TWI753336B - 用於製備二芳基硫乙內醯脲化合物之方法 - Google Patents
用於製備二芳基硫乙內醯脲化合物之方法 Download PDFInfo
- Publication number
- TWI753336B TWI753336B TW108146841A TW108146841A TWI753336B TW I753336 B TWI753336 B TW I753336B TW 108146841 A TW108146841 A TW 108146841A TW 108146841 A TW108146841 A TW 108146841A TW I753336 B TWI753336 B TW I753336B
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- Prior art keywords
- compound
- formula
- organic solvent
- thiocarbonyl
- source
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract 46
- 238000000034 method Methods 0.000 claims abstract 22
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical group CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 17
- KOSYAAIZOGNATQ-UHFFFAOYSA-N o-phenyl chloromethanethioate Chemical compound ClC(=S)OC1=CC=CC=C1 KOSYAAIZOGNATQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 15
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 10
- 239000012190 activator Substances 0.000 claims 10
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 10
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 9
- 229960000549 4-dimethylaminophenol Drugs 0.000 claims 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 8
- 238000006243 chemical reaction Methods 0.000 claims 8
- 150000007530 organic bases Chemical class 0.000 claims 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 5
- 235000011056 potassium acetate Nutrition 0.000 claims 4
- KXMMNJQMGILZDB-UHFFFAOYSA-N 1-(2-oxopyridine-1-carbothioyl)pyridin-2-one Chemical compound O=C1C=CC=CN1C(=S)N1C(=O)C=CC=C1 KXMMNJQMGILZDB-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims 3
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 229910052802 copper Inorganic materials 0.000 claims 3
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical class Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims 3
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 claims 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims 2
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims 2
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical class [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 claims 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N acetaldehyde dimethyl acetal Natural products COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 2
- KUSNXMZPSJPTRZ-UHFFFAOYSA-N bis(2h-benzotriazol-4-yl)methanethione Chemical compound C1=CC2=NNN=C2C(C(C=2C3=NNN=C3C=CC=2)=S)=C1 KUSNXMZPSJPTRZ-UHFFFAOYSA-N 0.000 claims 2
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical class [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 claims 2
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical class [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(II) bromide Chemical class [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 claims 2
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical class I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims 2
- 229940045803 cuprous chloride Drugs 0.000 claims 2
- 235000019439 ethyl acetate Nutrition 0.000 claims 2
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- 150000003839 salts Chemical group 0.000 claims 2
- SJRDNQOIQZOVQD-UHFFFAOYSA-M sodium;2,2-dimethylpropanoate Chemical compound [Na+].CC(C)(C)C([O-])=O SJRDNQOIQZOVQD-UHFFFAOYSA-M 0.000 claims 2
- -1 thioketone chloroformate ester Chemical class 0.000 claims 2
- 125000005323 thioketone group Chemical group 0.000 claims 2
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- KFYRJJBUHYILSO-YFKPBYRVSA-N (2s)-2-amino-3-dimethylarsanylsulfanyl-3-methylbutanoic acid Chemical compound C[As](C)SC(C)(C)[C@@H](N)C(O)=O KFYRJJBUHYILSO-YFKPBYRVSA-N 0.000 claims 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 1
- OEKATORRSPXJHE-UHFFFAOYSA-N 2-acetylcyclohexan-1-one Chemical compound CC(=O)C1CCCCC1=O OEKATORRSPXJHE-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 229910021590 Copper(II) bromide Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 claims 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims 1
- 229910000024 caesium carbonate Inorganic materials 0.000 claims 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Inorganic materials [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000001879 copper Chemical class 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 235000010378 sodium ascorbate Nutrition 0.000 claims 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 claims 1
- 229960005055 sodium ascorbate Drugs 0.000 claims 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 abstract 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 0 C*(C)c(ccc(*)c1)c1F Chemical compound C*(C)c(ccc(*)c1)c1F 0.000 description 13
- TVOWJVSSBFMCFC-UHFFFAOYSA-N NC1(CCC1)C(Nc1cc(C(F)(F)F)c(C#N)nc1)=O Chemical compound NC1(CCC1)C(Nc1cc(C(F)(F)F)c(C#N)nc1)=O TVOWJVSSBFMCFC-UHFFFAOYSA-N 0.000 description 3
- UNSKLGZBNPPGOW-UHFFFAOYSA-N C[N]C(c(ccc(N(C1(CCC1)C(N1c(cc2C(F)(F)F)cnc2C#N)=O)C1=S)c1)c1F)=O Chemical compound C[N]C(c(ccc(N(C1(CCC1)C(N1c(cc2C(F)(F)F)cnc2C#N)=O)C1=S)c1)c1F)=O UNSKLGZBNPPGOW-UHFFFAOYSA-N 0.000 description 2
- FZPPYLRITDYSAU-UHFFFAOYSA-N CC(C)N(C1(CCC1)C(N1c2cc(C(F)(F)F)c(C#N)nc2)=O)C1=S Chemical compound CC(C)N(C1(CCC1)C(N1c2cc(C(F)(F)F)c(C#N)nc2)=O)C1=S FZPPYLRITDYSAU-UHFFFAOYSA-N 0.000 description 1
- GQAOAEZHNFTLFF-UHFFFAOYSA-N CC(Oc1ccccc1)=N Chemical compound CC(Oc1ccccc1)=N GQAOAEZHNFTLFF-UHFFFAOYSA-N 0.000 description 1
- UNSQCGADQNHVCI-UHFFFAOYSA-N CC1(C=CC(N(C2(CCC2)C2OC2N2c3cc(C(F)(F)F)c(C#N)nc3)C2=S)=CC1F)C(NC)=O Chemical compound CC1(C=CC(N(C2(CCC2)C2OC2N2c3cc(C(F)(F)F)c(C#N)nc3)C2=S)=CC1F)C(NC)=O UNSQCGADQNHVCI-UHFFFAOYSA-N 0.000 description 1
- HJBWBFZLDZWPHF-UHFFFAOYSA-N CNC(c(ccc(N(C1(CCC1)C(N1c(cc2C(F)(F)F)cnc2C#N)=O)C1=S)c1)c1F)=O Chemical compound CNC(c(ccc(N(C1(CCC1)C(N1c(cc2C(F)(F)F)cnc2C#N)=O)C1=S)c1)c1F)=O HJBWBFZLDZWPHF-UHFFFAOYSA-N 0.000 description 1
- KFMBNGTYWNTYRW-UHFFFAOYSA-N Cc(ccc(NC1(CCC1)C1OC1Nc1cc(C(F)(F)F)c(C#N)nc1)c1)c1F Chemical compound Cc(ccc(NC1(CCC1)C1OC1Nc1cc(C(F)(F)F)c(C#N)nc1)c1)c1F KFMBNGTYWNTYRW-UHFFFAOYSA-N 0.000 description 1
- LLBBRWYUDHRSAA-UHFFFAOYSA-N Cc1c(C#N)ncc(NC(C2(CCC2)Nc(cc2)cc(F)c2C(NC)=O)=O)c1 Chemical compound Cc1c(C#N)ncc(NC(C2(CCC2)Nc(cc2)cc(F)c2C(NC)=O)=O)c1 LLBBRWYUDHRSAA-UHFFFAOYSA-N 0.000 description 1
- IDGUNYFTVCEPGA-UHFFFAOYSA-N N#Cc(nc1)c(C(F)(F)F)cc1[N+]([O-])=O Chemical compound N#Cc(nc1)c(C(F)(F)F)cc1[N+]([O-])=O IDGUNYFTVCEPGA-UHFFFAOYSA-N 0.000 description 1
- WLMSCOVORZUSNW-UHFFFAOYSA-N Nc1cc(C(F)(F)F)c(C#N)nc1 Chemical compound Nc1cc(C(F)(F)F)c(C#N)nc1 WLMSCOVORZUSNW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; Compounds thereof
- B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J27/195—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with vanadium, niobium or tantalum
- B01J27/198—Vanadium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/04—Mixing
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/60—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 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
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/60—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 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462094436P | 2014-12-19 | 2014-12-19 | |
| US62/094,436 | 2014-12-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW202031639A TW202031639A (zh) | 2020-09-01 |
| TWI753336B true TWI753336B (zh) | 2022-01-21 |
Family
ID=55168400
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
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| RS58454B1 (sr) * | 2014-12-19 | 2019-04-30 | Aragon Pharmaceuticals Inc | Postupak za pripremu jedinjenja diariltiohidantoina |
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| CN108069869B (zh) * | 2016-11-09 | 2022-03-01 | 上海医药工业研究院 | 一种Apalutamide的制备方法及其中间体 |
| TW201831461A (zh) * | 2017-01-18 | 2018-09-01 | 台灣神隆股份有限公司 | 製備阿帕魯醯胺的方法 |
| US10364245B2 (en) | 2017-06-07 | 2019-07-30 | Chiesi Farmaceutici S.P.A. | Kinase inhibitors |
| CN107501237B (zh) * | 2017-08-17 | 2022-03-22 | 上海西浦医药科技有限公司 | 一种Apalutamide的合成方法 |
| CN108383749B (zh) * | 2018-01-30 | 2021-03-09 | 杭州科巢生物科技有限公司 | 阿帕鲁胺的合成方法及其中间体 |
| US10513504B2 (en) | 2018-03-08 | 2019-12-24 | Apotex Inc. | Processes for the preparation of apalutamide and intermediates thereof |
| CN108314646B (zh) * | 2018-04-11 | 2021-03-19 | 武汉慧敏科技中心 | 一种高分散双金属纳米材料制备泌尿生殖系统用药物中间体的方法 |
| CN109651256A (zh) * | 2018-11-20 | 2019-04-19 | 上海健康医学院 | 一种式（viii）的恩杂鲁胺的制备方法 |
| CN110511207A (zh) * | 2019-06-17 | 2019-11-29 | 扬子江药业集团江苏海慈生物药业有限公司 | 芳基-2-硫代海因类化合物中间体、其制备方法及应用 |
| CN110511206A (zh) * | 2019-06-17 | 2019-11-29 | 扬子江药业集团江苏海慈生物药业有限公司 | 芳基-2-硫代海因类化合物中间体、其制备方法及应用 |
| CN113968815B (zh) * | 2020-07-24 | 2025-11-18 | 苏州科伦药物研究有限公司 | 一种硫代二氮杂螺类化合物的合成方法、其中间体及其合成方法 |
| EP4541786A3 (en) | 2020-09-04 | 2025-08-06 | Synthon B.V. | Improved process for preparation of apalutamide |
| AR124105A1 (es) | 2020-11-20 | 2023-02-15 | Amgen Inc | Procedimiento para preparar 7-cloro-6-fluoro-1-(2-isopropil-4-metilpiridin-3-il)pirido[2,3-d]pirimidino-2,4(1h,3h)-diona |
| CN113402466B (zh) * | 2021-06-18 | 2022-08-16 | 南京方生和医药科技有限公司 | 一种阿帕鲁胺中间体及制备阿帕鲁胺的方法 |
| CN113292535B (zh) * | 2021-06-18 | 2022-07-01 | 南京方生和医药科技有限公司 | 一种制备阿帕鲁胺中间体及阿帕鲁胺的方法 |
| CN115572264B (zh) * | 2021-07-06 | 2025-12-05 | 山东新时代药业有限公司 | 一种恩杂鲁胺的制备方法 |
| CN115850233B (zh) * | 2021-09-24 | 2024-12-10 | 南京方生和医药科技有限公司 | 一种阿帕鲁胺的合成方法 |
| CN116239536A (zh) * | 2021-12-08 | 2023-06-09 | 山东新时代药业有限公司 | 一种阿帕鲁胺中间体化合物 |
| CN115536634B (zh) * | 2022-10-17 | 2024-06-11 | 上海博悦生物科技有限公司 | 一种阿帕他胺的合成方法 |
| CN116332907A (zh) * | 2023-03-16 | 2023-06-27 | 奥锐特药业股份有限公司 | 一种无定形阿帕他胺的制备方法 |
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