DD141023A5 - Verfahren zur herstellung eines 2,3-dihydrobenzofuranderivats - Google Patents

Verfahren zur herstellung eines 2,3-dihydrobenzofuranderivats Download PDF

Info

Publication number: DD141023A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; group; compound; carbon atoms; mixture
Prior art date: 1977-06-30

Application number

DD78206342A

Other languages

German (de)

English (en)

Inventor

Donald T Witiak

John B Carr

Harry J Mersmann

Original Assignee

Shell Int Research

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.)

1977-06-30

Filing date

1978-06-28

Publication date

1980-04-09

1978-06-28 Application filed by Shell Int Research filed Critical Shell Int Research

1980-04-09 Publication of DD141023A5 publication Critical patent/DD141023A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 9
238000000034 method Methods 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 6
-1 phenoxy, Benzyl Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
OFFSPAZVIVZPHU-UHFFFAOYSA-N 1-benzofuran-2-carboxylic acid Chemical compound C1=CC=C2OC(C(=O)O)=CC2=C1 OFFSPAZVIVZPHU-UHFFFAOYSA-N 0.000 claims 1
SFLGSKRGOWRGBR-UHFFFAOYSA-N phthalane Chemical class C1=CC=C2COCC2=C1 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
150000001875 compounds Chemical class 0.000 description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 18
239000000243 solution Substances 0.000 description 17
241001465754 Metazoa Species 0.000 description 12
230000004132 lipogenesis Effects 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
150000002989 phenols Chemical class 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
239000000284 extract Substances 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000000047 product Substances 0.000 description 4
HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical class C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
229940125904 compound 1 Drugs 0.000 description 3
229940126214 compound 3 Drugs 0.000 description 3
239000013078 crystal Substances 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
210000001519 tissue Anatomy 0.000 description 3
QJPQHYIOZBKAKO-UHFFFAOYSA-N 5-phenyl-2,3-dihydro-1-benzofuran-2-carboxylic acid Chemical compound C=1C=C2OC(C(=O)O)CC2=CC=1C1=CC=CC=C1 QJPQHYIOZBKAKO-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
241000282887 Suidae Species 0.000 description 2
239000002253 acid Substances 0.000 description 2
210000000577 adipose tissue Anatomy 0.000 description 2
125000003302 alkenyloxy group Chemical group 0.000 description 2
125000005133 alkynyloxy group Chemical group 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
229940125782 compound 2 Drugs 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000008103 glucose Substances 0.000 description 2
238000011534 incubation Methods 0.000 description 2
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
239000010410 layer Substances 0.000 description 2
150000002632 lipids Chemical class 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
235000015277 pork Nutrition 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002243 precursor Substances 0.000 description 2
230000002285 radioactive effect Effects 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000003826 tablet Substances 0.000 description 2
BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
NAUBSKHQFFCEMQ-UHFFFAOYSA-N 2-hydroxy-5-phenylbenzaldehyde Chemical compound C1=C(C=O)C(O)=CC=C1C1=CC=CC=C1 NAUBSKHQFFCEMQ-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
241000283707 Capra Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
241000283086 Equidae Species 0.000 description 1
241000283074 Equus asinus Species 0.000 description 1
241001331845 Equus asinus x caballus Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
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 1
102000004877 Insulin Human genes 0.000 description 1
108090001061 Insulin Proteins 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000772415 Neovison vison Species 0.000 description 1
241001494479 Pecora Species 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
240000004808 Saccharomyces cerevisiae Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229920004890 Triton X-100 Polymers 0.000 description 1
239000013504 Triton X-100 Substances 0.000 description 1
229920001938 Vegetable gum Polymers 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
239000003405 delayed action preparation Substances 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000015872 dietary supplement Nutrition 0.000 description 1
FNJVDWXUKLTFFL-UHFFFAOYSA-N diethyl 2-bromopropanedioate Chemical compound CCOC(=O)C(Br)C(=O)OCC FNJVDWXUKLTFFL-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
244000144980 herd Species 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
239000007943 implant Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229940125396 insulin Drugs 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
238000007911 parenteral administration Methods 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
229910000027 potassium carbonate Inorganic materials 0.000 description 1
244000144977 poultry Species 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000003345 scintillation counting Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910001023 sodium amalgam Inorganic materials 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical class [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000002627 tracheal intubation Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
- C07D307/84—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D307/85—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/008—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with tri- or tetrahalomethyl compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Hematology (AREA)
Diabetes (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Obesity (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Furan Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

DD78206342A 1977-06-30 1978-06-28 Verfahren zur herstellung eines 2,3-dihydrobenzofuranderivats DD141023A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US81164777A	1977-06-30	1977-06-30
US81789877A	1977-07-21	1977-07-21

Publications (1)

Publication Number	Publication Date
DD141023A5 true DD141023A5 (de)	1980-04-09

Family

ID=27123512

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD78206342A DD141023A5 (de)	1977-06-30	1978-06-28	Verfahren zur herstellung eines 2,3-dihydrobenzofuranderivats

Country Status (9)

Country	Link
AU (1)	AU520682B2 (da)
DD (1)	DD141023A5 (da)
DE (1)	DE2828396A1 (da)
DK (1)	DK292678A (da)
FR (1)	FR2401146A1 (da)
GB (1)	GB2007973B (da)
IT (1)	IT1113147B (da)
NL (1)	NL7806944A (da)
SE (1)	SE7807338L (da)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0019955A1 (en) *	1979-05-16	1980-12-10	Shell Internationale Researchmaatschappij B.V.	Benzofurancarboxylic acid derivatives, their preparation and their inclusion in lipogenesis inhibiting compositions
US4229467A (en) *	1979-08-16	1980-10-21	Richardson-Merrell Inc.	Alkoxy benzofuran carboxylic acids and salts and esters thereof as hypolipidemic agents
US4663347A (en) *	1983-10-31	1987-05-05	Merck Frosst Canada, Inc.	Benzofuran 2-carboxylic acid esters useful as inhibitors of leukotriene biosynthesis
US4933351A (en) *	1983-10-31	1990-06-12	Merck Frosst Canada, Inc.	Benzofuran 2-carbox amides useful as inhibitors of leukoriene biosynthesis
US4822803A (en) *	1983-10-31	1989-04-18	Merck Frosst Canada, Inc.	Benzofuran 2-carboxylic acid hydrazides useful as inhibitors of leukotriene biosynthesis
EP0146243A1 (en) *	1983-10-31	1985-06-26	Merck Frosst Canada Inc.	Lipoxygenase inhibitors
JP3093507B2 (ja) *	1993-02-15	2000-10-03	キヤノン株式会社	液晶性化合物、これを含む液晶組成物、それを有する液晶素子、それらを用いた表示方法および表示装置
US7435837B2 (en)	2003-10-24	2008-10-14	Wyeth	Dihydrobenzofuranyl alkanamine derivatives and methods for using same

1978
- 1978-06-28 AU AU37515/78A patent/AU520682B2/en not_active Expired
- 1978-06-28 DD DD78206342A patent/DD141023A5/de unknown
- 1978-06-28 FR FR7819308A patent/FR2401146A1/fr active Granted
- 1978-06-28 NL NL7806944A patent/NL7806944A/xx not_active Application Discontinuation
- 1978-06-28 GB GB7828225A patent/GB2007973B/en not_active Expired
- 1978-06-28 DE DE19782828396 patent/DE2828396A1/de not_active Withdrawn
- 1978-06-28 DK DK292678A patent/DK292678A/da not_active Application Discontinuation
- 1978-06-28 SE SE7807338A patent/SE7807338L/xx unknown
- 1978-06-28 IT IT25091/78A patent/IT1113147B/it active

Also Published As

Publication number	Publication date
SE7807338L (sv)	1978-12-31
GB2007973A (en)	1979-05-31
GB2007973B (en)	1982-04-21
NL7806944A (nl)	1979-01-03
AU520682B2 (en)	1982-02-18
FR2401146B1 (da)	1983-03-18
IT7825091A0 (it)	1978-06-28
FR2401146A1 (fr)	1979-03-23
IT1113147B (it)	1986-01-20
AU3751578A (en)	1980-01-03
DE2828396A1 (de)	1979-01-11
DK292678A (da)	1978-12-31

Publication	Publication Date	Title
DE3751006T2 (de)	1995-05-24	Psychostimulierendes mittel.
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DE2108438A1 (de)	1971-09-09	Benzylimidazolidinone
DD159071A5 (de)	1983-02-16	Verfahren zur darstellung von pyridoxinderivaten und ihre verwendung in therapeutica
DE3037770C2 (de)	1994-11-10	N-Niedrigalkyl-3-phenoxy-1-azetidincarboxamide und diese Verbindungen enthaltende Zubereitungen
DE2160148C2 (de)	1984-07-19	Arzneimittel und bestimmte Sulfoxide als solche
DD235065A5 (de)	1986-04-23	Verfahren zur herstellung von n-(2-(4-fluorphenyl)-1-methyl)-n-methyl-n-propinylamin
DE2501834C2 (de)	1987-01-08	Neue Appetitzügler
DE2828396A1 (de)	1979-01-11	Benzofuran- bzw. dihydrobenzofuranderivate
DE2157272C3 (de)	1979-03-01	Verwendung von bis-(p-Chlorphenoxy)acetylharnstoff
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DE2703652C2 (da)	1988-01-21
DE1493083B1 (de)	1972-08-17	Linolsaeureamide und Verfahren zu ihrer Herstellung
DE3142559A1 (de)	1982-09-02	"pyrimidin-derivate"
DE2113489C3 (de)	1980-05-08	2-Nitro-benzofuranderivate, ein Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
DE2738131A1 (de)	1978-03-09	Aminoketone, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE1695231B1 (de)	1972-05-04	3-Carbalkoxy-4-hydroxy-chinolinderivate
DE3324727C2 (da)	1988-09-22
DE3706399A1 (de)	1988-09-08	Mittel mit antidepressiver wirkung
DE3220185A1 (de)	1982-12-23	4-amino-benzylamin-derivate, verfahren zu ihrer herstellung, sowie ihre verwendung als pharmazeutica
DE2909646B1 (de)	1980-01-10	N-Alkenylmoranolinderivate
DE2811236A1 (de)	1978-09-28	Biologisch wirksame mittel
DE2848493A1 (de)	1979-05-10	Pharmazeutische zusammensetzung zum abtoeten von inneren parasiten bei warmbluetern, welche als wirkstoff ein dinitriertes diphenylmethanderivat enthalten
DE2828358A1 (de)	1979-01-11	2,3-dihydro-1,4-benzoxathiine
AT347456B (de)	1978-12-27	Verfahren zur herstellung von neuen 5-methyl-7- hydroxy-isoflavon-derivaten