CA1084502A - Preparation de benzimidazo- 1,2-a -quinolines - Google Patents

Preparation de benzimidazo- 1,2-a -quinolines

Info

Publication number: CA1084502A
Authority: CA; Canada
Prior art keywords: formula; compounds; lower alkyl; carbonamido; hydrogen
Prior art date: 1976-09-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA286,306A

Other languages

English (en)

Inventor

Dieter Gunther

Rudiger Erckel

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

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.)

1976-09-09

Filing date

1977-09-08

Publication date

1980-08-26

1977-09-08 Application filed by Hoechst AG filed Critical Hoechst AG

1980-08-26 Application granted granted Critical

1980-08-26 Publication of CA1084502A publication Critical patent/CA1084502A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 11
238000002360 preparation method Methods 0.000 title claims abstract description 7
229940111121 antirheumatic drug quinolines Drugs 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 45
125000000217 alkyl group Chemical group 0.000 claims description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
-1 nitro, amino Chemical group 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
125000003545 alkoxy group Chemical group 0.000 claims description 11
KASCQZOWHVVARL-UHFFFAOYSA-N carboxy cyanoformate Chemical compound C(=O)(O)OC(=O)C#N KASCQZOWHVVARL-UHFFFAOYSA-N 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
239000012442 inert solvent Substances 0.000 claims description 7
150000007530 organic bases Chemical class 0.000 claims description 7
125000004442 acylamino group Chemical group 0.000 claims description 5
150000001299 aldehydes Chemical class 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000003277 amino group Chemical group 0.000 claims description 4
238000007363 ring formation reaction Methods 0.000 claims description 4
125000005208 trialkylammonium group Chemical group 0.000 claims description 4
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
125000004663 dialkyl amino group Chemical group 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000003262 carboxylic acid ester group Chemical class [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
238000002955 isolation Methods 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 2
125000005157 alkyl carboxy group Chemical group 0.000 claims 1
RMGVZKRVHHSUIM-UHFFFAOYSA-N dithionic acid Chemical compound OS(=O)(=O)S(O)(=O)=O RMGVZKRVHHSUIM-UHFFFAOYSA-N 0.000 claims 1
230000003287 optical effect Effects 0.000 abstract description 4
238000006467 substitution reaction Methods 0.000 abstract description 3
239000000543 intermediate Substances 0.000 abstract description 2
239000007787 solid Substances 0.000 abstract description 2
QQYLPRKCBLKCJM-UHFFFAOYSA-N benzimidazolo[1,2-a]quinoline Chemical class C1=CC=C2N3C4=CC=CC=C4N=C3C=CC2=C1 QQYLPRKCBLKCJM-UHFFFAOYSA-N 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 8
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
239000008096 xylene Substances 0.000 description 7
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
239000013078 crystal Substances 0.000 description 6
150000003254 radicals Chemical group 0.000 description 6
239000003054 catalyst Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 5
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
238000009833 condensation Methods 0.000 description 4
230000005494 condensation Effects 0.000 description 4
RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 3
238000001035 drying Methods 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
239000007858 starting material Substances 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
LWRSYTXEQUUTKW-UHFFFAOYSA-N 2,4-dimethoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(OC)=C1 LWRSYTXEQUUTKW-UHFFFAOYSA-N 0.000 description 2
BWOVACANEIVHST-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)acetonitrile Chemical compound C1=CC=C2NC(CC#N)=NC2=C1 BWOVACANEIVHST-UHFFFAOYSA-N 0.000 description 2
MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 2
DHLFXZQEAWYQLC-UHFFFAOYSA-N 4-(dimethylamino)-2-nitrobenzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C([N+]([O-])=O)=C1 DHLFXZQEAWYQLC-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
229910052742 iron Inorganic materials 0.000 description 2
239000000203 mixture Substances 0.000 description 2
VQTGUFBGYOIUFS-UHFFFAOYSA-N nitrosylsulfuric acid Chemical compound OS(=O)(=O)ON=O VQTGUFBGYOIUFS-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 2
238000005406 washing Methods 0.000 description 2
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
ZECUELAGGOAWOP-UHFFFAOYSA-N 1-(1h-benzimidazol-2-yl)propan-2-one Chemical compound C1=CC=C2NC(CC(=O)C)=NC2=C1 ZECUELAGGOAWOP-UHFFFAOYSA-N 0.000 description 1
PYEOIKOGBCTVOM-UHFFFAOYSA-N 2-(benzenesulfonylmethylidene)benzimidazole Chemical class N1=C2C=CC=CC2=NC1=CS(=O)(=O)C1=CC=CC=C1 PYEOIKOGBCTVOM-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
PKZJLOCLABXVMC-BJUDXGSMSA-N 2-methoxybenzaldehyde Chemical compound [11CH3]OC1=CC=CC=C1C=O PKZJLOCLABXVMC-BJUDXGSMSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
241000728904 Iais Species 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
229920002292 Nylon 6 Polymers 0.000 description 1
229920002302 Nylon 6,6 Polymers 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
SMEGJBVQLJJKKX-HOTMZDKISA-N [(2R,3S,4S,5R,6R)-5-acetyloxy-3,4,6-trihydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O)OC(=O)C)O)O SMEGJBVQLJJKKX-HOTMZDKISA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
229940081735 acetylcellulose Drugs 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
150000003935 benzaldehydes Chemical class 0.000 description 1
150000001556 benzimidazoles Chemical class 0.000 description 1
238000004061 bleaching Methods 0.000 description 1
125000005521 carbonamide group Chemical group 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000011888 foil Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000004002 naphthaldehydes Chemical class 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
PKZJLOCLABXVMC-UHFFFAOYSA-N ortho-Methoxybenzaldehyde Natural products COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
OSHVGUAPPIYWIS-UHFFFAOYSA-N piperazin-1-ium;acetate Chemical compound CC(O)=O.C1CNCCN1 OSHVGUAPPIYWIS-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000098 polyolefin Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000036647 reaction Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000004627 regenerated cellulose Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000017550 sodium carbonate Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
210000002268 wool Anatomy 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CA286,306A 1976-09-09 1977-09-08 Preparation de benzimidazo- 1,2-a -quinolines Expired CA1084502A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DEP2640549.2		1976-09-09
DE19762640549 DE2640549A1 (de)	1976-09-09	1976-09-09	Benzimidazo- eckige klammer auf 1,2-a eckige klammer zu -chinoline und verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
CA1084502A true CA1084502A (fr)	1980-08-26

Family

ID=5987507

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA286,306A Expired CA1084502A (fr)	1976-09-09	1977-09-08	Preparation de benzimidazo- 1,2-a -quinolines

Country Status (4)

Country	Link
BE (1)	BE858575A (fr)
CA (1)	CA1084502A (fr)
DE (1)	DE2640549A1 (fr)
GB (1)	GB1590680A (fr)

1976
- 1976-09-09 DE DE19762640549 patent/DE2640549A1/de not_active Withdrawn
1977
- 1977-09-07 GB GB3732277A patent/GB1590680A/en not_active Expired
- 1977-09-08 CA CA286,306A patent/CA1084502A/fr not_active Expired
- 1977-09-09 BE BE180807A patent/BE858575A/fr unknown

Also Published As

Publication number	Publication date
BE858575A (fr)	1978-03-09
GB1590680A (en)	1981-06-03
DE2640549A1 (de)	1978-03-23

Legal Events

Date	Code	Title	Description
1997-08-26	MKEX	Expiry

Publication	Publication Date	Title
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US4326066A (en)	1982-04-20	Triazolyl coumarin compounds, processes for their preparation and their use as whiteners and laser dyestuffs
US3013013A (en)	1961-12-12	5-cyanomethylene-2-oxo-3-pyrrolines
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US4594420A (en)	1986-06-10	Perylene-3,4,9,10-tetracarboxylic acid monoanhydride monoimide and monoimidazolide compounds, processes for their preparation and their use
US4897494A (en)	1990-01-30	Bis(indolyl)ethylene process
US3334113A (en)	1967-08-01	9b-phenyl-1, 2, 3, 9b-tetrahydro-5h-imidazo[2,1-a]isoindol-5-ones
CA1042899A (fr)	1978-11-21	Synthese de composes furaniques
CA1084502A (fr)	1980-08-26	Preparation de benzimidazo- 1,2-a -quinolines
DE2000027A1 (de)	1971-07-08	Optische Aufheller
US3202657A (en)	1965-08-24	Nu-aralkyl- and nu-aryl derivatives of tetrahydro-oxathiazine-(1, 4, 5)-dioxide-(4, 4) and process for preparing them
US3926969A (en)	1975-12-16	Triazole-bis(benzoxazole) optical brighteners
Nguyen et al.	1985	Oxidation of aldehyde semicarbazones with lead dioxide: Application to the syntheses of 2‐amino‐1, 3, 4‐oxadiazoles and 2, 4‐dihydro‐1, 2, 4‐triazol‐3‐ones
JPS5928589B2 (ja)	1984-07-13	ペリノン染料並びにその製法
Duncan Jr et al.	1973	Synthesis of Indolo and benzimidazoquinazolines and benzodiazepines
US4219651A (en)	1980-08-26	Benzimidazo-[1,2-a]-quinolines
US3940410A (en)	1976-02-24	Bis-benzonazoledicarbonitriles
Dhamnaskar et al.	1988	Synthesis of triazoflo [4, 5-b] pyrido [1', 2'-a] benzimidazole derivatives as fluorescent disperse dyes and whiteners for polyester fibre
US3840552A (en)	1974-10-08	Azolindolines and azolindoline dyestuffs
US3507863A (en)	1970-04-21	Isoindolones and method for preparing same
US4423226A (en)	1983-12-27	Zinc chloride complex compounds
US3880841A (en)	1975-04-29	Triazolyl ethenyl phenylene derivatives
US4016172A (en)	1977-04-05	Azolindolines and azolindoline dyestuffs