NO333504B1 - Farmasoytisk sammensetning for a forbedre hjernefunksjon samt et alkyleterderivat som inngar i denne sammensetningen - Google Patents

Farmasoytisk sammensetning for a forbedre hjernefunksjon samt et alkyleterderivat som inngar i denne sammensetningen Download PDF

Info

Publication number: NO333504B1
Authority: NO; Norway
Prior art keywords: salt; hydroxyl group; component; alkyl ether; group
Prior art date: 2002-06-14

Application number

NO20045158A

Other languages

English (en)

Norwegian (no)

Other versions

NO20045158L (no

Inventor

Masaya Nakagawa

Satoshi Ono

Yasushi Nakada

Original Assignee

Toyama Chemical Co Ltd

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.)

2002-06-14

Filing date

2004-11-25

Publication date

2013-06-24

2004-11-25 Application filed by Toyama Chemical Co Ltd filed Critical Toyama Chemical Co Ltd

2005-03-10 Publication of NO20045158L publication Critical patent/NO20045158L/no

2013-06-24 Publication of NO333504B1 publication Critical patent/NO333504B1/no

Links

150000005215 alkyl ethers Chemical class 0.000 title claims abstract description 13
239000008194 pharmaceutical composition Substances 0.000 title abstract 2
230000003925 brain function Effects 0.000 title description 4
239000000203 mixture Substances 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 27
ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 claims abstract description 22
230000002490 cerebral effect Effects 0.000 claims abstract description 17
229960003530 donepezil Drugs 0.000 claims abstract description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
229960001685 tacrine Drugs 0.000 claims abstract description 8
YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 claims abstract description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 4
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
125000002393 azetidinyl group Chemical group 0.000 claims abstract 3
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 3
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 7
HQNACSFBDBYLJP-UHFFFAOYSA-N 1-[3-[2-(1-benzothiophen-5-yl)ethoxy]propyl]azetidin-3-ol Chemical compound C1C(O)CN1CCCOCCC1=CC=C(SC=C2)C2=C1 HQNACSFBDBYLJP-UHFFFAOYSA-N 0.000 claims 2
YJFGQHCDMAPJFY-UHFFFAOYSA-N 2-[3-[2-(1-benzothiophen-5-yl)ethoxy]propyl-methylamino]ethanol Chemical compound OCCN(C)CCCOCCC1=CC=C2SC=CC2=C1 YJFGQHCDMAPJFY-UHFFFAOYSA-N 0.000 claims 2
208000024827 Alzheimer disease Diseases 0.000 abstract description 9
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 abstract description 8
229960004373 acetylcholine Drugs 0.000 abstract description 8
210000002569 neuron Anatomy 0.000 abstract description 8
230000016273 neuron death Effects 0.000 abstract description 6
230000004064 dysfunction Effects 0.000 abstract description 5
206010008190 Cerebrovascular accident Diseases 0.000 abstract description 4
206010039966 Senile dementia Diseases 0.000 abstract description 4
208000006011 Stroke Diseases 0.000 abstract description 4
208000013677 cerebrovascular dementia Diseases 0.000 abstract description 4
230000000302 ischemic effect Effects 0.000 abstract description 4
230000003902 lesion Effects 0.000 abstract description 4
206010027175 memory impairment Diseases 0.000 abstract description 4
230000002265 prevention Effects 0.000 abstract description 2
239000004615 ingredient Substances 0.000 abstract 3
238000004519 manufacturing process Methods 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 29
230000002401 inhibitory effect Effects 0.000 description 12
102000012440 Acetylcholinesterase Human genes 0.000 description 11
108010022752 Acetylcholinesterase Proteins 0.000 description 11
229940022698 acetylcholinesterase Drugs 0.000 description 11
230000000141 anti-hypoxic effect Effects 0.000 description 9
BKMCUGFGPQNYHG-RSAXXLAASA-N (1r)-1-(1-benzothiophen-5-yl)-2-[2-(diethylamino)ethoxy]ethanol;hydrochloride Chemical compound Cl.CCN(CC)CCOC[C@H](O)C1=CC=C2SC=CC2=C1 BKMCUGFGPQNYHG-RSAXXLAASA-N 0.000 description 8
210000004556 brain Anatomy 0.000 description 7
230000000694 effects Effects 0.000 description 7
238000012360 testing method Methods 0.000 description 6
229940079593 drug Drugs 0.000 description 5
239000003814 drug Substances 0.000 description 5
238000000034 method Methods 0.000 description 5
230000000324 neuroprotective effect Effects 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012153 distilled water Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000000243 solution Substances 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
229940100578 Acetylcholinesterase inhibitor Drugs 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000000544 cholinesterase inhibitor Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
ASUTZQLVASHGKV-JDFRZJQESA-N galanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CN(C)CC[C@]23[C@@H]1C[C@@H](O)C=C2 ASUTZQLVASHGKV-JDFRZJQESA-N 0.000 description 2
239000008246 gaseous mixture Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
JGPMMRGNQUBGND-UHFFFAOYSA-N idebenone Chemical compound COC1=C(OC)C(=O)C(CCCCCCCCCCO)=C(C)C1=O JGPMMRGNQUBGND-UHFFFAOYSA-N 0.000 description 2
229960004135 idebenone Drugs 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
-1 nitrogen-containing organic base Chemical class 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
230000004083 survival effect Effects 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
LXFQSRIDYRFTJW-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonic acid Chemical compound CC1=CC(C)=C(S(O)(=O)=O)C(C)=C1 LXFQSRIDYRFTJW-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
SFHYNDMGZXWXBU-LIMNOBDPSA-N 6-amino-2-[[(e)-(3-formylphenyl)methylideneamino]carbamoylamino]-1,3-dioxobenzo[de]isoquinoline-5,8-disulfonic acid Chemical compound O=C1C(C2=3)=CC(S(O)(=O)=O)=CC=3C(N)=C(S(O)(=O)=O)C=C2C(=O)N1NC(=O)N\N=C\C1=CC=CC(C=O)=C1 SFHYNDMGZXWXBU-LIMNOBDPSA-N 0.000 description 1
208000000044 Amnesia Diseases 0.000 description 1
208000031091 Amnestic disease Diseases 0.000 description 1
102000013455 Amyloid beta-Peptides Human genes 0.000 description 1
108010090849 Amyloid beta-Peptides Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
206010012735 Diarrhoea Diseases 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
206010023644 Lacrimation increased Diseases 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
NSGDYZCDUPSTQT-UHFFFAOYSA-N N-[5-bromo-1-[(4-fluorophenyl)methyl]-4-methyl-2-oxopyridin-3-yl]cycloheptanecarboxamide Chemical compound Cc1c(Br)cn(Cc2ccc(F)cc2)c(=O)c1NC(=O)C1CCCCCC1 NSGDYZCDUPSTQT-UHFFFAOYSA-N 0.000 description 1
108010025020 Nerve Growth Factor Proteins 0.000 description 1
102000015336 Nerve Growth Factor Human genes 0.000 description 1
102000000728 Nerve growth factor-like Human genes 0.000 description 1
108050008149 Nerve growth factor-like Proteins 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
206010039424 Salivary hypersecretion Diseases 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
UPABQMWFWCMOFV-UHFFFAOYSA-N benethamine Chemical compound C=1C=CC=CC=1CNCCC1=CC=CC=C1 UPABQMWFWCMOFV-UHFFFAOYSA-N 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
230000037396 body weight Effects 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
208000026106 cerebrovascular disease Diseases 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
229940021171 curative drug Drugs 0.000 description 1
230000034994 death Effects 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000003889 eye drop Substances 0.000 description 1
239000004503 fine granule Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
230000006870 function Effects 0.000 description 1
229960003980 galantamine Drugs 0.000 description 1
ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000010005 growth-factor like effect Effects 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
ZUFVXZVXEJHHBN-UHFFFAOYSA-N hydron;1,2,3,4-tetrahydroacridin-9-amine;chloride Chemical compound [Cl-].C1=CC=C2C([NH3+])=C(CCCC3)C3=NC2=C1 ZUFVXZVXEJHHBN-UHFFFAOYSA-N 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000004317 lacrimation Effects 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
239000011707 mineral Substances 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229940053128 nerve growth factor Drugs 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
210000001002 parasympathetic nervous system Anatomy 0.000 description 1
210000001428 peripheral nervous system Anatomy 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000011160 research Methods 0.000 description 1
208000026451 salivation Diseases 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000002636 symptomatic treatment Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
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239000003826 tablet Substances 0.000 description 1
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230000001225 therapeutic effect Effects 0.000 description 1
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IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- 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
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
- 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
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
- 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
- A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
- 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
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/473—Quinolines; Isoquinolines ortho- or peri-condensed with carbocyclic ring systems, e.g. acridines, phenanthridines
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- 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

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Veterinary Medicine (AREA)
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Public Health (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
General Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Emergency Medicine (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Hospice & Palliative Care (AREA)
Urology & Nephrology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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NO20045158A 2002-06-14 2004-11-25 Farmasoytisk sammensetning for a forbedre hjernefunksjon samt et alkyleterderivat som inngar i denne sammensetningen NO333504B1 (no)

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Application Number	Priority Date	Filing Date	Title
JP2002173483		2002-06-14
PCT/JP2003/004292 WO2003105830A1 (ja)	2002-06-14	2003-04-03	脳機能を改善する医薬組成物および脳機能を改善するための方法

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NO20045158L NO20045158L (no)	2005-03-10
NO333504B1 true NO333504B1 (no)	2013-06-24

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NO20045158A NO333504B1 (no)	2002-06-14	2004-11-25	Farmasoytisk sammensetning for a forbedre hjernefunksjon samt et alkyleterderivat som inngar i denne sammensetningen

Country Status (23)

Country	Link
US (3)	US7342043B2 (de)
EP (2)	EP1514542B1 (de)
JP (1)	JP4675103B2 (de)
KR (1)	KR100935615B1 (de)
CN (1)	CN100375619C (de)
AT (1)	ATE546140T1 (de)
AU (1)	AU2003236364C1 (de)
BR (1)	BRPI0311780B8 (de)
CA (1)	CA2488120C (de)
CY (2)	CY1112958T1 (de)
DK (2)	DK2389937T3 (de)
ES (2)	ES2379948T3 (de)
HU (1)	HUE041842T2 (de)
IL (1)	IL165589A (de)
MX (1)	MXPA04012534A (de)
NO (1)	NO333504B1 (de)
NZ (1)	NZ537090A (de)
PL (1)	PL217394B1 (de)
PT (2)	PT2389937T (de)
SI (2)	SI2389937T1 (de)
TR (1)	TR201816386T4 (de)
WO (1)	WO2003105830A1 (de)
ZA (1)	ZA200409901B (de)

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2003
- 2003-04-03 HU HUE11006318A patent/HUE041842T2/hu unknown
- 2003-04-03 KR KR1020047020053A patent/KR100935615B1/ko not_active Expired - Lifetime
- 2003-04-03 JP JP2004512734A patent/JP4675103B2/ja not_active Expired - Lifetime
- 2003-04-03 SI SI200332578T patent/SI2389937T1/sl unknown
- 2003-04-03 NZ NZ537090A patent/NZ537090A/en not_active IP Right Cessation
- 2003-04-03 SI SI200332141T patent/SI1514542T1/sl unknown
- 2003-04-03 US US10/516,320 patent/US7342043B2/en not_active Ceased
- 2003-04-03 MX MXPA04012534A patent/MXPA04012534A/es active IP Right Grant
- 2003-04-03 PT PT11006318T patent/PT2389937T/pt unknown
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- 2003-04-03 AU AU2003236364A patent/AU2003236364C1/en not_active Expired
- 2003-04-03 EP EP03760132A patent/EP1514542B1/de not_active Expired - Lifetime
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- 2003-04-03 BR BRPI0311780A patent/BRPI0311780B8/pt not_active IP Right Cessation
- 2003-04-03 DK DK11006318.7T patent/DK2389937T3/en active
- 2003-04-03 TR TR2018/16386T patent/TR201816386T4/tr unknown
- 2003-04-03 PT PT03760132T patent/PT1514542E/pt unknown
- 2003-04-03 DK DK03760132.5T patent/DK1514542T3/da active
- 2003-04-03 IL IL165589A patent/IL165589A/en active IP Right Grant
- 2003-04-03 EP EP11006318.7A patent/EP2389937B1/de not_active Expired - Lifetime
- 2003-04-03 US US12/683,813 patent/USRE42327E1/en not_active Expired - Lifetime
- 2003-04-03 ES ES11006318.7T patent/ES2685923T3/es not_active Expired - Lifetime
- 2003-04-03 WO PCT/JP2003/004292 patent/WO2003105830A1/ja not_active Ceased
- 2003-04-03 AT AT03760132T patent/ATE546140T1/de active
- 2003-04-03 CA CA2488120A patent/CA2488120C/en not_active Expired - Lifetime
2004
- 2004-11-25 NO NO20045158A patent/NO333504B1/no not_active IP Right Cessation
- 2004-12-07 ZA ZA200409901A patent/ZA200409901B/xx unknown
2007
- 2007-12-17 US US11/957,832 patent/US7834053B2/en not_active Expired - Lifetime
2012
- 2012-05-08 CY CY20121100432T patent/CY1112958T1/el unknown
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Publication number	Publication date
US7834053B2 (en)	2010-11-16
EP1514542B1 (de)	2012-02-22
PL217394B1 (pl)	2014-07-31
DK1514542T3 (da)	2012-04-10
HUE041842T2 (hu)	2019-05-28
JPWO2003105830A1 (ja)	2005-10-13
PT1514542E (pt)	2012-03-27
EP2389937B1 (de)	2018-08-15
MXPA04012534A (es)	2005-04-19
NZ537090A (en)	2006-02-24
DK2389937T3 (en)	2018-11-12
AU2003236364B2 (en)	2008-08-21
ZA200409901B (en)	2006-07-26
EP1514542A1 (de)	2005-03-16
BR0311780A (pt)	2005-03-15
EP2389937A1 (de)	2011-11-30
WO2003105830A1 (ja)	2003-12-24
CA2488120C (en)	2012-04-17
PT2389937T (pt)	2018-10-26
NO20045158L (no)	2005-03-10
KR100935615B1 (ko)	2010-01-07
IL165589A0 (en)	2006-01-15
USRE42327E1 (en)	2011-05-03
ATE546140T1 (de)	2012-03-15
IL165589A (en)	2012-04-30
CY1112958T1 (el)	2016-04-13
ES2379948T3 (es)	2012-05-07
ES2685923T3 (es)	2018-10-15
TR201816386T4 (tr)	2018-11-21
CA2488120A1 (en)	2003-12-24
CN1662232A (zh)	2005-08-31
PL372934A1 (en)	2005-08-08
US20050250843A1 (en)	2005-11-10
US7342043B2 (en)	2008-03-11
SI1514542T1 (sl)	2012-06-29
CN100375619C (zh)	2008-03-19
BRPI0311780B1 (pt)	2017-09-26
AU2003236364A1 (en)	2003-12-31
CY1120591T1 (el)	2019-12-11
AU2003236364C1 (en)	2009-12-24
SI2389937T1 (sl)	2018-10-30
EP1514542A4 (de)	2009-06-03
JP4675103B2 (ja)	2011-04-20
KR20050010877A (ko)	2005-01-28
US20080103126A1 (en)	2008-05-01
BRPI0311780B8 (pt)	2021-05-25

Legal Events

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2023-04-11	MK1K	Patent expired

Publication	Publication Date	Title
NO333504B1 (no)	2013-06-24	Farmasoytisk sammensetning for a forbedre hjernefunksjon samt et alkyleterderivat som inngar i denne sammensetningen
US20240261288A1 (en)	2024-08-08	Combination of a 3-(imidazol-4-yl)-4-(amino)-benzenesulfonamide tead inhibitor with an egfr inhibitor and/or mek inhibitor for use in the treatment of lung cancer
JP5280357B2 (ja)	2013-09-04	Ｐｄｅ４の二環式ヘテロアリール阻害剤
EP2813498B1 (de)	2016-04-20	Verbindungen gegen Alzheimerkrankheit
TW202115065A (zh)	2021-04-16	Kras突變蛋白抑制劑
CA2615271C (en)	2011-02-15	Novel use of 1-[4-(5-cyanoindol-3-yl)butyl]-4-(2-carbamoyl-benzofuran-5-yl)-piperazine and its physiologically acceptable salts
TW200932249A (en)	2009-08-01	Combination therapy comprising SGLT inhibitors and DPP4 inhibitors
US7563795B2 (en)	2009-07-21	Phenyl-piperazine derivatives as modulators of muscarinic receptors
JP2022532379A (ja)	2022-07-14	神経変性および代謝障害の処置のための化合物
WO2015095337A2 (en)	2015-06-25	PYRAZOLO[1,5-a]PYRIMIDINECARBOXAMIDE DERIVATIVES FOR TREATING COGNITIVE IMPAIRMENT
CA3091012A1 (en)	2019-08-15	A method of treating pain
JPWO2004011430A1 (ja)	2005-11-24	ナトリウムチャネル阻害剤
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