NO328597B1 - Vitamin D analoger, deres anvendelse samt farmasoytisk og kosmetisk preparat inneholdende de samme - Google Patents

Vitamin D analoger, deres anvendelse samt farmasoytisk og kosmetisk preparat inneholdende de samme Download PDF

Info

Publication number: NO328597B1
Authority: NO; Norway
Prior art keywords: phenyl; bis; mmol; vinyl; hydroxy
Prior art date: 1998-11-02

Application number

NO20012116A

Other languages

English (en)

Norwegian (no)

Other versions

NO20012116D0 (no

NO20012116L (no

Inventor

Jean Michel Bernardon

Original Assignee

Galderma Res & Dev

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.)

1998-11-02

Filing date

2001-04-27

Publication date

2010-03-29

2001-04-27 Application filed by Galderma Res & Dev filed Critical Galderma Res & Dev

2001-04-27 Publication of NO20012116D0 publication Critical patent/NO20012116D0/no

2001-07-02 Publication of NO20012116L publication Critical patent/NO20012116L/no

2010-03-29 Publication of NO328597B1 publication Critical patent/NO328597B1/no

Links

238000002360 preparation method Methods 0.000 title claims description 23
QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 title claims description 13
239000002537 cosmetic Substances 0.000 title claims description 12
239000011710 vitamin D Substances 0.000 title description 11
235000019166 vitamin D Nutrition 0.000 title description 11
229930003316 Vitamin D Natural products 0.000 title description 10
150000003710 vitamin D derivatives Chemical class 0.000 title description 10
229940046008 vitamin d Drugs 0.000 title description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 109
239000000203 mixture Substances 0.000 claims description 97
-1 alkyl radical Chemical class 0.000 claims description 91
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 67
150000001875 compounds Chemical class 0.000 claims description 58
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 42
229920002554 vinyl polymer Polymers 0.000 claims description 37
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 30
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
206010000496 acne Diseases 0.000 claims description 23
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
208000002874 Acne Vulgaris Diseases 0.000 claims description 19
208000035475 disorder Diseases 0.000 claims description 19
150000003254 radicals Chemical class 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 7
230000003780 keratinization Effects 0.000 claims description 7
230000035755 proliferation Effects 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 6
QJBFEMQIYYQIHV-UHFFFAOYSA-N 5-[2-[3-(6-hydroxy-6-methylheptyl)phenyl]ethenyl]benzene-1,3-diol Chemical compound CC(C)(O)CCCCCC1=CC=CC(C=CC=2C=C(O)C=C(O)C=2)=C1 QJBFEMQIYYQIHV-UHFFFAOYSA-N 0.000 claims description 5
WTTQQQWLLKQEOW-UHFFFAOYSA-N 5-[2-[4-(5-hydroxy-5-methylhexyl)phenyl]ethenyl]benzene-1,3-diol Chemical compound C1=CC(CCCCC(C)(O)C)=CC=C1C=CC1=CC(O)=CC(O)=C1 WTTQQQWLLKQEOW-UHFFFAOYSA-N 0.000 claims description 5
AKXYIGCQNUWBRE-UHFFFAOYSA-N 5-[2-[4-(6-hydroxy-6-methylheptyl)phenyl]ethenyl]benzene-1,3-diol Chemical compound C1=CC(CCCCCC(C)(O)C)=CC=C1C=CC1=CC(O)=CC(O)=C1 AKXYIGCQNUWBRE-UHFFFAOYSA-N 0.000 claims description 5
201000004384 Alopecia Diseases 0.000 claims description 5
210000004027 cell Anatomy 0.000 claims description 5
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 5
239000000825 pharmaceutical preparation Substances 0.000 claims description 5
WBFBUXVWFDCGOB-KLZBSXJWSA-N (3e,5e)-6-[3-[[3,4-bis(hydroxymethyl)phenoxy]methyl]phenyl]-2-methylhepta-3,5-dien-2-ol Chemical compound CC(O)(C)\C=C\C=C(/C)C1=CC=CC(COC=2C=C(CO)C(CO)=CC=2)=C1 WBFBUXVWFDCGOB-KLZBSXJWSA-N 0.000 claims description 4
OQWVSCCJZONDIX-RIBZZYNNSA-N (4e,6z)-7-[3-[[3,4-bis(hydroxymethyl)phenyl]methoxy]phenyl]-3-ethylocta-4,6-dien-3-ol Chemical compound CCC(O)(CC)\C=C\C=C(\C)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1 OQWVSCCJZONDIX-RIBZZYNNSA-N 0.000 claims description 4
ZTESJVNMSBWHTR-VZUCSPMQSA-N (e)-6-[3-[[3,4-bis(hydroxymethyl)phenyl]methoxy]phenyl]-2-methylhept-3-en-2-ol Chemical compound CC(O)(C)/C=C/CC(C)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1 ZTESJVNMSBWHTR-VZUCSPMQSA-N 0.000 claims description 4
XPXVWDQJJIIPJX-DNTJNYDQSA-N (e)-7-[3-[2-[3,4-bis(hydroxymethyl)phenyl]ethylamino]phenyl]-3-ethyloct-6-en-3-ol Chemical compound CCC(O)(CC)CC\C=C(/C)C1=CC=CC(NCCC=2C=C(CO)C(CO)=CC=2)=C1 XPXVWDQJJIIPJX-DNTJNYDQSA-N 0.000 claims description 4
ZQMFBXZFLWRMDI-UFWORHAWSA-N (e)-7-[3-[[3,4-bis(hydroxymethyl)phenyl]methylsulfanyl]phenyl]-3-ethyloct-6-en-3-ol Chemical compound CCC(O)(CC)CC\C=C(/C)C1=CC=CC(SCC=2C=C(CO)C(CO)=CC=2)=C1 ZQMFBXZFLWRMDI-UFWORHAWSA-N 0.000 claims description 4
HZZFZHRFLPADQC-UWVJOHFNSA-N (z)-8-[3-[[3,4-bis(hydroxymethyl)phenyl]methoxy]phenyl]-2-methylnon-7-en-2-ol Chemical compound CC(O)(C)CCCC/C=C(/C)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1 HZZFZHRFLPADQC-UWVJOHFNSA-N 0.000 claims description 4
JQJMQUBAJTUVQZ-UKWGHVSLSA-N (z)-8-[3-[[3,4-bis(hydroxymethyl)phenyl]methoxy]phenyl]-3-ethylnon-7-en-3-ol Chemical compound CCC(O)(CC)CCC\C=C(\C)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1 JQJMQUBAJTUVQZ-UKWGHVSLSA-N 0.000 claims description 4
MMWPHWOYUMZSAJ-UHFFFAOYSA-N 1-[1-[3-[[3,4-bis(hydroxymethyl)phenyl]methoxy]phenyl]propoxy]-3-ethylpentan-3-ol Chemical compound CCC(O)(CC)CCOC(CC)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1 MMWPHWOYUMZSAJ-UHFFFAOYSA-N 0.000 claims description 4
YXFNCHQERWQYRK-UHFFFAOYSA-N 2-(hydroxymethyl)-4-[2-[3-(5-hydroxy-5-methylhexyl)phenyl]ethenyl]phenol Chemical compound CC(C)(O)CCCCC1=CC=CC(C=CC=2C=C(CO)C(O)=CC=2)=C1 YXFNCHQERWQYRK-UHFFFAOYSA-N 0.000 claims description 4
ZTEZQRGNNBOSMB-UHFFFAOYSA-N 2-(hydroxymethyl)-4-[2-[3-(6-hydroxy-6-methylheptyl)phenyl]ethenyl]phenol Chemical compound CC(C)(O)CCCCCC1=CC=CC(C=CC=2C=C(CO)C(O)=CC=2)=C1 ZTEZQRGNNBOSMB-UHFFFAOYSA-N 0.000 claims description 4
CNMGLNUGTBHCMV-UHFFFAOYSA-N 2-(hydroxymethyl)-4-[2-[4-(6-hydroxy-6-methylheptyl)phenyl]ethenyl]phenol Chemical compound C1=CC(CCCCCC(C)(O)C)=CC=C1C=CC1=CC=C(O)C(CO)=C1 CNMGLNUGTBHCMV-UHFFFAOYSA-N 0.000 claims description 4
USKHWUWDTXUFAG-UHFFFAOYSA-N 2-(hydroxymethyl)-4-[[3-(6-hydroxy-6-methylheptan-2-yl)phenoxy]methyl]phenol Chemical compound CC(O)(C)CCCC(C)C1=CC=CC(OCC=2C=C(CO)C(O)=CC=2)=C1 USKHWUWDTXUFAG-UHFFFAOYSA-N 0.000 claims description 4
OIPNOSDQTIBAFY-UHFFFAOYSA-N 3-(hydroxymethyl)-5-[2-[3-(5-hydroxy-5-methylhexyl)phenyl]ethenyl]phenol Chemical compound CC(C)(O)CCCCC1=CC=CC(C=CC=2C=C(CO)C=C(O)C=2)=C1 OIPNOSDQTIBAFY-UHFFFAOYSA-N 0.000 claims description 4
CTCBJIKWJPZIID-UHFFFAOYSA-N 3-[2-[3-(7-hydroxy-7-methyloctyl)phenyl]ethenyl]phenol Chemical compound CC(C)(O)CCCCCCC1=CC=CC(C=CC=2C=C(O)C=CC=2)=C1 CTCBJIKWJPZIID-UHFFFAOYSA-N 0.000 claims description 4
NYZSXIOGAKTTGQ-UHFFFAOYSA-N 4-[2-[3-(7-hydroxy-7-methyloct-1-enyl)phenyl]ethenyl]benzene-1,2-diol Chemical compound CC(C)(O)CCCCC=CC1=CC=CC(C=CC=2C=C(O)C(O)=CC=2)=C1 NYZSXIOGAKTTGQ-UHFFFAOYSA-N 0.000 claims description 4
GNPNOSQGMNNEJL-UHFFFAOYSA-N 5-[2-[3-(5-hydroxy-5-methylhexyl)phenyl]ethenyl]benzene-1,3-diol Chemical compound CC(C)(O)CCCCC1=CC=CC(C=CC=2C=C(O)C=C(O)C=2)=C1 GNPNOSQGMNNEJL-UHFFFAOYSA-N 0.000 claims description 4
UDWQFQNEKHJKGV-UHFFFAOYSA-N 5-[2-[3-(5-hydroxy-6-methylheptyl)phenyl]ethenyl]benzene-1,3-diol Chemical compound CC(C)C(O)CCCCC1=CC=CC(C=CC=2C=C(O)C=C(O)C=2)=C1 UDWQFQNEKHJKGV-UHFFFAOYSA-N 0.000 claims description 4
SKBCDPGXHVVENY-UHFFFAOYSA-N 5-[2-[3-(5-hydroxypentyl)phenyl]ethenyl]benzene-1,3-diol Chemical compound OCCCCCC1=CC=CC(C=CC=2C=C(O)C=C(O)C=2)=C1 SKBCDPGXHVVENY-UHFFFAOYSA-N 0.000 claims description 4
QLKNKELCQGLJPJ-UHFFFAOYSA-N 5-[2-[3-(6-hydroxy-6-methylhept-1-enyl)phenyl]ethenyl]benzene-1,3-diol Chemical compound CC(C)(O)CCCC=CC1=CC=CC(C=CC=2C=C(O)C=C(O)C=2)=C1 QLKNKELCQGLJPJ-UHFFFAOYSA-N 0.000 claims description 4
PSDGCTCPUYVNCY-UHFFFAOYSA-N 5-[2-[3-(6-hydroxy-7-methyloct-1-enyl)phenyl]ethenyl]benzene-1,3-diol Chemical compound CC(C)C(O)CCCC=CC1=CC=CC(C=CC=2C=C(O)C=C(O)C=2)=C1 PSDGCTCPUYVNCY-UHFFFAOYSA-N 0.000 claims description 4
CQFSZZJTRREKMM-UHFFFAOYSA-N 5-[2-[3-(6-hydroxy-7-methyloctyl)phenyl]ethenyl]benzene-1,3-diol Chemical compound CC(C)C(O)CCCCCC1=CC=CC(C=CC=2C=C(O)C=C(O)C=2)=C1 CQFSZZJTRREKMM-UHFFFAOYSA-N 0.000 claims description 4
BMWNVZBRCMXPKR-UHFFFAOYSA-N 5-[2-[3-(7-ethyl-7-hydroxynon-1-enyl)phenyl]ethenyl]benzene-1,3-diol Chemical compound CCC(O)(CC)CCCCC=CC1=CC=CC(C=CC=2C=C(O)C=C(O)C=2)=C1 BMWNVZBRCMXPKR-UHFFFAOYSA-N 0.000 claims description 4
ZBKJQVUYFMDDFG-UHFFFAOYSA-N 5-[2-[3-(7-hydroxy-7-methyloct-1-enyl)phenyl]ethenyl]benzene-1,3-diol Chemical compound CC(C)(O)CCCCC=CC1=CC=CC(C=CC=2C=C(O)C=C(O)C=2)=C1 ZBKJQVUYFMDDFG-UHFFFAOYSA-N 0.000 claims description 4
GFZYCKCZDOWCAM-UHFFFAOYSA-N 5-[2-[3-(7-hydroxy-7-methyloctyl)phenyl]ethenyl]benzene-1,3-diol Chemical compound CC(C)(O)CCCCCCC1=CC=CC(C=CC=2C=C(O)C=C(O)C=2)=C1 GFZYCKCZDOWCAM-UHFFFAOYSA-N 0.000 claims description 4
LYBRVAJJIUUOGN-UHFFFAOYSA-N 5-[2-[3-(8-hydroxy-2-methoxy-8-methylnonan-2-yl)phenyl]ethenyl]benzene-1,3-diol Chemical compound CC(O)(C)CCCCCC(C)(OC)C1=CC=CC(C=CC=2C=C(O)C=C(O)C=2)=C1 LYBRVAJJIUUOGN-UHFFFAOYSA-N 0.000 claims description 4
BCHSUPNZBWLIFN-UHFFFAOYSA-N 5-[[3-(6-hydroxy-6-methylheptyl)phenoxy]methyl]benzene-1,3-diol Chemical compound CC(C)(O)CCCCCC1=CC=CC(OCC=2C=C(O)C=C(O)C=2)=C1 BCHSUPNZBWLIFN-UHFFFAOYSA-N 0.000 claims description 4
GLJKHUPNJBDEGA-UHFFFAOYSA-N 6-[3-[[3,4-bis(hydroxymethyl)phenyl]methoxy]phenyl]-2-methylhepta-3,5-dien-2-ol Chemical compound CC(O)(C)C=CC=C(C)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1 GLJKHUPNJBDEGA-UHFFFAOYSA-N 0.000 claims description 4
VOLPGXDXLHJHPD-UHFFFAOYSA-N 6-[3-[[3,4-bis(hydroxymethyl)phenyl]methoxy]phenyl]-2-methylheptan-2-ol Chemical compound CC(O)(C)CCCC(C)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1 VOLPGXDXLHJHPD-UHFFFAOYSA-N 0.000 claims description 4
VTPBXFAFKKBLOF-UHFFFAOYSA-N 6-[4-[2-[3,4-bis(hydroxymethyl)phenyl]ethenyl]phenyl]-2-methylhexan-2-ol Chemical compound C1=CC(CCCCC(C)(O)C)=CC=C1C=CC1=CC=C(CO)C(CO)=C1 VTPBXFAFKKBLOF-UHFFFAOYSA-N 0.000 claims description 4
UPMONUHDKZCFJB-UHFFFAOYSA-N 7-[3-[2-[3,4-bis(hydroxymethyl)phenyl]ethenyl]phenyl]-2-methylheptan-2-ol Chemical compound CC(C)(O)CCCCCC1=CC=CC(C=CC=2C=C(CO)C(CO)=CC=2)=C1 UPMONUHDKZCFJB-UHFFFAOYSA-N 0.000 claims description 4
BLSGLYJDBUXROP-UHFFFAOYSA-N 7-[3-[2-[4-(hydroxymethyl)phenyl]ethenyl]phenyl]-2-methylheptan-2-ol Chemical compound CC(C)(O)CCCCCC1=CC=CC(C=CC=2C=CC(CO)=CC=2)=C1 BLSGLYJDBUXROP-UHFFFAOYSA-N 0.000 claims description 4
ZJZCFWWTVKDXNV-UHFFFAOYSA-N 7-[3-[[3,4-bis(hydroxymethyl)phenyl]methoxy]phenyl]-3-ethyloctan-3-ol Chemical compound CCC(O)(CC)CCCC(C)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1 ZJZCFWWTVKDXNV-UHFFFAOYSA-N 0.000 claims description 4
FBJBSAAFPLXEJF-UHFFFAOYSA-N 7-[4-[2-[3,4-bis(hydroxymethyl)phenyl]ethenyl]phenyl]-2-methylheptan-2-ol Chemical compound C1=CC(CCCCCC(C)(O)C)=CC=C1C=CC1=CC=C(CO)C(CO)=C1 FBJBSAAFPLXEJF-UHFFFAOYSA-N 0.000 claims description 4
JVSJJHHFFBHVTL-UHFFFAOYSA-N 8-[3-[[3,4-bis(hydroxymethyl)phenyl]methoxy]phenyl]-3-ethylnonan-3-ol Chemical compound CCC(O)(CC)CCCCC(C)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1 JVSJJHHFFBHVTL-UHFFFAOYSA-N 0.000 claims description 4
FYTDUZBTYKDHBX-UHFFFAOYSA-N 9-[3-[[3,4-bis(hydroxymethyl)phenyl]methoxy]phenyl]-3-ethyldecan-3-ol Chemical compound CCC(O)(CC)CCCCCC(C)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1 FYTDUZBTYKDHBX-UHFFFAOYSA-N 0.000 claims description 4
206010003645 Atopy Diseases 0.000 claims description 4
HQTUUNVWTXUWDC-UHFFFAOYSA-N CC(O)(C)CON=C(C)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1 Chemical compound CC(O)(C)CON=C(C)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1 HQTUUNVWTXUWDC-UHFFFAOYSA-N 0.000 claims description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
230000032683 aging Effects 0.000 claims description 4
231100000360 alopecia Toxicity 0.000 claims description 4
230000001900 immune effect Effects 0.000 claims description 4
210000000987 immune system Anatomy 0.000 claims description 4
230000004968 inflammatory condition Effects 0.000 claims description 4
206010025135 lupus erythematosus Diseases 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
230000005855 radiation Effects 0.000 claims description 4
208000008742 seborrheic dermatitis Diseases 0.000 claims description 4
201000010153 skin papilloma Diseases 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
230000003612 virological effect Effects 0.000 claims description 4
102000009310 vitamin D receptors Human genes 0.000 claims description 4
108050000156 vitamin D receptors Proteins 0.000 claims description 4
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims description 3
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OQWVSCCJZONDIX-PBONPNGBSA-N (4e,6e)-7-[3-[[3,4-bis(hydroxymethyl)phenyl]methoxy]phenyl]-3-ethylocta-4,6-dien-3-ol Chemical compound CCC(O)(CC)\C=C\C=C(/C)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1 OQWVSCCJZONDIX-PBONPNGBSA-N 0.000 claims description 3
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WAWVURZLUIYBCV-UWVJOHFNSA-N (z)-7-[3-[[3,4-bis(hydroxymethyl)phenyl]methoxy]phenyl]-3-ethyloct-6-en-3-ol Chemical compound CCC(O)(CC)CC\C=C(\C)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1 WAWVURZLUIYBCV-UWVJOHFNSA-N 0.000 claims description 3
YVKKSQWZXZGSKI-FBHDLOMBSA-N (z)-9-[3-[[3,4-bis(hydroxymethyl)phenyl]methoxy]phenyl]-3-ethyldec-8-en-3-ol Chemical compound CCC(O)(CC)CCCC\C=C(\C)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1 YVKKSQWZXZGSKI-FBHDLOMBSA-N 0.000 claims description 3
XAOSELNBSGBNNM-UHFFFAOYSA-N 2-(hydroxymethyl)-4-[2-[4-(5-hydroxy-5-methylhexyl)phenyl]ethenyl]phenol Chemical compound C1=CC(CCCCC(C)(O)C)=CC=C1C=CC1=CC=C(O)C(CO)=C1 XAOSELNBSGBNNM-UHFFFAOYSA-N 0.000 claims description 3
FPIYJVGOVYKUSQ-UHFFFAOYSA-N 2-(hydroxymethyl)-4-[2-[4-(6-hydroxy-6-methylheptyl)phenyl]ethyl]phenol Chemical compound C1=CC(CCCCCC(C)(O)C)=CC=C1CCC1=CC=C(O)C(CO)=C1 FPIYJVGOVYKUSQ-UHFFFAOYSA-N 0.000 claims description 3
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125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 3
230000004071 biological effect Effects 0.000 description 3
229960005084 calcitriol Drugs 0.000 description 3
230000024245 cell differentiation Effects 0.000 description 3
230000004663 cell proliferation Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 3
239000006196 drop Substances 0.000 description 3
STQMKFRXZFSYKL-UHFFFAOYSA-N ethyl 5-(5-hydroxy-2-methoxyphenyl)hepta-2,4-dienoate Chemical compound CCOC(=O)C=CC=C(CC)C1=CC(O)=CC=C1OC STQMKFRXZFSYKL-UHFFFAOYSA-N 0.000 description 3
JAWLSZZXWMTAAS-UHFFFAOYSA-N ethyl 5-[3-[tert-butyl(dimethyl)silyl]oxyphenyl]hexa-2,4-dienoate Chemical compound CCOC(=O)C=CC=C(C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1 JAWLSZZXWMTAAS-UHFFFAOYSA-N 0.000 description 3
AMDDVCWJNUODOE-UHFFFAOYSA-N ethyl 6-(3-hydroxyphenyl)heptanoate Chemical compound CCOC(=O)CCCCC(C)C1=CC=CC(O)=C1 AMDDVCWJNUODOE-UHFFFAOYSA-N 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
150000002632 lipids Chemical class 0.000 description 3
238000000034 method Methods 0.000 description 3
VWGVMCOHXMWJLZ-UHFFFAOYSA-N methyl 6-[3-[2-[3,5-bis(ethoxymethoxy)phenyl]ethenyl]phenyl]hex-5-enoate Chemical compound CCOCOC1=CC(OCOCC)=CC(C=CC=2C=C(C=CCCCC(=O)OC)C=CC=2)=C1 VWGVMCOHXMWJLZ-UHFFFAOYSA-N 0.000 description 3
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 3
239000004005 microsphere Substances 0.000 description 3
239000002077 nanosphere Substances 0.000 description 3
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
230000028327 secretion Effects 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
229940088594 vitamin Drugs 0.000 description 3
229930003231 vitamin Natural products 0.000 description 3
235000013343 vitamin Nutrition 0.000 description 3
239000011782 vitamin Substances 0.000 description 3
150000003722 vitamin derivatives Chemical class 0.000 description 3
NRFVKNVNKOTCBH-UHFFFAOYSA-N (2,2-dimethyl-4h-1,3-benzodioxin-6-yl)methanol Chemical compound OCC1=CC=C2OC(C)(C)OCC2=C1 NRFVKNVNKOTCBH-UHFFFAOYSA-N 0.000 description 2
XIZMSRYVKCOADR-FLFUNREMSA-N (3e,5e)-6-[3-[[3,4-bis[[tert-butyl(dimethyl)silyl]oxymethyl]phenoxy]methyl]phenyl]-2-methylhepta-3,5-dien-2-ol Chemical compound CC(O)(C)\C=C\C=C(/C)C1=CC=CC(COC=2C=C(CO[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)=CC=2)=C1 XIZMSRYVKCOADR-FLFUNREMSA-N 0.000 description 2
OURCJXVOBHLREF-UHFFFAOYSA-N (4-bromophenyl)methoxy-tert-butyl-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCC1=CC=C(Br)C=C1 OURCJXVOBHLREF-UHFFFAOYSA-N 0.000 description 2
STKMZFRDOZNNCO-ZTJKHUJPSA-N (4e,6e)-7-[3-[2-[3,4-bis(hydroxymethyl)phenyl]ethyl]phenyl]-3-ethylocta-4,6-dien-3-ol Chemical compound CCC(O)(CC)\C=C\C=C(/C)C1=CC=CC(CCC=2C=C(CO)C(CO)=CC=2)=C1 STKMZFRDOZNNCO-ZTJKHUJPSA-N 0.000 description 2
GCVFYGFAFAZGJQ-ZTJKHUJPSA-N (4e,6e)-7-[3-[2-[3,4-bis(hydroxymethyl)phenyl]ethynyl]phenyl]-3-ethylocta-4,6-dien-3-ol Chemical compound CCC(O)(CC)\C=C\C=C(/C)C1=CC=CC(C#CC=2C=C(CO)C(CO)=CC=2)=C1 GCVFYGFAFAZGJQ-ZTJKHUJPSA-N 0.000 description 2
NZHVHIHWJMEJCV-IHQYTQDJSA-N (4e,6e)-7-[3-[2-[3,4-bis[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]ethyl]phenyl]-3-ethylocta-4,6-dien-3-ol Chemical compound CCC(O)(CC)\C=C\C=C(/C)C1=CC=CC(CCC=2C=C(CO[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)=CC=2)=C1 NZHVHIHWJMEJCV-IHQYTQDJSA-N 0.000 description 2
SOWLXVXVDVACPG-HOOXIVPBSA-N (4e,6e)-7-[3-[[3,4-bis(hydroxymethyl)phenyl]methoxy]-2-methoxyphenyl]-3-ethylnona-4,6-dien-3-ol Chemical compound CCC(O)(CC)\C=C\C=C(/CC)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1OC SOWLXVXVDVACPG-HOOXIVPBSA-N 0.000 description 2
WAGINFINHMUKEL-CZVBWLIWSA-N (4e,6e)-7-[3-[[3,4-bis(hydroxymethyl)phenyl]methoxy]-4-methylphenyl]-3-ethylnona-4,6-dien-3-ol Chemical compound CCC(O)(CC)\C=C\C=C(/CC)C1=CC=C(C)C(OCC=2C=C(CO)C(CO)=CC=2)=C1 WAGINFINHMUKEL-CZVBWLIWSA-N 0.000 description 2
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CPVWNAIYVCCXNG-SOYATDBDSA-N (4z)-7-[3-[tert-butyl(dimethyl)silyl]oxyphenyl]-3-ethylocta-4,6-dien-3-ol Chemical compound CCC(O)(CC)\C=C/C=C(C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1 CPVWNAIYVCCXNG-SOYATDBDSA-N 0.000 description 2
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JQJMQUBAJTUVQZ-AWQFTUOYSA-N (e)-8-[3-[[3,4-bis(hydroxymethyl)phenyl]methoxy]phenyl]-3-ethylnon-7-en-3-ol Chemical compound CCC(O)(CC)CCC\C=C(/C)C1=CC=CC(OCC=2C=C(CO)C(CO)=CC=2)=C1 JQJMQUBAJTUVQZ-AWQFTUOYSA-N 0.000 description 2
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RSBWEXIPLBQKSD-UHFFFAOYSA-N 1-[3-(methoxymethoxy)phenyl]propan-1-ol Chemical compound CCC(O)C1=CC=CC(OCOC)=C1 RSBWEXIPLBQKSD-UHFFFAOYSA-N 0.000 description 2
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JGDZOSUPBIEWFL-UHFFFAOYSA-N 2-[2-(carboxymethyl)-4-[[3-[[(5-hydroxy-5-methylhexyl)amino]methyl]phenoxy]methyl]phenyl]acetic acid Chemical compound CC(C)(O)CCCCNCC1=CC=CC(OCC=2C=C(CC(O)=O)C(CC(O)=O)=CC=2)=C1 JGDZOSUPBIEWFL-UHFFFAOYSA-N 0.000 description 2
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KOIFSQCCDJGMKJ-UHFFFAOYSA-N 5-[2-[3-(2,7-dihydroxy-7-methyloctan-2-yl)phenyl]ethenyl]benzene-1,3-diol Chemical compound CC(C)(O)CCCCC(C)(O)C1=CC=CC(C=CC=2C=C(O)C=C(O)C=2)=C1 KOIFSQCCDJGMKJ-UHFFFAOYSA-N 0.000 description 2
MYVMVWIKFDNNDE-UHFFFAOYSA-N 5-[3-[2-[3,5-bis(ethoxymethoxy)phenyl]ethenyl]phenyl]pent-4-en-1-ol Chemical compound CCOCOC1=CC(OCOCC)=CC(C=CC=2C=C(C=CCCCO)C=CC=2)=C1 MYVMVWIKFDNNDE-UHFFFAOYSA-N 0.000 description 2
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KKJTZQGDSHPBKQ-UHFFFAOYSA-N 5-[3-[2-[3,5-bis(ethoxymethoxy)phenyl]ethenyl]phenyl]pentanal Chemical compound CCOCOC1=CC(OCOCC)=CC(C=CC=2C=C(CCCCC=O)C=CC=2)=C1 KKJTZQGDSHPBKQ-UHFFFAOYSA-N 0.000 description 2
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KSIMEFUZDCSEDB-UHFFFAOYSA-N dimethyl 4-[[3-(6-ethyl-6-hydroxyoctan-2-yl)phenoxy]methyl]benzene-1,2-dicarboxylate Chemical compound CCC(O)(CC)CCCC(C)C1=CC=CC(OCC=2C=C(C(C(=O)OC)=CC=2)C(=O)OC)=C1 KSIMEFUZDCSEDB-UHFFFAOYSA-N 0.000 description 2
UWDOFIIIDIREHO-MPGSNBGNSA-N dimethyl 4-[[3-[(2e,4e)-6-ethyl-6-hydroxyocta-2,4-dien-2-yl]phenoxy]methyl]benzene-1,2-dicarboxylate Chemical compound CCC(O)(CC)\C=C\C=C(/C)C1=CC=CC(OCC=2C=C(C(C(=O)OC)=CC=2)C(=O)OC)=C1 UWDOFIIIDIREHO-MPGSNBGNSA-N 0.000 description 2
UWDOFIIIDIREHO-RCYCHHRUSA-N dimethyl 4-[[3-[(2z,4e)-6-ethyl-6-hydroxyocta-2,4-dien-2-yl]phenoxy]methyl]benzene-1,2-dicarboxylate Chemical compound CCC(O)(CC)\C=C\C=C(\C)C1=CC=CC(OCC=2C=C(C(C(=O)OC)=CC=2)C(=O)OC)=C1 UWDOFIIIDIREHO-RCYCHHRUSA-N 0.000 description 2
OSSAXUNBSYCDLM-VXLYETTFSA-N dimethyl 4-[[3-[(e)-6-ethyl-6-hydroxyoct-2-en-2-yl]phenoxy]methyl]benzene-1,2-dicarboxylate Chemical compound CCC(O)(CC)CC\C=C(/C)C1=CC=CC(OCC=2C=C(C(C(=O)OC)=CC=2)C(=O)OC)=C1 OSSAXUNBSYCDLM-VXLYETTFSA-N 0.000 description 2
OSSAXUNBSYCDLM-GRSHGNNSSA-N dimethyl 4-[[3-[(z)-6-ethyl-6-hydroxyoct-2-en-2-yl]phenoxy]methyl]benzene-1,2-dicarboxylate Chemical compound CCC(O)(CC)CC\C=C(\C)C1=CC=CC(OCC=2C=C(C(C(=O)OC)=CC=2)C(=O)OC)=C1 OSSAXUNBSYCDLM-GRSHGNNSSA-N 0.000 description 2
XFWJPIUEOUHHHT-UHFFFAOYSA-N dimethyl 4-[[tert-butyl(dimethyl)silyl]oxymethyl]benzene-1,2-dicarboxylate Chemical compound COC(=O)C1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1C(=O)OC XFWJPIUEOUHHHT-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
ALTJYQYUCMCZGA-NTUHNPAUSA-N ethyl (E)-5-[3-(methoxymethoxy)phenyl]hex-4-en-2-ynoate Chemical compound CCOC(=O)C#C\C=C(/C)C1=CC=CC(OCOC)=C1 ALTJYQYUCMCZGA-NTUHNPAUSA-N 0.000 description 2
XFGHQFOVDPJUKC-UHFFFAOYSA-N ethyl 3-[1-(3-hydroxyphenyl)propoxy]propanoate Chemical compound CCOC(=O)CCOC(CC)C1=CC=CC(O)=C1 XFGHQFOVDPJUKC-UHFFFAOYSA-N 0.000 description 2
UBVIRDJFTNBAEE-UHFFFAOYSA-N ethyl 3-[1-[3-(methoxymethoxy)phenyl]propoxy]propanoate Chemical compound CCOC(=O)CCOC(CC)C1=CC=CC(OCOC)=C1 UBVIRDJFTNBAEE-UHFFFAOYSA-N 0.000 description 2
STIYGCTXGNDFRA-UHFFFAOYSA-N ethyl 3-[3-[tert-butyl(dimethyl)silyl]oxyphenyl]butanoate Chemical compound CCOC(=O)CC(C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1 STIYGCTXGNDFRA-UHFFFAOYSA-N 0.000 description 2
JIFXJTKZAUXXAQ-UHFFFAOYSA-N ethyl 5-[3-[[3,4-bis[[tert-butyl(dimethyl)silyl]oxymethyl]phenoxy]methyl]phenyl]hexanoate Chemical compound CCOC(=O)CCCC(C)C1=CC=CC(COC=2C=C(CO[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)=CC=2)=C1 JIFXJTKZAUXXAQ-UHFFFAOYSA-N 0.000 description 2
JGBBXUQOMHBBBK-UHFFFAOYSA-N ethyl 5-[3-[tert-butyl(dimethyl)silyl]oxyphenyl]hexanoate Chemical compound CCOC(=O)CCCC(C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1 JGBBXUQOMHBBBK-UHFFFAOYSA-N 0.000 description 2
AFRWBGJRWRHQOV-UHFFFAOYSA-N ethyl 5-bromopentanoate Chemical compound CCOC(=O)CCCCBr AFRWBGJRWRHQOV-UHFFFAOYSA-N 0.000 description 2
ZUFBFEKKFIGTKA-UHFFFAOYSA-N ethyl 6-(3-hydroxyphenyl)hept-5-enoate Chemical compound CCOC(=O)CCCC=C(C)C1=CC=CC(O)=C1 ZUFBFEKKFIGTKA-UHFFFAOYSA-N 0.000 description 2
BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 2
239000000499 gel Substances 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000006210 lotion Substances 0.000 description 2
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 2
OSDVLFXRFXCYML-UHFFFAOYSA-N methyl 2-[3-[tert-butyl(dimethyl)silyl]oxyphenyl]acetate Chemical compound COC(=O)CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1 OSDVLFXRFXCYML-UHFFFAOYSA-N 0.000 description 2
UXMCNFUMKIAQDC-UHFFFAOYSA-N methyl 3,5-bis(ethoxymethoxy)benzoate Chemical compound CCOCOC1=CC(OCOCC)=CC(C(=O)OC)=C1 UXMCNFUMKIAQDC-UHFFFAOYSA-N 0.000 description 2
HREIROHQAJIJHT-UHFFFAOYSA-N methyl 3-hydroxy-5-(hydroxymethyl)benzoate Chemical compound COC(=O)C1=CC(O)=CC(CO)=C1 HREIROHQAJIJHT-UHFFFAOYSA-N 0.000 description 2
GQHGOWFFIRBMAR-UHFFFAOYSA-N methyl 5-[3-[2-[3,5-bis(ethoxymethoxy)phenyl]ethenyl]phenyl]pent-4-enoate Chemical compound CCOCOC1=CC(OCOCC)=CC(C=CC=2C=C(C=CCCC(=O)OC)C=CC=2)=C1 GQHGOWFFIRBMAR-UHFFFAOYSA-N 0.000 description 2
JFIIBXCJPPSILE-UHFFFAOYSA-N methyl 5-[3-[2-[3,5-bis(ethoxymethoxy)phenyl]ethenyl]phenyl]pentanoate Chemical compound CCOCOC1=CC(OCOCC)=CC(C=CC=2C=C(CCCCC(=O)OC)C=CC=2)=C1 JFIIBXCJPPSILE-UHFFFAOYSA-N 0.000 description 2
GOBCFXLZEBEYBL-UHFFFAOYSA-N methyl 5-[3-[2-[3,5-bis[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]ethenyl]phenyl]pentanoate Chemical compound COC(=O)CCCCC1=CC=CC(C=CC=2C=C(CO[Si](C)(C)C(C)(C)C)C=C(CO[Si](C)(C)C(C)(C)C)C=2)=C1 GOBCFXLZEBEYBL-UHFFFAOYSA-N 0.000 description 2
CVOFADIQMPPSOB-UHFFFAOYSA-N methyl 6-[3-[2-[3,5-bis(ethoxymethoxy)phenyl]ethenyl]phenyl]hexanoate Chemical compound CCOCOC1=CC(OCOCC)=CC(C=CC=2C=C(CCCCCC(=O)OC)C=CC=2)=C1 CVOFADIQMPPSOB-UHFFFAOYSA-N 0.000 description 2
BEAUQZLEEKWDRB-UHFFFAOYSA-N methyl 7-[3-[2-[3,4-bis[[tert-butyl(dimethyl)silyl]oxy]phenyl]ethenyl]phenyl]hept-6-enoate Chemical compound COC(=O)CCCCC=CC1=CC=CC(C=CC=2C=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=CC=2)=C1 BEAUQZLEEKWDRB-UHFFFAOYSA-N 0.000 description 2
BHQDABIPVVYSGZ-UHFFFAOYSA-N methyl 7-[3-[2-[3,5-bis(ethoxymethoxy)phenyl]ethenyl]phenyl]hept-6-enoate Chemical compound CCOCOC1=CC(OCOCC)=CC(C=CC=2C=C(C=CCCCCC(=O)OC)C=CC=2)=C1 BHQDABIPVVYSGZ-UHFFFAOYSA-N 0.000 description 2
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210000004080 milk Anatomy 0.000 description 2
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230000003020 moisturizing effect Effects 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
UFLFHDVSGSPVLA-UHFFFAOYSA-N n-[2-[3-[tert-butyl(dimethyl)silyl]oxyphenyl]ethyl]-4-hydroxy-4-methylpentanamide Chemical compound CC(C)(O)CCC(=O)NCCC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1 UFLFHDVSGSPVLA-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
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230000002062 proliferating effect Effects 0.000 description 2
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108020003175 receptors Proteins 0.000 description 2
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230000008439 repair process Effects 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
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SSNDSBVMRHZXMR-UHFFFAOYSA-N tert-butyl-[[2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-ethynylphenyl]methoxy]-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCC1=CC=C(C#C)C=C1CO[Si](C)(C)C(C)(C)C SSNDSBVMRHZXMR-UHFFFAOYSA-N 0.000 description 2
NKAKWDGJDMYFGJ-UHFFFAOYSA-N tert-butyl-dimethyl-[3-[2-[3-[6-methyl-6-(oxan-2-yloxy)heptyl]phenyl]ethenyl]phenoxy]silane Chemical compound C1CCCOC1OC(C)(C)CCCCCC(C=1)=CC=CC=1C=CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1 NKAKWDGJDMYFGJ-UHFFFAOYSA-N 0.000 description 2
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229910052723 transition metal Inorganic materials 0.000 description 2
150000003624 transition metals Chemical class 0.000 description 2
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ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 2
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GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
150000002681 magnesium compounds Chemical class 0.000 description 1
YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002523 mercuric chloride Drugs 0.000 description 1
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
XOPUORAQCYGJPT-UHFFFAOYSA-N methanesulfonic acid;hydrochloride Chemical compound Cl.CS(O)(=O)=O XOPUORAQCYGJPT-UHFFFAOYSA-N 0.000 description 1
GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 1
NTNUDYROPUKXNA-UHFFFAOYSA-N methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC)C1=CC=CC=C1 NTNUDYROPUKXNA-UHFFFAOYSA-N 0.000 description 1
ODCVCBLUFQCUHW-UHFFFAOYSA-N methyl 3,5-bis[[tert-butyl(dimethyl)silyl]oxy]benzoate Chemical compound COC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1 ODCVCBLUFQCUHW-UHFFFAOYSA-N 0.000 description 1
GQSYFVZOEVJLOB-UHFFFAOYSA-N methyl 3-(ethoxymethoxy)-5-(ethoxymethoxymethyl)benzoate Chemical compound CCOCOCC1=CC(OCOCC)=CC(C(=O)OC)=C1 GQSYFVZOEVJLOB-UHFFFAOYSA-N 0.000 description 1
ZOZUVUDGBLYGQE-UHFFFAOYSA-N methyl 5-(3-hydroxyphenyl)-5-methylhexanoate Chemical compound COC(=O)CCCC(C)(C)C1=CC=CC(O)=C1 ZOZUVUDGBLYGQE-UHFFFAOYSA-N 0.000 description 1
NGNBVJZQXJNPGZ-UHFFFAOYSA-N methyl 5-(3-hydroxyphenyl)hex-4-enoate Chemical compound COC(=O)CCC=C(C)C1=CC=CC(O)=C1 NGNBVJZQXJNPGZ-UHFFFAOYSA-N 0.000 description 1
MJPGJHWIEQWOEO-UHFFFAOYSA-N methyl 5-[3-[2-[3-(ethoxymethoxy)-5-(ethoxymethoxymethyl)phenyl]ethenyl]phenyl]pentanoate Chemical compound CCOCOCC1=CC(OCOCC)=CC(C=CC=2C=C(CCCCC(=O)OC)C=CC=2)=C1 MJPGJHWIEQWOEO-UHFFFAOYSA-N 0.000 description 1
JOQSMGKXMZPPPX-UHFFFAOYSA-N methyl 5-[3-[[3,4-bis[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]methoxy]phenyl]pentanoate Chemical compound COC(=O)CCCCC1=CC=CC(OCC=2C=C(CO[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)=CC=2)=C1 JOQSMGKXMZPPPX-UHFFFAOYSA-N 0.000 description 1
NQPRTQUVWURUGZ-UHFFFAOYSA-N methyl 6-[3-[2-[3,4-bis[[tert-butyl(dimethyl)silyl]oxymethyl]phenyl]ethynyl]phenyl]hexanoate Chemical compound COC(=O)CCCCCC1=CC=CC(C#CC=2C=C(CO[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)=CC=2)=C1 NQPRTQUVWURUGZ-UHFFFAOYSA-N 0.000 description 1
DCPSPNNTXSKBBU-UHFFFAOYSA-N methyl 7-[3-[2-[3,5-bis(oxan-2-yloxy)phenyl]ethenyl]phenyl]hept-6-enoate Chemical compound COC(=O)CCCCC=CC1=CC=CC(C=CC=2C=C(OC3OCCCC3)C=C(OC3OCCCC3)C=2)=C1 DCPSPNNTXSKBBU-UHFFFAOYSA-N 0.000 description 1
CKBLOFYULAYLTQ-UHFFFAOYSA-N methyl 7-[3-[2-[3,5-bis(oxan-2-yloxy)phenyl]ethenyl]phenyl]heptanoate Chemical compound COC(=O)CCCCCCC1=CC=CC(C=CC=2C=C(OC3OCCCC3)C=C(OC3OCCCC3)C=2)=C1 CKBLOFYULAYLTQ-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000008267 milk Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
PGNHFRVPUAKQOI-UHFFFAOYSA-N n-[2-[3-[tert-butyl(dimethyl)silyl]oxyphenyl]ethyl]-4-oxopentanamide Chemical compound CC(=O)CCC(=O)NCCC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1 PGNHFRVPUAKQOI-UHFFFAOYSA-N 0.000 description 1
HOSDXRPMYVXNHK-UHFFFAOYSA-N n-[3-[tert-butyl(dimethyl)silyl]oxyphenyl]-n-ethyl-4-oxopentanamide Chemical compound CC(=O)CCC(=O)N(CC)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1 HOSDXRPMYVXNHK-UHFFFAOYSA-N 0.000 description 1
229960004927 neomycin Drugs 0.000 description 1
XAQDNRLCLMAVQN-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O.CCCCCCC(C)O XAQDNRLCLMAVQN-UHFFFAOYSA-N 0.000 description 1
SJWFXCIHNDVPSH-UHFFFAOYSA-N octane-2-ol Natural products CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
VEDDBHYQWFOITD-UHFFFAOYSA-N para-bromobenzyl alcohol Chemical compound OCC1=CC=C(Br)C=C1 VEDDBHYQWFOITD-UHFFFAOYSA-N 0.000 description 1
239000000199 parathyroid hormone Substances 0.000 description 1
229960001319 parathyroid hormone Drugs 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000003395 phenylethylamino group Chemical group [H]N(*)C([H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
229960002036 phenytoin Drugs 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
239000013612 plasmid Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
NPCOQXAVBJJZBQ-UHFFFAOYSA-N reduced coenzyme Q9 Natural products COC1=C(O)C(C)=C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C(O)=C1OC NPCOQXAVBJJZBQ-UHFFFAOYSA-N 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
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108090000064 retinoic acid receptors Proteins 0.000 description 1
238000012552 review Methods 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
KXRDRWRYDHFBBZ-UHFFFAOYSA-N s-(3-acetylphenyl) n,n-dimethylcarbamothioate Chemical compound CN(C)C(=O)SC1=CC=CC(C(C)=O)=C1 KXRDRWRYDHFBBZ-UHFFFAOYSA-N 0.000 description 1
229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
150000003872 salicylic acid derivatives Chemical class 0.000 description 1
238000012216 screening Methods 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
239000000344 soap Substances 0.000 description 1
HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000001433 sodium tartrate Substances 0.000 description 1
229960002167 sodium tartrate Drugs 0.000 description 1
235000011004 sodium tartrates Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007940 sugar coated tablet Substances 0.000 description 1
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239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
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239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
ZIXYMEYGDPKBLR-UHFFFAOYSA-N tert-butyl-[3-[tert-butyl(dimethyl)silyl]oxy-5-[[3-[6-methyl-6-(oxan-2-yloxy)heptyl]phenoxy]methyl]phenoxy]-dimethylsilane Chemical compound C1CCCOC1OC(C)(C)CCCCCC(C=1)=CC=CC=1OCC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C1 ZIXYMEYGDPKBLR-UHFFFAOYSA-N 0.000 description 1
KXWVLIUVNMCAMP-UHFFFAOYSA-N tert-butyl-[[2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[2-[4-[5-methyl-5-(oxan-2-yloxy)hexyl]phenyl]ethenyl]phenyl]methoxy]-dimethylsilane Chemical compound C1CCCOC1OC(C)(C)CCCCC(C=C1)=CC=C1C=CC1=CC=C(CO[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)=C1 KXWVLIUVNMCAMP-UHFFFAOYSA-N 0.000 description 1
VABQLIMLIHTZRU-UHFFFAOYSA-N tert-butyl-[[2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-[2-[4-[6-methyl-6-(oxan-2-yloxy)heptyl]phenyl]ethenyl]phenyl]methoxy]-dimethylsilane Chemical compound C1CCCOC1OC(C)(C)CCCCCC(C=C1)=CC=C1C=CC1=CC=C(CO[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)=C1 VABQLIMLIHTZRU-UHFFFAOYSA-N 0.000 description 1
UJZXNYFJCUDGEY-UHFFFAOYSA-N tert-butyl-[[2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-iodophenyl]methoxy]-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)OCC1=CC=C(I)C=C1CO[Si](C)(C)C(C)(C)C UJZXNYFJCUDGEY-UHFFFAOYSA-N 0.000 description 1
RMZZVEJWAWRYKY-UHFFFAOYSA-N tert-butyl-[[3-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-[2-[3-[6-methyl-6-(oxan-2-yloxy)heptyl]phenyl]ethenyl]phenyl]methoxy]-dimethylsilane Chemical compound C1CCCOC1OC(C)(C)CCCCCC(C=1)=CC=CC=1C=CC1=CC(CO[Si](C)(C)C(C)(C)C)=CC(CO[Si](C)(C)C(C)(C)C)=C1 RMZZVEJWAWRYKY-UHFFFAOYSA-N 0.000 description 1
KSHZXTRSNXBCGT-UHFFFAOYSA-N tert-butyl-dimethyl-[[4-[2-[3-[6-methyl-6-(oxan-2-yloxy)heptyl]phenyl]ethenyl]phenyl]methoxy]silane Chemical compound C1CCCOC1OC(C)(C)CCCCCC(C=1)=CC=CC=1C=CC1=CC=C(CO[Si](C)(C)C(C)(C)C)C=C1 KSHZXTRSNXBCGT-UHFFFAOYSA-N 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
229940040944 tetracyclines Drugs 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
229960000984 tocofersolan Drugs 0.000 description 1
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229960001295 tocopherol Drugs 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
238000013518 transcription Methods 0.000 description 1
230000035897 transcription Effects 0.000 description 1
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Substances CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 1
QXTIBZLKQPJVII-UHFFFAOYSA-N triethylsilicon Chemical compound CC[Si](CC)CC QXTIBZLKQPJVII-UHFFFAOYSA-N 0.000 description 1
STMPXDBGVJZCEX-UHFFFAOYSA-N triethylsilyl trifluoromethanesulfonate Chemical compound CC[Si](CC)(CC)OS(=O)(=O)C(F)(F)F STMPXDBGVJZCEX-UHFFFAOYSA-N 0.000 description 1
SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
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QNTNKSLOFHEFPK-UPTCCGCDSA-N ubiquinol-10 Chemical compound COC1=C(O)C(C)=C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)C(O)=C1OC QNTNKSLOFHEFPK-UPTCCGCDSA-N 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
150000003703 vitamin D2 derivatives Chemical class 0.000 description 1
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239000002023 wood Substances 0.000 description 1
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OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 1

Classifications

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- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/205—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings
- C07C39/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing only six-membered aromatic rings as cyclic parts with unsaturation outside the rings with at least one hydroxy group on a non-condensed ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C401/00—Irradiation products of cholesterol or its derivatives; Vitamin D derivatives, 9,10-seco cyclopenta[a]phenanthrene or analogues obtained by chemical preparation without irradiation
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- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A—HUMAN NECESSITIES
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- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- C07—ORGANIC CHEMISTRY
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- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/26—Polyhydroxylic alcohols containing only six-membered aromatic rings as cyclic part
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- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
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- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/178—Unsaturated ethers containing hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
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- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups

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NO20012116A 1998-11-02 2001-04-27 Vitamin D analoger, deres anvendelse samt farmasoytisk og kosmetisk preparat inneholdende de samme NO328597B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9813747A FR2785284B1 (fr)	1998-11-02	1998-11-02	Analogues de la vitamine d
PCT/FR1999/002637 WO2000026167A1 (fr)	1998-11-02	1999-10-28	Analogues de la vitamine d

Publications (3)

Publication Number	Publication Date
NO20012116D0 NO20012116D0 (no)	2001-04-27
NO20012116L NO20012116L (no)	2001-07-02
NO328597B1 true NO328597B1 (no)	2010-03-29

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Application Number	Title	Priority Date	Filing Date
NO20012116A NO328597B1 (no)	1998-11-02	2001-04-27	Vitamin D analoger, deres anvendelse samt farmasoytisk og kosmetisk preparat inneholdende de samme

Country Status (25)

Country	Link
US (1)	US6689922B1 (es)
EP (1)	EP1124779B1 (es)
JP (2)	JP3869658B2 (es)
KR (2)	KR100595958B1 (es)
CN (1)	CN1282636C (es)
AR (1)	AR024516A1 (es)
AT (1)	ATE288410T1 (es)
AU (1)	AU762056B2 (es)
BR (1)	BR9915247B1 (es)
CA (1)	CA2348725C (es)
DE (1)	DE69923573T2 (es)
DK (1)	DK1124779T3 (es)
ES (1)	ES2237947T3 (es)
FR (1)	FR2785284B1 (es)
HK (1)	HK1043588B (es)
HU (1)	HUP0104195A3 (es)
IL (1)	IL142759A (es)
NO (1)	NO328597B1 (es)
NZ (1)	NZ511239A (es)
PL (1)	PL197341B1 (es)
PT (1)	PT1124779E (es)
RU (1)	RU2208601C2 (es)
TW (1)	TWI242001B (es)
WO (1)	WO2000026167A1 (es)
ZA (1)	ZA200103186B (es)

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1998
- 1998-11-02 FR FR9813747A patent/FR2785284B1/fr not_active Expired - Fee Related
1999
- 1999-10-16 TW TW088117922A patent/TWI242001B/zh not_active IP Right Cessation
- 1999-10-28 BR BRPI9915247-9A patent/BR9915247B1/pt not_active IP Right Cessation
- 1999-10-28 DK DK99950869T patent/DK1124779T3/da active
- 1999-10-28 ES ES99950869T patent/ES2237947T3/es not_active Expired - Lifetime
- 1999-10-28 DE DE69923573T patent/DE69923573T2/de not_active Expired - Lifetime
- 1999-10-28 AT AT99950869T patent/ATE288410T1/de active
- 1999-10-28 HU HU0104195A patent/HUP0104195A3/hu unknown
- 1999-10-28 JP JP2000579557A patent/JP3869658B2/ja not_active Expired - Fee Related
- 1999-10-28 NZ NZ511239A patent/NZ511239A/en not_active IP Right Cessation
- 1999-10-28 KR KR1020057008184A patent/KR100595958B1/ko not_active Expired - Fee Related
- 1999-10-28 PT PT99950869T patent/PT1124779E/pt unknown
- 1999-10-28 CA CA002348725A patent/CA2348725C/fr not_active Expired - Fee Related
- 1999-10-28 PL PL347548A patent/PL197341B1/pl unknown
- 1999-10-28 RU RU2001115100/04A patent/RU2208601C2/ru not_active IP Right Cessation
- 1999-10-28 KR KR10-2001-7005428A patent/KR100525022B1/ko not_active Expired - Fee Related
- 1999-10-28 CN CNB998153516A patent/CN1282636C/zh not_active Expired - Fee Related
- 1999-10-28 EP EP99950869A patent/EP1124779B1/fr not_active Expired - Lifetime
- 1999-10-28 AU AU63476/99A patent/AU762056B2/en not_active Ceased
- 1999-10-28 IL IL142759A patent/IL142759A/en not_active IP Right Cessation
- 1999-10-28 US US09/830,973 patent/US6689922B1/en not_active Expired - Fee Related
- 1999-10-28 WO PCT/FR1999/002637 patent/WO2000026167A1/fr not_active Ceased
- 1999-10-28 HK HK02105220.9A patent/HK1043588B/zh not_active IP Right Cessation
- 1999-11-01 AR ARP990105514A patent/AR024516A1/es active IP Right Grant
2001
- 2001-04-19 ZA ZA200103186A patent/ZA200103186B/en unknown
- 2001-04-27 NO NO20012116A patent/NO328597B1/no not_active IP Right Cessation
2005
- 2005-07-15 JP JP2005207861A patent/JP2006028185A/ja active Pending

Also Published As

Publication number	Publication date
PT1124779E (pt)	2005-06-30
HK1043588A1 (en)	2002-09-20
KR100525022B1 (ko)	2005-10-31
WO2000026167A1 (fr)	2000-05-11
AU6347699A (en)	2000-05-22
TWI242001B (en)	2005-10-21
CA2348725A1 (fr)	2000-05-11
NO20012116D0 (no)	2001-04-27
US6689922B1 (en)	2004-02-10
BR9915247B1 (pt)	2012-05-29
HUP0104195A2 (hu)	2002-03-28
HUP0104195A3 (en)	2002-04-29
CA2348725C (fr)	2007-04-17
IL142759A (en)	2008-06-05
RU2208601C2 (ru)	2003-07-20
KR20050047142A (ko)	2005-05-19
CN1282636C (zh)	2006-11-01
AU762056B2 (en)	2003-06-19
ZA200103186B (en)	2001-11-22
FR2785284B1 (fr)	2000-12-01
BR9915247A (pt)	2001-10-30
KR100595958B1 (ko)	2006-07-03
JP3869658B2 (ja)	2007-01-17
EP1124779A1 (fr)	2001-08-22
CN1332711A (zh)	2002-01-23
HK1043588B (zh)	2007-06-15
NO20012116L (no)	2001-07-02
IL142759A0 (en)	2002-03-10
NZ511239A (en)	2003-11-28
AR024516A1 (es)	2002-10-16
DE69923573T2 (de)	2006-01-05
PL347548A1 (en)	2002-04-08
JP2002528523A (ja)	2002-09-03
ATE288410T1 (de)	2005-02-15
KR20010081102A (ko)	2001-08-27
PL197341B1 (pl)	2008-03-31
DK1124779T3 (da)	2005-06-06
EP1124779B1 (fr)	2005-02-02
DE69923573D1 (de)	2005-03-10
JP2006028185A (ja)	2006-02-02
ES2237947T3 (es)	2005-08-01
FR2785284A1 (fr)	2000-05-05

Publication	Publication Date	Title
NO328597B1 (no)	2010-03-29	Vitamin D analoger, deres anvendelse samt farmasoytisk og kosmetisk preparat inneholdende de samme
CA2392165C (fr)	2008-08-26	Analogues de la vitamine d
JP2011037859A (ja)	2011-02-24	ビタミンｄ類似体
KR19990078359A (ko)	1999-10-25	이환성 방향족 화합물 및 인간 또는 수의학용 의약 및 화장학에서 그의 용도
US7700657B2 (en)	2010-04-20	Vitamin D analogs
US6924400B2 (en)	2005-08-02	Triaromatic vitamin D analogues

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