AR125205A1 - Nuevo proceso para la síntesis de derivados del ácido 5-{5-cloro-2-[(3s)-3-[(morfolin-4-il)metil]-3,4-dihidroisoquinolina-2(1h)-carbonil]fenil}-1,2-dimetil-1h-pirrol-3-carboxílico y su aplicación para la producción de compuestos farmacéuticos - Google Patents
Nuevo proceso para la síntesis de derivados del ácido 5-{5-cloro-2-[(3s)-3-[(morfolin-4-il)metil]-3,4-dihidroisoquinolina-2(1h)-carbonil]fenil}-1,2-dimetil-1h-pirrol-3-carboxílico y su aplicación para la producción de compuestos farmacéuticosInfo
- Publication number
- AR125205A1 AR125205A1 ARP220100687A ARP220100687A AR125205A1 AR 125205 A1 AR125205 A1 AR 125205A1 AR P220100687 A ARP220100687 A AR P220100687A AR P220100687 A ARP220100687 A AR P220100687A AR 125205 A1 AR125205 A1 AR 125205A1
- Authority
- AR
- Argentina
- Prior art keywords
- compound
- formula
- group
- yield
- pharmaceutically acceptable
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 19
- 238000004519 manufacturing process Methods 0.000 title abstract 5
- FWEOQOXTVHGIFQ-UHFFFAOYSA-N 8-anilinonaphthalene-1-sulfonic acid Chemical class C=12C(S(=O)(=O)O)=CC=CC2=CC=CC=1NC1=CC=CC=C1 FWEOQOXTVHGIFQ-UHFFFAOYSA-N 0.000 title 1
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000002904 solvent Substances 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 239000000010 aprotic solvent Substances 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000007822 coupling agent Substances 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical group CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229910052763 palladium Inorganic materials 0.000 abstract 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical group CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 abstract 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 abstract 2
- UHQUHRWIIMVTTJ-UHFFFAOYSA-N CC(N(C)C(C#N)=C1)=C1NC(C=C1)=CC=C1OCC1=CC=CC=C1 Chemical compound CC(N(C)C(C#N)=C1)=C1NC(C=C1)=CC=C1OCC1=CC=CC=C1 UHQUHRWIIMVTTJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- 150000002825 nitriles Chemical group 0.000 abstract 1
- 238000005897 peptide coupling reaction Methods 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/50—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/10—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using coupling agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Epidemiology (AREA)
- Analytical Chemistry (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
La presente invención se refiere a un nuevo proceso para preparar derivados del ácido 5-{5-cloro-2-[(3S)-3-[(morfolin-4-il)metil]-3,4-dihidroisoquinolina-2(1H)-carbonil]fenil}-1,2-dimetil-1H-pirrol-3-carboxílico y a su aplicación para la producción de compuestos farmacéuticos. Reivindicación 1: Un proceso para preparar un compuesto de fórmula (5) en donde: Z es un grupo seleccionado de -COOR y -CN, y R representa un grupo alquilo(C₁-C₆), un grupo alilo o un grupo -CH₂-arilo, que comprende la etapa de hacer reaccionar un compuesto de fórmula (3) en donde Z es como se ha definido anteriormente, con un compuesto de fórmula (4) en donde W representa un grupo saliente seleccionado de átomo de halógeno, grupo trifluorometanosulfonato, grupo metanosulfonato y grupo para-toluenosulfonato, en un disolvente o una mezcla de disolventes, a una temperatura superior a 70ºC en presencia de: (i) un catalizador de paladio; (ii) opcionalmente una fosfina; y (iii) una base. Reivindicación 39: Un proceso para preparar el Compuesto de fórmula (A) caracterizado porque el compuesto de fórmula (1) o una sal de adición del mismo con un ácido farmacéuticamente aceptable, se somete a una reacción de acoplamiento con el compuesto de fórmula (2) en donde W representa un grupo saliente seleccionado de átomo de halógeno, grupo trifluorometanosulfonato, grupo metanosulfonato y grupo para-toluenosulfonato, en un disolvente aprótico en presencia de una base amina y un agente de acoplamiento a una temperatura comprendida entre 20 y 50ºC, para rendir el compuesto de fórmula (4), o una sal de adición del mismo con un ácido farmacéuticamente aceptable, compuesto de fórmula (4) que se hace reaccionar con un compuesto de fórmula (3) en donde: Z es un grupo seleccionado de -COOR y -CN, y R representa un grupo alquilo(C₁-C₆), un grupo alilo o un grupo -CH₂-arilo, en un disolvente o una mezcla de disolventes, a una temperatura superior a 70ºC en presencia de: (iv) un catalizador de paladio; (v) opcionalmente una fosfina; y (vi) una base, para rendir el compuesto de fórmula (5) la función éster o nitrilo de dicho compuesto de fórmula (5) se hidroliza además en un medio prótico para rendir el compuesto de fórmula (6), compuesto de fórmula (6) que se aísla además como un zwitterión o en la forma de una sal de adición del mismo con un ácido farmacéuticamente aceptable, antes de ser sometido a un acoplamiento peptídico con 4-[4-(benciloxi)anilino]-1,5-dimetil-1H-pirrol-2-carbonitrilo de fórmula (7) en un disolvente aprótico en presencia de un agente de acoplamiento y opcionalmente en presencia de una base amina, para rendir el compuesto de fórmula (8), compuesto de fórmula (8) que se desprotege en condiciones ácidas para rendir el Compuesto de fórmula (A), compuesto que se aísla y puede convertirse además en sus sales de adición con un ácido o base farmacéuticamente aceptable.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP21305366 | 2021-03-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
AR125205A1 true AR125205A1 (es) | 2023-06-21 |
Family
ID=75497873
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP220100687A AR125205A1 (es) | 2021-03-24 | 2022-03-23 | Nuevo proceso para la síntesis de derivados del ácido 5-{5-cloro-2-[(3s)-3-[(morfolin-4-il)metil]-3,4-dihidroisoquinolina-2(1h)-carbonil]fenil}-1,2-dimetil-1h-pirrol-3-carboxílico y su aplicación para la producción de compuestos farmacéuticos |
Country Status (12)
Country | Link |
---|---|
US (1) | US20240208926A1 (es) |
EP (1) | EP4313964A1 (es) |
JP (1) | JP2024511422A (es) |
KR (1) | KR20230160303A (es) |
CN (1) | CN116997544A (es) |
AR (1) | AR125205A1 (es) |
AU (1) | AU2022245255A1 (es) |
BR (1) | BR112023018582A2 (es) |
CA (1) | CA3214107A1 (es) |
IL (1) | IL306011A (es) |
MX (1) | MX2023011196A (es) |
WO (1) | WO2022200444A1 (es) |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR3008975A1 (fr) | 2013-07-23 | 2015-01-30 | Servier Lab | Nouveaux derives de pyrrole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
UY38431A (es) | 2018-10-31 | 2020-05-29 | Servier Lab | Formulación basada en ciclodextrina de un inhibidor de bcl-2 |
LT3873894T (lt) | 2018-10-31 | 2023-06-26 | Les Laboratoires Servier | Naujoji bcl-2 inhibitoriaus druska, susijusi kristalinė forma, jos gamybos būdas ir farmacinės kompozicijos, kurių sudėtyje ji yra |
-
2022
- 2022-03-23 IL IL306011A patent/IL306011A/en unknown
- 2022-03-23 EP EP22717584.1A patent/EP4313964A1/en active Pending
- 2022-03-23 KR KR1020237035515A patent/KR20230160303A/ko unknown
- 2022-03-23 AR ARP220100687A patent/AR125205A1/es unknown
- 2022-03-23 AU AU2022245255A patent/AU2022245255A1/en active Pending
- 2022-03-23 US US18/551,033 patent/US20240208926A1/en active Pending
- 2022-03-23 CN CN202280020952.2A patent/CN116997544A/zh active Pending
- 2022-03-23 MX MX2023011196A patent/MX2023011196A/es unknown
- 2022-03-23 BR BR112023018582A patent/BR112023018582A2/pt unknown
- 2022-03-23 CA CA3214107A patent/CA3214107A1/en active Pending
- 2022-03-23 JP JP2023558161A patent/JP2024511422A/ja active Pending
- 2022-03-23 WO PCT/EP2022/057655 patent/WO2022200444A1/en active Application Filing
Also Published As
Publication number | Publication date |
---|---|
CN116997544A (zh) | 2023-11-03 |
KR20230160303A (ko) | 2023-11-23 |
BR112023018582A2 (pt) | 2023-10-24 |
IL306011A (en) | 2023-11-01 |
AU2022245255A1 (en) | 2023-09-28 |
EP4313964A1 (en) | 2024-02-07 |
WO2022200444A1 (en) | 2022-09-29 |
WO2022200444A8 (en) | 2023-09-28 |
CA3214107A1 (en) | 2022-09-29 |
US20240208926A1 (en) | 2024-06-27 |
MX2023011196A (es) | 2023-12-05 |
JP2024511422A (ja) | 2024-03-13 |
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