ZA200403240B - Therapeutic isoquinoline compounds. - Google Patents
Therapeutic isoquinoline compounds. Download PDFInfo
- Publication number
- ZA200403240B ZA200403240B ZA200403240A ZA200403240A ZA200403240B ZA 200403240 B ZA200403240 B ZA 200403240B ZA 200403240 A ZA200403240 A ZA 200403240A ZA 200403240 A ZA200403240 A ZA 200403240A ZA 200403240 B ZA200403240 B ZA 200403240B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- aryl
- composition
- integer selected
- recited
- Prior art date
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- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title claims 2
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 125000000623 heterocyclic group Chemical group 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 24
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 206010012289 Dementia Diseases 0.000 claims description 4
- 208000030814 Eating disease Diseases 0.000 claims description 4
- 208000017701 Endocrine disease Diseases 0.000 claims description 4
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 4
- 208000019430 Motor disease Diseases 0.000 claims description 4
- 206010047163 Vasospasm Diseases 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 235000014632 disordered eating Nutrition 0.000 claims description 4
- 208000037870 generalized anxiety Diseases 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 208000019906 panic disease Diseases 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 208000019116 sleep disease Diseases 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 3
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 5
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 2
- 208000020401 Depressive disease Diseases 0.000 claims 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 240000008042 Zea mays Species 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- -1 ISOQUINOLINE COMPOUNDS Chemical class 0.000 description 25
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 5
- CBWFYDBQVWIORH-UHFFFAOYSA-N 5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-2-carboxylic acid Chemical compound C1=2CN(C(O)=O)CCC=2C(OC)=CC=C1N1CCN(C)CC1 CBWFYDBQVWIORH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 229940076279 serotonin Drugs 0.000 description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 2
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- RAYMXZBXQCGRGX-UHFFFAOYSA-N quinoline-5-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=N1 RAYMXZBXQCGRGX-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical compound C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 description 1
- DLUHKZZEEHQFAS-UHFFFAOYSA-N 1-[8-(4-methylpiperazin-1-yl)-5-phenylmethoxy-3,4-dihydro-1h-isoquinolin-2-yl]-2-(4-propan-2-ylphenyl)ethanone Chemical compound C1=CC(C(C)C)=CC=C1CC(=O)N1CC2=C(N3CCN(C)CC3)C=CC(OCC=3C=CC=CC=3)=C2CC1 DLUHKZZEEHQFAS-UHFFFAOYSA-N 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- YHCUZRJTNSWYCY-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1h-azepine Chemical compound C1CNCC=CC1 YHCUZRJTNSWYCY-UHFFFAOYSA-N 0.000 description 1
- OZIJESHLNXSUNE-UHFFFAOYSA-N 2,3-dihydrofuran;thiolane 1,1-dioxide Chemical compound C1CC=CO1.O=S1(=O)CCCC1 OZIJESHLNXSUNE-UHFFFAOYSA-N 0.000 description 1
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
- GSUPYHWEFVSXBA-UHFFFAOYSA-N 2,5-dihydrofuran;oxolane Chemical compound C1CCOC1.C1OCC=C1 GSUPYHWEFVSXBA-UHFFFAOYSA-N 0.000 description 1
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
- VMUXSMXIQBNMGZ-UHFFFAOYSA-N 3,4-dihydrocoumarin Chemical compound C1=CC=C2OC(=O)CCC2=C1 VMUXSMXIQBNMGZ-UHFFFAOYSA-N 0.000 description 1
- GOLORTLGFDVFDW-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2NC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 GOLORTLGFDVFDW-UHFFFAOYSA-N 0.000 description 1
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 description 1
- BAKUAUDFCNFLBX-UHFFFAOYSA-N 4,7-dihydro-1,3-dioxepine Chemical compound C1OCC=CCO1 BAKUAUDFCNFLBX-UHFFFAOYSA-N 0.000 description 1
- RLQPVZWUVYDRCF-UHFFFAOYSA-N 4-[2-[5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinolin-2-yl]-2-oxoethyl]-n,n-dimethylbenzenesulfonamide Chemical compound C1=2CN(C(=O)CC=3C=CC(=CC=3)S(=O)(=O)N(C)C)CCC=2C(OC)=CC=C1N1CCN(C)CC1 RLQPVZWUVYDRCF-UHFFFAOYSA-N 0.000 description 1
- HPXODHAETLLQAK-UHFFFAOYSA-N 4-[2-[5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinolin-2-yl]-2-oxoethyl]-n-[(2-methoxyphenyl)methyl]benzenesulfonamide Chemical compound COC1=CC=CC=C1CNS(=O)(=O)C(C=C1)=CC=C1CC(=O)N1CC2=C(N3CCN(C)CC3)C=CC(OC)=C2CC1 HPXODHAETLLQAK-UHFFFAOYSA-N 0.000 description 1
- IDSMZQMBPIKUEV-UHFFFAOYSA-N 4-[2-[5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinolin-2-yl]-2-oxoethyl]-n-propan-2-ylbenzenesulfonamide Chemical compound C1=2CN(C(=O)CC=3C=CC(=CC=3)S(=O)(=O)NC(C)C)CCC=2C(OC)=CC=C1N1CCN(C)CC1 IDSMZQMBPIKUEV-UHFFFAOYSA-N 0.000 description 1
- SEQAJKKHHDYWMK-UHFFFAOYSA-N 4-[2-[5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinolin-2-yl]-2-oxoethyl]-n-propylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCCC)=CC=C1CC(=O)N1CC2=C(N3CCN(C)CC3)C=CC(OC)=C2CC1 SEQAJKKHHDYWMK-UHFFFAOYSA-N 0.000 description 1
- GUJCQDJRUBKPDO-UHFFFAOYSA-N 4-amino-n-[(3-methoxyphenyl)methyl]benzenesulfonamide Chemical compound COC1=CC=CC(CNS(=O)(=O)C=2C=CC(N)=CC=2)=C1 GUJCQDJRUBKPDO-UHFFFAOYSA-N 0.000 description 1
- ZHKXBELKPQXYEH-UHFFFAOYSA-N 4-amino-n-benzylbenzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NCC1=CC=CC=C1 ZHKXBELKPQXYEH-UHFFFAOYSA-N 0.000 description 1
- KXZDFXPPYYWDLO-UHFFFAOYSA-N 4-amino-n-cyclobutylbenzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1CCC1 KXZDFXPPYYWDLO-UHFFFAOYSA-N 0.000 description 1
- KOLXPLAKQKRJLH-UHFFFAOYSA-N 4-amino-n-cyclopropylbenzenesulfonamide Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1CC1 KOLXPLAKQKRJLH-UHFFFAOYSA-N 0.000 description 1
- JCEYVRUMWHHLOJ-UHFFFAOYSA-N 4-methoxy-n-[4-[5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinolin-2-yl]-4-oxobutyl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NCCCC(=O)N1CC2=C(N3CCN(C)CC3)C=CC(OC)=C2CC1 JCEYVRUMWHHLOJ-UHFFFAOYSA-N 0.000 description 1
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
- MQUHMXXEYUDZCE-UHFFFAOYSA-N 5-methoxy-8-(4-methylpiperazin-1-yl)-n-[4-(propylsulfamoyl)phenyl]-3,4-dihydro-1h-isoquinoline-2-carboxamide Chemical compound C1=CC(S(=O)(=O)NCCC)=CC=C1NC(=O)N1CC2=C(N3CCN(C)CC3)C=CC(OC)=C2CC1 MQUHMXXEYUDZCE-UHFFFAOYSA-N 0.000 description 1
- DUNIZOQXLBPDJG-UHFFFAOYSA-N 5-methoxy-n-[4-[(4-methoxyphenyl)methylsulfamoyl]phenyl]-8-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-2-carboxamide Chemical compound C1=CC(OC)=CC=C1CNS(=O)(=O)C(C=C1)=CC=C1NC(=O)N1CC2=C(N3CCN(C)CC3)C=CC(OC)=C2CC1 DUNIZOQXLBPDJG-UHFFFAOYSA-N 0.000 description 1
- YPWFNLSXQIGJCK-UHFFFAOYSA-N 7-oxabicyclo[2.2.1]heptane Chemical compound C1CC2CCC1O2 YPWFNLSXQIGJCK-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910014585 C2-Ce Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
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- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- UAPBVAZHMSASOG-UHFFFAOYSA-N [4-(butylamino)phenyl]-[5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinolin-2-yl]methanone Chemical compound C1=CC(NCCCC)=CC=C1C(=O)N1CC2=C(N3CCN(C)CC3)C=CC(OC)=C2CC1 UAPBVAZHMSASOG-UHFFFAOYSA-N 0.000 description 1
- PAPLBFUWNOTOMO-UHFFFAOYSA-N [5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinolin-2-yl]-(4-phenoxyphenyl)methanone Chemical compound C1=2CN(C(=O)C=3C=CC(OC=4C=CC=CC=4)=CC=3)CCC=2C(OC)=CC=C1N1CCN(C)CC1 PAPLBFUWNOTOMO-UHFFFAOYSA-N 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000003302 alkenyloxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005360 alkyl sulfoxide group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000005133 alkynyloxy group Chemical group 0.000 description 1
- 125000005336 allyloxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- DMSHWWDRAYHEBS-UHFFFAOYSA-N dihydrocoumarin Natural products C1CC(=O)OC2=C1C=C(OC)C(OC)=C2 DMSHWWDRAYHEBS-UHFFFAOYSA-N 0.000 description 1
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- 125000002541 furyl group Chemical group 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- 125000002883 imidazolyl group Chemical group 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
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- 229910052740 iodine Inorganic materials 0.000 description 1
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- 150000002537 isoquinolines Chemical class 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
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- XUMLIZOFOQXFHF-UHFFFAOYSA-N n-(4-aminophenyl)sulfonylbutanamide Chemical compound CCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 XUMLIZOFOQXFHF-UHFFFAOYSA-N 0.000 description 1
- JAFZLCMNRPFRKY-UHFFFAOYSA-N n-[2-[5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinolin-2-yl]-2-oxoethyl]benzamide Chemical compound C1=2CN(C(=O)CNC(=O)C=3C=CC=CC=3)CCC=2C(OC)=CC=C1N1CCN(C)CC1 JAFZLCMNRPFRKY-UHFFFAOYSA-N 0.000 description 1
- ITSDPQNGMJJJDY-UHFFFAOYSA-N n-[2-[5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinolin-2-yl]-2-oxoethyl]pyridine-4-carboxamide Chemical compound C1=2CN(C(=O)CNC(=O)C=3C=CN=CC=3)CCC=2C(OC)=CC=C1N1CCN(C)CC1 ITSDPQNGMJJJDY-UHFFFAOYSA-N 0.000 description 1
- FMMDIRPXNKWYFV-UHFFFAOYSA-N n-[4-(tert-butylsulfamoyl)phenyl]-5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-2-carboxamide Chemical compound C1=2CN(C(=O)NC=3C=CC(=CC=3)S(=O)(=O)NC(C)(C)C)CCC=2C(OC)=CC=C1N1CCN(C)CC1 FMMDIRPXNKWYFV-UHFFFAOYSA-N 0.000 description 1
- ZOIQFKHVXIRSFF-UHFFFAOYSA-N n-[4-[5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinolin-2-yl]-4-oxobutyl]benzamide Chemical compound C1=2CN(C(=O)CCCNC(=O)C=3C=CC=CC=3)CCC=2C(OC)=CC=C1N1CCN(C)CC1 ZOIQFKHVXIRSFF-UHFFFAOYSA-N 0.000 description 1
- WHJZKYHMAFEQGO-UHFFFAOYSA-N n-[5-[5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinolin-2-yl]-5-oxopentyl]benzamide Chemical compound C1=2CN(C(=O)CCCCNC(=O)C=3C=CC=CC=3)CCC=2C(OC)=CC=C1N1CCN(C)CC1 WHJZKYHMAFEQGO-UHFFFAOYSA-N 0.000 description 1
- UETYMVIIPPTAGV-UHFFFAOYSA-N n-[5-[5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinolin-2-yl]-5-oxopentyl]quinoline-5-carboxamide Chemical compound C1=2CN(C(=O)CCCCNC(=O)C=3C4=CC=CN=C4C=CC=3)CCC=2C(OC)=CC=C1N1CCN(C)CC1 UETYMVIIPPTAGV-UHFFFAOYSA-N 0.000 description 1
- FWWQGESITJCOFZ-UHFFFAOYSA-N n-ethyl-4-[2-[5-methoxy-8-(4-methylpiperazin-1-yl)-3,4-dihydro-1h-isoquinolin-2-yl]-2-oxoethyl]benzenesulfonamide Chemical group C1=CC(S(=O)(=O)NCC)=CC=C1CC(=O)N1CC2=C(N3CCN(C)CC3)C=CC(OC)=C2CC1 FWWQGESITJCOFZ-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
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- UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 description 1
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- 125000005646 oximino group Chemical group 0.000 description 1
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- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 125000004585 polycyclic heterocycle group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- LJPZHJUSICYOIX-UHFFFAOYSA-N quinolizidine Chemical compound C1CCCC2CCCCN21 LJPZHJUSICYOIX-UHFFFAOYSA-N 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- IBBLKSWSCDAPIF-UHFFFAOYSA-N thiopyran Chemical compound S1C=CC=C=C1 IBBLKSWSCDAPIF-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Anesthesiology (AREA)
- Gynecology & Obstetrics (AREA)
- Obesity (AREA)
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- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Reproductive Health (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
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|---|---|---|---|
| SE0103644A SE0103644D0 (sv) | 2001-11-01 | 2001-11-01 | Therapeutic isoquinoline compounds |
Publications (1)
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|---|---|
| ZA200403240B true ZA200403240B (en) | 2005-04-07 |
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| ZA200403240A ZA200403240B (en) | 2001-11-01 | 2004-04-29 | Therapeutic isoquinoline compounds. |
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| US (1) | US20070010526A1 (es) |
| EP (1) | EP1451172A1 (es) |
| JP (1) | JP2005516896A (es) |
| KR (1) | KR20050042223A (es) |
| CN (1) | CN1608061A (es) |
| BR (1) | BR0213778A (es) |
| CA (1) | CA2464342A1 (es) |
| CO (1) | CO5580832A2 (es) |
| HU (1) | HUP0501089A2 (es) |
| IL (1) | IL161511A0 (es) |
| IS (1) | IS7236A (es) |
| MX (1) | MXPA04004076A (es) |
| NO (1) | NO20042154L (es) |
| PL (1) | PL370058A1 (es) |
| RU (1) | RU2004112423A (es) |
| SE (1) | SE0103644D0 (es) |
| WO (1) | WO2003037887A1 (es) |
| ZA (1) | ZA200403240B (es) |
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| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| US7101881B2 (en) * | 2003-06-11 | 2006-09-05 | Pfizer Inc | Tetrahydroquinolines |
| EP1673357A2 (en) | 2003-08-08 | 2006-06-28 | Vertex Pharmaceuticals Incorporated | Heteroarylaminosulfonylphenyl derivatives for use as sodium or calcium channel blockers in the treatment of pain |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| US7572805B2 (en) * | 2004-07-14 | 2009-08-11 | Bristol-Myers Squibb Company | Pyrrolo(oxo)isoquinolines as 5HT ligands |
| JP2006056881A (ja) * | 2004-07-21 | 2006-03-02 | Takeda Chem Ind Ltd | 縮合環化合物 |
| US7211584B2 (en) | 2004-08-18 | 2007-05-01 | Laboratorios Del Dr. Esteve, S.A. | 5-HT7 receptor ligands |
| EP1630158A1 (en) * | 2004-08-18 | 2006-03-01 | Laboratorios Del Dr. Esteve, S.A. | 5-HT7 receptor antagonists |
| ES2257168B1 (es) | 2004-08-18 | 2007-06-01 | Laboratorios Del Dr Esteve, S.A. | Ligandos del receptor 5-ht7. |
| ES2257167B1 (es) * | 2004-08-18 | 2007-06-01 | Laboratorios Del Dr Esteve, S.A. | Inhibidores del receptor 5-ht7. |
| US7211585B2 (en) | 2004-08-18 | 2007-05-01 | Laboratorios Del Dr. Esteve, S.A. | 5-HT7 receptor antagonists |
| ES2465469T3 (es) | 2005-01-14 | 2014-06-05 | Gilead Connecticut, Inc. | Diaril ureas 1,3-sustituidas como moduladores de la actividad quinasa |
| US7777040B2 (en) | 2005-05-03 | 2010-08-17 | Cgi Pharmaceuticals, Inc. | Certain substituted ureas, as modulators of kinase activity |
| US20080051387A1 (en) * | 2006-06-09 | 2008-02-28 | Yuelian Xu | Tetrahydropyrido[3,4-d]pyrimidines and related analogues |
| US9623021B2 (en) | 2007-01-22 | 2017-04-18 | Gtx, Inc. | Nuclear receptor binding agents |
| US9604931B2 (en) | 2007-01-22 | 2017-03-28 | Gtx, Inc. | Nuclear receptor binding agents |
| CN101641013B (zh) | 2007-01-22 | 2014-07-30 | Gtx公司 | 核受体结合剂 |
| US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
| ES2393885T7 (es) | 2007-06-04 | 2014-01-30 | Synergy Pharmaceuticals Inc. | Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| SE531698C2 (sv) | 2007-07-12 | 2009-07-07 | Respiratorius Ab | Nya bronkdilaterande a,b-omättade amider |
| ES2522968T3 (es) | 2008-06-04 | 2014-11-19 | Synergy Pharmaceuticals Inc. | Agonistas de guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros trastornos |
| AU2009270833B2 (en) | 2008-07-16 | 2015-02-19 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal, inflammation, cancer and other disorders |
| US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
| ES2553237T3 (es) * | 2011-02-02 | 2015-12-07 | Astellas Pharma Inc. | Derivado de tetrahidroisoquinolina |
| JP6251038B2 (ja) | 2011-03-01 | 2017-12-20 | シナジー ファーマシューティカルズ インコーポレイテッド | グアニル酸シクラーゼｃアゴニストの調製方法 |
| CN104011021B (zh) * | 2011-12-21 | 2016-08-24 | 埃科特莱茵药品有限公司 | 杂环衍生物及其作为前列腺素d2受体调节剂的用途 |
| WO2014028669A1 (en) * | 2012-08-15 | 2014-02-20 | Biogen Idec Ma Inc. | Novel compounds for modulation of ror-gamma activity |
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| US9315464B1 (en) * | 2013-01-31 | 2016-04-19 | Nant Holdings Ip, Llc | Small molecule inhibitors of influenza A RNA-dependent RNA polymerase |
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| BR112020010322A2 (pt) | 2017-11-24 | 2020-11-17 | Jubilant Episcribe Llc | composto da fórmula i; composto da fórmula ia; composto da fórmula ib; processo de preparação de compostos da fórmula i; composição farmacêutica; método para o tratamento e/ou prevenção de várias doenças; uso dos compostos; método para o tratamento de câncer; e método para o tratamento e/ou prevenção de uma afecção mediada por prmt5 ou um distúrbio proliferativo ou câncer |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT689536E (pt) * | 1993-03-16 | 2001-11-30 | Pfizer | Derivados de naftaleno |
| WO1995006637A1 (en) * | 1993-09-03 | 1995-03-09 | Smithkline Beecham Plc | Indole and indoline derivatives as 5ht1d receptor antagonists |
| FR2744450A1 (fr) * | 1996-02-02 | 1997-08-08 | Pf Medicament | Nouvelles naphtylpiperazines derivees de cycloazanes substitues, ainsi que leur procede de preparation, les compositions pharmaceutiques et leur utilisation comme medicaments |
| JP2001506995A (ja) * | 1996-12-19 | 2001-05-29 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | Ｎ−ピペラジン−１−イルフェニル−ベンズアミド誘導体 |
| DZ2376A1 (fr) * | 1996-12-19 | 2002-12-28 | Smithkline Beecham Plc | Dérivés de sulfonamides nouveaux procédé pour leurpréparation et compositions pharmaceutiques les c ontenant. |
| SE9702799D0 (sv) * | 1997-07-25 | 1997-07-25 | Astra Ab | New compounds |
| HUP0102622A3 (en) * | 1998-07-20 | 2002-12-28 | Merck Patent Gmbh | Biphenyl derivatives, process for producing them and pharmaceutical compositions containing them |
| GB9926302D0 (en) * | 1999-11-05 | 2000-01-12 | Smithkline Beecham Plc | Novel compounds |
-
2001
- 2001-11-01 SE SE0103644A patent/SE0103644D0/xx unknown
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2002
- 2002-11-01 CA CA002464342A patent/CA2464342A1/en not_active Abandoned
- 2002-11-01 CN CNA028262816A patent/CN1608061A/zh active Pending
- 2002-11-01 PL PL02370058A patent/PL370058A1/xx not_active Application Discontinuation
- 2002-11-01 KR KR1020047006593A patent/KR20050042223A/ko not_active Application Discontinuation
- 2002-11-01 EP EP02780244A patent/EP1451172A1/en not_active Withdrawn
- 2002-11-01 HU HU0501089A patent/HUP0501089A2/hu unknown
- 2002-11-01 IL IL16151102A patent/IL161511A0/xx unknown
- 2002-11-01 RU RU2004112423/04A patent/RU2004112423A/ru not_active Application Discontinuation
- 2002-11-01 MX MXPA04004076A patent/MXPA04004076A/es not_active Application Discontinuation
- 2002-11-01 JP JP2003540168A patent/JP2005516896A/ja active Pending
- 2002-11-01 BR BR0213778-0A patent/BR0213778A/pt not_active IP Right Cessation
- 2002-11-01 WO PCT/SE2002/001988 patent/WO2003037887A1/en not_active Application Discontinuation
- 2002-11-01 US US10/494,424 patent/US20070010526A1/en not_active Abandoned
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2004
- 2004-04-28 IS IS7236A patent/IS7236A/is unknown
- 2004-04-29 ZA ZA200403240A patent/ZA200403240B/en unknown
- 2004-04-30 CO CO04039910A patent/CO5580832A2/es not_active Application Discontinuation
- 2004-05-25 NO NO20042154A patent/NO20042154L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN1608061A (zh) | 2005-04-20 |
| BR0213778A (pt) | 2004-11-09 |
| US20070010526A1 (en) | 2007-01-11 |
| IS7236A (is) | 2004-04-28 |
| RU2004112423A (ru) | 2005-10-10 |
| KR20050042223A (ko) | 2005-05-06 |
| PL370058A1 (en) | 2005-05-16 |
| SE0103644D0 (sv) | 2001-11-01 |
| EP1451172A1 (en) | 2004-09-01 |
| WO2003037887A1 (en) | 2003-05-08 |
| WO2003037887A8 (en) | 2005-03-17 |
| IL161511A0 (en) | 2004-09-27 |
| CA2464342A1 (en) | 2003-05-08 |
| NO20042154L (no) | 2004-07-29 |
| MXPA04004076A (es) | 2004-07-23 |
| HUP0501089A2 (en) | 2007-09-28 |
| JP2005516896A (ja) | 2005-06-09 |
| CO5580832A2 (es) | 2005-11-30 |
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