PH27153A - Benzopyran derivatives - Google Patents

Benzopyran derivatives Download PDF

Info

Publication number: PH27153A
Authority: PH; Philippines
Prior art keywords: benzopyran; oxide; dimethyl; dihydro; pyridine
Prior art date: 1987-07-06

Application number

PH37176A

Other languages

English (en)

Inventor

Michael Richard Attwood

Philip Stephen Jones

Sally Redshaw

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

1987-07-06

Filing date

1988-07-06

Publication date

1993-04-02

1987-07-06 Priority claimed from GB878715839A external-priority patent/GB8715839D0/en

1988-07-06 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1993-04-02 Publication of PH27153A publication Critical patent/PH27153A/en

Links

150000001562 benzopyrans Chemical class 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 160
-1 nitrobenzoyl Chemical group 0.000 claims description 74
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims description 63
229910052739 hydrogen Inorganic materials 0.000 claims description 60
239000001257 hydrogen Substances 0.000 claims description 58
125000000217 alkyl group Chemical group 0.000 claims description 56
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
238000000034 method Methods 0.000 claims description 34
150000001204 N-oxides Chemical class 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 22
125000004093 cyano group Chemical group *C#N 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 20
229910052736 halogen Inorganic materials 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
125000000815 N-oxide group Chemical group 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 17
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 17
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 14
238000011282 treatment Methods 0.000 claims description 14
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 12
150000002431 hydrogen Chemical group 0.000 claims description 12
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
125000004414 alkyl thio group Chemical group 0.000 claims description 11
125000001589 carboacyl group Chemical group 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 7
239000000546 pharmaceutical excipient Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
230000002265 prevention Effects 0.000 claims description 7
206010002383 Angina Pectoris Diseases 0.000 claims description 6
206010007559 Cardiac failure congestive Diseases 0.000 claims description 6
206010019280 Heart failures Diseases 0.000 claims description 6
206010020772 Hypertension Diseases 0.000 claims description 6
208000029578 Muscle disease Diseases 0.000 claims description 6
208000021642 Muscular disease Diseases 0.000 claims description 6
230000002490 cerebral effect Effects 0.000 claims description 6
230000002093 peripheral effect Effects 0.000 claims description 6
210000002460 smooth muscle Anatomy 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
208000019553 vascular disease Diseases 0.000 claims description 6
OOKJTGMLXKUVOW-UHFFFAOYSA-N 2,2-dimethyl-4-pyrimidin-2-yl-3,4-dihydrochromene-6-carbonitrile Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C1=NC=CC=N1 OOKJTGMLXKUVOW-UHFFFAOYSA-N 0.000 claims description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
VJFKERVNQSGERR-UHFFFAOYSA-N 2,2-dimethyl-4-(4-methyl-1-oxidopyridin-1-ium-2-yl)chromene-6-carbonitrile Chemical compound CC1=CC=[N+]([O-])C(C=2C3=CC(=CC=C3OC(C)(C)C=2)C#N)=C1 VJFKERVNQSGERR-UHFFFAOYSA-N 0.000 claims description 3
VBUWHWHLKQVZNI-UHFFFAOYSA-N 2,2-dimethyl-4-pyrazin-2-yl-3,4-dihydrochromene-6-carbonitrile Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C1=CN=CC=N1 VBUWHWHLKQVZNI-UHFFFAOYSA-N 0.000 claims description 3
DVOHDQNIFVLXOL-UHFFFAOYSA-N 2-(2,2-dimethyl-6-methylsulfanyl-3,4-dihydrochromen-4-yl)-1-oxidopyridin-1-ium Chemical compound C12=CC(SC)=CC=C2OC(C)(C)CC1C1=CC=CC=[N+]1[O-] DVOHDQNIFVLXOL-UHFFFAOYSA-N 0.000 claims description 3
YNTSDNKWTDAYAT-UHFFFAOYSA-N 4-(2,2-dimethylchromen-4-yl)pyridin-3-ol Chemical compound C=1C(C)(C)OC2=CC=CC=C2C=1C1=CC=NC=C1O YNTSDNKWTDAYAT-UHFFFAOYSA-N 0.000 claims description 3
JDLRFGAYBSYNSO-UHFFFAOYSA-N 4-(5-hydroxy-1-oxidopyridin-1-ium-2-yl)-2,2-dimethylchromene-6-carbonitrile Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C1=CC=C(O)C=[N+]1[O-] JDLRFGAYBSYNSO-UHFFFAOYSA-N 0.000 claims description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
KIIGVFITJOATPV-UHFFFAOYSA-N 2,2-dimethyl-4-(1-oxido-5-phenylpyridin-1-ium-2-yl)chromene-6-carbonitrile Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C([N+](=C1)[O-])=CC=C1C1=CC=CC=C1 KIIGVFITJOATPV-UHFFFAOYSA-N 0.000 claims description 2
PQVILGHAVGQHRP-UHFFFAOYSA-N 2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)chromene-6-carbonitrile Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C1=CC=CC=[N+]1[O-] PQVILGHAVGQHRP-UHFFFAOYSA-N 0.000 claims description 2
SQPQBCKNVMBCEE-UHFFFAOYSA-N 2,2-dimethyl-4-[5-(4-methylphenyl)-1-oxidopyridin-1-ium-2-yl]chromene-6-carbonitrile Chemical compound C1=CC(C)=CC=C1C(C=[N+]1[O-])=CC=C1C1=CC(C)(C)OC2=CC=C(C#N)C=C12 SQPQBCKNVMBCEE-UHFFFAOYSA-N 0.000 claims description 2
SDUIPMRMROTXEI-UHFFFAOYSA-N 2-(2,2-dimethyl-6-nitro-3,4-dihydrochromen-4-yl)-1-oxidopyridin-1-ium Chemical compound C12=CC([N+]([O-])=O)=CC=C2OC(C)(C)CC1C1=CC=CC=[N+]1[O-] SDUIPMRMROTXEI-UHFFFAOYSA-N 0.000 claims description 2
VZONCHQVBLCHLM-UHFFFAOYSA-N 2-(6-bromo-2,2-dimethyl-3,4-dihydrochromen-4-yl)-1-oxidopyridin-1-ium Chemical compound C12=CC(Br)=CC=C2OC(C)(C)CC1C1=CC=CC=[N+]1[O-] VZONCHQVBLCHLM-UHFFFAOYSA-N 0.000 claims description 2
AYRYWZHUJGNCCF-UHFFFAOYSA-N 2-(6-bromo-2,2-dimethylchromen-4-yl)-1-oxidopyridin-1-ium Chemical compound C=1C(C)(C)OC2=CC=C(Br)C=C2C=1C1=CC=CC=[N+]1[O-] AYRYWZHUJGNCCF-UHFFFAOYSA-N 0.000 claims description 2
IZVIEWXJZOFDHI-UHFFFAOYSA-N 4-(5-chloro-1-oxidopyridin-1-ium-2-yl)-2,2-dimethyl-3,4-dihydrochromene-6-carbonitrile Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C1=CC=C(Cl)C=[N+]1[O-] IZVIEWXJZOFDHI-UHFFFAOYSA-N 0.000 claims description 2
HJCWJPIYOSBUJJ-UHFFFAOYSA-N 4-(5-cyano-2-hydroxyphenyl)-2,2-dimethylchromene-6-carbonitrile Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C1=CC(C#N)=CC=C1O HJCWJPIYOSBUJJ-UHFFFAOYSA-N 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims 2
WZFNSLZNUQFRHC-UHFFFAOYSA-N 1-[2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)chromen-6-yl]ethanone Chemical compound C12=CC(C(=O)C)=CC=C2OC(C)(C)C=C1C1=CC=CC=[N+]1[O-] WZFNSLZNUQFRHC-UHFFFAOYSA-N 0.000 claims 1
KZNFWTUXXSJNNN-UHFFFAOYSA-N 1-[2-methyl-4-(1-oxidopyridin-1-ium-2-yl)-2h-chromen-6-yl]ethanone Chemical compound C=1C(C)OC2=CC=C(C(C)=O)C=C2C=1C1=CC=CC=[N+]1[O-] KZNFWTUXXSJNNN-UHFFFAOYSA-N 0.000 claims 1
ZLHVCYUISHRODZ-UHFFFAOYSA-N 2,2-dimethyl-4-(1-oxido-5-phenylpyridin-1-ium-2-yl)-3,4-dihydrochromene-6-carbonitrile Chemical compound C12=CC(C#N)=CC=C2OC(C)(C)CC1C([N+](=C1)[O-])=CC=C1C1=CC=CC=C1 ZLHVCYUISHRODZ-UHFFFAOYSA-N 0.000 claims 1
BQEBAKFDIRCXSI-UHFFFAOYSA-N 2,2-dimethyl-4-(5-methyl-1-oxidopyridin-1-ium-2-yl)-3,4-dihydrochromene-6-carbonitrile Chemical compound [O-][N+]1=CC(C)=CC=C1C1C2=CC(C#N)=CC=C2OC(C)(C)C1 BQEBAKFDIRCXSI-UHFFFAOYSA-N 0.000 claims 1
NYWWLAGHUMTSBB-UHFFFAOYSA-N 2-methoxy-1-oxidopyridin-1-ium Chemical compound COC1=CC=CC=[N+]1[O-] NYWWLAGHUMTSBB-UHFFFAOYSA-N 0.000 claims 1
KHCVUHPZYJUXLC-UHFFFAOYSA-N 4-(2-hydroxyphenyl)-2,2-dimethylchromene-6-carbonitrile Chemical compound C=1C(C)(C)OC2=CC=C(C#N)C=C2C=1C1=CC=CC=C1O KHCVUHPZYJUXLC-UHFFFAOYSA-N 0.000 claims 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
YRSPCPACGOAQTP-UHFFFAOYSA-N [2,2-dimethyl-4-(1-oxidopyridin-1-ium-2-yl)-3,4-dihydrochromen-6-yl]-phenylmethanone Chemical compound C=1C=C2OC(C)(C)CC(C=3[N+](=CC=CC=3)[O-])C2=CC=1C(=O)C1=CC=CC=C1 YRSPCPACGOAQTP-UHFFFAOYSA-N 0.000 claims 1
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
125000003373 pyrazinyl group Chemical group 0.000 claims 1
125000000714 pyrimidinyl group Chemical group 0.000 claims 1
125000005493 quinolyl group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 516
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 252
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 194
239000000243 solution Substances 0.000 description 173
239000000203 mixture Substances 0.000 description 154
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 153
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 138
238000002844 melting Methods 0.000 description 99
230000008018 melting Effects 0.000 description 99
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 94
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 91
238000010828 elution Methods 0.000 description 91
239000000741 silica gel Substances 0.000 description 87
229910002027 silica gel Inorganic materials 0.000 description 87
229910052938 sodium sulfate Inorganic materials 0.000 description 77
235000011152 sodium sulphate Nutrition 0.000 description 77
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 74
239000007858 starting material Substances 0.000 description 71
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 69
239000012074 organic phase Substances 0.000 description 66
239000003208 petroleum Substances 0.000 description 59
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 55
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
239000007787 solid Substances 0.000 description 46
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 42
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 39
235000017557 sodium bicarbonate Nutrition 0.000 description 37
229910000030 sodium bicarbonate Inorganic materials 0.000 description 37
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
229960001407 sodium bicarbonate Drugs 0.000 description 36
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 32
238000010992 reflux Methods 0.000 description 32
238000003756 stirring Methods 0.000 description 32
239000003921 oil Substances 0.000 description 30
235000019198 oils Nutrition 0.000 description 30
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
238000001953 recrystallisation Methods 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
239000003960 organic solvent Substances 0.000 description 24
239000002904 solvent Substances 0.000 description 24
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 23
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 21
238000001704 evaporation Methods 0.000 description 21
230000008020 evaporation Effects 0.000 description 21
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 20
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 20
239000004289 sodium hydrogen sulphite Substances 0.000 description 20
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 20
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 18
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 17
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
229960004592 isopropanol Drugs 0.000 description 16
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
230000008569 process Effects 0.000 description 16
239000011780 sodium chloride Substances 0.000 description 16
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
238000000746 purification Methods 0.000 description 15
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000003054 catalyst Substances 0.000 description 14
239000000284 extract Substances 0.000 description 14
238000004519 manufacturing process Methods 0.000 description 14
239000000706 filtrate Substances 0.000 description 13
230000003647 oxidation Effects 0.000 description 13
238000007254 oxidation reaction Methods 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 12
238000010438 heat treatment Methods 0.000 description 12
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
239000012299 nitrogen atmosphere Substances 0.000 description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 10
229910052783 alkali metal Inorganic materials 0.000 description 10
125000004433 nitrogen atom Chemical group N* 0.000 description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
NXUSMKWUASVPPO-UHFFFAOYSA-N 2-(2,2-dimethyl-3,4-dihydrochromen-4-yl)pyridine Chemical compound C12=CC=CC=C2OC(C)(C)CC1C1=CC=CC=N1 NXUSMKWUASVPPO-UHFFFAOYSA-N 0.000 description 9
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
239000008346 aqueous phase Substances 0.000 description 9
125000003118 aryl group Chemical group 0.000 description 9
239000012298 atmosphere Substances 0.000 description 9
235000011167 hydrochloric acid Nutrition 0.000 description 9
229960000443 hydrochloric acid Drugs 0.000 description 9
239000012312 sodium hydride Substances 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 8
239000002585 base Substances 0.000 description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 8
235000019253 formic acid Nutrition 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
150000001340 alkali metals Chemical class 0.000 description 7
229960001701 chloroform Drugs 0.000 description 7
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
BJBUSSBIFHSXBR-UHFFFAOYSA-N 4-(2-methylbut-3-yn-2-yloxy)benzonitrile Chemical compound C#CC(C)(C)OC1=CC=C(C#N)C=C1 BJBUSSBIFHSXBR-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
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CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 4
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YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
235000013681 dietary sucrose Nutrition 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 1
WZXCIFKOMSLSHM-UHFFFAOYSA-N ethyl 2-methyl-2-(4-methylphenyl)sulfanylpropanoate Chemical compound CCOC(=O)C(C)(C)SC1=CC=C(C)C=C1 WZXCIFKOMSLSHM-UHFFFAOYSA-N 0.000 description 1
IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229960001031 glucose Drugs 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
208000024963 hair loss Diseases 0.000 description 1
230000003676 hair loss Effects 0.000 description 1
125000006331 halo benzoyl group Chemical group 0.000 description 1
230000002140 halogenating effect Effects 0.000 description 1
230000002440 hepatic effect Effects 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000008011 inorganic excipient Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
208000002551 irritable bowel syndrome Diseases 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000011968 lewis acid catalyst Substances 0.000 description 1
AHNJTQYTRPXLLG-UHFFFAOYSA-N lithium;diethylazanide Chemical compound [Li+].CC[N-]CC AHNJTQYTRPXLLG-UHFFFAOYSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
PRDBTKCIWKBMCD-UHFFFAOYSA-N methyl 2,2-dimethyl-4-pyridin-2-yl-3,4-dihydrochromene-6-carboxylate Chemical compound C12=CC(C(=O)OC)=CC=C2OC(C)(C)CC1C1=CC=CC=N1 PRDBTKCIWKBMCD-UHFFFAOYSA-N 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
125000006606 n-butoxy group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
IOVCWXUNBOPUCH-UHFFFAOYSA-O nitrosooxidanium Chemical compound [OH2+]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-O 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
239000008012 organic excipient Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000003444 phase transfer catalyst Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
CFZKDDTWZYUZKS-UHFFFAOYSA-N picoline N-oxide Chemical compound CC1=CC=CC=[N+]1[O-] CFZKDDTWZYUZKS-UHFFFAOYSA-N 0.000 description 1
210000003240 portal vein Anatomy 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
CDZWVGRGLGHQIQ-UHFFFAOYSA-N pyridin-3-yl n,n-diethylcarbamate Chemical compound CCN(CC)C(=O)OC1=CC=CN=C1 CDZWVGRGLGHQIQ-UHFFFAOYSA-N 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000009466 transformation Effects 0.000 description 1
BTMMIGGFWWXPEE-UHFFFAOYSA-N trimethyl-(4-methylphenyl)stannane Chemical compound CC1=CC=C([Sn](C)(C)C)C=C1 BTMMIGGFWWXPEE-UHFFFAOYSA-N 0.000 description 1
BJAARRARQJZURR-UHFFFAOYSA-N trimethylazanium;hydroxide Chemical compound O.CN(C)C BJAARRARQJZURR-UHFFFAOYSA-N 0.000 description 1
210000001635 urinary tract Anatomy 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrane Compounds (AREA)

PH37176A 1987-07-06 1988-07-06 Benzopyran derivatives PH27153A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB878715839A GB8715839D0 (en)	1987-07-06	1987-07-06	Benzopyran derivatives
GB888810212A GB8810212D0 (en)	1987-07-06	1988-04-29	Benzopyran derivatives

Publications (1)

Publication Number	Publication Date
PH27153A true PH27153A (en)	1993-04-02

Family

ID=26292440

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH37176A PH27153A (en)	1987-07-06	1988-07-06	Benzopyran derivatives

Country Status (27)

Country	Link
US (2)	US4971982A (pt)
EP (1)	EP0298452B1 (pt)
JP (1)	JP2683581B2 (pt)
CN (1)	CN1023404C (pt)
AR (1)	AR245710A1 (pt)
AT (1)	ATE91127T1 (pt)
AU (1)	AU613646B2 (pt)
CA (1)	CA1334094C (pt)
CZ (1)	CZ285970B6 (pt)
DE (1)	DE3882095D1 (pt)
DK (1)	DK370988A (pt)
DZ (1)	DZ1227A1 (pt)
ES (1)	ES2056859T3 (pt)
FI (1)	FI90079C (pt)
HU (2)	HU202513B (pt)
IE (1)	IE62258B1 (pt)
IL (1)	IL86923A (pt)
IS (1)	IS1596B (pt)
MC (1)	MC1953A1 (pt)
MX (1)	MX174083B (pt)
NO (1)	NO170727C (pt)
NZ (1)	NZ225163A (pt)
PH (1)	PH27153A (pt)
PT (1)	PT87913B (pt)
SK (1)	SK484188A3 (pt)
SU (1)	SU1757466A3 (pt)
YU (1)	YU46918B (pt)

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DE3918041A1 (de) *	1989-06-02	1990-12-06	Merck Patent Gmbh	Chromanderivate
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CA2061179A1 (en) *	1991-02-18	1992-08-19	Ryuji Tsuzuki	Oxzazinobenzazole compounds
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US5470861A (en) *	1994-08-04	1995-11-28	Hoffmann-La Roche Inc.	Method of promoting hair growth
US5629429A (en) *	1995-06-07	1997-05-13	Bristol-Myers Squibb Company	Process for preparing 4-arylamino-benzopyran and related compounds
US5869478A (en) *	1995-06-07	1999-02-09	Bristol-Myers Squibb Company	Sulfonamido substituted benzopyran derivatives
US5612323A (en) *	1995-06-07	1997-03-18	Bristol-Myers Squibb Company	Phosphinic ester substituted benzopyran derivatives
US5612370A (en) *	1995-06-07	1997-03-18	Bristol-Myers Squibb Company	Phenylglycine and phenylalaninen amido benzopyran derivatives
KR100691511B1 (ko) *	1995-11-09	2007-04-19	다우 아그로사이언시즈 엘엘씨	크로만카복실레이트의제조방법
JP3885900B2 (ja) *	1996-03-22	2007-02-28	大日本インキ化学工業株式会社	ベンゾピラン誘導体及びそれを有効成分とする心臓疾患治療剤
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US7045519B2 (en)	1998-06-19	2006-05-16	Chiron Corporation	Inhibitors of glycogen synthase kinase 3
EP1087963B1 (en)	1998-06-19	2004-08-25	Chiron Corporation	Inhibitors of glycogen synthase kinase 3
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1988
- 1988-06-23 US US07/210,692 patent/US4971982A/en not_active Expired - Fee Related
- 1988-06-24 NZ NZ225163A patent/NZ225163A/en unknown
- 1988-06-30 AU AU18556/88A patent/AU613646B2/en not_active Ceased
- 1988-06-30 IL IL8692388A patent/IL86923A/en not_active IP Right Cessation
- 1988-07-03 DZ DZ880098A patent/DZ1227A1/fr active
- 1988-07-04 MC MC881987A patent/MC1953A1/xx unknown
- 1988-07-04 DK DK370988A patent/DK370988A/da not_active Application Discontinuation
- 1988-07-04 AR AR88311317A patent/AR245710A1/es active
- 1988-07-04 SK SK4841-88A patent/SK484188A3/sk unknown
- 1988-07-04 HU HU883471A patent/HU202513B/hu not_active IP Right Cessation
- 1988-07-04 CZ CS884841A patent/CZ285970B6/cs not_active IP Right Cessation
- 1988-07-05 NO NO883007A patent/NO170727C/no not_active IP Right Cessation
- 1988-07-05 JP JP63166068A patent/JP2683581B2/ja not_active Expired - Lifetime
- 1988-07-05 CA CA000571115A patent/CA1334094C/en not_active Expired - Fee Related
- 1988-07-05 IE IE204388A patent/IE62258B1/en not_active IP Right Cessation
- 1988-07-05 CN CN88104200A patent/CN1023404C/zh not_active Expired - Fee Related
- 1988-07-05 SU SU884356220A patent/SU1757466A3/ru active
- 1988-07-05 PT PT87913A patent/PT87913B/pt not_active IP Right Cessation
- 1988-07-05 IS IS3369A patent/IS1596B/is unknown
- 1988-07-05 YU YU130288A patent/YU46918B/sh unknown
- 1988-07-05 MX MX1216888A patent/MX174083B/es unknown
- 1988-07-06 FI FI883232A patent/FI90079C/fi not_active IP Right Cessation
- 1988-07-06 EP EP88110789A patent/EP0298452B1/de not_active Expired - Lifetime
- 1988-07-06 PH PH37176A patent/PH27153A/en unknown
- 1988-07-06 AT AT88110789T patent/ATE91127T1/de not_active IP Right Cessation
- 1988-07-06 DE DE8888110789T patent/DE3882095D1/de not_active Expired - Fee Related
- 1988-07-06 ES ES88110789T patent/ES2056859T3/es not_active Expired - Lifetime
1990
- 1990-09-11 US US07/580,881 patent/US5118694A/en not_active Expired - Fee Related
1995
- 1995-06-19 HU HU95P/P00257P patent/HU211870A9/hu unknown

Also Published As

Publication number	Publication date
DK370988D0 (da)	1988-07-04
EP0298452A2 (de)	1989-01-11
JP2683581B2 (ja)	1997-12-03
AU613646B2 (en)	1991-08-08
SK279037B6 (sk)	1998-05-06
IL86923A (en)	1994-02-27
IE62258B1 (en)	1995-01-11
NO170727B (no)	1992-08-17
ES2056859T3 (es)	1994-10-16
YU130288A (en)	1990-06-30
FI883232A0 (fi)	1988-07-06
FI90079B (fi)	1993-09-15
NO883007L (no)	1989-01-09
CZ285970B6 (cs)	1999-12-15
JPS6438087A (en)	1989-02-08
NZ225163A (en)	1991-04-26
YU46918B (sh)	1994-06-24
EP0298452B1 (de)	1993-06-30
IL86923A0 (en)	1988-11-30
AU1855688A (en)	1989-01-12
US5118694A (en)	1992-06-02
NO170727C (no)	1992-11-25
SK484188A3 (en)	1998-05-06
PT87913A (pt)	1989-06-30
HU202513B (en)	1991-03-28
DE3882095D1 (de)	1993-08-05
IE882043L (en)	1989-01-06
EP0298452A3 (en)	1989-04-05
HU211870A9 (en)	1995-12-28
FI90079C (fi)	1993-12-27
MX12168A (es)	1993-10-01
SU1757466A3 (ru)	1992-08-23
CN1023404C (zh)	1994-01-05
NO883007D0 (no)	1988-07-05
PT87913B (pt)	1995-03-01
FI883232A (fi)	1989-01-07
DZ1227A1 (fr)	2004-09-13
CN1030582A (zh)	1989-01-25
CA1334094C (en)	1995-01-24
HUT50152A (en)	1989-12-28
MC1953A1 (fr)	1989-06-30
US4971982A (en)	1990-11-20
MX174083B (es)	1994-04-20
DK370988A (da)	1989-01-07
AR245710A1 (es)	1994-02-28
ATE91127T1 (de)	1993-07-15
IS3369A7 (is)	1989-01-07
IS1596B (is)	1996-04-12
CZ484188A3 (cs)	1999-10-13

Publication	Publication Date	Title
PH27153A (en)	1993-04-02	Benzopyran derivatives
US5998451A (en)	1999-12-07	Substituted tetralins, chromans and related compounds in the treatment and related compounds in the treatment of asthma, arthritis and related diseases
EP0420511B1 (en)	1994-08-17	Heterocyclic derivatives
US20080280891A1 (en)	2008-11-13	Anti-cancer agents and uses thereof
CS203970B2 (en)	1981-03-31	Method of producing novel heterocyclyl-oxy-hydroxy-amino-propanes
EP0385663B1 (en)	1995-12-06	Heterocyclic cycloalkanes as inhibitors of 5-lipoxygenase
KR19990067377A (ko)	1999-08-16	치환비닐피리딘유도체및이를함유하는의약
EP0381375A1 (en)	1990-08-08	Heterocyclic derivatives
US5350754A (en)	1994-09-27	Heterocyclic cycloalkanes
EP0385680A2 (en)	1990-09-05	Heterocyclic ethers as 5-lipoxygenase inhibitors
HU217812B (hu)	2000-04-28	Kromán-származékok, a vegyületeket hatóanyagként tartalmazó gyógyszerkészítmények és eljárás előállításukra
IE53005B1 (en)	1988-05-11	Process for preparing substituted pyrimidinones and intermediates therefor
US5045550A (en)	1991-09-03	Substituted tetrahydropyridines as central nervous system agents
KR960012213B1 (ko)	1996-09-16	벤조피란 유도체, 이의 제조방법 및 이를 함유하는 약제
US5734059A (en)	1998-03-31	Production intermediate and process for producing pyridine derivative
EP0586405B1 (de)	1997-09-10	NEUE IN 4-STELLUNG DURCH ARYL ODER N-HETEROARYL SUBSTITUIERTE 2H-BENZO[b]PYRAN-DERIVATE, VERFAHREN ZU IHRER HERSTELLUNG UND IHRE VERWENDUNG SOWIE DIE VERBINDUNGEN ENTHALTENDE ZUBEREITUNGEN
CA1166254A (en)	1984-04-24	4-substituted-6-(pyridinyl)-3(2h)-pyridazinones, preparation and cardiotonic use
Usui et al.	1994	SYNTHESIS AND BIOLOGICAL ACTIVITIES OF NEW HMG-COA SYNTHASE INHIBITORS: 2-OXETANONES WITH A SIDE CHAIN CONTAINING BIPHENYL, TERPHENYL OR PHENYLPYIUDINE
CA1166255A (en)	1984-04-24	4,5-dihydro-2-substituted-6-(pyridinyl)-3(2h)- pyridazinones, preparation and cardiotonic use thereof
NO834436L (no)	1984-06-04	Fremgangsmaate for fremstilling av terapeutisk aktive pyridon-derivater
KR20050112948A (ko)	2005-12-01	1ｈ-피리딘-2-온 유도체
GB2076807A (en)	1981-12-09	4,5-Dihydro-6(pyridinyl)-3(2H)- pyridazinones