HRP20080253T3 - Method for producing (3-oxo-2,3-dihydro-1h-isoindol-1-yl) acetylguanidine derivatives - Google Patents
Method for producing (3-oxo-2,3-dihydro-1h-isoindol-1-yl) acetylguanidine derivativesInfo
- Publication number
- HRP20080253T3 HRP20080253T3 HR20080253T HRP20080253T HRP20080253T3 HR P20080253 T3 HRP20080253 T3 HR P20080253T3 HR 20080253 T HR20080253 T HR 20080253T HR P20080253 T HRP20080253 T HR P20080253T HR P20080253 T3 HRP20080253 T3 HR P20080253T3
- Authority
- HR
- Croatia
- Prior art keywords
- formula
- compound
- carbon atoms
- isoindol
- dihydro
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- HLFLSXJZAJUCFK-UHFFFAOYSA-N n-carbamimidoyl-n-(3-oxo-1,2-dihydroisoindol-1-yl)acetamide Chemical class C1=CC=C2C(N(C(=O)C)C(N)=N)NC(=O)C2=C1 HLFLSXJZAJUCFK-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 abstract 1
- FCSKOFQQCWLGMV-UHFFFAOYSA-N 5-{5-[2-chloro-4-(4,5-dihydro-1,3-oxazol-2-yl)phenoxy]pentyl}-3-methylisoxazole Chemical compound O1N=C(C)C=C1CCCCCOC1=CC=C(C=2OCCN=2)C=C1Cl FCSKOFQQCWLGMV-UHFFFAOYSA-N 0.000 abstract 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
Classifications
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- 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
- C07D209/46—Iso-indoles; Hydrogenated iso-indoles with an oxygen atom in position 1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- 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
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- 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
- A61P25/08—Antiepileptics; Anticonvulsants
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- 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
- A61P25/22—Anxiolytics
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- 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
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Toxicology (AREA)
- Biochemistry (AREA)
- Oncology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Psychiatry (AREA)
- Rheumatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Postupak za pripravljanje spojeva formule I,gdjeR1 i R2 su međusobno neovisno vodik, F, Cl, trifluorometoksi, 2,2,2,-trifluoroetoksi, trifluorometil,2,2,2-trifluoroetil ili alkil koji ima 1, 2, 3 ili 4 atoma ugljika; R3 je alk-R4 ili trifluorometil; Alk je alkil koji ima 1, 2, 3 ili 4 atoma ugljika; R4 je vodik, trifluorometil ili cikloalkil kojiima 3, 4, 5, 6 ili 7 atoma ugljika; i njihove soli; koji obuhvaća, kao što je prikazano u shemi 1, a) formiliranje amida formule IV te zatim cikliziranje spoja formule VI, b) reakciju spoja formule VI s alkoksikarbonilmetilentrifenilfosforanom, te s1-alkoksi-1-trimetilsiloksietilenom ili s trialkilfosfonoacetatom, da se dobije spoj formule VII, ic) reakciju spoja formule VII s gvanidinom da se dobije spoj formule I, gdje, u spojevima formula IV, VI i VII, R1 do R3 su kao što je definirano u formuli I iR5 je alkoksi koji ima 1, 2, 3 ili 4 atoma ugljika; i njihove soli. Patent sadrži još 22 patentna zahtjeva.A process for the preparation of compounds of formula I, wherein R 1 and R 2 are independently hydrogen, F, Cl, trifluoromethoxy, 2,2,2, -trifluoroethoxy, trifluoromethyl, 2,2,2-trifluoroethyl or alkyl having 1, 2, 3 or 4. carbon atoms; R3 is alk-R4 or trifluoromethyl; Alk is alkyl having 1, 2, 3 or 4 carbon atoms; R 4 is hydrogen, trifluoromethyl or cycloalkyl having 3, 4, 5, 6 or 7 carbon atoms; and their salts; comprising, as shown in Scheme 1, a) formylating an amide of formula IV and then cyclizing a compound of formula VI, b) reacting a compound of formula VI with alkoxycarbonylmethylenetriphenylphosphorane, and s1-alkoxy-1-trimethylsiloxyethylene or trialkylphosphonoacetate to form a compound VII, and c) reacting a compound of formula VII with guanidine to give a compound of formula I, wherein, in the compounds of formulas IV, VI and VII, R 1 to R 3 are as defined in formula I and R 5 is alkoxy having 1, 2, 3 or 4 carbon atoms; and their salts. The patent contains 22 more patent claims.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10356717A DE10356717A1 (en) | 2003-12-02 | 2003-12-02 | Process for the preparation of (3-oxo-2,3-dihydro-1H-isoindol-1-yl) -acetylguanidine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20080253T3 true HRP20080253T3 (en) | 2008-09-30 |
Family
ID=34638338
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20080253T HRP20080253T3 (en) | 2003-12-02 | 2008-06-09 | Method for producing (3-oxo-2,3-dihydro-1h-isoindol-1-yl) acetylguanidine derivatives |
Country Status (38)
| Country | Link |
|---|---|
| EP (1) | EP1692105B1 (en) |
| JP (1) | JP4809774B2 (en) |
| KR (1) | KR101202604B1 (en) |
| CN (1) | CN100526297C (en) |
| AR (1) | AR046733A1 (en) |
| AT (1) | ATE395334T1 (en) |
| AU (1) | AU2004295056B2 (en) |
| BR (1) | BRPI0417147A (en) |
| CA (1) | CA2548020C (en) |
| CR (1) | CR8376A (en) |
| CY (1) | CY1108187T1 (en) |
| DE (2) | DE10356717A1 (en) |
| DK (1) | DK1692105T3 (en) |
| EC (1) | ECSP066597A (en) |
| EG (1) | EG25498A (en) |
| ES (1) | ES2304634T3 (en) |
| HK (1) | HK1097525A1 (en) |
| HR (1) | HRP20080253T3 (en) |
| IL (1) | IL175834A (en) |
| JO (1) | JO2498B1 (en) |
| MA (1) | MA28220A1 (en) |
| MY (1) | MY136467A (en) |
| NO (1) | NO20063058L (en) |
| NZ (1) | NZ547625A (en) |
| OA (1) | OA13293A (en) |
| PA (1) | PA8618701A1 (en) |
| PE (1) | PE20051037A1 (en) |
| PL (1) | PL1692105T3 (en) |
| PT (1) | PT1692105E (en) |
| RS (1) | RS50571B (en) |
| RU (1) | RU2397159C2 (en) |
| SI (1) | SI1692105T1 (en) |
| TN (1) | TNSN06167A1 (en) |
| TW (1) | TWI334348B (en) |
| UA (1) | UA83883C2 (en) |
| UY (1) | UY28648A1 (en) |
| WO (1) | WO2005054195A1 (en) |
| ZA (1) | ZA200603338B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200812962A (en) * | 2006-07-12 | 2008-03-16 | Astrazeneca Ab | New compounds I/418 |
| CA2725230C (en) * | 2008-04-16 | 2016-05-17 | Kissei Pharmaceutical Co., Ltd. | Hemifumarate of a pyrazole derivative |
| RU2518740C1 (en) * | 2013-03-22 | 2014-06-10 | Федеральное государственное автономное образовательное учреждение высшего профессионального образования "ЮЖНЫЙ ФЕДЕРАЛЬНЫЙ УНИВЕРСИТЕТ" | METHOD, INHIBITING Na+/H+-EXCHANGE, AND DIHYDROCHLORIDE OF 2-(3,4-METHYLENEDIOXYPHENYL)-9-MORPHOLINOETHYLIMIDAZO[1,2-a]BENZIMIDAZOLE |
| CN107778238B (en) * | 2016-08-29 | 2022-07-22 | 中山大学 | Novel synthesis method of 3, 4-dihydroisoquinoline-1-ketone |
| CN107286074B (en) * | 2017-08-16 | 2019-08-20 | 厦门华厦学院 | 3- hydroxyl iso-indoles -1- ketone derivatives and preparation method thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU581324B2 (en) * | 1985-07-05 | 1989-02-16 | Smith Kline & French Laboratories Limited | Substituted 6-phenyl-4,5-dihydro pyradazin-3-ones |
| DE19737224A1 (en) * | 1997-08-27 | 1999-03-18 | Hoechst Marion Roussel De Gmbh | Pharmaceutical preparation for cardiovascular treatment |
| DE19832429A1 (en) * | 1998-07-18 | 2000-01-20 | Hoechst Marion Roussel De Gmbh | New imidazolylmethyl-biphenyl-sulfonylcyanamides, are sodium-dependent bicarbonate/chloride exchanger inhibitors used e.g. for treating cardiovascular disorders such as cardiac infarction |
| EP1767525A1 (en) | 2001-04-09 | 2007-03-28 | Novartis Vaccines and Diagnostics, Inc. | Guanidino compounds as melanocortin-4 receptor (MC4-R) agonists |
| FR2840302B1 (en) * | 2002-06-03 | 2004-07-16 | Aventis Pharma Sa | ISOINDOLONE DERIVATIVES, PREPARATION METHOD AND INTERMEDIARY THEREOF AS MEDICAMENTS AND PHARMACEUTICAL COMPOSITIONS COMPRISING SAME |
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2003
- 2003-12-02 DE DE10356717A patent/DE10356717A1/en not_active Withdrawn
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2004
- 2004-11-04 JO JO2004155A patent/JO2498B1/en active
- 2004-11-19 JP JP2006541829A patent/JP4809774B2/en not_active Expired - Fee Related
- 2004-11-19 AT AT04803188T patent/ATE395334T1/en active
- 2004-11-19 CN CNB2004800348122A patent/CN100526297C/en not_active Expired - Fee Related
- 2004-11-19 PL PL04803188T patent/PL1692105T3/en unknown
- 2004-11-19 OA OA1200600177A patent/OA13293A/en unknown
- 2004-11-19 EP EP04803188A patent/EP1692105B1/en active Active
- 2004-11-19 PT PT04803188T patent/PT1692105E/en unknown
- 2004-11-19 SI SI200430747T patent/SI1692105T1/en unknown
- 2004-11-19 DE DE502004007177T patent/DE502004007177D1/en active Active
- 2004-11-19 RU RU2006123410/04A patent/RU2397159C2/en not_active IP Right Cessation
- 2004-11-19 BR BRPI0417147-0A patent/BRPI0417147A/en not_active IP Right Cessation
- 2004-11-19 DK DK04803188T patent/DK1692105T3/en active
- 2004-11-19 UA UAA200607292A patent/UA83883C2/en unknown
- 2004-11-19 KR KR1020067010920A patent/KR101202604B1/en not_active IP Right Cessation
- 2004-11-19 CA CA2548020A patent/CA2548020C/en not_active Expired - Fee Related
- 2004-11-19 RS RSP-2008/0311A patent/RS50571B/en unknown
- 2004-11-19 WO PCT/EP2004/013153 patent/WO2005054195A1/en active Application Filing
- 2004-11-19 ES ES04803188T patent/ES2304634T3/en active Active
- 2004-11-19 NZ NZ547625A patent/NZ547625A/en not_active IP Right Cessation
- 2004-11-19 AU AU2004295056A patent/AU2004295056B2/en not_active Ceased
- 2004-11-29 PE PE2004001175A patent/PE20051037A1/en not_active Application Discontinuation
- 2004-11-30 AR ARP040104450A patent/AR046733A1/en not_active Application Discontinuation
- 2004-11-30 TW TW093136804A patent/TWI334348B/en not_active IP Right Cessation
- 2004-12-01 PA PA20048618701A patent/PA8618701A1/en unknown
- 2004-12-01 MY MYPI20044973A patent/MY136467A/en unknown
- 2004-12-02 UY UY28648A patent/UY28648A1/en not_active Application Discontinuation
-
2006
- 2006-04-26 ZA ZA200603338A patent/ZA200603338B/en unknown
- 2006-04-28 CR CR8376A patent/CR8376A/en unknown
- 2006-05-22 IL IL175834A patent/IL175834A/en not_active IP Right Cessation
- 2006-06-01 TN TNP2006000167A patent/TNSN06167A1/en unknown
- 2006-06-01 EC EC2006006597A patent/ECSP066597A/en unknown
- 2006-06-01 EG EGNA2006000508 patent/EG25498A/en active
- 2006-06-02 MA MA29077A patent/MA28220A1/en unknown
- 2006-06-30 NO NO20063058A patent/NO20063058L/en unknown
-
2007
- 2007-03-09 HK HK07102616.3A patent/HK1097525A1/en not_active IP Right Cessation
-
2008
- 2008-06-09 HR HR20080253T patent/HRP20080253T3/en unknown
- 2008-07-11 CY CY20081100727T patent/CY1108187T1/en unknown
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