TW200403995A - New thiazole derivatives as NPY receptor antagonists - Google Patents

Info

Publication number

TW200403995A

TW200403995A TW092104045A TW92104045A TW200403995A TW 200403995 A TW200403995 A TW 200403995A TW 092104045 A TW092104045 A TW 092104045A TW 92104045 A TW92104045 A TW 92104045A TW 200403995 A TW200403995 A TW 200403995A

Authority

TW

Taiwan

Prior art keywords

methyl

ylamino

benzylidene

propyl

pyrazol

Prior art date

2002-02-28

Links

• Espacenet
• Global Dossier
• Discuss

• 101710151321 Melanostatin Proteins 0.000 title description 8
• 102100028427 Pro-neuropeptide Y Human genes 0.000 title description 8
• 150000007979 thiazole derivatives Chemical class 0.000 title description 8
• 239000002464 receptor antagonist Substances 0.000 title description 2
• 229940044551 receptor antagonist Drugs 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 209
• 150000003839 salts Chemical class 0.000 claims abstract description 49
• 208000008589 Obesity Diseases 0.000 claims abstract description 26
• 235000020824 obesity Nutrition 0.000 claims abstract description 26
• 150000002148 esters Chemical class 0.000 claims abstract description 24
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 15
• 208000001647 Renal Insufficiency Diseases 0.000 claims abstract description 14
• 206010003246 arthritis Diseases 0.000 claims abstract description 14
• 201000006370 kidney failure Diseases 0.000 claims abstract description 14
• 230000002265 prevention Effects 0.000 claims abstract description 14
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 13
• 208000030814 Eating disease Diseases 0.000 claims abstract description 13
• 208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 13
• 235000014632 disordered eating Nutrition 0.000 claims abstract description 13
• -1 methyl-benzylidene Chemical group 0.000 claims description 602
• 238000006243 chemical reaction Methods 0.000 claims description 151
• 238000000034 method Methods 0.000 claims description 82
• 125000000217 alkyl group Chemical group 0.000 claims description 41
• 150000001412 amines Chemical class 0.000 claims description 38
• 239000002253 acid Substances 0.000 claims description 31
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 239000001257 hydrogen Substances 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 17
• 229940086609 Lipase inhibitor Drugs 0.000 claims description 16
• 238000004519 manufacturing process Methods 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 12
• 239000000460 chlorine Substances 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 150000002367 halogens Chemical class 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• BYBCSHJGFWTWAB-UHFFFAOYSA-N pyrimidine-2-sulfonic acid Chemical compound OS(=O)(=O)C1=NC=CC=N1 BYBCSHJGFWTWAB-UHFFFAOYSA-N 0.000 claims description 9
• 239000000126 substance Substances 0.000 claims description 9
• 241001069925 Orestes Species 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 229940079593 drug Drugs 0.000 claims description 8
• BSXLLFUSNQCWJP-UHFFFAOYSA-N thiophene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CS1 BSXLLFUSNQCWJP-UHFFFAOYSA-N 0.000 claims description 8
• 125000001072 heteroaryl group Chemical group 0.000 claims description 7
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
• 229910052794 bromium Inorganic materials 0.000 claims description 6
• 201000010099 disease Diseases 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
• BLKOSTJSUMJMSR-UHFFFAOYSA-N 5-chlorothiophene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Cl)S1 BLKOSTJSUMJMSR-UHFFFAOYSA-N 0.000 claims description 4
• 229940127470 Lipase Inhibitors Drugs 0.000 claims description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 3
• 239000013543 active substance Substances 0.000 claims description 3
• 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000001188 haloalkyl group Chemical group 0.000 claims description 3
• 230000001225 therapeutic effect Effects 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical group 0.000 claims 4
• KXZIBRUIJDEWKY-UHFFFAOYSA-N 2,5-dimethoxyfuran Chemical group COC1=CC=C(OC)O1 KXZIBRUIJDEWKY-UHFFFAOYSA-N 0.000 claims 1
• 150000001924 cycloalkanes Chemical group 0.000 claims 1
• 238000010586 diagram Methods 0.000 claims 1
• AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical group CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims 1
• 229960001243 orlistat Drugs 0.000 claims 1
• MAGSSGQAJNNDLU-UHFFFAOYSA-N s-phenylthiohydroxylamine Chemical compound NSC1=CC=CC=C1 MAGSSGQAJNNDLU-UHFFFAOYSA-N 0.000 claims 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
• 229910052740 iodine Inorganic materials 0.000 abstract description 4
• 239000000825 pharmaceutical preparation Substances 0.000 abstract description 4
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 263
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 73
• 239000000047 product Substances 0.000 description 58
• 239000000203 mixture Substances 0.000 description 56
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
• 239000003153 chemical reaction reagent Substances 0.000 description 48
• 239000002904 solvent Substances 0.000 description 46
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
• DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 38
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 25
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
• 239000000243 solution Substances 0.000 description 24
• 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 description 21
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
• 230000015572 biosynthetic process Effects 0.000 description 21
• 238000004458 analytical method Methods 0.000 description 20
• 238000003786 synthesis reaction Methods 0.000 description 20
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 19
• 238000004949 mass spectrometry Methods 0.000 description 19
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
• 238000010992 reflux Methods 0.000 description 17
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
• 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 description 16
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
• 229960001701 chloroform Drugs 0.000 description 13
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
• 230000002829 reductive effect Effects 0.000 description 12
• 238000005160 1H NMR spectroscopy Methods 0.000 description 11
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 11
• 238000010438 heat treatment Methods 0.000 description 11
• XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 11
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 11
• BJYNYQGJTZULJI-UHFFFAOYSA-N 2-methoxy-5-methylbenzenesulfonyl chloride Chemical compound COC1=CC=C(C)C=C1S(Cl)(=O)=O BJYNYQGJTZULJI-UHFFFAOYSA-N 0.000 description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
• 239000003795 chemical substances by application Substances 0.000 description 10
• 231100000989 no adverse effect Toxicity 0.000 description 10
• 239000007787 solid Substances 0.000 description 10
• 125000001424 substituent group Chemical group 0.000 description 10
• 229940124530 sulfonamide Drugs 0.000 description 10
• 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 description 10
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• 239000004202 carbamide Substances 0.000 description 9
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
• 239000003921 oil Substances 0.000 description 9
• 235000019198 oils Nutrition 0.000 description 9
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 9
• 125000006308 propyl amino group Chemical group 0.000 description 9
• FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 9
• MXVMRHIWTSFDPU-UHFFFAOYSA-N 2-chlorobenzenecarboximidamide Chemical compound NC(=N)C1=CC=CC=C1Cl MXVMRHIWTSFDPU-UHFFFAOYSA-N 0.000 description 8
• JHJKSEKUZNJKGO-UHFFFAOYSA-N 3-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=CC(S(Cl)(=O)=O)=C1 JHJKSEKUZNJKGO-UHFFFAOYSA-N 0.000 description 8
• VMXLZAVIEYWCLQ-UHFFFAOYSA-N 4-(4-aminophenyl)-3-methylaniline Chemical compound CC1=CC(N)=CC=C1C1=CC=C(N)C=C1 VMXLZAVIEYWCLQ-UHFFFAOYSA-N 0.000 description 8
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 8
• 239000000741 silica gel Substances 0.000 description 8
• 229910002027 silica gel Inorganic materials 0.000 description 8
• 150000003456 sulfonamides Chemical class 0.000 description 8
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
• BFXHJFKKRGVUMU-UHFFFAOYSA-N 4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1 BFXHJFKKRGVUMU-UHFFFAOYSA-N 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
• IXPYHTLBJSMNQF-UHFFFAOYSA-N CC(C)(C)OC(NCCCNC(NCN(C)C)=S)=O Chemical compound CC(C)(C)OC(NCCCNC(NCN(C)C)=S)=O IXPYHTLBJSMNQF-UHFFFAOYSA-N 0.000 description 7
• 238000003818 flash chromatography Methods 0.000 description 7
• 235000019253 formic acid Nutrition 0.000 description 7
• 239000007903 gelatin capsule Substances 0.000 description 7
• 239000012071 phase Substances 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• 108020003175 receptors Proteins 0.000 description 7
• 102000005962 receptors Human genes 0.000 description 7
• ZEYKLMDPUOVUCR-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=C(Cl)C(S(Cl)(=O)=O)=C1 ZEYKLMDPUOVUCR-UHFFFAOYSA-N 0.000 description 6
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
• DTJVECUKADWGMO-UHFFFAOYSA-N 4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1 DTJVECUKADWGMO-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• 229920002261 Corn starch Polymers 0.000 description 6
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 235000013877 carbamide Nutrition 0.000 description 6
• 125000004432 carbon atom Chemical group C* 0.000 description 6
• 239000000084 colloidal system Substances 0.000 description 6
• 239000008120 corn starch Substances 0.000 description 6
• NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 6
• 238000001704 evaporation Methods 0.000 description 6
• 230000008020 evaporation Effects 0.000 description 6
• 239000012948 isocyanate Substances 0.000 description 6
• 235000019341 magnesium sulphate Nutrition 0.000 description 6
• URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 6
• 238000002953 preparative HPLC Methods 0.000 description 6
• 150000003217 pyrazoles Chemical class 0.000 description 6
• 239000007858 starting material Substances 0.000 description 6
• 238000003756 stirring Methods 0.000 description 6
• 239000000454 talc Substances 0.000 description 6
• 229910052623 talc Inorganic materials 0.000 description 6
• IXRQTCDPQZMNSN-UHFFFAOYSA-N (2-methylphenyl)methylhydrazine Chemical compound CC1=CC=CC=C1CNN IXRQTCDPQZMNSN-UHFFFAOYSA-N 0.000 description 5
• DERNFYMWIOSZRC-UHFFFAOYSA-N (2-methylphenyl)phosphanium;bromide Chemical compound [Br-].CC1=CC=CC=C1[PH3+] DERNFYMWIOSZRC-UHFFFAOYSA-N 0.000 description 5
• JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 5
• HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 5
• 125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 description 5
• OKYSUJVCDXZGKE-UHFFFAOYSA-N 3-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC(S(Cl)(=O)=O)=C1 OKYSUJVCDXZGKE-UHFFFAOYSA-N 0.000 description 5
• QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 5
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 5
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
• 101100460785 Mus musculus Npy5r gene Proteins 0.000 description 5
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
• HLABGJLUTKJSBA-UHFFFAOYSA-N [2-(3-aminopropylamino)-1,3-thiazol-5-yl]-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)C1=CN=C(NCCCN)S1 HLABGJLUTKJSBA-UHFFFAOYSA-N 0.000 description 5
• 239000002671 adjuvant Substances 0.000 description 5
• 125000000304 alkynyl group Chemical group 0.000 description 5
• 150000001409 amidines Chemical class 0.000 description 5
• 125000003277 amino group Chemical group 0.000 description 5
• CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
• KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 125000000524 functional group Chemical group 0.000 description 5
• 239000004615 ingredient Substances 0.000 description 5
• 150000002513 isocyanates Chemical class 0.000 description 5
• 239000008101 lactose Substances 0.000 description 5
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 5
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 5
• 229920005862 polyol Polymers 0.000 description 5
• 150000003077 polyols Chemical class 0.000 description 5
• 125000006239 protecting group Chemical group 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
• 238000000926 separation method Methods 0.000 description 5
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
• 229940005605 valeric acid Drugs 0.000 description 5
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