JPH0465076B2 - - Google Patents

Info

Publication number: JPH0465076B2
Authority: JP; Japan
Prior art keywords: compound; solution; acetate; nmr; minutes
Prior art date: 1980-11-18
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 - Lifetime

Application number

JP2134241A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0314581A (ja

Inventor

Uiirenja Uenderu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pharmacia and Upjohn Co

Original Assignee

Upjohn Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-11-18

Filing date

1990-05-25

Publication date

1992-10-16

1990-05-25 Application filed by Upjohn Co filed Critical Upjohn Co

1991-01-23 Publication of JPH0314581A publication Critical patent/JPH0314581A/ja

1992-10-16 Publication of JPH0465076B2 publication Critical patent/JPH0465076B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 47
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 12
-1 alkanesulfonyl chloride Chemical compound 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 6
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 55
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
239000000243 solution Substances 0.000 description 28
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
235000019439 ethyl acetate Nutrition 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 20
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
239000000460 chlorine Substances 0.000 description 19
239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
238000000034 method Methods 0.000 description 16
239000011734 sodium Substances 0.000 description 16
239000000203 mixture Substances 0.000 description 15
239000000047 product Substances 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 13
238000003756 stirring Methods 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
239000012141 concentrate Substances 0.000 description 11
239000012074 organic phase Substances 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
238000004458 analytical method Methods 0.000 description 10
239000002585 base Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
241000699660 Mus musculus Species 0.000 description 9
238000003556 assay Methods 0.000 description 9
208000032839 leukemia Diseases 0.000 description 9
229910052757 nitrogen Inorganic materials 0.000 description 9
238000006722 reduction reaction Methods 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
238000010790 dilution Methods 0.000 description 8
239000012895 dilution Substances 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
239000007787 solid Substances 0.000 description 8
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 7
239000001963 growth medium Substances 0.000 description 7
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
UOWVMDUEMSNCAV-UHFFFAOYSA-N antibiotic cc 1065 Chemical compound N1C=2C(OC)=C(O)C=3N(C(N)=O)CCC=3C=2C=C1C(=O)N1CCC(C=2C=3)=C1C(O)=C(OC)C=2NC=3C(=O)N1CC2CC22C1=CC(=O)C1=C2C(C)=CN1 UOWVMDUEMSNCAV-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
239000007858 starting material Substances 0.000 description 5
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
CCSGOHJZAGSHLL-UHFFFAOYSA-N acetic acid;6-methoxy-2,3-dihydro-1h-indol-5-amine Chemical compound CC(O)=O.C1=C(N)C(OC)=CC2=C1CCN2 CCSGOHJZAGSHLL-UHFFFAOYSA-N 0.000 description 4
YDWBIFYCNXZGRG-UHFFFAOYSA-N acetic acid;6-methoxy-5-nitro-2,3-dihydro-1h-indole Chemical compound CC(O)=O.C1=C([N+]([O-])=O)C(OC)=CC2=C1CCN2 YDWBIFYCNXZGRG-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000010511 deprotection reaction Methods 0.000 description 4
239000003480 eluent Substances 0.000 description 4
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 4
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 4
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
239000010410 layer Substances 0.000 description 4
OOWQNQYIQCQFLQ-UHFFFAOYSA-N methanesulfonic acid 6-methoxy-2,3-dihydro-1H-indole Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.COC1=CC=C2CCNC2=C1 OOWQNQYIQCQFLQ-UHFFFAOYSA-N 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000003921 oil Substances 0.000 description 4
229920000166 polytrimethylene carbonate Polymers 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
238000007363 ring formation reaction Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
241000894006 Bacteria Species 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
239000012359 Methanesulfonyl chloride Substances 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
241000191967 Staphylococcus aureus Species 0.000 description 3
VTDQWOKIFUURHG-UHFFFAOYSA-N acetic acid;6-methoxy-2,3-dihydro-1h-indole Chemical compound CC(O)=O.COC1=CC=C2CCNC2=C1 VTDQWOKIFUURHG-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
125000005605 benzo group Chemical group 0.000 description 3
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 3
150000002475 indoles Chemical class 0.000 description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
238000010898 silica gel chromatography Methods 0.000 description 3
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
244000063299 Bacillus subtilis Species 0.000 description 2
235000014469 Bacillus subtilis Nutrition 0.000 description 2
241000588747 Klebsiella pneumoniae Species 0.000 description 2
241000191938 Micrococcus luteus Species 0.000 description 2
241000186367 Mycobacterium avium Species 0.000 description 2
239000007832 Na2SO4 Substances 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000010306 acid treatment Methods 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
230000003385 bacteriostatic effect Effects 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 2
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
235000017168 chlorine Nutrition 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
238000010828 elution Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012634 fragment Substances 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
KBVSLZUSXJNLNP-UHFFFAOYSA-N n-phenyl-2,3-dihydroindol-1-amine Chemical compound C1CC2=CC=CC=C2N1NC1=CC=CC=C1 KBVSLZUSXJNLNP-UHFFFAOYSA-N 0.000 description 2
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000001665 trituration Methods 0.000 description 2
DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 1
125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
GJFNRSDCSTVPCJ-UHFFFAOYSA-N 1,8-bis(dimethylamino)naphthalene Chemical compound C1=CC(N(C)C)=C2C(N(C)C)=CC=CC2=C1 GJFNRSDCSTVPCJ-UHFFFAOYSA-N 0.000 description 1
BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
ZRIKGOFPDBUWRK-UHFFFAOYSA-N 1-methoxy-2,3-dihydroindole Chemical compound C1=CC=C2N(OC)CCC2=C1 ZRIKGOFPDBUWRK-UHFFFAOYSA-N 0.000 description 1
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
ULUNQYODBKLBOE-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)-1h-pyrrole Chemical compound C1=CNC(C=2NC=CC=2)=C1 ULUNQYODBKLBOE-UHFFFAOYSA-N 0.000 description 1
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 1
HRADVHZVMOMEPU-UHFFFAOYSA-N 3-iodopyrrolidine-2,5-dione Chemical compound IC1CC(=O)NC1=O HRADVHZVMOMEPU-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 1
QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical class ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
MDIAKIHKBBNYHF-UHFFFAOYSA-N Ethyl 2-(methylthio)acetate Chemical compound CCOC(=O)CSC MDIAKIHKBBNYHF-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
XCOBLONWWXQEBS-KPKJPENVSA-N N,O-bis(trimethylsilyl)trifluoroacetamide Chemical compound C[Si](C)(C)O\C(C(F)(F)F)=N\[Si](C)(C)C XCOBLONWWXQEBS-KPKJPENVSA-N 0.000 description 1
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
229910019020 PtO2 Inorganic materials 0.000 description 1
241000872198 Serjania polyphylla Species 0.000 description 1
238000007137 Sommelet-Hauser rearrangement reaction Methods 0.000 description 1
239000000370 acceptor Substances 0.000 description 1
238000007171 acid catalysis Methods 0.000 description 1
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
125000001309 chloro group Chemical class Cl* 0.000 description 1
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000012973 diazabicyclooctane Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000005187 foaming Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
230000037406 food intake Effects 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000008241 heterogeneous mixture Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
150000002476 indolines Chemical class 0.000 description 1
238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
150000002690 malonic acid derivatives Chemical class 0.000 description 1
229960002523 mercuric chloride Drugs 0.000 description 1
LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
238000009629 microbiological culture Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
125000004971 nitroalkyl group Chemical group 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
150000005623 oxindoles Chemical class 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000012071 phase Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical class 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
UOWVMDUEMSNCAV-WYENRQIDSA-N rachelmycin Chemical compound C1([C@]23C[C@@H]2CN1C(=O)C=1NC=2C(OC)=C(O)C4=C(C=2C=1)CCN4C(=O)C1=CC=2C=4CCN(C=4C(O)=C(C=2N1)OC)C(N)=O)=CC(=O)C1=C3C(C)=CN1 UOWVMDUEMSNCAV-WYENRQIDSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006476 reductive cyclization reaction Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000006884 silylation reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
XDLNRRRJZOJTRW-UHFFFAOYSA-N thiohypochlorous acid Chemical compound ClS XDLNRRRJZOJTRW-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 description 1
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Oncology (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Hematology (AREA)
Communicable Diseases (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

JP2134241A 1980-11-18 1990-05-25 抗生物質ｃｃ―１０６５断片 Granted JPH0314581A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US20783880A	1980-11-18	1980-11-18
US207,838		1980-11-18

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
JP56183170A Division JPS57114589A (en)	1980-11-18	1981-11-17	Antibiotic cc-1065 fragment

Publications (2)

Publication Number	Publication Date
JPH0314581A JPH0314581A (ja)	1991-01-23
JPH0465076B2 true JPH0465076B2 (fr)	1992-10-16

Family

ID=22772188

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
JP56183170A Granted JPS57114589A (en)	1980-11-18	1981-11-17	Antibiotic cc-1065 fragment
JP2134243A Granted JPH0314561A (ja)	1980-11-18	1990-05-25	抗生物質ｃｃ―１０６５断片
JP2134241A Granted JPH0314581A (ja)	1980-11-18	1990-05-25	抗生物質ｃｃ―１０６５断片
JP2134242A Granted JPH0314545A (ja)	1980-11-18	1990-05-25	抗生物質ｃｃ―１０６５断片製造の中間体

Family Applications Before (2)

Application Number	Title	Priority Date	Filing Date
JP56183170A Granted JPS57114589A (en)	1980-11-18	1981-11-17	Antibiotic cc-1065 fragment
JP2134243A Granted JPH0314561A (ja)	1980-11-18	1990-05-25	抗生物質ｃｃ―１０６５断片

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
JP2134242A Granted JPH0314545A (ja)	1980-11-18	1990-05-25	抗生物質ｃｃ―１０６５断片製造の中間体

Country Status (8)

Country	Link
JP (4)	JPS57114589A (fr)
CH (2)	CH655726A5 (fr)
DE (2)	DE3142143A1 (fr)
FR (1)	FR2494273B1 (fr)
GB (1)	GB2087884B (fr)
HK (1)	HK89990A (fr)
IT (1)	IT1143242B (fr)
SU (1)	SU1318165A3 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3300522A1 (de) *	1982-01-21	1983-07-28	Sandoz-Patent-GmbH, 7850 Lörrach	3,3-dialkyl- und 3,3-alkylen-indolinderivate, verfahren zu ihrer herstellung und pharmazeutische praeparate sie enthaltend
JP2598116B2 (ja) *	1988-12-28	1997-04-09	協和醗酵工業株式会社	新規物質ｄｃ１１３
JP4733303B2 (ja) *	2001-07-17	2011-07-27	株式会社日本製鋼所	テンタオーブン装置
JP2004278639A (ja)	2003-03-14	2004-10-07	Nabco Ltd	脈動吸収装置およびクラッチマスタシリンダ

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4169888A (en) *	1977-10-17	1979-10-02	The Upjohn Company	Composition of matter and process

1981
- 1981-10-07 IT IT49446/81A patent/IT1143242B/it active
- 1981-10-23 DE DE19813142143 patent/DE3142143A1/de active Granted
- 1981-10-23 DE DE3153725A patent/DE3153725C2/de not_active Expired - Fee Related
- 1981-10-28 CH CH4003/84A patent/CH655726A5/de not_active IP Right Cessation
- 1981-10-28 CH CH6895/81A patent/CH655724A5/de not_active IP Right Cessation
- 1981-11-16 GB GB8134453A patent/GB2087884B/en not_active Expired
- 1981-11-17 SU SU813353089A patent/SU1318165A3/ru active
- 1981-11-17 JP JP56183170A patent/JPS57114589A/ja active Granted
- 1981-11-17 FR FR8121480A patent/FR2494273B1/fr not_active Expired
1990
- 1990-05-25 JP JP2134243A patent/JPH0314561A/ja active Granted
- 1990-05-25 JP JP2134241A patent/JPH0314581A/ja active Granted
- 1990-05-25 JP JP2134242A patent/JPH0314545A/ja active Granted
- 1990-11-01 HK HK899/90A patent/HK89990A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
IT1143242B (it)	1986-10-22
JPS57114589A (en)	1982-07-16
JPH0427231B2 (fr)	1992-05-11
IT8149446A0 (it)	1981-10-07
JPH0460594B2 (fr)	1992-09-28
CH655726A5 (de)	1986-05-15
DE3153725C2 (fr)	1993-03-18
CH655724A5 (de)	1986-05-15
SU1318165A3 (ru)	1987-06-15
GB2087884B (en)	1985-06-05
HK89990A (en)	1990-11-09
JPH0310629B2 (fr)	1991-02-14
FR2494273A1 (fr)	1982-05-21
JPH0314581A (ja)	1991-01-23
GB2087884A (en)	1982-06-03
FR2494273B1 (fr)	1985-12-20
DE3142143C2 (fr)	1992-07-30
JPH0314545A (ja)	1991-01-23
JPH0314561A (ja)	1991-01-23
DE3142143A1 (de)	1982-06-24

Publication	Publication Date	Title
KR900001509B1 (ko)	1990-03-12	(트레오) - 1 - 아릴 - 2 - 아실아미도 - 3 - 플루오로 - 1 - 프로판올 및 그의 제조방법
US4413132A (en)	1983-11-01	Antibiotic CC-1065 indoline intermediates
US4423229A (en)	1983-12-27	Composition of matter and process
JP2002533430A (ja)	2002-10-08	アリールエーテルの調製方法
JPH0465076B2 (fr)	1992-10-16
US4423228A (en)	1983-12-27	Process for preparing N-(methyl-sulfonyl)-1,2,8,8a-cyclopropa[c]benzo[1,2-b:4,3-b']dipyrrol-4(5H)-one
US4400518A (en)	1983-08-23	Composition of matter and process
WO2002066457A1 (fr)	2002-08-29	Derive benzo[b]thiophene et procede de production correspondant
US4423230A (en)	1983-12-27	Preparation of an intermediate for N-(methylsulfonyl)-1,2,8,8a-cyclopropa[c][1,2-b:-4,3-b']dipyrol-4(5H)-one
FR2692574A1 (fr)	1993-12-24	Dérivés hydroxy-4 benzènethio, leur préparation ainsi que leur utilisation pour la préparation de dérivés aminoalkoxybenzènesulfonyles.
EP0086678B1 (fr)	1985-07-03	Procédé pour la préparation d'acyl-2 hexahydro-1,3,4,6,7,11b-2H-pyrazino (2,1-a)isoquinoléinones-4 et intermédiaires
US4424365A (en)	1984-01-03	1,2,8,8a-Cyclopropa c!benzo 1,2,-b:-4,3-b'!dipyrrol-4(5H)-ones
US4431820A (en)	1984-02-14	6-Methoxy indoline acetate and its 5-nitro and 5-amino derivatives
EP0713865B1 (fr)	1999-02-10	Dérivés d'acide 2-aminobenzènesulfonique et de chlorure de 2-aminobenzènesulfonyle, leur préparation et leur utilisation comme intermédiaires de synthèse
US4496492A (en)	1985-01-29	Substituted phenylalkyl compounds
JPS61186381A (ja)	1986-08-20	エルゴリン−誘導体の製法
JP4399885B2 (ja)	2010-01-20	４−メチルテトラフルオロベンジルアルコール誘導体の製造法
CN114605309B (zh)	2023-07-21	一种氮杂双环衍生物的合成方法
JPS6241510B2 (fr)	1987-09-03
JP4499847B2 (ja)	2010-07-07	ミルベマイシン類の１３−エステル誘導体の製造法
JP3799722B2 (ja)	2006-07-19	エノールチオエーテルの製造法
JPH0511110B2 (fr)	1993-02-12
JPH0714949B2 (ja)	1995-02-22	光学活性なヘキサン酸誘導体の製造法
JPS6251664A (ja)	1987-03-06	γ−イオノンの製法
JPH0798796B2 (ja)	1995-10-25	イソカルバサイクリン類の製造方法