SE460903B - Nya 6-substituerade furo-(3,4-c)-pyridinderivat, saett foer deras framstaellning och terapeutiska kompositioner, innehaallande foereningarna - Google Patents
Nya 6-substituerade furo-(3,4-c)-pyridinderivat, saett foer deras framstaellning och terapeutiska kompositioner, innehaallande foereningarnaInfo
- Publication number
- SE460903B SE460903B SE8500460A SE8500460A SE460903B SE 460903 B SE460903 B SE 460903B SE 8500460 A SE8500460 A SE 8500460A SE 8500460 A SE8500460 A SE 8500460A SE 460903 B SE460903 B SE 460903B
- Authority
- SE
- Sweden
- Prior art keywords
- furo
- group
- hydroxy
- carbon atoms
- dihydro
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 10
- -1 6-SUBSTITUTED FURO- (3,4-C) PYRIDINE Chemical class 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 4
- 230000001225 therapeutic effect Effects 0.000 title claims description 3
- 239000000126 substance Substances 0.000 title 1
- 238000000034 method Methods 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- AVZNLXBMQVKETP-UHFFFAOYSA-M [Br-].CN(C)CC([Mg+])=C Chemical compound [Br-].CN(C)CC([Mg+])=C AVZNLXBMQVKETP-UHFFFAOYSA-M 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 239000000047 product Substances 0.000 description 22
- 238000000354 decomposition reaction Methods 0.000 description 13
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 11
- 229960000317 yohimbine Drugs 0.000 description 11
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 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 3
- 208000009132 Catalepsy Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 206010047853 Waxy flexibility Diseases 0.000 description 3
- 230000008485 antagonism Effects 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229960003878 haloperidol Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 2
- 229960004801 imipramine Drugs 0.000 description 2
- 229940090044 injection Drugs 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- QSLMDECMDJKHMQ-GSXCWMCISA-N maprotiline Chemical compound C12=CC=CC=C2[C@@]2(CCCNC)C3=CC=CC=C3[C@@H]1CC2 QSLMDECMDJKHMQ-GSXCWMCISA-N 0.000 description 2
- 229960004090 maprotiline Drugs 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- XXZCIYUJYUESMD-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(morpholin-4-ylmethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCOCC1 XXZCIYUJYUESMD-UHFFFAOYSA-N 0.000 description 1
- IFJZVCLSQSAWGK-UHFFFAOYSA-N 3-(4-fluorophenyl)-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound C1=CC(F)=CC=C1C1C(C=NC(C=O)=C2OCC=3C=CC=CC=3)=C2CO1 IFJZVCLSQSAWGK-UHFFFAOYSA-N 0.000 description 1
- JIKJILFVLFMUCI-UHFFFAOYSA-N 3-(4-methoxyphenyl)-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound C1=CC(OC)=CC=C1C1C(C=NC(C=O)=C2OCC=3C=CC=CC=3)=C2CO1 JIKJILFVLFMUCI-UHFFFAOYSA-N 0.000 description 1
- USTNIIZBJYORCP-UHFFFAOYSA-N 3-(4-methylphenyl)-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound C1=CC(C)=CC=C1C1C(C=NC(C=O)=C2OCC=3C=CC=CC=3)=C2CO1 USTNIIZBJYORCP-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- HMBHHFXXQSIBOD-UHFFFAOYSA-N 3-cyclohexyl-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound O=CC1=NC=C2C(C3CCCCC3)OCC2=C1OCC1=CC=CC=C1 HMBHHFXXQSIBOD-UHFFFAOYSA-N 0.000 description 1
- MPMVOFSNRBUECK-UHFFFAOYSA-N 3-methyl-3-pentyl-7-phenylmethoxy-1h-furo[3,4-c]pyridine-6-carbaldehyde Chemical compound CCCCCC1(C)OCC2=C1C=NC(C=O)=C2OCC1=CC=CC=C1 MPMVOFSNRBUECK-UHFFFAOYSA-N 0.000 description 1
- XEBTVOMLXWHIGD-UHFFFAOYSA-N 3-methyl-3-phenyl-7-phenylmethoxy-1h-furo[3,4-c]pyridine-6-carbaldehyde Chemical compound C=1C=CC=CC=1C1(C)OCC2=C1C=NC(C=O)=C2OCC1=CC=CC=C1 XEBTVOMLXWHIGD-UHFFFAOYSA-N 0.000 description 1
- SCQIMPRIQLPLOK-UHFFFAOYSA-N 3-methyl-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound CC1OCC2=C1C=NC(C=O)=C2OCC1=CC=CC=C1 SCQIMPRIQLPLOK-UHFFFAOYSA-N 0.000 description 1
- ICHFFBICRZKEFR-UHFFFAOYSA-N 3-phenyl-7-phenylmethoxy-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound O=CC1=NC=C2C(C=3C=CC=CC=3)OCC2=C1OCC1=CC=CC=C1 ICHFFBICRZKEFR-UHFFFAOYSA-N 0.000 description 1
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 1
- 229940000681 5-hydroxytryptophan Drugs 0.000 description 1
- HGFPAHJKZGSJSA-UHFFFAOYSA-N 7-phenylmethoxy-3-propyl-1,3-dihydrofuro[3,4-c]pyridine-6-carbaldehyde Chemical compound CCCC1OCC2=C1C=NC(C=O)=C2OCC1=CC=CC=C1 HGFPAHJKZGSJSA-UHFFFAOYSA-N 0.000 description 1
- ZHOAIFGYDPORCW-UHFFFAOYSA-N 7-phenylmethoxyfuro[3,4-c]pyridine-6-carbaldehyde Chemical class O=CC=1N=CC2=COC=C2C=1OCC1=CC=CC=C1 ZHOAIFGYDPORCW-UHFFFAOYSA-N 0.000 description 1
- 206010024264 Lethargy Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 229920005372 Plexiglas® Polymers 0.000 description 1
- BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000006264 debenzylation reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000002896 effect on catalepsy Effects 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229940047551 haloperidol injection Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 206010025482 malaise Diseases 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- WAEXFXRVDQXREF-UHFFFAOYSA-N vorinostat Chemical compound ONC(=O)CCCCCCC(=O)NC1=CC=CC=C1 WAEXFXRVDQXREF-UHFFFAOYSA-N 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848402740A GB8402740D0 (en) | 1984-02-02 | 1984-02-02 | Furo-(3 4-c)-pyridine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE460903B true SE460903B (sv) | 1989-12-04 |
Family
ID=10555953
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8500460A SE460903B (sv) | 1984-02-02 | 1985-02-01 | Nya 6-substituerade furo-(3,4-c)-pyridinderivat, saett foer deras framstaellning och terapeutiska kompositioner, innehaallande foereningarna |
| SE8500460D SE8500460L (sv) | 1984-02-02 | 1985-02-01 | Nya 6-substituerade furo-(3,4-c)-pyridin-derivat, sett for deras framstellning och terapeutiska kompositioner, innehallande foreningarna |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE8500460D SE8500460L (sv) | 1984-02-02 | 1985-02-01 | Nya 6-substituerade furo-(3,4-c)-pyridin-derivat, sett for deras framstellning och terapeutiska kompositioner, innehallande foreningarna |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4581362A (en, 2012) |
| JP (1) | JPS60181088A (en, 2012) |
| AT (1) | AT391700B (en, 2012) |
| BE (1) | BE901545A (en, 2012) |
| CA (1) | CA1300148C (en, 2012) |
| CH (1) | CH663023A5 (en, 2012) |
| DE (1) | DE3503435A1 (en, 2012) |
| DK (1) | DK158951C (en, 2012) |
| DZ (1) | DZ743A1 (en, 2012) |
| ES (1) | ES8607308A1 (en, 2012) |
| FI (1) | FI82051C (en, 2012) |
| FR (2) | FR2559062B1 (en, 2012) |
| GB (1) | GB8402740D0 (en, 2012) |
| HK (1) | HK92587A (en, 2012) |
| IE (1) | IE58229B1 (en, 2012) |
| IT (1) | IT1200587B (en, 2012) |
| LU (1) | LU85744A1 (en, 2012) |
| MA (1) | MA20342A1 (en, 2012) |
| NL (1) | NL8500241A (en, 2012) |
| NO (1) | NO160369C (en, 2012) |
| OA (1) | OA07947A (en, 2012) |
| PT (1) | PT79913B (en, 2012) |
| SE (2) | SE460903B (en, 2012) |
| ZA (1) | ZA85508B (en, 2012) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8427218D0 (en) * | 1984-10-27 | 1984-12-05 | Scras | 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 |
| JPH054664A (ja) * | 1991-06-21 | 1993-01-14 | Yoozuri:Kk | 運搬等用の包装体及び包装方法 |
| WO2013102145A1 (en) | 2011-12-28 | 2013-07-04 | Global Blood Therapeutics, Inc. | Substituted heteroaryl aldehyde compounds and methods for their use in increasing tissue oxygenation |
| SI3141542T1 (sl) | 2011-12-28 | 2020-11-30 | Global Blood Therapeutics, Inc. | Substituirane spojine benzaldehida in metode njihove uporabe pri povečanju oksigenacije tkiva |
| US9802900B2 (en) | 2013-03-15 | 2017-10-31 | Global Blood Therapeutics, Inc. | Bicyclic heteroaryl compounds and uses thereof for the modulation of hemoglobin |
| US10266551B2 (en) | 2013-03-15 | 2019-04-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9458139B2 (en) | 2013-03-15 | 2016-10-04 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US9422279B2 (en) | 2013-03-15 | 2016-08-23 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| ES2852054T3 (es) | 2013-03-15 | 2021-09-10 | Global Blood Therapeutics Inc | Compuestos y usos de los mismos para la modulación de hemoglobina |
| US8952171B2 (en) | 2013-03-15 | 2015-02-10 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| WO2014145040A1 (en) | 2013-03-15 | 2014-09-18 | Global Blood Therapeutics, Inc. | Substituted aldehyde compounds and methods for their use in increasing tissue oxygenation |
| US9604999B2 (en) | 2013-03-15 | 2017-03-28 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| EP2970308B1 (en) | 2013-03-15 | 2021-07-14 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| US20140274961A1 (en) | 2013-03-15 | 2014-09-18 | Global Blood Therapeutics, Inc. | Compounds and uses thereof for the modulation of hemoglobin |
| AP2015008718A0 (en) | 2013-03-15 | 2015-09-30 | Global Blood Therapeutics Inc | Compounds and uses thereof for the modulation of hemoglobin |
| EA202092627A1 (ru) | 2013-11-18 | 2021-09-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
| CN105431147A (zh) | 2014-02-07 | 2016-03-23 | 全球血液疗法股份有限公司 | 2-羟基-6-((2-(1-异丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)苯甲醛的游离碱的结晶多晶型物 |
| MA41841A (fr) | 2015-03-30 | 2018-02-06 | Global Blood Therapeutics Inc | Composés aldéhyde pour le traitement de la fibrose pulmonaire, de l'hypoxie, et de maladies auto-immunes et des tissus conjonctifs |
| WO2017096230A1 (en) | 2015-12-04 | 2017-06-08 | Global Blood Therapeutics, Inc. | Dosing regimens for 2-hydroxy-6-((2-(1-isopropyl-1h-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde |
| TWI752307B (zh) | 2016-05-12 | 2022-01-11 | 美商全球血液治療公司 | 新穎化合物及製造化合物之方法 |
| TWI778983B (zh) | 2016-10-12 | 2022-10-01 | 美商全球血液治療公司 | 包含2-羥基-6-((2-(1-異丙基-1h-吡唑-5-基)吡啶-3-基)甲氧基)-苯甲醛之片劑 |
| ES2966707T3 (es) | 2018-10-01 | 2024-04-23 | Global Blood Therapeutics Inc | Moduladores de la hemoglobina para el tratamiento de la drepanocitosis |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA786269B (en) * | 1977-11-25 | 1979-10-31 | Scras | New pyridine derivative,its preparation and use |
| IN156817B (en, 2012) * | 1981-02-10 | 1985-11-09 | Scras | |
| GB8330517D0 (en) * | 1983-11-16 | 1983-12-21 | Scras | 6-vinyl-furo-(3,4-c)pyridine derivatives |
| GB8330658D0 (en) * | 1983-11-17 | 1983-12-29 | Scras | 7-carboxymethoxy-furo-(3,4-c)-pyridine derivatives |
-
1984
- 1984-02-02 GB GB848402740A patent/GB8402740D0/en active Pending
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1985
- 1985-01-22 ZA ZA85508A patent/ZA85508B/xx unknown
- 1985-01-22 BE BE0/214370A patent/BE901545A/fr not_active IP Right Cessation
- 1985-01-22 FI FI850275A patent/FI82051C/fi not_active IP Right Cessation
- 1985-01-23 US US06/693,715 patent/US4581362A/en not_active Expired - Lifetime
- 1985-01-24 CH CH312/85A patent/CH663023A5/fr not_active IP Right Cessation
- 1985-01-25 LU LU85744A patent/LU85744A1/fr unknown
- 1985-01-26 DZ DZ850024A patent/DZ743A1/fr active
- 1985-01-29 NL NL8500241A patent/NL8500241A/nl not_active Application Discontinuation
- 1985-01-31 AT AT0027585A patent/AT391700B/de not_active IP Right Cessation
- 1985-01-31 OA OA58520A patent/OA07947A/xx unknown
- 1985-01-31 CA CA000473302A patent/CA1300148C/en not_active Expired - Lifetime
- 1985-02-01 IE IE24185A patent/IE58229B1/en not_active IP Right Cessation
- 1985-02-01 DK DK045585A patent/DK158951C/da not_active IP Right Cessation
- 1985-02-01 NO NO850399A patent/NO160369C/no unknown
- 1985-02-01 JP JP60016713A patent/JPS60181088A/ja active Granted
- 1985-02-01 PT PT79913A patent/PT79913B/pt not_active IP Right Cessation
- 1985-02-01 ES ES540080A patent/ES8607308A1/es not_active Expired
- 1985-02-01 SE SE8500460A patent/SE460903B/sv not_active IP Right Cessation
- 1985-02-01 FR FR8501402A patent/FR2559062B1/fr not_active Expired
- 1985-02-01 SE SE8500460D patent/SE8500460L/xx not_active Application Discontinuation
- 1985-02-01 FR FR8501401A patent/FR2559152B1/fr not_active Expired
- 1985-02-01 IT IT19327/85A patent/IT1200587B/it active
- 1985-02-01 MA MA20566A patent/MA20342A1/fr unknown
- 1985-02-01 DE DE19853503435 patent/DE3503435A1/de active Granted
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1987
- 1987-12-03 HK HK925/87A patent/HK92587A/xx not_active IP Right Cessation
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