CA2495502A1 - Methods for treating carbonic anhydrase mediated disorders - Google Patents
Methods for treating carbonic anhydrase mediated disorders Download PDFInfo
- Publication number
- CA2495502A1 CA2495502A1 CA002495502A CA2495502A CA2495502A1 CA 2495502 A1 CA2495502 A1 CA 2495502A1 CA 002495502 A CA002495502 A CA 002495502A CA 2495502 A CA2495502 A CA 2495502A CA 2495502 A1 CA2495502 A1 CA 2495502A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- hydrocarbyl
- aryl
- halo
- carboxyl
- 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
- 238000000034 method Methods 0.000 title claims abstract description 78
- 102000003846 Carbonic anhydrases Human genes 0.000 title claims abstract description 61
- 108090000209 Carbonic anhydrases Proteins 0.000 title claims abstract description 61
- 230000001404 mediated effect Effects 0.000 title claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 65
- 208000035475 disorder Diseases 0.000 claims abstract description 52
- -1 cyano, carboxyl Chemical group 0.000 claims description 221
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 100
- 239000003795 chemical substances by application Substances 0.000 claims description 88
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 68
- 125000003118 aryl group Chemical group 0.000 claims description 63
- 125000000623 heterocyclic group Chemical group 0.000 claims description 50
- 239000003489 carbonate dehydratase inhibitor Substances 0.000 claims description 49
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 47
- 210000001742 aqueous humor Anatomy 0.000 claims description 36
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 229940122072 Carbonic anhydrase inhibitor Drugs 0.000 claims description 30
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000004043 oxo group Chemical group O=* 0.000 claims description 29
- 150000003180 prostaglandins Chemical class 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 26
- 125000002837 carbocyclic group Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 206010030113 Oedema Diseases 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000002252 acyl group Chemical group 0.000 claims description 16
- 208000008445 altitude sickness Diseases 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 229940079593 drug Drugs 0.000 claims description 13
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
- 239000003112 inhibitor Substances 0.000 claims description 13
- 229940002612 prodrug Drugs 0.000 claims description 13
- 239000000651 prodrug Substances 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical group CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 claims description 12
- 208000010412 Glaucoma Diseases 0.000 claims description 12
- BZKPWHYZMXOIDC-UHFFFAOYSA-N acetazolamide Chemical group CC(=O)NC1=NN=C(S(N)(=O)=O)S1 BZKPWHYZMXOIDC-UHFFFAOYSA-N 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 208000029308 periodic paralysis Diseases 0.000 claims description 12
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 12
- 229930182837 (R)-adrenaline Natural products 0.000 claims description 11
- 229960000571 acetazolamide Drugs 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 239000002934 diuretic Substances 0.000 claims description 11
- 229960005139 epinephrine Drugs 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 239000000048 adrenergic agonist Substances 0.000 claims description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- IAVUPMFITXYVAF-XPUUQOCRSA-N dorzolamide Chemical compound CCN[C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2 IAVUPMFITXYVAF-XPUUQOCRSA-N 0.000 claims description 10
- 229960003933 dorzolamide Drugs 0.000 claims description 10
- 241001465754 Metazoa Species 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 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 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- UGAMYTZPFRXCOG-PPHPATTJSA-N (4r)-4-(ethylamino)-2-(3-methoxypropyl)-1,1-dioxo-3,4-dihydrothieno[3,2-e]thiazine-6-sulfonamide;hydrochloride Chemical compound Cl.CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2 UGAMYTZPFRXCOG-PPHPATTJSA-N 0.000 claims description 8
- 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 8
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 claims description 8
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 claims description 8
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 239000002876 beta blocker Substances 0.000 claims description 8
- HCRKCZRJWPKOAR-JTQLQIEISA-N brinzolamide Chemical compound CCN[C@H]1CN(CCCOC)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2 HCRKCZRJWPKOAR-JTQLQIEISA-N 0.000 claims description 8
- 229960000722 brinzolamide Drugs 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229960003067 cystine Drugs 0.000 claims description 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 8
- 229960004083 methazolamide Drugs 0.000 claims description 8
- 229940116269 uric acid Drugs 0.000 claims description 8
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 7
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- AQOKCDNYWBIDND-FTOWTWDKSA-N bimatoprost Chemical compound CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=CC=C1 AQOKCDNYWBIDND-FTOWTWDKSA-N 0.000 claims description 7
- 229960002470 bimatoprost Drugs 0.000 claims description 7
- 230000001882 diuretic effect Effects 0.000 claims description 7
- 230000004406 elevated intraocular pressure Effects 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 6
- 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 6
- 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 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 6
- DZUXGQBLFALXCR-UHFFFAOYSA-N (+)-(9alpha,11alpha,13E,15S)-9,11,15-trihydroxyprost-13-en-1-oic acid Natural products CCCCCC(O)C=CC1C(O)CC(O)C1CCCCCCC(O)=O DZUXGQBLFALXCR-UHFFFAOYSA-N 0.000 claims description 5
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 claims description 5
- 229960002576 amiloride Drugs 0.000 claims description 5
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 5
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
- 229960003199 etacrynic acid Drugs 0.000 claims description 5
- 229960003883 furosemide Drugs 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 claims description 4
- WTPCCFHCHCMJIT-UHFFFAOYSA-N 1,2,5-oxathiazine Chemical compound O1SC=CN=C1 WTPCCFHCHCMJIT-UHFFFAOYSA-N 0.000 claims description 4
- YHWMFDLNZGIJSD-UHFFFAOYSA-N 2h-1,4-oxazine Chemical compound C1OC=CN=C1 YHWMFDLNZGIJSD-UHFFFAOYSA-N 0.000 claims description 4
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 4
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 4
- 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims description 4
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 4
- 210000002159 anterior chamber Anatomy 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 125000005110 aryl thio group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 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 4
- 229960004064 bumetanide Drugs 0.000 claims description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 229960002155 chlorothiazide Drugs 0.000 claims description 4
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 4
- 229940014142 ethacrynate Drugs 0.000 claims description 4
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 4
- 229960002003 hydrochlorothiazide Drugs 0.000 claims description 4
- 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 4
- 229960004569 indapamide Drugs 0.000 claims description 4
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 4
- 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 4
- 229960002817 metolazone Drugs 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229940054534 ophthalmic solution Drugs 0.000 claims description 4
- 239000002997 ophthalmic solution Substances 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
- 229960001416 pilocarpine Drugs 0.000 claims description 4
- 239000011591 potassium Substances 0.000 claims description 4
- 229910052700 potassium Inorganic materials 0.000 claims description 4
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 claims description 4
- 229960002256 spironolactone Drugs 0.000 claims description 4
- 229960005461 torasemide Drugs 0.000 claims description 4
- MKPLKVHSHYCHOC-AHTXBMBWSA-N travoprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)COC1=CC=CC(C(F)(F)F)=C1 MKPLKVHSHYCHOC-AHTXBMBWSA-N 0.000 claims description 4
- 229960002368 travoprost Drugs 0.000 claims description 4
- 229960001288 triamterene Drugs 0.000 claims description 4
- 102100024644 Carbonic anhydrase 4 Human genes 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 claims description 3
- 229960004324 betaxolol Drugs 0.000 claims description 3
- NWIUTZDMDHAVTP-UHFFFAOYSA-N betaxolol Chemical compound C1=CC(OCC(O)CNC(C)C)=CC=C1CCOCC1CC1 NWIUTZDMDHAVTP-UHFFFAOYSA-N 0.000 claims description 3
- 229960004484 carbachol Drugs 0.000 claims description 3
- LWAFSWPYPHEXKX-UHFFFAOYSA-N carteolol Chemical compound N1C(=O)CCC2=C1C=CC=C2OCC(O)CNC(C)(C)C LWAFSWPYPHEXKX-UHFFFAOYSA-N 0.000 claims description 3
- 230000007423 decrease Effects 0.000 claims description 3
- OCUJLLGVOUDECM-UHFFFAOYSA-N dipivefrin Chemical compound CNCC(O)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1 OCUJLLGVOUDECM-UHFFFAOYSA-N 0.000 claims description 3
- 229960000966 dipivefrine Drugs 0.000 claims description 3
- OSRUSFPMRGDLAG-QMGYSKNISA-N dorzolamide hydrochloride Chemical compound [Cl-].CC[NH2+][C@H]1C[C@H](C)S(=O)(=O)C2=C1C=C(S(N)(=O)=O)S2 OSRUSFPMRGDLAG-QMGYSKNISA-N 0.000 claims description 3
- 229960002017 echothiophate Drugs 0.000 claims description 3
- BJOLKYGKSZKIGU-UHFFFAOYSA-N ecothiopate Chemical compound CCOP(=O)(OCC)SCC[N+](C)(C)C BJOLKYGKSZKIGU-UHFFFAOYSA-N 0.000 claims description 3
- IXHBTMCLRNMKHZ-LBPRGKRZSA-N levobunolol Chemical compound O=C1CCCC2=C1C=CC=C2OC[C@@H](O)CNC(C)(C)C IXHBTMCLRNMKHZ-LBPRGKRZSA-N 0.000 claims description 3
- 229960000831 levobunolol Drugs 0.000 claims description 3
- 229960001697 physostigmine Drugs 0.000 claims description 3
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 claims description 3
- RNAICSBVACLLGM-GNAZCLTHSA-N pilocarpine hydrochloride Chemical compound Cl.C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C RNAICSBVACLLGM-GNAZCLTHSA-N 0.000 claims description 3
- 229940044551 receptor antagonist Drugs 0.000 claims description 3
- 239000002464 receptor antagonist Substances 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 229960004605 timolol Drugs 0.000 claims description 3
- BGKHCLZFGPIKKU-UHFFFAOYSA-N (13E,15S)-15-hydroxy-9-oxo-prosta-10,13-dienoic acid Natural products CCCCCC(O)C=CC1C=CC(=O)C1CCCCCCC(O)=O BGKHCLZFGPIKKU-UHFFFAOYSA-N 0.000 claims description 2
- NWIUTZDMDHAVTP-KRWDZBQOSA-N (S)-betaxolol Chemical compound C1=CC(OC[C@@H](O)CNC(C)C)=CC=C1CCOCC1CC1 NWIUTZDMDHAVTP-KRWDZBQOSA-N 0.000 claims description 2
- JZTKNVMVUVSGJF-UHFFFAOYSA-N 1,2,3,5-oxatriazole Chemical group C=1N=NON=1 JZTKNVMVUVSGJF-UHFFFAOYSA-N 0.000 claims description 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 2
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 2
- PPYNEJLGBMVWMC-UHFFFAOYSA-N 1,2,6-oxathiazine Chemical compound O1SC=CC=N1 PPYNEJLGBMVWMC-UHFFFAOYSA-N 0.000 claims description 2
- VCZQYTJRWNRPHF-UHFFFAOYSA-N 1,2-dioxin Chemical compound O1OC=CC=C1 VCZQYTJRWNRPHF-UHFFFAOYSA-N 0.000 claims description 2
- PCGDBWLKAYKBTN-UHFFFAOYSA-N 1,2-dithiole Chemical group C1SSC=C1 PCGDBWLKAYKBTN-UHFFFAOYSA-N 0.000 claims description 2
- FFJBRYXQVYFDEQ-UHFFFAOYSA-N 1,3,2-dioxazole Chemical group N1OC=CO1 FFJBRYXQVYFDEQ-UHFFFAOYSA-N 0.000 claims description 2
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 2
- IVJFXSLMUSQZMC-UHFFFAOYSA-N 1,3-dithiole Chemical group C1SC=CS1 IVJFXSLMUSQZMC-UHFFFAOYSA-N 0.000 claims description 2
- OHOXMCCFSFSRMD-UHFFFAOYSA-N 1,3-oxathiole Chemical group C1OC=CS1 OHOXMCCFSFSRMD-UHFFFAOYSA-N 0.000 claims description 2
- ZWEGOVJVJZJDQJ-UHFFFAOYSA-N 1,4,2-dioxazole Chemical group C1OC=NO1 ZWEGOVJVJZJDQJ-UHFFFAOYSA-N 0.000 claims description 2
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical group C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 2
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical group N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 claims description 2
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 2
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 2
- JZIBVTUXIVIFGC-UHFFFAOYSA-N 2H-pyrrole Chemical group C1C=CC=N1 JZIBVTUXIVIFGC-UHFFFAOYSA-N 0.000 claims description 2
- HPYLZSUEFFQHRS-UHFFFAOYSA-N 2h-1,2,4-oxadiazine Chemical compound N1OC=CN=C1 HPYLZSUEFFQHRS-UHFFFAOYSA-N 0.000 claims description 2
- KGWNRZLPXLBMPS-UHFFFAOYSA-N 2h-1,3-oxazine Chemical compound C1OC=CC=N1 KGWNRZLPXLBMPS-UHFFFAOYSA-N 0.000 claims description 2
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| US10/213,793 | 2002-08-07 | ||
| US10/213,793 US20030100594A1 (en) | 2001-08-10 | 2002-08-07 | Carbonic anhydrase inhibitor |
| PCT/US2003/004494 WO2004014352A2 (en) | 2002-08-07 | 2003-02-14 | Methods for treating carbonic anhydrase mediated disorders |
Publications (1)
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| CA2495502A1 true CA2495502A1 (en) | 2004-02-19 |
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| CA002495502A Abandoned CA2495502A1 (en) | 2002-08-07 | 2003-02-14 | Methods for treating carbonic anhydrase mediated disorders |
| CA002495516A Abandoned CA2495516A1 (en) | 2002-08-07 | 2003-02-14 | Compositions of a cyclooxygenase-2 selective inhibitor and a carbonic anhydrase inhibitor for the treatment of neoplasia |
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| CA002495516A Abandoned CA2495516A1 (en) | 2002-08-07 | 2003-02-14 | Compositions of a cyclooxygenase-2 selective inhibitor and a carbonic anhydrase inhibitor for the treatment of neoplasia |
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| JP (2) | JP2005539022A (enExample) |
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| DE10035227A1 (de) * | 2000-07-20 | 2002-01-31 | Solvay Pharm Gmbh | Verfahren zum Auffinden von Verbindungen, welche zur Behandlung und/oder Prophylaxe von Fettleibigkeit geeignet sind |
| US6946243B2 (en) * | 2000-07-20 | 2005-09-20 | Solvay Pharmaceuticals Gmbh | Method of identifying compounds suitable for treatment and/or prophylaxis of obesity |
| US20100135980A1 (en) * | 2000-10-16 | 2010-06-03 | Rodriguez Victorio C | Therapeutic and prophylactic uses of cell specific carbonic anhydrase enzymes in treating aging, disorders of aging, cancer, as growth factors, and as an alternative to stem cell therapy |
| US20030220376A1 (en) * | 2001-08-10 | 2003-11-27 | Pharmacia Corporation | Methods for treating carbonic anhydrase mediated disorders |
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| AU2003225571A1 (en) | 2004-02-25 |
| CA2495516A1 (en) | 2004-02-19 |
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