TW498076B - Modified amino acids and pharmaceutical compositions containing these compounds - Google Patents

Info

Publication number

TW498076B

TW498076B TW089125839A TW89125839A TW498076B TW 498076 B TW498076 B TW 498076B TW 089125839 A TW089125839 A TW 089125839A TW 89125839 A TW89125839 A TW 89125839A TW 498076 B TW498076 B TW 498076B

Authority

TW

Taiwan

Prior art keywords

dihydro

hexahydropyridyl

dibromo

carbonyl

hexahydro

Prior art date

1996-09-10

Links

• Espacenet
• Global Dossier
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• 150000001413 amino acids Chemical class 0.000 title claims abstract description 19
• 239000008194 pharmaceutical composition Chemical class 0.000 title claims abstract description 5
• 150000001875 compounds Chemical class 0.000 title abstract description 88
• 150000003839 salts Chemical class 0.000 claims abstract description 34
• 239000000203 mixture Substances 0.000 claims abstract description 19
• 150000007524 organic acids Chemical class 0.000 claims abstract description 4
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 907
• -1 Nitro, methoxy, trifluorofluorenyl Chemical group 0.000 claims description 852
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 290
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 240
• 125000001424 substituent group Chemical group 0.000 claims description 191
• 229910052757 nitrogen Inorganic materials 0.000 claims description 181
• 229960000632 dexamfetamine Drugs 0.000 claims description 174
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 158
• 230000002079 cooperative effect Effects 0.000 claims description 145
• 125000000217 alkyl group Chemical group 0.000 claims description 144
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 127
• 125000004076 pyridyl group Chemical group 0.000 claims description 114
• 150000001412 amines Chemical class 0.000 claims description 105
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 95
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 93
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 91
• 229910052799 carbon Inorganic materials 0.000 claims description 90
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 85
• 229960003732 tyramine Drugs 0.000 claims description 77
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 76
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 75
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 74
• 229910052739 hydrogen Inorganic materials 0.000 claims description 74
• 239000001257 hydrogen Substances 0.000 claims description 74
• 150000001721 carbon Chemical group 0.000 claims description 70
• 238000011049 filling Methods 0.000 claims description 69
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 68
• 229910052801 chlorine Inorganic materials 0.000 claims description 67
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 67
• 239000000460 chlorine Substances 0.000 claims description 65
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 64
• 229910052731 fluorine Inorganic materials 0.000 claims description 60
• 239000011737 fluorine Substances 0.000 claims description 60
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 59
• 229910052760 oxygen Inorganic materials 0.000 claims description 59
• 239000001301 oxygen Substances 0.000 claims description 59
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 54
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 54
• PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 54
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 53
• 125000003277 amino group Chemical group 0.000 claims description 51
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 47
• 125000004432 carbon atom Chemical group C* 0.000 claims description 47
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 46
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 45
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 40
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 40
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
• 229950005223 levamfetamine Drugs 0.000 claims description 39
• 125000003545 alkoxy group Chemical group 0.000 claims description 37
• 235000010290 biphenyl Nutrition 0.000 claims description 37
• 239000004305 biphenyl Substances 0.000 claims description 37
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 36
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 36
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 35
• VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 35
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 35
• 150000003254 radicals Chemical class 0.000 claims description 32
• 125000003282 alkyl amino group Chemical group 0.000 claims description 29
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 27
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 26
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 26
• 125000002950 monocyclic group Chemical group 0.000 claims description 26
• KWTSXDURSIMDCE-MRVPVSSYSA-N (R)-amphetamine Chemical compound C[C@@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-MRVPVSSYSA-N 0.000 claims description 24
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 24
• 125000004429 atom Chemical group 0.000 claims description 23
• 229940025084 amphetamine Drugs 0.000 claims description 22
• 239000002253 acid Substances 0.000 claims description 21
• 230000027455 binding Effects 0.000 claims description 21
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 21
• 125000001246 bromo group Chemical group Br* 0.000 claims description 21
• 150000002431 hydrogen Chemical group 0.000 claims description 21
• 239000007789 gas Substances 0.000 claims description 20
• 125000004747 1,1-dimethylethoxycarbonyl group Chemical group CC(C)(OC(=O)*)C 0.000 claims description 19
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 19
• 125000000304 alkynyl group Chemical group 0.000 claims description 19
• 229940024606 amino acid Drugs 0.000 claims description 19
• 125000003118 aryl group Chemical group 0.000 claims description 19
• 125000006267 biphenyl group Chemical group 0.000 claims description 19
• 229910052794 bromium Inorganic materials 0.000 claims description 19
• 239000003574 free electron Substances 0.000 claims description 19
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 19
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 18
• 238000012360 testing method Methods 0.000 claims description 18
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 17
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 17
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 16
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 16
• 208000011580 syndromic disease Diseases 0.000 claims description 16
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 15
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 15
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 14
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
• XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 13
• RGBWBVGQZFJTEO-UHFFFAOYSA-N 4-piperidin-4-ylpyridine Chemical compound C1CNCCC1C1=CC=NC=C1 RGBWBVGQZFJTEO-UHFFFAOYSA-N 0.000 claims description 13
• 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 13
• 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 13
• FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims description 12
• 229960001915 hexamidine Drugs 0.000 claims description 12
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 11
• 238000009434 installation Methods 0.000 claims description 11
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 10
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 10
• 238000006467 substitution reaction Methods 0.000 claims description 10
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 9
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 9
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 9
• 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 9
• UKWJATKQEKITFM-UHFFFAOYSA-N 1-methyl-4-piperidin-4-ylpiperidine Chemical compound C1CN(C)CCC1C1CCNCC1 UKWJATKQEKITFM-UHFFFAOYSA-N 0.000 claims description 8
• 101100181929 Caenorhabditis elegans lin-3 gene Proteins 0.000 claims description 8
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 8
• DZGWFCGJZKJUFP-UHFFFAOYSA-N Tyramine Natural products NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 claims description 8
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 8
• 150000007857 hydrazones Chemical class 0.000 claims description 8
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 8
• 125000001624 naphthyl group Chemical group 0.000 claims description 8
• 238000012856 packing Methods 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 7
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 7
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
• 125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 7
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 7
• 229920002770 condensed tannin Polymers 0.000 claims description 7
• 235000018192 pine bark supplement Nutrition 0.000 claims description 7
• 229940106796 pycnogenol Drugs 0.000 claims description 7
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
• 108010078311 Calcitonin Gene-Related Peptide Receptors Proteins 0.000 claims description 6
• 239000005018 casein Substances 0.000 claims description 6
• 201000010099 disease Diseases 0.000 claims description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
• XRRDFIPYLFCYLU-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical group [CH2]C1=CC(C)=CC(C)=C1 XRRDFIPYLFCYLU-UHFFFAOYSA-N 0.000 claims description 5
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 5
• 102000008323 calcitonin gene-related peptide receptor activity proteins Human genes 0.000 claims description 5
• 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 5
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 5
• 239000010948 rhodium Substances 0.000 claims description 5
• 239000002689 soil Chemical group 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 4
• QFDISQIDKZUABE-UHFFFAOYSA-N 1,1'-bipiperidine Chemical compound C1CCCCN1N1CCCCC1 QFDISQIDKZUABE-UHFFFAOYSA-N 0.000 claims description 4
• FNRMMDCDHWCQTH-UHFFFAOYSA-N 2-chloropyridine;3-chloropyridine;4-chloropyridine Chemical compound ClC1=CC=NC=C1.ClC1=CC=CN=C1.ClC1=CC=CC=N1 FNRMMDCDHWCQTH-UHFFFAOYSA-N 0.000 claims description 4
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 4
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 4
• MTPBUCCXRGSDCR-UHFFFAOYSA-N 4-piperidin-1-ylpyridine Chemical compound C1CCCCN1C1=CC=NC=C1 MTPBUCCXRGSDCR-UHFFFAOYSA-N 0.000 claims description 4
• 206010019233 Headaches Diseases 0.000 claims description 4
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 4
• ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 4
• 239000003795 chemical substances by application Substances 0.000 claims description 4
• 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 4
• 231100000869 headache Toxicity 0.000 claims description 4
• 239000010985 leather Substances 0.000 claims description 4
• 229960005181 morphine Drugs 0.000 claims description 4
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
• 125000006308 propyl amino group Chemical group 0.000 claims description 4
• 125000001725 pyrenyl group Chemical group 0.000 claims description 4
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
• 229910052703 rhodium Inorganic materials 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims description 3
• SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims description 3
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
• 230000033228 biological regulation Effects 0.000 claims description 3
• 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
• 238000011068 loading method Methods 0.000 claims description 3
• 125000002971 oxazolyl group Chemical group 0.000 claims description 3
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
• 230000036961 partial effect Effects 0.000 claims description 3
• 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 description 3
• 230000003449 preventive effect Effects 0.000 claims description 3
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 3
• RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 claims description 3
• 125000003944 tolyl group Chemical group 0.000 claims description 3
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 3
• 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
• 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 2
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
• 241000283074 Equus asinus Species 0.000 claims description 2
• YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 2
• 206010039085 Rhinitis allergic Diseases 0.000 claims description 2
• 206010040047 Sepsis Diseases 0.000 claims description 2
• 229920002472 Starch Polymers 0.000 claims description 2
• 201000010105 allergic rhinitis Diseases 0.000 claims description 2
• 125000000539 amino acid group Chemical group 0.000 claims description 2
• 208000006673 asthma Diseases 0.000 claims description 2
• 238000007664 blowing Methods 0.000 claims description 2
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 2
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000003963 dichloro group Chemical group Cl* 0.000 claims description 2
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
• 210000004209 hair Anatomy 0.000 claims description 2
• 239000004312 hexamethylene tetramine Substances 0.000 claims description 2
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• 125000001041 indolyl group Chemical group 0.000 claims description 2
• 208000027866 inflammatory disease Diseases 0.000 claims description 2
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
• BGPNDOBOLHJJEE-UHFFFAOYSA-N n-(2-aminophenyl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC=C1N BGPNDOBOLHJJEE-UHFFFAOYSA-N 0.000 claims description 2
• TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 230000002829 reductive effect Effects 0.000 claims description 2
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• 208000017520 skin disease Diseases 0.000 claims description 2
• 239000008107 starch Substances 0.000 claims description 2
• 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000005289 uranyl group Chemical group 0.000 claims description 2
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