US3551437A - Certain 4-(1,2,4-oxadiazole-3 or 5-yl) pyridinium salts and derivatives thereof - Google Patents
Certain 4-(1,2,4-oxadiazole-3 or 5-yl) pyridinium salts and derivatives thereof Download PDFInfo
- Publication number
- US3551437A US3551437A US875527A US87552769A US3551437A US 3551437 A US3551437 A US 3551437A US 875527 A US875527 A US 875527A US 87552769 A US87552769 A US 87552769A US 3551437 A US3551437 A US 3551437A
- Authority
- US
- United States
- Prior art keywords
- oxadiazol
- oxadiazole
- derivatives
- certain
- methyl
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 239000008280 blood Substances 0.000 description 8
- 210000004369 blood Anatomy 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 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 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 230000002218 hypoglycaemic effect Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- ZUUATXHRJFHSGO-UHFFFAOYSA-N chembl1896408 Chemical compound O/N=C(/N)C1=CC=NC=C1 ZUUATXHRJFHSGO-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- GPTVQTPMFOLLOA-UHFFFAOYSA-N 1-chloro-2-ethoxyethane Chemical compound CCOCCCl GPTVQTPMFOLLOA-UHFFFAOYSA-N 0.000 description 1
- SMANNJALMIGASX-UHFFFAOYSA-N 1-chloro-3-(3-chloropropoxy)propane Chemical compound ClCCCOCCCCl SMANNJALMIGASX-UHFFFAOYSA-N 0.000 description 1
- QODHJTGZDDJFDK-UHFFFAOYSA-N 1-chloro-3-propoxypropane Chemical compound CCCOCCCCl QODHJTGZDDJFDK-UHFFFAOYSA-N 0.000 description 1
- ZAAIEOSUVDRLGD-UHFFFAOYSA-N 3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound O1C=NC(C=2N=CC=CC=2)=N1 ZAAIEOSUVDRLGD-UHFFFAOYSA-N 0.000 description 1
- HAHABUMKGNVBHA-UHFFFAOYSA-N 4-pyridin-1-ium-1-yloxadiazole Chemical group O1N=NC(=C1)[N+]1=CC=CC=C1 HAHABUMKGNVBHA-UHFFFAOYSA-N 0.000 description 1
- RGTBLCLLSZPOKR-UHFFFAOYSA-N 5-methyl-1,2,4-oxadiazole Chemical compound CC1=NC=NO1 RGTBLCLLSZPOKR-UHFFFAOYSA-N 0.000 description 1
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- -1 alkyl 1,2,4-oxadiazolylpyridinium salts Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000005233 alkylalcohol group Chemical group 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 229940126904 hypoglycaemic agent Drugs 0.000 description 1
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 1
- 229940060367 inert ingredients Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
- BJDYCCHRZIFCGN-UHFFFAOYSA-N pyridin-1-ium;iodide Chemical compound I.C1=CC=NC=C1 BJDYCCHRZIFCGN-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B63—SHIPS OR OTHER WATERBORNE VESSELS; RELATED EQUIPMENT
- B63H—MARINE PROPULSION OR STEERING
- B63H1/00—Propulsive elements directly acting on water
- B63H1/02—Propulsive elements directly acting on water of rotary type
- B63H1/04—Propulsive elements directly acting on water of rotary type with rotation axis substantially at right angles to propulsive direction
- B63H1/06—Propulsive elements directly acting on water of rotary type with rotation axis substantially at right angles to propulsive direction with adjustable vanes or blades
- B63H1/08—Propulsive elements directly acting on water of rotary type with rotation axis substantially at right angles to propulsive direction with adjustable vanes or blades with cyclic adjustment
Definitions
- This invention relates to new quaternary lower alkoxy- (lower)alkyl-1,2,4-oxadiazolylpyridinium salts which may be illustrated by the following formula:
- R is lower alkyl
- R is lower alkoxy(lower)alkyl
- X is a pharmaceutically acceptable anion
- Z is a trivalent radical selected from the group consisting of and The dotted line represents one double bond, the position of which is dependent upon the definition of Z. When Z is the double bond is between the N and carbon containing R, and when Z has the other meaning, the double bond is in the other position.
- the terms lower alkyl and lower alkoxy include those radicals having 1 to 4 carbon atoms.
- the compounds are crysaalline solids, soluble in water.
- the compounds of the present invention may be prepared by reaction of a 1,2,4-oxadiazolylpyridine with a lower alkoxy(lower)alkyl halide at a temperature of to 200 C. with or without a solvent, such as a lower alkyl alcohol, for a time of one minute to twenty-four hours in an open vessel or a sealed bomb.
- quaternary compounds of the present inven tion are, for example: 1-(2-ethoxyethyl)-4-(5-methyl-1,2, 4-oxadiazol 3 yl)pyridinium chloride, 1-(2-methoxyethyl) -4- (S-methyl-1,2,4-oxadiazol-3 -yl) pyridinium chloride, 1-(2-propoxyethyl) 4 (S-methyl-1,2,4-oxadiazol- 3-yl)pyridinium bromide, 1-(2-ethoxymethyl) 4 (5- methyl-1,2,4-oxadiazol 3 yl)pyridinium iodide, 1-(2- propoxypropyl) 4 (S-methyl-1,2,4-oxadiazol-3-yl)- pyridinium chloride.
- the quaternary compounds of the present invention show hypoglycemic activity which indicates they are use ful as medicaments in the lowering of blood sugar levels.
- the compounds of this invention are administered by gavage as saline solutions to CF1 mice (Carworth Farms, 18-25 grams (4-6 animals). Control animals receive an equivalent volume of saline. Food is withheld from animals after dosing. Blood glucose is determined on 0.05 ml. samples of blood by the method of Hotfman [1. Biol. Chem, 120, 51 (1937)] as adapted to the Technicon AutoAnalyzer and is expressed as percent change from predose values. The data are shown in the table hereinafter. These results show that the compounds of the present invention are useful in lowering the blood glucose concentrations of warm-blooded animals.
- hypoglycemic agents can be incorporated in various pharmaceutical forms such as tablets, capsules, pills and so forth, for immediate or sustained release, by combining with suitable carriers. They may be in the form of dosage units for a single therapeutic dose or in small units for multiple dosages or in larger units for division into single doses. Obviously, in addition to the therapeutic hypoglycemic compounds, there may be present excipients, binders, fillers and other therapeutically inert ingredients necessary in the formulation of the desired pharmaceutical preparation.
- EXAM PLE 1 Preparation of 4-(S-methyl-1,2,4-oxadiazol-3-yl)pyridine 'A mixture of 27 g. of isonicotinamidoxime and 50 ml. of acetic anhydride is warmed on a steam bath for 2 hours, and then heated under reflux for 3 hours. The solvent is distilled and the dark liquid residue is diluted with water. The crystals which form are collected, washed with water, and recrystallized from ethanol to provide colorless crystals, melting point 92-93 C.
- EXAMPLE 2 Preparation of l-(2-ethoxyethyl)-4-(5-methyl-l,2,4-oxadiazol-3-yl)pyridinium chloride A mixture of 5.0 g. of 4-(S-methyl-1,2,4-oxadiazol-3- yl)pyridine and 15 ml. of 2-chloroethyl ethyl ether is heated in a bomb at C. for 20 hours. The excess 2-chloroethyl ether is evaporated and the black residue is recrystallized from isopropyl alcohol-ether to give offwhite crystals, melting point l87188 C.
- EXAMPLE 4 Preparation of l-(3-propoxypropyl)-4-(5-ethyl-1,2,4-oxa diaZol-3-yl)pyridinium chloride A mixture of 5.0 g. of 4-(5-ethyl-l,2,4-oxadiazol-3-yl) pyridine and 15 ml. of 3-chloropropyl propyl ether is heated in a bomb at 130 C. for 20 hours. The excess 3- chloropropyl ether is evaporated and the residue is recrystallized to give the product of the example.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- Ocean & Marine Engineering (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
United States Patent 01 free ABSTRACT OF THE DISCLOSURE Quaternary lower alkoxy(lower) alkyl-1,2,4-oxadiazolylpyridinium salts are described along with methods of preparing the same. These compounds show hypoglycemic activity evidenced by their ability to lower blood sugar levels.
The present application is a continuation-in-part of our application Ser. No. 676,706 filed Oct. 20, 1967, now abandoned.
PRIOR ART Applicants are aware of British Pat. 875,887 directed to pyridinium salts. However the present invention is directed to subject matter and utility not disclosed therein.
SUMMARY OF THE INVENTION This invention relates to new quaternary lower alkoxy- (lower)alkyl-1,2,4-oxadiazolylpyridinium salts which may be illustrated by the following formula:
wherein R is lower alkyl, R is lower alkoxy(lower)alkyl, X is a pharmaceutically acceptable anion and Z is a trivalent radical selected from the group consisting of and The dotted line represents one double bond, the position of which is dependent upon the definition of Z. When Z is the double bond is between the N and carbon containing R, and when Z has the other meaning, the double bond is in the other position. The terms lower alkyl and lower alkoxy include those radicals having 1 to 4 carbon atoms.
In general, the compounds are crysaalline solids, soluble in water.
The compounds of the present invention may be prepared by reaction of a 1,2,4-oxadiazolylpyridine with a lower alkoxy(lower)alkyl halide at a temperature of to 200 C. with or without a solvent, such as a lower alkyl alcohol, for a time of one minute to twenty-four hours in an open vessel or a sealed bomb.
The reaction is illustrated schematically below:
3,551,437 Patented Dec. 29, 1970 wherein R, R Z and X are as hereinbefore defined.
Among the quaternary compounds of the present inven tion are, for example: 1-(2-ethoxyethyl)-4-(5-methyl-1,2, 4-oxadiazol 3 yl)pyridinium chloride, 1-(2-methoxyethyl) -4- (S-methyl-1,2,4-oxadiazol-3 -yl) pyridinium chloride, 1-(2-propoxyethyl) 4 (S-methyl-1,2,4-oxadiazol- 3-yl)pyridinium bromide, 1-(2-ethoxymethyl) 4 (5- methyl-1,2,4-oxadiazol 3 yl)pyridinium iodide, 1-(2- propoxypropyl) 4 (S-methyl-1,2,4-oxadiazol-3-yl)- pyridinium chloride.
The quaternary compounds of the present invention show hypoglycemic activity which indicates they are use ful as medicaments in the lowering of blood sugar levels. When the quaternary compounds are administered orally to normal mice, a reduction of blood sugar levels is observed. The compounds of this invention are administered by gavage as saline solutions to CF1 mice (Carworth Farms, 18-25 grams (4-6 animals). Control animals receive an equivalent volume of saline. Food is withheld from animals after dosing. Blood glucose is determined on 0.05 ml. samples of blood by the method of Hotfman [1. Biol. Chem, 120, 51 (1937)] as adapted to the Technicon AutoAnalyzer and is expressed as percent change from predose values. The data are shown in the table hereinafter. These results show that the compounds of the present invention are useful in lowering the blood glucose concentrations of warm-blooded animals.
TABLE Decrease in blood glucose in normal mice after oral administration of 1,2,4-0xadiazolylpyridinium salts Compound--l (2 ethoxyethyl)-4-(5-methyl-l,2,4-oxadiazol-3-yl)pyridinium chloride:
Dose, mmoles/kg. 3.0 Hours after dosing 3 Percent decrease in blood glucose 27:4
The products of the present invention as hypoglycemic agents can be incorporated in various pharmaceutical forms such as tablets, capsules, pills and so forth, for immediate or sustained release, by combining with suitable carriers. They may be in the form of dosage units for a single therapeutic dose or in small units for multiple dosages or in larger units for division into single doses. Obviously, in addition to the therapeutic hypoglycemic compounds, there may be present excipients, binders, fillers and other therapeutically inert ingredients necessary in the formulation of the desired pharmaceutical preparation.
DETAILED DESCRIPTION The following examples describe in detail the preparation of representative quaternary lower alkoxy(lower) alkyl 1,2,4-oxadiazolylpyridinium salts of this invention.
EXAM PLE 1 Preparation of 4-(S-methyl-1,2,4-oxadiazol-3-yl)pyridine 'A mixture of 27 g. of isonicotinamidoxime and 50 ml. of acetic anhydride is warmed on a steam bath for 2 hours, and then heated under reflux for 3 hours. The solvent is distilled and the dark liquid residue is diluted with water. The crystals which form are collected, washed with water, and recrystallized from ethanol to provide colorless crystals, melting point 92-93 C.
EXAMPLE 2 Preparation of l-(2-ethoxyethyl)-4-(5-methyl-l,2,4-oxadiazol-3-yl)pyridinium chloride A mixture of 5.0 g. of 4-(S-methyl-1,2,4-oxadiazol-3- yl)pyridine and 15 ml. of 2-chloroethyl ethyl ether is heated in a bomb at C. for 20 hours. The excess 2-chloroethyl ether is evaporated and the black residue is recrystallized from isopropyl alcohol-ether to give offwhite crystals, melting point l87188 C.
EXAMPLE 3 Preparation of 4-(5-ethyl-l,2,4-oxadiazol-3-yl)pyridine A mixture of 27 g. of isonicotinamidoxime and 60 ml. of propionic anhydride is warmed on a steam bath for 2 hours and then heated at 145 C. for 4 hours. The solvent is distilled and the dark liquid residue is diluted with water. The crystals which form are collected, washed with water, and recrystallized from petroleum ether to provide colorless crystals, melting point 42-44" C.
EXAMPLE 4 Preparation of l-(3-propoxypropyl)-4-(5-ethyl-1,2,4-oxa diaZol-3-yl)pyridinium chloride A mixture of 5.0 g. of 4-(5-ethyl-l,2,4-oxadiazol-3-yl) pyridine and 15 ml. of 3-chloropropyl propyl ether is heated in a bomb at 130 C. for 20 hours. The excess 3- chloropropyl ether is evaporated and the residue is recrystallized to give the product of the example.
We claim:
1. A quaternary oxadiazolylpyridinium salt of the wherein R is lower alkyl, R is lower alkoxy(lower)alkyl, X is a pharmaceutically acceptable anion, Z is a trivalent radical selected from the group consisting of and References Cited FOREIGN PATENTS 875,887 8/l96l Great Britain 260296 ALAN L. ROTMAN, Primary Examiner US. Cl. X.R. 260999
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6813336A NL6813336A (en) | 1967-09-22 | 1968-09-18 | Process for preparing pyridine derivatives. |
| DE19681795369 DE1795369A1 (en) | 1967-09-22 | 1968-09-20 | New pyridinium salts and processes for their preparation |
| BE721158D BE721158A (en) | 1967-09-22 | 1968-09-20 | |
| FR166958A FR8478M (en) | 1967-09-22 | 1968-09-20 | New pyridine derivatives and their pyridinium salts, useful as muscle relaxants and antiepileptics. |
| FR166957A FR1598975A (en) | 1967-09-22 | 1968-09-20 | Process for the preparation of pyridinium salts. |
| CH1413168A CH521371A (en) | 1967-09-22 | 1968-09-20 | Process for the preparation of new cyclopropyl-1,2,4-oxadiazolylpyridines |
| US875526A US3555036A (en) | 1967-09-22 | 1969-11-10 | Cyclopropyl-1,2,4-oxadiazolylpyridines |
| US875527A US3551437A (en) | 1967-09-22 | 1969-11-10 | Certain 4-(1,2,4-oxadiazole-3 or 5-yl) pyridinium salts and derivatives thereof |
| US875525A US3551436A (en) | 1967-09-22 | 1969-11-10 | Certain 4-(thiazolyl) and 4-(oxazolyl) pyridinium salts |
| US127023A US3703577A (en) | 1967-09-22 | 1971-03-22 | 4-(thiazolyl) pyridinium salts and 4-(oxazolyl) pyridinium salts for lowering blood glucose levels |
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66970567A | 1967-09-22 | 1967-09-22 | |
| US67670667A | 1967-10-20 | 1967-10-20 | |
| US69038267A | 1967-12-14 | 1967-12-14 | |
| US875526A US3555036A (en) | 1967-09-22 | 1969-11-10 | Cyclopropyl-1,2,4-oxadiazolylpyridines |
| US875527A US3551437A (en) | 1967-09-22 | 1969-11-10 | Certain 4-(1,2,4-oxadiazole-3 or 5-yl) pyridinium salts and derivatives thereof |
| US875525A US3551436A (en) | 1967-09-22 | 1969-11-10 | Certain 4-(thiazolyl) and 4-(oxazolyl) pyridinium salts |
| US127023A US3703577A (en) | 1967-09-22 | 1971-03-22 | 4-(thiazolyl) pyridinium salts and 4-(oxazolyl) pyridinium salts for lowering blood glucose levels |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3551437A true US3551437A (en) | 1970-12-29 |
Family
ID=27568835
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US875525A Expired - Lifetime US3551436A (en) | 1967-09-22 | 1969-11-10 | Certain 4-(thiazolyl) and 4-(oxazolyl) pyridinium salts |
| US875526A Expired - Lifetime US3555036A (en) | 1967-09-22 | 1969-11-10 | Cyclopropyl-1,2,4-oxadiazolylpyridines |
| US875527A Expired - Lifetime US3551437A (en) | 1967-09-22 | 1969-11-10 | Certain 4-(1,2,4-oxadiazole-3 or 5-yl) pyridinium salts and derivatives thereof |
| US127023A Expired - Lifetime US3703577A (en) | 1967-09-22 | 1971-03-22 | 4-(thiazolyl) pyridinium salts and 4-(oxazolyl) pyridinium salts for lowering blood glucose levels |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US875525A Expired - Lifetime US3551436A (en) | 1967-09-22 | 1969-11-10 | Certain 4-(thiazolyl) and 4-(oxazolyl) pyridinium salts |
| US875526A Expired - Lifetime US3555036A (en) | 1967-09-22 | 1969-11-10 | Cyclopropyl-1,2,4-oxadiazolylpyridines |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US127023A Expired - Lifetime US3703577A (en) | 1967-09-22 | 1971-03-22 | 4-(thiazolyl) pyridinium salts and 4-(oxazolyl) pyridinium salts for lowering blood glucose levels |
Country Status (6)
| Country | Link |
|---|---|
| US (4) | US3551436A (en) |
| BE (1) | BE721158A (en) |
| CH (1) | CH521371A (en) |
| DE (1) | DE1795369A1 (en) |
| FR (2) | FR8478M (en) |
| NL (1) | NL6813336A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4571402A (en) * | 1982-06-22 | 1986-02-18 | Schering Corporation | Anti-bronchoconstriction 2-(4'-pyridinyl)-thiazole derivatives, composition, and method of use therefor |
| US20080108799A1 (en) * | 2004-09-02 | 2008-05-08 | Andre Weiss | Use Of Thiazolyl-Pyridinium Based Dyes In Optical Layers For Optical Data Recording |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3985754A (en) * | 1975-05-08 | 1976-10-12 | American Cyanamid Company | Para-fluorobenzoylpropyl-N-heterocyclic substituted quaternary salts |
| US4528291A (en) * | 1982-06-22 | 1985-07-09 | Schering Corporation | 2-(4'-Pyridinyl)-thiazole compounds and their use in increasing cardiac contractility |
| US4488647A (en) * | 1983-07-18 | 1984-12-18 | Paramount Packaging Corporation | Flexible package with easy opening peel seal |
-
1968
- 1968-09-18 NL NL6813336A patent/NL6813336A/en unknown
- 1968-09-20 CH CH1413168A patent/CH521371A/en not_active IP Right Cessation
- 1968-09-20 DE DE19681795369 patent/DE1795369A1/en active Pending
- 1968-09-20 FR FR166958A patent/FR8478M/en not_active Expired
- 1968-09-20 FR FR166957A patent/FR1598975A/en not_active Expired
- 1968-09-20 BE BE721158D patent/BE721158A/xx unknown
-
1969
- 1969-11-10 US US875525A patent/US3551436A/en not_active Expired - Lifetime
- 1969-11-10 US US875526A patent/US3555036A/en not_active Expired - Lifetime
- 1969-11-10 US US875527A patent/US3551437A/en not_active Expired - Lifetime
-
1971
- 1971-03-22 US US127023A patent/US3703577A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4571402A (en) * | 1982-06-22 | 1986-02-18 | Schering Corporation | Anti-bronchoconstriction 2-(4'-pyridinyl)-thiazole derivatives, composition, and method of use therefor |
| US20080108799A1 (en) * | 2004-09-02 | 2008-05-08 | Andre Weiss | Use Of Thiazolyl-Pyridinium Based Dyes In Optical Layers For Optical Data Recording |
| US7655767B2 (en) | 2004-09-02 | 2010-02-02 | Clariant Finance (Bvi) Limited | Use of thiazolyl-pyridinium based dyes in optical layers for optical data recording |
Also Published As
| Publication number | Publication date |
|---|---|
| BE721158A (en) | 1969-03-20 |
| US3551436A (en) | 1970-12-29 |
| US3555036A (en) | 1971-01-12 |
| FR8478M (en) | 1972-06-09 |
| CH521371A (en) | 1972-04-15 |
| FR1598975A (en) | 1970-07-15 |
| US3703577A (en) | 1972-11-21 |
| NL6813336A (en) | 1969-03-25 |
| DE1795369A1 (en) | 1972-01-05 |
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