BR112013030973A2 - processo para a preparação de amidas de prostaglandina - Google Patents
processo para a preparação de amidas de prostaglandinaInfo
- Publication number
- BR112013030973A2 BR112013030973A2 BR112013030973A BR112013030973A BR112013030973A2 BR 112013030973 A2 BR112013030973 A2 BR 112013030973A2 BR 112013030973 A BR112013030973 A BR 112013030973A BR 112013030973 A BR112013030973 A BR 112013030973A BR 112013030973 A2 BR112013030973 A2 BR 112013030973A2
- Authority
- BR
- Brazil
- Prior art keywords
- group
- formula
- atom
- general formula
- meanings
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- -1 prostaglandin amides Chemical class 0.000 title abstract 3
- 125000004429 atom Chemical group 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000001072 heteroaryl group Chemical group 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 abstract 2
- PTDNHYVEBIHJBK-UHFFFAOYSA-M 2-chloro-1,3-dimethylimidazol-1-ium;chloride Chemical compound [Cl-].CN1C=C[N+](C)=C1Cl PTDNHYVEBIHJBK-UHFFFAOYSA-M 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- AQOKCDNYWBIDND-FTOWTWDKSA-N bimatoprost Chemical compound CCNC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)CCC1=CC=CC=C1 AQOKCDNYWBIDND-FTOWTWDKSA-N 0.000 abstract 1
- 229960002470 bimatoprost Drugs 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0016—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing only hydroxy, etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/50—Iso-indoles; Hydrogenated iso-indoles with oxygen and nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
- Furan Compounds (AREA)
Abstract
resumo patente de invenção: "processo para a preparação de amidas de prostaglandina". a presente invenção refere-se a um processo para a preparação de amidas de prostaglandina da fórmula geral (i), em que na fórmula, as ligações marcadas com linhas pontilhadas podem ser ligações simples ou duplas, no caso de ligações duplas nas posições 5,6 e 13,14, essas podem estar na orientação cis ou trans, q representa um grupo hidroxila e z representa um grupo hidroxila ou oxo, r1 e r2 independentemente, representam um átomo de hidrogênio ou um grupo c1-10-alquila ou aralquila em cadeia linear ou ramificada, opcionalmente substituído com um grupo -ono2 ou um grupo aralquila ou arila, que contém heteroátomo, r3 representa um grupo c4-6 hidrocarboneto saturado ou insaturado, em cadeia linear ou ramificada ou um grupo c4-10 alquilcicloalquila ou cicloalquila ou um grupo fenila, c7-10 alquilarila ou hetarila opcionalmente substituído com um grupo alquila ou com um átomo de halogênio, y representa um grupo (ch2)n ou um átomo de o ou átomo de s e em que n=0-3, caracterizado pelo fato de que um ácido de fórmula geral (ii), em que na fórmula as ligações marcadas com linhas pontilhadas podem ser ligações simples ou duplas, no caso de ligações duplas nas posições 5,6 e 13,14, essas podem estar na orientação cis ou trans, q representa um grupo hidroxila e z representa um grupo hidroxila ou oxo, r3 representa um grupo c4-6 hidrocarboneto saturado ou insaturado, em cadeia linear ou ramificada ou um grupo c4-10 alquilcicloalquila ou cicloalquila ou um grupo fenila, c7-10 alquilarila ou hetarila opcionalmente substituído com um grupo alquila ou com um átomo de halogênio, y representa um grupo (ch2)n ou um átomo de o ou átomo de s e em que n=0-3, é reagido i) com um composto adequado para introduzir o grupo r4, em que r4 representa a.) o grupo da fórmula a.) e a amida resultante da fórmula geral (iii), em que os significados de r3, r4, y e n são como definidos acima, é reagida com uma amina da fórmula geral (iv), nhr1r2 iv. em que os significados de r1 e r2 são definidos acima ou ii) com um composto adequado para introduzir o grupo r5 - em que r5 representa um grupo da fórmula b.), c.), d.) ou e.), em que (x) representa um átomo de halogênio ou um átomo de hidrogênio e o éster ativado resultante da fórmula geral (v), em que os significados de r3, r5, y e n são como definidos acima, é reagido com uma amina da fórmula geral (iv) ou iii.) com uma amina da fórmula geral (iv) - em que os significados de r1 e r2 são como definidos acima - na presença de cloreto de 2-cloro-1,3-dimetilimidazolínio e uma base. outra concretização da nossa invenção é um processo para a preparação de uma forma cristalina de ponto de fusão elevado de bimatoprosta da fórmula (ib). outra concretização da invenção é um processo para a preparação de um composto da fórmula (iib) em forma cristalina.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BR122021008918-3A BR122021008918B1 (pt) | 2011-06-02 | 2012-05-25 | Forma cristalina ii de bimatoproposta e processo para a preparação da mesma |
| BR122021008946-9A BR122021008946B1 (pt) | 2011-06-02 | 2012-05-25 | Composto em sua forma cristalina e processo para a preparação do mesmo |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU1100291A HU230703B1 (hu) | 2011-06-02 | 2011-06-02 | Új eljárás prosztaglandin amidok előállítására |
| HU1100292A HU231134B1 (hu) | 2011-06-02 | 2011-06-02 | Eljárás a bimatoprost kémiailag stabil új kristályformájának előállítására |
| HUP1100291 | 2011-06-02 | ||
| HUP1100292 | 2011-06-02 | ||
| PCT/HU2012/000045 WO2012164324A1 (en) | 2011-06-02 | 2012-05-25 | Novel processes for the preparation of prostaglandin amides |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| BR112013030973A2 true BR112013030973A2 (pt) | 2016-08-16 |
| BR112013030973A8 BR112013030973A8 (pt) | 2021-03-30 |
| BR112013030973B1 BR112013030973B1 (pt) | 2021-08-10 |
Family
ID=89990312
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112013030973-3A BR112013030973B1 (pt) | 2011-06-02 | 2012-05-25 | Processo para a preparação de amidas de prostaglandina |
| BR122021008946-9A BR122021008946B1 (pt) | 2011-06-02 | 2012-05-25 | Composto em sua forma cristalina e processo para a preparação do mesmo |
| BR122021008918-3A BR122021008918B1 (pt) | 2011-06-02 | 2012-05-25 | Forma cristalina ii de bimatoproposta e processo para a preparação da mesma |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR122021008946-9A BR122021008946B1 (pt) | 2011-06-02 | 2012-05-25 | Composto em sua forma cristalina e processo para a preparação do mesmo |
| BR122021008918-3A BR122021008918B1 (pt) | 2011-06-02 | 2012-05-25 | Forma cristalina ii de bimatoproposta e processo para a preparação da mesma |
Country Status (17)
| Country | Link |
|---|---|
| US (3) | US9238621B2 (pt) |
| EP (1) | EP2723714B1 (pt) |
| JP (3) | JP6212485B2 (pt) |
| KR (3) | KR102135550B1 (pt) |
| CN (4) | CN106278982B (pt) |
| BR (3) | BR112013030973B1 (pt) |
| CA (3) | CA2837261C (pt) |
| ES (1) | ES2636756T3 (pt) |
| HU (1) | HUE033642T2 (pt) |
| IL (1) | IL229647A (pt) |
| MX (1) | MX341839B (pt) |
| PL (1) | PL2723714T3 (pt) |
| PT (1) | PT2723714T (pt) |
| RU (1) | RU2618223C2 (pt) |
| TW (3) | TWI653222B (pt) |
| WO (1) | WO2012164324A1 (pt) |
| ZA (1) | ZA201309357B (pt) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU231203B1 (hu) | 2011-12-21 | 2021-10-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Új eljárás travoprost előállítására |
| CN104884006B (zh) | 2012-10-26 | 2017-12-15 | 弗赛特影像5股份有限公司 | 用于持续释放药物到眼睛的眼科系统 |
| US9447014B2 (en) | 2012-12-28 | 2016-09-20 | Allergan, Inc. | Tromethamine salt of bimatoprost acid in crystalline form, methods for preparation, and methods for use thereof |
| US9120738B2 (en) * | 2012-12-28 | 2015-09-01 | Allergan, Inc. | Crystalline forms of bimatoprost acid, methods for preparation, and methods for use thereof |
| HU231214B1 (hu) * | 2014-03-13 | 2021-11-29 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Új eljárás nagytisztaságú prosztaglandinok előállítására |
| US10273206B2 (en) | 2014-06-27 | 2019-04-30 | Allergan, Inc. | Tromethamine salt of bimatoprost acid in crystalline form 1, methods for preparation, and methods for use thereof |
| WO2015199729A1 (en) * | 2014-06-27 | 2015-12-30 | Allergan, Inc. | Tromethamine salt of bimatoprost acid in crystalline form 1, methods for preparation, and methods for use thereof |
| US20160296532A1 (en) | 2015-04-13 | 2016-10-13 | Forsight Vision5, Inc. | Ocular Insert Composition of a Semi-Crystalline or Crystalline Pharmaceutically Active Agent |
| HU231185B1 (hu) * | 2017-07-11 | 2021-07-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Eljárás Misoprostol előállítására és tisztítására |
| CN113548993B (zh) * | 2021-09-01 | 2022-05-27 | 河北化工医药职业技术学院 | 一种卡前列素的制备方法 |
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| HU175889B (en) | 1976-04-08 | 1980-11-28 | Chinoin Gyogyszer Es Vegyeszet | New process for preparing lactol-alcohol derivatives |
| HU175217B (hu) * | 1977-08-03 | 1980-06-28 | Chinoin Gyogyszer Es Vegyeszet | Novyj sposob poluchenija biciklicheskikh laktol-metil-ehfirov |
| HU178202B (en) * | 1977-09-26 | 1982-03-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing new,optically active and racemic bicyclic acetals and merkaptals |
| FR2550799B1 (fr) * | 1983-08-17 | 1986-02-21 | Commissariat Energie Atomique | Compose marque par une enzyme, son procede de preparation et son utilisation en enzymoimmunologie |
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| IN2012DN05209A (pt) * | 2009-11-23 | 2015-10-23 | Allergan Inc | |
| EP2495235B1 (en) * | 2011-03-04 | 2015-08-05 | Newchem S.p.A. | Process for the synthesis of prostaglandins and intermediates thereof |
| HU231203B1 (hu) * | 2011-12-21 | 2021-10-28 | CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. | Új eljárás travoprost előállítására |
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