CS258492B2 - Method of new dihydropyridine-lactols production - Google Patents
Method of new dihydropyridine-lactols production Download PDFInfo
- Publication number
- CS258492B2 CS258492B2 CS867923A CS792386A CS258492B2 CS 258492 B2 CS258492 B2 CS 258492B2 CS 867923 A CS867923 A CS 867923A CS 792386 A CS792386 A CS 792386A CS 258492 B2 CS258492 B2 CS 258492B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- alkyl group
- carbon atoms
- compounds
- group
- lactols
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- -1 dihydropyridine lactones Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000217 alkyl group Chemical group 0.000 claims description 6
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- 229910052794 bromium Inorganic materials 0.000 claims description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
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- 239000012188 paraffin wax Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 235000019477 peppermint oil Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- GJGNPYHBMNPBRG-UHFFFAOYSA-N propan-2-yl 1-ethyl-7-hydroxy-2-methyl-4-(2-methylphenyl)-5-oxo-4,7-dihydrofuro[3,4-b]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=C(C)N(CC)C(C(OC2=O)O)=C2C1C1=CC=CC=C1C GJGNPYHBMNPBRG-UHFFFAOYSA-N 0.000 description 1
- RDNYWZSSVWSDGE-UHFFFAOYSA-N propan-2-yl 1-ethyl-7-hydroxy-2-methyl-4-(3-nitrophenyl)-5-oxo-4,7-dihydrofuro[3,4-b]pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=C(C)N(CC)C(C(OC2=O)O)=C2C1C1=CC=CC([N+]([O-])=O)=C1 RDNYWZSSVWSDGE-UHFFFAOYSA-N 0.000 description 1
- VSRSQDMWBSKNSF-UHFFFAOYSA-N propan-2-yl pyridine-3-carboxylate Chemical compound CC(C)OC(=O)C1=CC=CN=C1 VSRSQDMWBSKNSF-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Steroid Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicinal Preparation (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS873846A CS258499B2 (cs) | 1986-01-17 | 1987-05-27 | Způsob výroby nových dihydropyridinlaktolů |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19863601226 DE3601226A1 (de) | 1986-01-17 | 1986-01-17 | Dihydropyridinlactole, verfahren zur herstellung und ihre verwendung in arzneimitteln |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS792386A2 CS792386A2 (en) | 1988-01-15 |
| CS258492B2 true CS258492B2 (en) | 1988-08-16 |
Family
ID=6292033
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS867923A CS258492B2 (en) | 1986-01-17 | 1986-11-03 | Method of new dihydropyridine-lactols production |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4721719A (pl) |
| EP (1) | EP0235347B1 (pl) |
| JP (1) | JPH0762018B2 (pl) |
| KR (1) | KR870007179A (pl) |
| CN (2) | CN1019488B (pl) |
| AT (1) | ATE68184T1 (pl) |
| AU (1) | AU587068B2 (pl) |
| CA (1) | CA1293508C (pl) |
| CS (1) | CS258492B2 (pl) |
| DD (1) | DD268945A5 (pl) |
| DE (2) | DE3601226A1 (pl) |
| DK (1) | DK161252C (pl) |
| EG (1) | EG18031A (pl) |
| ES (1) | ES2009209A6 (pl) |
| FI (1) | FI870151A7 (pl) |
| GR (1) | GR862107B (pl) |
| HU (1) | HU196804B (pl) |
| IL (1) | IL81258A (pl) |
| NO (1) | NO164597C (pl) |
| NZ (1) | NZ217308A (pl) |
| PH (1) | PH23676A (pl) |
| PL (2) | PL149184B1 (pl) |
| PT (1) | PT84120B (pl) |
| SU (1) | SU1440345A3 (pl) |
| ZA (1) | ZA865968B (pl) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3410645A1 (de) * | 1984-03-23 | 1985-09-26 | Bayer Ag, 5090 Leverkusen | L-alkylsubstituierte 1,4-dihydropyridinlactone, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| JP2594809B2 (ja) * | 1988-04-02 | 1997-03-26 | 日本ゼオン株式会社 | タイヤトレッド用ゴム組成物 |
| KR100860067B1 (ko) * | 2001-01-17 | 2008-09-24 | 아무라 테라피틱스 리미티드 | 크루지페인 및 기타 시스테인 프로테아제의 억제제 |
| JP4860050B2 (ja) * | 2001-04-23 | 2012-01-25 | 富士重工業株式会社 | 溶断装置による穿孔方法及び溶断装置 |
| CA2538188A1 (en) * | 2003-09-10 | 2005-03-24 | Synta Pharmaceuticals Corp. | Dihydropyridine compounds for treating or preventing metabolic disorders |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3269219D1 (en) * | 1981-11-17 | 1986-03-27 | Fisons Plc | Dihydropyridines, methods for their production and their formulation and use as pharmaceuticals |
| EP0111455A3 (de) * | 1982-12-10 | 1984-07-25 | Ciba-Geigy Ag | Ungesättigte Lactone |
| DE3343658A1 (de) * | 1983-12-02 | 1985-06-13 | Bayer Ag, 5090 Leverkusen | Hydroxy-tetrahydropyridinlactone, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
-
1986
- 1986-01-17 DE DE19863601226 patent/DE3601226A1/de not_active Withdrawn
- 1986-08-05 DK DK372586A patent/DK161252C/da not_active IP Right Cessation
- 1986-08-06 DE DE8686110896T patent/DE3681913D1/de not_active Expired - Lifetime
- 1986-08-06 AT AT86110896T patent/ATE68184T1/de active
- 1986-08-06 EP EP86110896A patent/EP0235347B1/de not_active Expired - Lifetime
- 1986-08-08 ZA ZA865968A patent/ZA865968B/xx unknown
- 1986-08-08 DD DD86293531A patent/DD268945A5/de not_active IP Right Cessation
- 1986-08-11 GR GR862107A patent/GR862107B/el unknown
- 1986-08-15 PL PL1986261050A patent/PL149184B1/pl unknown
- 1986-08-15 PL PL1986271190A patent/PL149694B1/pl unknown
- 1986-08-19 ES ES8601187A patent/ES2009209A6/es not_active Expired
- 1986-08-21 NZ NZ217308A patent/NZ217308A/xx unknown
- 1986-08-22 JP JP61195704A patent/JPH0762018B2/ja not_active Expired - Lifetime
- 1986-08-25 EG EG536/86A patent/EG18031A/xx active
- 1986-08-27 SU SU864028009A patent/SU1440345A3/ru active
- 1986-08-27 US US06/900,866 patent/US4721719A/en not_active Expired - Lifetime
- 1986-08-29 PH PH34199A patent/PH23676A/en unknown
- 1986-09-02 CA CA000517282A patent/CA1293508C/en not_active Expired - Lifetime
- 1986-09-16 KR KR1019860007764A patent/KR870007179A/ko not_active Ceased
- 1986-09-29 AU AU63233/86A patent/AU587068B2/en not_active Ceased
- 1986-10-04 CN CN86106735A patent/CN1019488B/zh not_active Expired
- 1986-10-04 CN CN91108007A patent/CN1061528A/zh active Pending
- 1986-11-03 CS CS867923A patent/CS258492B2/cs unknown
- 1986-12-29 NO NO865324A patent/NO164597C/no unknown
-
1987
- 1987-01-14 IL IL81258A patent/IL81258A/xx unknown
- 1987-01-15 FI FI870151A patent/FI870151A7/fi not_active Application Discontinuation
- 1987-01-16 HU HU87122A patent/HU196804B/hu not_active IP Right Cessation
- 1987-01-16 PT PT84120A patent/PT84120B/pt not_active IP Right Cessation
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