OA11024A - Sulfonamides and derivatives thereof that modulatethe activity of endothelin - Google Patents

Info

Publication number

OA11024A

OA11024A OA9900058A OA9900058A OA11024A OA 11024 A OA11024 A OA 11024A OA 9900058 A OA9900058 A OA 9900058A OA 9900058 A OA9900058 A OA 9900058A OA 11024 A OA11024 A OA 11024A

Authority

OA

OAPI

Prior art keywords

methyl

sulfonamide

chloro

isoxazolyl

thiophene

Prior art date

1996-09-27

Links

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• 229940124530 sulfonamide Drugs 0.000 title claims abstract description 239
• 108050009340 Endothelin Proteins 0.000 title claims abstract description 139
• 102000002045 Endothelin Human genes 0.000 title claims abstract description 127
• ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 title claims abstract description 124
• 230000000694 effects Effects 0.000 title claims abstract description 87
• 150000003456 sulfonamides Chemical class 0.000 title claims abstract description 76
• 239000000203 mixture Substances 0.000 claims abstract description 158
• 102000005962 receptors Human genes 0.000 claims abstract description 84
• 108020003175 receptors Proteins 0.000 claims abstract description 84
• 238000000034 method Methods 0.000 claims abstract description 73
• 238000009472 formulation Methods 0.000 claims abstract description 72
• 150000003839 salts Chemical class 0.000 claims abstract description 62
• 230000001404 mediated effect Effects 0.000 claims abstract description 33
• 108090000765 processed proteins & peptides Proteins 0.000 claims abstract description 24
• 102000010180 Endothelin receptor Human genes 0.000 claims abstract description 16
• 108050001739 Endothelin receptor Proteins 0.000 claims abstract description 16
• 230000002401 inhibitory effect Effects 0.000 claims abstract description 10
• -1 hetercar / l Chemical group 0.000 claims description 540
• BWJZHYWAXLWLTB-UHFFFAOYSA-N thiophene-3-sulfonamide Chemical compound NS(=O)(=O)C=1C=CSC=1 BWJZHYWAXLWLTB-UHFFFAOYSA-N 0.000 claims description 293
• 150000001875 compounds Chemical class 0.000 claims description 259
• 125000000217 alkyl group Chemical group 0.000 claims description 162
• 125000003118 aryl group Chemical group 0.000 claims description 139
• 239000002253 acid Substances 0.000 claims description 105
• 239000000243 solution Substances 0.000 claims description 89
• 229910052739 hydrogen Inorganic materials 0.000 claims description 67
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 67
• 125000003342 alkenyl group Chemical group 0.000 claims description 64
• 125000000304 alkynyl group Chemical group 0.000 claims description 62
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 62
• 150000002148 esters Chemical class 0.000 claims description 59
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
• 125000001072 heteroaryl group Chemical group 0.000 claims description 54
• 239000001257 hydrogen Substances 0.000 claims description 54
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 54
• 125000003545 alkoxy group Chemical group 0.000 claims description 47
• 150000004820 halides Chemical class 0.000 claims description 46
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 42
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 41
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 37
• 239000011734 sodium Substances 0.000 claims description 37
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
• 201000010099 disease Diseases 0.000 claims description 36
• 125000001188 haloalkyl group Chemical group 0.000 claims description 36
• 229910052708 sodium Inorganic materials 0.000 claims description 35
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 33
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 32
• 125000000623 heterocyclic group Chemical group 0.000 claims description 32
• 125000002577 pseudohalo group Chemical group 0.000 claims description 32
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 31
• 150000001413 amino acids Chemical class 0.000 claims description 28
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 27
• 235000001014 amino acid Nutrition 0.000 claims description 26
• 208000035475 disorder Diseases 0.000 claims description 26
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
• 239000002775 capsule Substances 0.000 claims description 23
• 239000000843 powder Substances 0.000 claims description 23
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
• 125000001424 substituent group Chemical group 0.000 claims description 22
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 21
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 20
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 19
• 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 19
• 150000002402 hexoses Chemical class 0.000 claims description 19
• 125000003282 alkyl amino group Chemical group 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 18
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 18
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 208000024891 symptom Diseases 0.000 claims description 18
• 150000007513 acids Chemical class 0.000 claims description 17
• 125000004104 aryloxy group Chemical group 0.000 claims description 17
• 206010020772 Hypertension Diseases 0.000 claims description 16
• 229930182473 O-glycoside Natural products 0.000 claims description 15
• 150000008444 O-glycosides Chemical class 0.000 claims description 15
• 206010047139 Vasoconstriction Diseases 0.000 claims description 15
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 15
• 125000004414 alkyl thio group Chemical group 0.000 claims description 15
• 239000003937 drug carrier Substances 0.000 claims description 15
• 230000025033 vasoconstriction Effects 0.000 claims description 15
• 125000001769 aryl amino group Chemical group 0.000 claims description 14
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 14
• 125000004122 cyclic group Chemical group 0.000 claims description 14
• 125000003106 haloaryl group Chemical group 0.000 claims description 14
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 14
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 13
• 125000005110 aryl thio group Chemical group 0.000 claims description 13
• 229910052799 carbon Inorganic materials 0.000 claims description 13
• 239000008121 dextrose Substances 0.000 claims description 13
• 125000005843 halogen group Chemical group 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 12
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 12
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 12
• 239000008176 lyophilized powder Substances 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
• 208000006673 asthma Diseases 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 10
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 9
• HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 9
• PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 9
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
• HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 9
• MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 9
• 125000002950 monocyclic group Chemical group 0.000 claims description 9
• 208000002815 pulmonary hypertension Diseases 0.000 claims description 9
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 9
• 150000003334 secondary amides Chemical class 0.000 claims description 9
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
• 229910052717 sulfur Inorganic materials 0.000 claims description 8
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 7
• 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 7
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 7
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
• 208000027866 inflammatory disease Diseases 0.000 claims description 7
• 239000005022 packaging material Substances 0.000 claims description 7
• 230000000063 preceeding effect Effects 0.000 claims description 7
• 150000003291 riboses Chemical class 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 206010040070 Septic Shock Diseases 0.000 claims description 6
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 6
• 230000003042 antagnostic effect Effects 0.000 claims description 6
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 6
• 238000000576 coating method Methods 0.000 claims description 6
• 229940079593 drug Drugs 0.000 claims description 6
• 238000001914 filtration Methods 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
• XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims description 5
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 5
• 125000003423 D-mannosyl group Chemical group C1([C@@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims description 5
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 5
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
• 229920001223 polyethylene glycol Polymers 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
• 239000012064 sodium phosphate buffer Substances 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• 125000001425 triazolyl group Chemical group 0.000 claims description 5
• 229920000623 Cellulose acetate phthalate Polymers 0.000 claims description 4
• 239000002202 Polyethylene glycol Substances 0.000 claims description 4
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 4
• 239000003153 chemical reaction reagent Substances 0.000 claims description 4
• 239000003112 inhibitor Substances 0.000 claims description 4
• ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 claims description 4
• 125000001749 primary amide group Chemical group 0.000 claims description 4
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 4
• 229930192474 thiophene Natural products 0.000 claims description 4
• 206010011416 Croup infectious Diseases 0.000 claims description 3
• 206010052428 Wound Diseases 0.000 claims description 3
• 208000027418 Wounds and injury Diseases 0.000 claims description 3
• AJDYXXCWHDGBML-UHFFFAOYSA-N [3-[[3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]thiophene-2-carbonyl]amino]-2,4,6-trimethylphenyl]methyl acetate Chemical compound CC(=O)OCC1=C(C)C=C(C)C(NC(=O)C2=C(C=CS2)S(=O)(=O)NC2=C(C(C)=NO2)Cl)=C1C AJDYXXCWHDGBML-UHFFFAOYSA-N 0.000 claims description 3
• 125000005136 alkenylsulfinyl group Chemical group 0.000 claims description 3
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
• 125000005154 alkyl sulfonyl amino alkyl group Chemical group 0.000 claims description 3
• 125000002947 alkylene group Chemical group 0.000 claims description 3
• 150000001408 amides Chemical class 0.000 claims description 3
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
• 229910002091 carbon monoxide Inorganic materials 0.000 claims description 3
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• 201000010549 croup Diseases 0.000 claims description 3
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 3
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
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• 125000006684 polyhaloalkyl group Polymers 0.000 claims description 3
• 230000008569 process Effects 0.000 claims description 3
• UXNJXSWMWFYCEM-UHFFFAOYSA-N 3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]-n-[3-(hydroxymethyl)-2,4,6-trimethylphenyl]thiophene-2-carboxamide Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)NC=2C(=C(CO)C(C)=CC=2C)C)=C1Cl UXNJXSWMWFYCEM-UHFFFAOYSA-N 0.000 claims description 2
• 101100244083 Arabidopsis thaliana PKL gene Proteins 0.000 claims description 2
• 241000790917 Dioxys <bee> Species 0.000 claims description 2
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 2
• 229910006074 SO2NH2 Inorganic materials 0.000 claims description 2
• 125000006323 alkenyl amino group Chemical group 0.000 claims description 2
• 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 2
• 235000003704 aspartic acid Nutrition 0.000 claims description 2
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
• 125000005019 carboxyalkenyl group Chemical group 0.000 claims description 2
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
• 239000002158 endotoxin Substances 0.000 claims description 2
• 235000013922 glutamic acid Nutrition 0.000 claims description 2
• 239000004220 glutamic acid Substances 0.000 claims description 2
• 229960003444 immunosuppressant agent Drugs 0.000 claims description 2
• 239000003018 immunosuppressive agent Substances 0.000 claims description 2
• GLFFKEDSTKDWRX-UHFFFAOYSA-N methyl 3-[[3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]thiophene-2-carbonyl]amino]-2,4,6-trimethylbenzoate Chemical compound COC(=O)C1=C(C)C=C(C)C(NC(=O)C2=C(C=CS2)S(=O)(=O)NC2=C(C(C)=NO2)Cl)=C1C GLFFKEDSTKDWRX-UHFFFAOYSA-N 0.000 claims description 2
• 229960000969 phenyl salicylate Drugs 0.000 claims description 2
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
• FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 2
• 239000010931 gold Substances 0.000 claims 36
• 229910052737 gold Inorganic materials 0.000 claims 36
• PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims 10
• ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims 7
• 150000003140 primary amides Chemical class 0.000 claims 5
• BNMNQUBPZZSXQU-UHFFFAOYSA-N 1,3-dioxole-4-carboxylic acid Chemical compound OC(=O)C1=COCO1 BNMNQUBPZZSXQU-UHFFFAOYSA-N 0.000 claims 2
• 101100001672 Emericella variicolor andG gene Proteins 0.000 claims 2
• 206010028980 Neoplasm Diseases 0.000 claims 2
• 201000011510 cancer Diseases 0.000 claims 2
• 150000002343 gold Chemical class 0.000 claims 2
• NIUJNUGCJBDKOC-UHFFFAOYSA-N 1-thiophen-3-ylsulfonyl-3-(2,4,6-trimethyl-3-sulfamoylphenyl)urea Chemical compound S1C=C(C=C1)S(=O)(=O)NC(=O)NC1=C(C(=C(C=C1C)C)S(N)(=O)=O)C NIUJNUGCJBDKOC-UHFFFAOYSA-N 0.000 claims 1
• DJXXZZHIAPUFSR-UHFFFAOYSA-N 3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]-n-(2,4,6-trimethyl-3-sulfamoylphenyl)thiophene-2-carboxamide Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)NC=2C(=C(C(C)=CC=2C)S(N)(=O)=O)C)=C1Cl DJXXZZHIAPUFSR-UHFFFAOYSA-N 0.000 claims 1
• HHUKPBDPFCMJOZ-UHFFFAOYSA-N 3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]-n-[2,4,6-trimethyl-3-(pyridin-2-ylmethyl)phenyl]thiophene-2-carboxamide Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)NC=2C(=C(CC=3N=CC=CC=3)C(C)=CC=2C)C)=C1Cl HHUKPBDPFCMJOZ-UHFFFAOYSA-N 0.000 claims 1
• BRBNADNNVQYSRU-UHFFFAOYSA-N 3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]-n-[3-[(dimethylamino)methyl]-2,4,6-trimethylphenyl]thiophene-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CN(C)CC1=C(C)C=C(C)C(NC(=O)C2=C(C=CS2)S(=O)(=O)NC2=C(C(C)=NO2)Cl)=C1C BRBNADNNVQYSRU-UHFFFAOYSA-N 0.000 claims 1
• 239000001856 Ethyl cellulose Substances 0.000 claims 1
• ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 claims 1
• OTCCIMWXFLJLIA-BYPYZUCNSA-N N-acetyl-L-aspartic acid Chemical compound CC(=O)N[C@H](C(O)=O)CC(O)=O OTCCIMWXFLJLIA-BYPYZUCNSA-N 0.000 claims 1
• BTIYYMLKVODXLC-UHFFFAOYSA-N NS([S+]1C=CC=C1)(=O)=O Chemical compound NS([S+]1C=CC=C1)(=O)=O BTIYYMLKVODXLC-UHFFFAOYSA-N 0.000 claims 1
• 239000004698 Polyethylene Substances 0.000 claims 1
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• 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims 1
• 206010049771 Shock haemorrhagic Diseases 0.000 claims 1
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• SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
• 229910052783 alkali metal Inorganic materials 0.000 claims 1
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• 125000005025 alkynylaryl group Chemical group 0.000 claims 1
• 230000002052 anaphylactic effect Effects 0.000 claims 1
• ULBTUVJTXULMLP-UHFFFAOYSA-N butyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCC ULBTUVJTXULMLP-UHFFFAOYSA-N 0.000 claims 1
• 239000004359 castor oil Substances 0.000 claims 1
• 229960001777 castor oil Drugs 0.000 claims 1
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• 125000002993 cycloalkylene group Chemical group 0.000 claims 1
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• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims 1
• 229930182470 glycoside Natural products 0.000 claims 1
• 230000001861 immunosuppressant effect Effects 0.000 claims 1
• NLVILCRFJNVIEX-UHFFFAOYSA-N n-[3-(aminomethyl)-2,4,6-trimethylphenyl]-3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]thiophene-2-carboxamide Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)NC=2C(=C(CN)C(C)=CC=2C)C)=C1Cl NLVILCRFJNVIEX-UHFFFAOYSA-N 0.000 claims 1
• 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims 1
• QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims 1
• OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
• WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 claims 1
• 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
• ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical class [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims 1
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