HUP0303873A2 - Mikanolide derivatives, process for their preparation and their therapeutic uses as a medicine - Google Patents
Mikanolide derivatives, process for their preparation and their therapeutic uses as a medicineInfo
- Publication number
- HUP0303873A2 HUP0303873A2 HU0303873A HUP0303873A HUP0303873A2 HU P0303873 A2 HUP0303873 A2 HU P0303873A2 HU 0303873 A HU0303873 A HU 0303873A HU P0303873 A HUP0303873 A HU P0303873A HU P0303873 A2 HUP0303873 A2 HU P0303873A2
- Authority
- HU
- Hungary
- Prior art keywords
- group
- aryl
- alkyl
- aralkyl
- hydrogen atom
- Prior art date
Links
- 239000003814 drug Substances 0.000 title abstract 2
- JRZGAAFGODYEEA-ATNXOXLHSA-N Mikanolide Chemical class C([C@]1([C@H]([C@@H]2O[C@@H]22)O1)C)[C@@H]1OC(=O)C(=C)[C@H]1[C@@H]1OC(=O)C2=C1 JRZGAAFGODYEEA-ATNXOXLHSA-N 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 6
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 5
- 125000003118 aryl group Chemical group 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 2
- 150000001413 amino acids Chemical class 0.000 abstract 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 2
- 125000004475 heteroaralkyl group Chemical group 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 101100240522 Caenorhabditis elegans nhr-18 gene Proteins 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000001093 anti-cancer Effects 0.000 abstract 1
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- 239000003443 antiviral agent Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
- C07D493/18—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
A találmány tárgya új mikanolidszármazékok, eljárás a vegyületekelőállítására, valamint alkalmazásuk gyógyszerként, különösenrákellenes, baktériumellenes és vírusellenes szerként. Jelen találmánytárgya (I) általános képletű vegyületek, közelebbről az (I)1 és (I)2képletű vegyületek, ahol R1 jelentése hidrogénatom vagy SR4 vagyNR4R5; R2 jelentése SR6 vagy NR6R7; R3 jelentése OH, O(CO)R14,OSiR15R16R17, O(CO)OR18 vagy O(CO)NHR18; R4 és R6 jelentése alkil-,cikloalkil-, cikloalkil-alkil-, hidroxialkil-csoport, vagy adottesetben az arilcsoporton szubsztituált aril- vagy aralkilcsoport; R5és R7 jelentése hidrogénatom, alkil-, cikloalkil-, cikloalkilalkil-,hidroxi-alkil-csoport, vagy adott esetben az arilcsoportonszubsztituált aril- vagy aralkilcsoport; R4 és R5 együtt anitrogénatommal, melyhez kapcsolódik, 5-7-tagú heterociklust képezhet,és a további tagok lehetnek -CR8R9-, -NR10-, -O- vagy -S- csoport,azonban a heterociklusban csak az egyik tag lehet oxigén- vagykénatom; és R6 és R7 együtt a nitrogénatommal, melyhez kapcsolódik, 5-7-tagú heterociklust képezhet, ahol a további tag lehet -CR11R12, -NR13-, -O- vagy -S- csoport, de csak az egyik tag lehet -0- vagy -S- aheterociklusban; R8, R10, R11 és R13 jelentése hidrogénatom, alkil-,alkoxikarbonil- vagy aralkilcsoport; R9 és R12 jelentése hidrogénatom,vagy R9 vagy R12 együtt R8-cal és R11-gyel az őket hordozó szénatomhozbármelyik oldalon kapcsolódó -O-(CH2)2-O- csoportot képez, az ilyencsoport azonban csak maximum egyszer lehet jelen NR4R5 vagy NR6R7csoportonként, és jelentése hidrogénatom vagy alkilcsoport; R14jelentése alkil-, cikloalkil- vagy adamantilcsoport, vagy adottesetben az aril- vagy heteroarilcsoporton szubsztituált aril-,heteroaril-, aralkil- vagy heteroaralkilcsoport; vagy R14 is olyan,hogy R14-COOH jelentése természetes aminosav vagy az ilyen aminosavoptikailag aktív enantiomerje; R15, R16 és R17 jelentése alkil- vagyfenilcsoport; R18 jelentése alkil-, cikloalkil-vagy adamantilcsoport,vagy adott esetben az aril- vagy heteroarilcsoporton szubsztituáltaril-, heteroaril-, aralkil- vagy heteroaralkilcsoport; azonbanmagától értetődik, hogy ha a vegyületek (I)2 általános képletteljellemezhetők, akkor R1 nem lehet hidrogénatom; vagy utóbbi sói. ÓThe subject of the invention is new micanolide derivatives, a process for the production of the compounds, and their use as medicine, especially as an anticancer, antibacterial and antiviral agent. The subject of the present invention is compounds of general formula (I), more specifically compounds of formulas (I)1 and (I)2, where R1 is a hydrogen atom or SR4 or NR4R5; R 2 is SR 6 or NR 6 R 7 ; R 3 is OH, O(CO)R 14 , OSiR 15 R 16 R 17 , O(CO)OR 18 or O(CO)NHR 18 ; R4 and R6 are alkyl, cycloalkyl, cycloalkylalkyl, hydroxyalkyl, or optionally substituted aryl or aralkyl on the aryl group; R5 and R7 represent a hydrogen atom, an alkyl, cycloalkyl, cycloalkylalkyl, hydroxyalkyl group, or optionally the aryl group substituted aryl or aralkyl group; R4 and R5, together with the nitrogen atom to which it is connected, can form a 5-7-membered heterocycle, and the additional members can be -CR8R9-, -NR10-, -O- or -S- groups, however, only one member in the heterocycle can be an oxygen or sulfur atom ; and R6 and R7 together with the nitrogen atom to which it is attached can form a 5-7 membered heterocycle, where the additional member can be -CR11R12, -NR13-, -O- or -S-, but only one member can be -0- or -S- in a heterocycle; R 8 , R 10 , R 11 and R 13 are a hydrogen atom, an alkyl, alkoxycarbonyl or aralkyl group; R9 and R12 are hydrogen atoms, or R9 or R12 together with R8 and R11 form a -O-(CH2)2-O- group attached to the carbon atom carrying them on either side, but such a group can only be present at most once per NR4R5 or NR6R7 group, and is a hydrogen atom or an alkyl group; R14 is an alkyl, cycloalkyl or adamantyl group, or an aryl, heteroaryl, aralkyl or heteroaralkyl group optionally substituted on the aryl or heteroaryl group; or R14 is also such that R14-COOH is a natural amino acid or an optically active enantiomer of such an amino acid; R15, R16 and R17 are alkyl or phenyl; R 18 is an alkyl, cycloalkyl or adamantyl group, or an aryl, heteroaryl, aralkyl or heteroaralkyl group optionally substituted on the aryl or heteroaryl group; however, it is understood that if the compounds can be represented by the general formula (I) 2 , then R 1 cannot be a hydrogen atom; or salts of the latter. HE
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0100397A FR2819513B1 (en) | 2001-01-12 | 2001-01-12 | NOVEL MIKANOLIDE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATIONS |
| PCT/FR2002/000092 WO2002055523A1 (en) | 2001-01-12 | 2002-01-11 | Mikanolide derivatives, their preparation and therapeutic uses |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUP0303873A2 true HUP0303873A2 (en) | 2004-03-29 |
| HUP0303873A3 HUP0303873A3 (en) | 2005-02-28 |
Family
ID=8858748
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0303873A HUP0303873A3 (en) | 2001-01-12 | 2002-01-11 | Mikanolide derivatives, process for their preparation and their therapeutic uses as a medicine |
Country Status (6)
| Country | Link |
|---|---|
| FR (1) | FR2819513B1 (en) |
| HK (1) | HK1063793A1 (en) |
| HU (1) | HUP0303873A3 (en) |
| IL (1) | IL156593A0 (en) |
| NO (1) | NO20033118L (en) |
| ZA (1) | ZA200305313B (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2801792B1 (en) * | 1999-12-01 | 2003-04-18 | Sod Conseils Rech Applic | A NEW MEDICINE, DIHYDROMIKANOLIDE, ITS PRODUCTION BY EXTRACTION OF THE PLANT MIKANIA MICRANTHA AND ITS USE AS ANTI-PROLIFERATIVE AGENT |
-
2001
- 2001-01-12 FR FR0100397A patent/FR2819513B1/en not_active Expired - Fee Related
-
2002
- 2002-01-11 HU HU0303873A patent/HUP0303873A3/en unknown
- 2002-01-11 IL IL15659302A patent/IL156593A0/en unknown
-
2003
- 2003-07-08 NO NO20033118A patent/NO20033118L/en not_active Application Discontinuation
- 2003-07-09 ZA ZA200305313A patent/ZA200305313B/en unknown
-
2004
- 2004-09-03 HK HK04106637A patent/HK1063793A1/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2819513A1 (en) | 2002-07-19 |
| NO20033118L (en) | 2003-07-11 |
| ZA200305313B (en) | 2004-06-14 |
| FR2819513B1 (en) | 2005-06-17 |
| NO20033118D0 (en) | 2003-07-08 |
| IL156593A0 (en) | 2004-01-04 |
| HUP0303873A3 (en) | 2005-02-28 |
| HK1063793A1 (en) | 2005-01-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HC9A | Change of name, address |
Owner name: IPSEN PHARMA S.A.S., FR Free format text: FORMER OWNER(S): SOCIETE DE CONSEILS DE RECHERCHES ET D'APPLICATIONS SCIENTIFIQUES (S.C.R.A.S.), FR |
|
| FD9A | Lapse of provisional protection due to non-payment of fees |