JP4854856B2 - 黄体化ホルモン作動薬として有用な二環式へテロ芳香族化合物 - Google Patents

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Publication number

JP4854856B2

JP4854856B2 JP2000610857A JP2000610857A JP4854856B2 JP 4854856 B2 JP4854856 B2 JP 4854856B2 JP 2000610857 A JP2000610857 A JP 2000610857A JP 2000610857 A JP2000610857 A JP 2000610857A JP 4854856 B2 JP4854856 B2 JP 4854856B2

Authority

JP

Japan

Prior art keywords

amino

thieno

pyrimidine

ethyl

silica gel

Prior art date

1999-04-08

Legal status (The legal status 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 status listed.)

Expired - Fee Related

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• -1 Bicyclic heteroaromatic compounds Chemical class 0.000 title claims description 47
• 108010073521 Luteinizing Hormone Proteins 0.000 title description 25
• 102000009151 Luteinizing Hormone Human genes 0.000 title description 25
• 229940040129 luteinizing hormone Drugs 0.000 title description 25
• 239000000556 agonist Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims description 117
• 125000003118 aryl group Chemical group 0.000 claims description 53
• 125000000217 alkyl group Chemical group 0.000 claims description 52
• 125000001072 heteroaryl group Chemical group 0.000 claims description 42
• 125000003545 alkoxy group Chemical group 0.000 claims description 32
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 24
• 125000001424 substituent group Chemical group 0.000 claims description 24
• 125000003342 alkenyl group Chemical group 0.000 claims description 23
• 125000000304 alkynyl group Chemical group 0.000 claims description 21
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 19
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 125000003282 alkyl amino group Chemical group 0.000 claims description 15
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 10
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
• 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 9
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 9
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 8
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 8
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
• 150000001412 amines Chemical class 0.000 claims description 8
• 125000001769 aryl amino group Chemical group 0.000 claims description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 7
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 6
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 239000002671 adjuvant Substances 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 4
• 230000035558 fertility Effects 0.000 claims description 4
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
• VXZTYHHYHXHGNN-UHFFFAOYSA-N o-ethyl 5-amino-2-methyl-4-phenylthieno[2,3-d]pyrimidine-6-carbothioate Chemical compound C=12C(N)=C(C(=S)OCC)SC2=NC(C)=NC=1C1=CC=CC=C1 VXZTYHHYHXHGNN-UHFFFAOYSA-N 0.000 claims description 4
• OEUOXBJHGMAALZ-UHFFFAOYSA-N 1-(6-acetyl-5-amino-4-phenylthieno[2,3-d]pyrimidin-2-yl)sulfanylpropan-2-one Chemical compound C=12C(N)=C(C(C)=O)SC2=NC(SCC(=O)C)=NC=1C1=CC=CC=C1 OEUOXBJHGMAALZ-UHFFFAOYSA-N 0.000 claims description 3
• CFOXWCSTGROSDJ-UHFFFAOYSA-N 2-(5-amino-6-benzoyl-4-phenylthieno[2,3-d]pyrimidin-2-yl)sulfanyl-1-phenylethanone Chemical compound N=1C(C=2C=CC=CC=2)=C2C(N)=C(C(=O)C=3C=CC=CC=3)SC2=NC=1SCC(=O)C1=CC=CC=C1 CFOXWCSTGROSDJ-UHFFFAOYSA-N 0.000 claims description 3
• PXUOQUMRMYJMJB-UHFFFAOYSA-N ethyl 2-(5-amino-6-ethoxycarbothioyl-4-phenylthieno[2,3-d]pyrimidin-2-yl)acetate Chemical compound C=12C(N)=C(C(=S)OCC)SC2=NC(CC(=O)OCC)=NC=1C1=CC=CC=C1 PXUOQUMRMYJMJB-UHFFFAOYSA-N 0.000 claims description 3
• DZZZVDUQTNCWDN-UHFFFAOYSA-N o-methyl 5-amino-2-methyl-4-phenylthieno[2,3-d]pyrimidine-6-carbothioate Chemical compound C=12C(N)=C(C(=S)OC)SC2=NC(C)=NC=1C1=CC=CC=C1 DZZZVDUQTNCWDN-UHFFFAOYSA-N 0.000 claims description 2
• 230000001105 regulatory effect Effects 0.000 claims description 2
• 239000012453 solvate Substances 0.000 claims 2
• KQEJRGGNDSECOH-UHFFFAOYSA-N 2-[5-amino-6-(4-chlorobenzoyl)-4-phenylthieno[2,3-d]pyrimidin-2-yl]sulfanyl-1-(4-chlorophenyl)ethanone Chemical compound N=1C(C=2C=CC=CC=2)=C2C(N)=C(C(=O)C=3C=CC(Cl)=CC=3)SC2=NC=1SCC(=O)C1=CC=C(Cl)C=C1 KQEJRGGNDSECOH-UHFFFAOYSA-N 0.000 claims 1
• PPDHQXKWDDNEKZ-UHFFFAOYSA-N 2-[5-amino-6-(4-methylbenzoyl)-4-phenylthieno[2,3-d]pyrimidin-2-yl]sulfanyl-1-(4-methylphenyl)ethanone Chemical compound C1=CC(C)=CC=C1C(=O)CSC1=NC(C=2C=CC=CC=2)=C(C(N)=C(S2)C(=O)C=3C=CC(C)=CC=3)C2=N1 PPDHQXKWDDNEKZ-UHFFFAOYSA-N 0.000 claims 1
• PXCZIBJFJNWCJD-UHFFFAOYSA-N ethyl 5-amino-2-(2-ethoxy-2-oxoethyl)sulfanyl-4-pyridin-4-ylthieno[2,3-d]pyrimidine-6-carboxylate Chemical compound C=12C(N)=C(C(=O)OCC)SC2=NC(SCC(=O)OCC)=NC=1C1=CC=NC=C1 PXCZIBJFJNWCJD-UHFFFAOYSA-N 0.000 claims 1
• OYDUXFWQTZSKLB-UHFFFAOYSA-N o-ethyl 5-amino-4-(4-chlorophenyl)-2-methylthieno[2,3-d]pyrimidine-6-carbothioate Chemical compound C=12C(N)=C(C(=S)OCC)SC2=NC(C)=NC=1C1=CC=C(Cl)C=C1 OYDUXFWQTZSKLB-UHFFFAOYSA-N 0.000 claims 1
• WYAWOQKAAKLMLU-UHFFFAOYSA-N o-ethyl 5-amino-4-(4-methoxyphenyl)-2-methylthieno[2,3-d]pyrimidine-6-carbothioate Chemical compound C=12C(N)=C(C(=S)OCC)SC2=NC(C)=NC=1C1=CC=C(OC)C=C1 WYAWOQKAAKLMLU-UHFFFAOYSA-N 0.000 claims 1
• YXJVZXJVXAXLLD-UHFFFAOYSA-N o-methyl 5-amino-4-(4-chlorophenyl)-2-methylthieno[2,3-d]pyrimidine-6-carbothioate Chemical compound C=12C(N)=C(C(=S)OC)SC2=NC(C)=NC=1C1=CC=C(Cl)C=C1 YXJVZXJVXAXLLD-UHFFFAOYSA-N 0.000 claims 1
• JVAYTXIFJIERGY-UHFFFAOYSA-N o-methyl 5-amino-4-(4-methoxyphenyl)-2-methylthieno[2,3-d]pyrimidine-6-carbothioate Chemical compound C=12C(N)=C(C(=S)OC)SC2=NC(C)=NC=1C1=CC=C(OC)C=C1 JVAYTXIFJIERGY-UHFFFAOYSA-N 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 552
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 172
• 239000000741 silica gel Substances 0.000 description 170
• 229910002027 silica gel Inorganic materials 0.000 description 170
• 238000004809 thin layer chromatography Methods 0.000 description 132
• 238000000034 method Methods 0.000 description 129
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 121
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 120
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 102
• 238000007363 ring formation reaction Methods 0.000 description 65
• 239000003480 eluent Substances 0.000 description 58
• 238000010517 secondary reaction Methods 0.000 description 54
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
• 235000019439 ethyl acetate Nutrition 0.000 description 45
• PVBRSNZAOAJRKO-UHFFFAOYSA-N ethyl 2-sulfanylacetate Chemical compound CCOC(=O)CS PVBRSNZAOAJRKO-UHFFFAOYSA-N 0.000 description 44
• JXBPSENIJJPTCI-UHFFFAOYSA-N ethyl cyanate Chemical compound CCOC#N JXBPSENIJJPTCI-UHFFFAOYSA-N 0.000 description 43
• 239000000047 product Substances 0.000 description 43
• RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 40
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 36
• 125000004432 carbon atom Chemical group C* 0.000 description 32
• GSKZNNQWJVVTRT-UHFFFAOYSA-N 5-amino-2-methylsulfanyl-4-phenylthieno[2,3-d]pyrimidine-6-carboxylic acid Chemical compound C=12C(N)=C(C(O)=O)SC2=NC(SC)=NC=1C1=CC=CC=C1 GSKZNNQWJVVTRT-UHFFFAOYSA-N 0.000 description 30
• 239000011541 reaction mixture Substances 0.000 description 28
• 239000000243 solution Substances 0.000 description 26
• 238000006243 chemical reaction Methods 0.000 description 25
• 238000010898 silica gel chromatography Methods 0.000 description 25
• 239000002253 acid Substances 0.000 description 24
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
• NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 18
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 18
• 150000001408 amides Chemical class 0.000 description 17
• 150000002576 ketones Chemical class 0.000 description 17
• BHPYMZQTCPRLNR-UHFFFAOYSA-N 2-cyanoethanethioamide Chemical compound NC(=S)CC#N BHPYMZQTCPRLNR-UHFFFAOYSA-N 0.000 description 16
• WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 16
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
• 230000032050 esterification Effects 0.000 description 16
• 238000005886 esterification reaction Methods 0.000 description 16
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• 238000005882 aldol condensation reaction Methods 0.000 description 15
• VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 15
• 239000000203 mixture Substances 0.000 description 15
• 238000012360 testing method Methods 0.000 description 15
• MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 14
• 210000004027 cell Anatomy 0.000 description 14
• 102000005962 receptors Human genes 0.000 description 14
• 108020003175 receptors Proteins 0.000 description 14
• JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 13
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
• 108010011942 LH Receptors Proteins 0.000 description 11
• 238000010992 reflux Methods 0.000 description 11
• 239000007787 solid Substances 0.000 description 11
• 102000023108 LH Receptors Human genes 0.000 description 10
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 102000011022 Chorionic Gonadotropin Human genes 0.000 description 9
• 108010062540 Chorionic Gonadotropin Proteins 0.000 description 9
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
• CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 9
• 229940084986 human chorionic gonadotropin Drugs 0.000 description 9
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
• WYJOVVXUZNRJQY-UHFFFAOYSA-N 2-Acetylthiophene Chemical compound CC(=O)C1=CC=CS1 WYJOVVXUZNRJQY-UHFFFAOYSA-N 0.000 description 8
• IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 8
• KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
• 238000003556 assay Methods 0.000 description 8
• 230000027455 binding Effects 0.000 description 8
• 210000002332 leydig cell Anatomy 0.000 description 8
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
• 235000019341 magnesium sulphate Nutrition 0.000 description 8
• 239000012044 organic layer Substances 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 229910052938 sodium sulfate Inorganic materials 0.000 description 8
• 235000011152 sodium sulphate Nutrition 0.000 description 8
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
• IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 7
• 108010079345 Follicle Stimulating Hormone Proteins 0.000 description 7
• 102000012673 Follicle Stimulating Hormone Human genes 0.000 description 7
• 102000006771 Gonadotropins Human genes 0.000 description 7
• 108010086677 Gonadotropins Proteins 0.000 description 7
• 241000699670 Mus sp. Species 0.000 description 7
• IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 7
• 239000012267 brine Substances 0.000 description 7
• 229940095074 cyclic amp Drugs 0.000 description 7
• 238000001914 filtration Methods 0.000 description 7
• 239000002622 gonadotropin Substances 0.000 description 7
• 229940094892 gonadotropins Drugs 0.000 description 7
• 230000016087 ovulation Effects 0.000 description 7
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• 229920006395 saturated elastomer Polymers 0.000 description 7
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
• 239000002904 solvent Substances 0.000 description 7
• 230000000638 stimulation Effects 0.000 description 7
• 239000000126 substance Substances 0.000 description 7
• 229910052717 sulfur Inorganic materials 0.000 description 7
• 229960003604 testosterone Drugs 0.000 description 7
• XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 description 6
• AZVSIHIBYRHSLB-UHFFFAOYSA-N 3-furaldehyde Chemical compound O=CC=1C=COC=1 AZVSIHIBYRHSLB-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
• 239000004480 active ingredient Substances 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
• 229940028334 follicle stimulating hormone Drugs 0.000 description 6
• 238000000338 in vitro Methods 0.000 description 6
• 229910052757 nitrogen Inorganic materials 0.000 description 6
• 229910052760 oxygen Inorganic materials 0.000 description 6
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• 108020004414 DNA Proteins 0.000 description 5
• 229910019213 POCl3 Inorganic materials 0.000 description 5
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 5
• LZCZIHQBSCVGRD-UHFFFAOYSA-N benzenecarboximidamide;hydron;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=CC=C1 LZCZIHQBSCVGRD-UHFFFAOYSA-N 0.000 description 5
• 125000005842 heteroatom Chemical group 0.000 description 5
• 238000002844 melting Methods 0.000 description 5
• 230000008018 melting Effects 0.000 description 5
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
• 235000017557 sodium bicarbonate Nutrition 0.000 description 5
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
• 238000003756 stirring Methods 0.000 description 5
• YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 5
• HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
• 241000699666 Mus <mouse, genus> Species 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• 108700008625 Reporter Genes Proteins 0.000 description 4
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
• IONKMFGAXKCLMI-UHFFFAOYSA-N [amino(pyridin-4-yl)methylidene]azanium;chloride Chemical compound [Cl-].NC(=[NH2+])C1=CC=NC=C1 IONKMFGAXKCLMI-UHFFFAOYSA-N 0.000 description 4
• 230000015572 biosynthetic process Effects 0.000 description 4
• 239000012043 crude product Substances 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 238000001727 in vivo Methods 0.000 description 4
• 230000006698 induction Effects 0.000 description 4
• 238000005259 measurement Methods 0.000 description 4
• FNGJSZCRFIPBPK-UHFFFAOYSA-N o-ethyl 5-amino-4-(3-methoxyphenyl)-2-methylthieno[2,3-d]pyrimidine-6-carbothioate Chemical compound C=12C(N)=C(C(=S)OCC)SC2=NC(C)=NC=1C1=CC=CC(OC)=C1 FNGJSZCRFIPBPK-UHFFFAOYSA-N 0.000 description 4
• 229910000027 potassium carbonate Inorganic materials 0.000 description 4
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