ES357503A1 - Procedimiento para la preparacion de derivados de oxazolo (4,3-a) isoquinolina. - Google Patents

Procedimiento para la preparacion de derivados de oxazolo (4,3-a) isoquinolina.

Info

Publication number: ES357503A1
Authority: ES; Spain
Prior art keywords: general formula; acid addition; addition salt; tetrahydroisoquinoline; alpha
Prior art date: 1967-08-25
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.): Expired

Application number

ES357503A

Other languages

English (en)

Spanish (es)

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.)

1967-08-25

Filing date

1968-08-23

Publication date

1970-03-16

1968-08-23 Application filed by Sandoz AG filed Critical Sandoz AG

1970-03-16 Publication of ES357503A1 publication Critical patent/ES357503A1/es

Status Expired legal-status Critical Current

Links

BNZWLTVMPQNISM-UHFFFAOYSA-N [1,3]oxazolo[4,5-h]isoquinoline Chemical class C1=CN=CC2=C(OC=N3)C3=CC=C21 BNZWLTVMPQNISM-UHFFFAOYSA-N 0.000 title 1
239000002253 acid Substances 0.000 abstract 11
150000003839 salts Chemical group 0.000 abstract 10
150000001875 compounds Chemical class 0.000 abstract 7
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 5
238000006243 chemical reaction Methods 0.000 abstract 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
229910052801 chlorine Inorganic materials 0.000 abstract 3
229910052739 hydrogen Inorganic materials 0.000 abstract 3
239000001257 hydrogen Substances 0.000 abstract 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
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 abstract 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 2
125000001309 chloro group Chemical group Cl* 0.000 abstract 2
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 abstract 2
229910052731 fluorine Inorganic materials 0.000 abstract 2
239000011737 fluorine Substances 0.000 abstract 2
239000012442 inert solvent Substances 0.000 abstract 2
229910052744 lithium Inorganic materials 0.000 abstract 2
239000003960 organic solvent Substances 0.000 abstract 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
229910052700 potassium Inorganic materials 0.000 abstract 2
229910052708 sodium Inorganic materials 0.000 abstract 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
BQIIGTSQOCWPDH-UHFFFAOYSA-N 1-benzyl-3,4-dihydroisoquinoline Chemical compound N=1CCC2=CC=CC=C2C=1CC1=CC=CC=C1 BQIIGTSQOCWPDH-UHFFFAOYSA-N 0.000 abstract 1
XZRLWBLXXXGHIR-UHFFFAOYSA-N 1-phenyl-1,5,6,10b-tetrahydro-[1,3]oxazolo[4,3-a]isoquinolin-3-imine Chemical class C1(=CC=CC=C1)C1OC(N2C1C1=CC=CC=C1CC2)=N XZRLWBLXXXGHIR-UHFFFAOYSA-N 0.000 abstract 1
HIRCCKPODGFADB-UHFFFAOYSA-N 2-benzoyl-1h-isoquinoline-1-carbonitrile Chemical compound C1=CC2=CC=CC=C2C(C#N)N1C(=O)C1=CC=CC=C1 HIRCCKPODGFADB-UHFFFAOYSA-N 0.000 abstract 1
SERBNUYNEAQHNJ-UHFFFAOYSA-N 2-phenyl-n-(2-phenylethyl)acetamide Chemical compound C=1C=CC=CC=1CCNC(=O)CC1=CC=CC=C1 SERBNUYNEAQHNJ-UHFFFAOYSA-N 0.000 abstract 1
GXMIBCBYYGBDOM-UHFFFAOYSA-N 3,4-dihydroisoquinolin-1-yl(phenyl)methanone Chemical compound N=1CCC2=CC=CC=C2C=1C(=O)C1=CC=CC=C1 GXMIBCBYYGBDOM-UHFFFAOYSA-N 0.000 abstract 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
230000002378 acidificating effect Effects 0.000 abstract 1
239000004480 active ingredient Substances 0.000 abstract 1
229910052783 alkali metal Inorganic materials 0.000 abstract 1
-1 alkali metal isocyanate Chemical class 0.000 abstract 1
125000000217 alkyl group Chemical group 0.000 abstract 1
230000000578 anorexic effect Effects 0.000 abstract 1
230000001430 anti-depressive effect Effects 0.000 abstract 1
239000000935 antidepressant agent Substances 0.000 abstract 1
229940005513 antidepressants Drugs 0.000 abstract 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
150000003935 benzaldehydes Chemical class 0.000 abstract 1
239000011575 calcium Substances 0.000 abstract 1
229910052791 calcium Inorganic materials 0.000 abstract 1
VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 abstract 1
239000001639 calcium acetate Substances 0.000 abstract 1
235000011092 calcium acetate Nutrition 0.000 abstract 1
229960005147 calcium acetate Drugs 0.000 abstract 1
125000004432 carbon atom Chemical group C* 0.000 abstract 1
239000003054 catalyst Substances 0.000 abstract 1
238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
239000000460 chlorine Substances 0.000 abstract 1
239000003085 diluting agent Substances 0.000 abstract 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 abstract 1
239000003937 drug carrier Substances 0.000 abstract 1
239000012458 free base Substances 0.000 abstract 1
239000012948 isocyanate Substances 0.000 abstract 1
150000002642 lithium compounds Chemical class 0.000 abstract 1
229910052760 oxygen Inorganic materials 0.000 abstract 1
239000001301 oxygen Substances 0.000 abstract 1
239000008194 pharmaceutical composition Substances 0.000 abstract 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 1
229910052697 platinum Inorganic materials 0.000 abstract 1
239000011591 potassium Substances 0.000 abstract 1
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Substances [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 abstract 1
235000011056 potassium acetate Nutrition 0.000 abstract 1
238000007363 ring formation reaction Methods 0.000 abstract 1
239000011734 sodium Substances 0.000 abstract 1
239000001632 sodium acetate Substances 0.000 abstract 1
235000017281 sodium acetate Nutrition 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)

ES357503A 1967-08-25 1968-08-23 Procedimiento para la preparacion de derivados de oxazolo (4,3-a) isoquinolina. Expired ES357503A1 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US66321867A	1967-08-25	1967-08-25
US73095768A	1968-05-21	1968-05-21

Publications (1)

Publication Number	Publication Date
ES357503A1 true ES357503A1 (es)	1970-03-16

Family

ID=27098701

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
ES357503A Expired ES357503A1 (es)	1967-08-25	1968-08-23	Procedimiento para la preparacion de derivados de oxazolo (4,3-a) isoquinolina.
ES373529A Expired ES373529A1 (es)	1967-08-25	1969-11-14	Procedimiento para la preparacion de derivados de oxazolo (4,3-a) isoquinolina.
ES389793A Expired ES389793A1 (es)	1967-08-25	1971-04-01	Procedimiento para la obtencion de derivados de tetrahi- droisoquinolina.

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
ES373529A Expired ES373529A1 (es)	1967-08-25	1969-11-14	Procedimiento para la preparacion de derivados de oxazolo (4,3-a) isoquinolina.
ES389793A Expired ES389793A1 (es)	1967-08-25	1971-04-01	Procedimiento para la obtencion de derivados de tetrahi- droisoquinolina.

Country Status (8)

Country	Link
JP (1)	JPS4826019B1 (de)
BE (1)	BE719921A (de)
CH (2)	CH498145A (de)
DE (1)	DE1795189A1 (de)
ES (3)	ES357503A1 (de)
FR (2)	FR1587682A (de)
GB (1)	GB1235002A (de)
SE (1)	SE333144B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS51147818A (en) *	1975-06-11	1976-12-18	Aisin Seiki Co Ltd	Seat slide adjusting device
DE102007006795B3 (de) *	2007-02-12	2008-04-03	Takraf Gmbh	Einrichtung zur staubfreien Schüttgutübergabe

1968
- 1968-08-02 CH CH1327170A patent/CH498145A/de not_active IP Right Cessation
- 1968-08-02 CH CH1157968A patent/CH498144A/de not_active IP Right Cessation
- 1968-08-09 GB GB38266/68A patent/GB1235002A/en not_active Expired
- 1968-08-20 SE SE1118068A patent/SE333144B/xx unknown
- 1968-08-21 DE DE19681795189 patent/DE1795189A1/de active Pending
- 1968-08-23 BE BE719921D patent/BE719921A/xx unknown
- 1968-08-23 ES ES357503A patent/ES357503A1/es not_active Expired
- 1968-08-23 FR FR1587682D patent/FR1587682A/fr not_active Expired
- 1968-11-21 FR FR174697A patent/FR8101M/fr not_active Expired
1969
- 1969-11-14 ES ES373529A patent/ES373529A1/es not_active Expired
1971
- 1971-04-01 ES ES389793A patent/ES389793A1/es not_active Expired
- 1971-09-17 JP JP7185671A patent/JPS4826019B1/ja active Pending

Also Published As

Publication number	Publication date
SE333144B (sv)	1971-03-08
CH498145A (de)	1970-10-31
JPS4826019B1 (de)	1973-08-03
ES373529A1 (es)	1972-06-01
FR1587682A (de)	1970-03-27
GB1235002A (en)	1971-06-09
ES389793A1 (es)	1974-03-01
CH498144A (de)	1970-10-31
DE1795189A1 (de)	1972-01-05
FR8101M (de)	1970-07-27
BE719921A (de)	1969-02-24

Publication	Publication Date	Title
NO810479L (no)	1981-08-14	Fremgangsmaate for fremstilling av terapeutisk aktive substituerte imidazolderivater
GB1178034A (en)	1970-01-14	Hydroxy-Cyclohexylamines
GB1294763A (en)	1972-11-01	3-oxo-2,3-dihydro-1,4-benzoxazine derivatives
NO824062L (no)	1983-06-06	Fremgangsmaate for fremstilling av terapeutisk aktive imidazol-derivater.
GB1237008A (en)	1971-06-30	Novel indoline derivatives
GB1503091A (en)	1978-03-08	Thiazolo(3,4-b)isoquinoline derivatives
GB1511463A (en)	1978-05-17	1-acylamino methyl-1,2,3,4-tetrahydroisoquinolines
GB1513320A (en)	1978-06-07	N-propargyl-2-phenylamino-2-imidazolines
ES357503A1 (es)	1970-03-16	Procedimiento para la preparacion de derivados de oxazolo (4,3-a) isoquinolina.
GB1425578A (en)	1976-02-18	Piperidine derivatives
GB1131164A (en)	1968-10-23	Novel halogen-substituted tetrahydroquinazoline derivatives, their preparation and compositions containing them
GB1198931A (en)	1970-07-15	Benzoxazine Derivatives, the preparation thereof and Compositions containing the same
GB1529251A (en)	1978-10-18	9,10-dihydroergopeptines
GB1306511A (en)	1973-02-14	Imidazoline derivatives
GB1183673A (en)	1970-03-11	Novel Quinazolinone Derivatives
IE34139B1 (en)	1975-02-19	4-phenyl-butric acid derivatives
GB1242096A (en)	1971-08-11	Benzobenzofuranooxepine compounds and process for preparing the same
GB1276719A (en)	1972-06-07	Benzomorphan derivatives and their salts
GB1445127A (en)	1976-08-04	Benzocycloheptathiophene derivatives
GB1341401A (en)	1973-12-19	Methylenedioxy quinazoline derivatives
GB1334296A (en)	1973-10-17	3-aryloxy-8-carbamoylnortropanes
GB1453910A (en)	1976-10-27	Benzazepine derivatives
GB1182639A (en)	1970-02-25	Novel Tricyclic Amines and a Process for the Manufacture Thereof
ES369679A1 (es)	1971-06-01	Procedimiento para la preparacion de n-(diaril-piridil-me- til)-imidazoles.
Vaughan Jr et al.	1948	Antihistamine Agents. II. Furan Derivatives