DE2148552A1 - Verfahren zur Herstellung neuer heterocyclischer Verbindungen - Google Patents

Verfahren zur Herstellung neuer heterocyclischer Verbindungen

Info

Publication number: DE2148552A1
Authority: DE; Germany
Prior art keywords: formula; compounds; addition salts; indole; acid addition
Prior art date: 1970-09-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

DE19712148552

Other languages

German (de)

English (en)

Inventor

Fritz Seemann

Franz Troxler

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Sandoz AG

Original Assignee

Sandoz 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.)

1970-09-30

Filing date

1971-09-29

Publication date

1972-04-06

1971-09-29 Application filed by Sandoz AG filed Critical Sandoz AG

1972-04-06 Publication of DE2148552A1 publication Critical patent/DE2148552A1/de

Status Pending legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 11
238000002360 preparation method Methods 0.000 title claims description 3
150000002391 heterocyclic compounds Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 21
-1 2-methoxyethoxy Chemical group 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 5
150000004678 hydrides Chemical class 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 4
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
239000012279 sodium borohydride Substances 0.000 claims description 4
229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
125000000304 alkynyl group Chemical group 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
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 claims description 2
150000004645 aluminates Chemical class 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
GQOGWJCFXDCGIB-UHFFFAOYSA-N 2-(4-phenylmethoxy-1H-indol-2-yl)acetic acid Chemical compound C(C1=CC=CC=C1)OC1=C2C=C(NC2=CC=C1)CC(=O)O GQOGWJCFXDCGIB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
238000011282 treatment Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
MPNNSHITDFJMOW-UHFFFAOYSA-N CC(C)NCC(COC1=C(C=C(CC(OC)=O)N2)C2=CC=C1)O Chemical compound CC(C)NCC(COC1=C(C=C(CC(OC)=O)N2)C2=CC=C1)O MPNNSHITDFJMOW-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
238000006264 debenzylation reaction Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
PXYRYFLSOOBYGT-UHFFFAOYSA-N 2-(4-phenylmethoxy-1H-indol-2-yl)acetonitrile Chemical compound C(C1=CC=CC=C1)OC1=C2C=C(NC2=CC=C1)CC#N PXYRYFLSOOBYGT-UHFFFAOYSA-N 0.000 description 1
MAYWEFVBIQEREO-UHFFFAOYSA-N 2-(4-phenylmethoxy-1H-indol-2-yl)acetyl chloride Chemical compound C(C1=CC=CC=C1)OC1=C2C=C(NC2=CC=C1)CC(=O)Cl MAYWEFVBIQEREO-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
208000001871 Tachycardia Diseases 0.000 description 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
230000001800 adrenalinergic effect Effects 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
238000010009 beating Methods 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
208000029078 coronary artery disease Diseases 0.000 description 1
239000013078 crystal Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
230000001834 epinephrinelike Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
210000002837 heart atrium Anatomy 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
230000001660 hyperkinetic effect Effects 0.000 description 1
230000001969 hypertrophic effect Effects 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
LYBKPDDZTNUNNM-UHFFFAOYSA-N isopropylbenzylamine Chemical compound CC(C)NCC1=CC=CC=C1 LYBKPDDZTNUNNM-UHFFFAOYSA-N 0.000 description 1
229940039009 isoproterenol Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
HBQGEXLBXNFINE-UHFFFAOYSA-N methyl 2-[4-[2-hydroxy-4-phenyl-3-(propan-2-ylamino)butoxy]-1H-indol-2-yl]acetate Chemical compound COC(CC=1NC2=CC=CC(=C2C1)OCC(C(CC1=CC=CC=C1)NC(C)C)O)=O HBQGEXLBXNFINE-UHFFFAOYSA-N 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
239000000203 mixture Substances 0.000 description 1
230000003387 muscular Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
206010042431 subvalvular aortic stenosis Diseases 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- 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)
Indole Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DE19712148552 1970-09-30 1971-09-29 Verfahren zur Herstellung neuer heterocyclischer Verbindungen Pending DE2148552A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1446570A CH535762A (de)	1970-09-30	1970-09-30	Verfahren zur Herstellung neuer Indolderivate

Publications (1)

Publication Number	Publication Date
DE2148552A1 true DE2148552A1 (de)	1972-04-06

Family

ID=4401057

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19712148552 Pending DE2148552A1 (de)	1970-09-30	1971-09-29	Verfahren zur Herstellung neuer heterocyclischer Verbindungen

Country Status (10)

Country	Link
US (1)	US3758502A (2)
AU (1)	AU3403771A (2)
BE (1)	BE773205A (2)
CH (1)	CH535762A (2)
DE (1)	DE2148552A1 (2)
ES (1)	ES395495A1 (2)
FR (1)	FR2108099B1 (2)
GB (1)	GB1356406A (2)
NL (1)	NL7112937A (2)
SE (1)	SE369523B (2)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4076829A (en) *	1974-11-16	1978-02-28	Boehringer Mannheim Gmbh	Aminopropanol compounds and compositions for the treatment of cardiac and circulatory diseases
US4152446A (en) *	1974-11-16	1979-05-01	Boehringer Mannheim Gmbh	Aminopropanol compounds and compositions for the treatment of cardiac and circulatory diseases
CA1139760A (en) *	1979-03-07	1983-01-18	Makiko Sakai	1,4-dioxaspiro¬4,5\| decene compounds
EP0068563A3 (en) *	1981-06-23	1983-06-15	THE PROCTER & GAMBLE COMPANY	Heterocyclic acetic acid compounds and compositions for treating bone diseases

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1948507C2 (de) *	1969-09-25	1982-10-21	Sandoz-Patent-GmbH, 7850 Lörrach	4-(2-Hydroxy-3-aminopropoxy)-indolderivate, ihre Salze, Verfahren zu ihrer Herstellung und Heilmittel

1970
- 1970-09-30 CH CH1446570A patent/CH535762A/de not_active IP Right Cessation
1971
- 1971-09-21 NL NL7112937A patent/NL7112937A/xx unknown
- 1971-09-22 US US00182911A patent/US3758502A/en not_active Expired - Lifetime
- 1971-09-27 GB GB4481471A patent/GB1356406A/en not_active Expired
- 1971-09-28 ES ES395495A patent/ES395495A1/es not_active Expired
- 1971-09-28 BE BE773205A patent/BE773205A/xx unknown
- 1971-09-28 SE SE12236/71A patent/SE369523B/xx unknown
- 1971-09-29 AU AU34037/71A patent/AU3403771A/en not_active Expired
- 1971-09-29 FR FR7134985A patent/FR2108099B1/fr not_active Expired
- 1971-09-29 DE DE19712148552 patent/DE2148552A1/de active Pending

Also Published As

Publication number	Publication date
AU3403771A (en)	1973-04-05
FR2108099B1 (2)	1975-04-18
FR2108099A1 (2)	1972-05-12
SE369523B (2)	1974-09-02
US3758502A (en)	1973-09-11
ES395495A1 (es)	1974-11-01
GB1356406A (en)	1974-06-12
NL7112937A (2)	1972-04-05
BE773205A (fr)	1972-03-28
CH535762A (de)	1973-04-15

Publication	Publication Date	Title
DE2113379A1 (de)	1971-10-07	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
DE2447756A1 (de)	1975-04-10	Verfahren zur herstellung neuer heterocyclischer verbindungen
DE2230426A1 (de)	1973-01-11	Verfahren zur herstellung neuer heterocyclischer verbindungen
DE2038482A1 (de)	1971-02-18	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
DE2148552A1 (de)	1972-04-06	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
AT266832B (de)	1968-12-10	Verfahren zur Herstellung von neuen Oxazolidinderivaten und ihren Salzen
DE3102597C2 (2)	1990-07-05
DE2025790A1 (de)	1970-12-17	Verfahren zur Herstellung neuer tricyclischer Verbindungen
DE2235667A1 (de)	1973-03-01	Hexahydrobenz/e/indolderivate
DE2200204A1 (de)	1972-07-27	Verfahren zur Herstellung neuer heterozyklischer Verbindungen
AT213885B (de)	1961-03-10	Verfahren zur Herstellung von neuen Indol-Derivaten
AT241463B (de)	1965-07-26	Verfahren zur Herstellung neuer Dibenzocycloheptanderivate
AT313893B (de)	1974-03-11	Verfahren zur Herstellung neuer Indolderivate und ihrer Salze
AT303025B (de)	1972-10-15	Verfahren zur herstellung neuer indolderivate und ihrer saeureadditionssalze
DE1470275C (de)	1973-04-19	Oxazohdon (2)-denvate und Ver fahren zu ihrer Herstellung
AT205038B (de)	1959-08-25	Verfahren zur Herstellung neuer, in 10-Stellung substituierter 11-Oxo-dibenzo-[b, f]-thia-[1]-aza-[4]-cycloheptadien-[2,6]-Verbindungen
CH514615A (de)	1971-10-31	Verfahren zur Herstellung von neuen Oxazolidinderivaten
CH548390A (de)	1974-04-30	Verfahren zur herstellung neuer oxindole.
CH535764A (de)	1973-04-15	Verfahren zur Herstellung neuer Indolderivate
CH547801A (de)	1974-04-11	Verfahren zur herstellung neuer oxindole.
CH621330A5 (2)	1981-01-30
DE2621090A1 (de)	1976-11-25	2-(p-hydroxyphenyl)-3-amino-1-propanol-derivate, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
CH527188A (de)	1972-08-31	Verfahren zur Herstellung neuer Indolderivate
CH513854A (de)	1971-10-15	Verfahren zur Herstellung neuer Indolderivate
CH545784A (en)	1974-02-15	Beta blocking and anti-arrhythmic indole derivs - prepd by catalytic de-benzylation of 4-(3-benzyl aminopropoxy) indoles