US3840663A - 5-alkylpipecolic acids as anti-hypertensive agents - Google Patents
5-alkylpipecolic acids as anti-hypertensive agents Download PDFInfo
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- US3840663A US3840663A US00237527A US23752772A US3840663A US 3840663 A US3840663 A US 3840663A US 00237527 A US00237527 A US 00237527A US 23752772 A US23752772 A US 23752772A US 3840663 A US3840663 A US 3840663A
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- United States
- Prior art keywords
- alkylpipecolic
- acids
- trans
- blood pressure
- hypertensive agents
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- 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
- 239000002253 acid Substances 0.000 title description 13
- 150000007513 acids Chemical class 0.000 title description 6
- 229940030600 antihypertensive agent Drugs 0.000 title description 4
- 239000002220 antihypertensive agent Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 11
- 206010020772 Hypertension Diseases 0.000 claims abstract description 7
- 230000036772 blood pressure Effects 0.000 claims abstract description 7
- 230000001631 hypertensive effect Effects 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 4
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims abstract description 3
- 150000003839 salts Chemical class 0.000 abstract description 8
- 125000000217 alkyl group Chemical group 0.000 description 5
- 241000906446 Theraps Species 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002552 dosage form 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
- 238000007911 parenteral administration Methods 0.000 description 2
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 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
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229940035674 anesthetics Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- WXQWKYFPCLREEY-UHFFFAOYSA-N azane;ethanol Chemical class N.CCO.CCO.CCO WXQWKYFPCLREEY-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
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-O benzylaminium Chemical compound [NH3+]CC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000003193 general anesthetic agent Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- -1 npropyl Chemical group 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- LJPZHJUSICYOIX-UHFFFAOYSA-N quinolizidine Chemical class C1CCCC2CCCCN21 LJPZHJUSICYOIX-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
Definitions
- This invention relates to a method of treating hypertension using 5-alkylpipecolic acids as the antihypertensive agents.
- 5-Alkylpipecolic acids have previously been reported to be useful as intermediates in the preparation of certain quinolizidines, and as anesthetics and antibacterial agents. It has now been found that compounds of the formula lCOOH wherein R is C -C alkyl or a salt thereof are useful in lowering blood pressure in hypertensive patients.
- C -C alkyl refers to both straight and branched chain alkyl groups having from 1 to 8 carbon atoms, and including methyl, ethyl, npropyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neo-pentyl, n-hexyl and the like.
- salts refers to salts such as the alkali metal, alkaline earth metal, ammonium and substituted ammonium salts including the sodium, potassium, lithium, calcium, magnesium, barium, methyl ammonium, diethylammonium, benzylammonium, triethanol ammonium salts and the like, as well as the pharmaceutically acceptable acid addition salts including the hydrochloride, hydrobromide, sulfate, bisulfate, acetate, valerate, oleate, laurate, borate, benzoate, lactate, phosphate, tosylate, citrate, maleate, fumarate, succinate, tartrate and the like.
- Such salts are prepared by methods well known in the art.
- the compounds useful in the practice of this invention have been separated into the cisand trans-isomers While the mixture and the trans-isomers exhibit antihypertensive activity, the cis-isomers are inactive as antihypertensive agents.
- the compounds useful in the practice of this invention exhibit activity by both the oral and intraperitioneal routes; however, the oral route is the preferred route of administration. Accordingly, the compounds of this invention are administered to hypertensive patients at dosages of from 0.1 to mg./kg. of body weight daily, preferably in divided doses, i.e., three to four times daily.
- the presently preferred compound is dl-trans-S-n-butylpipecolic acid which reduced blood pressure in spontaneously hypertensive rats up to 18% for 28 hours after oral administration of 10 mg./kg. dose.
- suitable agents useful in the practice of this invention include S-methylpipecolic acid, S-n-propylpipecolic acid, S-neopentylpipecolic acid, S-n-hexylpipecolic acid and the like.
- the 5-alkylpipecolic acids can be co-administered with, for example, diuretics or tranquilizers.
- the compounds can be administered alone, that is, as the sole component of a filled capsule, it is preferred to formulate the compound in various dosage forms for oral or parenteral administration such as tablets, syrups, sterile aqueous or non-aqueous suspensions and the like.
- the oral dosage forms are prepared by methods well known in the art, and generally include a pharmaceutically acceptable carrier or diluent such as lactose, starch or sucrose, along with lubricating agents such as magnesium stearate and flavoring and sweetening agents and the like.
- the dosage forms for parenteral administration are also prepared by methods well known in the art.
- a method of lowering blood pressure in hypertensive patient comprising administering a therapeutically effective amount of a compound selected from the group consisting of the trans isomer and a mixture of the trans and cis isomers represented by the formula J COOH wherein R is C -C alkyl or a salt thereof to said patient.
- a compound selected from the group consisting of the trans isomer and a mixture of the trans and cis isomers represented by the formula J COOH wherein R is C -C alkyl or a salt thereof to said patient.
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- 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)
Abstract
WHEREIN R IS C1-C8 ALKYL OR A SALT THEREOF TO SAID PATIENT.
2-(HOOC-),5-R1-PIPERIDINE
1. A METHOD OF LOWERING BLOOD PRESSURE IN HYPERTENSIVE PATIENT COMPRISING ADMINISTERING A THERAPEUTICALLY EFFECTIVE AMOUNT OF A COMPOUND SELECTED FROM THE GROUP CONSISTING OF THE TRANS ISOMER AND A MIXTURE OF THE TRANS AND CIS ISOMERS REPRESENTED BY THE FORMULA
2-(HOOC-),5-R1-PIPERIDINE
1. A METHOD OF LOWERING BLOOD PRESSURE IN HYPERTENSIVE PATIENT COMPRISING ADMINISTERING A THERAPEUTICALLY EFFECTIVE AMOUNT OF A COMPOUND SELECTED FROM THE GROUP CONSISTING OF THE TRANS ISOMER AND A MIXTURE OF THE TRANS AND CIS ISOMERS REPRESENTED BY THE FORMULA
Description
United States Patent 3,840,663 S-ALKYLPIPECOLIC ACIDS AS ANTI- HY PERTENSIVE AGENTS Peter Hadley Jones, Lake Forest, and Pitambar Somani,
Libertlylyille, 111., assignors to Abbott Laboratories, Chicago,
No Drawing. Filed Mar. 23, 1972, Ser. No. 237,527 Int. Cl. A61]: 27/00 US. Cl. 424-267 3 Claims ABSTRACT OF THE DISCLOSURE A method of lowering blood pressure in hypertensive patients comprising administering a therapeutically effective amount of a compound of the formula l \N o 0 OH wherein R is C -C alkyl or a salt thereof.
DETAILED DESCRIPTION OF THE INVENTION This invention relates to a method of treating hypertension using 5-alkylpipecolic acids as the antihypertensive agents.
5-Alkylpipecolic acids have previously been reported to be useful as intermediates in the preparation of certain quinolizidines, and as anesthetics and antibacterial agents. It has now been found that compounds of the formula lCOOH wherein R is C -C alkyl or a salt thereof are useful in lowering blood pressure in hypertensive patients.
As used herein, the term C -C alkyl refers to both straight and branched chain alkyl groups having from 1 to 8 carbon atoms, and including methyl, ethyl, npropyl, iso-propyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neo-pentyl, n-hexyl and the like.
The term salts refers to salts such as the alkali metal, alkaline earth metal, ammonium and substituted ammonium salts including the sodium, potassium, lithium, calcium, magnesium, barium, methyl ammonium, diethylammonium, benzylammonium, triethanol ammonium salts and the like, as well as the pharmaceutically acceptable acid addition salts including the hydrochloride, hydrobromide, sulfate, bisulfate, acetate, valerate, oleate, laurate, borate, benzoate, lactate, phosphate, tosylate, citrate, maleate, fumarate, succinate, tartrate and the like. Such salts are prepared by methods well known in the art.
The synthesis of the S-alkylpipecolic acids is disclosed in French Patent No. M1599 1963) and in Arch. Pharm. (Weinheim) 301 (10); 728-35 (1968).
The compounds useful in the practice of this invention have been separated into the cisand trans-isomers While the mixture and the trans-isomers exhibit antihypertensive activity, the cis-isomers are inactive as antihypertensive agents.
"Ice
The antihypertensive activity of the compounds useful in the practice of this invention was first established in the spontaneously hypertensive rat procedure, Tabei et al.,
Clin. Pharmac. Therap., 11 (2); 269-274 (1970), wherein significant decreases in blood pressure were observed at oral dosages of 10 mg./kg. of body weight and I at 30 mg./kg. i.p.
The compounds useful in the practice of this invention exhibit activity by both the oral and intraperitioneal routes; however, the oral route is the preferred route of administration. Accordingly, the compounds of this invention are administered to hypertensive patients at dosages of from 0.1 to mg./kg. of body weight daily, preferably in divided doses, i.e., three to four times daily.
The presently preferred compound is dl-trans-S-n-butylpipecolic acid which reduced blood pressure in spontaneously hypertensive rats up to 18% for 28 hours after oral administration of 10 mg./kg. dose. However, other suitable agents useful in the practice of this invention include S-methylpipecolic acid, S-n-propylpipecolic acid, S-neopentylpipecolic acid, S-n-hexylpipecolic acid and the like.
As is the case with other antihypertensive agents, the 5-alkylpipecolic acids can be co-administered with, for example, diuretics or tranquilizers.
While the compounds can be administered alone, that is, as the sole component of a filled capsule, it is preferred to formulate the compound in various dosage forms for oral or parenteral administration such as tablets, syrups, sterile aqueous or non-aqueous suspensions and the like. The oral dosage forms are prepared by methods well known in the art, and generally include a pharmaceutically acceptable carrier or diluent such as lactose, starch or sucrose, along with lubricating agents such as magnesium stearate and flavoring and sweetening agents and the like. The dosage forms for parenteral administration are also prepared by methods well known in the art.
We claim:
1. A method of lowering blood pressure in hypertensive patient comprising administering a therapeutically effective amount of a compound selected from the group consisting of the trans isomer and a mixture of the trans and cis isomers represented by the formula J COOH wherein R is C -C alkyl or a salt thereof to said patient. 2. The method of Claim 1 wherein said compound is S-n-butylpipecolic acid.
3. The method of Claim 1 wherein said compound is dl-trans-S-n-butylpipecolic acid.
References Cited Clin. Pharmac. & Therap., 11(2); 269-274 (1970).
ALBERT T. MEYERS, Primary Examiner D. M. STEPHENS, Assistant Examiner US. Cl. X.R. 424263 Patented Oct. 8, 197 4
Claims (1)
1. A METHOD OF LOWERING BLOOD PRESSURE IN HYPERTENSIVE PATIENT COMPRISING ADMINISTERING A THERAPEUTICALLY EFFECTIVE AMOUNT OF A COMPOUND SELECTED FROM THE GROUP CONSISTING OF THE TRANS ISOMER AND A MIXTURE OF THE TRANS AND CIS ISOMERS REPRESENTED BY THE FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00237527A US3840663A (en) | 1972-03-23 | 1972-03-23 | 5-alkylpipecolic acids as anti-hypertensive agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00237527A US3840663A (en) | 1972-03-23 | 1972-03-23 | 5-alkylpipecolic acids as anti-hypertensive agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3840663A true US3840663A (en) | 1974-10-08 |
Family
ID=22894108
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00237527A Expired - Lifetime US3840663A (en) | 1972-03-23 | 1972-03-23 | 5-alkylpipecolic acids as anti-hypertensive agents |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3840663A (en) |
-
1972
- 1972-03-23 US US00237527A patent/US3840663A/en not_active Expired - Lifetime
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