NZ547897A - Therapeutic methods and uses of sapogenins and their derivatives - Google Patents

Therapeutic methods and uses of sapogenins and their derivatives

Info

Publication number: NZ547897A
Authority: NZ; New Zealand
Prior art keywords: pharmaceutically acceptable; acceptable salts; alkyl; sarsasapogenin; smilagenin
Prior art date: 2002-03-27

Application number

NZ547897A

Other languages

English (en)

Inventor

Daryl Rees

Phil Gunning

Antonia Orsi

Zongqin Xia

Yaer Hu

Original Assignee

Phytopharm Plc

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.)

2002-03-27

Filing date

2003-03-27

Publication date

2008-02-29

2002-03-27 Priority claimed from ARP020101170A external-priority patent/AR033079A1/es

2003-03-27 Application filed by Phytopharm Plc filed Critical Phytopharm Plc

2003-03-27 Priority to NZ563183A priority Critical patent/NZ563183A/en

2008-02-29 Publication of NZ547897A publication Critical patent/NZ547897A/en

Links

INLFWQCRAJUDCR-IQVMEADQSA-N (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane] Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CCCCC4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 INLFWQCRAJUDCR-IQVMEADQSA-N 0.000 title claims abstract description 19
238000002560 therapeutic procedure Methods 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 99
150000003839 salts Chemical class 0.000 claims abstract description 79
230000004770 neurodegeneration Effects 0.000 claims abstract description 59
239000013543 active substance Substances 0.000 claims abstract description 47
238000011282 treatment Methods 0.000 claims abstract description 32
230000001149 cognitive effect Effects 0.000 claims abstract description 31
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
239000000203 mixture Substances 0.000 claims abstract description 24
201000010099 disease Diseases 0.000 claims abstract description 21
230000002232 neuromuscular Effects 0.000 claims abstract description 21
208000010877 cognitive disease Diseases 0.000 claims abstract description 18
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208000024891 symptom Diseases 0.000 claims abstract description 17
230000006735 deficit Effects 0.000 claims abstract description 11
230000004064 dysfunction Effects 0.000 claims abstract description 11
230000001537 neural effect Effects 0.000 claims abstract description 11
230000002265 prevention Effects 0.000 claims abstract description 9
239000003814 drug Substances 0.000 claims abstract description 6
238000004519 manufacturing process Methods 0.000 claims abstract description 4
RTMWIZOXNKJHRE-UHFFFAOYSA-N Tigogenin Natural products CC1COC2CC(C)(OC12)C3CCC4C5CCC6CC(O)CCC6(C)C5CCC34C RTMWIZOXNKJHRE-UHFFFAOYSA-N 0.000 claims description 351
GMBQZIIUCVWOCD-WWASVFFGSA-N Sarsapogenine Chemical group O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 GMBQZIIUCVWOCD-WWASVFFGSA-N 0.000 claims description 226
GMBQZIIUCVWOCD-UQHLGXRBSA-N (25R)-5beta-spirostan-3beta-ol Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 GMBQZIIUCVWOCD-UQHLGXRBSA-N 0.000 claims description 212
229950002323 smilagenin Drugs 0.000 claims description 106
125000000217 alkyl group Chemical group 0.000 claims description 86
GMBQZIIUCVWOCD-RHHRBMONSA-N (1R,2S,4S,5'S,6R,7S,8R,9S,12S,13S,16R,18R)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-ol Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@H](C)CO1 GMBQZIIUCVWOCD-RHHRBMONSA-N 0.000 claims description 80
GMBQZIIUCVWOCD-SGKIHABASA-N epismilagenin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)CC[C@@H](O)C[C@H]4CC[C@H]3[C@@H]2C1)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 GMBQZIIUCVWOCD-SGKIHABASA-N 0.000 claims description 56
125000002252 acyl group Chemical group 0.000 claims description 39
102000005962 receptors Human genes 0.000 claims description 35
108020003175 receptors Proteins 0.000 claims description 35
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
125000005843 halogen group Chemical group 0.000 claims description 26
-1 sulpho Chemical class 0.000 claims description 20
DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 claims description 18
WQLVFSAGQJTQCK-UHFFFAOYSA-N diosgenin Natural products CC1C(C2(CCC3C4(C)CCC(O)CC4=CCC3C2C2)C)C2OC11CCC(C)CO1 WQLVFSAGQJTQCK-UHFFFAOYSA-N 0.000 claims description 17
239000008103 glucose Substances 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims description 15
239000000651 prodrug Substances 0.000 claims description 14
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125000001424 substituent group Chemical group 0.000 claims description 13
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CIBAPVLFORANSS-UHFFFAOYSA-N Smilagenone Natural products CC1C(C2(CCC3C4(C)CCC(=O)CC4CCC3C2C2)C)C2OC11CCC(C)CO1 CIBAPVLFORANSS-UHFFFAOYSA-N 0.000 claims description 10
125000001475 halogen functional group Chemical group 0.000 claims description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 9
AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims description 9
QNAYBMKLOCPYGJ-UHFFFAOYSA-M alaninate Chemical compound CC(N)C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-M 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
FFEARJCKVFRZRR-UHFFFAOYSA-M methioninate Chemical compound CSCCC(N)C([O-])=O FFEARJCKVFRZRR-UHFFFAOYSA-M 0.000 claims description 9
COLNVLDHVKWLRT-UHFFFAOYSA-M phenylalaninate Chemical compound [O-]C(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-M 0.000 claims description 9
NWMIYTWHUDFRPL-UHFFFAOYSA-N sapogenin Natural products COC(=O)C1(CO)C(O)CCC2(C)C1CCC3(C)C2CC=C4C5C(C)(O)C(C)CCC5(CCC34C)C(=O)O NWMIYTWHUDFRPL-UHFFFAOYSA-N 0.000 claims description 9
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KZSNJWFQEVHDMF-UHFFFAOYSA-M valinate Chemical compound CC(C)C(N)C([O-])=O KZSNJWFQEVHDMF-UHFFFAOYSA-M 0.000 claims description 9
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SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 claims description 8
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CIBAPVLFORANSS-OHEGQEBBSA-N SMILAGENONE Chemical compound CC1C([C@]2(CCC3[C@@]4(C)CCC(=O)C[C@H]4CCC3C2C2)C)C2OC11CC[C@@H](C)CO1 CIBAPVLFORANSS-OHEGQEBBSA-N 0.000 claims description 8
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FZFIXAWDCINUNL-HUJMDDBMSA-N (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O FZFIXAWDCINUNL-HUJMDDBMSA-N 0.000 claims description 6
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 6
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PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 claims description 6
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PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 6
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 6
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239000008194 pharmaceutical composition Substances 0.000 claims description 5
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YAHHFDSODKFKOV-OTEWLTGOSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;(2r,3r,4s,5s)-2,3,4,5-tetrahydroxyhexanal Chemical compound C[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O YAHHFDSODKFKOV-OTEWLTGOSA-N 0.000 claims description 4
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AUTALUGDOGWPQH-SPWJBRMPSA-N (2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal;(2s,3r,4r)-2,3,4,5-tetrahydroxypentanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O AUTALUGDOGWPQH-SPWJBRMPSA-N 0.000 claims description 3
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- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
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Life Sciences & Earth Sciences (AREA)
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Public Health (AREA)
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Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
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Neurology (AREA)
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Biomedical Technology (AREA)
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Steroid Compounds (AREA)
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NZ547897A 2002-03-27 2003-03-27 Therapeutic methods and uses of sapogenins and their derivatives NZ547897A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
NZ563183A NZ563183A (en)	2002-03-27	2003-03-27	Therapeutic methods and uses of sapogenins and their derivatives

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
ARP020101170A AR033079A1 (es)	2001-03-28	2002-03-27	Derivados de sapogeninas, sintesis y uso, y metodos en base a su uso
US36817802P	2002-03-28	2002-03-28
PCT/GB2002/001578 WO2002079221A2 (en)	2001-03-28	2002-03-28	Sapogenin derivatives, their synthesis and use

Publications (1)

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NZ547897A true NZ547897A (en)	2008-02-29

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NZ547897A NZ547897A (en)	2002-03-27	2003-03-27	Therapeutic methods and uses of sapogenins and their derivatives
NZ547344A NZ547344A (en)	2002-03-27	2003-03-27	Therapeutic methods and uses of sapogenins and their derivatives

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NZ547344A NZ547344A (en)	2002-03-27	2003-03-27	Therapeutic methods and uses of sapogenins and their derivatives

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KR (1)	KR20100093621A (de)
CN (1)	CN1642558B (de)
AT (1)	ATE424211T1 (de)
IL (1)	IL164161A0 (de)
NZ (2)	NZ547897A (de)
PE (1)	PE20040306A1 (de)
PL (1)	PL213697B1 (de)
RU (1)	RU2332999C2 (de)
TW (1)	TWI329016B (de)
WO (1)	WO2003082893A2 (de)

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JP7149266B2 (ja)	2016-09-30	2022-10-06	セージセラピューティクス，インコーポレイテッド	Ｃ７置換オキシステロールおよびｎｍｄａモジュレーターとしての方法
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2003
- 2003-03-27 PL PL372941A patent/PL213697B1/pl not_active IP Right Cessation
- 2003-03-27 WO PCT/GB2003/001380 patent/WO2003082893A2/en not_active Ceased
- 2003-03-27 RU RU2004130281/15A patent/RU2332999C2/ru not_active IP Right Cessation
- 2003-03-27 PE PE2003000315A patent/PE20040306A1/es not_active Application Discontinuation
- 2003-03-27 AT AT03722713T patent/ATE424211T1/de active
- 2003-03-27 CN CN038071886A patent/CN1642558B/zh not_active Expired - Fee Related
- 2003-03-27 IL IL16416103A patent/IL164161A0/xx unknown
- 2003-03-27 KR KR1020107017081A patent/KR20100093621A/ko not_active Abandoned
- 2003-03-27 NZ NZ547897A patent/NZ547897A/en unknown
- 2003-03-27 NZ NZ547344A patent/NZ547344A/en unknown
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Also Published As

Publication number	Publication date
WO2003082893A2 (en)	2003-10-09
WO2003082893A3 (en)	2004-04-15
PL372941A1 (en)	2005-08-08
PE20040306A1 (es)	2004-05-29
RU2332999C2 (ru)	2008-09-10
TW200400042A (en)	2004-01-01
PL213697B1 (pl)	2013-04-30
WO2003082893A8 (en)	2003-12-31
RU2004130281A (ru)	2006-01-20
CN1642558A (zh)	2005-07-20
CN1642558B (zh)	2012-05-30
KR20100093621A (ko)	2010-08-25
ATE424211T1 (de)	2009-03-15
NZ547344A (en)	2007-11-30
TWI329016B (en)	2010-08-21
IL164161A0 (en)	2005-12-18

Legal Events

Date	Code	Title	Description
2008-07-31	PSEA	Patent sealed
2008-07-31	RENW	Renewal (renewal fees accepted)

Publication	Publication Date	Title
WO2003082893A2 (en)	2003-10-09	Theraputic methods and uses of sapogenins and their derivatives
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AU2008207565A1 (en)	2008-09-18	Therapeutic methods and uses of sapogenins and their derivatives
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