CH655724A5 - 1,2,8,8a-tetrahydro-cyclopropa(c)-benzo(1,2-b:-4,3-b')-dipyrol-4(5h)-on-verbindungen sowie ein verfahren zu ihrer herstellung. - Google Patents

1,2,8,8a-tetrahydro-cyclopropa(c)-benzo(1,2-b:-4,3-b')-dipyrol-4(5h)-on-verbindungen sowie ein verfahren zu ihrer herstellung. Download PDF

Info

Publication number: CH655724A5
Authority: CH; Switzerland
Prior art keywords: preparation; compound; formula; level; phenyl
Prior art date: 1980-11-18

Application number

CH6895/81A

Other languages

German (de)

English (en)

Inventor

Wendell Wierenga

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

1981-10-28

Publication date

1986-05-15

1981-10-28 Application filed by Upjohn Co filed Critical Upjohn Co

1986-05-15 Publication of CH655724A5 publication Critical patent/CH655724A5/de

Links

150000001875 compounds Chemical class 0.000 title claims description 36
238000000034 method Methods 0.000 title claims description 18
238000004519 manufacturing process Methods 0.000 title description 3
238000002360 preparation method Methods 0.000 claims description 41
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 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
239000007858 starting material Substances 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 2
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 14
239000000741 silica gel Substances 0.000 description 13
229910002027 silica gel Inorganic materials 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
239000012074 organic phase Substances 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
238000003756 stirring Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
239000003480 eluent Substances 0.000 description 9
208000032839 leukemia Diseases 0.000 description 9
239000012299 nitrogen atmosphere Substances 0.000 description 9
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 8
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
238000010790 dilution Methods 0.000 description 8
239000012895 dilution Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
230000009467 reduction Effects 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
239000007832 Na2SO4 Substances 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
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 7
238000004458 analytical method Methods 0.000 description 7
238000001819 mass spectrum Methods 0.000 description 7
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 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
229910001868 water Inorganic materials 0.000 description 7
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
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 6
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 6
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 5
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 5
125000006239 protecting group Chemical group 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000007363 ring formation reaction Methods 0.000 description 5
YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
229920000166 polytrimethylene carbonate Polymers 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 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
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000007787 solid Substances 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 3
125000005869 (methoxyethoxy)methanyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
241000588747 Klebsiella pneumoniae Species 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
241000191938 Micrococcus luteus Species 0.000 description 2
241000186367 Mycobacterium avium Species 0.000 description 2
ZMXDDKWLCZADIW-YYWVXINBSA-N N,N-dimethylformamide-d7 Chemical compound [2H]C(=O)N(C([2H])([2H])[2H])C([2H])([2H])[2H] ZMXDDKWLCZADIW-YYWVXINBSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 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
-1 alkyl carboxylic acid Chemical class 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
235000013305 food Nutrition 0.000 description 2
239000012634 fragment Substances 0.000 description 2
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture 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
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
150000005623 oxindoles Chemical class 0.000 description 2
238000000746 purification Methods 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000006894 reductive elimination reaction Methods 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
239000000758 substrate Substances 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
238000012360 testing method Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
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
XVOAHPOEMCETJM-UHFFFAOYSA-N 1-n,8-n-dimethylnaphthalene-1,8-diamine Chemical compound C1=CC(NC)=C2C(NC)=CC=CC2=C1 XVOAHPOEMCETJM-UHFFFAOYSA-N 0.000 description 1
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229910015845 BBr3 Inorganic materials 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
235000014469 Bacillus subtilis Nutrition 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
201000008225 Klebsiella pneumonia Diseases 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
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 1
206010035717 Pneumonia klebsiella Diseases 0.000 description 1
241000191940 Staphylococcus Species 0.000 description 1
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
229910010062 TiCl3 Inorganic materials 0.000 description 1
229910003074 TiCl4 Inorganic materials 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
239000000370 acceptor Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
238000013459 approach Methods 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
230000003385 bacteriostatic effect Effects 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
229910000085 borane Inorganic materials 0.000 description 1
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Substances BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 1
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 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
239000003054 catalyst Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000005661 deetherification reaction Methods 0.000 description 1
239000012973 diazabicyclooctane Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000010828 elution Methods 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
239000004744 fabric Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000007789 gas 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
238000005984 hydrogenation reaction Methods 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
239000005457 ice water Substances 0.000 description 1
230000006872 improvement Effects 0.000 description 1
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 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
229910052742 iron 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
238000005259 measurement Methods 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
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000004971 nitroalkyl group Chemical group 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000012071 phase Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
238000011084 recovery Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000006884 silylation reaction Methods 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
235000011150 stannous chloride Nutrition 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000002653 sulfanylmethyl group Chemical group [H]SC([H])([H])[*] 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 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
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 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
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000002211 ultraviolet spectrum Methods 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)

CH6895/81A 1980-11-18 1981-10-28 1,2,8,8a-tetrahydro-cyclopropa(c)-benzo(1,2-b:-4,3-b')-dipyrol-4(5h)-on-verbindungen sowie ein verfahren zu ihrer herstellung. CH655724A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US20783880A	1980-11-18	1980-11-18

Publications (1)

Publication Number	Publication Date
CH655724A5 true CH655724A5 (de)	1986-05-15

Family

ID=22772188

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH6895/81A CH655724A5 (de)	1980-11-18	1981-10-28	1,2,8,8a-tetrahydro-cyclopropa(c)-benzo(1,2-b:-4,3-b')-dipyrol-4(5h)-on-verbindungen sowie ein verfahren zu ihrer herstellung.
CH4003/84A CH655726A5 (de)	1980-11-18	1981-10-28	1,2,8,8a-tetrahydro-cyclopropa(c)-benzo(1,2-b:-4,3-b')-dipyrrol-4(5h)-on-verbindungen sowie verfahren zur herstellung dieser verbindungen.

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH4003/84A CH655726A5 (de)	1980-11-18	1981-10-28	1,2,8,8a-tetrahydro-cyclopropa(c)-benzo(1,2-b:-4,3-b')-dipyrrol-4(5h)-on-verbindungen sowie verfahren zur herstellung dieser verbindungen.

Country Status (8)

Country	Link
JP (4)	JPS57114589A (da)
CH (2)	CH655724A5 (da)
DE (2)	DE3142143A1 (da)
FR (1)	FR2494273B1 (da)
GB (1)	GB2087884B (da)
HK (1)	HK89990A (da)
IT (1)	IT1143242B (da)
SU (1)	SU1318165A3 (da)

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 CH6895/81A patent/CH655724A5/de not_active IP Right Cessation
- 1981-10-28 CH CH4003/84A patent/CH655726A5/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 FR FR8121480A patent/FR2494273B1/fr not_active Expired
- 1981-11-17 JP JP56183170A patent/JPS57114589A/ja active Granted
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
HK89990A (en)	1990-11-09
JPH0427231B2 (da)	1992-05-11
DE3142143C2 (da)	1992-07-30
JPH0314581A (ja)	1991-01-23
SU1318165A3 (ru)	1987-06-15
JPS57114589A (en)	1982-07-16
JPH0314545A (ja)	1991-01-23
JPH0314561A (ja)	1991-01-23
CH655726A5 (de)	1986-05-15
IT1143242B (it)	1986-10-22
FR2494273A1 (fr)	1982-05-21
FR2494273B1 (fr)	1985-12-20
DE3142143A1 (de)	1982-06-24
DE3153725C2 (da)	1993-03-18
JPH0460594B2 (da)	1992-09-28
GB2087884A (en)	1982-06-03
JPH0465076B2 (da)	1992-10-16
JPH0310629B2 (da)	1991-02-14
GB2087884B (en)	1985-06-05
IT8149446A0 (it)	1981-10-07

Legal Events

Date	Code	Title	Description
1997-12-15	PFA	Name/firm changed	Owner name: THE UPJOHN COMPANY TRANSFER- PHARMACIA & UPJOHN CO
1999-06-15	PL	Patent ceased

Publication	Publication Date	Title
DE69736704T2 (de)	2007-09-13	Piperazin- und piperidin- derivate
DE3010195C2 (da)	1990-10-25
DE69204840T2 (de)	1996-02-22	Verfahren zur Herstellung von Sertralin.
DD156369A5 (de)	1982-08-18	Herstellung von rechtsdrehenden 5-aryl-2,3,4,4a,5,9b-hexahydro-1h-pyrido[4,3b]-indolen
EP0606661A1 (de)	1994-07-20	Octahydrophenanthrenderivate
DE3406805C2 (da)	1987-12-10
EP0273270A1 (de)	1988-07-06	Verfahren zur Herstellung von (+)-Biotin
CH617934A5 (da)	1980-06-30
DE9101348U1 (de)	1991-06-06	Trizyklisch-zyklische Amine als neue Cholinesterease-Inhibitoren
EP0219055B1 (de)	1989-06-07	Verfahren zur Herstellung von Clausenamid
DE3142143C2 (da)	1992-07-30
DE3632589A1 (de)	1987-04-23	Verfahren zur herstellung von (gamma)-butyrolactamen
DE3919255A1 (de)	1990-12-20	Dibenzo/1,5/dioxocin-5-one-derivate, ihre verwendung in arzneimitteln und verfahren zu ihrer herstellung
EP1010684B1 (en)	2008-07-16	Process for producing 3,4-dihydroxy-3-cyclobutene-1,2-dione
DE2922800A1 (de)	1979-12-13	Zwischenprodukte zur synthese von 4-demethoxydaunorubicin
EP0492401B1 (de)	1996-01-24	Asymmetrische Hydrierung
EP1844019B1 (de)	2009-09-02	Verfahren zur herstellung von losartan
CH633561A5 (de)	1982-12-15	Verfahren zum herstellen eines gold-komplexes.
AT392782B (de)	1991-06-10	Verfahren zur herstellung von alpha-(p-tent.- butylphenyl)-4-(hydroxydiphenylmethyl)-1- piperidinobutanol
DE69005852T2 (de)	1994-04-28	Entzündungshemmende Benzoxazolone.
EP0513700B1 (de)	1997-07-23	Verfahren zur Herstellung von Imidazothiazolon-Derivaten
DE3906174A1 (de)	1990-08-30	Verfahren zur herstellung von d-mannosaminderivaten
DE69411273T2 (de)	1998-12-03	Verfahren zur herstellung von hydrochinon-und benzochinon-derivaten
AT371445B (de)	1983-06-27	Verfahren zur herstellung von neuen cis-4a-phenyl-isochinolinderivaten und ihren saeureadditionssalzen
DE3640591A1 (de)	1988-06-01	Neue 2-substituierte 4-isopropyl-cyclohex-2-en-1-one