CA2873977C - N-methyl-4-benzylcarbamidopyridinium chloride and a process for its preparation - Google Patents
N-methyl-4-benzylcarbamidopyridinium chloride and a process for its preparation Download PDFInfo
- Publication number
- CA2873977C CA2873977C CA2873977A CA2873977A CA2873977C CA 2873977 C CA2873977 C CA 2873977C CA 2873977 A CA2873977 A CA 2873977A CA 2873977 A CA2873977 A CA 2873977A CA 2873977 C CA2873977 C CA 2873977C
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- chloromethane
- range
- isonicotinic acid
- benzylcarbamidopyridinium
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 title claims description 26
- 201000010099 disease Diseases 0.000 claims abstract description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 230000003612 virological effect Effects 0.000 claims abstract description 8
- 230000002265 prevention Effects 0.000 claims abstract description 6
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 60
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 39
- YIGMDKYIWMVZDV-UHFFFAOYSA-N n-benzylpyridine-4-carboxamide Chemical compound C=1C=NC=CC=1C(=O)NCC1=CC=CC=C1 YIGMDKYIWMVZDV-UHFFFAOYSA-N 0.000 claims description 36
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 27
- 239000002775 capsule Substances 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000012535 impurity Substances 0.000 claims description 13
- 238000002844 melting Methods 0.000 claims description 13
- 230000008018 melting Effects 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 206010022000 influenza Diseases 0.000 claims description 6
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 206010062106 Respiratory tract infection viral Diseases 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 239000013049 sediment Substances 0.000 description 20
- 239000000203 mixture Substances 0.000 description 18
- 239000011521 glass Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 13
- 238000003556 assay Methods 0.000 description 10
- ILSOAHPXYZRFBA-UHFFFAOYSA-N n-benzyl-1-methylpyridin-1-ium-4-carboxamide;iodide Chemical compound [I-].C1=C[N+](C)=CC=C1C(=O)NCC1=CC=CC=C1 ILSOAHPXYZRFBA-UHFFFAOYSA-N 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 238000013480 data collection Methods 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 238000006073 displacement reaction Methods 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000007853 buffer solution Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229940126601 medicinal product Drugs 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000008351 acetate buffer Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000877 morphologic effect Effects 0.000 description 2
- 239000008055 phosphate buffer solution Substances 0.000 description 2
- 238000012935 Averaging Methods 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241000712431 Influenza A virus Species 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical class NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010972 statistical evaluation Methods 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EPPCT/EP2012/059258 | 2012-05-18 | ||
| PCT/EP2012/059258 WO2013170901A1 (en) | 2012-05-18 | 2012-05-18 | N-methyl-4-benzylcarbamidopyridinium chloride and a process for its preparation |
| PCT/EP2013/060158 WO2013171307A1 (en) | 2012-05-18 | 2013-05-16 | N-methyl-4-benzylcarbamidopyridinium chloride and a process for its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2873977A1 CA2873977A1 (en) | 2013-11-21 |
| CA2873977C true CA2873977C (en) | 2019-09-17 |
Family
ID=48483057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2873977A Expired - Fee Related CA2873977C (en) | 2012-05-18 | 2013-05-16 | N-methyl-4-benzylcarbamidopyridinium chloride and a process for its preparation |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US9493416B2 (OSRAM) |
| EP (1) | EP2850063B1 (OSRAM) |
| JP (1) | JP2015517513A (OSRAM) |
| KR (1) | KR101777561B1 (OSRAM) |
| BR (1) | BR112014028576B1 (OSRAM) |
| CA (1) | CA2873977C (OSRAM) |
| EA (1) | EA025409B1 (OSRAM) |
| ES (1) | ES2573286T3 (OSRAM) |
| IN (1) | IN2014DN10683A (OSRAM) |
| PL (1) | PL2850063T3 (OSRAM) |
| UA (1) | UA110889C2 (OSRAM) |
| WO (2) | WO2013170901A1 (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2689775C1 (ru) * | 2018-11-02 | 2019-05-29 | Открытое акционерное общество "Авексима" | Способ промышленного производства N-метил-4-бензилкарбамидопиридиния йодида |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU58612A1 (ru) | 1939-10-29 | 1939-11-30 | П.С. Мордовин | Устройство дл включени в одну станционную линию двухабонентских аппаратов |
| SU548612A1 (ru) | 1975-07-18 | 1977-02-28 | Казанский Химико-Технологический Институт Им.С.М.Кирова | Способ получени 10-хлорфеноксарсина |
| US4115390A (en) * | 1977-08-19 | 1978-09-19 | Nardi John C | Method for the preparation of 1-alkyl pyridinium chlorides |
| EP0791586B1 (en) * | 1992-06-04 | 2000-07-26 | Micro-Flo Company | Mepiquat chloride, sealed with a water soluble polymer |
| WO2011158058A1 (en) | 2010-06-17 | 2011-12-22 | Farmak International Holding Gmbh | α-CRYSTALLINE FORM OF CARBABENZPYRIDE |
-
2012
- 2012-05-18 WO PCT/EP2012/059258 patent/WO2013170901A1/en not_active Ceased
- 2012-05-18 UA UAA201412193A patent/UA110889C2/uk unknown
-
2013
- 2013-05-16 PL PL13724564.3T patent/PL2850063T3/pl unknown
- 2013-05-16 JP JP2015512063A patent/JP2015517513A/ja active Pending
- 2013-05-16 WO PCT/EP2013/060158 patent/WO2013171307A1/en not_active Ceased
- 2013-05-16 US US14/368,505 patent/US9493416B2/en active Active
- 2013-05-16 EA EA201492161A patent/EA025409B1/ru not_active IP Right Cessation
- 2013-05-16 ES ES13724564.3T patent/ES2573286T3/es active Active
- 2013-05-16 CA CA2873977A patent/CA2873977C/en not_active Expired - Fee Related
- 2013-05-16 BR BR112014028576-4A patent/BR112014028576B1/pt not_active IP Right Cessation
- 2013-05-16 KR KR1020147028207A patent/KR101777561B1/ko not_active Expired - Fee Related
- 2013-05-16 IN IN10683DEN2014 patent/IN2014DN10683A/en unknown
- 2013-05-16 EP EP13724564.3A patent/EP2850063B1/en active Active
-
2016
- 2016-10-20 US US15/298,400 patent/US20170037011A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| KR101777561B1 (ko) | 2017-09-12 |
| JP2015517513A (ja) | 2015-06-22 |
| WO2013170901A1 (en) | 2013-11-21 |
| EP2850063B1 (en) | 2016-04-13 |
| US20140357677A1 (en) | 2014-12-04 |
| UA110889C2 (uk) | 2016-02-25 |
| EA025409B1 (ru) | 2016-12-30 |
| EP2850063A1 (en) | 2015-03-25 |
| CA2873977A1 (en) | 2013-11-21 |
| EA201492161A1 (ru) | 2015-03-31 |
| KR20150013124A (ko) | 2015-02-04 |
| US20170037011A1 (en) | 2017-02-09 |
| CN104321312A (zh) | 2015-01-28 |
| BR112014028576A2 (pt) | 2017-06-27 |
| WO2013171307A1 (en) | 2013-11-21 |
| ES2573286T3 (es) | 2016-06-07 |
| BR112014028576B1 (pt) | 2020-11-03 |
| PL2850063T3 (pl) | 2016-10-31 |
| US9493416B2 (en) | 2016-11-15 |
| IN2014DN10683A (OSRAM) | 2015-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20160415 |
|
| MKLA | Lapsed |
Effective date: 20210517 |