US3501577A - Method of treating hypertension with alkali metal salts of zinc diethylenetriaminepentaacetate - Google Patents
Method of treating hypertension with alkali metal salts of zinc diethylenetriaminepentaacetate Download PDFInfo
- Publication number
- US3501577A US3501577A US684637A US3501577DA US3501577A US 3501577 A US3501577 A US 3501577A US 684637 A US684637 A US 684637A US 3501577D A US3501577D A US 3501577DA US 3501577 A US3501577 A US 3501577A
- Authority
- US
- United States
- Prior art keywords
- zinc
- zndtpa
- hexahydrate
- alkali metal
- metal salts
- 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
- 239000011701 zinc Substances 0.000 title description 18
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 title description 16
- 229910052725 zinc Inorganic materials 0.000 title description 15
- 206010020772 Hypertension Diseases 0.000 title description 10
- QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 title description 7
- 238000000034 method Methods 0.000 title description 7
- -1 alkali metal salts Chemical class 0.000 title description 4
- 229910052783 alkali metal Inorganic materials 0.000 title description 2
- HVASDHJNLYRZEA-UHFFFAOYSA-I trisodium;zinc;2-[bis[2-[bis(carboxylatomethyl)amino]ethyl]amino]acetate Chemical compound [Na+].[Na+].[Na+].[Zn+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC(=O)[O-])CCN(CC([O-])=O)CC([O-])=O HVASDHJNLYRZEA-UHFFFAOYSA-I 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- 150000004687 hexahydrates Chemical class 0.000 description 14
- 239000011734 sodium Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 8
- 239000002775 capsule Substances 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229960003330 pentetic acid Drugs 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000001828 Gelatine Substances 0.000 description 3
- 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 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002671 adjuvant Substances 0.000 description 3
- 239000013522 chelant Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 229940099112 cornstarch Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002662 enteric coated tablet Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 239000003182 parenteral nutrition solution Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- YZYKBQUWMPUVEN-UHFFFAOYSA-N zafuleptine Chemical compound OC(=O)CCCCCC(C(C)C)NCC1=CC=C(F)C=C1 YZYKBQUWMPUVEN-UHFFFAOYSA-N 0.000 description 2
- UVJDUBUJJFBKLD-UHFFFAOYSA-L zinc;2-[bis[2-[bis(carboxylatomethyl)amino]ethyl]amino]acetate;hydron Chemical compound [H+].[H+].[H+].[Zn+2].[O-]C(=O)CN(CC([O-])=O)CCN(CC(=O)[O-])CCN(CC([O-])=O)CC([O-])=O UVJDUBUJJFBKLD-UHFFFAOYSA-L 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 241000748691 Furia Species 0.000 description 1
- 208000001953 Hypotension Diseases 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
- 235000021355 Stearic acid Nutrition 0.000 description 1
- IJLZPISNKPJMNS-UHFFFAOYSA-N [Zn].[Na].[Na].[Na] Chemical compound [Zn].[Na].[Na].[Na] IJLZPISNKPJMNS-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- IWZKICVEHNUQTL-UHFFFAOYSA-M potassium hydrogen phthalate Chemical compound [K+].OC(=O)C1=CC=CC=C1C([O-])=O IWZKICVEHNUQTL-UHFFFAOYSA-M 0.000 description 1
- 229910001414 potassium ion Chemical group 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
Definitions
- Na ZnDTPA and K ZnDTPA can be used orally and parenterally in doses to provide the equivalent of as much as 40 mg. of zinc daily per kilogram of body weight. Generally lower levels are preferred.
- the preferred route of administration is intermuscularly.
- the Na ZnDTPA and K ZnDTPA can be associated with a carrier which can be either a solid material or a sterile parenteral liquid.
- a carrier which can be either a solid material or a sterile parenteral liquid.
- the compositions can take the form of tablets, powders, capsules, or other dosage forms which are particularly useful for oral ingestion. Liquid diluents are emplayed in sterile condition for parenteral use, that is, by injecttion.
- a medium can be a sterile solvent such as water.
- compositions can take the form of active material, namely, Na ZnDTPA or K ZnDTPA or both, admixed with solid diluents, tableting adjuvants, such as cornstarch, lactose, talc, stearic acid, magnesium stearate, gums, or the like.
- tableting adjuvants such as cornstarch, lactose, talc, stearic acid, magnesium stearate, gums, or the like.
- the material can be tableted with or without adjuvants.
- Na Zn-DTPA or K ZnDTPA or both with adjuvant material can be placed in the usual capsule or resorbable material such as the usual gelatine capsule and administered in that form.
- Na ZnDTPA and CHzCOO M -nHzO K ZnDTPA can also be put up into powder packets.
- Na ZnDTPA or K3ZHDTPA or both can be prepared in the form of a suspension in a material in which Na Zn'DTPA and K ZnDTPA are not soluble.
- Example I A sample of the hexahydrate of Example I was analyzed for carbon, hydrogen, nitrogen and zinc, as follows:
- the loss-on-drying at 110 C. was 18.2%.
- the hexahydrate of Example I is a colorless, free-flowing powder which appeared to be wholly crystalline when viewed under plane polarized light. It had no precise melting po nt; a sample showed shrinking and effervescence at 110 C. and then gradual sintering and decomposition above 300 C.
- the compounds of the present invention are highly useful in solution form because of their high solubility in Water and because aqueous solutions of these compounds can be buffered to an essentially neutral pH without affecting their water solubility. These properties are illustrated in Example III.
- the following examples are illustrative of typical dosage forms for administering the compounds of this invention to animals in the treatment of hypertension.
- the formulations are made by the usual procedures for making tablets, enteric coated tablets, gelatine capsules, packets and oral and parenteral solutions.
- the above formulations are each mixed and tabletted to form 500 mg. tablets which are suitable for oral administration in treatment of hypertension to provide the equivalent of 25 mg. zinc per tablet.
- Example V When desired any of the tablets of Example IV can be coated with a solution of cellulose acetate phthalate to comply with U.S.P. specifications for enteric coated tablets.
- EXAMPLE VI.GELATIN CAPSULES (EQUIVALENT TO 50 MG. ZINC) Parts by Weight Example VI(A) VI(B) VI(C) Hexahydrate of Example I 480 240 Hexahydrate of Example II 520 260 Corn starch 120 80 100
- the above ingredients are mixed and dispensed in gelatine capsules, 600 mg. per capsule, to provide a suitable dosage form for oral administration in treatment of hypertension at a rate of 50 mg. zinc per capsule.
- a method of treating hypertension in animals which comprises administering to an animal afflicted with hypertension a hypotensive amount of a compound selected from the group consisting of the sodium salt of the zinc chelate of diethylenetriaminepentaacetic acid and the potassium salt of the zinc chelate of diethylenetriaminepentaacetic acid.
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US68463767A | 1967-11-21 | 1967-11-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3501577A true US3501577A (en) | 1970-03-17 |
Family
ID=24748904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US684637A Expired - Lifetime US3501577A (en) | 1967-11-21 | 1967-11-21 | Method of treating hypertension with alkali metal salts of zinc diethylenetriaminepentaacetate |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3501577A (en)van) |
| BE (1) | BE724229A (en)van) |
| DE (1) | DE1809651A1 (en)van) |
| FR (1) | FR8233M (en)van) |
| GB (1) | GB1205094A (en)van) |
| NL (1) | NL6816504A (en)van) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4292324A (en) * | 1974-05-02 | 1981-09-29 | Aktiebolaget Draco | Aqueous zinc solutions for medical use |
| WO2012142666A1 (en) * | 2011-04-19 | 2012-10-26 | The Mental Health Research Institute Of Victoria | Method of modulating amine oxidase activity and agents useful for same |
| US20180125885A1 (en) * | 2015-06-05 | 2018-05-10 | Nestec S.A. | Compositions comprising cinnamaldehyde and zinc and methods of using such compositions |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2805957A1 (de) * | 2013-05-23 | 2014-11-26 | hameln rds gmbh | Kristalline Formen von Trinatrium-Zink-Diethylen-triaminpentaessigsäure |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2781291A (en) * | 1953-08-21 | 1957-02-12 | Dow Chemical Co | Magnesium chelate of ethylenediaminetetraacetic acid for treatment of hypertension |
| US3172898A (en) * | 1965-03-09 | Process for preparation of metal chelates of aminopolycarboxylic acid compounds | ||
| US3240701A (en) * | 1961-08-21 | 1966-03-15 | Geigy Chem Corp | Inhibiting growth of bacteria in fluids |
-
1967
- 1967-11-21 US US684637A patent/US3501577A/en not_active Expired - Lifetime
-
1968
- 1968-11-19 DE DE19681809651 patent/DE1809651A1/de active Pending
- 1968-11-19 NL NL6816504A patent/NL6816504A/xx unknown
- 1968-11-20 GB GB55029/68A patent/GB1205094A/en not_active Expired
- 1968-11-21 FR FR174705A patent/FR8233M/fr not_active Expired
- 1968-11-21 BE BE724229D patent/BE724229A/xx unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3172898A (en) * | 1965-03-09 | Process for preparation of metal chelates of aminopolycarboxylic acid compounds | ||
| US2781291A (en) * | 1953-08-21 | 1957-02-12 | Dow Chemical Co | Magnesium chelate of ethylenediaminetetraacetic acid for treatment of hypertension |
| US3240701A (en) * | 1961-08-21 | 1966-03-15 | Geigy Chem Corp | Inhibiting growth of bacteria in fluids |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4292324A (en) * | 1974-05-02 | 1981-09-29 | Aktiebolaget Draco | Aqueous zinc solutions for medical use |
| DK152173B (da) * | 1974-05-02 | 1988-02-08 | Draco Ab | Fremgangsmaade til fremstilling af en farmaceutisk zinkkompleksoploesning til oral indgift |
| WO2012142666A1 (en) * | 2011-04-19 | 2012-10-26 | The Mental Health Research Institute Of Victoria | Method of modulating amine oxidase activity and agents useful for same |
| US20180125885A1 (en) * | 2015-06-05 | 2018-05-10 | Nestec S.A. | Compositions comprising cinnamaldehyde and zinc and methods of using such compositions |
| US11110120B2 (en) * | 2015-06-05 | 2021-09-07 | Societe Des Produits Nestle S.A. | Compositions comprising cinnamaldehyde and zinc and methods of using such compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1205094A (en) | 1970-09-16 |
| FR8233M (en)van) | 1970-09-28 |
| BE724229A (en)van) | 1969-05-21 |
| DE1809651A1 (de) | 1969-07-17 |
| NL6816504A (en)van) | 1969-05-23 |
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