NO309265B1 - Fremgangsmåte for fremstilling av 1-aryl-1-cyanocyklobutan- derivater - Google Patents

Fremgangsmåte for fremstilling av 1-aryl-1-cyanocyklobutan- derivater Download PDF

Info

Publication number: NO309265B1
Authority: NO; Norway
Prior art keywords: formula; dimethylsulfoxide; temperature; compound; water
Prior art date: 1995-12-02

Application number

NO982474A

Other languages

English (en)

Norwegian (no)

Other versions

NO982474D0 (no

NO982474L (no

Inventor

Stephen John Barker

Sharon Michelle Clark

Original Assignee

Knoll Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1995-12-02

Filing date

1998-05-29

Publication date

2001-01-08

1998-05-29 Application filed by Knoll Ag filed Critical Knoll Ag

1998-05-29 Publication of NO982474D0 publication Critical patent/NO982474D0/no

1998-05-29 Publication of NO982474L publication Critical patent/NO982474L/no

2001-01-08 Publication of NO309265B1 publication Critical patent/NO309265B1/no

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)
Catalysts (AREA)
Crystals, And After-Treatments Of Crystals (AREA)

NO982474A 1995-12-02 1998-05-29 Fremgangsmåte for fremstilling av 1-aryl-1-cyanocyklobutan- derivater NO309265B1 (no)

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 (de)
EP (1)	EP0863868B1 (de)
JP (1)	JP2000501402A (de)
KR (1)	KR19990071838A (de)
CN (1)	CN1075057C (de)
AT (1)	ATE199247T1 (de)
AU (1)	AU717603B2 (de)
BG (1)	BG63498B1 (de)
BR (1)	BR9611683A (de)
CA (1)	CA2235043A1 (de)
CZ (1)	CZ164798A3 (de)
DE (1)	DE69611835T2 (de)
DK (1)	DK0863868T3 (de)
ES (1)	ES2154848T3 (de)
GB (1)	GB9524681D0 (de)
GR (1)	GR3035572T3 (de)
HU (1)	HUP9903481A3 (de)
IL (1)	IL124341A (de)
MX (1)	MX9804022A (de)
NO (1)	NO309265B1 (de)
NZ (1)	NZ323896A (de)
PL (1)	PL185047B1 (de)
PT (1)	PT863868E (de)
RU (1)	RU2179168C2 (de)
SI (1)	SI0863868T1 (de)
SK (1)	SK282470B6 (de)
TR (1)	TR199800987T2 (de)
WO (1)	WO1997020810A1 (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19756091A1 (de) *	1997-12-17	1999-06-24	Hoechst Marion Roussel De Gmbh	Verfahren zur Alkylierung von Alkyl- oder Benzylcyanderivaten in Gegenwart von Trialkylaminen oder -phosphinen
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
US6339106B1 (en)	1999-08-11	2002-01-15	Sepracor, Inc.	Methods and compositions for the treatment and prevention of sexual dysfunction
US6974838B2 (en)	1998-08-24	2005-12-13	Sepracor Inc.	Methods of treating or preventing pain using sibutramine metabolites
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 (11)

* Cited by examiner, † Cited by third party
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
IE52768B1 (en)	1981-04-06	1988-02-17	Boots Co Ltd	1-arylcyclobutylalkylamine compounds useful as therapeutic agents
ZA821577B (en) *	1981-04-06	1983-03-30	Boots Co Plc	Therapeutic agents
GB8501192D0 (en) *	1985-01-17	1985-02-20	Boots Co Plc	Therapeutic agents
SU1705280A1 (ru) *	1989-08-14	1992-01-15	Новосибирский институт органической химии СО АН СССР	Способ получени пара-алкилбензонитрилов
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
AU679765B2 (en)	1993-06-22	1997-07-10	Abbott Gmbh & Co. Kg	Isoquinoline derivatives as therapeutic agents

1995
- 1995-12-02 GB GBGB9524681.5A patent/GB9524681D0/en active Pending
1996
- 1996-11-28 PT PT96941602T patent/PT863868E/pt unknown
- 1996-11-28 AU AU10939/97A patent/AU717603B2/en not_active Ceased
- 1996-11-28 DK DK96941602T patent/DK0863868T3/da active
- 1996-11-28 BR BR9611683A patent/BR9611683A/pt not_active Application Discontinuation
- 1996-11-28 CN CN96198731A patent/CN1075057C/zh not_active Expired - Fee Related
- 1996-11-28 RU RU98112599/04A patent/RU2179168C2/ru active
- 1996-11-28 JP JP9520945A patent/JP2000501402A/ja active Pending
- 1996-11-28 WO PCT/EP1996/005246 patent/WO1997020810A1/en not_active Ceased
- 1996-11-28 KR KR1019980704120A patent/KR19990071838A/ko not_active Ceased
- 1996-11-28 DE DE69611835T patent/DE69611835T2/de not_active Expired - Fee Related
- 1996-11-28 SI SI9630254T patent/SI0863868T1/xx unknown
- 1996-11-28 US US09/077,698 patent/US6545173B1/en not_active Expired - Fee Related
- 1996-11-28 CA CA002235043A patent/CA2235043A1/en not_active Abandoned
- 1996-11-28 PL PL96326926A patent/PL185047B1/pl unknown
- 1996-11-28 NZ NZ323896A patent/NZ323896A/xx unknown
- 1996-11-28 EP EP96941602A patent/EP0863868B1/de not_active Expired - Lifetime
- 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 SK SK626-98A patent/SK282470B6/sk unknown
- 1996-11-28 HU HU9903481A patent/HUP9903481A3/hu unknown
- 1996-11-28 ES ES96941602T patent/ES2154848T3/es not_active Expired - Lifetime
- 1996-11-28 TR TR1998/00987T patent/TR199800987T2/xx unknown
- 1996-11-28 AT AT96941602T patent/ATE199247T1/de not_active IP Right Cessation
1998
- 1998-05-21 BG BG102473A patent/BG63498B1/bg unknown
- 1998-05-21 MX MX9804022A patent/MX9804022A/es unknown
- 1998-05-29 NO NO982474A patent/NO309265B1/no not_active IP Right Cessation
2001
- 2001-03-13 GR GR20010400419T patent/GR3035572T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU717603B2 (en)	2000-03-30
SI0863868T1 (en)	2001-06-30
CN1203585A (zh)	1998-12-30
KR19990071838A (ko)	1999-09-27
RU2179168C2 (ru)	2002-02-10
HUP9903481A1 (hu)	2001-01-29
DK0863868T3 (da)	2001-03-19
IL124341A0 (en)	1998-12-06
AU1093997A (en)	1997-06-27
ATE199247T1 (de)	2001-03-15
ES2154848T3 (es)	2001-04-16
BG63498B1 (bg)	2002-03-29
CA2235043A1 (en)	1997-06-12
CZ164798A3 (cs)	1998-09-16
GR3035572T3 (en)	2001-06-29
WO1997020810A8 (en)	2000-10-05
SK282470B6 (sk)	2002-02-05
EP0863868A1 (de)	1998-09-16
EP0863868B1 (de)	2001-02-21
WO1997020810A1 (en)	1997-06-12
CN1075057C (zh)	2001-11-21
NO982474D0 (no)	1998-05-29
BR9611683A (pt)	1999-03-02
NO982474L (no)	1998-05-29
JP2000501402A (ja)	2000-02-08
DE69611835T2 (de)	2001-06-07
HUP9903481A3 (en)	2001-11-28
PL185047B1 (pl)	2003-02-28
DE69611835D1 (de)	2001-03-29
IL124341A (en)	2001-09-13
PT863868E (pt)	2001-06-29
MX9804022A (es)	1998-09-30
US6545173B1 (en)	2003-04-08
TR199800987T2 (xx)	1998-09-21
BG102473A (en)	1999-05-31
SK62698A3 (en)	1999-02-11
PL326926A1 (en)	1998-11-09
GB9524681D0 (en)	1996-01-31
NZ323896A (en)	2000-01-28

Legal Events

Date	Code	Title	Description
2003-06-30	MM1K	Lapsed by not paying the annual fees	Free format text: LAPSED IN MAY 2003

Publication	Publication Date	Title
CA1197525A (fr)	1985-12-03	Procede de fabrication de chlorure de vinyle
US6545173B1 (en)	2003-04-08	Process for the preparation of 1-aryl-1-cyanocyclobutane derivatives
JPH09176140A (ja)	1997-07-08	２−クロロ−５−クロロメチルチアゾールの製造方法
KR101126825B1 (ko)	2012-03-23	(ｚ)-1-페닐-1-디에틸아미노카르보닐-2-아미노메틸시클로프로판 염산염의 제조 방법
US5463138A (en)	1995-10-31	Process for preparing difluoromethoxyarenes and difluoromethylthioarenes
US20020087008A1 (en)	2002-07-04	Process for preparing 2-chloro-5-chloromethylthiazole
JP3557624B2 (ja)	2004-08-25	４，６−ジニトロハロベンゼンの製造方法
WO2004009520A1 (ja)	2004-01-29	３級炭素塩素化炭化水素の製造方法
JP4038024B2 (ja)	2008-01-23	１−クロロ−４−アリールブタン類の製造方法
JP4270524B2 (ja)	2009-06-03	シクロアルキルおよびハロアルキルｏ−アミノフエニルケトン類の改良された製造方法
EP0003242B1 (de)	1982-01-20	Verfahren zur Herstellung von alpha-Cyanobenzylestern
JP2024522900A (ja)	2024-06-21	イソオキサゾリンカルボン酸誘導体の製造方法
US6069255A (en)	2000-05-30	Preparation of vinyl isothiocyanates
RU2167140C1 (ru)	2001-05-20	Способ получения винилиденхлорида
US5719294A (en)	1998-02-17	Process for preparing N-cyclohexylthiophthalimide
NZ224723A (en)	1991-07-26	Process for preparing substituted alpha-methylstyrene
US4861927A (en)	1989-08-29	Dehydrohalogenation of ring-halogenated α-halocumenes
PL118592B1 (en)	1981-10-31	Process for preparing novel 2-cyano-3-azabicyclo/3,1,0/hexanesana
US5841004A (en)	1998-11-24	3-substituted-α, β-dibromoethylbenzene and process for preparing the same
HUT61274A (en)	1992-12-28	Process for regioselective production of 3-substituted 3-aryloxy propaneamine compounds
CA1193616A (en)	1985-09-17	1,2-dihalogenoalkylsulfonyl isocyanates and 1,2- dihalogenocycloalkylsulfonyl isocyanates and process for their manufacture
JPH09143106A (ja)	1997-06-03	塩素化反応による芳香族置換塩素化炭化水素の製造法
WO2002050022A1 (en)	2002-06-27	Process for the production of carotenoids
JPH0530827B2 (de)	1993-05-11