CA2320757A1 - New use - Google Patents
New use Download PDFInfo
- Publication number
- CA2320757A1 CA2320757A1 CA002320757A CA2320757A CA2320757A1 CA 2320757 A1 CA2320757 A1 CA 2320757A1 CA 002320757 A CA002320757 A CA 002320757A CA 2320757 A CA2320757 A CA 2320757A CA 2320757 A1 CA2320757 A1 CA 2320757A1
- Authority
- CA
- Canada
- Prior art keywords
- dione
- indole
- phenyl
- group
- compound
- Prior art date
- Legal status (The legal status 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 status listed.)
- Abandoned
Links
- 239000003814 drug Substances 0.000 claims abstract description 14
- 208000027531 mycobacterial infectious disease Diseases 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 63
- 201000008827 tuberculosis Diseases 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000012453 solvate Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 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 description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000002671 adjuvant Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- FYNPBAGLSDDVHU-UHFFFAOYSA-N 1-(4-bromobutyl)-7-phenylindole-2,3-dione Chemical compound C=12N(CCCCBr)C(=O)C(=O)C2=CC=CC=1C1=CC=CC=C1 FYNPBAGLSDDVHU-UHFFFAOYSA-N 0.000 claims description 2
- FBPDWXJUQMMZPX-UHFFFAOYSA-N 1-[2-(1-benzylpiperidin-4-yl)ethyl]-5-cyclohexylindole-2,3-dione Chemical compound C12=CC=C(C3CCCCC3)C=C2C(=O)C(=O)N1CCC(CC1)CCN1CC1=CC=CC=C1 FBPDWXJUQMMZPX-UHFFFAOYSA-N 0.000 claims description 2
- IHGVCDFVQAKCCY-UHFFFAOYSA-N 1-[2-(4-benzylpiperazin-1-yl)ethyl]-5-phenylindole-2,3-dione Chemical compound C12=CC=C(C=3C=CC=CC=3)C=C2C(=O)C(=O)N1CCN(CC1)CCN1CC1=CC=CC=C1 IHGVCDFVQAKCCY-UHFFFAOYSA-N 0.000 claims description 2
- LYMFGNADTQJWEY-UHFFFAOYSA-N 1-[2-(4-benzylpiperazin-1-yl)ethyl]-5-piperidin-1-ylindole-2,3-dione Chemical compound C12=CC=C(N3CCCCC3)C=C2C(=O)C(=O)N1CCN(CC1)CCN1CC1=CC=CC=C1 LYMFGNADTQJWEY-UHFFFAOYSA-N 0.000 claims description 2
- SRPUPFCUMOTDJP-UHFFFAOYSA-N 1-[2-(4-benzylpiperazin-1-yl)ethyl]-7-cycloheptylindole-2,3-dione Chemical compound C1=CC=C(C2CCCCCC2)C2=C1C(=O)C(=O)N2CCN(CC1)CCN1CC1=CC=CC=C1 SRPUPFCUMOTDJP-UHFFFAOYSA-N 0.000 claims description 2
- FOEBGLTZGPBDTC-UHFFFAOYSA-N 1-[2-(4-benzylpiperazin-1-yl)ethyl]-7-cyclopentylindole-2,3-dione Chemical compound C1=CC=C(C2CCCC2)C2=C1C(=O)C(=O)N2CCN(CC1)CCN1CC1=CC=CC=C1 FOEBGLTZGPBDTC-UHFFFAOYSA-N 0.000 claims description 2
- YUOZUICINOLYIL-UHFFFAOYSA-N 1-[4-[benzyl(ethyl)amino]butyl]indole-2,3-dione Chemical compound O=C1C(=O)C2=CC=CC=C2N1CCCCN(CC)CC1=CC=CC=C1 YUOZUICINOLYIL-UHFFFAOYSA-N 0.000 claims description 2
- WQMCPSQJWFURHH-UHFFFAOYSA-N 1-decyl-7-phenylindole-2,3-dione Chemical compound C=12N(CCCCCCCCCC)C(=O)C(=O)C2=CC=CC=1C1=CC=CC=C1 WQMCPSQJWFURHH-UHFFFAOYSA-N 0.000 claims description 2
- PSIVGOLCMDGIJJ-UHFFFAOYSA-N 1-dodecyl-7-phenylindole-2,3-dione Chemical compound C=12N(CCCCCCCCCCCC)C(=O)C(=O)C2=CC=CC=1C1=CC=CC=C1 PSIVGOLCMDGIJJ-UHFFFAOYSA-N 0.000 claims description 2
- MNSNZIGPMZSRLW-UHFFFAOYSA-N 1-hexyl-7-phenylindole-2,3-dione Chemical compound C=12N(CCCCCC)C(=O)C(=O)C2=CC=CC=1C1=CC=CC=C1 MNSNZIGPMZSRLW-UHFFFAOYSA-N 0.000 claims description 2
- AEQJGHYAIWZFJM-UHFFFAOYSA-N 1-nonyl-7-phenylindole-2,3-dione Chemical compound C=12N(CCCCCCCCC)C(=O)C(=O)C2=CC=CC=1C1=CC=CC=C1 AEQJGHYAIWZFJM-UHFFFAOYSA-N 0.000 claims description 2
- FXAMFTNJEXSPKQ-UHFFFAOYSA-N 1-(2-methylpropyl)-7-phenylindole-2,3-dione Chemical compound C=12N(CC(C)C)C(=O)C(=O)C2=CC=CC=1C1=CC=CC=C1 FXAMFTNJEXSPKQ-UHFFFAOYSA-N 0.000 claims 1
- JPONAGGTSYTWGV-UHFFFAOYSA-N 1-(4-bromobutyl)-5-cyclohexylindole-2,3-dione Chemical compound C=1C=C2N(CCCCBr)C(=O)C(=O)C2=CC=1C1CCCCC1 JPONAGGTSYTWGV-UHFFFAOYSA-N 0.000 claims 1
- HMRLMUUHEHQXDR-UHFFFAOYSA-N 1-[2-(1-benzylpiperidin-4-yl)ethyl]-5-cyclohexyl-3h-indol-2-one Chemical compound O=C1CC2=CC(C3CCCCC3)=CC=C2N1CCC(CC1)CCN1CC1=CC=CC=C1 HMRLMUUHEHQXDR-UHFFFAOYSA-N 0.000 claims 1
- RLCCRJVHOVASFS-UHFFFAOYSA-N 1-[5-[benzyl(ethyl)amino]pentyl]-5-cyclohexylindole-2,3-dione Chemical compound C=1C=CC=CC=1CN(CC)CCCCCN(C1=CC=2)C(=O)C(=O)C1=CC=2C1CCCCC1 RLCCRJVHOVASFS-UHFFFAOYSA-N 0.000 claims 1
- MLDLCKKTWKFMCA-UHFFFAOYSA-N 1-butyl-7-phenylindole-2,3-dione Chemical compound C=12N(CCCC)C(=O)C(=O)C2=CC=CC=1C1=CC=CC=C1 MLDLCKKTWKFMCA-UHFFFAOYSA-N 0.000 claims 1
- FJYVWONIMYBYLF-UHFFFAOYSA-N 1-heptyl-7-phenylindole-2,3-dione Chemical compound C=12N(CCCCCCC)C(=O)C(=O)C2=CC=CC=1C1=CC=CC=C1 FJYVWONIMYBYLF-UHFFFAOYSA-N 0.000 claims 1
- BQXOOXFULFBRMA-UHFFFAOYSA-N 1-octyl-7-phenylindole-2,3-dione Chemical compound C=12N(CCCCCCCC)C(=O)C(=O)C2=CC=CC=1C1=CC=CC=C1 BQXOOXFULFBRMA-UHFFFAOYSA-N 0.000 claims 1
- QEDOTJXIRMMBJY-UHFFFAOYSA-N 1-pentyl-7-phenylindole-2,3-dione Chemical compound C=12N(CCCCC)C(=O)C(=O)C2=CC=CC=1C1=CC=CC=C1 QEDOTJXIRMMBJY-UHFFFAOYSA-N 0.000 claims 1
- YORJORPLRWESAS-UHFFFAOYSA-N 7-phenyl-1-undecylindole-2,3-dione Chemical compound C=12N(CCCCCCCCCCC)C(=O)C(=O)C2=CC=CC=1C1=CC=CC=C1 YORJORPLRWESAS-UHFFFAOYSA-N 0.000 claims 1
- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 abstract description 9
- 150000005623 oxindoles Chemical class 0.000 abstract description 3
- 229940079593 drug Drugs 0.000 description 9
- 201000009671 multidrug-resistant tuberculosis Diseases 0.000 description 9
- 229960003350 isoniazid Drugs 0.000 description 8
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 8
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 8
- -1 pyrrolidinyI Chemical group 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 230000034994 death Effects 0.000 description 6
- 231100000517 death Toxicity 0.000 description 6
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 description 5
- 229960001225 rifampicin Drugs 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 229960005322 streptomycin Drugs 0.000 description 4
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- KGTSLTYUUFWZNW-PPJQWWMSSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-2,15,17,27,29-pentahydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-26-[(E)-(4-methylpiperazin-1-yl)iminomethyl]-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate pyridine-4-carbohydrazide Chemical compound NNC(=O)c1ccncc1.CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C2=O)c2c(O)c(\C=N\N4CCN(C)CC4)c(NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)c(O)c2c(O)c3C KGTSLTYUUFWZNW-PPJQWWMSSA-N 0.000 description 3
- 238000002512 chemotherapy Methods 0.000 description 3
- 229960000285 ethambutol Drugs 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 241000186367 Mycobacterium avium Species 0.000 description 2
- 241000186366 Mycobacterium bovis Species 0.000 description 2
- 241000187492 Mycobacterium marinum Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 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 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000003745 diagnosis Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000001717 pathogenic effect Effects 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
- MPPPKRYCTPRNTB-DOMIDYPGSA-N 1-bromobutane Chemical group CCC[14CH2]Br MPPPKRYCTPRNTB-DOMIDYPGSA-N 0.000 description 1
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- LSXKDWGTSHCFPP-UHFFFAOYSA-N 1-bromoheptane Chemical compound CCCCCCCBr LSXKDWGTSHCFPP-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-IDEBNGHGSA-N 1-bromohexane Chemical group [13CH3][13CH2][13CH2][13CH2][13CH2][13CH2]Br MNDIARAMWBIKFW-IDEBNGHGSA-N 0.000 description 1
- AYMUQTNXKPEMLM-UHFFFAOYSA-N 1-bromononane Chemical compound CCCCCCCCCBr AYMUQTNXKPEMLM-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical group CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- JBLPOKSPLRNMDC-UHFFFAOYSA-N 7-phenyl-1h-indole-2,3-dione Chemical compound O=C1C(=O)NC2=C1C=CC=C2C1=CC=CC=C1 JBLPOKSPLRNMDC-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000272165 Charadriidae Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 201000010374 Down Syndrome Diseases 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 206010044688 Trisomy 21 Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 229920005557 bromobutyl Polymers 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000544 cholinesterase inhibitor Substances 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 230000001332 colony forming effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- QNLOWBMKUIXCOW-UHFFFAOYSA-N indol-2-one Chemical compound C1=CC=CC2=NC(=O)C=C21 QNLOWBMKUIXCOW-UHFFFAOYSA-N 0.000 description 1
- 239000012678 infectious agent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 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 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 239000000814 tuberculostatic agent Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A61P31/06—Antibacterial agents for tuberculosis
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN464/MAS/98 | 1998-03-06 | ||
| IN464MA1998 | 1998-03-06 | ||
| SE98013270-9 | 1998-04-20 | ||
| SE9801370A SE9801370D0 (sv) | 1998-04-20 | 1998-04-20 | New use |
| PCT/SE1999/000319 WO1999044608A1 (en) | 1998-03-06 | 1999-03-04 | New use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2320757A1 true CA2320757A1 (en) | 1999-09-10 |
Family
ID=26324794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002320757A Abandoned CA2320757A1 (en) | 1998-03-06 | 1999-03-04 | New use |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6906090B1 (enExample) |
| EP (1) | EP1058548B1 (enExample) |
| JP (1) | JP2002505286A (enExample) |
| KR (1) | KR20010041625A (enExample) |
| CN (1) | CN100391455C (enExample) |
| AT (1) | ATE249828T1 (enExample) |
| AU (1) | AU735381B2 (enExample) |
| BR (1) | BR9908510A (enExample) |
| CA (1) | CA2320757A1 (enExample) |
| DE (1) | DE69911380T2 (enExample) |
| NO (1) | NO20004419L (enExample) |
| NZ (1) | NZ506217A (enExample) |
| WO (1) | WO1999044608A1 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6329416B1 (en) | 1999-05-04 | 2001-12-11 | American Home Products Corporation | Combination regimens using 3,3-substituted indoline derivatives |
| US6380235B1 (en) | 1999-05-04 | 2002-04-30 | American Home Products Corporation | Benzimidazolones and analogues |
| US6399593B1 (en) | 1999-05-04 | 2002-06-04 | Wyeth | Cyclic regimens using cyclic urea and cyclic amide derivatives |
| US6407101B1 (en) | 1999-05-04 | 2002-06-18 | American Home Products Corporation | Cyanopyrroles |
| US6444668B1 (en) | 1999-05-04 | 2002-09-03 | Wyeth | Combination regimens using progesterone receptor modulators |
| US6319912B1 (en) | 1999-05-04 | 2001-11-20 | American Home Products Corporation | Cyclic regimens using 2,1-benzisothiazoline 2,2-dioxides |
| US6369056B1 (en) | 1999-05-04 | 2002-04-09 | American Home Products Corporation | Cyclic urea and cyclic amide derivatives |
| US6306851B1 (en) | 1999-05-04 | 2001-10-23 | American Home Products Corporation | Cyclocarbamate and cyclic amide derivatives |
| US6509334B1 (en) | 1999-05-04 | 2003-01-21 | American Home Products Corporation | Cyclocarbamate derivatives as progesterone receptor modulators |
| US6391907B1 (en) | 1999-05-04 | 2002-05-21 | American Home Products Corporation | Indoline derivatives |
| US6355648B1 (en) | 1999-05-04 | 2002-03-12 | American Home Products Corporation | Thio-oxindole derivatives |
| US6423699B1 (en) | 1999-05-04 | 2002-07-23 | American Home Products Corporation | Combination therapies using benzimidazolones |
| US6498154B1 (en) | 1999-05-04 | 2002-12-24 | Wyeth | Cyclic regimens using quinazolinone and benzoxazine derivatives |
| US6380178B1 (en) | 1999-05-04 | 2002-04-30 | American Home Products Corporation | Cyclic regimens using cyclocarbamate and cyclic amide derivatives |
| US6358947B1 (en) | 1999-05-04 | 2002-03-19 | American Home Products Corporation | Tetracyclic progesterone receptor modulator compounds and methods |
| US6358948B1 (en) | 1999-05-04 | 2002-03-19 | American Home Products Corporation | Quinazolinone and benzoxazine derivatives as progesterone receptor modulators |
| US6339098B1 (en) | 1999-05-04 | 2002-01-15 | American Home Products Corporation | 2,1-benzisothiazoline 2,2-dioxides |
| US6417214B1 (en) | 1999-05-04 | 2002-07-09 | Wyeth | 3,3-substituted indoline derivatives |
| US6462032B1 (en) | 1999-05-04 | 2002-10-08 | Wyeth | Cyclic regimens utilizing indoline derivatives |
| US6372752B1 (en) * | 2000-02-07 | 2002-04-16 | Genzyme Corporation | Inha inhibitors and methods of use thereof |
| UA73119C2 (en) | 2000-04-19 | 2005-06-15 | American Home Products Corpoir | Derivatives of cyclic thiocarbamates, pharmaceutical composition including noted derivatives of cyclic thiocarbamates and active ingredients of medicines as modulators of progesterone receptors |
| CN101863823B (zh) * | 2010-06-03 | 2012-02-08 | 山东大学 | 吲哚二酮类化合物及其扩环衍生物、制备方法及应用 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR65270B (en) * | 1978-10-10 | 1980-07-31 | Fujisawa Pharmaceutical Co | Isatin derivatives and processes for the preparation thereof |
| IE69677B1 (en) | 1989-12-11 | 1996-10-02 | Neurosearch As | Isatine derivatives their preparation and use |
| US5164404A (en) | 1991-03-15 | 1992-11-17 | Neurosearch A/S | Hydrazone derivatives and their use |
| SE9103752D0 (sv) | 1991-12-18 | 1991-12-18 | Astra Ab | New compounds |
| US5206366A (en) * | 1992-08-26 | 1993-04-27 | Pfizer Inc. | Process for preparing aryl piperazinyl-heterocyclic compounds |
| US5270331A (en) * | 1993-01-26 | 1993-12-14 | Pfizer, Inc. | Prodrugs of antiinflammatory 3-acyl-2-oxindole-1-carboxamides |
| SE9302080D0 (sv) * | 1993-06-16 | 1993-06-16 | Ab Astra | New compounds |
-
1999
- 1999-03-04 BR BR9908510-0A patent/BR9908510A/pt not_active Application Discontinuation
- 1999-03-04 AU AU27573/99A patent/AU735381B2/en not_active Ceased
- 1999-03-04 JP JP2000534210A patent/JP2002505286A/ja active Pending
- 1999-03-04 WO PCT/SE1999/000319 patent/WO1999044608A1/en not_active Ceased
- 1999-03-04 CA CA002320757A patent/CA2320757A1/en not_active Abandoned
- 1999-03-04 CN CNB998037249A patent/CN100391455C/zh not_active Expired - Fee Related
- 1999-03-04 AT AT99908059T patent/ATE249828T1/de not_active IP Right Cessation
- 1999-03-04 DE DE69911380T patent/DE69911380T2/de not_active Expired - Fee Related
- 1999-03-04 KR KR1020007009824A patent/KR20010041625A/ko not_active Ceased
- 1999-03-04 EP EP99908059A patent/EP1058548B1/en not_active Expired - Lifetime
- 1999-03-04 US US09/284,516 patent/US6906090B1/en not_active Expired - Fee Related
- 1999-03-04 NZ NZ506217A patent/NZ506217A/en unknown
-
2000
- 2000-09-05 NO NO20004419A patent/NO20004419L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK1030885A1 (en) | 2001-05-25 |
| EP1058548A1 (en) | 2000-12-13 |
| WO1999044608A1 (en) | 1999-09-10 |
| DE69911380T2 (de) | 2004-07-01 |
| JP2002505286A (ja) | 2002-02-19 |
| CN100391455C (zh) | 2008-06-04 |
| AU735381B2 (en) | 2001-07-05 |
| WO1999044608A8 (en) | 2005-01-06 |
| AU2757399A (en) | 1999-09-20 |
| NZ506217A (en) | 2002-05-31 |
| NO20004419L (no) | 2000-10-20 |
| KR20010041625A (ko) | 2001-05-25 |
| ATE249828T1 (de) | 2003-10-15 |
| NO20004419D0 (no) | 2000-09-05 |
| DE69911380D1 (de) | 2003-10-23 |
| BR9908510A (pt) | 2000-11-21 |
| CN1292694A (zh) | 2001-04-25 |
| US6906090B1 (en) | 2005-06-14 |
| EP1058548B1 (en) | 2003-09-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |