CA2837261C - Novel processes for the preparation of prostaglandin amides - Google Patents

Novel processes for the preparation of prostaglandin amides Download PDF

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Publication number
CA2837261C
CA2837261C CA2837261A CA2837261A CA2837261C CA 2837261 C CA2837261 C CA 2837261C CA 2837261 A CA2837261 A CA 2837261A CA 2837261 A CA2837261 A CA 2837261A CA 2837261 C CA2837261 C CA 2837261C
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Canada
Prior art keywords
group
atom
formula
process according
general formula
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Active
Application number
CA2837261A
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English (en)
French (fr)
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CA2837261A1 (en
Inventor
Gabor Havasi
Tibor Kiss
Iren Hortobagyi
Zsuzsanna Kardos
Istvan Laszlofi
Zoltan Bischof
Adam Bodis
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Chinoin Private Co Ltd
Original Assignee
Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
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Filing date
Publication date
Priority claimed from HU1100291A external-priority patent/HU230703B1/hu
Priority claimed from HU1100292A external-priority patent/HU231134B1/hu
Application filed by Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
Priority to CA3094762A priority Critical patent/CA3094762C/en
Publication of CA2837261A1 publication Critical patent/CA2837261A1/en
Application granted granted Critical
Publication of CA2837261C publication Critical patent/CA2837261C/en
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00Compounds 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
    • C07C405/0008Analogues having the carboxyl group in the side-chains replaced by other functional groups
    • C07C405/0016Analogues having the carboxyl group in the side-chains replaced by other functional groups containing only hydroxy, etherified or esterified hydroxy groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00Compounds 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C405/00Compounds 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
    • C07C405/0008Analogues having the carboxyl group in the side-chains replaced by other functional groups
    • C07C405/0041Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D207/00Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/46Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44Iso-indoles; Hydrogenated iso-indoles
    • C07D209/50Iso-indoles; Hydrogenated iso-indoles with oxygen and nitrogen atoms in positions 1 and 3
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic 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
    • C07D233/56Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic 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
    • C07D233/56Heterocyclic 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
    • C07D233/60Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77Heterocyclic 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
    • C07D307/93Heterocyclic 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
    • C07D307/935Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13Crystalline forms, e.g. polymorphs
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00Systems containing only non-condensed rings
    • C07C2601/06Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • YGENERAL 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
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02PCLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00Technologies relating to chemical industry
    • Y02P20/50Improvements relating to the production of bulk chemicals
    • Y02P20/55Design 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)
  • Furan Compounds (AREA)
  • Pyrrole Compounds (AREA)
  • Indole Compounds (AREA)
CA2837261A 2011-06-02 2012-05-25 Novel processes for the preparation of prostaglandin amides Active CA2837261C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA3094762A CA3094762C (en) 2011-06-02 2012-05-25 Novel processes for the preparation of prostaglandin amides

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
HUP1100292 2011-06-02
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
PCT/HU2012/000045 WO2012164324A1 (en) 2011-06-02 2012-05-25 Novel processes for the preparation of prostaglandin amides

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA3094762A Division CA3094762C (en) 2011-06-02 2012-05-25 Novel processes for the preparation of prostaglandin amides

Publications (2)

Publication Number Publication Date
CA2837261A1 CA2837261A1 (en) 2012-12-06
CA2837261C true CA2837261C (en) 2020-12-15

Family

ID=89990312

Family Applications (3)

Application Number Title Priority Date Filing Date
CA2837261A Active CA2837261C (en) 2011-06-02 2012-05-25 Novel processes for the preparation of prostaglandin amides
CA3094762A Active CA3094762C (en) 2011-06-02 2012-05-25 Novel processes for the preparation of prostaglandin amides
CA3209613A Pending CA3209613A1 (en) 2011-06-02 2012-05-25 Novel processes for the preparation of prostaglandin amides

Family Applications After (2)

Application Number Title Priority Date Filing Date
CA3094762A Active CA3094762C (en) 2011-06-02 2012-05-25 Novel processes for the preparation of prostaglandin amides
CA3209613A Pending CA3209613A1 (en) 2011-06-02 2012-05-25 Novel processes for the preparation of prostaglandin amides

Country Status (17)

Country Link
US (3) US9238621B2 (https=)
EP (1) EP2723714B1 (https=)
JP (3) JP6212485B2 (https=)
KR (3) KR102135550B1 (https=)
CN (4) CN103649047B (https=)
BR (3) BR112013030973B1 (https=)
CA (3) CA2837261C (https=)
ES (1) ES2636756T3 (https=)
HU (1) HUE033642T2 (https=)
IL (1) IL229647A (https=)
MX (1) MX341839B (https=)
PL (1) PL2723714T3 (https=)
PT (1) PT2723714T (https=)
RU (1) RU2618223C2 (https=)
TW (3) TWI632131B (https=)
WO (1) WO2012164324A1 (https=)
ZA (1) ZA201309357B (https=)

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* Cited by examiner, † Cited by third party
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HU231203B1 (hu) 2011-12-21 2021-10-28 CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. Új eljárás travoprost előállítására
DK2911623T3 (da) 2012-10-26 2019-10-28 Forsight Vision5 Inc Oftalmisk system til langvarig frigivelse af lægemiddel til øjet
US9120738B2 (en) * 2012-12-28 2015-09-01 Allergan, Inc. Crystalline forms of bimatoprost acid, methods for preparation, and methods for use thereof
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
HU231214B1 (hu) * 2014-03-13 2021-11-29 CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. Új eljárás nagytisztaságú prosztaglandinok előállítására
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
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
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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US3984424A (en) * 1972-11-08 1976-10-05 Pfizer Inc. P-biphenyl esters of 15-substituted-ω-pentanorprostaglandins
HU171155B (hu) * 1973-04-30 1977-11-28 Pfizer Sposob poluchenija oksa-prostaglandinov
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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Also Published As

Publication number Publication date
US20140135503A1 (en) 2014-05-15
US9573892B2 (en) 2017-02-21
KR20200087871A (ko) 2020-07-21
BR122021008946B1 (pt) 2021-08-10
HUE033642T2 (en) 2017-12-28
JP6487410B2 (ja) 2019-03-20
TW201311629A (zh) 2013-03-16
CN103649047A (zh) 2014-03-19
BR122021008918B1 (pt) 2021-08-10
KR20190124804A (ko) 2019-11-05
TWI632131B (zh) 2018-08-11
US20160137602A1 (en) 2016-05-19
JP6212485B2 (ja) 2017-10-11
US9856213B2 (en) 2018-01-02
CN106316910A (zh) 2017-01-11
JP2014527026A (ja) 2014-10-09
CA3094762C (en) 2023-09-26
CA2837261A1 (en) 2012-12-06
PT2723714T (pt) 2017-08-18
WO2012164324A9 (en) 2014-01-09
RU2013158952A (ru) 2015-07-20
EP2723714B1 (en) 2017-06-21
JP2017075165A (ja) 2017-04-20
TW201708191A (zh) 2017-03-01
BR112013030973B1 (pt) 2021-08-10
CN106278982A (zh) 2017-01-04
CN106349138A (zh) 2017-01-25
WO2012164324A1 (en) 2012-12-06
TWI653222B (zh) 2019-03-11
CA3209613A1 (en) 2012-12-06
BR112013030973A2 (pt) 2016-08-16
PL2723714T3 (pl) 2018-02-28
JP6693859B2 (ja) 2020-05-13
KR102038048B1 (ko) 2019-10-30
US20160145207A1 (en) 2016-05-26
TW201708190A (zh) 2017-03-01
IL229647A (en) 2017-09-28
ES2636756T3 (es) 2017-10-09
EP2723714A1 (en) 2014-04-30
ZA201309357B (en) 2014-08-27
RU2618223C2 (ru) 2017-05-03
IL229647A0 (en) 2014-01-30
CN103649047B (zh) 2017-01-11
CA3094762A1 (en) 2012-12-06
JP2017061555A (ja) 2017-03-30
CN106278982B (zh) 2019-06-14
KR20140053941A (ko) 2014-05-08
MX2013014034A (es) 2015-06-17
US9238621B2 (en) 2016-01-19
MX341839B (es) 2016-09-05
TWI653223B (zh) 2019-03-11
KR102277188B1 (ko) 2021-07-15
BR112013030973A8 (pt) 2021-03-30
KR102135550B1 (ko) 2020-07-21

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