CA1066283A - 2,5-dimethyl-thieno-(3,2-f)-morphan and intermediates - Google Patents

2,5-dimethyl-thieno-(3,2-f)-morphan and intermediates

Info

Publication number: CA1066283A
Authority: CA; Canada
Prior art keywords: thenyl; methyl; dimethyl; iii; pyridine
Prior art date: 1975-09-20
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

CA261,490A

Other languages

English (en)

French (fr)

Inventor

Cristobal Martinez Roldan

Jorge Canals Cabiro

Fernando Rabadan Peinado

Ricardo Granados Jarque

Mercedes Alvarez Domingo

Juan Bosch Cartes

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.)

Laboratorios Made SA

Original Assignee

Laboratorios Made SA

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.)

1975-09-20

Filing date

1976-09-17

Publication date

1979-11-13

1976-09-17 Application filed by Laboratorios Made SA filed Critical Laboratorios Made SA

1979-11-13 Application granted granted Critical

1979-11-13 Publication of CA1066283A publication Critical patent/CA1066283A/en

Status Expired legal-status Critical Current

Links

239000000543 intermediate Substances 0.000 title 1
238000000034 method Methods 0.000 claims abstract description 11
DKPLVYXZLOSLLD-UHFFFAOYSA-N 4-methyl-2-(thiophen-2-ylmethyl)pyridine Chemical compound CC1=CC=NC(CC=2SC=CC=2)=C1 DKPLVYXZLOSLLD-UHFFFAOYSA-N 0.000 claims abstract description 10
KTZOLNLKPVUPHL-UHFFFAOYSA-N (4-methylpyridin-2-yl)-thiophen-2-ylmethanone Chemical compound CC1=CC=NC(C(=O)C=2SC=CC=2)=C1 KTZOLNLKPVUPHL-UHFFFAOYSA-N 0.000 claims abstract description 6
239000000126 substance Substances 0.000 claims description 5
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 3
WSKDRFSCITZFTP-UHFFFAOYSA-N 1,4-dimethyl-6-(thiophen-2-ylmethyl)-3,6-dihydro-2h-pyridine Chemical compound CN1CCC(C)=CC1CC1=CC=CS1 WSKDRFSCITZFTP-UHFFFAOYSA-N 0.000 abstract description 10
OMIUYBJMABKWDL-UHFFFAOYSA-M 1,4-dimethyl-2-(thiophen-2-ylmethyl)pyridin-1-ium;bromide Chemical compound [Br-].CC1=CC=[N+](C)C(CC=2SC=CC=2)=C1 OMIUYBJMABKWDL-UHFFFAOYSA-M 0.000 abstract description 9
230000000202 analgesic effect Effects 0.000 abstract description 5
239000002253 acid Substances 0.000 abstract description 4
150000003840 hydrochlorides Chemical class 0.000 abstract description 3
150000003839 salts Chemical class 0.000 abstract description 3
HJTYNMYGDFPROI-UHFFFAOYSA-N 1,4-dimethyl-2-(thiophen-2-ylmethyl)-3,6-dihydro-2h-pyridine Chemical compound CN1CC=C(C)CC1CC1=CC=CS1 HJTYNMYGDFPROI-UHFFFAOYSA-N 0.000 abstract description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000000047 product Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
238000010992 reflux Methods 0.000 description 8
239000002904 solvent Substances 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
238000004821 distillation Methods 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000000243 solution Substances 0.000 description 6
150000001875 compounds Chemical class 0.000 description 5
238000000605 extraction Methods 0.000 description 5
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
LQAWSWUFSHYCHP-UHFFFAOYSA-N 4-methylpyridine-2-carbonitrile Chemical compound CC1=CC=NC(C#N)=C1 LQAWSWUFSHYCHP-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
235000011118 potassium hydroxide Nutrition 0.000 description 3
229940093932 potassium hydroxide Drugs 0.000 description 3
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
231100000111 LD50 Toxicity 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229960004193 dextropropoxyphene Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
SNHOZPMHMQQMNI-UHFFFAOYSA-N lithium;2h-thiophen-2-ide Chemical compound [Li+].C=1C=[C-]SC=1 SNHOZPMHMQQMNI-UHFFFAOYSA-N 0.000 description 2
229940102396 methyl bromide Drugs 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
-1 methyl halide Chemical class 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
229930192474 thiophene Natural products 0.000 description 2
238000005303 weighing Methods 0.000 description 2
SZZYUGFMACAIRV-UHFFFAOYSA-N 1,4-dimethyl-2-(thiophen-2-ylmethyl)pyridin-1-ium Chemical compound CC1=CC=[N+](C)C(CC=2SC=CC=2)=C1 SZZYUGFMACAIRV-UHFFFAOYSA-N 0.000 description 1
BYKSINWBBKKRQC-UHFFFAOYSA-N 2,6-dimethyl-1,2,3,6-tetrahydropyridine Chemical compound CC1CC=CC(C)N1 BYKSINWBBKKRQC-UHFFFAOYSA-N 0.000 description 1
VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-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
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
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 description 1
241001465754 Metazoa Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000009877 rendering Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
125000004853 tetrahydropyridinyl group Chemical class N1(CCCC=C1)* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/08—Bridged systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pain & Pain Management (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)
Saccharide Compounds (AREA)

CA261,490A 1975-09-20 1976-09-17 2,5-dimethyl-thieno-(3,2-f)-morphan and intermediates Expired CA1066283A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
ES441142A ES441142A1 (es)	1975-09-20	1975-09-20	Un procedimiento para la obtencion de 2, 5-dimetil-tieno (3,2-f) morfano.

Publications (1)

Publication Number	Publication Date
CA1066283A true CA1066283A (en)	1979-11-13

Family

ID=8470020

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA261,490A Expired CA1066283A (en)	1975-09-20	1976-09-17	2,5-dimethyl-thieno-(3,2-f)-morphan and intermediates

Country Status (16)

Country	Link
JP (1)	JPS5257193A (de)
AR (1)	AR214297A1 (de)
AT (1)	AT352299B (de)
AU (1)	AU502649B2 (de)
BE (1)	BE845756A (de)
CA (1)	CA1066283A (de)
CH (1)	CH615682A5 (de)
DE (1)	DE2641320C3 (de)
ES (1)	ES441142A1 (de)
FR (5)	FR2324302A1 (de)
GB (1)	GB1553614A (de)
NL (1)	NL7610438A (de)
NZ (1)	NZ181891A (de)
PT (1)	PT65595B (de)
SE (2)	SE7610336L (de)
SU (5)	SU604494A3 (de)

1975
- 1975-09-20 ES ES441142A patent/ES441142A1/es not_active Expired
1976
- 1976-08-30 NZ NZ181891A patent/NZ181891A/xx unknown
- 1976-09-01 BE BE170278A patent/BE845756A/xx unknown
- 1976-09-06 AT AT657776A patent/AT352299B/de not_active IP Right Cessation
- 1976-09-09 GB GB37473/76A patent/GB1553614A/en not_active Expired
- 1976-09-10 AU AU17623/76A patent/AU502649B2/en not_active Expired
- 1976-09-13 CH CH1161476A patent/CH615682A5/fr not_active IP Right Cessation
- 1976-09-14 DE DE2641320A patent/DE2641320C3/de not_active Expired
- 1976-09-15 PT PT65595A patent/PT65595B/pt unknown
- 1976-09-15 SU SU762396747A patent/SU604494A3/ru active
- 1976-09-17 JP JP51110937A patent/JPS5257193A/ja active Pending
- 1976-09-17 CA CA261,490A patent/CA1066283A/en not_active Expired
- 1976-09-17 SE SE7610336A patent/SE7610336L/xx unknown
- 1976-09-20 NL NL7610438A patent/NL7610438A/xx not_active Application Discontinuation
- 1976-09-20 FR FR7628180A patent/FR2324302A1/fr active Granted
- 1976-11-27 AR AR264477A patent/AR214297A1/es active
1977
- 1977-04-22 SU SU772474104A patent/SU633481A3/ru active
- 1977-04-22 SU SU772472888A patent/SU625611A3/ru active
- 1977-04-22 SU SU772473620A patent/SU626699A3/ru active
- 1977-04-22 SU SU772472890A patent/SU637084A3/ru active
- 1977-06-03 FR FR7717089A patent/FR2339608A1/fr not_active Withdrawn
- 1977-06-03 FR FR7717091A patent/FR2339610A1/fr not_active Withdrawn
- 1977-06-03 FR FR7717090A patent/FR2339609A1/fr not_active Withdrawn
- 1977-06-03 FR FR7717092A patent/FR2339611A1/fr not_active Withdrawn
1980
- 1980-01-10 SE SE8000206A patent/SE8000206L/sv unknown

Also Published As

Publication number	Publication date
PT65595B (fr)	1978-03-28
FR2339611A1 (fr)	1977-08-26
FR2324302B1 (de)	1978-12-15
JPS5257193A (en)	1977-05-11
AU502649B2 (en)	1979-08-02
FR2324302A1 (fr)	1977-04-15
FR2339609A1 (fr)	1977-08-26
DE2641320A1 (de)	1977-03-24
CH615682A5 (en)	1980-02-15
SU637084A3 (ru)	1978-12-05
BE845756A (fr)	1977-03-01
SU626699A3 (ru)	1978-09-30
DE2641320C3 (de)	1980-04-03
DE2641320B2 (de)	1979-08-02
SU625611A3 (ru)	1978-09-25
FR2339608A1 (fr)	1977-08-26
SE7610336L (sv)	1977-03-21
NL7610438A (nl)	1977-03-22
PT65595A (fr)	1976-10-01
FR2339610A1 (fr)	1977-08-26
SE8000206L (sv)	1980-01-10
SU604494A3 (ru)	1978-04-25
ATA657776A (de)	1979-02-15
AR214297A1 (es)	1979-05-31
ES441142A1 (es)	1977-07-01
AT352299B (de)	1979-09-10
AU1762376A (en)	1978-03-16
SU633481A3 (ru)	1978-11-15
GB1553614A (en)	1979-09-26
NZ181891A (en)	1979-01-11

Publication	Publication Date	Title
EP1246801B1 (de)	2006-09-20	Verfahren zur herstellung von alfentanil, sufentanil und remifentanil
US4039676A (en)	1977-08-02	2-piperidinoalkyl-1,4-benzodioxans
EP1274685B1 (de)	2006-07-12	Ein pyridin-n-oxid-derivat und ein prozess zu seiner umsetzung in pharmazeutische wirkstoffe
CA1041513A (en)	1978-10-31	N-(1-(PHENYLALKYL)-PIPERIDYL-4)-N-(.alpha.-PYRIDYL)-CARBONIC ACID AMIDES, THEIR ACID ADDITION SALTS, PROCESSES FOR THEIR PRODUCTION AS WELL AS THEIR USE AS PHARMACEUTICALS
US5364943A (en)	1994-11-15	Preparation of substituted piperidines
AU2001254997A1 (en)	2002-01-17	A pyridine-1-oxide derivative, and process for its transformation into pharmaceutically effective compounds
NO811229L (no)	1981-10-12	Fremgangsmaate ved fremstilling av nye tricykliske etere
DK147318B (da)	1984-06-18	Analogifremgangsmaade til fremstilling af racemiske eller optisk aktive c-(2-benzofuranyl)-tetrahydropyridiner eller -piperidiner eller syreadditionssalte deraf
Cope et al.	1966	Clarke—Eschweiler Cyclization. Scope and Mechanism1a
US4172201A (en)	1979-10-23	Alpha-2,5,9-trimethyl-benzo(b)thiene(2,3-f)morphan and precursor thereof
Bosch et al.	1975	Benzomorphan related compounds. II. New synthesis route to thienomorphans
US3055888A (en)	1962-09-25	2-alkylmercapto-9-[2'-(n-alkylpiperidyl-2" and pyrrolidyl-2")-ethylidene-1']-thiaxanthenes
EP0053949B1 (de)	1983-12-28	Verfahren zur Herstellung von 5,6,7,7a-4H-Tetrahydrothieno(3,2-c)pyridin-2-onen
US3324139A (en)	1967-06-06	3-(3-hydroxyphenyl)-1-phenacylpiperidine compounds
US4178450A (en)	1979-12-11	2,5-Dimethyl-benzo(b) thiene (3,2-f) morphan and precursor thereof
CA1298832C (en)	1992-04-14	3-phenyl-1-propanones, process of preparing thereof and method of treating arrhythmias
Wibaut et al.	1950	The preparation of pyridine derivatives from halogenopyridines by means of the grignard reaction III. Application of the reaction to 3‐bromopyridine
US4174396A (en)	1979-11-13	7,10-Dimethyl-5,9-imino-4,5,8,9-tetrahydro-cyclooct[b]thiophenes and a process for obtaining it
US3313822A (en)	1967-04-11	Diphenyl substituted aminoalkyl pyridines
FI78912C (fi)	1989-10-10	Foerfarande foer framstaellning av terapeutiskt anvaendbara, nya -etyl- -(2-metoxifenyl)-4-/(4-benshydryl piperazin-1-yl)-alkoxi/-bensylalkoholderivat.
CA1047499A (en)	1979-01-30	Process for the preparation of 3,4,5-trimethoxy-phenyl-(1,4-dimethyl-1,2,-3,6- tetrahydro-2-pyridyl)-carbinol
CA1068279A (en)	1979-12-18	2,4,5-trimethyl-thieno (3,2-f) morphan, and intermediates
CH615682A5 (en)	1980-02-15	Process for the preparation of a thienomorphane derivative
US3167562A (en)	1965-01-26	New j-azabicyclo
US3196161A (en)	1965-07-20	Process for preparing alkyl 3-alkyl-isoxazole-5-carboxylate