CA1068279A - 2,4,5-trimethyl-thieno(3,2-f)-morphane et composes intermediaires - Google Patents

2,4,5-trimethyl-thieno(3,2-f)-morphane et composes intermediaires

Info

Publication number: CA1068279A
Authority: CA; Canada
Prior art keywords: thenyl; dimethyl; thienyl; formula; dimethylpyridine
Prior art date: 1975-09-19
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

CA261,567A

Other languages

English (en)

Inventor

Francisco Lopez Calahorra

Cristobal Martinez Roldan

Ricardo Granados Jarque

Juan Bosch Cartes

Fernando Rabadan Peinado

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.)

1975-09-19

Filing date

1976-09-20

Publication date

1979-12-18

1976-09-20 Application filed by Laboratorios Made SA filed Critical Laboratorios Made SA

1979-12-18 Application granted granted Critical

1979-12-18 Publication of CA1068279A publication Critical patent/CA1068279A/fr

Status Expired legal-status Critical Current

Links

ZPAPCUKKKOSLPZ-UHFFFAOYSA-N morphan Chemical compound C1CNC2CCCC1C2 ZPAPCUKKKOSLPZ-UHFFFAOYSA-N 0.000 title claims abstract description 13
239000000543 intermediate Substances 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 29
230000000694 effects Effects 0.000 claims abstract description 3
SIKROJBXSDVEOZ-UHFFFAOYSA-N 4,5-dimethyl-2-(thiophen-2-ylmethyl)pyridine Chemical compound C1=C(C)C(C)=CN=C1CC1=CC=CS1 SIKROJBXSDVEOZ-UHFFFAOYSA-N 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 8
SJSJDKXIYIGGOO-UHFFFAOYSA-N 4,5-dimethylpyridine-2-carbonitrile Chemical compound CC1=CN=C(C#N)C=C1C SJSJDKXIYIGGOO-UHFFFAOYSA-N 0.000 claims description 7
SNHOZPMHMQQMNI-UHFFFAOYSA-N lithium;2h-thiophen-2-ide Chemical compound [Li+].C=1C=[C-]SC=1 SNHOZPMHMQQMNI-UHFFFAOYSA-N 0.000 claims description 5
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 4
VSNZRKOZJCMAAO-UHFFFAOYSA-N (4,5-dimethylpyridin-2-yl)-thiophen-2-ylmethanone Chemical compound C1=C(C)C(C)=CN=C1C(=O)C1=CC=CS1 VSNZRKOZJCMAAO-UHFFFAOYSA-N 0.000 claims description 4
239000012298 atmosphere Substances 0.000 claims description 4
239000012458 free base Substances 0.000 claims description 4
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
239000012279 sodium borohydride Substances 0.000 claims description 4
229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 2
238000007363 ring formation reaction Methods 0.000 claims description 2
OFBRUTLUTMYUGK-UHFFFAOYSA-N 1,4,5-trimethyl-2-(thiophen-2-ylmethyl)-3,6-dihydro-2h-pyridine Chemical compound CN1CC(C)=C(C)CC1CC1=CC=CS1 OFBRUTLUTMYUGK-UHFFFAOYSA-N 0.000 claims 2
JYPAFRFYGHDXER-UHFFFAOYSA-M 1,4,5-trimethyl-2-(thiophen-2-ylmethyl)pyridin-1-ium;iodide Chemical compound [I-].C1=C(C)C(C)=CC(CC=2SC=CC=2)=[N+]1C JYPAFRFYGHDXER-UHFFFAOYSA-M 0.000 claims 1
230000000202 analgesic effect Effects 0.000 abstract description 14
LYFNWGOUBVRWRG-UHFFFAOYSA-N 3,4-dimethyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=[N+]([O-])C=C1C LYFNWGOUBVRWRG-UHFFFAOYSA-N 0.000 abstract description 2
ZNOZSWWXTNOCLB-UHFFFAOYSA-N 1,4,5-trimethyl-2-thiophen-2-yl-3,6-dihydro-2H-pyridine Chemical compound S1C(=CC=C1)C1N(CC(=C(C1)C)C)C ZNOZSWWXTNOCLB-UHFFFAOYSA-N 0.000 abstract 1
XLNIRNAYIMZQLV-UHFFFAOYSA-N 4,5-dimethyl-2-thiophen-2-ylpyridine Chemical compound S1C(=CC=C1)C1=NC=C(C(=C1)C)C XLNIRNAYIMZQLV-UHFFFAOYSA-N 0.000 abstract 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 13
229960004193 dextropropoxyphene Drugs 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
239000000203 mixture Substances 0.000 description 9
238000010992 reflux Methods 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
239000000243 solution 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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
239000002904 solvent Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
238000004821 distillation Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
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
238000009835 boiling Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
NURQLCJSMXZBPC-UHFFFAOYSA-N 3,4-dimethylpyridine Chemical compound CC1=CC=NC=C1C NURQLCJSMXZBPC-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
230000007059 acute toxicity Effects 0.000 description 3
231100000403 acute toxicity Toxicity 0.000 description 3
239000010410 layer Substances 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
235000011118 potassium hydroxide Nutrition 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
238000013019 agitation Methods 0.000 description 2
-1 alkali metal cyanide Chemical class 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
238000011835 investigation Methods 0.000 description 2
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
229930192474 thiophene Natural products 0.000 description 2
FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical class N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
OPNUUWMXUITYNB-UHFFFAOYSA-N 3,4-dimethylpyridine-2-carbonitrile Chemical compound CC1=CC=NC(C#N)=C1C OPNUUWMXUITYNB-UHFFFAOYSA-N 0.000 description 1
101100001675 Emericella variicolor andJ gene Proteins 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
150000001204 N-oxides Chemical class 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000036592 analgesia Effects 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
239000012431 aqueous reaction media Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
244000144993 groups of animals Species 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
- 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
- A61P25/20—Hypnotics; Sedatives
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16C—SHAFTS; FLEXIBLE SHAFTS; ELEMENTS OR CRANKSHAFT MECHANISMS; ROTARY BODIES OTHER THAN GEARING ELEMENTS; BEARINGS
- F16C2300/00—Application independent of particular apparatuses
- F16C2300/10—Application independent of particular apparatuses related to size
- F16C2300/14—Large applications, e.g. bearings having an inner diameter exceeding 500 mm

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Neurosurgery (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Anesthesiology (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (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)
Hydrogenated Pyridines (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)

CA261,567A 1975-09-19 1976-09-20 2,4,5-trimethyl-thieno(3,2-f)-morphane et composes intermediaires Expired CA1068279A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
ES441097A ES441097A1 (es)	1975-09-19	1975-09-19	Procedimiento para la obtencion de 2,4, 5-trimetil-tieno (3,2-f) morfano.

Publications (1)

Publication Number	Publication Date
CA1068279A true CA1068279A (fr)	1979-12-18

Family

ID=8470007

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA261,567A Expired CA1068279A (fr)	1975-09-19	1976-09-20	2,4,5-trimethyl-thieno(3,2-f)-morphane et composes intermediaires

Country Status (15)

Country	Link
JP (1)	JPS5248694A (fr)
AR (1)	AR210612A1 (fr)
AT (1)	AT347051B (fr)
BE (1)	BE845755A (fr)
CA (1)	CA1068279A (fr)
CH (1)	CH617195A5 (fr)
DE (1)	DE2639181C3 (fr)
ES (1)	ES441097A1 (fr)
FR (5)	FR2362128A1 (fr)
GB (1)	GB1513980A (fr)
NL (1)	NL7610437A (fr)
NZ (1)	NZ181870A (fr)
PT (1)	PT65547B (fr)
SE (2)	SE7609357L (fr)
SU (3)	SU620210A3 (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1274913A (fr) *	1959-09-09	1961-11-03	Rohm & Haas	Procédé de cyanuration de composés nu-hétérocycliques et nitriles ainsi obtenus

1975
- 1975-09-19 ES ES441097A patent/ES441097A1/es not_active Expired
1976
- 1976-08-24 SE SE7609357A patent/SE7609357L/xx not_active Application Discontinuation
- 1976-08-25 GB GB35397/76A patent/GB1513980A/en not_active Expired
- 1976-08-26 NZ NZ181870A patent/NZ181870A/xx unknown
- 1976-08-26 AR AR264463A patent/AR210612A1/es active
- 1976-08-31 DE DE2639181A patent/DE2639181C3/de not_active Expired
- 1976-09-01 BE BE170277A patent/BE845755A/fr unknown
- 1976-09-02 PT PT65547A patent/PT65547B/pt unknown
- 1976-09-09 FR FR7627080A patent/FR2362128A1/fr not_active Withdrawn
- 1976-09-16 AT AT687976A patent/AT347051B/de not_active IP Right Cessation
- 1976-09-17 CH CH1182776A patent/CH617195A5/fr not_active IP Right Cessation
- 1976-09-17 SU SU762401851A patent/SU620210A3/ru active
- 1976-09-17 JP JP51110886A patent/JPS5248694A/ja active Pending
- 1976-09-20 NL NL7610437A patent/NL7610437A/xx not_active Application Discontinuation
- 1976-09-20 CA CA261,567A patent/CA1068279A/fr not_active Expired
1977
- 1977-02-21 SU SU772453400A patent/SU650506A3/ru active
- 1977-02-21 SU SU772455453A patent/SU671731A3/ru active
- 1977-03-30 FR FR7709582A patent/FR2361397A1/fr not_active Withdrawn
- 1977-03-30 FR FR7709584A patent/FR2361389A1/fr not_active Withdrawn
- 1977-03-30 FR FR7709585A patent/FR2361390A1/fr not_active Withdrawn
- 1977-03-30 FR FR7709583A patent/FR2361388A1/fr not_active Withdrawn
1979
- 1979-08-27 SE SE7907106A patent/SE7907106L/sv not_active Application Discontinuation

Also Published As

Publication number	Publication date
DE2639181A1 (de)	1977-03-31
FR2361389A1 (fr)	1978-03-10
NZ181870A (en)	1978-11-13
PT65547A (en)	1976-10-01
SU650506A3 (ru)	1979-02-28
FR2362128A1 (fr)	1978-03-17
JPS5248694A (en)	1977-04-18
SU620210A3 (ru)	1978-08-15
NL7610437A (nl)	1977-03-22
FR2361390A1 (fr)	1978-03-10
DE2639181C3 (de)	1979-05-31
PT65547B (en)	1978-03-24
GB1513980A (en)	1978-06-14
CH617195A5 (en)	1980-05-14
SU671731A3 (ru)	1979-06-30
AU1715576A (en)	1978-03-02
SE7907106L (sv)	1979-08-27
FR2361388A1 (fr)	1978-03-10
BE845755A (fr)	1977-03-01
DE2639181B2 (de)	1978-10-05
FR2361397A1 (fr)	1978-03-10
AT347051B (de)	1978-12-11
SE7609357L (sv)	1977-03-20
ES441097A1 (es)	1977-03-16
ATA687976A (de)	1978-04-15
AR210612A1 (es)	1977-08-31

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NO174506B (no)	1994-02-07	Analogifremgangsmaate ved fremstilling av terapeutisk aktive forbindelser
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NO141898B (no)	1980-02-18	Fremgangsmaate for fremstilling av 6,7-dimetoksy-4-amino-2-(4-(2-furoyl)-piperazin-1-yl)-kinazolin
CA1107729A (fr)	1981-08-25	Preparation de derives de fluorenes et de fluoranthenes
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JPS6047255B2 (ja)	1985-10-21	２−アミノ−５−スルフアモイル−安息香酸アミドの製法
DE2056407A1 (de)	1971-05-27	Verfahren zur Herstellung von 1 Alkyl 4,5 diphenyl bzw 4 (2 thienyl) 5 phenyl pynmidin 2(1H) onen
US2723268A (en)	1955-11-08	Process and intermediates for preparing
US3201406A (en)	1965-08-17	Pyridylcoumarins
US4827020A (en)	1989-05-02	Propargyl amide precursor to 1-propargyl-2,4-dioxoimidazolidine
WO1989006230A1 (fr)	1989-07-13	Cyano-dienes, halopyridines, intermediaires et un procede de leur preparation
NO147838B (no)	1983-03-14	Mellomprodukt til bruk ved fremstilling av det hypotensive middel 2-(4-(2-furoyl)piperazin-1-yl)-4-amino-6,7-dimetoksykinazolin
JPH11130752A (ja)	1999-05-18	ヘテロアリールカルボン酸アミド類およびエステル類の製造方法
EP0062068B1 (fr)	1985-06-12	Derives de n-phthalidyl-5-fluorouracile
US4127582A (en)	1978-11-28	Method of preparing alkyl halopyridinyloxyalkanoates
EP0236754B1 (fr)	1990-08-29	Procédé pour la préparation de composés acétyl-4-isoquinoléiniques
US3663554A (en)	1972-05-16	Preparation of beta-collidine
SU679143A3 (ru)	1979-08-05	Способ получени производных ариламинопиримидинов
JPS5982366A (ja)	1984-05-12	ケト中間体ならびにその用法および製造方法
US2775592A (en)	1956-12-25	Z-methyl -
KR20080027885A (ko)	2008-03-28	１-벤질-４-[(５,６-디메톡시-１-인다논)-２-일리덴]메틸피페리딘의 제조 방법
JPS6152826B2 (fr)	1986-11-14
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