KR900003193A - 과혈당증 및/또는 당뇨병 치료용 신규 유기 화합물 및 그 제조방법 - Google Patents
과혈당증 및/또는 당뇨병 치료용 신규 유기 화합물 및 그 제조방법 Download PDFInfo
- Publication number
- KR900003193A KR900003193A KR1019890011552A KR890011552A KR900003193A KR 900003193 A KR900003193 A KR 900003193A KR 1019890011552 A KR1019890011552 A KR 1019890011552A KR 890011552 A KR890011552 A KR 890011552A KR 900003193 A KR900003193 A KR 900003193A
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- South Korea
- Prior art keywords
- bis
- alkyl
- deoxy
- hydrogen
- anhydro
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims 2
- 206010012601 diabetes mellitus Diseases 0.000 title 1
- 201000001421 hyperglycemia Diseases 0.000 title 1
- 150000002894 organic compounds Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims 26
- 229910052739 hydrogen Inorganic materials 0.000 claims 26
- 239000001257 hydrogen Substances 0.000 claims 26
- 150000001875 compounds Chemical class 0.000 claims 20
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims 17
- 150000002431 hydrogen Chemical class 0.000 claims 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 8
- -1 diphenyl phosphinyl Chemical group 0.000 claims 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 6
- 229910019142 PO4 Inorganic materials 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 239000010452 phosphate Substances 0.000 claims 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 5
- ASMQGLCHMVWBQR-UHFFFAOYSA-M diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)([O-])OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-M 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 5
- LGTAJYUNDJNIRA-PBXRRBTRSA-N (3s,4s,5r)-2,2,5-tris(hydroxymethyl)oxolane-3,4-diol Chemical compound OC[C@H]1OC(CO)(CO)[C@@H](O)[C@@H]1O LGTAJYUNDJNIRA-PBXRRBTRSA-N 0.000 claims 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 4
- ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 claims 4
- UCQFCFPECQILOL-UHFFFAOYSA-N diethyl hydrogen phosphate Chemical compound CCOP(O)(=O)OCC UCQFCFPECQILOL-UHFFFAOYSA-N 0.000 claims 4
- 150000002148 esters Chemical class 0.000 claims 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- ZDSMGJUMXUHTMZ-DBRKOABJSA-N (2r,3s,4s,5r)-2-(2-hydroxyethyl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound OCC[C@H]1O[C@H](CO)[C@@H](O)[C@@H]1O ZDSMGJUMXUHTMZ-DBRKOABJSA-N 0.000 claims 3
- ZDSMGJUMXUHTMZ-BDVNFPICSA-N (2s,3s,4s,5r)-2-(2-hydroxyethyl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound OCC[C@@H]1O[C@H](CO)[C@@H](O)[C@@H]1O ZDSMGJUMXUHTMZ-BDVNFPICSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- KGQMTAIRDRAQGH-BMJXUZCVSA-N OC[C@H]1OC(O)(C(F)(F)C(O)=O)[C@@H](O)[C@@H]1O Chemical compound OC[C@H]1OC(O)(C(F)(F)C(O)=O)[C@@H](O)[C@@H]1O KGQMTAIRDRAQGH-BMJXUZCVSA-N 0.000 claims 3
- JRARXDKGHXHPTE-KENYUPALSA-N OC[C@H]1OC(O)(C(F)(F)CO)[C@@H](O)[C@@H]1O Chemical compound OC[C@H]1OC(O)(C(F)(F)CO)[C@@H](O)[C@@H]1O JRARXDKGHXHPTE-KENYUPALSA-N 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- 229960002920 sorbitol Drugs 0.000 claims 3
- QYPXNIGPYJTYIS-SVXWRWBYSA-N (3s,4s,5r)-2-(difluoromethyl)-5-(hydroxymethyl)oxolane-2,3,4-triol Chemical compound OC[C@H]1OC(O)(C(F)F)[C@@H](O)[C@@H]1O QYPXNIGPYJTYIS-SVXWRWBYSA-N 0.000 claims 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims 2
- 101150065749 Churc1 gene Proteins 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 102100038239 Protein Churchill Human genes 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- GCCFBDFJFARWGD-IYWMVGAKSA-N [(2s,3r,4r,5r)-5-(hydroxymethyl)-3,4-bis(phenylmethoxy)oxolan-2-yl]methanol Chemical compound O([C@@H]1[C@H](CO)O[C@@H]([C@H]1OCC=1C=CC=CC=1)CO)CC1=CC=CC=C1 GCCFBDFJFARWGD-IYWMVGAKSA-N 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 2
- 150000001241 acetals Chemical class 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 229940126214 compound 3 Drugs 0.000 claims 2
- 229910000365 copper sulfate Inorganic materials 0.000 claims 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 claims 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000004494 ethyl ester group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims 2
- 159000000000 sodium salts Chemical class 0.000 claims 2
- MCHWWJLLPNDHGL-KVTDHHQDSA-N (2r,3s,4s,5r)-2,5-bis(hydroxymethyl)oxolane-3,4-diol Chemical compound OC[C@H]1O[C@H](CO)[C@@H](O)[C@@H]1O MCHWWJLLPNDHGL-KVTDHHQDSA-N 0.000 claims 1
- JDHHBUCLJPCRNJ-BNWJMWRWSA-N (2r,3s,4s,5r)-2-[(1r)-1,2-dihydroxyethyl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1O[C@H](CO)[C@@H](O)[C@@H]1O JDHHBUCLJPCRNJ-BNWJMWRWSA-N 0.000 claims 1
- MCHWWJLLPNDHGL-JGWLITMVSA-N (2s,3s,4s,5r)-2,5-bis(hydroxymethyl)oxolane-3,4-diol Chemical compound OC[C@H]1O[C@@H](CO)[C@@H](O)[C@@H]1O MCHWWJLLPNDHGL-JGWLITMVSA-N 0.000 claims 1
- PJSWWCRHWGIKFU-NGJRWZKOSA-N (2s,3s,4s,5r)-2-(2-hydroxyethyl)-2,5-bis(hydroxymethyl)oxolane-3,4-diol Chemical compound OCC[C@@]1(CO)O[C@H](CO)[C@@H](O)[C@@H]1O PJSWWCRHWGIKFU-NGJRWZKOSA-N 0.000 claims 1
- GJTPBPMZCJHTSH-UHFFFAOYSA-N C1C=COP(=O)(O1)O Chemical compound C1C=COP(=O)(O1)O GJTPBPMZCJHTSH-UHFFFAOYSA-N 0.000 claims 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 229920002472 Starch Polymers 0.000 claims 1
- VYBVJMKEOXQQBK-MVIOUDGNSA-N [(2r,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]methyl dihydrogen phosphate Chemical compound OC[C@H]1O[C@](CO)(COP(O)(O)=O)[C@@H](O)[C@@H]1O VYBVJMKEOXQQBK-MVIOUDGNSA-N 0.000 claims 1
- AWCVCDVQWUWOCX-PFBJBMPXSA-N [(3s,4r,5r)-2-(hydroxymethyl)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]methanol Chemical compound C([C@H]1OC([C@H]([C@@H]1OCC=1C=CC=CC=1)OCC=1C=CC=CC=1)(CO)CO)OCC1=CC=CC=C1 AWCVCDVQWUWOCX-PFBJBMPXSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- 125000006267 biphenyl group Chemical group 0.000 claims 1
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 claims 1
- 150000001722 carbon compounds Chemical class 0.000 claims 1
- 230000015556 catabolic process Effects 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- JFBJUMZWZDHTIF-UHFFFAOYSA-N chloro chlorite Chemical compound ClOCl=O JFBJUMZWZDHTIF-UHFFFAOYSA-N 0.000 claims 1
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical class OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 claims 1
- 238000006731 degradation reaction Methods 0.000 claims 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 239000012280 lithium aluminium hydride Substances 0.000 claims 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 1
- 229910003446 platinum oxide Inorganic materials 0.000 claims 1
- MHZDONKZSXBOGL-UHFFFAOYSA-N propyl dihydrogen phosphate Chemical compound CCCOP(O)(O)=O MHZDONKZSXBOGL-UHFFFAOYSA-N 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 230000002786 root growth Effects 0.000 claims 1
- 239000012279 sodium borohydride Substances 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 239000008107 starch Substances 0.000 claims 1
- 235000019698 starch Nutrition 0.000 claims 1
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-UHFFFAOYSA-N 0.000 claims 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 claims 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 claims 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
- C07H11/04—Phosphates; Phosphites; Polyphosphates
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- 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
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Diabetes (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biochemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cultivation Of Plants (AREA)
- Furan Compounds (AREA)
- Saccharide Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (21)
- 하기 일반 구조식의 화합물로부터 선택된 화합물 :상기식에서, A 및 B는 서로 독립적으로 C₁내지 C₄알킬렌 및 C₂내지 C₄히드록시알킬렌으로 구성된 군으로부터 선택되며; R1은 수소, C₁내지 C₄알킬, C₁내지 C₄ 히드록시알킬, C₂내지 C₄디히드록시알킬, C₃또는 C₄트리히드록시 알킬 및 C₄테트라히드록시알킬로 구성된 군으로부터 선택되며; R', R", R"' 및 R""는 독립적으로 수소, C₁내지 C1알킬, C₃내지 C6시클로알킬, 페닐, 이소알킬(C3- C8), -Cl3CCH2-, CH2=CHCH2-, ZCH2CH2-(여기서 Z는SO2R2, SR2, OR₂또는 Si(R2)3, 이며, R2는 알킬(C1-C3)임),, 할로[여기서 R3는 수소, 알킬(C1-C18)이며 R3-R3은 알킬렌 또는 아세탈임],(여기서 R4는 수소 또는, 메틸임),(여기서 R5=R6일때, 이들은 둘다, 수소, 플루오로 또는 알킬(C1-C4)이며 R5=수소, R6=플루오로, 히드록시 또는 OR7[여기서 R7=알킬(C1-C6), 시클로알킬(C₃-C6) 또는 아릴]임],[여기서 R8=수소 또는 알킬(C1-C8)],, 페닐메틸, 치환제가 알킬(C1-C18), 알콕시(C1-C6), NO₂및 할로겐으로부터 치환되는 치환된 페닐 메틸 및 치환제가 알킬(C₁-C8), 알콕시(C₁-C6), NO₂및 할로겐으로부터 선택되는 단일- 및 이치환된 페닐로부터 선택되며; 단, A 및 B가 둘다 -CH2-일때 R1은 수소일 수 없고, R',R",R"' 또는 R""중 하나 이상이 수소일때, 약리학적으로 허용가능한 이들의 염도 제공된다.
- 제 1 항에 있어서, 3,6-언히드로-2-데옥시-D-글루코-헵티톨, 1,7-비스(디페닐 포스페이트); 3,6-언히드로-2-데옥시-D-글르코-헵티톨, 1,7-비스(디에틸 포스페인트); 3,6-언히드로-2-데옥시-D-만노-헵티톨, 1,7-비스(디페닐 포스페인트); 3,6-언히드로-2-데옥시-D-만노-헵티톨, 1,7-비스(디에틸 포스페인트); 3,6-언히드로-2-데옥시-D-글루코-헵티톨, 1,7-비스-(디히드로겐 포스페이트); 및 3,6-언히드로-2-데옥시-D-만노-헵티톨, 1,7-비스)디히드로겐 포스페인트)인 화합물.
- 제 1항에 있어서, 4,7-언히드로-2,3-디데옥시-D-글루코-옥티톨, 1,8-비스-(디페닐 포스페이트) ; 4,7-언히드로-2,3-디데옥시-D-글루코-옥티톨, 1,8-비스(디에틸 포스페이트) ; 4,7-언히드로-2,3-디데옥시-D-만노-옥티톨, 1,8-비스(디페닐 포스페이트) ; 4,7-언히드로-2,3-디데옥시-D-만노-옥티톨, 1,8-비스(디에틸 포스페이트) ; 4,7-언히드로-2,3-디데옥시-D-글루코-옥티톨, 1,8-비스(디히드로겐 포스페이트) ; 및 4,7-언히드로-2,3-디데옥시-D-만노-옥티톨, 1,8-비스-(디히드로겐 포스페이트)인 화합물.
- 제 1항에 있어서, 2,5-언히드로-D-글리세로-D-만노-헵티톨, 1,7-비스-(디히드로겐 포스페이트)인 화합물.
- 제 1항에 있어서, 2,5-언히드로-2-C-(히드록시메틸)-D-글루시톨, 1,6-비스-(디페닐 포스페이트) ; 2,5-언히드로-2-C-(히드록시메틸)-D-글루시톨, 1,6-비스(디에틸 포스페이트) ; 및 2,5-언히드로-2-C-(히드록시메틸)-D-글루시톨, 1,6-비스(디히드로겐 포스페이트)인 화합물.
- 제 1항에 있어서, 2,5-언히드로-2-C-[[(디페녹시 포스피닐)옥시]메틸]-D-글루시톨, 6-(디페닐 포스페이트) ; 2,5-언히드로-2-C-[[(디페닐 포스피닐)옥시]메틸]-D-글루시톨, 6-(디에틸포스페이트) ; 및 2,5-언히드로-2-C-[(포스포노옥시)메틸]-D-글루시톨, 6-(디히드로겐 포스페이트)인 화합물.
- 제 1항에 있어서, 3,6-언히드로-2-데옥시-3-C-(히드록시메틸)-D-만노-헵티톨, 1,7-비스(디히드로겐 포스페이트)인 화합물.
- 하기 일반구조식의 화합물로부터 선택된 화합물 :상기식에서 A는 C₁내지 C₄알킬렌 및 C₂내지 C₄히드록시알킬렌으로 구성된 군으로부터 선택되며 ; R', R", R'" 및 R""는 독립적으로 수소, C₁내지 C18알킬, C₃내지 C6시클로알킬, 페닐, 이소알킬(C3-C8), Cl3CCH2-,CH2=CHCH₂-,ZCH2CH2-(여기서 Z는 SO2R2, SR2, OR₂또는 Si(R2)3, 이며 R2는 알킬(C1-C3)임),할로,[여기서 R3는 수소, 알킬(C1-C18)이며 R₃- R3는 알킬렌 또는 아세틸임],(여기서 R4는 수소 또는 메틸임),(여기서 R5=R6일때, 이들은 둘다, 수소, 플루오로 또는 알킬(C1-C₄)이며, R5=수소, R6=플루오로, 히드록시 또는 OR7[여기서 R7=알킬(C1-C6), 시클로알킬(C3-C6)또는 아릴임],[여기서 R8=수소 또는 알킬(C₁-C18)],, 페닐 메틸, 치환체가 알킬(C1-C18), 알콕시(C1-C6), NO₂및 할로겐으로부터 선택되는 치환된 페닐 메틸 및 치환체가 알킬(C1-C18), 알콕시(C1-C6), NO₂및 할로겐으로부터 선택되는 단일- 및 이치환된 페닐로부터 선택되며 ; Y는 수소, COOR9및 CH2OH(여기서 R9는 수소 또는 이들의 염임) 또는 알킬(C₁-C6)로 구성된 군으로부터 선택된다.
- 제 8항에 있어서, 2-데옥시-2,2-디플루오로-D-아라비노-3-헵툴로푸라노손산, 에틸 에스테르-, 3,7-비스(디히드로겐 포스페이트), β-아노머, 이나트륨염 ; 및 2-데옥시-2,2-디플루오로-D-아라비노-3-헵툴로푸라노손산, 에틸에스테르-, 3,7-비스(디히드로겐 포스페이트),-아노머, 이나트륨염인 화합물.
- 제 8항에 있어서, 1-데옥시-1,1-디플루오로-D-푸룩토푸라노스, 2,6-비스(디히드로겐 포스페이트), β-아노머, 이나트륨염 ; 및 1-데옥시-1,1-디플루오로-D-푸룩토푸라노스, 2,6-비스-(디히드로겐 포스페이트), α-아노머, 이나트륨염인 화합물.
- 제 8항에 있어서, 1-데옥시-1,1-디플루오로-D-프룩토푸라노스, 2,6-비스(디히드로겐 포스페이트), β-아노머, 시나트륨염 ; 및 1-데옥시-1,1-디플루오르-D-프룩토푸라노스, 2,6-비스-)디히드로겐 포스페이트), β-아노머, 사나트륨염인 화합물.
- 제 8항에 있어서, 2-데옥시-2,2-디플루오로-D-아라비노-3-헵툴로푸라노스, 3,7-비스(디히드로겐 포스페이트), β-아노머, 이나트륨염 ; 및 2-데옥시-2,2-디플루오로-D-아라비노-3-헵툴로푸라노스, 3,7-비스(디히드로겐 포스페이트), α-아노머, 이나트륨염인 화합물.
- 하기 일반 구조식의 화합물들로부터 선택되는 화합물 및 이들의 약리학적으로 허용가능한 염 ;상기식에서 A는 C₁내지 C₄알킬렌 및 C₂내지 C₄히드록시알킬렌으로 구성된 군으로부터 선택되며 ; R'" 및 R""는 독립적으로 수소, C₁내지 C18알킬, C₃내지 C6시클로알킬, 페닐, 이소알킬(C3-C8), Cl3CCH2-, CH2=CHCH2-, ZCH2CH2-(여기서 Z는 SO2R₂, SR2, OR2또는 Si(R2)3, 이며 R2는 알킬(C1-C3)임], -할로,CH₂[여기서 R₃는 수소, 알킬(C₁-C18)이며 R₃-R₃는 알킬렌 또는 아세탈임.(여기서 R4는 수소 또는 메틸임),(여기서 R5=R6일때, 이들은 둘다, 수소, 플루오로 또는 알킬(C1-C₄)이며 R5=수소, R6=플루오로, 수소 또는 OR7[여기서 R7=알킬(C1-C6), 시클로알킬(C3-C6) 또는 아릴임],[여기서 R8=수소 또는 알킬(C1-C18)],페닐 메틸, 치환체가 알킬(C1-C18), 알콕시(C1-C6), NO₂및 할로겐으로부터 선택되는 치환된 페닐 메틸 및 치환체가 알킬(C1-C18), 알콕시(C1-C6), NO2및 할로겐으로부터 선택되는 단일- 및 이치환된 페닐,[여기서 R10은 수소 또는 C₁내지 C₃알킬임] 및[여기서 Q는 결합, -(CH2)n 또는 -(CH₂)n-O-이며 n=1-3임]으로 구성된 군으로부터 선택되며, W는 -CFH2, -CF2H, -CF3, CF2CH₂OH, -CF2COOH, COOH 및 -COOCH3로 구성된 군으로부터 선택된다.
- 제 13항에 있어서, 1-데옥시-1,1-디플루오로푸룩토푸라노스, 6-[2-메톡시-3-(헥사데실옥실)프로필히드로겐 포스페이트 ; 1-데옥시-1,1-디플루오로-D-푸룩토푸라노스, 6-(2-히드록시-1,3,2-디옥사포스포리난-2-옥사이드) ; 1-데옥시-1,1-디플루오로-D-푸룩토푸라노스, 6-(디히드로겐 포스페이트), 나트륨 염 ; 2-데옥시-2,2-디플루오로-D-아라비노-3-헵툴로푸라노손산, 7-(디히드로겐 포스페이트), 삼나트륨염 ; 1-데옥시-1-플루오로-D-푸룩토푸라노스, 6-(디히드로겐 포스페이트), 이나트륨염 ; 2-데옥시-2,2-디플루오로-D-아라비노-3-헵툴로푸라노스, 7-(디히드로겐 포스페이트), 이나트륨염 ; 및 D-아라비노-2-헥술로푸라노손산, 6-(디히드로겐 포스페이트) 이나트륨염인 화합물.
- 피리딘내 트리틸 클로라이드와 2,5-언히드로-D-글루시톨을 반응시켜 2,5-언히드로-1,6-비스-O-(트리페닐메틸)-D-글루시톨을 얻은후, 디메틸 포름아미드내 수소화나트륨 및 벤질 브로마이드와 반응 시켜, 2,5-언히드로-3,4-비스-O-(페닐메틸)-1,6-비스-O-(트리페닐메틸)-D-글루시톨을 얻고, 이것을 아세트산과 함께 가열시켜, 2,5-언히드로-3,4-비스-O-(페닐메틸)-D-글루시톨을 얻고, 감소된 온도에서 피리딘내 이치환된 포스포로클로리데이트와 반응시켜, 2,5-언히드로-3,4-비스-O-(페닐메틸)-D-글루시톨, 1,6-비스(이치환된 포스페이트)를 얻고, 이것을 탄소상 팔라듐에서 메탄올-아세트산으로 수소화시키는 것으로 구성된, 화합물 2,5-언히드로-D-글루시톨, 1,6-비스(이치환된 포스페이트)[여기서 포스페이트상의 치환체는 제1항에서 정의된 R', R", R"' 및 R"""임]의 제조방법.
- 불활성 분위기하에 낮은 온도에서 에테르내 리튬 알루미늄 하이드라이드와 2,5-언히드로-3,46-트리스-O-(페닐메틸)-D-만노스를 반응시킨후, 환류시켜 2,5-언히드로-1,3,4-트리스-O-(페닐메틸)-D-만니톨을 얻고, 이것을 탄소상 팔라듐에서 메탄올-아세트산으로 수소화시켜, 2,5-언히드로-D-만니톨을 얻고 이것을 감소된 온도에서 피리딘내 이치환된 포스포로클로리데이트와 반응시키는 것으로 구성된, 화합물 2,5-언히드로-D-만니톨, 1,6-비스(이치환된 포스페이트)[여기서 포스페이트상 치환체는 제 1항에 정의된 R', R", R"' 및 R""이다]의 제조방법.
- 탄소상 팔라듐상에서 메탄올-아세트산내에서 2,5-언히드로-2-C-(히드록시메틸)-3,4,6-트리스-O-(페닐메틸)-D-글루시톨을 수소화시켜, 2,5-언히드로-2-C-(히드록시메틸)-D-글루시톨을 얻고, 이것을 아세톤내에서 황산구리 및 황산으로 처리한후, 중화시켜 2,5-언히드로-2-C-(히드록시메틸)-2¹, 3-O-(1-메틸에틸리덴)-D-글루시톨을 얻고 이것을 낮은 온도에서 피리딘내 이치환된 포스포로클로리데이트와 반응시키는 것으로 구성된, 화합물 3,5-인히드로-2-C-[[(이치환된 포스피닐)옥시]메틸]-1, 3-0-(1-메틸에틸리덴0-D-글루시톨, 6-(이치환된 포스페이트)(여기서 포스페이트상 치환체는 제 1항에 정의된 R', R", R"' 및 R""임)의 제조방법.
- 낮은 온도에서 아세토니트릴 내에서-D-프룩토루파노스, 펜타벤조에이트 및 알릴트리메틸실란을 반응 시킨후, 보론 트리플루오라이드 에테레이트와 반응시켜, 4,7-언히드로-4-C-[(벤조일옥시)메틸]-1,2,3-트리데옥시-D-아라비노-옥트-1-에니톨, 5,6,8-트리벤조에이트를 얻고, 이것을 메탄올내 나트륨 메톡시드와 반응시켜, 4,7-언히드로-1,2,3-트리데옥시-4-C-(히드록시메틸)-D-만노-옥트-1-에니톨을 얻고, 이것을 아세톤내 황산구리 및 황산과 반응시킨후, 중화시켜 4註,5:4,7-디히드로-1,2,3-트리데옥시-4-C-[(1-히드록시-1-메틸옥시)메틸]-6,8-비스-O-(페닐메틸)-D-만노-옥트-1-에니톨을 얻고, 이것을 우선 피리딘 및 디클로로메탄의 혼합물내에서 가오존 분해시킨후, 에탄올 내에서 붕수소화 나트륨으로 처리하여, 3,6:3¹,4-디언히드로-2-데옥시-3-C-[(1-히드록시-1-메닐-에톡시)메틸]-5, 7-비스-O-(페닐메틸)-D-만노-헵티톨을 얻고, 이것을 탄소상 팔라듐에서 메탄올-아세트산 내에서 수소화 시켜, 3,6:3¹,4-디언히드로-2-데옥시-3-C-[(1-디히드록시-1-메틸에톡시)메틸]-D-만노-헵티톨을 얻고, 이것을 낮은 온도에서 피리딘내 이치환된 판포로클로리레이트와 반응시키는 것으로 구성된, 화합물 3, 6:3'ㅡ 4-디언히드로-2-데옥시-3-C-[(1-히드록시-1-메틸에톡시0메틸]-D-만노-헵티톨, 1,7-비스(이치환된 포스페이트)[여기서 포스페이트상 치환체는 제 1항에서 정의된 R', R", R"' 및 R""임]의 제조방법.
- R', R", R"' 및 R""가 페닐 또는 치환된 페닐인 경우, 산화 백금상에서 메탄올 또는 에탄올내 임의의 에스테르를 충분한 시간동안 수소화시켜 에스테르를 디히드로겐 포스페이트 유도체로 환원시키는 것으로 구성되거나, R', R", R"' 및 R""가 에틸인 경우, 에스테르를 우선 트리메틸실릴 브로마이드로 충분한 시간동안 처리한후 물로 처리하여 디히드겐 포스페이트 유도체를 생성시키는 것으로 구성된, 제 1항의 에스테르 화합물을 디히드로겐 포스페이트 유도체로 전환시키는 방법.
- 0-5℃에서 무수 에탄올내 CH2N2, CH3CHN2, (CH3)2CN2또는로 구성된 군으로부터 선택된 디아조시약으로 R', R", R"' 및 R""가 각각 수소인, 제 1항 또는 제 8항의 임의의 화합물을 알킬화시킨후, 모든 에스테르 치환체가 결과 테트라에스테르내에서 동일하도록, 아세트산을 첨가하는 것으로 구성된 테트라에스테르의 제조방법.
- 제 1항, 제 8항 또는 제13항의 것으로부터 선택된 화합물의 효과량을 식물에 투여하는 것으로 구성된, 식물내 전분 생성을 증가시키고 뿌리 성장을 감소시키는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23233288A | 1988-08-12 | 1988-08-12 | |
| US7/232,332 | 1988-08-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR900003193A true KR900003193A (ko) | 1990-03-26 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019890011552A KR900003193A (ko) | 1988-08-12 | 1989-08-11 | 과혈당증 및/또는 당뇨병 치료용 신규 유기 화합물 및 그 제조방법 |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0354323A3 (ko) |
| JP (1) | JPH02124896A (ko) |
| KR (1) | KR900003193A (ko) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5391785A (en) * | 1990-01-16 | 1995-02-21 | La Jolla Pharmaceutial Company | Intermediates for providing functional groups on the 5' end of oligonucleotides |
| ES2019839A6 (es) * | 1990-05-10 | 1991-07-01 | Europharma Sa | Procedimiento de obtencion de derivados polifosforilados de galactosa con actividad insulinica. |
| JP2899111B2 (ja) * | 1991-07-15 | 1999-06-02 | ラ ホヤ ファーマシューティカル カンパニー | オリゴヌクレオチドの５’末端へ官能基を提供するための修飾された亜リン酸中間体 |
| FR2818547B1 (fr) | 2000-12-22 | 2006-11-17 | Oreal | Nouveaux derives c-glycosides et utilisation |
| FR2842810B1 (fr) * | 2002-07-25 | 2006-01-27 | Inst Nat Sciences Appliq | Nouveaux composes gem difluores, leur procedes de preparation et leurs applications. |
| FR2900405B1 (fr) | 2006-04-27 | 2013-11-29 | Inst Nat Sciences Appliq | Nouveaux composes c-glycosides monofluores, leurs procedes de preparation et leurs applications |
| FR2900406B1 (fr) * | 2006-04-27 | 2013-09-06 | Inst Nat Sciences Appliq | Mimes stables de sucres de type c-glycosides et c-glycoconjugues,leur procede de preparation et leurs applications notamment dans le domaine de la cosmetique et du medicament. |
| EP2513251B1 (de) * | 2009-12-16 | 2015-05-13 | Basf Se | Flammschutzmittel |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4745185A (en) * | 1984-05-29 | 1988-05-17 | Mcneilab, Inc. | D-arabinose-1,5-diphosphate salts and methods for the treatment of diabetes |
| ES8602951A1 (es) * | 1985-03-15 | 1985-12-16 | Vinas Lab | Procedimiento para la preparacion de un nuevo derivado de lafructosa |
-
1989
- 1989-06-16 EP EP89110990A patent/EP0354323A3/en not_active Withdrawn
- 1989-08-11 JP JP1209515A patent/JPH02124896A/ja active Pending
- 1989-08-11 KR KR1019890011552A patent/KR900003193A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
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| EP0354323A3 (en) | 1990-06-13 |
| JPH02124896A (ja) | 1990-05-14 |
| EP0354323A2 (en) | 1990-02-14 |
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