HU226961B1 - Pharmaceutical compositions comprising s-(-)-n-propargyl-1-amino indan - Google Patents
Pharmaceutical compositions comprising s-(-)-n-propargyl-1-amino indan Download PDFInfo
- Publication number
- HU226961B1 HU226961B1 HU9904525A HUP9904525A HU226961B1 HU 226961 B1 HU226961 B1 HU 226961B1 HU 9904525 A HU9904525 A HU 9904525A HU P9904525 A HUP9904525 A HU P9904525A HU 226961 B1 HU226961 B1 HU 226961B1
- Authority
- HU
- Hungary
- Prior art keywords
- propargyl
- pai
- aminoindan
- mao
- medicament
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title description 8
- 239000003814 drug Substances 0.000 claims description 28
- 238000011282 treatment Methods 0.000 claims description 26
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 21
- 208000018652 Closed Head injury Diseases 0.000 claims description 20
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 14
- 208000014674 injury Diseases 0.000 claims description 12
- 206010021143 Hypoxia Diseases 0.000 claims description 9
- 230000006378 damage Effects 0.000 claims description 9
- 208000027418 Wounds and injury Diseases 0.000 claims description 7
- 230000007954 hypoxia Effects 0.000 claims description 6
- 210000003169 central nervous system Anatomy 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 210000005036 nerve Anatomy 0.000 claims description 4
- 230000008733 trauma Effects 0.000 claims description 4
- 206010002660 Anoxia Diseases 0.000 claims description 3
- 241000976983 Anoxia Species 0.000 claims description 3
- 230000007953 anoxia Effects 0.000 claims description 3
- 238000001990 intravenous administration Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000004770 neurodegeneration Effects 0.000 claims description 3
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 3
- 231100000189 neurotoxic Toxicity 0.000 claims description 3
- 230000002887 neurotoxic effect Effects 0.000 claims description 3
- 210000001428 peripheral nervous system Anatomy 0.000 claims description 3
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 208000028389 Nerve injury Diseases 0.000 claims description 2
- 208000006011 Stroke Diseases 0.000 claims description 2
- 230000034994 death Effects 0.000 claims description 2
- 208000037906 ischaemic injury Diseases 0.000 claims description 2
- 230000008764 nerve damage Effects 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 206010027175 memory impairment Diseases 0.000 claims 1
- 230000006993 memory improvement Effects 0.000 claims 1
- 230000008736 traumatic injury Effects 0.000 claims 1
- 241000700159 Rattus Species 0.000 description 42
- 102000010909 Monoamine Oxidase Human genes 0.000 description 39
- 108010062431 Monoamine oxidase Proteins 0.000 description 39
- 230000000694 effects Effects 0.000 description 39
- MEZLKOACVSPNER-GFCCVEGCSA-N selegiline Chemical group C#CCN(C)[C@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-GFCCVEGCSA-N 0.000 description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 20
- 241000699670 Mus sp. Species 0.000 description 17
- 229960003946 selegiline Drugs 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229940079593 drug Drugs 0.000 description 12
- 210000003414 extremity Anatomy 0.000 description 12
- 239000011780 sodium chloride Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 11
- RUOKEQAAGRXIBM-UHFFFAOYSA-N n-prop-2-ynyl-2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(NCC#C)CCC2=C1 RUOKEQAAGRXIBM-UHFFFAOYSA-N 0.000 description 11
- 230000000324 neuroprotective effect Effects 0.000 description 11
- 230000000926 neurological effect Effects 0.000 description 10
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 9
- 230000008859 change Effects 0.000 description 9
- 230000001684 chronic effect Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 229960002748 norepinephrine Drugs 0.000 description 9
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 9
- 230000011514 reflex Effects 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 8
- 230000004872 arterial blood pressure Effects 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 210000004556 brain Anatomy 0.000 description 7
- 210000003141 lower extremity Anatomy 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 230000035488 systolic blood pressure Effects 0.000 description 7
- 206010061216 Infarction Diseases 0.000 description 6
- 229940082992 antihypertensives mao inhibitors Drugs 0.000 description 6
- 230000007574 infarction Effects 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 6
- XBQBIMOUVWKNGG-UHFFFAOYSA-N 1-prop-2-ynyl-2,3-dihydroinden-1-amine Chemical compound C1=CC=C2C(N)(CC#C)CCC2=C1 XBQBIMOUVWKNGG-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 206010015995 Eyelid ptosis Diseases 0.000 description 5
- 241000282326 Felis catus Species 0.000 description 5
- 206010020772 Hypertension Diseases 0.000 description 5
- 230000036772 blood pressure Effects 0.000 description 5
- 150000003943 catecholamines Chemical class 0.000 description 5
- 230000002526 effect on cardiovascular system Effects 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 239000004090 neuroprotective agent Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 201000003004 ptosis Diseases 0.000 description 5
- QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 5
- 230000004083 survival effect Effects 0.000 description 5
- 239000008399 tap water Substances 0.000 description 5
- 235000020679 tap water Nutrition 0.000 description 5
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 4
- 206010013710 Drug interaction Diseases 0.000 description 4
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 4
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 4
- 210000000748 cardiovascular system Anatomy 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 230000033001 locomotion Effects 0.000 description 4
- 230000006742 locomotor activity Effects 0.000 description 4
- 238000003359 percent control normalization Methods 0.000 description 4
- 230000002093 peripheral effect Effects 0.000 description 4
- 229960003147 reserpine Drugs 0.000 description 4
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 4
- 230000002269 spontaneous effect Effects 0.000 description 4
- 238000001356 surgical procedure Methods 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- MEZLKOACVSPNER-LBPRGKRZSA-N (2s)-n-methyl-1-phenyl-n-prop-2-ynylpropan-2-amine Chemical group C#CCN(C)[C@@H](C)CC1=CC=CC=C1 MEZLKOACVSPNER-LBPRGKRZSA-N 0.000 description 3
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical class C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 206010002091 Anaesthesia Diseases 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 230000037005 anaesthesia Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 206010008118 cerebral infarction Diseases 0.000 description 3
- 230000015271 coagulation Effects 0.000 description 3
- 238000005345 coagulation Methods 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000001631 hypertensive effect Effects 0.000 description 3
- 229940098779 methanesulfonic acid Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000001537 neural effect Effects 0.000 description 3
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 210000003625 skull Anatomy 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- PKDBCJSWQUOKDO-UHFFFAOYSA-M 2,3,5-triphenyltetrazolium chloride Chemical compound [Cl-].C1=CC=CC=C1C(N=[N+]1C=2C=CC=CC=2)=NN1C1=CC=CC=C1 PKDBCJSWQUOKDO-UHFFFAOYSA-M 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- 206010008089 Cerebral artery occlusion Diseases 0.000 description 2
- 208000025103 Congenital isolated hyperinsulinism Diseases 0.000 description 2
- 206010011953 Decreased activity Diseases 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 206010016948 Food interaction Diseases 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 208000026139 Memory disease Diseases 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- DPWPWRLQFGFJFI-UHFFFAOYSA-N Pargyline Chemical compound C#CCN(C)CC1=CC=CC=C1 DPWPWRLQFGFJFI-UHFFFAOYSA-N 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- 208000020339 Spinal injury Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic propargylamine derivatives Chemical class 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 2
- 229960003529 diazepam Drugs 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 229940052764 dopaminergic anti-parkinson drug mao b inhibitors Drugs 0.000 description 2
- SDJLVPMBBFRBLL-UHFFFAOYSA-N dsp-4 Chemical compound ClCCN(CC)CC1=CC=CC=C1Br SDJLVPMBBFRBLL-UHFFFAOYSA-N 0.000 description 2
- 229940084238 eldepryl Drugs 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000000099 in vitro assay Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000005462 in vivo assay Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 208000028867 ischemia Diseases 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 230000007659 motor function Effects 0.000 description 2
- 230000006576 neuronal survival Effects 0.000 description 2
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 description 2
- 229960001779 pargyline Drugs 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 229960001412 pentobarbital Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- RUOKEQAAGRXIBM-GFCCVEGCSA-N rasagiline Chemical compound C1=CC=C2[C@H](NCC#C)CCC2=C1 RUOKEQAAGRXIBM-GFCCVEGCSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 210000000966 temporal muscle Anatomy 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 208000035657 Abasia Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010005746 Blood pressure fluctuation Diseases 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 1
- 102100034127 Dual specificity protein phosphatase 26 Human genes 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- 206010019468 Hemiplegia Diseases 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- 101001017415 Homo sapiens Dual specificity protein phosphatase 26 Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-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
- 241000176964 Mononeuron Species 0.000 description 1
- 238000012347 Morris Water Maze Methods 0.000 description 1
- 208000016285 Movement disease Diseases 0.000 description 1
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010035039 Piloerection Diseases 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 241000452413 Sabra Species 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- DDPMGIMJSRUULN-UHFFFAOYSA-N buphedrone Chemical compound CCC(NC)C(=O)C1=CC=CC=C1 DDPMGIMJSRUULN-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000009084 cardiovascular function Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000030833 cell death Effects 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 1
- 229960002327 chloral hydrate Drugs 0.000 description 1
- 230000004087 circulation Effects 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- 229960001270 d- tartaric acid Drugs 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 229960003914 desipramine Drugs 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 230000001815 facial effect Effects 0.000 description 1
- 210000003191 femoral vein Anatomy 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000011990 functional testing Methods 0.000 description 1
- 230000005021 gait Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000013038 irreversible inhibitor Substances 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000003137 locomotive effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 210000003657 middle cerebral artery Anatomy 0.000 description 1
- 230000037230 mobility Effects 0.000 description 1
- 230000009526 moderate injury Effects 0.000 description 1
- 230000001722 neurochemical effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 230000016273 neuron death Effects 0.000 description 1
- 230000004112 neuroprotection Effects 0.000 description 1
- 230000002474 noradrenergic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 210000002475 olfactory pathway Anatomy 0.000 description 1
- 238000003305 oral gavage Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 210000003516 pericardium Anatomy 0.000 description 1
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
- 229960001802 phenylephrine Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000005371 pilomotor reflex Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical class NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
- LJZPPWWHKPGCHS-UHFFFAOYSA-N propargyl chloride Chemical compound ClCC#C LJZPPWWHKPGCHS-UHFFFAOYSA-N 0.000 description 1
- 230000004224 protection Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000005245 right atrium Anatomy 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 210000001364 upper extremity Anatomy 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 238000011706 wistar kyoto rat Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
- C07C211/42—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems with six-membered aromatic rings being part of the condensed ring systems
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL11883696A IL118836A (en) | 1996-07-11 | 1996-07-11 | Pharmaceutical compositions comprising s-(-)-n-propargyl-1-aminoindan |
| PCT/IL1997/000205 WO1998002152A1 (en) | 1996-07-11 | 1997-06-20 | Pharmaceutical compositions comprising s-(-)-n-propargyl-1-amino indan |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HUP9904525A2 HUP9904525A2 (hu) | 2000-11-28 |
| HUP9904525A3 HUP9904525A3 (en) | 2000-12-28 |
| HU226961B1 true HU226961B1 (en) | 2010-03-29 |
Family
ID=11069065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9904525A HU226961B1 (en) | 1996-07-11 | 1997-06-20 | Pharmaceutical compositions comprising s-(-)-n-propargyl-1-amino indan |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6277886B1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP0929298B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4368421B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN1149985C (cg-RX-API-DMAC7.html) |
| AT (1) | ATE328590T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU3188097A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2260037C (cg-RX-API-DMAC7.html) |
| DE (1) | DE69736066T2 (cg-RX-API-DMAC7.html) |
| HU (1) | HU226961B1 (cg-RX-API-DMAC7.html) |
| IL (1) | IL118836A (cg-RX-API-DMAC7.html) |
| NO (1) | NO326052B1 (cg-RX-API-DMAC7.html) |
| WO (1) | WO1998002152A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5744500A (en) * | 1990-01-03 | 1998-04-28 | Teva Pharmaceutical Industries, Ltd. | Use of R-enantiomer of N-propargyl-1-aminoindan, salts, and compositions thereof |
| IL118836A (en) | 1996-07-11 | 2001-01-11 | Teva Pharma | Pharmaceutical compositions comprising s-(-)-n-propargyl-1-aminoindan |
| AU2002244247B2 (en) | 2001-03-01 | 2007-12-13 | Harbor Biosciences, Inc. | Use of certain steroids for treatment of blood cell deficiencies |
| CA2496867A1 (en) | 2002-08-28 | 2004-03-11 | Hollis-Eden Pharmaceuticals, Inc. | Therapeutic treatment methods |
| AU2003282337B2 (en) * | 2002-11-07 | 2009-07-16 | Technion Research And Development Foundation Ltd. | Neuroprotective iron chelators and pharmaceutical compositions comprising them |
| US7396860B2 (en) | 2002-11-15 | 2008-07-08 | Teva Pharmaceutical Industries, Ltd. | Use of rasagiline with or without riluzole to treat amyotrophic lateral sclerosis |
| CA2547053C (en) | 2003-11-25 | 2014-05-27 | Technion Research & Development Foundation Ltd. | Compositions and methods for treatment of cardiovascular disorders and diseases |
| US8097608B2 (en) * | 2003-11-25 | 2012-01-17 | Technion Research And Development Foundation Ltd. | Methods for treatment of cardiovascular disorders and diseases |
| JP2005232148A (ja) * | 2004-02-03 | 2005-09-02 | Technion Research & Development Foundation Ltd | 神経保護剤としてプロパルギルアミンの使用 |
| WO2006014973A2 (en) * | 2004-07-26 | 2006-02-09 | Teva Pharmaceutical Industries, Ltd. | Pharmaceutical dosage forms including rasagiline |
| US20060025446A1 (en) * | 2004-07-27 | 2006-02-02 | Jeffrey Sterling | Propargyl nitroxides and indanyl nitroxides and their use for the treatment of neurologic diseases and disorders |
| AU2005330504B2 (en) | 2004-09-29 | 2010-10-28 | Harbor Biosciences, Inc. | Steroid analogs and characterization and treatment methods |
| US20080261894A1 (en) * | 2005-02-17 | 2008-10-23 | Rivka Kreitman | Combination Therapy with Glatiramer Acetate and Rasagiline for the Treatment of Multiple Sclerosis |
| RU2404746C2 (ru) | 2005-02-23 | 2010-11-27 | Тева Фармасьютикал Индастриз, Лтд. | Композиции разагилина с улучшенной однородностью содержимого |
| US8263655B2 (en) * | 2005-10-06 | 2012-09-11 | Technion Research And Development Foundation Ltd | Methods for treatment of renal failure |
| CN101622225B (zh) * | 2005-11-17 | 2015-04-15 | 泰华制药工业有限公司 | 炔丙基氨基茚分离方法 |
| US7572834B1 (en) | 2005-12-06 | 2009-08-11 | Teva Pharmaceutical Industries, Ltd. | Rasagiline formulations and processes for their preparation |
| JP2009518433A (ja) * | 2005-12-09 | 2009-05-07 | イッサム リサーチ ディベロップメント カンパニー オブ ザ ヘブライ ユニバーシティー オブ エルサレム | 神経保護用の低用量ラドスチギルの使用 |
| AU2007217349B9 (en) | 2006-02-21 | 2013-06-27 | Teva Pharmaceutical Industries, Ltd. | Use of rasagiline for the treatment of Multiple System Atrophy |
| TW200744576A (en) | 2006-02-24 | 2007-12-16 | Teva Pharma | Propargylated aminoindans, processes for preparation, and uses thereof |
| EP2007369A4 (en) | 2006-04-03 | 2009-07-01 | Teva Pharma | USE OF RASAGILINE FOR THE TREATMENT OF LEG SYNDROME WITHOUT REST |
| EP1892233A1 (de) * | 2006-08-18 | 2008-02-27 | Ratiopharm GmbH | Neue Salze des Wirkstoffs Rasagilin |
| CA2672452C (en) * | 2006-12-14 | 2012-07-03 | Teva Pharmaceutical Industries Ltd. | Tannate salt of rasagiline |
| US7750051B2 (en) * | 2006-12-14 | 2010-07-06 | Teva Pharmaceutical Industries, Ltd. | Crystalline solid rasagiline base |
| EP1987816A1 (de) * | 2007-04-30 | 2008-11-05 | Ratiopharm GmbH | Adsorbate eines Rasagilinsalzes mit einem wasserlöslichen Hilfsstoff |
| EP2194780A4 (en) * | 2007-09-05 | 2010-10-27 | Teva Pharma | METHOD FOR TREATING GLAUCOMA BY RASAGILINE |
| US8188149B2 (en) * | 2007-09-17 | 2012-05-29 | Teva Pharmaceutical Industries, Ltd. | Use of R(+)-N-propargy1-1-aminoindan to treat or prevent hearing loss |
| MX2010007601A (es) * | 2008-01-11 | 2010-08-03 | Teva Pharma | Formulaciones de rasagilina, su preparacion y uso. |
| WO2009122351A2 (en) * | 2008-04-01 | 2009-10-08 | Kangwon National University | Anti-parkinsonian compounds mppe |
| US20100008983A1 (en) * | 2008-06-10 | 2010-01-14 | Muhammad Safadi | Rasagiline soft gelatin capsules |
| BRPI0909894A2 (pt) * | 2008-06-13 | 2015-07-28 | Teva Pharma | "método de redução da velocidade de progressão de mal de parkinson em um paciente com mal de parkinson em estágio inicial, método de redução da velocidade de progressão de mal de parkinson, método de atraso da necessidade de terapia antiparkinsoniana sintomática em um paciente de mal de parkinson em estágio inicial, método de redução do risco de um paciente com mal de parkinson que necessita de terapia antiparkinsoniana, método de redução do declínio funcional de um paciente com mal de parkinson em estágio inicial, método de redução do declínio funcional em um paciente com mal de parkinson, método de tratamento de um paciente que exibe sinais iniciais de mal de parkinson, método de redução da fadiga em um paciente com mal de parkinson em estágio inicial, método de redução da velocidade de progressão clínica e tratamento de sintomas de mal de parkinson em um paciente com mal de parkinson, rasagilina ou um sal farmaceuticamente aceitável de rasagilina, composição farmacêutica. |
| US7968749B2 (en) * | 2008-06-19 | 2011-06-28 | Teva Pharmaceutical Industries, Ltd. | Process for preparing and drying solid rasagiline base |
| US8334409B2 (en) * | 2008-06-19 | 2012-12-18 | Teva Pharmaceutical Industries, Ltd. | Process for purifying rasagiline base |
| US20100189791A1 (en) * | 2009-01-23 | 2010-07-29 | Teva Pharmaceutical Industries, Ltd. | Delayed release rasagiline malate formulation |
| DK2451771T3 (da) | 2009-07-09 | 2014-09-08 | Ratiopharm Gmbh | Salte af rasagilin og farmaceutiske fremstillingsmåder heraf |
| JP6045347B2 (ja) | 2010-02-03 | 2016-12-14 | ファーマ ツー ビー リミテッド | ラサギリンの持続放出性製剤およびその使用 |
| EP2603212A4 (en) | 2010-07-27 | 2014-01-08 | Teva Pharma | USE OF RASAGILINE FOR THE TREATMENT OF SMOKING DISORDER |
| JP2013537530A (ja) | 2010-07-27 | 2013-10-03 | テバ ファーマシューティカル インダストリーズ リミティド | ラサギリンシトレートの分散物 |
| BR112014008555A2 (pt) | 2011-10-10 | 2017-04-18 | Teva Pharma | r(+)-n-formil-propargil-aminoindano |
| EA201490760A1 (ru) | 2011-10-10 | 2014-09-30 | Тева Фармасьютикал Индастриз Лтд. | R(+)-n-метилпропаргиламиноиндан |
| EP2884972A4 (en) | 2012-08-17 | 2016-05-11 | Teva Pharma | PARENTERAL FORMULATION OF RASAGILINE |
| CN104177610A (zh) * | 2013-05-27 | 2014-12-03 | 韩文毅 | 一种非线性的聚合物及其制备和用途 |
| CN104177611A (zh) * | 2013-05-27 | 2014-12-03 | 韩文毅 | 一种非线性的聚合物及其制备和用途 |
| CN111333517A (zh) * | 2018-12-19 | 2020-06-26 | 上海奥博生物医药技术有限公司 | 一种制备雷沙吉兰的改进方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1187017A (en) * | 1966-07-16 | 1970-04-08 | Aspro Nicholas Ltd | Substituted 1-Amino Indanes and Tetrahydronaphthalens |
| US5744500A (en) * | 1990-01-03 | 1998-04-28 | Teva Pharmaceutical Industries, Ltd. | Use of R-enantiomer of N-propargyl-1-aminoindan, salts, and compositions thereof |
| IL92952A (en) * | 1990-01-03 | 1994-06-24 | Teva Pharma | R-enantiomers of n-propargyl-1-aminoindan compounds, their preparation and pharmaceutical compositions containing them |
| IL99759A (en) * | 1991-10-16 | 1997-06-10 | Teva Pharma | Mono-fluorinated derivatives of n-propargyl-1-aminoindan, their preparation and pharmaceutical compositions containing them |
| IL111240A (en) * | 1993-10-18 | 2001-10-31 | Teva Pharma | Salts of r(+) - enantiomers of n- propargyl-1-aminoindan and pharmaceutical compositions comprising them |
| DE69535315T2 (de) * | 1994-01-10 | 2007-06-28 | Teva Pharmaceutical Industries Ltd. | 1-aminoindanderivate und zusammensetzungen hiervon |
| IL115357A (en) * | 1995-09-20 | 2000-01-31 | Teva Pharma | Stable compositions containing N-propargyl-1-aminoindan and polyhydric alcohols |
| IL118836A (en) | 1996-07-11 | 2001-01-11 | Teva Pharma | Pharmaceutical compositions comprising s-(-)-n-propargyl-1-aminoindan |
-
1996
- 1996-07-11 IL IL11883696A patent/IL118836A/xx not_active IP Right Cessation
-
1997
- 1997-06-20 JP JP50580698A patent/JP4368421B2/ja not_active Expired - Lifetime
- 1997-06-20 DE DE69736066T patent/DE69736066T2/de not_active Expired - Lifetime
- 1997-06-20 HU HU9904525A patent/HU226961B1/hu unknown
- 1997-06-20 AT AT97927353T patent/ATE328590T1/de not_active IP Right Cessation
- 1997-06-20 WO PCT/IL1997/000205 patent/WO1998002152A1/en not_active Ceased
- 1997-06-20 EP EP97927353A patent/EP0929298B1/en not_active Expired - Lifetime
- 1997-06-20 CN CNB971971994A patent/CN1149985C/zh not_active Expired - Lifetime
- 1997-06-20 AU AU31880/97A patent/AU3188097A/en not_active Abandoned
- 1997-06-20 CA CA002260037A patent/CA2260037C/en not_active Expired - Lifetime
-
1999
- 1999-01-08 NO NO19990088A patent/NO326052B1/no not_active IP Right Cessation
- 1999-01-11 US US09/228,153 patent/US6277886B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US6277886B1 (en) | 2001-08-21 |
| HUP9904525A3 (en) | 2000-12-28 |
| DE69736066D1 (de) | 2006-07-20 |
| EP0929298A1 (en) | 1999-07-21 |
| JP2000514453A (ja) | 2000-10-31 |
| EP0929298B1 (en) | 2006-06-07 |
| CN1149985C (zh) | 2004-05-19 |
| CA2260037A1 (en) | 1998-01-22 |
| CA2260037C (en) | 2007-01-23 |
| HUP9904525A2 (hu) | 2000-11-28 |
| NO990088L (no) | 1999-03-10 |
| AU3188097A (en) | 1998-02-09 |
| NO990088D0 (no) | 1999-01-08 |
| DE69736066T2 (de) | 2006-12-28 |
| WO1998002152A1 (en) | 1998-01-22 |
| CN1227486A (zh) | 1999-09-01 |
| IL118836A (en) | 2001-01-11 |
| IL118836A0 (en) | 1996-10-31 |
| NO326052B1 (no) | 2008-09-08 |
| ATE328590T1 (de) | 2006-06-15 |
| JP4368421B2 (ja) | 2009-11-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU226961B1 (en) | Pharmaceutical compositions comprising s-(-)-n-propargyl-1-amino indan | |
| JP3341898B2 (ja) | Ｎ−プロパルギル−１−アミノインダンのｒ−エナンチオマー、その塩および組成物の使用 | |
| US5532415A (en) | R-enantiomer of N-propargyl-1-aminoindan, salts, compositions and uses thereof | |
| CA2174449C (en) | R-enantiomer of n-propargyl-1-aminoindan, salts, compositions and uses thereof | |
| MXPA06006696A (es) | (s)-2-n-propilamino-5-hidroxitetralina como un agonista-d3. | |
| WO2019036624A1 (en) | MONOAMINE PAMOATE SALT TYPE ANTI-PARKINSON AGENTS, PROCESS FOR PREPARING AND USING SAME | |
| BR112020009361A2 (pt) | composto de fórmula i, composição farmacêutica para tratar um distúrbio ocular ou complicações do mesmo, método de síntese de composto, método de tratamento de um distúrbio ocular ou complicações do mesmo em um indivíduo que precisa do mesmo e uso de um composto | |
| WO1985005617A1 (en) | Phenylisopropylamine derivative and its preparation | |
| CZ2003497A3 (cs) | �@Aminoalkylcyklohexanová sloučenina a její použití | |
| RU2289570C2 (ru) | Кислотно-аддитивные соли тербинафина и яблочной кислоты, способ их получения и фармацевтическая композиция для лечения грибковой инфекции | |
| CA2353205C (en) | Agent for treating parkinson's disease comprising astrocyte function-improving agent as active ingredient | |
| AU2002238534A1 (en) | Malic acid addition salts of terbinafine | |
| EP0519925A1 (en) | Use of optically pure s(-) atenolol for the treatment of cardiovascular disorders | |
| US4141993A (en) | Compounds of diphenylcyclopentylamine type and methods for their preparation | |
| EA005499B1 (ru) | 1-аминоалкилциклогексаны в качестве трипаноцидных агентов | |
| MX2009000792A (es) | Inhibidores de monoamina oxidasa utiles para tratar trastornos de la retina externa. | |
| JPH0346471B2 (cg-RX-API-DMAC7.html) |