NO309265B1 - Fremgangsmåte for fremstilling av 1-aryl-1-cyanocyklobutan- derivater - Google Patents
Fremgangsmåte for fremstilling av 1-aryl-1-cyanocyklobutan- derivater Download PDFInfo
- Publication number
- NO309265B1 NO309265B1 NO982474A NO982474A NO309265B1 NO 309265 B1 NO309265 B1 NO 309265B1 NO 982474 A NO982474 A NO 982474A NO 982474 A NO982474 A NO 982474A NO 309265 B1 NO309265 B1 NO 309265B1
- Authority
- NO
- Norway
- Prior art keywords
- formula
- dimethylsulfoxide
- temperature
- compound
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 44
- 238000002360 preparation method Methods 0.000 title claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 64
- 239000002904 solvent Substances 0.000 claims description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 239000000725 suspension Substances 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 12
- IVYMIRMKXZAHRV-UHFFFAOYSA-N 4-chlorophenylacetonitrile Chemical group ClC1=CC=C(CC#N)C=C1 IVYMIRMKXZAHRV-UHFFFAOYSA-N 0.000 claims description 10
- 239000003444 phase transfer catalyst Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical group [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 150000003983 crown ethers Chemical class 0.000 claims description 3
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 claims description 3
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- QWZNCAFWRZZJMA-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)acetonitrile Chemical group ClC1=CC=C(CC#N)C=C1Cl QWZNCAFWRZZJMA-UHFFFAOYSA-N 0.000 claims 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 31
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000002699 waste material Substances 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- XQONXPWVIZZJIL-UHFFFAOYSA-N 1-(4-chlorophenyl)cyclobutane-1-carbonitrile Chemical compound C1=CC(Cl)=CC=C1C1(C#N)CCC1 XQONXPWVIZZJIL-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 235000011121 sodium hydroxide Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- IBYHHJPAARCAIE-UHFFFAOYSA-N 1-bromo-2-chloroethane Chemical compound ClCCBr IBYHHJPAARCAIE-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 230000003111 delayed effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 3
- 229960004425 sibutramine Drugs 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- CTKUIZGFDSJHPY-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)cyclobutane-1-carbonitrile Chemical compound C1=C(Cl)C(Cl)=CC=C1C1(C#N)CCC1 CTKUIZGFDSJHPY-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- -1 aryl cyclobutyl cyanides Chemical class 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
- 238000003672 processing method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- ATWLRNODAYAMQS-UHFFFAOYSA-N 1,1-dibromopropane Chemical compound CCC(Br)Br ATWLRNODAYAMQS-UHFFFAOYSA-N 0.000 description 1
- XZNGUVQDFJHPLU-UHFFFAOYSA-N 1,3-dibromobutane Chemical compound CC(Br)CCBr XZNGUVQDFJHPLU-UHFFFAOYSA-N 0.000 description 1
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
- QNTNAULRPWEWSU-UHFFFAOYSA-N 1-[4-(trifluoromethoxy)phenyl]cyclobutane-1-carbonitrile Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1(C#N)CCC1 QNTNAULRPWEWSU-UHFFFAOYSA-N 0.000 description 1
- YMHXXJJTAGKFBA-UHFFFAOYSA-N 1-bromo-2-chloropropane Chemical compound CC(Cl)CBr YMHXXJJTAGKFBA-UHFFFAOYSA-N 0.000 description 1
- KVBQNFMTEUEOCD-UHFFFAOYSA-M 1-butylpyridin-1-ium;bromide Chemical compound [Br-].CCCC[N+]1=CC=CC=C1 KVBQNFMTEUEOCD-UHFFFAOYSA-M 0.000 description 1
- DHIDUDPFTZJPCQ-UHFFFAOYSA-N 1-phenylcyclobutane-1-carbonitrile Chemical compound C=1C=CC=CC=1C1(C#N)CCC1 DHIDUDPFTZJPCQ-UHFFFAOYSA-N 0.000 description 1
- GAEVNPHZQRROPK-UHFFFAOYSA-N 1-pyridin-2-ylcyclopropane-1-carbonitrile Chemical compound C=1C=CC=NC=1C1(C#N)CC1 GAEVNPHZQRROPK-UHFFFAOYSA-N 0.000 description 1
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 1
- UKVQBONVSSLJBB-UHFFFAOYSA-N 2-pyridin-2-ylacetonitrile Chemical compound N#CCC1=CC=CC=N1 UKVQBONVSSLJBB-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical compound ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 208000008589 Obesity Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- KFSZGBHNIHLIAA-UHFFFAOYSA-M benzyl(trimethyl)azanium;fluoride Chemical compound [F-].C[N+](C)(C)CC1=CC=CC=C1 KFSZGBHNIHLIAA-UHFFFAOYSA-M 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- URWCEDLDYLLXCC-UHFFFAOYSA-M decyl(triethyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCC[N+](CC)(CC)CC URWCEDLDYLLXCC-UHFFFAOYSA-M 0.000 description 1
- YSSSPARMOAYJTE-UHFFFAOYSA-N dibenzo-18-crown-6 Chemical compound O1CCOCCOC2=CC=CC=C2OCCOCCOC2=CC=CC=C21 YSSSPARMOAYJTE-UHFFFAOYSA-N 0.000 description 1
- BBGKDYHZQOSNMU-UHFFFAOYSA-N dicyclohexano-18-crown-6 Chemical compound O1CCOCCOC2CCCCC2OCCOCCOC2CCCCC21 BBGKDYHZQOSNMU-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- VVNBOKHXEBSBQJ-UHFFFAOYSA-M dodecyl(triethyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](CC)(CC)CC VVNBOKHXEBSBQJ-UHFFFAOYSA-M 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JDZSWRCOINFOQI-UHFFFAOYSA-M methyl(triphenyl)azanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[N+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 JDZSWRCOINFOQI-UHFFFAOYSA-M 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- KRRBFUJMQBDDPR-UHFFFAOYSA-N tetrabutylazanium;cyanide Chemical compound N#[C-].CCCC[N+](CCCC)(CCCC)CCCC KRRBFUJMQBDDPR-UHFFFAOYSA-N 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- NRZGVGVFPHPXEO-UHFFFAOYSA-M tetraphenylarsanium;chloride Chemical compound [Cl-].C1=CC=CC=C1[As+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 NRZGVGVFPHPXEO-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
- HNJXPTMEWIVQQM-UHFFFAOYSA-M triethyl(hexadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](CC)(CC)CC HNJXPTMEWIVQQM-UHFFFAOYSA-M 0.000 description 1
- MBXYEKQOJQZLHR-UHFFFAOYSA-M triethyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CC)(CC)CC MBXYEKQOJQZLHR-UHFFFAOYSA-M 0.000 description 1
- NAWZSHBMUXXTGV-UHFFFAOYSA-M triethyl(hexyl)azanium;bromide Chemical compound [Br-].CCCCCC[N+](CC)(CC)CC NAWZSHBMUXXTGV-UHFFFAOYSA-M 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- WFEXFNMTEBFLMM-UHFFFAOYSA-M trioctyl(propyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CCC)(CCCCCCCC)CCCCCCCC WFEXFNMTEBFLMM-UHFFFAOYSA-M 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Crystals, And After-Treatments Of Crystals (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9524681.5A GB9524681D0 (en) | 1995-12-02 | 1995-12-02 | Chemical process |
| PCT/EP1996/005246 WO1997020810A1 (en) | 1995-12-02 | 1996-11-28 | Process for the preparation of 1-aryl-1-cyanocyclobutane derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO982474D0 NO982474D0 (no) | 1998-05-29 |
| NO982474L NO982474L (no) | 1998-05-29 |
| NO309265B1 true NO309265B1 (no) | 2001-01-08 |
Family
ID=10784817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO982474A NO309265B1 (no) | 1995-12-02 | 1998-05-29 | Fremgangsmåte for fremstilling av 1-aryl-1-cyanocyklobutan- derivater |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US6545173B1 (sk) |
| EP (1) | EP0863868B1 (sk) |
| JP (1) | JP2000501402A (sk) |
| KR (1) | KR19990071838A (sk) |
| CN (1) | CN1075057C (sk) |
| AT (1) | ATE199247T1 (sk) |
| AU (1) | AU717603B2 (sk) |
| BG (1) | BG63498B1 (sk) |
| BR (1) | BR9611683A (sk) |
| CA (1) | CA2235043A1 (sk) |
| CZ (1) | CZ164798A3 (sk) |
| DE (1) | DE69611835T2 (sk) |
| DK (1) | DK0863868T3 (sk) |
| ES (1) | ES2154848T3 (sk) |
| GB (1) | GB9524681D0 (sk) |
| GR (1) | GR3035572T3 (sk) |
| HU (1) | HUP9903481A3 (sk) |
| IL (1) | IL124341A (sk) |
| MX (1) | MX9804022A (sk) |
| NO (1) | NO309265B1 (sk) |
| NZ (1) | NZ323896A (sk) |
| PL (1) | PL185047B1 (sk) |
| PT (1) | PT863868E (sk) |
| RU (1) | RU2179168C2 (sk) |
| SI (1) | SI0863868T1 (sk) |
| SK (1) | SK282470B6 (sk) |
| TR (1) | TR199800987T2 (sk) |
| WO (1) | WO1997020810A1 (sk) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6476078B2 (en) | 1999-08-11 | 2002-11-05 | Sepracor, Inc. | Methods of using sibutramine metabolites in combination with a phosphodiesterase inhibitor to treat sexual dysfunction |
| US6974838B2 (en) | 1998-08-24 | 2005-12-13 | Sepracor Inc. | Methods of treating or preventing pain using sibutramine metabolites |
| US6339106B1 (en) | 1999-08-11 | 2002-01-15 | Sepracor, Inc. | Methods and compositions for the treatment and prevention of sexual dysfunction |
| US6331571B1 (en) | 1998-08-24 | 2001-12-18 | Sepracor, Inc. | Methods of treating and preventing attention deficit disorders |
| US6399826B1 (en) | 1999-08-11 | 2002-06-04 | Sepracor Inc. | Salts of sibutramine metabolites, methods of making sibutramine metabolites and intermediates useful in the same, and methods of treating pain |
| US6504044B2 (en) | 2001-02-28 | 2003-01-07 | Council Of Scientific And Industrial Research | Process for the preparation of 1-[cyano(aryl)methyl] cyclohexanol |
| DE60110364T2 (de) * | 2001-02-28 | 2006-02-16 | Council Of Scientific And Industrial Research | Verfahren zur Herstellung von 1-(Cyan(aryl)methyl)cyclohexanol |
| WO2002083631A1 (en) | 2001-04-13 | 2002-10-24 | Sepracor Inc. | Methods of preparing didesmethylsibutramine and other sibutramine derivatives |
| AT503354B1 (de) * | 2006-02-22 | 2008-07-15 | Dsm Fine Chem Austria Gmbh | Verfahren zur herstellung von 3,4-disubstituierten phenylessigsäuren, sowie neue zwischenverbindungen |
| CZ300903B6 (cs) * | 2008-06-09 | 2009-09-09 | Lucební závody Draslovka a. s. Kolín | Zpusob výroby cykloalkankarbonitrilu |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3526656A (en) | 1967-05-25 | 1970-09-01 | Parke Davis & Co | (1-arylcyclobutyl)carbonyl carbamic acid derivatives |
| US4220591A (en) | 1975-11-26 | 1980-09-02 | Commonwealth Scientific And Industrial Research Organization | Insecticidal esters |
| AU4244478A (en) | 1977-12-19 | 1979-06-28 | Commw Scient Ind Res Org | Cyclobutane carboxylic acids and esters and insecticides |
| ZA821577B (en) * | 1981-04-06 | 1983-03-30 | Boots Co Plc | Therapeutic agents |
| IE52768B1 (en) * | 1981-04-06 | 1988-02-17 | Boots Co Ltd | 1-arylcyclobutylalkylamine compounds useful as therapeutic agents |
| ZA925185B (en) | 1991-07-18 | 1993-04-29 | Hoffmann La Roche | Dithianes. |
| GB9127306D0 (en) * | 1991-12-23 | 1992-02-19 | Boots Co Plc | Therapeutic agents |
| GB9309749D0 (en) | 1993-05-12 | 1993-06-23 | Boots Co Plc | Therapeutic agents |
| EP0707570B1 (en) | 1993-06-22 | 1998-05-06 | Knoll AG | Isoquinoline derivatives as therapeutic agents |
-
1995
- 1995-12-02 GB GBGB9524681.5A patent/GB9524681D0/en active Pending
-
1996
- 1996-11-28 AT AT96941602T patent/ATE199247T1/de not_active IP Right Cessation
- 1996-11-28 AU AU10939/97A patent/AU717603B2/en not_active Ceased
- 1996-11-28 JP JP9520945A patent/JP2000501402A/ja active Pending
- 1996-11-28 DE DE69611835T patent/DE69611835T2/de not_active Expired - Fee Related
- 1996-11-28 KR KR1019980704120A patent/KR19990071838A/ko not_active Application Discontinuation
- 1996-11-28 ES ES96941602T patent/ES2154848T3/es not_active Expired - Lifetime
- 1996-11-28 BR BR9611683A patent/BR9611683A/pt not_active Application Discontinuation
- 1996-11-28 CA CA002235043A patent/CA2235043A1/en not_active Abandoned
- 1996-11-28 IL IL12434196A patent/IL124341A/en not_active IP Right Cessation
- 1996-11-28 CZ CZ981647A patent/CZ164798A3/cs unknown
- 1996-11-28 RU RU98112599/04A patent/RU2179168C2/ru active
- 1996-11-28 PL PL96326926A patent/PL185047B1/pl unknown
- 1996-11-28 SI SI9630254T patent/SI0863868T1/xx unknown
- 1996-11-28 DK DK96941602T patent/DK0863868T3/da active
- 1996-11-28 WO PCT/EP1996/005246 patent/WO1997020810A1/en not_active Application Discontinuation
- 1996-11-28 PT PT96941602T patent/PT863868E/pt unknown
- 1996-11-28 SK SK626-98A patent/SK282470B6/sk unknown
- 1996-11-28 NZ NZ323896A patent/NZ323896A/xx unknown
- 1996-11-28 US US09/077,698 patent/US6545173B1/en not_active Expired - Fee Related
- 1996-11-28 EP EP96941602A patent/EP0863868B1/en not_active Expired - Lifetime
- 1996-11-28 HU HU9903481A patent/HUP9903481A3/hu unknown
- 1996-11-28 TR TR1998/00987T patent/TR199800987T2/xx unknown
- 1996-11-28 CN CN96198731A patent/CN1075057C/zh not_active Expired - Fee Related
-
1998
- 1998-05-21 MX MX9804022A patent/MX9804022A/es unknown
- 1998-05-21 BG BG102473A patent/BG63498B1/bg unknown
- 1998-05-29 NO NO982474A patent/NO309265B1/no not_active IP Right Cessation
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2001
- 2001-03-13 GR GR20010400419T patent/GR3035572T3/el not_active IP Right Cessation
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