UA77265C2 - Pyrrolopyrimidine or pyrrolopyridine derivative substituted with a cyclic amino group - Google Patents

Info

Publication number

UA77265C2

UA77265C2 UA20040907464A UA20040907464A UA77265C2 UA 77265 C2 UA77265 C2 UA 77265C2 UA 20040907464 A UA20040907464 A UA 20040907464A UA 20040907464 A UA20040907464 A UA 20040907464A UA 77265 C2 UA77265 C2 UA 77265C2

Authority

UA

Ukraine

Prior art keywords

pyrrolo

alkyl

piperidin

dimethyl

hydrogen

Prior art date

2002-12-26

Links

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• Global Dossier
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• 125000003277 amino group Chemical group 0.000 title claims abstract description 126
• 125000004122 cyclic group Chemical group 0.000 title claims abstract description 126
• XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical group C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 title claims abstract description 19
• KDOPAZIWBAHVJB-UHFFFAOYSA-N 5h-pyrrolo[3,2-d]pyrimidine Chemical group C1=NC=C2NC=CC2=N1 KDOPAZIWBAHVJB-UHFFFAOYSA-N 0.000 title claims abstract description 7
• 239000005557 antagonist Substances 0.000 claims abstract description 4
• WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 695
• -1 saturated cyclic amine Chemical class 0.000 claims description 407
• 229910052739 hydrogen Inorganic materials 0.000 claims description 328
• 239000001257 hydrogen Substances 0.000 claims description 292
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 265
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 140
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 138
• 150000001875 compounds Chemical class 0.000 claims description 114
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 113
• 239000000203 mixture Substances 0.000 claims description 90
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 80
• 125000001424 substituent group Chemical group 0.000 claims description 73
• 229910052736 halogen Inorganic materials 0.000 claims description 71
• 150000002367 halogens Chemical class 0.000 claims description 71
• 125000000217 alkyl group Chemical group 0.000 claims description 63
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 62
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 62
• 150000003839 salts Chemical class 0.000 claims description 52
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 52
• 150000002431 hydrogen Chemical class 0.000 claims description 45
• 150000004677 hydrates Chemical class 0.000 claims description 39
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 37
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 35
• 125000004432 carbon atom Chemical group C* 0.000 claims description 32
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
• 125000004076 pyridyl group Chemical group 0.000 claims description 25
• 239000000460 chlorine Substances 0.000 claims description 23
• 125000001072 heteroaryl group Chemical group 0.000 claims description 23
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 22
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
• 229910052794 bromium Inorganic materials 0.000 claims description 22
• 229910052801 chlorine Inorganic materials 0.000 claims description 22
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
• 125000003118 aryl group Chemical group 0.000 claims description 20
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 12
• 239000002253 acid Substances 0.000 claims description 12
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 11
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
• 125000004429 atom Chemical group 0.000 claims description 9
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
• CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
• 150000001412 amines Chemical class 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
• 125000002252 acyl group Chemical group 0.000 claims description 6
• 150000004944 pyrrolopyrimidines Chemical class 0.000 claims description 6
• 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
• 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 5
• GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 4
• GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 4
• 230000009471 action Effects 0.000 claims description 4
• BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 4
• SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 4
• 229910052717 sulfur Inorganic materials 0.000 claims description 4
• MYLBTCQBKAKUTJ-UHFFFAOYSA-N 7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine Chemical compound C1=CN=CC2=C(SC)C(C)=C(SC)N21 MYLBTCQBKAKUTJ-UHFFFAOYSA-N 0.000 claims description 3
• HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
• RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 claims description 3
• SMHORIXQSMDYEY-UHFFFAOYSA-N 2-ethylheptanenitrile Chemical compound CCCCCC(CC)C#N SMHORIXQSMDYEY-UHFFFAOYSA-N 0.000 claims description 2
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
• MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 2
• 229910052731 fluorine Inorganic materials 0.000 claims description 2
• 239000002464 receptor antagonist Substances 0.000 claims description 2
• 229940044551 receptor antagonist Drugs 0.000 claims description 2
• 229960004756 ethanol Drugs 0.000 claims 43
• KCTZOTUQSGYWLV-UHFFFAOYSA-N N1C=NC=C2N=CC=C21 Chemical group N1C=NC=C2N=CC=C21 KCTZOTUQSGYWLV-UHFFFAOYSA-N 0.000 claims 17
• 150000005255 pyrrolopyridines Chemical class 0.000 claims 11
• 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 2
• 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
• 241001404126 Gyas Species 0.000 claims 1
• 239000013543 active substance Substances 0.000 claims 1
• 229910052799 carbon Inorganic materials 0.000 claims 1
• 238000004651 near-field scanning optical microscopy Methods 0.000 claims 1
• 229910052698 phosphorus Inorganic materials 0.000 claims 1
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
• 238000012876 topography Methods 0.000 claims 1
• 201000010099 disease Diseases 0.000 abstract description 16
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 16
• 102100021752 Corticoliberin Human genes 0.000 abstract description 14
• 206010008118 cerebral infarction Diseases 0.000 abstract description 10
• 208000019901 Anxiety disease Diseases 0.000 abstract description 6
• 208000024827 Alzheimer disease Diseases 0.000 abstract description 5
• 201000006474 Brain Ischemia Diseases 0.000 abstract description 5
• 206010048962 Brain oedema Diseases 0.000 abstract description 5
• 206010008120 Cerebral ischaemia Diseases 0.000 abstract description 5
• 208000030814 Eating disease Diseases 0.000 abstract description 5
• 208000019454 Feeding and Eating disease Diseases 0.000 abstract description 5
• 208000023105 Huntington disease Diseases 0.000 abstract description 5
• 206010020772 Hypertension Diseases 0.000 abstract description 5
• 206010061218 Inflammation Diseases 0.000 abstract description 5
• 208000018737 Parkinson disease Diseases 0.000 abstract description 5
• 208000027418 Wounds and injury Diseases 0.000 abstract description 5
• 230000036506 anxiety Effects 0.000 abstract description 5
• 208000006752 brain edema Diseases 0.000 abstract description 5
• 208000026106 cerebrovascular disease Diseases 0.000 abstract description 5
• 235000014632 disordered eating Nutrition 0.000 abstract description 5
• 206010013663 drug dependence Diseases 0.000 abstract description 5
• 206010015037 epilepsy Diseases 0.000 abstract description 5
• 230000004054 inflammatory process Effects 0.000 abstract description 5
• 208000018556 stomach disease Diseases 0.000 abstract description 5
• 208000011117 substance-related disease Diseases 0.000 abstract description 5
• 201000004384 Alopecia Diseases 0.000 abstract description 4
• 108010056643 Corticotropin-Releasing Hormone Receptors Proteins 0.000 abstract description 4
• 201000004624 Dermatitis Diseases 0.000 abstract description 4
• 231100000360 alopecia Toxicity 0.000 abstract description 4
• 208000002551 irritable bowel syndrome Diseases 0.000 abstract description 4
• 201000000980 schizophrenia Diseases 0.000 abstract description 4
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• 239000003795 chemical substances by application Substances 0.000 abstract description 3
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• 206010052428 Wound Diseases 0.000 abstract description 2
• 230000001225 therapeutic effect Effects 0.000 abstract description 2
• 230000036039 immunity Effects 0.000 abstract 1
• 239000012071 phase Substances 0.000 description 380
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 184
• 230000014759 maintenance of location Effects 0.000 description 158
• 238000004128 high performance liquid chromatography Methods 0.000 description 153
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 134
• 239000005695 Ammonium acetate Substances 0.000 description 134
• 235000019257 ammonium acetate Nutrition 0.000 description 134
• 229940043376 ammonium acetate Drugs 0.000 description 134
• 239000007864 aqueous solution Substances 0.000 description 122
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 121
• VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 85
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 74
• 239000002904 solvent Substances 0.000 description 69
• 229960000583 acetic acid Drugs 0.000 description 62
• 235000011054 acetic acid Nutrition 0.000 description 61
• 229910021529 ammonia Inorganic materials 0.000 description 59
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 42
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
• 239000012442 inert solvent Substances 0.000 description 33
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 32
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 31
• 239000000243 solution Substances 0.000 description 30
• LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 28
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 23
• 239000002244 precipitate Substances 0.000 description 23
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 21
• 206010028980 Neoplasm Diseases 0.000 description 19
• 201000011510 cancer Diseases 0.000 description 19
• 150000001408 amides Chemical class 0.000 description 18
• 239000000741 silica gel Substances 0.000 description 18
• 229910002027 silica gel Inorganic materials 0.000 description 18
• 239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 17
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
• 229910052740 iodine Inorganic materials 0.000 description 17
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 16
• 229910052751 metal Inorganic materials 0.000 description 16
• 239000002184 metal Substances 0.000 description 16
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
• 101000957708 Catostomus commersonii Corticoliberin-2 Proteins 0.000 description 13
• 230000015572 biosynthetic process Effects 0.000 description 13
• 238000001816 cooling Methods 0.000 description 13
• 239000011541 reaction mixture Substances 0.000 description 13
• 239000003480 eluent Substances 0.000 description 12
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
• 150000002170 ethers Chemical class 0.000 description 11
• 239000000706 filtrate Substances 0.000 description 11
• 229930195733 hydrocarbon Natural products 0.000 description 11
• 150000002430 hydrocarbons Chemical class 0.000 description 11
• 229910052757 nitrogen Inorganic materials 0.000 description 11
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
• 238000006243 chemical reaction Methods 0.000 description 10
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• 238000003786 synthesis reaction Methods 0.000 description 10
• 150000001298 alcohols Chemical class 0.000 description 9
• 238000010992 reflux Methods 0.000 description 9
• 239000007787 solid Substances 0.000 description 9
• 239000000725 suspension Substances 0.000 description 9
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 8
• 239000012267 brine Substances 0.000 description 8
• 150000007529 inorganic bases Chemical class 0.000 description 8
• 238000000034 method Methods 0.000 description 8
• 235000011118 potassium hydroxide Nutrition 0.000 description 8
• 230000007958 sleep Effects 0.000 description 8
• 235000011121 sodium hydroxide Nutrition 0.000 description 8
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
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• 229910001863 barium hydroxide Inorganic materials 0.000 description 7
• 238000004440 column chromatography Methods 0.000 description 7
• NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 7
• 238000002844 melting Methods 0.000 description 7
• 230000008018 melting Effects 0.000 description 7
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• 229910000027 potassium carbonate Inorganic materials 0.000 description 7
• 235000011181 potassium carbonates Nutrition 0.000 description 7
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 7
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
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• 239000012312 sodium hydride Substances 0.000 description 7
• 229910000104 sodium hydride Inorganic materials 0.000 description 7
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• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
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• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 6
• 230000035939 shock Effects 0.000 description 6
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• CONWVZWHEGJGII-UHFFFAOYSA-N C(C1=CC(C(=O)O)=CC=C1)(=O)O.CCCCCC Chemical compound C(C1=CC(C(=O)O)=CC=C1)(=O)O.CCCCCC CONWVZWHEGJGII-UHFFFAOYSA-N 0.000 description 4
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