NO813446L - 1,5-bis(1,4-benzodioksin-2yl)-3-azapentan-1,5-dioler, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse forbindelser samt deres terapeutiske anvendelse - Google Patents

1,5-bis(1,4-benzodioksin-2yl)-3-azapentan-1,5-dioler, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse forbindelser samt deres terapeutiske anvendelse

Info

Publication number: NO813446L
Authority: NO; Norway
Prior art keywords: benzodioxin; dihydro; compound; mixture; formula
Prior art date: 1980-10-14

Application number

NO813446A

Other languages

English (en)

Norwegian (no)

Inventor

Charles Ferdinand Muebner

Heinz Werner Gschwend

Original Assignee

Ciba Geigy 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.)

1980-10-14

Filing date

1981-10-13

Publication date

1982-04-15

1981-10-13 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1982-04-15 Publication of NO813446L publication Critical patent/NO813446L/no

Links

150000001875 compounds Chemical class 0.000 title claims description 58
238000000034 method Methods 0.000 title claims description 25
238000002360 preparation method Methods 0.000 title claims description 9
-1 1,4-BENZODIOXIN-2YL Chemical class 0.000 title description 11
239000000825 pharmaceutical preparation Substances 0.000 title description 4
230000001225 therapeutic effect Effects 0.000 title description 2
239000000203 mixture Substances 0.000 claims description 60
150000003839 salts Chemical class 0.000 claims description 32
239000002253 acid Substances 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 15
239000007858 starting material Substances 0.000 claims description 15
238000010992 reflux Methods 0.000 claims description 13
125000002252 acyl group Chemical group 0.000 claims description 11
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
229910021529 ammonia Inorganic materials 0.000 claims description 5
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 claims description 4
238000004587 chromatography analysis Methods 0.000 claims description 3
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239000011260 aqueous acid Substances 0.000 claims description 2
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150000004681 metal hydrides Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
239000000243 solution Substances 0.000 description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
239000002585 base Substances 0.000 description 15
239000000155 melt Substances 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
239000000047 product Substances 0.000 description 12
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239000012299 nitrogen atmosphere Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
239000000706 filtrate Substances 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
230000003276 anti-hypertensive effect Effects 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
206010020772 Hypertension Diseases 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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229920002472 Starch Polymers 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
239000013543 active substance Substances 0.000 description 6
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
238000009835 boiling Methods 0.000 description 6
235000013877 carbamide Nutrition 0.000 description 6
239000012458 free base Substances 0.000 description 6
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 5
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239000003054 catalyst Substances 0.000 description 5
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239000012948 isocyanate Substances 0.000 description 5
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IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
239000000908 ammonium hydroxide Substances 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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229960000583 acetic acid Drugs 0.000 description 3
238000010171 animal model Methods 0.000 description 3
229940030600 antihypertensive agent Drugs 0.000 description 3
239000002220 antihypertensive agent Substances 0.000 description 3
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125000001589 carboacyl group Chemical group 0.000 description 3
239000003795 chemical substances by application Substances 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
238000003776 cleavage reaction Methods 0.000 description 3
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230000000694 effects Effects 0.000 description 3
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238000006460 hydrolysis reaction Methods 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
229940098779 methanesulfonic acid Drugs 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
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239000002904 solvent Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
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YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
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DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
AQWBILDHBRYPRN-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-3-yl)-2-[[2-(2,3-dihydro-1,4-benzodioxin-3-yl)-2-hydroxyethyl]amino]ethanol;hydrochloride Chemical compound Cl.C1OC2=CC=CC=C2OC1C(O)CNCC(O)C1OC2=CC=CC=C2OC1 AQWBILDHBRYPRN-UHFFFAOYSA-N 0.000 description 2
YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 2
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
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OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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125000001931 aliphatic group Chemical group 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
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239000007864 aqueous solution Substances 0.000 description 2
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238000007327 hydrogenolysis reaction Methods 0.000 description 2
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238000002211 ultraviolet spectrum Methods 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO813446A 1980-10-14 1981-10-13 1,5-bis(1,4-benzodioksin-2yl)-3-azapentan-1,5-dioler, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse forbindelser samt deres terapeutiske anvendelse NO813446L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/196,503 US4313955A (en)	1980-10-14	1980-10-14	1,5-Bis(1,4-benzodioxin-2-yl)-3-azapentane-1,5-diols

Publications (1)

Publication Number	Publication Date
NO813446L true NO813446L (no)	1982-04-15

Family

ID=22725667

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO813446A NO813446L (no)	1980-10-14	1981-10-13	1,5-bis(1,4-benzodioksin-2yl)-3-azapentan-1,5-dioler, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse forbindelser samt deres terapeutiske anvendelse

Country Status (21)

Country	Link
US (1)	US4313955A (es)
EP (1)	EP0050585B1 (es)
JP (1)	JPS5795982A (es)
KR (1)	KR830007618A (es)
AR (1)	AR227441A1 (es)
AT (1)	ATE9694T1 (es)
AU (1)	AU548164B2 (es)
DD (1)	DD201678A5 (es)
DE (1)	DE3166503D1 (es)
DK (1)	DK454181A (es)
ES (3)	ES8303403A1 (es)
FI (1)	FI813154L (es)
GB (1)	GB2085008B (es)
GR (1)	GR75089B (es)
HU (1)	HU187378B (es)
IE (1)	IE51645B1 (es)
IL (1)	IL64033A (es)
NO (1)	NO813446L (es)
NZ (1)	NZ198619A (es)
PT (1)	PT73812B (es)
ZA (1)	ZA817048B (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4380653A (en) *	1980-10-14	1983-04-19	Ciba-Geigy Corporation	1,5-Bis-(1,4-benzodioxin-2-yl)-3-azapentane-1,5-diols
US4471128A (en) *	1981-09-08	1984-09-11	Ciba-Geigy Corporation	1,5-Bis-(1,4-benzodioxin-2-yl)-3-azapentane-1,5-diols
CA1337429C (en) *	1983-12-05	1995-10-24	Guy Rosalia Eugene Van Lommen	Derivatives of 2,2'-iminobisethanol
US4654362A (en) *	1983-12-05	1987-03-31	Janssen Pharmaceutica, N.V.	Derivatives of 2,2'-iminobisethanol

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1038333A (en) *	1963-02-13	1966-08-10	Ici Ltd	Pharmaceutical compositions
US4187313A (en) *	1978-01-30	1980-02-05	Ciba-Geigy Corporation	2-Aminoethyl-1,4-benzodioxans
US4261907A (en) *	1978-01-30	1981-04-14	Ciba-Geigy Corporation	Stereospecific process
DE2827801A1 (de) *	1978-06-24	1980-01-10	Kali Chemie Pharma Gmbh	Neue n tief 1 -benzoyl-n tief 2 -phenyl-1,3-diaminopropan-2-ole, verfahren zu deren herstellung und arzneimittel
US4212808A (en) *	1979-03-09	1980-07-15	Ciba-Geigy Corporation	2-Oxiranyl-1,4-benzodioxans

1980
- 1980-10-14 US US06/196,503 patent/US4313955A/en not_active Expired - Lifetime
1981
- 1981-10-08 AT AT81810403T patent/ATE9694T1/de not_active IP Right Cessation
- 1981-10-08 DE DE8181810403T patent/DE3166503D1/de not_active Expired
- 1981-10-08 EP EP81810403A patent/EP0050585B1/de not_active Expired
- 1981-10-09 GR GR66245A patent/GR75089B/el unknown
- 1981-10-12 IL IL64033A patent/IL64033A/xx unknown
- 1981-10-12 FI FI813154A patent/FI813154L/fi not_active Application Discontinuation
- 1981-10-12 GB GB8130712A patent/GB2085008B/en not_active Expired
- 1981-10-13 PT PT73812A patent/PT73812B/pt unknown
- 1981-10-13 AU AU76290/81A patent/AU548164B2/en not_active Ceased
- 1981-10-13 IE IE2399/81A patent/IE51645B1/en unknown
- 1981-10-13 HU HU812953A patent/HU187378B/hu unknown
- 1981-10-13 DK DK454181A patent/DK454181A/da not_active Application Discontinuation
- 1981-10-13 ZA ZA817048A patent/ZA817048B/xx unknown
- 1981-10-13 NO NO813446A patent/NO813446L/no unknown
- 1981-10-13 ES ES506212A patent/ES8303403A1/es not_active Expired
- 1981-10-13 AR AR287078A patent/AR227441A1/es active
- 1981-10-13 NZ NZ198619A patent/NZ198619A/en unknown
- 1981-10-14 JP JP56162905A patent/JPS5795982A/ja active Pending
- 1981-10-14 DD DD81234081A patent/DD201678A5/de unknown
- 1981-10-14 KR KR1019810003878A patent/KR830007618A/ko unknown
1982
- 1982-10-06 ES ES516272A patent/ES516272A0/es active Granted
1983
- 1983-11-30 ES ES527677A patent/ES527677A0/es active Granted

Also Published As

Publication number	Publication date
JPS5795982A (en)	1982-06-15
ZA817048B (en)	1982-09-29
ATE9694T1 (de)	1984-10-15
GB2085008B (en)	1984-04-18
ES8600282A1 (es)	1985-10-01
EP0050585B1 (de)	1984-10-03
DK454181A (da)	1982-04-15
IE812399L (en)	1982-04-14
ES8502437A1 (es)	1985-01-01
HU187378B (en)	1985-12-28
KR830007618A (ko)	1983-11-04
GB2085008A (en)	1982-04-21
ES506212A0 (es)	1983-02-01
NZ198619A (en)	1985-07-31
PT73812A (en)	1981-11-01
AR227441A1 (es)	1982-10-29
DD201678A5 (de)	1983-08-03
DE3166503D1 (en)	1984-11-08
GR75089B (es)	1984-07-13
EP0050585A1 (de)	1982-04-28
ES516272A0 (es)	1985-01-01
AU7629081A (en)	1982-04-22
IL64033A0 (en)	1982-01-31
US4313955A (en)	1982-02-02
ES527677A0 (es)	1985-10-01
IL64033A (en)	1984-08-31
PT73812B (en)	1983-06-20
FI813154L (fi)	1982-04-15
IE51645B1 (en)	1987-01-21
ES8303403A1 (es)	1983-02-01
AU548164B2 (en)	1985-11-28

Publication	Publication Date	Title
CA1263653A (en)	1989-12-05	Tetrahydro-benzthiazoles, the preparation thereof and their use as intermediate products or as pharmaceuticals
CA1124241A (en)	1982-05-25	N-alkylated aminoalcohols and their salts, processes for their preparation and pharmaceutical preparations containing these compounds
FI76331B (fi)	1988-06-30	Foerfarande foer framstaellning av terapeutiskt aktiva substituerade 4-aminometylenkromaner och kromener.
NO174467B (no)	1994-01-31	Analogifremgangsmaate for fremstilling av terapeutisk aktive kromanderivater
IL110689A (en)	1998-12-27	Vasodilators containing aryloxylalkyldiamine, certain new compounds and their preparation
NO316990B1 (no)	2004-07-19	Fremgangsmate for fremstilling av en blanding av 1,4-benzodioksanderivater og et 1,4-benzodioksanderivat
NO167658B (no)	1991-08-19	Analogifremgangsmaate for fremstilling av nye, terapeutiskaktive difenylpropylaminderivater.
CZ54095A3 (en)	1995-11-15	Acetamides as such and for suppressing diseases, process of their preparation and their use for the preparation of medicaments, pharmaceutical preparations based thereon and process of their preparation
KR0150780B1 (ko)	1998-10-15	크로만 유도체
US4187313A (en)	1980-02-05	2-Aminoethyl-1,4-benzodioxans
NO813446L (no)	1982-04-15	1,5-bis(1,4-benzodioksin-2yl)-3-azapentan-1,5-dioler, fremgangsmaate til deres fremstilling, farmasoeytiske preparater inneholdende disse forbindelser samt deres terapeutiske anvendelse
US4397860A (en)	1983-08-09	Benzodioxanyl imidazoline compounds, compositions and use
CA2722986A1 (en)	2009-11-05	Modulators of dopamine neurotransmission
DE69507652T2 (de)	1999-09-09	Alkylaminoindanverbindungen, Verfahren zu deren Herstellung und diese enthaltenden pharmazeutische Zusammenstellungen
NO143625B (no)	1980-12-08	Analogifremgangsmaate for fremstilling av 2-metoksy-benzamider
CA1185606A (en)	1985-04-16	Benzodioxane imidazoline compounds as antihypertensives
US4380653A (en)	1983-04-19	1,5-Bis-(1,4-benzodioxin-2-yl)-3-azapentane-1,5-diols
NO841661L (no)	1984-10-29	Analogifremgangsmaate for fremstilling av terapeutisk aktive 4-fenyl-tetrahydro-furano-pyridin-derivater
CA1263656A (en)	1989-12-05	Aryloxycycloalkanolaminoalkylene aryl ketones
US4471127A (en)	1984-09-11	1-5-Bis-(1,4-benzodioxin-2-yl)-3-azapentane-1,5-diols
CA1169079A (en)	1984-06-12	1,5-bis-(1,4-benzodioxin-2-yl)-3-azapentane-1,5-diols, process for their manufacture, pharmaceutical preparations containing these compounds and their therapeutic application
US4471128A (en)	1984-09-11	1,5-Bis-(1,4-benzodioxin-2-yl)-3-azapentane-1,5-diols
JPH01102080A (ja)	1989-04-19	アザクロマン誘導体
NO142103B (no)	1980-03-24	Soppdrepende middel for anvendelse i og paa landbruksprodukter
JPS5931753A (ja)	1984-02-20	３−（ウレイドシクロヘキシルアミノ）−プロパン−１，２−ジオ−ル誘導体及びその製造方法、並びに該誘導体を含有する医薬