IL88011A - Pharmacological preparations for the treatment of psoriasis, psoriatic arthritis, neurodermatitis and regionalitis entitis - Google Patents

Pharmacological preparations for the treatment of psoriasis, psoriatic arthritis, neurodermatitis and regionalitis entitis

Info

Publication number: IL88011A
Authority: IL; Israel
Prior art keywords: fumaric acid; weight; pharmaceutical composition; salt; parts
Prior art date: 1987-10-19

Application number

IL8801188A

Other languages

English (en)

Hebrew (he)

Other versions

IL88011A0 (en

Original Assignee

Speiser Peter Paul

Joshi Rajendra K

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.)

1987-10-19

Filing date

1988-10-12

Publication date

1994-10-07

1987-10-19 Priority claimed from US07/109,780 external-priority patent/US4959389A/en

1988-10-12 Application filed by Speiser Peter Paul, Joshi Rajendra K filed Critical Speiser Peter Paul

1989-06-30 Publication of IL88011A0 publication Critical patent/IL88011A0/xx

1994-10-07 Publication of IL88011A publication Critical patent/IL88011A/en

Links

VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 title claims description 74
150000003839 salts Chemical class 0.000 title claims description 54
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 title claims description 39
239000001530 fumaric acid Substances 0.000 title claims description 36
201000004681 Psoriasis Diseases 0.000 title claims description 20
208000011231 Crohn disease Diseases 0.000 title claims description 13
201000009053 Neurodermatitis Diseases 0.000 title claims description 12
201000001263 Psoriatic Arthritis Diseases 0.000 title claims description 8
208000036824 Psoriatic arthropathy Diseases 0.000 title claims description 8
239000000825 pharmaceutical preparation Substances 0.000 title description 8
150000002148 esters Chemical class 0.000 title description 3
239000000203 mixture Substances 0.000 claims description 53
XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical class CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 claims description 35
XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 claims description 35
239000011575 calcium Substances 0.000 claims description 26
239000011777 magnesium Substances 0.000 claims description 25
LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 claims description 21
239000011701 zinc Substances 0.000 claims description 19
229960004419 dimethyl fumarate Drugs 0.000 claims description 18
239000013543 active substance Substances 0.000 claims description 16
239000002671 adjuvant Substances 0.000 claims description 14
159000000007 calcium salts Chemical class 0.000 claims description 14
239000008194 pharmaceutical composition Substances 0.000 claims description 14
239000002775 capsule Substances 0.000 claims description 13
238000009505 enteric coating Methods 0.000 claims description 13
239000002702 enteric coating Substances 0.000 claims description 13
150000003751 zinc Chemical class 0.000 claims description 10
229910052791 calcium Inorganic materials 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
229910052749 magnesium Inorganic materials 0.000 claims description 7
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
229910052725 zinc Inorganic materials 0.000 claims description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
159000000003 magnesium salts Chemical class 0.000 claims description 4
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
-1 plasters Substances 0.000 claims description 3
208000004232 Enteritis Diseases 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
229940059082 douche Drugs 0.000 claims description 2
239000007920 enema Substances 0.000 claims description 2
229940079360 enema for constipation Drugs 0.000 claims description 2
210000004905 finger nail Anatomy 0.000 claims description 2
210000004209 hair Anatomy 0.000 claims description 2
159000000014 iron salts Chemical class 0.000 claims description 2
239000006210 lotion Substances 0.000 claims description 2
239000007764 o/w emulsion Substances 0.000 claims description 2
239000002674 ointment Substances 0.000 claims description 2
239000000829 suppository Substances 0.000 claims description 2
210000004906 toe nail Anatomy 0.000 claims description 2
239000006185 dispersion Substances 0.000 claims 1
238000007911 parenteral administration Methods 0.000 claims 1
239000003826 tablet Substances 0.000 description 41
229920000036 polyvinylpyrrolidone Polymers 0.000 description 28
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 28
238000000034 method Methods 0.000 description 23
229940074369 monoethyl fumarate Drugs 0.000 description 23
239000001267 polyvinylpyrrolidone Substances 0.000 description 19
239000008187 granular material Substances 0.000 description 18
NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 17
NKHAVTQWNUWKEO-NSCUHMNNSA-N monomethyl fumarate Chemical compound COC(=O)\C=C\C(O)=O NKHAVTQWNUWKEO-NSCUHMNNSA-N 0.000 description 17
229940005650 monomethyl fumarate Drugs 0.000 description 17
238000002360 preparation method Methods 0.000 description 17
238000004519 manufacturing process Methods 0.000 description 13
239000011230 binding agent Substances 0.000 description 12
230000001681 protective effect Effects 0.000 description 12
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 12
235000012239 silicon dioxide Nutrition 0.000 description 12
239000000454 talc Substances 0.000 description 12
235000012222 talc Nutrition 0.000 description 12
229910052623 talc Inorganic materials 0.000 description 12
239000011248 coating agent Substances 0.000 description 11
238000000576 coating method Methods 0.000 description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
229920000168 Microcrystalline cellulose Polymers 0.000 description 10
239000007864 aqueous solution Substances 0.000 description 10
201000010099 disease Diseases 0.000 description 10
239000007888 film coating Substances 0.000 description 10
238000009501 film coating Methods 0.000 description 10
229940016286 microcrystalline cellulose Drugs 0.000 description 10
235000019813 microcrystalline cellulose Nutrition 0.000 description 10
239000008108 microcrystalline cellulose Substances 0.000 description 10
230000029058 respiratory gaseous exchange Effects 0.000 description 10
229920000881 Modified starch Polymers 0.000 description 9
238000009472 formulation Methods 0.000 description 9
235000019426 modified starch Nutrition 0.000 description 9
238000002560 therapeutic procedure Methods 0.000 description 9
AYAUWVRAUCDBFR-ONEGZZNKSA-N (e)-4-oxo-4-propoxybut-2-enoic acid Chemical compound CCCOC(=O)\C=C\C(O)=O AYAUWVRAUCDBFR-ONEGZZNKSA-N 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
239000008385 outer phase Substances 0.000 description 8
229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 8
239000000843 powder Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
229910002012 Aerosil® Inorganic materials 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
239000007962 solid dispersion Substances 0.000 description 6
238000001694 spray drying Methods 0.000 description 6
230000000694 effects Effects 0.000 description 5
229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
125000003158 alcohol group Chemical group 0.000 description 4
125000005233 alkylalcohol group Chemical group 0.000 description 4
238000001035 drying Methods 0.000 description 4
239000002662 enteric coated tablet Substances 0.000 description 4
150000002237 fumaric acid derivatives Chemical class 0.000 description 4
230000000977 initiatory effect Effects 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 3
229920003080 Povidone K 25 Polymers 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000002411 adverse Effects 0.000 description 3
239000004359 castor oil Substances 0.000 description 3
235000019438 castor oil Nutrition 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
150000005690 diesters Chemical class 0.000 description 3
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 3
239000004922 lacquer Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000011877 solvent mixture Substances 0.000 description 3
229920000623 Cellulose acetate phthalate Polymers 0.000 description 2
239000001828 Gelatine Substances 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
NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
NWIIWBQGYVVMHT-UHFFFAOYSA-N [O-2].[O-2].[O-2].[Ti+6] Chemical compound [O-2].[O-2].[O-2].[Ti+6] NWIIWBQGYVVMHT-UHFFFAOYSA-N 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
229940081734 cellulose acetate phthalate Drugs 0.000 description 2
DSTWFRCNXMNXTR-AATRIKPKSA-N dipropyl (e)-but-2-enedioate Chemical compound CCCOC(=O)\C=C\C(=O)OCCC DSTWFRCNXMNXTR-AATRIKPKSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003814 drug Substances 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
229960004592 isopropanol Drugs 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
229940093429 polyethylene glycol 6000 Drugs 0.000 description 2
210000002784 stomach Anatomy 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
238000011287 therapeutic dose Methods 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
BSSNZUFKXJJCBG-OWOJBTEDSA-N (e)-but-2-enediamide Chemical compound NC(=O)\C=C\C(N)=O BSSNZUFKXJJCBG-OWOJBTEDSA-N 0.000 description 1
KYPOHTVBFVELTG-OWOJBTEDSA-N (e)-but-2-enedinitrile Chemical compound N#C\C=C\C#N KYPOHTVBFVELTG-OWOJBTEDSA-N 0.000 description 1
WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
229930195730 Aflatoxin Natural products 0.000 description 1
XWIYFDMXXLINPU-UHFFFAOYSA-N Aflatoxin G Chemical compound O=C1OCCC2=C1C(=O)OC1=C2C(OC)=CC2=C1C1C=COC1O2 XWIYFDMXXLINPU-UHFFFAOYSA-N 0.000 description 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
LBQUJVJZHVBJTO-UHFFFAOYSA-M C(C=CC(=O)[O-])(=O)OC.[Ca+] Chemical compound C(C=CC(=O)[O-])(=O)OC.[Ca+] LBQUJVJZHVBJTO-UHFFFAOYSA-M 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
208000003468 Ehrlich Tumor Carcinoma Diseases 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
229920003148 Eudragit® E polymer Polymers 0.000 description 1
206010022653 Intestinal haemorrhages Diseases 0.000 description 1
206010022714 Intestinal ulcer Diseases 0.000 description 1
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 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
102100037611 Lysophospholipase Human genes 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
108010058864 Phospholipases A2 Proteins 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
KKGWFBLJHIPEFA-BJILWQEISA-M [Ca+].C(CC)OC(\C=C\C(=O)[O-])=O Chemical compound [Ca+].C(CC)OC(\C=C\C(=O)[O-])=O KKGWFBLJHIPEFA-BJILWQEISA-M 0.000 description 1
OGGYHLYPOPHHHH-BJILWQEISA-M [Ca+].CCOC(=O)\C=C\C([O-])=O Chemical compound [Ca+].CCOC(=O)\C=C\C([O-])=O OGGYHLYPOPHHHH-BJILWQEISA-M 0.000 description 1
231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
239000005409 aflatoxin Substances 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
230000002682 anti-psoriatic effect Effects 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
238000004820 blood count Methods 0.000 description 1
NEDGUIRITORSKL-UHFFFAOYSA-N butyl 2-methylprop-2-enoate;2-(dimethylamino)ethyl 2-methylprop-2-enoate;methyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.CCCCOC(=O)C(C)=C.CN(C)CCOC(=O)C(C)=C NEDGUIRITORSKL-UHFFFAOYSA-N 0.000 description 1
WOONQYHBMBCNDD-SYWGCQIGSA-L calcium;(e)-4-ethoxy-4-oxobut-2-enoate Chemical compound [Ca+2].CCOC(=O)\C=C\C([O-])=O.CCOC(=O)\C=C\C([O-])=O WOONQYHBMBCNDD-SYWGCQIGSA-L 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
BZCOSCNPHJNQBP-OWOJBTEDSA-N dihydroxyfumaric acid Chemical compound OC(=O)C(\O)=C(/O)C(O)=O BZCOSCNPHJNQBP-OWOJBTEDSA-N 0.000 description 1
238000009826 distribution Methods 0.000 description 1
230000002500 effect on skin Effects 0.000 description 1
210000002615 epidermis Anatomy 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000011389 fruit/vegetable juice Nutrition 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
230000002008 hemorrhagic effect Effects 0.000 description 1
231100000086 high toxicity Toxicity 0.000 description 1
239000008240 homogeneous mixture Substances 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
206010021198 ichthyosis Diseases 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
230000003907 kidney function Effects 0.000 description 1
TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
230000003908 liver function Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
230000010534 mechanism of action Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
235000006109 methionine Nutrition 0.000 description 1
229960004857 mitomycin Drugs 0.000 description 1
238000005498 polishing Methods 0.000 description 1
230000001185 psoriatic effect Effects 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
210000000813 small intestine Anatomy 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
210000000952 spleen Anatomy 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000004102 tricarboxylic acid cycle Effects 0.000 description 1
231100000397 ulcer Toxicity 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Landscapes

Medicinal Preparation (AREA)

IL8801188A 1987-10-19 1988-10-12 Pharmacological preparations for the treatment of psoriasis, psoriatic arthritis, neurodermatitis and regionalitis entitis IL88011A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US07/109,780 US4959389A (en)	1987-10-19	1987-10-19	Pharmaceutical preparation for the treatment of psoriatic arthritis
EP88109783A EP0312697B1 (de)	1987-10-19	1988-06-20	Pharmazeutische Zubereitungen zur Behandlung der Psoriasis, psoriatischen Arthritis, Neurodermitis und Enteritis regionalis Crohn

Publications (2)

Publication Number	Publication Date
IL88011A0 IL88011A0 (en)	1989-06-30
IL88011A true IL88011A (en)	1994-10-07

Family

ID=26114146

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL8801188A IL88011A (en)	1987-10-19	1988-10-12	Pharmacological preparations for the treatment of psoriasis, psoriatic arthritis, neurodermatitis and regionalitis entitis

Country Status (2)

Country	Link
AT (1)	ATE88342T1 (de)
IL (1)	IL88011A (de)

1988
- 1988-06-20 AT AT88109783T patent/ATE88342T1/de not_active IP Right Cessation
- 1988-10-12 IL IL8801188A patent/IL88011A/en active Protection Beyond IP Right Term

Also Published As

Publication number	Publication date
IL88011A0 (en)	1989-06-30
ATE88342T1 (de)	1993-05-15

Legal Events

Date	Code	Title
1999-03-12	KB	Patent renewed
2002-12-01	KB	Patent renewed
2006-12-07	KB	Patent renewed
2009-05-03	EXTN	Extension order renewed

Publication	Publication Date	Title
US4959389A (en)	1990-09-25	Pharmaceutical preparation for the treatment of psoriatic arthritis
US5424332A (en)	1995-06-13	Pharmaceutical composition and process for the production thereof
US6436992B1 (en)	2002-08-20	Use of fumaric acid derivatives
AU746958B2 (en)	2002-05-09	The use of fumaric acid derivatives in transplant medicine
RU2197233C2 (ru)	2003-01-27	Применение кислых алкилфумаратов для лечения псориаза, псориатического артрита, нейродермита и регионального энтерита крона
AU745889B2 (en)	2002-04-11	Fumaric acid microtablets
AU2004269903B2 (en)	2010-09-02	The use of fumaric acid derivatives for treating cardiac insufficiency, and asthma
RU2459621C2 (ru)	2012-08-27	Применение производных фумаровой кислоты для лечения сердечной недостаточности, инфаркта миокарда и стенокардии
NO333257B1 (no)	2013-04-22	Anvendelse av dialkylfumarater for fremstilling av medikamenter til behandling av multippel sklerose
MXPA99010703A (en)	2000-09-04	Use of fumaric acid derivatives
HK1035134B (en)	2005-03-11	The use of alkyl hydrogen fumarates for preparing a pharmaceutical composition in the form of microtablets
JP7195354B2 (ja)	2022-12-23	浸食マトリックス中に１またはそれ以上のフマル酸エステルを含む医薬製剤
MXPA00007089A (en)	2001-06-26	Utilization of alkyl hydrogen fumerates for treating psoriasis, psoriatic arthritis, neurodermatitis and regional enteritis