WO1996025933A2 - Use of vinyl carboxylic acid compounds for the treatment or prevention of transient ischaemic attacks - Google Patents
Use of vinyl carboxylic acid compounds for the treatment or prevention of transient ischaemic attacks Download PDFInfo
- Publication number
- WO1996025933A2 WO1996025933A2 PCT/JP1996/000394 JP9600394W WO9625933A2 WO 1996025933 A2 WO1996025933 A2 WO 1996025933A2 JP 9600394 W JP9600394 W JP 9600394W WO 9625933 A2 WO9625933 A2 WO 9625933A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- group
- formula
- compound
- pyridyl
- hydrogen atom
- Prior art date
Links
- 0 [*-]=C(c1ccccc1)c1cccnc1 Chemical compound [*-]=C(c1ccccc1)c1cccnc1 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
-
- 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
- A61K31/4406—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 3, e.g. zimeldine
-
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/443—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
-
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
-
- 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
- A61K31/47—Quinolines; Isoquinolines
Definitions
- the present invention relates to a pharmaceutical composition for treating or preventing a transient ischemic attack exhibiting therapeutic and prophylactic activities against transient ischemic attack (TIA).
- TIA transient ischemic attack
- TIA a symptom that precedes cerebral stroke and disappears in short time, is positioned as a prodromal or alerting attack in ischemic cerebral disease. It is
- TIA a severe cerebrovascular disorder, such as cerebral infarction
- a severe cerebrovascular disorder such as cerebral infarction
- TIA is an attack characterized by short-term onset of local cerebral dysfunction attributable to ischemia. It
- TIA 25 is normally confined to a single vascular system (left or right common carotid arterial system, or vertebral vasilar system), involving no other causes. It is common practice to define TIA as an attack that lasts for no longer than 24 hours. The longer the attack, the more often cerebral
- CT computed tomography
- MRI magnetic resonance imaging
- TIA does not leave permanent nerve lesions, there are often relapses. As well, there are atypical cases to which the above definition does not apply.
- TIA associated with the internal carotid arterial system is characterized by one or more symptoms of motor disorder, loss of vision, sensory disturbance and aphasia. Symptoms of TIA associated with the vertebral vasilar system also include nerve symptoms such as motor disorder, eye symptoms and vertigo, which develop singly or in combination.
- EP-B-98690 describes that the compound of the formula (I) below and salts thereof possess thromboxane synthetase-inhibiting activity.
- TIA cerebral vasospasm, microembolization, cerebrovascular failure and other factors have been proposed as causative, the latter two being viewed as likely.
- anticoagulation, antiplatelet and other therapies have been attempted, with some effect.
- Drugs used in such therapies include aspirin and ticlopidine; however, there is demand for a more effective drug that is clinically tolerable, with less severe adverse effects, in chronic administra ⁇ tion.
- the present inventors sought a compound that treats TIA, and clinically confirmed, for the first time, that a compound known as a thromboxane synthetase inhibitor is effective against TIA.
- the inventors investigated further based on this finding, and developed the present invention.
- the present invention relates to (1) a pharmaceutical composition for treating a transient ischemic attack (TIA) which comprises a compound of the formula:
- Ri is a pyridyl group
- R 2 is a phenyl, thienyl, furyl, naphthyl, benzothienyl or pyridyl group, which may be substituted with a lower alkoxy group, a lower alkyl group, a halogen atom, trifluoromethyl group, a lower alkenyl group or/and methylenedioxy group
- R3 is hydrogen atom or a lower alkyl group, and is an integer of 0 to 6
- Y is sulfur atom, methylene group or a group of the formula:
- R* is hydrogen atom or acetyl group, and m is 0 or 1, or a pharmaceutically acceptable salt,
- n is an integer of 2 to 6, or a pharmaceutically acceptable salt
- R 1 represents a pyridyl group
- R 2 represents a phenyl, thienyl, furyl, naphthyl, benzothienyl or pyridyl group, which may be substituted with a lower alkoxy group, a lower alkyl group, a halogen atom, trifluoromethyl group, a lower alkenyl group or/and methylenedioxy group.
- the pyridyl group of R 1 or R 2 is exemplified by 2-pyridyl, 3-pyridyl and 4-pyridyl
- the thienyl, furyl, naphthyl and benzothienyl are exemplified by 2-thienyl and 3-thienyl; 2-furyl and 3- furyl; ⁇ -naphthyl and /3-naphthyl; 2-benzothienyl, 3- benzothienyl, 4-benzothienyl, 5-benzothienyl, 6- benzothienyl and 7-benzothienyl.
- the phenyl, Q thienyl, furyl, naphthyl, benzothienyl or pyridyl of R 2 optionally has 1 to 5 of these substituents at any substituable positions of the ring.
- Ri includes 3-pyridyl.
- R 2 includes phenyl. 5
- R3 represents hydrogen atom or a lower alkyl group.
- R 3 in the above formula (I) mention is made of C 1 - alkyl groups of such as methyl, ethyl, n-propyl, i-propyl, n-butyl, i- butyl, s-butyl, t-butyl, etc.
- R 3 0 includes hydrogen atom.
- Y represents sulfur atom, methylene group or a group of the formula:
- R* is hydrogen atom or acetyl group, and m is 0 or 1.
- R4 represents hydrogen atom or acetyl group, and m represents 0 or 1.
- Y includes methylene group.
- e include an integer of 0 to 4, 2 is more preferably.
- Preferable examples of the compound of the formula (I) include a compound, wherein Ri is 3-pyridyl, R 2 is phenyl, R3 is hydrogen atom, Y is methylene group and € is an
- n represents an integer 2 to 6.
- Preferable example of the compound of the formula (II) include a compound, wherein n is 4.
- the pharmacologically acceptable salt of a compound of the formula (I) is exemplified by salts with mineral acids such as hydrochloric acid, sulfuric acid and phosphoric acid, salts with organic acids such as methanesulfonic acid, benzenesulfonic acid, malic acid, citric acid and
- succinic acid salts with alkali metals such as sodium and potassium, salts with alkaline earth metals such as calcium and magnesium, and salts with basic amino acids such as arginine.
- alkali metals such as sodium and potassium
- alkaline earth metals such as calcium and magnesium
- salts with basic amino acids such as arginine.
- the present composition comprising a compound of the formula (I) or a pharmacologically acceptable salt thereof has not significantly toxic to various animal species and very safe to humans. Therefore, the present composition is useful for treating or preventing TIA.
- a compound of the formula (I) or a pharmacologically acceptable salt thereof can be prepared as it is or together with pharmaceutically acceptable carriers and/or additives into preparations in dosage form such as tablets,
- the present composition comprising a compound of the formula (I) or a pharmacologically acceptable salt thereof is administered normally at 20-200 mg/day, preferably 20-150 mg/day as a 2 Q compound of the formula (I) or a pharmacologically acceptable salt thereof per adult (weighting 50-70 kg) for oral administration, dividing 1 to 4 times, for treating TIA, depending on symptoms, route of administration etc.
- the content of a compound of the formula (I) or a 2c pharmacologically salt thereof in the pharmaceutical preparation of the present invention ranges usually from 0.1 to 100 weight %, preferably from 1 to 50 weight %, relative to the whole weight of the pharmaceutical preparation.
- the carriers which the present pharmaceutical preparations include adequately is selected from excipients (e.g.
- binders e.g. dextrin, gum (e.g. arabic gum), alcoholated starch, gelatin, hydroxypropyl cellulose. hydroxypropyl methyl cellulose and pullulane
- disintegrants e.g. carboxymethyl cellulose calcium, closcarmellose sodium, clospovidone, low-substituted hydroxypropyl cellulose and partial o-starch
- lubricants e.g.
- magnesium stearate e.g., calcium stearate, talc, starch and sodium benzoate
- colorants e.g. tar pigment, caramel, iron sesquioxide, titanium oxide and riboflavins
- flavoring agents e.g. sweeteners and perfume
- stabilizers e.g. sodium sulfite
- preservatives e.g. parabens and
- sustained-release preparations can be produced by coating tablets, granules, fine granules or capsules with, for examples, oil and fat (e.g. triglyceride), ester of fatty acid of polyglycerine or hydroxypropyl cellulose, by per se
- oil and fat e.g. triglyceride
- ester of fatty acid of polyglycerine or hydroxypropyl cellulose by per se
- the carriers for injectable preparations use is made of, for examples, distilled water, physiological saline solution, glucose solution, an agent of infusion, sodium chloride and sodium hydroxide.
- the present composition comprising a compound of the
- blood flow-improving agents cerebral metabolism-improving agents, hypertension remedies, diabetes mellitus remedies, anti-cerebral edema agents, thrombolytic agents, lipid metabolism-improving agents and radical scavengers.
- Q cerebral circulation and blood flow-improving agents include Calan (trade name) (common name: vinpocetine) ; cerebral metabolism-improving agents including Avan (trade name) (common name: idebenone); hypertension remedies including Adecut (trade name) (common name: delapril
- Calslot (trade name) (common name: manidipine hydrochloride) and Candesartan cilexetil
- diabetes mellitus remedies including Basen (trade name) (common name: Voglibose) and sulfonyl urea agent
- anti- cerebral edema agents including glycerol
- thrombolytic agents including tissue plasminogen activator and prourokinase
- lipid metabolism-improving agents including Mevalotin (trade name) (common name: pravastatin sodium) and Amotril (trade name) (common name: clofibrate); and radical scavengers including vitamins E and C.
- Example 1 The present invention is hereinafter described in more detail by means of the following example.
- Example 1 The present invention is hereinafter described in more detail by means of the following example.
- Example 1 The tablet obtained in Example 1 was coated to give sugar coated tablet.
- Subjects and total number The subjects of this study were patients who developed one or more TIA attacks associated with the internal carotid arterial system (NIH Diagnostic Criteria, 1990) during the 3-month period before initial administration (171 for efficacy and utility, 175 for safety) .
- Investigational drug and method of administration Tablets each containing 50 mg or 100 mg of the subject compound obtained in Example 1 were orally administered after breakfast once daily for 18 months. The study was conducted in double blind fashion. Contraindicated concomitant drugs: Concomitant use of ticlopidine, aspirin preparations, heparin, warfarin and ozagrel was prohibited. If in use, they were discontinued.
- CT or MRI
- CT (or MRI) examination was 5 conducted before and after administration, in as similar a fashion as possible.
- cerebral angiography was performed to assess the affected blood vessel ⁇ Q before study initiation.
- ECG was performed before initial administration and at 18 months of administration.
- TIA internal carotid arterial system, vertebral vasilar system
- Duration @ Syndromes Sensory disturbance (numbness, anesthesia), motor disorder (site), 25 vision disorder (description), speech disorder (aphagia, alalia), others
- ⁇ Condition Diurnal activity, just after at attack wakening, at rest, at sleep, others
- Cerebral vascular Cerebral infarction disorder (severity: mild, moderate and higher)
- Mild was defined as a state of disease in which the syndrome lasts for not less than 24 hours and not more than 3 weeks. Cerebral hemorrhage, subarachnoid hemorrhage
- Hematology and liver function also were tested at 2 weeks, 1 month, 2 months, 9 months and 15 months of administration.
- Hematology Red blood cell count, hemoglobin content, hematocrit value, white blood cell count, platelet count, differential white blood cell count
- Blood bio- (Liver function) chemistry Total protein, GOT, GPT, y-GTP, Al-P, LDH CK, total cholesterol, HDL-choles- terol, triglyceride (at hunger), BUN, creatinine, fasted blood glucose
- ⁇ rinalysis Protein, sugar, urobilinogen, occult blood If an abnormal change (worsened from pre- administration value) is noted during the thera ⁇ Commissionic period, follow-up survey was performed to determine relation to the test drug. 8) Overall assessment
- the attack frequency at time of rating (during therapeutic period) 1 year and 18 months after 0 initial administration served as an efficacy rating index.
- rating at 6 months of adminis ⁇ tration and rating at less than 1 year due to discontinuation (adverse reactions etc.) was in regard to duration of administration
- the utility rates of the test compound in the 50 mg and 100 mg dose groups were 60.0 and 60.5%, respectively
- test compound is a useful drug for TIA patients.
- Drug Mo Slightly erably Very Inde ⁇ Number (dose/day) Problem Prob ⁇ termi ⁇ of lematic Prob ⁇ Prob ⁇ lematic lematic nable Patients
- Test compound 60.0 5.9 23.5 5.9 4.7 85 (50 mg)
- a compound of the formula (I) or a pharmacologically acceptable salt thereof treats or prevents transient ischemic attack.
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP96903205A EP0810862A2 (en) | 1995-02-22 | 1996-02-21 | Use of vinyl carboxylic acid compounds for the treatment or prevention of transient ischaemic attacks |
AU47309/96A AU4730996A (en) | 1995-02-22 | 1996-02-21 | Use of vinyl carboxylic acid compounds for the treatment or prevention of transient ischaemic attacks |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP7/33960 | 1995-02-22 | ||
JP3396095 | 1995-02-22 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US66931696A A-371-Of-International | 1995-02-22 | 1996-07-09 | |
US09/769,440 Continuation US20010003751A1 (en) | 1995-02-22 | 2001-01-26 | Pharmaceutical composition for treating transient ischemic attack |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1996025933A2 true WO1996025933A2 (en) | 1996-08-29 |
WO1996025933A3 WO1996025933A3 (en) | 1996-10-17 |
Family
ID=12401068
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1996/000394 WO1996025933A2 (en) | 1995-02-22 | 1996-02-21 | Use of vinyl carboxylic acid compounds for the treatment or prevention of transient ischaemic attacks |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0810862A2 (en) |
AU (1) | AU4730996A (en) |
CA (1) | CA2213507A1 (en) |
WO (1) | WO1996025933A2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003024457A1 (en) * | 2001-09-11 | 2003-03-27 | Asahi Kasei Kabushiki Kaisha | Medicinal composition for prevention of or treatment for cerebrovascular disorder and cardiopathy |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0098690A2 (en) * | 1982-06-14 | 1984-01-18 | Takeda Chemical Industries, Ltd. | Vinyl carboxylic acid derivatives, their production and use |
-
1996
- 1996-02-21 WO PCT/JP1996/000394 patent/WO1996025933A2/en not_active Application Discontinuation
- 1996-02-21 AU AU47309/96A patent/AU4730996A/en not_active Abandoned
- 1996-02-21 CA CA 2213507 patent/CA2213507A1/en not_active Abandoned
- 1996-02-21 EP EP96903205A patent/EP0810862A2/en not_active Withdrawn
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0098690A2 (en) * | 1982-06-14 | 1984-01-18 | Takeda Chemical Industries, Ltd. | Vinyl carboxylic acid derivatives, their production and use |
Non-Patent Citations (6)
Title |
---|
AMERICAN HEART JOURNAL, vol. 116, no. 6 pt. 1, December 1988, pages 1482-1487, XP000579143 AL-WATHIQUI, M. ET AL: "Cyclical carotid artery flow reduction in conscious dogs: Effect of a new thromboxane receptor antagonist" * |
DATABASE BIOSIS BIOSCIENCES INFORMATION SERVICE, PHILADELPHIA, PA, US OKAMOTO S ET AL: "TREATMENT OF OCCLUSIVE CEREBROVASCULAR DISEASE WITH A SELECTIVE THROMBOXANE A-2 SYNTHETASE INHIBITOR" XP002010663 & ARCH JPN CHIR, 55 (1). 1986. 251-259., * |
DATABASE EMBASE ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL IMURA Y. ET AL: "Protective effect of CV-4151 (isbogrel) on arachidonic acid-induced transient cerebral ischemia in dogs" XP002010662 & JAPANESE PHARMACOLOGY AND THERAPEUTICS, 1995, 23/4 (45-52), JAPAN, * |
DATABASE EMBASE ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL KATAYAMA Y. ET AL: "Protective effect of thromboxane Asub 2 synthetase inhibitor (trapidil) on acutely-induced cerebral ischemia" XP002010664 & BRAIN NERVE, 1986, 38/10 (925-931), JAPAN, * |
JAPANESE JOURNAL OF PHARMACOLOGY, vol. 65, no. 1, May 1994, page 45-50 XP000578984 SATOH, H. ET AL: "Protective effects of KW-3635, a thromboxane A2 antagonist on arachadonic acid-induced transient cerebral ischemia in dogs" * |
THROMB RES, MAY 1 1993, 70 (3) P233-44, UNITED STATES, XP000579091 FUJIMURA M ET AL: "Effect of Y-20811, a thromboxane synthetase inhibitor, on photochemically induced cerebral embolism in rabbits." * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003024457A1 (en) * | 2001-09-11 | 2003-03-27 | Asahi Kasei Kabushiki Kaisha | Medicinal composition for prevention of or treatment for cerebrovascular disorder and cardiopathy |
Also Published As
Publication number | Publication date |
---|---|
AU4730996A (en) | 1996-09-11 |
CA2213507A1 (en) | 1996-08-29 |
WO1996025933A3 (en) | 1996-10-17 |
EP0810862A2 (en) | 1997-12-10 |
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