SK6252000A3 - Indazole bioisostere replacement of catechol in therapeutically active compounds - Google Patents

Indazole bioisostere replacement of catechol in therapeutically active compounds Download PDF

Info

Publication number: SK6252000A3
Authority: SK; Slovakia
Prior art keywords: group; alkyl; carbon atoms; consisting essentially; independently selected
Prior art date: 1997-11-04

Application number

SK625-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Anthony Marfat

Original Assignee

Pfizer Prod Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-11-04

Filing date

1998-10-26

Publication date

2001-11-06

1998-10-26 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2001-11-06 Publication of SK6252000A3 publication Critical patent/SK6252000A3/sk

Links

YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 title claims abstract description 261
150000001875 compounds Chemical class 0.000 title claims abstract description 246
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title claims abstract description 108
239000001257 hydrogen Substances 0.000 claims abstract description 297
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 297
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 263
150000003839 salts Chemical class 0.000 claims abstract description 60
230000000694 effects Effects 0.000 claims abstract description 51
230000001225 therapeutic effect Effects 0.000 claims abstract description 32
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 25
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 abstract description 21
239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims abstract description 14
230000000118 anti-neoplastic effect Effects 0.000 claims abstract description 11
239000000951 adrenergic alpha-1 receptor antagonist Substances 0.000 claims abstract description 7
108090000312 Calcium Channels Proteins 0.000 claims abstract description 6
102000003922 Calcium Channels Human genes 0.000 claims abstract description 6
239000000203 mixture Substances 0.000 claims abstract description 6
239000000785 adrenergic beta-1 receptor agonist Substances 0.000 claims abstract description 3
-1 heterocyclyl radical Chemical class 0.000 claims description 569
125000004432 carbon atom Chemical group C* 0.000 claims description 410
125000000217 alkyl group Chemical group 0.000 claims description 270
125000001424 substituent group Chemical group 0.000 claims description 157
230000036961 partial effect Effects 0.000 claims description 138
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 131
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 100
239000000460 chlorine Substances 0.000 claims description 91
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 81
229910052801 chlorine Inorganic materials 0.000 claims description 81
229910052731 fluorine Inorganic materials 0.000 claims description 71
239000011737 fluorine Substances 0.000 claims description 70
125000003118 aryl group Chemical group 0.000 claims description 68
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 64
229910052794 bromium Inorganic materials 0.000 claims description 64
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 60
229910052799 carbon Inorganic materials 0.000 claims description 59
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 57
238000011282 treatment Methods 0.000 claims description 57
125000000623 heterocyclic group Chemical group 0.000 claims description 52
125000003545 alkoxy group Chemical group 0.000 claims description 51
125000003342 alkenyl group Chemical group 0.000 claims description 43
229910052757 nitrogen Inorganic materials 0.000 claims description 42
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 41
229910052760 oxygen Inorganic materials 0.000 claims description 40
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 38
125000004093 cyano group Chemical group *C#N 0.000 claims description 37
201000010099 disease Diseases 0.000 claims description 34
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 34
229910052717 sulfur Inorganic materials 0.000 claims description 34
125000000753 cycloalkyl group Chemical group 0.000 claims description 32
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 32
125000001153 fluoro group Chemical group F* 0.000 claims description 30
125000005842 heteroatom Chemical group 0.000 claims description 30
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 29
125000004076 pyridyl group Chemical group 0.000 claims description 29
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
125000004429 atom Chemical group 0.000 claims description 28
239000003795 chemical substances by application Substances 0.000 claims description 28
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 27
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 27
229910005965 SO 2 Inorganic materials 0.000 claims description 25
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
239000001301 oxygen Chemical group 0.000 claims description 24
125000001931 aliphatic group Chemical group 0.000 claims description 23
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 23
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 21
125000001246 bromo group Chemical group Br* 0.000 claims description 21
150000001721 carbon Chemical group 0.000 claims description 21
125000002541 furyl group Chemical group 0.000 claims description 21
150000002431 hydrogen Chemical class 0.000 claims description 21
102000005962 receptors Human genes 0.000 claims description 21
108020003175 receptors Proteins 0.000 claims description 21
239000000556 agonist Substances 0.000 claims description 20
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
125000001309 chloro group Chemical group Cl* 0.000 claims description 20
125000001544 thienyl group Chemical group 0.000 claims description 20
229940127291 Calcium channel antagonist Drugs 0.000 claims description 19
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 19
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
125000003831 tetrazolyl group Chemical group 0.000 claims description 18
125000000335 thiazolyl group Chemical group 0.000 claims description 18
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 17
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 17
125000001425 triazolyl group Chemical group 0.000 claims description 17
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 16
239000000544 cholinesterase inhibitor Substances 0.000 claims description 16
125000000714 pyrimidinyl group Chemical group 0.000 claims description 16
239000004480 active ingredient Substances 0.000 claims description 15
208000006673 asthma Diseases 0.000 claims description 15
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
125000002971 oxazolyl group Chemical group 0.000 claims description 15
125000003884 phenylalkyl group Chemical group 0.000 claims description 15
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 15
238000000034 method Methods 0.000 claims description 14
125000003226 pyrazolyl group Chemical group 0.000 claims description 14
238000006467 substitution reaction Methods 0.000 claims description 14
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 13
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
239000003112 inhibitor Substances 0.000 claims description 13
125000000160 oxazolidinyl group Chemical group 0.000 claims description 13
239000011593 sulfur Chemical group 0.000 claims description 13
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 12
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 12
101150065749 Churc1 gene Proteins 0.000 claims description 12
102100038239 Protein Churchill Human genes 0.000 claims description 12
125000006545 (C1-C9) alkyl group Chemical group 0.000 claims description 11
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 11
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
230000001965 increasing effect Effects 0.000 claims description 11
208000027866 inflammatory disease Diseases 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
125000001984 thiazolidinyl group Chemical group 0.000 claims description 11
WQADWIOXOXRPLN-UHFFFAOYSA-N 1,3-dithiane Chemical compound C1CSCSC1 WQADWIOXOXRPLN-UHFFFAOYSA-N 0.000 claims description 10
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 10
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
125000001589 carboacyl group Chemical group 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 10
125000001624 naphthyl group Chemical group 0.000 claims description 10
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
125000001113 thiadiazolyl group Chemical group 0.000 claims description 10
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 10
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 9
125000004414 alkyl thio group Chemical group 0.000 claims description 9
125000005530 alkylenedioxy group Chemical group 0.000 claims description 9
239000002131 composite material Substances 0.000 claims description 9
125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
125000001072 heteroaryl group Chemical group 0.000 claims description 9
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 9
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
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 9
125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 9
125000005493 quinolyl group Chemical group 0.000 claims description 9
WJJSZTJGFCFNKI-UHFFFAOYSA-N 1,3-oxathiolane Chemical compound C1CSCO1 WJJSZTJGFCFNKI-UHFFFAOYSA-N 0.000 claims description 8
NARVIWMVBMUEOG-UHFFFAOYSA-N 2-Hydroxy-propylene Natural products CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 claims description 8
229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 8
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
125000002837 carbocyclic group Chemical group 0.000 claims description 8
239000000812 cholinergic antagonist Substances 0.000 claims description 8
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 8
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 8
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
125000000842 isoxazolyl group Chemical group 0.000 claims description 8
239000003446 ligand Substances 0.000 claims description 8
125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 8
FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 7
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims description 7
IMLSAISZLJGWPP-UHFFFAOYSA-N 1,3-dithiolane Chemical compound C1CSCS1 IMLSAISZLJGWPP-UHFFFAOYSA-N 0.000 claims description 7
125000005955 1H-indazolyl group Chemical group 0.000 claims description 7
125000005236 alkanoylamino group Chemical group 0.000 claims description 7
150000005840 aryl radicals Chemical class 0.000 claims description 7
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 7
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 7
230000002265 prevention Effects 0.000 claims description 7
229940044551 receptor antagonist Drugs 0.000 claims description 7
239000002464 receptor antagonist Substances 0.000 claims description 7
125000004306 triazinyl group Chemical group 0.000 claims description 7
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims description 6
125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 6
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 6
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 6
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
239000013543 active substance Substances 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 6
230000001028 anti-proliverative effect Effects 0.000 claims description 6
125000005605 benzo group Chemical group 0.000 claims description 6
125000004181 carboxyalkyl group Chemical group 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 6
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 6
125000002950 monocyclic group Chemical group 0.000 claims description 6
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
229930192474 thiophene Natural products 0.000 claims description 6
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 5
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 5
125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 5
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 5
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
229940125388 beta agonist Drugs 0.000 claims description 5
125000002619 bicyclic group Chemical group 0.000 claims description 5
125000004663 dialkyl amino group Chemical group 0.000 claims description 5
125000000466 oxiranyl group Chemical group 0.000 claims description 5
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 5
125000004430 oxygen atom Chemical group O* 0.000 claims description 5
125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
239000000758 substrate Substances 0.000 claims description 5
125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 4
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 4
LQPOOAJESJYDLS-UHFFFAOYSA-N 1,3-oxazinane Chemical compound C1CNCOC1 LQPOOAJESJYDLS-UHFFFAOYSA-N 0.000 claims description 4
VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 4
MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 4
125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims description 4
WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 4
230000001800 adrenalinergic effect Effects 0.000 claims description 4
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 4
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
230000001419 dependent effect Effects 0.000 claims description 4
125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 4
125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
125000001207 fluorophenyl group Chemical group 0.000 claims description 4
229940097043 glucuronic acid Drugs 0.000 claims description 4
125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
125000000286 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
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
125000006413 ring segment Chemical group 0.000 claims description 4
125000004964 sulfoalkyl group Chemical group 0.000 claims description 4
229940124530 sulfonamide Drugs 0.000 claims description 4
150000003456 sulfonamides Chemical class 0.000 claims description 4
125000004434 sulfur atom Chemical group 0.000 claims description 4
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 4
125000004149 thio group Chemical group *S* 0.000 claims description 4
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 4
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 claims description 4
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 3
125000005862 (C1-C6)alkanoyl group Chemical group 0.000 claims description 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 3
125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 3
HKDFRDIIELOLTJ-UHFFFAOYSA-N 1,4-dithianyl Chemical group [CH]1CSCCS1 HKDFRDIIELOLTJ-UHFFFAOYSA-N 0.000 claims description 3
125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
125000003368 amide group Chemical group 0.000 claims description 3
125000002431 aminoalkoxy group Chemical group 0.000 claims description 3
125000004103 aminoalkyl group Chemical group 0.000 claims description 3
125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
125000001041 indolyl group Chemical group 0.000 claims description 3
230000003993 interaction Effects 0.000 claims description 3
230000001404 mediated effect Effects 0.000 claims description 3
AHKJGIUKIBGOKH-UHFFFAOYSA-N morpholine;piperidine Chemical compound C1CCNCC1.C1COCCN1 AHKJGIUKIBGOKH-UHFFFAOYSA-N 0.000 claims description 3
OZQGLZFAWYKKLQ-UHFFFAOYSA-N oxazinane Chemical compound C1CCONC1 OZQGLZFAWYKKLQ-UHFFFAOYSA-N 0.000 claims description 3
125000002071 phenylalkoxy group Chemical group 0.000 claims description 3
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 3
UBZJXAQDXUGXIZ-UHFFFAOYSA-N quinazoline;quinoline Chemical compound N1=CC=CC2=CC=CC=C21.N1=CN=CC2=CC=CC=C21 UBZJXAQDXUGXIZ-UHFFFAOYSA-N 0.000 claims description 3
230000000241 respiratory effect Effects 0.000 claims description 3
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 2
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 claims description 2
IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 claims description 2
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
OIMWEHOYHJJPJD-UHFFFAOYSA-N pyridine;pyrimidine Chemical compound C1=CC=NC=C1.C1=CN=CN=C1 OIMWEHOYHJJPJD-UHFFFAOYSA-N 0.000 claims description 2
125000000542 sulfonic acid group Chemical group 0.000 claims description 2
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
235000019000 fluorine Nutrition 0.000 claims 21
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 19
229940125400 channel inhibitor Drugs 0.000 claims 3
229940122041 Cholinesterase inhibitor Drugs 0.000 claims 2
IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 claims 2
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 2
239000003937 drug carrier Substances 0.000 claims 2
125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
125000006698 (C1-C3) dialkylamino group Chemical group 0.000 claims 1
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
240000006927 Foeniculum vulgare Species 0.000 claims 1
235000004204 Foeniculum vulgare Nutrition 0.000 claims 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
230000010799 Receptor Interactions Effects 0.000 claims 1
230000001476 alcoholic effect Effects 0.000 claims 1
239000000801 calcium channel stimulating agent Substances 0.000 claims 1
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
238000005266 casting Methods 0.000 claims 1
230000001351 cycling effect Effects 0.000 claims 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
RPAWVEMNAJPPEL-UHFFFAOYSA-N morpholine;thiomorpholine Chemical compound C1COCCN1.C1CSCCN1 RPAWVEMNAJPPEL-UHFFFAOYSA-N 0.000 claims 1
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
150000002916 oxazoles Chemical class 0.000 claims 1
125000003072 pyrazolidinyl group Chemical group 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
230000002401 inhibitory effect Effects 0.000 abstract description 5
102000003914 Cholinesterases Human genes 0.000 abstract 1
108090000322 Cholinesterases Proteins 0.000 abstract 1
229940048961 cholinesterase Drugs 0.000 abstract 1
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 52
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 47
150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 42
229940002612 prodrug Drugs 0.000 description 41
239000000651 prodrug Substances 0.000 description 41
239000002207 metabolite Substances 0.000 description 36
239000000126 substance Substances 0.000 description 30
239000003814 drug Substances 0.000 description 26
229960001722 verapamil Drugs 0.000 description 21
SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 20
150000003943 catecholamines Chemical class 0.000 description 17
229940124597 therapeutic agent Drugs 0.000 description 17
210000001519 tissue Anatomy 0.000 description 16
125000002883 imidazolyl group Chemical group 0.000 description 14
230000006870 function Effects 0.000 description 13
NOYPYLRCIDNJJB-UHFFFAOYSA-N trimetrexate Chemical compound COC1=C(OC)C(OC)=CC(NCC=2C(=C3C(N)=NC(N)=NC3=CC=2)C)=C1 NOYPYLRCIDNJJB-UHFFFAOYSA-N 0.000 description 13
229960001099 trimetrexate Drugs 0.000 description 13
MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 description 12
102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 12
108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 12
KEDQCFRVSHYKLR-UHFFFAOYSA-N 3-[3-[2-(3,4-dimethoxyphenyl)ethyl-methylamino]propyl]-7,8-dimethoxy-2,5-dihydro-1H-3-benzazepin-4-one Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCN1C(=O)CC2=CC(OC)=C(OC)C=C2CC1 KEDQCFRVSHYKLR-UHFFFAOYSA-N 0.000 description 11
102000001301 EGF receptor Human genes 0.000 description 11
108060006698 EGF receptor Proteins 0.000 description 11
XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 11
230000004044 response Effects 0.000 description 11
229950003419 zatebradine Drugs 0.000 description 11
JQSAYKKFZOSZGJ-UHFFFAOYSA-N 1-[bis(4-fluorophenyl)methyl]-4-[(2,3,4-trimethoxyphenyl)methyl]piperazine Chemical compound COC1=C(OC)C(OC)=CC=C1CN1CCN(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 JQSAYKKFZOSZGJ-UHFFFAOYSA-N 0.000 description 10
XQLWNAFCTODIRK-UHFFFAOYSA-N Gallopamil Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC(OC)=C(OC)C(OC)=C1 XQLWNAFCTODIRK-UHFFFAOYSA-N 0.000 description 10
102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 10
108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 10
206010040070 Septic Shock Diseases 0.000 description 10
239000005557 antagonist Substances 0.000 description 10
230000004071 biological effect Effects 0.000 description 10
229960000457 gallopamil Drugs 0.000 description 10
210000000056 organ Anatomy 0.000 description 10
206010028980 Neoplasm Diseases 0.000 description 9
201000004681 Psoriasis Diseases 0.000 description 9
125000003277 amino group Chemical group 0.000 description 9
229950007692 lomerizine Drugs 0.000 description 9
108060003345 Adrenergic Receptor Proteins 0.000 description 8
102000017910 Adrenergic receptor Human genes 0.000 description 8
102000016966 beta-2 Adrenergic Receptors Human genes 0.000 description 8
108010014499 beta-2 Adrenergic Receptors Proteins 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
XDUOTWNXVDBCDY-SREVYHEPSA-N cinepazet Chemical group C1CN(CC(=O)OCC)CCN1C(=O)\C=C/C1=CC(OC)=C(OC)C(OC)=C1 XDUOTWNXVDBCDY-SREVYHEPSA-N 0.000 description 8
229960000352 cinepazet Drugs 0.000 description 8
WMIYKQLTONQJES-UHFFFAOYSA-N hexafluoroethane Chemical compound FC(F)(F)C(F)(F)F WMIYKQLTONQJES-UHFFFAOYSA-N 0.000 description 8
WDKXLLJDNUBYCY-UHFFFAOYSA-N ibopamine Chemical compound CNCCC1=CC=C(OC(=O)C(C)C)C(OC(=O)C(C)C)=C1 WDKXLLJDNUBYCY-UHFFFAOYSA-N 0.000 description 8
208000015181 infectious disease Diseases 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
206010002383 Angina Pectoris Diseases 0.000 description 7
206010020772 Hypertension Diseases 0.000 description 7
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 7
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 7
206010040047 Sepsis Diseases 0.000 description 7
239000000150 Sympathomimetic Substances 0.000 description 7
230000009471 action Effects 0.000 description 7
239000002246 antineoplastic agent Substances 0.000 description 7
102000012740 beta Adrenergic Receptors Human genes 0.000 description 7
108010079452 beta Adrenergic Receptors Proteins 0.000 description 7
125000002632 imidazolidinyl group Chemical group 0.000 description 7
125000004193 piperazinyl group Chemical group 0.000 description 7
208000023504 respiratory system disease Diseases 0.000 description 7
206010001513 AIDS related complex Diseases 0.000 description 6
206010006895 Cachexia Diseases 0.000 description 6
206010067584 Type 1 diabetes mellitus Diseases 0.000 description 6
230000027455 binding Effects 0.000 description 6
206010006451 bronchitis Diseases 0.000 description 6
201000011510 cancer Diseases 0.000 description 6
208000026106 cerebrovascular disease Diseases 0.000 description 6
230000001713 cholinergic effect Effects 0.000 description 6
230000008602 contraction Effects 0.000 description 6
229940079593 drug Drugs 0.000 description 6
230000007246 mechanism Effects 0.000 description 6
125000002757 morpholinyl group Chemical group 0.000 description 6
125000005936 piperidyl group Chemical group 0.000 description 6
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 description 6
229960001289 prazosin Drugs 0.000 description 6
235000018102 proteins Nutrition 0.000 description 6
102000004169 proteins and genes Human genes 0.000 description 6
108090000623 proteins and genes Proteins 0.000 description 6
230000001975 sympathomimetic effect Effects 0.000 description 6
XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 5
QVZCXCJXTMIDME-UHFFFAOYSA-N Biopropazepan Trimethoxybenzoate Chemical compound COC1=C(OC)C(OC)=CC(C(=O)OCCCN2CCN(CCCOC(=O)C=3C=C(OC)C(OC)=C(OC)C=3)CCC2)=C1 QVZCXCJXTMIDME-UHFFFAOYSA-N 0.000 description 5
241000725303 Human immunodeficiency virus Species 0.000 description 5
108010044467 Isoenzymes Proteins 0.000 description 5
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 5
239000000464 adrenergic agent Substances 0.000 description 5
229940034982 antineoplastic agent Drugs 0.000 description 5
206010003119 arrhythmia Diseases 0.000 description 5
230000006793 arrhythmia Effects 0.000 description 5
HXLAFSUPPDYFEO-UHFFFAOYSA-N bevantolol Chemical compound C1=C(OC)C(OC)=CC=C1CCNCC(O)COC1=CC=CC(C)=C1 HXLAFSUPPDYFEO-UHFFFAOYSA-N 0.000 description 5
229960003588 bevantolol Drugs 0.000 description 5
FZGVEKPRDOIXJY-UHFFFAOYSA-N bitolterol Chemical compound C1=CC(C)=CC=C1C(=O)OC1=CC=C(C(O)CNC(C)(C)C)C=C1OC(=O)C1=CC=C(C)C=C1 FZGVEKPRDOIXJY-UHFFFAOYSA-N 0.000 description 5
229960004620 bitolterol Drugs 0.000 description 5
ZKSIPEYIAHUPNM-ZEQRLZLVSA-N butobendine Chemical compound C([C@H](CC)N(C)CCN(C)[C@@H](CC)COC(=O)C=1C=C(OC)C(OC)=C(OC)C=1)OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 ZKSIPEYIAHUPNM-ZEQRLZLVSA-N 0.000 description 5
229950001141 butobendine Drugs 0.000 description 5
230000002490 cerebral effect Effects 0.000 description 5
RCUDFXMNPQNBDU-VOTSOKGWSA-N cinepazide Chemical compound COC1=C(OC)C(OC)=CC(\C=C\C(=O)N2CCN(CC(=O)N3CCCC3)CC2)=C1 RCUDFXMNPQNBDU-VOTSOKGWSA-N 0.000 description 5
229960004201 cinepazide Drugs 0.000 description 5
VHSBBVZJABQOSG-MRXNPFEDSA-N denopamine Chemical compound C1=C(OC)C(OC)=CC=C1CCNC[C@@H](O)C1=CC=C(O)C=C1 VHSBBVZJABQOSG-MRXNPFEDSA-N 0.000 description 5
229950007304 denopamine Drugs 0.000 description 5
229960001079 dilazep Drugs 0.000 description 5
239000006274 endogenous ligand Substances 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
230000001613 neoplastic effect Effects 0.000 description 5
150000003254 radicals Chemical class 0.000 description 5
230000001105 regulatory effect Effects 0.000 description 5
238000010572 single replacement reaction Methods 0.000 description 5
VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 5
229960001693 terazosin Drugs 0.000 description 5
229960000195 terbutaline Drugs 0.000 description 5
YNZXWQJZEDLQEG-UHFFFAOYSA-N trimazosin Chemical compound N1=C2C(OC)=C(OC)C(OC)=CC2=C(N)N=C1N1CCN(C(=O)OCC(C)(C)O)CC1 YNZXWQJZEDLQEG-UHFFFAOYSA-N 0.000 description 5
229960002906 trimazosin Drugs 0.000 description 5
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical group [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 4
JRWZLRBJNMZMFE-UHFFFAOYSA-N Dobutamine Chemical compound C=1C=C(O)C(O)=CC=1CCNC(C)CCC1=CC=C(O)C=C1 JRWZLRBJNMZMFE-UHFFFAOYSA-N 0.000 description 4
102000004190 Enzymes Human genes 0.000 description 4
108090000790 Enzymes Proteins 0.000 description 4
108091006027 G proteins Proteins 0.000 description 4
102000030782 GTP binding Human genes 0.000 description 4
108091000058 GTP-Binding Proteins 0.000 description 4
206010061218 Inflammation Diseases 0.000 description 4
229940124639 Selective inhibitor Drugs 0.000 description 4
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 4
229960004373 acetylcholine Drugs 0.000 description 4
239000000048 adrenergic agonist Substances 0.000 description 4
239000002585 base Substances 0.000 description 4
230000000059 bradycardiac effect Effects 0.000 description 4
210000004556 brain Anatomy 0.000 description 4
239000011575 calcium Substances 0.000 description 4
239000000480 calcium channel blocker Substances 0.000 description 4
210000003169 central nervous system Anatomy 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
229960001089 dobutamine Drugs 0.000 description 4
ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 4
RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 4
229960001389 doxazosin Drugs 0.000 description 4
229940088598 enzyme Drugs 0.000 description 4
GTTBEUCJPZQMDZ-UHFFFAOYSA-N erlotinib hydrochloride Chemical compound [H+].[Cl-].C=12C=C(OCCOC)C(OCCOC)=CC2=NC=NC=1NC1=CC=CC(C#C)=C1 GTTBEUCJPZQMDZ-UHFFFAOYSA-N 0.000 description 4
239000004052 folic acid antagonist Substances 0.000 description 4
229960004370 ibopamine Drugs 0.000 description 4
230000004054 inflammatory process Effects 0.000 description 4
230000000302 ischemic effect Effects 0.000 description 4
230000002503 metabolic effect Effects 0.000 description 4
LMOINURANNBYCM-UHFFFAOYSA-N metaproterenol Chemical compound CC(C)NCC(O)C1=CC(O)=CC(O)=C1 LMOINURANNBYCM-UHFFFAOYSA-N 0.000 description 4
230000004899 motility Effects 0.000 description 4
239000002858 neurotransmitter agent Substances 0.000 description 4
229960002748 norepinephrine Drugs 0.000 description 4
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 4
229960002657 orciprenaline Drugs 0.000 description 4
201000008482 osteoarthritis Diseases 0.000 description 4
125000001715 oxadiazolyl group Chemical group 0.000 description 4
231100000915 pathological change Toxicity 0.000 description 4
230000036285 pathological change Effects 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
230000008569 process Effects 0.000 description 4
230000035755 proliferation Effects 0.000 description 4
125000000719 pyrrolidinyl group Chemical group 0.000 description 4
125000000168 pyrrolyl group Chemical group 0.000 description 4
206010039073 rheumatoid arthritis Diseases 0.000 description 4
230000036303 septic shock Effects 0.000 description 4
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
208000030507 AIDS Diseases 0.000 description 3
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 3
208000024827 Alzheimer disease Diseases 0.000 description 3
208000035143 Bacterial infection Diseases 0.000 description 3
208000006386 Bone Resorption Diseases 0.000 description 3
RHLJLALHBZGAFM-UHFFFAOYSA-N Bunazosinum Chemical compound C1CN(C(=O)CCC)CCCN1C1=NC(N)=C(C=C(OC)C(OC)=C2)C2=N1 RHLJLALHBZGAFM-UHFFFAOYSA-N 0.000 description 3
108010009685 Cholinergic Receptors Proteins 0.000 description 3
208000035473 Communicable disease Diseases 0.000 description 3
208000011231 Crohn disease Diseases 0.000 description 3
201000004624 Dermatitis Diseases 0.000 description 3
206010014824 Endotoxic shock Diseases 0.000 description 3
206010017533 Fungal infection Diseases 0.000 description 3
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 description 3
241000282412 Homo Species 0.000 description 3
208000022559 Inflammatory bowel disease Diseases 0.000 description 3
FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 3
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 3
208000019695 Migraine disease Diseases 0.000 description 3
229940121948 Muscarinic receptor antagonist Drugs 0.000 description 3
208000000112 Myalgia Diseases 0.000 description 3
208000031888 Mycoses Diseases 0.000 description 3
206010037660 Pyrexia Diseases 0.000 description 3
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 3
208000007536 Thrombosis Diseases 0.000 description 3
206010044248 Toxic shock syndrome Diseases 0.000 description 3
231100000650 Toxic shock syndrome Toxicity 0.000 description 3
208000036142 Viral infection Diseases 0.000 description 3
238000009825 accumulation Methods 0.000 description 3
102000034337 acetylcholine receptors Human genes 0.000 description 3
230000001154 acute effect Effects 0.000 description 3
238000007792 addition Methods 0.000 description 3
UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 3
229950006790 adenosine phosphate Drugs 0.000 description 3
201000000028 adult respiratory distress syndrome Diseases 0.000 description 3
WNMJYKCGWZFFKR-UHFFFAOYSA-N alfuzosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(C)CCCNC(=O)C1CCCO1 WNMJYKCGWZFFKR-UHFFFAOYSA-N 0.000 description 3
229960004607 alfuzosin Drugs 0.000 description 3
125000004450 alkenylene group Chemical group 0.000 description 3
230000003042 antagnostic effect Effects 0.000 description 3
230000003276 anti-hypertensive effect Effects 0.000 description 3
239000003416 antiarrhythmic agent Substances 0.000 description 3
239000002220 antihypertensive agent Substances 0.000 description 3
206010003246 arthritis Diseases 0.000 description 3
230000001580 bacterial effect Effects 0.000 description 3
208000022362 bacterial infectious disease Diseases 0.000 description 3
102000016967 beta-1 Adrenergic Receptors Human genes 0.000 description 3
108010014494 beta-1 Adrenergic Receptors Proteins 0.000 description 3
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
230000008499 blood brain barrier function Effects 0.000 description 3
210000001218 blood-brain barrier Anatomy 0.000 description 3
230000024279 bone resorption Effects 0.000 description 3
229960002467 bunazosin Drugs 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
230000015556 catabolic process Effects 0.000 description 3
230000001684 chronic effect Effects 0.000 description 3
230000007850 degeneration Effects 0.000 description 3
238000010573 double replacement reaction Methods 0.000 description 3
230000002526 effect on cardiovascular system Effects 0.000 description 3
239000008103 glucose Substances 0.000 description 3
230000003463 hyperproliferative effect Effects 0.000 description 3
208000026278 immune system disease Diseases 0.000 description 3
208000033065 inborn errors of immunity Diseases 0.000 description 3
230000002458 infectious effect Effects 0.000 description 3
230000002757 inflammatory effect Effects 0.000 description 3
206010022000 influenza Diseases 0.000 description 3
210000001503 joint Anatomy 0.000 description 3
208000032839 leukemia Diseases 0.000 description 3
230000007774 longterm Effects 0.000 description 3
206010025135 lupus erythematosus Diseases 0.000 description 3
230000003211 malignant effect Effects 0.000 description 3
230000007102 metabolic function Effects 0.000 description 3
201000006417 multiple sclerosis Diseases 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
208000028529 primary immunodeficiency disease Diseases 0.000 description 3
DRYRBWIFRVMRPV-UHFFFAOYSA-N quinazolin-4-amine Chemical group C1=CC=C2C(N)=NC=NC2=C1 DRYRBWIFRVMRPV-UHFFFAOYSA-N 0.000 description 3
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
230000002829 reductive effect Effects 0.000 description 3
230000019491 signal transduction Effects 0.000 description 3
230000011664 signaling Effects 0.000 description 3
208000017520 skin disease Diseases 0.000 description 3
229940127230 sympathomimetic drug Drugs 0.000 description 3
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 3
239000005483 tyrosine kinase inhibitor Substances 0.000 description 3
230000003612 virological effect Effects 0.000 description 3
PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
102100033639 Acetylcholinesterase Human genes 0.000 description 2
108010022752 Acetylcholinesterase Proteins 0.000 description 2
206010002556 Ankylosing Spondylitis Diseases 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
206010065929 Cardiovascular insufficiency Diseases 0.000 description 2
102000017063 Catecholamine Receptors Human genes 0.000 description 2
108010013659 Catecholamine Receptors Proteins 0.000 description 2
206010008111 Cerebral haemorrhage Diseases 0.000 description 2
108091006146 Channels Proteins 0.000 description 2
UDMBCSSLTHHNCD-UHFFFAOYSA-N Coenzym Q(11) Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1O UDMBCSSLTHHNCD-UHFFFAOYSA-N 0.000 description 2
206010052895 Coronary artery insufficiency Diseases 0.000 description 2
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
AEMOLEFTQBMNLQ-AQKNRBDQSA-N D-glucopyranuronic acid Chemical group OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O AEMOLEFTQBMNLQ-AQKNRBDQSA-N 0.000 description 2
229940117937 Dihydrofolate reductase inhibitor Drugs 0.000 description 2
208000005189 Embolism Diseases 0.000 description 2
108090000371 Esterases Proteins 0.000 description 2
208000010412 Glaucoma Diseases 0.000 description 2
206010018367 Glomerulonephritis chronic Diseases 0.000 description 2
102000009465 Growth Factor Receptors Human genes 0.000 description 2
108010009202 Growth Factor Receptors Proteins 0.000 description 2
206010018985 Haemorrhage intracranial Diseases 0.000 description 2
208000032843 Hemorrhage Diseases 0.000 description 2
208000001953 Hypotension Diseases 0.000 description 2
206010021143 Hypoxia Diseases 0.000 description 2
206010061216 Infarction Diseases 0.000 description 2
201000001429 Intracranial Thrombosis Diseases 0.000 description 2
108090000862 Ion Channels Proteins 0.000 description 2
102000004310 Ion Channels Human genes 0.000 description 2
241000233870 Pneumocystis Species 0.000 description 2
206010035664 Pneumonia Diseases 0.000 description 2
201000001068 Prinzmetal angina Diseases 0.000 description 2
102000001253 Protein Kinase Human genes 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
206010063837 Reperfusion injury Diseases 0.000 description 2
206010039085 Rhinitis allergic Diseases 0.000 description 2
201000010001 Silicosis Diseases 0.000 description 2
208000032851 Subarachnoid Hemorrhage Diseases 0.000 description 2
208000032109 Transient ischaemic attack Diseases 0.000 description 2
YPTFHLJNWSJXKG-UHFFFAOYSA-N Trepibutone Chemical compound CCOC1=CC(OCC)=C(C(=O)CCC(O)=O)C=C1OCC YPTFHLJNWSJXKG-UHFFFAOYSA-N 0.000 description 2
UHWVSEOVJBQKBE-UHFFFAOYSA-N Trimetazidine Chemical compound COC1=C(OC)C(OC)=CC=C1CN1CCNCC1 UHWVSEOVJBQKBE-UHFFFAOYSA-N 0.000 description 2
108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 2
229940022698 acetylcholinesterase Drugs 0.000 description 2
230000004913 activation Effects 0.000 description 2
102000030621 adenylate cyclase Human genes 0.000 description 2
108060000200 adenylate cyclase Proteins 0.000 description 2
239000000674 adrenergic antagonist Substances 0.000 description 2
239000000332 adrenergic beta-1 receptor antagonist Substances 0.000 description 2
239000000808 adrenergic beta-agonist Substances 0.000 description 2
229940126157 adrenergic receptor agonist Drugs 0.000 description 2
210000005091 airway smooth muscle Anatomy 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
201000010105 allergic rhinitis Diseases 0.000 description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
230000001466 anti-adreneric effect Effects 0.000 description 2
230000003432 anti-folate effect Effects 0.000 description 2
230000001022 anti-muscarinic effect Effects 0.000 description 2
229940127074 antifolate Drugs 0.000 description 2
229940030600 antihypertensive agent Drugs 0.000 description 2
229940125684 antimigraine agent Drugs 0.000 description 2
239000002282 antimigraine agent Substances 0.000 description 2
125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
206010003230 arteritis Diseases 0.000 description 2
125000004104 aryloxy group Chemical group 0.000 description 2
XXZSQOVSEBAPGS-UHFFFAOYSA-L atracurium besylate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1.[O-]S(=O)(=O)C1=CC=CC=C1.C1=C(OC)C(OC)=CC=C1CC1[N+](CCC(=O)OCCCCCOC(=O)CC[N+]2(C)C(C3=CC(OC)=C(OC)C=C3CC2)CC=2C=C(OC)C(OC)=CC=2)(C)CCC2=CC(OC)=C(OC)C=C21 XXZSQOVSEBAPGS-UHFFFAOYSA-L 0.000 description 2
229960002945 atracurium besylate Drugs 0.000 description 2
210000003403 autonomic nervous system Anatomy 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
230000017531 blood circulation Effects 0.000 description 2
150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
230000000747 cardiac effect Effects 0.000 description 2
206010008118 cerebral infarction Diseases 0.000 description 2
210000002932 cholinergic neuron Anatomy 0.000 description 2
208000010877 cognitive disease Diseases 0.000 description 2
210000004351 coronary vessel Anatomy 0.000 description 2
229940095074 cyclic amp Drugs 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
229940127089 cytotoxic agent Drugs 0.000 description 2
230000006378 damage Effects 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
230000002074 deregulated effect Effects 0.000 description 2
230000006866 deterioration Effects 0.000 description 2
239000003166 dihydrofolate reductase inhibitor Substances 0.000 description 2
230000006806 disease prevention Effects 0.000 description 2
229960003530 donepezil Drugs 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
230000003291 dopaminomimetic effect Effects 0.000 description 2
210000001339 epidermal cell Anatomy 0.000 description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
210000005003 heart tissue Anatomy 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
201000009939 hypertensive encephalopathy Diseases 0.000 description 2
208000021822 hypotensive Diseases 0.000 description 2
230000001077 hypotensive effect Effects 0.000 description 2
230000007574 infarction Effects 0.000 description 2
210000000936 intestine Anatomy 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
230000001057 ionotropic effect Effects 0.000 description 2
229940039009 isoproterenol Drugs 0.000 description 2
208000018937 joint inflammation Diseases 0.000 description 2
208000011379 keloid formation Diseases 0.000 description 2
229960000485 methotrexate Drugs 0.000 description 2
206010027599 migraine Diseases 0.000 description 2
230000002297 mitogenic effect Effects 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
210000002464 muscle smooth vascular Anatomy 0.000 description 2
208000031225 myocardial ischemia Diseases 0.000 description 2
210000004165 myocardium Anatomy 0.000 description 2
210000001640 nerve ending Anatomy 0.000 description 2
210000002569 neuron Anatomy 0.000 description 2
230000003836 peripheral circulation Effects 0.000 description 2
230000002093 peripheral effect Effects 0.000 description 2
239000000810 peripheral vasodilating agent Substances 0.000 description 2
229960002116 peripheral vasodilator Drugs 0.000 description 2
230000026731 phosphorylation Effects 0.000 description 2
238000006366 phosphorylation reaction Methods 0.000 description 2
201000000317 pneumocystosis Diseases 0.000 description 2
238000011321 prophylaxis Methods 0.000 description 2
108060006633 protein kinase Proteins 0.000 description 2
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 2
208000037803 restenosis Diseases 0.000 description 2
231100000241 scar Toxicity 0.000 description 2
230000028327 secretion Effects 0.000 description 2
210000002460 smooth muscle Anatomy 0.000 description 2
239000011734 sodium Substances 0.000 description 2
230000000638 stimulation Effects 0.000 description 2
230000002889 sympathetic effect Effects 0.000 description 2
238000002636 symptomatic treatment Methods 0.000 description 2
208000011580 syndromic disease Diseases 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 2
230000009772 tissue formation Effects 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
201000010875 transient cerebral ischemia Diseases 0.000 description 2
229960004974 trepibutone Drugs 0.000 description 2
229960001177 trimetazidine Drugs 0.000 description 2
102000003390 tumor necrosis factor Human genes 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical class C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 1
125000006536 (C1-C2)alkoxy group Chemical group 0.000 description 1
125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 description 1
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 description 1
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 description 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
229930182837 (R)-adrenaline Natural products 0.000 description 1
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 1
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
MXBVNILGVJVVMH-UHFFFAOYSA-N 1,7-naphthyridine Chemical compound C1=NC=CC2=CC=CN=C21 MXBVNILGVJVVMH-UHFFFAOYSA-N 0.000 description 1
FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
UFEHHWAXLUKWBV-UHFFFAOYSA-N 1-(1-cyclohexyl-3-ethylindazol-6-yl)-4-oxocyclohexane-1-carbonitrile Chemical compound C12=CC(C3(CCC(=O)CC3)C#N)=CC=C2C(CC)=NN1C1CCCCC1 UFEHHWAXLUKWBV-UHFFFAOYSA-N 0.000 description 1
SXBFINKPTJKSJC-UHFFFAOYSA-N 1-benzyl-2-methoxypiperazine Chemical class COC1CNCCN1CC1=CC=CC=C1 SXBFINKPTJKSJC-UHFFFAOYSA-N 0.000 description 1
NLHOVYMVGLRDPF-UHFFFAOYSA-N 1-oxidoquinazolin-1-ium Chemical compound C1=CC=C2[N+]([O-])=CN=CC2=C1 NLHOVYMVGLRDPF-UHFFFAOYSA-N 0.000 description 1
OARGFWQSVACNCO-UHFFFAOYSA-N 1-oxidoquinoxalin-1-ium Chemical compound C1=CC=C2[N+]([O-])=CC=NC2=C1 OARGFWQSVACNCO-UHFFFAOYSA-N 0.000 description 1
QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 description 1
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 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
125000001963 4 membered heterocyclic group Chemical group 0.000 description 1
IJALWSVNUBBQRA-UHFFFAOYSA-N 4-Isopropyl-3-methylphenol Chemical compound CC(C)C1=CC=C(O)C=C1C IJALWSVNUBBQRA-UHFFFAOYSA-N 0.000 description 1
UKVJLLRHTQPKJR-UHFFFAOYSA-N 4-[3-ethyl-1-(4-fluorophenyl)indazol-6-yl]cyclohex-3-ene-1-carboxylic acid Chemical compound C12=CC(C=3CCC(CC=3)C(O)=O)=CC=C2C(CC)=NN1C1=CC=C(F)C=C1 UKVJLLRHTQPKJR-UHFFFAOYSA-N 0.000 description 1
GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 1
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
GQJHRXMJKSJWLV-UHFFFAOYSA-N 6-bromo-3-ethyl-1-(4-fluorophenyl)indazole Chemical compound C12=CC(Br)=CC=C2C(CC)=NN1C1=CC=C(F)C=C1 GQJHRXMJKSJWLV-UHFFFAOYSA-N 0.000 description 1
KLCMEUJCIYXCHD-UHFFFAOYSA-N 7,8-dimethoxy-3-benzazepin-2-one Chemical compound C1=NC(=O)C=C2C=C(OC)C(OC)=CC2=C1 KLCMEUJCIYXCHD-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
244000235603 Acacia catechu Species 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
229940100578 Acetylcholinesterase inhibitor Drugs 0.000 description 1
206010002388 Angina unstable Diseases 0.000 description 1
235000006226 Areca catechu Nutrition 0.000 description 1
208000023275 Autoimmune disease Diseases 0.000 description 1
210000002237 B-cell of pancreatic islet Anatomy 0.000 description 1
101001131238 Bos taurus Caltrin Proteins 0.000 description 1
206010006458 Bronchitis chronic Diseases 0.000 description 1
125000004399 C1-C4 alkenyl group Chemical group 0.000 description 1
125000004648 C2-C8 alkenyl group Chemical group 0.000 description 1
125000001313 C5-C10 heteroaryl group Chemical group 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
108020002739 Catechol O-methyltransferase Proteins 0.000 description 1
102000006378 Catechol O-methyltransferase Human genes 0.000 description 1
206010008088 Cerebral artery embolism Diseases 0.000 description 1
206010008132 Cerebral thrombosis Diseases 0.000 description 1
102000019034 Chemokines Human genes 0.000 description 1
108010012236 Chemokines Proteins 0.000 description 1
USDIRSJFHPHMAS-UHFFFAOYSA-N ClC1=NC=C(C=2C1=NC=CN=2)F Chemical compound ClC1=NC=C(C=2C1=NC=CN=2)F USDIRSJFHPHMAS-UHFFFAOYSA-N 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 1
206010061818 Disease progression Diseases 0.000 description 1
206010014561 Emphysema Diseases 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 1
108091006065 Gs proteins Proteins 0.000 description 1
108010081348 HRT1 protein Hairy Proteins 0.000 description 1
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 1
101001131237 Homo sapiens Putative peptide YY-2 Proteins 0.000 description 1
101001050288 Homo sapiens Transcription factor Jun Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010021118 Hypotonia Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 1
206010061598 Immunodeficiency Diseases 0.000 description 1
208000029462 Immunodeficiency disease Diseases 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
208000017657 Menopausal disease Diseases 0.000 description 1
206010027603 Migraine headaches Diseases 0.000 description 1
102000008109 Mixed Function Oxygenases Human genes 0.000 description 1
108010074633 Mixed Function Oxygenases Proteins 0.000 description 1
101001135087 Mus musculus Prostate and testis expressed protein 4 Proteins 0.000 description 1
101000909851 Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv) cAMP/cGMP dual specificity phosphodiesterase Rv0805 Proteins 0.000 description 1
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical group NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
229940099471 Phosphodiesterase inhibitor Drugs 0.000 description 1
108091000080 Phosphotransferase Proteins 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
102000003923 Protein Kinase C Human genes 0.000 description 1
108090000315 Protein Kinase C Proteins 0.000 description 1
102100034367 Putative peptide YY-2 Human genes 0.000 description 1
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
GIIWGCBLYNDKBO-UHFFFAOYSA-N Quinoline 1-oxide Chemical compound C1=CC=C2[N+]([O-])=CC=CC2=C1 GIIWGCBLYNDKBO-UHFFFAOYSA-N 0.000 description 1
101000598321 Rattus norvegicus Serine protease inhibitor Kazal-type 1-like Proteins 0.000 description 1
102000004278 Receptor Protein-Tyrosine Kinases Human genes 0.000 description 1
108090000873 Receptor Protein-Tyrosine Kinases Proteins 0.000 description 1
206010038687 Respiratory distress Diseases 0.000 description 1
241000901714 Spondylis Species 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
102100023132 Transcription factor Jun Human genes 0.000 description 1
108091000117 Tyrosine 3-Monooxygenase Proteins 0.000 description 1
102000048218 Tyrosine 3-monooxygenases Human genes 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
208000007814 Unstable Angina Diseases 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
ZVNYJIZDIRKMBF-UHFFFAOYSA-N Vesnarinone Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)N1CCN(C=2C=C3CCC(=O)NC3=CC=2)CC1 ZVNYJIZDIRKMBF-UHFFFAOYSA-N 0.000 description 1
241000700605 Viruses Species 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
XLIJUKVKOIMPKW-BTVCFUMJSA-N [O].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O Chemical compound [O].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O XLIJUKVKOIMPKW-BTVCFUMJSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
210000001789 adipocyte Anatomy 0.000 description 1
210000001943 adrenal medulla Anatomy 0.000 description 1
239000000533 adrenergic alpha-1 receptor agonist Substances 0.000 description 1
239000000614 adrenergic beta-2 receptor agonist Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
238000004220 aggregation Methods 0.000 description 1
125000003806 alkyl carbonyl amino group Chemical group 0.000 description 1
125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000005263 alkylenediamine group Chemical group 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
230000008856 allosteric binding Effects 0.000 description 1
125000000746 allylic group Chemical group 0.000 description 1
102000004305 alpha Adrenergic Receptors Human genes 0.000 description 1
108090000861 alpha Adrenergic Receptors Proteins 0.000 description 1
239000002160 alpha blocker Substances 0.000 description 1
102000030619 alpha-1 Adrenergic Receptor Human genes 0.000 description 1
108020004102 alpha-1 Adrenergic Receptor Proteins 0.000 description 1
102000030484 alpha-2 Adrenergic Receptor Human genes 0.000 description 1
108020004101 alpha-2 Adrenergic Receptor Proteins 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
229940025084 amphetamine Drugs 0.000 description 1
208000003455 anaphylaxis Diseases 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
230000002921 anti-spasmodic effect Effects 0.000 description 1
238000011394 anticancer treatment Methods 0.000 description 1
230000006502 antiplatelets effects Effects 0.000 description 1
239000003699 antiulcer agent Substances 0.000 description 1
210000002565 arteriole Anatomy 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N aspartic acid group Chemical group N[C@@H](CC(=O)O)C(=O)O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
230000035578 autophosphorylation Effects 0.000 description 1
101150099549 azo1 gene Proteins 0.000 description 1
FYJJXENSONZJRG-UHFFFAOYSA-N bencyclane Chemical compound C=1C=CC=CC=1CC1(OCCCN(C)C)CCCCCC1 FYJJXENSONZJRG-UHFFFAOYSA-N 0.000 description 1
AITBHTAFQQYBHP-UHFFFAOYSA-N benzene;pyridine Chemical class C1=CC=CC=C1.C1=CC=NC=C1 AITBHTAFQQYBHP-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical group [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
229940124748 beta 2 agonist Drugs 0.000 description 1
102000015005 beta-adrenergic receptor activity proteins Human genes 0.000 description 1
108040006818 beta-adrenergic receptor activity proteins Proteins 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
230000006696 biosynthetic metabolic pathway Effects 0.000 description 1
UKRHKPCWTGYGIN-UHFFFAOYSA-K bis[(4,7,7-trimethyl-3-oxobicyclo[2.2.1]heptane-2-carbonyl)oxy]bismuthanyl 4,7,7-trimethyl-3-oxobicyclo[2.2.1]heptane-2-carboxylate Chemical compound [Bi+3].C1CC2(C)C(=O)C(C([O-])=O)C1C2(C)C.C1CC2(C)C(=O)C(C([O-])=O)C1C2(C)C.C1CC2(C)C(=O)C(C([O-])=O)C1C2(C)C UKRHKPCWTGYGIN-UHFFFAOYSA-K 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
150000001669 calcium Chemical class 0.000 description 1
125000002843 carboxylic acid group Chemical class 0.000 description 1
230000022900 cardiac muscle contraction Effects 0.000 description 1
229940124461 cardiostimulant Drugs 0.000 description 1
239000000496 cardiotonic agent Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
235000005487 catechin Nutrition 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
230000020411 cell activation Effects 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
230000003727 cerebral blood flow Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 description 1
208000007451 chronic bronchitis Diseases 0.000 description 1
229950001002 cianidanol Drugs 0.000 description 1
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
206010009887 colitis Diseases 0.000 description 1
230000009137 competitive binding Effects 0.000 description 1
239000003218 coronary vasodilator agent Substances 0.000 description 1
238000012937 correction Methods 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
229960000729 cyclandelate Drugs 0.000 description 1
VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
125000005046 dihydronaphthyl group Chemical group 0.000 description 1
125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 description 1
125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
239000000539 dimer Substances 0.000 description 1
125000005879 dioxolanyl group Chemical group 0.000 description 1
230000005750 disease progression Effects 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
239000003136 dopamine receptor stimulating agent Substances 0.000 description 1
239000012636 effector Substances 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
239000002532 enzyme inhibitor Substances 0.000 description 1
229960002179 ephedrine Drugs 0.000 description 1
210000002615 epidermis Anatomy 0.000 description 1
229960005139 epinephrine Drugs 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
UVCLSOSCOBDAOJ-UHFFFAOYSA-N ethyl 4-[3-ethyl-1-(4-fluorophenyl)indazol-6-yl]-4-hydroxycyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OCC)CCC1(O)C1=CC=C(C(CC)=NN2C=3C=CC(F)=CC=3)C2=C1 UVCLSOSCOBDAOJ-UHFFFAOYSA-N 0.000 description 1
PNNVKHPICCNMIV-UHFFFAOYSA-N ethyl 4-[3-ethyl-1-(4-fluorophenyl)indazol-6-yl]cyclohex-3-ene-1-carboxylate Chemical compound C1C(C(=O)OCC)CCC(C=2C=C3N(C=4C=CC(F)=CC=4)N=C(CC)C3=CC=2)=C1 PNNVKHPICCNMIV-UHFFFAOYSA-N 0.000 description 1
YFQVGIOCBQEVGB-UHFFFAOYSA-N ethyl 4-cyano-4-(1-cyclohexyl-3-ethylindazol-6-yl)cyclohexane-1-carboxylate Chemical compound C1CC(C(=O)OCC)CCC1(C#N)C1=CC=C(C(CC)=NN2C3CCCCC3)C2=C1 YFQVGIOCBQEVGB-UHFFFAOYSA-N 0.000 description 1
230000006355 external stress Effects 0.000 description 1
ITAMRBIZWGDOHW-UHFFFAOYSA-N fantofarone Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCOC1=CC=C(S(=O)(=O)C2=C3C=CC=CN3C=C2C(C)C)C=C1 ITAMRBIZWGDOHW-UHFFFAOYSA-N 0.000 description 1
229950009236 fantofarone Drugs 0.000 description 1
239000000835 fiber Substances 0.000 description 1
210000000540 fraction c Anatomy 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
230000004116 glycogenolysis Effects 0.000 description 1
208000024908 graft versus host disease Diseases 0.000 description 1
230000012010 growth Effects 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000033444 hydroxylation Effects 0.000 description 1
238000005805 hydroxylation reaction Methods 0.000 description 1
210000000987 immune system Anatomy 0.000 description 1
230000007813 immunodeficiency Effects 0.000 description 1
230000006872 improvement Effects 0.000 description 1
LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 1
230000006698 induction Effects 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
230000028709 inflammatory response Effects 0.000 description 1
208000014674 injury Diseases 0.000 description 1
201000004332 intermediate coronary syndrome Diseases 0.000 description 1
208000028774 intestinal disease Diseases 0.000 description 1
210000004347 intestinal mucosa Anatomy 0.000 description 1
230000003834 intracellular effect Effects 0.000 description 1
201000010849 intracranial embolism Diseases 0.000 description 1
230000009545 invasion Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 description 1
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
239000010410 layer Substances 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
210000005228 liver tissue Anatomy 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
238000007726 management method Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229960001252 methamphetamine Drugs 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
244000005700 microbiome Species 0.000 description 1
230000003278 mimic effect Effects 0.000 description 1
125000002911 monocyclic heterocycle group Chemical group 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
230000036640 muscle relaxation Effects 0.000 description 1
239000002637 mydriatic agent Substances 0.000 description 1
230000002911 mydriatic effect Effects 0.000 description 1
LXSGLQWIWZCVRB-UHFFFAOYSA-N n-(1h-indol-5-yl)quinazolin-4-amine Chemical class C1=CC=C2C(NC=3C=C4C=CNC4=CC=3)=NC=NC2=C1 LXSGLQWIWZCVRB-UHFFFAOYSA-N 0.000 description 1
GYNAVKULVOETAD-UHFFFAOYSA-N n-phenoxyaniline Chemical compound C=1C=CC=CC=1NOC1=CC=CC=C1 GYNAVKULVOETAD-UHFFFAOYSA-N 0.000 description 1
MTSNDBYBIZSILH-UHFFFAOYSA-N n-phenylquinazolin-4-amine Chemical compound N=1C=NC2=CC=CC=C2C=1NC1=CC=CC=C1 MTSNDBYBIZSILH-UHFFFAOYSA-N 0.000 description 1
YDOIROSDACUFLW-UHFFFAOYSA-N naphthalene;quinoline Chemical compound C1=CC=CC2=CC=CC=C21.N1=CC=CC2=CC=CC=C21 YDOIROSDACUFLW-UHFFFAOYSA-N 0.000 description 1
150000002790 naphthalenes Chemical class 0.000 description 1
210000005036 nerve Anatomy 0.000 description 1
230000007383 nerve stimulation Effects 0.000 description 1
238000005457 optimization Methods 0.000 description 1
210000001428 peripheral nervous system Anatomy 0.000 description 1
229960001802 phenylephrine Drugs 0.000 description 1
SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
102000020233 phosphotransferase Human genes 0.000 description 1
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
230000035479 physiological effects, processes and functions Effects 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
230000001242 postsynaptic effect Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000002062 proliferating effect Effects 0.000 description 1
CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
WMBBDTKWKVKSEO-UHFFFAOYSA-N pyrrolidine;1,3-thiazolidine Chemical compound C1CCNC1.C1CSCN1 WMBBDTKWKVKSEO-UHFFFAOYSA-N 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 1
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
238000009790 rate-determining step (RDS) Methods 0.000 description 1
229940044601 receptor agonist Drugs 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
230000010410 reperfusion Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical group COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 1
229950005741 rolipram Drugs 0.000 description 1
210000003079 salivary gland Anatomy 0.000 description 1
230000007017 scission Effects 0.000 description 1
125000003607 serino group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 description 1
230000035939 shock Effects 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229940083542 sodium Drugs 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
210000005070 sphincter Anatomy 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
230000035882 stress Effects 0.000 description 1
238000005556 structure-activity relationship Methods 0.000 description 1
125000005504 styryl group Chemical group 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
210000002820 sympathetic nervous system Anatomy 0.000 description 1
229940064707 sympathomimetics Drugs 0.000 description 1
230000001839 systemic circulation Effects 0.000 description 1
150000003527 tetrahydropyrans Chemical group 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000005304 thiadiazolidinyl group Chemical group 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
230000032258 transport Effects 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000004417 unsaturated alkyl group Chemical group 0.000 description 1
230000002792 vascular Effects 0.000 description 1
210000005166 vasculature Anatomy 0.000 description 1
RYJXBGGBZJGVQF-UHFFFAOYSA-N veralipride Chemical compound COC1=CC(S(N)(=O)=O)=CC(C(=O)NCC2N(CCC2)CC=C)=C1OC RYJXBGGBZJGVQF-UHFFFAOYSA-N 0.000 description 1
229960001968 veralipride Drugs 0.000 description 1
229950005577 vesnarinone Drugs 0.000 description 1
230000035899 viability Effects 0.000 description 1
230000009385 viral infection Effects 0.000 description 1
230000003313 weakening effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pulmonology (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Indole Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

SK625-2000A 1997-11-04 1998-10-26 Indazole bioisostere replacement of catechol in therapeutically active compounds SK6252000A3 (en)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US6422897P	1997-11-04	1997-11-04
US6422997P	1997-11-04	1997-11-04
US6419897P	1997-11-04	1997-11-04
US6402497P	1997-11-04	1997-11-04
US6418797P	1997-11-04	1997-11-04
PCT/IB1998/001710 WO1999023077A1 (fr)	1997-11-04	1998-10-26	Remplacement bioisosthere du catechol par l'indazole dans des composes therapeutiquement actifs

Publications (1)

Publication Number	Publication Date
SK6252000A3 true SK6252000A3 (en)	2001-11-06

Family

ID=27535645

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK625-2000A SK6252000A3 (en)	1997-11-04	1998-10-26	Indazole bioisostere replacement of catechol in therapeutically active compounds

Country Status (29)

Country	Link
US (1)	US6391872B1 (fr)
EP (1)	EP1028946A1 (fr)
JP (1)	JP2001521926A (fr)
CN (1)	CN1284948A (fr)
AP (1)	AP910A (fr)
AR (1)	AR013746A1 (fr)
AU (1)	AU754734B2 (fr)
BG (1)	BG104450A (fr)
BR (1)	BR9813926A (fr)
CA (1)	CA2309150A1 (fr)
CZ (1)	CZ20001621A3 (fr)
DZ (1)	DZ2640A1 (fr)
EA (1)	EA200000488A1 (fr)
HR (1)	HRP20000253A2 (fr)
HU (1)	HUP0004150A3 (fr)
ID (1)	ID23921A (fr)
IL (1)	IL135900A0 (fr)
IS (1)	IS5465A (fr)
MA (1)	MA26563A1 (fr)
NO (1)	NO20002129L (fr)
NZ (1)	NZ503918A (fr)
OA (1)	OA11354A (fr)
PE (1)	PE129199A1 (fr)
PL (1)	PL340753A1 (fr)
SK (1)	SK6252000A3 (fr)
TN (1)	TNSN98200A1 (fr)
TR (1)	TR200001234T2 (fr)
WO (1)	WO1999023077A1 (fr)
YU (1)	YU25000A (fr)

Families Citing this family (50)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6716978B2 (en) *	1997-11-04	2004-04-06	Pfizer Inc	Therapeutically active compounds based on indazole bioisostere replacement of catechol in PDE4 inhibitors
UA71971C2 (en)	1999-06-04	2005-01-17	Agoron Pharmaceuticals Inc	Diaminothiazoles, composition based thereon, a method for modulation of protein kinases activity, a method for the treatment of diseases mediated by protein kinases
TWI262914B (en)	1999-07-02	2006-10-01	Agouron Pharma	Compounds and pharmaceutical compositions for inhibiting protein kinases
US7141581B2 (en)	1999-07-02	2006-11-28	Agouron Pharmaceuticals, Inc.	Indazole compounds and pharmaceutical compositions for inhibiting protein kinases, and methods for their use
PE20010306A1 (es) *	1999-07-02	2001-03-29	Agouron Pharma	Compuestos de indazol y composiciones farmaceuticas que los contienen utiles para la inhibicion de proteina kinasa
JP2001031549A (ja) *	1999-07-14	2001-02-06	Pola Chem Ind Inc	真皮コラーゲン線維束再構築剤及びそれを含有する化粧料
US6432979B1 (en)	1999-08-12	2002-08-13	American Cyanamid Company	Method of treating or inhibiting colonic polyps and colorectal cancer
JP2003507342A (ja) *	1999-08-12	2003-02-25	アメリカン・サイアナミド・カンパニー	結腸ポリープおよび直腸結腸癌の処置または抑制のためのｎｓａｉｄおよびｅｇｆｒキナーゼインヒビターを含有する組成物
YU54202A (sh)	2000-01-18	2006-01-16	Agouron Pharmaceuticals Inc.	Jedinjenja indazola, farmaceutske smeše i postupci za stimulisanje i inhibiranje ćelijske proliferacije
HN2001000008A (es)	2000-01-21	2003-12-11	Inc Agouron Pharmaceuticals	Compuesto de amida y composiciones farmaceuticas para inhibir proteinquinasas, y su modo de empleo
US7005443B1 (en) *	2000-03-17	2006-02-28	Alcon, Inc.	5-Hydroxy indazole derivatives for treating glaucoma
JP2004501083A (ja)	2000-04-18	2004-01-15	アゴーロン・ファーマシューティカルズ・インコーポレイテッド	プロテインキナーゼを阻害するためのピラゾール
AU2002255263B2 (en)	2001-04-16	2006-12-14	Eisai R&D Management Co., Ltd.	Novel 1H-indazole compound
NZ532278A (en)	2001-09-19	2006-02-24	Altana Pharma Ag	Combination of a PDE inhibitor and an NSAID
WO2003024456A1 (fr) *	2001-09-20	2003-03-27	Eisai Co., Ltd.	Methodes de traitement et de prevention des migraines
AU2003201149A1 (en) *	2002-02-13	2003-09-04	Koninklijke Philips Electronics N.V.	Integrated semiconductor optical device, method and apparatus for manufacturing such a device
US7972632B2 (en)	2003-02-28	2011-07-05	Unigen Pharmaceuticals, Inc.	Identification of Free-B-Ring flavonoids as potent COX-2 inhibitors
US7108868B2 (en)	2002-03-22	2006-09-19	Unigen Pharmaceuticals, Inc.	Isolation of a dual cox-2 and 5-lipoxygenase inhibitor from acacia
US8034387B2 (en)	2002-04-30	2011-10-11	Unigen, Inc.	Formulation of a mixture of free-B-ring flavonoids and flavans for use in the prevention and treatment of cognitive decline and age-related memory impairments
EP2108370A1 (fr) *	2002-04-30	2009-10-14	Unigen Pharmaceuticals, Inc.	Formulation d'un mélange de flavonoïdes et de flavanes à cycle B libre et de flavanes en tant qu'agent thérapeutique
BR0316950A (pt)	2002-12-02	2006-01-17	Hoffmann La Roche	Derivados de indazol como antagonistas de crf
BRPI0407253A (pt) *	2003-02-14	2006-01-31	Wyeth Corp	Heterociclil-3-sulfonilindazóis como ligandos 5-hidroxitriptamina-6 processo de preparação dos mesmos, seus usos na preparação de uma composição farmacêutica e composição farmacêutica compreendendo os referidos compostos
US7135575B2 (en)	2003-03-03	2006-11-14	Array Biopharma, Inc.	P38 inhibitors and methods of use thereof
US20040220119A1 (en) *	2003-04-04	2004-11-04	Unigen Pharmaceuticals, Inc.	Formulation of dual cycloxygenase (COX) and lipoxygenase (LOX) inhibitors for mammal skin care
US6984652B2 (en) *	2003-09-05	2006-01-10	Warner-Lambert Company Llc	Gyrase inhibitors
RU2006134022A (ru)	2004-02-27	2008-04-10	Ф.Хоффманн-Ля Рош Аг (Ch)	Производные индазола и содержащие их фармацевтические композиции
US7844309B2 (en) *	2004-02-27	2010-11-30	Nokia Corporation	Exchangeable keymat
CA2557575A1 (fr)	2004-02-27	2005-09-15	F. Hoffmann-La Roche Ag	Derives fusionnes de pyrazole
CA2558109A1 (fr)	2004-02-27	2005-09-15	F. Hoffmann-La Roche Ag	Derives pyrazolo heteroaryl-condenses
US7601847B2 (en)	2004-10-26	2009-10-13	Wyeth	Preparation and purification of 4-(indazol-3-yl)phenols
CN101111494A (zh) *	2004-11-29	2008-01-23	沃纳-兰伯特有限公司	具有治疗作用的吡唑并[3,4-b]吡啶和吲唑
NZ565872A (en) *	2005-08-15	2011-06-30	Wyeth Corp	Substituted-3-sulfonylindazole derivatives as 5-hydroxytryptamine-6 ligands
WO2007032833A1 (fr) *	2005-08-15	2007-03-22	Wyeth	Dérivés d’azinyl-3-sulfonylindazole en tant que ligands de 5-hydroxytryptamine-6
WO2007023111A2 (fr)	2005-08-25	2007-03-01	F. Hoffmann-La Roche Ag	Inhibiteurs de la map-kinase p38 et leurs methodes d'utilisation
EP1928866A1 (fr)	2005-09-05	2008-06-11	Ranbaxy Laboratories Limited	Indazoles substitues utilises en tant qu'inhibiteurs de phosphodiesterase de type-iv
US7915286B2 (en)	2005-09-16	2011-03-29	Ranbaxy Laboratories Limited	Substituted pyrazolo [3,4-b] pyridines as phosphodiesterase inhibitors
EP2628725A1 (fr) *	2005-11-03	2013-08-21	Allergan, Inc.	Prostaglandines et analogues en tant qu'agents pour abaisser la pression intraoculaire
CN101370775A (zh)	2006-01-13	2009-02-18	惠氏公司	作为5-羟基色胺受体配体的经磺酰基取代1h-吲哚
SI1981851T1 (sl)	2006-01-31	2012-05-31	Array Biopharma Inc	Kinazni inhibitorji in postopki za njihovo uporabo
US7829713B2 (en)	2006-02-28	2010-11-09	Helicon Therapeutics, Inc.	Therapeutic piperazines
US8084485B2 (en)	2006-03-31	2011-12-27	Vitae Pharmaceuticals, Inc.	6-(aminoalkyl)indazoles
EP2001865A1 (fr) *	2006-04-05	2008-12-17	Wyeth a Corporation of the State of Delaware	Dérivés de sulfonyl-3-hétérocyclylindazole utilisés en tant que ligands de la 5-hydroxytryptamine-6
WO2007120596A1 (fr) *	2006-04-12	2007-10-25	Wyeth	DÉRIVÉS DE DIHYDRO[1,4]DIOXINO[2,3-e]INDAZOLE EN TANT QUE LIGANDS DE 5-HYDROXYTRYPTAMINE-6
US8012886B2 (en) *	2007-03-07	2011-09-06	Asm Assembly Materials Ltd	Leadframe treatment for enhancing adhesion of encapsulant thereto
SI2124944T1 (sl)	2007-03-14	2012-05-31	Ranbaxy Lab Ltd	Derivati pirazolo b piridina kot inhibitorji fosfodiesteraze
US8558016B2 (en) *	2009-09-18	2013-10-15	Kabaushiki Kaisha Riverson	Polyphenol derivative and method for producing the same
EP2569301A1 (fr)	2010-05-12	2013-03-20	Abbvie Inc.	Inhibiteurs indazoliques des kinases
CN103709146B (zh) *	2014-01-15	2015-11-25	中国药科大学	一类含苯并咪唑结构的喹啉-4-胺衍生物、其制法及医药用途
US12441707B2 (en)	2019-12-30	2025-10-14	Tyra Biosciences, Inc.	Indazole compounds
MX2023007793A (es)	2020-12-30	2023-09-22	Tyra Biosciences Inc	Compuestos de indazol como inhibidores de cinasas.

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0338087A4 (en) *	1987-10-13	1991-07-24	Yoshitomi Pharmaceutical Industries, Ltd.	Fused pyrazole compounds, process for their preparation, and their medicinal use
WO1989003385A1 (fr) *	1987-10-13	1989-04-20	Yoshitomi Pharmaceutical Industries, Ltd.	Composes de pyrazole fusionnes, procede de preparation et utilisation en medecine
US5593997A (en) *	1995-05-23	1997-01-14	Pfizer Inc.	4-aminopyrazolo(3-,4-D)pyrimidine and 4-aminopyrazolo-(3,4-D)pyridine tyrosine kinase inhibitors
AP1147A (en) *	1996-05-03	2003-02-25	Pfizer	Substituted indazole derivatives and related compounds.
EP0912558B1 (fr) *	1996-06-25	2003-07-09	Pfizer Inc.	Derives d'indazole substitues et leur utilisation en tant qu'inhibiteurs de phosphodiesterase (pde) type iv et du facteur de necrose tumorale (tnf)
DE69709493T2 (de) *	1996-06-27	2002-10-31	Pfizer Inc., New York	Substituierte Indazolderivate
CA2264798A1 (fr) *	1996-09-04	1998-03-12	Pfizer Inc.	Derives d'indazole et leur utilisation en tant qu'inhibiteurs de phosphodiesterase (pde) de type iv et de la production du facteur de necrose des tumeurs (tnf)
US6716978B2 (en) *	1997-11-04	2004-04-06	Pfizer Inc	Therapeutically active compounds based on indazole bioisostere replacement of catechol in PDE4 inhibitors

1998
- 1998-10-26 US US09/381,425 patent/US6391872B1/en not_active Expired - Fee Related
- 1998-10-26 HR HR20000253A patent/HRP20000253A2/hr not_active Application Discontinuation
- 1998-10-26 SK SK625-2000A patent/SK6252000A3/sk unknown
- 1998-10-26 EP EP98947732A patent/EP1028946A1/fr not_active Withdrawn
- 1998-10-26 AU AU94552/98A patent/AU754734B2/en not_active Ceased
- 1998-10-26 WO PCT/IB1998/001710 patent/WO1999023077A1/fr not_active Ceased
- 1998-10-26 ID IDW20000819A patent/ID23921A/id unknown
- 1998-10-26 JP JP2000518952A patent/JP2001521926A/ja active Pending
- 1998-10-26 BR BR9813926-6A patent/BR9813926A/pt not_active IP Right Cessation
- 1998-10-26 CN CN98812929A patent/CN1284948A/zh active Pending
- 1998-10-26 HU HU0004150A patent/HUP0004150A3/hu unknown
- 1998-10-26 EA EA200000488A patent/EA200000488A1/ru unknown
- 1998-10-26 PL PL98340753A patent/PL340753A1/xx not_active Application Discontinuation
- 1998-10-26 IL IL13590098A patent/IL135900A0/xx unknown
- 1998-10-26 TR TR2000/01234T patent/TR200001234T2/xx unknown
- 1998-10-26 CA CA002309150A patent/CA2309150A1/fr not_active Abandoned
- 1998-10-26 CZ CZ20001621A patent/CZ20001621A3/cs unknown
- 1998-10-26 YU YU25000A patent/YU25000A/sh unknown
- 1998-10-26 NZ NZ503918A patent/NZ503918A/en unknown
- 1998-10-29 AP APAP/P/1998/001375A patent/AP910A/en active
- 1998-11-03 TN TNTNSN98200A patent/TNSN98200A1/fr unknown
- 1998-11-03 DZ DZ980250A patent/DZ2640A1/fr active
- 1998-11-03 AR ARP980105534A patent/AR013746A1/es not_active Application Discontinuation
- 1998-11-03 MA MA25332A patent/MA26563A1/fr unknown
- 1998-11-03 PE PE1998001041A patent/PE129199A1/es not_active Application Discontinuation
2000
- 2000-04-19 IS IS5465A patent/IS5465A/is unknown
- 2000-04-26 NO NO20002129A patent/NO20002129L/no not_active Application Discontinuation
- 2000-04-28 OA OA1200000127A patent/OA11354A/en unknown
- 2000-05-17 BG BG104450A patent/BG104450A/xx unknown

Also Published As

Publication number	Publication date
PL340753A1 (en)	2001-02-26
IS5465A (is)	2000-04-19
TNSN98200A1 (fr)	2005-03-15
TR200001234T2 (tr)	2000-08-21
DZ2640A1 (fr)	2003-03-08
WO1999023077A1 (fr)	1999-05-14
EA200000488A1 (ru)	2000-10-30
NO20002129L (no)	2000-07-03
AU9455298A (en)	1999-05-24
OA11354A (en)	2003-12-23
HUP0004150A2 (hu)	2001-05-28
NO20002129D0 (no)	2000-04-26
JP2001521926A (ja)	2001-11-13
IL135900A0 (en)	2001-05-20
HUP0004150A3 (en)	2001-08-28
YU25000A (sh)	2003-12-31
BR9813926A (pt)	2000-09-19
ID23921A (id)	2000-05-25
CA2309150A1 (fr)	1999-05-14
EP1028946A1 (fr)	2000-08-23
CZ20001621A3 (cs)	2001-08-15
AP910A (en)	2000-12-05
NZ503918A (en)	2002-03-28
US6391872B1 (en)	2002-05-21
BG104450A (en)	2000-12-29
MA26563A1 (fr)	2004-12-20
AP9801375A0 (en)	1998-12-31
CN1284948A (zh)	2001-02-21
HRP20000253A2 (en)	2001-06-30
PE129199A1 (es)	1999-12-16
AU754734B2 (en)	2002-11-21
AR013746A1 (es)	2001-01-10

Publication	Publication Date	Title
SK6252000A3 (en)	2001-11-06	Indazole bioisostere replacement of catechol in therapeutically active compounds
CN113717156B (zh)	2023-05-09	Egfr抑制剂、其制备方法及用途
JP4685243B2 (ja)	2011-05-18	ピリミド［６，１−ａ］イソキノリン−４−オン誘導体
ES2821018T3 (es)	2021-04-23	Nuevos agentes antiinflamatorios
RU2518073C2 (ru)	2014-06-10	Новое бициклическое гетероциклическое соединение
AU2002364549B2 (en)	2007-11-22	Vanilloid receptor ligands and their use in treatments
WO2007101270A1 (fr)	2007-09-07	MODULATEURS DE LA 11β-HYDROXYSTEROIDE DESHYDROGENASE DE TYPE 1, COMPOSITIONS PHARMACEUTIQUES LES COMPRENANT ET PROCEDE D'UTILISATION DESDITS MODULATEURS
SK6262000A3 (en)	2002-03-05	Therapeutically active compounds based on indazole bioisostere replacement of catechol in pde4 inhibitors
JPWO2020017587A1 (ja)	2021-08-05	ピリダジノン誘導体
MXPA03009083A (es)	2004-11-22	Tiohidantoinas y su utilizacion en el tratamiento de diabetes.
CZ300754B6 (cs)	2009-08-05	Arylsulfonamidy a jejich analogy, zpusob jejich výroby, meziprodukty pro jejich výrobu, farmaceutické prostredky tyto látky obsahující a jejich použití
EP3200589B1 (fr)	2026-03-11	Nouveaux modulateurs de l'activité du récepteur de 5-hydroxytryptamine 7 et leur procédé d'utilisation
CA2870062A1 (fr)	2013-12-27	Inhibiteurs de tankyrase de type pyrrolopyrazone
JP2009538358A (ja)	2009-11-05	脂肪酸アミド加水分解酵素のオキサゾリルピペリジン・モジュレーター
DE4101686A1 (de)	1992-07-23	Indolderivate
EP3738955A1 (fr)	2020-11-18	Nouveaux modulateurs de l'activité du récepteur 7 de la 5-hydroxytryptamine et leur procédé d'utilisation
EP1830852A2 (fr)	2007-09-12	Composes a activite a la fois inhibitrice de la pde et antagoniste ou agoniste partielle des recepteurs beta-adrenergiques pour le traitement de l'insuffisance cardiaque
JPH0550512B2 (fr)	1993-07-29
CA3161590A1 (fr)	2021-05-20	Nouvelles lactones fonctionnalisees constituant des modulateurs du recepteur de la 5-hydroxytryptamine 7 et leur procede d'utilisation
TW200533351A (en)	2005-10-16	Compounds for the treatment of diseases
WO2011148956A1 (fr)	2011-12-01	Dérivé d'imidazole condensé
US7456208B2 (en)	2008-11-25	CCK-1 receptor modulators
DE4226527A1 (de)	1994-02-17	1,4-Benzodioxanderivate
Gao et al.	2019	Design, synthesis and biological evaluation of N1-(isoquinolin-5-yl)-N2-phenylpyrrolidine-1, 2-dicarboxamide derivatives as potent TRPV1 antagonists
WO2019105234A1 (fr)	2019-06-06	Composé aromatique, composition pharmaceutique et utilisation associées