CA2100676A1 - Proprietes anticoagulantes de composes macrocycliques et methode de traitement - Google Patents
Proprietes anticoagulantes de composes macrocycliques et methode de traitementInfo
- Publication number
- CA2100676A1 CA2100676A1 CA002100676A CA2100676A CA2100676A1 CA 2100676 A1 CA2100676 A1 CA 2100676A1 CA 002100676 A CA002100676 A CA 002100676A CA 2100676 A CA2100676 A CA 2100676A CA 2100676 A1 CA2100676 A1 CA 2100676A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- ester
- group
- compound
- subunits
- 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
- 150000002678 macrocyclic compounds Chemical class 0.000 title claims abstract description 78
- 238000000034 method Methods 0.000 title description 52
- 238000011282 treatment Methods 0.000 title description 18
- 230000002429 anti-coagulating effect Effects 0.000 title description 8
- 239000000203 mixture Substances 0.000 claims abstract description 43
- 125000001424 substituent group Chemical group 0.000 claims abstract description 34
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract description 25
- 125000003118 aryl group Chemical group 0.000 claims abstract description 24
- 230000023555 blood coagulation Effects 0.000 claims abstract description 17
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 10
- 239000003937 drug carrier Substances 0.000 claims abstract 3
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 119
- -1 sulfinate ester Chemical class 0.000 claims description 33
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 29
- 230000015271 coagulation Effects 0.000 claims description 21
- 238000005345 coagulation Methods 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 229940124530 sulfonamide Drugs 0.000 claims description 13
- 150000003456 sulfonamides Chemical class 0.000 claims description 13
- 150000008054 sulfonate salts Chemical class 0.000 claims description 11
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical class [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 claims description 9
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 8
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 150000008378 aryl ethers Chemical class 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- QPILZZVXGUNELN-UHFFFAOYSA-M sodium;4-amino-5-hydroxynaphthalene-2,7-disulfonate;hydron Chemical compound [Na+].OS(=O)(=O)C1=CC(O)=C2C(N)=CC(S([O-])(=O)=O)=CC2=C1 QPILZZVXGUNELN-UHFFFAOYSA-M 0.000 claims description 3
- 230000000694 effects Effects 0.000 description 82
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- 238000003556 assay Methods 0.000 description 50
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 47
- 230000035602 clotting Effects 0.000 description 45
- 206010053567 Coagulopathies Diseases 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- HLVXFWDLRHCZEI-UHFFFAOYSA-N chromotropic acid Chemical group OS(=O)(=O)C1=CC(O)=C2C(O)=CC(S(O)(=O)=O)=CC2=C1 HLVXFWDLRHCZEI-UHFFFAOYSA-N 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000000523 sample Substances 0.000 description 32
- 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 description 30
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- 230000014508 negative regulation of coagulation Effects 0.000 description 14
- 238000007363 ring formation reaction Methods 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 238000002560 therapeutic procedure Methods 0.000 description 14
- 125000006413 ring segment Chemical group 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
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- 210000004623 platelet-rich plasma Anatomy 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
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- 108010035532 Collagen Proteins 0.000 description 9
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- 102000009123 Fibrin Human genes 0.000 description 9
- BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 9
- 229940127219 anticoagulant drug Drugs 0.000 description 9
- 229910052791 calcium Inorganic materials 0.000 description 9
- 239000011575 calcium Substances 0.000 description 9
- 229920001436 collagen Polymers 0.000 description 9
- 229950003499 fibrin Drugs 0.000 description 9
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 229940012957 plasmin Drugs 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
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- 239000011734 sodium Substances 0.000 description 8
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 229910006069 SO3H Inorganic materials 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 239000001509 sodium citrate Substances 0.000 description 7
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 7
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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- 150000003839 salts Chemical class 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/647,720 US5196452A (en) | 1991-01-29 | 1991-01-29 | Macrocyclic anti-viral compound and method |
US07/647,469 US5166173A (en) | 1991-01-29 | 1991-01-29 | Method of treating herpes simplex virus infection |
US647,469 | 1991-01-29 | ||
US647,720 | 1991-01-29 | ||
US79213591A | 1991-11-13 | 1991-11-13 | |
US792,135 | 1991-11-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2100676A1 true CA2100676A1 (fr) | 1992-07-30 |
Family
ID=27417790
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002100676A Abandoned CA2100676A1 (fr) | 1991-01-29 | 1992-01-21 | Proprietes anticoagulantes de composes macrocycliques et methode de traitement |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0569479A1 (fr) |
JP (1) | JPH06505477A (fr) |
KR (1) | KR930702967A (fr) |
AU (1) | AU657308B2 (fr) |
CA (1) | CA2100676A1 (fr) |
WO (1) | WO1992012708A1 (fr) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5409959A (en) * | 1991-01-29 | 1995-04-25 | Genelabs Incorporated | Antithrombotic treatment with calix(n)arene compounds |
US5952526A (en) * | 1996-06-26 | 1999-09-14 | Transdiffusia S.A. | Process for the dealkylating sulfonation of p-alkyl calixarenes |
AU2003212974B2 (en) | 2002-02-07 | 2008-08-14 | Covalent Partners, Llc | Macrocyclic module compositions |
CA2475567A1 (fr) | 2002-02-07 | 2003-08-14 | Covalent Partners, Llc | Compositions pour nanofilms et membrane |
US20040106741A1 (en) | 2002-09-17 | 2004-06-03 | Kriesel Joshua W. | Nanofilm compositions with polymeric components |
WO2005030711A2 (fr) | 2003-08-06 | 2005-04-07 | Covalent Partners Llc | Compositions modulaires macrocycliques pontees |
KR100707163B1 (ko) * | 2005-10-12 | 2007-04-13 | 삼성에스디아이 주식회사 | 고체산, 이를 포함하는 고분자 전해질막 및 이를 채용한연료전지 |
KR101264331B1 (ko) | 2006-02-25 | 2013-05-14 | 삼성에스디아이 주식회사 | 고분자 전해질막, 이의 제조 방법 및 이를 구비한 연료전지 |
DE102006036326A1 (de) * | 2006-08-03 | 2008-02-07 | Charité - Universitätsmedizin Berlin | Dendritische Polyglycerolsulfate und -sulfonate und deren Verwendung bei entzündlichen Erkrankungen |
JP5700269B1 (ja) * | 2013-07-19 | 2015-04-15 | Dic株式会社 | フェノール性水酸基含有化合物、感光性組成物、レジスト用組成物、レジスト塗膜、硬化性組成物、レジスト下層膜用組成物、及びレジスト下層膜 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL87444A0 (en) * | 1988-08-12 | 1989-01-31 | Hadassah Med Org | Pharmaceutical compositions containing polyaromatic compounds |
-
1992
- 1992-01-21 KR KR1019930702267A patent/KR930702967A/ko not_active Application Discontinuation
- 1992-01-21 EP EP92904689A patent/EP0569479A1/fr not_active Ceased
- 1992-01-21 AU AU12645/92A patent/AU657308B2/en not_active Ceased
- 1992-01-21 JP JP4505406A patent/JPH06505477A/ja active Pending
- 1992-01-21 CA CA002100676A patent/CA2100676A1/fr not_active Abandoned
- 1992-01-21 WO PCT/US1992/000501 patent/WO1992012708A1/fr not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
JPH06505477A (ja) | 1994-06-23 |
AU1264592A (en) | 1992-08-27 |
WO1992012708A1 (fr) | 1992-08-06 |
EP0569479A1 (fr) | 1993-11-18 |
AU657308B2 (en) | 1995-03-09 |
KR930702967A (ko) | 1993-11-29 |
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