PT97688B - Processo para a preparacao de amidas, esteres, acidos alfa-oxo-pirrolo{2,3-b}indol-acetico e analogos relacionados e de composicoes farmaceuticas que os contem - Google Patents
Processo para a preparacao de amidas, esteres, acidos alfa-oxo-pirrolo{2,3-b}indol-acetico e analogos relacionados e de composicoes farmaceuticas que os contem Download PDFInfo
- Publication number
- PT97688B PT97688B PT97688A PT9768891A PT97688B PT 97688 B PT97688 B PT 97688B PT 97688 A PT97688 A PT 97688A PT 9768891 A PT9768891 A PT 9768891A PT 97688 B PT97688 B PT 97688B
- Authority
- PT
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- Prior art keywords
- formula
- compound
- preparation
- pharmaceutical composition
- quot
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 59
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 28
- 150000002148 esters Chemical class 0.000 title claims 3
- 150000001408 amides Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 88
- 238000002360 preparation method Methods 0.000 claims description 59
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 claims description 21
- 101150035983 str1 gene Proteins 0.000 claims description 21
- 239000003814 drug Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 9
- -1 1,2,3,3a, 8,8a-hexahydro-6-oxo, 1,3a, 8-trimethyl-5-pyrrolo [2,3-b] indol-acetic acid Chemical compound 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims 2
- 239000003617 indole-3-acetic acid Substances 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- LDECUSDQMXVUMP-UHFFFAOYSA-N benzyl 3-[6-[[2-(butylamino)-1-[3-methoxycarbonyl-4-(2-methoxy-2-oxoethoxy)phenyl]-2-oxoethyl]-hexylamino]-6-oxohexyl]-4-methyl-2-oxo-6-(4-phenylphenyl)-1,6-dihydropyrimidine-5-carboxylate Chemical compound O=C1NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)C(C(=O)OCC=2C=CC=CC=2)=C(C)N1CCCCCC(=O)N(CCCCCC)C(C(=O)NCCCC)C1=CC=C(OCC(=O)OC)C(C(=O)OC)=C1 LDECUSDQMXVUMP-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 claims 1
- 238000001471 micro-filtration Methods 0.000 claims 1
- 230000003287 optical effect Effects 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 description 8
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 210000003754 fetus Anatomy 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 201000002909 Aspergillosis Diseases 0.000 description 1
- 208000036641 Aspergillus infections Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- QBQQKHZEHKZMJF-NXUSYKNTSA-N mioe Chemical compound C=1([C@@H]2OC(=O)C[C@@H]3[C@@]2(C)CC[C@H]2C3=C[C@@H]3[C@@H](OC(=O)C(C)C)C(C)(C)[C@@H]([C@@]2(C)C3=O)CC(=O)OC)C=COC=1 QBQQKHZEHKZMJF-NXUSYKNTSA-N 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
Classifications
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Description
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Claims (1)
- om ψ írf= · Μ. 0xai-gçcI He $ιν&ιφ&&φ as «wjs%iya ¥*x- ®ft- #»--i;êfM!^l% pâlsea *etífr*&mâ3» Ma?®»-» w&* : . mm§& as i^tSf ^**fte^s«^feii^êfcâx^cea-âiaffiiits m se®*-iwMl^· _ .; -.mà&tíai-pis ee e&ter.tta mmpb&fcõ â& #%a»M 1 «p ®|' ."' ISL·. «aarfSt .gsi—ia^ft /áÉ»«i .ι-i. .-.-. mÍ(3Í i^SkSfiKÍÊfráÊbMfejS " r fôss®.s gagK3j?akesça© sp§si%ca* as ,« %$ ' ff!? ******* g^t^aa^^aga^a· viyrt Qotpprmjbo fia tfMvtenÊa pjn - qfg' '. _-.1| â ·@1ιρ3®@ a» sfttaâs áe iitta&s ι «/&ιή âa --; £t*»I& $£4É9 m í«í§ :% I. a^jaUte* s#i!% egttledttedl»^ '. awtla«a.tjyf^·». - I'~ áfjp$®flÈFâ#l?$ &td|iifaiiâSii» * &&££&&** - aft -: esfera ô gi?sp: acitsíiâftdlis psa?' «--W —·.^--j-..8¾ .^g. iff^hw-*-W . —gC-aK-^jte-aB Wfr~^g. *=* ™·*=—-^** AtiJti»*< m* wíl.'_ -ip^sisiâyij^ priaxiriiQ ®gt. iieca^s^a^is*-®!^6 - fptSll- ρι®Γβ§..#^ΐϋ* ιϊρ asmpast© éé; flfatatílii 1!§ @0 a»*®, a», - -y*· yg rTTí^ ji jyaffi jaraft·· ffi 3¾.¾¾.^¾^^¾. .^¾ ^¾¾jfe--¾.¾¾¾ -Φ «Hrawi * jW)j,tc VjL· . * ^§Β@ B§ .- pííS®Í® ®.-wBI %|- @1 -eo íMb? râi&eip aplaiiâistêala aitt Cfimfe' S- te# _ ϋϋϋρ wêéí . pââts: s| .m' li * ss® as mmsm m mm fcsss ste* . itfm «taspalé ás J$ma«i 1* m..qm 1| i ei fasiip^a psag®r. a® aaispst# as fQ^asis x¥-!»!/iB.ipe u&t M4imgtó4* aifili® • eEHSfflPaSFp-mFmm .mm ST^M&WMQE&JtO xni€írjuOF fla pF©»eM<|a IH® I® . e tl^^^ãfl^fcil^fellesô iteáaa h Hj, ll®ÍÍt -€®§Ι®®§ pIlFâ' §Sfl: miám w ftmposfà 4a fmmúm M§m tp@. IJ *®»t l-^i«l& m: iiifs^isr e 31$ M M4ftgli#iif M'fUriUb4ftQàÍl9- ÉrttoriN -<BPè;': '· · · -. .· , = · : ; . «sf; --:.--- " ; á?<aôêâs® ie m&Pã& côBi çt j?ê4wÉfi44<$a-êitô) f p ^aefeei^zftÉ^ psiF l|g ^ |$^ @ 1|$- sere® -# 1 ««r &&» ^ 4& mõFââ mm m ʧ/m» pu* .1. ecé» **®· -® 'B| mr &ΛφΑ%Μ m -'»&βφΧφΛίι6' Jto»' fe^* *ev: S* <=-> ' .dSbaa,. ‘#6ι*|ί.<ίίίβ#Μΐϊ»·ί- ·^ <&.ϋΐί. · «s . pÉp- &44a S^t ^ @ ^ - .^ep sel4®o* .-.ÉNBEMSé» _ÉÍ- S§SPɧ -@e:âff .fH »: racterizado por se obter o n-butil éster do ácido 1,2,3,3a,8,8a -hexa-hidro-o(-oxo,1,3a,8-tri-metil~5-pirrolo[2,3-b]Índol-acétÍ-co. Processo de acordo com a reivindicação 1, ea-racterizado por se obter o n-pentil ester do ácido 1,2,3,3a,8, 8a-hexa-hidro-fl(-oxo-1,3a.8-tr£metil-5-pirrolo[2,3-b3indol-ace-tico. - 73 - Processo de acordo com a reivindicação 1, carácter izado por se obter o fenilmetil ester do ácido 1,2,3, 3a, 8, 8a-hexa-hidr o-«(-oxo- 1,3a, 8-1 r imet il-5~pirrolo[2,3-b 1-indol-acético. - 83 - Processo de acordo com a reivindicação 1, ca-racterizado por se obter o fenil-etil ester do ácido 1,2,3,3a, 8,8a-hexa-hidro-c(-oxo- 1,3a, 8-trimetil-5-pirrolo 12,3-b 3-indol-acético. - 9» - Processo para a preparação de uma composição farmacêutico caracterizado por se incorporar como ingrediente activo um composto de fórmula I quando preparado de acordo com a reivindicação 1.  requerente reivindica a prioridade do pedido de patente norte-americano apresentado em 17 de Maio de 1990, sob o numero de série 52*1,627* - 34 - Lisboa, 16 de Maio de 199135 - RESUMO "PROCESSO PARA A PREPARAÇgQ DE ÃMIDAS, ESTERES» ÁCIDOS q-OXO--PIRROLOE 2, 3-b 3ISDOL-ACÉTICO K ANÁLOGOS RELACIONADOS E BE COM-POSIÇÕES FARMACÊUTICAS QOE OS CONTfiM» A invenção refere-se a um processo para a preparação de um composto da fórmula IR3 Ri| (I) dos seus sais de adição de ácido farmaceutieamente aceitáveis, e quando aplicável, dos seus isómeros geométricos e opticos e misturas racómicas, a) que compreende nomeadamente fazer-se reagir um composto da fórmula IVR3 R4 (IV) com um oxalato de di-alquilo da fórmula VII O(VII) na presença de Ν,Ν,Ν’,Ν’-tetra-metil-etileno-diamina e sec-bu-til-litio, para se obter um composto da fórmula I*
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US52462790A | 1990-05-17 | 1990-05-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT97688A PT97688A (pt) | 1992-02-28 |
| PT97688B true PT97688B (pt) | 1998-08-31 |
Family
ID=24090019
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT97688A PT97688B (pt) | 1990-05-17 | 1991-05-16 | Processo para a preparacao de amidas, esteres, acidos alfa-oxo-pirrolo{2,3-b}indol-acetico e analogos relacionados e de composicoes farmaceuticas que os contem |
Country Status (22)
| Country | Link |
|---|---|
| EP (1) | EP0457318B1 (pt) |
| JP (1) | JPH0826024B2 (pt) |
| KR (2) | KR100215615B1 (pt) |
| AR (1) | AR247888A1 (pt) |
| AT (1) | ATE141273T1 (pt) |
| AU (1) | AU634380B2 (pt) |
| CA (1) | CA2042737A1 (pt) |
| CZ (1) | CZ280922B6 (pt) |
| DE (1) | DE69121299T2 (pt) |
| DK (1) | DK0457318T3 (pt) |
| ES (1) | ES2094768T3 (pt) |
| FI (1) | FI96689C (pt) |
| GR (1) | GR3021043T3 (pt) |
| HU (1) | HU210179B (pt) |
| IE (1) | IE76318B1 (pt) |
| IL (1) | IL98162A (pt) |
| MX (2) | MX25777A (pt) |
| NO (1) | NO177710C (pt) |
| NZ (2) | NZ260210A (pt) |
| PL (1) | PL290273A1 (pt) |
| PT (1) | PT97688B (pt) |
| ZA (1) | ZA913711B (pt) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4983616A (en) * | 1990-02-01 | 1991-01-08 | Hoechst-Roussel Pharmaceuticals Inc. | Hexahydropyrrolo(2,3-B)indole carbamates, ureas, amides and related compounds |
| AU634654B2 (en) * | 1990-05-11 | 1993-02-25 | Hoechst-Roussel Pharmaceuticals Incorporated | Pyrrolo(2,3-b)indole-ketones and analogs, a process for their preparation and their use as medicaments |
| SG70968A1 (en) * | 1990-06-27 | 2000-03-21 | Hoechst Marion Roussel Inc | Tetrahydroisquinolinylcarbamates of 1,2,3,3A,8,8A-hexahydro-1,3A-8-trimethylpyrrolo(2,3-b) indole |
| CA2408913A1 (en) | 2000-05-16 | 2001-11-22 | Takeda Chemical Industries, Ltd. | Melanin-concentrating hormone antagonist |
| WO2010027334A1 (en) | 2008-09-03 | 2010-03-11 | Nanyang Technological University | Novel tricyclic chiral compounds and their use in asymmetric catalysis |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1199076B (it) * | 1984-03-01 | 1988-12-30 | Consiglio Nazionale Ricerche | Derivati della fisostigmina con proprieta'di inibizione della aceticolinesterasi e relativo procedimento di produzione |
| US4791107A (en) * | 1986-07-16 | 1988-12-13 | Hoechst-Roussel Pharmaceuticals, Inc. | Memory enhancing and analgesic 1,2,3,3A,8,8A-hexahydro-3A,8 (and) 1,3A,8)-di(and tri)methylpyrrolo(2,3-B)indoles, compositions and use |
| US4971992A (en) * | 1989-03-27 | 1990-11-20 | Hoechst-Roussel Pharmaceuticals Inc. | Carbonate derivatives of eseroline |
-
1991
- 1991-04-29 AU AU76182/91A patent/AU634380B2/en not_active Ceased
- 1991-05-14 AR AR91319694A patent/AR247888A1/es active
- 1991-05-14 MX MX2577791A patent/MX25777A/es unknown
- 1991-05-15 FI FI912363A patent/FI96689C/fi active
- 1991-05-15 NZ NZ260210A patent/NZ260210A/en unknown
- 1991-05-15 NZ NZ238151A patent/NZ238151A/en unknown
- 1991-05-15 CZ CS911429A patent/CZ280922B6/cs not_active IP Right Cessation
- 1991-05-15 NO NO911892A patent/NO177710C/no not_active IP Right Cessation
- 1991-05-16 DE DE69121299T patent/DE69121299T2/de not_active Expired - Fee Related
- 1991-05-16 EP EP91107942A patent/EP0457318B1/en not_active Expired - Lifetime
- 1991-05-16 KR KR1019910007922A patent/KR100215615B1/ko not_active Expired - Fee Related
- 1991-05-16 MX MX2581691A patent/MX25816A/es unknown
- 1991-05-16 AT AT91107942T patent/ATE141273T1/de not_active IP Right Cessation
- 1991-05-16 PT PT97688A patent/PT97688B/pt not_active IP Right Cessation
- 1991-05-16 DK DK91107942.4T patent/DK0457318T3/da active
- 1991-05-16 JP JP3139418A patent/JPH0826024B2/ja not_active Expired - Lifetime
- 1991-05-16 CA CA002042737A patent/CA2042737A1/en not_active Abandoned
- 1991-05-16 ES ES91107942T patent/ES2094768T3/es not_active Expired - Lifetime
- 1991-05-16 IL IL9816291A patent/IL98162A/en unknown
- 1991-05-16 PL PL29027391A patent/PL290273A1/xx unknown
- 1991-05-16 ZA ZA913711A patent/ZA913711B/xx unknown
- 1991-05-16 IE IE167891A patent/IE76318B1/en not_active IP Right Cessation
- 1991-05-17 HU HU911658A patent/HU210179B/hu not_active IP Right Cessation
-
1996
- 1996-09-13 GR GR960402402T patent/GR3021043T3/el unknown
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1999
- 1999-02-03 KR KR1019990003497A patent/KR100227715B1/ko not_active Expired - Fee Related
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