CA2430190A1

CA2430190A1 - Inositol derivatives for increasing chloride secretion and inhibiting inflammation

Inositol derivatives for increasing chloride secretion and inhibiting inflammation Download PDF

Info

Publication number: CA2430190A1
Authority: CA; Canada
Prior art keywords: alkyl; straight; branched chain; group; hydrogen
Prior art date: 2000-11-21
Legal status : Abandoned

Application number

CA002430190A

Other languages

English (en)

French (fr)

Inventor

Alexis Traynor-Kaplan

Carsten Schultz

Tanja Meyerdierks

Mark Moody

Andrew Schnaars

Jane Smith

Current Assignee

Inologic Inc

Original Assignee

Individual

Priority date

2000-11-21

Filing date

2001-11-21

Publication date

2002-05-30

2001-11-21 Application filed by Individual filed Critical Individual

2002-05-30 Publication of CA2430190A1 publication Critical patent/CA2430190A1/en

Status Abandoned legal-status Critical Current

Links

230000028327 secretion Effects 0.000 title claims abstract description 125
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 title claims abstract description 102
206010061218 Inflammation Diseases 0.000 title claims abstract description 48
230000004054 inflammatory process Effects 0.000 title claims abstract description 48
230000002401 inhibitory effect Effects 0.000 title claims description 37
150000004001 inositols Chemical class 0.000 title abstract description 31
230000001965 increasing effect Effects 0.000 title description 14
238000000034 method Methods 0.000 claims abstract description 79
125000000217 alkyl group Chemical group 0.000 claims description 304
150000001875 compounds Chemical class 0.000 claims description 204
229910052739 hydrogen Inorganic materials 0.000 claims description 201
239000001257 hydrogen Substances 0.000 claims description 195
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 143
-1 acetoxymethyl Chemical group 0.000 claims description 111
125000000304 alkynyl group Chemical group 0.000 claims description 109
125000003342 alkenyl group Chemical group 0.000 claims description 106
150000002148 esters Chemical class 0.000 claims description 80
150000003839 salts Chemical class 0.000 claims description 80
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 69
229960000367 inositol Drugs 0.000 claims description 62
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
230000001105 regulatory effect Effects 0.000 claims description 55
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 40
229910052736 halogen Inorganic materials 0.000 claims description 38
150000002431 hydrogen Chemical class 0.000 claims description 38
LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 31
HOXINJBQVZWYGZ-UHFFFAOYSA-N fenbutatin oxide Chemical compound C=1C=CC=CC=1C(C)(C)C[Sn](O[Sn](CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C=1C=CC=CC=1)(CC(C)(C)C=1C=CC=CC=1)CC(C)(C)C1=CC=CC=C1 HOXINJBQVZWYGZ-UHFFFAOYSA-N 0.000 claims description 16
241001465754 Metazoa Species 0.000 claims description 15
150000002367 halogens Chemical group 0.000 claims description 14
125000004122 cyclic group Chemical group 0.000 claims description 10
229910019142 PO4 Inorganic materials 0.000 claims description 6
239000010452 phosphate Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 14
HZTJDBWXSVQJFY-UHFFFAOYSA-N [acetyloxymethoxy-[[4,6,7-tris[bis(acetyloxymethoxy)phosphoryloxy]-2,2-dimethyl-7a-propyl-4,5,6,7-tetrahydro-3aH-1,3-benzodioxol-5-yl]oxy]phosphoryl]oxymethyl acetate Chemical compound C(C)(=O)OCOP(=O)(OCOC(C)=O)OC1C(C(C(C2OC(OC21CCC)(C)C)OP(=O)(OCOC(C)=O)OCOC(C)=O)OP(=O)(OCOC(C)=O)OCOC(C)=O)OP(=O)(OCOC(C)=O)OCOC(C)=O HZTJDBWXSVQJFY-UHFFFAOYSA-N 0.000 claims 3
239000000203 mixture Substances 0.000 abstract description 144
238000011282 treatment Methods 0.000 abstract description 29
230000003213 activating effect Effects 0.000 abstract description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 76
CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 66
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 62
210000004027 cell Anatomy 0.000 description 58
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 57
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239000003981 vehicle Substances 0.000 description 50
238000005160 1H NMR spectroscopy Methods 0.000 description 48
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
230000015572 biosynthetic process Effects 0.000 description 45
238000003786 synthesis reaction Methods 0.000 description 43
201000003883 Cystic fibrosis Diseases 0.000 description 41
238000009472 formulation Methods 0.000 description 41
239000000243 solution Substances 0.000 description 41
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XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 36
238000002953 preparative HPLC Methods 0.000 description 32
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 31
239000000443 aerosol Substances 0.000 description 31
230000002829 reductive effect Effects 0.000 description 30
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 29
230000000694 effects Effects 0.000 description 29
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239000003795 chemical substances by application Substances 0.000 description 28
239000007787 solid Substances 0.000 description 28
239000003937 drug carrier Substances 0.000 description 27
125000005843 halogen group Chemical group 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 26
229910000069 nitrogen hydride Inorganic materials 0.000 description 26
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 24
229960004484 carbachol Drugs 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
239000011575 calcium Substances 0.000 description 23
235000002949 phytic acid Nutrition 0.000 description 23
239000002904 solvent Substances 0.000 description 22
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 21
239000012300 argon atmosphere Substances 0.000 description 21
229910052791 calcium Inorganic materials 0.000 description 21
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 20
238000005481 NMR spectroscopy Methods 0.000 description 20
239000008363 phosphate buffer Substances 0.000 description 20
MRVYFOANPDTYBY-UZAAGFTCSA-N 1D-myo-inositol 3,4,5,6-tetrakisphosphate Chemical compound O[C@H]1[C@@H](O)[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H]1OP(O)(O)=O MRVYFOANPDTYBY-UZAAGFTCSA-N 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 19
239000012267 brine Substances 0.000 description 19
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
229910052786 argon Inorganic materials 0.000 description 18
239000002245 particle Substances 0.000 description 18
230000004044 response Effects 0.000 description 18
230000000112 colonic effect Effects 0.000 description 17
239000000706 filtrate Substances 0.000 description 17
ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 description 17
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 16
239000012230 colorless oil Substances 0.000 description 16
239000003814 drug Substances 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
HATRDXDCPOXQJX-UHFFFAOYSA-N Thapsigargin Natural products CCCCCCCC(=O)OC1C(OC(O)C(=C/C)C)C(=C2C3OC(=O)C(C)(O)C3(O)C(CC(C)(OC(=O)C)C12)OC(=O)CCC)C HATRDXDCPOXQJX-UHFFFAOYSA-N 0.000 description 15
IXFPJGBNCFXKPI-FSIHEZPISA-N thapsigargin Chemical compound CCCC(=O)O[C@H]1C[C@](C)(OC(C)=O)[C@H]2[C@H](OC(=O)CCCCCCC)[C@@H](OC(=O)C(\C)=C/C)C(C)=C2[C@@H]2OC(=O)[C@@](C)(O)[C@]21O IXFPJGBNCFXKPI-FSIHEZPISA-N 0.000 description 15
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
210000004072 lung Anatomy 0.000 description 14
239000012044 organic layer Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000012298 atmosphere Substances 0.000 description 13
210000003097 mucus Anatomy 0.000 description 13
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KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
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210000002919 epithelial cell Anatomy 0.000 description 11
230000003834 intracellular effect Effects 0.000 description 11
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125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 11
UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 description 11
ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 10
ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 10
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
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XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 10
CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 10
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229940126062 Compound A Drugs 0.000 description 8
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NHYXMAKLBXBVEO-UHFFFAOYSA-N bromomethyl acetate Chemical compound CC(=O)OCBr NHYXMAKLBXBVEO-UHFFFAOYSA-N 0.000 description 7
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SQUHHTBVTRBESD-UHFFFAOYSA-N Hexa-Ac-myo-Inositol Natural products CC(=O)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O SQUHHTBVTRBESD-UHFFFAOYSA-N 0.000 description 5
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