FI102166B - Menetelmä N,N-dimetyyliaminometyyliaryyliyhdisteiden valmistamiseksi - Google Patents
Menetelmä N,N-dimetyyliaminometyyliaryyliyhdisteiden valmistamiseksi Download PDFInfo
- Publication number
- FI102166B FI102166B FI903457A FI903457A FI102166B FI 102166 B FI102166 B FI 102166B FI 903457 A FI903457 A FI 903457A FI 903457 A FI903457 A FI 903457A FI 102166 B FI102166 B FI 102166B
- Authority
- FI
- Finland
- Prior art keywords
- formula
- mmol
- compound
- group
- preparation
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 title description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 42
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- UCBFBQXXPWLTSZ-UHFFFAOYSA-O dimethyl-[1-(methylamino)ethylidene]azanium Chemical class CNC(C)=[N+](C)C UCBFBQXXPWLTSZ-UHFFFAOYSA-O 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- UXKUODQYLDZXDL-UHFFFAOYSA-N fulminic acid Chemical compound [O-][N+]#C UXKUODQYLDZXDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 2
- 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 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 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
- 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 10
- 229960000620 ranitidine Drugs 0.000 description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- YECZTTHHUYWDCA-UHFFFAOYSA-N dimethyl-[1-(methylamino)ethylidene]azanium;chloride Chemical compound [Cl-].CNC(C)=[N+](C)C YECZTTHHUYWDCA-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000000284 extract Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000203 mixture Substances 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
- 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
- LARJDTRRRDBHNV-UHFFFAOYSA-N 1-n'-[2-[[5-[(dimethylamino)methyl]furan-2-yl]methylsulfanyl]ethyl]-1-n-methyl-2-nitroethane-1,1-diamine Chemical compound [O-][N+](=O)CC(NC)NCCSCC1=CC=C(CN(C)C)O1 LARJDTRRRDBHNV-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
- SPJRYDGGIPREOP-UHFFFAOYSA-N CNC(C[N+](=O)[O-])NCCSCC1=CC=C(O1)CO Chemical compound CNC(C[N+](=O)[O-])NCCSCC1=CC=C(O1)CO SPJRYDGGIPREOP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- 208000025865 Ulcer Diseases 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001541 aziridines Chemical class 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000004656 dimethylamines Chemical class 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- WVRIJHGUJNXDRZ-UHFFFAOYSA-N ethane-1,1-diamine Chemical compound CC(N)N WVRIJHGUJNXDRZ-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- HRUBXJBPLLZTAN-UHFFFAOYSA-N n,n-dimethyl-1-pyridin-2-ylmethanamine Chemical compound CN(C)CC1=CC=CC=N1 HRUBXJBPLLZTAN-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
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 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
- 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 210000002268 wool Anatomy 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK340089 | 1989-07-10 | ||
| DK340089A DK161513C (da) | 1989-07-10 | 1989-07-10 | Fremgangsmaade til fremstilling af n,n-dimethylaminomethylarylforbindelser |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI903457A0 FI903457A0 (fi) | 1990-07-09 |
| FI102166B1 FI102166B1 (fi) | 1998-10-30 |
| FI102166B true FI102166B (fi) | 1998-10-30 |
Family
ID=8122450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI903457A FI102166B (fi) | 1989-07-10 | 1990-07-09 | Menetelmä N,N-dimetyyliaminometyyliaryyliyhdisteiden valmistamiseksi |
Country Status (8)
| Country | Link |
|---|---|
| AT (1) | AT398565B (de) |
| DD (1) | DD296481A5 (de) |
| DE (1) | DE4020964A1 (de) |
| DK (1) | DK161513C (de) |
| FI (1) | FI102166B (de) |
| HU (1) | HU206076B (de) |
| NO (1) | NO170578C (de) |
| SE (1) | SE501162C2 (de) |
Families Citing this family (1)
| 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 NO NO903062A patent/NO170578C/no unknown
- 1990-07-09 HU HU414390A patent/HU206076B/hu not_active IP Right Cessation
- 1990-07-09 FI FI903457A patent/FI102166B/fi not_active IP Right Cessation
- 1990-07-09 DD DD34263490A patent/DD296481A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| AT398565B (de) | 1994-12-27 |
| NO170578C (no) | 1992-11-04 |
| DE4020964A1 (de) | 1991-01-17 |
| SE9002363D0 (sv) | 1990-07-05 |
| SE9002363L (sv) | 1991-01-11 |
| NO170578B (no) | 1992-07-27 |
| HU206076B (en) | 1992-08-28 |
| FI102166B1 (fi) | 1998-10-30 |
| DK340089A (da) | 1991-01-11 |
| FI903457A0 (fi) | 1990-07-09 |
| DK161513B (da) | 1991-07-15 |
| NO903062L (no) | 1991-01-11 |
| DK340089D0 (da) | 1989-07-10 |
| ATA131390A (de) | 1994-05-15 |
| DK161513C (da) | 1991-12-23 |
| DD296481A5 (de) | 1991-12-05 |
| SE501162C2 (sv) | 1994-11-28 |
| HU904143D0 (en) | 1990-12-28 |
| NO903062D0 (no) | 1990-07-09 |
| HUT54615A (en) | 1991-03-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IE43517B1 (en) | Substituted imidazoles and their use as fungicides | |
| WO2009155386A1 (en) | A process for the preparation of the apoptosis promoter abt-263 | |
| SG176212A1 (en) | Process for the production of dronedarone intermediates | |
| US4727142A (en) | Process for the preparation of imidates | |
| CN111233617A (zh) | 一种1-碘代炔烃类化合物的合成方法 | |
| NL8700976A (nl) | Pyrazoolderivaten, werkwijze voor het bereiden ervan alsmede voor toepassing in de land- en tuinbouw geschikte fungicide preparaten, die deze verbindingen bevatten. | |
| Nussbaumer et al. | Synthesis and structure-activity relationships of naphthalene-substituted derivatives of the allylamine antimycotic terbinafine | |
| US2706195A (en) | Bis(5, 5, 7, 7-tetramethyl-2-octenyl) dialkylammonium salts | |
| FI89596C (fi) | Foerfarande foer framstaellning av ranitidin eller syraadditionssalter daerav | |
| AT398565B (de) | Verfahren zur herstellung von n,n-dimethylaminomethylaryl- oder n,n-dimethylaminomethylheteroarylverbindungen | |
| US2734920A (en) | New chemical compounds and their | |
| JPS6227059B2 (de) | ||
| US5276169A (en) | Antimycotic carbonyl- and amino-substituted tetrahydrofurans | |
| JPH062747B2 (ja) | 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 | |
| KR100941174B1 (ko) | 퓨란 유도체와 은 촉매를 이용한 이의 제조방법 | |
| KR920000266B1 (ko) | N-(2-프로폭시에틸)-2',6'-디에틸아닐린의 제조방법 | |
| FI64580C (fi) | Foerfarande foer framstaellning av terapeutiskt aktiv n,n-dimetyl-3-(4-bromfenyl)-3-(3-pyridyl)-allylamin och den som mellanprodukt anvaendbara foereningen 1-(4-bromfenyl)-1-(3-pyridyl)-eten | |
| US20040097740A1 (en) | Method for producing delta 1-pyrrolines | |
| CN121426762A (zh) | 一种3,5-二(三氟甲基)苯基取代的噻唑类化合物及其用途 | |
| KR910003632B1 (ko) | N-(2-알콕시에틸)-2',6'-디에틸아닐린의 제조방법 | |
| SU1659400A1 (ru) | Способ получени гидрохлорида N, N-диметил-N-(2,3-дихлорпропил)амина | |
| FI90061C (fi) | Foerfarande foer framstaellning av aminderivat | |
| CA1042463A (en) | Tertiary-alkylamino-lower acyl-xylidides | |
| FI62534B (fi) | Som mellanprodukt vid framstaellning av 2-hydroximetyl-3-hydroxi-6-(1-hydroxi-2-t-butylaminoetyl)-pyridin anvaendbar 2-hydroximetyl-3-benzyloxipyridin-6-epoxietan | |
| KR900003882B1 (ko) | H₂항히스타민 활성을 갖는 화합물의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: A/S GEA FARMACEUTISK FABRIK |