DE2638827A1 - Neue 11-deoxy-prostaglandine e, f tief alpha und f tief beta - Google Patents
Neue 11-deoxy-prostaglandine e, f tief alpha und f tief betaInfo
- Publication number
- DE2638827A1 DE2638827A1 DE19762638827 DE2638827A DE2638827A1 DE 2638827 A1 DE2638827 A1 DE 2638827A1 DE 19762638827 DE19762638827 DE 19762638827 DE 2638827 A DE2638827 A DE 2638827A DE 2638827 A1 DE2638827 A1 DE 2638827A1
- Authority
- DE
- Germany
- Prior art keywords
- compound according
- hydrogen
- methyl
- fluorine
- radicals
- 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.)
- Withdrawn
Links
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- 150000001875 compounds Chemical class 0.000 claims description 340
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- 239000001257 hydrogen Substances 0.000 claims description 138
- -1 alkyl radical Chemical class 0.000 claims description 132
- 239000000203 mixture Substances 0.000 claims description 118
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- 229910052731 fluorine Inorganic materials 0.000 claims description 94
- 239000011737 fluorine Substances 0.000 claims description 93
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 84
- 150000004702 methyl esters Chemical class 0.000 claims description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 150000002148 esters Chemical class 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 239000000460 chlorine Substances 0.000 claims description 12
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 10
- 125000004494 ethyl ester group Chemical group 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 9
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 241000490229 Eucephalus Species 0.000 claims 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 1
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- 238000000034 method Methods 0.000 description 110
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- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 12
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- 235000011152 sodium sulphate Nutrition 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 11
- 239000007795 chemical reaction product Substances 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 10
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- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 10
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- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229960005205 prednisolone Drugs 0.000 description 1
- OIGNJSKKLXVSLS-VWUMJDOOSA-N prednisolone Chemical compound O=C1C=C[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 OIGNJSKKLXVSLS-VWUMJDOOSA-N 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 description 1
- DZUXGQBLFALXCR-CDIPTNKSSA-N prostaglandin F1alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1CCCCCCC(O)=O DZUXGQBLFALXCR-CDIPTNKSSA-N 0.000 description 1
- 230000002997 prostaglandinlike Effects 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 229960003908 pseudoephedrine Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 210000005241 right ventricle Anatomy 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical group [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 description 1
- 238000003307 slaughter Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- CWXOAQXKPAENDI-UHFFFAOYSA-N sodium methylsulfinylmethylide Chemical compound [Na+].CS([CH2-])=O CWXOAQXKPAENDI-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- WZUZROCCERRXFZ-UHFFFAOYSA-N sodium;bis(methylsulfinyl)methane Chemical compound [Na+].CS(=O)[CH-]S(C)=O WZUZROCCERRXFZ-UHFFFAOYSA-N 0.000 description 1
- DZXBHDRHRFLQCJ-UHFFFAOYSA-M sodium;methyl sulfate Chemical compound [Na+].COS([O-])(=O)=O DZXBHDRHRFLQCJ-UHFFFAOYSA-M 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000019100 sperm motility Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000009885 systemic effect Effects 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
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 239000006216 vaginal suppository Substances 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 125000000391 vinyl group Chemical class [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
- C07C53/21—Acids containing three or more carbon atoms containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5407—Acyclic saturated phosphonium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
- Pyrane Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60941075A | 1975-09-02 | 1975-09-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2638827A1 true DE2638827A1 (de) | 1977-03-10 |
Family
ID=24440691
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762638827 Withdrawn DE2638827A1 (de) | 1975-09-02 | 1976-08-28 | Neue 11-deoxy-prostaglandine e, f tief alpha und f tief beta |
Country Status (9)
| Country | Link |
|---|---|
| US (6) | US4126754A (cg-RX-API-DMAC7.html) |
| JP (1) | JPS5233651A (cg-RX-API-DMAC7.html) |
| AU (1) | AU502427B2 (cg-RX-API-DMAC7.html) |
| BE (1) | BE845780A (cg-RX-API-DMAC7.html) |
| DE (1) | DE2638827A1 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2322593A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1528074A (cg-RX-API-DMAC7.html) |
| NL (1) | NL7609538A (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA764727B (cg-RX-API-DMAC7.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4187381A (en) * | 1973-08-06 | 1980-02-05 | Hoffmann-La Roche Inc. | 16-Substituted prostaglandins |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4293704A (en) * | 1975-09-25 | 1981-10-06 | American Cyanamid Company | Novel 2-substituted-3,4-epoxycyclopentan-1-ones, 2-substituted-3,4-epoxycyclopentan-1-ols, and various 2-substituted-cyclopentenones |
| ZA777142B (en) * | 1976-12-08 | 1978-09-27 | Hoffmann La Roche | Novel prostaglandins |
| DE2702366A1 (de) * | 1977-01-21 | 1978-08-03 | Hoechst Ag | Neue prostaglandin-analoge und verfahren zu ihrer herstellung |
| US4163016A (en) * | 1977-07-05 | 1979-07-31 | Hoffmann-La Roche Inc. | 16-Substituted prostaglandins |
| DE2742407A1 (de) * | 1977-09-21 | 1979-03-29 | Hoechst Ag | Neue fluorhaltige prostaglandinderivate |
| US4312810A (en) * | 1978-11-22 | 1982-01-26 | The Upjohn Company | 2,5-Inter-o-phenylene-3,4-dinor-5,9α-epoxy-9-deoxy-PGF1 compounds |
| US4306078A (en) * | 1979-12-03 | 1981-12-15 | Hoffmann-La Roche Inc. | 16-Substituted prostaglandins |
| US6808933B1 (en) * | 2000-10-19 | 2004-10-26 | Agilent Technologies, Inc. | Methods of enhancing confidence in assays for analytes |
| AU2006209072B2 (en) * | 2005-01-27 | 2011-02-24 | Sucampo Ag | Method and composition for treating central nervous system disorders |
| DE602006018583D1 (de) * | 2005-03-04 | 2011-01-13 | Sucampo Ag | Verfahren und zusammensetzung zur behandlung von peripheren gefässkrankheiten |
| US20180016230A1 (en) * | 2014-12-10 | 2018-01-18 | Apotex Inc. | Salts of Prostaglandin Analog Intermediates |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3935261A (en) * | 1970-01-23 | 1976-01-27 | May & Baker Limited | Cyclopentane derivatives |
| US3932479A (en) * | 1973-04-27 | 1976-01-13 | American Cyanamid Company | Lithium 3-triphenylmethoxy-1-trans-alkenyl-dialkyl alanates |
-
1976
- 1976-08-05 ZA ZA764727A patent/ZA764727B/xx unknown
- 1976-08-06 AU AU16625/76A patent/AU502427B2/en not_active Expired
- 1976-08-19 GB GB34528/76A patent/GB1528074A/en not_active Expired
- 1976-08-27 NL NL7609538A patent/NL7609538A/xx not_active Application Discontinuation
- 1976-08-28 DE DE19762638827 patent/DE2638827A1/de not_active Withdrawn
- 1976-08-28 JP JP51102223A patent/JPS5233651A/ja active Pending
- 1976-09-01 FR FR7626393A patent/FR2322593A1/fr active Granted
- 1976-09-02 BE BE170294A patent/BE845780A/xx not_active IP Right Cessation
-
1978
- 1978-04-17 US US05/897,225 patent/US4126754A/en not_active Expired - Lifetime
- 1978-04-17 US US05/897,222 patent/US4163110A/en not_active Expired - Lifetime
- 1978-04-17 US US05/897,219 patent/US4138577A/en not_active Expired - Lifetime
- 1978-04-17 US US05/897,217 patent/US4138575A/en not_active Expired - Lifetime
- 1978-04-17 US US05/897,220 patent/US4138573A/en not_active Expired - Lifetime
- 1978-04-17 US US05/897,218 patent/US4138576A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4187381A (en) * | 1973-08-06 | 1980-02-05 | Hoffmann-La Roche Inc. | 16-Substituted prostaglandins |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2322593B1 (cg-RX-API-DMAC7.html) | 1983-10-21 |
| BE845780A (fr) | 1977-03-02 |
| ZA764727B (en) | 1977-07-27 |
| US4138577A (en) | 1979-02-06 |
| GB1528074A (en) | 1978-10-11 |
| JPS5233651A (en) | 1977-03-14 |
| US4138575A (en) | 1979-02-06 |
| NL7609538A (nl) | 1977-03-04 |
| US4126754A (en) | 1978-11-21 |
| FR2322593A1 (fr) | 1977-04-01 |
| AU502427B2 (en) | 1979-07-26 |
| US4138573A (en) | 1979-02-06 |
| US4163110A (en) | 1979-07-31 |
| AU1662576A (en) | 1978-02-09 |
| US4138576A (en) | 1979-02-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |