FR2526025A1 - Analogues des prostaglandines constitues par des 7-oxabicycloheptane hydrazones a action therapeutique - Google Patents
Analogues des prostaglandines constitues par des 7-oxabicycloheptane hydrazones a action therapeutique Download PDFInfo
- Publication number
- FR2526025A1 FR2526025A1 FR8307341A FR8307341A FR2526025A1 FR 2526025 A1 FR2526025 A1 FR 2526025A1 FR 8307341 A FR8307341 A FR 8307341A FR 8307341 A FR8307341 A FR 8307341A FR 2526025 A1 FR2526025 A1 FR 2526025A1
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- FR
- France
- Prior art keywords
- acid
- methyl
- oxabicyclol
- heptenoic
- compound according
- 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.)
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- 150000003180 prostaglandins Chemical class 0.000 title description 3
- DYWAPFDKPAHSED-UHFFFAOYSA-N 2-cycloheptyloxepane Chemical compound C1CCCCCC1C1OCCCCC1 DYWAPFDKPAHSED-UHFFFAOYSA-N 0.000 title description 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- -1 ARYLOXY Chemical class 0.000 claims abstract description 71
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 150000003973 alkyl amines Chemical class 0.000 claims abstract description 3
- 150000004982 aromatic amines Chemical class 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 61
- 239000000203 mixture Substances 0.000 claims description 30
- 150000004702 methyl esters Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 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 claims 2
- 206010006482 Bronchospasm Diseases 0.000 claims 1
- 229940114079 arachidonic acid Drugs 0.000 claims 1
- 235000021342 arachidonic acid Nutrition 0.000 claims 1
- 230000007885 bronchoconstriction Effects 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical group [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 abstract 1
- 101150065749 Churc1 gene Proteins 0.000 abstract 1
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- FIULGFJIHJJXMT-UHFFFAOYSA-N [C]1[N]C=CC=C1 Chemical class [C]1[N]C=CC=C1 FIULGFJIHJJXMT-UHFFFAOYSA-N 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 61
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 39
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- 238000000034 method Methods 0.000 description 23
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- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 19
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
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- 239000000047 product Substances 0.000 description 18
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
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- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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- 150000003254 radicals Chemical class 0.000 description 6
- 239000012047 saturated solution Substances 0.000 description 6
- YURNCBVQZBJDAJ-UHFFFAOYSA-N 2-heptenoic acid Chemical compound CCCCC=CC(O)=O YURNCBVQZBJDAJ-UHFFFAOYSA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- ABZURHNFFCKUPB-UHFFFAOYSA-N propyl n-aminocarbamate Chemical compound CCCOC(=O)NN ABZURHNFFCKUPB-UHFFFAOYSA-N 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- CXELRCIDWNLRMQ-UHFFFAOYSA-N 3-methyl-2-pent-3-enyloctanoic acid Chemical compound CCCCCC(C)C(C(O)=O)CCC=CC CXELRCIDWNLRMQ-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229940117975 chromium trioxide Drugs 0.000 description 4
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 150000007857 hydrazones Chemical class 0.000 description 4
- ZAAVDOZSQRXIGQ-UHFFFAOYSA-N n-methylpentanehydrazide Chemical compound CCCCC(=O)N(C)N ZAAVDOZSQRXIGQ-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
- PMZIRHXXHUHWNK-UHFFFAOYSA-N 1-amino-1-methyl-3-phenylurea Chemical compound CN(N)C(=O)NC1=CC=CC=C1 PMZIRHXXHUHWNK-UHFFFAOYSA-N 0.000 description 3
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 description 3
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- 208000007536 Thrombosis Diseases 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
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- 238000004587 chromatography analysis Methods 0.000 description 3
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KPSZWAJWFMFMFF-UHFFFAOYSA-N delta-Hexylen-alpha-carbonsaeure Natural products CC=CCCCC(O)=O KPSZWAJWFMFMFF-UHFFFAOYSA-N 0.000 description 1
- KPSZWAJWFMFMFF-NSCUHMNNSA-N delta-heptenoic acid Chemical compound C\C=C\CCCC(O)=O KPSZWAJWFMFMFF-NSCUHMNNSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- VUPKGFBOKBGHFZ-UHFFFAOYSA-N dipropyl carbonate Chemical compound CCCOC(=O)OCCC VUPKGFBOKBGHFZ-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UDKCUBDOEBCLPA-UHFFFAOYSA-N hydrazine;propyl n-aminocarbamate;hydrate Chemical compound O.NN.CCCOC(=O)NN UDKCUBDOEBCLPA-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- KXMTXZACPVCDMH-UHFFFAOYSA-N methyl 4-[5-(hydroxymethyl)-7-methoxy-1,3-benzodioxol-4-yl]-7-methoxy-1,3-benzodioxole-5-carboxylate Chemical compound COC(=O)C1=CC(OC)=C2OCOC2=C1C1=C2OCOC2=C(OC)C=C1CO KXMTXZACPVCDMH-UHFFFAOYSA-N 0.000 description 1
- RAVVJKCSZXAIQP-UHFFFAOYSA-N methyl 5-bromopentanoate Chemical compound COC(=O)CCCCBr RAVVJKCSZXAIQP-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- CFOCBLCVQJMSDR-UHFFFAOYSA-N n-methylpyridine-3-carbohydrazide Chemical compound CN(N)C(=O)C1=CC=CN=C1 CFOCBLCVQJMSDR-UHFFFAOYSA-N 0.000 description 1
- HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- PJBQYCIDGYKEMN-UHFFFAOYSA-N pentanehydrazide Chemical compound CCCCC(=O)NN PJBQYCIDGYKEMN-UHFFFAOYSA-N 0.000 description 1
- XGISHOFUAFNYQF-UHFFFAOYSA-N pentanoyl chloride Chemical compound CCCCC(Cl)=O XGISHOFUAFNYQF-UHFFFAOYSA-N 0.000 description 1
- 229960001206 phenicarbazide Drugs 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- JKTPENFGPKUYTP-UHFFFAOYSA-N phenyl n-amino-n-methylcarbamate Chemical compound CN(N)C(=O)OC1=CC=CC=C1 JKTPENFGPKUYTP-UHFFFAOYSA-N 0.000 description 1
- DNDTZRSLSJSECH-UHFFFAOYSA-N phenyl n-aminocarbamate Chemical compound NNC(=O)OC1=CC=CC=C1 DNDTZRSLSJSECH-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- KFUSANSHCADHNJ-UHFFFAOYSA-N pyridine-3-carbohydrazide Chemical compound NNC(=O)C1=CC=CN=C1 KFUSANSHCADHNJ-UHFFFAOYSA-N 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/374,125 US4418076A (en) | 1982-05-03 | 1982-05-03 | 7-Oxabicycloheptane hydrazone prostaglandin analogs useful in treating thrombolytic diseases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2526025A1 true FR2526025A1 (fr) | 1983-11-04 |
Family
ID=23475402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8307341A Pending FR2526025A1 (fr) | 1982-05-03 | 1983-05-03 | Analogues des prostaglandines constitues par des 7-oxabicycloheptane hydrazones a action therapeutique |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4418076A (enExample) |
| JP (1) | JPS58203980A (enExample) |
| DE (1) | DE3315902A1 (enExample) |
| FR (1) | FR2526025A1 (enExample) |
| GB (1) | GB2119375B (enExample) |
| IT (1) | IT1161242B (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4837234A (en) * | 1981-12-23 | 1989-06-06 | National Research Development Corporation | Prostaglandins |
| AU561739B2 (en) * | 1981-12-23 | 1987-05-14 | British Technology Group Limited | Prostaglandins |
| GB8501035D0 (en) * | 1985-01-16 | 1985-02-20 | Senior J | Prostaglandins |
| DE3683749D1 (de) * | 1985-12-09 | 1992-03-12 | American Cyanamid Co | Insektentoetende diacylhydrazinverbindungen. |
| US4652578A (en) * | 1986-02-24 | 1987-03-24 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane substituted amide prostaglandin analogs |
| US4883809A (en) * | 1988-11-17 | 1989-11-28 | Misra Raj N | 7-Oxabicycloheptane imino interphenyleneoxy substituted prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease |
| US4883811A (en) * | 1988-11-17 | 1989-11-28 | Misra Raj N | 7-Oxabicycloheptane imino interphenylene substituted prostaglandin analogs useful in the treatment of thrombotic disease |
| US5153327A (en) * | 1988-12-23 | 1992-10-06 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptyl substituted heterocyclic amide or ester prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease |
| US5100889A (en) * | 1989-04-03 | 1992-03-31 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptyl substituted heterocyclic amide or ester prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease |
| US4977174A (en) * | 1989-06-12 | 1990-12-11 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane imidazole prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease |
| US5126370A (en) * | 1990-12-24 | 1992-06-30 | E. R. Squibb & Sons, Inc. | Anti-thrombotic heterocyclic amido prostaglandin analogs |
| US5135939A (en) * | 1991-01-28 | 1992-08-04 | E. R. Squibb & Sons, Inc. | Heterocyclic ketone prostaglandin analogs |
| US5158967A (en) * | 1991-06-12 | 1992-10-27 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptyl substituted heterocyclic amide prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease |
| US5280034A (en) * | 1991-08-23 | 1994-01-18 | E. R. Squibb & Sons, Inc. | Bis-heterocyclic prostaglandin analogs |
| US5827868A (en) * | 1991-10-07 | 1998-10-27 | E. R. Squibb & Sons, Inc. | Prostaglandin analogs |
| CA2450073C (en) | 2001-07-25 | 2017-08-29 | Biomarin Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
| EP2392258B1 (en) | 2005-04-28 | 2014-10-08 | Proteus Digital Health, Inc. | Pharma-informatics system |
| JP2010503710A (ja) | 2006-09-18 | 2010-02-04 | ラプトール ファーマシューティカル インコーポレイテッド | 受容体関連タンパク質（ｒａｐ）結合体の投与による肝障害の処置 |
| PT2398500T (pt) | 2009-02-20 | 2019-06-14 | 2 Bbb Medicines B V | Sistema de entrega de medicamentos à base de glutationas |
| EP2427178B1 (en) | 2009-05-06 | 2023-01-04 | Laboratory Skin Care, Inc. | Dermal delivery compositions comprising active agent-calcium phosphate particle complexes and methods of using the same |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4220594A (en) * | 1977-11-04 | 1980-09-02 | E. R. Squibb & Sons, Inc. | Hexa- and octahydro-4,7-epoxyisobenzofuran-1-ol and hexa- and octahydro-5,8-epoxy-1H-2-benzopyran-3-ol |
| US4254044A (en) * | 1977-11-04 | 1981-03-03 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane- and 7-oxabicycloheptene compounds |
| US4143054A (en) * | 1977-11-04 | 1979-03-06 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane- and 7-oxabicycloheptene compounds |
| US4187236A (en) * | 1977-11-04 | 1980-02-05 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane compounds |
| GB2039909B (en) | 1979-01-05 | 1983-06-15 | Wilson N | Prostaglandins |
| US4228180A (en) * | 1979-11-01 | 1980-10-14 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane and 7-oxabicycloheptene prostaglandin analogs |
| ZA829068B (en) * | 1980-07-01 | 1983-02-23 | Nat Res Dev | Prostaglandins |
-
1982
- 1982-05-03 US US06/374,125 patent/US4418076A/en not_active Expired - Fee Related
-
1983
- 1983-04-27 GB GB08311405A patent/GB2119375B/en not_active Expired
- 1983-05-02 DE DE3315902A patent/DE3315902A1/de not_active Withdrawn
- 1983-05-02 JP JP58078114A patent/JPS58203980A/ja active Granted
- 1983-05-03 FR FR8307341A patent/FR2526025A1/fr active Pending
- 1983-05-03 IT IT20905/83A patent/IT1161242B/it active
Also Published As
| Publication number | Publication date |
|---|---|
| GB2119375B (en) | 1985-10-02 |
| IT1161242B (it) | 1987-03-18 |
| JPH0480915B2 (enExample) | 1992-12-21 |
| JPS58203980A (ja) | 1983-11-28 |
| DE3315902A1 (de) | 1983-11-24 |
| IT8320905A0 (it) | 1983-05-03 |
| GB8311405D0 (en) | 1983-06-02 |
| GB2119375A (en) | 1983-11-16 |
| US4418076A (en) | 1983-11-29 |
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