MA33375B1 - Procédé de préparation de l'ibodutant (men15596) et intermédiaires apparentés - Google Patents
Procédé de préparation de l'ibodutant (men15596) et intermédiaires apparentésInfo
- Publication number
- MA33375B1 MA33375B1 MA34472A MA34472A MA33375B1 MA 33375 B1 MA33375 B1 MA 33375B1 MA 34472 A MA34472 A MA 34472A MA 34472 A MA34472 A MA 34472A MA 33375 B1 MA33375 B1 MA 33375B1
- Authority
- MA
- Morocco
- Prior art keywords
- ibodutant
- men15596
- preparing
- alpha
- coupling
- Prior art date
Links
- YQYSVMKCMIUCHY-WJOKGBTCSA-N 6-methyl-n-[1-[[(2r)-1-[[1-(oxan-4-ylmethyl)piperidin-4-yl]methylamino]-1-oxo-3-phenylpropan-2-yl]carbamoyl]cyclopentyl]-1-benzothiophene-2-carboxamide Chemical compound S1C2=CC(C)=CC=C2C=C1C(=O)NC1(C(=O)N[C@H](CC=2C=CC=CC=2)C(=O)NCC2CCN(CC3CCOCC3)CC2)CCCC1 YQYSVMKCMIUCHY-WJOKGBTCSA-N 0.000 title abstract 3
- 108010091949 ibodutant Proteins 0.000 title abstract 2
- 229950007749 ibodutant Drugs 0.000 title abstract 2
- 108010048200 6-methylbenzo(b)thiophene-2-carboxylic acid (1-(2-phenyl-((1-(tetrahydropyran-4-ylmethyl)piperidin-4-ylmethyl)carbamoyl)ethylcarbamoyl)cyclophenyl)amide Proteins 0.000 title 1
- 239000000543 intermediate Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- KQRBOHOKLNORTA-UHFFFAOYSA-N 6-methyl-1-benzothiophene-2-carboxylic acid Chemical compound CC1=CC=C2C=C(C(O)=O)SC2=C1 KQRBOHOKLNORTA-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000008878 coupling Effects 0.000 abstract 2
- 238000010168 coupling process Methods 0.000 abstract 2
- 238000005859 coupling reaction Methods 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical compound O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 238000007306 functionalization reaction Methods 0.000 abstract 1
- LTEKQAPRXFBRNN-UHFFFAOYSA-N piperidin-4-ylmethanamine Chemical compound NCC1CCNCC1 LTEKQAPRXFBRNN-UHFFFAOYSA-N 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4433—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with oxygen as a ring hetero atom
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Compounds Of Unknown Constitution (AREA)
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
La présente invention concerne un nouveau procédé de synthèse du produit nommé ibodutant présenté sur la figure ci-jointe, constitué de peu d'étapes à haut rendement faisant intervenir des réactifs et des solvants présentant un faible impact sur l'environnement. Ledit procédé est caractérisé par le couplage de deux parties, à savoir les composés (3) et (4), l'un d'eux (3) étant synthétisé par couplage de l'acide 6-méthyl-2-benzo[b]thiophènecarboxylique (1) avec l'acide 1-amino-alpha-alpha-cyclopentanecarboxylique et cyclisation ultérieure avec l'oxazolone, tandis que l'autre, le composé (4), est obtenu à partir de fonctionnalisations hautement sélectives appropriées de la 4-aminométhylpipéridine (2).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI2009A000897A IT1394304B1 (it) | 2009-05-21 | 2009-05-21 | Processo per la preparazione di ibodutant (men15596) e relativi intermedi |
| PCT/EP2010/002884 WO2010133306A1 (fr) | 2009-05-21 | 2010-05-11 | Procédé de préparation de l'ibodutant (men15596) et intermédiaires apparentés |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MA33375B1 true MA33375B1 (fr) | 2012-06-01 |
Family
ID=41264221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MA34472A MA33375B1 (fr) | 2009-05-21 | 2010-05-11 | Procédé de préparation de l'ibodutant (men15596) et intermédiaires apparentés |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US8431684B2 (fr) |
| EP (1) | EP2432778B1 (fr) |
| JP (1) | JP5645926B2 (fr) |
| KR (1) | KR101695346B1 (fr) |
| CN (1) | CN102428081B (fr) |
| AR (1) | AR076785A1 (fr) |
| AU (1) | AU2010251514B2 (fr) |
| BR (1) | BRPI1013073A2 (fr) |
| CA (1) | CA2762625A1 (fr) |
| CY (1) | CY1114079T1 (fr) |
| DK (1) | DK2432778T3 (fr) |
| EA (1) | EA019777B1 (fr) |
| EG (1) | EG27000A (fr) |
| ES (1) | ES2409705T3 (fr) |
| HR (1) | HRP20130380T1 (fr) |
| IL (1) | IL216400A (fr) |
| IT (1) | IT1394304B1 (fr) |
| MA (1) | MA33375B1 (fr) |
| MX (1) | MX2011012317A (fr) |
| NZ (1) | NZ596523A (fr) |
| PL (1) | PL2432778T3 (fr) |
| PT (1) | PT2432778E (fr) |
| SG (1) | SG176171A1 (fr) |
| SI (1) | SI2432778T1 (fr) |
| TW (1) | TWI424996B (fr) |
| UA (1) | UA105523C2 (fr) |
| WO (1) | WO2010133306A1 (fr) |
| ZA (1) | ZA201108483B (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20240010642A1 (en) * | 2021-01-05 | 2024-01-11 | Southern Research Institute | Modulators of programmed death-ligand-1 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY130373A (en) * | 2001-10-29 | 2007-06-29 | Malesci Sas | Linear basic compounds having nk-2 antagonist activity and formulations thereof |
| ITFI20040221A1 (it) * | 2004-10-27 | 2005-01-27 | Guidotti & C Spa | Composizioni farmaceutiche a base di nk2 antagonisti per uso pediatrico |
| WO2007080884A1 (fr) * | 2006-01-11 | 2007-07-19 | Seikagaku Corporation | Derive d'ester d'acide cycloalkylcarbonylamino et son procede de production |
-
2009
- 2009-05-21 IT ITMI2009A000897A patent/IT1394304B1/it active
-
2010
- 2010-05-11 EA EA201190267A patent/EA019777B1/ru not_active IP Right Cessation
- 2010-05-11 MX MX2011012317A patent/MX2011012317A/es active IP Right Grant
- 2010-05-11 EP EP10721687A patent/EP2432778B1/fr active Active
- 2010-05-11 CN CN201080021722.5A patent/CN102428081B/zh not_active Expired - Fee Related
- 2010-05-11 BR BRPI1013073A patent/BRPI1013073A2/pt not_active IP Right Cessation
- 2010-05-11 UA UAA201113614A patent/UA105523C2/uk unknown
- 2010-05-11 WO PCT/EP2010/002884 patent/WO2010133306A1/fr not_active Ceased
- 2010-05-11 CA CA2762625A patent/CA2762625A1/fr not_active Abandoned
- 2010-05-11 MA MA34472A patent/MA33375B1/fr unknown
- 2010-05-11 ES ES10721687T patent/ES2409705T3/es active Active
- 2010-05-11 US US13/321,501 patent/US8431684B2/en not_active Expired - Fee Related
- 2010-05-11 HR HRP20130380AT patent/HRP20130380T1/hr unknown
- 2010-05-11 SI SI201030192T patent/SI2432778T1/sl unknown
- 2010-05-11 DK DK10721687.1T patent/DK2432778T3/da active
- 2010-05-11 SG SG2011085545A patent/SG176171A1/en unknown
- 2010-05-11 NZ NZ596523A patent/NZ596523A/xx not_active IP Right Cessation
- 2010-05-11 KR KR1020117027585A patent/KR101695346B1/ko not_active Expired - Fee Related
- 2010-05-11 PL PL10721687T patent/PL2432778T3/pl unknown
- 2010-05-11 AU AU2010251514A patent/AU2010251514B2/en not_active Ceased
- 2010-05-11 JP JP2012511171A patent/JP5645926B2/ja not_active Expired - Fee Related
- 2010-05-11 PT PT107216871T patent/PT2432778E/pt unknown
- 2010-05-20 AR ARP100101759A patent/AR076785A1/es unknown
- 2010-05-20 TW TW099116060A patent/TWI424996B/zh not_active IP Right Cessation
-
2011
- 2011-11-17 IL IL216400A patent/IL216400A/en not_active IP Right Cessation
- 2011-11-17 EG EG2011111951A patent/EG27000A/xx active
- 2011-11-18 ZA ZA2011/08483A patent/ZA201108483B/en unknown
-
2013
- 2013-05-16 CY CY20131100392T patent/CY1114079T1/el unknown
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