NO841163L - Nye n-fenyl-n`-cykloalkylalkanoyl-piperaziner, og fremgangsmaate til deres fremstilling - Google Patents

Nye n-fenyl-n`-cykloalkylalkanoyl-piperaziner, og fremgangsmaate til deres fremstilling

Info

Publication number: NO841163L
Authority: NO; Norway
Prior art keywords: group; residue; groups; radical; phenyl
Prior art date: 1983-03-25

Application number

NO841163A

Other languages

English (en)

Norwegian (no)

Inventor

Gerhard Oepen

Juergen Engel

Vladimir Jakovlev

Klaus Thiemer

Original Assignee

Degussa

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.)

1983-03-25

Filing date

1984-03-23

Publication date

1984-09-26

1984-03-23 Application filed by Degussa filed Critical Degussa

1984-09-26 Publication of NO841163L publication Critical patent/NO841163L/no

Links

238000000034 method Methods 0.000 title claims description 16
238000002360 preparation method Methods 0.000 title claims description 5
150000004885 piperazines Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 46
229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 10
239000000460 chlorine Substances 0.000 claims abstract description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052794 bromium Inorganic materials 0.000 claims abstract description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 4
125000003277 amino group Chemical group 0.000 claims abstract description 4
229910052731 fluorine Inorganic materials 0.000 claims abstract description 4
239000011737 fluorine Substances 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims abstract description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 4
229920006395 saturated elastomer Polymers 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
239000002253 acid Substances 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 8
125000003373 pyrazinyl group Chemical group 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 abstract 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 28
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
239000000203 mixture Substances 0.000 description 22
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000003513 alkali Substances 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
125000000217 alkyl group Chemical group 0.000 description 14
-1 Piperazine compound Chemical class 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 13
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
239000003814 drug Substances 0.000 description 8
230000000694 effects Effects 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
239000013543 active substance Substances 0.000 description 6
238000005804 alkylation reaction Methods 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000000126 substance Substances 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
230000029936 alkylation Effects 0.000 description 5
150000004649 carbonic acid derivatives Chemical class 0.000 description 5
229940079593 drug Drugs 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
230000010933 acylation Effects 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
230000001476 alcoholic effect Effects 0.000 description 4
229910001854 alkali hydroxide Inorganic materials 0.000 description 4
150000008044 alkali metal hydroxides Chemical class 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
230000000202 analgesic effect Effects 0.000 description 4
230000037396 body weight Effects 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000000746 purification Methods 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
PZIBVWUXWNYTNL-UHFFFAOYSA-N 1-(3-methoxyphenyl)piperazine Chemical compound COC1=CC=CC(N2CCNCC2)=C1 PZIBVWUXWNYTNL-UHFFFAOYSA-N 0.000 description 3
JUADTOTVJUYCRQ-UHFFFAOYSA-N 3-cyclohexylpropanoyl chloride Chemical compound ClC(=O)CCC1CCCCC1 JUADTOTVJUYCRQ-UHFFFAOYSA-N 0.000 description 3
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
125000002252 acyl group Chemical group 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
125000002723 alicyclic group Chemical group 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
229910052799 carbon Inorganic materials 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
HJZLEGIHUQOJBA-UHFFFAOYSA-N cyclohexane propionic acid Chemical compound OC(=O)CCC1CCCCC1 HJZLEGIHUQOJBA-UHFFFAOYSA-N 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
239000003480 eluent Substances 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 3
239000008096 xylene Substances 0.000 description 3
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 2
RRCBMWDMWLJRAV-UHFFFAOYSA-N 1-[4-(2-aminophenyl)piperazin-1-yl]-3-cyclohexylpropan-1-one Chemical compound NC1=CC=CC=C1N1CCN(C(=O)CCC2CCCCC2)CC1 RRCBMWDMWLJRAV-UHFFFAOYSA-N 0.000 description 2
IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 2
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 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
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
208000002193 Pain Diseases 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000000370 acceptor Substances 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
150000001242 acetic acid derivatives Chemical class 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
125000003302 alkenyloxy group Chemical group 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229940035676 analgesics Drugs 0.000 description 2
239000000730 antalgic agent Substances 0.000 description 2
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
239000000010 aprotic solvent Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
125000003118 aryl group Chemical group 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
239000002585 base Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 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
239000002775 capsule Substances 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
125000000068 chlorophenyl group Chemical group 0.000 description 2
150000004292 cyclic ethers Chemical class 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000008298 dragée Substances 0.000 description 2
239000006196 drop Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000012467 final product Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
239000011630 iodine Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
230000036407 pain Effects 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
239000000825 pharmaceutical preparation Substances 0.000 description 2
239000006187 pill Substances 0.000 description 2
125000004193 piperazinyl group Chemical group 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
235000017550 sodium carbonate Nutrition 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
150000003388 sodium compounds Chemical class 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000003826 tablet Substances 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
125000004417 unsaturated alkyl group Chemical group 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
125000004178 (C1-C4) alkyl 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
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
AXOFFTWUWPCDGJ-UHFFFAOYSA-N 2,2-dichloroethanamine;hydrochloride Chemical compound Cl.NCC(Cl)Cl AXOFFTWUWPCDGJ-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
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
YWCZQSUDAPCKRG-UHFFFAOYSA-N 3-cyclohexyl-1-[4-(2-propoxyphenyl)piperazin-1-yl]propan-1-one Chemical compound CCCOC1=CC=CC=C1N1CCN(C(=O)CCC2CCCCC2)CC1 YWCZQSUDAPCKRG-UHFFFAOYSA-N 0.000 description 1
MZLVBPWJRGVASD-UHFFFAOYSA-N 3-cyclohexyl-1-[4-(3-methoxyphenyl)piperazin-1-yl]propan-1-one Chemical compound COC1=CC=CC(N2CCN(CC2)C(=O)CCC2CCCCC2)=C1 MZLVBPWJRGVASD-UHFFFAOYSA-N 0.000 description 1
BMHCBXXRCCTXEO-UHFFFAOYSA-N 3-cyclohexyl-1-[4-[2-(methylamino)phenyl]piperazin-1-yl]propan-1-one Chemical compound CNC1=CC=CC=C1N1CCN(C(=O)CCC2CCCCC2)CC1 BMHCBXXRCCTXEO-UHFFFAOYSA-N 0.000 description 1
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 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
229940090248 4-hydroxybenzoic acid Drugs 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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010003591 Ataxia Diseases 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-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
241000282326 Felis catus Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
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208000004550 Postoperative Pain Diseases 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
206010039897 Sedation Diseases 0.000 description 1
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229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000005236 alkanoylamino group Chemical group 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
150000001347 alkyl bromides Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 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
150000001412 amines Chemical class 0.000 description 1
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229960004909 aminosalicylic acid Drugs 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000003708 ampul Substances 0.000 description 1
230000036592 analgesia Effects 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
230000008485 antagonism Effects 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
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239000007900 aqueous suspension Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
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230000001977 ataxic effect Effects 0.000 description 1
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235000010233 benzoic acid Nutrition 0.000 description 1
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PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
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125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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230000000994 depressogenic effect Effects 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
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239000000428 dust Substances 0.000 description 1
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235000019439 ethyl acetate Nutrition 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
230000027119 gastric acid secretion Effects 0.000 description 1
239000000499 gel Substances 0.000 description 1
150000005826 halohydrocarbons Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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238000005984 hydrogenation reaction Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-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
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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PPALFHZGSIENQB-UHFFFAOYSA-N methyl 3-cyclohexylpropanoate Chemical compound COC(=O)CCC1CCCCC1 PPALFHZGSIENQB-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
229960004127 naloxone Drugs 0.000 description 1
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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
125000001624 naphthyl group Chemical group 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000000945 opiatelike Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 description 1
229960005301 pentazocine Drugs 0.000 description 1
229960000482 pethidine Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229940072033 potash Drugs 0.000 description 1
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000003222 pyridines Chemical class 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
238000001953 recrystallisation Methods 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
230000036280 sedation Effects 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
150000003511 tertiary amides Chemical class 0.000 description 1
238000010998 test method Methods 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
229940125725 tranquilizer Drugs 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
150000003628 tricarboxylic acids Chemical class 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
230000007306 turnover Effects 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 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
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
- 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
- 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
- C07D241/20—Nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Pain & Pain Management (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Rheumatology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Photoreceptors In Electrophotography (AREA)
Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pyridine Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)

NO841163A 1983-03-25 1984-03-23 Nye n-fenyl-n`-cykloalkylalkanoyl-piperaziner, og fremgangsmaate til deres fremstilling NO841163L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3310871		1983-03-25

Publications (1)

Publication Number	Publication Date
NO841163L true NO841163L (no)	1984-09-26

Family

ID=6194617

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO841163A NO841163L (no)	1983-03-25	1984-03-23	Nye n-fenyl-n`-cykloalkylalkanoyl-piperaziner, og fremgangsmaate til deres fremstilling

Country Status (17)

Country	Link
US (1)	US4547505A (fi)
EP (1)	EP0120465B1 (fi)
JP (1)	JPS59205362A (fi)
AT (1)	ATE20887T1 (fi)
AU (1)	AU560579B2 (fi)
CA (1)	CA1211435A (fi)
DD (1)	DD213215A5 (fi)
DE (1)	DE3460325D1 (fi)
DK (1)	DK142084A (fi)
ES (2)	ES530902A0 (fi)
FI (1)	FI841181A (fi)
HU (1)	HU191643B (fi)
IL (1)	IL71324A (fi)
NO (1)	NO841163L (fi)
PT (1)	PT78304B (fi)
SU (1)	SU1297727A3 (fi)
ZA (1)	ZA842185B (fi)

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EP0533240A3 (en) *	1991-09-16	1993-09-29	Merck & Co. Inc.	Substituted amine derivatives of piperazinylcamphorsulfonyl oxytocin antagonists
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EP0533241A3 (en) *	1991-09-16	1993-09-29	Merck & Co. Inc.	Substituted alkyl derivatives of piperazinylcamphorsulfonyl oxytocin antagonists
JPH05255089A (ja) *	1991-12-18	1993-10-05	Sanwa Kagaku Kenkyusho Co Ltd	抗ウイルス剤
HU209678B (en) *	1992-06-09	1994-10-28	Richter Gedeon Vegyeszet	Process for producing biologically active eburnamenin-14-carbonyl-amino derivatives and pharmaceutical compositions containing them
EP0708765A4 (en) *	1993-07-16	1996-06-26	Merck & Co Inc	PIPERAZINYLCAMPHER DERIVATIVES SUBSTITUTED AS OXYTOCIN ANTAGONISTS
ES2125206B1 (es) *	1997-07-21	1999-11-16	Esteve Labor Dr	Derivados de acil-piperazinil-pirimidinas, su preparacion y su aplicacion como medicamentos.
ES2167276B1 (es) *	2000-10-20	2003-04-01	Esteve Labor Dr	Nuevos derivados de cianoaril (o cianoheteroaril)-carbonil-piperazinil-pirimidinas, su preparacion y su aplicacion como medicamentos.
US7589199B2 (en)	2002-06-12	2009-09-15	Chemocentryx, Inc.	Substituted piperazines
US20050256130A1 (en) *	2002-06-12	2005-11-17	Chemocentryx, Inc.	Substituted piperazines
KR101255356B1 (ko)	2002-06-12	2013-04-17	케모센트릭스, 인크.	염증 및 면역 질병의 치료를 위한 ｃｃｒ１ 길항물질로서사용하기 위한 1-아릴-4-치환된 피페라진 유도체
US7842693B2 (en) *	2002-06-12	2010-11-30	Chemocentryx, Inc.	Substituted piperazines
US8013156B2 (en) *	2003-03-19	2011-09-06	Exelixis, Inc.	Tie-2 modulators and methods of use
JP4845873B2 (ja) *	2004-03-03	2011-12-28	ケモセントリックスインコーポレーティッド	二環式および架橋した窒素複素環
US7435831B2 (en) *	2004-03-03	2008-10-14	Chemocentryx, Inc.	Bicyclic and bridged nitrogen heterocycles
US8389510B2 (en) *	2005-11-18	2013-03-05	Astrazeneca Ab	Crystalline forms
CN101616585A (zh) *	2006-12-20	2009-12-30	阿斯利康(瑞典)有限公司	化合物及其用途
PL2195293T3 (pl) *	2007-08-22	2014-03-31	Astrazeneca Ab	Pochodne cyklopropyloamidu
TW201039825A (en) *	2009-02-20	2010-11-16	Astrazeneca Ab	Cyclopropyl amide derivatives 983
NZ602110A (en)	2010-02-18	2014-09-26	Astrazeneca Ab	Processes for making cyclopropyl amide derivatives and intermediates associated therewith
KR20130034009A (ko) *	2010-02-18	2013-04-04	아스트라제네카 아베	시클로프로필 아미드 유도체를 포함하는 고체 형태
FR3000065A1 (fr)	2012-12-21	2014-06-27	Univ Lille Ii Droit & Sante	Composes bicycliques ayant une activite potentialisatrice de l'activite d'un antibiotique actif contre les mycobacteries-composition et produit pharmaceutiques comprenant de tels composes
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JPS52286A (en) *	1975-05-27	1977-01-05	Kyorin Pharmaceut Co Ltd	Method of preparing 1-(3-phenylpropyl)-4-acylpiperazine derivatives
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US4666911A (en) *	1981-07-14	1987-05-19	Taiho Pharmaceutical Company Limited	Allophanoylpiperazine compound and analgesic composition containing same as active ingredient
JPS591474A (ja) *	1982-06-07	1984-01-06	Nippon Iyakuhin Kogyo Kk	ピペラジン環を有するゲラニルゲラニル酢酸アミド化合物またはその塩類

1984
- 1984-02-24 US US06/583,324 patent/US4547505A/en not_active Expired - Fee Related
- 1984-02-29 DK DK142084A patent/DK142084A/da not_active Application Discontinuation
- 1984-03-21 JP JP59052465A patent/JPS59205362A/ja active Pending
- 1984-03-22 DE DE8484103136T patent/DE3460325D1/de not_active Expired
- 1984-03-22 DD DD84261152A patent/DD213215A5/de unknown
- 1984-03-22 EP EP84103136A patent/EP0120465B1/de not_active Expired
- 1984-03-22 AT AT84103136T patent/ATE20887T1/de not_active IP Right Cessation
- 1984-03-23 NO NO841163A patent/NO841163L/no unknown
- 1984-03-23 IL IL71324A patent/IL71324A/xx not_active IP Right Cessation
- 1984-03-23 HU HU841168A patent/HU191643B/hu unknown
- 1984-03-23 ZA ZA842185A patent/ZA842185B/xx unknown
- 1984-03-23 ES ES530902A patent/ES530902A0/es active Granted
- 1984-03-23 CA CA000450313A patent/CA1211435A/en not_active Expired
- 1984-03-23 AU AU26057/84A patent/AU560579B2/en not_active Ceased
- 1984-03-23 PT PT78304A patent/PT78304B/pt unknown
- 1984-03-23 ES ES530901A patent/ES8501383A1/es not_active Expired
- 1984-03-23 SU SU843713674A patent/SU1297727A3/ru active
- 1984-03-23 FI FI841181A patent/FI841181A/fi not_active Application Discontinuation

Also Published As

Publication number	Publication date
FI841181A (fi)	1984-09-26
HU191643B (en)	1987-03-30
EP0120465B1 (de)	1986-07-23
DE3460325D1 (en)	1986-08-28
SU1297727A3 (ru)	1987-03-15
ES530901A0 (es)	1984-11-16
DK142084A (da)	1984-09-26
ZA842185B (en)	1984-10-31
IL71324A (en)	1987-08-31
IL71324A0 (en)	1984-06-29
US4547505A (en)	1985-10-15
PT78304A (de)	1984-04-01
AU560579B2 (en)	1987-04-09
CA1211435A (en)	1986-09-16
DK142084D0 (da)	1984-02-29
DD213215A5 (de)	1984-09-05
FI841181A0 (fi)	1984-03-23
JPS59205362A (ja)	1984-11-20
ES8501384A1 (es)	1984-11-16
AU2605784A (en)	1984-09-27
EP0120465A1 (de)	1984-10-03
ES530902A0 (es)	1984-11-16
PT78304B (de)	1986-04-22
ATE20887T1 (de)	1986-08-15
ES8501383A1 (es)	1984-11-16

Publication	Publication Date	Title
NO841163L (no)	1984-09-26	Nye n-fenyl-n`-cykloalkylalkanoyl-piperaziner, og fremgangsmaate til deres fremstilling
CA2874938C (en)	2021-02-23	Heterocycles capable of modulating t-cell responses, and methods of using same
KR100254105B1 (ko)	2000-05-01	치환피페리딘유도체
AU2010200815B2 (en)	2015-05-07	New benzothiadiazepine compounds, a process for their preparation and pharmaceutical compositions containing them
KR101178658B1 (ko)	2012-08-30	오렉신 길항제로서의 설폰아마이드
NZ212856A (en)	1988-05-30	Glutarimide derivatives and pharmaceutical compositions
KR20070050076A (ko)	2007-05-14	아미도 화합물 및 약제로서의 이의 용도
CA2180238A1 (en)	1995-07-13	Novel heterocyclic compounds
JPH10506922A (ja)	1998-07-07	２−ウレイド−ベンズアミド誘導体
JPH0597805A (ja)	1993-04-20	新規シクロヘキシルベンズアミド誘導体、それらの調製法及びそれらの医薬への適用
WO2010077976A2 (en)	2010-07-08	Prokineticin receptor antagonists and uses thereof
Gupta et al.	2005	A convenient one pot synthesis of fentanyl
RU2039043C1 (ru)	1995-07-09	Производное n-замещенного 1-гексил-4-фенил-4-пиперидинкарбоксамида или его фармацевтически приемлемая соль и способ его получения
NO160995B (no)	1989-03-13	Analogifremgangsmaate for fremstilling av terapeutisk aktive bis -(4-aminofenyl)-sulfoner.
UA116542C2 (uk)	2018-04-10	Сполуки сечовини та їх застосування як інгібіторів ферментів
FI67373C (fi)	1985-03-11	Foerfarande foer framstaellning av 6,7-bensomorfanderivat vilka aer anvaendbara som analgetiska medel antagonister foer nakotiska medel och inhibitorer foer sekretion av det luten isrande hormonet
Leclerc et al.	1998	Synthesis and structure–activity relationships of novel naphthalenic and bioisosteric related amidic derivatives as melatonin receptor ligands
US3882236A (en)	1975-05-06	Pharmaceutical compositions containing substituted 2-oxo-indolines and the use thereof to treat anxiety and tension
US6362203B1 (en)	2002-03-26	4-hydroxy-4-phenylpiperidine derivatives and pharmaceuticals containing the same
US4032658A (en)	1977-06-28	Alkanolamine derivatives
US3953449A (en)	1976-04-27	2-(4-M-CF3 or -SCF3 phenylpiperazino)-ethyl benzoates
CS203940B2 (en)	1981-03-31	Process for preparing aryloktahydropyridines
CS268189B2 (en)	1990-03-14	Method of quinazolinediones and pyridopyrimidinodiones production
CA1148150A (en)	1983-06-14	Phenylmorphans, intermediates and method of preparation
US4123531A (en)	1978-10-31	Anti-convulsant N-ethanolamine diphenyl acetamides