SI3077355T1 - Novi postopek za sintezo 7-metoksi-naftalen-1-karbaldehida in njegova uporaba pri sintezi agomelatina - Google Patents
Novi postopek za sintezo 7-metoksi-naftalen-1-karbaldehida in njegova uporaba pri sintezi agomelatina Download PDFInfo
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- SI3077355T1 SI3077355T1 SI201430642T SI201430642T SI3077355T1 SI 3077355 T1 SI3077355 T1 SI 3077355T1 SI 201430642 T SI201430642 T SI 201430642T SI 201430642 T SI201430642 T SI 201430642T SI 3077355 T1 SI3077355 T1 SI 3077355T1
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- 230000015572 biosynthetic process Effects 0.000 title claims abstract 27
- 238000003786 synthesis reaction Methods 0.000 title claims abstract 27
- 238000000034 method Methods 0.000 title claims abstract 19
- YJYPHIXNFHFHND-UHFFFAOYSA-N agomelatine Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(OC)=CC=C21 YJYPHIXNFHFHND-UHFFFAOYSA-N 0.000 title claims 5
- 229960002629 agomelatine Drugs 0.000 title claims 5
- WYDUFXRPFJPXGH-UHFFFAOYSA-N 7-methoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C(C=O)C2=CC(OC)=CC=C21 WYDUFXRPFJPXGH-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 55
- 238000006243 chemical reaction Methods 0.000 claims 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 229910052723 transition metal Inorganic materials 0.000 claims 3
- 150000003624 transition metals Chemical class 0.000 claims 3
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 229910052763 palladium Inorganic materials 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims 2
- 125000005425 toluyl group Chemical group 0.000 claims 2
- FWZRNGJNGNRONB-UHFFFAOYSA-N (1-formyl-7-methoxynaphthalen-2-yl) 4-methylbenzenesulfonate Chemical compound CC1=CC=C(C=C1)S(=O)(=O)OC1=C(C2=CC(=CC=C2C=C1)OC)C=O FWZRNGJNGNRONB-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- UNFNRIIETORURP-UHFFFAOYSA-N 7-methoxynaphthalen-2-ol Chemical compound C1=CC(O)=CC2=CC(OC)=CC=C21 UNFNRIIETORURP-UHFFFAOYSA-N 0.000 claims 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical group [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims 1
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 150000002940 palladium Chemical class 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 238000005694 sulfonylation reaction Methods 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/11—Aldehydes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/86—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (22)
- NOVI POSTOPEK ZA SINTEZO 7-METOKSI-NAFTALEN-1-KARBALDEHIDA IN NJEGOVA UPORABA PRI SINTEZI AGOMELATINA Patentni zahtevki1. Postopek za industrijsko sintezo spojine s formulo (I):označen s tem, da 7-metoksi-naftalen-2-ol s formulo (III):reagira, pri čemer se na mestu 1 uvede formilna skupina, da se tvori spojina s formulo (IV):pri čemer je spojina s formulo (IV) izpostavljena reakciji sulfonilacije, da se tvori spojina s formulo (V):pri čemer R predstavlja skupino -CH3, -(CH2)2-CH3, -CF3 oziroma toluil; pri čemer je spojina s formulo (V) izpostavljena reakciji deoksigenacije v prisotnosti prehodne kovine in redukcijskega sredstva, da se tvori spojina s formulo (I), ki se izolira v obliki trdne snovi.
- 2. Postopek za industrijsko sintezo spojine s formulo (I) po zahtevku 1, označen s tem, da R predstavlja skupino -CH3 oziroma toluil.
- 3. Postopek za industrijsko sintezo spojine s formulo (I) po zahtevku 1, označen s tem, da se konverzija spojine s formulo (IV) v spojino s formulo (V) izvede s pomočjo delovanja sulfonil klorida, sulfonskega anhidrida ali sulfonamida.
- 4. Postopek za industrijsko sintezo spojine s formulo (I) po zahtevku 3, označen s tem, da se konverzija spojine s formulo (IV) v spojino s formulo (V) izvede s pomočjo delovanja sulfonil klorida.
- 5. Postopek za industrijsko sintezo spojine s formulo (I) po zahtevku 1, označen s tem, da je v konverziji spojine s formulo (V) v spojino s formulo (I) prehodna kovina nikelj, paladij ali platina.
- 6. Postopek za industrijsko sintezo spojine s formulo (I) po zahtevku 1, označen s tem, da je v konverziji spojine s formulo (V) v spojino s formulo (I) prehodna kovina paladijeva sol.
- 7. Postopek za industrijsko sintezo spojine s formulo (I) po zahtevku 1, označen s tem, da se konverzija spojine s formulo (V) v spojino s formulo (I) izvede v dimetilformamidu, dioksanu, tetrahidrofuranu ali toluenu.
- 8. Postopek za industrijsko sintezo spojine s formulo (I) po zahtevku 7, označen s tem, da se konverzija spojine s formulo (V) v spojino s formulo (I) izvede v dimetilformamidu.
- 9. Postopek za industrijsko sintezo spojine s formulo (I) po zahtevku 1, označen s tem, da se konverzija spojine s formulo (V) v spojino s formulo (I) izvede pri temperaturi med 25 °C in 110 °C.
- 10. Postopek za industrijsko sintezo spojine s formulo (I) po zahtevku 9, označen s tem, da se konverzija spojine s formulo (V) v spojino s formulo (I) izvede pri temperaturi med 40 °C in 95 °C.
- 11. Postopek za industrijsko sintezo spojine s formulo (I) po zahtevku 1, označen s tem, da je v konverziji spojine s formulo (V) v spojino s formulo (I) redukcijsko sredstvo dihidrogen.
- 12. Postopek za industrijsko sintezo spojine s formulo (I) po zahtevku 11, označen s tem, da se dihidrogen pridobi z razpadom amonijevega formata.
- 13. Postopek za industrijsko sintezo spojine s formulo (I) po zahtevku 1, označen s tem, da se konverzija spojine s formulo (V) v spojino s formulo (I) izvede v prisotnosti paladija in dihidrogena.
- 14. Postopek za industrijsko sintezo spojine s formulo (I) po zahtevku 1, označen s tem, da se konverzija spojine s formulo (V) v spojino s formulo (I) izvede v prisotnosti (9,9-dimetil-9/-/-ksanten-4,5-diil)bis(difenilfosfana) ali 1,3-bis(difenilfosfino)propana.
- 15. Spojina s formulo (I) po zahtevku 1 za uporabo kot intermediat za sintezo spojine s formulo (I).
- 16. Spojina s formulo (V) po zahtevku 15 za uporabo kot intermediat za sintezo agomelatina s formulo (II).
- 17. Spojina s formulo (V) po zahtevkih 15 in 16, ki je izbrana izmed naslednjih spojin: - 1-formil-7-metoksinaftalen-2-il 4-metilbenzensulfonat; - 1-formil-7-metoksinaftalen-2-il metansulfonat.
- 18. Uporaba spojine s formulo (V) po katerem koli izmed zahtevkov od 15 do 17 pri sintezi spojine s formulo (I).
- 19. Uporaba spojine s formulo (V) po zahtevku 18 pri sintezi agomelatina s formulo (II).
- 20. Uporaba spojine s formulo (III) po zahtevku 1 pri sintezi spojine s formulo (I).
- 21. Uporaba spojine s formulo (lil) po zahtevku 20 pri sintezi agomelatina s formulo (II).
- 22. Postopek za sintezo agomelatina iz spojine s formulo (V), označen s tem, da se spojina s formulo (V) pridobi s postopkom sinteze po katerem koli izmed zahtevkov od 1 do 4.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1362200A FR3014434B1 (fr) | 2013-12-05 | 2013-12-05 | Nouveau procede de synthese du 7-methoxy-naphtalene-1-carbaldehyde et application a la synthese de l'agomelatine |
| PCT/FR2014/053159 WO2015082849A2 (fr) | 2013-12-05 | 2014-12-04 | Nouveau procede de synthese du 7-methoxy-naphtalene-1-carbaldehyde et application a la synthese de l'agomelatine |
| EP14821796.1A EP3077355B1 (fr) | 2013-12-05 | 2014-12-04 | Nouveau procede de synthese du 7-methoxy-naphtalene-1-carbaldehyde et application a la synthese de l'agomelatine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI3077355T1 true SI3077355T1 (sl) | 2018-04-30 |
Family
ID=50482960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI201430642T SI3077355T1 (sl) | 2013-12-05 | 2014-12-04 | Novi postopek za sintezo 7-metoksi-naftalen-1-karbaldehida in njegova uporaba pri sintezi agomelatina |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US9701608B2 (sl) |
| EP (1) | EP3077355B1 (sl) |
| JP (1) | JP2016539169A (sl) |
| KR (1) | KR20170018799A (sl) |
| CN (1) | CN105793226B (sl) |
| AU (1) | AU2014358967B2 (sl) |
| CA (1) | CA2932196C (sl) |
| CY (1) | CY1120160T1 (sl) |
| DK (1) | DK3077355T3 (sl) |
| EA (1) | EA031684B1 (sl) |
| ES (1) | ES2668527T3 (sl) |
| FR (1) | FR3014434B1 (sl) |
| GE (1) | GEP20186847B (sl) |
| HR (1) | HRP20180693T1 (sl) |
| HU (1) | HUE036874T2 (sl) |
| LT (1) | LT3077355T (sl) |
| MA (1) | MA39062B1 (sl) |
| MD (1) | MD20160072A2 (sl) |
| ME (1) | ME03048B (sl) |
| MX (1) | MX2016007130A (sl) |
| NO (1) | NO3077355T3 (sl) |
| PL (1) | PL3077355T3 (sl) |
| PT (1) | PT3077355T (sl) |
| RS (1) | RS56933B1 (sl) |
| RU (1) | RU2680243C1 (sl) |
| SI (1) | SI3077355T1 (sl) |
| TR (1) | TR201802197T4 (sl) |
| UA (1) | UA117940C2 (sl) |
| WO (1) | WO2015082849A2 (sl) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2658818B1 (fr) * | 1990-02-27 | 1993-12-31 | Adir Cie | Nouveaux derives a structure naphtalenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| KR100849559B1 (ko) * | 2004-01-22 | 2008-07-31 | 일라이 릴리 앤드 캄파니 | 혈관운동 증상의 치료를 위한 선택적 에스트로겐 수용체조절제 |
| FR2866337B1 (fr) * | 2004-02-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese du (7-methoxy-1-naphtyl) acetonitrile et application a la synthese de l'aglomelatine |
| FR2866335B1 (fr) | 2004-02-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
| FR2918369B1 (fr) * | 2007-07-02 | 2009-08-28 | Servier Lab | Nouveaux derives naphtaleniques,leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| CN101638376B (zh) * | 2008-07-29 | 2011-04-27 | 江苏恩华药业股份有限公司 | 阿戈美拉汀的制备方法及其中间体 |
| FR2934859B1 (fr) * | 2008-08-05 | 2010-08-13 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
-
2013
- 2013-12-05 FR FR1362200A patent/FR3014434B1/fr not_active Expired - Fee Related
-
2014
- 2014-04-12 UA UAA201606901A patent/UA117940C2/uk unknown
- 2014-12-04 SI SI201430642T patent/SI3077355T1/sl unknown
- 2014-12-04 AU AU2014358967A patent/AU2014358967B2/en not_active Ceased
- 2014-12-04 CN CN201480066210.9A patent/CN105793226B/zh not_active Expired - Fee Related
- 2014-12-04 RU RU2016126660A patent/RU2680243C1/ru active
- 2014-12-04 GE GEAP201414198A patent/GEP20186847B/en unknown
- 2014-12-04 CA CA2932196A patent/CA2932196C/fr not_active Expired - Fee Related
- 2014-12-04 MD MDA20160072A patent/MD20160072A2/ro not_active Application Discontinuation
- 2014-12-04 JP JP2016536761A patent/JP2016539169A/ja not_active Ceased
- 2014-12-04 KR KR1020167017809A patent/KR20170018799A/ko not_active Application Discontinuation
- 2014-12-04 WO PCT/FR2014/053159 patent/WO2015082849A2/fr active Application Filing
- 2014-12-04 HU HUE14821796A patent/HUE036874T2/hu unknown
- 2014-12-04 ES ES14821796.1T patent/ES2668527T3/es active Active
- 2014-12-04 LT LTEP14821796.1T patent/LT3077355T/lt unknown
- 2014-12-04 EA EA201600439A patent/EA031684B1/ru not_active IP Right Cessation
- 2014-12-04 DK DK14821796.1T patent/DK3077355T3/en active
- 2014-12-04 MX MX2016007130A patent/MX2016007130A/es unknown
- 2014-12-04 US US15/101,120 patent/US9701608B2/en active Active
- 2014-12-04 ME MEP-2018-43A patent/ME03048B/me unknown
- 2014-12-04 TR TR2018/02197T patent/TR201802197T4/tr unknown
- 2014-12-04 RS RS20180247A patent/RS56933B1/sr unknown
- 2014-12-04 PL PL14821796T patent/PL3077355T3/pl unknown
- 2014-12-04 EP EP14821796.1A patent/EP3077355B1/fr active Active
- 2014-12-04 PT PT148217961T patent/PT3077355T/pt unknown
- 2014-12-04 MA MA39062A patent/MA39062B1/fr unknown
- 2014-12-04 NO NO14821796A patent/NO3077355T3/no unknown
-
2018
- 2018-05-02 CY CY20181100451T patent/CY1120160T1/el unknown
- 2018-05-03 HR HRP20180693TT patent/HRP20180693T1/hr unknown
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