CA1138468A - Composes tricycliques - Google Patents

Composes tricycliques

Info

Publication number: CA1138468A
Authority: CA; Canada
Prior art keywords: formula; compound; preparation; alkyl; ivb
Prior art date: 1978-02-08
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

CA000393611A

Other languages

English (en)

Inventor

Angelo Storni

Hans Zweifel

Walter Schilling

Daniel Bellus

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.)

BASF Schweiz AG

Original Assignee

Ciba Geigy Investments Ltd

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.)

1978-02-08

Filing date

1982-01-05

Publication date

1982-12-28

1979-02-06 Priority claimed from CA320,890A external-priority patent/CA1128950A/fr

1982-01-05 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1982-01-05 Priority to CA000393611A priority Critical patent/CA1138468A/fr

1982-12-28 Application granted granted Critical

1982-12-28 Publication of CA1138468A publication Critical patent/CA1138468A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 19
238000002360 preparation method Methods 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
239000001257 hydrogen Substances 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
125000003118 aryl group Chemical group 0.000 claims abstract description 3
229910052736 halogen Inorganic materials 0.000 claims abstract description 3
150000002367 halogens Chemical class 0.000 claims abstract description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 2
-1 oxalic acid diester Chemical class 0.000 claims description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 2
238000000034 method Methods 0.000 claims description 2
235000006408 oxalic acid Nutrition 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
229920000642 polymer Polymers 0.000 abstract description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
239000011541 reaction mixture Substances 0.000 description 9
239000012071 phase Substances 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
239000003921 oil Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 3
150000003949 imides Chemical class 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
239000001117 sulphuric acid Substances 0.000 description 3
235000011149 sulphuric acid Nutrition 0.000 description 3
239000000725 suspension Substances 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
239000000178 monomer Substances 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
238000006068 polycondensation reaction Methods 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
ZTWMBHJPUJJJME-UHFFFAOYSA-N 3,4-dimethylpyrrole-2,5-dione Chemical compound CC1=C(C)C(=O)NC1=O ZTWMBHJPUJJJME-UHFFFAOYSA-N 0.000 description 1
YGJRRQQARFWGEY-UHFFFAOYSA-N 3a,4,5,10b-tetrahydrofuro[3,4-d][1]benzoxepine-1,3-dione Chemical compound C1COC2=CC=CC=C2C2C(=O)OC(=O)C21 YGJRRQQARFWGEY-UHFFFAOYSA-N 0.000 description 1
GUHDWFDSRPYWNN-UHFFFAOYSA-N 4,5-dihydrofuro[3,4-d][1]benzoxepine-1,3-dione Chemical compound C1COC2=CC=CC=C2C2=C1C(=O)OC2=O GUHDWFDSRPYWNN-UHFFFAOYSA-N 0.000 description 1
WKNRJYNQSWPAIB-UHFFFAOYSA-N 5,6-dihydro-4h-benzo[1,2]cyclohepta[6,7-b]furan-1,3-dione Chemical compound C1CCC2=CC=CC=C2C2=C1C(=O)OC2=O WKNRJYNQSWPAIB-UHFFFAOYSA-N 0.000 description 1
BYHDDXPKOZIZRV-UHFFFAOYSA-N 5-phenylpentanoic acid Chemical compound OC(=O)CCCCC1=CC=CC=C1 BYHDDXPKOZIZRV-UHFFFAOYSA-N 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
239000004642 Polyimide Substances 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
239000000470 constituent Substances 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
230000006324 decarbonylation Effects 0.000 description 1
238000006606 decarbonylation reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
IHASFDBVENKSHI-UHFFFAOYSA-N ethyl 2-phenoxybutanoate Chemical compound CCOC(=O)C(CC)OC1=CC=CC=C1 IHASFDBVENKSHI-UHFFFAOYSA-N 0.000 description 1
QCHDRUGIAZBPGB-UHFFFAOYSA-N ethyl 5-phenylpentanoate Chemical compound CCOC(=O)CCCCC1=CC=CC=C1 QCHDRUGIAZBPGB-UHFFFAOYSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
150000004676 glycans Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
GPIUUMROPXDNRH-UMRXKNAASA-N molport-035-395-376 Chemical compound O=C1NC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 GPIUUMROPXDNRH-UMRXKNAASA-N 0.000 description 1
125000000896 monocarboxylic acid 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
229910052757 nitrogen Inorganic materials 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
MVIMPQVBUPCHEV-UHFFFAOYSA-N phenyl pentanoate Chemical compound CCCCC(=O)OC1=CC=CC=C1 MVIMPQVBUPCHEV-UHFFFAOYSA-N 0.000 description 1
125000005543 phthalimide group Chemical group 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920001721 polyimide Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Indole Compounds (AREA)

CA000393611A 1978-02-08 1982-01-05 Composes tricycliques Expired CA1138468A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000393611A CA1138468A (fr)	1978-02-08	1982-01-05	Composes tricycliques

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
CH140078		1978-02-08
CH1400/78-3		1978-02-08
CA320,890A CA1128950A (fr)	1978-02-08	1979-02-06	Derives d'imidyles tricycliques
CA000393611A CA1138468A (fr)	1978-02-08	1982-01-05	Composes tricycliques

Publications (1)

Publication Number	Publication Date
CA1138468A true CA1138468A (fr)	1982-12-28

Family

ID=27166066

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000393611A Expired CA1138468A (fr)	1978-02-08	1982-01-05	Composes tricycliques

Country Status (1)

Country	Link
CA (1)	CA1138468A (fr)

1982
- 1982-01-05 CA CA000393611A patent/CA1138468A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1999-12-29	MKEX	Expiry

Publication	Publication Date	Title
EP0916675B1 (fr)	2003-07-30	Procédé pour la préparation de sildenafil
CA1312613C (fr)	1993-01-12	Procede pour la preparation de moncesters ou de diesters de l'acide 9,10-endoethano-9,10-dihydroxyanthracene-11, 11-dicarboxylique, nouveaux monoesters ou diesters obtenus a l'aide de ce procede et son utilisation pour la preparation de methylidenemalonates asymetriques ou
US4769493A (en)	1988-09-06	Process for producing tetrafluorophthalic acid
CA1128950A (fr)	1982-08-03	Derives d'imidyles tricycliques
CA1138468A (fr)	1982-12-28	Composes tricycliques
US5286874A (en)	1994-02-15	Process for the production of bismaleinimide derivatives
US4125563A (en)	1978-11-14	Process for making nitroarylacetylenes and nitroarylaldehydes
Igglessi‐Markopoulou et al.	1982	Acylaminoacetyl derivatives of active methylene compounds. 1. The cyclization of the benzoylaminoacetyl derivatives to α‐substituted tetramic acids
US5047553A (en)	1991-09-10	Tetrafluoro-N-phenylphthalimide
US5466808A (en)	1995-11-14	8-sulfo-3-quinoline carboxylic acids and process therefore
US4691062A (en)	1987-09-01	Process for the production of 4-chloro-butanals
EP0370357B1 (fr)	1994-06-22	Procédé pour la production de 3-iminonitriles
US5672708A (en)	1997-09-30	Process for the preparation of N-arylaminoacrylic acid derivatives and the use of N-arylaminoacrylic acid derivatives thus prepared for the preparation of 4-quinolone-3-carboxylic acid derivatives
US3996289A (en)	1976-12-07	Process for the preparation of 2-nitrobenzaldehyde
JP2000053643A (ja)	2000-02-22	芳香族マレイミドの製造方法
JPH03170451A (ja)	1991-07-24	クロロフタル酸化合物からの塩素の選択的除去方法
US4421918A (en)	1983-12-20	Process for the preparation of 7-chloro-1,2,3,4-tetrahydroquinolin-4-one
EP0232992A1 (fr)	1987-08-19	Cétones aromatiques
US4994580A (en)	1991-02-19	Producing bis (alicyclic) thioethers
US3346638A (en)	1967-10-10	Alpha-phenyl-2-amino-benzylmercaptanes
Matsumoto et al.	1974	An Improved Synthesis of DL-Histidine
US4798900A (en)	1989-01-17	Producing bis(alicyclic) thioethers
JPH05194484A (ja)	1993-08-03	ベンゾ〔ｂ〕チオフェン−２−カルボン酸の製造法
SU1426971A1 (ru)	1988-09-30	1,7-Бис-/2-аминофенил/ - 1,7 -дитиагептаны в качестве промежуточных продуктов в синтезе 8,9: 17,18 - дибензо-1,7-дитиа-10,16-диазациклооктадеканов
KR820000581B1 (ko)	1982-04-15	6,11-디하이드로-11 옥소디벤즈 [b,e]-옥세핀-2-아세트산의 제조방법