OA11354A - 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: OA11354A
Authority: OA; OAPI
Prior art keywords: group; alkyl; consisting essentially; independently selected; hydrogen
Prior art date: 1997-11-04

Application number

OA1200000127A

Other languages

English (en)

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

2000-04-28

Publication date

2003-12-23

2000-04-28 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2003-12-23 Publication of OA11354A publication Critical patent/OA11354A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 328
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 title claims abstract description 122
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title claims abstract description 94
239000001257 hydrogen Substances 0.000 claims abstract description 247
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 247
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 214
150000003839 salts Chemical class 0.000 claims abstract description 59
230000000694 effects Effects 0.000 claims abstract description 46
230000001225 therapeutic effect Effects 0.000 claims abstract description 40
239000000203 mixture Substances 0.000 claims abstract description 39
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 26
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 19
230000002401 inhibitory effect Effects 0.000 claims abstract description 15
239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims abstract description 15
230000000118 anti-neoplastic effect Effects 0.000 claims abstract description 9
108090000312 Calcium Channels Proteins 0.000 claims abstract description 7
102000003922 Calcium Channels Human genes 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims description 377
-1 heterocyciyl Chemical group 0.000 claims description 286
125000001424 substituent group Chemical group 0.000 claims description 160
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 142
230000036961 partial effect Effects 0.000 claims description 137
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 95
125000003545 alkoxy group Chemical group 0.000 claims description 90
125000001246 bromo group Chemical group Br* 0.000 claims description 75
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 73
125000001309 chloro group Chemical group Cl* 0.000 claims description 72
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 59
125000001153 fluoro group Chemical group F* 0.000 claims description 59
125000003118 aryl group Chemical group 0.000 claims description 56
201000010099 disease Diseases 0.000 claims description 56
238000011282 treatment Methods 0.000 claims description 47
229940002612 prodrug Drugs 0.000 claims description 46
239000000651 prodrug Substances 0.000 claims description 46
125000000623 heterocyclic group Chemical group 0.000 claims description 45
229910052760 oxygen Inorganic materials 0.000 claims description 44
238000000034 method Methods 0.000 claims description 43
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 42
125000003342 alkenyl group Chemical group 0.000 claims description 39
125000004093 cyano group Chemical group *C#N 0.000 claims description 39
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 38
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 38
125000004076 pyridyl group Chemical group 0.000 claims description 35
229910052717 sulfur Inorganic materials 0.000 claims description 34
229910052799 carbon Inorganic materials 0.000 claims description 33
125000005842 heteroatom Chemical group 0.000 claims description 33
239000003795 chemical substances by application Substances 0.000 claims description 30
125000002883 imidazolyl group Chemical group 0.000 claims description 27
125000000714 pyrimidinyl group Chemical group 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 26
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 26
125000002971 oxazolyl group Chemical group 0.000 claims description 25
239000008194 pharmaceutical composition Substances 0.000 claims description 25
125000003226 pyrazolyl group Chemical group 0.000 claims description 25
125000000335 thiazolyl group Chemical group 0.000 claims description 25
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 24
150000002431 hydrogen Chemical class 0.000 claims description 24
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 23
150000001721 carbon Chemical class 0.000 claims description 22
125000001544 thienyl group Chemical group 0.000 claims description 22
229940127291 Calcium channel antagonist Drugs 0.000 claims description 21
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
208000006673 asthma Diseases 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 21
239000000556 agonist Substances 0.000 claims description 20
125000003282 alkyl amino group Chemical group 0.000 claims description 20
239000005557 antagonist Substances 0.000 claims description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 19
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 19
125000001425 triazolyl group Chemical group 0.000 claims description 19
229910052731 fluorine Inorganic materials 0.000 claims description 18
125000002541 furyl group Chemical group 0.000 claims description 18
229910052757 nitrogen Inorganic materials 0.000 claims description 18
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 17
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 17
125000002947 alkylene group Chemical group 0.000 claims description 17
239000000460 chlorine Substances 0.000 claims description 17
229910052801 chlorine Inorganic materials 0.000 claims description 17
239000011737 fluorine Substances 0.000 claims description 17
125000003386 piperidinyl group Chemical group 0.000 claims description 17
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 16
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 16
125000002632 imidazolidinyl group Chemical group 0.000 claims description 16
239000003112 inhibitor Substances 0.000 claims description 16
125000003831 tetrazolyl group Chemical group 0.000 claims description 16
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 15
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 15
125000002757 morpholinyl group Chemical group 0.000 claims description 15
125000004193 piperazinyl group Chemical group 0.000 claims description 15
125000000168 pyrrolyl group Chemical group 0.000 claims description 15
125000004429 atom Chemical group 0.000 claims description 14
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 14
125000001113 thiadiazolyl group Chemical group 0.000 claims description 14
125000000842 isoxazolyl group Chemical group 0.000 claims description 13
125000001715 oxadiazolyl group Chemical group 0.000 claims description 13
125000000160 oxazolidinyl group Chemical group 0.000 claims description 13
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 12
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 12
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 11
229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 11
230000001800 adrenalinergic effect Effects 0.000 claims description 11
125000001589 carboacyl group Chemical group 0.000 claims description 11
125000002837 carbocyclic group Chemical group 0.000 claims description 11
125000001041 indolyl group Chemical group 0.000 claims description 11
208000027866 inflammatory disease Diseases 0.000 claims description 11
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims description 11
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 11
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 10
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
229910052792 caesium Inorganic materials 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 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
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 10
125000003373 pyrazinyl group Chemical group 0.000 claims description 10
125000003072 pyrazolidinyl group Chemical group 0.000 claims description 10
125000002098 pyridazinyl group Chemical group 0.000 claims description 10
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 10
150000003254 radicals Chemical class 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
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 9
125000005605 benzo group Chemical group 0.000 claims description 9
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 9
229910052794 bromium Inorganic materials 0.000 claims description 9
239000000544 cholinesterase inhibitor Substances 0.000 claims description 9
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 9
239000003446 ligand 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
125000001984 thiazolidinyl group Chemical group 0.000 claims description 9
125000004568 thiomorpholinyl group Chemical group 0.000 claims description 9
125000004306 triazinyl group Chemical group 0.000 claims description 9
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 8
125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 8
125000005236 alkanoylamino group Chemical group 0.000 claims description 8
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 8
125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
125000001072 heteroaryl group Chemical group 0.000 claims description 8
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 8
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 8
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 8
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 8
125000001786 isothiazolyl group Chemical group 0.000 claims description 8
125000000466 oxiranyl group Chemical group 0.000 claims description 8
125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 claims description 8
125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 claims description 8
125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 claims description 8
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 8
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 8
125000002755 pyrazolinyl group Chemical group 0.000 claims description 8
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 8
RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 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
VXPGKSAYOBZMSX-UHFFFAOYSA-N 1,3-dioxane;1,3-dioxolane Chemical compound C1COCO1.C1COCOC1 VXPGKSAYOBZMSX-UHFFFAOYSA-N 0.000 claims description 7
WJJSZTJGFCFNKI-UHFFFAOYSA-N 1,3-oxathiolane Chemical compound C1CSCO1 WJJSZTJGFCFNKI-UHFFFAOYSA-N 0.000 claims description 7
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 7
125000005530 alkylenedioxy group Chemical group 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
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 7
239000000812 cholinergic antagonist Substances 0.000 claims description 7
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 7
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims description 7
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 7
125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 6
IMHJVJUMANXYCI-UHFFFAOYSA-N 1,3-dithiane;1,3-dithiolane Chemical compound C1CSCS1.C1CSCSC1 IMHJVJUMANXYCI-UHFFFAOYSA-N 0.000 claims description 6
NARVIWMVBMUEOG-UHFFFAOYSA-N 2-Hydroxy-propylene Natural products CC(O)=C NARVIWMVBMUEOG-UHFFFAOYSA-N 0.000 claims description 6
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 6
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 6
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 6
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 6
125000002636 imidazolinyl group Chemical group 0.000 claims description 6
230000000241 respiratory effect Effects 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
125000005955 1H-indazolyl group Chemical group 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 5
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
125000003368 amide group Chemical group 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 5
125000002619 bicyclic group Chemical group 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 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
229930192474 thiophene Natural products 0.000 claims description 5
125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 4
125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 4
LQPOOAJESJYDLS-UHFFFAOYSA-N 1,3-oxazinane Chemical compound C1CNCOC1 LQPOOAJESJYDLS-UHFFFAOYSA-N 0.000 claims description 4
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 4
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 4
IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 4
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 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
125000002471 4H-quinolizinyl group Chemical group C=1(C=CCN2C=CC=CC12)* 0.000 claims description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
229910052684 Cerium Inorganic materials 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
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 4
150000001408 amides Chemical class 0.000 claims description 4
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 4
125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 4
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
229940097043 glucuronic acid Drugs 0.000 claims description 4
125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
125000002950 monocyclic group Chemical group 0.000 claims description 4
AHKJGIUKIBGOKH-UHFFFAOYSA-N morpholine;piperidine Chemical compound C1CCNCC1.C1COCCN1 AHKJGIUKIBGOKH-UHFFFAOYSA-N 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 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
OIMWEHOYHJJPJD-UHFFFAOYSA-N pyridine;pyrimidine Chemical compound C1=CC=NC=C1.C1=CN=CN=C1 OIMWEHOYHJJPJD-UHFFFAOYSA-N 0.000 claims description 4
125000000446 sulfanediyl group Chemical group *S* 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
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 4
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 4
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 3
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 3
125000005940 1,4-dioxanyl group Chemical group 0.000 claims description 3
101100294113 Caenorhabditis elegans nhr-48 gene Proteins 0.000 claims description 3
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
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 3
125000005879 dioxolanyl group Chemical group 0.000 claims description 3
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238000012546 transfer Methods 0.000 description 1
229960005294 triamcinolone Drugs 0.000 description 1
GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
229960005345 trimebutine Drugs 0.000 description 1
125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
125000004417 unsaturated alkyl group Chemical group 0.000 description 1
229940093257 valacyclovir Drugs 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
229940088594 vitamin Drugs 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
238000010792 warming Methods 0.000 description 1
235000019386 wax ester Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
239000003357 wound healing promoting agent Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 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)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Pulmonology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

OA1200000127A 1997-11-04 2000-04-28 Indazole bioisostere replacement of catechol in therapeutically active compounds. OA11354A (en)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date
US6422997P	1997-11-04	1997-11-04
US6422897P	1997-11-04	1997-11-04
US6419897P	1997-11-04	1997-11-04
US6418797P	1997-11-04	1997-11-04
US6402497P	1997-11-04	1997-11-04

Publications (1)

Publication Number	Publication Date
OA11354A true OA11354A (en)	2003-12-23

Family

ID=27535645

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200000127A OA11354A (en)	1997-11-04	2000-04-28	Indazole bioisostere replacement of catechol in therapeutically active compounds.

Country Status (29)

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

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1998
- 1998-10-26 PL PL98340753A patent/PL340753A1/xx not_active Application Discontinuation
- 1998-10-26 YU YU25000A patent/YU25000A/sh unknown
- 1998-10-26 WO PCT/IB1998/001710 patent/WO1999023077A1/en not_active Ceased
- 1998-10-26 EP EP98947732A patent/EP1028946A1/en not_active Withdrawn
- 1998-10-26 JP JP2000518952A patent/JP2001521926A/ja active Pending
- 1998-10-26 US US09/381,425 patent/US6391872B1/en not_active Expired - Fee Related
- 1998-10-26 AU AU94552/98A patent/AU754734B2/en not_active Ceased
- 1998-10-26 CA CA002309150A patent/CA2309150A1/en not_active Abandoned
- 1998-10-26 BR BR9813926-6A patent/BR9813926A/pt not_active IP Right Cessation
- 1998-10-26 SK SK625-2000A patent/SK6252000A3/sk unknown
- 1998-10-26 EA EA200000488A patent/EA200000488A1/ru unknown
- 1998-10-26 CN CN98812929A patent/CN1284948A/zh active Pending
- 1998-10-26 IL IL13590098A patent/IL135900A0/xx unknown
- 1998-10-26 HR HR20000253A patent/HRP20000253A2/hr not_active Application Discontinuation
- 1998-10-26 NZ NZ503918A patent/NZ503918A/en unknown
- 1998-10-26 CZ CZ20001621A patent/CZ20001621A3/cs unknown
- 1998-10-26 ID IDW20000819A patent/ID23921A/id unknown
- 1998-10-26 HU HU0004150A patent/HUP0004150A3/hu unknown
- 1998-10-26 TR TR2000/01234T patent/TR200001234T2/xx unknown
- 1998-10-29 AP APAP/P/1998/001375A patent/AP910A/en active
- 1998-11-03 DZ DZ980250A patent/DZ2640A1/xx active
- 1998-11-03 MA MA25332A patent/MA26563A1/fr unknown
- 1998-11-03 TN TNTNSN98200A patent/TNSN98200A1/fr unknown
- 1998-11-03 PE PE1998001041A patent/PE129199A1/es not_active Application Discontinuation
- 1998-11-03 AR ARP980105534A patent/AR013746A1/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
CN1284948A (zh)	2001-02-21
SK6252000A3 (en)	2001-11-06
HUP0004150A2 (hu)	2001-05-28
EA200000488A1 (ru)	2000-10-30
ID23921A (id)	2000-05-25
AP9801375A0 (en)	1998-12-31
HUP0004150A3 (en)	2001-08-28
NO20002129L (no)	2000-07-03
BR9813926A (pt)	2000-09-19
AU754734B2 (en)	2002-11-21
PL340753A1 (en)	2001-02-26
EP1028946A1 (en)	2000-08-23
BG104450A (en)	2000-12-29
TNSN98200A1 (fr)	2005-03-15
NO20002129D0 (no)	2000-04-26
DZ2640A1 (fr)	2003-03-08
IL135900A0 (en)	2001-05-20
YU25000A (sh)	2003-12-31
HRP20000253A2 (en)	2001-06-30
AR013746A1 (es)	2001-01-10
TR200001234T2 (tr)	2000-08-21
CZ20001621A3 (cs)	2001-08-15
US6391872B1 (en)	2002-05-21
JP2001521926A (ja)	2001-11-13
AP910A (en)	2000-12-05
NZ503918A (en)	2002-03-28
CA2309150A1 (en)	1999-05-14
MA26563A1 (fr)	2004-12-20
WO1999023077A1 (en)	1999-05-14
PE129199A1 (es)	1999-12-16
AU9455298A (en)	1999-05-24
IS5465A (is)	2000-04-19

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