DD231354A5 - Verfahren zur herstellung neuer pyridin-2-ether beziehungsweise pyridin-2-thio-ether mit einem stickstoffhaltigem cycloaliphatischen ring - Google Patents

Verfahren zur herstellung neuer pyridin-2-ether beziehungsweise pyridin-2-thio-ether mit einem stickstoffhaltigem cycloaliphatischen ring Download PDF

Info

Publication number: DD231354A5
Authority: DD; German Democratic Republic
Prior art keywords: group; radical; groups; formula; compounds
Prior art date: 1983-12-28

Application number

DD84271863A

Other languages

German (de)

English (en)

Inventor

Gerhard Scheffler

Juergen Engel

Vladimir Jakovlev

Bernd Nickel

Klaus Thiemer

Original Assignee

��@��k��

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.)

1983-12-28

Filing date

1984-12-27

Publication date

1985-12-24

1984-12-27 Application filed by ��@��k�� filed Critical ��@��k��

1985-12-24 Publication of DD231354A5 publication Critical patent/DD231354A5/de

Links

238000004519 manufacturing process Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 85
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 39
239000001257 hydrogen Substances 0.000 claims abstract description 37
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 26
150000003839 salts Chemical class 0.000 claims abstract description 25
150000002431 hydrogen Chemical class 0.000 claims abstract description 23
125000005843 halogen group Chemical group 0.000 claims abstract description 19
229910052717 sulfur Inorganic materials 0.000 claims abstract description 18
238000000034 method Methods 0.000 claims abstract description 17
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 12
239000011593 sulfur Chemical group 0.000 claims abstract description 12
125000003277 amino group Chemical group 0.000 claims abstract description 11
150000001412 amines Chemical class 0.000 claims abstract description 8
229910052799 carbon Inorganic materials 0.000 claims abstract description 8
125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
125000002947 alkylene group Chemical group 0.000 claims abstract description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 claims abstract description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
239000001301 oxygen Substances 0.000 claims abstract description 5
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
-1 methylenedioxy group Chemical group 0.000 claims description 58
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 12
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
239000000460 chlorine Substances 0.000 claims description 11
150000003457 sulfones Chemical class 0.000 claims description 9
150000003462 sulfoxides Chemical class 0.000 claims description 9
125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
125000002252 acyl group Chemical group 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
125000005236 alkanoylamino group Chemical group 0.000 claims description 4
125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
LCIYFINKFGDAHD-UHFFFAOYSA-N azepane;3-nitrobenzoic acid Chemical compound C1CCCNCC1.OC(=O)C1=CC=CC([N+]([O-])=O)=C1 LCIYFINKFGDAHD-UHFFFAOYSA-N 0.000 claims 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 9
230000000202 analgesic effect Effects 0.000 abstract description 4
125000000304 alkynyl group Chemical group 0.000 abstract description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 65
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 53
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 45
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 35
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 32
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
239000002904 solvent Substances 0.000 description 30
150000003254 radicals Chemical class 0.000 description 28
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 23
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 23
125000001309 chloro group Chemical group Cl* 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
238000003756 stirring Methods 0.000 description 19
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
239000000203 mixture Substances 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
229960000583 acetic acid Drugs 0.000 description 12
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 11
MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 11
238000005804 alkylation reaction Methods 0.000 description 11
239000002585 base Substances 0.000 description 11
239000002253 acid Substances 0.000 description 10
125000003545 alkoxy group Chemical group 0.000 description 10
230000029936 alkylation Effects 0.000 description 10
238000001816 cooling Methods 0.000 description 10
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 10
239000007858 starting material Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000003513 alkali Substances 0.000 description 9
229910052783 alkali metal Inorganic materials 0.000 description 9
229960001760 dimethyl sulfoxide Drugs 0.000 description 9
150000004820 halides Chemical class 0.000 description 9
230000003647 oxidation Effects 0.000 description 9
238000007254 oxidation reaction Methods 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
238000010992 reflux Methods 0.000 description 9
239000000126 substance Substances 0.000 description 9
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 8
229910052736 halogen Inorganic materials 0.000 description 8
239000000047 product Substances 0.000 description 8
239000011734 sodium Substances 0.000 description 8
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
238000005917 acylation reaction Methods 0.000 description 7
239000012362 glacial acetic acid Substances 0.000 description 7
125000006239 protecting group Chemical group 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
230000010933 acylation Effects 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
238000005984 hydrogenation reaction Methods 0.000 description 6
239000002609 medium Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
125000000547 substituted alkyl group Chemical group 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
239000008096 xylene Substances 0.000 description 6
FILKGCRCWDMBKA-UHFFFAOYSA-N 2,6-dichloropyridine Chemical compound ClC1=CC=CC(Cl)=N1 FILKGCRCWDMBKA-UHFFFAOYSA-N 0.000 description 5
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
125000003710 aryl alkyl group Chemical group 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
238000009835 boiling Methods 0.000 description 5
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
125000005346 substituted cycloalkyl group Chemical group 0.000 description 5
239000000375 suspending agent Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
150000007514 bases Chemical class 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
238000003776 cleavage reaction Methods 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
239000007800 oxidant agent Substances 0.000 description 4
229910052700 potassium Inorganic materials 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
230000007017 scission Effects 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
125000005017 substituted alkenyl group Chemical group 0.000 description 4
150000003512 tertiary amines Chemical class 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
239000005708 Sodium hypochlorite Substances 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
125000001931 aliphatic group Chemical group 0.000 description 3
150000008044 alkali metal hydroxides Chemical class 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 3
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 3
238000004140 cleaning Methods 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
150000004292 cyclic ethers Chemical class 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000012458 free base Substances 0.000 description 3
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 3
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910017604 nitric acid Inorganic materials 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
150000004965 peroxy acids Chemical class 0.000 description 3
ZVMBSTCFPATRKJ-UHFFFAOYSA-N piperidine-4-thiol;hydrochloride Chemical compound Cl.SC1CCNCC1 ZVMBSTCFPATRKJ-UHFFFAOYSA-N 0.000 description 3
125000003386 piperidinyl group Chemical group 0.000 description 3
229940072033 potash Drugs 0.000 description 3
239000011591 potassium Substances 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
235000015320 potassium carbonate Nutrition 0.000 description 3
239000012286 potassium permanganate Substances 0.000 description 3
150000003222 pyridines Chemical class 0.000 description 3
238000000926 separation method Methods 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
239000000725 suspension Substances 0.000 description 3
TXVSXWOWWHALFQ-UHFFFAOYSA-N 1-methylpiperidine-4-thiol Chemical compound CN1CCC(S)CC1 TXVSXWOWWHALFQ-UHFFFAOYSA-N 0.000 description 2
RFOMGVDPYLWLOC-UHFFFAOYSA-N 2,6-dichloro-1-oxidopyridin-1-ium Chemical compound [O-][N+]1=C(Cl)C=CC=C1Cl RFOMGVDPYLWLOC-UHFFFAOYSA-N 0.000 description 2
LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
HCYYIDRHRNVEPU-UHFFFAOYSA-N 6-chloro-1h-pyridine-2-thione Chemical compound SC1=CC=CC(Cl)=N1 HCYYIDRHRNVEPU-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-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
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
229910000102 alkali metal hydride Inorganic materials 0.000 description 2
150000008046 alkali metal hydrides Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
235000011114 ammonium hydroxide Nutrition 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 2
QXYJCZRRLLQGCR-UHFFFAOYSA-N dioxomolybdenum Chemical compound O=[Mo]=O QXYJCZRRLLQGCR-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000008282 halocarbons Chemical class 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 2
239000005457 ice water Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
150000002688 maleic acid derivatives Chemical class 0.000 description 2
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
239000002504 physiological saline solution Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
150000004763 sulfides Chemical class 0.000 description 2
125000004434 sulfur atom Chemical group 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
HFVMEOPYDLEHBR-UHFFFAOYSA-N (2-fluorophenyl)-phenylmethanol Chemical compound C=1C=CC=C(F)C=1C(O)C1=CC=CC=C1 HFVMEOPYDLEHBR-UHFFFAOYSA-N 0.000 description 1
OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
IIFVWLUQBAIPMJ-UHFFFAOYSA-N (4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C=C1 IIFVWLUQBAIPMJ-UHFFFAOYSA-N 0.000 description 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
KYGMSTKBHJVPJK-UHFFFAOYSA-N 1-(2-phenylethyl)piperidin-4-ol Chemical compound C1CC(O)CCN1CCC1=CC=CC=C1 KYGMSTKBHJVPJK-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 1
WSNDAYQNZRJGMJ-UHFFFAOYSA-N 2,2,2-trifluoroethanone Chemical compound FC(F)(F)[C]=O WSNDAYQNZRJGMJ-UHFFFAOYSA-N 0.000 description 1
UMYMWCKSANKFPI-UHFFFAOYSA-N 2-(2-chloroethyl)-1-methylpiperidine Chemical compound CN1CCCCC1CCCl UMYMWCKSANKFPI-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
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
FNRMMDCDHWCQTH-UHFFFAOYSA-N 2-chloropyridine;3-chloropyridine;4-chloropyridine Chemical compound ClC1=CC=NC=C1.ClC1=CC=CN=C1.ClC1=CC=CC=N1 FNRMMDCDHWCQTH-UHFFFAOYSA-N 0.000 description 1
MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 1
ATTRMYMZQWIZOR-RRKCRQDMSA-N 4-amino-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-methyl-1,3,5-triazin-2-one Chemical compound CC1=NC(N)=NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)C1 ATTRMYMZQWIZOR-RRKCRQDMSA-N 0.000 description 1
QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
FUUQRXRAKROWFH-UHFFFAOYSA-N 6-chloro-1h-pyridine-2-thione;sodium Chemical compound [Na].ClC1=CC=CC(=S)N1 FUUQRXRAKROWFH-UHFFFAOYSA-N 0.000 description 1
AULWPXHFRBLPAE-UHFFFAOYSA-N 6-chloropyridine Chemical compound ClC1=C=CC=C[N]1 AULWPXHFRBLPAE-UHFFFAOYSA-N 0.000 description 1
YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
101150065749 Churc1 gene Proteins 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
230000005526 G1 to G0 transition Effects 0.000 description 1
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
230000006181 N-acylation Effects 0.000 description 1
238000007126 N-alkylation reaction Methods 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
102100038239 Protein Churchill Human genes 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000000370 acceptor Substances 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000004973 alkali metal peroxides Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 1
125000004448 alkyl carbonyl group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
125000005530 alkylenedioxy group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
230000001741 anti-phlogistic effect Effects 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004531 blood pressure lowering effect Effects 0.000 description 1
UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 description 1
125000005621 boronate group Chemical class 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000012320 chlorinating reagent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
125000000950 dibromo group Chemical group Br* 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
MKALGZPKLBJCTR-UHFFFAOYSA-N ethyl 1-methyl-2-sulfanylpiperidine-4-carboxylate Chemical compound CCOC(=O)C1CCN(C)C(S)C1 MKALGZPKLBJCTR-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
150000005826 halohydrocarbons Chemical class 0.000 description 1
125000005059 halophenyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 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
150000002432 hydroperoxides Chemical class 0.000 description 1
150000002440 hydroxy compounds Chemical class 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
JYJVVHFRSFVEJM-UHFFFAOYSA-N iodosobenzene Chemical compound O=IC1=CC=CC=C1 JYJVVHFRSFVEJM-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
PZILXGBGUICZBR-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]pyridin-2-amine Chemical compound C1=CC(F)=CC=C1CNC1=CC=CC=N1 PZILXGBGUICZBR-UHFFFAOYSA-N 0.000 description 1
ISRXMEYARGEVIU-UHFFFAOYSA-N n-methyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C)C(C)C ISRXMEYARGEVIU-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
238000000039 preparative column chromatography Methods 0.000 description 1
WMIUEDNYZNJORC-UHFFFAOYSA-N propan-2-ol sulfane Chemical compound S.C(C)(C)O WMIUEDNYZNJORC-UHFFFAOYSA-N 0.000 description 1
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical class OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridine hydrochloride Substances [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical group C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
150000003388 sodium compounds Chemical class 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000012128 staining reagent Substances 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229950000244 sulfanilic acid Drugs 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003511 tertiary amides Chemical class 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003609 titanium compounds Chemical class 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
150000003628 tricarboxylic acids Chemical class 0.000 description 1
DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
125000006004 trihaloethyl group Chemical group 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/54—Sulfur atoms
- 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
- C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D451/04—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system
- C07D451/06—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Pain & Pain Management (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Biomedical Technology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

DD84271863A 1983-12-28 1984-12-27 Verfahren zur herstellung neuer pyridin-2-ether beziehungsweise pyridin-2-thio-ether mit einem stickstoffhaltigem cycloaliphatischen ring DD231354A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3347276		1983-12-28

Publications (1)

Publication Number	Publication Date
DD231354A5 true DD231354A5 (de)	1985-12-24

Family

ID=6218282

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD84271863A DD231354A5 (de)	1983-12-28	1984-12-27	Verfahren zur herstellung neuer pyridin-2-ether beziehungsweise pyridin-2-thio-ether mit einem stickstoffhaltigem cycloaliphatischen ring

Country Status (20)

Country	Link
US (1)	US4643995A (da)
EP (1)	EP0149088B1 (da)
JP (1)	JPS60169476A (da)
KR (1)	KR870000354B1 (da)
CN (1)	CN85101353A (da)
AT (1)	ATE40131T1 (da)
AU (1)	AU566560B2 (da)
DD (1)	DD231354A5 (da)
DE (2)	DE3476205D1 (da)
DK (1)	DK613384A (da)
ES (1)	ES8607014A1 (da)
FI (1)	FI84062C (da)
GB (1)	GB2152048B (da)
GR (1)	GR82596B (da)
HU (1)	HU194209B (da)
IL (1)	IL73608A (da)
NO (1)	NO164237C (da)
PT (1)	PT79736B (da)
SU (1)	SU1417796A3 (da)
ZA (1)	ZA848275B (da)

Families Citing this family (54)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA836994B (en) *	1982-09-30	1984-05-30	Robins Co Inc A H	Fused aromatic oxazepinones and sulfur analogs thereof
DK623586A (da) *	1985-12-27	1987-06-28	Eisai Co Ltd	Piperidinderivater eller salte deraf og farmaceutiske kompositioner indeholdende forbindelserne
US4853027A (en) *	1986-09-08	1989-08-01	E. I. Du Pont De Nemours And Company	Phytotoxic 2-alkyl-5-(heterocyclic)-pyrrole-3,4-dicarboxylates
EP0287908A3 (de) *	1987-04-18	1989-12-27	ASTA Medica Aktiengesellschaft	Neue stickstoffhaltige, cycloaliphatische Verbindungen mit einem Aminosäurerest sowie einem Pyridinrest
CA1307790C (en) *	1987-08-04	1992-09-22	Ian Anthony Cliffe	Ethers
GB8718445D0 (en) *	1987-08-04	1987-09-09	Wyeth John & Brother Ltd	Pyridyl-ethers
FR2655649B1 (fr) *	1989-12-12	1994-07-08	Adir	Nouveaux derives de la piperidine, leur procede de preparation et les compositions pharmaceutiques les renfermant.
MX9100517A (es) *	1990-08-06	1992-04-01	Smith Kline French Lab	Compuestos
US5914328A (en) *	1992-10-09	1999-06-22	Abbott Laboratories	Heterocyclic ether compounds useful in controlling neurotransmitter release
US5948793A (en) *	1992-10-09	1999-09-07	Abbott Laboratories	3-pyridyloxymethyl heterocyclic ether compounds useful in controlling neurotransmitter release
IL107184A (en) *	1992-10-09	1997-08-14	Abbott Lab	Heterocyclic ether compounds that enhance cognitive function
ZA9610738B (en)	1995-12-22	1997-06-24	Warner Lambert Co	Subtype selective nmda receptor ligands and the use thereof
ZA9610741B (en)	1995-12-22	1997-06-24	Warner Lambert Co	4-Substituted piperidine analogs and their use as subtype selective nmda receptor antagonists
ZA9610736B (en)	1995-12-22	1997-06-27	Warner Lambert Co	2-Substituted piperidine analogs and their use as subtypeselective nmda receptor antagonists
ZA9610745B (en) *	1995-12-22	1997-06-24	Warner Lambert Co	4-Subsituted piperidine analogs and their use as subtype selective nmda receptor antagonists
US6437138B1 (en)	1996-06-06	2002-08-20	Abbott Laboratories	3-pyridyloxymethyl heterocyclic ether compounds useful in controlling chemical synaptic transmission
US5629325A (en) *	1996-06-06	1997-05-13	Abbott Laboratories	3-pyridyloxymethyl heterocyclic ether compounds useful in controlling chemical synaptic transmission
US6133253A (en) *	1996-12-10	2000-10-17	Abbott Laboratories	3-Pyridyl enantiomers and their use as analgesics
CA2306477A1 (en) *	1997-11-05	1999-05-20	Neurosearch A/S	Azaring-ether derivatives and their use as nicotinic ach receptor modulators
US6632823B1 (en) *	1997-12-22	2003-10-14	Merck & Co., Inc.	Substituted pyridine compounds useful as modulators of acetylcholine receptors
PE20000728A1 (es) *	1998-06-26	2000-08-21	Cocensys Inc	Heterociclos 4-bencil piperidina alquilsulfoxido y su uso como antagonistas receptores subtipo-selectivo nmda
CA2381252A1 (en) *	1999-09-14	2001-03-22	Abbott Laboratories	3-pyrrolidinyloxy-3'-pyridyl ether compounds useful for controlling chemical synaptic transmission
AU779063B2 (en) *	1999-12-06	2005-01-06	F. Hoffmann-La Roche Ag	4-pyridinyl-N-acyl-L-phenylalanines
DE10000739A1 (de) *	2000-01-11	2001-07-12	Merck Patent Gmbh	Piperidin- und Piperazinderivate
US6436916B1 (en)	2000-10-12	2002-08-20	Alvin Guttag	Ibuprofen-aspirin and hydroxymethylacylfulvene analogs
WO2003062224A1 (en)	2002-01-17	2003-07-31	Eli Lilly And Company	Aza-cyclic compounds as modulators of acetylcholine receptors
GB0220581D0 (en)	2002-09-04	2002-10-09	Novartis Ag	Organic Compound
CN102558155A (zh)	2003-01-14	2012-07-11	阿伦纳药品公司	作为代谢调节剂的芳基和杂芳基衍生物及其所涉及的疾病如糖尿病和高血糖症的预防和治疗
UA82517C2 (uk) *	2003-06-24	2008-04-25	Ньюросерч А/С	Нові похідні 8-аза-біцикло[3.2.1]октану та їх застосування як інгібіторів ресорбції моноамінових медіаторів
AR045047A1 (es)	2003-07-11	2005-10-12	Arena Pharm Inc	Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos
HRP20090093T3 (en) *	2004-06-04	2009-03-31	Arena Pharmaceuticals Inc.	Substituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto
PE20060437A1 (es)	2004-06-18	2006-06-08	Novartis Ag	COMPUESTOS AZA-BICICLONONANOS COMO LIGANDOS COLINERGICOS DE nAChR
GB0415746D0 (en)	2004-07-14	2004-08-18	Novartis Ag	Organic compounds
MY148521A (en)	2005-01-10	2013-04-30	Arena Pharm Inc	Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto
DOP2006000010A (es)	2005-01-10	2006-07-31	Arena Pharm Inc	Procedimiento para preparar eteres aromáticos
US7413805B2 (en) *	2005-02-25	2008-08-19	Fry's Metals, Inc.	Preparation of metallic particles for electrokinetic or electrostatic deposition
GEP20104966B (en) *	2005-09-16	2010-04-26	Arena Pharm Inc	Modulators of metabolism and the treatment of disorders related thereto
GB0521508D0 (en)	2005-10-21	2005-11-30	Novartis Ag	Organic compounds
GB0525672D0 (en)	2005-12-16	2006-01-25	Novartis Ag	Organic compounds
GB0525673D0 (en)	2005-12-16	2006-01-25	Novartis Ag	Organic compounds
RS52062B (sr)	2006-05-19	2012-06-30	Abbott Laboratories	Cns aktivni azabiciklični alkanski derivati koji su supstituisani spojenim bicikloheterociklom
TW200811147A (en) *	2006-07-06	2008-03-01	Arena Pharm Inc	Modulators of metabolism and the treatment of disorders related thereto
TW200811140A (en) *	2006-07-06	2008-03-01	Arena Pharm Inc	Modulators of metabolism and the treatment of disorders related thereto
WO2008147518A1 (en) *	2007-05-23	2008-12-04	Merck & Co., Inc.	Pyridyl piperidine orexin receptor antagonists
AU2009307916A1 (en)	2008-10-21	2010-04-29	Merck Sharp & Dohme Corp.	2,5-disubstituted morpholine orexin receptor antagonists
AU2009307918A1 (en) *	2008-10-21	2010-04-29	Merck Sharp & Dohme Corp.	2,4-disubstituted pyrrolidine orexin receptor antagonists
CA2739915A1 (en)	2008-10-21	2010-04-29	Merck Sharp & Dohme Corp.	2,5-disubstituted piperidine orexin receptor antagonists
CA2786994C (en)	2010-01-27	2018-01-16	Arena Pharmaceuticals, Inc.	Processes for the preparation of (r)-2-(7-(4-cyclopentyl-3-(trifluoromethyl)benzyloxy)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid and salts thereof
MX2013003184A (es)	2010-09-22	2013-06-07	Arena Pharm Inc	Moduladores del receptor gpr119 y el tratamiento de transtornos relacionados con el mismo.
AR088352A1 (es)	2011-10-19	2014-05-28	Merck Sharp & Dohme	Antagonistas del receptor de 2-piridiloxi-4-nitrilo orexina
AU2016205361C1 (en)	2015-01-06	2021-04-08	Arena Pharmaceuticals, Inc.	Methods of treating conditions related to the S1P1 receptor
PL3310760T3 (pl)	2015-06-22	2023-03-06	Arena Pharmaceuticals, Inc.	Krystaliczna sól L-argininy kwasu (R)-2-(7-(4-cyklopentylo-3-(trifluorometylo)benzyloksy)- 1,2,3,4-tetrahydrocyklo-penta[b]indol-3-ilo)octowego do zastosowania w zaburzeniach związanych z receptorem S1P1
KR20190116416A (ko)	2017-02-16	2019-10-14	아레나 파마슈티칼스, 인크.	원발 담즙성 담관염을 치료하기 위한 화합물 및 방법
AU2019280822A1 (en)	2018-06-06	2021-01-07	Arena Pharmaceuticals, Inc.	Methods of treating conditions related to the S1P1 receptor

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE630125A (da) *
GB1041342A (en) *	1962-03-27	1966-09-07	Degussa	New pyridine derivatives
NL122313C (da) *	1963-07-11
US3308129A (en) *	1964-06-05	1967-03-07	Smith Kline French Lab	3-tropanyl esters of atropic and thioatropic acids
GB1306139A (da) *	1970-08-06	1973-02-07
US3905984A (en) *	1971-03-09	1975-09-16	Smith Kline French Lab	Pyridyl substituted thioalkyl-and oxyalkyl-thioureas and ureas
FR2187317B2 (da) *	1972-06-07	1975-06-20	Hexachimie
US3954782A (en) *	1972-06-22	1976-05-04	Cassella Farbwerke Mainkur Aktiengesellschaft	2,6-Hydrazino-3-pyridine carboxyamides
US3947463A (en) *	1972-06-22	1976-03-30	Cassella Farbwerke Mainkur Ag	Certain 2-amino-nicotinonitrile derivatives
US3980659A (en) *	1972-06-22	1976-09-14	Cassella Farbwerke Mainkur Aktiengesellschaft	Certain 6-amino-4-hydrocarbyl-nicotinamides
US4061642A (en) *	1972-06-22	1977-12-06	Cassella Farbwerke Mainkur Ag	2,4,6-Trisubstituted-3-pyridine carboxamides
US3956294A (en) *	1972-06-22	1976-05-11	Cassella Farbwerke Mainkur Aktiengesellschaft	Substituted pyridine compounds
US3946024A (en) *	1972-06-22	1976-03-23	Cassella Farbwerke Mainkur Ag	2-Hydrocarbyloxy-pyridine compounds
DE2549999A1 (de) *	1975-11-07	1977-05-12	Boehringer Mannheim Gmbh	Piperidin-derivate und verfahren zu ihrer herstellung
DE2905876A1 (de) *	1979-02-16	1980-08-28	Boehringer Mannheim Gmbh	Neue piperidinopropylderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
US4203990A (en) *	1979-04-30	1980-05-20	G. D. Searle & Co.	Anti-diarrheal 2-substituted quinuclidines
FR2459240A1 (fr) *	1979-06-21	1981-01-09	Cm Ind	Aminopiperidines anorexigenes, procede pour leur preparation, intermediaires dans ledit procede et medicaments qui les contiennent
DE3045688A1 (de) *	1980-12-04	1982-07-08	C.H. Boehringer Sohn, 6507 Ingelheim	Neue 8-arylalkyl-3-phenyl-3-nortropanole, deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zu ihrer herstellung
IT1190942B (it) *	1982-08-04	1988-02-24	Poli Ind Chimica Spa	Composto ad attivita' analgesica ed antiinfiammatoria,suo procedimento di preparazione e relative composizioni farmaceutiche

1984
- 1984-10-23 ZA ZA848275A patent/ZA848275B/xx unknown
- 1984-11-23 IL IL73608A patent/IL73608A/xx unknown
- 1984-12-01 DE DE8484114607T patent/DE3476205D1/de not_active Expired
- 1984-12-01 DE DE19843443968 patent/DE3443968A1/de not_active Withdrawn
- 1984-12-01 AT AT84114607T patent/ATE40131T1/de not_active IP Right Cessation
- 1984-12-01 EP EP84114607A patent/EP0149088B1/de not_active Expired
- 1984-12-17 US US06/682,773 patent/US4643995A/en not_active Expired - Fee Related
- 1984-12-20 DK DK613384A patent/DK613384A/da not_active Application Discontinuation
- 1984-12-20 AU AU36996/84A patent/AU566560B2/en not_active Ceased
- 1984-12-20 GB GB08432162A patent/GB2152048B/en not_active Expired
- 1984-12-21 SU SU843826165A patent/SU1417796A3/ru active
- 1984-12-21 PT PT79736A patent/PT79736B/pt not_active IP Right Cessation
- 1984-12-25 JP JP59272172A patent/JPS60169476A/ja active Pending
- 1984-12-27 ES ES539076A patent/ES8607014A1/es not_active Expired
- 1984-12-27 GR GR82596A patent/GR82596B/el unknown
- 1984-12-27 NO NO845250A patent/NO164237C/no unknown
- 1984-12-27 FI FI845126A patent/FI84062C/fi not_active IP Right Cessation
- 1984-12-27 DD DD84271863A patent/DD231354A5/de unknown
- 1984-12-28 HU HU844869A patent/HU194209B/hu not_active IP Right Cessation
- 1984-12-28 KR KR1019840008498A patent/KR870000354B1/ko not_active Expired
1985
- 1985-04-01 CN CN198585101353A patent/CN85101353A/zh active Pending

Also Published As

Publication number	Publication date
FI84062C (fi)	1991-10-10
AU566560B2 (en)	1987-10-22
GR82596B (en)	1985-04-29
FI84062B (fi)	1991-06-28
IL73608A0 (en)	1985-02-28
US4643995A (en)	1987-02-17
HUT36115A (en)	1985-08-28
DE3476205D1 (en)	1989-02-23
AU3699684A (en)	1985-07-04
JPS60169476A (ja)	1985-09-02
SU1417796A3 (ru)	1988-08-15
FI845126L (fi)	1985-06-29
NO845250L (no)	1985-07-01
ES8607014A1 (es)	1986-05-16
HU194209B (en)	1988-01-28
DK613384D0 (da)	1984-12-20
NO164237B (no)	1990-06-05
NO164237C (no)	1990-09-12
PT79736B (de)	1986-12-30
GB2152048A (en)	1985-07-31
KR870000354B1 (ko)	1987-03-05
EP0149088A1 (de)	1985-07-24
GB2152048B (en)	1987-11-11
EP0149088B1 (de)	1989-01-18
KR850004755A (ko)	1985-07-27
ZA848275B (en)	1985-08-28
PT79736A (de)	1985-01-01
DK613384A (da)	1985-06-29
FI845126A0 (fi)	1984-12-27
ES539076A0 (es)	1986-05-16
IL73608A (en)	1987-12-31
GB8432162D0 (en)	1985-01-30
CN85101353A (zh)	1986-10-15
ATE40131T1 (de)	1989-02-15
DE3443968A1 (de)	1985-10-31

Publication	Publication Date	Title
DE3443968A1 (de)	1985-10-31	Neue pyridin-2-ether beziehungsweise pyridin-2-thioether mit einem stickstoffhaltigen cycloaliphatischen ring
EP0667341B1 (de)	2001-08-29	4-Amino-1-piperidylbenzoylguanidine als Na+/H+-antiporter Inhibitoren
EP0722942A1 (de)	1996-07-24	Indolpiperidin-Derivate
DE10046029A1 (de)	2002-03-28	Indazole
DE1117584B (de)	1961-11-23	Verfahren zur Herstellung von Phentiazinderivaten
DE2635516C3 (de)	1981-04-16	Neue Derivate des Thiazolo[3,4-b]isochinolins, ihre Herstellung und die sie enthaltenden Zusammensetzungen
EP0206225A2 (de)	1986-12-30	Indolderivate
DE69200284T2 (de)	1995-03-02	Verwendung von 4-(3-trifluormethylphenyl)-1,2,3,6-Tetrahydropyridinderivaten als freie Radikalfänger.
DE4324393A1 (de)	1995-01-26	4-Aryloxy- und 4-Arylthiopiperidinderivate
DE69031845T2 (de)	1998-05-07	6,11-Dihydro-5H-pyrido(2,3-b)(1,5)benzodiazepin-5-one und Thione und ihre Verwendung für die Vorbeugung oder Behandlung von AIDS
DE2252612A1 (de)	1973-05-10	Derivate von 1-oxa-3,8-diaza-spiro(4,5)-decan und verfahren zu ihrer herstellung
DE60206376T2 (de)	2006-06-22	Faktor xa inhibitor
DE69627346T2 (de)	2004-03-04	4-aryl-thio-pyridin-2(1h)-onen, diese enthaltende arzneimittel und ihre anwendungen bei der behandlung von mit hiv zusammenhängenden krankheiten
DD293349A5 (de)	1991-08-29	Verfahren zur herstellung neuer thiouracilderivate und ihrer saeureadditionssalze
EP0362632A2 (de)	1990-04-11	Basische 4-Aryl-DHP-amide, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
EP0287908A2 (de)	1988-10-26	Neue stickstoffhaltige, cycloaliphatische Verbindungen mit einem Aminosäurerest sowie einem Pyridinrest
EP0763535A1 (de)	1997-03-19	Piperidinylmethyloxazolidin-2-on Derivate, deren Herstellung und deren Verwendung als ZNS wirksame Verbindungen
DE102004012365A1 (de)	2005-09-29	Substituierte Dihydropyridine
DE69200840T2 (de)	1995-06-29	Harnstoff- und Thioharnstoffderivate, Herstellung und therapeutische Verwendung.
EP1664058B1 (de)	2007-11-14	Substituierte thienoimidazole, verfahren zu ihrer herstellung, ihre verwendung als medikament oder diagnostikum sowie sie enthaltende medikamente
DD259401A5 (de)	1988-08-24	Verfahren zur herstellung von 2-alkylbenzimidazol-derivaten
EP0362635A1 (de)	1990-04-11	Verfahren von basischen Nitrophenyl-dihydropyridinamiden als Arzneimittel, neue Verbindungen und Verfahren zu ihrer Herstellung über neue Zwischenprodukte
DE2848926C3 (de)	1981-09-10	Derivate des 1,6,11,11a-Tetrahydro-[1,3-thiazino][3,4-b]isochinolins, ihre Herstellung und die sie enthaltenden Zusammensetzungen
EP0124630A1 (de)	1984-11-14	Pyrimidin-Thioalkylpyridin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindung enthaltende Arzneimittel
WO2007107246A2 (de)	2007-09-27	Substituierte 2-amino-4-phenyl-dihydrochnoline, verfahren zu ihrer herstellung, ihre verwendung als medikament, sowie sie enthaltendes medikament