CH658247A5 - Analogues de la prostaglandine substitues au 7-oxabicycloheptane. - Google Patents
Analogues de la prostaglandine substitues au 7-oxabicycloheptane. Download PDFInfo
- Publication number
- CH658247A5 CH658247A5 CH1244/84A CH124484A CH658247A5 CH 658247 A5 CH658247 A5 CH 658247A5 CH 1244/84 A CH1244/84 A CH 1244/84A CH 124484 A CH124484 A CH 124484A CH 658247 A5 CH658247 A5 CH 658247A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- hept
- heptenoic
- oxabicyclo
- procedure
- Prior art date
Links
- DYWAPFDKPAHSED-UHFFFAOYSA-N 2-cycloheptyloxepane Chemical compound C1CCCCCC1C1OCCCCC1 DYWAPFDKPAHSED-UHFFFAOYSA-N 0.000 title 1
- 150000003180 prostaglandins Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 172
- 239000000203 mixture Substances 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000007983 Tris buffer Chemical group 0.000 claims description 3
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 238000004220 aggregation Methods 0.000 claims description 2
- 230000002776 aggregation Effects 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 210000001772 blood platelet Anatomy 0.000 claims description 2
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 206010006482 Bronchospasm Diseases 0.000 claims 1
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 1
- 230000007885 bronchoconstriction Effects 0.000 claims 1
- 125000005357 cycloalkylalkynyl group Chemical group 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 239000002253 acid Substances 0.000 description 168
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 150
- 238000000034 method Methods 0.000 description 149
- PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 146
- -1 prostaglandin 7-oxabicycloheptane analogs Chemical class 0.000 description 139
- 239000000243 solution Substances 0.000 description 115
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- 150000004702 methyl esters Chemical class 0.000 description 86
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 72
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 70
- ZRKMQKLGEQPLNS-UHFFFAOYSA-N 1-Pentanethiol Chemical compound CCCCCS ZRKMQKLGEQPLNS-UHFFFAOYSA-N 0.000 description 62
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- 239000007864 aqueous solution Substances 0.000 description 32
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- 238000004458 analytical method Methods 0.000 description 30
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- 235000019341 magnesium sulphate Nutrition 0.000 description 24
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- 238000000746 purification Methods 0.000 description 21
- 229920006395 saturated elastomer Polymers 0.000 description 21
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 17
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 15
- 238000003818 flash chromatography Methods 0.000 description 15
- 239000011780 sodium chloride Substances 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 239000012300 argon atmosphere Substances 0.000 description 14
- URIRDRHUUFRHAS-UHFFFAOYSA-N hexyl methanesulfonate Chemical compound CCCCCCOS(C)(=O)=O URIRDRHUUFRHAS-UHFFFAOYSA-N 0.000 description 14
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 14
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 14
- 239000012267 brine Substances 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 13
- 239000002024 ethyl acetate extract Substances 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- ZMRFRBHYXOQLDK-UHFFFAOYSA-N 2-phenylethanethiol Chemical compound SCCC1=CC=CC=C1 ZMRFRBHYXOQLDK-UHFFFAOYSA-N 0.000 description 11
- 101150041968 CDC13 gene Proteins 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
- 150000001299 aldehydes Chemical class 0.000 description 11
- FWBXAOOHHILPSR-UHFFFAOYSA-N cyclohexylmethanethiol Chemical compound SCC1CCCCC1 FWBXAOOHHILPSR-UHFFFAOYSA-N 0.000 description 11
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- CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical compound SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 description 10
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- 238000004587 chromatography analysis Methods 0.000 description 9
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 9
- 239000012043 crude product Substances 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 7
- IUSDGVJFDZRIBR-UHFFFAOYSA-N 3-phenylpropane-1-thiol Chemical compound SCCCC1=CC=CC=C1 IUSDGVJFDZRIBR-UHFFFAOYSA-N 0.000 description 7
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 6
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- WVDYBOADDMMFIY-UHFFFAOYSA-N Cyclopentanethiol Chemical compound SC1CCCC1 WVDYBOADDMMFIY-UHFFFAOYSA-N 0.000 description 5
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- 239000002585 base Substances 0.000 description 5
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- 125000004356 hydroxy functional group Chemical group O* 0.000 description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 5
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 4
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 4
- 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 description 4
- ZDKRMIJRCHPKLW-UHFFFAOYSA-N benzyl methanesulfonate Chemical compound CS(=O)(=O)OCC1=CC=CC=C1 ZDKRMIJRCHPKLW-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
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- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
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- 125000005977 3-phenylpropyloxy group Chemical group 0.000 description 3
- VPIAKHNXCOTPAY-UHFFFAOYSA-N Heptane-1-thiol Chemical compound CCCCCCCS VPIAKHNXCOTPAY-UHFFFAOYSA-N 0.000 description 3
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- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
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- FYFFGSSZFBZTAH-UHFFFAOYSA-N methylaminomethanetriol Chemical compound CNC(O)(O)O FYFFGSSZFBZTAH-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- ZVEZMVFBMOOHAT-UHFFFAOYSA-N nonane-1-thiol Chemical compound CCCCCCCCCS ZVEZMVFBMOOHAT-UHFFFAOYSA-N 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
- GRJPLADOIKKOGS-UHFFFAOYSA-N octyl methanesulfonate Chemical compound CCCCCCCCOS(C)(=O)=O GRJPLADOIKKOGS-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- GZQUFIUZBLOTMM-UHFFFAOYSA-N pentyl methanesulfonate Chemical compound CCCCCOS(C)(=O)=O GZQUFIUZBLOTMM-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002599 prostaglandin synthase inhibitor Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000003826 tablet Substances 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
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000002537 thrombolytic effect Effects 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0025—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing keto groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/474,913 US4474803A (en) | 1983-03-14 | 1983-03-14 | 7-Oxabicycloheptane substituted thio prostaglandin analogs useful in treating platelet aggregation and bronchoconstriction |
| US52332083A | 1983-08-15 | 1983-08-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH658247A5 true CH658247A5 (fr) | 1986-10-31 |
Family
ID=27044617
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1244/84A CH658247A5 (fr) | 1983-03-14 | 1984-03-13 | Analogues de la prostaglandine substitues au 7-oxabicycloheptane. |
Country Status (24)
| Country | Link |
|---|---|
| KR (1) | KR840009085A (xx) |
| AT (1) | AT383600B (xx) |
| AU (1) | AU567919B2 (xx) |
| CA (1) | CA1256887A (xx) |
| CH (1) | CH658247A5 (xx) |
| DD (1) | DD216932A5 (xx) |
| DE (1) | DE3409124A1 (xx) |
| DK (1) | DK155584A (xx) |
| ES (1) | ES8506270A1 (xx) |
| FI (1) | FI841008A (xx) |
| FR (1) | FR2542743B1 (xx) |
| GB (1) | GB2136428B (xx) |
| GR (1) | GR79881B (xx) |
| HU (1) | HU190530B (xx) |
| IE (1) | IE57027B1 (xx) |
| IL (1) | IL71184A0 (xx) |
| IT (1) | IT1173442B (xx) |
| LU (1) | LU85249A1 (xx) |
| NL (1) | NL8400797A (xx) |
| NO (1) | NO840960L (xx) |
| NZ (1) | NZ207361A (xx) |
| PL (1) | PL246663A1 (xx) |
| PT (1) | PT78242B (xx) |
| SE (1) | SE8401398L (xx) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4513103A (en) * | 1983-10-21 | 1985-04-23 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane ethers useful in the treatment of thrombolytic disease |
| US4526900A (en) * | 1984-01-26 | 1985-07-02 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane substituted oxa prostaglandin analogs and their use in the treatment of thrombolytic disease |
| US4542157A (en) * | 1984-04-27 | 1985-09-17 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane substituted oxa prostaglandin analogs and their use in the treatment of thrombolytic disease |
| US4560698A (en) * | 1984-06-04 | 1985-12-24 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane substituted thio prostaglandin analogs and their use in the treatment in thrombolytic disease |
| US4661506A (en) * | 1984-11-30 | 1987-04-28 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane substituted ox prostaglandin analogs |
| US4588743A (en) * | 1985-01-22 | 1986-05-13 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane-substituted oxa prostaglandin analogs and their use in the treatment of thrombolytic disease |
| US4607049A (en) * | 1985-04-22 | 1986-08-19 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane substituted thio prostaglandin analogs useful in the treatment of thrombolytic disease |
| US4608386A (en) * | 1985-04-26 | 1986-08-26 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane ethers useful in the treatment of thrombotic diseases |
| US4611006A (en) * | 1985-06-28 | 1986-09-09 | E. R. Squibb & Sons, Inc. | 5,6-epoxy-7-oxabicycloheptane substituted ethers useful in the treatment of thrombotic disease |
| US4654356A (en) * | 1985-08-01 | 1987-03-31 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane substituted diacid diamide prostaglandin analogs |
| US4673685A (en) * | 1986-07-23 | 1987-06-16 | E. R. Squibb & Sons, Inc. | Hydroximic acids of 7-oxabicycloheptane substituted ethers and thioethers useful in the treatment of thrombotic disease |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4143054A (en) * | 1977-11-04 | 1979-03-06 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane- and 7-oxabicycloheptene compounds |
| ZA829068B (en) * | 1980-07-01 | 1983-02-23 | Nat Res Dev | Prostaglandins |
| AU561739B2 (en) * | 1981-12-23 | 1987-05-14 | British Technology Group Limited | Prostaglandins |
| US4549030A (en) * | 1982-12-13 | 1985-10-22 | The Upjohn Company | Organic compounds and process |
| US4526900A (en) * | 1984-01-26 | 1985-07-02 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane substituted oxa prostaglandin analogs and their use in the treatment of thrombolytic disease |
| US4542157A (en) * | 1984-04-27 | 1985-09-17 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane substituted oxa prostaglandin analogs and their use in the treatment of thrombolytic disease |
-
1984
- 1984-03-01 CA CA000448662A patent/CA1256887A/en not_active Expired
- 1984-03-02 AU AU25235/84A patent/AU567919B2/en not_active Ceased
- 1984-03-02 NZ NZ207361A patent/NZ207361A/en unknown
- 1984-03-05 IE IE525/84A patent/IE57027B1/xx unknown
- 1984-03-06 GR GR73998A patent/GR79881B/el unknown
- 1984-03-08 IL IL71184A patent/IL71184A0/xx unknown
- 1984-03-08 GB GB08406100A patent/GB2136428B/en not_active Expired
- 1984-03-13 SE SE8401398A patent/SE8401398L/xx not_active Application Discontinuation
- 1984-03-13 KR KR1019840001248A patent/KR840009085A/ko not_active Application Discontinuation
- 1984-03-13 NL NL8400797A patent/NL8400797A/nl not_active Application Discontinuation
- 1984-03-13 PT PT78242A patent/PT78242B/pt unknown
- 1984-03-13 NO NO840960A patent/NO840960L/no unknown
- 1984-03-13 DE DE19843409124 patent/DE3409124A1/de not_active Withdrawn
- 1984-03-13 FI FI841008A patent/FI841008A/fi not_active Application Discontinuation
- 1984-03-13 HU HU841001A patent/HU190530B/hu unknown
- 1984-03-13 AT AT0083484A patent/AT383600B/de not_active IP Right Cessation
- 1984-03-13 ES ES530548A patent/ES8506270A1/es not_active Expired
- 1984-03-13 FR FR8403835A patent/FR2542743B1/fr not_active Expired
- 1984-03-13 DK DK155584A patent/DK155584A/da not_active IP Right Cessation
- 1984-03-13 CH CH1244/84A patent/CH658247A5/fr not_active IP Right Cessation
- 1984-03-14 IT IT20049/84A patent/IT1173442B/it active
- 1984-03-14 DD DD84260892A patent/DD216932A5/de unknown
- 1984-03-14 PL PL24666384A patent/PL246663A1/xx unknown
- 1984-03-14 LU LU85249A patent/LU85249A1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB2136428A (en) | 1984-09-19 |
| AU2523584A (en) | 1984-09-20 |
| ATA83484A (de) | 1986-12-15 |
| AT383600B (de) | 1987-07-27 |
| IT1173442B (it) | 1987-06-24 |
| FR2542743B1 (fr) | 1987-10-30 |
| HU190530B (en) | 1986-09-29 |
| SE8401398D0 (sv) | 1984-03-13 |
| PL246663A1 (en) | 1985-03-26 |
| FI841008A (fi) | 1984-09-15 |
| PT78242A (en) | 1984-04-01 |
| ES530548A0 (es) | 1985-07-01 |
| NL8400797A (nl) | 1984-10-01 |
| SE8401398L (sv) | 1984-09-15 |
| DE3409124A1 (de) | 1984-09-27 |
| KR840009085A (ko) | 1984-12-24 |
| NO840960L (no) | 1984-09-17 |
| PT78242B (en) | 1986-05-27 |
| LU85249A1 (fr) | 1984-11-14 |
| NZ207361A (en) | 1986-12-05 |
| CA1256887A (en) | 1989-07-04 |
| FR2542743A1 (fr) | 1984-09-21 |
| DD216932A5 (de) | 1985-01-02 |
| DK155584D0 (da) | 1984-03-13 |
| IE57027B1 (en) | 1992-03-25 |
| DK155584A (da) | 1984-09-15 |
| GB8406100D0 (en) | 1984-04-11 |
| GB2136428B (en) | 1986-09-10 |
| IE840525L (en) | 1984-09-14 |
| GR79881B (xx) | 1984-10-31 |
| ES8506270A1 (es) | 1985-07-01 |
| IT8420049A0 (it) | 1984-03-14 |
| HUT34179A (en) | 1985-02-28 |
| IL71184A0 (en) | 1984-06-29 |
| FI841008A0 (fi) | 1984-03-13 |
| AU567919B2 (en) | 1987-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |