NO120583B - - Google Patents

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Info

Publication number: NO120583B
Authority: NO; Norway
Prior art keywords: furan; formula; bromo; ethanol; ethyl
Prior art date: 1966-04-29

Application number

NO167947A

Other languages

English (en)

Norwegian (no)

Inventor

J Osbond

G Fothergill

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1966-04-29

Filing date

1967-04-28

Publication date

1970-11-09

1967-04-28 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1970-11-09 Publication of NO120583B publication Critical patent/NO120583B/no

Links

238000000034 method Methods 0.000 claims description 12
150000001907 coumarones Chemical class 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
239000000243 solution Substances 0.000 description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
230000008018 melting Effects 0.000 description 13
238000002844 melting Methods 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
-1 halogen ketones Chemical class 0.000 description 12
150000001412 amines Chemical class 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
150000003944 halohydrins Chemical class 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
150000001875 compounds Chemical class 0.000 description 8
239000000203 mixture Substances 0.000 description 8
239000002253 acid Substances 0.000 description 7
150000003839 salts Chemical class 0.000 description 7
150000002118 epoxides Chemical class 0.000 description 6
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
238000009835 boiling Methods 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
239000000155 melt Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
239000011230 binding agent Substances 0.000 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000012458 free base Substances 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
239000000725 suspension Substances 0.000 description 3
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
SUYTZVAKEJARFN-UHFFFAOYSA-N BrC1=CC2=C(OC(=C2)C(CCl)O)C=2CCCCC12 Chemical compound BrC1=CC2=C(OC(=C2)C(CCl)O)C=2CCCCC12 SUYTZVAKEJARFN-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000005660 chlorination reaction Methods 0.000 description 2
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
238000006704 dehydrohalogenation reaction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000001640 fractional crystallisation Methods 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
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229920000084 Gum arabic Polymers 0.000 description 1
241000978776 Senegalia senegal Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000012223 aqueous fraction Substances 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
239000002585 base Substances 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 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
125000005283 haloketone group Chemical group 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000013081 microcrystal Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical class OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 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
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
PRXNKYBFWAWBNZ-UHFFFAOYSA-N trimethylphenylammonium tribromide Chemical compound Br[Br-]Br.C[N+](C)(C)C1=CC=CC=C1 PRXNKYBFWAWBNZ-UHFFFAOYSA-N 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 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
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
- 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
- C07D307/93—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 condensed with a ring other than six-membered

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Furan Compounds (AREA)

NO167947A 1966-04-29 1967-04-28 NO120583B (fi)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB18815/66A GB1152871A (en)	1966-04-29	1966-04-29	Benzofuran Derivatives and the manufacture thereof

Publications (1)

Publication Number	Publication Date
NO120583B true NO120583B (fi)	1970-11-09

Family

ID=10118891

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO167947A NO120583B (fi)	1966-04-29	1967-04-28

Country Status (15)

Country	Link
US (1)	US3551458A (fi)
BE (1)	BE697507A (fi)
CH (1)	CH485701A (fi)
DE (1)	DE1593895C3 (fi)
DK (1)	DK123770B (fi)
ES (1)	ES339972A1 (fi)
FI (1)	FI47661C (fi)
FR (1)	FR6313M (fi)
GB (1)	GB1152871A (fi)
GR (1)	GR35813B (fi)
IL (1)	IL27440A (fi)
NL (1)	NL6705952A (fi)
NO (1)	NO120583B (fi)
SE (1)	SE346106B (fi)
YU (1)	YU33109B (fi)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
YU178168A (en) *	1967-07-28	1974-02-28	Geigy Ag J R	Postopek za pripravo novih heterociklicnih amino-karboksilnih kislin
US3716539A (en) *	1971-05-19	1973-02-13	Aldrich Chem Co Inc	1(2-dibenzofuryl)4-piperazino butanols

1966
- 1966-04-29 GB GB18815/66A patent/GB1152871A/en not_active Expired
1967
- 1967-02-15 IL IL27440A patent/IL27440A/en unknown
- 1967-03-31 CH CH459667A patent/CH485701A/de not_active IP Right Cessation
- 1967-04-04 DE DE1593895A patent/DE1593895C3/de not_active Expired
- 1967-04-18 FR FR103063A patent/FR6313M/fr not_active Expired
- 1967-04-19 US US631867A patent/US3551458A/en not_active Expired - Lifetime
- 1967-04-24 FI FI671197A patent/FI47661C/fi active
- 1967-04-25 BE BE697507D patent/BE697507A/xx unknown
- 1967-04-26 DK DK223367AA patent/DK123770B/da unknown
- 1967-04-27 NL NL6705952A patent/NL6705952A/xx unknown
- 1967-04-27 GR GR670135813A patent/GR35813B/el unknown
- 1967-04-28 NO NO167947A patent/NO120583B/no unknown
- 1967-04-28 ES ES339972A patent/ES339972A1/es not_active Expired
- 1967-04-29 YU YU876/67A patent/YU33109B/xx unknown
- 1967-06-28 SE SE6111/67A patent/SE346106B/xx unknown

Also Published As

Publication number	Publication date
DE1593895B2 (de)	1975-01-09
GR35813B (el)	1968-11-04
FR6313M (fi)	1968-09-16
NL6705952A (fi)	1967-10-30
GB1152871A (en)	1969-05-21
ES339972A1 (es)	1968-09-01
DK123770B (da)	1972-07-31
DE1593895A1 (de)	1971-02-18
FI47661B (fi)	1973-10-31
US3551458A (en)	1970-12-29
SE346106B (fi)	1972-06-26
YU33109B (en)	1976-04-30
BE697507A (fi)	1967-10-25
FI47661C (fi)	1974-02-11
DE1593895C3 (de)	1975-08-14
IL27440A (en)	1970-09-17
YU87667A (en)	1975-10-31
CH485701A (de)	1970-02-15

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NO167947B (no)	1991-09-16	Lagringsanordning for baand- eller plate-registreringsmedier
DE69113148T2 (de)	1996-03-28	Thioxo-Heterocyclen und ihre pharmazeutische Verwendung.
BR112014030091B1 (pt)	2019-01-15	processos para produzir certos 2-(piridina-3-il)tiazóis
DE69117355T2 (de)	1996-08-08	Bizyklische Pyran-Derivate und ihre Verwendung als 5-Lipoxygenasehemmer
NO146540B (no)	1982-07-12	Fremgangsmaate ved fremstilling av furocumariner
AU626549B2 (en)	1992-08-06	Chroman derivatives
NO176477B (no)	1995-01-02	Analogifremgangsmåte for fremstilling av terpaeutisk aktive 2-alkoksymetylsubstituerte kromanderivater
DK168010B1 (da)	1994-01-17	Tetrahydroisoquinolinforbindelser og farmaceutisk middel indeholdende en saadan forbindelse
SUGIHARA et al.	1987	1, 5-Benzoxathiepin Derivatives. II. Synthesis and Serotonin S2-Receptor-Blocking Activity of Aminoalkyl-Substituted 3, 4-Dihydro-2H-1, 5-benzoxathiepin-3-ols and Related Compounds
JP2874912B2 (ja)	1999-03-24	クロマン誘導体
DE2333847A1 (de)	1974-01-24	Tetrahydronaphthole, ihre salze und diese verbindungen enthaltende arzneimittel
NO770161L (no)	1977-07-21	Tiazolidinderivater og fremgangsm}te til deres fremstilling.
NO120583B (fi)	1970-11-09
NO144039B (no)	1981-03-02	Analogifremgangsmaate ved fremstilling av nye, terapeutisk virksomme benzofuranderivater
US3073826A (en)	1963-01-15	3-pyrrolidylmethyl-4-quinazolones
JPH04300880A (ja)	1992-10-23	クロマン誘導体
NO119593B (fi)	1970-06-08
NO130329B (fi)	1974-08-12
NO149775B (no)	1984-03-12	Analogifremgangsmaate for fremstilling av fenyl-pyridylamin-derivater med antidepressiv virkning
JPS59130874A (ja)	1984-07-27	アミノ基で置換された新規複素環式誘導体、その製造方法並びにこれらを含有する薬理組成物
NO120270B (fi)	1970-09-28
NO120231B (fi)	1970-09-21
DE2333846A1 (de)	1974-01-24	Aminopropanolderivate, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DK157865B (da)	1990-02-26	Fremgangsmaade til fremstilling af ranitidin og ethyleniminoderivat til anvendelse som udgangsmateriale ved fremgangsmaaden
NO164845B (no)	1990-08-13	Fremgangsmaate ved fremstilling av indanylderivater.