OA12298A - Cyclic ketones, their preparation and their use inthe synthesis of amino acids. - Google Patents

Cyclic ketones, their preparation and their use inthe synthesis of amino acids. Download PDF

Info

Publication number: OA12298A
Authority: OA; OAPI
Prior art keywords: formula; compound; cyclopentanone; methyl; ethyl
Prior art date: 2000-06-28

Application number

OA1200200391A

Other languages

English (en)

Inventor

David Clive Blakemore

Justin Stephen Bryans

Original Assignee

Warner Lambert Co

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.)

2000-06-28

Filing date

2001-06-28

Publication date

2004-03-18

2001-06-28 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2004-03-18 Publication of OA12298A publication Critical patent/OA12298A/en

Links

230000015572 biosynthetic process Effects 0.000 title description 7
238000003786 synthesis reaction Methods 0.000 title description 7
150000003997 cyclic ketones Chemical class 0.000 title description 2
150000001413 amino acids Chemical class 0.000 title 1
238000002360 preparation method Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 60
238000000034 method Methods 0.000 claims abstract description 50
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims abstract description 14
125000001424 substituent group Chemical group 0.000 claims abstract description 12
-1 acetoxy compound Chemical class 0.000 claims abstract description 11
239000012038 nucleophile Substances 0.000 claims abstract description 7
125000002524 organometallic group Chemical group 0.000 claims abstract description 6
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims abstract description 5
BZKFMUIJRXWWQK-UHFFFAOYSA-N cyclopenten-2-one Natural products O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 54
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 44
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 42
239000002904 solvent Substances 0.000 claims description 40
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
238000006243 chemical reaction Methods 0.000 claims description 20
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical group C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 12
125000002843 carboxylic acid group Chemical group 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 8
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 8
NRPKBHXHDVUDQQ-BQBZGAKWSA-N (3s,4s)-3-ethyl-4-methylcyclopentan-1-one Chemical compound CC[C@H]1CC(=O)C[C@@H]1C NRPKBHXHDVUDQQ-BQBZGAKWSA-N 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
230000001131 transforming effect Effects 0.000 claims description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
239000007818 Grignard reagent Substances 0.000 claims description 4
LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
239000003153 chemical reaction reagent Substances 0.000 claims description 4
230000001590 oxidative effect Effects 0.000 claims description 4
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 4
235000005074 zinc chloride Nutrition 0.000 claims description 4
239000011592 zinc chloride Substances 0.000 claims description 4
AOKRXIIIYJGNNU-RXMQYKEDSA-N (3r)-3-methylcyclopentan-1-one Chemical compound C[C@@H]1CCC(=O)C1 AOKRXIIIYJGNNU-RXMQYKEDSA-N 0.000 claims description 3
ZMGMYCHEWPVBEL-PHDIDXHHSA-N (3r,4r)-3,4-dimethylcyclopentan-1-one Chemical compound C[C@@H]1CC(=O)C[C@H]1C ZMGMYCHEWPVBEL-PHDIDXHHSA-N 0.000 claims description 3
AOKRXIIIYJGNNU-YFKPBYRVSA-N (3s)-3-methylcyclopentan-1-one Chemical compound C[C@H]1CCC(=O)C1 AOKRXIIIYJGNNU-YFKPBYRVSA-N 0.000 claims description 3
XISLEOYIFRZKLT-YUMQZZPRSA-N (3s,4s)-3,4-diethylcyclopentan-1-one Chemical compound CC[C@H]1CC(=O)C[C@@H]1CC XISLEOYIFRZKLT-YUMQZZPRSA-N 0.000 claims description 3
VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims description 3
239000007868 Raney catalyst Substances 0.000 claims description 3
229910000564 Raney nickel Inorganic materials 0.000 claims description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000001979 organolithium group Chemical group 0.000 claims description 3
XERALSLWOPMNRJ-ZCFIWIBFSA-N (3r)-3-ethylcyclopentan-1-one Chemical compound CC[C@@H]1CCC(=O)C1 XERALSLWOPMNRJ-ZCFIWIBFSA-N 0.000 claims description 2
NRPKBHXHDVUDQQ-RNFRBKRXSA-N (3r,4r)-3-ethyl-4-methylcyclopentan-1-one Chemical compound CC[C@@H]1CC(=O)C[C@H]1C NRPKBHXHDVUDQQ-RNFRBKRXSA-N 0.000 claims description 2
CGTHIZOWBBAQMQ-RKDXNWHRSA-N (3r,4r)-3-ethyl-4-propylcyclopentan-1-one Chemical compound CCC[C@@H]1CC(=O)C[C@H]1CC CGTHIZOWBBAQMQ-RKDXNWHRSA-N 0.000 claims description 2
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 claims description 2
229910000103 lithium hydride Inorganic materials 0.000 claims description 2
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 2
229910003446 platinum oxide Inorganic materials 0.000 claims description 2
239000012312 sodium hydride Substances 0.000 claims description 2
229910000104 sodium hydride Inorganic materials 0.000 claims description 2
XISLEOYIFRZKLT-HTQZYQBOSA-N (3r,4r)-3,4-diethylcyclopentan-1-one Chemical compound CC[C@@H]1CC(=O)C[C@H]1CC XISLEOYIFRZKLT-HTQZYQBOSA-N 0.000 claims 2
OQIDMDSYGYPBCR-HTQZYQBOSA-N (3r,4r)-3-methyl-4-propylcyclopentan-1-one Chemical compound CCC[C@@H]1CC(=O)C[C@H]1C OQIDMDSYGYPBCR-HTQZYQBOSA-N 0.000 claims 2
TWKQLPXRUHHFBU-SSDOTTSWSA-N (3r)-3-propylcyclopentan-1-one Chemical compound CCC[C@@H]1CCC(=O)C1 TWKQLPXRUHHFBU-SSDOTTSWSA-N 0.000 claims 1
XERALSLWOPMNRJ-LURJTMIESA-N (3s)-3-ethylcyclopentan-1-one Chemical compound CC[C@H]1CCC(=O)C1 XERALSLWOPMNRJ-LURJTMIESA-N 0.000 claims 1
CGTHIZOWBBAQMQ-IUCAKERBSA-N (3s,4s)-3-ethyl-4-propylcyclopentan-1-one Chemical compound CCC[C@H]1CC(=O)C[C@@H]1CC CGTHIZOWBBAQMQ-IUCAKERBSA-N 0.000 claims 1
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
150000004678 hydrides Chemical class 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
150000007530 organic bases Chemical class 0.000 claims 1
229910052703 rhodium Inorganic materials 0.000 claims 1
239000010948 rhodium Substances 0.000 claims 1
125000002130 sulfonic acid ester group Chemical group 0.000 claims 1
UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical class OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 abstract description 11
YNCKAQVPQJWLJW-ZETCQYMHSA-N [(1r)-4-oxocyclopent-2-en-1-yl] acetate Chemical compound CC(=O)O[C@@H]1CC(=O)C=C1 YNCKAQVPQJWLJW-ZETCQYMHSA-N 0.000 abstract description 9
YNCKAQVPQJWLJW-SSDOTTSWSA-N [(1s)-4-oxocyclopent-2-en-1-yl] acetate Chemical compound CC(=O)O[C@H]1CC(=O)C=C1 YNCKAQVPQJWLJW-SSDOTTSWSA-N 0.000 abstract description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 36
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 31
101150041968 CDC13 gene Proteins 0.000 description 29
239000000203 mixture Substances 0.000 description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
150000001241 acetals Chemical class 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 19
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
OWBTYPJTUOEWEK-UHFFFAOYSA-N (-)-(2R,3R)--2,3-butanediol Natural products CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 17
238000003756 stirring Methods 0.000 description 17
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
239000012267 brine Substances 0.000 description 14
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
150000002576 ketones Chemical class 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
229910052786 argon Inorganic materials 0.000 description 9
DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000000543 intermediate Substances 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
238000010992 reflux Methods 0.000 description 8
RBEIPUMJEQUKIW-UHFFFAOYSA-N (2-oxocyclopentyl) acetate Chemical compound CC(=O)OC1CCCC1=O RBEIPUMJEQUKIW-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
AXAZMDOAUQTMOW-UHFFFAOYSA-N dimethylzinc Chemical compound C[Zn]C AXAZMDOAUQTMOW-UHFFFAOYSA-N 0.000 description 7
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
229910052681 coesite Inorganic materials 0.000 description 6
229910052906 cristobalite Inorganic materials 0.000 description 6
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 6
235000011167 hydrochloric acid Nutrition 0.000 description 6
229960000443 hydrochloric acid Drugs 0.000 description 6
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 6
229910052682 stishovite Inorganic materials 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
229910052905 tridymite Inorganic materials 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 5
239000010410 layer Substances 0.000 description 5
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
ZMGMYCHEWPVBEL-WDSKDSINSA-N (3s,4s)-3,4-dimethylcyclopentan-1-one Chemical compound C[C@H]1CC(=O)C[C@@H]1C ZMGMYCHEWPVBEL-WDSKDSINSA-N 0.000 description 4
ZSBWUNDRDHVNJL-UHFFFAOYSA-N 2-Methyl-2-cyclopenten-1-one Chemical compound CC1=CCCC1=O ZSBWUNDRDHVNJL-UHFFFAOYSA-N 0.000 description 4
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
239000007858 starting material Substances 0.000 description 4
230000000707 stereoselective effect Effects 0.000 description 4
GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
206010015037 epilepsy Diseases 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000012948 isocyanate Substances 0.000 description 3
150000002513 isocyanates Chemical class 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
OQIDMDSYGYPBCR-YUMQZZPRSA-N (3s,4s)-3-methyl-4-propylcyclopentan-1-one Chemical compound CCC[C@H]1CC(=O)C[C@@H]1C OQIDMDSYGYPBCR-YUMQZZPRSA-N 0.000 description 2
GKDBCXCOTZXACW-UHFFFAOYSA-N 2-ethylcyclopent-2-en-1-one Chemical compound CCC1=CCCC1=O GKDBCXCOTZXACW-UHFFFAOYSA-N 0.000 description 2
ZIXLDMFVRPABBX-UHFFFAOYSA-N 2-methylcyclopentan-1-one Chemical compound CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 2
AOKRXIIIYJGNNU-UHFFFAOYSA-N 3-methylcyclopentan-1-one Chemical compound CC1CCC(=O)C1 AOKRXIIIYJGNNU-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
101500028027 Mus musculus Cathelin-related antimicrobial peptide Proteins 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
238000005349 anion exchange Methods 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
208000002173 dizziness Diseases 0.000 description 2
229960002870 gabapentin Drugs 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
208000002551 irritable bowel syndrome Diseases 0.000 description 2
229940072228 neurontin Drugs 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
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 description 2
ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
JRPGMCRJPQJYPE-UHFFFAOYSA-N zinc;carbanide Chemical compound [CH3-].[CH3-].[Zn+2] JRPGMCRJPQJYPE-UHFFFAOYSA-N 0.000 description 2
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
KDPMHQOKQNEGGO-GMIYPCFNSA-N (3R,4R)-3,4-dimethylcyclopentan-1-one (3S,4S)-3-ethyl-4-methylcyclopentan-1-one Chemical compound C(C)[C@H]1CC(C[C@@H]1C)=O.C[C@@H]1CC(C[C@H]1C)=O KDPMHQOKQNEGGO-GMIYPCFNSA-N 0.000 description 1
UCAZBEGHYMABBR-HNZGJALOSA-N (3S,4S)-3,4-dimethylcyclopentan-1-one (3R)-3-propylcyclopentan-1-one Chemical compound C[C@H]1CC(C[C@@H]1C)=O.C(CC)[C@H]1CC(CC1)=O UCAZBEGHYMABBR-HNZGJALOSA-N 0.000 description 1
TWKQLPXRUHHFBU-ZETCQYMHSA-N (3s)-3-propylcyclopentan-1-one Chemical compound CCC[C@H]1CCC(=O)C1 TWKQLPXRUHHFBU-ZETCQYMHSA-N 0.000 description 1
IJDYOKVVRXZCFD-UHFFFAOYSA-N (4-hydroxycyclopent-2-en-1-yl) acetate Chemical class CC(=O)OC1CC(O)C=C1 IJDYOKVVRXZCFD-UHFFFAOYSA-N 0.000 description 1
OWBTYPJTUOEWEK-QWWZWVQMSA-N (R,R)-butane-2,3-diol Chemical compound C[C@@H](O)[C@@H](C)O OWBTYPJTUOEWEK-QWWZWVQMSA-N 0.000 description 1
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
FTGZMZBYOHMEPS-UHFFFAOYSA-N 2,2-dimethylcyclopentan-1-one Chemical compound CC1(C)CCCC1=O FTGZMZBYOHMEPS-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
OCFRCAFXNXHIIX-UHFFFAOYSA-N 2-propylcyclopent-2-en-1-one Chemical compound CCCC1=CCCC1=O OCFRCAFXNXHIIX-UHFFFAOYSA-N 0.000 description 1
XERALSLWOPMNRJ-UHFFFAOYSA-N 3-ethylcyclopentan-1-one Chemical compound CCC1CCC(=O)C1 XERALSLWOPMNRJ-UHFFFAOYSA-N 0.000 description 1
TWKQLPXRUHHFBU-UHFFFAOYSA-N 3-propylcyclopentan-1-one Chemical compound CCCC1CCC(=O)C1 TWKQLPXRUHHFBU-UHFFFAOYSA-N 0.000 description 1
DHNDDRBMUVFQIZ-UHFFFAOYSA-N 4-hydroxycyclopent-2-en-1-one Chemical compound OC1CC(=O)C=C1 DHNDDRBMUVFQIZ-UHFFFAOYSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
NEEWCQYLRTYKSG-MENMJLHVSA-N C(C)[C@@H]1CC(CC1)=O.C[C@@H]1CC(CC1)=O Chemical compound C(C)[C@@H]1CC(CC1)=O.C[C@@H]1CC(CC1)=O NEEWCQYLRTYKSG-MENMJLHVSA-N 0.000 description 1
OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 1
QQQCHERHJXDQAT-UHFFFAOYSA-N CC(=O)OC1CC(=O)C=C1.CC(=O)OC1CC(=O)C=C1 Chemical compound CC(=O)OC1CC(=O)C=C1.CC(=O)OC1CC(=O)C=C1 QQQCHERHJXDQAT-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
101100001670 Emericella variicolor andE gene Proteins 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
208000018522 Gastrointestinal disease Diseases 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
208000006083 Hypokinesia Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
238000006845 Michael addition reaction Methods 0.000 description 1
241000972349 Ocoa Species 0.000 description 1
208000002193 Pain Diseases 0.000 description 1
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
CGWVBPMMLKULCR-UHFFFAOYSA-N acetic acid;cyclohexylmethanamine Chemical group CC(O)=O.NCC1CCCCC1 CGWVBPMMLKULCR-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
229940125681 anticonvulsant agent Drugs 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
238000013459 approach Methods 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
LRHPLDYGYMQRHN-UHFFFAOYSA-N butyl alcohol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
230000003483 hypokinetic effect Effects 0.000 description 1
239000012535 impurity Substances 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
208000014674 injury Diseases 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
ZRKSVHFXTRFQFL-UHFFFAOYSA-N isocyanomethane Chemical compound C[N+]#[C-] ZRKSVHFXTRFQFL-UHFFFAOYSA-N 0.000 description 1
YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 description 1
239000000463 material Substances 0.000 description 1
ZKUUVVYMPUDTGJ-UHFFFAOYSA-N methyl 5-hydroxy-4-methoxy-2-nitrobenzoate Chemical compound COC(=O)C1=CC(O)=C(OC)C=C1[N+]([O-])=O ZKUUVVYMPUDTGJ-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
208000004296 neuralgia Diseases 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
230000002981 neuropathic effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
229960005152 pentetrazol Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
BPEVHDGLPIIAGH-UHFFFAOYSA-N ruthenium(3+) Chemical compound [Ru+3] BPEVHDGLPIIAGH-UHFFFAOYSA-N 0.000 description 1
YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
HNMWIKVFYHYBKX-UHFFFAOYSA-N tert-butyl 3-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC11CC(=O)NC1 HNMWIKVFYHYBKX-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
230000008733 trauma Effects 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/28—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and containing rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/395—Saturated compounds containing a keto group being part of a ring of a five-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

OA1200200391A 2000-06-28 2001-06-28 Cyclic ketones, their preparation and their use inthe synthesis of amino acids. OA12298A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB0015771A GB2364049A (en)	2000-06-28	2000-06-28	Cyclic ketones and their use in the synthesis of amino acids

Publications (1)

Publication Number	Publication Date
OA12298A true OA12298A (en)	2004-03-18

Family

ID=9894534

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200200391A OA12298A (en)	2000-06-28	2001-06-28	Cyclic ketones, their preparation and their use inthe synthesis of amino acids.

Country Status (24)

Country	Link
US (2)	US6872856B2 (is)
EP (1)	EP1296921A1 (is)
JP (1)	JP2004501884A (is)
KR (1)	KR100778953B1 (is)
CN (1)	CN1438985A (is)
AP (1)	AP2002002699A0 (is)
AU (2)	AU2001266208B2 (is)
BR (1)	BR0112076A (is)
CA (1)	CA2411808A1 (is)
EA (1)	EA200201202A1 (is)
GB (1)	GB2364049A (is)
HR (1)	HRP20021017A2 (is)
HU (1)	HUP0301306A2 (is)
IL (2)	IL153704A0 (is)
IS (1)	IS6636A (is)
MA (1)	MA26921A1 (is)
MX (1)	MXPA03000076A (is)
NO (1)	NO20026198D0 (is)
NZ (1)	NZ523218A (is)
OA (1)	OA12298A (is)
PL (1)	PL359107A1 (is)
WO (1)	WO2002000584A1 (is)
YU (1)	YU93702A (is)
ZA (1)	ZA200300243B (is)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2364049A (en) *	2000-06-28	2002-01-16	Warner Lambert Co	Cyclic ketones and their use in the synthesis of amino acids
US6818787B2 (en)	2001-06-11	2004-11-16	Xenoport, Inc.	Prodrugs of GABA analogs, compositions and uses thereof
US8048917B2 (en)	2005-04-06	2011-11-01	Xenoport, Inc.	Prodrugs of GABA analogs, compositions and uses thereof
US7186855B2 (en)	2001-06-11	2007-03-06	Xenoport, Inc.	Prodrugs of GABA analogs, compositions and uses thereof
US7232924B2 (en)	2001-06-11	2007-06-19	Xenoport, Inc.	Methods for synthesis of acyloxyalkyl derivatives of GABA analogs
CA2615490A1 (en) *	2005-07-18	2007-01-25	Pharmacia & Upjohn Company Llc	Stereoselective synthesis of 3,4-disubstituted cyclopentanones and related compounds
CN102190536A (zh) *	2010-03-08	2011-09-21	华东理工大学	一种有机催化烯酮与有机膦化合物不对称共轭加成的方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2460891C2 (de) *	1974-12-21	1982-09-23	Gödecke AG, 1000 Berlin	1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
US4087544A (en) *	1974-12-21	1978-05-02	Warner-Lambert Company	Treatment of cranial dysfunctions using novel cyclic amino acids
US5254708A (en) *	1987-06-16	1993-10-19	Nissan Chemical Industries, Ltd.	Substituted cyclic ketones, substituted cyclic enones, and process for producing the same
US5134238A (en) *	1990-05-24	1992-07-28	Brigham Young University	Chiral copper amine complexes
US5480962A (en)	1993-07-22	1996-01-02	Eastman Chemical Company	Copolyesters having repeat units derived from succinic acid
DE69834204T2 (de)	1997-10-27	2007-03-29	Warner-Lambert Co. Llc	Zyklische aminosäuren und deren derivate als arzneimittel
GB2364049A (en) *	2000-06-28	2002-01-16	Warner Lambert Co	Cyclic ketones and their use in the synthesis of amino acids

2000
- 2000-06-28 GB GB0015771A patent/GB2364049A/en not_active Withdrawn
2001
- 2001-06-28 YU YU93702A patent/YU93702A/sh unknown
- 2001-06-28 PL PL01359107A patent/PL359107A1/xx not_active IP Right Cessation
- 2001-06-28 NZ NZ523218A patent/NZ523218A/en unknown
- 2001-06-28 EP EP01943670A patent/EP1296921A1/en not_active Withdrawn
- 2001-06-28 CN CN01811912A patent/CN1438985A/zh active Pending
- 2001-06-28 IL IL15370401A patent/IL153704A0/xx unknown
- 2001-06-28 AU AU2001266208A patent/AU2001266208B2/en not_active Ceased
- 2001-06-28 EA EA200201202A patent/EA200201202A1/ru unknown
- 2001-06-28 WO PCT/GB2001/002900 patent/WO2002000584A1/en not_active Ceased
- 2001-06-28 AU AU6620801A patent/AU6620801A/xx active Pending
- 2001-06-28 KR KR1020027017858A patent/KR100778953B1/ko not_active Expired - Fee Related
- 2001-06-28 CA CA002411808A patent/CA2411808A1/en not_active Abandoned
- 2001-06-28 BR BR0112076-0A patent/BR0112076A/pt not_active IP Right Cessation
- 2001-06-28 OA OA1200200391A patent/OA12298A/en unknown
- 2001-06-28 AP APAP/P/2002/002699A patent/AP2002002699A0/en unknown
- 2001-06-28 MX MXPA03000076A patent/MXPA03000076A/es active IP Right Grant
- 2001-06-28 HR HR20021017A patent/HRP20021017A2/xx not_active Application Discontinuation
- 2001-06-28 US US10/312,065 patent/US6872856B2/en not_active Expired - Fee Related
- 2001-06-28 JP JP2002505335A patent/JP2004501884A/ja not_active Withdrawn
- 2001-06-28 HU HU0301306A patent/HUP0301306A2/hu unknown
2002
- 2002-11-28 IS IS6636A patent/IS6636A/is unknown
- 2002-12-23 NO NO20026198A patent/NO20026198D0/no not_active Application Discontinuation
- 2002-12-24 MA MA26977A patent/MA26921A1/fr unknown
2003
- 2003-01-09 ZA ZA200300243A patent/ZA200300243B/en unknown
2005
- 2005-03-07 US US11/074,250 patent/US20050215816A1/en not_active Abandoned
2008
- 2008-03-27 IL IL190490A patent/IL190490A0/en unknown

Also Published As

Publication number	Publication date
US20050215816A1 (en)	2005-09-29
CA2411808A1 (en)	2002-01-03
GB2364049A (en)	2002-01-16
IL153704A0 (en)	2003-07-06
AP2002002699A0 (en)	2002-12-31
IS6636A (is)	2002-11-28
IL190490A0 (en)	2008-11-03
NO20026198L (no)	2002-12-23
MA26921A1 (fr)	2004-12-20
CN1438985A (zh)	2003-08-27
EA200201202A1 (ru)	2003-06-26
KR100778953B1 (ko)	2007-11-27
BR0112076A (pt)	2003-09-02
JP2004501884A (ja)	2004-01-22
EP1296921A1 (en)	2003-04-02
PL359107A1 (en)	2004-08-23
MXPA03000076A (es)	2003-10-15
KR20030016311A (ko)	2003-02-26
HUP0301306A2 (hu)	2003-08-28
NZ523218A (en)	2004-06-25
HRP20021017A2 (en)	2004-02-29
AU6620801A (en)	2002-01-08
WO2002000584A1 (en)	2002-01-03
AU2001266208B2 (en)	2006-11-23
YU93702A (sh)	2006-08-17
US6872856B2 (en)	2005-03-29
ZA200300243B (en)	2004-06-14
US20030187296A1 (en)	2003-10-02
NO20026198D0 (no)	2002-12-23
GB0015771D0 (en)	2000-08-16

Publication	Publication Date	Title
OA12298A (en)	2004-03-18	Cyclic ketones, their preparation and their use inthe synthesis of amino acids.
AU2001266208A1 (en)	2002-03-28	Cyclic ketones, their preparation and their use in the synthesis of amino acids
AU725484B2 (en)	2000-10-12	Compounds and method for preparing substituted 4-phenyl-4-cyanocyclohexanoic acids
KR102472541B1 (ko)	2022-11-30	막사칼시톨의 제조방법 및 그를 위한 중간체
US20030083520A1 (en)	2003-05-01	Process for preparing bicyclic amino acid
JP3896774B2 (ja)	2007-03-22	ビスイソオキサゾリン誘導体、その製造法およびその金属錯体からなる触媒
US6921832B2 (en)	2005-07-26	Optically active fluorine-containing compounds and processes for their production
JP3852122B2 (ja)	2006-11-29	錯体及びそれを用いたヒドロキシスルフィド類の製造方法
US20030050497A1 (en)	2003-03-13	Process and intermediates for preparing a cyclohexylnitrile
JP2004175758A (ja)	2004-06-24	β−ケトエステルを用いてアルキル化物を立体選択的に製造するための方法
Bhattacharyya	2003	Stereoselective synthesis of alpha-hydroxy acid derivatives and studies on the synthesis of ethophenprox
NZ519800A (en)	2004-11-26	Process and intermediates for preparing a cyclohexylnitrile
AU2004205303A1 (en)	2004-09-23	Process and intermediates for preparing a cyclohexylnitrile
JP2003313147A (ja)	2003-11-06	光学活性アダマンタン誘導体及びその製造方法
GB2375108A (en)	2002-11-06	Production of a bicycloheptanone
JP2007238526A (ja)	2007-09-20	不斉２−アザ−コープ転位を用いる光学活性ホモアリル第一級アミンの製造方法
NZ535657A (en)	2006-05-26	Process and intermediates for preparing a cyclohexylnitrile
JPH07316086A (ja)	1995-12-05	１，２，２−トリメチル−シクロペンチル−メチルケトン誘導体の製造方法、３，４，５，５−テトラメチル−３−シクロヘキセン−誘導体および７−オキサ−１，５，５，６−テトラメチル−ビシクロ［４．１．０ヘプタン−誘導体
MXPA00003405A (en)	2002-02-26	Method for preparing substituted 4-phenyl-4-cyanocyclohexanoic acids