IL96161A - Use of 1-Oxides of -N Methyl-2- (3-Pyridyl) -Tetrahydrotheopyran-2 for the preparation of medical products for the treatment of renal artery failure - Google Patents

Use of 1-Oxides of -N Methyl-2- (3-Pyridyl) -Tetrahydrotheopyran-2 for the preparation of medical products for the treatment of renal artery failure

Info

Publication number: IL96161A
Authority: IL; Israel
Prior art keywords: methyl; pyridyl; oxide; carbothioamide; preparation
Prior art date: 1989-10-31

Application number

IL9616190A

Other languages

English (en)

Hebrew (he)

Other versions

IL96161A0 (en

Original Assignee

Rhone Poulenc Sante

Priority date (The priority date 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 date listed.)

1989-10-31

Filing date

1990-10-29

Publication date

1996-12-05

1990-10-29 Application filed by Rhone Poulenc Sante filed Critical Rhone Poulenc Sante

1991-07-18 Publication of IL96161A0 publication Critical patent/IL96161A0/xx

1996-12-05 Publication of IL96161A publication Critical patent/IL96161A/en

Links

238000002360 preparation method Methods 0.000 title claims abstract description 11
206010052895 Coronary artery insufficiency Diseases 0.000 title claims abstract description 8
GKEMHVLBZNVZOI-MTATWXBHSA-N (2r)-n-methyl-1-oxo-2-pyridin-3-ylthiane-2-carbothioamide Chemical compound C=1C=CN=CC=1[C@@]1(C(=S)NC)CCCCS1=O GKEMHVLBZNVZOI-MTATWXBHSA-N 0.000 title claims description 9
229940126601 medicinal product Drugs 0.000 title description 7
239000000203 mixture Substances 0.000 claims abstract description 29
206010002383 Angina Pectoris Diseases 0.000 claims description 4
229940045200 cardioprotective agent Drugs 0.000 claims description 4
239000012659 cardioprotective agent Substances 0.000 claims description 4
238000002560 therapeutic procedure Methods 0.000 claims description 3
239000003814 drug Substances 0.000 abstract 1
GKEMHVLBZNVZOI-UHFFFAOYSA-N n-methyl-1-oxo-2-pyridin-3-ylthiane-2-carbothioamide Chemical compound C=1C=CN=CC=1C1(C(=S)NC)CCCCS1=O GKEMHVLBZNVZOI-UHFFFAOYSA-N 0.000 abstract 1
239000000047 product Substances 0.000 description 12
230000000694 effects Effects 0.000 description 11
230000010412 perfusion Effects 0.000 description 6
241000282472 Canis lupus familiaris Species 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
LGDSHSYDSCRFAB-UHFFFAOYSA-N Methyl isothiocyanate Chemical compound CN=C=S LGDSHSYDSCRFAB-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000003158 myorelaxant agent Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
-1 tetrahydrofuran Chemical compound 0.000 description 4
230000002792 vascular Effects 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
230000003276 anti-hypertensive effect Effects 0.000 description 3
230000004872 arterial blood pressure Effects 0.000 description 3
230000000747 cardiac effect Effects 0.000 description 3
230000004087 circulation Effects 0.000 description 3
239000003218 coronary vasodilator agent Substances 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
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 2
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 2
102000004257 Potassium Channel Human genes 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
LCKIEQZJEYYRIY-UHFFFAOYSA-N Titanium ion Chemical class [Ti+4] LCKIEQZJEYYRIY-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
239000008101 lactose Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
238000000034 method Methods 0.000 description 2
108020001213 potassium channel Proteins 0.000 description 2
239000003223 protective agent Substances 0.000 description 2
239000000523 sample Substances 0.000 description 2
239000008247 solid mixture Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
YBQVLKIMKZFEIM-UHFFFAOYSA-N 1-oxo-2-pyridin-3-ylthiane-2-carbothioamide Chemical compound C=1C=CN=CC=1C1(C(=S)N)CCCCS1=O YBQVLKIMKZFEIM-UHFFFAOYSA-N 0.000 description 1
FGRBYDKOBBBPOI-UHFFFAOYSA-N 10,10-dioxo-2-[4-(N-phenylanilino)phenyl]thioxanthen-9-one Chemical compound O=C1c2ccccc2S(=O)(=O)c2ccc(cc12)-c1ccc(cc1)N(c1ccccc1)c1ccccc1 FGRBYDKOBBBPOI-UHFFFAOYSA-N 0.000 description 1
DYTUAOUIQFNOIH-UHFFFAOYSA-N 2,3-diethyl-2,3-dihydroxybutanedioic acid Chemical compound CCC(O)(C(O)=O)C(O)(CC)C(O)=O DYTUAOUIQFNOIH-UHFFFAOYSA-N 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
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
241000892910 Aspergillus foetidus Species 0.000 description 1
241000700198 Cavia Species 0.000 description 1
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
241000233866 Fungi Species 0.000 description 1
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
208000009989 Posterior Leukoencephalopathy Syndrome Diseases 0.000 description 1
229920002472 Starch Polymers 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
229930006000 Sucrose Natural products 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
239000012190 activator Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
230000003257 anti-anginal effect Effects 0.000 description 1
229940124345 antianginal agent Drugs 0.000 description 1
210000002376 aorta thoracic Anatomy 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
210000004413 cardiac myocyte Anatomy 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000004040 coloring Methods 0.000 description 1
YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical group OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
210000003191 femoral vein Anatomy 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000000411 inducer Substances 0.000 description 1
229940102223 injectable solution Drugs 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
230000003601 intercostal effect Effects 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 1
CYEBJEDOHLIWNP-UHFFFAOYSA-N methanethioamide Chemical class NC=S CYEBJEDOHLIWNP-UHFFFAOYSA-N 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
SBWUJGPHNXIUAV-UHFFFAOYSA-N n-methyl-2-pyridin-3-ylthiane-2-carbothioamide Chemical compound C=1C=CN=CC=1C1(C(=S)NC)CCCCS1 SBWUJGPHNXIUAV-UHFFFAOYSA-N 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229960002275 pentobarbital sodium Drugs 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000001839 systemic circulation Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
SIYDRZWHWOOPRY-UHFFFAOYSA-N thiane-2-carbothioamide Chemical compound NC(=S)C1CCCCS1 SIYDRZWHWOOPRY-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
239000002966 varnish Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 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
- A61K31/38—Heterocyclic compounds 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Public Health (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Plural Heterocyclic Compounds (AREA)

IL9616190A 1989-10-31 1990-10-29 Use of 1-Oxides of -N Methyl-2- (3-Pyridyl) -Tetrahydrotheopyran-2 for the preparation of medical products for the treatment of renal artery failure IL96161A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR8914272A FR2653662B1 (fr)	1989-10-31	1989-10-31	Application du n-methyl (pyridyl-3)-2 tetrahydrothiopyranne-carbothioamide-2-oxyde-1 a la preparation de medicaments destines au traitement de l'insuffisance coronarienne.

Publications (2)

Publication Number	Publication Date
IL96161A0 IL96161A0 (en)	1991-07-18
IL96161A true IL96161A (en)	1996-12-05

Family

ID=9386962

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9616190A IL96161A (en)	1989-10-31	1990-10-29	Use of 1-Oxides of -N Methyl-2- (3-Pyridyl) -Tetrahydrotheopyran-2 for the preparation of medical products for the treatment of renal artery failure

Country Status (17)

Country	Link
US (1)	US5426117A (de)
EP (1)	EP0429324B1 (de)
JP (1)	JPH03153683A (de)
KR (1)	KR910007524A (de)
AT (1)	ATE135910T1 (de)
AU (1)	AU637419B2 (de)
CA (1)	CA2028986A1 (de)
DE (1)	DE69026204T2 (de)
DK (1)	DK0429324T3 (de)
ES (1)	ES2084679T3 (de)
FR (1)	FR2653662B1 (de)
GR (1)	GR3019441T3 (de)
HU (1)	HU212502B (de)
IE (1)	IE72476B1 (de)
IL (1)	IL96161A (de)
PT (1)	PT95757B (de)
ZA (1)	ZA908678B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR100373173B1 (ko) *	1996-11-18	2003-08-19	주식회사 코오롱	차광성 및 성형성이 우수한 폴리에틸렌테레프탈레이트 수지 조성물
KR102068928B1 (ko) *	2019-05-17	2020-01-21	민은홍	광고수단으로 전환사용이 가능한 레일 조명

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2528849B1 (fr) *	1982-06-17	1985-06-21	Rhone Poulenc Sante	Nouveaux derives de la thioformamide, leur preparation et les medicaments qui les contiennent
GB8800199D0 (en) *	1988-01-06	1988-02-10	Beecham Group Plc	Pharmaceutical preparation

1989
- 1989-10-31 FR FR8914272A patent/FR2653662B1/fr not_active Expired - Fee Related
1990
- 1990-10-29 AU AU65547/90A patent/AU637419B2/en not_active Ceased
- 1990-10-29 IL IL9616190A patent/IL96161A/en not_active IP Right Cessation
- 1990-10-30 ZA ZA908678A patent/ZA908678B/xx unknown
- 1990-10-30 CA CA002028986A patent/CA2028986A1/fr not_active Abandoned
- 1990-10-30 AT AT90403060T patent/ATE135910T1/de not_active IP Right Cessation
- 1990-10-30 DE DE69026204T patent/DE69026204T2/de not_active Expired - Fee Related
- 1990-10-30 ES ES90403060T patent/ES2084679T3/es not_active Expired - Lifetime
- 1990-10-30 IE IE390190A patent/IE72476B1/en not_active IP Right Cessation
- 1990-10-30 EP EP90403060A patent/EP0429324B1/de not_active Expired - Lifetime
- 1990-10-30 KR KR1019900017458A patent/KR910007524A/ko not_active Ceased
- 1990-10-30 HU HU906946A patent/HU212502B/hu not_active IP Right Cessation
- 1990-10-30 DK DK90403060.8T patent/DK0429324T3/da active
- 1990-10-31 PT PT95757A patent/PT95757B/pt not_active IP Right Cessation
- 1990-10-31 JP JP2292248A patent/JPH03153683A/ja active Pending
1993
- 1993-02-04 US US08/013,549 patent/US5426117A/en not_active Expired - Fee Related
1996
- 1996-03-28 GR GR950403074T patent/GR3019441T3/el unknown

Also Published As

Publication number	Publication date
IL96161A0 (en)	1991-07-18
ATE135910T1 (de)	1996-04-15
JPH03153683A (ja)	1991-07-01
ES2084679T3 (es)	1996-05-16
ZA908678B (en)	1991-08-28
EP0429324A2 (de)	1991-05-29
FR2653662A1 (fr)	1991-05-03
AU6554790A (en)	1991-05-09
IE72476B1 (en)	1997-04-23
HU906946D0 (en)	1991-05-28
IE903901A1 (en)	1991-05-08
HUT59312A (en)	1992-05-28
PT95757A (pt)	1991-09-13
CA2028986A1 (fr)	1991-05-01
PT95757B (pt)	1997-09-30
EP0429324B1 (de)	1996-03-27
FR2653662B1 (fr)	1994-05-13
DE69026204T2 (de)	1996-09-05
US5426117A (en)	1995-06-20
EP0429324A3 (en)	1992-05-27
GR3019441T3 (en)	1996-06-30
HU212502B (en)	1996-07-29
AU637419B2 (en)	1993-05-27
KR910007524A (ko)	1991-05-30
DE69026204D1 (de)	1996-05-02
DK0429324T3 (da)	1996-04-29

Legal Events

Date	Code	Title	Description
2001-06-14	RH	Patent void

Publication	Publication Date	Title
KR100386229B1 (ko)	2003-08-21	히드록시카르바졸화합물의평활근유주및증식의억제
EP0622076B1 (de)	1997-04-02	Restenosehemmer nach perkutaner koronarer arterioplastie
KR0148645B1 (ko)	1998-11-02	심장 보호제
WO1988005044A1 (en)	1988-07-14	Nitroxide compounds for the preparation of a pharmaceutical composition intended for the prophylaxis and treatment of ischemic cell damage
SK287533B6 (sk)	2011-01-04	Liečivo na liečenie viacpočetných rezistentných nádorov alebo na inhibíciu angiogenézy a metastáz
JP4306825B2 (ja)	2009-08-05	インスリン抵抗性が関与する血管機能異常を伴う疾患の予防または治療剤
EP0682947A1 (de)	1995-11-22	Arzneimittel zur therapeutischen und prophylaktischen Behandlung von Krankheiten, die durch Hyperplasie der glatten Muskelzellen bedingt sind
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