NO972898L - 4,4-(Disubstituerte)cykloheksan-1-on-monomerer og beslektede forbindelser - Google Patents
4,4-(Disubstituerte)cykloheksan-1-on-monomerer og beslektede forbindelserInfo
- Publication number
- NO972898L NO972898L NO972898A NO972898A NO972898L NO 972898 L NO972898 L NO 972898L NO 972898 A NO972898 A NO 972898A NO 972898 A NO972898 A NO 972898A NO 972898 L NO972898 L NO 972898L
- Authority
- NO
- Norway
- Prior art keywords
- cyclopentyloxy
- methoxyphenyl
- cyclohexan
- substituted
- methyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 87
- 239000000178 monomer Substances 0.000 title description 2
- -1 thiopyranyl Chemical group 0.000 claims description 122
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 49
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 125000001153 fluoro group Chemical group F* 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 241000124008 Mammalia Species 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 9
- 208000006673 asthma Diseases 0.000 claims description 9
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000002541 furyl group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 150000001721 carbon Chemical group 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- PQCOFAMMLMWAPY-UHFFFAOYSA-N methyl 5-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]thiophene-3-carboxylate Chemical compound COC(=O)C1=CSC(C#CC2(CCC(=O)CC2)C=2C=C(OC3CCCC3)C(OC)=CC=2)=C1 PQCOFAMMLMWAPY-UHFFFAOYSA-N 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000005592 polycycloalkyl group Polymers 0.000 claims description 6
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 6
- BNSRVFGXRITOQK-UHFFFAOYSA-N 2-(1,2-dichloroethyl)-4-methyl-1,3-dioxolane Chemical compound CC1COC(C(Cl)CCl)O1 BNSRVFGXRITOQK-UHFFFAOYSA-N 0.000 claims description 5
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- UPAIKKUUDSCSGH-UHFFFAOYSA-N 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-[2-(2-methylsulfonylpyrimidin-4-yl)ethynyl]cyclohexan-1-one Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2N=C(N=CC=2)S(C)(=O)=O)C=C1OC1CCCC1 UPAIKKUUDSCSGH-UHFFFAOYSA-N 0.000 claims description 5
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- YZZMAPQBGMEPOH-UHFFFAOYSA-N methyl 4-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC(C#CC2(CCC(=O)CC2)C=2C=C(OC3CCCC3)C(OC)=CC=2)=C1 YZZMAPQBGMEPOH-UHFFFAOYSA-N 0.000 claims description 5
- QONKATUTAVPMPB-UHFFFAOYSA-N n-[5-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]pyrimidin-2-yl]acetamide Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=NC(NC(C)=O)=NC=2)C=C1OC1CCCC1 QONKATUTAVPMPB-UHFFFAOYSA-N 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- GHSUAYJATHEYRB-UHFFFAOYSA-N 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-[2-(1-methylimidazol-2-yl)ethynyl]cyclohexan-1-one Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2N(C=CN=2)C)C=C1OC1CCCC1 GHSUAYJATHEYRB-UHFFFAOYSA-N 0.000 claims description 4
- GKGZXRPUJIVXIJ-UHFFFAOYSA-N 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-[2-(1h-imidazol-2-yl)ethynyl]cyclohexan-1-one Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2NC=CN=2)C=C1OC1CCCC1 GKGZXRPUJIVXIJ-UHFFFAOYSA-N 0.000 claims description 4
- MRBDWNYBAKMRIJ-UHFFFAOYSA-N 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-[2-[3-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]ethynyl]cyclohexan-1-one Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=C(C=CC=2)C=2OC(C)=NN=2)C=C1OC1CCCC1 MRBDWNYBAKMRIJ-UHFFFAOYSA-N 0.000 claims description 4
- SOGZELQPHYHBLV-UHFFFAOYSA-N 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-[2-[4-(2-hydroxyethoxy)phenyl]ethynyl]cyclohexan-1-one Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=CC(OCCO)=CC=2)C=C1OC1CCCC1 SOGZELQPHYHBLV-UHFFFAOYSA-N 0.000 claims description 4
- ZAQOROPCKJSDHE-UHFFFAOYSA-N 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-[2-[5-(5-methyl-3h-1,2,4-oxadiazol-2-yl)thiophen-2-yl]ethynyl]cyclohexan-1-one Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2SC(=CC=2)N2OC(C)=NC2)C=C1OC1CCCC1 ZAQOROPCKJSDHE-UHFFFAOYSA-N 0.000 claims description 4
- GGVQJHMRAKQTGI-UHFFFAOYSA-N 4-[2-(4-aminophenyl)ethynyl]-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one Chemical group COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=CC(N)=CC=2)C=C1OC1CCCC1 GGVQJHMRAKQTGI-UHFFFAOYSA-N 0.000 claims description 4
- CFMIEXHHNJUFDJ-UHFFFAOYSA-N 4-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]thiophene-2-carbonitrile Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=C(SC=2)C#N)C=C1OC1CCCC1 CFMIEXHHNJUFDJ-UHFFFAOYSA-N 0.000 claims description 4
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 4
- PWTNZZXGLVTVSC-UHFFFAOYSA-N 5-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]thiophene-2-carbonitrile Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2SC(=CC=2)C#N)C=C1OC1CCCC1 PWTNZZXGLVTVSC-UHFFFAOYSA-N 0.000 claims description 4
- 125000002632 imidazolidinyl 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
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- WQOJNOZZBJMQMQ-UHFFFAOYSA-N methyl 5-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1C#CC1(C=2C=C(OC3CCCC3)C(OC)=CC=2)CCC(=O)CC1 WQOJNOZZBJMQMQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 4
- 125000002971 oxazolyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 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
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- WQADWIOXOXRPLN-UHFFFAOYSA-N 1,3-Dithiane Natural products C1CSCSC1 WQADWIOXOXRPLN-UHFFFAOYSA-N 0.000 claims description 3
- AFQJKPNNOYLICR-UHFFFAOYSA-N 2-[4-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]phenoxy]acetic acid Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=CC(OCC(O)=O)=CC=2)C=C1OC1CCCC1 AFQJKPNNOYLICR-UHFFFAOYSA-N 0.000 claims description 3
- XSDNYFRALCNYCN-SDNWHVSQSA-N 3-[(e)-2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethenyl]benzonitrile Chemical compound COC1=CC=C(C2(CCC(=O)CC2)\C=C\C=2C=C(C=CC=2)C#N)C=C1OC1CCCC1 XSDNYFRALCNYCN-SDNWHVSQSA-N 0.000 claims description 3
- GFLBPVIEEFQLOV-UHFFFAOYSA-N 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-[2-[3-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]ethynyl]cyclohexan-1-one Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=C(C=CC=2)C=2ON=C(C)N=2)C=C1OC1CCCC1 GFLBPVIEEFQLOV-UHFFFAOYSA-N 0.000 claims description 3
- IYQHKYPUTCZXMV-UHFFFAOYSA-N 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-[2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]ethynyl]cyclohexan-1-one Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=C(C=CC=2)C=2N=C(C)ON=2)C=C1OC1CCCC1 IYQHKYPUTCZXMV-UHFFFAOYSA-N 0.000 claims description 3
- RNPWAEZKPANYEE-UHFFFAOYSA-N 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-[2-[3-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]ethynyl]cyclohexan-1-one Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=C(C=CC=2)C=2SC(C)=NN=2)C=C1OC1CCCC1 RNPWAEZKPANYEE-UHFFFAOYSA-N 0.000 claims description 3
- ULLKHRMLQCHIJG-UHFFFAOYSA-N 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-[2-[4-(2-oxo-2-piperidin-1-ylethoxy)phenyl]ethynyl]cyclohexan-1-one Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=CC(OCC(=O)N3CCCCC3)=CC=2)C=C1OC1CCCC1 ULLKHRMLQCHIJG-UHFFFAOYSA-N 0.000 claims description 3
- CEXQPHHHGAOPFH-UHFFFAOYSA-N 4-[2-(2-aminopyrimidin-4-yl)ethynyl]-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2N=C(N)N=CC=2)C=C1OC1CCCC1 CEXQPHHHGAOPFH-UHFFFAOYSA-N 0.000 claims description 3
- REMPSJPKUJWIEV-UHFFFAOYSA-N 4-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]thiophene-2-carboxylic acid Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=C(SC=2)C(O)=O)C=C1OC1CCCC1 REMPSJPKUJWIEV-UHFFFAOYSA-N 0.000 claims description 3
- MDABIOVATNGUMY-UHFFFAOYSA-N 5-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]benzene-1,3-dicarbonitrile Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=C(C=C(C=2)C#N)C#N)C=C1OC1CCCC1 MDABIOVATNGUMY-UHFFFAOYSA-N 0.000 claims description 3
- GUHILKPTRCRGDY-UHFFFAOYSA-N 5-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]thiophene-2-carboxylic acid Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2SC(=CC=2)C(O)=O)C=C1OC1CCCC1 GUHILKPTRCRGDY-UHFFFAOYSA-N 0.000 claims description 3
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims description 3
- HXNHYDIUEOQPCI-UHFFFAOYSA-N n-[3-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]phenyl]acetamide Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=C(NC(C)=O)C=CC=2)C=C1OC1CCCC1 HXNHYDIUEOQPCI-UHFFFAOYSA-N 0.000 claims description 3
- RUZUMLRXFIWQDX-UHFFFAOYSA-N n-[4-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]phenyl]acetamide Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=CC(NC(C)=O)=CC=2)C=C1OC1CCCC1 RUZUMLRXFIWQDX-UHFFFAOYSA-N 0.000 claims description 3
- 159000000000 sodium salts Chemical class 0.000 claims description 3
- OSFRSOQZKOUNSM-UHFFFAOYSA-N 3-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]benzoic acid Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=C(C=CC=2)C(O)=O)C=C1OC1CCCC1 OSFRSOQZKOUNSM-UHFFFAOYSA-N 0.000 claims description 2
- IYMZDMRADUXWTJ-UHFFFAOYSA-N 3-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]benzonitrile Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=C(C=CC=2)C#N)C=C1OC1CCCC1 IYMZDMRADUXWTJ-UHFFFAOYSA-N 0.000 claims description 2
- DCQZVDIWFVZXQC-UHFFFAOYSA-N 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(2-pyridin-3-ylethynyl)cyclohexan-1-one Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=NC=CC=2)C=C1OC1CCCC1 DCQZVDIWFVZXQC-UHFFFAOYSA-N 0.000 claims description 2
- OALNZVNDXPRGOI-UHFFFAOYSA-N 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-[2-(4-hydroxyphenyl)ethynyl]cyclohexan-1-one Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=CC(O)=CC=2)C=C1OC1CCCC1 OALNZVNDXPRGOI-UHFFFAOYSA-N 0.000 claims description 2
- GYCHZZBQNARFNA-UHFFFAOYSA-N 4-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]benzoic acid Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2C=CC(=CC=2)C(O)=O)C=C1OC1CCCC1 GYCHZZBQNARFNA-UHFFFAOYSA-N 0.000 claims description 2
- RBDCVGMXFOMVRK-UHFFFAOYSA-N 5-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]thiophene-3-carboxylic acid Chemical compound COC1=CC=C(C2(CCC(=O)CC2)C#CC=2SC=C(C=2)C(O)=O)C=C1OC1CCCC1 RBDCVGMXFOMVRK-UHFFFAOYSA-N 0.000 claims description 2
- DEASWVOFDHVYOZ-UHFFFAOYSA-N C1=CC(OCC(=O)OC)=CC=C1C#CC1(C=2C=C(OC3CCCC3)C(OC)=CC=2)CCC(=O)CC1 Chemical compound C1=CC(OCC(=O)OC)=CC=C1C#CC1(C=2C=C(OC3CCCC3)C(OC)=CC=2)CCC(=O)CC1 DEASWVOFDHVYOZ-UHFFFAOYSA-N 0.000 claims description 2
- UZFWTXBRCHVPJL-UHFFFAOYSA-N ClC1=CC=C(C=C1)C#CC1(CCC(CC1)=O)C1=CC(=C(C=C1)OC)OC1CCCC1 Chemical compound ClC1=CC=C(C=C1)C#CC1(CCC(CC1)=O)C1=CC(=C(C=C1)OC)OC1CCCC1 UZFWTXBRCHVPJL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- LJRZMMXYTMEPMM-UHFFFAOYSA-N dimethyl 5-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC(C(=O)OC)=CC(C#CC2(CCC(=O)CC2)C=2C=C(OC3CCCC3)C(OC)=CC=2)=C1 LJRZMMXYTMEPMM-UHFFFAOYSA-N 0.000 claims description 2
- IADGSCAEXZYIGV-UHFFFAOYSA-N methyl 2-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1C#CC1(C=2C=C(OC3CCCC3)C(OC)=CC=2)CCC(=O)CC1 IADGSCAEXZYIGV-UHFFFAOYSA-N 0.000 claims description 2
- KKEFHSDGKPYUKL-UHFFFAOYSA-N methyl 3-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]benzoate Chemical compound COC(=O)C1=CC=CC(C#CC2(CCC(=O)CC2)C=2C=C(OC3CCCC3)C(OC)=CC=2)=C1 KKEFHSDGKPYUKL-UHFFFAOYSA-N 0.000 claims description 2
- YHZXBABVHHMCSN-UHFFFAOYSA-N methyl 4-[2-[1-(3-cyclopentyloxy-4-methoxyphenyl)-4-oxocyclohexyl]ethynyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C#CC1(C=2C=C(OC3CCCC3)C(OC)=CC=2)CCC(=O)CC1 YHZXBABVHHMCSN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 228
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 172
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 91
- 239000000203 mixture Substances 0.000 description 83
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 72
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 70
- 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 62
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C217/80—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of non-condensed six-membered aromatic rings
-
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
- C07C233/33—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/56—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and doubly-bound oxygen atoms bound to the carbon skeleton
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- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
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- 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
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/02—Esters of acyclic saturated monocarboxylic acids having the carboxyl group bound to an acyclic carbon atom or to hydrogen
- C07C69/12—Acetic acid esters
- C07C69/14—Acetic acid esters of monohydroxylic compounds
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- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
- C07C69/712—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members 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
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
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- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
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- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
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- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
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- C—CHEMISTRY; METALLURGY
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- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/08—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing alicyclic rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US45623494A | 1994-12-23 | 1994-12-23 | |
US45579695A | 1995-05-31 | 1995-05-31 | |
PCT/US1995/016858 WO1996019995A1 (en) | 1994-12-23 | 1995-12-21 | 4,4-(disubstituted)cyclohexan-1-one monomers and related compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
NO972898D0 NO972898D0 (no) | 1997-06-20 |
NO972898L true NO972898L (no) | 1997-08-20 |
Family
ID=27037990
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO972898A NO972898L (no) | 1994-12-23 | 1997-06-20 | 4,4-(Disubstituerte)cykloheksan-1-on-monomerer og beslektede forbindelser |
Country Status (12)
Country | Link |
---|---|
EP (1) | EP0800393A4 (cs) |
CN (1) | CN1175211A (cs) |
AU (1) | AU708349B2 (cs) |
BR (1) | BR9510521A (cs) |
CA (1) | CA2208456A1 (cs) |
CZ (1) | CZ196297A3 (cs) |
FI (1) | FI972673A7 (cs) |
HU (1) | HUT78042A (cs) |
NO (1) | NO972898L (cs) |
NZ (1) | NZ301453A (cs) |
PL (1) | PL321001A1 (cs) |
WO (1) | WO1996019995A1 (cs) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR0013230A (pt) * | 1999-08-10 | 2002-04-23 | Smithkline Beecham Corp | 4,4-diaril-(ciclo-hexanos) 1,4-substituìdos |
DK3209655T3 (da) * | 2014-10-24 | 2020-09-28 | Landos Biopharma Inc | Lanthioninsyntease C-lignende 2-baserede Therapeutica |
CN104649882A (zh) * | 2015-02-11 | 2015-05-27 | 南通恒盛精细化工有限公司 | 一种磷酸二酯酶抑制剂的中间体制备工艺 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3192424B2 (ja) * | 1992-04-02 | 2001-07-30 | スミスクライン・ビーチャム・コーポレイション | アレルギーまたは炎症疾患の治療用化合物 |
-
1995
- 1995-12-21 WO PCT/US1995/016858 patent/WO1996019995A1/en not_active Application Discontinuation
- 1995-12-21 CZ CZ971962A patent/CZ196297A3/cs unknown
- 1995-12-21 AU AU46883/96A patent/AU708349B2/en not_active Ceased
- 1995-12-21 BR BR9510521A patent/BR9510521A/pt not_active Application Discontinuation
- 1995-12-21 HU HU9802635A patent/HUT78042A/hu unknown
- 1995-12-21 EP EP95944527A patent/EP0800393A4/en not_active Withdrawn
- 1995-12-21 CA CA002208456A patent/CA2208456A1/en not_active Abandoned
- 1995-12-21 NZ NZ301453A patent/NZ301453A/xx not_active IP Right Cessation
- 1995-12-21 FI FI972673A patent/FI972673A7/fi unknown
- 1995-12-21 PL PL95321001A patent/PL321001A1/xx unknown
- 1995-12-21 CN CN95197681A patent/CN1175211A/zh active Pending
-
1997
- 1997-06-20 NO NO972898A patent/NO972898L/no not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
CZ196297A3 (cs) | 1998-01-14 |
FI972673L (fi) | 1997-08-19 |
CN1175211A (zh) | 1998-03-04 |
NO972898D0 (no) | 1997-06-20 |
NZ301453A (en) | 1999-02-25 |
PL321001A1 (en) | 1997-11-24 |
FI972673A7 (fi) | 1997-08-19 |
EP0800393A4 (en) | 1998-05-06 |
BR9510521A (pt) | 1998-07-14 |
HUT78042A (hu) | 1999-06-28 |
FI972673A0 (fi) | 1997-06-19 |
WO1996019995A1 (en) | 1996-07-04 |
MX9704733A (es) | 1997-10-31 |
AU708349B2 (en) | 1999-08-05 |
EP0800393A1 (en) | 1997-10-15 |
AU4688396A (en) | 1996-07-19 |
CA2208456A1 (en) | 1996-07-04 |
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