patent/BE782220A/xx unknown
- 1972-04-19 GB GB1808672A patent/GB1369888A/en not_active Expired
- 1972-04-21 CA CA140,214A patent/CA978971A/en not_active Expired
- 1972-04-25 NL NL7205584A patent/NL7205584A/xx not_active Application Discontinuation
- 1972-04-26 US US00247833A patent/US3833605A/en not_active Expired - Lifetime
- 1972-04-27 ES ES402179A patent/ES402179A1/es not_active Expired
- 1972-04-28 CH CH641572A patent/CH545292A/fr not_active IP Right Cessation
- 1972-04-29 DE DE2221281A patent/DE2221281C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CA978971A (en) | 1975-12-02 |
| CH545292A (fr) | 1973-12-15 |
| US3833605A (en) | 1974-09-03 |
| BE782220A (fr) | 1972-07-31 |
| GB1369888A (en) | 1974-10-09 |
| DE2221281A1 (de) | 1972-11-16 |
| DE2221281B2 (de) | 1979-01-18 |
| NL7205584A (enExample) | 1972-11-01 |
| ES402179A1 (es) | 1976-01-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| OI | Miscellaneous see part 1 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| EHJ | Ceased/non-payment of the annual fee |