NL7908868A - Gesubstitueerde furopyridinonen en furopyrazinonen. - Google Patents

Gesubstitueerde furopyridinonen en furopyrazinonen. Download PDF

Info

Publication number: NL7908868A
Authority: NL; Netherlands
Prior art keywords: pyridine; furo; group; formula; phenyl
Prior art date: 1978-12-11

Application number

NL7908868A

Other languages

English (en)

Dutch (nl)

Original Assignee

Sterling Drug Inc

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.)

1978-12-11

Filing date

1979-12-10

Publication date

1980-06-13

1978-12-11 Priority claimed from US05/968,082 external-priority patent/US4211872A/en

1979-06-14 Priority claimed from US06/048,534 external-priority patent/US4243250A/en

1979-12-10 Application filed by Sterling Drug Inc filed Critical Sterling Drug Inc

1980-06-13 Publication of NL7908868A publication Critical patent/NL7908868A/nl

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WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 118
239000000203 mixture Substances 0.000 claims description 87
-1 diphenylamino Chemical group 0.000 claims description 58
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 51
239000002253 acid Substances 0.000 claims description 40
238000000034 method Methods 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 36
150000001875 compounds Chemical class 0.000 claims description 34
238000006243 chemical reaction Methods 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 25
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 16
239000000463 material Substances 0.000 claims description 16
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000005266 diarylamine group Chemical group 0.000 claims description 15
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 12
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 9
150000008064 anhydrides Chemical class 0.000 claims description 9
239000004202 carbamide Substances 0.000 claims description 9
239000003094 microcapsule Substances 0.000 claims description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
150000007530 organic bases Chemical class 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
CONPTSNKVLMTKN-UHFFFAOYSA-N 5-[4-(diethylamino)-2-methylphenyl]-5-(4-octyl-n-(4-octylphenyl)anilino)furo[3,4-b]pyridin-7-one Chemical compound C1=CC(CCCCCCCC)=CC=C1N(C1(C2=CC=CN=C2C(=O)O1)C=1C(=CC(=CC=1)N(CC)CC)C)C1=CC=C(CCCCCCCC)C=C1 CONPTSNKVLMTKN-UHFFFAOYSA-N 0.000 claims description 3
DFADXROPGFEYQO-UHFFFAOYSA-N 5-[4-(dimethylamino)phenyl]-5-(n-phenylanilino)furo[3,4-b]pyridin-7-one Chemical compound C1=CC(N(C)C)=CC=C1C1(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C2=CC=CN=C2C(=O)O1 DFADXROPGFEYQO-UHFFFAOYSA-N 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 3
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 3
FXYZUEIKGNOPJZ-UHFFFAOYSA-N 5-(1-ethyl-2-methylindol-3-yl)-5-(4-octyl-n-(4-octylphenyl)anilino)furo[3,4-b]pyridin-7-one Chemical compound C1=CC(CCCCCCCC)=CC=C1N(C1(C2=CC=CN=C2C(=O)O1)C=1C2=CC=CC=C2N(CC)C=1C)C1=CC=C(CCCCCCCC)C=C1 FXYZUEIKGNOPJZ-UHFFFAOYSA-N 0.000 claims description 2
JNNWUOOUVVLIEN-UHFFFAOYSA-N 5-(1-ethyl-2-methylindol-3-yl)-5-(n-phenylanilino)furo[3,4-b]pyridin-7-one Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C1(C2=CC=CN=C2C(=O)O1)N(C=1C=CC=CC=1)C1=CC=CC=C1 JNNWUOOUVVLIEN-UHFFFAOYSA-N 0.000 claims description 2
ZRDSFLUWAOLMLJ-UHFFFAOYSA-N 5-[4-(dimethylamino)phenyl]-5-(4-octyl-n-(4-octylphenyl)anilino)furo[3,4-b]pyridin-7-one Chemical compound C1=CC(CCCCCCCC)=CC=C1N(C1(C2=CC=CN=C2C(=O)O1)C=1C=CC(=CC=1)N(C)C)C1=CC=C(CCCCCCCC)C=C1 ZRDSFLUWAOLMLJ-UHFFFAOYSA-N 0.000 claims description 2
VNFSWLNUTFYSSU-UHFFFAOYSA-N 7-(1-ethyl-2-methylindol-3-yl)-7-(4-octyl-n-(4-octylphenyl)anilino)furo[3,4-b]pyridin-5-one Chemical compound C1=CC(CCCCCCCC)=CC=C1N(C1(C2=NC=CC=C2C(=O)O1)C=1C2=CC=CC=C2N(CC)C=1C)C1=CC=C(CCCCCCCC)C=C1 VNFSWLNUTFYSSU-UHFFFAOYSA-N 0.000 claims description 2
HKKHHCKIYKZAQI-UHFFFAOYSA-N 7-[4-(diethylamino)-2-methylphenyl]-7-(4-octyl-n-(4-octylphenyl)anilino)furo[3,4-b]pyridin-5-one Chemical compound C1=CC(CCCCCCCC)=CC=C1N(C1(C2=NC=CC=C2C(=O)O1)C=1C(=CC(=CC=1)N(CC)CC)C)C1=CC=C(CCCCCCCC)C=C1 HKKHHCKIYKZAQI-UHFFFAOYSA-N 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
239000006193 liquid solution Substances 0.000 claims description 2
150000007522 mineralic acids Chemical class 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
229910052739 hydrogen Inorganic materials 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 129
239000000047 product Substances 0.000 description 66
239000000243 solution Substances 0.000 description 44
239000004927 clay Substances 0.000 description 39
239000005011 phenolic resin Substances 0.000 description 39
229920001568 phenolic resin Polymers 0.000 description 39
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 38
239000007787 solid Substances 0.000 description 35
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 22
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
229940035422 diphenylamine Drugs 0.000 description 11
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 11
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 10
238000000354 decomposition reaction Methods 0.000 description 10
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
229920006395 saturated elastomer Polymers 0.000 description 10
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
QAPVYZRWKDXNDK-UHFFFAOYSA-N P,P-Dioctyldiphenylamine Chemical compound C1=CC(CCCCCCCC)=CC=C1NC1=CC=C(CCCCCCCC)C=C1 QAPVYZRWKDXNDK-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000000908 ammonium hydroxide Substances 0.000 description 9
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
230000002378 acidificating effect Effects 0.000 description 7
238000003756 stirring Methods 0.000 description 7
HGLISOFZJUBYPD-UHFFFAOYSA-N 2-(1-ethyl-2-methylindole-3-carbonyl)pyridine-3-carboxylic acid Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C(=O)C1=NC=CC=C1C(O)=O HGLISOFZJUBYPD-UHFFFAOYSA-N 0.000 description 6
YSJHADWSLVFGGT-UHFFFAOYSA-N 7h-furo[3,4-b]pyridin-5-one Chemical compound C1=CC=C2C(=O)OCC2=N1 YSJHADWSLVFGGT-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
239000004372 Polyvinyl alcohol Substances 0.000 description 6
229960003512 nicotinic acid Drugs 0.000 description 6
239000011664 nicotinic acid Substances 0.000 description 6
229920002451 polyvinyl alcohol Polymers 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
238000007796 conventional method Methods 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 5
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
ZPGZNKGKCSYBGK-UHFFFAOYSA-N 1-n-[4-(dimethylamino)phenyl]-4-n,4-n-dimethylbenzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=CC=C(N(C)C)C=C1 ZPGZNKGKCSYBGK-UHFFFAOYSA-N 0.000 description 4
ZVCFSCXUODRMKI-UHFFFAOYSA-N 3-(1-ethyl-2-methylindole-3-carbonyl)pyridine-2-carboxylic acid Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C(=O)C1=CC=CN=C1C(O)=O ZVCFSCXUODRMKI-UHFFFAOYSA-N 0.000 description 4
YKCFUMLMIBXYIO-UHFFFAOYSA-N 3-[4-(diethylamino)benzoyl]pyrazine-2-carboxylic acid Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=NC=CN=C1C(O)=O YKCFUMLMIBXYIO-UHFFFAOYSA-N 0.000 description 4
VIOWHEUVJPTYGV-UHFFFAOYSA-N 4-[4-(diethylamino)benzoyl]pyridine-3-carboxylic acid Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=NC=C1C(O)=O VIOWHEUVJPTYGV-UHFFFAOYSA-N 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 4
229940106691 bisphenol a Drugs 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
RHXUZKJNHAMZEP-LWTKGLMZSA-N europium;(z)-5-hydroxy-2,2,6,6-tetramethylhept-4-en-3-one Chemical compound [Eu].CC(C)(C)C(\O)=C\C(=O)C(C)(C)C.CC(C)(C)C(\O)=C\C(=O)C(C)(C)C.CC(C)(C)C(\O)=C\C(=O)C(C)(C)C RHXUZKJNHAMZEP-LWTKGLMZSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
MCQOWYALZVKMAR-UHFFFAOYSA-N furo[3,4-b]pyridine-5,7-dione Chemical compound C1=CC=C2C(=O)OC(=O)C2=N1 MCQOWYALZVKMAR-UHFFFAOYSA-N 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
125000001041 indolyl group Chemical group 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
QRBYEBPQYCYKFF-UHFFFAOYSA-N 2-[4-(diethylamino)-2-ethoxybenzoyl]pyridine-3-carboxylic acid Chemical compound CCOC1=CC(N(CC)CC)=CC=C1C(=O)C1=NC=CC=C1C(O)=O QRBYEBPQYCYKFF-UHFFFAOYSA-N 0.000 description 3
JKMIKHPSBSYDEM-UHFFFAOYSA-N 2-[4-(diethylamino)benzoyl]pyridine-3-carboxylic acid Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=NC=CC=C1C(O)=O JKMIKHPSBSYDEM-UHFFFAOYSA-N 0.000 description 3
FMHDTYNGPJYEHT-UHFFFAOYSA-N 3-(1-ethyl-2-methylindole-3-carbonyl)pyrazine-2-carboxylic acid Chemical compound C12=CC=CC=C2N(CC)C(C)=C1C(=O)C1=NC=CN=C1C(O)=O FMHDTYNGPJYEHT-UHFFFAOYSA-N 0.000 description 3
HUUXBGAMSUMHDT-UHFFFAOYSA-N 3-[4-(diethylamino)-2-methylbenzoyl]pyrazine-2-carboxylic acid Chemical compound CC1=CC(N(CC)CC)=CC=C1C(=O)C1=NC=CN=C1C(O)=O HUUXBGAMSUMHDT-UHFFFAOYSA-N 0.000 description 3
SGSDQRVVHKCRTB-UHFFFAOYSA-N 3-[4-(diethylamino)-2-methylbenzoyl]pyridine-2-carboxylic acid Chemical compound CC1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=CN=C1C(O)=O SGSDQRVVHKCRTB-UHFFFAOYSA-N 0.000 description 3
KPZVVDZELZBJMZ-UHFFFAOYSA-N 3-[4-(diethylamino)benzoyl]pyridine-2-carboxylic acid Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=CN=C1C(O)=O KPZVVDZELZBJMZ-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000000284 extract Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000005457 ice water Substances 0.000 description 3
239000003701 inert diluent Substances 0.000 description 3
CVVFFUKULYKOJR-UHFFFAOYSA-N n-phenyl-4-propan-2-yloxyaniline Chemical compound C1=CC(OC(C)C)=CC=C1NC1=CC=CC=C1 CVVFFUKULYKOJR-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000012429 reaction media Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
238000000859 sublimation Methods 0.000 description 3
230000008022 sublimation Effects 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
QAUIZSWZXQFEJL-UHFFFAOYSA-N 1h-furo[3,4-c]pyridin-3-one Chemical compound C1=NC=C2C(=O)OCC2=C1 QAUIZSWZXQFEJL-UHFFFAOYSA-N 0.000 description 2
HTAJBQSBGDNHEQ-UHFFFAOYSA-N 2-[4-(diethylamino)-2-methylbenzoyl]pyridine-3-carboxylic acid Chemical compound CC1=CC(N(CC)CC)=CC=C1C(=O)C1=NC=CC=C1C(O)=O HTAJBQSBGDNHEQ-UHFFFAOYSA-N 0.000 description 2
OQMUNHLSHKTQJP-UHFFFAOYSA-N 2-[4-(dimethylamino)benzoyl]pyridine-3-carboxylic acid Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=NC=CC=C1C(O)=O OQMUNHLSHKTQJP-UHFFFAOYSA-N 0.000 description 2
JIRNEGFECKQOEQ-UHFFFAOYSA-N 3-[4-(diethylamino)-2-ethoxybenzoyl]pyridine-2-carboxylic acid Chemical compound CCOC1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=CN=C1C(O)=O JIRNEGFECKQOEQ-UHFFFAOYSA-N 0.000 description 2
JJBNTOMVVMSKID-UHFFFAOYSA-N 3-[4-(diethylamino)-2-methylbenzoyl]pyridine-4-carboxylic acid Chemical compound CC1=CC(N(CC)CC)=CC=C1C(=O)C1=CN=CC=C1C(O)=O JJBNTOMVVMSKID-UHFFFAOYSA-N 0.000 description 2
BBMNAWISDWEKDJ-UHFFFAOYSA-N 3-[4-(dimethylamino)benzoyl]pyridine-2-carboxylic acid Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=CN=C1C(O)=O BBMNAWISDWEKDJ-UHFFFAOYSA-N 0.000 description 2
GSVGNTLLELAQEF-UHFFFAOYSA-N 3h-furo[3,4-c]pyridin-1-one Chemical compound N1=CC=C2C(=O)OCC2=C1 GSVGNTLLELAQEF-UHFFFAOYSA-N 0.000 description 2
UTIWLZCXXCBHGG-UHFFFAOYSA-N 4-[4-(diethylamino)-2-methylbenzoyl]pyridine-3-carboxylic acid Chemical compound CC1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=NC=C1C(O)=O UTIWLZCXXCBHGG-UHFFFAOYSA-N 0.000 description 2
SEKMXHXGKOKENQ-UHFFFAOYSA-N 4-ethoxy-n-phenylaniline Chemical compound C1=CC(OCC)=CC=C1NC1=CC=CC=C1 SEKMXHXGKOKENQ-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
244000144730 Amygdalus persica Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
238000004566 IR spectroscopy Methods 0.000 description 2
239000002841 Lewis acid Substances 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
235000006040 Prunus persica var persica Nutrition 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
239000002775 capsule Substances 0.000 description 2
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125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002245 particle Substances 0.000 description 1
125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
150000007965 phenolic acids Chemical class 0.000 description 1
150000002990 phenothiazines Chemical class 0.000 description 1
238000003825 pressing Methods 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000003579 shift reagent Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000126 substance Substances 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
VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
150000004992 toluidines Chemical class 0.000 description 1
125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001665 trituration Methods 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 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
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
- B41M5/132—Chemical colour-forming components; Additives or binders therefor
- B41M5/136—Organic colour formers, e.g. leuco dyes
- B41M5/145—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
- B—PERFORMING OPERATIONS; TRANSPORTING
- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/26—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used
- B41M5/30—Thermography ; Marking by high energetic means, e.g. laser otherwise than by burning, and characterised by the material used using chemical colour formers
- B41M5/323—Organic colour formers, e.g. leuco dyes
- B41M5/327—Organic colour formers, e.g. leuco dyes with a lactone or lactam ring
- 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
- C07D213/04—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 having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—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 having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- 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
- C07D213/04—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 having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—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 having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Color Printing (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heat Sensitive Colour Forming Recording (AREA)

NL7908868A 1978-12-11 1979-12-10 Gesubstitueerde furopyridinonen en furopyrazinonen. NL7908868A (nl)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US05/968,082 US4211872A (en)	1978-12-11	1978-12-11	Substituted furopyridinones and furopyrazinones
US96808278		1978-12-11
US4853479		1979-06-14
US06/048,534 US4243250A (en)	1979-06-14	1979-06-14	Carbonless duplicating systems

Publications (1)

Publication Number	Publication Date
NL7908868A true NL7908868A (nl)	1980-06-13

Family

ID=26726232

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7908868A NL7908868A (nl)	1978-12-11	1979-12-10	Gesubstitueerde furopyridinonen en furopyrazinonen.

Country Status (15)

Country	Link
KR (1)	KR830001841B1 (el)
AU (1)	AU527175B2 (el)
BR (1)	BR7908016A (el)
CA (1)	CA1137477A (el)
CH (1)	CH645112A5 (el)
DE (1)	DE2949804A1 (el)
DK (1)	DK524079A (el)
ES (2)	ES8102123A1 (el)
FR (1)	FR2444039A1 (el)
GB (1)	GB2037799B (el)
GR (1)	GR73183B (el)
IE (1)	IE49314B1 (el)
IT (1)	IT1127277B (el)
MX (1)	MX151977A (el)
NL (1)	NL7908868A (el)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH652733A5 (de) *	1983-04-07	1985-11-29	Ciba Geigy Ag	Verfahren zur herstellung von 4-azaphthalidverbindungen.
GB8504631D0 (en) *	1985-02-22	1985-03-27	Ici Plc	Chromogenic compounds

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE791793A (fr) *	1971-12-06	1973-03-16	Ncr Co	Composes chromogenes
GB1564559A (en) *	1976-12-29	1980-04-10	Sterling Drug Inc	3(diphenylamino) phthalides

1979
- 1979-11-28 IE IE2282/79A patent/IE49314B1/en unknown
- 1979-11-28 CA CA000340769A patent/CA1137477A/en not_active Expired
- 1979-12-03 AU AU53404/79A patent/AU527175B2/en not_active Expired - Fee Related
- 1979-12-04 IT IT27840/79A patent/IT1127277B/it active
- 1979-12-07 MX MX180378A patent/MX151977A/es unknown
- 1979-12-07 GR GR60713A patent/GR73183B/el unknown
- 1979-12-07 FR FR7930155A patent/FR2444039A1/fr active Granted
- 1979-12-10 ES ES486713A patent/ES8102123A1/es not_active Expired
- 1979-12-10 BR BR7908016A patent/BR7908016A/pt unknown
- 1979-12-10 KR KR1019790004349A patent/KR830001841B1/ko not_active Expired
- 1979-12-10 NL NL7908868A patent/NL7908868A/nl not_active Application Discontinuation
- 1979-12-10 DK DK524079A patent/DK524079A/da not_active Application Discontinuation
- 1979-12-10 GB GB7942548A patent/GB2037799B/en not_active Expired
- 1979-12-11 DE DE19792949804 patent/DE2949804A1/de not_active Ceased
- 1979-12-11 CH CH1097479A patent/CH645112A5/fr not_active IP Right Cessation
1980
- 1980-07-31 ES ES493884A patent/ES8106668A1/es not_active Expired

Also Published As

Publication number	Publication date
KR830001287A (ko)	1983-04-30
BR7908016A (pt)	1980-09-23
DE2949804A1 (de)	1980-06-19
ES493884A0 (es)	1981-08-01
IE49314B1 (en)	1985-09-18
FR2444039A1 (fr)	1980-07-11
FR2444039B1 (el)	1983-08-05
KR830001841B1 (ko)	1983-09-14
DK524079A (da)	1980-06-12
ES486713A0 (es)	1980-12-16
ES8102123A1 (es)	1980-12-16
ES8106668A1 (es)	1981-08-01
IT1127277B (it)	1986-05-21
GB2037799A (en)	1980-07-16
GR73183B (el)	1984-02-14
AU5340479A (en)	1980-06-19
IE792282L (en)	1980-06-11
GB2037799B (en)	1983-01-06
IT7927840A0 (it)	1979-12-04
CH645112A5 (fr)	1984-09-14
AU527175B2 (en)	1983-02-17
MX151977A (es)	1985-05-23
CA1137477A (en)	1982-12-14

Legal Events

Date	Code	Title	Description
1983-08-01	BV	The patent application has lapsed

Publication	Publication Date	Title
US4189171A (en)	1980-02-19	Marking systems containing 3-aryl-3-heterylphthalides and 3,3-bis(heteryl)phthalides
JPS5827824B2 (ja)	1983-06-11	ベンゾインド−ルフタリド呈色性染料
NL7908868A (nl)	1980-06-13	Gesubstitueerde furopyridinonen en furopyrazinonen.
US4660060A (en)	1987-04-21	Imaging systems containing 3-(indol-3-yl)-3-(4-substituted aminophenyl)phthalides
US4168378A (en)	1979-09-18	3-(9-Julolidinyl)-3-(diphenylamino)phthalides
US4251446A (en)	1981-02-17	Phthalide compounds, processes and marking systems
DE2537776A1 (de)	1976-03-11	Phthalidverbindungen
DE2435408C2 (de)	1982-04-22	2(3)-[&alpha;-Aminophenyl-&alpha;-tetrahydrochinolin-&alpha;-hydroxy]-methylpyridincarbonsäuren-3(2)-lactone
CA1082708A (en)	1980-07-29	3- (diphenylamino) phthalides
US4431819A (en)	1984-02-14	3-(Pyrrolo and 3-indolyl)-3-diphenylamino substituted phthalides
US4351768A (en)	1982-09-28	2-[(3-Indolyl)carbonyl]-4/5-carboxybenzoic acids
US4337340A (en)	1982-06-29	Processes for preparing substituted furopyridinones and furopyrazinones
US4322352A (en)	1982-03-30	Indolyl phthalide compounds
US4211872A (en)	1980-07-08	Substituted furopyridinones and furopyrazinones
US4182714A (en)	1980-01-08	Carbazole containing phthalides
US4243250A (en)	1981-01-06	Carbonless duplicating systems
US4736027A (en)	1988-04-05	Indole-phthalide derivatives
US4251092A (en)	1981-02-17	Pressure sensitive carbonless duplicating systems and thermal marking systems
US4187223A (en)	1980-02-05	3-[4-(Disubstituted-amino)phenyl]-3-(diphenylamino)phthalides
US4697018A (en)	1987-09-29	9-julolidinyl derivatives and process of preparing them
US4788285A (en)	1988-11-29	Indole-phthalide derivatives
EP0108382A1 (en)	1984-05-16	Hydrazine derivatives of phthalides and furopyridinones, methods for making and for using said compounds
US4307018A (en)	1981-12-22	Heteroarylphthalides
US4558137A (en)	1985-12-10	Bis phenyl (2 carboxylic acid or ester indol-3-yl)methanes
CA1167856A (en)	1984-05-22	Pyromellitide color formers for carbonless duplicating systems