LU87412A1 - Nouvelle utilisation d'inhibiteurs de catechol-0-methyl transferase(comt)et de leurs esters et sels physiologiquement acceptables - Google Patents

Nouvelle utilisation d'inhibiteurs de catechol-0-methyl transferase(comt)et de leurs esters et sels physiologiquement acceptables Download PDF

Info

Publication number: LU87412A1
Authority: LU; Luxembourg
Prior art keywords: radical; use according; compound used; dihydroxy; optionally substituted
Prior art date: 1987-12-24

Application number

LU87412A

Other languages

English (en)

French (fr)

Inventor

Aho Paeivi

Pohto Pentti

Linden Inge-Britt

Baeckstroem Reijo

Honkanen Erkki

Nissinen Erkki

Original Assignee

Orion Yhtymae Oy

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.)

1987-12-24

Filing date

1988-12-22

Publication date

1989-06-14

1987-12-24 Priority claimed from GB878730190A external-priority patent/GB8730190D0/en

1988-12-22 Application filed by Orion Yhtymae Oy filed Critical Orion Yhtymae Oy

1989-06-14 Publication of LU87412A1 publication Critical patent/LU87412A1/fr

Links

150000002148 esters Chemical class 0.000 title claims description 12
239000003112 inhibitor Substances 0.000 title claims description 5
102000004357 Transferases Human genes 0.000 title description 2
108090000992 Transferases Proteins 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 54
-1 3,4-dihydroxy-5-nitrophenyl Chemical group 0.000 claims description 26
208000025865 Ulcer Diseases 0.000 claims description 21
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 17
231100000397 ulcer Toxicity 0.000 claims description 16
230000003902 lesion Effects 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 12
UPMRZALMHVUCIN-UHFFFAOYSA-N Nitecapone Chemical compound CC(=O)C(C(C)=O)=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 UPMRZALMHVUCIN-UHFFFAOYSA-N 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
VDCDWNDTNSWDFJ-UHFFFAOYSA-N 3,5-dinitrocatechol Chemical compound OC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O VDCDWNDTNSWDFJ-UHFFFAOYSA-N 0.000 claims description 7
JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 claims description 7
239000004215 Carbon black (E152) Substances 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
229930195733 hydrocarbon Natural products 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
239000003543 catechol methyltransferase inhibitor Substances 0.000 claims description 5
210000001035 gastrointestinal tract Anatomy 0.000 claims description 5
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
125000004430 oxygen atom Chemical group O* 0.000 claims description 5
238000011282 treatment Methods 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
125000003435 aroyl group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
125000000623 heterocyclic group Chemical group 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
238000011321 prophylaxis Methods 0.000 claims description 3
ORFIOGODBKQBRD-UHFFFAOYSA-N 3-[(3-chloro-5-ethoxy-4-hydroxyphenyl)methylidene]pentane-2,4-dione Chemical compound CCOC1=CC(C=C(C(C)=O)C(C)=O)=CC(Cl)=C1O ORFIOGODBKQBRD-UHFFFAOYSA-N 0.000 claims description 2
RGJOEKWQDUBAIZ-HDCXRZRFSA-N [[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3s)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphate Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@H](O)C(=O)NCCC(=O)NCCS)O[C@H]1N1C2=NC=NC(N)=C2N=C1 RGJOEKWQDUBAIZ-HDCXRZRFSA-N 0.000 claims description 2
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000005518 carboxamido group Chemical group 0.000 claims description 2
125000005019 carboxyalkenyl group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
TZMFJUDUGYTVRY-UHFFFAOYSA-N ethyl methyl diketone Natural products CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 claims description 2
150000002430 hydrocarbons Chemical class 0.000 claims description 2
125000001841 imino group Chemical group [H]N=* 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
150000001408 amides Chemical class 0.000 claims 3
239000002253 acid Substances 0.000 claims 2
150000001299 aldehydes Chemical class 0.000 claims 2
125000001589 carboacyl group Chemical group 0.000 claims 2
ILPPXXONOPVBRH-UHFFFAOYSA-N (2-acetyloxy-3,5-dinitrophenyl) acetate Chemical compound CC(=O)OC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(C)=O ILPPXXONOPVBRH-UHFFFAOYSA-N 0.000 claims 1
VWMRQPVPRMUIRP-UHFFFAOYSA-N (2-hydroxy-3,5-dinitrophenyl) 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O VWMRQPVPRMUIRP-UHFFFAOYSA-N 0.000 claims 1
UTCONHFSIFTRPV-HMMKTVFPSA-N (2e,5e)-2,5-bis[(3,4-dihydroxy-5-nitrophenyl)methylidene]cyclopentan-1-one Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(\C=C/2C(C(=C/C=3C=C(C(O)=C(O)C=3)[N+]([O-])=O)/CC\2)=O)=C1 UTCONHFSIFTRPV-HMMKTVFPSA-N 0.000 claims 1
RZTRFWLYXYIRAX-UHFFFAOYSA-N 1-(3,4-dihydroxy-5-nitrophenyl)ethanone Chemical compound CC(=O)C1=CC(O)=C(O)C([N+]([O-])=O)=C1 RZTRFWLYXYIRAX-UHFFFAOYSA-N 0.000 claims 1
BBFJODMCHICIAA-UHFFFAOYSA-N 3,4-dihydroxy-5-nitrobenzaldehyde Chemical compound OC1=CC(C=O)=CC([N+]([O-])=O)=C1O BBFJODMCHICIAA-UHFFFAOYSA-N 0.000 claims 1
JRBDMOJXCREXNN-UHFFFAOYSA-N 3,4-dihydroxy-5-nitrobenzonitrile Chemical compound OC1=CC(C#N)=CC([N+]([O-])=O)=C1O JRBDMOJXCREXNN-UHFFFAOYSA-N 0.000 claims 1
DRUCSFHPUMZHFZ-UHFFFAOYSA-N 3-(3,4-dihydroxy-5-nitrophenyl)-1-(3,4,5-trimethoxyphenyl)prop-2-en-1-one Chemical compound COC1=C(OC)C(OC)=CC(C(=O)C=CC=2C=C(C(O)=C(O)C=2)[N+]([O-])=O)=C1 DRUCSFHPUMZHFZ-UHFFFAOYSA-N 0.000 claims 1
HIEZRGPTEOHFQX-UHFFFAOYSA-N 3-[(3-hydroxy-4-methoxy-5-nitrophenyl)methylidene]pentane-2,4-dione Chemical compound COC1=C(O)C=C(C=C(C(C)=O)C(C)=O)C=C1[N+]([O-])=O HIEZRGPTEOHFQX-UHFFFAOYSA-N 0.000 claims 1
MJUWWBJMGJMFRR-UHFFFAOYSA-N 5-(3,4-dihydroxy-5-nitrophenyl)pentanoic acid Chemical compound OC(=O)CCCCC1=CC(O)=C(O)C([N+]([O-])=O)=C1 MJUWWBJMGJMFRR-UHFFFAOYSA-N 0.000 claims 1
WWDJBWMMHXMHND-UHFFFAOYSA-N 5-(3-hydroxy-2-methylbut-1-enyl)-3-nitrobenzene-1,2-diol Chemical compound CC(O)C(C)=CC1=CC(O)=C(O)C([N+]([O-])=O)=C1 WWDJBWMMHXMHND-UHFFFAOYSA-N 0.000 claims 1
YUMZFEGWCGNXHR-UHFFFAOYSA-N 5-chloro-3-nitrobenzene-1,2-diol Chemical compound OC1=CC(Cl)=CC([N+]([O-])=O)=C1O YUMZFEGWCGNXHR-UHFFFAOYSA-N 0.000 claims 1
125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
229910052801 chlorine Inorganic materials 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 1
241000700159 Rattus Species 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 11
208000000718 duodenal ulcer Diseases 0.000 description 11
229960003151 mercaptamine Drugs 0.000 description 11
150000003254 radicals Chemical class 0.000 description 8
210000001198 duodenum Anatomy 0.000 description 7
230000002496 gastric effect Effects 0.000 description 7
102000006378 Catechol O-methyltransferase Human genes 0.000 description 6
108020002739 Catechol O-methyltransferase Proteins 0.000 description 6
230000006378 damage Effects 0.000 description 6
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 6
238000000034 method Methods 0.000 description 6
239000003826 tablet Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 5
230000036269 ulceration Effects 0.000 description 5
229940079593 drug Drugs 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
208000008469 Peptic Ulcer Diseases 0.000 description 3
239000003699 antiulcer agent Substances 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
229960003638 dopamine Drugs 0.000 description 3
230000000694 effects Effects 0.000 description 3
210000000664 rectum Anatomy 0.000 description 3
210000002784 stomach Anatomy 0.000 description 3
239000000829 suppository Substances 0.000 description 3
150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
230000003187 abdominal effect Effects 0.000 description 2
238000010171 animal model Methods 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
210000001072 colon Anatomy 0.000 description 2
230000002183 duodenal effect Effects 0.000 description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
210000004877 mucosa Anatomy 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
230000008506 pathogenesis Effects 0.000 description 2
208000011906 peptic ulcer disease Diseases 0.000 description 2
230000003449 preventive effect Effects 0.000 description 2
210000000813 small intestine Anatomy 0.000 description 2
206010009900 Colitis ulcerative Diseases 0.000 description 1
208000007882 Gastritis Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
241000282412 Homo Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
125000002066 L-histidyl group Chemical group [H]N1C([H])=NC(C([H])([H])[C@](C(=O)[*])([H])N([H])[H])=C1[H] 0.000 description 1
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 1
206010028813 Nausea Diseases 0.000 description 1
206010030201 Oesophageal ulcer Diseases 0.000 description 1
208000027089 Parkinsonian disease Diseases 0.000 description 1
206010034010 Parkinsonism Diseases 0.000 description 1
240000007591 Tilia tomentosa Species 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000013475 authorization Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical class C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 1
230000001120 cytoprotective effect Effects 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
229940052760 dopamine agonists Drugs 0.000 description 1
239000003210 dopamine receptor blocking agent Substances 0.000 description 1
239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000003628 erosive effect Effects 0.000 description 1
208000028299 esophageal disease Diseases 0.000 description 1
208000019064 esophageal ulcer Diseases 0.000 description 1
210000003238 esophagus Anatomy 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000002008 hemorrhagic effect Effects 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
208000014674 injury Diseases 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N malonic acid group Chemical group C(CC(=O)O)(=O)O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
230000004899 motility Effects 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
230000008693 nausea Effects 0.000 description 1
208000013435 necrotic lesion Diseases 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
230000007310 pathophysiology Effects 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000029305 taxis Effects 0.000 description 1

Classifications

- 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
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/05—Phenols
- A61K31/06—Phenols the aromatic ring being substituted by nitro groups
- 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
- 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
- A61K31/12—Ketones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

LU87412A 1987-12-24 1988-12-22 Nouvelle utilisation d'inhibiteurs de catechol-0-methyl transferase(comt)et de leurs esters et sels physiologiquement acceptables LU87412A1 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB8730190		1987-12-24
GB878730190A GB8730190D0 (en)	1987-12-24	1987-12-24	New use of catechol-o-methyl transferase(comt)inhibitors & their physiologically acceptable salts & esters
GB8820729		1988-09-01
GB888820729A GB8820729D0 (en)	1987-12-24	1988-09-01	Substituted beta-diketones

Publications (1)

Publication Number	Publication Date
LU87412A1 true LU87412A1 (fr)	1989-06-14

Family

ID=26293247

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU87412A LU87412A1 (fr)	1987-12-24	1988-12-22	Nouvelle utilisation d'inhibiteurs de catechol-0-methyl transferase(comt)et de leurs esters et sels physiologiquement acceptables

Country Status (17)

Country	Link
US (1)	US5001152A (de)
EP (1)	EP0323162B1 (de)
JP (1)	JPH02196715A (de)
AU (1)	AU617397B2 (de)
BE (1)	BE1003759A5 (de)
CH (1)	CH683395A5 (de)
DE (1)	DE3843324A1 (de)
DK (1)	DK713288A (de)
ES (1)	ES2059546T3 (de)
HU (1)	HU200684B (de)
IE (1)	IE883816L (de)
IL (1)	IL88734A (de)
IT (1)	IT1227914B (de)
LU (1)	LU87412A1 (de)
MT (1)	MTP1031B (de)
PH (1)	PH27037A (de)
SE (1)	SE8804608L (de)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5283352A (en) *	1986-11-28	1994-02-01	Orion-Yhtyma Oy	Pharmacologically active compounds, methods for the preparation thereof and compositions containing the same
GB9004348D0 (en) *	1990-02-27	1990-04-25	Orion Yhtymae Oy	New use of catechol derivatives and their physiologically acceptable salts and esters
US5185370A (en) *	1988-09-01	1993-02-09	Orion-Yhtyma Oy	Substituted β-diketones and their use
IL91382A (en) *	1988-09-01	1995-06-29	Orion Yhtymae Oy	Alkenyl or arylmethylene-substituted beta-diketones their preparation and pharmaceutical compositions containing them
GB9002337D0 (en) *	1990-02-02	1990-04-04	Orion Yhtymae Oy	Compounds useful in treating inflammatory bowel disease
JPH05301838A (ja) *	1991-10-15	1993-11-16	Mitsubishi Kasei Corp	スチレン誘導体
GB9626472D0 (en) *	1996-12-20	1997-02-05	Aperia Anita C	New use of comt inhibitors
FI981521A0 (fi)	1998-07-01	1998-07-01	Orion Corp	Substituoidut beta-diketonit ja niiden käyttö
FI20000635A0 (fi) *	2000-03-17	2000-03-17	Orion Yhtymae Oyj	COMT-inhibiittoreiden käyttö analgeettina
GB0015228D0 (en) *	2000-06-21	2000-08-16	Portela & Ca Sa	Substituted nitrated catechols, their use in the treatment of some central and peripheral nervous system disorders

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB902586A (en) *	1960-01-01	1962-08-01	Shell Res Ltd	Herbicidal compositions and novel compounds for use therein
GB1188364A (en) *	1967-05-02	1970-04-15	May & Baker Ltd	Quinoline Derivatives
BE759266A (fr) *	1969-11-24	1971-05-24	Hoffmann La Roche	Procede pour la preparation de derives de l'indole
CA1190223A (en) *	1977-11-01	1985-07-09	National Research Development Corporation	Substrates for enzymes
FR2504004A1 (fr) *	1981-04-17	1982-10-22	Roussel Uclaf	Application a titre de medicaments de derives d'acides phenyl aliphatique carboxyliques
JPS5890534A (ja) *	1981-11-25	1983-05-30	Ono Pharmaceut Co Ltd	２−アミノフエノ−ル誘導体、その製造方法およびその誘導体を有効成分として含有する治療剤
ES8505914A1 (es) *	1983-05-13	1985-06-16	Yamanouchi Pharma Co Ltd	Un procedimiento para la produccion de un derivado de catecol
FR2557098B1 (fr) *	1983-12-22	1986-06-13	Rhone Poulenc Spec Chim	Procede de preparation de bromobenzaldehydes hydroxy et/ou alkoxy substitues
FR2557097B1 (fr) *	1983-12-22	1986-06-13	Rhone Poulenc Spec Chim	Procede de preparation de bromobenzaldehydes hydroxy et/ou alkoxy substitues
US4760089A (en) *	1985-09-09	1988-07-26	Smithkline Beckman Corporation	Irreversible dopamine-β-hydroxylase inhibitors
DK175069B1 (da) *	1986-03-11	2004-05-24	Hoffmann La Roche	Pyrocatecholderivater
YU213587A (en) *	1986-11-28	1989-06-30	Orion Yhtymae Oy	Process for obtaining new pharmacologic active cateholic derivatives
DK49688A (da) *	1987-03-20	1988-09-21	Hoffmann La Roche	Propiolophenonderivater

1988
- 1988-12-16 MT MT1031A patent/MTP1031B/xx unknown
- 1988-12-20 IL IL8873488A patent/IL88734A/en not_active IP Right Cessation
- 1988-12-21 DK DK713288A patent/DK713288A/da not_active Application Discontinuation
- 1988-12-21 SE SE8804608A patent/SE8804608L/xx not_active Application Discontinuation
- 1988-12-21 IE IE883816A patent/IE883816L/xx unknown
- 1988-12-22 DE DE3843324A patent/DE3843324A1/de not_active Withdrawn
- 1988-12-22 ES ES88312228T patent/ES2059546T3/es not_active Expired - Lifetime
- 1988-12-22 LU LU87412A patent/LU87412A1/fr unknown
- 1988-12-22 CH CH4750/88A patent/CH683395A5/de not_active IP Right Cessation
- 1988-12-22 EP EP88312228A patent/EP0323162B1/de not_active Expired - Lifetime
- 1988-12-22 PH PH37972A patent/PH27037A/en unknown
- 1988-12-23 AU AU27459/88A patent/AU617397B2/en not_active Ceased
- 1988-12-23 BE BE8801433A patent/BE1003759A5/fr not_active IP Right Cessation
- 1988-12-23 IT IT8823107A patent/IT1227914B/it active
- 1988-12-23 US US07/288,979 patent/US5001152A/en not_active Expired - Fee Related
- 1988-12-23 JP JP63327515A patent/JPH02196715A/ja active Pending
- 1988-12-23 HU HU886594A patent/HU200684B/hu not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK713288D0 (da)	1988-12-21
EP0323162B1 (de)	1993-09-15
IE883816L (en)	1989-06-24
DE3843324A1 (de)	1989-07-06
AU2745988A (en)	1989-06-29
IT8823107A0 (it)	1988-12-23
JPH02196715A (ja)	1990-08-03
AU617397B2 (en)	1991-11-28
IT1227914B (it)	1991-05-14
PH27037A (en)	1993-02-01
MTP1031B (en)	1990-10-04
HUT49053A (en)	1989-08-28
IL88734A0 (en)	1989-07-31
ES2059546T3 (es)	1994-11-16
IL88734A (en)	1994-01-25
CH683395A5 (de)	1994-03-15
SE8804608D0 (sv)	1988-12-21
DK713288A (da)	1989-06-25
HU200684B (en)	1990-08-28
SE8804608L (sv)	1989-06-25
US5001152A (en)	1991-03-19
BE1003759A5 (fr)	1992-06-09
EP0323162A2 (de)	1989-07-05
EP0323162A3 (en)	1990-11-14

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