NO327959B1 - Anvendelse av 7-hydroksyepiandrosteron for fremstilling av et medikament for beskyttelse mot akutt eller kronisk nevronskade - Google Patents

Anvendelse av 7-hydroksyepiandrosteron for fremstilling av et medikament for beskyttelse mot akutt eller kronisk nevronskade Download PDF

Info

Publication number: NO327959B1
Authority: NO; Norway
Prior art keywords: epia; hydroxyepiandrosterone; hydroxy; dhea; ischemia
Prior art date: 2000-06-29

Application number

NO20026243A

Other languages

English (en)

Norwegian (no)

Other versions

NO20026243D0 (no

NO20026243L (no

Inventor

Ernst Wulfert

Ashley Ker Pringle

Lars Eric Sundstrom

Original Assignee

Hunter Fleming 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.)

2000-06-29

Filing date

2002-12-27

Publication date

2009-10-26

2002-12-27 Application filed by Hunter Fleming Ltd filed Critical Hunter Fleming Ltd

2002-12-27 Publication of NO20026243D0 publication Critical patent/NO20026243D0/no

2003-02-27 Publication of NO20026243L publication Critical patent/NO20026243L/no

2009-10-26 Publication of NO327959B1 publication Critical patent/NO327959B1/no

Links

230000004224 protection Effects 0.000 title claims abstract description 6
230000006378 damage Effects 0.000 title claims description 10
230000001684 chronic effect Effects 0.000 title claims description 7
230000001154 acute effect Effects 0.000 title claims description 5
239000003814 drug Substances 0.000 title claims description 5
238000004519 manufacturing process Methods 0.000 title claims description 5
208000027418 Wounds and injury Diseases 0.000 title description 4
229940079593 drug Drugs 0.000 title description 4
230000001537 neural effect Effects 0.000 title description 4
208000014674 injury Diseases 0.000 title description 3
230000003961 neuronal insult Effects 0.000 claims abstract description 12
239000000203 mixture Substances 0.000 claims description 5
208000024827 Alzheimer disease Diseases 0.000 claims description 4
208000030886 Traumatic Brain injury Diseases 0.000 claims description 3
208000028698 Cognitive impairment Diseases 0.000 claims description 2
206010012289 Dementia Diseases 0.000 claims description 2
208000018737 Parkinson disease Diseases 0.000 claims description 2
208000010877 cognitive disease Diseases 0.000 claims description 2
210000000578 peripheral nerve Anatomy 0.000 claims description 2
210000000278 spinal cord Anatomy 0.000 claims description 2
150000002148 esters Chemical class 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
150000001875 compounds Chemical class 0.000 description 22
208000028867 ischemia Diseases 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
206010021143 Hypoxia Diseases 0.000 description 13
241001465754 Metazoa Species 0.000 description 12
230000007954 hypoxia Effects 0.000 description 12
230000000694 effects Effects 0.000 description 11
210000002569 neuron Anatomy 0.000 description 11
230000000324 neuroprotective effect Effects 0.000 description 11
VFPMCLQMAUVEHD-UHFFFAOYSA-N 7alpha hydroxy isoandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3C(O)CC21 VFPMCLQMAUVEHD-UHFFFAOYSA-N 0.000 description 10
239000000243 solution Substances 0.000 description 10
VFPMCLQMAUVEHD-KMQZSKAMSA-N (3beta,5alpha,7alpha)-3,7-dihydroxyandrostan-17-one Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3[C@H](O)C[C@H]21 VFPMCLQMAUVEHD-KMQZSKAMSA-N 0.000 description 9
FMGSKLZLMKYGDP-USOAJAOKSA-N dehydroepiandrosterone Chemical class C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC=C21 FMGSKLZLMKYGDP-USOAJAOKSA-N 0.000 description 9
UQNAFPHGVPVTAL-UHFFFAOYSA-N 2,3-Dihydroxy-6-nitro-7-sulfamoyl-benzo(f)quinoxaline Chemical compound N1C(=O)C(=O)NC2=C1C=C([N+]([O-])=O)C1=C2C=CC=C1S(=O)(=O)N UQNAFPHGVPVTAL-UHFFFAOYSA-N 0.000 description 8
XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical compound [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 description 8
210000004556 brain Anatomy 0.000 description 7
238000002474 experimental method Methods 0.000 description 7
238000002347 injection Methods 0.000 description 7
239000007924 injection Substances 0.000 description 7
238000000034 method Methods 0.000 description 7
230000004112 neuroprotection Effects 0.000 description 7
FMGSKLZLMKYGDP-UHFFFAOYSA-N Dehydroepiandrosterone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CC=C21 FMGSKLZLMKYGDP-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
208000006011 Stroke Diseases 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
229960002847 prasterone Drugs 0.000 description 6
210000002763 pyramidal cell Anatomy 0.000 description 6
-1 7-keto compound Chemical class 0.000 description 5
VFPMCLQMAUVEHD-UCPSWNCLSA-N 7beta-hydroxyepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3[C@@H](O)C[C@H]21 VFPMCLQMAUVEHD-UCPSWNCLSA-N 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
241000700159 Rattus Species 0.000 description 5
210000001320 hippocampus Anatomy 0.000 description 5
150000003431 steroids Chemical class 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
206010002091 Anaesthesia Diseases 0.000 description 4
201000006474 Brain Ischemia Diseases 0.000 description 4
206010008120 Cerebral ischaemia Diseases 0.000 description 4
GQPLMRYTRLFLPF-UHFFFAOYSA-N Nitrous Oxide Chemical compound [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
230000037005 anaesthesia Effects 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
230000003197 catalytic effect Effects 0.000 description 4
230000000302 ischemic effect Effects 0.000 description 4
239000002609 medium Substances 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
239000012981 Hank's balanced salt solution Substances 0.000 description 3
238000010826 Nissl staining Methods 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000002411 adverse Effects 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
230000037396 body weight Effects 0.000 description 3
208000029028 brain injury Diseases 0.000 description 3
206010008118 cerebral infarction Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
239000008103 glucose Substances 0.000 description 3
230000000971 hippocampal effect Effects 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
230000004770 neurodegeneration Effects 0.000 description 3
230000004083 survival effect Effects 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
OLPSAOWBSPXZEA-JIEICEMKSA-N 7alpha-hydroxydehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3[C@H](O)C=C21 OLPSAOWBSPXZEA-JIEICEMKSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000795424 Epia Species 0.000 description 2
206010019196 Head injury Diseases 0.000 description 2
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 2
241000700157 Rattus norvegicus Species 0.000 description 2
229910004298 SiO 2 Inorganic materials 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
230000005540 biological transmission Effects 0.000 description 2
230000006931 brain damage Effects 0.000 description 2
231100000874 brain damage Toxicity 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
210000001715 carotid artery Anatomy 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 2
BCQZXOMGPXTTIC-UHFFFAOYSA-N halothane Chemical compound FC(F)(F)C(Cl)Br BCQZXOMGPXTTIC-UHFFFAOYSA-N 0.000 description 2
229960003132 halothane Drugs 0.000 description 2
238000005805 hydroxylation reaction Methods 0.000 description 2
238000010253 intravenous injection Methods 0.000 description 2
238000011835 investigation Methods 0.000 description 2
QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
210000004185 liver Anatomy 0.000 description 2
239000001272 nitrous oxide Substances 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
229960001412 pentobarbital Drugs 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000011084 recovery Methods 0.000 description 2
230000010410 reperfusion Effects 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229950003937 tolonium Drugs 0.000 description 2
HNONEKILPDHFOL-UHFFFAOYSA-M tolonium chloride Chemical compound [Cl-].C1=C(C)C(N)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 HNONEKILPDHFOL-UHFFFAOYSA-M 0.000 description 2
210000002385 vertebral artery Anatomy 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
OLPSAOWBSPXZEA-GCNMQWDSSA-N 7beta-hydroxydehydroepiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3[C@@H](O)C=C21 OLPSAOWBSPXZEA-GCNMQWDSSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
208000017701 Endocrine disease Diseases 0.000 description 1
QGXBDMJGAMFCBF-UHFFFAOYSA-N Etiocholanolone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC21 QGXBDMJGAMFCBF-UHFFFAOYSA-N 0.000 description 1
208000013016 Hypoglycemia Diseases 0.000 description 1
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
206010056677 Nerve degeneration Diseases 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
ORNBQBCIOKFOEO-YQUGOWONSA-N Pregnenolone Natural products O=C(C)[C@@H]1[C@@]2(C)[C@H]([C@H]3[C@@H]([C@]4(C)C(=CC3)C[C@@H](O)CC4)CC2)CC1 ORNBQBCIOKFOEO-YQUGOWONSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
238000000692 Student's t-test Methods 0.000 description 1
208000032851 Subarachnoid Hemorrhage Diseases 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
206010052428 Wound Diseases 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
239000002253 acid Substances 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
239000003855 balanced salt solution Substances 0.000 description 1
230000003542 behavioural effect Effects 0.000 description 1
238000007664 blowing Methods 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000005779 cell damage Effects 0.000 description 1
208000037887 cell injury Diseases 0.000 description 1
210000001175 cerebrospinal fluid Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000003920 cognitive function Effects 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
108050003126 conotoxin Proteins 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
229910052593 corundum Inorganic materials 0.000 description 1
230000001086 cytosolic effect Effects 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000002716 delivery method Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
QLTXKCWMEZIHBJ-PJGJYSAQSA-N dizocilpine maleate Chemical compound OC(=O)\C=C/C(O)=O.C12=CC=CC=C2[C@]2(C)C3=CC=CC=C3C[C@H]1N2 QLTXKCWMEZIHBJ-PJGJYSAQSA-N 0.000 description 1
QGXBDMJGAMFCBF-LUJOEAJASA-N epiandrosterone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 QGXBDMJGAMFCBF-LUJOEAJASA-N 0.000 description 1
210000000918 epididymis Anatomy 0.000 description 1
201000010063 epididymitis Diseases 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
230000001605 fetal effect Effects 0.000 description 1
239000000834 fixative Substances 0.000 description 1
238000002073 fluorescence micrograph Methods 0.000 description 1
230000006870 function Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
244000144993 groups of animals Species 0.000 description 1
230000036541 health Effects 0.000 description 1
210000005003 heart tissue Anatomy 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000033444 hydroxylation Effects 0.000 description 1
230000001146 hypoxic effect Effects 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
208000026278 immune system disease Diseases 0.000 description 1
238000013383 initial experiment Methods 0.000 description 1
229960004194 lidocaine Drugs 0.000 description 1
210000001853 liver microsome Anatomy 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
FJQXCDYVZAHXNS-UHFFFAOYSA-N methadone hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 FJQXCDYVZAHXNS-UHFFFAOYSA-N 0.000 description 1
230000001095 motoneuron effect Effects 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
239000004090 neuroprotective agent Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
210000002741 palatine tonsil Anatomy 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
239000013641 positive control Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000002243 precursor Substances 0.000 description 1
ORNBQBCIOKFOEO-QGVNFLHTSA-N pregnenolone Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 ORNBQBCIOKFOEO-QGVNFLHTSA-N 0.000 description 1
229960000249 pregnenolone Drugs 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
210000002307 prostate Anatomy 0.000 description 1
238000001243 protein synthesis Methods 0.000 description 1
230000000506 psychotropic effect Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
210000003705 ribosome Anatomy 0.000 description 1
229930187593 rose bengal Natural products 0.000 description 1
AZJPTIGZZTZIDR-UHFFFAOYSA-L rose bengal Chemical compound [K+].[K+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 AZJPTIGZZTZIDR-UHFFFAOYSA-L 0.000 description 1
229940081623 rose bengal Drugs 0.000 description 1
STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
210000003935 rough endoplasmic reticulum Anatomy 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000007789 sealing Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000012679 serum free medium Substances 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
210000002536 stromal cell Anatomy 0.000 description 1
239000000758 substrate Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
230000014616 translation Effects 0.000 description 1
230000000472 traumatic effect Effects 0.000 description 1
210000002700 urine Anatomy 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
229910001845 yogo sapphire Inorganic materials 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
- A61K31/568—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone
- A61K31/5685—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol substituted in positions 10 and 13 by a chain having at least one carbon atom, e.g. androstanes, e.g. testosterone having an oxo group in position 17, e.g. androsterone
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Biomedical Technology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Epidemiology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Psychology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO20026243A 2000-06-29 2002-12-27 Anvendelse av 7-hydroksyepiandrosteron for fremstilling av et medikament for beskyttelse mot akutt eller kronisk nevronskade NO327959B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB0016022A GB2363983A (en)	2000-06-29	2000-06-29	Protection against neuronal damage using 7-hydroxyepiandrosterone
PCT/GB2001/002937 WO2002000225A1 (fr)	2000-06-29	2001-06-29	7-hydroepiandrosterone presentant une activite neuroprotectrice

Publications (3)

Publication Number	Publication Date
NO20026243D0 NO20026243D0 (no)	2002-12-27
NO20026243L NO20026243L (no)	2003-02-27
NO327959B1 true NO327959B1 (no)	2009-10-26

Family

ID=9894707

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20026243A NO327959B1 (no)	2000-06-29	2002-12-27	Anvendelse av 7-hydroksyepiandrosteron for fremstilling av et medikament for beskyttelse mot akutt eller kronisk nevronskade

Country Status (24)

Country	Link
US (2)	US7718639B2 (fr)
EP (1)	EP1294382B1 (fr)
JP (1)	JP4942905B2 (fr)
KR (1)	KR100786284B1 (fr)
CN (1)	CN100459980C (fr)
AT (1)	ATE401897T1 (fr)
AU (2)	AU6770901A (fr)
CA (1)	CA2414584C (fr)
CY (1)	CY1108773T1 (fr)
CZ (1)	CZ299676B6 (fr)
DE (1)	DE60134979D1 (fr)
DK (1)	DK1294382T3 (fr)
ES (1)	ES2310182T3 (fr)
GB (1)	GB2363983A (fr)
HK (1)	HK1052300B (fr)
HU (1)	HU227152B1 (fr)
IL (2)	IL153541A0 (fr)
NO (1)	NO327959B1 (fr)
PL (1)	PL200699B1 (fr)
PT (1)	PT1294382E (fr)
RU (1)	RU2307654C2 (fr)
SI (1)	SI1294382T1 (fr)
WO (1)	WO2002000225A1 (fr)
ZA (1)	ZA200300085B (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2363984A (en) *	2000-06-29	2002-01-16	Hunter Fleming Ltd	Protection against neuronal damage using 3-hydroxy-7 -hydroxy steroids and 3-oxo-7 -hydroxy steroids
GB2378898A (en) *	2001-08-14	2003-02-26	Hunter Fleming Ltd	Prophylactic and therapeutic use of hydroxysteroids
JP2006506445A (ja) *	2002-08-28	2006-02-23	ホリス − イーデンファーマスーティカルズ、インコーポレイテッド	治療処置の方法
GB0409498D0 (en) *	2004-04-28	2004-06-02	Hunter Fleming Ltd	Transdermal steroid formulation
MX2009005335A (es) *	2006-11-21	2009-06-08	Umecrine Ab	El uso de esteroides de pregnano y androstano para la fabricacion de una composicion farmaceutica para el tratamiento de trastornos del snc.
GB0623971D0 (en) *	2006-11-30	2007-01-10	Hunter Fleming Ltd	Modulation of prostaglandin/cyclooxygenase metabolic pathways
HRP20120687T1 (hr)	2006-11-30	2012-09-30	Hunter-Fleming Limited	Moduliranje metabolizma prostaglandina/ciklooksigenaze

Family Cites Families (33)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
YU243975A (en)	1974-10-14	1982-06-30	Schering Ag	Process for obtaining 7-hydroxyestradiols
US5707983A (en)	1990-08-29	1998-01-13	Humanetics Corporation	Treatment of alzheimer's disease and modulation of immune system with Δ5-androstenes
US5292730A (en) *	1990-08-29	1994-03-08	Humanetics Corporation	Modulation of immune system with Δ5-androstenes
US5212167A (en) *	1991-09-12	1993-05-18	Trustees Of Boston University	Modulation of receptor-mediated ion transport
FR2696934B1 (fr) *	1992-10-20	1995-06-02	Conservatoire Nal Arts Metiers	Dérivés de stéroïdes naturels 3B hydroxyles ayant des propriétés de déclenchement et de stimulation de l'immunité, composition les contenant et procédé pour les obtenir.
SK103195A3 (en)	1993-03-09	1996-12-04	Univ Utah Res Found	Use of dehydroepiandrosterone derivative for pharmaceutical compositions production and pharmaceutical composition containing dehydroepiandrosterone derivative
US5846963A (en)	1995-06-07	1998-12-08	University Of Utah Research Foundation	Methods for preventing progressive tissue necrosis, reperfusion injury, bacterial translocation and adult respiratory distress syndrome
US5387583A (en) *	1993-04-20	1995-02-07	Loria; Roger M.	Compositions containing corticosteroids or analogues thereof and corticosteroid buffering effective amounts of 5-androstene 3B, 17B or 5-androstene 3B, 7B, 17B triol or analogues thereof
US5554601A (en) *	1993-11-05	1996-09-10	University Of Florida	Methods for neuroprotection
US5877169A (en)	1993-11-05	1999-03-02	University Of Florida Research Foundation, Inc.	Methods of treatment of ischemic damage
US5976850A (en)	1994-10-19	1999-11-02	University Of Edinburgh	Hippocampus-associated proteins; DNA sequences coding therefor and uses thereof
US5556847A (en) *	1994-10-27	1996-09-17	Duquesne University Of The Holy Ghost	Methods of effecting memory enhancement mediated by steroid sulfatase inhibitors
EP1288220A3 (fr)	1995-06-06	2004-07-21	Euro-Celtique	Dérivés neuroactifs 3.alpha.-Hydroxy-Andsrostanes et -Pregnanes
EP0840612A1 (fr)	1995-07-24	1998-05-13	Trustees Of Boston University	Inhibition de l'activite des recepteurs du n-methyl-d-aspartate au moyen de derives de sulfate de pregnenolone
GB2317826B (en) *	1995-08-29	1999-12-15	Univ Edinburgh	Regulation of intracellular glucocorticoid concentrations
US5985242A (en)	1995-10-27	1999-11-16	Praecis Pharmaceuticals, Inc.	Modulators of β-amyloid peptide aggregation comprising D-amino acids
NZ331975A (en) *	1996-04-09	2000-12-22	Btg Int Ltd	Use of 7 alpha-substituted steroids to treat neuropsychriatic disorders or enhance cognition
CA2262453A1 (fr)	1996-08-27	1998-03-05	Praecis Pharmaceuticals Incorporated	Modulateurs de l'agregation de peptides beta-amyloides, comprenant des d-aminoacides
FR2760362B1 (fr)	1997-03-10	2000-08-11	Vitasterol	Utilisation cosmetique ou dermatologique de steroides 7-hydroxyles
WO1998043647A1 (fr)	1997-03-28	1998-10-08	Massachusetts Institute Of Technology, Inc.	Regulation de l'expression de la proteine precurseur amyloide (app) au moyen de composes oestrogeniques
GB9708716D0 (en) *	1997-04-29	1997-06-18	Imperial College	Chronic heart failure
US6544972B1 (en) *	1997-09-25	2003-04-08	Regents Of The University Of Minnesota	Methods of limiting apoptosis of cells
WO1999024400A1 (fr)	1997-11-10	1999-05-20	Vyrex Corporation	Esters de probucol et leurs utilisations
JP2004515446A (ja) *	1997-11-24	2004-05-27	ユニバーシティ・オブ・フロリダ・リサーチ・ファンデーション・インコーポレーテッド	テストステロン阻害剤及びニューロンの保護のためのその用途
GB9726569D0 (en)	1997-12-16	1998-02-11	Univ Southampton	Neuroprotective agents
WO1999052532A1 (fr) *	1998-04-14	1999-10-21	Pharmadigm, Inc.	Procede permettant de reduire la deterioration du systeme nerveux central
FR2786102B1 (fr)	1998-11-20	2001-02-16	Monique Vincens	Utilisation de sulfate de dehydroepiandrosterone pour augmenter le nombre de recepteurs nmda chez un mammifere
US20030083231A1 (en)	1998-11-24	2003-05-01	Ahlem Clarence N.	Blood cell deficiency treatment method
US6667299B1 (en)	2000-03-16	2003-12-23	Hollis-Eden Pharmaceuticals, Inc.	Pharmaceutical compositions and treatment methods
EP1226155B1 (fr)	1999-11-02	2007-05-02	Bayer Schering Pharma AG	18-nor-steroides utilises comme oestrogenes a effet selectif
GB0003524D0 (en)	2000-02-15	2000-04-05	Btg Int Ltd	Cytoprotective steroids (II)
GB2363984A (en)	2000-06-29	2002-01-16	Hunter Fleming Ltd	Protection against neuronal damage using 3-hydroxy-7 -hydroxy steroids and 3-oxo-7 -hydroxy steroids
EP1557166A1 (fr) *	2004-01-21	2005-07-27	Newron Pharmaceuticals S.p.A.	Derives d'alpha-aminoamides pour le traitement des désordres de l'appareil urinaire inférieur

2000
- 2000-06-29 GB GB0016022A patent/GB2363983A/en not_active Withdrawn
2001
- 2001-06-29 DE DE60134979T patent/DE60134979D1/de not_active Expired - Lifetime
- 2001-06-29 EP EP01945494A patent/EP1294382B1/fr not_active Expired - Lifetime
- 2001-06-29 HK HK03104578.9A patent/HK1052300B/en not_active IP Right Cessation
- 2001-06-29 CN CNB018121098A patent/CN100459980C/zh not_active Expired - Fee Related
- 2001-06-29 HU HU0301134A patent/HU227152B1/hu not_active IP Right Cessation
- 2001-06-29 KR KR1020027017898A patent/KR100786284B1/ko not_active Expired - Fee Related
- 2001-06-29 US US10/312,533 patent/US7718639B2/en not_active Expired - Fee Related
- 2001-06-29 DK DK01945494T patent/DK1294382T3/da active
- 2001-06-29 ES ES01945494T patent/ES2310182T3/es not_active Expired - Lifetime
- 2001-06-29 CZ CZ20030077A patent/CZ299676B6/cs not_active IP Right Cessation
- 2001-06-29 PT PT01945494T patent/PT1294382E/pt unknown
- 2001-06-29 AT AT01945494T patent/ATE401897T1/de active
- 2001-06-29 JP JP2002505007A patent/JP4942905B2/ja not_active Expired - Fee Related
- 2001-06-29 IL IL15354101A patent/IL153541A0/xx active IP Right Grant
- 2001-06-29 AU AU6770901A patent/AU6770901A/xx active Pending
- 2001-06-29 RU RU2003102437/15A patent/RU2307654C2/ru not_active IP Right Cessation
- 2001-06-29 AU AU2001267709A patent/AU2001267709B2/en not_active Ceased
- 2001-06-29 SI SI200130866T patent/SI1294382T1/sl unknown
- 2001-06-29 CA CA002414584A patent/CA2414584C/fr not_active Expired - Fee Related
- 2001-06-29 WO PCT/GB2001/002937 patent/WO2002000225A1/fr not_active Ceased
- 2001-06-29 PL PL359108A patent/PL200699B1/pl not_active IP Right Cessation
2002
- 2002-12-19 IL IL153541A patent/IL153541A/en not_active IP Right Cessation
- 2002-12-27 NO NO20026243A patent/NO327959B1/no not_active IP Right Cessation
2003
- 2003-01-03 ZA ZA200300085A patent/ZA200300085B/en unknown
2008
- 2008-10-20 CY CY20081101165T patent/CY1108773T1/el unknown
2009
- 2009-12-16 US US12/639,708 patent/US20100173883A1/en not_active Abandoned

Also Published As

Publication number	Publication date
SI1294382T1 (sl)	2009-02-28
EP1294382A1 (fr)	2003-03-26
HK1052300B (en)	2009-01-30
RU2003102437A (ru)	2005-01-27
EP1294382B1 (fr)	2008-07-23
CN100459980C (zh)	2009-02-11
ZA200300085B (en)	2004-04-21
DK1294382T3 (da)	2008-11-24
CY1108773T1 (el)	2014-04-09
ATE401897T1 (de)	2008-08-15
NO20026243D0 (no)	2002-12-27
CZ299676B6 (cs)	2008-10-15
ES2310182T3 (es)	2009-01-01
KR100786284B1 (ko)	2007-12-18
KR20030034113A (ko)	2003-05-01
CA2414584C (fr)	2009-10-27
AU2001267709B2 (en)	2005-07-28
WO2002000225A1 (fr)	2002-01-03
PL200699B1 (pl)	2009-01-30
RU2307654C2 (ru)	2007-10-10
CN1440290A (zh)	2003-09-03
US7718639B2 (en)	2010-05-18
JP4942905B2 (ja)	2012-05-30
IL153541A0 (en)	2003-07-06
HU227152B1 (en)	2010-08-30
US20030166626A1 (en)	2003-09-04
CA2414584A1 (fr)	2002-01-03
HUP0301134A3 (en)	2006-06-28
NO20026243L (no)	2003-02-27
DE60134979D1 (de)	2008-09-04
AU6770901A (en)	2002-01-08
GB0016022D0 (en)	2000-08-23
PL359108A1 (en)	2004-08-23
JP2004501196A (ja)	2004-01-15
HUP0301134A2 (hu)	2003-08-28
HK1052300A1 (en)	2003-09-11
IL153541A (en)	2008-03-20
US20100173883A1 (en)	2010-07-08
PT1294382E (pt)	2008-10-21
GB2363983A (en)	2002-01-16
CZ200377A3 (cs)	2003-06-18

Legal Events

Date	Code	Title	Description
2014-02-03	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
US20100130459A1 (en)	2010-05-27	Neuroprotective 7-beta-hydroxysteroids
US20100173883A1 (en)	2010-07-08	7-hydroxyepiandrosterone having neuroprotective activity
Liu et al.	2007	Dose dependence and therapeutic window for the neuroprotective effects of 17β-estradiol when administered after cerebral ischemia
AU2001267705A1 (en)	2002-03-28	Neuroprotective 7-beta-hydroxysteroids
AU2001267709A1 (en)	2002-03-28	7-hydroxyepiandrosterone having neuroprotective activity
CN101346144B (zh)	2011-07-20	类固醇化合物衍生物在制备药物中的用途
KR101357980B1 (ko)	2014-02-05	유제놀을 포함하는 기계적 이질통 치료용 약학적 조성물