NO328584B1 - Derivater av isosorbidmononitrat, farmasoytiske preparater som omfatter disse og deres anvendelse for fremstilling av medikamenter - Google Patents

Derivater av isosorbidmononitrat, farmasoytiske preparater som omfatter disse og deres anvendelse for fremstilling av medikamenter Download PDF

Info

Publication number: NO328584B1
Authority: NO; Norway
Prior art keywords: isosorbide; mononitrate; group; compounds; connection according
Prior art date: 1998-10-07

Application number

NO20011778A

Other languages

English (en)

Norwegian (no)

Other versions

NO20011778D0 (no

NO20011778L (no

Inventor

Francisco Pubill Coy

Jose Repolles Moliner

Lydia Cabeza Llorente

Marcelli Carbo Banus

Christina Negrie Rofes

Juan-Antonio Cerda Riudavets

Alicia Ferrer Siso

Marek W Radomski

Eduardo Salas Perez-Rasilla

Juan Martinez Bonnin

Original Assignee

Lacer Sa

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.)

1998-10-07

Filing date

2001-04-06

Publication date

2010-03-22

2001-04-06 Application filed by Lacer Sa filed Critical Lacer Sa

2001-04-06 Publication of NO20011778D0 publication Critical patent/NO20011778D0/no

2001-04-06 Publication of NO20011778L publication Critical patent/NO20011778L/no

2010-03-22 Publication of NO328584B1 publication Critical patent/NO328584B1/no

Links

YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical class [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 title claims description 18
239000003814 drug Substances 0.000 title claims description 7
238000004519 manufacturing process Methods 0.000 title claims description 3
239000008194 pharmaceutical composition Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 35
KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical group O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 claims description 23
229960002479 isosorbide Drugs 0.000 claims description 23
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 16
235000001968 nicotinic acid Nutrition 0.000 claims description 16
239000011664 nicotinic acid Substances 0.000 claims description 16
230000000304 vasodilatating effect Effects 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 9
229910004679 ONO2 Inorganic materials 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 7
125000004434 sulfur atom Chemical group 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
125000004430 oxygen atom Chemical group O* 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
229940079593 drug Drugs 0.000 claims description 5
230000004064 dysfunction Effects 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000012190 activator Substances 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
230000002526 effect on cardiovascular system Effects 0.000 claims description 2
239000003381 stabilizer Substances 0.000 claims description 2
MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 claims 1
229910002651 NO3 Inorganic materials 0.000 claims 1
239000002738 chelating agent Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
239000000047 product Substances 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
239000002904 solvent Substances 0.000 description 21
239000000203 mixture Substances 0.000 description 18
239000007787 solid Substances 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000000243 solution Substances 0.000 description 14
238000010992 reflux Methods 0.000 description 13
239000011521 glass Substances 0.000 description 12
239000012298 atmosphere Substances 0.000 description 11
238000003760 magnetic stirring Methods 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
229960003827 isosorbide mononitrate Drugs 0.000 description 10
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 9
238000000034 method Methods 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
150000002894 organic compounds Chemical class 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
238000005481 NMR spectroscopy Methods 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
238000001035 drying Methods 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
238000004566 IR spectroscopy Methods 0.000 description 5
241001465754 Metazoa Species 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
239000012043 crude product Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000001228 spectrum Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 3
238000003556 assay Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000001110 calcium chloride Substances 0.000 description 3
235000011148 calcium chloride Nutrition 0.000 description 3
229910001628 calcium chloride Inorganic materials 0.000 description 3
238000011161 development Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000004237 preparative chromatography Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
KHLBHKYZTXYEHP-UHFFFAOYSA-N 2-methylpyridine-3-carbothioyl chloride Chemical compound CC1=NC=CC=C1C(Cl)=S KHLBHKYZTXYEHP-UHFFFAOYSA-N 0.000 description 2
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
JYWNYMJKURVPFH-UHFFFAOYSA-N N-gamma-Acetyl-N-2-Formyl-5-Methoxykynurenamine Chemical compound COC1=CC=C(NC=O)C(C(=O)CCNC(C)=O)=C1 JYWNYMJKURVPFH-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
208000006906 Vascular Ring Diseases 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
229940125898 compound 5 Drugs 0.000 description 2
229910052805 deuterium Inorganic materials 0.000 description 2
239000003480 eluent Substances 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000003818 flash chromatography Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
125000003396 thiol group Chemical group [H]S* 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 2
230000024883 vasodilation Effects 0.000 description 2
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
JYWKEVKEKOTYEX-UHFFFAOYSA-N 2,6-dibromo-4-chloroiminocyclohexa-2,5-dien-1-one Chemical compound ClN=C1C=C(Br)C(=O)C(Br)=C1 JYWKEVKEKOTYEX-UHFFFAOYSA-N 0.000 description 1
GOTPCIOLZMWNHT-UHFFFAOYSA-N 2-ethylpyridine-3-carbothioic s-acid Chemical compound CCC1=NC=CC=C1C(O)=S GOTPCIOLZMWNHT-UHFFFAOYSA-N 0.000 description 1
GNYWBJRDQHPSJL-UHFFFAOYSA-N 6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carboxylic acid Chemical compound CC(=O)C1(O)C=CC=CC1C(O)=O GNYWBJRDQHPSJL-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
241000819038 Chichester Species 0.000 description 1
241000021559 Dicerandra Species 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
235000010654 Melissa officinalis Nutrition 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
206010043087 Tachyphylaxis Diseases 0.000 description 1
206010047141 Vasodilatation Diseases 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000002744 anti-aggregatory effect Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
210000002565 arteriole Anatomy 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
239000000539 dimer Substances 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
MAHNFPMIPQKPPI-UHFFFAOYSA-N disulfur Chemical class S=S MAHNFPMIPQKPPI-UHFFFAOYSA-N 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000006345 epimerization reaction Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
210000002196 fr. b Anatomy 0.000 description 1
210000003918 fraction a Anatomy 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
230000010354 integration Effects 0.000 description 1
239000000865 liniment Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
239000000178 monomer Substances 0.000 description 1
230000000802 nitrating effect Effects 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229960002748 norepinephrine Drugs 0.000 description 1
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
-1 pomades Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
208000002815 pulmonary hypertension Diseases 0.000 description 1
238000000746 purification Methods 0.000 description 1
KOUKXHPPRFNWPP-UHFFFAOYSA-N pyrazine-2,5-dicarboxylic acid;hydrate Chemical compound O.OC(=O)C1=CN=C(C(O)=O)C=N1 KOUKXHPPRFNWPP-UHFFFAOYSA-N 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
238000011160 research Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
208000037905 systemic hypertension Diseases 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003566 thiocarboxylic acids Chemical class 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
230000002792 vascular Effects 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
- 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
- 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

NO20011778A 1998-10-07 2001-04-06 Derivater av isosorbidmononitrat, farmasoytiske preparater som omfatter disse og deres anvendelse for fremstilling av medikamenter NO328584B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ES009802076A ES2142773B1 (es)	1998-10-07	1998-10-07	Derivados de mononitrato de isosorbida y su empleo como agentes vasodilatadores con tolerancia desminuida.
PCT/ES1999/000316 WO2000020420A1 (es)	1998-10-07	1999-10-04	Derivados de mononitrato de isosorbida y su empleo como agentes vasodilatadores con tolerancia disminuida

Publications (3)

Publication Number	Publication Date
NO20011778D0 NO20011778D0 (no)	2001-04-06
NO20011778L NO20011778L (no)	2001-04-06
NO328584B1 true NO328584B1 (no)	2010-03-22

Family

ID=8305360

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20011778A NO328584B1 (no)	1998-10-07	2001-04-06	Derivater av isosorbidmononitrat, farmasoytiske preparater som omfatter disse og deres anvendelse for fremstilling av medikamenter

Country Status (40)

Country	Link
US (2)	US20010051735A1 (is)
EP (1)	EP1120419B1 (is)
JP (1)	JP4659214B2 (is)
KR (1)	KR100641801B1 (is)
CN (1)	CN1096465C (is)
AP (1)	AP1555A (is)
AR (1)	AR020538A1 (is)
AT (1)	ATE323707T1 (is)
AU (1)	AU762724B2 (is)
BG (1)	BG65135B1 (is)
BR (1)	BR9914355B1 (is)
CA (1)	CA2346010C (is)
CO (1)	CO5180544A1 (is)
CU (1)	CU23162A3 (is)
CZ (1)	CZ294551B6 (is)
DE (2)	DE69930949T2 (is)
DK (1)	DK1120419T3 (is)
EA (1)	EA003360B1 (is)
EE (1)	EE04374B1 (is)
ES (2)	ES2142773B1 (is)
GB (1)	GB2359810B (is)
GE (1)	GEP20043162B (is)
GT (1)	GT199900173A (is)
HR (1)	HRP20010256B1 (is)
HU (1)	HUP0103937A3 (is)
ID (1)	ID29946A (is)
IL (2)	IL142391A0 (is)
IS (1)	IS2312B (is)
NO (1)	NO328584B1 (is)
NZ (1)	NZ510855A (is)
OA (1)	OA11661A (is)
PA (1)	PA8483901A1 (is)
PE (1)	PE20001083A1 (is)
PL (1)	PL200028B1 (is)
PT (1)	PT1120419E (is)
RS (1)	RS50112B (is)
TR (1)	TR200100961T2 (is)
WO (1)	WO2000020420A1 (is)
YU (1)	YU25201A (is)
ZA (1)	ZA200102836B (is)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES2258365B1 (es) *	2003-10-03	2007-12-01	Lacer, S.A.	Derivados de disulfuro, sulfuro, sulfoxido y sulfona de azucares ciclicos y sus usos.
EP1941876A1 (en) *	2006-12-28	2008-07-09	Lacer, S.A.	Isosorbide mononitrate derivatives for the treatment of Inflammation and ocular hypertension
ES2332565B1 (es) *	2007-01-23	2010-10-21	Lacer, S.A.	Uso de derivados de mononitrato de dianhidrohexita como agentes antiinflamatorios.
IE20070934A1 (en)	2007-12-21	2009-06-24	Trinity College Dublin	Efficient aspirin prodrugs
JP5587790B2 (ja)	2008-01-09	2014-09-10	アミュラセラピューティクスリミティド	化合物
ES2393049T3 (es) *	2008-02-07	2012-12-18	Nicox S.A.	Compuestos donantes de óxido nítrico
EP2149576A1 (en) *	2008-07-22	2010-02-03	Lacer, S.A.	Isosorbide Nitrates having vasodilating activity
EP2149577B1 (en)	2008-07-22	2011-04-27	Lacer, S.A.	New stereospecific method for the preparation of dioxa-bicyclooctane compounds
EP2177216A1 (en) *	2008-10-13	2010-04-21	Lacer, S.A.	Use of dianhydrohexite mononitrate derivatives as healing agents
WO2010055138A1 (en) *	2008-11-14	2010-05-20	Lacer, S.A.	New stereospecific method for the preparation of dioxa-bicyclooctane compounds
EP2199294A1 (en)	2008-12-19	2010-06-23	Lacer, S.A.	New stereospecific method for the preparation of dioxa bicyclooctane nitrate compounds
ES2423939T3 (es) *	2009-09-10	2013-09-25	Cognis Ip Management Gmbh	Derivados de isosorburo gliceril éter y su empleo en aplicaciones de uso doméstico
DK2515899T3 (en)	2009-12-23	2016-08-15	Arca Biopharma Inc	METHODS AND COMPOSITIONS FOR CARDIOVASCULAR DISEASES AND CONDITIONS
CN102241687A (zh) *	2011-05-23	2011-11-16	中国人民解放军第四军医大学	抗缺血/再灌注损伤的药物
WO2013060673A1 (en)	2011-10-24	2013-05-02	Nicox S.A.	Quinone based nitric oxide donating compounds
KR20150123324A (ko) *	2013-03-05	2015-11-03	아처 다니엘 미드랜드 캄파니	이소헥시드 모노트리플레이트 및 이의 합성 방법
WO2014169976A1 (en)	2013-04-18	2014-10-23	Nicox Science Ireland	Quinone based nitric oxide donating compounds
CN104650108B (zh) *	2013-11-18	2017-05-24	富力	连翘脂素硫酸酯及其衍生物、制备方法及其应用
CN105461731B (zh) *	2014-08-07	2017-05-24	富力	连翘脂素布洛芬酯、其制备及其应用

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1356374A (fr)	1963-02-12	1964-03-27		Machine à fonctions multiples pour le travail du bois
GB1356374A (en)	1971-04-29	1974-06-12	American Home Prod	Mononitrate esters of 1,3 3,6-dianhydro-d-glucitol
US3886196A (en)	1973-02-07	1975-05-27	Phillips Petroleum Co	Magnesium-aluminum-silicate-phosphate catalysts for ammonialytic cleavage of lactams to form omega-aminonitriles
DE3028289C2 (de) *	1980-07-25	1986-11-27	Dr. Willmar Schwabe GmbH & Co, 7500 Karlsruhe	2-O- und 5-O-substituierte 1.4;3.6-Dianhydro-hexit-mononitrate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen
DE3248548A1 (de) *	1982-12-29	1984-07-05	Heinrich Mack Nachf., 7918 Illertissen	Acylderivate von 1,4:3,6-dianhydro-hexiten, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE3421072A1 (de)	1984-06-06	1985-12-12	Heinrich Mack Nachf., 7918 Illertissen	1,4:3,6-dianhydro-hexit-derivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE3602067A1 (de)	1986-01-24	1987-07-30	Mack Chem Pharm	2,6-dioxabicyclo(3.3.0)octan-derivate, ihre herstellung und verwendung als arzneimittel
DE3606634A1 (de)	1986-02-28	1987-09-03	Mack Chem Pharm	Isohexid-nucleoside, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
IT1204571B (it) *	1987-05-08	1989-03-10	Chiesi Farma Spa	Esteri di 1,4:3,6-dianidrosorbitolo-2-mononitrato e 5-mononitrato,loro procedimento di preparazione e loro composizioni farmaceutiche
DE3741005A1 (de)	1987-12-03	1989-06-15	Mack Chem Pharm	Aminopropanol-derivate von 1,4:3,6-dianhydro-hexit-nitraten, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
JP2628756B2 (ja) *	1988-09-15	1997-07-09	シュバルツファルマアクチェンゲゼルシャフト	新規有機ニトレート及びそれらの製造方法
US5428061A (en)	1988-09-15	1995-06-27	Schwarz Pharma Ag	Organic nitrates and method for their preparation
US4891373A (en) *	1988-11-23	1990-01-02	Pfizer Inc.	Aminopropanol derivatives of 1,4:3,6-dianhydrohexitol nitrates, processes for their preparation and their use as medicaments
CA2014520C (en)	1989-04-17	1996-07-16	Fumio Suzuki	Hexitol derivatives
NL9001955A (nl) *	1990-09-05	1992-04-01	Cedona Pharm Bv	Nieuwe thiazolidinederivaten.
FR2680173A1 (fr) *	1991-08-07	1993-02-12	Hoechst Lab	Nitrates organiques, leurs procedes de preparation et leur utilisation dans le traitement de maladies cardiovasculaires .
DE69321596T2 (de) *	1992-07-30	1999-04-22	Cal International Ltd	Ester und kombinationen von einem organischen nitrat und einem salicyclat
IL120531A (en)	1997-03-26	2006-12-31	Yissum Res Dev Co	Nitric oxide donors and pharmaceutical compositions containing them

1998
- 1998-10-07 ES ES009802076A patent/ES2142773B1/es not_active Expired - Fee Related
1999
- 1999-09-30 AR ARP990104928A patent/AR020538A1/es active IP Right Grant
- 1999-10-04 IL IL14239199A patent/IL142391A0/xx active IP Right Grant
- 1999-10-04 EP EP99949015A patent/EP1120419B1/en not_active Expired - Lifetime
- 1999-10-04 ES ES99949015T patent/ES2257871T3/es not_active Expired - Lifetime
- 1999-10-04 YU YU25201A patent/YU25201A/sh unknown
- 1999-10-04 TR TR2001/00961T patent/TR200100961T2/xx unknown
- 1999-10-04 CN CN99811802A patent/CN1096465C/zh not_active Expired - Fee Related
- 1999-10-04 CA CA002346010A patent/CA2346010C/en not_active Expired - Fee Related
- 1999-10-04 PT PT99949015T patent/PT1120419E/pt unknown
- 1999-10-04 AT AT99949015T patent/ATE323707T1/de not_active IP Right Cessation
- 1999-10-04 EE EEP200100207A patent/EE04374B1/xx not_active IP Right Cessation
- 1999-10-04 JP JP2000574532A patent/JP4659214B2/ja not_active Expired - Fee Related
- 1999-10-04 DE DE69930949T patent/DE69930949T2/de not_active Expired - Lifetime
- 1999-10-04 AU AU62041/99A patent/AU762724B2/en not_active Ceased
- 1999-10-04 EA EA200100422A patent/EA003360B1/ru not_active IP Right Cessation
- 1999-10-04 DE DE19983612T patent/DE19983612T1/de not_active Ceased
- 1999-10-04 NZ NZ510855A patent/NZ510855A/xx not_active IP Right Cessation
- 1999-10-04 OA OA1200100085A patent/OA11661A/en unknown
- 1999-10-04 WO PCT/ES1999/000316 patent/WO2000020420A1/es not_active Application Discontinuation
- 1999-10-04 PL PL347030A patent/PL200028B1/pl not_active IP Right Cessation
- 1999-10-04 GE GEAP19995886A patent/GEP20043162B/en unknown
- 1999-10-04 GB GB0111172A patent/GB2359810B/en not_active Expired - Fee Related
- 1999-10-04 PE PE1999001005A patent/PE20001083A1/es not_active Application Discontinuation
- 1999-10-04 KR KR1020017004374A patent/KR100641801B1/ko not_active IP Right Cessation
- 1999-10-04 BR BRPI9914355-0A patent/BR9914355B1/pt not_active IP Right Cessation
- 1999-10-04 DK DK99949015T patent/DK1120419T3/da active
- 1999-10-04 ID IDW00200101008A patent/ID29946A/id unknown
- 1999-10-04 HU HU0103937A patent/HUP0103937A3/hu unknown
- 1999-10-04 RS YUP-252/01A patent/RS50112B/sr unknown
- 1999-10-04 CZ CZ20011257A patent/CZ294551B6/cs not_active IP Right Cessation
- 1999-10-04 AP APAP/P/2001/002128A patent/AP1555A/en active
- 1999-10-06 CO CO99063420A patent/CO5180544A1/es not_active Application Discontinuation
- 1999-10-07 GT GT199900173A patent/GT199900173A/es unknown
- 1999-10-07 PA PA19998483901A patent/PA8483901A1/es unknown
2001
- 2001-03-29 IS IS5910A patent/IS2312B/is unknown
- 2001-04-03 IL IL142391A patent/IL142391A/en not_active IP Right Cessation
- 2001-04-04 CU CU83A patent/CU23162A3/es not_active IP Right Cessation
- 2001-04-05 ZA ZA200102836A patent/ZA200102836B/xx unknown
- 2001-04-06 NO NO20011778A patent/NO328584B1/no not_active IP Right Cessation
- 2001-04-06 US US09/827,868 patent/US20010051735A1/en not_active Abandoned
- 2001-04-06 HR HR20010256A patent/HRP20010256B1/xx not_active IP Right Cessation
- 2001-04-06 BG BG105417A patent/BG65135B1/bg unknown
2003
- 2003-04-28 US US10/424,828 patent/US6858632B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ES2142773B1 (es)	2001-01-01
KR100641801B1 (ko)	2006-11-02
GT199900173A (es)	2001-03-30
ES2142773A1 (es)	2000-04-16
GB0111172D0 (en)	2001-06-27
AP2001002128A0 (en)	2001-06-30
EA003360B1 (ru)	2003-04-24
PL347030A1 (en)	2002-03-11
CZ294551B6 (cs)	2005-01-12
BR9914355B1 (pt)	2014-10-21
KR20010088848A (ko)	2001-09-28
PL200028B1 (pl)	2008-11-28
CN1322205A (zh)	2001-11-14
PA8483901A1 (es)	2000-09-29
BR9914355A (pt)	2001-06-26
HUP0103937A3 (en)	2003-11-28
CN1096465C (zh)	2002-12-18
NO20011778D0 (no)	2001-04-06
ATE323707T1 (de)	2006-05-15
IL142391A0 (en)	2002-03-10
DE69930949D1 (de)	2006-05-24
CA2346010C (en)	2010-01-12
EE200100207A (et)	2002-06-17
HUP0103937A2 (hu)	2002-02-28
AU762724B2 (en)	2003-07-03
EA200100422A1 (ru)	2001-10-22
US6858632B2 (en)	2005-02-22
CO5180544A1 (es)	2002-07-30
PT1120419E (pt)	2006-07-31
YU25201A (sh)	2003-04-30
DK1120419T3 (da)	2006-07-03
JP2002526544A (ja)	2002-08-20
IL142391A (en)	2007-07-24
IS5910A (is)	2001-03-29
NZ510855A (en)	2004-02-27
ES2257871T3 (es)	2006-08-01
HRP20010256A2 (en)	2002-04-30
US20030225134A1 (en)	2003-12-04
EP1120419B1 (en)	2006-04-19
CU23162A3 (es)	2006-07-18
CA2346010A1 (en)	2000-04-13
NO20011778L (no)	2001-04-06
AU6204199A (en)	2000-04-26
AP1555A (en)	2006-01-18
RS50112B (sr)	2009-03-25
WO2000020420A1 (es)	2000-04-13
PE20001083A1 (es)	2000-11-28
ZA200102836B (en)	2002-09-25
US20010051735A1 (en)	2001-12-13
DE19983612T1 (de)	2001-09-27
TR200100961T2 (tr)	2003-02-21
EP1120419A1 (en)	2001-08-01
HRP20010256B1 (en)	2009-08-31
DE69930949T2 (de)	2006-12-28
IS2312B (is)	2007-11-15
BG65135B1 (bg)	2007-03-30
JP4659214B2 (ja)	2011-03-30
OA11661A (en)	2004-12-08
AR020538A1 (es)	2002-05-15
BG105417A (en)	2001-12-29
EE04374B1 (et)	2004-10-15
GEP20043162B (en)	2004-01-26
ID29946A (id)	2001-10-25
CZ20011257A3 (cs)	2001-08-15
GB2359810A (en)	2001-09-05
GB2359810B (en)	2003-12-03

Legal Events

Date	Code	Title	Description
2011-05-30	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
NO328584B1 (no)	2010-03-22	Derivater av isosorbidmononitrat, farmasoytiske preparater som omfatter disse og deres anvendelse for fremstilling av medikamenter
CZ294549B6 (cs)	2005-01-12	Montážní spojka pro úseky vedení kabelů a výsledné úseky vedení kabelů
CA2540500C (en)	2012-08-28	Disulfide, sulfide, sulfoxide, and sulfone derivatives of cyclic sugars and uses thereof
TW200815456A (en)	2008-04-01	Artemisinin derivative dimers, their preparation and their therapeutic application
WO2014138212A1 (en)	2014-09-12	CaMKII INHIBITORS AND USES THEREOF
KR960014797B1 (ko)	1996-10-19	벤조피란 유도체, 그의 제조법 및 그것을 함유하는 의약 조성물
JP2021525784A (ja)	2021-09-27	チエノ［２，３−ｃ］ピリダジン−４（１Ｈ）−オン系誘導体及びその使用
CA3210658A1 (en)	2022-08-18	Oxadiazolyl dihydropyrano[2,3-b]pyridine inhibitors of hipk2 for treating kidney fibrosis
JPH05186458A (ja)	1993-07-27	新規なベンゾピラン誘導体
SK43499A3 (en)	2000-02-14	New pentaerythritol derivatives, their production and use and intermediates for their synthesis
EP0842924B1 (en)	2003-08-20	Pyridine intermediates, useful in the synthesis of beta-adrenergic receptor agonists
JPH04221380A (ja)	1992-08-11	ベンズオキサジン誘導体、その製法および疾患の治療または予防のためのその使用
JPS637549B2 (is)	1988-02-17
CN116655557A (zh)	2023-08-29	苯并噻唑类化合物、其制备方法及应用
MXPA01003568A (en)	2002-06-05	Derivatives of isosorbid mononitrate, utilization as vasodilator agents with reduced tolerance
CN111689977A (zh)	2020-09-22	一种喜树碱20-位修饰的磺酰脲类化合物及其制备方法和用途
WO2018149991A1 (fr)	2018-08-23	Dérivés sulfonamides hydroxylés en tant qu'agonistes inverses du récepteur gamma orphelin associé aux rétinoïdes ror gamma (t)
JPH08113574A (ja)	1996-05-07	ピリダジノインドール誘導体
WO1995023796A1 (fr)	1995-09-08	Derive de guanylhydrazone
NO152750B (no)	1985-08-05	Fremgangsmaate for fremstilling av nitrogen brohode-kondenserte pyrimidinforbindelser
JPS62153263A (ja)	1987-07-08	三環性又は四環性化合物
JPH04270291A (ja)	1992-09-25	チアジノ〔６，５−ｂ〕インドリジン誘導体
JPH02247161A (ja)	1990-10-02	ペンタジエン酸誘導体及びその製造法
JPH04270289A (ja)	1992-09-25	オキサジノ〔６，５−ｂ〕インドリジン誘導体