NO316379B1 - Nye taxoider, deres fremstilling og farmas degree ytiske preparater inneholdende forbindelsene - Google Patents
Nye taxoider, deres fremstilling og farmas degree ytiske preparater inneholdende forbindelsene Download PDFInfo
- Publication number
- NO316379B1 NO316379B1 NO19973922A NO973922A NO316379B1 NO 316379 B1 NO316379 B1 NO 316379B1 NO 19973922 A NO19973922 A NO 19973922A NO 973922 A NO973922 A NO 973922A NO 316379 B1 NO316379 B1 NO 316379B1
- Authority
- NO
- Norway
- Prior art keywords
- residue
- general formula
- compound
- alkyl
- phenyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 116
- 238000002360 preparation method Methods 0.000 title claims description 15
- -1 C4_&-cycloalkenyl Chemical group 0.000 claims description 52
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 50
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 125000006239 protecting group Chemical group 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 14
- 150000003254 radicals Chemical class 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Chemical group 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 7
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
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- 125000001424 substituent group Chemical group 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
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- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000000460 chlorine Chemical group 0.000 claims description 6
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- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical class [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 5
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- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 5
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
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- 150000002170 ethers Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 150000007579 7-membered cyclic compounds Chemical class 0.000 claims description 4
- 150000001336 alkenes Chemical group 0.000 claims description 4
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
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- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims description 3
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- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000001769 aryl amino group Chemical group 0.000 claims description 3
- 125000005110 aryl thio group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000005118 N-alkylcarbamoyl group Chemical group 0.000 claims description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000004423 acyloxy group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000006633 tert-butoxycarbonylamino group Chemical group 0.000 claims description 2
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 5
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- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
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- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
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- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- Y—GENERAL 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Medicines Containing Plant Substances (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9503545A FR2732340B1 (fr) | 1995-03-27 | 1995-03-27 | Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent |
FR9515381A FR2742754B1 (fr) | 1995-12-22 | 1995-12-22 | Procede de preparation de taxoides |
PCT/FR1996/000441 WO1996030356A1 (fr) | 1995-03-27 | 1996-03-25 | Nouveaux taxoïdes, leur preparation et les compositions pharmaceutiques qui les contiennent |
Publications (3)
Publication Number | Publication Date |
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NO973922D0 NO973922D0 (no) | 1997-08-26 |
NO973922L NO973922L (no) | 1997-08-26 |
NO316379B1 true NO316379B1 (no) | 2004-01-19 |
Family
ID=26231838
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO973923A NO316607B1 (no) | 1995-03-27 | 1997-08-26 | Nye taxoider, deres fremstilling, mellomprodukter samt farmasøytiske preparater inneholdende forbindelsene |
NO19973922A NO316379B1 (no) | 1995-03-27 | 1997-08-26 | Nye taxoider, deres fremstilling og farmas degree ytiske preparater inneholdende forbindelsene |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO973923A NO316607B1 (no) | 1995-03-27 | 1997-08-26 | Nye taxoider, deres fremstilling, mellomprodukter samt farmasøytiske preparater inneholdende forbindelsene |
Country Status (41)
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US (3) | US5889043A (tr) |
EP (2) | EP0817779B1 (tr) |
JP (2) | JP2941951B2 (tr) |
KR (2) | KR100297196B1 (tr) |
CN (2) | CN1213042C (tr) |
AP (2) | AP753A (tr) |
AR (1) | AR001440A1 (tr) |
AT (2) | ATE188471T1 (tr) |
AU (2) | AU703278B2 (tr) |
BG (2) | BG63009B1 (tr) |
BR (2) | BR9607929A (tr) |
CA (2) | CA2214319C (tr) |
CO (1) | CO4700576A1 (tr) |
CZ (2) | CZ287326B6 (tr) |
DE (2) | DE69606028T2 (tr) |
DK (2) | DK0817779T3 (tr) |
DZ (1) | DZ2009A1 (tr) |
EA (2) | EA000709B1 (tr) |
EE (2) | EE03609B1 (tr) |
ES (2) | ES2143187T3 (tr) |
GE (2) | GEP20002211B (tr) |
GR (2) | GR3031526T3 (tr) |
HU (2) | HU223732B1 (tr) |
IL (1) | IL117636A (tr) |
IS (2) | IS2058B (tr) |
MA (1) | MA23823A1 (tr) |
MY (1) | MY121225A (tr) |
NO (2) | NO316607B1 (tr) |
NZ (2) | NZ304900A (tr) |
OA (2) | OA10513A (tr) |
PE (1) | PE51097A1 (tr) |
PL (2) | PL188284B1 (tr) |
PT (1) | PT817779E (tr) |
RO (2) | RO115877B1 (tr) |
SK (2) | SK281927B6 (tr) |
TN (1) | TNSN96043A1 (tr) |
TR (2) | TR199701042T1 (tr) |
TW (1) | TW394765B (tr) |
UY (2) | UY24192A1 (tr) |
WO (2) | WO1996030355A1 (tr) |
ZA (1) | ZA962399B (tr) |
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FR2771092B1 (fr) | 1997-11-18 | 1999-12-17 | Rhone Poulenc Rorer Sa | Procede de preparation de derives de la classe des taxoides |
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1996
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- 1996-03-25 JP JP8528995A patent/JP2941951B2/ja not_active Expired - Lifetime
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- 1996-03-25 AP APAP/P/1997/001093A patent/AP753A/en active
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- 1996-03-25 EP EP96909192A patent/EP0817779B1/fr not_active Expired - Lifetime
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- 1996-03-25 ES ES96909193T patent/ES2140075T3/es not_active Expired - Lifetime
- 1996-03-25 GE GEAP19963957A patent/GEP20002211B/en unknown
- 1996-03-25 EP EP96909193A patent/EP0817780B1/fr not_active Expired - Lifetime
- 1996-03-25 CA CA002214321A patent/CA2214321C/fr not_active Expired - Fee Related
- 1996-03-25 WO PCT/FR1996/000441 patent/WO1996030356A1/fr not_active Application Discontinuation
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- 1996-03-25 JP JP52899696A patent/JP3790826B2/ja not_active Expired - Fee Related
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- 1996-03-25 EE EE9700315A patent/EE03608B1/xx unknown
- 1996-03-25 CZ CZ19973030A patent/CZ287326B6/cs not_active IP Right Cessation
- 1996-03-25 AT AT96909192T patent/ATE188471T1/de active
- 1996-03-25 EA EA199700270A patent/EA000709B1/ru not_active IP Right Cessation
- 1996-03-25 AT AT96909193T patent/ATE185562T1/de active
- 1996-03-25 BR BR9607930A patent/BR9607930A/pt not_active IP Right Cessation
- 1996-03-25 RO RO97-01793A patent/RO115877B1/ro unknown
- 1996-03-25 AP APAP/P/1997/001090A patent/AP785A/en active
- 1996-03-25 AU AU52780/96A patent/AU711227B2/en not_active Expired
- 1996-03-25 DK DK96909193T patent/DK0817780T3/da active
- 1996-03-25 EA EA199700269A patent/EA000567B1/ru not_active IP Right Cessation
- 1996-03-25 NZ NZ304901A patent/NZ304901A/xx not_active IP Right Cessation
- 1996-03-25 GE GEAP19963956A patent/GEP20002188B/en unknown
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- 1996-03-25 SK SK1302-97A patent/SK281928B6/sk not_active IP Right Cessation
- 1996-03-25 CZ CZ19973032A patent/CZ287468B6/cs not_active IP Right Cessation
- 1996-03-25 US US08/913,972 patent/US5889043A/en not_active Expired - Lifetime
- 1996-03-25 CN CNB961928840A patent/CN1152870C/zh not_active Expired - Fee Related
- 1996-03-26 DZ DZ960050A patent/DZ2009A1/fr active
- 1996-03-26 TW TW085103611A patent/TW394765B/zh not_active IP Right Cessation
- 1996-03-26 TN TNTNSN96043A patent/TNSN96043A1/fr unknown
- 1996-03-26 ZA ZA962399A patent/ZA962399B/xx unknown
- 1996-03-26 MY MYPI96001132A patent/MY121225A/en unknown
- 1996-03-27 AR AR33592996A patent/AR001440A1/es active IP Right Grant
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- 1996-11-20 UY UY24370A patent/UY24370A1/es not_active IP Right Cessation
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1997
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- 1997-08-26 NO NO973923A patent/NO316607B1/no not_active IP Right Cessation
- 1997-08-26 NO NO19973922A patent/NO316379B1/no not_active IP Right Cessation
- 1997-09-23 IS IS4567A patent/IS2056B/is unknown
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- 1997-09-26 OA OA70086A patent/OA10513A/fr unknown
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1998
- 1998-04-28 US US09/066,929 patent/US6331635B1/en not_active Expired - Lifetime
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1999
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2000
- 2000-01-07 GR GR990402501T patent/GR3032316T3/el unknown
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2001
- 2001-09-25 US US09/985,956 patent/US6387946B1/en not_active Expired - Lifetime
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2007
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