NO800265L - Fremgangsmaate til selektiv fremstilling av isosorbid-5-nitrat - Google Patents

Fremgangsmaate til selektiv fremstilling av isosorbid-5-nitrat

Info

Publication number: NO800265L
Authority: NO; Norway
Prior art keywords: acid; isomannide; isosorbide; ester; nitrate
Prior art date: 1979-02-02

Application number

NO800265A

Other languages

English (en)

Norwegian (no)

Inventor

Klaus Sandrock

Guenter Cordes

Original Assignee

Sanol Arznei Schwarz Gmbh

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.)

1979-02-02

Filing date

1980-02-01

Publication date

1980-08-04

1980-02-01 Application filed by Sanol Arznei Schwarz Gmbh filed Critical Sanol Arznei Schwarz Gmbh

1980-08-04 Publication of NO800265L publication Critical patent/NO800265L/no

Links

238000000034 method Methods 0.000 title claims description 20
229910002651 NO3 Inorganic materials 0.000 title claims description 12
238000002360 preparation method Methods 0.000 title description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 title 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 45
YWXYYJSYQOXTPL-SLPGGIOYSA-N isosorbide mononitrate Chemical compound [O-][N+](=O)O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-SLPGGIOYSA-N 0.000 claims description 22
229960003827 isosorbide mononitrate Drugs 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 20
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 20
KLDXJTOLSGUMSJ-BXKVDMCESA-N (3s,3as,6s,6as)-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3,6-diol Chemical compound O[C@H]1CO[C@H]2[C@@H](O)CO[C@H]21 KLDXJTOLSGUMSJ-BXKVDMCESA-N 0.000 claims description 16
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 12
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
-1 alkane carboxylic acid Chemical class 0.000 claims description 8
239000003960 organic solvent Substances 0.000 claims description 7
239000005711 Benzoic acid Substances 0.000 claims description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
235000010233 benzoic acid Nutrition 0.000 claims description 6
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
229910017604 nitric acid Inorganic materials 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
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 claims description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
150000003863 ammonium salts Chemical class 0.000 claims description 4
150000008064 anhydrides Chemical class 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 4
150000004820 halides Chemical class 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
239000012430 organic reaction media Substances 0.000 claims description 4
239000002244 precipitate Substances 0.000 claims description 4
150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
229940098779 methanesulfonic acid Drugs 0.000 claims description 3
239000012074 organic phase Substances 0.000 claims description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
235000019253 formic acid Nutrition 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
239000004300 potassium benzoate Substances 0.000 claims description 2
235000010235 potassium benzoate Nutrition 0.000 claims description 2
229940103091 potassium benzoate Drugs 0.000 claims description 2
239000002516 radical scavenger Substances 0.000 claims description 2
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 claims 4
150000001340 alkali metals Chemical class 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000005605 benzo group Chemical group 0.000 claims 1
MCZDHTKJGDCTAE-UHFFFAOYSA-M tetrabutylazanium;acetate Chemical compound CC([O-])=O.CCCC[N+](CCCC)(CCCC)CCCC MCZDHTKJGDCTAE-UHFFFAOYSA-M 0.000 claims 1
SNMZANHSFVMKKA-UHFFFAOYSA-M tetrabutylazanium;formate Chemical compound [O-]C=O.CCCC[N+](CCCC)(CCCC)CCCC SNMZANHSFVMKKA-UHFFFAOYSA-M 0.000 claims 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
KLDXJTOLSGUMSJ-JGWLITMVSA-N Isosorbide Chemical compound O[C@@H]1CO[C@@H]2[C@@H](O)CO[C@@H]21 KLDXJTOLSGUMSJ-JGWLITMVSA-N 0.000 description 11
229960002479 isosorbide Drugs 0.000 description 11
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
MOYKHGMNXAOIAT-JGWLITMVSA-N isosorbide dinitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O[N+](=O)[O-])CO[C@@H]21 MOYKHGMNXAOIAT-JGWLITMVSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 5
239000002027 dichloromethane extract Substances 0.000 description 5
238000006396 nitration reaction Methods 0.000 description 5
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YWXYYJSYQOXTPL-JGWLITMVSA-N [(3r,3ar,6s,6as)-3-hydroxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl] nitrate Chemical compound [O-][N+](=O)O[C@H]1CO[C@@H]2[C@H](O)CO[C@@H]21 YWXYYJSYQOXTPL-JGWLITMVSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
238000000926 separation method Methods 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
238000013375 chromatographic separation Methods 0.000 description 2
238000001035 drying Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
150000002148 esters Chemical group 0.000 description 2
MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000010579 first pass effect Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000011835 investigation Methods 0.000 description 2
230000004060 metabolic process Effects 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000000047 product Substances 0.000 description 2
239000005695 Ammonium acetate Substances 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
241000906446 Theraps Species 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
125000005210 alkyl ammonium group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
208000029078 coronary artery disease Diseases 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
239000002360 explosive Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229960000201 isosorbide dinitrate Drugs 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
238000005406 washing Methods 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO800265A 1979-02-02 1980-02-01 Fremgangsmaate til selektiv fremstilling av isosorbid-5-nitrat NO800265L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2903927A DE2903927C2 (de)	1979-02-02	1979-02-02	Verfahren zur selektiven Herstellung von Isosorbid-5-nitrat

Publications (1)

Publication Number	Publication Date
NO800265L true NO800265L (no)	1980-08-04

Family

ID=6061975

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO800265A NO800265L (no)	1979-02-02	1980-02-01	Fremgangsmaate til selektiv fremstilling av isosorbid-5-nitrat

Country Status (28)

Country	Link
US (1)	US4297286A (de)
JP (1)	JPS5943959B2 (de)
AR (1)	AR229959A1 (de)
AT (1)	AT363958B (de)
AU (1)	AU526422B2 (de)
BE (1)	BE881487A (de)
CA (1)	CA1132993A (de)
CH (1)	CH649296A5 (de)
CS (1)	CS214821B2 (de)
DD (1)	DD148948A5 (de)
DE (1)	DE2903927C2 (de)
DK (1)	DK45280A (de)
ES (1)	ES488225A1 (de)
FI (1)	FI800314A (de)
FR (1)	FR2447933A1 (de)
GB (1)	GB2042527B (de)
GR (1)	GR68419B (de)
IE (1)	IE49380B1 (de)
IL (1)	IL59144A (de)
IT (1)	IT1151079B (de)
LU (1)	LU82116A1 (de)
NL (1)	NL8000669A (de)
NO (1)	NO800265L (de)
NZ (1)	NZ192638A (de)
PL (1)	PL221750A1 (de)
PT (1)	PT70770A (de)
SE (1)	SE447479B (de)
YU (1)	YU27380A (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
DE3028340A1 (de) *	1980-07-25	1982-02-25	Fa. Dr. Willmar Schwabe, 7500 Karlsruhe	Amino-desoxy-1.4;3.6-dianhydro-hexit-nitrate
DE3028873C2 (de) *	1980-07-30	1983-10-27	Boehringer Mannheim Gmbh, 6800 Mannheim	Verfahren zur Herstellung von 1,4 zu 3,6-Dianhydro-D-glucit-5-nitrat (Isosorbid-5-nitrat)
DE3102947A1 (de)	1981-01-29	1982-09-02	Heinrich Mack Nachf., 7918 Illertissen	Verfahren zur herstellung von isosorbid-5-nitrat
DE3117612A1 (de) *	1981-05-05	1982-11-25	Cassella Ag, 6000 Frankfurt	Verfahren zur herstellung von isosorbid-5-nitrat
DE3123719C1 (de) *	1981-06-15	1983-01-13	Boehringer Ingelheim KG, 6507 Ingelheim	Verfahren zur Herstellung von Isomannidmononitrat
JPS5818385A (ja) *	1981-07-27	1983-02-02	Toa Eiyou Kagaku Kogyo Kk	イソソルビド−５−ニトレ−トの製造法
US4518817A (en) *	1983-02-22	1985-05-21	Kirby James R	Buried conductor cable energy distribution system with conductor loop enclosure
DE4410997A1 (de) *	1994-03-30	1995-10-26	Isis Pharma Gmbh	Pharmazeutische Zubereitungen und Arzneistoffe zur Prävention und Behandlung endothelialer Dysfunktionen
JP4188058B2 (ja) *	2002-11-05	2008-11-26	ダイセル化学工業株式会社	フォトレジスト用高分子化合物及びフォトレジスト用樹脂組成物
DE102008050597A1 (de)	2008-10-09	2010-04-15	Actavis Deutschland Gmbh & Co. Kg	Pharmazeutische Zubereitungen zur Anwendung in einem Verfahren zur therapeutischen Behandlung von Hörsturz
US9447230B2 (en) *	2010-03-18	2016-09-20	New Jersey Institute Of Technology	Polyester ethers derived from asymmetrical monomers based upon bisanydrohexitols

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3886186A (en) *	1971-04-29	1975-05-27	American Home Prod	Mononitrate esters of 1,4:3,6-dianhydro-d-glucitol
US4156736A (en) *	1976-05-28	1979-05-29	Sanol Schwarz-Monheim Gmbh	Supersaturated isosorbide dinitrate solution, process for its production and its use
US4065488A (en) *	1977-02-24	1977-12-27	American Home Products Corporation	Process for preparing 1,4:3,6-dianhydro-D-glucitol 2-nitrate

1979
- 1979-02-02 DE DE2903927A patent/DE2903927C2/de not_active Expired
1980
- 1980-01-15 CH CH290/80A patent/CH649296A5/de not_active IP Right Cessation
- 1980-01-16 GR GR60973A patent/GR68419B/el unknown
- 1980-01-16 IL IL59144A patent/IL59144A/xx unknown
- 1980-01-17 NZ NZ192638A patent/NZ192638A/xx unknown
- 1980-01-23 AU AU54847/80A patent/AU526422B2/en not_active Ceased
- 1980-01-24 US US06/114,906 patent/US4297286A/en not_active Expired - Lifetime
- 1980-01-28 IT IT19504/80A patent/IT1151079B/it active
- 1980-01-29 AT AT0046780A patent/AT363958B/de not_active IP Right Cessation
- 1980-01-29 AR AR276777A patent/AR229959A1/es active
- 1980-01-29 GB GB8002881A patent/GB2042527B/en not_active Expired
- 1980-01-31 FR FR8002108A patent/FR2447933A1/fr active Granted
- 1980-01-31 DD DD80218772A patent/DD148948A5/de unknown
- 1980-01-31 LU LU82116A patent/LU82116A1/de unknown
- 1980-02-01 JP JP55011948A patent/JPS5943959B2/ja not_active Expired
- 1980-02-01 DK DK45280A patent/DK45280A/da not_active Application Discontinuation
- 1980-02-01 FI FI800314A patent/FI800314A/fi not_active Application Discontinuation
- 1980-02-01 CS CS80700A patent/CS214821B2/cs unknown
- 1980-02-01 ES ES488225A patent/ES488225A1/es not_active Expired
- 1980-02-01 IE IE208/80A patent/IE49380B1/en unknown
- 1980-02-01 BE BE2/58379A patent/BE881487A/fr not_active IP Right Cessation
- 1980-02-01 PT PT70770A patent/PT70770A/pt not_active IP Right Cessation
- 1980-02-01 NO NO800265A patent/NO800265L/no unknown
- 1980-02-01 SE SE8000844A patent/SE447479B/sv not_active IP Right Cessation
- 1980-02-01 CA CA344,874A patent/CA1132993A/en not_active Expired
- 1980-02-01 YU YU00273/80A patent/YU27380A/xx unknown
- 1980-02-01 PL PL22175080A patent/PL221750A1/xx unknown
- 1980-02-01 NL NL8000669A patent/NL8000669A/nl not_active Application Discontinuation

Also Published As

Publication number	Publication date
SE8000844L (sv)	1980-08-03
PT70770A (en)	1980-03-01
AU526422B2 (en)	1983-01-06
ES488225A1 (es)	1980-09-16
DE2903927C2 (de)	1981-03-12
FR2447933A1 (fr)	1980-08-29
DE2903927B1 (de)	1980-06-19
CH649296A5 (de)	1985-05-15
PL221750A1 (de)	1980-12-01
SE447479B (sv)	1986-11-17
GB2042527A (en)	1980-09-24
AT363958B (de)	1981-09-10
DK45280A (da)	1980-08-03
US4297286A (en)	1981-10-27
NZ192638A (en)	1981-03-16
JPS55127393A (en)	1980-10-02
IL59144A0 (en)	1980-05-30
DD148948A5 (de)	1981-06-17
JPS5943959B2 (ja)	1984-10-25
GR68419B (de)	1981-12-29
IT1151079B (it)	1986-12-17
YU27380A (en)	1983-01-21
LU82116A1 (de)	1980-04-23
BE881487A (fr)	1980-05-30
IT8019504A0 (it)	1980-01-28
AU5484780A (en)	1980-08-07
IE49380B1 (en)	1985-10-02
NL8000669A (nl)	1980-08-05
IL59144A (en)	1982-08-31
GB2042527B (en)	1982-12-15
IE800208L (en)	1980-08-02
FI800314A (fi)	1980-08-03
CS214821B2 (en)	1982-06-25
AR229959A1 (es)	1984-01-31
CA1132993A (en)	1982-10-05
FR2447933B1 (de)	1983-11-10
ATA46780A (de)	1981-02-15

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