BR0002070A - Processo para preparar 8-ciclopentil-6 etil-3-[substituìdo]-5,8-dihidro-4h-1,2,3a, 7,8-pentaaza-as-indacenos e intermediários úteis no mesmo - Google Patents
Processo para preparar 8-ciclopentil-6 etil-3-[substituìdo]-5,8-dihidro-4h-1,2,3a, 7,8-pentaaza-as-indacenos e intermediários úteis no mesmoInfo
- Publication number
- BR0002070A BR0002070A BR0002070-2A BR0002070A BR0002070A BR 0002070 A BR0002070 A BR 0002070A BR 0002070 A BR0002070 A BR 0002070A BR 0002070 A BR0002070 A BR 0002070A
- Authority
- BR
- Brazil
- Prior art keywords
- formula
- compound
- produced
- methoxybenzyl
- protected
- Prior art date
Links
- -1 8-cyclopentyl-6 ethyl-3- [substituted] -5,8-dihydro-4h-1,2,3a, 7,8-pentaaza-as-indacenes Chemical class 0.000 title abstract 22
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000000543 intermediate Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 abstract 2
- IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 abstract 1
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- NXHFZUVHADJHDW-UHFFFAOYSA-N cyclopentylhydrazine Chemical compound NNC1CCCC1 NXHFZUVHADJHDW-UHFFFAOYSA-N 0.000 abstract 1
- RZMZBHSKPLVQCP-UHFFFAOYSA-N ethyl 2-amino-2-oxoacetate Chemical compound CCOC(=O)C(N)=O RZMZBHSKPLVQCP-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 235000012054 meals Nutrition 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical compound NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 abstract 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 150000003839 salts Chemical group 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 238000006561 solvent free reaction Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Patente de Invenção: <B>"PROCESSO PARA PREPARAR 8-CICLOPENTIL-6-ETIL-3-[SUBSTITUìDO]-5,8-DI-HIDRO-4H-1,2, 3A, 7,8-PENTAAZA-AS-INDACENOS E INTERMEDIáRIOS úTEIS NO MESMO"<D>. A invenção visa um método de preparar um composto de 8-ciclopentil-6-etil-3-[substituído]-5,8-di-hidro-4H-1,2,3a,7,8-pentaaz a-as-indaceno de fórmula (1.0.0): e formas de sal farmaceuticamente aceitáveis dos mesmos, onde R¹ é hidrogênio; alquila; alcóxi; alcoxialquila; alquenila; cicloalquila; um grupo heterocíclico-(CH~ 2~)~ n~-, saturado ou insaturado; ou um grupo de Fórmula (1.1.0): onde todos os referidos substituintes são definidos em mais pormenor na presente descrição; compreendendo: (a) submeter uma mistura de reação isenta de solvente de y-caprolactona e p-metoxibenzilamina a aquecimento pelo que se produz um composto amida N-protegido por p-metoxibenzila, de Fórmula (2.0.0): (b) reduzir o referido composto amida de Fórmula (2.0.0) pelo que se produz um composto de amino-álcool N-protegido por p-metoxibenzila, de Fórmula (3.0.0): (c) acilar o referido composto de amino-álcool de Fórmula (3.0.0) com cloreto de etil-oxalila pelo que é produzido um composto de éster etílico de ácido oxalâmico N-protegido por p-metoxibenzila, de Fórmula (4.0.0): (d) oxidar o referido composto de éster etílico de ácido oxalâmico de Fórmula (4.0.0) pelo que se produz um composto de cetona de oxalamida N-protegido por p-metoxibenzila, de Fórmula (5.0.0): (e) fechar o anel do referido composto de cetona de oxalamida de Fórmula (5.0.0) pelo que se produz um composto de piridinona N-protegido por p-metoxibenzila, de Fórmula (6.0.0): (f) O-metilar o referido composto de piridinona de Fórmula (6.0.0) pelo que se produz um composto de 3-metóxi-piridinona N-protegido por p-metoxibenzila, de Fórmula (7.0.0): (g) tratar o referido composto 3-metóxi-piridinona de Fórmula (7.0.0) com ciclopentil-hidrazina, pelo que se produz um composto de pirazolopiridinona N-protegido por p-metoxibenzila, de Fórmula (8.0.0): (h) desproteger o referido composto de pirazolopiridinona de Fórmula (8.0.0) pela remoção do referido grupo p-metoxibenzila, pelo que se produz um composto de lactama de Fórmula (9.0.0): (i) esterificar o referido composto de lactama de Fórmula (9.0.0) pelo que se produz um composto de imino-éster (imidato) correspondente de Fórmula (10.0.0): (j) tratar o referido composto de imino-éster (imidato) de Fórmula (10.0.0) com um composto de hidrazida carboxílica de Fórmula (11.0.0): onde R¹ tem o mesmo significado como acima determinado; pelo que se produz o referido composto de 8-ciclopentil-6-etil-3-[substituído]5,8-di-hidro-4H-1,2,3,a7,8-pentaaz a-as-indaceno de Fórmula (1.0.0).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13194999P | 1999-04-30 | 1999-04-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BR0002070A true BR0002070A (pt) | 2000-10-31 |
Family
ID=22451736
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR0002070-2A BR0002070A (pt) | 1999-04-30 | 2000-05-02 | Processo para preparar 8-ciclopentil-6 etil-3-[substituìdo]-5,8-dihidro-4h-1,2,3a, 7,8-pentaaza-as-indacenos e intermediários úteis no mesmo |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US6326495B2 (pt) |
| EP (1) | EP1048667B1 (pt) |
| JP (1) | JP3510560B2 (pt) |
| KR (1) | KR100346619B1 (pt) |
| CN (2) | CN1249064C (pt) |
| AR (1) | AR029450A1 (pt) |
| AT (2) | ATE282039T1 (pt) |
| AU (1) | AU761391B2 (pt) |
| BR (1) | BR0002070A (pt) |
| CA (1) | CA2307080C (pt) |
| DE (2) | DE60015819T2 (pt) |
| DK (2) | DK1048667T3 (pt) |
| ES (2) | ES2207464T3 (pt) |
| HK (2) | HK1031881A1 (pt) |
| HU (1) | HUP0001700A3 (pt) |
| ID (1) | ID25705A (pt) |
| IL (1) | IL135809A0 (pt) |
| IN (1) | IN192746B (pt) |
| MX (1) | MXPA00004214A (pt) |
| PL (1) | PL339985A1 (pt) |
| PT (2) | PT1048667E (pt) |
| RU (1) | RU2189985C2 (pt) |
| TR (1) | TR200001161A2 (pt) |
| TW (1) | TWI256392B (pt) |
| ZA (1) | ZA200002057B (pt) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE557044T1 (de) | 2009-08-13 | 2012-05-15 | China Petroleum & Chemical | Katalysatorkomponente zur olefinpolymerisierung und katalysator damit |
| WO2012033225A1 (en) | 2010-09-08 | 2012-03-15 | Sumitomo Chemical Company, Limited | Method for producing pyridazinone compounds and intermediate thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2131876C1 (ru) | 1993-07-06 | 1999-06-20 | Пфайзер Инк. | Бициклические тетрагидропиразолпиридины или их фармацевтически приемлемые соли, фармацевтическая композиция, способ ингибирования фосфодиэстеразы, способ лечения |
| HUT77517A (hu) | 1994-10-20 | 1998-05-28 | Pfizer Inc. | Biciklusos tetrahidro-pirazolo-piridin-származékok, alkalmazásuk és ilyen vegyületeket tartalmazó gyógyászati készítmények |
| WO1996039408A1 (en) | 1995-06-06 | 1996-12-12 | Pfizer Inc. | TRICYCLIC 5,6-DIHYDRO-9H-PYRAZOLO[3,4-c]-1,2,4-TRIAZOLO[4,3-α]PYRIDINES |
-
2000
- 2000-03-01 US US09/516,549 patent/US6326495B2/en not_active Expired - Fee Related
- 2000-04-07 DK DK00302947T patent/DK1048667T3/da active
- 2000-04-07 ES ES00302947T patent/ES2207464T3/es not_active Expired - Lifetime
- 2000-04-07 EP EP00302947A patent/EP1048667B1/en not_active Expired - Lifetime
- 2000-04-07 PT PT00302947T patent/PT1048667E/pt unknown
- 2000-04-07 PT PT03024166T patent/PT1380585E/pt unknown
- 2000-04-07 AT AT03024166T patent/ATE282039T1/de not_active IP Right Cessation
- 2000-04-07 DE DE60015819T patent/DE60015819T2/de not_active Expired - Fee Related
- 2000-04-07 DK DK03024166T patent/DK1380585T3/da active
- 2000-04-07 AT AT00302947T patent/ATE252582T1/de not_active IP Right Cessation
- 2000-04-07 DE DE60006026T patent/DE60006026T2/de not_active Expired - Fee Related
- 2000-04-07 ES ES03024166T patent/ES2232805T3/es not_active Expired - Lifetime
- 2000-04-24 IN IN447DE2000 patent/IN192746B/en unknown
- 2000-04-24 IL IL13580900A patent/IL135809A0/xx unknown
- 2000-04-25 TW TW089107724A patent/TWI256392B/zh not_active IP Right Cessation
- 2000-04-26 ZA ZA200002057A patent/ZA200002057B/xx unknown
- 2000-04-26 JP JP2000125351A patent/JP3510560B2/ja not_active Expired - Fee Related
- 2000-04-27 TR TR2000/01161A patent/TR200001161A2/xx unknown
- 2000-04-27 AR ARP000102007A patent/AR029450A1/es unknown
- 2000-04-28 CA CA002307080A patent/CA2307080C/en not_active Expired - Fee Related
- 2000-04-28 ID IDP20000356D patent/ID25705A/id unknown
- 2000-04-28 AU AU30180/00A patent/AU761391B2/en not_active Ceased
- 2000-04-28 CN CNB031476457A patent/CN1249064C/zh not_active Expired - Fee Related
- 2000-04-28 RU RU2000111018/04A patent/RU2189985C2/ru not_active IP Right Cessation
- 2000-04-28 HU HU0001700A patent/HUP0001700A3/hu unknown
- 2000-04-28 MX MXPA00004214A patent/MXPA00004214A/es active IP Right Grant
- 2000-04-28 CN CNB001081403A patent/CN1160353C/zh not_active Expired - Fee Related
- 2000-04-29 KR KR1020000023025A patent/KR100346619B1/ko not_active IP Right Cessation
- 2000-04-30 PL PL00339985A patent/PL339985A1/xx not_active Application Discontinuation
- 2000-05-02 BR BR0002070-2A patent/BR0002070A/pt not_active IP Right Cessation
-
2001
- 2001-04-10 HK HK01102535A patent/HK1031881A1/xx not_active IP Right Cessation
-
2004
- 2004-07-27 HK HK04105520A patent/HK1062678A1/xx not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B08F | Application dismissed because of non-payment of annual fees [chapter 8.6 patent gazette] |
Free format text: REFERENTE A 8O E 9O ANUIDADES. |
|
| B08K | Patent lapsed as no evidence of payment of the annual fee has been furnished to inpi [chapter 8.11 patent gazette] |
Free format text: REFERENTE AO DESPACHO 8.6 NA RPI2003 DE 26/05/2009. |