OA12880A - Novel thiophenylglycoside derivatives, methods forproduction thereof, medicaments comprising said c ompounds and use thereof. - Google Patents

Novel thiophenylglycoside derivatives, methods forproduction thereof, medicaments comprising said c ompounds and use thereof. Download PDF

Info

Publication number: OA12880A
Authority: OA; OAPI
Prior art keywords: alkyl; formula; compound; hydrogen; compounds
Prior art date: 2002-07-11

Application number

OA1200500001A

Other languages

English (en)

Inventor

Heiner Glombik

Wendelin Frick

Hubert Heuer

Werner Kramer

Harm Brummerhop

Oliver Plettenburg

Original Assignee

Aventis Pharma Gmbh

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.)

2002-07-11

Filing date

2003-06-27

Publication date

2006-09-15

2003-06-27 Application filed by Aventis Pharma Gmbh filed Critical Aventis Pharma Gmbh

2006-09-15 Publication of OA12880A publication Critical patent/OA12880A/en

Links

238000000034 method Methods 0.000 title claims description 21
239000003814 drug Substances 0.000 title description 2
229910052731 fluorine Inorganic materials 0.000 claims abstract description 28
229910052801 chlorine Inorganic materials 0.000 claims abstract description 20
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
229910052794 bromium Inorganic materials 0.000 claims abstract description 13
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 11
229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
229920006395 saturated elastomer Polymers 0.000 claims abstract description 11
229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 8
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 217
150000001875 compounds Chemical class 0.000 claims description 161
239000001257 hydrogen Substances 0.000 claims description 37
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 28
-1 S-(Ci-C4)-alkyl Chemical group 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
150000002431 hydrogen Chemical class 0.000 claims description 14
230000008569 process Effects 0.000 claims description 14
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 14
229910052740 iodine Inorganic materials 0.000 claims description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
239000008280 blood Substances 0.000 claims description 9
210000004369 blood Anatomy 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
238000002156 mixing Methods 0.000 claims description 5
125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
239000008103 glucose Substances 0.000 claims description 4
230000010030 glucose lowering effect Effects 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
239000012528 membrane Substances 0.000 abstract description 20
150000003839 salts Chemical class 0.000 abstract description 14
230000000694 effects Effects 0.000 abstract description 6
241000283973 Oryctolagus cuniculus Species 0.000 abstract description 5
125000003342 alkenyl group Chemical group 0.000 abstract description 4
230000003178 anti-diabetic effect Effects 0.000 abstract description 4
125000000304 alkynyl group Chemical group 0.000 abstract description 3
238000003556 assay Methods 0.000 abstract description 2
125000001475 halogen functional group Chemical group 0.000 abstract 3
PQZBNRCHAHHPNS-UHFFFAOYSA-N 2-[2-[2-(4-chlorophenyl)ethyl]thiophen-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound OC1C(O)C(O)C(CO)OC1OC1=C(CCC=2C=CC(Cl)=CC=2)SC=C1 PQZBNRCHAHHPNS-UHFFFAOYSA-N 0.000 abstract 2
125000004442 acylamino group Chemical group 0.000 abstract 2
125000004448 alkyl carbonyl group Chemical group 0.000 abstract 2
239000003146 anticoagulant agent Substances 0.000 abstract 2
230000006377 glucose transport Effects 0.000 abstract 2
101100062121 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) cyc-1 gene Proteins 0.000 abstract 1
125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
125000004457 alkyl amino carbonyl group Chemical group 0.000 abstract 1
230000001539 anorectic effect Effects 0.000 abstract 1
230000001088 anti-asthma Effects 0.000 abstract 1
230000000844 anti-bacterial effect Effects 0.000 abstract 1
230000036436 anti-hiv Effects 0.000 abstract 1
230000003110 anti-inflammatory effect Effects 0.000 abstract 1
230000002682 anti-psoriatic effect Effects 0.000 abstract 1
239000000924 antiasthmatic agent Substances 0.000 abstract 1
229940127219 anticoagulant drug Drugs 0.000 abstract 1
239000003472 antidiabetic agent Substances 0.000 abstract 1
239000000824 cytostatic agent Substances 0.000 abstract 1
230000001085 cytostatic effect Effects 0.000 abstract 1
206010061428 decreased appetite Diseases 0.000 abstract 1
230000001506 immunosuppresive effect Effects 0.000 abstract 1
230000010534 mechanism of action Effects 0.000 abstract 1
239000003176 neuroleptic agent Substances 0.000 abstract 1
230000000701 neuroleptic effect Effects 0.000 abstract 1
230000000324 neuroprotective effect Effects 0.000 abstract 1
230000001777 nootropic effect Effects 0.000 abstract 1
230000002537 thrombolytic effect Effects 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 126
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
239000000243 solution Substances 0.000 description 54
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
239000000203 mixture Substances 0.000 description 41
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 37
239000000047 product Substances 0.000 description 34
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
239000011541 reaction mixture Substances 0.000 description 21
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 17
239000012074 organic phase Substances 0.000 description 17
229910052681 coesite Inorganic materials 0.000 description 16
229910052906 cristobalite Inorganic materials 0.000 description 16
229940093499 ethyl acetate Drugs 0.000 description 16
235000019439 ethyl acetate Nutrition 0.000 description 16
229910052682 stishovite Inorganic materials 0.000 description 16
229910052905 tridymite Inorganic materials 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
210000000110 microvilli Anatomy 0.000 description 15
235000002639 sodium chloride Nutrition 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
238000004440 column chromatography Methods 0.000 description 14
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 14
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 13
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
239000000556 agonist Substances 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
229910000027 potassium carbonate Inorganic materials 0.000 description 12
229940093956 potassium carbonate Drugs 0.000 description 12
235000011181 potassium carbonates Nutrition 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
239000007983 Tris buffer Substances 0.000 description 11
239000012043 crude product Substances 0.000 description 10
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
102000004877 Insulin Human genes 0.000 description 8
108090001061 Insulin Proteins 0.000 description 8
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 8
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 8
125000000896 monocarboxylic acid group Chemical group 0.000 description 8
CYAYKKUWALRRPA-UHFFFAOYSA-N (3,4,5-triacetyloxy-6-bromooxan-2-yl)methyl acetate Chemical compound CC(=O)OCC1OC(Br)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O CYAYKKUWALRRPA-UHFFFAOYSA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
229940125396 insulin Drugs 0.000 description 7
229940073584 methylene chloride Drugs 0.000 description 7
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
239000008194 pharmaceutical composition Substances 0.000 description 7
210000000813 small intestine Anatomy 0.000 description 7
239000000126 substance Substances 0.000 description 7
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
241000700159 Rattus Species 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
239000005557 antagonist Substances 0.000 description 6
QMMFVYPAHWMCMS-UHFFFAOYSA-N dimethylsulfide Substances CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 6
229960000443 hydrochloric acid Drugs 0.000 description 6
235000011167 hydrochloric acid Nutrition 0.000 description 6
239000003112 inhibitor Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 6
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 5
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 5
229930195725 Mannitol Natural products 0.000 description 5
229940100389 Sulfonylurea Drugs 0.000 description 5
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 5
239000000872 buffer Substances 0.000 description 5
238000001914 filtration Methods 0.000 description 5
229930182470 glycoside Natural products 0.000 description 5
239000000594 mannitol Substances 0.000 description 5
235000010355 mannitol Nutrition 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
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 4
YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
238000005119 centrifugation Methods 0.000 description 4
238000009472 formulation Methods 0.000 description 4
238000011534 incubation Methods 0.000 description 4
210000003734 kidney Anatomy 0.000 description 4
229910001629 magnesium chloride Inorganic materials 0.000 description 4
XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 4
229960003105 metformin Drugs 0.000 description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
239000012071 phase Substances 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 4
239000000843 powder Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 4
239000000725 suspension Substances 0.000 description 4
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 3
QPJIXBYRIWNFKT-UHFFFAOYSA-N 2-(hydroxymethyl)-6-[2-[2-(4-methoxyphenyl)ethenyl]thiophen-3-yl]oxyoxane-3,4,5-triol Chemical compound C1=CC(OC)=CC=C1C=CC1=C(OC2C(C(O)C(O)C(CO)O2)O)C=CS1 QPJIXBYRIWNFKT-UHFFFAOYSA-N 0.000 description 3
RFSKGCVUDQRZSD-UHFFFAOYSA-N 3-methoxythiophene Chemical compound COC=1C=CSC=1 RFSKGCVUDQRZSD-UHFFFAOYSA-N 0.000 description 3
XQBKMDLTVLHZKS-UHFFFAOYSA-N 3-phenylmethoxy-5-propan-2-ylthiophene-2-carboxylic acid Chemical compound S1C(C(C)C)=CC(OCC=2C=CC=CC=2)=C1C(O)=O XQBKMDLTVLHZKS-UHFFFAOYSA-N 0.000 description 3
240000008886 Ceratonia siliqua Species 0.000 description 3
235000013912 Ceratonia siliqua Nutrition 0.000 description 3
YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
102000016267 Leptin Human genes 0.000 description 3
108010092277 Leptin Proteins 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
QECDWQWVLGULPZ-UHFFFAOYSA-N [3,4,5-triacetyloxy-6-[2-(4-methoxybenzoyl)-5-propan-2-ylthiophen-3-yl]oxyoxan-2-yl]methyl acetate Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(OC2C(C(OC(C)=O)C(OC(C)=O)C(COC(C)=O)O2)OC(C)=O)C=C(C(C)C)S1 QECDWQWVLGULPZ-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
230000001419 dependent effect Effects 0.000 description 3
DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 3
150000002338 glycosides Chemical class 0.000 description 3
210000000936 intestine Anatomy 0.000 description 3
NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 3
229940039781 leptin Drugs 0.000 description 3
210000004877 mucosa Anatomy 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
229940002612 prodrug Drugs 0.000 description 3
239000000651 prodrug Substances 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000007787 solid Substances 0.000 description 3
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OA1200500001A 2002-07-11 2003-06-27 Novel thiophenylglycoside derivatives, methods forproduction thereof, medicaments comprising said c ompounds and use thereof. OA12880A (en)

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DE10231370A DE10231370B4 (de)	2002-07-11	2002-07-11	Thiophenglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel

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US (2)	US7101856B2 (fr)
EP (4)	EP1967523B1 (fr)
JP (1)	JP4511927B2 (fr)
KR (1)	KR20050021452A (fr)
CN (2)	CN100384863C (fr)
AR (1)	AR040474A1 (fr)
AT (4)	ATE477266T1 (fr)
AU (1)	AU2003246620B2 (fr)
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CA (1)	CA2493391C (fr)
CR (1)	CR7718A (fr)
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DE (5)	DE10231370B4 (fr)
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EC (1)	ECSP055531A (fr)
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OA (1)	OA12880A (fr)
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TN (1)	TNSN05007A1 (fr)
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2002
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2003
- 2003-06-23 JO JOP/2003/0068A patent/JO2707B1/ar active
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Also Published As

Publication number	Publication date
TW200410979A (en)	2004-07-01
EP1523488A1 (fr)	2005-04-20
MA27366A1 (fr)	2005-06-01
ATE479697T1 (de)	2010-09-15
JP2005536497A (ja)	2005-12-02
DE50310783D1 (de)	2008-12-24
UY27891A1 (es)	2003-12-31
DE50312984D1 (de)	2010-09-23
NO20050649L (no)	2005-04-01
DE10231370B4 (de)	2006-04-06
ATE414095T1 (de)	2008-11-15
UA78823C2 (en)	2007-04-25
EP1967523A1 (fr)	2008-09-10
ECSP055531A (es)	2005-03-10
TWI318981B (en)	2010-01-01
TNSN05007A1 (en)	2007-05-14
CN101240000A (zh)	2008-08-13
EP1964845A1 (fr)	2008-09-03
ES2316818T3 (es)	2009-04-16
RS115004A (sr)	2007-02-05
RU2317300C2 (ru)	2008-02-20
IL166058A0 (en)	2006-01-15
DE50313056D1 (de)	2010-10-14
MXPA05000044A (es)	2005-04-08
JP4511927B2 (ja)	2010-07-28
ATE477265T1 (de)	2010-08-15
AU2003246620A1 (en)	2004-02-02
BR0312513A (pt)	2005-04-12
PL372931A1 (en)	2005-08-08
IL191926A0 (en)	2008-12-29
RS51002B (sr)	2010-10-31
EP1964845B1 (fr)	2010-08-11
HK1080482A1 (en)	2006-04-28
AU2003246620B2 (en)	2009-03-19
US7666848B2 (en)	2010-02-23
DE50312983D1 (de)	2010-09-23
KR20050021452A (ko)	2005-03-07
RU2005103602A (ru)	2005-07-20
CA2493391A1 (fr)	2004-01-22
ATE477266T1 (de)	2010-08-15
US20060293252A1 (en)	2006-12-28
HRP20050014A2 (hr)	2006-04-30
CR7718A (es)	2006-05-11
SI1523488T1 (sl)	2009-04-30
CA2493391C (fr)	2010-06-15
US20040138143A1 (en)	2004-07-15
PT1523488E (pt)	2009-01-30
PE20040655A1 (es)	2004-11-15
ZA200409779B (en)	2006-06-28
JO2707B1 (ar)	2014-03-15
EP1523488B1 (fr)	2008-11-12
DE10231370A1 (de)	2004-02-05
EP1964844B1 (fr)	2010-09-01
WO2004007517A1 (fr)	2004-01-22
CN1668628A (zh)	2005-09-14
EP1964844A1 (fr)	2008-09-03
EP1967523B1 (fr)	2010-08-11
US7101856B2 (en)	2006-09-05
AR040474A1 (es)	2005-04-06
PA8577101A1 (es)	2004-02-07
CN100384863C (zh)	2008-04-30
MY137039A (en)	2008-12-31
DK1523488T3 (da)	2009-03-16
HN2003000215A (es)	2004-07-27
CY1108754T1 (el)	2014-04-09
MEP60708A (en)	2011-05-10

Publication	Publication Date	Title
OA12880A (en)	2006-09-15	Novel thiophenylglycoside derivatives, methods forproduction thereof, medicaments comprising said c ompounds and use thereof.
AU2003289911B2 (en)	2009-09-17	Novel fluoroglycoside heterocyclic derivatives, pharmaceutical products containing said compounds and the use thereof
CA2508024C (fr)	2012-06-05	Nouveaux derives de fluorglycoside aromatiques, produits pharmaceutiques contenant ces composes et leur utilisation
AU2005252329A1 (en)	2005-12-22	Novel fluoroglycoside derivatives of pyrazoles, medicaments containing these compounds, and the use thereof
WO2009138195A2 (fr)	2009-11-19	Utilisation de dérivés de thiophène-glycoside dans la production de médicaments destinés au traitement de l’hypertension
NZ537583A (en)	2006-08-31	Novel thiophene glycoside derivatives, methods for production thereof, medicaments comprising said compounds and use thereof
AU2004261371A1 (en)	2005-02-10	Substituted benzoylureido-o-benzoylamides, method for the production thereof and use of the same
HK1123307A (en)	2009-06-12	Novel thiophenylglycoside derivatives, methods for production thereof, medicaments comprising said compounds and use thereof
HK1080482B (en)	2009-01-02	Novel thiophenylglycoside derivatives, methods for production thereof, medicaments comprising said compounds and use thereof