UA81136C2 - Fluoroglycoside heterocyclic derivatives, pharmaceutical products containing said compounds and the use thereof - Google Patents

Fluoroglycoside heterocyclic derivatives, pharmaceutical products containing said compounds and the use thereof Download PDF

Info

Publication number: UA81136C2
Authority: UA; Ukraine
Prior art keywords: alkyl; mean; phenyl; replaced; compounds
Prior art date: 2002-12-12

Application number

UAA200506789A

Other languages

English (en)

Ukrainian (uk)

Inventor

Wendelin Frick

Heiner Glombik

Werner Kramer

Hubert Heuer

Harm Brummerhop

Oliver Plettenburg

Original Assignee

Sanofi Aventis Deutschland

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.)

2002-12-12

Filing date

2003-11-28

Publication date

2007-12-10

2003-11-28 Application filed by Sanofi Aventis Deutschland filed Critical Sanofi Aventis Deutschland

2007-12-10 Publication of UA81136C2 publication Critical patent/UA81136C2/uk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 113
125000000623 heterocyclic group Chemical group 0.000 title abstract description 5
239000000825 pharmaceutical preparation Substances 0.000 title 1
229940127557 pharmaceutical product Drugs 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 19
150000003839 salts Chemical class 0.000 claims abstract description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
125000004432 carbon atom Chemical group C* 0.000 claims description 32
239000000203 mixture Substances 0.000 claims description 25
229910052799 carbon Inorganic materials 0.000 claims description 19
239000013543 active substance Substances 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 17
229940088623 biologically active substance Drugs 0.000 claims description 17
239000008103 glucose Substances 0.000 claims description 14
-1 respectively Chemical group 0.000 claims description 14
229920006395 saturated elastomer Polymers 0.000 claims description 13
101000920618 Homo sapiens Transcription and mRNA export factor ENY2 Proteins 0.000 claims description 10
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 10
102100031954 Transcription and mRNA export factor ENY2 Human genes 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
229940126601 medicinal product Drugs 0.000 claims description 9
239000008280 blood Substances 0.000 claims description 8
210000004369 blood Anatomy 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
239000011737 fluorine Substances 0.000 claims description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical group 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
229930192474 thiophene Natural products 0.000 claims description 5
206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
150000001720 carbohydrates Chemical group 0.000 claims description 4
229910052698 phosphorus Inorganic materials 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
125000006530 (C4-C6) alkyl group Chemical group 0.000 claims 2
239000003937 drug carrier Substances 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 11
229940125708 antidiabetic agent Drugs 0.000 abstract description 4
239000003472 antidiabetic agent Substances 0.000 abstract description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
239000000243 solution Substances 0.000 description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
230000015572 biosynthetic process Effects 0.000 description 27
238000003786 synthesis reaction Methods 0.000 description 25
239000007787 solid Substances 0.000 description 22
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
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239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 16
239000000556 agonist Substances 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
210000000110 microvilli Anatomy 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 13
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 13
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 12
239000007983 Tris buffer Substances 0.000 description 10
239000000872 buffer Substances 0.000 description 10
239000003112 inhibitor Substances 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
239000000126 substance Substances 0.000 description 10
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 9
229930195725 Mannitol Natural products 0.000 description 9
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
239000000594 mannitol Substances 0.000 description 9
235000010355 mannitol Nutrition 0.000 description 9
239000008194 pharmaceutical composition Substances 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 8
239000012043 crude product Substances 0.000 description 8
210000000813 small intestine Anatomy 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
102000004877 Insulin Human genes 0.000 description 7
108090001061 Insulin Proteins 0.000 description 7
241000700159 Rattus Species 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
239000005557 antagonist Substances 0.000 description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
239000013049 sediment Substances 0.000 description 7
SQDGXUZQIIYYSD-UHFFFAOYSA-N (3-hydroxythiophen-2-yl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(O)C=CS1 SQDGXUZQIIYYSD-UHFFFAOYSA-N 0.000 description 6
BDYYNVGGIQIVCZ-UHFFFAOYSA-N 4-[(4-methoxyphenyl)methyl]-5-methyl-1,2-dihydropyrazol-3-one Chemical compound C1=CC(OC)=CC=C1CC1=C(C)NNC1=O BDYYNVGGIQIVCZ-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
239000002253 acid Substances 0.000 description 6
229940125396 insulin Drugs 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
239000006228 supernatant Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
229940100389 Sulfonylurea Drugs 0.000 description 5
230000001133 acceleration Effects 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000003826 tablet Substances 0.000 description 5
WZMPOCLULGAHJR-UHFFFAOYSA-N thiophen-2-ol Chemical class OC1=CC=CS1 WZMPOCLULGAHJR-UHFFFAOYSA-N 0.000 description 5
UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 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 description 4
241000283973 Oryctolagus cuniculus Species 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
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
229940125936 compound 42 Drugs 0.000 description 4
206010012601 diabetes mellitus Diseases 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
230000003993 interaction Effects 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
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
125000006239 protecting group Chemical group 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
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AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 3
OMBVEVHRIQULKW-DNQXCXABSA-M (3r,5r)-7-[3-(4-fluorophenyl)-8-oxo-7-phenyl-1-propan-2-yl-5,6-dihydro-4h-pyrrolo[2,3-c]azepin-2-yl]-3,5-dihydroxyheptanoate Chemical compound O=C1C=2N(C(C)C)C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C(C=3C=CC(F)=CC=3)C=2CCCN1C1=CC=CC=C1 OMBVEVHRIQULKW-DNQXCXABSA-M 0.000 description 3
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 3
FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 description 3
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MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
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UAA200506789A 2002-12-12 2003-11-28 Fluoroglycoside heterocyclic derivatives, pharmaceutical products containing said compounds and the use thereof UA81136C2 (en)

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DE10258008A DE10258008B4 (de)	2002-12-12	2002-12-12	Heterocyclische Fluorglycosidderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zur Herstellung dieser Arzneimittel
PCT/EP2003/013455 WO2004052903A1 (de)	2002-12-12	2003-11-28	Neue heterocyclische fluorglykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung

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Publication number	Publication date
WO2004052903A1 (de)	2004-06-24
JP2006510644A (ja)	2006-03-30
JP4806193B2 (ja)	2011-11-02
NO20053201L (no)	2005-08-04
DE10258008A1 (de)	2004-07-08
ECSP055853A (es)	2005-09-20
MXPA05005821A (es)	2005-08-29
CY1105621T1 (el)	2010-12-22
TW200418870A (en)	2004-10-01
ES2261993T3 (es)	2006-11-16
ATE323713T1 (de)	2006-05-15
DK1572708T3 (da)	2006-08-21
MY139302A (en)	2009-09-30
HN2003000408A (es)	2006-01-07
MEP40908A (en)	2011-02-10
EP1572708A1 (de)	2005-09-14
KR101160061B1 (ko)	2012-06-26
CA2508226C (en)	2011-12-20
HRP20050532A2 (en)	2006-09-30
US20040259819A1 (en)	2004-12-23
NZ540695A (en)	2007-02-23
UY28122A1 (es)	2004-07-30
JO2353B1 (en)	2006-12-12
PA8592301A1 (es)	2004-07-26
IL168876A (en)	2010-06-30
RS20050432A (en)	2007-06-04
KR20050085482A (ko)	2005-08-29
AU2003289911A1 (en)	2004-06-30
MA27560A1 (fr)	2005-10-03
AR042437A1 (es)	2005-06-22
HK1084123A1 (en)	2006-07-21
PL375790A1 (en)	2005-12-12
ZA200503365B (en)	2006-11-29
CN1304406C (zh)	2007-03-14
RS50908B (sr)	2010-08-31
EP1572708B1 (de)	2006-04-19
OA12972A (en)	2006-10-13
US20100261664A1 (en)	2010-10-14
PE20040771A1 (es)	2005-01-21
SI1572708T1 (sl)	2006-08-31
NO330299B1 (no)	2011-03-28
GT200300268A (es)	2004-03-03
AU2003289911B2 (en)	2009-09-17
NO20053201D0 (no)	2005-06-30
CA2508226A1 (en)	2004-06-24
SV2004001690A (es)	2004-03-19
RU2005121893A (ru)	2006-01-20
PT1572708E (pt)	2006-07-31
BR0317283A (pt)	2005-11-08
TWI320044B (en)	2010-02-01
CN1723214A (zh)	2006-01-18
CR7820A (es)	2008-11-25
PL212080B1 (pl)	2012-08-31
RU2339641C2 (ru)	2008-11-27
DE10258008B4 (de)	2006-02-02
TNSN05160A1 (en)	2007-05-14
DE50303067D1 (de)	2006-05-24

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