JP2010538023A5 - - Google Patents

Info

Publication number

JP2010538023A5

JP2010538023A5 JP2010523259A JP2010523259A JP2010538023A5 JP 2010538023 A5 JP2010538023 A5 JP 2010538023A5 JP 2010523259 A JP2010523259 A JP 2010523259A JP 2010523259 A JP2010523259 A JP 2010523259A JP 2010538023 A5 JP2010538023 A5 JP 2010538023A5

Authority

JP

Japan

Prior art keywords

formula

compound

alkyl

dithiolopyrrolone

pharmaceutically acceptable

Prior art date

2008-08-29

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.)

Granted

Links

• Espacenet
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• 125000000217 alkyl group Chemical group 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 16
• -1 dithiolopyrrolone compound Chemical class 0.000 claims description 13
• 150000001875 compounds Chemical class 0.000 claims description 9
• 125000003118 aryl group Chemical group 0.000 claims description 8
• 125000005842 heteroatom Chemical group 0.000 claims description 8
• 229910052739 hydrogen Inorganic materials 0.000 claims description 7
• 239000001257 hydrogen Substances 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
• 125000006618 5- to 10-membered aromatic heterocyclic group Chemical group 0.000 claims description 3
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
• 125000000623 heterocyclic group Chemical group 0.000 claims description 3
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 2
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 2
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
• 125000002541 furyl group Chemical group 0.000 claims description 2
• 229910052736 halogen Inorganic materials 0.000 claims description 2
• 150000002367 halogens Chemical class 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 2
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
• 125000004076 pyridyl group Chemical group 0.000 claims description 2
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
• 229910052717 sulfur Inorganic materials 0.000 claims description 2
• 125000001544 thienyl group Chemical group 0.000 claims description 2
• 238000000034 method Methods 0.000 claims 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
• KDDABMWLWNRHGO-UHFFFAOYSA-N dithiolo[4,3-b]pyrrole 1-oxide Chemical class N1=CC=C2S(=O)SC=C21 KDDABMWLWNRHGO-UHFFFAOYSA-N 0.000 claims 5
• 150000007530 organic bases Chemical class 0.000 claims 5
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
• 210000000265 leukocyte Anatomy 0.000 claims 4
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
• 239000002253 acid Substances 0.000 claims 3
• 239000000010 aprotic solvent Substances 0.000 claims 3
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
• 239000003513 alkali Substances 0.000 claims 2
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
• FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims 2
• 238000004519 manufacturing process Methods 0.000 claims 2
• 210000000440 neutrophil Anatomy 0.000 claims 2
• 230000002093 peripheral effect Effects 0.000 claims 2
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
• UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• FJDAWPHHQRPQHM-UHFFFAOYSA-N C=CS(NC(CC1)CN1S(C(C1=C2)=C(C(N)=O)NC1=CC=C2Br)(=O)=O)(=O)=O Chemical compound C=CS(NC(CC1)CN1S(C(C1=C2)=C(C(N)=O)NC1=CC=C2Br)(=O)=O)(=O)=O FJDAWPHHQRPQHM-UHFFFAOYSA-N 0.000 claims 1
• CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims 1
• LFAWYQWJAQRLPJ-UHFFFAOYSA-N [Cl].NC=O Chemical compound [Cl].NC=O LFAWYQWJAQRLPJ-UHFFFAOYSA-N 0.000 claims 1
• 230000002378 acidificating effect Effects 0.000 claims 1
• 239000002671 adjuvant Substances 0.000 claims 1
• AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 1
• 239000000920 calcium hydroxide Substances 0.000 claims 1
• 229910001861 calcium hydroxide Inorganic materials 0.000 claims 1
• 238000002512 chemotherapy Methods 0.000 claims 1
• 239000003814 drug Substances 0.000 claims 1
• 230000002401 inhibitory effect Effects 0.000 claims 1
• 150000007522 mineralic acids Chemical class 0.000 claims 1
• 150000007524 organic acids Chemical class 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• 239000011736 potassium bicarbonate Substances 0.000 claims 1
• 229910000028 potassium bicarbonate Inorganic materials 0.000 claims 1
• 235000015497 potassium bicarbonate Nutrition 0.000 claims 1
• TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims 1
• 229940086066 potassium hydrogencarbonate Drugs 0.000 claims 1
• 238000001959 radiotherapy Methods 0.000 claims 1
• 230000035484 reaction time Effects 0.000 claims 1
• 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
• 238000004809 thin layer chromatography Methods 0.000 claims 1
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
• 0 C*C(N(*)C1=C2SSC=C2N(*)C1=O)=O Chemical compound C*C(N(*)C1=C2SSC=C2N(*)C1=O)=O 0.000 description 1
• 150000002431 hydrogen Chemical class 0.000 description 1
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
• 150000003384 small molecules Chemical class 0.000 description 1