SK4182002A3 - Compounds for the treatment of ischemia - Google Patents

Info

Publication number

SK4182002A3

SK4182002A3 SK418-2002A SK4182002A SK4182002A3 SK 4182002 A3 SK4182002 A3 SK 4182002A3 SK 4182002 A SK4182002 A SK 4182002A SK 4182002 A3 SK4182002 A3 SK 4182002A3

Authority

SK

Slovakia

Prior art keywords

alkyl

carbon atoms

compounds

guanidine

pyrazole

Prior art date

1999-09-30

Links

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• 208000028867 ischemia Diseases 0.000 title claims abstract description 30
• 150000001875 compounds Chemical class 0.000 title claims description 394
• 238000000034 method Methods 0.000 claims abstract description 207
• 206010021143 Hypoxia Diseases 0.000 claims abstract description 32
• 230000000451 tissue damage Effects 0.000 claims abstract description 26
• 231100000827 tissue damage Toxicity 0.000 claims abstract description 26
• 230000007954 hypoxia Effects 0.000 claims abstract description 17
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
• -1 oxy, methylene Chemical group 0.000 claims description 400
• 125000004432 carbon atom Chemical group C* 0.000 claims description 193
• 125000000217 alkyl group Chemical group 0.000 claims description 172
• 229910052757 nitrogen Inorganic materials 0.000 claims description 160
• 150000003839 salts Chemical class 0.000 claims description 113
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 88
• 229910052739 hydrogen Inorganic materials 0.000 claims description 86
• 239000001257 hydrogen Substances 0.000 claims description 86
• 229920006395 saturated elastomer Polymers 0.000 claims description 86
• 239000000203 mixture Substances 0.000 claims description 75
• 229940002612 prodrug Drugs 0.000 claims description 69
• 239000000651 prodrug Substances 0.000 claims description 69
• 125000003545 alkoxy group Chemical group 0.000 claims description 67
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 61
• 229910052760 oxygen Inorganic materials 0.000 claims description 61
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 60
• 239000001301 oxygen Substances 0.000 claims description 60
• 229910052736 halogen Inorganic materials 0.000 claims description 59
• 150000002367 halogens Chemical class 0.000 claims description 56
• ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 54
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 51
• 229910052717 sulfur Inorganic materials 0.000 claims description 51
• 239000011593 sulfur Chemical group 0.000 claims description 51
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 50
• 125000005842 heteroatom Chemical group 0.000 claims description 48
• 239000003112 inhibitor Substances 0.000 claims description 46
• 125000001424 substituent group Chemical group 0.000 claims description 46
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 44
• 150000002431 hydrogen Chemical class 0.000 claims description 44
• 210000001519 tissue Anatomy 0.000 claims description 43
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 38
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
• 241000124008 Mammalia Species 0.000 claims description 33
• 210000002216 heart Anatomy 0.000 claims description 33
• 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 description 32
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 29
• 239000000460 chlorine Substances 0.000 claims description 28
• CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 27
• SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 27
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
• OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 25
• 229910052801 chlorine Inorganic materials 0.000 claims description 23
• 125000002541 furyl group Chemical group 0.000 claims description 23
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 22
• 239000002552 dosage form Substances 0.000 claims description 22
• 125000005699 methyleneoxy group Chemical group [H]C([H])([*:1])O[*:2] 0.000 claims description 22
• 125000002619 bicyclic group Chemical group 0.000 claims description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 125000004545 purin-9-yl group Chemical group N1=CN=C2N(C=NC2=C1)* 0.000 claims description 21
• 125000002757 morpholinyl group Chemical group 0.000 claims description 20
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 20
• 125000003386 piperidinyl group Chemical group 0.000 claims description 20
• 238000001356 surgical procedure Methods 0.000 claims description 20
• 239000003937 drug carrier Substances 0.000 claims description 19
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
• 239000003795 chemical substances by application Substances 0.000 claims description 18
• 125000000335 thiazolyl group Chemical group 0.000 claims description 18
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 17
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 17
• WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 16
• 125000004043 oxo group Chemical group O=* 0.000 claims description 16
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 15
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 15
• 239000003085 diluting agent Substances 0.000 claims description 15
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 15
• 239000003981 vehicle Substances 0.000 claims description 15
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 15
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 14
• 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 14
• 229960005305 adenosine Drugs 0.000 claims description 14
• 239000002327 cardiovascular agent Substances 0.000 claims description 14
• 229940125692 cardiovascular agent Drugs 0.000 claims description 14
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 14
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 14
• 125000002971 oxazolyl group Chemical group 0.000 claims description 14
• 125000004193 piperazinyl group Chemical group 0.000 claims description 14
• 230000001225 therapeutic effect Effects 0.000 claims description 13
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 12
• 239000012190 activator Substances 0.000 claims description 12
• 125000001153 fluoro group Chemical group F* 0.000 claims description 12
• 210000004185 liver Anatomy 0.000 claims description 12
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 12
• 210000004556 brain Anatomy 0.000 claims description 11
• 125000001786 isothiazolyl group Chemical group 0.000 claims description 11
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
• 239000011734 sodium Substances 0.000 claims description 11
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
• 102100030980 Sodium/hydrogen exchanger 1 Human genes 0.000 claims description 10
• 108010093115 growth factor-activatable Na-H exchanger NHE-1 Proteins 0.000 claims description 10
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 10
• 125000001544 thienyl group Chemical group 0.000 claims description 10
• 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 9
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 8
• 239000001103 potassium chloride Substances 0.000 claims description 8
• 235000011164 potassium chloride Nutrition 0.000 claims description 8
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 8
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 7
• 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 7
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
• 125000002393 azetidinyl group Chemical group 0.000 claims description 7
• 239000003379 purinergic P1 receptor agonist Substances 0.000 claims description 7
• 125000004149 thio group Chemical group *S* 0.000 claims description 7
• 229940043355 kinase inhibitor Drugs 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
• 239000011575 calcium Substances 0.000 claims description 5
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 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 5
• 239000003909 protein kinase inhibitor Substances 0.000 claims description 5
• 230000002537 thrombolytic effect Effects 0.000 claims description 5
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 4
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 4
• 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 4
• 239000005541 ACE inhibitor Substances 0.000 claims description 4
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 4
• 229940123208 Biguanide Drugs 0.000 claims description 4
• 229940127291 Calcium channel antagonist Drugs 0.000 claims description 4
• 229910002651 NO3 Inorganic materials 0.000 claims description 4
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 4
• 102000012751 Pyruvate Dehydrogenase Complex Human genes 0.000 claims description 4
• 108010090051 Pyruvate Dehydrogenase Complex Proteins 0.000 claims description 4
• 229960001138 acetylsalicylic acid Drugs 0.000 claims description 4
• 125000004414 alkyl thio group Chemical group 0.000 claims description 4
• 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 claims description 4
• 239000005557 antagonist Substances 0.000 claims description 4
• 125000005605 benzo group Chemical group 0.000 claims description 4
• 239000002876 beta blocker Substances 0.000 claims description 4
• 229940097320 beta blocking agent Drugs 0.000 claims description 4
• 239000000480 calcium channel blocker Substances 0.000 claims description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 239000002934 diuretic Substances 0.000 claims description 4
• 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 claims description 4
• 229930182470 glycoside Natural products 0.000 claims description 4
• 150000002338 glycosides Chemical class 0.000 claims description 4
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
• 210000000936 intestine Anatomy 0.000 claims description 4
• 210000003734 kidney Anatomy 0.000 claims description 4
• 210000004072 lung Anatomy 0.000 claims description 4
• XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 4
• 229960003105 metformin Drugs 0.000 claims description 4
• 230000003647 oxidation Effects 0.000 claims description 4
• 238000007254 oxidation reaction Methods 0.000 claims description 4
• 230000036961 partial effect Effects 0.000 claims description 4
• 239000008024 pharmaceutical diluent Substances 0.000 claims description 4
• IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 claims description 4
• 229960001289 prazosin Drugs 0.000 claims description 4
• 125000005493 quinolyl group Chemical group 0.000 claims description 4
• 210000001525 retina Anatomy 0.000 claims description 4
• 210000002027 skeletal muscle Anatomy 0.000 claims description 4
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 3
• JVGJINYQXKIBDT-UHFFFAOYSA-N 1-(2-bromophenyl)-5-cyclopropyl-n-(diaminomethylidene)pyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C(=CC=CC=2)Br)C=1C1CC1 JVGJINYQXKIBDT-UHFFFAOYSA-N 0.000 claims description 3
• DZXZXYVVTHIODU-UHFFFAOYSA-N 1-(2-chloro-5-methoxyphenyl)-5-cyclopropyl-n-(diaminomethylidene)pyrazole-4-carboxamide Chemical compound COC1=CC=C(Cl)C(N2C(=C(C(=O)NC(N)=N)C=N2)C2CC2)=C1 DZXZXYVVTHIODU-UHFFFAOYSA-N 0.000 claims description 3
• KTMBRLHJWLVWJN-UHFFFAOYSA-N 1-(2-chloro-5-methylsulfonylphenyl)-5-cyclopropyl-n-(diaminomethylidene)pyrazole-4-carboxamide Chemical compound CS(=O)(=O)C1=CC=C(Cl)C(N2C(=C(C(=O)NC(N)=N)C=N2)C2CC2)=C1 KTMBRLHJWLVWJN-UHFFFAOYSA-N 0.000 claims description 3
• BINSRSZWKJTYQD-UHFFFAOYSA-N 1-(2-chloro-5-sulfamoylphenyl)-5-cyclopropyl-n-(diaminomethylidene)pyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C(=CC=C(C=2)S(N)(=O)=O)Cl)C=1C1CC1 BINSRSZWKJTYQD-UHFFFAOYSA-N 0.000 claims description 3
• OBARLXYWADULRB-UHFFFAOYSA-N 1-(2-chlorophenyl)-5-cyclopropyl-n-(diaminomethylidene)pyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C(=CC=CC=2)Cl)C=1C1CC1 OBARLXYWADULRB-UHFFFAOYSA-N 0.000 claims description 3
• PJRZFTYVWGASFT-UHFFFAOYSA-N 1-(3h-benzimidazol-5-yl)-n-(diaminomethylidene)-5-ethylpyrazole-4-carboxamide Chemical compound CCC1=C(C(=O)NC(N)=N)C=NN1C1=CC=C(N=CN2)C2=C1 PJRZFTYVWGASFT-UHFFFAOYSA-N 0.000 claims description 3
• XRJAKWJGDAHTMH-UHFFFAOYSA-N 1-(5-carbamoyl-2-chlorophenyl)-5-cyclopropyl-n-(diaminomethylidene)pyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C(=CC=C(C=2)C(N)=O)Cl)C=1C1CC1 XRJAKWJGDAHTMH-UHFFFAOYSA-N 0.000 claims description 3
• HQMDTNPGJUCYMV-UHFFFAOYSA-N 1-[2-chloro-4-(methylsulfamoyl)phenyl]-5-cyclopropyl-n-(diaminomethylidene)pyrazole-4-carboxamide Chemical compound ClC1=CC(S(=O)(=O)NC)=CC=C1N1C(C2CC2)=C(C(=O)NC(N)=N)C=N1 HQMDTNPGJUCYMV-UHFFFAOYSA-N 0.000 claims description 3
• QDEGSGKUDYTYJV-UHFFFAOYSA-N 1-[4-chloro-2-(trifluoromethyl)phenyl]-5-cyclopropyl-n-(diaminomethylidene)pyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C(=CC(Cl)=CC=2)C(F)(F)F)C=1C1CC1 QDEGSGKUDYTYJV-UHFFFAOYSA-N 0.000 claims description 3
• ZWKXLNHOSNQZLS-UHFFFAOYSA-N 5-cyclopropyl-n-(diaminomethylidene)-1-(1h-indazol-7-yl)pyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C=3NN=CC=3C=CC=2)C=1C1CC1 ZWKXLNHOSNQZLS-UHFFFAOYSA-N 0.000 claims description 3
• LGOPZILIFLMNPA-UHFFFAOYSA-N 5-cyclopropyl-n-(diaminomethylidene)-1-(2,3-dichlorophenyl)pyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C(=C(Cl)C=CC=2)Cl)C=1C1CC1 LGOPZILIFLMNPA-UHFFFAOYSA-N 0.000 claims description 3
• NVPIIEFYJSAEED-UHFFFAOYSA-N 5-cyclopropyl-n-(diaminomethylidene)-1-(2,5-dichlorophenyl)pyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C(=CC=C(Cl)C=2)Cl)C=1C1CC1 NVPIIEFYJSAEED-UHFFFAOYSA-N 0.000 claims description 3
• PTVBGVLITQPZTD-UHFFFAOYSA-N 5-cyclopropyl-n-(diaminomethylidene)-1-(2,6-dichlorophenyl)pyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C(=CC=CC=2Cl)Cl)C=1C1CC1 PTVBGVLITQPZTD-UHFFFAOYSA-N 0.000 claims description 3
• HMCQXPJNWHQROJ-UHFFFAOYSA-N 5-cyclopropyl-n-(diaminomethylidene)-1-(2-fluorophenyl)pyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C(=CC=CC=2)F)C=1C1CC1 HMCQXPJNWHQROJ-UHFFFAOYSA-N 0.000 claims description 3
• SSQWWXQZCXSTHE-UHFFFAOYSA-N 5-cyclopropyl-n-(diaminomethylidene)-1-[2-fluoro-6-(trifluoromethyl)phenyl]pyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C(=CC=CC=2F)C(F)(F)F)C=1C1CC1 SSQWWXQZCXSTHE-UHFFFAOYSA-N 0.000 claims description 3
• DJEYTYIFAGYQSJ-UHFFFAOYSA-N 5-cyclopropyl-n-(diaminomethylidene)-1-[4-fluoro-2-(trifluoromethyl)phenyl]pyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C(=CC(F)=CC=2)C(F)(F)F)C=1C1CC1 DJEYTYIFAGYQSJ-UHFFFAOYSA-N 0.000 claims description 3
• YZLNQKMWEXOAPY-UHFFFAOYSA-N 5-cyclopropyl-n-(diaminomethylidene)-1-phenylpyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C=CC=CC=2)C=1C1CC1 YZLNQKMWEXOAPY-UHFFFAOYSA-N 0.000 claims description 3
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• GDXBRVCQGGKXJY-UHFFFAOYSA-N 5-cyclopropyl-n-(diaminomethylidene)-1-quinolin-5-ylpyrazole-4-carboxamide Chemical compound NC(N)=NC(=O)C=1C=NN(C=2C3=CC=CN=C3C=CC=2)C=1C1CC1 GDXBRVCQGGKXJY-UHFFFAOYSA-N 0.000 claims description 3
• LFOAPSAWYUILCY-UHFFFAOYSA-N 5-cyclopropyl-n-(diaminomethylidene)-1-quinolin-8-ylpyrazole-4-carboxamide Chemical compound NC(=N)NC(=O)C=1C=NN(C=2C3=NC=CC=C3C=CC=2)C=1C1CC1 LFOAPSAWYUILCY-UHFFFAOYSA-N 0.000 claims description 3
• AEOBEOJCBAYXBA-UHFFFAOYSA-N A2P5P Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1OP(O)(O)=O AEOBEOJCBAYXBA-UHFFFAOYSA-N 0.000 claims description 3
• 102000000452 Acetyl-CoA carboxylase Human genes 0.000 claims description 3
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• 101000914947 Bungarus multicinctus Long neurotoxin homolog TA-bm16 Proteins 0.000 claims description 3
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• 102000003923 Protein Kinase C Human genes 0.000 claims description 3
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• 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
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• 150000004665 fatty acids Chemical class 0.000 claims description 3
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• DPPAQYSYEWTCPT-UHFFFAOYSA-N n-(diaminomethylidene)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)-5-ethylpyrazole-4-carboxamide Chemical compound CCC1=C(C(=O)NC(N)=N)C=NN1C1=CC=C(OCCO2)C2=C1 DPPAQYSYEWTCPT-UHFFFAOYSA-N 0.000 claims description 3
• USEQIAAJQHCEER-UHFFFAOYSA-N n-(diaminomethylidene)-5-methyl-1-[2-(trifluoromethyl)phenyl]pyrazole-4-carboxamide Chemical compound CC1=C(C(=O)NC(N)=N)C=NN1C1=CC=CC=C1C(F)(F)F USEQIAAJQHCEER-UHFFFAOYSA-N 0.000 claims description 3
• 239000002777 nucleoside Substances 0.000 claims description 3
• 210000000496 pancreas Anatomy 0.000 claims description 3
• 210000001032 spinal nerve Anatomy 0.000 claims description 3
• 210000000952 spleen Anatomy 0.000 claims description 3
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• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
• ZJQFENWMXOATQM-UHFFFAOYSA-N 1-(2-chloro-4-methylsulfonylphenyl)-5-cyclopropyl-n-(diaminomethylidene)pyrazole-4-carboxamide Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1N1C(C2CC2)=C(C(=O)NC(N)=N)C=N1 ZJQFENWMXOATQM-UHFFFAOYSA-N 0.000 claims description 2
• FQKVIFIBQBRQEY-UHFFFAOYSA-N 1-(2h-benzotriazol-5-yl)-n-(diaminomethylidene)-5-ethylpyrazole-4-carboxamide Chemical compound CCC1=C(C(=O)NC(N)=N)C=NN1C1=CC=C(NN=N2)C2=C1 FQKVIFIBQBRQEY-UHFFFAOYSA-N 0.000 claims description 2
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