NZ570943A - Polymorphs of sitaxsentan - Google Patents

Info

Publication number

NZ570943A

NZ570943A NZ570943A NZ57094307A NZ570943A NZ 570943 A NZ570943 A NZ 570943A NZ 570943 A NZ570943 A NZ 570943A NZ 57094307 A NZ57094307 A NZ 57094307A NZ 570943 A NZ570943 A NZ 570943A

Authority

NZ

New Zealand

Prior art keywords

methyl

polymorph

sodium

certain embodiments

amount

Prior art date

2006-03-13

Links

• Espacenet
• Global Dossier
• Discuss

• PHWXUGHIIBDVKD-UHFFFAOYSA-N sitaxentan Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)CC=2C(=CC=3OCOC=3C=2)C)=C1Cl PHWXUGHIIBDVKD-UHFFFAOYSA-N 0.000 title description 8
• 229960002578 sitaxentan Drugs 0.000 title description 8
• 159000000000 sodium salts Chemical class 0.000 claims abstract description 35
• BWJZHYWAXLWLTB-UHFFFAOYSA-N thiophene-3-sulfonamide Chemical compound NS(=O)(=O)C=1C=CSC=1 BWJZHYWAXLWLTB-UHFFFAOYSA-N 0.000 claims abstract description 34
• 108050009340 Endothelin Proteins 0.000 claims abstract description 32
• 102000002045 Endothelin Human genes 0.000 claims abstract description 28
• ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 claims abstract description 28
• 238000011282 treatment Methods 0.000 claims abstract description 20
• 230000001404 mediated effect Effects 0.000 claims abstract description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 76
• 239000007787 solid Substances 0.000 claims description 69
• 239000000243 solution Substances 0.000 claims description 69
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 67
• 150000001875 compounds Chemical class 0.000 claims description 62
• 239000002904 solvent Substances 0.000 claims description 57
• 238000000034 method Methods 0.000 claims description 54
• 238000000634 powder X-ray diffraction Methods 0.000 claims description 53
• -1 methylenedioxy Chemical group 0.000 claims description 52
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 41
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 35
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 28
• 201000010099 disease Diseases 0.000 claims description 26
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
• 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 claims description 23
• 239000012296 anti-solvent Substances 0.000 claims description 23
• 239000003814 drug Substances 0.000 claims description 23
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 21
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 21
• 239000011734 sodium Substances 0.000 claims description 21
• 229910052708 sodium Inorganic materials 0.000 claims description 21
• 230000008569 process Effects 0.000 claims description 20
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 19
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 19
• 208000035475 disorder Diseases 0.000 claims description 15
• 239000003937 drug carrier Substances 0.000 claims description 15
• 238000001237 Raman spectrum Methods 0.000 claims description 14
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 14
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 13
• JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 12
• 239000012047 saturated solution Substances 0.000 claims description 11
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 10
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
• 208000003037 Diastolic Heart Failure Diseases 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 206010020772 Hypertension Diseases 0.000 claims description 7
• 206010047139 Vasoconstriction Diseases 0.000 claims description 6
• 230000000052 comparative effect Effects 0.000 claims description 6
• 229940011051 isopropyl acetate Drugs 0.000 claims description 6
• 230000025033 vasoconstriction Effects 0.000 claims description 6
• 208000002815 pulmonary hypertension Diseases 0.000 claims description 5
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 4
• 208000029523 Interstitial Lung disease Diseases 0.000 claims description 4
• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 4
• 238000001816 cooling Methods 0.000 claims description 4
• 229960003444 immunosuppressant agent Drugs 0.000 claims description 4
• 239000003018 immunosuppressive agent Substances 0.000 claims description 4
• 229920006395 saturated elastomer Polymers 0.000 claims description 4
• 206010002199 Anaphylactic shock Diseases 0.000 claims description 3
• 208000032456 Hemorrhagic Shock Diseases 0.000 claims description 3
• 208000019255 Menstrual disease Diseases 0.000 claims description 3
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 3
• 208000001647 Renal Insufficiency Diseases 0.000 claims description 3
• 206010040070 Septic Shock Diseases 0.000 claims description 3
• 206010049771 Shock haemorrhagic Diseases 0.000 claims description 3
• 208000003455 anaphylaxis Diseases 0.000 claims description 3
• 208000027866 inflammatory disease Diseases 0.000 claims description 3
• 201000006370 kidney failure Diseases 0.000 claims description 3
• 239000002831 pharmacologic agent Substances 0.000 claims description 3
• 208000010228 Erectile Dysfunction Diseases 0.000 claims description 2
• 108090000394 Erythropoietin Proteins 0.000 claims description 2
• 208000001132 Osteoporosis Diseases 0.000 claims description 2
• 230000002238 attenuated effect Effects 0.000 claims description 2
• 229940105423 erythropoietin Drugs 0.000 claims description 2
• 208000019622 heart disease Diseases 0.000 claims description 2
• 230000001861 immunosuppressant effect Effects 0.000 claims description 2
• 201000001881 impotence Diseases 0.000 claims description 2
• 230000009245 menopause Effects 0.000 claims description 2
• 230000002611 ovarian Effects 0.000 claims description 2
• OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 claims description 2
• 201000011461 pre-eclampsia Diseases 0.000 claims description 2
• 239000002244 precipitate Substances 0.000 claims description 2
• 230000035935 pregnancy Effects 0.000 claims description 2
• 230000009467 reduction Effects 0.000 claims description 2
• 208000023504 respiratory system disease Diseases 0.000 claims description 2
• 125000003944 tolyl group Chemical group 0.000 claims description 2
• GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 2
• 208000020446 Cardiac disease Diseases 0.000 claims 1
• 102000003951 Erythropoietin Human genes 0.000 claims 1
• 208000030136 Marchiafava-Bignami Disease Diseases 0.000 claims 1
• MDTNUYUCUYPIHE-UHFFFAOYSA-N sodium;(4-chloro-3-methyl-1,2-oxazol-5-yl)-[2-[2-(6-methyl-1,3-benzodioxol-5-yl)acetyl]thiophen-3-yl]sulfonylazanide Chemical compound [Na+].CC1=NOC([N-]S(=O)(=O)C2=C(SC=C2)C(=O)CC=2C(=CC=3OCOC=3C=2)C)=C1Cl MDTNUYUCUYPIHE-UHFFFAOYSA-N 0.000 abstract description 78
• 239000000203 mixture Substances 0.000 description 163
• 239000003826 tablet Substances 0.000 description 81
• 238000009472 formulation Methods 0.000 description 70
• 239000008176 lyophilized powder Substances 0.000 description 58
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 36
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 32
• 239000004480 active ingredient Substances 0.000 description 31
• 239000000463 material Substances 0.000 description 30
• 239000007935 oral tablet Substances 0.000 description 26
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
• 235000019441 ethanol Nutrition 0.000 description 25
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 24
• 239000002552 dosage form Substances 0.000 description 24
• 229940096978 oral tablet Drugs 0.000 description 24
• WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 description 22
• 229960001021 lactose monohydrate Drugs 0.000 description 22
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 21
• AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 21
• 230000000694 effects Effects 0.000 description 21
• 229940080313 sodium starch Drugs 0.000 description 21
• 229920000168 Microcrystalline cellulose Polymers 0.000 description 19
• 235000019813 microcrystalline cellulose Nutrition 0.000 description 19
• 239000008108 microcrystalline cellulose Substances 0.000 description 19
• 229940016286 microcrystalline cellulose Drugs 0.000 description 19
• 235000015424 sodium Nutrition 0.000 description 19
• 239000000725 suspension Substances 0.000 description 19
• 229960005070 ascorbic acid Drugs 0.000 description 18
• GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 18
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
• 239000002775 capsule Substances 0.000 description 17
• 239000003795 chemical substances by application Substances 0.000 description 17
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 16
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 16
• 239000003112 inhibitor Substances 0.000 description 16
• 235000019359 magnesium stearate Nutrition 0.000 description 16
• 235000010355 mannitol Nutrition 0.000 description 16
• 235000010323 ascorbic acid Nutrition 0.000 description 15
• 239000011668 ascorbic acid Substances 0.000 description 15
• 238000000576 coating method Methods 0.000 description 15
• 238000001914 filtration Methods 0.000 description 15
• 239000000126 substance Substances 0.000 description 15
• 230000004584 weight gain Effects 0.000 description 15
• 235000019786 weight gain Nutrition 0.000 description 15
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 14
• 239000003963 antioxidant agent Substances 0.000 description 14
• 235000006708 antioxidants Nutrition 0.000 description 14
• 239000011248 coating agent Substances 0.000 description 14
• 229940009662 edetate Drugs 0.000 description 14
• 238000002474 experimental method Methods 0.000 description 14
• 239000007788 liquid Substances 0.000 description 14
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• 208000024891 symptom Diseases 0.000 description 14
• 238000004458 analytical method Methods 0.000 description 13
• 229940079593 drug Drugs 0.000 description 13
• 102000005962 receptors Human genes 0.000 description 13
• 108020003175 receptors Proteins 0.000 description 13
• 238000002336 sorption--desorption measurement Methods 0.000 description 13
• QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 12
• 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 12
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• 239000005557 antagonist Substances 0.000 description 12
• 235000010385 ascorbyl palmitate Nutrition 0.000 description 12
• 238000013270 controlled release Methods 0.000 description 12
• 239000003085 diluting agent Substances 0.000 description 12
• 235000019439 ethyl acetate Nutrition 0.000 description 12
• 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 12
• 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 12
• 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 12
• UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 12
• 239000000843 powder Substances 0.000 description 12
• 238000005185 salting out Methods 0.000 description 12
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
• 238000002425 crystallisation Methods 0.000 description 11
• 230000008025 crystallization Effects 0.000 description 11
• 238000000113 differential scanning calorimetry Methods 0.000 description 11
• BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 11
• 239000000839 emulsion Substances 0.000 description 11
• 239000000546 pharmaceutical excipient Substances 0.000 description 11
• 238000012360 testing method Methods 0.000 description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
• QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 10
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• 239000008121 dextrose Substances 0.000 description 10
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• BBMHARZCALWXSL-UHFFFAOYSA-M sodium dihydrogenphosphate monohydrate Chemical compound O.[Na+].OP(O)([O-])=O BBMHARZCALWXSL-UHFFFAOYSA-M 0.000 description 10
• 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 10
• 229920003084 Avicel® PH-102 Polymers 0.000 description 9
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• 239000000314 lubricant Substances 0.000 description 9
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• 230000001225 therapeutic effect Effects 0.000 description 9
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• JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 7
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 7
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• PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 7
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• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
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• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Natural products OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 5
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