MXPA04002438A

MXPA04002438A - Preparacion y uso de derivados de pirroll para el tratamiento de la obesidad.

Preparacion y uso de derivados de pirroll para el tratamiento de la obesidad.

Info

Publication number: MXPA04002438A
Authority: MX; Mexico
Prior art keywords: alkyl; hydroxy; alkoxy; optionally substituted; trifluoromethyl
Prior art date: 2001-09-24

Application number

MXPA04002438A

Other languages

English (en)

Spanish (es)

Inventor

C E Kluender Harold

Original Assignee

Bayer Pharmaceuticals Corp

Priority date

2001-09-24

Filing date

2002-09-24

Publication date

2004-06-29

2002-09-24 Application filed by Bayer Pharmaceuticals Corp filed Critical Bayer Pharmaceuticals Corp

2004-06-29 Publication of MXPA04002438A publication Critical patent/MXPA04002438A/es

Links

208000008589 Obesity Diseases 0.000 title claims abstract description 41
235000020824 obesity Nutrition 0.000 title claims abstract description 40
150000003233 pyrroles Chemical class 0.000 title abstract description 8
238000002360 preparation method Methods 0.000 title description 23
150000001875 compounds Chemical class 0.000 claims abstract description 146
238000000034 method Methods 0.000 claims abstract description 75
239000000203 mixture Substances 0.000 claims abstract description 53
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
235000019789 appetite Nutrition 0.000 claims abstract description 6
230000036528 appetite Effects 0.000 claims abstract description 6
-1 hydroxy, benzyloxy Chemical group 0.000 claims description 152
125000000217 alkyl group Chemical group 0.000 claims description 114
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 60
125000003545 alkoxy group Chemical group 0.000 claims description 58
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 50
239000003795 chemical substances by application Substances 0.000 claims description 42
150000002148 esters Chemical class 0.000 claims description 38
229910052736 halogen Inorganic materials 0.000 claims description 36
150000002367 halogens Chemical class 0.000 claims description 36
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
229910052757 nitrogen Inorganic materials 0.000 claims description 33
125000004433 nitrogen atom Chemical group N* 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 33
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 30
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 29
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
125000004093 cyano group Chemical group *C#N 0.000 claims description 21
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 18
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
239000011737 fluorine Substances 0.000 claims description 18
229910052731 fluorine Inorganic materials 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
239000003981 vehicle Substances 0.000 claims description 16
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 14
125000001153 fluoro group Chemical group F* 0.000 claims description 13
239000003937 drug carrier Substances 0.000 claims description 12
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
229920006395 saturated elastomer Polymers 0.000 claims description 11
206010020772 Hypertension Diseases 0.000 claims description 10
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 10
201000010099 disease Diseases 0.000 claims description 9
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
239000003472 antidiabetic agent Substances 0.000 claims description 8
235000012631 food intake Nutrition 0.000 claims description 8
238000010521 absorption reaction Methods 0.000 claims description 7
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
230000029087 digestion Effects 0.000 claims description 7
229940126904 hypoglycaemic agent Drugs 0.000 claims description 7
230000004060 metabolic process Effects 0.000 claims description 7
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
CYAYCOCJAVHQSD-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid Chemical compound CC=1C(C(O)=O)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 CYAYCOCJAVHQSD-UHFFFAOYSA-N 0.000 claims description 6
208000032928 Dyslipidaemia Diseases 0.000 claims description 6
239000011230 binding agent Substances 0.000 claims description 6
206010012601 diabetes mellitus Diseases 0.000 claims description 6
230000037406 food intake Effects 0.000 claims description 6
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 6
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 6
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
125000003386 piperidinyl group Chemical group 0.000 claims description 6
125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 5
125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 5
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical class OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
208000017170 Lipid metabolism disease Diseases 0.000 claims description 5
235000012000 cholesterol Nutrition 0.000 claims description 5
239000003112 inhibitor Substances 0.000 claims description 5
230000000968 intestinal effect Effects 0.000 claims description 5
230000004130 lipolysis Effects 0.000 claims description 5
230000036186 satiety Effects 0.000 claims description 5
235000019627 satiety Nutrition 0.000 claims description 5
230000035924 thermogenesis Effects 0.000 claims description 5
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
206010028980 Neoplasm Diseases 0.000 claims description 4
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 4
230000003143 atherosclerotic effect Effects 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
201000011510 cancer Diseases 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
229940125753 fibrate Drugs 0.000 claims description 4
208000006575 hypertriglyceridemia Diseases 0.000 claims description 4
201000008482 osteoarthritis Diseases 0.000 claims description 4
208000011580 syndromic disease Diseases 0.000 claims description 4
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
208000032841 Bulimia Diseases 0.000 claims description 3
206010006550 Bulimia nervosa Diseases 0.000 claims description 3
208000024172 Cardiovascular disease Diseases 0.000 claims description 3
102000004877 Insulin Human genes 0.000 claims description 3
108090001061 Insulin Proteins 0.000 claims description 3
229940122199 Insulin secretagogue Drugs 0.000 claims description 3
229940100389 Sulfonylurea Drugs 0.000 claims description 3
239000000556 agonist Substances 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
208000026106 cerebrovascular disease Diseases 0.000 claims description 3
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
208000001130 gallstones Diseases 0.000 claims description 3
239000003316 glycosidase inhibitor Substances 0.000 claims description 3
208000000509 infertility Diseases 0.000 claims description 3
231100000535 infertility Toxicity 0.000 claims description 3
230000036512 infertility Effects 0.000 claims description 3
229940125396 insulin Drugs 0.000 claims description 3
231100000551 menstrual abnormality Toxicity 0.000 claims description 3
230000002093 peripheral effect Effects 0.000 claims description 3
201000002859 sleep apnea Diseases 0.000 claims description 3
BLARRMGRSJWTAH-UHFFFAOYSA-N 1-(2-chlorophenyl)-5-(4-chlorophenyl)-2-methyl-n-piperidin-1-ylpyrrole-3-carboxamide;hydrochloride Chemical compound Cl.C=1C=CC=C(Cl)C=1N1C(C)=C(C(=O)NN2CCCCC2)C=C1C1=CC=C(Cl)C=C1 BLARRMGRSJWTAH-UHFFFAOYSA-N 0.000 claims description 2
229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 2
206010036049 Polycystic ovaries Diseases 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims description 2
230000006399 behavior Effects 0.000 claims description 2
230000003542 behavioural effect Effects 0.000 claims description 2
210000001672 ovary Anatomy 0.000 claims description 2
201000010065 polycystic ovary syndrome Diseases 0.000 claims description 2
239000000126 substance Substances 0.000 claims description 2
208000011117 substance-related disease Diseases 0.000 claims description 2
HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 4
239000003613 bile acid Substances 0.000 claims 4
206010012335 Dependence Diseases 0.000 claims 3
102000004316 Oxidoreductases Human genes 0.000 claims 3
108090000854 Oxidoreductases Proteins 0.000 claims 3
208000015114 central nervous system disease Diseases 0.000 claims 2
125000004193 piperazinyl group Chemical group 0.000 claims 2
230000001105 regulatory effect Effects 0.000 claims 2
GATYVSWNUQBZOD-UHFFFAOYSA-N 1-(2-chlorophenyl)-5-(4-chlorophenyl)-2-methyl-n'-[2-(trifluoromethyl)phenyl]pyrrole-3-carbohydrazide;hydrochloride Chemical compound Cl.C=1C=CC=C(Cl)C=1N1C(C)=C(C(=O)NNC=2C(=CC=CC=2)C(F)(F)F)C=C1C1=CC=C(Cl)C=C1 GATYVSWNUQBZOD-UHFFFAOYSA-N 0.000 claims 1
OVECUJXUUDOLJS-NFBKMPQASA-N 1-(2-chlorophenyl)-5-(4-chlorophenyl)-n-[(1r,2r)-2-hydroxycyclohexyl]-2-methylpyrrole-3-carboxamide Chemical compound C=1C=CC=C(Cl)C=1N1C(C)=C(C(=O)N[C@H]2[C@@H](CCCC2)O)C=C1C1=CC=C(Cl)C=C1 OVECUJXUUDOLJS-NFBKMPQASA-N 0.000 claims 1
WGXPKLSREJJEQA-UHFFFAOYSA-N 1-(2-chlorophenyl)-5-(4-methoxyphenyl)-2-methyl-n'-[2-(trifluoromethyl)phenyl]pyrrole-3-carbohydrazide;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1C1=CC(C(=O)NNC=2C(=CC=CC=2)C(F)(F)F)=C(C)N1C1=CC=CC=C1Cl WGXPKLSREJJEQA-UHFFFAOYSA-N 0.000 claims 1
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 abstract description 7
238000003786 synthesis reaction Methods 0.000 abstract description 7
230000004580 weight loss Effects 0.000 abstract description 7
230000001939 inductive effect Effects 0.000 abstract description 2
230000014759 maintenance of location Effects 0.000 description 57
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 55
238000004128 high performance liquid chromatography Methods 0.000 description 54
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 52
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
239000003826 tablet Substances 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
235000013305 food Nutrition 0.000 description 17
239000000243 solution Substances 0.000 description 17
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
241000700159 Rattus Species 0.000 description 16
230000037396 body weight Effects 0.000 description 16
239000003814 drug Substances 0.000 description 16
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 15
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
238000012360 testing method Methods 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 14
RDOXTESZEPMUJZ-UHFFFAOYSA-N methyl phenyl ether Natural products COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
241001465754 Metazoa Species 0.000 description 13
239000004480 active ingredient Substances 0.000 description 13
235000014113 dietary fatty acids Nutrition 0.000 description 13
239000000194 fatty acid Substances 0.000 description 13
229930195729 fatty acid Natural products 0.000 description 13
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 12
235000019441 ethanol Nutrition 0.000 description 12
238000009472 formulation Methods 0.000 description 12
239000000463 material Substances 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 11
239000007787 solid Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
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 10
239000002775 capsule Substances 0.000 description 10
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
229940079593 drug Drugs 0.000 description 10
150000004665 fatty acids Chemical class 0.000 description 10
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 10
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
239000000725 suspension Substances 0.000 description 9
238000005481 NMR spectroscopy Methods 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 8
239000002480 mineral oil Substances 0.000 description 8
235000010446 mineral oil Nutrition 0.000 description 8
239000003921 oil Substances 0.000 description 8
235000019198 oils Nutrition 0.000 description 8
239000001768 carboxy methyl cellulose Substances 0.000 description 7
235000019439 ethyl acetate Nutrition 0.000 description 7
235000011187 glycerol Nutrition 0.000 description 7
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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108010010803 Gelatin Proteins 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
210000004556 brain Anatomy 0.000 description 6
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235000011852 gelatine desserts Nutrition 0.000 description 6
239000008103 glucose Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
229920000609 methyl cellulose Polymers 0.000 description 6
235000010981 methylcellulose Nutrition 0.000 description 6
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229920002261 Corn starch Polymers 0.000 description 5
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
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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 5
150000001412 amines Chemical class 0.000 description 5
239000007859 condensation product Substances 0.000 description 5
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
239000000312 peanut oil Substances 0.000 description 5
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