ZA200305694B

ZA200305694B - Combinations of sterol absorption inhibitor(s) with blood modifier(s) for treating vascular conditions.

Combinations of sterol absorption inhibitor(s) with blood modifier(s) for treating vascular conditions. Download PDF

Info

Publication number: ZA200305694B
Authority: ZA; South Africa
Prior art keywords: alkyl; group; aryl; independently selected; substituted
Prior art date: 2001-01-26

Application number

ZA200305694A

Other languages

English (en)

Inventor

Teddy Kosoglou

Rudyard Joseph Ress

John Strony

Enrico P Veltri

Original Assignee

Schering Corp

Priority date

2001-01-26

Filing date

2003-07-23

Publication date

2004-10-25

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=34572580&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ZA200305694(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2003-07-23 Application filed by Schering Corp filed Critical Schering Corp

2004-10-25 Publication of ZA200305694B publication Critical patent/ZA200305694B/en

Links

239000003112 inhibitor Substances 0.000 title claims description 114
229930182558 Sterol Natural products 0.000 title claims description 94
235000003702 sterols Nutrition 0.000 title claims description 94
150000003432 sterols Chemical class 0.000 title claims description 90
238000010521 absorption reaction Methods 0.000 title claims description 73
210000004369 blood Anatomy 0.000 title claims description 70
239000008280 blood Substances 0.000 title claims description 70
239000003607 modifier Substances 0.000 title claims description 57
230000002792 vascular Effects 0.000 title claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 240
150000001875 compounds Chemical class 0.000 claims description 201
239000000203 mixture Substances 0.000 claims description 138
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 136
-1 R7-benzyl Chemical group 0.000 claims description 106
229910052739 hydrogen Inorganic materials 0.000 claims description 106
125000003118 aryl group Chemical group 0.000 claims description 86
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 77
150000003839 salts Chemical class 0.000 claims description 74
239000001257 hydrogen Substances 0.000 claims description 69
239000012453 solvate Substances 0.000 claims description 61
125000003545 alkoxy group Chemical group 0.000 claims description 57
125000005843 halogen group Chemical class 0.000 claims description 55
125000001424 substituent group Chemical group 0.000 claims description 55
238000011282 treatment Methods 0.000 claims description 48
229910052799 carbon Inorganic materials 0.000 claims description 45
238000000034 method Methods 0.000 claims description 44
230000001225 therapeutic effect Effects 0.000 claims description 43
230000015572 biosynthetic process Effects 0.000 claims description 34
229940002612 prodrug Drugs 0.000 claims description 33
239000000651 prodrug Substances 0.000 claims description 33
125000002947 alkylene group Chemical group 0.000 claims description 31
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
241000124008 Mammalia Species 0.000 claims description 29
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
235000012000 cholesterol Nutrition 0.000 claims description 28
239000003795 chemical substances by application Substances 0.000 claims description 26
239000012190 activator Substances 0.000 claims description 25
125000001072 heteroaryl group Chemical group 0.000 claims description 24
229920000669 heparin Polymers 0.000 claims description 22
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
102100030951 Tissue factor pathway inhibitor Human genes 0.000 claims description 13
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 13
108010013555 lipoprotein-associated coagulation inhibitor Proteins 0.000 claims description 13
125000003003 spiro group Chemical group 0.000 claims description 13
125000001544 thienyl group Chemical group 0.000 claims description 13
229940123583 Factor Xa inhibitor Drugs 0.000 claims description 12
208000008589 Obesity Diseases 0.000 claims description 12
239000003146 anticoagulant agent Substances 0.000 claims description 12
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
235000020824 obesity Nutrition 0.000 claims description 12
125000004076 pyridyl group Chemical group 0.000 claims description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 10
125000002541 furyl group Chemical group 0.000 claims description 10
125000002883 imidazolyl group Chemical group 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
125000003226 pyrazolyl group Chemical group 0.000 claims description 10
125000000168 pyrrolyl group Chemical group 0.000 claims description 10
125000000335 thiazolyl group Chemical group 0.000 claims description 10
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims description 9
229920000080 bile acid sequestrant Polymers 0.000 claims description 9
229960002897 heparin Drugs 0.000 claims description 9
239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims description 9
125000003386 piperidinyl group Chemical group 0.000 claims description 9
239000000106 platelet aggregation inhibitor Substances 0.000 claims description 9
229920001499 Heparinoid Polymers 0.000 claims description 8
BYPFEZZEUUWMEJ-UHFFFAOYSA-N Pentoxifylline Chemical compound O=C1N(CCCCC(=O)C)C(=O)N(C)C2=C1N(C)C=N2 BYPFEZZEUUWMEJ-UHFFFAOYSA-N 0.000 claims description 8
125000003282 alkyl amino group Chemical group 0.000 claims description 8
125000002993 cycloalkylene group Chemical group 0.000 claims description 8
206010012601 diabetes mellitus Diseases 0.000 claims description 8
239000002554 heparinoid Substances 0.000 claims description 8
125000000592 heterocycloalkyl group Chemical class 0.000 claims description 8
125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 8
125000000842 isoxazolyl group Chemical group 0.000 claims description 8
125000002757 morpholinyl group Chemical group 0.000 claims description 8
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
230000002265 prevention Effects 0.000 claims description 8
125000003373 pyrazinyl group Chemical group 0.000 claims description 8
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
LMHIPJMTZHDKEW-XQYLJSSYSA-M Epoprostenol sodium Chemical compound [Na+].O1\C(=C/CCCC([O-])=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 LMHIPJMTZHDKEW-XQYLJSSYSA-M 0.000 claims description 7
125000004450 alkenylene group Chemical group 0.000 claims description 7
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 7
125000001624 naphthyl group Chemical group 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
229960001476 pentoxifylline Drugs 0.000 claims description 7
108090000765 processed proteins & peptides Proteins 0.000 claims description 7
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 7
ZTHSAEXVSBEBHE-BDQAORGHSA-N 2-[(2s)-4-methyl-3-oxo-7-(4-piperidin-4-ylpiperidine-1-carbonyl)-2,5-dihydro-1h-1,4-benzodiazepin-2-yl]acetic acid;hydrochloride Chemical compound Cl.O=C([C@H](CC(O)=O)NC1=CC=2)N(C)CC1=CC=2C(=O)N(CC1)CCC1C1CCNCC1 ZTHSAEXVSBEBHE-BDQAORGHSA-N 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
RRGUKTPIGVIEKM-UHFFFAOYSA-N cilostazol Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCC1=NN=NN1C1CCCCC1 RRGUKTPIGVIEKM-UHFFFAOYSA-N 0.000 claims description 6
239000002319 fibrinogen receptor antagonist Substances 0.000 claims description 6
125000002971 oxazolyl group Chemical group 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 claims description 6
108010001831 LDL receptors Proteins 0.000 claims description 5
RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 claims description 5
WBNUCLPUOSXSNJ-ZDUSSCGKSA-N Sibrafiban Chemical compound C1CC(OCC(=O)OCC)CCN1C(=O)[C@H](C)NC(=O)C1=CC=C(C(=N)NO)C=C1 WBNUCLPUOSXSNJ-ZDUSSCGKSA-N 0.000 claims description 5
229940127218 antiplatelet drug Drugs 0.000 claims description 5
229960004676 antithrombotic agent Drugs 0.000 claims description 5
CTPOHARTNNSRSR-APJZLKAGSA-N beraprost Chemical compound O([C@H]1C[C@@H](O)[C@@H]([C@@H]21)/C=C/[C@@H](O)C(C)CC#CC)C1=C2C=CC=C1CCCC(O)=O CTPOHARTNNSRSR-APJZLKAGSA-N 0.000 claims description 5
OIRCOABEOLEUMC-GEJPAHFPSA-N bivalirudin Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 OIRCOABEOLEUMC-GEJPAHFPSA-N 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 5
229960002855 simvastatin Drugs 0.000 claims description 5
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 4
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims description 4
229910052684 Cerium Inorganic materials 0.000 claims description 4
229960000446 abciximab Drugs 0.000 claims description 4
SVMJTTTTYFMATC-QSGPNNMYSA-N acetic acid;ethyl 3-[[(3s)-1-(4-carbamimidoylphenyl)-2-oxopyrrolidin-3-yl]carbamoylamino]propanoate;hydrate Chemical compound O.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.O=C1[C@@H](NC(=O)NCCC(=O)OCC)CCN1C1=CC=C(C(N)=N)C=C1.O=C1[C@@H](NC(=O)NCCC(=O)OCC)CCN1C1=CC=C(C(N)=N)C=C1.O=C1[C@@H](NC(=O)NCCC(=O)OCC)CCN1C1=CC=C(C(N)=N)C=C1.O=C1[C@@H](NC(=O)NCCC(=O)OCC)CCN1C1=CC=C(C(N)=N)C=C1 SVMJTTTTYFMATC-QSGPNNMYSA-N 0.000 claims description 4
WDEMHBVIYZGQCD-KALLACGZSA-N acetic acid;methyl (2s)-2-(butoxycarbonylamino)-3-[[2-[(5r)-3-(4-carbamimidoylphenyl)-4,5-dihydro-1,2-oxazol-5-yl]acetyl]amino]propanoate Chemical compound CC(O)=O.O1[C@@H](CC(=O)NC[C@H](NC(=O)OCCCC)C(=O)OC)CC(C=2C=CC(=CC=2)C(N)=N)=N1 WDEMHBVIYZGQCD-KALLACGZSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 4
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 4
229940127219 anticoagulant drug Drugs 0.000 claims description 4
239000003963 antioxidant agent Substances 0.000 claims description 4
125000004104 aryloxy group Chemical class 0.000 claims description 4
125000002047 benzodioxolyl group Chemical class O1OC(C2=C1C=CC=C2)* 0.000 claims description 4
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
125000000051 benzyloxy group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
229960002890 beraprost Drugs 0.000 claims description 4
108010055460 bivalirudin Proteins 0.000 claims description 4
229960001500 bivalirudin Drugs 0.000 claims description 4
229960004588 cilostazol Drugs 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
229940018872 dalteparin sodium Drugs 0.000 claims description 4
125000005879 dioxolanyl group Chemical group 0.000 claims description 4
IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 claims description 4
OEHFRZLKGRKFAS-UHFFFAOYSA-N droxicam Chemical compound C12=CC=CC=C2S(=O)(=O)N(C)C(C2=O)=C1OC(=O)N2C1=CC=CC=N1 OEHFRZLKGRKFAS-UHFFFAOYSA-N 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
ZHCINJQZDFCSEL-CYBMUJFWSA-N ethyl (3s)-3-[[4-(4-carbamimidoylanilino)-4-oxobutanoyl]amino]pent-4-ynoate Chemical compound CCOC(=O)C[C@@H](C#C)NC(=O)CCC(=O)NC1=CC=C(C(N)=N)C=C1 ZHCINJQZDFCSEL-CYBMUJFWSA-N 0.000 claims description 4
VJDOPFARMOLELX-ZDUSSCGKSA-N ethyl 3-[[(3s)-1-(4-carbamimidoylphenyl)-2-oxopyrrolidin-3-yl]carbamoylamino]propanoate Chemical compound O=C1[C@@H](NC(=O)NCCC(=O)OCC)CCN1C1=CC=C(C(N)=N)C=C1 VJDOPFARMOLELX-ZDUSSCGKSA-N 0.000 claims description 4
IKZACQMAVUIGPY-HOTGVXAUSA-N fradafiban Chemical compound C1=CC(C(=N)N)=CC=C1C(C=C1)=CC=C1OC[C@H]1NC(=O)[C@H](CC(O)=O)C1 IKZACQMAVUIGPY-HOTGVXAUSA-N 0.000 claims description 4
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 4
HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 claims description 4
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 4
125000004043 oxo group Chemical group O=* 0.000 claims description 4
QYSPLQLAKJAUJT-UHFFFAOYSA-N piroxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=CC=CC=N1 QYSPLQLAKJAUJT-UHFFFAOYSA-N 0.000 claims description 4
102000004196 processed proteins & peptides Human genes 0.000 claims description 4
125000002098 pyridazinyl group Chemical group 0.000 claims description 4
229950005747 sibrafiban Drugs 0.000 claims description 4
208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
238000006467 substitution reaction Methods 0.000 claims description 4
125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
MTKNGOHFNXIVOS-UHFFFAOYSA-N ticlopidine hydrochloride Chemical compound [H+].[Cl-].ClC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 MTKNGOHFNXIVOS-UHFFFAOYSA-N 0.000 claims description 4
229940064689 tinzaparin sodium Drugs 0.000 claims description 4
COKMIXFXJJXBQG-NRFANRHFSA-N tirofiban Chemical compound C1=CC(C[C@H](NS(=O)(=O)CCCC)C(O)=O)=CC=C1OCCCCC1CCNCC1 COKMIXFXJJXBQG-NRFANRHFSA-N 0.000 claims description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
229940088594 vitamin Drugs 0.000 claims description 4
235000013343 vitamin Nutrition 0.000 claims description 4
239000011782 vitamin Substances 0.000 claims description 4
229930003231 vitamin Natural products 0.000 claims description 4
BISKEOIROPAOGY-RXQQAGQTSA-N (2s)-n-[(2s)-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-1-[(2r)-2-(methylamino)-3-phenylpropanoyl]pyrrolidine-2-carboxamide;sulfuric acid Chemical compound OS(O)(=O)=O.C([C@@H](NC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C=O)C1=CC=CC=C1 BISKEOIROPAOGY-RXQQAGQTSA-N 0.000 claims description 3
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 3
YETULFFXNIHQLK-UHFFFAOYSA-N 1-ethynyl-4-(2-fluorophenyl)benzene Chemical compound FC1=CC=CC=C1C1=CC=C(C#C)C=C1 YETULFFXNIHQLK-UHFFFAOYSA-N 0.000 claims description 3
KGVYOGLFOPNPDJ-UHFFFAOYSA-N 2-[2-(4,5-diphenyl-1h-imidazol-2-yl)phenoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOC1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 KGVYOGLFOPNPDJ-UHFFFAOYSA-N 0.000 claims description 3
BYDKEYCXCIVOOV-JTSKRJEESA-N 2-[[(2s)-4-[[(3s)-1-carbamimidoylpiperidin-3-yl]methylamino]-2-(naphthalen-2-ylsulfonylamino)-4-oxobutanoyl]-cyclopropylamino]acetic acid Chemical compound C1N(C(=N)N)CCC[C@H]1CNC(=O)C[C@@H](C(=O)N(CC(O)=O)C1CC1)NS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 BYDKEYCXCIVOOV-JTSKRJEESA-N 0.000 claims description 3
CIPBQTCSXVEDSG-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-2-(trifluoromethyl)-1,3-thiazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2C=CC(OC)=CC=2)SC(C(F)(F)F)=N1 CIPBQTCSXVEDSG-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
229960001138 acetylsalicylic acid Drugs 0.000 claims description 3
NJTMVDAFPIEZAJ-BMKVUGPNSA-L calcium;(5z)-5-[(3ar,4r,5r,6as)-5-hydroxy-4-[(e,3s)-3-hydroxyoct-1-enyl]-6a-methyl-1,3,3a,4,5,6-hexahydropentalen-2-ylidene]pentanoate Chemical compound [Ca+2].C1\C(=C/CCCC([O-])=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@]21C.C1\C(=C/CCCC([O-])=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@]21C NJTMVDAFPIEZAJ-BMKVUGPNSA-L 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
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