FI112357B - Retinohapon X-reseptoriligandit - Google Patents

Retinohapon X-reseptoriligandit Download PDF

Info

Publication number: FI112357B
Authority: FI; Finland
Prior art keywords: formula; tetramethyl; methyl; compounds; penta
Prior art date: 1994-08-10

Application number

FI970547A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI970547A0 (fi

FI970547L (fi

Inventor

Michael Klaus

Allen John Lovey

Michael Rosenberger

Peter Mohr

Original Assignee

Hoffmann La Roche

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.)

1994-08-10

Filing date

1997-02-07

Publication date

2003-11-28

1997-02-07 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1997-02-07 Publication of FI970547A0 publication Critical patent/FI970547A0/fi

1997-02-07 Publication of FI970547L publication Critical patent/FI970547L/fi

2003-11-28 Application granted granted Critical

2003-11-28 Publication of FI112357B publication Critical patent/FI112357B/fi

Links

SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 title description 6
229930002330 retinoic acid Natural products 0.000 title description 6
229960001727 tretinoin Drugs 0.000 title description 5
239000003446 ligand Substances 0.000 title description 4
101000804917 Homo sapiens Xenotropic and polytropic retrovirus receptor 1 Proteins 0.000 title 1
102100036974 Xenotropic and polytropic retrovirus receptor 1 Human genes 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 100
-1 tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl Chemical group 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 20
150000003839 salts Chemical class 0.000 claims description 14
SDVVLIIVFBKBMG-ONEGZZNKSA-N (E)-penta-2,4-dienoic acid Chemical compound OC(=O)\C=C\C=C SDVVLIIVFBKBMG-ONEGZZNKSA-N 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000003118 aryl group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 7
150000001721 carbon Chemical group 0.000 claims description 7
150000001735 carboxylic acids Chemical class 0.000 claims description 7
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
150000002431 hydrogen Chemical group 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
208000002874 Acne Vulgaris Diseases 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
206010000496 acne Diseases 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
208000032839 leukemia Diseases 0.000 claims description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
125000003627 8 membered carbocyclic group Chemical group 0.000 claims description 2
201000004681 Psoriasis Diseases 0.000 claims description 2
MIJRBLKOFZPSDD-QFJHZUDSSA-N ethyl (2e,4e)-3-methyl-5-[2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)cyclopenten-1-yl]penta-2,4-dienoate Chemical compound C1CCC(/C=C/C(/C)=C/C(=O)OCC)=C1C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 MIJRBLKOFZPSDD-QFJHZUDSSA-N 0.000 claims description 2
239000000463 material Substances 0.000 claims description 2
239000000825 pharmaceutical preparation Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
IAAPVNQZSBLWKH-ICDJNDDTSA-N (2e,4e,6e)-octa-2,4,6-trienoic acid Chemical compound C\C=C\C=C\C=C\C(O)=O IAAPVNQZSBLWKH-ICDJNDDTSA-N 0.000 claims 1
101100440696 Caenorhabditis elegans cor-1 gene Proteins 0.000 claims 1
125000002619 bicyclic group Chemical group 0.000 claims 1
125000004122 cyclic group Chemical group 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
XTGVFTSNFUPNDL-WQUQCEJDSA-N ethyl (2e,4e,6e)-6-bromo-3-methyl-7-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)octa-2,4,6-trienoate Chemical compound CC1(C)CCC(C)(C)C=2C1=CC(C(\C)=C(\Br)/C=C/C(/C)=C/C(=O)OCC)=CC=2 XTGVFTSNFUPNDL-WQUQCEJDSA-N 0.000 claims 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
150000004492 retinoid derivatives Chemical class 0.000 abstract description 6
230000000771 oncological effect Effects 0.000 abstract description 2
230000001028 anti-proliverative effect Effects 0.000 abstract 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 81
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
239000000243 solution Substances 0.000 description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
239000000203 mixture Substances 0.000 description 26
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
229910052938 sodium sulfate Inorganic materials 0.000 description 16
235000011152 sodium sulphate Nutrition 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
239000000741 silica gel Substances 0.000 description 14
229910002027 silica gel Inorganic materials 0.000 description 14
239000013078 crystal Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
238000003818 flash chromatography Methods 0.000 description 12
239000002904 solvent Substances 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
239000000460 chlorine Substances 0.000 description 11
238000004817 gas chromatography Methods 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
238000003756 stirring Methods 0.000 description 9
WQXIOLXRWLPJLQ-UKRGKPDNSA-N (2e,4e)-3-methyl-5-[2-(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)phenyl]penta-2,4-dienoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C1=CC=CC=C1C1=CC=C2C(C)(C)CCC(C)(C)C2=C1 WQXIOLXRWLPJLQ-UKRGKPDNSA-N 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
239000012267 brine Substances 0.000 description 8
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
102000003702 retinoic acid receptors Human genes 0.000 description 7
108090000064 retinoic acid receptors Proteins 0.000 description 7
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
239000002775 capsule Substances 0.000 description 6
238000009472 formulation Methods 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
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 5
239000002585 base Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 5
229920002261 Corn starch Polymers 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000008120 corn starch Substances 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
238000000034 method Methods 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
239000011701 zinc Substances 0.000 description 4
NLOOVMVNNNYLFS-UHFFFAOYSA-N 6-bromo-1,1,4,4-tetramethyl-2,3-dihydronaphthalene Chemical compound BrC1=CC=C2C(C)(C)CCC(C)(C)C2=C1 NLOOVMVNNNYLFS-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
229920000168 Microcrystalline cellulose Polymers 0.000 description 3
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000006071 cream Substances 0.000 description 3
230000004069 differentiation Effects 0.000 description 3
238000001035 drying Methods 0.000 description 3
OQKGPUSERILONW-CSKARUKUSA-N ethyl (e)-4-diethoxyphosphoryl-3-methylbut-2-enoate Chemical compound CCOC(=O)\C=C(/C)CP(=O)(OCC)OCC OQKGPUSERILONW-CSKARUKUSA-N 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000002609 medium Substances 0.000 description 3
239000008108 microcrystalline cellulose Substances 0.000 description 3
235000019813 microcrystalline cellulose Nutrition 0.000 description 3
229940016286 microcrystalline cellulose Drugs 0.000 description 3
239000002480 mineral oil Substances 0.000 description 3
235000010446 mineral oil Nutrition 0.000 description 3
239000002674 ointment Substances 0.000 description 3
XUYJLQHKOGNDPB-UHFFFAOYSA-N phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O XUYJLQHKOGNDPB-UHFFFAOYSA-N 0.000 description 3
238000000746 purification Methods 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 3
WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 2
OPDGWSYNXPRREB-UHFFFAOYSA-N 5,6,7,8-tetramethyl-1,2,3,4-tetrahydronaphthalene Chemical compound C1CCCC2=C(C)C(C)=C(C)C(C)=C21 OPDGWSYNXPRREB-UHFFFAOYSA-N 0.000 description 2
HVGUEOSJZVJXSA-BSWSSELBSA-N BrC1=C(CCC1)/C=C/C(=C/C(=O)O)/C Chemical compound BrC1=C(CCC1)/C=C/C(=C/C(=O)O)/C HVGUEOSJZVJXSA-BSWSSELBSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
229920003081 Povidone K 30 Polymers 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 2
238000007239 Wittig reaction Methods 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
230000024245 cell differentiation Effects 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 2
WCASXYBKJHWFMY-UHFFFAOYSA-N crotyl alcohol Chemical compound CC=CCO WCASXYBKJHWFMY-UHFFFAOYSA-N 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
238000005888 cyclopropanation reaction Methods 0.000 description 2
GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 2
238000005695 dehalogenation reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
239000008187 granular material Substances 0.000 description 2
230000001965 increasing effect Effects 0.000 description 2
230000001939 inductive effect Effects 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
125000006574 non-aromatic ring group Chemical group 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 2
LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
229930192474 thiophene Natural products 0.000 description 2
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GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical group C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
235000019166 vitamin D Nutrition 0.000 description 1
239000011710 vitamin D Substances 0.000 description 1
229940046008 vitamin d Drugs 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
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 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/56—Crotonic acid esters; Vinyl acetic acid esters
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/24—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
- C07C57/50—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid containing condensed ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Dermatology (AREA)
Hematology (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Obesity (AREA)
Oncology (AREA)
Diabetes (AREA)
Nutrition Science (AREA)
Epidemiology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Steroid Compounds (AREA)
Paints Or Removers (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

FI970547A 1994-08-10 1997-02-07 Retinohapon X-reseptoriligandit FI112357B (fi)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
EP94112461		1994-08-10
EP94112461		1994-08-10
EP95110460		1995-07-05
EP95110460		1995-07-05
PCT/EP1995/003021 WO1996005165A1 (fr)	1994-08-10	1995-07-29	Ligands des recepteurs x de l'acide retinoique
EP9503021		1995-07-29

Publications (3)

Publication Number	Publication Date
FI970547A0 FI970547A0 (fi)	1997-02-07
FI970547L FI970547L (fi)	1997-02-07
FI112357B true FI112357B (fi)	2003-11-28

Family

ID=26135772

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI970547A FI112357B (fi)	1994-08-10	1997-02-07	Retinohapon X-reseptoriligandit

Country Status (24)

Country	Link
US (1)	US5801253A (fr)
EP (1)	EP0775103B1 (fr)
JP (1)	JP2848964B2 (fr)
KR (1)	KR100363545B1 (fr)
CN (1)	CN1091092C (fr)
AT (1)	ATE181052T1 (fr)
AU (1)	AU696501B2 (fr)
BR (1)	BR9508985A (fr)
CA (1)	CA2196197C (fr)
CY (1)	CY2170B1 (fr)
CZ (1)	CZ288526B6 (fr)
DE (1)	DE69510203T2 (fr)
DK (1)	DK0775103T3 (fr)
ES (1)	ES2133798T3 (fr)
FI (1)	FI112357B (fr)
GR (1)	GR3031154T3 (fr)
HU (1)	HU218268B (fr)
MX (1)	MX9700778A (fr)
NO (1)	NO307702B1 (fr)
NZ (1)	NZ292121A (fr)
PL (1)	PL180048B1 (fr)
RU (1)	RU2146241C1 (fr)
TR (1)	TR199500976A2 (fr)
WO (1)	WO1996005165A1 (fr)

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US6028052A (en)	1995-09-18	2000-02-22	Ligand Pharmaceuticals Incorporated	Treating NIDDM with RXR agonists
CA2233888A1 (fr)	1995-10-06	1997-04-10	Ligand Pharmaceuticals Incorporated	Modulateurs rxr selectifs pour les dimeres et leurs methodes d'utilisation
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US6403638B1 (en) *	1998-10-01	2002-06-11	Allergan Sales, Inc.	2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors
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EP1212322A2 (fr)	1999-08-27	2002-06-12	Ligand Pharmaceuticals Incorporated	Composes de 6-trifluoromethyl-9-pyrido[3,2-g]quinoline 8-substitues utilises comme modulateurs de recepteurs androgenes
US6566372B1 (en)	1999-08-27	2003-05-20	Ligand Pharmaceuticals Incorporated	Bicyclic androgen and progesterone receptor modulator compounds and methods
TR200200507T2 (tr)	1999-08-27	2002-10-21	Ligand Pharmaceuticals Inc	Androjen reseptörü modülatör bileşikleri ve metotları
AU7586600A (en)	1999-09-14	2001-04-17	Ligand Pharmaceuticals Incorporated	Rxr modulators with improved pharmacologic profile
PT1741446E (pt)	2000-01-21	2008-05-09	Novartis Pharma Ag	Combinações incluindo inibidores da dipeptidilpeptidase-iv e agentes anti-diabéticos
US6369225B1 (en)	2000-08-29	2002-04-09	Allergan Sales, Inc.	Compounds having activity as inhibitors of cytochrome P450RAI
US6313107B1 (en)	2000-08-29	2001-11-06	Allergan Sales, Inc.	Methods of providing and using compounds having activity as inhibitors of cytochrome P450RAI
US6380256B1 (en)	2000-08-29	2002-04-30	Allergan Sales, Inc.	Compounds having activity as inhibitors of cytochrome P450RAI
DE60136477D1 (de) *	2000-10-02	2008-12-18	Hoffmann La Roche	Retinoide zur behandlung von emphysem
EP1373240B1 (fr) *	2001-03-14	2005-06-15	Eli Lilly And Company	Modulateurs des recepteurs x de retinoides
US6720423B2 (en)	2002-04-30	2004-04-13	Allergan, Inc.	Dihydrobenzofuran and dihydrobenzothiophene 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors
WO2004048390A1 (fr) *	2002-11-25	2004-06-10	Amedis Pharmaceuticals Ltd.	Composes de silicium
US6759547B1 (en)	2003-01-14	2004-07-06	Allergan, Inc.	5,6,7,8-tetrahydronaphthalen-2-yl 2,6-difluoroheptatrienoic acid derivatives having serum glucose reducing activity
US7019034B2 (en) *	2003-01-28	2006-03-28	Allergan, Inc.	Compositions and methods for reducing serum glucose and triglyceride levels in diabetic mammals
US6759546B1 (en)	2003-02-04	2004-07-06	Allergan, Inc.	3,5-di-iso-propyl-heptatrienoic acid derivatives having serum glucose reducing activity
US6884820B2 (en) *	2003-04-03	2005-04-26	Allergan, Inc.	5,6,7,8-tetrahydronaphthalen-2-yl-7-fluoroalkyl-heptatrienoic acid derivatives having serum glucose reducing activity
US6734193B1 (en)	2003-06-03	2004-05-11	Allergan, Inc.	(1,2,3,4-tetrahydroquinolin-8-yl)-heptatrienoic acid derivatives having serum glucose reducing activity
AU2004263156B2 (en) *	2003-08-07	2009-02-26	Allergan, Inc.	Method for treating cachexia with retinoid ligands
US6887896B1 (en)	2003-10-29	2005-05-03	Allergan, Inc.	7-[(7-Alkoxy)-chrom-3-en-6-yl]-heptatrienoic acid and 7-[(3-alkoxy)-5,6-dihydronaphthalen-2-yl]-heptatrienoic acid derivatives having serum glucose reducing activity
US9050310B2 (en)	2004-06-25	2015-06-09	Minas Theodore Coroneo	Treatment of ocular lesions
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1995
- 1995-07-29 ES ES95930430T patent/ES2133798T3/es not_active Expired - Lifetime
- 1995-07-29 HU HU9700356A patent/HU218268B/hu not_active IP Right Cessation
- 1995-07-29 BR BR9508985A patent/BR9508985A/pt not_active IP Right Cessation
- 1995-07-29 EP EP95930430A patent/EP0775103B1/fr not_active Expired - Lifetime
- 1995-07-29 NZ NZ292121A patent/NZ292121A/xx unknown
- 1995-07-29 CZ CZ1997382A patent/CZ288526B6/cs not_active IP Right Cessation
- 1995-07-29 JP JP8506962A patent/JP2848964B2/ja not_active Expired - Fee Related
- 1995-07-29 MX MX9700778A patent/MX9700778A/es not_active IP Right Cessation
- 1995-07-29 CN CN95194064A patent/CN1091092C/zh not_active Expired - Fee Related
- 1995-07-29 US US08/776,087 patent/US5801253A/en not_active Expired - Fee Related
- 1995-07-29 WO PCT/EP1995/003021 patent/WO1996005165A1/fr not_active Ceased
- 1995-07-29 DE DE69510203T patent/DE69510203T2/de not_active Expired - Fee Related
- 1995-07-29 PL PL95318557A patent/PL180048B1/pl not_active IP Right Cessation
- 1995-07-29 AT AT95930430T patent/ATE181052T1/de not_active IP Right Cessation
- 1995-07-29 AU AU33821/95A patent/AU696501B2/en not_active Ceased
- 1995-07-29 CA CA002196197A patent/CA2196197C/fr not_active Expired - Fee Related
- 1995-07-29 RU RU97106022A patent/RU2146241C1/ru not_active IP Right Cessation
- 1995-07-29 DK DK95930430T patent/DK0775103T3/da active
- 1995-07-29 KR KR1019970700814A patent/KR100363545B1/ko not_active Expired - Fee Related
- 1995-08-08 TR TR95/00976A patent/TR199500976A2/xx unknown
1997
- 1997-02-07 FI FI970547A patent/FI112357B/fi not_active IP Right Cessation
- 1997-02-07 NO NO970580A patent/NO307702B1/no unknown
1999
- 1999-09-03 GR GR990402243T patent/GR3031154T3/el unknown
2000
- 2000-05-08 CY CY0000016A patent/CY2170B1/xx unknown

Also Published As

Publication number	Publication date
JP2848964B2 (ja)	1999-01-20
PL180048B1 (en)	2000-12-29
NZ292121A (en)	1998-10-28
JPH09512830A (ja)	1997-12-22
FI970547A0 (fi)	1997-02-07
PL318557A1 (en)	1997-06-23
CN1091092C (zh)	2002-09-18
AU3382195A (en)	1996-03-07
KR970704663A (ko)	1997-09-06
HUT76839A (en)	1997-11-28
CN1152302A (zh)	1997-06-18
GR3031154T3 (en)	1999-12-31
NO970580L (no)	1997-02-07
CA2196197C (fr)	2007-04-17
WO1996005165A1 (fr)	1996-02-22
FI970547L (fi)	1997-02-07
BR9508985A (pt)	1998-01-06
EP0775103B1 (fr)	1999-06-09
NO307702B1 (no)	2000-05-15
DK0775103T3 (da)	1999-11-15
CA2196197A1 (fr)	1996-02-22
HU218268B (hu)	2000-06-28
AU696501B2 (en)	1998-09-10
DE69510203D1 (de)	1999-07-15
KR100363545B1 (ko)	2003-02-19
TR199500976A2 (tr)	1996-06-21
NO970580D0 (no)	1997-02-07
CY2170B1 (en)	2002-08-23
EP0775103A1 (fr)	1997-05-28
DE69510203T2 (de)	1999-12-23
ATE181052T1 (de)	1999-06-15
RU2146241C1 (ru)	2000-03-10
CZ38297A3 (en)	1997-06-11
US5801253A (en)	1998-09-01
ES2133798T3 (es)	1999-09-16
MX9700778A (es)	1997-05-31
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Date	Code	Title	Description
2007-01-31	MA	Patent expired

Publication	Publication Date	Title
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DE69623300T2 (de)	2003-03-20	2,4 pentadiensaurederivate mit retinoidartigen biologischen aktivität
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JP4001913B2 (ja)	2007-10-31	新規なトリエンレチノイド化合物および方法
RU2166499C2 (ru)	2001-05-10	Ретиноиды
KR100335540B1 (ko)	2002-10-25	방향족카복실산유도체및이를포함하는약학적제제
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