NL8403318A - Nieuwe 7-carboxymethoxy-furo-(3,4-c)-pyridinederivaten, hun bereiding en therapeutische preparaten die ze bevatten. - Google Patents
Nieuwe 7-carboxymethoxy-furo-(3,4-c)-pyridinederivaten, hun bereiding en therapeutische preparaten die ze bevatten. Download PDFInfo
- Publication number
- NL8403318A NL8403318A NL8403318A NL8403318A NL8403318A NL 8403318 A NL8403318 A NL 8403318A NL 8403318 A NL8403318 A NL 8403318A NL 8403318 A NL8403318 A NL 8403318A NL 8403318 A NL8403318 A NL 8403318A
- Authority
- NL
- Netherlands
- Prior art keywords
- furo
- dihydro
- pyridine
- methyl
- carboxymethoxy
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title description 6
- 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 3
- 230000001225 therapeutic effect Effects 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 34
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 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 description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 1
- 238000002844 melting Methods 0.000 description 31
- 230000008018 melting Effects 0.000 description 31
- 238000000034 method Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 238000000921 elemental analysis Methods 0.000 description 16
- -1 1,3-dihydro-3-p-chlorophenyl-6-methyl-7-carboxy-methoxy-furo (3,4-c) -pyridine Chemical compound 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 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
- 230000009467 reduction Effects 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
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000000739 antihistaminic agent Substances 0.000 description 3
- 229960003699 evans blue Drugs 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 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 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
- 108010058846 Ovalbumin Proteins 0.000 description 2
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000001387 anti-histamine Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000028709 inflammatory response Effects 0.000 description 2
- 229960005042 mequitazine Drugs 0.000 description 2
- 229940092253 ovalbumin Drugs 0.000 description 2
- 229960003910 promethazine Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229960000278 theophylline Drugs 0.000 description 2
- HETVMPXLRIBHPB-UHFFFAOYSA-N 2-[(3-ethyl-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl)oxy]acetic acid Chemical compound C1=NC(C)=C(OCC(O)=O)C2=C1C(CC)OC2 HETVMPXLRIBHPB-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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
- 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 description 1
- 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 description 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 description 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 description 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 description 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 description 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 description 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 description 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 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
- LOPQXLOIRYZLMN-UHFFFAOYSA-N 3,6-dimethylfuro[3,4-c]pyridin-7-ol Chemical compound CC=1OC=C2C=1C=NC(=C2O)C LOPQXLOIRYZLMN-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
- 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
- XIUDHWARDNZSSX-UHFFFAOYSA-N 3-butyl-3-ethyl-6-methyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound C1=NC(C)=C(O)C2=C1C(CCCC)(CC)OC2 XIUDHWARDNZSSX-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- GBXNEXHTLHJCCQ-UHFFFAOYSA-N 4-bromo-3-(4-chlorophenyl)-3,6-dimethyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC(Br)=C2C=1COC2(C)C1=CC=C(Cl)C=C1 GBXNEXHTLHJCCQ-UHFFFAOYSA-N 0.000 description 1
- WYAPBLOJYSXOBY-UHFFFAOYSA-N 4-bromo-3-(4-methoxyphenyl)-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound C1=CC(OC)=CC=C1C1C(C(Br)=NC(C)=C2O)=C2CO1 WYAPBLOJYSXOBY-UHFFFAOYSA-N 0.000 description 1
- FXNRMPYJNRGEAG-UHFFFAOYSA-N 4-chloro-3,3,6-trimethyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound CC1=NC(Cl)=C2C(C)(C)OCC2=C1O FXNRMPYJNRGEAG-UHFFFAOYSA-N 0.000 description 1
- JNXCOPPTXGMZCF-UHFFFAOYSA-N 4-chloro-3,3-bis(4-chlorophenyl)-6-methyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC(Cl)=C2C=1COC2(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 JNXCOPPTXGMZCF-UHFFFAOYSA-N 0.000 description 1
- MZLLECZYEGRZSK-UHFFFAOYSA-N 4-chloro-3,6-dimethyl-3-phenyl-1h-furo[3,4-c]pyridin-7-ol Chemical compound OC=1C(C)=NC(Cl)=C2C=1COC2(C)C1=CC=CC=C1 MZLLECZYEGRZSK-UHFFFAOYSA-N 0.000 description 1
- VBLXCSRFMPHRMN-UHFFFAOYSA-N 4-chloro-3-ethyl-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound ClC1=NC(C)=C(O)C2=C1C(CC)OC2 VBLXCSRFMPHRMN-UHFFFAOYSA-N 0.000 description 1
- AWSNANLRLHTJCZ-UHFFFAOYSA-N 6-methyl-3-phenyl-1,3-dihydrofuro[3,4-c]pyridin-7-ol Chemical compound O1CC2=C(O)C(C)=NC=C2C1C1=CC=CC=C1 AWSNANLRLHTJCZ-UHFFFAOYSA-N 0.000 description 1
- NZOCLVWZHBNOKT-UHFFFAOYSA-N 6-methylfuro[3,4-c]pyridin-7-ol Chemical compound OC1=C(C)N=CC2=COC=C21 NZOCLVWZHBNOKT-UHFFFAOYSA-N 0.000 description 1
- 206010002198 Anaphylactic reaction Diseases 0.000 description 1
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
- 229940125715 antihistaminic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- YVECRCZZSGAGOW-UHFFFAOYSA-N furo[3,4-c]pyridin-1-ol Chemical compound C1=NC=CC2=C(O)OC=C21 YVECRCZZSGAGOW-UHFFFAOYSA-N 0.000 description 1
- BIRWRIAEWIXFHT-UHFFFAOYSA-N furo[3,4-c]pyridin-7-ol Chemical compound OC1=CN=CC2=COC=C12 BIRWRIAEWIXFHT-UHFFFAOYSA-N 0.000 description 1
- GJVNMIQVQXYJCP-UHFFFAOYSA-N furo[3,4-c]pyridine Chemical compound C1=NC=CC2=[C]OC=C21 GJVNMIQVQXYJCP-UHFFFAOYSA-N 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- PPZMYIBUHIPZOS-UHFFFAOYSA-N histamine dihydrochloride Chemical compound Cl.Cl.NCCC1=CN=CN1 PPZMYIBUHIPZOS-UHFFFAOYSA-N 0.000 description 1
- 229960000645 histamine hydrochloride Drugs 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 210000005164 penile vein Anatomy 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 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 |
|---|---|
| NL8403318A true NL8403318A (nl) | 1985-06-17 |
Family
ID=10551897
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8403318A NL8403318A (nl) | 1983-11-17 | 1984-11-01 | Nieuwe 7-carboxymethoxy-furo-(3,4-c)-pyridinederivaten, hun bereiding en therapeutische preparaten die ze bevatten. |
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
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