HRP20211099T1 - Postupak za pripreme gabapentina - Google Patents
Postupak za pripreme gabapentina Download PDFInfo
- Publication number
- HRP20211099T1 HRP20211099T1 HRP20211099TT HRP20211099T HRP20211099T1 HR P20211099 T1 HRP20211099 T1 HR P20211099T1 HR P20211099T T HRP20211099T T HR P20211099TT HR P20211099 T HRP20211099 T HR P20211099T HR P20211099 T1 HRP20211099 T1 HR P20211099T1
- Authority
- HR
- Croatia
- Prior art keywords
- alkali
- specified
- formula
- reaction
- stated
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 9
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 title claims 6
- 229960002870 gabapentin Drugs 0.000 title claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- 239000003513 alkali Substances 0.000 claims 5
- 238000006243 chemical reaction Methods 0.000 claims 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims 2
- YDDZHTSOBDNNMZ-UHFFFAOYSA-N 2,4-dioxo-3-azaspiro[5.5]undecane-1,5-dicarbonitrile Chemical compound N#CC1C(=O)NC(=O)C(C#N)C11CCCCC1 YDDZHTSOBDNNMZ-UHFFFAOYSA-N 0.000 claims 1
- QJGSJXLCJRXTRY-UHFFFAOYSA-N 2-[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid Chemical compound NC(=O)CC1(CC(O)=O)CCCCC1 QJGSJXLCJRXTRY-UHFFFAOYSA-N 0.000 claims 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
- 238000006105 Hofmann reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- CVLJNRXJLADZPU-UHFFFAOYSA-N spiro[3,7-diazabicyclo[3.3.1]nonane-9,1'-cyclohexane]-2,4,6,8-tetrone Chemical compound C12C(NC(C(C(NC1=O)=O)C21CCCCC1)=O)=O CVLJNRXJLADZPU-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/88—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having the nitrogen atom of at least one of the carboxamide groups further acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/20—Spiro-condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Claims (8)
1. Postupak pripreme gabapentina koji obuhvaća korake:
a) reakcije spiro[cikloheksan-1,9’-(3,7-diazabiciklo-[3.3.1]nonan)]-2’,4’,6’,8’-tetraona iz formule VI:
[image]
s lužinom kako bi se dobio 1,1-cikloheksan dioctena kiselina monoamid iz formule IV i
[image]
b) pretvaranja spoja IV dobivenog u koraku-a u gabapentin I putem Hofmannove reakcije koristeći alkalni hipohalit.
2. Postupak kao što je navedeno u zahtjevu 1, naznačen time što je lužina odabrana iz skupine koja se sastoji od natrijevog hidroksida, kalijevog hidroksida, litijevog hidroksida, natrijevog tert-butoksida i kalijevog tert-butoksida.
3. Postupak kao što je navedeno u zahtjevu 2, naznačen time što je lužina natrijev hidroksid.
4. Postupak kao što je navedeno u zahtjevu 3, naznačen time što je koncentracija lužine u rasponu od 5% do 50% ( w/V - mase po volumenu).
5. Postupak kao što je navedeno u zahtjevu 3, naznačen time što je koncentracija lužine u rasponu od 15% do 25% ( w/V - mase po volumenu).
6. Postupak kao što je navedeno u zahtjevu 1, naznačen time što se u koraku – a reakcija izvodi na temperaturi refluksa kroz vremenski period od 6 do 24 sata.
7. Postupak kao što je navedeno u zahtjevu 6, naznačen time što se u koraku – a reakcija izvodi kroz vremenski period od 15 do 20 sati.
8. Postupak kao što je navedeno u zahtjevu 1, naznačen time što se spoj formule VI korišten u koraku – a priprema reakcijom 2,4-diokso-3-aza-spiro[5.5]undekan-1,5-dikarbonitrila formule V
[image]
s 50% do 70% otopine sumporne kiseline na 90°C do 110°C.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN201841028887 | 2018-08-01 | ||
| EP18199836.0A EP3604272B1 (en) | 2018-08-01 | 2018-10-11 | Process for the preparation of gabapentin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20211099T1 true HRP20211099T1 (hr) | 2021-10-15 |
Family
ID=63833896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20211099TT HRP20211099T1 (hr) | 2018-08-01 | 2021-07-09 | Postupak za pripreme gabapentina |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US10399926B1 (hr) |
| EP (1) | EP3604272B1 (hr) |
| DK (1) | DK3604272T5 (hr) |
| ES (1) | ES2880403T3 (hr) |
| HR (1) | HRP20211099T1 (hr) |
| PL (1) | PL3604272T3 (hr) |
| PT (1) | PT3604272T (hr) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2960441A (en) | 1957-09-17 | 1960-11-15 | Warner Lambert Pharmaceutical | Therapeutic compositions of salts of 3, 3-pentamethylene-4-hydroxybutyric acid |
| US4087544A (en) | 1974-12-21 | 1978-05-02 | Warner-Lambert Company | Treatment of cranial dysfunctions using novel cyclic amino acids |
| DE2460891C2 (de) | 1974-12-21 | 1982-09-23 | Gödecke AG, 1000 Berlin | 1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE3234697A1 (de) | 1982-09-18 | 1984-03-22 | Kali-Chemie Pharma Gmbh, 3000 Hannover | Neue diazabicyclo-(3,3,1)-nonane |
| IL144063A0 (en) | 2001-06-28 | 2002-04-21 | Bromine Compounds Ltd | Process for the preparation of 1,1-cyclohexanediacetic acid |
| ITMI20041271A1 (it) | 2004-06-24 | 2004-09-24 | Zambon Spa | Processo di preparazione di gabapentina |
| US8431739B2 (en) | 2010-06-14 | 2013-04-30 | Divi's Laboratories, Ltd. | Process for the preparation of gabapentin |
| CN105061239A (zh) | 2015-08-18 | 2015-11-18 | 太仓运通生物化工有限公司 | 一种加巴喷丁的合成方法 |
-
2018
- 2018-10-03 US US16/150,517 patent/US10399926B1/en active Active
- 2018-10-11 PL PL18199836T patent/PL3604272T3/pl unknown
- 2018-10-11 PT PT181998360T patent/PT3604272T/pt unknown
- 2018-10-11 ES ES18199836T patent/ES2880403T3/es active Active
- 2018-10-11 DK DK18199836.0T patent/DK3604272T5/da active
- 2018-10-11 EP EP18199836.0A patent/EP3604272B1/en active Active
-
2021
- 2021-07-09 HR HRP20211099TT patent/HRP20211099T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK3604272T3 (da) | 2021-07-12 |
| ES2880403T3 (es) | 2021-11-24 |
| PL3604272T3 (pl) | 2021-10-25 |
| EP3604272A1 (en) | 2020-02-05 |
| DK3604272T5 (da) | 2021-08-02 |
| US10399926B1 (en) | 2019-09-03 |
| EP3604272B1 (en) | 2021-04-14 |
| PT3604272T (pt) | 2021-06-30 |
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