ZA200200965B - Process for preparing acids via Alpha-chloroepoxy esters. - Google Patents
Process for preparing acids via Alpha-chloroepoxy esters. Download PDFInfo
- Publication number
- ZA200200965B ZA200200965B ZA200200965A ZA200200965A ZA200200965B ZA 200200965 B ZA200200965 B ZA 200200965B ZA 200200965 A ZA200200965 A ZA 200200965A ZA 200200965 A ZA200200965 A ZA 200200965A ZA 200200965 B ZA200200965 B ZA 200200965B
- Authority
- ZA
- South Africa
- Prior art keywords
- substituted
- alkyl
- cr4r5
- unsubstituted
- hydrogen
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000002253 acid Substances 0.000 title description 23
- 150000007513 acids Chemical class 0.000 title description 8
- -1 alkali metal salt Chemical class 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims description 48
- 239000001257 hydrogen Substances 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 239000002585 base Substances 0.000 claims description 14
- 235000019000 fluorine Nutrition 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 13
- 150000002118 epoxides Chemical class 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical class OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 150000002576 ketones Chemical class 0.000 claims description 8
- 239000011780 sodium chloride Substances 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- CFBUZOUXXHZCFB-UHFFFAOYSA-N 4-cyano-4-(3-cyclopentyloxy-4-methoxyphenyl)-1-cyclohexanecarboxylic acid Chemical compound COC1=CC=C(C2(CCC(CC2)C(O)=O)C#N)C=C1OC1CCCC1 CFBUZOUXXHZCFB-UHFFFAOYSA-N 0.000 claims description 5
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical group [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 229960005235 piperonyl butoxide Drugs 0.000 claims description 4
- 125000005592 polycycloalkyl group Polymers 0.000 claims description 4
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 4
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 4
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- 125000003107 substituted aryl group Chemical group 0.000 claims 3
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 claims 1
- 125000006539 C12 alkyl 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])C([H])([H])C([H])([H])* 0.000 claims 1
- 240000007175 Datura inoxia Species 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 229940120124 dichloroacetate Drugs 0.000 claims 1
- IWYBVQLPTCMVFO-UHFFFAOYSA-N ethyl 2,2-dichloroacetate Chemical compound CCOC(=O)C(Cl)Cl IWYBVQLPTCMVFO-UHFFFAOYSA-N 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000003921 oil Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000011067 equilibration Methods 0.000 description 4
- LWIYARDMKJONLK-UHFFFAOYSA-N methyl 2-chloro-6-cyano-6-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxaspiro[2.5]octane-2-carboxylate Chemical compound COC(=O)C1(Cl)OC11CCC(C=2C=C(OC3CCCC3)C(OC)=CC=2)(C#N)CC1 LWIYARDMKJONLK-UHFFFAOYSA-N 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- OOLNHSCKYYQXFO-UHFFFAOYSA-N 2-chloro-6-cyano-6-(3-cyclopentyloxy-4-methoxyphenyl)-1-oxaspiro[2.5]octane-2-carboxylic acid Chemical compound COC1=CC=C(C2(CCC3(CC2)C(O3)(Cl)C(O)=O)C#N)C=C1OC1CCCC1 OOLNHSCKYYQXFO-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 125000005469 ethylenyl group Chemical group 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 210000000440 neutrophil Anatomy 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000007970 thio esters Chemical class 0.000 description 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- URXUAYQZIDJXGT-UHFFFAOYSA-N 1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexane-1-carbonitrile Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#N)C=C1OC1CCCC1 URXUAYQZIDJXGT-UHFFFAOYSA-N 0.000 description 1
- ZUYKJZQOPXDNOK-UHFFFAOYSA-N 2-(ethylamino)-2-thiophen-2-ylcyclohexan-1-one;hydrochloride Chemical class Cl.C=1C=CSC=1C1(NCC)CCCCC1=O ZUYKJZQOPXDNOK-UHFFFAOYSA-N 0.000 description 1
- KJZWYCAIEUYAIW-UHFFFAOYSA-N 4-cyanocyclohexane-1-carboxylic acid Chemical class OC(=O)C1CCC(C#N)CC1 KJZWYCAIEUYAIW-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010015866 Extravasation Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 208000019693 Lung disease Diseases 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- 101150107341 RERE gene Proteins 0.000 description 1
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 1
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 1
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002497 edematous effect Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000036251 extravasation Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- HKMLRUAPIDAGIE-UHFFFAOYSA-N methyl 2,2-dichloroacetate Chemical compound COC(=O)C(Cl)Cl HKMLRUAPIDAGIE-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 230000011242 neutrophil chemotaxis Effects 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000009919 sequestration Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
- C07C2601/06—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14757699P | 1999-08-06 | 1999-08-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200200965B true ZA200200965B (en) | 2003-04-30 |
Family
ID=22522121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200200965A ZA200200965B (en) | 1999-08-06 | 2002-02-04 | Process for preparing acids via Alpha-chloroepoxy esters. |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP1200394B1 (pt) |
| JP (1) | JP2003506431A (pt) |
| KR (1) | KR20020022793A (pt) |
| CN (4) | CN1266119C (pt) |
| AR (1) | AR025028A1 (pt) |
| AT (1) | ATE340780T1 (pt) |
| AU (1) | AU774582B2 (pt) |
| BR (1) | BR0013025A (pt) |
| CA (1) | CA2381010A1 (pt) |
| CO (1) | CO5190744A1 (pt) |
| CZ (1) | CZ2002428A3 (pt) |
| DE (1) | DE60030981T2 (pt) |
| EC (1) | ECSP003599A (pt) |
| ES (1) | ES2272310T3 (pt) |
| HK (1) | HK1047080A1 (pt) |
| HU (1) | HUP0202453A2 (pt) |
| IL (1) | IL147365A0 (pt) |
| MX (1) | MXPA02001337A (pt) |
| NO (1) | NO20020561L (pt) |
| NZ (1) | NZ516945A (pt) |
| PE (1) | PE20010398A1 (pt) |
| PL (1) | PL353347A1 (pt) |
| TR (1) | TR200200307T2 (pt) |
| UY (1) | UY26268A1 (pt) |
| WO (1) | WO2001010822A1 (pt) |
| ZA (1) | ZA200200965B (pt) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101116828B (zh) * | 2006-08-03 | 2011-06-01 | 中国科学院大连化学物理研究所 | 手性吡啶双噁唑啉催化剂及制备方法和应用 |
| US10526287B2 (en) | 2015-04-23 | 2020-01-07 | Constellation Pharmaceuticals, Inc. | LSD1 inhibitors and uses thereof |
| AU2017348100B2 (en) | 2016-10-26 | 2021-08-26 | Constellation Pharmaceuticals, Inc. | LSD1 inhibitors and medical uses thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK279958B6 (sk) * | 1992-04-02 | 1999-06-11 | Smithkline Beecham Corporation | Zlúčeniny s protialergickým a protizápalovým účink |
| AU3803593A (en) * | 1992-04-02 | 1993-11-08 | Smithkline Beecham Corporation | Compounds |
| EP0634930A4 (en) * | 1992-04-02 | 1995-02-22 | Smithkline Beecham Corporation | Compounds useful for treating allergic and inflammatory diseases. |
| DE69331265T2 (de) * | 1992-04-02 | 2002-08-08 | Smithkline Beecham Corp., Philadelphia | Verbindungen zur behandlung von entzündlichen erkrankungen und zur hemmung der produktion von tumornekrosefaktor |
| GB9404706D0 (en) * | 1994-03-11 | 1994-04-27 | Smithkline Beecham Corp | Compounds |
| MY118813A (en) * | 1997-02-12 | 2005-01-31 | Smithkline Beecham Corp | Compounds and method for preparing substituted 4-phenyl-4-cyanocyclohexanoic acids |
-
2000
- 2000-08-02 UY UY26268A patent/UY26268A1/es not_active Application Discontinuation
- 2000-08-02 EC EC2000003599A patent/ECSP003599A/es unknown
- 2000-08-03 CO CO00058243A patent/CO5190744A1/es not_active Application Discontinuation
- 2000-08-03 AR ARP000104011A patent/AR025028A1/es not_active Application Discontinuation
- 2000-08-04 JP JP2001515289A patent/JP2003506431A/ja not_active Withdrawn
- 2000-08-04 AT AT00953844T patent/ATE340780T1/de not_active IP Right Cessation
- 2000-08-04 CZ CZ2002428A patent/CZ2002428A3/cs unknown
- 2000-08-04 PE PE2000000790A patent/PE20010398A1/es not_active Application Discontinuation
- 2000-08-04 CN CNB2004100321653A patent/CN1266119C/zh not_active Expired - Fee Related
- 2000-08-04 CN CNA2004100321634A patent/CN1530362A/zh active Pending
- 2000-08-04 ES ES00953844T patent/ES2272310T3/es not_active Expired - Lifetime
- 2000-08-04 CN CN008113440A patent/CN1217923C/zh not_active Expired - Fee Related
- 2000-08-04 TR TR2002/00307T patent/TR200200307T2/xx unknown
- 2000-08-04 WO PCT/US2000/021394 patent/WO2001010822A1/en active IP Right Grant
- 2000-08-04 MX MXPA02001337A patent/MXPA02001337A/es unknown
- 2000-08-04 PL PL00353347A patent/PL353347A1/xx not_active Application Discontinuation
- 2000-08-04 CN CNA2004100321649A patent/CN1597675A/zh active Pending
- 2000-08-04 DE DE60030981T patent/DE60030981T2/de not_active Expired - Lifetime
- 2000-08-04 AU AU66222/00A patent/AU774582B2/en not_active Ceased
- 2000-08-04 KR KR1020027001574A patent/KR20020022793A/ko active IP Right Grant
- 2000-08-04 CA CA002381010A patent/CA2381010A1/en not_active Abandoned
- 2000-08-04 NZ NZ516945A patent/NZ516945A/en unknown
- 2000-08-04 HU HU0202453A patent/HUP0202453A2/hu unknown
- 2000-08-04 IL IL14736500A patent/IL147365A0/xx unknown
- 2000-08-04 EP EP00953844A patent/EP1200394B1/en not_active Expired - Lifetime
- 2000-08-04 BR BR0013025-7A patent/BR0013025A/pt not_active IP Right Cessation
-
2002
- 2002-02-04 ZA ZA200200965A patent/ZA200200965B/en unknown
- 2002-02-05 NO NO20020561A patent/NO20020561L/no not_active Application Discontinuation
- 2002-09-27 HK HK02107178.7A patent/HK1047080A1/zh unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Munavalli et al. | Trifluoromethylsulfenylation of masked carbonyl compounds | |
| KR20150006076A (ko) | 광학 활성 사이클로프로필아민의 제조 방법 | |
| EP1328506B1 (fr) | Intermediaires utiles pour la synthese de retinoides | |
| US3853951A (en) | Preparation of 9-oxo-13-trans-prostenoic acid esters by alanate addition to cyclopentenone | |
| Auria et al. | Photochemical dimerization of methoxy substituted cinnamic acid methyl esters | |
| ZA200200965B (en) | Process for preparing acids via Alpha-chloroepoxy esters. | |
| JPS6030300B2 (ja) | 高シス３‐（２，２，２‐トリクロロエチル）‐２，２‐ジメチルシクロプロパン‐１‐カルボキシレ−ト類の製造方法 | |
| JPH0449533B2 (pt) | ||
| IE45008B1 (en) | Allethrolone sulphonates | |
| KR100412008B1 (ko) | 치환된 4-페닐-4-시아노시클로헥산산의 제조를 위한 화합물 및방법 | |
| US20040220424A1 (en) | Process for preparing acids via alpha-chloroepoxy esters | |
| US4800230A (en) | Preparation of alpha-cyano-phenoxybenzyl esters | |
| MXPA02001338A (es) | Metodo para preparar acidos ciclohexancarboxilicos. | |
| Crenshaw et al. | Potential antifertility agents. 4. Biological properties of diastereoisomeric 4-aryl-2-methylcyclohexanecarboxylic acids and related compounds | |
| JP3497528B2 (ja) | ペルヒドロ−５，５，８ａ−トリメチル−２−ナフタレノンの製法及び該製法のための出発化合物 | |
| US6740765B1 (en) | Method for preparing cyclohexane carboxylic acids | |
| Reiher | Solutions to Longstanding Problems of Chemoselectivity and Stereocontrol in Kalihinol Synthesis | |
| CN117623995A (zh) | 一种6-酮-乙烯基磺酰氟类化合物、其制备方法和应用 | |
| JPH04124157A (ja) | 光学活性４―クロロ―３―ヒドロキシブタン酸及びそのエステルの製法 | |
| Babakhanyan et al. | Cyclodimerization of the Stevens Rearrangement Products from 4-Alkoxy-2-butynyl (alkoxycarbonylmethyl) dimethyl-ammonium Salts into Cyclohexene Derivatives | |
| AU2004205303A1 (en) | Process and intermediates for preparing a cyclohexylnitrile | |
| AU2941301A (en) | Process and intermediates for preparing a cyclohexylnitrile | |
| MXPA99007441A (en) | Compounds and method for preparing substituted 4-phenyl-4-cyanocyclohexanoic acids | |
| CA2444210A1 (en) | Compounds and method for preparing substituted 4-phenyl-4-cyanocyclohexanoic acids | |
| JP2003509405A (ja) | ４−シアノ置換シクロヘキサン酸の製法および中間体 |