DD249700A5 - Verfahren zur herstellung des r-allenstereoisomer von 16-phenoxy- und 16-substituierten phenoxyprostatrien-saeurederivaten - Google Patents
Verfahren zur herstellung des r-allenstereoisomer von 16-phenoxy- und 16-substituierten phenoxyprostatrien-saeurederivaten Download PDFInfo
- Publication number
- DD249700A5 DD249700A5 DD84294680A DD29468084A DD249700A5 DD 249700 A5 DD249700 A5 DD 249700A5 DD 84294680 A DD84294680 A DD 84294680A DD 29468084 A DD29468084 A DD 29468084A DD 249700 A5 DD249700 A5 DD 249700A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- phenoxy
- substituted
- stereoisomer
- acid derivatives
- formula
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims abstract description 4
- 150000003180 prostaglandins Chemical class 0.000 claims abstract description 4
- 239000003814 drug Substances 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 16
- -1 16-substituted phenoxyprostatrienoic acid Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
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- 125000003118 aryl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
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- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
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- 229910052740 iodine Inorganic materials 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- 229960000281 trometamol Drugs 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
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- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001361 allenes Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000001262 anti-secretory effect Effects 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
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- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
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- 125000004122 cyclic group Chemical group 0.000 description 1
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- 210000003238 esophagus Anatomy 0.000 description 1
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- 229940012017 ethylenediamine Drugs 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
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- 235000013305 food Nutrition 0.000 description 1
- 229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
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- VJKYNWPQVZHJAR-UHFFFAOYSA-H hexasodium trisulfate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VJKYNWPQVZHJAR-UHFFFAOYSA-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
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
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- 239000008101 lactose Substances 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- 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
- C07C405/0016—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing only hydroxy, etherified or esterified hydroxy groups
-
- 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
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/564,386 US4600785A (en) | 1983-12-22 | 1983-12-22 | Processes and intermediates for making 16-phenoxy and 16-substituted phenoxy-prostatrienoic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD249700A5 true DD249700A5 (de) | 1987-09-16 |
Family
ID=24254259
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD84294680A DD249700A5 (de) | 1983-12-22 | 1984-12-20 | Verfahren zur herstellung des r-allenstereoisomer von 16-phenoxy- und 16-substituierten phenoxyprostatrien-saeurederivaten |
| DD84271309A DD241254A5 (de) | 1983-12-22 | 1984-12-20 | Verfahren zur herstellung von 16-substituierten phenoxyprostatriensaeurederivaten |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD84271309A DD241254A5 (de) | 1983-12-22 | 1984-12-20 | Verfahren zur herstellung von 16-substituierten phenoxyprostatriensaeurederivaten |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US4600785A (cs) |
| EP (1) | EP0146935B1 (cs) |
| JP (3) | JPH0635431B2 (cs) |
| KR (1) | KR900000684B1 (cs) |
| CN (1) | CN85101840A (cs) |
| AR (1) | AR241015A1 (cs) |
| AT (1) | ATE50986T1 (cs) |
| AU (1) | AU585844B2 (cs) |
| CA (4) | CA1267892A (cs) |
| CS (5) | CS600784A2 (cs) |
| DD (2) | DD249700A5 (cs) |
| DE (1) | DE3481610D1 (cs) |
| DK (1) | DK617084A (cs) |
| ES (4) | ES8604389A1 (cs) |
| FI (1) | FI845069L (cs) |
| GR (1) | GR82514B (cs) |
| HU (2) | HU196732B (cs) |
| IL (1) | IL73881A (cs) |
| IN (1) | IN160437B (cs) |
| MX (2) | MX158754A (cs) |
| NO (1) | NO845148L (cs) |
| NZ (1) | NZ210667A (cs) |
| PH (2) | PH22893A (cs) |
| PL (2) | PL154330B1 (cs) |
| PT (1) | PT79720A (cs) |
| RO (2) | RO94561A7 (cs) |
| SU (3) | SU1473709A3 (cs) |
| ZA (1) | ZA849967B (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ213749A (en) * | 1984-10-09 | 1989-01-06 | Syntex Inc | Ethers for use as intermediates in the preparation of 16-phenoxy and 16-substituted phenoxy-prostatrienoic acid derivatives |
| US4929740A (en) * | 1984-10-09 | 1990-05-29 | Syntex (U.S.A.) Inc. | Process for making 16-phenoxy- and 16-(substituted phenoxy)-prostatrienoic acid derivatives |
| US4778904A (en) * | 1985-09-13 | 1988-10-18 | Syntex (U.S.A.) Inc. | Intermediates for making 16-phenoxy- and 16-(substituted phenoxy)-prostatrienoic acid derivatives |
| US4755531A (en) * | 1986-08-11 | 1988-07-05 | Syntex (U.S.A.) Inc. | Thiol esters of 4,5-allenyl prostaglandins and use thereof as antigastric secretion agents |
| US4689419A (en) * | 1986-11-14 | 1987-08-25 | G. D. Searle & Co. | Novel intermediate compounds in a process for producing 16-phenoxy- and 16-substituted phenoxy-9-keto-prostatrienoic acid derivatives |
| US5248788A (en) * | 1988-12-13 | 1993-09-28 | Syntex (U.S.A.) Inc. | Process for preparing allenic prostanoic acid derivatives |
| US4916238A (en) * | 1988-12-13 | 1990-04-10 | Syntex (U.S.A.) Inc. | Process for preparing allenic prostanoic acid derivatives |
| US5571936A (en) * | 1994-09-30 | 1996-11-05 | Korea Institute Of Science And Technology | Intermediates for the synthesis of 16-phenoxy-prostatrienoic acid derivatives and a preparing method thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4304907A (en) * | 1972-05-10 | 1981-12-08 | The Upjohn Company | Bicyclo lactone intermediates for prostaglandin analogs |
| JPS5434724B2 (cs) * | 1974-09-19 | 1979-10-29 | ||
| GB1590022A (en) * | 1976-08-23 | 1981-05-28 | Ono Pharmaceutical Co | Prostaglandin analogues |
| US4178457A (en) * | 1978-07-10 | 1979-12-11 | Syntex (U.S.A.) Inc. | (dl)-16-Phenoxy- and 16-substituted phenoxy-9-keto prostatrienoic acid derivatives and processes for the production thereof |
| DE3030477C2 (de) * | 1980-08-12 | 1986-10-16 | Dr. Willmar Schwabe GmbH & Co, 7500 Karlsruhe | Iridoid-Derivate, Verfahren zu ihrer Herstellung und deren Verwendung |
| US4389414A (en) * | 1981-05-11 | 1983-06-21 | Syntex (U.S.A.) Inc. | Prostaglandin compositions |
| CA1216793A (en) * | 1982-07-19 | 1987-01-20 | Cheng-Der Yu | Pge-type compositions encapsulated by acid isolated gelatin |
| ES8607921A1 (es) * | 1984-07-31 | 1986-06-16 | Syntex Inc | Procedimiento para preparar derivados de acidos 11-sustitui-dos-16-fenoxi y 16-fenoxi sustituido-prostatrienoicos |
| US4618696A (en) * | 1984-07-31 | 1986-10-21 | Syntex (U.S.A.) Inc. | 9-oxo-15α-hydroxy-16-phenoxy and 16-substituted phenoxy 17,18,19,20-tetranorprosta-4,5,13,(E)-trienoates |
| NZ213749A (en) * | 1984-10-09 | 1989-01-06 | Syntex Inc | Ethers for use as intermediates in the preparation of 16-phenoxy and 16-substituted phenoxy-prostatrienoic acid derivatives |
-
1983
- 1983-12-22 US US06/564,386 patent/US4600785A/en not_active Expired - Fee Related
-
1984
- 1984-12-19 GR GR82514A patent/GR82514B/el unknown
- 1984-12-20 DD DD84294680A patent/DD249700A5/de unknown
- 1984-12-20 PL PL1984251088A patent/PL154330B1/pl unknown
- 1984-12-20 ES ES538899A patent/ES8604389A1/es not_active Expired
- 1984-12-20 FI FI845069A patent/FI845069L/fi not_active Application Discontinuation
- 1984-12-20 AT AT84115950T patent/ATE50986T1/de not_active IP Right Cessation
- 1984-12-20 HU HU863355A patent/HU196732B/hu not_active IP Right Cessation
- 1984-12-20 NZ NZ210667A patent/NZ210667A/xx unknown
- 1984-12-20 DK DK617084A patent/DK617084A/da not_active Application Discontinuation
- 1984-12-20 PL PL25572384A patent/PL255723A1/xx unknown
- 1984-12-20 CS CS866007A patent/CS600784A2/cs unknown
- 1984-12-20 PH PH31623A patent/PH22893A/en unknown
- 1984-12-20 IL IL73881A patent/IL73881A/xx unknown
- 1984-12-20 EP EP84115950A patent/EP0146935B1/en not_active Expired - Lifetime
- 1984-12-20 NO NO845148A patent/NO845148L/no unknown
- 1984-12-20 SU SU843828202A patent/SU1473709A3/ru active
- 1984-12-20 AR AR299047A patent/AR241015A1/es active
- 1984-12-20 JP JP59270571A patent/JPH0635431B2/ja not_active Expired - Lifetime
- 1984-12-20 RO RO84124019A patent/RO94561A7/ro unknown
- 1984-12-20 PT PT79720A patent/PT79720A/pt unknown
- 1984-12-20 AU AU37120/84A patent/AU585844B2/en not_active Ceased
- 1984-12-20 MX MX203853A patent/MX158754A/es unknown
- 1984-12-20 DD DD84271309A patent/DD241254A5/de not_active IP Right Cessation
- 1984-12-20 CA CA000470699A patent/CA1267892A/en not_active Expired - Fee Related
- 1984-12-20 ZA ZA849967A patent/ZA849967B/xx unknown
- 1984-12-20 HU HU844754A patent/HU197302B/hu not_active IP Right Cessation
- 1984-12-20 IN IN1020/MAS/84A patent/IN160437B/en unknown
- 1984-12-20 CS CS8410132A patent/CS257784B2/cs unknown
- 1984-12-20 CS CS866008A patent/CS600884A2/cs unknown
- 1984-12-20 RO RO116780A patent/RO91666B/ro unknown
- 1984-12-20 KR KR1019840008147A patent/KR900000684B1/ko not_active IP Right Cessation
- 1984-12-20 DE DE8484115950T patent/DE3481610D1/de not_active Expired - Fee Related
-
1985
- 1985-04-01 CN CN198585101840A patent/CN85101840A/zh active Pending
- 1985-09-24 SU SU853955489A patent/SU1342411A3/ru active
- 1985-09-24 SU SU853955491A patent/SU1356959A3/ru active
- 1985-10-31 ES ES548459A patent/ES8609234A1/es not_active Expired
- 1985-10-31 ES ES548453A patent/ES8607228A1/es not_active Expired
- 1985-10-31 ES ES548460A patent/ES8607229A1/es not_active Expired
-
1986
- 1986-05-09 PH PH33751A patent/PH23728A/en unknown
- 1986-08-14 CS CS866007A patent/CS257796B2/cs unknown
- 1986-08-14 CS CS866008A patent/CS257797B2/cs unknown
-
1988
- 1988-08-09 MX MX1259988A patent/MX12599A/es unknown
- 1988-08-11 CA CA000574537A patent/CA1276931C/en not_active Expired - Fee Related
- 1988-08-11 CA CA000574538A patent/CA1283408C/en not_active Expired - Fee Related
- 1988-08-12 CA CA000574703A patent/CA1283409C/en not_active Expired - Fee Related
-
1991
- 1991-12-19 JP JP3336857A patent/JPH0772170B2/ja not_active Expired - Lifetime
- 1991-12-19 JP JP3336862A patent/JPH0717597B2/ja not_active Expired - Lifetime
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