DD263058A5 - Verfahren zur herstellung von 4-benzyl-1-(2h)-phthalazinon-derivaten - Google Patents

Verfahren zur herstellung von 4-benzyl-1-(2h)-phthalazinon-derivaten Download PDF

Info

Publication number: DD263058A5
Authority: DD; German Democratic Republic
Prior art keywords: radical; formula; group; alkyl; compounds
Prior art date: 1985-11-11

Application number

DD86296130A

Other languages

German (de)

English (en)

Inventor

Juergen Engel

Gerhard Scheffler

Original Assignee

��`��@��k��@��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.)

1985-11-11

Filing date

1986-11-10

Publication date

1988-12-21

1986-11-10 Application filed by ��`��@��k��@��k�� filed Critical ��`��@��k��@��k��

1988-12-21 Publication of DD263058A5 publication Critical patent/DD263058A5/de

Links

JUCCMEHWBGPJKS-UHFFFAOYSA-N 4-benzyl-2h-phthalazin-1-one Chemical class C12=CC=CC=C2C(=O)NN=C1CC1=CC=CC=C1 JUCCMEHWBGPJKS-UHFFFAOYSA-N 0.000 title claims abstract description 10
238000000034 method Methods 0.000 title claims description 21
238000002360 preparation method Methods 0.000 title claims description 12
230000008569 process Effects 0.000 title claims description 7
-1 C2-C6-alkanoyloxy Chemical group 0.000 claims abstract description 51
239000001257 hydrogen Substances 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
229910052801 chlorine Inorganic materials 0.000 claims abstract description 13
239000000460 chlorine Chemical group 0.000 claims abstract description 13
229910052731 fluorine Inorganic materials 0.000 claims abstract description 11
150000002431 hydrogen Chemical class 0.000 claims abstract description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
229910052794 bromium Inorganic materials 0.000 claims abstract description 10
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 9
239000011737 fluorine Substances 0.000 claims abstract description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 6
150000002367 halogens Chemical class 0.000 claims abstract description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 63
239000002253 acid Substances 0.000 claims description 28
150000003839 salts Chemical class 0.000 claims description 21
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 10
230000010933 acylation Effects 0.000 claims description 9
238000005917 acylation reaction Methods 0.000 claims description 9
238000005804 alkylation reaction Methods 0.000 claims description 9
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
230000029936 alkylation Effects 0.000 claims description 7
125000001424 substituent group Chemical group 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 5
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
125000005236 alkanoylamino group Chemical group 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000002130 sulfonic acid ester group Chemical group 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
239000008024 pharmaceutical diluent Substances 0.000 claims description 2
125000003282 alkyl amino group Chemical group 0.000 claims 3
MJPPGVVIDGQOQT-UHFFFAOYSA-N 2-bromo-5-(2-bromo-2-nitroethenyl)furan Chemical compound [O-][N+](=O)C(Br)=CC1=CC=C(Br)O1 MJPPGVVIDGQOQT-UHFFFAOYSA-N 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
239000012059 conventional drug carrier Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 abstract description 4
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 1
MOFINMJRLYEONQ-UHFFFAOYSA-N [N].C=1C=CNC=1 Chemical compound [N].C=1C=CNC=1 MOFINMJRLYEONQ-UHFFFAOYSA-N 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 38
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
239000000243 solution Substances 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 30
239000007858 starting material Substances 0.000 description 29
150000003254 radicals Chemical class 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
238000003756 stirring Methods 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 23
239000002904 solvent Substances 0.000 description 23
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 21
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000000047 product Substances 0.000 description 17
239000002585 base Substances 0.000 description 16
239000000126 substance Substances 0.000 description 16
239000003921 oil Substances 0.000 description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
125000001309 chloro group Chemical group Cl* 0.000 description 13
238000001816 cooling Methods 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
239000005711 Benzoic acid Substances 0.000 description 10
239000003795 chemical substances by application Substances 0.000 description 10
238000010992 reflux Methods 0.000 description 10
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 9
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000013543 active substance Substances 0.000 description 8
235000010233 benzoic acid Nutrition 0.000 description 8
239000007795 chemical reaction product Substances 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
239000000155 melt Substances 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
229910021529 ammonia Inorganic materials 0.000 description 7
238000001035 drying Methods 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 6
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
239000003513 alkali Substances 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
239000012458 free base Substances 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
BTBUNPKEXDCSGD-UHFFFAOYSA-N O=C1CC=CC=CN1CC1=CC=CC=C1 Chemical compound O=C1CC=CC=CN1CC1=CC=CC=C1 BTBUNPKEXDCSGD-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000002270 dispersing agent Substances 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
238000010626 work up procedure Methods 0.000 description 5
229920002261 Corn starch Polymers 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
150000008044 alkali metal hydroxides Chemical class 0.000 description 4
150000001408 amides Chemical group 0.000 description 4
208000006673 asthma Diseases 0.000 description 4
WARCRYXKINZHGQ-UHFFFAOYSA-N benzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1 WARCRYXKINZHGQ-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
230000037396 body weight Effects 0.000 description 4
239000002775 capsule Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000008120 corn starch Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
229960001760 dimethyl sulfoxide Drugs 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000003480 eluent Substances 0.000 description 4
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 4
238000010438 heat treatment Methods 0.000 description 4
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
239000005457 ice water Substances 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
230000009471 action Effects 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
230000000202 analgesic effect Effects 0.000 description 3
150000007514 bases Chemical class 0.000 description 3
239000006071 cream Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
229910000042 hydrogen bromide Inorganic materials 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000011630 iodine Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
125000005936 piperidyl group Chemical group 0.000 description 3
150000003462 sulfoxides Chemical class 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
239000008096 xylene Substances 0.000 description 3
GSUCKVZTSXHESM-UHFFFAOYSA-N (1-methylpiperidin-4-yl)hydrazine Chemical compound CN1CCC(NN)CC1 GSUCKVZTSXHESM-UHFFFAOYSA-N 0.000 description 2
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
YLPXXNXZXVKZQA-UHFFFAOYSA-N 2-(azepan-4-yl)-4-[(4-fluorophenyl)methyl]phthalazin-1-one Chemical compound C1=CC(F)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C1CCNCCC1 YLPXXNXZXVKZQA-UHFFFAOYSA-N 0.000 description 2
QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 2
LYESPCDUHISKFI-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-2-(1-methylpiperidin-4-yl)phthalazin-1-one Chemical compound C1CN(C)CCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(F)=CC=2)=N1 LYESPCDUHISKFI-UHFFFAOYSA-N 0.000 description 2
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 2
241000700198 Cavia Species 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
150000008041 alkali metal carbonates Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000004448 alkyl carbonyl group Chemical group 0.000 description 2
230000000172 allergic effect Effects 0.000 description 2
230000003266 anti-allergic effect Effects 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
208000010668 atopic eczema Diseases 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
229940073608 benzyl chloride Drugs 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
229960000541 cetyl alcohol Drugs 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
150000003997 cyclic ketones Chemical class 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
125000004175 fluorobenzyl group Chemical group 0.000 description 2
238000005187 foaming Methods 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
239000008187 granular material Substances 0.000 description 2
230000001558 histaminolytic effect Effects 0.000 description 2
150000003840 hydrochlorides Chemical class 0.000 description 2
238000002955 isolation Methods 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
YGQLAWOSCOSWLT-UHFFFAOYSA-N n'-(1-benzylazepan-4-yl)benzohydrazide Chemical compound C=1C=CC=CC=1C(=O)NNC(CC1)CCCN1CC1=CC=CC=C1 YGQLAWOSCOSWLT-UHFFFAOYSA-N 0.000 description 2
NNALKJUMRUSNQD-UHFFFAOYSA-N n'-(1-methylpiperidin-4-yl)benzohydrazide Chemical compound C1CN(C)CCC1NNC(=O)C1=CC=CC=C1 NNALKJUMRUSNQD-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
239000002674 ointment Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
229960005323 phenoxyethanol Drugs 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical group OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 description 2
229940072033 potash Drugs 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
235000015320 potassium carbonate Nutrition 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
230000009467 reduction Effects 0.000 description 2
230000007017 scission Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 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
238000011282 treatment Methods 0.000 description 2
QQXLDOJGLXJCSE-KNVOCYPGSA-N tropinone Chemical compound C1C(=O)C[C@H]2CC[C@@H]1N2C QQXLDOJGLXJCSE-KNVOCYPGSA-N 0.000 description 2
238000005406 washing Methods 0.000 description 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
DMHZDOTYAVHSEH-UHFFFAOYSA-N 1-(chloromethyl)-4-methylbenzene Chemical compound CC1=CC=C(CCl)C=C1 DMHZDOTYAVHSEH-UHFFFAOYSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
HUUPVABNAQUEJW-UHFFFAOYSA-N 1-methylpiperidin-4-one Chemical compound CN1CCC(=O)CC1 HUUPVABNAQUEJW-UHFFFAOYSA-N 0.000 description 1
UEAMWAQNJCNODY-UHFFFAOYSA-N 2-(1-benzylazepan-4-yl)-4-[(4-fluorophenyl)methyl]phthalazin-1-one Chemical compound C1=CC(F)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C1CCN(CC=2C=CC=CC=2)CCC1 UEAMWAQNJCNODY-UHFFFAOYSA-N 0.000 description 1
BYCRIEOMHORWBN-UHFFFAOYSA-N 2-(1-benzylazepan-4-yl)-4-[(4-methylphenyl)methyl]phthalazin-1-one Chemical compound C1=CC(C)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C1CCN(CC=2C=CC=CC=2)CCC1 BYCRIEOMHORWBN-UHFFFAOYSA-N 0.000 description 1
LGVCQKVONFMUGU-UHFFFAOYSA-N 2-(1-methylazepin-4-yl)-3,4,4a,5,6,7-hexahydrophthalazin-1-one Chemical compound C1=CN(C)C=CC=C1N1C(=O)C2=CCCCC2CN1 LGVCQKVONFMUGU-UHFFFAOYSA-N 0.000 description 1
FZJYRHRUFUUOMN-UHFFFAOYSA-N 2-(azepan-4-yl)-4-[(4-chlorophenyl)methyl]phthalazin-1-one;hydrobromide Chemical compound Br.C1=CC(Cl)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C1CCNCCC1 FZJYRHRUFUUOMN-UHFFFAOYSA-N 0.000 description 1
WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
OHRFHJYUEWVXBD-UHFFFAOYSA-N 3-[(4-chlorophenyl)methylidene]-2-benzofuran-1-one Chemical compound C1=CC(Cl)=CC=C1C=C1C2=CC=CC=C2C(=O)O1 OHRFHJYUEWVXBD-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
LTUABJAYJRTHEH-UHFFFAOYSA-N 3-ethyl-1,2-oxazole Chemical compound CCC=1C=CON=1 LTUABJAYJRTHEH-UHFFFAOYSA-N 0.000 description 1
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
ADTDXDKSKMFLLM-UHFFFAOYSA-N 4-[(3,4-dichlorophenyl)methyl]-2-[1-(1-phenylethyl)azepan-4-yl]phthalazin-1-one Chemical compound ClC=1C=C(CC2=NN(C(C3=CC=CC=C23)=O)C2CCN(CCC2)C(C)C2=CC=CC=C2)C=CC1Cl ADTDXDKSKMFLLM-UHFFFAOYSA-N 0.000 description 1
PFGUEWFNDYGZAB-UHFFFAOYSA-N 4-[(4-fluorophenyl)methyl]-2-piperidin-4-ylphthalazin-1-one Chemical compound C1=CC(F)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C1CCNCC1 PFGUEWFNDYGZAB-UHFFFAOYSA-N 0.000 description 1
JCPPPVWWHKRXJB-UHFFFAOYSA-N 4-[fluoro(phenyl)methyl]-2-(1-methylazepan-4-yl)phthalazin-1-one Chemical compound C1CN(C)CCCC1N1C(=O)C2=CC=CC=C2C(C(F)C=2C=CC=CC=2)=N1 JCPPPVWWHKRXJB-UHFFFAOYSA-N 0.000 description 1
VSINVRRTOCMTHU-UHFFFAOYSA-N 4-chloro-1-(3,4,5-trimethoxyphenyl)butan-1-one Chemical compound COC1=CC(C(=O)CCCCl)=CC(OC)=C1OC VSINVRRTOCMTHU-UHFFFAOYSA-N 0.000 description 1
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
MBUVEWMHONZEQD-UHFFFAOYSA-N Azeptin Chemical compound C1CN(C)CCCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(Cl)=CC=2)=N1 MBUVEWMHONZEQD-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
239000001828 Gelatine Substances 0.000 description 1
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 1
206010065390 Inflammatory pain Diseases 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 description 1
241001274216 Naso Species 0.000 description 1
108010058846 Ovalbumin Proteins 0.000 description 1
238000003684 Perkin reaction Methods 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
150000003855 acyl compounds Chemical class 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
229910021486 amorphous silicon dioxide Inorganic materials 0.000 description 1
239000003708 ampul Substances 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
230000001387 anti-histamine Effects 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
238000005574 benzylation reaction Methods 0.000 description 1
235000019658 bitter taste Nutrition 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000008504 concentrate Nutrition 0.000 description 1
239000012043 crude product Substances 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
WRYCMIFVXDQIKN-UHFFFAOYSA-N desmethylazelastine Chemical compound C1=CC(Cl)=CC=C1CC(C1=CC=CC=C1C1=O)=NN1C1CCNCCC1 WRYCMIFVXDQIKN-UHFFFAOYSA-N 0.000 description 1
RDXABLXNTVBVML-UHFFFAOYSA-N diethoxyphosphanyl diethyl phosphite Chemical compound CCOP(OCC)OP(OCC)OCC RDXABLXNTVBVML-UHFFFAOYSA-N 0.000 description 1
150000004683 dihydrates Chemical class 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000010410 dusting Methods 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
DWJKOGVXRRLNOK-UHFFFAOYSA-N ethyl 4-[4-[(4-fluorophenyl)methyl]-1-oxophthalazin-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1N1C(=O)C2=CC=CC=C2C(CC=2C=CC(F)=CC=2)=N1 DWJKOGVXRRLNOK-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
YSPVHAUJXLGZHP-UHFFFAOYSA-N ethyl piperidine-1-carboxylate Chemical class CCOC(=O)N1CCCCC1 YSPVHAUJXLGZHP-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
150000002429 hydrazines Chemical class 0.000 description 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
150000007857 hydrazones Chemical class 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000008309 hydrophilic cream Substances 0.000 description 1
230000000774 hypoallergenic effect Effects 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
235000015110 jellies Nutrition 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
GWNVDXQDILPJIG-NXOLIXFESA-N leukotriene C4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-NXOLIXFESA-N 0.000 description 1
239000008308 lipophilic cream Substances 0.000 description 1
244000144972 livestock Species 0.000 description 1
239000006210 lotion Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000012875 nonionic emulsifier Substances 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
229940092253 ovalbumin Drugs 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
239000006201 parenteral dosage form Substances 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000008389 polyethoxylated castor oil Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000008707 rearrangement Effects 0.000 description 1
239000013557 residual solvent Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
150000003388 sodium compounds Chemical class 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003511 tertiary amides Chemical class 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
210000004885 white matter Anatomy 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pulmonology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Immunology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

DD86296130A 1985-11-11 1986-11-10 Verfahren zur herstellung von 4-benzyl-1-(2h)-phthalazinon-derivaten DD263058A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3539873		1985-11-11

Publications (1)

Publication Number	Publication Date
DD263058A5 true DD263058A5 (de)	1988-12-21

Family

ID=6285623

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86296130A DD263058A5 (de)	1985-11-11	1986-11-10	Verfahren zur herstellung von 4-benzyl-1-(2h)-phthalazinon-derivaten

Country Status (20)

Country	Link
US (1)	US4841047A (es)
EP (1)	EP0222191B1 (es)
JP (1)	JPH0780871B2 (es)
CN (1)	CN86107627A (es)
AT (1)	ATE60598T1 (es)
AU (1)	AU593593B2 (es)
CA (1)	CA1295613C (es)
DD (1)	DD263058A5 (es)
DE (1)	DE3677322D1 (es)
DK (1)	DK172076B1 (es)
ES (1)	ES2031813T3 (es)
FI (1)	FI88504C (es)
GR (1)	GR3001412T3 (es)
HU (1)	HU196793B (es)
IE (1)	IE59056B1 (es)
IL (1)	IL80560A0 (es)
NO (1)	NO864474L (es)
PT (1)	PT83713B (es)
SU (1)	SU1454251A3 (es)
ZA (1)	ZA868531B (es)

Families Citing this family (34)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT88984B (pt) *	1987-11-13	1993-01-29	Asta Medica Ag	Processo para a preparação de embonato de azelastina e de composições earmacâutxcas que 0 contêm como ingrediente activo
EP0322153A3 (en) *	1987-12-21	1990-08-16	Pfizer Inc.	Heterocyclic oxophtalazinyl acetic acids
FR2643373B1 (fr) *	1989-01-10	1993-12-31	Adir Cie	Nouveaux derives des bisarylalcenes, leurs procedes de preparation et les compositions pharmaceutiques qui les contiennent
EP0396069B1 (de) *	1989-05-05	1994-06-22	ASTA Medica Aktiengesellschaft	Salze des Azelastins mit verbesserter Löslichkeit
JPH04198180A (ja) *	1990-11-28	1992-07-17	Eezai Kagaku Kk	ベンジルフタラゾン誘導体の製造方法
DE4207234A1 (de) *	1992-03-07	1993-09-09	Asta Medica Ag	Neue aminocarbonsaeure-derivate mit antiallergischer/antiasthmatischer wirkung und verfahren zu deren herstellung
EP0561166A1 (de) *	1992-03-17	1993-09-22	ASTA Medica Aktiengesellschaft	Dosieraerosole enthaltend den Wirkstoff D-18024 und verwandte Strukturen
CZ199593A3 (en) *	1992-10-02	1994-04-13	Asta Medica Ag	Phthalazinone derivatives exhibiting anti-arrhythmic and analgesic activity and eliminating resistance to a plurality of medicaments (mdr)
US7151102B2 (en) *	2000-10-30	2006-12-19	Kudos Pharmaceuticals Limited	Phthalazinone derivatives
ES2357057T3 (es) *	2002-04-30	2011-04-15	Kudos Pharmaceuticals Limited	Derivados de ftalazinona.
US7449464B2 (en) *	2003-03-12	2008-11-11	Kudos Pharmaceuticals Limited	Phthalazinone derivatives
GB0305681D0 (en)	2003-03-12	2003-04-16	Kudos Pharm Ltd	Phthalazinone derivatives
GB0419072D0 (en)	2004-08-26	2004-09-29	Kudos Pharm Ltd	Phthalazinone derivatives
US8758816B2 (en)	2004-11-24	2014-06-24	Meda Pharmaceuticals Inc.	Compositions comprising azelastine and methods of use thereof
US20070020330A1 (en) *	2004-11-24	2007-01-25	Medpointe Healthcare Inc.	Compositions comprising azelastine and methods of use thereof
LT2522365T (lt)	2004-11-24	2017-02-10	Meda Pharmaceuticals Inc.	Kompozicijos, apimančios azelastiną, ir jų panaudojimo būdai
GB0428111D0 (en) *	2004-12-22	2005-01-26	Kudos Pharm Ltd	Pthalazinone derivatives
GB0521373D0 (en) *	2005-10-20	2005-11-30	Kudos Pharm Ltd	Pthalazinone derivatives
KR20090007604A (ko) *	2006-04-20	2009-01-19	글락소 그룹 리미티드	히스타민 ｈ１ 및 ｈ３ 길항제로서의 2―치환된 4―벤질프탈라지논 유도체
WO2007144652A2 (en) *	2006-06-15	2007-12-21	Kudos Pharmaceuticals Limited	Parp inhibitors
WO2007144639A1 (en) *	2006-06-15	2007-12-21	Kudos Pharmaceuticals Limited	2 -oxybenzamide derivatives as parp inhibitors
US20090281086A1 (en) *	2006-06-15	2009-11-12	Kudos Pharmaceuticals Limited	2 -oxyheteroarylamide derivatives as parp inhibitors
UY30639A1 (es) *	2006-10-17	2008-05-31	Kudos Pharm Ltd	Derivados sustituidos de 2h-ftalazin-1-ona, sus formas cristalinas, proceso de preparacion y aplicaciones
DE602007005167D1 (de) *	2006-12-20	2010-04-15	Glaxo Group Ltd	4-benzyl-1(2h)-phthalazinone als h1-rezeptor-antagonisten
US20080280910A1 (en) *	2007-03-22	2008-11-13	Keith Allan Menear	Phthalazinone derivatives
TW200900396A (en) *	2007-04-10	2009-01-01	Kudos Pharm Ltd	Phthalazinone derivatives
US20090023727A1 (en) *	2007-07-05	2009-01-22	Muhammad Hashim Javaid	Phthalazinone derivatives
US7981890B2 (en)	2007-09-14	2011-07-19	Astrazeneca Ab	Phthalazinone derivatives
ATE525370T1 (de) *	2007-10-11	2011-10-15	Glaxo Group Ltd	Phthalazin- und pyridoä3,4- düpyridazinverbindungen als h1-rezeptor- antagonisten
EP2212296B1 (en) *	2007-10-17	2014-12-03	Kudos Pharmaceuticals Limited	4- [3- (4-cyclopropanecarbonyl-piperazine-i-carbonyl) -4 -fluoro-benzyl]-2h-phthalaz in-1-one
UY31603A1 (es)	2008-01-23	2009-08-31		Derivados de ftalazinona
MY160340A (en)	2008-10-07	2017-02-28	Astrazeneca Uk Ltd	Pharmaceutical formulation 514
TW201114756A (en) *	2009-07-15	2011-05-01	Astrazeneca Ab	Phthalazinone compound
CN113956239A (zh) *	2021-10-28	2022-01-21	昆明源瑞制药有限公司	一种盐酸氮卓斯汀及其制备方法和应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3017411A (en) *		1962-01-16		New substituted phthalazones and proc-
DE2114884A1 (de) *	1971-03-27	1972-10-12	Cassella Farbwerke Mainkur Ag, 6000 Frankfurt	Basisch substituierte Derivate des 1(2H)-Phthalazinons
US3813384A (en) *	1972-01-17	1974-05-28	Asta Werke Ag Chem Fab	Basically substituted benzyl phthalazone derivatives,acid salts thereof and process for the production thereof
DE3530793A1 (de) *	1984-09-14	1986-03-27	Asta-Werke Ag Chemische Fabrik, 4800 Bielefeld	Substituierte benzylphthalazinon-derivate
ATE49205T1 (de) *	1984-09-14	1990-01-15	Asta Pharma Ag	Substituierte benzylphthalazinon-derivate.

1986
- 1986-10-15 AT AT86114241T patent/ATE60598T1/de active
- 1986-10-15 EP EP86114241A patent/EP0222191B1/de not_active Expired - Lifetime
- 1986-10-15 DE DE8686114241T patent/DE3677322D1/de not_active Expired - Lifetime
- 1986-10-15 ES ES198686114241T patent/ES2031813T3/es not_active Expired - Lifetime
- 1986-11-06 SU SU864028445A patent/SU1454251A3/ru active
- 1986-11-10 US US06/928,458 patent/US4841047A/en not_active Expired - Fee Related
- 1986-11-10 AU AU64982/86A patent/AU593593B2/en not_active Ceased
- 1986-11-10 CN CN198686107627A patent/CN86107627A/zh active Pending
- 1986-11-10 IE IE296086A patent/IE59056B1/en not_active IP Right Cessation
- 1986-11-10 DK DK536486A patent/DK172076B1/da active
- 1986-11-10 DD DD86296130A patent/DD263058A5/de unknown
- 1986-11-10 FI FI864555A patent/FI88504C/fi not_active IP Right Cessation
- 1986-11-10 IL IL80560A patent/IL80560A0/xx unknown
- 1986-11-10 ZA ZA868531A patent/ZA868531B/xx unknown
- 1986-11-10 PT PT83713A patent/PT83713B/pt not_active IP Right Cessation
- 1986-11-10 CA CA000522580A patent/CA1295613C/en not_active Expired - Lifetime
- 1986-11-10 HU HU864642A patent/HU196793B/hu not_active IP Right Cessation
- 1986-11-10 NO NO864474A patent/NO864474L/no unknown
- 1986-11-11 JP JP61266808A patent/JPH0780871B2/ja not_active Expired - Lifetime
1991
- 1991-01-31 GR GR91400092T patent/GR3001412T3/el unknown

Also Published As

Publication number	Publication date
ATE60598T1 (de)	1991-02-15
ES2031813T3 (es)	1993-01-01
AU593593B2 (en)	1990-02-15
CA1295613C (en)	1992-02-11
NO864474D0 (no)	1986-11-10
FI88504C (fi)	1993-05-25
FI864555A7 (fi)	1987-05-12
SU1454251A3 (ru)	1989-01-23
IE862960L (en)	1987-05-11
PT83713B (pt)	1989-06-30
ZA868531B (en)	1987-07-29
US4841047A (en)	1989-06-20
DK536486D0 (da)	1986-11-10
FI88504B (fi)	1993-02-15
CN86107627A (zh)	1987-07-15
HU196793B (en)	1989-01-30
GR3001412T3 (en)	1992-09-25
DK172076B1 (da)	1997-10-13
PT83713A (de)	1986-12-01
HUT42084A (en)	1987-06-29
EP0222191B1 (de)	1991-01-30
IE59056B1 (en)	1993-12-15
FI864555A0 (fi)	1986-11-10
JPS62114987A (ja)	1987-05-26
DE3677322D1 (de)	1991-03-07
DK536486A (da)	1987-05-12
AU6498286A (en)	1987-05-14
EP0222191A1 (de)	1987-05-20
NO864474L (no)	1987-05-12
IL80560A0 (en)	1987-02-27
JPH0780871B2 (ja)	1995-08-30

Publication	Publication Date	Title
DD263058A5 (de)	1988-12-21	Verfahren zur herstellung von 4-benzyl-1-(2h)-phthalazinon-derivaten
DE69325199T2 (de)	1999-12-16	Triazolopyridazine als Antiasthmatika
DE60309057T2 (de)	2007-04-12	Azabicycloderivate als antagonisten des muscarinischen rezeptors
DE2027645A1 (de)	1971-12-09	Piperazinylalkyl chinazolon (4) den vate, Verfahren zu deren Herstellung und sie enthaltende Arzneimittel
DE3443968A1 (de)	1985-10-31	Neue pyridin-2-ether beziehungsweise pyridin-2-thioether mit einem stickstoffhaltigen cycloaliphatischen ring
DE19512639A1 (de)	1996-10-10	Benzonitrile und -fluoride
DE2706977A1 (de)	1978-08-24	Benzoesaeuren und deren derivate sowie verfahren zu ihrer herstellung
DE69330754T2 (de)	2002-07-04	2,5-DIOXO-2,5-DIHYDRO-1H-BENZ[b]AZEPINE ALS NMDA REZEPTOR ANTAGONISTEN
DE69007471T2 (de)	1994-06-23	Verfahren zur verhütung oder zur begrenzung einer reperfusionsschädigung.
DE10046029A1 (de)	2002-03-28	Indazole
DE69130192T2 (de)	1999-03-25	Benzimidazol-Derivate, Verfahren und Zwischenprodukte zu ihrer Herstellung, ihre Anwendung als Arzneimittel und diese enthaltende pharmazeutische Zusammensetzungen
DE2164058B2 (de)	1980-10-23	Basisch substituierte Benzylphthalazinon-Derivate, ihre Salze, Verfahren zu ihrer Herstellung und diese Produkte enthaltende pharmazeutische Präparate
DE3813531A1 (de)	1988-11-10	Neue 2-aminoalkyl-4-benzyl-1-(2h)-phthalazinon-derivate
EP0557879A1 (de)	1993-09-01	4-Amino-2-ureido-pyrimidin-5-carbonsäureamide, Verfahren zu deren Herstellung, diese Verbindungen enthaltende Arzneimittel und deren Verwendung
DE3634942A1 (de)	1987-05-14	Neue 4-benzyl-1-(2h)-phthalazinon-derivate
DE69414716T2 (de)	1999-04-08	Pyridazinonderivate oder deren salze, verfahren zu ihrer herstellung und diese enthaltende antischockmittel
DE3305495A1 (de)	1983-08-18	Piperazin- und homopiperazinderivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische zubereitungen
DE60217934T2 (de)	2007-05-24	Verfahren zur herstellung von desloratadin
EP0171645A1 (de)	1986-02-19	Neue 2H-1-Benzopyran-2-on-Derivate, Verfahren zu ihrer Herstellung und Arzneimittel, die diese Verbindungen enthalten
DE1967080C3 (de)	1979-08-09	t-(3,4-Methylendioxybeiizoyl)-2methyl-5-methoxy-3-indolylessigsäureester, Verfahren zu ihrer Herstellung und Arzneipräparate
DE3132915A1 (de)	1983-03-03	1,5-diphenylpyrazolin-3-on-verbindungen sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE2757532A1 (de)	1979-07-05	N,n'-disubstituiertes cyclisches diamin und verfahren zu dessen herstellung
DE69715196T2 (de)	2003-05-15	Modifizierte form des hydrochlorids der r(-)-n-(4,4-di(-3-methylthien-2-yl)but-3-enyl)-nipecotinsäure
DE2748466A1 (de)	1978-05-03	4a-aryloctahydro-1h-2-pyrindine
EP0289881A2 (de)	1988-11-09	Neue 2-Aminoalkyl-4-bennzyl-1-(2H)-phthalazinon-Derivate