HRP20210376T1 - Novi intermedijeri za pripremu remifentanil hidroklorida - Google Patents
Novi intermedijeri za pripremu remifentanil hidroklorida Download PDFInfo
- Publication number
- HRP20210376T1 HRP20210376T1 HRP20210376TT HRP20210376T HRP20210376T1 HR P20210376 T1 HRP20210376 T1 HR P20210376T1 HR P20210376T T HRP20210376T T HR P20210376TT HR P20210376 T HRP20210376 T HR P20210376T HR P20210376 T1 HRP20210376 T1 HR P20210376T1
- Authority
- HR
- Croatia
- Prior art keywords
- compound
- image
- remifentanil
- sodium
- converted
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims 2
- WFBMIPUMYUHANP-UHFFFAOYSA-N remifentanil hydrochloride Chemical compound [Cl-].C1C[NH+](CCC(=O)OC)CCC1(C(=O)OC)N(C(=O)CC)C1=CC=CC=C1 WFBMIPUMYUHANP-UHFFFAOYSA-N 0.000 title claims 2
- 229960003011 remifentanil hydrochloride Drugs 0.000 title claims 2
- 239000000543 intermediate Substances 0.000 title 1
- 229940125810 compound 20 Drugs 0.000 claims 9
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 claims 9
- 238000000034 method Methods 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- ZTVQQQVZCWLTDF-UHFFFAOYSA-N Remifentanil Chemical compound C1CN(CCC(=O)OC)CCC1(C(=O)OC)N(C(=O)CC)C1=CC=CC=C1 ZTVQQQVZCWLTDF-UHFFFAOYSA-N 0.000 claims 4
- 229960003394 remifentanil Drugs 0.000 claims 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 3
- 230000015572 biosynthetic process Effects 0.000 claims 3
- 238000003786 synthesis reaction Methods 0.000 claims 3
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 claims 2
- IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- 229940100198 alkylating agent Drugs 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 229940125797 compound 12 Drugs 0.000 claims 2
- 229940126086 compound 21 Drugs 0.000 claims 2
- -1 cyanide compound Chemical class 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 2
- JRGDCDUZKXETSW-UHFFFAOYSA-N 2-cyanoethyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCCC#N)C=C1 JRGDCDUZKXETSW-UHFFFAOYSA-N 0.000 claims 1
- XZXUHRRXUGMTRH-UHFFFAOYSA-N 2-cyanoethyl methanesulfonate Chemical compound CS(=O)(=O)OCCC#N XZXUHRRXUGMTRH-UHFFFAOYSA-N 0.000 claims 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- CQZIEDXCLQOOEH-UHFFFAOYSA-N 3-bromopropanenitrile Chemical compound BrCCC#N CQZIEDXCLQOOEH-UHFFFAOYSA-N 0.000 claims 1
- GNHMRTZZNHZDDM-UHFFFAOYSA-N 3-chloropropionitrile Chemical group ClCCC#N GNHMRTZZNHZDDM-UHFFFAOYSA-N 0.000 claims 1
- YYZBPKCINJVSGH-UHFFFAOYSA-N 3-iodopropanenitrile Chemical compound ICCC#N YYZBPKCINJVSGH-UHFFFAOYSA-N 0.000 claims 1
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- SXWRTZOXMUOJER-UHFFFAOYSA-N hydron;piperidin-4-one;chloride;hydrate Chemical compound O.Cl.O=C1CCNCC1 SXWRTZOXMUOJER-UHFFFAOYSA-N 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 claims 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical group CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/98—Nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/66—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having a hetero atom as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (15)
1. Spoj formule 20 i njegove soli:
[image]
2. Uporaba spoja 20 za sintezu remifentanila (1).
3. Uporaba spoja 20 prema patentnom zahtjevu 2 naznačena time, što se spoj 20 prvo pretvara u spoj 21.
[image]
4. Uporaba spoja 20 prema patentnom zahtjevu 3, naznačena time, što je sredstvo za acilaciju propionski anhidrid ili propionil klorid.
5. Uporaba spoja 20 prema patentnom zahtjevu 4, naznačena time, što se koristi neutralizator kiseline odabran od trietilamina, morfolina, piperidina, piridina ili druge organske baze.
6. Uporaba spoja 20 prema patentnom zahtjevu 3 naznačena time, što se spoj 21 pretvara u remifentanil (1).
7. Uporaba spoja 20 za sintezu remifentanila prema patentnom zahtjevu 2 naznačena time, što se spoj 20 prvo pretvara u spoj 12.
[image]
8. Uporaba spoja 20 prema patentnom zahtjevu 7 naznačena time, što se spoj 12 pretvara u remifentanil (1).
9. Postupak za pripremu spoja prema patentnom zahtjevu 1 naznačen time što se spoj priprema reakcijom spoja 19 sa fenilaminom u prisustvu cijanidnog spoja.
[image]
10. Postupak prema patentnom zahtjevu 9 naznačen time što je cijanidni spoj natrijev cijanid.
11. Postupak za pripremu spoja 19 naznačen time što se spoj priprema alkilacijom 4-piperidon hidroklorid monohidrata odgovarajućim alkilirajućim sredstvom u prisustvu baznog katalizatora.
12. Postupak prema patentnom zahtjevu 11 naznačen time što je odgovarajuće alkilirajuće sredstvo 3-kloropropionitril, 3-bromopropionitril, 3-jodopropionitril, 2-cijanoetil metansulfonat, 2-cijanoetil 4-metilbenzensulfonat.
13. Postupak prema patentnom zahtjevu 12 naznačen time što je bazni katalizator natrij ili kalij karbonat, natrij-hidrogen karbonat, natrij ili kalij hidroksid, natrij-amid, kalij terc-butoksid, natrij-etoksid.
14. Postupak prema patentnom zahtjevu 13 naznačen time što je korišteno otapalo aceton, metil-etil keton, izopropanol, acetonitril, N,N-dimetilacetamid, N,N-dimetilformamid, tetrahidrofuran, 2-metil tetrahidrofuran.
15. Uporaba spoja prema patentnom zahtjevu 1 za sintezu remifentanil hidroklorida prema sljedećoj shemi:
[image]
[image]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18202878.7A EP3643704B1 (en) | 2018-10-26 | 2018-10-26 | New intermediates for the preparation of remifentanil hydrochloride |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20210376T1 true HRP20210376T1 (hr) | 2021-04-16 |
Family
ID=64051418
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20210376TT HRP20210376T1 (hr) | 2018-10-26 | 2021-03-03 | Novi intermedijeri za pripremu remifentanil hidroklorida |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10844014B2 (hr) |
| EP (1) | EP3643704B1 (hr) |
| DK (1) | DK3643704T3 (hr) |
| ES (1) | ES2858404T3 (hr) |
| HR (1) | HRP20210376T1 (hr) |
| PL (1) | PL3643704T3 (hr) |
| PT (1) | PT3643704T (hr) |
| RS (1) | RS61517B1 (hr) |
| SI (1) | SI3643704T1 (hr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB202010168D0 (en) * | 2020-07-02 | 2020-08-19 | Johnson Matthey Plc | Process for preparing remifentanil hydrochloride |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5019583A (en) | 1989-02-15 | 1991-05-28 | Glaxo Inc. | N-phenyl-N-(4-piperidinyl)amides useful as analgesics |
| WO2007061555A1 (en) | 2005-11-17 | 2007-05-31 | Mallinckrodt Inc. | Process for synthesizing remifentanil |
| EP1984336A2 (en) | 2006-01-24 | 2008-10-29 | Mallinckrodt, Inc. | Process for synthesizing remifentanil |
| EP1867635A1 (en) * | 2006-06-15 | 2007-12-19 | Kern Pharma, S.L. | Process for preparing remifentanil, intermediates thereof, use of said intermediates and processes for their preparation |
| WO2010053944A1 (en) | 2008-11-04 | 2010-05-14 | Cambrex Charles City, Inc. | Improved method of making piperidine derivatives |
-
2018
- 2018-10-26 PT PT182028787T patent/PT3643704T/pt unknown
- 2018-10-26 SI SI201830231T patent/SI3643704T1/sl unknown
- 2018-10-26 PL PL18202878T patent/PL3643704T3/pl unknown
- 2018-10-26 ES ES18202878T patent/ES2858404T3/es active Active
- 2018-10-26 DK DK18202878.7T patent/DK3643704T3/da active
- 2018-10-26 RS RS20210271A patent/RS61517B1/sr unknown
- 2018-10-26 EP EP18202878.7A patent/EP3643704B1/en active Active
-
2019
- 2019-10-25 US US16/664,464 patent/US10844014B2/en active Active
-
2021
- 2021-03-03 HR HRP20210376TT patent/HRP20210376T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SI3643704T1 (sl) | 2021-04-30 |
| PL3643704T3 (pl) | 2021-06-14 |
| EP3643704A1 (en) | 2020-04-29 |
| EP3643704B1 (en) | 2020-12-16 |
| US10844014B2 (en) | 2020-11-24 |
| PT3643704T (pt) | 2021-03-08 |
| ES2858404T3 (es) | 2021-09-30 |
| DK3643704T3 (da) | 2021-03-15 |
| RS61517B1 (sr) | 2021-03-31 |
| US20200131127A1 (en) | 2020-04-30 |
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