HRP20170711T1 - Kontinuirani postupak za alkilaciju cikličnih tercijarnih amina - Google Patents
Kontinuirani postupak za alkilaciju cikličnih tercijarnih amina Download PDFInfo
- Publication number
- HRP20170711T1 HRP20170711T1 HRP20170711TT HRP20170711T HRP20170711T1 HR P20170711 T1 HRP20170711 T1 HR P20170711T1 HR P20170711T T HRP20170711T T HR P20170711TT HR P20170711 T HRP20170711 T HR P20170711T HR P20170711 T1 HRP20170711 T1 HR P20170711T1
- Authority
- HR
- Croatia
- Prior art keywords
- solution
- bromide
- alkaline agent
- methyl
- cyclo
- Prior art date
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- -1 cyclic tertiary amines Chemical class 0.000 title claims 9
- 230000029936 alkylation Effects 0.000 title claims 2
- 238000005804 alkylation reaction Methods 0.000 title claims 2
- 238000010924 continuous production Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims 19
- 239000003795 chemical substances by application Substances 0.000 claims 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 229940102396 methyl bromide Drugs 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 claims 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 claims 1
- LERNTVKEWCAPOY-VOGVJGKGSA-N C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 Chemical compound C[N+]1(C)[C@H]2C[C@H](C[C@@H]1[C@H]1O[C@@H]21)OC(=O)C(O)(c1cccs1)c1cccs1 LERNTVKEWCAPOY-VOGVJGKGSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical group [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- VPNYRYCIDCJBOM-UHFFFAOYSA-M Glycopyrronium bromide Chemical compound [Br-].C1[N+](C)(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCC1 VPNYRYCIDCJBOM-UHFFFAOYSA-M 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229940100198 alkylating agent Drugs 0.000 claims 1
- 239000002168 alkylating agent Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical group [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 claims 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 229960003750 ethyl chloride Drugs 0.000 claims 1
- 229960002462 glycopyrronium bromide Drugs 0.000 claims 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 1
- 125000005204 heteroarylcarbonyloxy group Chemical group 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 1
- 229960001361 ipratropium bromide Drugs 0.000 claims 1
- KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 claims 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 claims 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 150000003462 sulfoxides Chemical class 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 229960000257 tiotropium bromide Drugs 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C07D451/12—Oxygen atoms acylated by aromatic or heteroaromatic carboxylic acids, e.g. cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
Claims (19)
1. Postupak za kontinuiranu alkilaciju ciklličnih tercijarnih amina koji sadrži:
- kontinuirano napajanje otopine cikličkog tercijarnog amina u pogodnoj otopini ili smjesi otopine i sredstva za alkilaciju, otopljenog u pogodnoj otopini ili smjesi otopine koje su aprotonske otopine odabrane od amida, nitrila i sulfoksida, u reaktor s kontinuiranim protokom;
- održavanje temperature unutar opsega od 20-200°C;
- sakupljanje otopine koja sadrži čisti kvaternarni ciklički amonijski spoj;
- izolaciju čistog kvaternarnog cikličkog amonijskog spoja,
pri čemu, navedeni ciklički tercijarni amini i kvaternarna ciklički amonijski spojevi su spojevi opće formule
[image]
respektivno,
gdje
R je linearna ili granata C1-C12 alkil skupina;
R1 je linearna ili granata C1-C3 alkil skupina;
X je atom halogena ili karbonat, sulfat ili triflat;
i A je radikal koji tvori odabrano supstituiran monocikličan, bicikličan ili tricikličan prsten s atomom dušika, pri čemu je navedeni prsten odabran od odabrano supstituiranih monocikličnih prstenova koj imaju od 4 do 7 atoma, odabrano uključujući 1 ili 2 heteroatoma odabrano od N, O i S, pored atoma dušika za koji su vezani; odabrano supstituiranih bicikličnih prstenova koji imaju od 6 do 9 atoma, odabrano uključujući 1 ili 2 heteroatoma odabrana od N, O i S, pored atoma dušika za koji su vezani; i odabrano supstituiranog tricikličnog prstena koji ima od 8 do 12 atoma, odabrano uključujući 1 ili 2 heteroatoma odabran od N, O i S, pored atoma dušika za koji su vezani.
2. Postupak u skladu s patentnim zahtjevom 1, naznačen time što R je C1-C4 alkil skupina.
3. Postupak u skladu s patentnim zahtjevom 2, naznačen time što R je metil ili izopropil.
4. Postupak u skladu s patentnim zahtjevom 1 naznačen time što R1 je metil.
5. Postupak u skladu s patentnim zahtjevom 1, naznačen time što navedeni monociklični, biciklični i triciklični prstenovi su prstenovi formule
[image]
i odgovarajuće kvaternarne amonijske soli
[image]
gdje R, R1 i X imaju gore prikazana značenja i Y je supstituent odabran iz (ciklo)alkil, aril, heteroaril, arilalkil, heteroarilalkil, (ciklo)alkoksi, ariloksi, heteroariloksi, (ciklo)alkilkarbonil, arilkarbonil, heteroarilkarbonil, (ciklo)alkilkarboniloksi, arilkarboniloksi, heteroarilkarboniloksi, arilalkilkarboniloksi, i heteroarilalkilkarboniloksi.
6. Postupak u skladu s patentnim zahtjevom 5, naznačen time što Y je odabran iz (ciklo)alkilkarboniloksi, arilalkilkarboniloksi i heteroarilalkilkarboniloksi skupine.
7. Postupak u skladu s patentnim zahtjevom 6, naznačen time što Y je skupina formule:
[image]
gdje R2, R3 i R4, isti ili različiti, su vodik, hidroksi, hidroksialkil, poželjno hidroksimetil, fenil, cikloalkil, poželjno ciklopentil, i heteroaril, poželjno tienil.
8. Postupak u skladu s patentnim zahtjevom 1, naznačen time što je alkalno sredstvo spoj formule R1X gde R1 i X imaju gore navedena značenja.
9. Postupak u skladu s patentnim zahtjevom 8, naznačen time što je alkalno sredstvo spoj formule R1X gdje X je atom halogena odabran iz Cl, Br i I.
10. Postupak u skladu s patentnim zahtjevom 9, naznačen time što je alkalno sredstvo odabrano iz metil klorida, metil bromida, metil jodida, etil klorida, etil bromida, etil jodida, n-propil klorida, n-propil bromida, n-propil jodida, izopropil klorida, izopropil bromida i izopropil jodida.
11. Postupak u skladu s patentnim zahtjevom 10, naznačen time što alkalno sredstvo je metil bromid.
12. Postupak u skladu s patentnim zahtjevom 1, naznačen time što je navedena polarna aprotonska otopina odabrana iz acetonitrila, dimetilformamida, dimetilacetamida, N-metilpirolidona i dimetilsulfoksida.
13. Postupak u skladu s patentnim zahtjevom 1, naznačen time što je alkalno sredstvo uvedeno čisto u reaktor s kontinuiranim protokom.
14. Postupak u skladu s patentnim zahtjevom 1, naznačen time što je alkalno sredstvo uvedeno u reaktor s kontinuiranim protokom kao otopina, odabrano prethodno pomješan s otopinom cikličnog tercijarnog amina.
15. Postupak u skladu s patentnim zahtjevom 14, naznačen time što je otopina za pripremu otopine alkalnog sredstva acetonitril.
16. Postupak u skladu s patentnim zahtjevom 1, naznačen time što je otopina za otapanje cikličnog tercijarnog amina odabrana iz dimetilacetamida, dimetilsulfoksida i N-metilpirolidona.
17. Postupak u skladu s patentnim zahtjevom 16, naznačen time što je otopina N-metilpirolidon.
18. Postupak u skladu s patentnim zahtjevom 1, naznačen time što je temperatura u opsegu od 20 do 200°C, poželjno od 40 do 85°C.
19. Postupak u skladu s bilo kojim od prethodnih patentnih zahtjeva za pripremu tiotropij bromida, glikopironij bromida i ipratropij bromida.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11195419.4A EP2607351B1 (en) | 2011-12-22 | 2011-12-22 | Continuous process for the alkylation of cyclic tertiary amines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20170711T1 true HRP20170711T1 (hr) | 2017-07-28 |
Family
ID=45445872
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20170711TT HRP20170711T1 (hr) | 2011-12-22 | 2017-05-12 | Kontinuirani postupak za alkilaciju cikličnih tercijarnih amina |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8865903B2 (hr) |
| EP (1) | EP2607351B1 (hr) |
| JP (1) | JP6045320B2 (hr) |
| CN (1) | CN103172481B (hr) |
| AU (1) | AU2012244237B2 (hr) |
| BR (1) | BR102012032754B8 (hr) |
| CA (1) | CA2793619C (hr) |
| CY (1) | CY1118937T1 (hr) |
| DK (1) | DK2607351T3 (hr) |
| ES (1) | ES2625498T3 (hr) |
| HR (1) | HRP20170711T1 (hr) |
| HU (1) | HUE034540T2 (hr) |
| IL (1) | IL223230B (hr) |
| LT (1) | LT2607351T (hr) |
| PL (1) | PL2607351T3 (hr) |
| PT (1) | PT2607351T (hr) |
| RS (1) | RS55996B1 (hr) |
| RU (1) | RU2614412C2 (hr) |
| SI (1) | SI2607351T1 (hr) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2789611A1 (en) * | 2013-04-08 | 2014-10-15 | Cerbios-Pharma S.A. | A crystalline form of tiotropium bromide |
| CN106831753B (zh) * | 2017-01-10 | 2019-02-22 | 武汉先路医药科技股份有限公司 | 一种异丙托溴铵的合成方法 |
| CN108911994A (zh) * | 2018-06-11 | 2018-11-30 | 上海华银日用品有限公司 | 一种环保长链烷基季铵盐溶液及其连续制备方法 |
| RU2677273C1 (ru) * | 2018-07-30 | 2019-01-16 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Чувашский государственный университет имени И.Н. Ульянова" | Способ получения четвертичных аммониевых соединений метил дицианоацетата |
| CN110183438A (zh) * | 2019-05-17 | 2019-08-30 | 南京望知星医药科技有限公司 | 一种异丙托溴铵的制备方法 |
| PT115583B (pt) | 2019-06-17 | 2022-05-02 | Hovione Farm S A | Processo contínuo para a preparação de medicamentos anticolinérgicos |
| CN111269226B (zh) * | 2020-04-13 | 2021-09-21 | 石家庄四药有限公司 | 异丙托溴铵的合成方法 |
| CN111978316B (zh) * | 2020-08-21 | 2021-06-04 | 华润双鹤药业股份有限公司沧州分公司 | 一种异丙托溴铵的合成方法 |
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|---|---|---|---|---|
| US2956062A (en) | 1959-02-26 | 1960-10-11 | Robins Co Inc A H | Esters of amino alcohols |
| NL172322C (nl) | 1969-02-25 | 1983-08-16 | Hoechst Ag | Werkwijze voor het bereiden van quaternaire ammoniumverbindingen. |
| JPS58174349A (ja) * | 1982-04-08 | 1983-10-13 | Yotsukaichi Gosei Kk | ３−クロル−２−オキシプロピルトリメチルアンモニウムクロライド水溶液の製造法 |
| DE3713996A1 (de) | 1987-04-27 | 1988-11-10 | Henkel Kgaa | Verfahren zur herstellung von quartaeren ammoniumhalogeniden |
| US5610163A (en) | 1989-09-16 | 1997-03-11 | Boehringer Ingelheim Gmbh | Esters of thienyl carboxylic acids and amino alcohols and their quaternization products |
| DE3931041C2 (de) * | 1989-09-16 | 2000-04-06 | Boehringer Ingelheim Kg | Ester von Thienylcarbonsäuren mit Aminoalkoholen, ihre Quaternierungsprodukte, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| US5041664A (en) | 1990-07-23 | 1991-08-20 | Texaco Chemical Company | Continuous process for preparing quaternary ammonium salts |
| JP2886990B2 (ja) * | 1990-12-20 | 1999-04-26 | 三井化学株式会社 | 不飽和第四級アンモニウム塩の製造方法 |
| US5491240A (en) | 1994-09-29 | 1996-02-13 | Witco Corporation | Quaternary compound of a tertiary amine and methyl chloride |
| DE69724967D1 (de) * | 1996-04-24 | 2003-10-23 | Novo Nordisk As | Heterozyklische verbindungen, ihre herstellung und ihre anwendung |
| EP0869114A1 (en) | 1997-04-04 | 1998-10-07 | Dow Europe S.A. | Composition useful for softening applications and processes for the preparation thereof |
| JP4774604B2 (ja) * | 2000-02-14 | 2011-09-14 | 和光純薬工業株式会社 | 第４級アンモニウム塩の製造方法 |
| DE10064816A1 (de) * | 2000-12-22 | 2002-06-27 | Boehringer Ingelheim Pharma | Verfahren zur Herstellung eines Anticholinergikums |
| FR2824062B1 (fr) * | 2001-04-27 | 2004-10-15 | Atofina | Procede de fabrication de solutions aqueuses de sels insatures d'ammonium quaternaire |
| US6610849B2 (en) * | 2001-06-28 | 2003-08-26 | Boehringer Ingelheim Pharma Kg | Process for the manufacture of tropenol |
| SE0104346L (sv) * | 2001-12-21 | 2003-06-22 | Akzo Nobel Nv | Process för kontinuerlig kvartärnering av tertiära aminer med en alkylhalid |
| JP4178837B2 (ja) * | 2002-05-29 | 2008-11-12 | 東亞合成株式会社 | ジアルキルアミノアルキル（メタ）アクリレート４級塩の製造方法 |
| JP4062055B2 (ja) * | 2002-11-01 | 2008-03-19 | 東亞合成株式会社 | ジアルキルアミノアルキル（メタ）アクリレート４級塩の製造方法 |
| AT412088B (de) * | 2002-12-18 | 2004-09-27 | Pharmacon Forschung & Beratung Gmbh | Verfahren zur herstellung der r,r oder s,s konfigurierten glycopyrronium-isomere |
| US8247597B2 (en) | 2010-01-21 | 2012-08-21 | Nalco Company | Continuous production of DMAEA quaternary salts |
-
2011
- 2011-12-22 EP EP11195419.4A patent/EP2607351B1/en active Active
- 2011-12-22 HU HUE11195419A patent/HUE034540T2/en unknown
- 2011-12-22 ES ES11195419.4T patent/ES2625498T3/es active Active
- 2011-12-22 DK DK11195419.4T patent/DK2607351T3/en active
- 2011-12-22 SI SI201131185A patent/SI2607351T1/sl unknown
- 2011-12-22 PL PL11195419T patent/PL2607351T3/pl unknown
- 2011-12-22 RS RS20170460A patent/RS55996B1/sr unknown
- 2011-12-22 PT PT111954194T patent/PT2607351T/pt unknown
- 2011-12-22 LT LTEP11195419.4T patent/LT2607351T/lt unknown
-
2012
- 2012-10-26 AU AU2012244237A patent/AU2012244237B2/en active Active
- 2012-10-29 CA CA2793619A patent/CA2793619C/en active Active
- 2012-11-19 CN CN201210467838.2A patent/CN103172481B/zh active Active
- 2012-11-21 US US13/683,448 patent/US8865903B2/en active Active
- 2012-11-25 IL IL223230A patent/IL223230B/en active IP Right Grant
- 2012-11-29 JP JP2012261150A patent/JP6045320B2/ja active Active
- 2012-12-06 RU RU2012152600A patent/RU2614412C2/ru active
- 2012-12-20 BR BR102012032754A patent/BR102012032754B8/pt active IP Right Grant
-
2017
- 2017-05-12 HR HRP20170711TT patent/HRP20170711T1/hr unknown
- 2017-05-16 CY CY20171100518T patent/CY1118937T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2012152600A (ru) | 2014-06-20 |
| CA2793619A1 (en) | 2013-06-22 |
| DK2607351T3 (en) | 2017-06-06 |
| RS55996B1 (sr) | 2017-09-29 |
| US8865903B2 (en) | 2014-10-21 |
| ES2625498T3 (es) | 2017-07-19 |
| CY1118937T1 (el) | 2018-01-10 |
| BR102012032754A2 (pt) | 2013-11-12 |
| AU2012244237B2 (en) | 2016-11-03 |
| HUE034540T2 (en) | 2018-02-28 |
| PT2607351T (pt) | 2017-05-26 |
| RU2614412C2 (ru) | 2017-03-28 |
| BR102012032754B8 (pt) | 2021-03-23 |
| EP2607351B1 (en) | 2017-03-15 |
| CA2793619C (en) | 2019-02-05 |
| AU2012244237A1 (en) | 2013-07-11 |
| JP6045320B2 (ja) | 2016-12-14 |
| JP2013133335A (ja) | 2013-07-08 |
| CN103172481B (zh) | 2017-05-10 |
| EP2607351A1 (en) | 2013-06-26 |
| PL2607351T3 (pl) | 2017-08-31 |
| US20130165656A1 (en) | 2013-06-27 |
| BR102012032754B1 (pt) | 2020-12-29 |
| LT2607351T (lt) | 2017-06-12 |
| IL223230B (en) | 2018-02-28 |
| SI2607351T1 (sl) | 2017-07-31 |
| CN103172481A (zh) | 2013-06-26 |
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