CA1257272A - 7-carboxymethoxy-furo-(3,4-c)-pyridine derivatives - Google Patents
7-carboxymethoxy-furo-(3,4-c)-pyridine derivativesInfo
- Publication number
- CA1257272A CA1257272A CA000467829A CA467829A CA1257272A CA 1257272 A CA1257272 A CA 1257272A CA 000467829 A CA000467829 A CA 000467829A CA 467829 A CA467829 A CA 467829A CA 1257272 A CA1257272 A CA 1257272A
- Authority
- CA
- Canada
- Prior art keywords
- furo
- dihydro
- pyridine
- carboxymethoxy
- 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.)
- Expired
Links
- VNNXQKIUVGKNHW-UHFFFAOYSA-N 2-furo[3,4-c]pyridin-7-yloxyacetic acid Chemical class OC(=O)COC1=CN=CC2=COC=C12 VNNXQKIUVGKNHW-UHFFFAOYSA-N 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 22
- IHWMIFMVQLOHLG-UHFFFAOYSA-N 6-methyl-1,3-dihydrofuro[3,4-c]pyridine Chemical class C1=NC(C)=CC2=C1COC2 IHWMIFMVQLOHLG-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 4
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 3
- GHTWTWDSJLSJPA-UHFFFAOYSA-N 2-[(3,6-dimethyl-3-pentyl-1h-furo[3,4-c]pyridin-7-yl)oxy]acetic acid Chemical compound C1=NC(C)=C(OCC(O)=O)C2=C1C(CCCCC)(C)OC2 GHTWTWDSJLSJPA-UHFFFAOYSA-N 0.000 claims description 2
- MYLUTUZSWPOIMC-UHFFFAOYSA-N 2-[(3-butyl-3-ethyl-6-methyl-1h-furo[3,4-c]pyridin-7-yl)oxy]acetic acid Chemical compound C1=NC(C)=C(OCC(O)=O)C2=C1C(CCCC)(CC)OC2 MYLUTUZSWPOIMC-UHFFFAOYSA-N 0.000 claims description 2
- CQCPTPPPRPYILP-UHFFFAOYSA-N 2-[(3-butyl-4-chloro-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl)oxy]acetic acid Chemical compound C(CCC)C1OCC2=C1C(=NC(=C2OCC(=O)O)C)Cl CQCPTPPPRPYILP-UHFFFAOYSA-N 0.000 claims description 2
- HTVZABPSDHVMDS-UHFFFAOYSA-N 2-[(4-chloro-3,6-dimethyl-3-phenyl-1h-furo[3,4-c]pyridin-7-yl)oxy]acetic acid Chemical compound OC(=O)COC=1C(C)=NC(Cl)=C2C=1COC2(C)C1=CC=CC=C1 HTVZABPSDHVMDS-UHFFFAOYSA-N 0.000 claims description 2
- QISDMJSLRIZXOZ-UHFFFAOYSA-N 2-[(4-chloro-3-ethyl-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl)oxy]acetic acid Chemical compound ClC1=NC(C)=C(OCC(O)=O)C2=C1C(CC)OC2 QISDMJSLRIZXOZ-UHFFFAOYSA-N 0.000 claims description 2
- RHMKBLSGUNJRJY-UHFFFAOYSA-N 2-[[3-(4-fluorophenyl)-3,6-dimethyl-1h-furo[3,4-c]pyridin-7-yl]oxy]acetic acid Chemical compound OC(=O)COC=1C(C)=NC=C2C=1COC2(C)C1=CC=C(F)C=C1 RHMKBLSGUNJRJY-UHFFFAOYSA-N 0.000 claims description 2
- CLQNYNHDJQJWNT-UHFFFAOYSA-N 2-[[3-(4-fluorophenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl]oxy]acetic acid Chemical compound O1CC2=C(OCC(O)=O)C(C)=NC=C2C1C1=CC=C(F)C=C1 CLQNYNHDJQJWNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- -1 1,3-dihydro-3-ethyl-6-methyl-7 carboxy-methoxy-furo-(3,4-c)-pyridine Chemical compound 0.000 claims 2
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- BSCJLMOJVKMPLM-UHFFFAOYSA-N 2-[(4-chloro-3,3,6-trimethyl-1h-furo[3,4-c]pyridin-7-yl)oxy]acetic acid Chemical compound CC1=NC(Cl)=C2C(C)(C)OCC2=C1OCC(O)=O BSCJLMOJVKMPLM-UHFFFAOYSA-N 0.000 claims 1
- NROQVFMIKHXZEE-UHFFFAOYSA-N 2-[[3-(3-chlorophenyl)-3,6-dimethyl-1H-furo[3,4-c]pyridin-7-yl]oxy]acetic acid Chemical compound ClC=1C=C(C=CC1)C1(OCC2=C1C=NC(=C2OCC(=O)O)C)C NROQVFMIKHXZEE-UHFFFAOYSA-N 0.000 claims 1
- PGHRBYISODHGNF-UHFFFAOYSA-N 2-[[3-(4-chlorophenyl)-3,6-dimethyl-1h-furo[3,4-c]pyridin-7-yl]oxy]acetic acid Chemical compound OC(=O)COC=1C(C)=NC=C2C=1COC2(C)C1=CC=C(Cl)C=C1 PGHRBYISODHGNF-UHFFFAOYSA-N 0.000 claims 1
- SFALQWYGIWKMFS-UHFFFAOYSA-N 2-[[3-(4-chlorophenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl]oxy]acetic acid Chemical compound O1CC2=C(OCC(O)=O)C(C)=NC=C2C1C1=CC=C(Cl)C=C1 SFALQWYGIWKMFS-UHFFFAOYSA-N 0.000 claims 1
- LKQNVACAQNLINB-UHFFFAOYSA-N 2-[[4-bromo-3-(4-chlorophenyl)-3,6-dimethyl-1h-furo[3,4-c]pyridin-7-yl]oxy]acetic acid Chemical compound OC(=O)COC=1C(C)=NC(Br)=C2C=1COC2(C)C1=CC=C(Cl)C=C1 LKQNVACAQNLINB-UHFFFAOYSA-N 0.000 claims 1
- STSQAMJMGVYCOA-UHFFFAOYSA-N 2-[[4-bromo-3-(4-chlorophenyl)-3-ethyl-6-methyl-1h-furo[3,4-c]pyridin-7-yl]oxy]acetic acid Chemical compound O1CC(C(=C(C)N=C2Br)OCC(O)=O)=C2C1(CC)C1=CC=C(Cl)C=C1 STSQAMJMGVYCOA-UHFFFAOYSA-N 0.000 claims 1
- SFRMZEBQCDKAKE-UHFFFAOYSA-N 2-[[4-bromo-3-(4-chlorophenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl]oxy]acetic acid Chemical compound O1CC2=C(OCC(O)=O)C(C)=NC(Br)=C2C1C1=CC=C(Cl)C=C1 SFRMZEBQCDKAKE-UHFFFAOYSA-N 0.000 claims 1
- ICMVCSDQLPEXIZ-UHFFFAOYSA-N 2-[[4-bromo-3-(4-chlorophenyl)-6-methyl-3-propyl-1h-furo[3,4-c]pyridin-7-yl]oxy]acetic acid Chemical compound O1CC(C(=C(C)N=C2Br)OCC(O)=O)=C2C1(CCC)C1=CC=C(Cl)C=C1 ICMVCSDQLPEXIZ-UHFFFAOYSA-N 0.000 claims 1
- LZUMPFSTYSAXPG-UHFFFAOYSA-N 2-[[4-chloro-3,3-bis(4-chlorophenyl)-6-methyl-1h-furo[3,4-c]pyridin-7-yl]oxy]acetic acid Chemical compound OC(=O)COC=1C(C)=NC(Cl)=C2C=1COC2(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 LZUMPFSTYSAXPG-UHFFFAOYSA-N 0.000 claims 1
- LAXBXEFVMKXAKS-UHFFFAOYSA-N 2-[[4-chloro-3-(4-methoxyphenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl]oxy]acetic acid Chemical compound C1=CC(OC)=CC=C1C1C(C(Cl)=NC(C)=C2OCC(O)=O)=C2CO1 LAXBXEFVMKXAKS-UHFFFAOYSA-N 0.000 claims 1
- GCQIFJXJHAXPNB-UHFFFAOYSA-N 2-[[6-methyl-3-(4-methylphenyl)-3-phenyl-1h-furo[3,4-c]pyridin-7-yl]oxy]acetic acid Chemical compound C1=CC(C)=CC=C1C1(C=2C=CC=CC=2)C(C=NC(C)=C2OCC(O)=O)=C2CO1 GCQIFJXJHAXPNB-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- 208000004880 Polyuria Diseases 0.000 abstract description 2
- 239000000739 antihistaminic agent Substances 0.000 abstract description 2
- 229940125715 antihistaminic agent Drugs 0.000 abstract description 2
- 230000036772 blood pressure Effects 0.000 abstract description 2
- 230000035619 diuresis Effects 0.000 abstract description 2
- 210000003734 kidney Anatomy 0.000 abstract description 2
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- 239000000047 product Substances 0.000 description 17
- 238000000921 elemental analysis Methods 0.000 description 16
- 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 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- 208000024780 Urticaria Diseases 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229960003699 evans blue Drugs 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 2
- HOKDBMAJZXIPGC-UHFFFAOYSA-N Mequitazine Chemical compound C12=CC=CC=C2SC2=CC=CC=C2N1CC1C(CC2)CCN2C1 HOKDBMAJZXIPGC-UHFFFAOYSA-N 0.000 description 2
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- DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 1
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- LRDLAQUPXWBSJX-UHFFFAOYSA-N 2-[(6-methyl-3-phenyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl)oxy]acetic acid Chemical compound O1CC2=C(OCC(O)=O)C(C)=NC=C2C1C1=CC=CC=C1 LRDLAQUPXWBSJX-UHFFFAOYSA-N 0.000 description 1
- NEZNJUSMHRVYMO-UHFFFAOYSA-N 2-[2-(4-methoxyphenoxy)acetyl]oxyethyl-dimethylazanium;chloride Chemical compound [Cl-].COC1=CC=C(OCC(=O)OCC[NH+](C)C)C=C1 NEZNJUSMHRVYMO-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- KWAHUCNBAOBTNK-UHFFFAOYSA-N 3,6-dimethyl-3-pentyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound C1=NC(C)=C(O)C2=C1C(CCCCC)(C)OC2 KWAHUCNBAOBTNK-UHFFFAOYSA-N 0.000 description 1
- HKUOMRSPQVGCHJ-UHFFFAOYSA-N 3-(3-chlorophenyl)-3,6-dimethyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC=C2C=1COC2(C)C1=CC=CC(Cl)=C1 HKUOMRSPQVGCHJ-UHFFFAOYSA-N 0.000 description 1
- GONPALGLQOQSAR-UHFFFAOYSA-N 3-(4-chlorophenoxy)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound O1CC2=C(O)C(C)=NC=C2C1OC1=CC=C(Cl)C=C1 GONPALGLQOQSAR-UHFFFAOYSA-N 0.000 description 1
- LQEMUWNIWKVWOP-UHFFFAOYSA-N 3-(4-chlorophenyl)-3,6-dimethyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC=C2C=1COC2(C)C1=CC=C(Cl)C=C1 LQEMUWNIWKVWOP-UHFFFAOYSA-N 0.000 description 1
- JWXDAFDYHBKRJI-UHFFFAOYSA-N 3-(4-fluorophenyl)-3,6-dimethyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC=C2C=1COC2(C)C1=CC=C(F)C=C1 JWXDAFDYHBKRJI-UHFFFAOYSA-N 0.000 description 1
- ANEYGXYUZGDDGH-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound O1CC2=C(O)C(C)=NC=C2C1C1=CC=C(F)C=C1 ANEYGXYUZGDDGH-UHFFFAOYSA-N 0.000 description 1
- PZMWHUMWOMSCRX-UHFFFAOYSA-N 3-butyl-4-chloro-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound ClC1=NC(C)=C(O)C2=C1C(CCCC)OC2 PZMWHUMWOMSCRX-UHFFFAOYSA-N 0.000 description 1
- MEVOEUZLYUNXHS-UHFFFAOYSA-N 3-ethyl-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C1=NC(C)=C(O)C2=C1C(CC)OC2 MEVOEUZLYUNXHS-UHFFFAOYSA-N 0.000 description 1
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- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D497/04—Ortho-condensed systems
-
- 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
-
- 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)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8330658 | 1983-11-17 | ||
| GB838330658A GB8330658D0 (en) | 1983-11-17 | 1983-11-17 | 7-carboxymethoxy-furo-(3,4-c)-pyridine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1257272A true CA1257272A (en) | 1989-07-11 |
Family
ID=10551897
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000467829A Expired CA1257272A (en) | 1983-11-17 | 1984-11-14 | 7-carboxymethoxy-furo-(3,4-c)-pyridine derivatives |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4569938A (en, 2012) |
| JP (1) | JPS60116685A (en, 2012) |
| AT (1) | AT391868B (en, 2012) |
| BE (1) | BE900941A (en, 2012) |
| CA (1) | CA1257272A (en, 2012) |
| CH (1) | CH660737A5 (en, 2012) |
| DE (1) | DE3441975A1 (en, 2012) |
| DK (1) | DK157932C (en, 2012) |
| DZ (1) | DZ702A1 (en, 2012) |
| ES (1) | ES537666A0 (en, 2012) |
| FI (1) | FI80701C (en, 2012) |
| FR (2) | FR2555181B1 (en, 2012) |
| GB (2) | GB8330658D0 (en, 2012) |
| HK (1) | HK77987A (en, 2012) |
| IE (1) | IE58097B1 (en, 2012) |
| IT (1) | IT1177185B (en, 2012) |
| LU (1) | LU85634A1 (en, 2012) |
| MA (1) | MA20263A1 (en, 2012) |
| MY (1) | MY100665A (en, 2012) |
| NL (1) | NL8403318A (en, 2012) |
| OA (1) | OA07865A (en, 2012) |
| SE (1) | SE458277B (en, 2012) |
| SG (1) | SG52687G (en, 2012) |
| ZA (1) | ZA848128B (en, 2012) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8402740D0 (en) * | 1984-02-02 | 1984-03-07 | Scras | Furo-(3 4-c)-pyridine derivatives |
| 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 |
| US5130252A (en) * | 1990-05-14 | 1992-07-14 | Synthetech, Inc. | Resolution of furopyridine enantiomers and synthetic precursors thereof |
| DK1169322T3 (da) | 1999-03-08 | 2006-03-06 | Medicure Inc | Pyridoxalanaloger til behandling af lidelser foranlediget af vitamin B6-mangel |
| AU5840200A (en) * | 1999-07-13 | 2001-01-30 | Medicure Inc. | Treatment of diabetes and related pathologies |
| EP1872797A3 (en) | 1999-08-24 | 2008-04-02 | Medicure International Inc. | Treatment of cardiovascular and related pathologies |
| US7442689B2 (en) * | 2000-02-29 | 2008-10-28 | Medicure International Inc. | Cardioprotective phosphonates and malonates |
| ES2305994T3 (es) | 2000-02-29 | 2008-11-01 | Medicure International Inc. | Fosfonatos cardioprotectores. |
| AU784840B2 (en) | 2000-03-28 | 2006-07-06 | Medicure International Inc. | Treatment of cerebrovascular disease |
| WO2002004421A2 (en) | 2000-07-07 | 2002-01-17 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: cardiovascular therapeutics |
| US6897228B2 (en) | 2000-07-07 | 2005-05-24 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: new uses |
| US6548519B1 (en) | 2001-07-06 | 2003-04-15 | Medicure International Inc. | Pyridoxine and pyridoxal analogues: novel uses |
| US20040121988A1 (en) * | 2001-03-28 | 2004-06-24 | Medicure International Inc. | Treatment of cerebrovascular disease |
| US20040186077A1 (en) * | 2003-03-17 | 2004-09-23 | Medicure International Inc. | Novel heteroaryl phosphonates as cardioprotective agents |
| US20060019929A1 (en) * | 2004-07-07 | 2006-01-26 | Albert Friesen | Combination therapies employing platelet aggregation drugs |
| US20070060549A1 (en) * | 2004-08-10 | 2007-03-15 | Friesen Albert D | Combination therapies employing ace inhibitors and uses thereof for the treatment of diabetic disorders |
| US7459468B2 (en) * | 2004-10-28 | 2008-12-02 | Medicure International, Inc. | Aryl sulfonic pyridoxines as antiplatelet agents |
| US20060094749A1 (en) * | 2004-10-28 | 2006-05-04 | Medicure International Inc. | Substituted pyridoxines as anti-platelet agents |
| AU2005304220A1 (en) * | 2004-10-28 | 2006-05-18 | Medicure International Inc. | Dual antiplatelet/anticoagulant pyridoxine analogs |
| US20070105817A1 (en) * | 2005-11-09 | 2007-05-10 | Jim Page | Use of cicletanine and other furopyridines for treatment of systolic-predominant hypertension, isolated systolic hypertension, elevated pulse pressure, and general hypertension |
| JP2009517411A (ja) * | 2005-11-28 | 2009-04-30 | メディキュア インターナショナル インコーポレーテッド | 心血管及び関連病状の処置のための調剤 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT297442B (de) * | 1970-04-01 | 1972-03-27 | Unilever Nv | Verfahren zum Reinigen, Entfetten, Entzundern und Beizen von Metallen |
| ZA786269B (en) * | 1977-11-25 | 1979-10-31 | Scras | New pyridine derivative,its preparation and use |
| GB2008582B (en) * | 1977-11-25 | 1982-04-28 | Scras | Pyridine derivative |
| IN156817B (en, 2012) * | 1981-02-10 | 1985-11-09 | Scras |
-
1983
- 1983-11-17 GB GB838330658A patent/GB8330658D0/en active Pending
-
1984
- 1984-10-17 ZA ZA848128A patent/ZA848128B/xx unknown
- 1984-10-19 GB GB08426489A patent/GB2149781B/en not_active Expired
- 1984-10-26 CH CH5127/84A patent/CH660737A5/fr not_active IP Right Cessation
- 1984-10-30 BE BE0/213925A patent/BE900941A/fr not_active IP Right Cessation
- 1984-11-01 NL NL8403318A patent/NL8403318A/nl not_active Application Discontinuation
- 1984-11-05 US US06/668,394 patent/US4569938A/en not_active Expired - Lifetime
- 1984-11-07 LU LU85634A patent/LU85634A1/fr unknown
- 1984-11-08 MA MA20487A patent/MA20263A1/fr unknown
- 1984-11-08 FI FI844383A patent/FI80701C/fi not_active IP Right Cessation
- 1984-11-14 DZ DZ847329A patent/DZ702A1/fr active
- 1984-11-14 IT IT23564/84A patent/IT1177185B/it active
- 1984-11-14 CA CA000467829A patent/CA1257272A/en not_active Expired
- 1984-11-15 ES ES537666A patent/ES537666A0/es active Granted
- 1984-11-16 SE SE8405754A patent/SE458277B/sv not_active IP Right Cessation
- 1984-11-16 DK DK545684A patent/DK157932C/da not_active IP Right Cessation
- 1984-11-16 FR FR8417478A patent/FR2555181B1/fr not_active Expired
- 1984-11-16 FR FR8417479A patent/FR2555049B1/fr not_active Expired
- 1984-11-16 IE IE294784A patent/IE58097B1/en not_active IP Right Cessation
- 1984-11-16 OA OA58442A patent/OA07865A/xx unknown
- 1984-11-16 DE DE19843441975 patent/DE3441975A1/de active Granted
- 1984-11-16 JP JP59240900A patent/JPS60116685A/ja active Granted
- 1984-11-19 AT AT0365584A patent/AT391868B/de not_active IP Right Cessation
-
1987
- 1987-06-17 SG SG52687A patent/SG52687G/en unknown
- 1987-07-01 MY MYPI87000926A patent/MY100665A/en unknown
- 1987-10-22 HK HK779/87A patent/HK77987A/xx not_active IP Right Cessation
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |