JPS60104090A - ４―クロロ―フロ―（３，４―ｃ）―ピリジン誘導体、その製造法並びに利尿及び降圧組成物 - Google Patents
４―クロロ―フロ―（３，４―ｃ）―ピリジン誘導体、その製造法並びに利尿及び降圧組成物Info
- Publication number
- JPS60104090A JPS60104090A JP59216483A JP21648384A JPS60104090A JP S60104090 A JPS60104090 A JP S60104090A JP 59216483 A JP59216483 A JP 59216483A JP 21648384 A JP21648384 A JP 21648384A JP S60104090 A JPS60104090 A JP S60104090A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- groups
- dihydro
- methyl
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000203 mixture Substances 0.000 title description 2
- REIGINRVLDUJCQ-UHFFFAOYSA-N 4-chlorofuro[3,4-c]pyridine Chemical class ClC1=NC=CC2=COC=C12 REIGINRVLDUJCQ-UHFFFAOYSA-N 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 26
- 238000000921 elemental analysis Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 19
- 238000002844 melting Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- BFJMHTOBRRZELQ-UHFFFAOYSA-N 3-iodo-2h-pyrazolo[3,4-c]pyridine Chemical compound N1=CC=C2C(I)=NNC2=C1 BFJMHTOBRRZELQ-UHFFFAOYSA-N 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000004880 Polyuria Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000035619 diuresis Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JJGRSVSRPHZQGZ-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)-6-methyl-3-phenyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC=C2C=1COC2(C=1C(=C(Cl)C=CC=1)Cl)C1=CC=CC=C1 JJGRSVSRPHZQGZ-UHFFFAOYSA-N 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 101150104041 eno2 gene Proteins 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- UDOZVPVDQKQJAP-UHFFFAOYSA-N trifluoroamine oxide Chemical compound [O-][N+](F)(F)F UDOZVPVDQKQJAP-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8327817 | 1983-10-18 | ||
| GB838327817A GB8327817D0 (en) | 1983-10-18 | 1983-10-18 | 4-halo-furo-(3 4-c)-pyridine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60104090A true JPS60104090A (ja) | 1985-06-08 |
| JPH0339513B2 JPH0339513B2 (en, 2012) | 1991-06-14 |
Family
ID=10550364
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59216483A Granted JPS60104090A (ja) | 1983-10-18 | 1984-10-17 | ４―クロロ―フロ―（３，４―ｃ）―ピリジン誘導体、その製造法並びに利尿及び降圧組成物 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4585776A (en, 2012) |
| JP (1) | JPS60104090A (en, 2012) |
| AT (1) | AT391699B (en, 2012) |
| BE (1) | BE900780A (en, 2012) |
| CA (1) | CA1257270A (en, 2012) |
| CH (1) | CH662118A5 (en, 2012) |
| DE (1) | DE3438244A1 (en, 2012) |
| DK (1) | DK158003C (en, 2012) |
| DZ (1) | DZ687A1 (en, 2012) |
| ES (1) | ES536814A0 (en, 2012) |
| FI (1) | FI80036C (en, 2012) |
| FR (2) | FR2553286B1 (en, 2012) |
| GB (2) | GB8327817D0 (en, 2012) |
| HK (1) | HK54787A (en, 2012) |
| IE (1) | IE58041B1 (en, 2012) |
| IT (1) | IT1176986B (en, 2012) |
| LU (1) | LU85583A1 (en, 2012) |
| MA (1) | MA20251A1 (en, 2012) |
| NL (1) | NL8403181A (en, 2012) |
| OA (1) | OA07840A (en, 2012) |
| PT (2) | PT79369B (en, 2012) |
| SE (1) | SE459093B (en, 2012) |
| SG (1) | SG25387G (en, 2012) |
| ZA (1) | ZA847961B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8808001D0 (en) * | 1988-04-06 | 1988-05-05 | Scras | Stereospecific preparative process for furol(3,4-c)pyridine derivatives |
| GB8907480D0 (en) * | 1989-04-03 | 1989-05-17 | Scaras Societe De Conseils De | Separation of insomers of furo(3,4-c)pyridine derivatives |
| GB8917168D0 (en) * | 1989-07-27 | 1989-09-13 | Scras | Asymmetric synthesis of furo(3,4-c)pyridine derivatives |
| US5130252A (en) * | 1990-05-14 | 1992-07-14 | Synthetech, Inc. | Resolution of furopyridine enantiomers and synthetic precursors thereof |
| US6865862B2 (en) * | 2000-11-20 | 2005-03-15 | C.G. Bretting Mfg. Co., Inc. | Log bander apparatus and method |
| GB0221494D0 (en) * | 2002-09-16 | 2002-10-23 | Generics Uk Ltd | Novel processes for the preparation of 1.3-dihydro-6-methylfuro (3,4-c) pyndin derivatives |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54109996A (en) * | 1977-11-25 | 1979-08-29 | Scras | Pridine derivative*manufacture thereof and kidney protection and diuretic composition containing said derivative |
| JPS57150688A (en) * | 1981-02-10 | 1982-09-17 | Do Konseiyu Do Rushierushie E | Furo(3,4-c)pyridine derivative, manufacture and medicinal composition containing same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5621578B2 (en, 2012) * | 1973-06-02 | 1981-05-20 | ||
| GB2008582B (en) * | 1977-11-25 | 1982-04-28 | Scras | Pyridine derivative |
-
1983
- 1983-10-18 GB GB838327817A patent/GB8327817D0/en active Pending
-
1984
- 1984-10-09 BE BE0/213802A patent/BE900780A/fr not_active IP Right Cessation
- 1984-10-10 LU LU85583A patent/LU85583A1/fr unknown
- 1984-10-10 CH CH4863/84A patent/CH662118A5/fr not_active IP Right Cessation
- 1984-10-11 ZA ZA847961A patent/ZA847961B/xx unknown
- 1984-10-11 GB GB08425704A patent/GB2148292B/en not_active Expired
- 1984-10-12 SE SE8405118A patent/SE459093B/sv not_active IP Right Cessation
- 1984-10-13 DZ DZ847301A patent/DZ687A1/fr active
- 1984-10-15 MA MA20475A patent/MA20251A1/fr unknown
- 1984-10-15 FI FI844034A patent/FI80036C/fi not_active IP Right Cessation
- 1984-10-16 US US06/661,376 patent/US4585776A/en not_active Expired - Lifetime
- 1984-10-17 IE IE266384A patent/IE58041B1/en not_active IP Right Cessation
- 1984-10-17 ES ES536814A patent/ES536814A0/es active Granted
- 1984-10-17 IT IT23176/84A patent/IT1176986B/it active
- 1984-10-17 DK DK495984A patent/DK158003C/da not_active IP Right Cessation
- 1984-10-17 JP JP59216483A patent/JPS60104090A/ja active Granted
- 1984-10-17 PT PT79369A patent/PT79369B/pt not_active IP Right Cessation
- 1984-10-18 FR FR8415947A patent/FR2553286B1/fr not_active Expired
- 1984-10-18 AT AT0332984A patent/AT391699B/de not_active IP Right Cessation
- 1984-10-18 CA CA000465804A patent/CA1257270A/en not_active Expired
- 1984-10-18 NL NL8403181A patent/NL8403181A/nl not_active Application Discontinuation
- 1984-10-18 FR FR8415948A patent/FR2553417B1/fr not_active Expired
- 1984-10-18 DE DE19843438244 patent/DE3438244A1/de active Granted
- 1984-10-18 OA OA58417A patent/OA07840A/xx unknown
- 1984-11-16 PT PT79512A patent/PT79512B/pt not_active IP Right Cessation
-
1987
- 1987-03-12 SG SG253/87A patent/SG25387G/en unknown
- 1987-07-23 HK HK547/87A patent/HK54787A/xx not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54109996A (en) * | 1977-11-25 | 1979-08-29 | Scras | Pridine derivative*manufacture thereof and kidney protection and diuretic composition containing said derivative |
| JPS57150688A (en) * | 1981-02-10 | 1982-09-17 | Do Konseiyu Do Rushierushie E | Furo(3,4-c)pyridine derivative, manufacture and medicinal composition containing same |
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