RU2008143670A - Новые фармацевтические соединения - Google Patents
Новые фармацевтические соединения Download PDFInfo
- Publication number
- RU2008143670A RU2008143670A RU2008143670/04A RU2008143670A RU2008143670A RU 2008143670 A RU2008143670 A RU 2008143670A RU 2008143670/04 A RU2008143670/04 A RU 2008143670/04A RU 2008143670 A RU2008143670 A RU 2008143670A RU 2008143670 A RU2008143670 A RU 2008143670A
- Authority
- RU
- Russia
- Prior art keywords
- diol
- oxadiazol
- nitrobenzene
- diyl
- compound
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract 28
- -1 1,3 , 4-oxadiazole-2,5-diyl Chemical group 0.000 claims abstract 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 3
- 125000003435 aroyl group Chemical group 0.000 claims abstract 3
- 230000004962 physiological condition Effects 0.000 claims abstract 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims abstract 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims abstract 2
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims abstract 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 2
- 125000003118 aryl group Chemical group 0.000 claims abstract 2
- 125000001589 carboacyl group Chemical group 0.000 claims abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 150000002431 hydrogen Chemical class 0.000 claims abstract 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims abstract 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 23
- 150000003839 salts Chemical class 0.000 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 11
- 150000002148 esters Chemical class 0.000 claims 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 8
- 208000019430 Motor disease Diseases 0.000 claims 8
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 208000035475 disorder Diseases 0.000 claims 8
- 210000001428 peripheral nervous system Anatomy 0.000 claims 8
- 239000000203 mixture Substances 0.000 claims 7
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 6
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 6
- QJOAGGIONCIMFQ-UHFFFAOYSA-N 5-[3-(2,5-dichloro-4,6-dimethylpyridin-3-yl)-1,2,4-oxadiazol-5-yl]-3-nitrobenzene-1,2-diol Chemical compound CC1=C(Cl)C(C)=NC(Cl)=C1C1=NOC(C=2C=C(C(O)=C(O)C=2)[N+]([O-])=O)=N1 QJOAGGIONCIMFQ-UHFFFAOYSA-N 0.000 claims 4
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 4
- 206010020772 Hypertension Diseases 0.000 claims 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 4
- 206010030113 Oedema Diseases 0.000 claims 4
- 208000018737 Parkinson disease Diseases 0.000 claims 4
- 208000027089 Parkinsonian disease Diseases 0.000 claims 4
- 206010034010 Parkinsonism Diseases 0.000 claims 4
- 230000015572 biosynthetic process Effects 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 208000010643 digestive system disease Diseases 0.000 claims 4
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 4
- 230000001575 pathological effect Effects 0.000 claims 4
- 238000002360 preparation method Methods 0.000 claims 4
- 238000007363 ring formation reaction Methods 0.000 claims 4
- 102000003823 Aromatic-L-amino-acid decarboxylases Human genes 0.000 claims 3
- 108090000121 Aromatic-L-amino-acid decarboxylases Proteins 0.000 claims 3
- 229940081615 DOPA decarboxylase inhibitor Drugs 0.000 claims 3
- 229940123736 Decarboxylase inhibitor Drugs 0.000 claims 3
- 210000004556 brain Anatomy 0.000 claims 3
- 238000009833 condensation Methods 0.000 claims 3
- 230000005494 condensation Effects 0.000 claims 3
- 239000003954 decarboxylase inhibitor Substances 0.000 claims 3
- 230000018044 dehydration Effects 0.000 claims 3
- 238000006297 dehydration reaction Methods 0.000 claims 3
- 239000000534 dopa decarboxylase inhibitor Substances 0.000 claims 3
- 208000011580 syndromic disease Diseases 0.000 claims 3
- PFDUUKDQEHURQC-ZETCQYMHSA-N 3-O-methyldopa Chemical compound COC1=CC(C[C@H](N)C(O)=O)=CC=C1O PFDUUKDQEHURQC-ZETCQYMHSA-N 0.000 claims 2
- 102100038238 Aromatic-L-amino-acid decarboxylase Human genes 0.000 claims 2
- 101710151768 Aromatic-L-amino-acid decarboxylase Proteins 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- BNQDCRGUHNALGH-UHFFFAOYSA-N benserazide Chemical compound OCC(N)C(=O)NNCC1=CC=C(O)C(O)=C1O BNQDCRGUHNALGH-UHFFFAOYSA-N 0.000 claims 2
- 229960000911 benserazide Drugs 0.000 claims 2
- QTAOMKOIBXZKND-PPHPATTJSA-N carbidopa Chemical compound O.NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 QTAOMKOIBXZKND-PPHPATTJSA-N 0.000 claims 2
- 229960004205 carbidopa Drugs 0.000 claims 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims 2
- 239000002738 chelating agent Substances 0.000 claims 2
- 238000004806 packaging method and process Methods 0.000 claims 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims 2
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 1
- QJRVGCGNQHXFGS-UHFFFAOYSA-N 3-nitro-5-[3-[2-(trifluoromethyl)pyridin-3-yl]-1,2,4-oxadiazol-5-yl]benzene-1,2-diol Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C=2ON=C(N=2)C=2C(=NC=CC=2)C(F)(F)F)=C1 QJRVGCGNQHXFGS-UHFFFAOYSA-N 0.000 claims 1
- MPMRHUUMBJSGKR-UHFFFAOYSA-N 3-nitro-5-[3-[5-(trifluoromethyl)pyridin-3-yl]-1,2,4-oxadiazol-5-yl]benzene-1,2-diol Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C=2ON=C(N=2)C=2C=C(C=NC=2)C(F)(F)F)=C1 MPMRHUUMBJSGKR-UHFFFAOYSA-N 0.000 claims 1
- DGLBFVOUTZCJIN-UHFFFAOYSA-N 3-nitro-5-[3-[6-(trifluoromethyl)pyridin-3-yl]-1,2,4-oxadiazol-5-yl]benzene-1,2-diol Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C=2ON=C(N=2)C=2C=NC(=CC=2)C(F)(F)F)=C1 DGLBFVOUTZCJIN-UHFFFAOYSA-N 0.000 claims 1
- AALAWVYPYCIVLB-UHFFFAOYSA-N 3-nitro-5-[5-[2-(trifluoromethyl)pyridin-3-yl]-1,2,4-oxadiazol-3-yl]benzene-1,2-diol Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C=2N=C(ON=2)C=2C(=NC=CC=2)C(F)(F)F)=C1 AALAWVYPYCIVLB-UHFFFAOYSA-N 0.000 claims 1
- TXOIAEIWHYEYGK-UHFFFAOYSA-N 3-nitro-5-[5-[4-(trifluoromethyl)pyridin-3-yl]-1,2,4-oxadiazol-3-yl]benzene-1,2-diol Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C=2N=C(ON=2)C=2C(=CC=NC=2)C(F)(F)F)=C1 TXOIAEIWHYEYGK-UHFFFAOYSA-N 0.000 claims 1
- LUMQLEJDPZJMOV-UHFFFAOYSA-N 3-nitro-5-[5-[5-(trifluoromethyl)pyridin-3-yl]-1,2,4-oxadiazol-3-yl]benzene-1,2-diol Chemical compound [O-][N+](=O)C1=C(O)C(O)=CC(C=2N=C(ON=2)C=2C=C(C=NC=2)C(F)(F)F)=C1 LUMQLEJDPZJMOV-UHFFFAOYSA-N 0.000 claims 1
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- 150000004677 hydrates Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 150000004866 oxadiazoles Chemical class 0.000 claims 1
- 229960003540 oxyquinoline Drugs 0.000 claims 1
- 208000027232 peripheral nervous system disease Diseases 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000005000 thioaryl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 0 *c1c(*)nc(*)c(*)c1C#N Chemical compound *c1c(*)nc(*)c(*)c1C#N 0.000 description 1
Classifications
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- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
- A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
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- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- 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
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Psychology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| EP06007534A EP1845097A1 (en) | 2006-04-10 | 2006-04-10 | Oxadiazole derivatives as COMT inhibitors |
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| IL169855A (en) * | 2005-07-25 | 2014-05-28 | Elta Systems Ltd | A system and method for locating a receiver location |
| SI1907382T1 (sl) * | 2005-07-26 | 2015-10-30 | Bial-Portela & Ca S.A., | Nitrokateholni derivati kot inhibitorji COMT |
| EP1845097A1 (en) | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| AU2007334436A1 (en) | 2006-12-15 | 2008-06-26 | Abbott Laboratories | Novel oxadiazole compounds |
| ES2597705T3 (es) * | 2007-01-31 | 2017-01-20 | Bial - Portela & Ca., S.A. | Derivados de nitrocatecol como inhibidores de COMT administrados con un régimen de dosificación específico |
| EP2217571A2 (en) * | 2007-10-24 | 2010-08-18 | BIAL - Portela & Ca., S.A. | Novel precursors |
| TWI415607B (zh) | 2007-12-25 | 2013-11-21 | Kissei Pharmaceutical | 新穎兒茶酚衍生物、含有其之醫藥組成物及該等之用途 |
| EP2259777A2 (en) * | 2008-02-28 | 2010-12-15 | BIAL - Portela & Ca., S.A. | Pharmaceutical composition for poorly soluble drugs |
| EP2276758B1 (en) | 2008-03-17 | 2016-01-06 | Bial-Portela & CA, S.A. | Crystal forms of 5- [3- (2, 5-dichloro-4, 6-dimethyl-1-oxy-pyridine-3-yl) [1,2,4] oxadiazol-5-yl]-3-nit robenzene-1, 2-diol |
| PT2307020T (pt) * | 2008-07-29 | 2019-05-28 | Bial Portela & Ca Sa | Regime de administração de nitrocatecólicos |
| KR102329271B1 (ko) | 2009-04-01 | 2021-11-22 | 바이알 - 포르텔라 앤드 씨에이 에스에이 | 니트로카테콜 유도체를 포함하는 제약 제제 및 그의 제조 방법 |
| AU2010231962B2 (en) * | 2009-04-01 | 2015-05-21 | Bial - Portela & Ca., S.A. | Pharmaceutical formulations comprising nitrocatechol derivatives and methods of making the same |
| JP5529639B2 (ja) * | 2009-06-18 | 2014-06-25 | キッセイ薬品工業株式会社 | 新規なカテコール−o−メチルトランスフェラーゼ阻害剤 |
| WO2011069075A2 (en) * | 2009-12-04 | 2011-06-09 | Grant Jon E | Treating impulse control disorders with catechol-o- methyl-transferase inhibitors |
| US20140045900A1 (en) | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| PL2791134T3 (pl) * | 2011-12-13 | 2020-03-31 | BIAL - PORTELA & Cª S.A. | Związek chemiczny użyteczny jako związek pośredni do wytwarzania inhibitora katechol-o-metylotransferazy |
| TWI638802B (zh) | 2012-05-24 | 2018-10-21 | 芬蘭商奧利安公司 | 兒茶酚o-甲基轉移酶活性抑制化合物 |
| RU2017120184A (ru) | 2014-11-28 | 2018-12-28 | БИАЛ - ПОРТЕЛА ЭНД Ка, С.А. | Лекарства для замедления течения болезни паркинсона |
| US10532976B2 (en) * | 2015-06-23 | 2020-01-14 | National Institute Of Biological Sciences, Beijing | FTO inhibitors |
| WO2016206573A1 (en) * | 2015-06-23 | 2016-12-29 | National Institute Of Biological Sciences, Beijing | Fto inhibitors |
| DE102016009081A1 (de) * | 2016-07-26 | 2018-02-01 | Man Truck & Bus Ag | Verfahren und Vorrichtung zur Steuerung oder Regelung einer Fahrerhaus-Lagerung |
| CN108314631A (zh) * | 2018-04-19 | 2018-07-24 | 中国科学院昆明植物研究所 | 二芳基乙烯类化合物及其药物组合物和其应用 |
| US12097193B2 (en) | 2018-10-05 | 2024-09-24 | Bial—Portela & Ca, S.A. | Methods for the administration of COMT inhibitors |
| CN112375014A (zh) * | 2020-12-17 | 2021-02-19 | 重庆柳江医药科技有限公司 | 一种奥匹卡朋工艺杂质及制备方法和用途 |
| CN116283664B (zh) * | 2023-01-12 | 2025-05-16 | 中国药科大学 | 一种硝基儿茶酚衍生物、包含其的药物组合物及其应用 |
| WO2024260874A1 (en) | 2023-06-19 | 2024-12-26 | Medichem, S.A. | Process for preparing opicapone |
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| US1532178A (en) * | 1921-07-25 | 1925-04-07 | Louis A Godbold | Lubricator |
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-
2006
- 2006-04-10 EP EP06007534A patent/EP1845097A1/en not_active Withdrawn
-
2007
- 2007-04-10 US US12/226,260 patent/US8536203B2/en not_active Expired - Fee Related
- 2007-04-10 RU RU2008143670/04A patent/RU2008143670A/ru not_active Application Discontinuation
- 2007-04-10 ES ES07747756.0T patent/ES2565019T3/es active Active
- 2007-04-10 CN CN2007800191312A patent/CN101454285B/zh not_active Expired - Fee Related
- 2007-04-10 MX MX2008013020A patent/MX2008013020A/es not_active Application Discontinuation
- 2007-04-10 WO PCT/PT2007/000016 patent/WO2007117165A1/en not_active Ceased
- 2007-04-10 AU AU2007235755A patent/AU2007235755A1/en not_active Abandoned
- 2007-04-10 AR ARP070101517A patent/AR060421A1/es unknown
- 2007-04-10 CA CA2648914A patent/CA2648914C/en active Active
- 2007-04-10 EP EP12179360.8A patent/EP2617713A1/en not_active Withdrawn
- 2007-04-10 KR KR1020087026652A patent/KR20080108327A/ko not_active Withdrawn
- 2007-04-10 BR BRPI0711538-5A patent/BRPI0711538A2/pt not_active IP Right Cessation
- 2007-04-10 EP EP07747756.0A patent/EP2027091B1/en active Active
- 2007-04-10 JP JP2009505314A patent/JP5442434B2/ja active Active
-
2008
- 2008-11-06 ZA ZA200809479A patent/ZA200809479B/xx unknown
- 2008-11-07 NO NO20084712A patent/NO20084712L/no not_active Application Discontinuation
-
2013
- 2013-08-30 US US14/014,548 patent/US9446012B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| KR20080108327A (ko) | 2008-12-12 |
| NO20084712L (no) | 2008-12-30 |
| CN101454285B (zh) | 2012-06-27 |
| EP2027091A1 (en) | 2009-02-25 |
| CN101454285A (zh) | 2009-06-10 |
| US20140024682A1 (en) | 2014-01-23 |
| EP2027091B1 (en) | 2016-01-06 |
| JP2009533423A (ja) | 2009-09-17 |
| WO2007117165A1 (en) | 2007-10-18 |
| EP2617713A1 (en) | 2013-07-24 |
| AU2007235755A1 (en) | 2007-10-18 |
| AR060421A1 (es) | 2008-06-18 |
| MX2008013020A (es) | 2008-12-18 |
| JP5442434B2 (ja) | 2014-03-12 |
| ES2565019T3 (es) | 2016-03-30 |
| US8536203B2 (en) | 2013-09-17 |
| EP1845097A1 (en) | 2007-10-17 |
| US9446012B2 (en) | 2016-09-20 |
| CA2648914A1 (en) | 2007-10-18 |
| BRPI0711538A2 (pt) | 2011-11-01 |
| US20100168113A1 (en) | 2010-07-01 |
| CA2648914C (en) | 2016-08-02 |
| ZA200809479B (en) | 2009-10-28 |
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Legal Events
| Date | Code | Title | Description |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20120426 |