KR101901836B1 - 식품 첨가물 또는 약제로 사용되는 신규 황 함유 지질 - Google Patents
식품 첨가물 또는 약제로 사용되는 신규 황 함유 지질 Download PDFInfo
- Publication number
- KR101901836B1 KR101901836B1 KR1020177020879A KR20177020879A KR101901836B1 KR 101901836 B1 KR101901836 B1 KR 101901836B1 KR 1020177020879 A KR1020177020879 A KR 1020177020879A KR 20177020879 A KR20177020879 A KR 20177020879A KR 101901836 B1 KR101901836 B1 KR 101901836B1
- Authority
- KR
- South Korea
- Prior art keywords
- lipid compound
- butanoic acid
- pentadeca
- icosa
- lipid
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 239000003814 drug Substances 0.000 title claims abstract description 25
- 150000002632 lipids Chemical class 0.000 title claims abstract description 17
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 235000015872 dietary supplement Nutrition 0.000 title description 4
- 239000005864 Sulphur Substances 0.000 title 1
- -1 lipid compound Chemical class 0.000 claims abstract description 111
- 150000001875 compounds Chemical class 0.000 claims abstract description 104
- 239000000203 mixture Substances 0.000 claims abstract description 52
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims abstract description 24
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 16
- 150000001733 carboxylic acid esters Chemical class 0.000 claims abstract description 14
- 150000003857 carboxamides Chemical class 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 150000003462 sulfoxides Chemical group 0.000 claims abstract description 11
- 150000003457 sulfones Chemical group 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 239000011593 sulfur Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 41
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 34
- 239000003921 oil Substances 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 18
- 229930195729 fatty acid Natural products 0.000 claims description 18
- 239000000194 fatty acid Substances 0.000 claims description 18
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 18
- 150000004665 fatty acids Chemical class 0.000 claims description 17
- 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 claims description 16
- DLRFUJBFSPOWAI-AFSLFLIVSA-N 2-[(3z,6z,9z,12z)-pentadeca-3,6,9,12-tetraenyl]sulfanylbutanoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/CCSC(CC)C(O)=O DLRFUJBFSPOWAI-AFSLFLIVSA-N 0.000 claims description 15
- 150000003626 triacylglycerols Chemical class 0.000 claims description 15
- NAEGIDHQGAYIFF-AFSLFLIVSA-N 2-[(3z,6z,9z,12z)-pentadeca-3,6,9,12-tetraenyl]sulfonylbutanoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/CCS(=O)(=O)C(CC)C(O)=O NAEGIDHQGAYIFF-AFSLFLIVSA-N 0.000 claims description 14
- JFNAMHYHCCNOIS-NEUKSRIFSA-N 2-ethyl-2-[(5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenyl]sulfanylbutanoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCSC(CC)(CC)C(O)=O JFNAMHYHCCNOIS-NEUKSRIFSA-N 0.000 claims description 12
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 12
- 208000024891 symptom Diseases 0.000 claims description 12
- CJKMCXKSRWOCNR-AFSLFLIVSA-N 2-[(3z,6z,9z,12z)-pentadeca-3,6,9,12-tetraenyl]sulfinylbutanoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/CCS(=O)C(CC)C(O)=O CJKMCXKSRWOCNR-AFSLFLIVSA-N 0.000 claims description 11
- FOVUVFJCIMQFJK-AAQCHOMXSA-N 2-[(5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenyl]sulfanyl-2-methylpropanoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCSC(C)(C)C(O)=O FOVUVFJCIMQFJK-AAQCHOMXSA-N 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims description 11
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 10
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 102000004877 Insulin Human genes 0.000 claims description 8
- 108090001061 Insulin Proteins 0.000 claims description 8
- 210000004369 blood Anatomy 0.000 claims description 8
- 239000008280 blood Substances 0.000 claims description 8
- 229940125396 insulin Drugs 0.000 claims description 8
- 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 7
- 241000124008 Mammalia Species 0.000 claims description 7
- 239000008103 glucose Substances 0.000 claims description 7
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 208000008589 Obesity Diseases 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 6
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 claims description 6
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 6
- 235000020824 obesity Nutrition 0.000 claims description 6
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 6
- 239000002775 capsule Substances 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 150000001924 cycloalkanes Chemical class 0.000 claims description 5
- 208000010706 fatty liver disease Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 206010022489 Insulin Resistance Diseases 0.000 claims description 4
- 238000008214 LDL Cholesterol Methods 0.000 claims description 4
- 206010033307 Overweight Diseases 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- 108010069201 VLDL Cholesterol Proteins 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 229940106134 krill oil Drugs 0.000 claims description 4
- 230000002093 peripheral effect Effects 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 210000002966 serum Anatomy 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 3
- 239000004475 Arginine Substances 0.000 claims description 2
- 229920001661 Chitosan Polymers 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- PDJNBVFLPYRGJI-AAQCHOMXSA-N ethyl 1-[(5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenyl]sulfanylcyclobutane-1-carboxylate Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCSC1(C(=O)OCC)CCC1 PDJNBVFLPYRGJI-AAQCHOMXSA-N 0.000 claims description 2
- 235000013373 food additive Nutrition 0.000 claims description 2
- 239000002778 food additive Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229960003194 meglumine Drugs 0.000 claims description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
- 229960001295 tocopherol Drugs 0.000 claims description 2
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- 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 claims description 2
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- UNUZTFMIJYFAPE-NEUKSRIFSA-N 2-ethyl-2-[(5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenyl]sulfinylbutanoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCS(=O)C(CC)(CC)C(O)=O UNUZTFMIJYFAPE-NEUKSRIFSA-N 0.000 claims 1
- LDQMFHGQNFLYJI-NEUKSRIFSA-N 2-ethyl-2-[(5z,8z,11z,14z,17z)-icosa-5,8,11,14,17-pentaenyl]sulfonylbutanoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCS(=O)(=O)C(CC)(CC)C(O)=O LDQMFHGQNFLYJI-NEUKSRIFSA-N 0.000 claims 1
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- 229910019142 PO4 Inorganic materials 0.000 claims 1
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
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- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 28
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- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/55—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
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- Coloring Foods And Improving Nutritive Qualities (AREA)
- Medicinal Preparation (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
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| US61/080,804 | 2008-07-15 | ||
| PCT/NO2009/000262 WO2010008299A1 (en) | 2008-07-15 | 2009-07-13 | Novel sulphur containing lipids for use as food supplement or as medicament |
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| KR101390589B1 (ko) * | 2012-05-30 | 2014-04-30 | 가천대학교 산학협력단 | 다이아민을 포함하는 당뇨병의 예방 또는 치료용 조성물 |
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| CN115025079A (zh) | 2015-04-28 | 2022-09-09 | 普罗诺瓦生物医药挪威公司 | 结构增强的含硫脂肪酸在预防和/或治疗非酒精性脂肪性肝炎中的用途 |
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| WO2018055062A1 (en) | 2016-09-21 | 2018-03-29 | Avexxin As | Pharmaceutical composition |
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| CA3084728A1 (en) | 2017-12-06 | 2019-06-13 | Basf As | Fatty acid derivatives for treating non-alcoholic steatohepatitis |
| WO2019222254A1 (en) * | 2018-05-16 | 2019-11-21 | Epitracker, Inc. | Compositions and methods for diagnosis and treatment of conditions related to aging |
| JP2021525249A (ja) | 2018-05-23 | 2021-09-24 | エピトラッカー インコーポレイテッドEpitracker, Inc. | 加齢及び長期性の質に関連する状態の診断及び治療のための組成物及び方法 |
| AU2019274203B2 (en) * | 2018-05-23 | 2025-01-02 | Basf As | Structurally modified fatty acids for improving glycemic control and treating inflammatory bowel disease |
| WO2020146263A1 (en) | 2019-01-09 | 2020-07-16 | Epitracker, Inc. | Compositions and methods for diagnosis and treatment of neurodegenerative diseases |
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Non-Patent Citations (1)
| Title |
|---|
| Lipids, Vol. 40, No. 1, pp.49-57, 2005 |
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