CH623307A5 - - Google Patents

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Info

Publication number: CH623307A5
Authority: CH; Switzerland
Prior art keywords: methyl; indole; propoxy; hydroxy; methylmercapto
Prior art date: 1974-11-16

Application number

CH345680A

Other languages

German (de)

English (en)

Inventor

Wolfgang Dr Rer Nat Kampe

Kurt Dr Ing Stach

Max Dr Rer Nat Thiel

Vet Wolfgang Dr Med Bartsch

Karl Dr Med Dietmann

Egon Dr Med Roesch

Wolfgang Prof Dr Med Schaumann

Original Assignee

Boehringer Mannheim Gmbh

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.)

1974-11-16

Filing date

1980-05-05

Publication date

1981-05-29

1974-11-16 Priority claimed from DE19742454406 external-priority patent/DE2454406A1/de

1975-02-11 Priority claimed from DE19752505681 external-priority patent/DE2505681A1/de

1975-02-26 Priority claimed from DE19752508251 external-priority patent/DE2508251C2/de

1975-06-27 Priority claimed from DE19752528771 external-priority patent/DE2528771A1/de

1980-05-05 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1981-05-29 Publication of CH623307A5 publication Critical patent/CH623307A5/de

Links

125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 39
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 26
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
150000001875 compounds Chemical class 0.000 description 18
239000000243 solution Substances 0.000 description 12
FGRJGEWVJCCOJJ-UHFFFAOYSA-N 2,2-dimethylaziridine Chemical compound CC1(C)CN1 FGRJGEWVJCCOJJ-UHFFFAOYSA-N 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 10
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
238000000034 method Methods 0.000 description 9
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
-1 pivaloyloxyalkyl Chemical group 0.000 description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
239000005711 Benzoic acid Substances 0.000 description 6
235000010233 benzoic acid Nutrition 0.000 description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
150000003839 salts Chemical class 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
CTWQPSSVUYPWOM-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-1h-indole Chemical compound C=1C=CC=2NC=CC=2C=1OCC1CO1 CTWQPSSVUYPWOM-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 description 3
125000000217 alkyl group Chemical group 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
239000000047 product Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000007787 solid Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000004183 alkoxy alkyl group Chemical group 0.000 description 2
238000001035 drying Methods 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
125000002768 hydroxyalkyl group Chemical group 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000007788 liquid Substances 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
KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
GWRBPJXLXXKTEL-UHFFFAOYSA-N 2-methyl-4-(oxiran-2-ylmethoxy)-1h-indole Chemical compound C1=CC=C2NC(C)=CC2=C1OCC1CO1 GWRBPJXLXXKTEL-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
BKAHBWRBBQERJX-UHFFFAOYSA-N 6-methyl-4-(oxiran-2-ylmethoxy)-1h-indole Chemical compound C=12C=CNC2=CC(C)=CC=1OCC1CO1 BKAHBWRBBQERJX-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 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
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
241000206672 Gelidium Species 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
229930195725 Mannitol Natural products 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
230000001800 adrenalinergic effect Effects 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000007664 blowing Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000007979 citrate buffer Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000008139 complexing agent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
ZQZRHAUMZCHPSM-UHFFFAOYSA-N indol-1-yl benzoate Chemical compound C1=CC2=CC=CC=C2N1OC(=O)C1=CC=CC=C1 ZQZRHAUMZCHPSM-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000005358 mercaptoalkyl group Chemical group 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 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
239000007858 starting material Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
239000003765 sweetening agent 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
229940095064 tartrate Drugs 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000011282 treatment Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Neurology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicinal Preparation (AREA)

CH345680A 1974-11-16 1980-05-05 CH623307A5 (es)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE19742454406 DE2454406A1 (de)	1974-11-16	1974-11-16	Neue aminopropanol-derivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
DE19752505681 DE2505681A1 (de)	1975-02-11	1975-02-11	Neue aminopropanol-derivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
DE19752508251 DE2508251C2 (de)	1975-02-26	1975-02-26	Derivate des Indols, Verfahren zu deren Herstellung sowie diese enthaltende Arzneimittel
DE19752528771 DE2528771A1 (de)	1975-06-27	1975-06-27	Neue aminopropanol-derivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel

Publications (1)

Publication Number	Publication Date
CH623307A5 true CH623307A5 (es)	1981-05-29

Family

ID=27431915

Family Applications (3)

Application Number	Title	Priority Date
CH1473575A CH622248A5 (es)	1974-11-16	1975-11-13
CH345780A CH623308A5 (es)	1974-11-16	1980-05-05
CH345680A CH623307A5 (es)	1974-11-16	1980-05-05

Family Applications Before (2)

Application Number	Title	Priority Date	Filing Date
CH1473575A CH622248A5 (es)	1974-11-16	1975-11-13
CH345780A CH623308A5 (es)	1974-11-16	1980-05-05

Country Status (21)

Country	Link
US (2)	US4076829A (es)
JP (1)	JPS5845423B2 (es)
AR (3)	AR208570A1 (es)
AT (1)	AT349004B (es)
AU (1)	AU473145B2 (es)
CA (1)	CA1051002A (es)
CH (3)	CH622248A5 (es)
CS (1)	CS199604B2 (es)
DD (1)	DD123460A5 (es)
DK (1)	DK140985C (es)
ES (1)	ES442648A1 (es)
FI (1)	FI61693C (es)
FR (1)	FR2290897A1 (es)
GB (1)	GB1471636A (es)
HU (1)	HU173308B (es)
IE (1)	IE42286B1 (es)
LU (1)	LU73808A1 (es)
NL (1)	NL7513336A (es)
PL (1)	PL100799B1 (es)
SE (1)	SE405598B (es)
SU (2)	SU649314A3 (es)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2815926A1 (de) *	1978-04-13	1979-10-18	Boehringer Mannheim Gmbh	Neue carbazolyl-(4)-oxy-propanolamin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
US4314943A (en) *	1977-07-13	1982-02-09	Mead Johnson & Company	Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols
DE2830211A1 (de) *	1977-07-21	1979-02-01	Sandoz Ag	Substituierte indol-derivate, ihre herstellung und verwendung
WO1980000152A1 (en) *	1978-07-03	1980-02-07	Sandoz Ag	3-aminopropoxy-aryl derivates,preparation and use thereof
US4495352A (en) *	1979-02-13	1985-01-22	Mead Johnson & Company	Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols
DE3068678D1 (en) *	1979-08-10	1984-08-30	Sandoz Ag	3-aminopropoxyaryl derivatives, their preparation and pharmaceutical compositions containing them
DE3030047A1 (de) *	1980-08-08	1982-03-11	Boehringer Mannheim Gmbh, 6800 Mannheim	Neue aminopropanol-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3115993A1 (de) *	1981-04-13	1982-11-11	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Neue indol-derivate, verfahren zu ihrer herstellung und pharmazeutische praeparate, die diese verbindungen enthalten
US5013732A (en) *	1984-08-06	1991-05-07	Sterling Drug Inc.	3-arylcarbonyl- and 3-cycloalkyl-carbonyl-1-aminoalkyl-1H-indoles
US5013761A (en) *	1988-06-03	1991-05-07	Eli Lilly And Company	Serotonin antagonists

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3471515A (en) *	1965-02-01	1969-10-07	Sandoz Ag	(2-hydroxy-3-substituted aminopropoxy)indoles
CH475981A (de) *	1966-12-13	1969-07-31	Sandoz Ag	Verfahren zur Herstellung neuer Indol-Derivate
GB1308029A (en) *	1969-07-25	1973-02-21	Sandoz Ltd	Indole derivatives
BE754360A (fr) *	1969-08-05	1971-02-03	Sandoz Sa	Nouveaux derives de l'indole, leur preparation et medicaments contenantdes derives
US3705907A (en) *	1970-02-19	1972-12-12	Sandoz Ltd	4-(2-hydroxy)-3-aminopropoxy)-indole derivatives
US3699123A (en) *	1970-03-24	1972-10-17	Sandoz Ltd	4-(3-amino-2-hydroxy-propoxy) indole derivatives
US3751429A (en) *	1970-03-24	1973-08-07	Sandoz Ltd	4-(3-amino-2-substituted propoxy)indole derivatives
CH535762A (de) *	1970-09-30	1973-04-15	Sandoz Ag	Verfahren zur Herstellung neuer Indolderivate
CH540253A (de) *	1971-01-07	1973-08-15	Sandoz Ag	Verfahren zur Herstellung neuer Indole

1975
- 1975-10-28 US US05/626,512 patent/US4076829A/en not_active Expired - Lifetime
- 1975-10-31 GB GB4529975A patent/GB1471636A/en not_active Expired
- 1975-11-13 CH CH1473575A patent/CH622248A5/de not_active IP Right Cessation
- 1975-11-14 AR AR261214A patent/AR208570A1/es active
- 1975-11-14 HU HU75BO1582A patent/HU173308B/hu unknown
- 1975-11-14 NL NL7513336A patent/NL7513336A/xx not_active Application Discontinuation
- 1975-11-14 CA CA239,645A patent/CA1051002A/en not_active Expired
- 1975-11-14 JP JP50137692A patent/JPS5845423B2/ja not_active Expired
- 1975-11-14 CS CS757720A patent/CS199604B2/cs unknown
- 1975-11-14 ES ES442648A patent/ES442648A1/es not_active Expired
- 1975-11-14 FR FR7534782A patent/FR2290897A1/fr active Granted
- 1975-11-14 DK DK513575A patent/DK140985C/da active
- 1975-11-14 FI FI753219A patent/FI61693C/fi not_active IP Right Cessation
- 1975-11-14 DD DD189466A patent/DD123460A5/xx unknown
- 1975-11-14 IE IE2476/75A patent/IE42286B1/en unknown
- 1975-11-14 AT AT870975A patent/AT349004B/de not_active IP Right Cessation
- 1975-11-14 SE SE7512823A patent/SE405598B/xx unknown
- 1975-11-14 SU SU752189622A patent/SU649314A3/ru active
- 1975-11-14 LU LU73808A patent/LU73808A1/xx unknown
- 1975-11-15 PL PL1975184778A patent/PL100799B1/pl unknown
- 1975-11-17 AU AU86692/75A patent/AU473145B2/en not_active Expired
1976
- 1976-05-31 AR AR263462A patent/AR213287A1/es active
- 1976-05-31 AR AR263461A patent/AR211268A1/es active
- 1976-07-19 SU SU762383853A patent/SU679135A3/ru active
1978
- 1978-09-18 US US05/943,512 patent/US4229464A/en not_active Expired - Lifetime
1980
- 1980-05-05 CH CH345780A patent/CH623308A5/de not_active IP Right Cessation
- 1980-05-05 CH CH345680A patent/CH623307A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU473145B2 (en)	1976-06-17
NL7513336A (nl)	1976-05-18
AR213287A1 (es)	1979-01-15
JPS5845423B2 (ja)	1983-10-08
JPS5175059A (es)	1976-06-29
CH622248A5 (es)	1981-03-31
AU8669275A (en)	1976-06-17
ES442648A1 (es)	1977-04-16
DD123460A5 (es)	1976-12-20
SE7512823L (sv)	1976-05-17
IE42286B1 (en)	1980-07-16
FI753219A (es)	1976-05-17
DK140985B (da)	1979-12-17
US4076829A (en)	1978-02-28
GB1471636A (en)	1977-04-27
AT349004B (de)	1979-03-12
FI61693C (fi)	1982-09-10
FI61693B (fi)	1982-05-31
AR211268A1 (es)	1977-11-15
IE42286L (en)	1976-05-16
CH623308A5 (es)	1981-05-29
ATA870975A (de)	1978-08-15
FR2290897B1 (es)	1978-11-10
LU73808A1 (es)	1976-06-11
US4229464A (en)	1980-10-21
DK513575A (da)	1976-05-17
CS199604B2 (en)	1980-07-31
HU173308B (hu)	1979-04-28
SU679135A3 (ru)	1979-08-05
FR2290897A1 (fr)	1976-06-11
SU649314A3 (ru)	1979-02-25
SE405598B (sv)	1978-12-18
CA1051002A (en)	1979-03-20
DK140985C (da)	1980-06-02
AR208570A1 (es)	1977-02-15
PL100799B1 (pl)	1978-11-30

Publication	Publication Date	Title
DE2335943C3 (de)	1979-08-09	Tricyclisch substituierte Aminoalkohole und ihre nichttoxischen Salze, Verfahren zu deren Herstellung und deren Verwendung bei der Bekämpfung von Herz- und Kreislauferkrankungen
CH623307A5 (es)	1981-05-29
CH629190A5 (en)	1982-04-15	Process for the preparation of 1-(triarylalkyl)-4-phenylpiperidine derivatives
DE1237574B (de)	1967-03-30	Verfahren zur Herstellung von Piperazinderivaten
DE2549568A1 (de)	1977-05-18	2,6-dimethyl-3-methoxycarbonyl-4- (2'-nitrophenyl)-1,4-dihydropyridin-5- carbonsaeureisobutylester, mehrere verfahren zu seiner herstellung sowie seine verwendung als coronartherapeutikum
EP0045911B1 (de)	1983-12-14	Neue Aminopropanol-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0003298B1 (de)	1981-03-25	4-Hydroxy-2-benzimidazolin-thion-Derivate, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende Arzneimittel
DE3414801A1 (de)	1985-10-24	4-(nitrophenyl)-tetrahydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE2432269A1 (de)	1976-01-22	Basisch substituierte derivate des 4-hydroxybenzimidazols und verfahren zu ihrer herstellung
DE2403786A1 (de)	1974-10-24	Neue derivate der cumarine
DE2427272A1 (de)	1976-01-08	1-(2-(beta-naphthyloxy)-aethyl)-3-methyl -pyrazolon-(5), verfahren sowie verwendung als antithrombotikum
CH630919A5 (de)	1982-07-15	Verfahren zur herstellung von aminopropanol-derivaten.
DE2235114A1 (de)	1973-02-01	Neue dioxocincarboxamidderivate
AT360515B (de)	1981-01-12	Verfahren zur herstellung von neuen 4-hydroxy- indol-derivaten und ihren salzen
DE2356005A1 (de)	1975-05-22	Neue 7-amino-imidazo eckige klammer auf 1,2-a eckige klammer zu pyrimidine, diese enthaltende arzneimittel sowie verfahren zu deren herstellung
DE1670143C3 (es)	1974-05-30
DE1545786A1 (de)	1969-12-11	Verfahren zur Herstellung von Carbonsaeure-N-methylpiperaziden
AT360514B (de)	1981-01-12	Verfahren zur herstellung von neuen 4-hydroxy- indol-derivaten und ihren salzen
AT334339B (de)	1976-01-10	Verfahren zur herstellung von neuen alpha- (1-bis-arylalkylaminoalkyl) -aralkoxybenzylalkoholen
DE2626890A1 (de)	1977-12-29	Neue derivate des indols, verfahren zu deren herstellung sowie diese enthaltende arzneimittel
AT315870B (de)	1974-06-10	Verfahren zur Herstellung von neuen Adenin-Derivaten und von deren Salzen
AT375650B (de)	1984-08-27	Verfahren zur herstellung von neuen 4-hydroxy-2 -benzimidazolinon-derivaten und von deren salzen, razematen und optisch aktiven formen
AT247345B (de)	1966-06-10	Verfahren zur Herstellung von neuen Piperazinverbindungen
DE2166258C3 (de)	1975-09-25	Aminoalkohole, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneipräparate
AT276372B (de)	1969-11-25	Verfahren zur Herstellung von neuen N-(tert.-Aminoalkyl)-amidderivaten und deren Säureadditionssalzen

Legal Events

Date	Code	Title	Description
1988-07-29	PL	Patent ceased
2024-10-31	PL	Patent ceased