US3890444A - Drug composition - Google Patents
Drug composition Download PDFInfo
- Publication number
- US3890444A US3890444A US354558A US35455873A US3890444A US 3890444 A US3890444 A US 3890444A US 354558 A US354558 A US 354558A US 35455873 A US35455873 A US 35455873A US 3890444 A US3890444 A US 3890444A
- Authority
- US
- United States
- Prior art keywords
- propoxyphene
- dextro
- phenyl butazone
- butazone
- phenyl
- 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
- 229940079593 drug Drugs 0.000 title claims abstract description 23
- 239000003814 drug Substances 0.000 title claims abstract description 22
- 239000000203 mixture Substances 0.000 title claims abstract 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 abstract description 38
- 229960002895 phenylbutazone Drugs 0.000 claims abstract description 34
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 claims abstract description 26
- 229960004193 dextropropoxyphene Drugs 0.000 claims abstract description 26
- 230000000202 analgesic effect Effects 0.000 claims abstract description 12
- 230000003356 anti-rheumatic effect Effects 0.000 claims abstract description 11
- 239000003435 antirheumatic agent Substances 0.000 claims abstract description 9
- 239000004480 active ingredient Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims description 4
- 208000025747 Rheumatic disease Diseases 0.000 claims description 3
- 230000000694 effects Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 208000011580 syndromic disease Diseases 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 3
- 230000036592 analgesia Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-SCSAIBSYSA-N D-Proline Chemical compound OC(=O)[C@H]1CCCN1 ONIBWKKTOPOVIA-SCSAIBSYSA-N 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- 206010029240 Neuritis Diseases 0.000 description 1
- 201000009859 Osteochondrosis Diseases 0.000 description 1
- 206010034464 Periarthritis Diseases 0.000 description 1
- 208000012287 Prolapse Diseases 0.000 description 1
- 206010037779 Radiculopathy Diseases 0.000 description 1
- 241000950638 Symphysodon discus Species 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 206010007821 cauda equina syndrome Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- HOQADATXFBOEGG-UHFFFAOYSA-N isofenphos Chemical compound CCOP(=S)(NC(C)C)OC1=CC=CC=C1C(=O)OC(C)C HOQADATXFBOEGG-UHFFFAOYSA-N 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 229960001797 methadone Drugs 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 206010061928 radiculitis Diseases 0.000 description 1
- 201000005671 spondyloarthropathy Diseases 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000000115 thoracic cavity Anatomy 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
- A61K31/415—1,2-Diazoles
Definitions
- the present invention relates to a drug compound antirheumatic and analgesic indication.
- phenyl butazone (1,2-diphenyl- 3,5-dioxo-4-n-butyl-pyrazolidine) has analgesic and antirheumatic effects.
- phenyl butazone was considered to be the most effective antirheumatic drug, apart from the steroids.
- the administration of phenyl butazone in effective dosages is accompanied by serious side effects, caused by its inhibiting action on certain enzymatic reactions taking place in the body.
- the objective underlying the present invention was therefore the discovery of a drug based on phenyl butazone which retains the known antirheumatic effects of phenyl butazone, while having a strong analgesic indication at reduced dosage, so that the known side effects are eliminated, or at least reduced.
- mice In a series of writhing tests performed on mice it was found that especially favorable results are obtained with a drug compound in which dextro-propoxyphene and phenyl butazone are present in a molar ratio of l to 2. These results are reflected in a table given below in which some of the readings obtained in the tests are listed by way of example. The effectiveness of the different drug compounds is stated as a percentage in relation to the l to 2 molar ratio.
- the extraordinary analgesic effects achieved are particularly evident in the category of post-traumatic conditions.
- the treatment results obtained in other typical categories of the rheumatoid group indicates that the antirheumatic effects of phenyl butazone in the disclosed combination fully match previously observed effects of treatment with phenyl butazone in its known large dosage, even though its dosage in the disclosed combination is substantially reduced.
- Drug composition having an antirheumatic and analgesic indication containing as active ingredients dextropropoxyphene and phenyl butazone in moleratio between 1 to l and l to 8.
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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2220500A DE2220500C3 (de) | 1972-04-26 | 1972-04-26 | Analgetikum |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3890444A true US3890444A (en) | 1975-06-17 |
Family
ID=5843353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US354558A Expired - Lifetime US3890444A (en) | 1972-04-26 | 1973-04-26 | Drug composition |
Country Status (12)
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3482021A (en) * | 1965-07-01 | 1969-12-02 | Geigy Chem Corp | Anti-phlogistic and analgesic compositions and methods for relieving inflammatory conditions |
| US3749797A (en) * | 1971-07-02 | 1973-07-31 | Lilly Co Eli | Analgesic compositions |
-
1972
- 1972-04-26 DE DE2220500A patent/DE2220500C3/de not_active Expired
-
1973
- 1973-04-24 FR FR7316250*A patent/FR2182249B1/fr not_active Expired
- 1973-04-25 GB GB1952573A patent/GB1431661A/en not_active Expired
- 1973-04-26 ZA ZA732847A patent/ZA732847B/xx unknown
- 1973-04-26 US US354558A patent/US3890444A/en not_active Expired - Lifetime
- 1973-04-26 NL NL7305850.A patent/NL160487C/xx not_active IP Right Cessation
- 1973-04-26 AT AT373873A patent/AT331967B/de not_active IP Right Cessation
- 1973-04-26 LU LU67498A patent/LU67498A1/xx unknown
- 1973-04-26 DD DD170455A patent/DD102916A1/xx unknown
- 1973-04-26 BE BE130448A patent/BE798758A/xx unknown
- 1973-04-26 CA CA170,092A patent/CA1014473A/en not_active Expired
- 1973-05-01 AU AU55048/73A patent/AU5504873A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3482021A (en) * | 1965-07-01 | 1969-12-02 | Geigy Chem Corp | Anti-phlogistic and analgesic compositions and methods for relieving inflammatory conditions |
| US3749797A (en) * | 1971-07-02 | 1973-07-31 | Lilly Co Eli | Analgesic compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2220500B2 (de) | 1980-06-19 |
| NL160487B (nl) | 1979-06-15 |
| FR2182249B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-07-02 |
| ZA732847B (en) | 1974-03-27 |
| DD102916A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-01-05 |
| ATA373873A (de) | 1975-12-15 |
| BE798758A (fr) | 1973-10-26 |
| FR2182249A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-12-07 |
| AU5504873A (en) | 1974-11-07 |
| LU67498A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-07-13 |
| DE2220500A1 (de) | 1973-11-08 |
| CA1014473A (en) | 1977-07-26 |
| NL160487C (nl) | 1979-11-15 |
| DE2220500C3 (de) | 1981-02-26 |
| NL7305850A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1973-10-30 |
| AT331967B (de) | 1976-09-10 |
| GB1431661A (en) | 1976-04-14 |
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