IL132819A - Use of fumaric acid derivatives in the preparation of medicaments - Google Patents

Use of fumaric acid derivatives in the preparation of medicaments

Info

Publication number: IL132819A
Authority: IL; Israel
Prior art keywords: fumaric acid; weight; parts; use according; salt
Prior art date: 1997-05-20

Application number

IL13281998A

Other languages

English (en)

Other versions

IL132819A0 (en

Original Assignee

Fumapharm Ag

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.)

1997-05-20

Filing date

1998-04-01

Publication date

2004-12-15

1998-04-01 Application filed by Fumapharm Ag filed Critical Fumapharm Ag

2001-03-19 Publication of IL132819A0 publication Critical patent/IL132819A0/xx

2004-12-15 Publication of IL132819A publication Critical patent/IL132819A/en

Links

238000002360 preparation method Methods 0.000 title description 19
239000003814 drug Substances 0.000 title description 11
150000002237 fumaric acid derivatives Chemical class 0.000 title description 8
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims abstract description 100
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract description 58
239000001530 fumaric acid Substances 0.000 claims abstract description 45
150000002148 esters Chemical class 0.000 claims abstract description 28
239000002253 acid Substances 0.000 claims abstract description 11
208000023275 Autoimmune disease Diseases 0.000 claims abstract description 5
239000004480 active ingredient Substances 0.000 claims description 40
239000011575 calcium Substances 0.000 claims description 37
239000002775 capsule Substances 0.000 claims description 35
239000008194 pharmaceutical composition Substances 0.000 claims description 26
LDCRTTXIJACKKU-ONEGZZNKSA-N dimethyl fumarate Chemical compound COC(=O)\C=C\C(=O)OC LDCRTTXIJACKKU-ONEGZZNKSA-N 0.000 claims description 25
239000008188 pellet Substances 0.000 claims description 25
239000011777 magnesium Substances 0.000 claims description 24
229960004419 dimethyl fumarate Drugs 0.000 claims description 23
159000000007 calcium salts Chemical class 0.000 claims description 21
239000011701 zinc Substances 0.000 claims description 21
-1 alkyl hydrogen fumarates Chemical class 0.000 claims description 20
NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 claims description 18
NKHAVTQWNUWKEO-NSCUHMNNSA-N monomethyl fumarate Chemical compound COC(=O)\C=C\C(O)=O NKHAVTQWNUWKEO-NSCUHMNNSA-N 0.000 claims description 18
238000011282 treatment Methods 0.000 claims description 16
150000001875 compounds Chemical class 0.000 claims description 13
150000001768 cations Chemical class 0.000 claims description 12
239000000546 pharmaceutical excipient Substances 0.000 claims description 12
XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 claims description 11
229910052749 magnesium Inorganic materials 0.000 claims description 11
150000003751 zinc Chemical class 0.000 claims description 11
206010036030 Polyarthritis Diseases 0.000 claims description 10
206010003246 arthritis Diseases 0.000 claims description 10
229910052791 calcium Inorganic materials 0.000 claims description 10
XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 claims description 10
208000030428 polyarticular arthritis Diseases 0.000 claims description 10
229910052725 zinc Inorganic materials 0.000 claims description 10
208000024908 graft versus host disease Diseases 0.000 claims description 9
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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 claims description 8
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
239000011591 potassium Substances 0.000 claims description 8
229910052700 potassium Inorganic materials 0.000 claims description 8
239000011734 sodium Substances 0.000 claims description 8
229910052708 sodium Inorganic materials 0.000 claims description 8
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
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239000003937 drug carrier Substances 0.000 claims description 4
208000006454 hepatitis Diseases 0.000 claims description 4
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XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
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239000002702 enteric coating Substances 0.000 claims 2
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150000003839 salts Chemical class 0.000 abstract description 56
238000000034 method Methods 0.000 abstract description 27
150000007513 acids Chemical class 0.000 abstract description 3
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239000003826 tablet Substances 0.000 description 45
235000011087 fumaric acid Nutrition 0.000 description 30
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 21
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230000000694 effects Effects 0.000 description 11
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RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 11
235000012239 silicon dioxide Nutrition 0.000 description 11
PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 10
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
239000008385 outer phase Substances 0.000 description 10
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229940050411 fumarate Drugs 0.000 description 9
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239000011230 binding agent Substances 0.000 description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
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230000005764 inhibitory process Effects 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
239000001828 Gelatine Substances 0.000 description 5
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238000012360 testing method Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
229920000623 Cellulose acetate phthalate Polymers 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000000427 antigen Substances 0.000 description 4
239000004359 castor oil Substances 0.000 description 4
235000019438 castor oil Nutrition 0.000 description 4
229940081734 cellulose acetate phthalate Drugs 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
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 4
230000001506 immunosuppresive effect Effects 0.000 description 4
238000002844 melting Methods 0.000 description 4
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229940074369 monoethyl fumarate Drugs 0.000 description 4
210000002966 serum Anatomy 0.000 description 4
239000000126 substance Substances 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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
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 3
239000004902 Softening Agent Substances 0.000 description 3
102000036639 antigens Human genes 0.000 description 3
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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 3
239000006185 dispersion Substances 0.000 description 3
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229940079360 enema for constipation Drugs 0.000 description 3
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239000004922 lacquer Substances 0.000 description 3
239000008101 lactose Substances 0.000 description 3
239000006210 lotion Substances 0.000 description 3
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
239000002674 ointment Substances 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
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206010028980 Neoplasm Diseases 0.000 description 2
229920003080 Povidone K 25 Polymers 0.000 description 2
229920002472 Starch Polymers 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
230000004523 agglutinating effect Effects 0.000 description 2
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239000007888 film coating Substances 0.000 description 2
238000009501 film coating Methods 0.000 description 2
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238000011835 investigation Methods 0.000 description 2
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230000007774 longterm Effects 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
229940005650 monomethyl fumarate Drugs 0.000 description 2
229940093429 polyethylene glycol 6000 Drugs 0.000 description 2
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
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235000019698 starch Nutrition 0.000 description 2
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230000004102 tricarboxylic acid cycle Effects 0.000 description 2
QBBTZXBTFYKMKT-UHFFFAOYSA-N 2,3-diacetyloxypropyl acetate Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O.CC(=O)OCC(OC(C)=O)COC(C)=O QBBTZXBTFYKMKT-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
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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
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BZCOSCNPHJNQBP-OWOJBTEDSA-N dihydroxyfumaric acid Chemical compound OC(=O)C(\O)=C(/O)C(O)=O BZCOSCNPHJNQBP-OWOJBTEDSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/593—Dicarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/60—Maleic acid esters; Fumaric acid esters
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- 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
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Immunology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Epidemiology (AREA)
Emergency Medicine (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Transplantation (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicinal Preparation (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL13281998A 1997-05-20 1998-04-01 Use of fumaric acid derivatives in the preparation of medicaments IL132819A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19721099A DE19721099C2 (de)	1997-05-20	1997-05-20	Verwendung von Fumarsäurederivaten
PCT/EP1998/001894 WO1998052549A2 (fr)	1997-05-20	1998-04-01	Utilisation de derives d'acide fumarique

Publications (2)

Publication Number	Publication Date
IL132819A0 IL132819A0 (en)	2001-03-19
IL132819A true IL132819A (en)	2004-12-15

Family

ID=7829995

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL13281998A IL132819A (en)	1997-05-20	1998-04-01	Use of fumaric acid derivatives in the preparation of medicaments

Country Status (24)

Country	Link
US (1)	US6436992B1 (fr)
EP (1)	EP0980242B1 (fr)
JP (1)	JP3881038B2 (fr)
CN (1)	CN1153569C (fr)
AT (1)	ATE232093T1 (fr)
AU (1)	AU730441B2 (fr)
BG (1)	BG64613B1 (fr)
BR (1)	BR9809655A (fr)
CA (1)	CA2248955C (fr)
CZ (1)	CZ299960B6 (fr)
DE (2)	DE19721099C2 (fr)
DK (1)	DK0980242T3 (fr)
EE (1)	EE03999B1 (fr)
ES (1)	ES2190588T3 (fr)
HU (1)	HU227697B1 (fr)
IL (1)	IL132819A (fr)
NO (1)	NO326815B1 (fr)
NZ (1)	NZ501755A (fr)
PL (1)	PL190864B1 (fr)
RS (1)	RS49654B (fr)
RU (1)	RU2197963C2 (fr)
SK (1)	SK285897B6 (fr)
TR (1)	TR199902587T2 (fr)
WO (1)	WO1998052549A2 (fr)

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1997
- 1997-05-20 DE DE19721099A patent/DE19721099C2/de not_active Expired - Lifetime
1998
- 1998-04-01 RS YUP-575/99A patent/RS49654B/sr unknown
- 1998-04-01 CN CNB98805308XA patent/CN1153569C/zh not_active Expired - Fee Related
- 1998-04-01 RU RU99127306/14A patent/RU2197963C2/ru not_active IP Right Cessation
- 1998-04-01 EE EEP199900535A patent/EE03999B1/xx unknown
- 1998-04-01 EP EP98919202A patent/EP0980242B1/fr not_active Expired - Lifetime
- 1998-04-01 CA CA002248955A patent/CA2248955C/fr not_active Expired - Fee Related
- 1998-04-01 TR TR1999/02587T patent/TR199902587T2/xx unknown
- 1998-04-01 DE DE59807122T patent/DE59807122D1/de not_active Expired - Lifetime
- 1998-04-01 NZ NZ501755A patent/NZ501755A/en not_active IP Right Cessation
- 1998-04-01 SK SK415-99A patent/SK285897B6/sk not_active IP Right Cessation
- 1998-04-01 US US09/194,862 patent/US6436992B1/en not_active Expired - Lifetime
- 1998-04-01 AU AU72136/98A patent/AU730441B2/en not_active Ceased
- 1998-04-01 HU HU0001684A patent/HU227697B1/hu not_active IP Right Cessation
- 1998-04-01 JP JP54984398A patent/JP3881038B2/ja not_active Expired - Fee Related
- 1998-04-01 DK DK98919202T patent/DK0980242T3/da active
- 1998-04-01 CZ CZ0108099A patent/CZ299960B6/cs not_active IP Right Cessation
- 1998-04-01 PL PL335381A patent/PL190864B1/pl unknown
- 1998-04-01 ES ES98919202T patent/ES2190588T3/es not_active Expired - Lifetime
- 1998-04-01 IL IL13281998A patent/IL132819A/en not_active IP Right Cessation
- 1998-04-01 AT AT98919202T patent/ATE232093T1/de active
- 1998-04-01 BR BR9809655-9A patent/BR9809655A/pt not_active Application Discontinuation
- 1998-04-01 WO PCT/EP1998/001894 patent/WO1998052549A2/fr not_active Ceased
1999
- 1999-03-19 NO NO991342A patent/NO326815B1/no not_active IP Right Cessation
- 1999-04-14 BG BG103335A patent/BG64613B1/bg unknown

Also Published As

Publication number	Publication date
JP3881038B2 (ja)	2007-02-14
DE19721099C2 (de)	1999-12-02
EP0980242B1 (fr)	2003-02-05
BR9809655A (pt)	2000-07-11
HUP0001684A3 (en)	2001-09-28
SK41599A3 (en)	2000-12-11
RU2197963C2 (ru)	2003-02-10
AU7213698A (en)	1998-12-11
WO1998052549B1 (fr)	1999-05-14
JP2000513023A (ja)	2000-10-03
WO1998052549A3 (fr)	1999-04-08
EP0980242A2 (fr)	2000-02-23
IL132819A0 (en)	2001-03-19
CA2248955C (fr)	2001-08-14
CZ108099A3 (cs)	1999-08-11
HK1027512A1 (en)	2001-01-19
SK285897B6 (sk)	2007-10-04
DE19721099A1 (de)	1998-11-26
ES2190588T3 (es)	2003-08-01
EE9900535A (et)	2000-06-15
RS49654B (sr)	2007-09-21
YU57599A (sh)	2001-12-26
NO326815B1 (no)	2009-02-23
PL335381A1 (en)	2000-04-25
US6436992B1 (en)	2002-08-20
EE03999B1 (et)	2003-04-15
TR199902587T2 (xx)	2000-08-21
NO991342L (no)	1999-11-16
BG64613B1 (bg)	2005-09-30
WO1998052549A2 (fr)	1998-11-26
ATE232093T1 (de)	2003-02-15
NO991342D0 (no)	1999-03-19
NZ501755A (en)	2001-07-27
CZ299960B6 (cs)	2009-01-07
HUP0001684A2 (hu)	2000-09-28
DK0980242T3 (da)	2003-04-14
DE59807122D1 (de)	2003-03-13
PL190864B1 (pl)	2006-02-28
HU227697B1 (en)	2011-12-28
CN1257426A (zh)	2000-06-21
CA2248955A1 (fr)	1997-05-20
CN1153569C (zh)	2004-06-16
BG103335A (en)	2000-04-28
AU730441B2 (en)	2001-03-08

Legal Events

Date	Code	Title
2005-05-17	FF	Patent granted
2005-07-25	KB	Patent renewed
2008-06-05	KB	Patent renewed
2012-04-30	KB	Patent renewed
2016-04-21	KB	Patent renewed
2018-10-31	EXP	Patent expired

Publication	Publication Date	Title
US6436992B1 (en)	2002-08-20	Use of fumaric acid derivatives
US6359003B1 (en)	2002-03-19	Use of fumaric acid derivatives in transplant medicine
US7803840B2 (en)	2010-09-28	Utilization of dialkylfumarates
CA2526586C (fr)	2010-03-16	Utilisation de derives d'acide fumarique pour traiter l'insuffisance cardiaque et l'asthme
AU745889B2 (en)	2002-04-11	Fumaric acid microtablets
RS57599B1 (sr)	2018-11-30	Supstituirani natrijum-1h-pirazol-5-olat
ZA200601985B (en)	2007-05-30	The use of fumaric acid derivatives for treating cardiac insufficiency, and asthma
MXPA99010703A (en)	2000-09-04	Use of fumaric acid derivatives