SE501162C2 - Förfarande för framställning av N,N- dimetylaminometylarylföreningar - Google Patents

Förfarande för framställning av N,N- dimetylaminometylarylföreningar

Info

Publication number: SE501162C2
Authority: SE; Sweden
Prior art keywords: formula; group; dimethylamine; mmol; compound
Prior art date: 1989-07-10

Application number

SE9002363A

Other languages

English (en)

Swedish (sv)

Other versions

SE9002363D0 (sv

SE9002363L (sv

Inventor

Boerge Alhede

Ole Buchardt

Finn Priess Clausen

Klaus K Mccluskey

Hans Petersen

Original Assignee

Gea Farmaceutisk Fabrik As

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.)

1989-07-10

Filing date

1990-07-05

Publication date

1994-11-28

1990-07-05 Application filed by Gea Farmaceutisk Fabrik As filed Critical Gea Farmaceutisk Fabrik As

1990-07-05 Publication of SE9002363D0 publication Critical patent/SE9002363D0/xx

1991-01-11 Publication of SE9002363L publication Critical patent/SE9002363L/xx

1994-11-28 Publication of SE501162C2 publication Critical patent/SE501162C2/sv

Links

238000000034 method Methods 0.000 title claims description 18
150000001875 compounds Chemical class 0.000 title claims description 13
238000002360 preparation method Methods 0.000 title claims description 10
229910052757 nitrogen Inorganic materials 0.000 title claims description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 32
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims abstract description 29
238000006243 chemical reaction Methods 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims abstract description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
UCBFBQXXPWLTSZ-UHFFFAOYSA-O dimethyl-[1-(methylamino)ethylidene]azanium Chemical class CNC(C)=[N+](C)C UCBFBQXXPWLTSZ-UHFFFAOYSA-O 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims abstract 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 1
UXKUODQYLDZXDL-UHFFFAOYSA-N fulminic acid Chemical compound [O-][N+]#C UXKUODQYLDZXDL-UHFFFAOYSA-N 0.000 claims 1
125000002541 furyl group Chemical group 0.000 claims 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
125000004076 pyridyl group Chemical group 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 abstract description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 2
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 abstract 1
235000019256 formaldehyde Nutrition 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 9
229960000620 ranitidine Drugs 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
-1 aziridine compound Chemical class 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
239000000284 extract Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
YECZTTHHUYWDCA-UHFFFAOYSA-N dimethyl-[1-(methylamino)ethylidene]azanium;chloride Chemical compound [Cl-].CNC(C)=[N+](C)C YECZTTHHUYWDCA-UHFFFAOYSA-N 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007858 starting material Substances 0.000 description 3
150000003573 thiols Chemical class 0.000 description 3
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
OTXQUGSUXRBUTC-UHFFFAOYSA-N butan-1-ol;toluene Chemical compound CCCCO.CC1=CC=CC=C1 OTXQUGSUXRBUTC-UHFFFAOYSA-N 0.000 description 2
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
239000002994 raw material Substances 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
MBYQPPXEXWRMQC-UHFFFAOYSA-N (2-chlorophenyl)methanol Chemical compound OCC1=CC=CC=C1Cl MBYQPPXEXWRMQC-UHFFFAOYSA-N 0.000 description 1
MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 1
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
XKNAIPOKZKWCES-UHFFFAOYSA-N C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.CN(C)CC=1C=NC=CC1 Chemical compound C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.CN(C)CC=1C=NC=CC1 XKNAIPOKZKWCES-UHFFFAOYSA-N 0.000 description 1
QADXZTLKPDLXFA-UHFFFAOYSA-N C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.CN(C)CC=1OC(=CC1)CN(C)C Chemical compound C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.C1([N+](=O)[O-])=CC([N+](=O)[O-])=CC([N+](=O)[O-])=C1O.CN(C)CC=1OC(=CC1)CN(C)C QADXZTLKPDLXFA-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
208000007107 Stomach Ulcer Diseases 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
BQRQOLQFLNSWNV-UHFFFAOYSA-N [5-[(dimethylamino)methyl]furan-2-yl]methanol Chemical compound CN(C)CC1=CC=C(CO)O1 BQRQOLQFLNSWNV-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000000767 anti-ulcer Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000001541 aziridines Chemical class 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
208000000718 duodenal ulcer Diseases 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
150000002240 furans Chemical class 0.000 description 1
201000005917 gastric ulcer Diseases 0.000 description 1
239000000499 gel Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
QSJNAFJALFWFMT-UHFFFAOYSA-N meridine Chemical compound N1C=CC(=O)C2=C1C(=O)C1=NC=CC3=C(C=CC=C4)C4=NC2=C13 QSJNAFJALFWFMT-UHFFFAOYSA-N 0.000 description 1
150000003956 methylamines Chemical class 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
238000003541 multi-stage reaction Methods 0.000 description 1
231100000219 mutagenic Toxicity 0.000 description 1
230000003505 mutagenic effect Effects 0.000 description 1
UGSSAVQQESETEY-UHFFFAOYSA-N n,n-dimethyl-1-phenylethanamine;2,4,6-trinitrophenol Chemical compound CN(C)C(C)C1=CC=CC=C1.OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O UGSSAVQQESETEY-UHFFFAOYSA-N 0.000 description 1
SLZCOYDOFRTTHF-UHFFFAOYSA-N n,n-dimethyl-1-pyridin-3-ylmethanamine Chemical compound CN(C)CC1=CC=CN=C1 SLZCOYDOFRTTHF-UHFFFAOYSA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229940075930 picrate Drugs 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
DFWRZHZPJJAJMX-UHFFFAOYSA-N propanimidamide;hydrochloride Chemical compound Cl.CCC(N)=N DFWRZHZPJJAJMX-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
SHNUBALDGXWUJI-UHFFFAOYSA-N pyridin-2-ylmethanol Chemical compound OCC1=CC=CC=N1 SHNUBALDGXWUJI-UHFFFAOYSA-N 0.000 description 1
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 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
- C07C209/16—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Furan Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SE9002363A 1989-07-10 1990-07-05 Förfarande för framställning av N,N- dimetylaminometylarylföreningar SE501162C2 (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DK340089A DK161513C (da)	1989-07-10	1989-07-10	Fremgangsmaade til fremstilling af n,n-dimethylaminomethylarylforbindelser

Publications (3)

Publication Number	Publication Date
SE9002363D0 SE9002363D0 (sv)	1990-07-05
SE9002363L SE9002363L (sv)	1991-01-11
SE501162C2 true SE501162C2 (sv)	1994-11-28

Family

ID=8122450

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE9002363A SE501162C2 (sv)	1989-07-10	1990-07-05	Förfarande för framställning av N,N- dimetylaminometylarylföreningar

Country Status (8)

Country	Link
AT (1)	AT398565B (no)
DD (1)	DD296481A5 (no)
DE (1)	DE4020964A1 (no)
DK (1)	DK161513C (no)
FI (1)	FI102166B1 (no)
HU (1)	HU206076B (no)
NO (1)	NO170578C (no)
SE (1)	SE501162C2 (no)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP5757480B2 (ja) *	2011-05-13	2015-07-29	国立大学法人広島大学	イオン液体、イオン液体の製造方法、および同イオン液体を含む蓄電装置

1989
- 1989-07-10 DK DK340089A patent/DK161513C/da not_active IP Right Cessation
1990
- 1990-06-20 AT AT131390A patent/AT398565B/de not_active IP Right Cessation
- 1990-06-30 DE DE19904020964 patent/DE4020964A1/de not_active Withdrawn
- 1990-07-05 SE SE9002363A patent/SE501162C2/sv unknown
- 1990-07-09 DD DD34263490A patent/DD296481A5/de not_active IP Right Cessation
- 1990-07-09 NO NO903062A patent/NO170578C/no unknown
- 1990-07-09 FI FI903457A patent/FI102166B1/fi not_active IP Right Cessation
- 1990-07-09 HU HU414390A patent/HU206076B/hu not_active IP Right Cessation

Also Published As

Publication number	Publication date
HUT54615A (en)	1991-03-28
FI903457A0 (fi)	1990-07-09
SE9002363D0 (sv)	1990-07-05
DK340089D0 (da)	1989-07-10
NO903062D0 (no)	1990-07-09
FI102166B (fi)	1998-10-30
NO903062L (no)	1991-01-11
DD296481A5 (de)	1991-12-05
SE9002363L (sv)	1991-01-11
HU206076B (en)	1992-08-28
NO170578C (no)	1992-11-04
HU904143D0 (en)	1990-12-28
DE4020964A1 (de)	1991-01-17
DK161513C (da)	1991-12-23
NO170578B (no)	1992-07-27
FI102166B1 (fi)	1998-10-30
AT398565B (de)	1994-12-27
DK340089A (da)	1991-01-11
DK161513B (da)	1991-07-15
ATA131390A (de)	1994-05-15

Publication	Publication Date	Title
US4968808A (en)	1990-11-06	Process for the preparation of nitroethene derivatives
KR920002295B1 (ko)	1992-03-21	프롤리디논 유도체의 제조방법
SE501162C2 (sv)	1994-11-28	Förfarande för framställning av N,N- dimetylaminometylarylföreningar
SU950188A3 (ru)	1982-08-07	Способ получени производных 4(5)-меркаптометилимидазолов
US5112995A (en)	1992-05-12	Preparation of substituted ethenes
KR840002007B1 (ko)	1984-10-27	푸란유도체의 제조방법
EP0219225B1 (en)	1989-02-22	Process for the preparation of ranitidine or acid addition salts thereof, and intermediates for this preparation
HU211774B (en)	1995-12-28	Improved process for the synthesis of n-[3-(1h-imidazol-1-yl)phenyl]-4-substituted-2-pyrimidinamines
FI76080B (fi)	1988-05-31	Foerfarande foer framstaellning av furanderivat.
US4925944A (en)	1990-05-15	Process for the preparation of o-carboxypyridyl- and o-carboxyquinolylimidazolinones
KR100429668B1 (ko)	2004-07-30	2-아미노벤젠술폰산및염화2-아미노벤젠술포닐의유도체와그제조법및합성중간체로서의사용
SE449747B (sv)	1987-05-18	Forfarande for framstellning av n-/2-//5-/(dimetylamino) metyl/-2-furanylmetyl/-tio/etyl/n'-metyl-2-nitro-1,1-etendiamin (ranitidin)
JPH062747B2 (ja)	1994-01-12	２‐アルキル‐４，５‐ジヒドロキシメチルイミダゾールの製法
EP0034421B1 (en)	1983-04-27	N-phenyl-n'-cyano-0-phenylisoureas and process for their preparation
US4460506A (en)	1984-07-17	Nitrovinyl aziridine derivative
DK153481B (da)	1988-07-18	Fremgangsmaade til fremstilling af ranitidin
RU2042671C1 (ru)	1995-08-27	Производное дикетен-имина в качестве промежуточного продукта для синтеза ранитидина и способ его получения
SU464116A3 (ru)	1975-03-15	Способ получени замещенных аминоалкильных эфиров тиолкарбаминовой кислоты
KR870000448B1 (ko)	1987-03-11	아미노 알킬 푸란 유도체의 제조방법
JP2007532505A (ja)	2007-11-15	アジドアルキルアミンの製造方法
DK153757B (da)	1988-08-29	Derivat af 5-((2-aminoethyl)-thiomethyl)-2-furanmethanol
HU180140B (en)	1983-02-28	New process for producing n-dialkylamino-methyl-s,s-diaryl-sulphoximide derivatives
JPH0442394B2 (no)	1992-07-13
HU193497B (en)	1987-10-28	Process for preparing sanitidine hydrogen halogenides
KR19980054707A (ko)	1998-09-25	N-니트로이소티오우레아 유도체 및 이의 제조방법