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
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- 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

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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Pulmonology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (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
US6402497P	1997-11-04	1997-11-04
US6422997P	1997-11-04	1997-11-04
US6418797P	1997-11-04	1997-11-04
US6422897P	1997-11-04	1997-11-04
US6419897P	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)

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1998
- 1998-10-26 IL IL13590098A patent/IL135900A0/xx unknown
- 1998-10-26 EP EP98947732A patent/EP1028946A1/fr not_active Withdrawn
- 1998-10-26 SK SK625-2000A patent/SK6252000A3/sk unknown
- 1998-10-26 HU HU0004150A patent/HUP0004150A3/hu unknown
- 1998-10-26 AU AU94552/98A patent/AU754734B2/en not_active Ceased
- 1998-10-26 CZ CZ20001621A patent/CZ20001621A3/cs unknown
- 1998-10-26 CN CN98812929A patent/CN1284948A/zh active Pending
- 1998-10-26 JP JP2000518952A patent/JP2001521926A/ja active Pending
- 1998-10-26 HR HR20000253A patent/HRP20000253A2/hr not_active Application Discontinuation
- 1998-10-26 WO PCT/IB1998/001710 patent/WO1999023077A1/fr not_active Ceased
- 1998-10-26 PL PL98340753A patent/PL340753A1/xx not_active Application Discontinuation
- 1998-10-26 TR TR2000/01234T patent/TR200001234T2/xx unknown
- 1998-10-26 YU YU25000A patent/YU25000A/sh unknown
- 1998-10-26 ID IDW20000819A patent/ID23921A/id unknown
- 1998-10-26 CA CA002309150A patent/CA2309150A1/fr not_active Abandoned
- 1998-10-26 BR BR9813926-6A patent/BR9813926A/pt not_active IP Right Cessation
- 1998-10-26 US US09/381,425 patent/US6391872B1/en not_active Expired - Fee Related
- 1998-10-26 EA EA200000488A patent/EA200000488A1/ru 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 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
- 1998-11-03 DZ DZ980250A patent/DZ2640A1/fr active
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
HRP20000253A2 (en)	2001-06-30
MA26563A1 (fr)	2004-12-20
NO20002129D0 (no)	2000-04-26
HUP0004150A3 (en)	2001-08-28
DZ2640A1 (fr)	2003-03-08
WO1999023077A1 (fr)	1999-05-14
NO20002129L (no)	2000-07-03
BR9813926A (pt)	2000-09-19
AR013746A1 (es)	2001-01-10
EP1028946A1 (fr)	2000-08-23
PL340753A1 (en)	2001-02-26
CZ20001621A3 (cs)	2001-08-15
CA2309150A1 (fr)	1999-05-14
ID23921A (id)	2000-05-25
YU25000A (sh)	2003-12-31
NZ503918A (en)	2002-03-28
US6391872B1 (en)	2002-05-21
AP9801375A0 (en)	1998-12-31
IS5465A (is)	2000-04-19
IL135900A0 (en)	2001-05-20
BG104450A (en)	2000-12-29
TR200001234T2 (tr)	2000-08-21
JP2001521926A (ja)	2001-11-13
AU9455298A (en)	1999-05-24
TNSN98200A1 (fr)	2005-03-15
CN1284948A (zh)	2001-02-21
HUP0004150A2 (hu)	2001-05-28
EA200000488A1 (ru)	2000-10-30
PE129199A1 (es)	1999-12-16
AP910A (en)	2000-12-05
AU754734B2 (en)	2002-11-21
OA11354A (en)	2003-12-23

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
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CA2585797C (fr)	2015-01-06	Composes de lactame et leur utilisation en temps que substances pharmaceutiques
ES2821018T3 (es)	2021-04-23	Nuevos agentes antiinflamatorios
RU2518073C2 (ru)	2014-06-10	Новое бициклическое гетероциклическое соединение
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
CA2468544A1 (fr)	2003-06-19	Ligands de recepteur vanilloide et utilisation de ceux-ci dans des traitements
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
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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
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CA3161590A1 (fr)	2021-05-20	Nouvelles lactones fonctionnalisees constituant des modulateurs du recepteur de la 5-hydroxytryptamine 7 et leur procede d'utilisation
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