IL97714A - Inclusion complexes of N-ethoxycarbonyl-3-morphonilo-Sidnonamine or salts formed with the history of cyclodextrin, their preparation and pharmaceutical preparations - Google Patents

Inclusion complexes of N-ethoxycarbonyl-3-morphonilo-Sidnonamine or salts formed with the history of cyclodextrin, their preparation and pharmaceutical preparations

Info

Publication number: IL97714A
Authority: IL; Israel
Prior art keywords: cyclodextrin; ethoxycarbonyl; morpholino; molsidomin; sydnonimine
Prior art date: 1990-03-28

Application number

IL9771491A

Other languages

English (en)

Hebrew (he)

Other versions

IL97714A0 (en

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

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.)

1990-03-28

Filing date

1991-03-28

Publication date

1995-03-30

1990-06-27 Priority claimed from HU904013A external-priority patent/HUT59399A/hu

1991-03-28 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1992-06-21 Publication of IL97714A0 publication Critical patent/IL97714A0/xx

1995-03-30 Publication of IL97714A publication Critical patent/IL97714A/en

Links

150000003839 salts Chemical class 0.000 title claims abstract description 17
238000002360 preparation method Methods 0.000 title claims description 15
239000008194 pharmaceutical composition Substances 0.000 title claims description 10
XLFWDASMENKTKL-UHFFFAOYSA-N molsidomine Chemical compound O1C(N=C([O-])OCC)=C[N+](N2CCOCC2)=N1 XLFWDASMENKTKL-UHFFFAOYSA-N 0.000 claims abstract description 72
229920000858 Cyclodextrin Polymers 0.000 claims abstract description 32
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 12
239000001116 FEMA 4028 Substances 0.000 claims abstract 4
229960004853 betadex Drugs 0.000 claims abstract 4
235000011175 beta-cyclodextrine Nutrition 0.000 claims abstract 3
239000004480 active ingredient Substances 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
238000000034 method Methods 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
238000004108 freeze drying Methods 0.000 claims description 6
235000019441 ethanol Nutrition 0.000 claims description 4
239000003094 microcapsule Substances 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
208000005156 Dehydration Diseases 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
238000010316 high energy milling Methods 0.000 claims description 2
238000001694 spray drying Methods 0.000 claims description 2
238000001291 vacuum drying Methods 0.000 claims description 2
238000007865 diluting Methods 0.000 claims 2
239000000463 material Substances 0.000 claims 2
ODLHGICHYURWBS-FOSILIAISA-N molport-023-220-444 Chemical compound CC(O)COC[C@@H]([C@@H]([C@H]([C@@H]1O)O)O[C@@H]2O[C@H]([C@H](O[C@@H]3O[C@@H](COCC(C)O)[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3O[C@@H](COCC(C)O)[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3O[C@@H](COCC(C)O)[C@@H]([C@H]([C@@H]3O)O)O[C@@H]3O[C@@H](COCC(C)O)[C@@H]([C@H]([C@@H]3O)O)O3)[C@@H](O)[C@@H]2O)COCC(O)C)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O)[C@H]3O[C@H]1COCC(C)O ODLHGICHYURWBS-FOSILIAISA-N 0.000 claims 2
229960004027 molsidomine Drugs 0.000 abstract description 55
206010002383 Angina Pectoris Diseases 0.000 abstract description 3
239000003795 chemical substances by application Substances 0.000 abstract description 3
230000002253 anti-ischaemic effect Effects 0.000 abstract description 2
230000002265 prevention Effects 0.000 abstract description 2
208000010110 spontaneous platelet aggregation Diseases 0.000 abstract description 2
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 abstract 2
230000003288 anthiarrhythmic effect Effects 0.000 abstract 1
239000003416 antiarrhythmic agent Substances 0.000 abstract 1
239000003527 fibrinolytic agent Substances 0.000 abstract 1
230000003480 fibrinolytic effect Effects 0.000 abstract 1
GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 abstract 1
229940080345 gamma-cyclodextrin Drugs 0.000 abstract 1
230000001077 hypotensive effect Effects 0.000 abstract 1
230000002401 inhibitory effect Effects 0.000 abstract 1
ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 abstract 1
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 22
239000003826 tablet Substances 0.000 description 18
239000000243 solution Substances 0.000 description 15
235000019359 magnesium stearate Nutrition 0.000 description 11
239000000203 mixture Substances 0.000 description 10
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 9
229920002261 Corn starch Polymers 0.000 description 7
235000019759 Maize starch Nutrition 0.000 description 7
239000012528 membrane Substances 0.000 description 7
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 6
210000004027 cell Anatomy 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
239000003814 drug Substances 0.000 description 5
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238000009472 formulation Methods 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
229930006000 Sucrose Natural products 0.000 description 4
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 4
235000013681 dietary sucrose Nutrition 0.000 description 4
238000001938 differential scanning calorimetry curve Methods 0.000 description 4
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238000004898 kneading Methods 0.000 description 4
239000008101 lactose Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000002674 ointment Substances 0.000 description 4
229920000642 polymer Polymers 0.000 description 4
239000000126 substance Substances 0.000 description 4
229960004793 sucrose Drugs 0.000 description 4
238000013268 sustained release Methods 0.000 description 4
239000012730 sustained-release form Substances 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
238000012360 testing method Methods 0.000 description 4
239000001856 Ethyl cellulose Substances 0.000 description 3
ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 3
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
230000037396 body weight Effects 0.000 description 3
238000010668 complexation reaction Methods 0.000 description 3
229940097362 cyclodextrins Drugs 0.000 description 3
230000003247 decreasing effect Effects 0.000 description 3
238000007907 direct compression Methods 0.000 description 3
229940079593 drug Drugs 0.000 description 3
229920001249 ethyl cellulose Polymers 0.000 description 3
235000019325 ethyl cellulose Nutrition 0.000 description 3
230000036470 plasma concentration Effects 0.000 description 3
229960004063 propylene glycol Drugs 0.000 description 3
235000013772 propylene glycol Nutrition 0.000 description 3
210000003370 receptor cell Anatomy 0.000 description 3
210000003491 skin Anatomy 0.000 description 3
238000002798 spectrophotometry method Methods 0.000 description 3
238000003756 stirring Methods 0.000 description 3
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
239000005642 Oleic acid Substances 0.000 description 2
238000002441 X-ray diffraction Methods 0.000 description 2
239000008186 active pharmaceutical agent Substances 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000011248 coating agent Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
230000009918 complex formation Effects 0.000 description 2
238000013270 controlled release Methods 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
230000003993 interaction Effects 0.000 description 2
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
230000002045 lasting effect Effects 0.000 description 2
239000000320 mechanical mixture Substances 0.000 description 2
239000004570 mortar (masonry) Substances 0.000 description 2
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
-1 oxycarbonyl-3-morpholino-sydnonimine Chemical class 0.000 description 2
239000008188 pellet Substances 0.000 description 2
229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
239000011148 porous material Substances 0.000 description 2
210000000434 stratum corneum Anatomy 0.000 description 2
239000000725 suspension Substances 0.000 description 2
GUBGYTABKSRVRQ-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol Chemical compound OCC1OC(OC2C(O)C(O)C(O)OC2CO)C(O)C(O)C1O GUBGYTABKSRVRQ-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
229920000298 Cellophane Polymers 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
229920003164 Eudragit® NE 40 D Polymers 0.000 description 1
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 1
206010019233 Headaches Diseases 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
241000897276 Termes Species 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000003257 anti-anginal effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
230000004888 barrier function Effects 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000036765 blood level Effects 0.000 description 1
210000001772 blood platelet Anatomy 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
JUNWLZAGQLJVLR-UHFFFAOYSA-J calcium diphosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])(=O)OP([O-])([O-])=O JUNWLZAGQLJVLR-UHFFFAOYSA-J 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
239000004203 carnauba wax Substances 0.000 description 1
235000013869 carnauba wax Nutrition 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
235000013339 cereals Nutrition 0.000 description 1
230000008859 change Effects 0.000 description 1
238000002144 chemical decomposition reaction Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000010586 diagram Methods 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
235000019821 dicalcium diphosphate Nutrition 0.000 description 1
229910000393 dicalcium diphosphate Inorganic materials 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
239000006196 drop Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000020764 fibrinolysis Effects 0.000 description 1
238000005243 fluidization Methods 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
229960003943 hypromellose Drugs 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
230000001795 light effect Effects 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
229940082615 organic nitrates used in cardiac disease Drugs 0.000 description 1
230000035515 penetration Effects 0.000 description 1
230000035699 permeability Effects 0.000 description 1
239000012466 permeate Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
239000006069 physical mixture Substances 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000011241 protective layer Substances 0.000 description 1
238000009790 rate-determining step (RDS) Methods 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
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238000002525 ultrasonication Methods 0.000 description 1
238000000870 ultraviolet spectroscopy Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/04—1,2,3-Oxadiazoles; Hydrogenated 1,2,3-oxadiazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Polymers & Plastics (AREA)
Biochemistry (AREA)
Veterinary Medicine (AREA)
Molecular Biology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Materials Engineering (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

IL9771491A 1990-03-28 1991-03-28 Inclusion complexes of N-ethoxycarbonyl-3-morphonilo-Sidnonamine or salts formed with the history of cyclodextrin, their preparation and pharmaceutical preparations IL97714A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU901868A HU210921B (en)	1990-03-28	1990-03-28	Process for preparing inclusion complexes of n-ethoxycarbonyl-3-morpholino-sydnonimine formed with cyclodextrines and pharmaceutical compositions containing them
HU904013A HUT59399A (en)	1989-11-30	1990-06-27	Process for producing substituted 3-aminosydnone imine derivatives and pharmaceutical compositions comprising same

Publications (2)

Publication Number	Publication Date
IL97714A0 IL97714A0 (en)	1992-06-21
IL97714A true IL97714A (en)	1995-03-30

Family

ID=10956592

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9771491A IL97714A (en)	1990-03-28	1991-03-28	Inclusion complexes of N-ethoxycarbonyl-3-morphonilo-Sidnonamine or salts formed with the history of cyclodextrin, their preparation and pharmaceutical preparations

Country Status (34)

Country	Link
US (1)	US5403840A (da)
EP (1)	EP0477315B1 (da)
JP (1)	JP2582497B2 (da)
KR (1)	KR950004705B1 (da)
CN (1)	CN1051080C (da)
AT (1)	ATE138656T1 (da)
AU (1)	AU638824B2 (da)
BG (1)	BG61689B1 (da)
BR (1)	BR9105136A (da)
CA (1)	CA2054188C (da)
CZ (1)	CZ287353B6 (da)
DE (1)	DE69119853T2 (da)
DK (1)	DK0477315T3 (da)
ES (1)	ES2090320T3 (da)
FI (1)	FI102460B1 (da)
GE (1)	GEP19991832B (da)
GR (1)	GR3020684T3 (da)
HR (1)	HRP920561B1 (da)
HU (1)	HU210921B (da)
IL (1)	IL97714A (da)
LT (1)	LT3394B (da)
LV (1)	LV10245B (da)
MC (1)	MC2185A1 (da)
MD (1)	MD679G2 (da)
NO (1)	NO179611C (da)
OA (1)	OA10029A (da)
PL (1)	PL165868B1 (da)
RO (1)	RO109649B1 (da)
RU (1)	RU2111216C1 (da)
SI (1)	SI9110908A (da)
SK (1)	SK279891B6 (da)
TJ (1)	TJ231R3 (da)
UA (1)	UA27226C2 (da)
WO (1)	WO1991014680A1 (da)

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ZA949182B (en) *	1993-12-02	1995-07-26	South African Druggists Ltd	Pharmaceutical composition
GB2290964A (en) *	1994-07-08	1996-01-17	Arto Olavi Urtti	Transdermal drug delivery system
US6046177A (en) *	1997-05-05	2000-04-04	Cydex, Inc.	Sulfoalkyl ether cyclodextrin based controlled release solid pharmaceutical formulations
GB9915231D0 (en)	1999-06-29	1999-09-01	Pfizer Ltd	Pharmaceutical complex
FR2805462B1 (fr) *	2000-02-24	2003-08-15	Therabel Res	Nouvelle forme galenique orale a liberation prolongee de la molsidomine
ITTO20120056A1 (it) *	2012-01-24	2013-07-25	Borla Ind	Connettore per linee medicali di infusione, trasfusione e simili
ITTO20130433A1 (it) *	2013-05-29	2014-11-30	Borla Ind	Connettore per linee medicali
BE1028879B1 (fr)	2020-12-11	2022-07-12	Europharmaceuticals	Comprimé à libération prolongée de la molsidomine

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DE1695897C3 (de) *	1966-07-04	1979-02-15	Takeda Chemical Industries Ltd	N-Acyl-sydnonimine, deren Salze, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE3221425A1 (de) *	1982-06-07	1983-12-08	Boehringer Ingelheim KG, 6507 Ingelheim	Hydrolyseempfindlichen wirkstoff enthaltende, lagerstabile tablette
DK243084A (da) *	1983-05-26	1984-11-27	Takeda Chemical Industries Ltd	Perkutane farmaceutiske praeparater til udvortes brug
DE3346614A1 (de) *	1983-12-23	1985-07-04	Anton Hummel Gmbh Metallwarenfabrik, 7808 Waldkirch	Entlueftungsventil insbesondere zum entlueften von heizsystemen
GB8506792D0 (en) *	1985-03-15	1985-04-17	Janssen Pharmaceutica Nv	Derivatives of y-cyclodextrin
DE3522191A1 (de) *	1985-06-21	1987-01-15	Cassella Ag	Photostabilisierung von sydnoniminen
GB8613688D0 (en) *	1986-06-05	1986-07-09	Euro Celtique Sa	Pharmaceutical composition
JPH0819004B2 (ja) *	1986-12-26	1996-02-28	日清製粉株式会社	徐放性医薬製剤
IT1204725B (it) *	1987-06-17	1989-03-10	Edmond Pharma Srl	Complessi di inclusione del dipiridamolo con ciclodestrine
DE68901043D1 (de) *	1988-01-14	1992-04-30	Akzo Nv	Waessriges pharmazeutisches praeparat.
US5120732A (en) *	1988-06-14	1992-06-09	Cassella Aktiengesellschaft	Substituted 3-aminosyndone imines, a process for their preparation and their use
IT1227626B (it) *	1988-11-28	1991-04-23	Vectorpharma Int	Farmaci supportati aventi velocita' di dissoluzione aumentata e procedimento per la loro preparazione
SE8904296D0 (sv) *	1989-12-21	1989-12-21	Pharmacia Ab	Transdermal system
HU212730B (en) *	1990-03-28	1996-10-28	Chinoin Gyogyszer Es Vegyeszet	Process for producing inclusion complexes of cyclodextrine or its derivative and 3-morpholino-sydnonimine or its salt or its tautomer and pharmaceutical compositions containing them

1990
- 1990-03-28 HU HU901868A patent/HU210921B/hu unknown
1991
- 1991-03-28 CA CA002054188A patent/CA2054188C/en not_active Expired - Lifetime
- 1991-03-28 ES ES91906726T patent/ES2090320T3/es not_active Expired - Lifetime
- 1991-03-28 SI SI9110908A patent/SI9110908A/sl unknown
- 1991-03-28 RO RO148827A patent/RO109649B1/ro unknown
- 1991-03-28 DK DK91906726.4T patent/DK0477315T3/da active
- 1991-03-28 UA UA5010581A patent/UA27226C2/uk unknown
- 1991-03-28 KR KR1019910701670A patent/KR950004705B1/ko not_active Expired - Fee Related
- 1991-03-28 MC MC@@@@D patent/MC2185A1/xx unknown
- 1991-03-28 IL IL9771491A patent/IL97714A/en not_active IP Right Cessation
- 1991-03-28 JP JP3507012A patent/JP2582497B2/ja not_active Expired - Lifetime
- 1991-03-28 AT AT91906726T patent/ATE138656T1/de not_active IP Right Cessation
- 1991-03-28 EP EP91906726A patent/EP0477315B1/en not_active Expired - Lifetime
- 1991-03-28 PL PL91293022A patent/PL165868B1/pl unknown
- 1991-03-28 US US07/807,852 patent/US5403840A/en not_active Expired - Lifetime
- 1991-03-28 CN CN91102687A patent/CN1051080C/zh not_active Expired - Fee Related
- 1991-03-28 CZ CS1991851A patent/CZ287353B6/cs not_active IP Right Cessation
- 1991-03-28 AU AU75745/91A patent/AU638824B2/en not_active Expired
- 1991-03-28 WO PCT/HU1991/000012 patent/WO1991014680A1/en active IP Right Grant
- 1991-03-28 SK SK851-91A patent/SK279891B6/sk unknown
- 1991-03-28 RU SU5010581A patent/RU2111216C1/ru active
- 1991-03-28 DE DE69119853T patent/DE69119853T2/de not_active Expired - Lifetime
- 1991-03-28 BR BR919105136A patent/BR9105136A/pt not_active Application Discontinuation
- 1991-11-08 OA OA60094A patent/OA10029A/en unknown
- 1991-11-26 FI FI915569A patent/FI102460B1/fi active
- 1991-11-27 BG BG95531A patent/BG61689B1/bg unknown
- 1991-11-27 NO NO914649A patent/NO179611C/no not_active IP Right Cessation
1992
- 1992-09-28 HR HRP-908/91A patent/HRP920561B1/xx not_active IP Right Cessation
- 1992-12-30 LV LVP-92-590A patent/LV10245B/en unknown
1993
- 1993-03-05 LT LTIP386A patent/LT3394B/lt not_active IP Right Cessation
- 1993-06-16 GE GEAP1993884A patent/GEP19991832B/en unknown
1994
- 1994-08-25 MD MD94-0333A patent/MD679G2/ro not_active IP Right Cessation
- 1994-11-28 TJ TJ94000007A patent/TJ231R3/xx unknown
1996
- 1996-07-31 GR GR960402042T patent/GR3020684T3/el unknown

Also Published As

Publication number	Publication date
FI102460B (fi)	1998-12-15
OA10029A (en)	1996-10-14
PL293022A1 (en)	1992-12-28
CS85191A3 (en)	1991-11-12
DK0477315T3 (da)	1996-09-30
LT3394B (en)	1995-09-25
JP2582497B2 (ja)	1997-02-19
LTIP386A (en)	1994-12-27
PL165868B1 (pl)	1995-02-28
AU638824B2 (en)	1993-07-08
BG95531A (bg)	1993-12-24
FI915569A0 (fi)	1991-11-26
ES2090320T3 (es)	1996-10-16
NO179611C (no)	1996-11-13
US5403840A (en)	1995-04-04
SK279891B6 (sk)	1999-05-07
NO914649L (no)	1991-11-27
EP0477315A1 (en)	1992-04-01
FI102460B1 (fi)	1998-12-15
ATE138656T1 (de)	1996-06-15
LV10245B (en)	1995-08-20
IL97714A0 (en)	1992-06-21
EP0477315B1 (en)	1996-05-29
BG61689B1 (bg)	1998-03-31
GEP19991832B (en)	1999-11-05
LV10245A (lv)	1994-10-20
NO914649D0 (no)	1991-11-27
HU210921B (en)	1995-09-28
BR9105136A (pt)	1992-08-04
DE69119853T2 (de)	1996-10-10
TJ231R3 (en)	1999-11-24
UA27226C2 (uk)	2000-08-15
DE69119853D1 (de)	1996-07-04
RO109649B1 (ro)	1995-04-28
CA2054188C (en)	1996-07-23
NO179611B (no)	1996-08-05
RU2111216C1 (ru)	1998-05-20
CN1056688A (zh)	1991-12-04
KR920701182A (ko)	1992-08-11
CA2054188A1 (en)	1991-09-29
MD679G2 (ro)	1997-11-30
HRP920561A2 (hr)	1994-04-30
MD679F1 (en)	1997-02-28
SI9110908A (sl)	1998-06-30
HRP920561B1 (en)	1999-12-31
HU901868D0 (en)	1990-08-28
CN1051080C (zh)	2000-04-05
MC2185A1 (fr)	1992-09-16
CZ287353B6 (cs)	2000-11-15
KR950004705B1 (ko)	1995-05-04
JPH04506362A (ja)	1992-11-05
WO1991014680A1 (en)	1991-10-03
GR3020684T3 (en)	1996-10-31
AU7574591A (en)	1991-10-21
HUT58109A (en)	1992-01-28

Publication	Publication Date	Title
US4869904A (en)	1989-09-26	Sustained release drug preparation
KR101275372B1 (ko)	2013-06-14	에스트로겐-시클로덱스트린 복합체의 조성물
US5244881A (en)	1993-09-14	Compositions based on imipyramine
JPS62103077A (ja)	1987-05-13	シクロデキストリンにより形成された７−イソプロポキシ−イソフラボンの包接複合体、その製造方法および活性成分として該化合物を含有する医薬組成物
US5403840A (en)	1995-04-04	Inclusion complexes of N-ethoxycarbonyl 1-3-morpholino-sydnonimine or salts formed with cyclodextrin-derivatives, preparation thereof and pharmaceutical compositions containing the same
JP3434828B2 (ja)	2003-08-11	Ｓｉｎ−１ａシクロデキストリン包接複合体
US20090023683A1 (en)	2009-01-22	Complexes comprising zoledronic acid and cyclodextrins
JP2549961B2 (ja)	1996-10-30	３ーモルホリノーシドノンイミン又はその塩又はその互変異性体の包接錯体、その製法、及び該包接錯体を含有する医薬組成物
HUT72055A (en)	1996-03-28	Ciklodextrin-vinpocetin complexes process for producing them and pharmaceutical compositions containing them
US20040127462A1 (en)	2004-07-01	Anilide and cyclodextrin complexes, their preparation and their use as medicine in particular for treating dyslipidemiae
JPH01287094A (ja)	1989-11-17	ダナゾール−シクロデキストリン包接化合物
HU211906A9 (en)	1996-01-29	Inclusion complexes of n-ethoxycarbonyl 1-3-morpholino-sydnonimine or salts formed with cyclodextrin-derivatives, preparation thereof and pharmaceutical compositions containing the same

Legal Events

Date	Code	Title	Description
1997-09-30	HP	Change in proprietorship
2011-12-29	EXP	Patent expired