CA2604446A1 - Methodes et compositions pour le traitement de troubles anxieux - Google Patents

Info

Publication number

CA2604446A1

CA2604446A1 CA002604446A CA2604446A CA2604446A1 CA 2604446 A1 CA2604446 A1 CA 2604446A1 CA 002604446 A CA002604446 A CA 002604446A CA 2604446 A CA2604446 A CA 2604446A CA 2604446 A1 CA2604446 A1 CA 2604446A1

Authority

CA

Canada

Prior art keywords

furosemide

ester

bumetanide

group

piretanide

Prior art date

2005-04-07

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

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 238000000034 method Methods 0.000 title claims abstract description 106
• 239000000203 mixture Substances 0.000 title claims abstract description 83
• 208000019901 Anxiety disease Diseases 0.000 title claims description 15
• 238000011282 treatment Methods 0.000 title description 92
• 101000640897 Squalus acanthias Solute carrier family 12 member 2 Proteins 0.000 claims abstract description 36
• 102000003673 Symporters Human genes 0.000 claims abstract description 34
• 108090000088 Symporters Proteins 0.000 claims abstract description 34
• -1 bumetanide aldehyde Chemical class 0.000 claims description 210
• 229960003883 furosemide Drugs 0.000 claims description 171
• ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 137
• 229960004064 bumetanide Drugs 0.000 claims description 132
• MAEIEVLCKWDQJH-UHFFFAOYSA-N bumetanide Chemical compound CCCCNC1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 MAEIEVLCKWDQJH-UHFFFAOYSA-N 0.000 claims description 105
• 229960001085 piretanide Drugs 0.000 claims description 100
• 150000001875 compounds Chemical class 0.000 claims description 77
• UJEWTUDSLQGTOA-UHFFFAOYSA-N Piretanide Chemical compound C=1C=CC=CC=1OC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1N1CCCC1 UJEWTUDSLQGTOA-UHFFFAOYSA-N 0.000 claims description 71
• 150000002148 esters Chemical class 0.000 claims description 71
• 229960004988 azosemide Drugs 0.000 claims description 42
• 150000003839 salts Chemical class 0.000 claims description 41
• 229960005461 torasemide Drugs 0.000 claims description 36
• NGBFQHCMQULJNZ-UHFFFAOYSA-N Torsemide Chemical compound CC(C)NC(=O)NS(=O)(=O)C1=CN=CC=C1NC1=CC=CC(C)=C1 NGBFQHCMQULJNZ-UHFFFAOYSA-N 0.000 claims description 26
• 230000001537 neural effect Effects 0.000 claims description 26
• 125000003545 alkoxy group Chemical group 0.000 claims description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 21
• 229940123259 Transporter antagonist Drugs 0.000 claims description 21
• 230000000946 synaptic effect Effects 0.000 claims description 19
• 125000003118 aryl group Chemical group 0.000 claims description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 13
• 239000002253 acid Substances 0.000 claims description 12
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
• 150000002500 ions Chemical class 0.000 claims description 12
• BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 claims description 11
• 229920000249 biocompatible polymer Polymers 0.000 claims description 11
• 239000012453 solvate Substances 0.000 claims description 11
• UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 claims description 9
• 239000001257 hydrogen Substances 0.000 claims description 9
• 125000005189 alkyl hydroxy group Chemical group 0.000 claims description 8
• 125000004104 aryloxy group Chemical group 0.000 claims description 7
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 7
• PXEMVEVMHVJJTK-UHFFFAOYSA-N n,n-dibenzyl-3-(butylamino)-4-phenoxy-5-sulfamoylbenzamide Chemical compound CCCCNC1=CC(C(=O)N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 PXEMVEVMHVJJTK-UHFFFAOYSA-N 0.000 claims description 7
• JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims description 6
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
• XQEQFAXBQUSPDR-UHFFFAOYSA-N ethyl 4-chloro-2-(furan-2-ylmethylamino)-5-sulfamoylbenzoate Chemical compound CCOC(=O)C1=CC(S(N)(=O)=O)=C(Cl)C=C1NCC1=CC=CO1 XQEQFAXBQUSPDR-UHFFFAOYSA-N 0.000 claims description 5
• 208000028173 post-traumatic stress disease Diseases 0.000 claims description 5
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
• 125000005210 alkyl ammonium group Chemical group 0.000 claims description 4
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
• 125000004986 diarylamino group Chemical group 0.000 claims description 4
• 229910052760 oxygen Inorganic materials 0.000 claims description 4
• JIVPVXMEBJLZRO-CQSZACIVSA-N 2-chloro-5-[(1r)-1-hydroxy-3-oxo-2h-isoindol-1-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC([C@@]2(O)C3=CC=CC=C3C(=O)N2)=C1 JIVPVXMEBJLZRO-CQSZACIVSA-N 0.000 claims description 3
• JBMKAUGHUNFTOL-UHFFFAOYSA-N Aldoclor Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC=NS2(=O)=O JBMKAUGHUNFTOL-UHFFFAOYSA-N 0.000 claims description 3
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 3
• KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
• CESYKOGBSMNBPD-UHFFFAOYSA-N Methyclothiazide Chemical compound ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)N(C)C(CCl)NC2=C1 CESYKOGBSMNBPD-UHFFFAOYSA-N 0.000 claims description 3
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 3
• CYLWJCABXYDINA-UHFFFAOYSA-N Polythiazide Polymers ClC1=C(S(N)(=O)=O)C=C2S(=O)(=O)N(C)C(CSCC(F)(F)F)NC2=C1 CYLWJCABXYDINA-UHFFFAOYSA-N 0.000 claims description 3
• 229960003515 bendroflumethiazide Drugs 0.000 claims description 3
• HDWIHXWEUNVBIY-UHFFFAOYSA-N bendroflumethiazidum Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1NC2CC1=CC=CC=C1 HDWIHXWEUNVBIY-UHFFFAOYSA-N 0.000 claims description 3
• NDTSRXAMMQDVSW-UHFFFAOYSA-N benzthiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1N=C2CSCC1=CC=CC=C1 NDTSRXAMMQDVSW-UHFFFAOYSA-N 0.000 claims description 3
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• 229960001523 chlortalidone Drugs 0.000 claims description 3
• AVOLMBLBETYQHX-UHFFFAOYSA-N etacrynic acid Chemical compound CCC(=C)C(=O)C1=CC=C(OCC(O)=O)C(Cl)=C1Cl AVOLMBLBETYQHX-UHFFFAOYSA-N 0.000 claims description 3
• 229960003199 etacrynic acid Drugs 0.000 claims description 3
• 229960002003 hydrochlorothiazide Drugs 0.000 claims description 3
• 229960003313 hydroflumethiazide Drugs 0.000 claims description 3
• DMDGGSIALPNSEE-UHFFFAOYSA-N hydroflumethiazide Chemical compound C1=C(C(F)(F)F)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O DMDGGSIALPNSEE-UHFFFAOYSA-N 0.000 claims description 3
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 3
• NDDAHWYSQHTHNT-UHFFFAOYSA-N indapamide Chemical compound CC1CC2=CC=CC=C2N1NC(=O)C1=CC=C(Cl)C(S(N)(=O)=O)=C1 NDDAHWYSQHTHNT-UHFFFAOYSA-N 0.000 claims description 3
• 229960004569 indapamide Drugs 0.000 claims description 3
• 229960003739 methyclothiazide Drugs 0.000 claims description 3
• AQCHWTWZEMGIFD-UHFFFAOYSA-N metolazone Chemical compound CC1NC2=CC(Cl)=C(S(N)(=O)=O)C=C2C(=O)N1C1=CC=CC=C1C AQCHWTWZEMGIFD-UHFFFAOYSA-N 0.000 claims description 3
• 229960002817 metolazone Drugs 0.000 claims description 3
• RLWRMIYXDPXIEX-UHFFFAOYSA-N muzolimine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C)N1N=C(N)CC1=O RLWRMIYXDPXIEX-UHFFFAOYSA-N 0.000 claims description 3
• 229960001788 muzolimine Drugs 0.000 claims description 3
• 208000019906 panic disease Diseases 0.000 claims description 3
• 229960005483 polythiazide Drugs 0.000 claims description 3
• 229920000046 polythiazide Polymers 0.000 claims description 3
• AGMMTXLNIQSRCG-UHFFFAOYSA-N quinethazone Chemical compound NS(=O)(=O)C1=C(Cl)C=C2NC(CC)NC(=O)C2=C1 AGMMTXLNIQSRCG-UHFFFAOYSA-N 0.000 claims description 3
• 229960000577 quinethazone Drugs 0.000 claims description 3
• 239000003451 thiazide diuretic agent Substances 0.000 claims description 3
• 239000005458 thiazide-like diuretic Substances 0.000 claims description 3
• 229960004813 trichlormethiazide Drugs 0.000 claims description 3
• LMJSLTNSBFUCMU-UHFFFAOYSA-N trichlormethiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NC(C(Cl)Cl)NS2(=O)=O LMJSLTNSBFUCMU-UHFFFAOYSA-N 0.000 claims description 3
• UHLOVGKIEARANS-QZHINBJYSA-N tripamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(=O)NN2C[C@@H]3[C@H]4CC[C@H](C4)[C@@H]3C2)=C1 UHLOVGKIEARANS-QZHINBJYSA-N 0.000 claims description 3
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• 125000001475 halogen functional group Chemical group 0.000 claims 4
• IIOPLILENRZKRV-UHFFFAOYSA-N azosemide Chemical compound C=1C=CSC=1CNC=1C=C(Cl)C(S(=O)(=O)N)=CC=1C1=NN=N[N]1 IIOPLILENRZKRV-UHFFFAOYSA-N 0.000 claims 2
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