FI61692C - Foerfarande foer framstaellning av farmakologiskt aktiva prostaglandinderivat - Google Patents
Foerfarande foer framstaellning av farmakologiskt aktiva prostaglandinderivat Download PDFInfo
- Publication number
- FI61692C FI61692C FI760744A FI760744A FI61692C FI 61692 C FI61692 C FI 61692C FI 760744 A FI760744 A FI 760744A FI 760744 A FI760744 A FI 760744A FI 61692 C FI61692 C FI 61692C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- pyrrolidinone
- compound
- solution
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 22
- 230000000144 pharmacologic effect Effects 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000002360 preparation method Methods 0.000 claims description 23
- 150000002148 esters Chemical class 0.000 claims description 20
- 150000003180 prostaglandins Chemical class 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- -1 alkali metal salt Chemical class 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
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- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
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- 235000019270 ammonium chloride Nutrition 0.000 description 1
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- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000004872 arterial blood pressure Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
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- 229910052805 deuterium Inorganic materials 0.000 description 1
- 230000004882 diastolic arterial blood pressure Effects 0.000 description 1
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- RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 description 1
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- 230000004530 effect on cardiovascular disease Effects 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
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- 239000012362 glacial acetic acid Substances 0.000 description 1
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
- XWCQLLDGXBLGMD-UHFFFAOYSA-M magnesium;pentane;bromide Chemical compound [Mg+2].[Br-].CCCC[CH2-] XWCQLLDGXBLGMD-UHFFFAOYSA-M 0.000 description 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- HWYHDWGGACRVEH-UHFFFAOYSA-N n-methyl-n-(4-pyrrolidin-1-ylbut-2-ynyl)acetamide Chemical compound CC(=O)N(C)CC#CCN1CCCC1 HWYHDWGGACRVEH-UHFFFAOYSA-N 0.000 description 1
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- 229960001789 papaverine Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 150000003138 primary alcohols Chemical group 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 230000009291 secondary effect Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
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- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
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- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
-
- 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
-
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
- C07C51/38—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by decarboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pulmonology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1203475 | 1975-03-21 | ||
GB12034/75A GB1529852A (en) | 1975-03-21 | 1975-03-21 | 8-azaprostaglandins and process for the preparation thereof |
Publications (3)
Publication Number | Publication Date |
---|---|
FI760744A FI760744A (xx) | 1976-09-22 |
FI61692B FI61692B (fi) | 1982-05-31 |
FI61692C true FI61692C (fi) | 1982-09-10 |
Family
ID=9997230
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
FI760744A FI61692C (fi) | 1975-03-21 | 1976-03-19 | Foerfarande foer framstaellning av farmakologiskt aktiva prostaglandinderivat |
Country Status (26)
Country | Link |
---|---|
JP (1) | JPS607602B2 (xx) |
AR (1) | AR213172A1 (xx) |
AT (1) | AT348163B (xx) |
AU (1) | AU501105B2 (xx) |
BE (1) | BE839761A (xx) |
CA (1) | CA1076587A (xx) |
CH (2) | CH611881A5 (xx) |
DE (1) | DE2612114A1 (xx) |
DK (1) | DK140937B (xx) |
ES (2) | ES446239A1 (xx) |
FI (1) | FI61692C (xx) |
FR (1) | FR2304340A1 (xx) |
GB (1) | GB1529852A (xx) |
HU (1) | HU173348B (xx) |
IE (1) | IE42966B1 (xx) |
IT (1) | IT1061011B (xx) |
MX (1) | MX3301E (xx) |
NL (1) | NL7602891A (xx) |
NO (1) | NO144147C (xx) |
NZ (1) | NZ180251A (xx) |
OA (1) | OA05279A (xx) |
PT (1) | PT64919B (xx) |
SE (1) | SE418290B (xx) |
SU (1) | SU614746A3 (xx) |
YU (1) | YU73876A (xx) |
ZA (1) | ZA761448B (xx) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4097489A (en) * | 1977-06-17 | 1978-06-27 | The Upjohn Company | 9-Deoxy-9α,6-nitrilo or 6,9α-imino-PGF compounds |
US5540618A (en) * | 1994-10-28 | 1996-07-30 | National University Of Singapore | Passive attenuator for shelter protection against explosions |
JP4547912B2 (ja) | 2002-03-05 | 2010-09-22 | 小野薬品工業株式会社 | 8−アザプロスタグランジン誘導体化合物およびその化合物を有効成分として含有する薬剤 |
-
1975
- 1975-03-21 GB GB12034/75A patent/GB1529852A/en not_active Expired
-
1976
- 1976-03-02 DK DK88276AA patent/DK140937B/da not_active IP Right Cessation
- 1976-03-09 NZ NZ180251A patent/NZ180251A/xx unknown
- 1976-03-09 ZA ZA761448A patent/ZA761448B/xx unknown
- 1976-03-11 AU AU11899/76A patent/AU501105B2/en not_active Expired
- 1976-03-15 IE IE545/76A patent/IE42966B1/en unknown
- 1976-03-17 AT AT195676A patent/AT348163B/de not_active IP Right Cessation
- 1976-03-18 IT IT21346/76A patent/IT1061011B/it active
- 1976-03-18 PT PT64919A patent/PT64919B/pt unknown
- 1976-03-18 FR FR7607794A patent/FR2304340A1/fr active Granted
- 1976-03-18 SE SE7603400A patent/SE418290B/xx unknown
- 1976-03-19 YU YU00738/76A patent/YU73876A/xx unknown
- 1976-03-19 CH CH844678A patent/CH611881A5/xx not_active IP Right Cessation
- 1976-03-19 BE BE165326A patent/BE839761A/xx not_active IP Right Cessation
- 1976-03-19 FI FI760744A patent/FI61692C/fi not_active IP Right Cessation
- 1976-03-19 HU HU76LA885A patent/HU173348B/hu unknown
- 1976-03-19 CH CH350176A patent/CH611604A5/xx not_active IP Right Cessation
- 1976-03-19 NL NL7602891A patent/NL7602891A/xx not_active Application Discontinuation
- 1976-03-19 AR AR262630A patent/AR213172A1/es active
- 1976-03-19 NO NO760994A patent/NO144147C/no unknown
- 1976-03-19 SU SU762334454A patent/SU614746A3/ru active
- 1976-03-19 CA CA248,275A patent/CA1076587A/en not_active Expired
- 1976-03-19 MX MX000100U patent/MX3301E/es unknown
- 1976-03-20 OA OA55774A patent/OA05279A/xx unknown
- 1976-03-20 ES ES446239A patent/ES446239A1/es not_active Expired
- 1976-03-22 DE DE19762612114 patent/DE2612114A1/de not_active Withdrawn
- 1976-03-22 JP JP51031889A patent/JPS607602B2/ja not_active Expired
-
1977
- 1977-05-03 ES ES458389A patent/ES458389A1/es not_active Expired
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Legal Events
Date | Code | Title | Description |
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MM | Patent lapsed |
Owner name: SANOFI |