FI90419C - Menetelmä 1- 2-/5-dimetyyliaminometyyli-2-(furyylimetyylitio)etyyli/ amino-1-metyyliamino-2-nitroeteenin ja sen hydrokloridin valmistamiseksi - Google Patents

Menetelmä 1- 2-/5-dimetyyliaminometyyli-2-(furyylimetyylitio)etyyli/ amino-1-metyyliamino-2-nitroeteenin ja sen hydrokloridin valmistamiseksi Download PDF

Info

Publication number: FI90419C
Authority: FI; Finland
Prior art keywords: formula; ethyl; hydrochloride; dimethylaminomethyl; compound
Prior art date: 1985-01-11

Application number

FI860123A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI90419B (fi

FI860123A0 (fi

FI860123A7 (fi

Inventor

Bela Stefko

Lajos Toldy

Endre Kasztreiner

Nandor Makk

Eszter Diesler

Peter Matyus

Tibor Balogh

Tibor Lang

Ferenc Szederkenyi

Gyula Horvath

Arpad Lazar

Tibor Somogyi

Nee Dievald Emilia Uskert

Nee Falta Eva Koczka

Nee Szekeres Dora Bobak

Original Assignee

Richter Gedeon Vegyeszet

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.)

1985-01-11

Filing date

1986-01-10

Publication date

1994-02-10

1986-01-10 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1986-01-10 Publication of FI860123A0 publication Critical patent/FI860123A0/fi

1986-07-12 Publication of FI860123A7 publication Critical patent/FI860123A7/fi

1993-10-29 Publication of FI90419B publication Critical patent/FI90419B/fi

1994-02-10 Application granted granted Critical

1994-02-10 Publication of FI90419C publication Critical patent/FI90419C/fi

Links

238000000034 method Methods 0.000 title claims description 36
238000002360 preparation method Methods 0.000 title claims description 17
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 title description 32
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 30
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
239000002253 acid Substances 0.000 claims description 4
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims description 4
238000011065 in-situ storage Methods 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910001923 silver oxide Inorganic materials 0.000 claims description 2
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
239000011230 binding agent Substances 0.000 claims 1
239000008012 organic excipient Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 40
SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
229910001961 silver nitrate Inorganic materials 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
229910052709 silver Inorganic materials 0.000 description 9
239000000047 product Substances 0.000 description 8
239000004332 silver Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
VMXUWOKSQNHOCA-UKTHLTGXSA-N ranitidine Chemical compound [O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-UKTHLTGXSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
-1 nitroketene imine Chemical class 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
238000007259 addition reaction Methods 0.000 description 4
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
229960000620 ranitidine Drugs 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
239000002516 radical scavenger Substances 0.000 description 3
ILRSPKULGBJLBZ-UHFFFAOYSA-N 2-nitroethenimine Chemical compound [O-][N+](=O)C=C=N ILRSPKULGBJLBZ-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical group Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000012535 impurity Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
230000001376 precipitating effect Effects 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
229960001520 ranitidine hydrochloride Drugs 0.000 description 2
GGWBHVILAJZWKJ-KJEVSKRMSA-N ranitidine hydrochloride Chemical compound [H+].[Cl-].[O-][N+](=O)\C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 GGWBHVILAJZWKJ-KJEVSKRMSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000012795 verification Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 1
208000007107 Stomach Ulcer Diseases 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
208000000718 duodenal ulcer Diseases 0.000 description 1
ZUKSLMGYYPZZJD-UHFFFAOYSA-N ethenimine Chemical compound C=C=N ZUKSLMGYYPZZJD-UHFFFAOYSA-N 0.000 description 1
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
239000003485 histamine H2 receptor antagonist Substances 0.000 description 1
150000002466 imines Chemical class 0.000 description 1
230000003993 interaction Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
SVIDAEJFBAYABG-UHFFFAOYSA-N n-methyl-2-nitroethenamine Chemical group CNC=C[N+]([O-])=O SVIDAEJFBAYABG-UHFFFAOYSA-N 0.000 description 1
RPMXALUWKZHYOV-UHFFFAOYSA-N nitroethene Chemical group [O-][N+](=O)C=C RPMXALUWKZHYOV-UHFFFAOYSA-N 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
125000005188 oxoalkyl group Chemical group 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000012545 processing Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
150000003378 silver Chemical class 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
238000012360 testing method Methods 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
238000007039 two-step reaction Methods 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants

Landscapes

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

FI860123A 1985-01-11 1986-01-10 Menetelmä 1- 2-/5-dimetyyliaminometyyli-2-(furyylimetyylitio)etyyli/ amino-1-metyyliamino-2-nitroeteenin ja sen hydrokloridin valmistamiseksi FI90419C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU10485		1985-01-11
HU85104A HU196979B (en)	1985-01-11	1985-01-11	Process for producing basic thioether and salt

Publications (4)

Publication Number	Publication Date
FI860123A0 FI860123A0 (fi)	1986-01-10
FI860123A7 FI860123A7 (fi)	1986-07-12
FI90419B FI90419B (fi)	1993-10-29
FI90419C true FI90419C (fi)	1994-02-10

Family

ID=10947932

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI860123A FI90419C (fi)	1985-01-11	1986-01-10	Menetelmä 1- 2-/5-dimetyyliaminometyyli-2-(furyylimetyylitio)etyyli/ amino-1-metyyliamino-2-nitroeteenin ja sen hydrokloridin valmistamiseksi

Country Status (16)

Country	Link
KR (1)	KR920010926B1 (de)
CN (1)	CN1005630B (de)
AR (1)	AR242200A1 (de)
AT (1)	AT391470B (de)
CA (1)	CA1262913A (de)
CS (1)	CS261232B2 (de)
DK (1)	DK10486A (de)
ES (1)	ES8703864A1 (de)
FI (1)	FI90419C (de)
GB (1)	GB2169600B (de)
GR (1)	GR860058B (de)
HU (1)	HU196979B (de)
IT (1)	IT1203727B (de)
NO (1)	NO170542C (de)
PT (1)	PT81824B (de)
SU (1)	SU1419519A3 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU210849B (en) *	1990-11-09	1995-08-28	Richter Gedeon Vegyeszet	Process for preparing furil derivatives
HU207308B (en) *	1990-11-09	1993-03-29	Richter Gedeon Vegyeszet	Process for producing 1- /2-/5-/dimethyl-amino-methyl/-2-/furyl-methyl-thio/-ethyl//- -amino-1-/methyl-amino-2-nitro-ethylene
CN1048984C (zh) *	1991-12-20	2000-02-02	多坎化学有限公司	晶形1呋喃硝胺氢氯化物的制备
CN102010388B (zh) *	2009-09-04	2012-09-05	江苏汉斯通药业有限公司	雷尼替丁的制备方法
CN102010389B (zh) *	2009-09-04	2012-11-14	江苏汉斯通药业有限公司	一种制备盐酸雷尼替丁的方法
CN110590717B (zh) *	2019-09-18	2022-08-26	上海大学	多取代烯酮亚胺及其合成方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2014561B (en) *	1977-12-23	1982-11-03	Glaxo Group Ltd	Amine derivatives their preparation and pharmaceutical compositions containing them
US4233302A (en) *	1977-12-23	1980-11-11	Glaxo Group Limited	Amine derivatives and pharmaceutical compositions containing them
US4203909A (en) *	1978-09-26	1980-05-20	Bristol-Myers Company	Furan compounds
ES497514A0 (es) *	1980-12-05	1981-10-16	Liade Sa Lab	Procedimiento de obtencion de un derivado de amina primaria heterociclica
EP0057981A3 (de) *	1981-02-09	1982-08-25	Beecham Group Plc	Aromatische Verbindungen, Verfahren zu deren Herstellung und ihre Verwendung
ES8300326A1 (es) *	1981-05-02	1982-11-01	Especialidades Farmaco Terape	Procedimiento para la obtencion de un compuesto derivado delaminometilfurano
ES507180A0 (es) *	1981-11-16	1982-08-16	Pharmedical Sa Lab	Procedimiento de preparacion de amino alcosi furanos o tio- fenos.
PT76557B (en) *	1982-04-16	1986-01-21	Inke Sa	Process for preparing furan derivatives and addition salts thereof and of pharmaceutical compositions containing the same

1985
- 1985-01-11 HU HU85104A patent/HU196979B/hu not_active IP Right Cessation
1986
- 1986-01-10 CA CA000499391A patent/CA1262913A/en not_active Expired
- 1986-01-10 FI FI860123A patent/FI90419C/fi not_active IP Right Cessation
- 1986-01-10 ES ES550809A patent/ES8703864A1/es not_active Expired
- 1986-01-10 NO NO860071A patent/NO170542C/no unknown
- 1986-01-10 SU SU864009783A patent/SU1419519A3/ru active
- 1986-01-10 AT AT0003486A patent/AT391470B/de not_active IP Right Cessation
- 1986-01-10 GR GR860058A patent/GR860058B/el unknown
- 1986-01-10 GB GB08600530A patent/GB2169600B/en not_active Expired
- 1986-01-10 CN CN86100111.7A patent/CN1005630B/zh not_active Expired
- 1986-01-10 IT IT47517/86A patent/IT1203727B/it active
- 1986-01-10 KR KR1019860000116A patent/KR920010926B1/ko not_active Expired
- 1986-01-10 DK DK10486A patent/DK10486A/da not_active Application Discontinuation
- 1986-01-10 PT PT81824A patent/PT81824B/pt not_active IP Right Cessation
- 1986-01-10 AR AR86302826A patent/AR242200A1/es active
- 1986-01-10 CS CS86230A patent/CS261232B2/cs unknown

Also Published As

Publication number	Publication date
CN1005630B (zh)	1989-11-01
GB8600530D0 (en)	1986-02-19
CA1262913A (en)	1989-11-14
KR860005802A (ko)	1986-08-13
HUT38922A (en)	1986-07-28
PT81824A (en)	1986-02-01
IT8647517A0 (it)	1986-01-10
AT391470B (de)	1990-10-10
FI90419B (fi)	1993-10-29
NO170542B (no)	1992-07-20
DK10486A (da)	1986-07-12
KR920010926B1 (ko)	1992-12-24
SU1419519A3 (ru)	1988-08-23
FI860123A0 (fi)	1986-01-10
AR242200A1 (es)	1993-03-31
PT81824B (pt)	1987-11-30
CN86100111A (zh)	1986-11-26
ES8703864A1 (es)	1987-03-01
FI860123A7 (fi)	1986-07-12
HU196979B (en)	1989-02-28
DK10486D0 (da)	1986-01-10
IT1203727B (it)	1989-02-23
NO170542C (no)	1992-10-28
GR860058B (en)	1986-05-13
GB2169600B (en)	1988-04-20
ATA3486A (de)	1990-04-15
GB2169600A (en)	1986-07-16
NO860071L (no)	1986-07-14
CS261232B2 (en)	1989-01-12
ES550809A0 (es)	1987-03-01

Legal Events

Date	Code	Title	Description
1993-10-04	BB	Publication of examined application
1996-08-15	MM	Patent lapsed
2004-08-31	MM	Patent lapsed	Owner name: RICHTER GEDEON VEGYESZETI GYAR R.T.

Publication	Publication Date	Title
HU180045B (en)	1983-01-28	Process for producing new amino-thiasole derivatives
FI78297C (fi)	1989-07-10	Foerfarande foer framstaellning av farmaceutiskt anvaendbara teofyllinderivat.
WO2020039030A1 (en)	2020-02-27	Succinate and fumarate acid addition salts of piperazine derivatives useful as glycosidase inhibitors
IE59713B1 (en)	1994-03-23	Amino-thiazole and oxazole derivatives
US5543414A (en)	1996-08-06	Achiral amino acid acyl esters of ganciclovir and its derivatives
FI90419B (fi)	1993-10-29	Menetelmä 1- 2-/5-dimetyyliaminometyyli-2-(furyylimetyylitio)etyyli/ amino-1-metyyliamino-2-nitroeteenin ja sen hydrokloridin valmistamiseksi
US4032559A (en)	1977-06-28	N,2-dicyanoacetimidates
CA2219308C (en)	2007-12-18	New process for the preparation of ropivacaine hydrochloride monohydrate
FI79301B (fi)	1989-08-31	Foerfarande foer framstaellning av 4-metyl-5- alkyltiometylimidazoler.
FI63753C (fi)	1987-02-19	Foerfarande foer framstaellning av kristallint simetidin.
KR890002427B1 (ko)	1989-07-03	니자티딘의 제조방법
CY1463A (en)	1989-07-21	A new crystal modification of cimetidine and process for preparing and using same
GB2230526A (en)	1990-10-24	Preparation of substituted ethenes
GB2067991A (en)	1981-08-05	Process for the Preparation of a Furan Derivative
CS250240B2 (en)	1987-04-16	Method of ethandiimidamide's derivatives production
GB2036723A (en)	1980-07-02	Mercaptoacylpiperazine carboxylic acid compounds
EP0320532A1 (de)	1989-06-21	Optisch aktives Carbonsäurederivat-l-Lysinsalz und Verfahren zu dessen Herstellung
FI58125C (fi)	1985-01-02	Foerfarande foer framstaellning av 6,7-dimetoxi-4-amino-2-(4-(2-furoyl)-1-piperazinyl)kinazolin med blodtryckssaenkande vekan
RU2204556C2 (ru)	2003-05-20	Способ получения 1-(парахлорбензгидрил)-4-(2-оксиэтил)пиперазина
WO2026077967A1 (en)	2026-04-16	Method for making syn3
RU2042671C1 (ru)	1995-08-27	Производное дикетен-имина в качестве промежуточного продукта для синтеза ранитидина и способ его получения
JPH0585545B2 (de)	1993-12-07
KR910001440B1 (ko)	1991-03-07	2-(N-벤질-N-메틸아미노)에틸메틸 2,6-디메틸-4-(m-니트로페닐)-1,4-디히드로피리딘-3,5-디카르복실레이트 및 그의 염산염의 제조방법
FI84059B (fi)	1991-06-28	Foerfarande foer framstaellning av n-/2-//5-/(dimetylamino)metyl/-2-furanylmetyl/tio/etyl/-n'-metyl-2- nitro-1,1-etendiamin.
KR790001647B1 (ko)	1979-12-01	N-치환 트리메톡시 벤질 피페라진 유도체의 제조방법