US3278379A - Pain-alleviating composition - Google Patents
Pain-alleviating composition Download PDFInfo
- Publication number
- US3278379A US3278379A US313792A US31379263A US3278379A US 3278379 A US3278379 A US 3278379A US 313792 A US313792 A US 313792A US 31379263 A US31379263 A US 31379263A US 3278379 A US3278379 A US 3278379A
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- US
- United States
- Prior art keywords
- weight
- parts
- less
- pain
- pyridine
- 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 description 11
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 18
- BSYNRYMUTXBXSQ-FOQJRBATSA-N 59096-14-9 Chemical compound CC(=O)OC1=CC=CC=C1[14C](O)=O BSYNRYMUTXBXSQ-FOQJRBATSA-N 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 1
- QLSJOGIENLKPTF-BTJKTKAUSA-N (z)-but-2-enedioic acid;pyridine Chemical class C1=CC=NC=C1.OC(=O)\C=C/C(O)=O QLSJOGIENLKPTF-BTJKTKAUSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 206010042496 Sunburn Diseases 0.000 description 3
- 239000000739 antihistaminic agent Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 150000003222 pyridines Chemical class 0.000 description 2
- 125000001302 tertiary amino group Chemical group 0.000 description 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 241000220479 Acacia Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 208000019872 Drug Eruptions Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- IJHNSHDBIRRJRN-UHFFFAOYSA-N N,N-dimethyl-3-phenyl-3-(2-pyridinyl)-1-propanamine Chemical compound C=1C=CC=NC=1C(CCN(C)C)C1=CC=CC=C1 IJHNSHDBIRRJRN-UHFFFAOYSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- SSOXZAQUVINQSA-BTJKTKAUSA-N Pheniramine maleate Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC=NC=1C(CCN(C)C)C1=CC=CC=C1 SSOXZAQUVINQSA-BTJKTKAUSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229960001190 pheniramine Drugs 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A61K31/60—Salicylic acid; Derivatives thereof
Definitions
- the present invention basically comprises a composition wherein the essential therapeutically-active components, similarly to the compositions disclosed in the aforementioned co-pending application, are (1) an analgesic such as a salicylate or its functional equivalents, (2) para aminobenzoic acid or its metal salts including the salts of the alkaline metals such as sodium and potassium; alkaline earth metals such as calcium and barium; magnesium, aluminum, iron, tin, antimony, etc., and (3) an antihistamine.
- an analgesic such as a salicylate or its functional equivalents
- para aminobenzoic acid or its metal salts including the salts of the alkaline metals such as sodium and potassium
- alkaline earth metals such as calcium and barium
- magnesium, aluminum, iron, tin, antimony, etc. and (3) an antihistamine.
- the essential factor in the composition is the relative proportions of the three therapeutically active components. When these proportions are within a certain range, there is a synergistic reaction which leads to completely unexpected and novel results whereby the pain-alleviating effect is greatly enchanced while deleterious side effects are almost entirely eliminated.
- the essential relative proportions of the active components were set forth as being about 12 parts by weight of the analgesic, about 3 parts by Weight of the para aminobenzoic acid or its salts and about 0.24-2 parts by Weight of the antihistamine. It has now been discovered, however, that certain antihistamines may be effectively utilized in the above composition at concentrations lower than 0.24 part by weight, specifically at a concentration of not less than 0.04 but less than 0.24 part by Weight.
- antihistaminically-active compounds which are effective at the aforesaid lower concentrations, particularly outstanding are pyridines and pyridine maleates having a tertiary amino ethyl group attached to a nonreactive cyclic ring through either an oxygen or carbon atom.
- Examples of this type of compound are 2[u-(2-dimethylaminoethyl) benzyl] pyridine and pyridine maleate (prophenpyridamine and prophenpyridamine maleate), both in the halogenated and unhalogenated form, 2-[pchloro-u-(Z-dimethylaminoethoxy) benzyl] pyridine maleate and di 2 ⁇ 1 [2 (2 dimethylaminoethyl) 3-indenyl] ethyl ⁇ pyridine maleate.
- a specific composition embodying the present invention comprises a tablet containing as the therapeutically-active components about 300-325 mg. of acetyl salicylic acid, about 75 mg. of para aminobenzoic acid and about 1 mg. of di-2 ⁇ 1[2-(Z-dimethylaminoethyl)-3-indenyl] ethyl ⁇ pyridine maleate.
- This composition has been found to be highly effective in the relief of peripheral pain, such as may result from sunburn or other causes, while being ice substantially free of such side effects as nausea, vomiting, anorexia, fever, dermatitis medicamentosa, etc.
- the present composition may include various diluents, fillers, neutralizers, etc. such as are common in the art.
- it may include among other ingredients bonding agents such as starch, neutralizing agents such as MgCO and diluents such as lactose, stearate, acacia, glucose, dextrose, etc.
- the tablets of the present invention are preferably orally administered in a dosage of about 1-2 tablets every 3, 4 or 6 hours.
- the initial dose is preferably 1 tablet taken not less than 1 hour prior to exposure to the sun followed by 1 tablet in successive doses at four hour intervals.
- the same dosage may be used to alleviate pain and edema by after-treatment of sunburn or other burns.
- a pharmaceutical composition consisting essentially of about 12 parts by weight acetyl salicylic acid, about 3 parts by weight para aminobenzoic acid and an amount not less than about 0.04 but less than 0.24 part by weight of an antihistaminically-active compound selected from the group consisting of pyridines and pyridine maleates having a tertiary amino ethyl group attached to a nonreactive cyclic ring through an atom selected from the group consisting of oxygen and carbon atoms.
- a pharmaceutical composition consisting essentially of about 12 parts by weight acetyl salicylic acid, about 3 parts by weight para aminobenzoic acid and an amount not less than about 0.04 but less than 0.24 part by weight of 2[tx-(Z-dimethylaminoethyl) benzyl] pyridine.
- a pharmaceutical composition consisting essentially of about 12 parts by weight acetyl salicylic acid, about 3 parts by weight para aminobenzoic acid and an amount not less than about 0.04 but less than 0.24 part by weight of 2[u-(2-dimethylaminoethyl) benzyl] pyridine maleate.
- a pharmaceutical composition consisting essentially of about 12 parts by weight acetyl salicylic acid, about 3 parts by weight para aminobenzoic acid and an amount not less than about 0.04 but less than 0.24 part by Weight of 2-p-chloro-a(Z-dimethylaminoethoxy) benzyl] pyridine maleate.
- a pharmaceutical composition consisting essentially of about 12 parts by Weight acetyl salicylic acid, about 3 parts by weight para aminobenzoic acid and an amount not less than about 0.04 but less than 024 part by weight of di-2 ⁇ 1[2-(Z-dimethylaminoethyl)-3-indenyl] ethyl ⁇ pyridine maletate.
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)
Description
United States Patent 3,278,379 PAlN-ALLEVIATING COMPOSITION Leo Manson, Roslyn, Pa., assignor to Edgewood Laboratories, Inc., Philadelphia, Pa., a corporation of Pennsylvania No Drawing. Filed Oct. 4, 1963, Ser. No. 313,792 The portion of the term of the patent subsequent to Jan. 30, 1979, has been disclaimed Claims. (Cl. 167-65) This invention relates to a therapeutically-active composition for internal administration, and it particularly relates to a composition of the aforesaid type which is highly effective in the alleviation of peripheral pain and irritation.
This application is a continuation-in-part of co-pending application Serial No. 137,003, filed September 11, 1961 and now abandoned, said application Serial No. 137,003 having itself been a continuation-in-part of application Serial No. 734,110, which was filed May 9, 1958 and issued as US. Patent No. 3,019,165 on January 30, 1962.
The present invention basically comprises a composition wherein the essential therapeutically-active components, similarly to the compositions disclosed in the aforementioned co-pending application, are (1) an analgesic such as a salicylate or its functional equivalents, (2) para aminobenzoic acid or its metal salts including the salts of the alkaline metals such as sodium and potassium; alkaline earth metals such as calcium and barium; magnesium, aluminum, iron, tin, antimony, etc., and (3) an antihistamine.
The essential factor in the composition is the relative proportions of the three therapeutically active components. When these proportions are within a certain range, there is a synergistic reaction which leads to completely unexpected and novel results whereby the pain-alleviating effect is greatly enchanced while deleterious side effects are almost entirely eliminated.
In the aforementioned co-pending application, the essential relative proportions of the active components were set forth as being about 12 parts by weight of the analgesic, about 3 parts by Weight of the para aminobenzoic acid or its salts and about 0.24-2 parts by Weight of the antihistamine. It has now been discovered, however, that certain antihistamines may be effectively utilized in the above composition at concentrations lower than 0.24 part by weight, specifically at a concentration of not less than 0.04 but less than 0.24 part by Weight.
Among the antihistaminically-active compounds which are effective at the aforesaid lower concentrations, particularly outstanding are pyridines and pyridine maleates having a tertiary amino ethyl group attached to a nonreactive cyclic ring through either an oxygen or carbon atom. Examples of this type of compound are 2[u-(2-dimethylaminoethyl) benzyl] pyridine and pyridine maleate (prophenpyridamine and prophenpyridamine maleate), both in the halogenated and unhalogenated form, 2-[pchloro-u-(Z-dimethylaminoethoxy) benzyl] pyridine maleate and di 2{1 [2 (2 dimethylaminoethyl) 3-indenyl] ethyl} pyridine maleate.
A specific composition embodying the present invention comprises a tablet containing as the therapeutically-active components about 300-325 mg. of acetyl salicylic acid, about 75 mg. of para aminobenzoic acid and about 1 mg. of di-2{1[2-(Z-dimethylaminoethyl)-3-indenyl] ethyl} pyridine maleate. This composition has been found to be highly effective in the relief of peripheral pain, such as may result from sunburn or other causes, while being ice substantially free of such side effects as nausea, vomiting, anorexia, fever, dermatitis medicamentosa, etc.
The present composition may include various diluents, fillers, neutralizers, etc. such as are common in the art. For example, it may include among other ingredients bonding agents such as starch, neutralizing agents such as MgCO and diluents such as lactose, stearate, acacia, glucose, dextrose, etc.
For the relief of peripheral pain and irritation, the tablets of the present invention are preferably orally administered in a dosage of about 1-2 tablets every 3, 4 or 6 hours.
To avoid the undesirable effects of sunburn, the initial dose is preferably 1 tablet taken not less than 1 hour prior to exposure to the sun followed by 1 tablet in successive doses at four hour intervals. The same dosage may be used to alleviate pain and edema by after-treatment of sunburn or other burns.
Obviously many modifications and variations of the present invention are possible in the light of the above teachings. It is, therefore, to be understood that within the scope of the appended claims, the invention may be practiced otherwise than as specifically described.
The invention claimed is:
1. A pharmaceutical composition consisting essentially of about 12 parts by weight acetyl salicylic acid, about 3 parts by weight para aminobenzoic acid and an amount not less than about 0.04 but less than 0.24 part by weight of an antihistaminically-active compound selected from the group consisting of pyridines and pyridine maleates having a tertiary amino ethyl group attached to a nonreactive cyclic ring through an atom selected from the group consisting of oxygen and carbon atoms.
2. A pharmaceutical composition consisting essentially of about 12 parts by weight acetyl salicylic acid, about 3 parts by weight para aminobenzoic acid and an amount not less than about 0.04 but less than 0.24 part by weight of 2[tx-(Z-dimethylaminoethyl) benzyl] pyridine.
3. A pharmaceutical composition consisting essentially of about 12 parts by weight acetyl salicylic acid, about 3 parts by weight para aminobenzoic acid and an amount not less than about 0.04 but less than 0.24 part by weight of 2[u-(2-dimethylaminoethyl) benzyl] pyridine maleate.
4. A pharmaceutical composition consisting essentially of about 12 parts by weight acetyl salicylic acid, about 3 parts by weight para aminobenzoic acid and an amount not less than about 0.04 but less than 0.24 part by Weight of 2-p-chloro-a(Z-dimethylaminoethoxy) benzyl] pyridine maleate.
5. A pharmaceutical composition consisting essentially of about 12 parts by Weight acetyl salicylic acid, about 3 parts by weight para aminobenzoic acid and an amount not less than about 0.04 but less than 024 part by weight of di-2{1[2-(Z-dimethylaminoethyl)-3-indenyl] ethyl} pyridine maletate.
References Cited by the Examiner UNITED STATES PATENTS 3,019,165 1/1962 Mansor 167-65 3,076,804 2/1963 Huebner 260240 OTHER REFERENCES Merck Index, 7th Ed. (1960), Merck & Co., Rahway, New Jersey, pp. 878-9.
JULIAN S. LEVITT, Primary Examiner.
MARTIN I COHEN, Assistant Examiner.
Claims (1)
- 2. A PHARMACEUTICAL COMPOSITION CONSISTING ESSENTIALLY OF ABOUT 12 PARTS BY WEIGHT ACETYL SALICYLIC ACID, ABOUT 3 PARTS BY WEIGHT PARA AMINOBENZOIC ACID AND AN AMOUNT NOT LESS THAN ABOUT 0.04 BUT LESS THAN 0.24 PART BY WEIGHT OF 2(A-(2-DIMETHYLAMINOETHYL) BENZYL) PYRIDINE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US313792A US3278379A (en) | 1963-10-04 | 1963-10-04 | Pain-alleviating composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US313792A US3278379A (en) | 1963-10-04 | 1963-10-04 | Pain-alleviating composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3278379A true US3278379A (en) | 1966-10-11 |
Family
ID=23217168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US313792A Expired - Lifetime US3278379A (en) | 1963-10-04 | 1963-10-04 | Pain-alleviating composition |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3278379A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4650789A (en) * | 1985-10-15 | 1987-03-17 | Commonwealth Medical Corporation Of America | Method and composition for increasing production of serotonin |
| EP2493465A4 (en) * | 2009-10-26 | 2012-09-05 | Sephoris Pharmaceuticals Llc | TREATMENT OF SUNSETS USING ANALGESICS AND ANTIHISTAMINES |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3019165A (en) * | 1958-05-09 | 1962-01-30 | Edgewood Lab Inc | Sunburn preventive and burn remedy |
| US3076804A (en) * | 1959-02-10 | 1963-02-05 | Ciba Geigy Corp | 2-(n, n-di-loweralkyl-amino-loweralkyl)-1-[pyridyl-methylidene]-indene and process |
-
1963
- 1963-10-04 US US313792A patent/US3278379A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3019165A (en) * | 1958-05-09 | 1962-01-30 | Edgewood Lab Inc | Sunburn preventive and burn remedy |
| US3076804A (en) * | 1959-02-10 | 1963-02-05 | Ciba Geigy Corp | 2-(n, n-di-loweralkyl-amino-loweralkyl)-1-[pyridyl-methylidene]-indene and process |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4650789A (en) * | 1985-10-15 | 1987-03-17 | Commonwealth Medical Corporation Of America | Method and composition for increasing production of serotonin |
| EP2493465A4 (en) * | 2009-10-26 | 2012-09-05 | Sephoris Pharmaceuticals Llc | TREATMENT OF SUNSETS USING ANALGESICS AND ANTIHISTAMINES |
| US8957095B2 (en) | 2009-10-26 | 2015-02-17 | Sephoris Pharmaceuticals, Llc | Treatment of sunburn using analgesics and antihistamines |
| EP2853262A1 (en) * | 2009-10-26 | 2015-04-01 | Sephoris Pharmaceuticals, LLC | Treatment of sunburn using analgesics and antihistamines |
| AU2010315561B2 (en) * | 2009-10-26 | 2016-10-20 | Sephoris Pharmaceuticals, Llc | Treatment of sunburn using analgesics and antihistamines |
| US9895360B2 (en) | 2009-10-26 | 2018-02-20 | Sephoris Pharmaceuticals, Llc | Treatment of sunburn using analgesics and antihistamines |
| US10751331B2 (en) | 2009-10-26 | 2020-08-25 | Sephoris Pharmaceuticals, Llc | Treatment of sunburn using analgesics and antihistamines |
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