DE10162684A1 - Verfahren zur Herstellung von Aminen - Google Patents
Verfahren zur Herstellung von AminenInfo
- Publication number
- DE10162684A1 DE10162684A1 DE10162684A DE10162684A DE10162684A1 DE 10162684 A1 DE10162684 A1 DE 10162684A1 DE 10162684 A DE10162684 A DE 10162684A DE 10162684 A DE10162684 A DE 10162684A DE 10162684 A1 DE10162684 A1 DE 10162684A1
- Authority
- DE
- Germany
- Prior art keywords
- solution
- stage
- chlorine
- range
- halogen
- Prior art date
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 title claims abstract description 41
- 150000001412 amines Chemical class 0.000 title claims abstract description 22
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 29
- 150000002367 halogens Chemical class 0.000 claims abstract description 29
- 239000012670 alkaline solution Substances 0.000 claims abstract description 20
- 150000001408 amides Chemical class 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 239000000243 solution Substances 0.000 claims description 51
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 18
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 239000000725 suspension Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- KTHSXUYBQBKHKL-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzamide Chemical compound NC(=O)C1=C(F)C(F)=CC(F)=C1F KTHSXUYBQBKHKL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- SPSWJTZNOXMMMV-UHFFFAOYSA-N 2,3,5,6-tetrafluoroaniline Chemical compound NC1=C(F)C(F)=CC(F)=C1F SPSWJTZNOXMMMV-UHFFFAOYSA-N 0.000 claims description 6
- -1 CF 3 - Chemical compound 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 239000005708 Sodium hypochlorite Substances 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 4
- 150000008430 aromatic amides Chemical class 0.000 claims description 3
- IBOZOWZSXZNIHI-UHFFFAOYSA-N 6-(trifluoromethyl)pyridin-3-amine Chemical compound NC1=CC=C(C(F)(F)F)N=C1 IBOZOWZSXZNIHI-UHFFFAOYSA-N 0.000 claims description 2
- RIKJKWNZUSPCCM-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=C(C(F)(F)F)N=C1 RIKJKWNZUSPCCM-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 abstract description 6
- 238000006731 degradation reaction Methods 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000004982 aromatic amines Chemical class 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- ODUZJBKKYBQIBX-UHFFFAOYSA-N 2,6-difluoroaniline Chemical compound NC1=C(F)C=CC=C1F ODUZJBKKYBQIBX-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000008707 rearrangement Effects 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- JDMFXJULNGEPOI-UHFFFAOYSA-N 2,6-dichloroaniline Chemical compound NC1=C(Cl)C=CC=C1Cl JDMFXJULNGEPOI-UHFFFAOYSA-N 0.000 description 2
- BNBRIFIJRKJGEI-UHFFFAOYSA-N 2,6-difluorobenzonitrile Chemical compound FC1=CC=CC(F)=C1C#N BNBRIFIJRKJGEI-UHFFFAOYSA-N 0.000 description 2
- KNRIBPGPMVZBDZ-UHFFFAOYSA-N 4-chloro-2,3,5,6-tetrafluoroaniline Chemical compound NC1=C(F)C(F)=C(Cl)C(F)=C1F KNRIBPGPMVZBDZ-UHFFFAOYSA-N 0.000 description 2
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 2
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- BEECAQIHCYTZHC-UHFFFAOYSA-N 2,3,4,5-tetrafluoroaniline Chemical compound NC1=CC(F)=C(F)C(F)=C1F BEECAQIHCYTZHC-UHFFFAOYSA-N 0.000 description 1
- SBYRHTZJKKWEMP-UHFFFAOYSA-N 2,3,4,6-tetrafluoroaniline Chemical compound NC1=C(F)C=C(F)C(F)=C1F SBYRHTZJKKWEMP-UHFFFAOYSA-N 0.000 description 1
- KVLBXIOFJUWSJQ-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzoic acid Chemical compound OC(=O)C1=C(F)C(F)=CC(F)=C1F KVLBXIOFJUWSJQ-UHFFFAOYSA-N 0.000 description 1
- IOQMWOBRUDNEOA-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzonitrile Chemical compound FC1=CC(F)=C(F)C(C#N)=C1F IOQMWOBRUDNEOA-UHFFFAOYSA-N 0.000 description 1
- AELMDUZWKHVPIF-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzoyl chloride Chemical compound FC1=CC(F)=C(F)C(C(Cl)=O)=C1F AELMDUZWKHVPIF-UHFFFAOYSA-N 0.000 description 1
- JHSPCUHPSIUQRB-UHFFFAOYSA-N 2,6-dichlorobenzamide Chemical compound NC(=O)C1=C(Cl)C=CC=C1Cl JHSPCUHPSIUQRB-UHFFFAOYSA-N 0.000 description 1
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 description 1
- AVRQBXVUUXHRMY-UHFFFAOYSA-N 2,6-difluorobenzamide Chemical compound NC(=O)C1=C(F)C=CC=C1F AVRQBXVUUXHRMY-UHFFFAOYSA-N 0.000 description 1
- WEJHBEDHLLBJFW-UHFFFAOYSA-N 4-(trifluoromethyl)benzamide Chemical compound NC(=O)C1=CC=C(C(F)(F)F)C=C1 WEJHBEDHLLBJFW-UHFFFAOYSA-N 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- 238000007167 Hofmann rearrangement reaction Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- XRKIHUXCUIFHAS-UHFFFAOYSA-N [4-(3-methoxy-3-oxopropyl)phenyl]boronic acid Chemical compound COC(=O)CCC1=CC=C(B(O)O)C=C1 XRKIHUXCUIFHAS-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005257 alkyl acyl group Chemical group 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical class Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004476 plant protection product Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000001256 steam distillation Methods 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/54—Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions
- C07C209/56—Preparation of compounds containing amino groups bound to a carbon skeleton by rearrangement reactions from carboxylic acids involving a Hofmann, Curtius, Schmidt, or Lossen-type rearrangement
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10162684A DE10162684A1 (de) | 2001-12-19 | 2001-12-19 | Verfahren zur Herstellung von Aminen |
| CNB028253159A CN1293036C (zh) | 2001-12-19 | 2002-12-17 | 胺的制备方法 |
| US10/499,876 US7205440B2 (en) | 2001-12-19 | 2002-12-17 | Method of producing amines |
| PCT/EP2002/014388 WO2003051817A1 (de) | 2001-12-19 | 2002-12-17 | Verfahren zur herstellung von aminen |
| AU2002360995A AU2002360995A1 (en) | 2001-12-19 | 2002-12-17 | Method for producing amines |
| JP2003552705A JP2005511779A (ja) | 2001-12-19 | 2002-12-17 | アミンを製造するための方法 |
| EP02795210A EP1472212A1 (de) | 2001-12-19 | 2002-12-17 | Verfahren zur herstellung von aminen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10162684A DE10162684A1 (de) | 2001-12-19 | 2001-12-19 | Verfahren zur Herstellung von Aminen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE10162684A1 true DE10162684A1 (de) | 2003-07-10 |
Family
ID=7709988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE10162684A Ceased DE10162684A1 (de) | 2001-12-19 | 2001-12-19 | Verfahren zur Herstellung von Aminen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7205440B2 (enExample) |
| EP (1) | EP1472212A1 (enExample) |
| JP (1) | JP2005511779A (enExample) |
| CN (1) | CN1293036C (enExample) |
| AU (1) | AU2002360995A1 (enExample) |
| DE (1) | DE10162684A1 (enExample) |
| WO (1) | WO2003051817A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7442834B2 (en) * | 2006-06-12 | 2008-10-28 | Zhejiang Chiral Medicine Chemicals Co., Ltd. | Process suitable for industrial scale production of gabapentin |
| JP5524491B2 (ja) * | 2008-03-04 | 2014-06-18 | 石原産業株式会社 | ３−アミノ−２−クロロ−６−トリフルオロメチルピリジンの製造方法 |
| CN102351713B (zh) * | 2011-08-11 | 2013-09-11 | 扬州天辰精细化工有限公司 | 2，6-二氟苯胺的工业化生产方法 |
| CN107445941A (zh) * | 2017-08-14 | 2017-12-08 | 河南科技大学第附属医院 | 具有免疫抑制活性的三氮唑类化合物的制备方法及应用 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES370147A1 (es) * | 1968-08-29 | 1971-04-01 | Gulf Research Development Co | Un procedimiento para fabricar ciclopropilamina. |
| JPS61271255A (ja) | 1985-05-25 | 1986-12-01 | Ihara Chem Ind Co Ltd | アニリン類の製造方法 |
| US4590292A (en) * | 1985-06-10 | 1986-05-20 | Ciba-Geigy Corporation | Process for the manufacture of cyclopropylamine |
| JPS63179856A (ja) | 1987-01-21 | 1988-07-23 | Kyorin Pharmaceut Co Ltd | キノロンカルボン酸誘導体の製造方法並びにその中間体 |
| DE3836782A1 (de) * | 1988-10-28 | 1990-05-31 | Bayer Ag | Verfahren zur herstellung von cyclopropancarbonsaeureamid |
| DE3836917A1 (de) * | 1988-10-29 | 1990-05-17 | Bayer Ag | Verfahren zur herstellung von cyclopropylamin |
| US5034410A (en) * | 1989-10-11 | 1991-07-23 | Syntex (U.S.A.) Inc. | Anthelmintically active benzenepropanamide derivatives |
| US5001124A (en) * | 1990-02-02 | 1991-03-19 | Syntex (U.S.A.) Inc. | 4-isoxazolecarboxamide derivatives |
| US5130441A (en) * | 1990-02-06 | 1992-07-14 | Allergan, Inc. | Method for producing amino-2-imidazoline derivatives |
| AU7745991A (en) | 1990-04-11 | 1991-10-30 | Warner-Lambert Company | Amide ester acat inhibitors |
| US5935978A (en) * | 1991-01-28 | 1999-08-10 | Rhone-Poulenc Rorer Limited | Compounds containing phenyl linked to aryl or heteroaryl by an aliphatic- or heteroatom-containing linking group |
| US5698711A (en) | 1991-01-28 | 1997-12-16 | Rhone-Poulenc Rorer Limited | Compounds containing phenyl linked to aryl or heteroaryl by an aliphatic- or heteroatom-containing linking group |
| DE4315623A1 (de) * | 1993-05-11 | 1994-11-17 | Hoechst Ag | Verfahren zur Herstellung von Aminen |
| JPH0827078A (ja) * | 1994-07-12 | 1996-01-30 | Nippon Kayaku Co Ltd | ２−アミノベンゾフェノン類の製造方法 |
| US5696711A (en) * | 1995-12-22 | 1997-12-09 | Intel Corporation | Apparatus and method for performing variable precision floating point rounding operations |
-
2001
- 2001-12-19 DE DE10162684A patent/DE10162684A1/de not_active Ceased
-
2002
- 2002-12-17 EP EP02795210A patent/EP1472212A1/de not_active Withdrawn
- 2002-12-17 US US10/499,876 patent/US7205440B2/en not_active Expired - Fee Related
- 2002-12-17 CN CNB028253159A patent/CN1293036C/zh not_active Expired - Fee Related
- 2002-12-17 WO PCT/EP2002/014388 patent/WO2003051817A1/de not_active Ceased
- 2002-12-17 JP JP2003552705A patent/JP2005511779A/ja not_active Withdrawn
- 2002-12-17 AU AU2002360995A patent/AU2002360995A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002360995A1 (en) | 2003-06-30 |
| JP2005511779A (ja) | 2005-04-28 |
| EP1472212A1 (de) | 2004-11-03 |
| CN1293036C (zh) | 2007-01-03 |
| CN1608047A (zh) | 2005-04-20 |
| US7205440B2 (en) | 2007-04-17 |
| US20050113582A1 (en) | 2005-05-26 |
| WO2003051817A1 (de) | 2003-06-26 |
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Owner name: BAYER CHEMICALS AG, 51373 LEVERKUSEN, DE |
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Owner name: LANXESS DEUTSCHLAND GMBH, 51373 LEVERKUSEN, DE |
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