DK169258B1 - Derivater af synergistiner, deres fremstilling og farmaceutiske præparater deraf - Google Patents

Derivater af synergistiner, deres fremstilling og farmaceutiske præparater deraf Download PDF

Info

Publication number: DK169258B1
Authority: DK; Denmark
Prior art keywords: compound; pristinamycin; group; optionally substituted; alkyl
Prior art date: 1983-07-13

Application number

DK342584A

Other languages

Danish (da)

English (en)

Other versions

DK342584A (da

DK342584D0 (da

Inventor

Jean-Pierre Corbet

Claude Cotrel

Daniel Farge

Jean-Marc Paris

Original Assignee

Rhone Poulenc Sante

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.)

1983-07-13

Filing date

1984-07-12

Publication date

1994-09-26

1984-07-12 Application filed by Rhone Poulenc Sante filed Critical Rhone Poulenc Sante

1984-07-12 Publication of DK342584D0 publication Critical patent/DK342584D0/da

1985-01-14 Publication of DK342584A publication Critical patent/DK342584A/da

1994-09-26 Application granted granted Critical

1994-09-26 Publication of DK169258B1 publication Critical patent/DK169258B1/da

Links

238000002360 preparation method Methods 0.000 title claims abstract description 16
239000000825 pharmaceutical preparation Substances 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 167
-1 piperidin-3-ylthio Chemical group 0.000 claims abstract description 151
125000000217 alkyl group Chemical group 0.000 claims abstract description 37
150000003839 salts Chemical class 0.000 claims abstract description 26
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 16
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 12
125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims abstract description 10
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 6
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims abstract description 5
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
239000000203 mixture Substances 0.000 claims description 83
238000000034 method Methods 0.000 claims description 28
229910052757 nitrogen Inorganic materials 0.000 claims description 26
125000004663 dialkyl amino group Chemical group 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 5
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 5
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
125000005358 mercaptoalkyl group Chemical group 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
125000005208 trialkylammonium group Chemical group 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
239000011593 sulfur Substances 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 2
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
229910006069 SO3H Inorganic materials 0.000 abstract 2
125000004574 piperidin-2-yl group Chemical group N1C(CCCC1)* 0.000 abstract 2
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 abstract 2
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 abstract 2
230000000844 anti-bacterial effect Effects 0.000 abstract 1
125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 189
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 139
229960003961 pristinamycin Drugs 0.000 description 122
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 112
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
238000003818 flash chromatography Methods 0.000 description 59
239000000843 powder Substances 0.000 description 59
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 57
239000007864 aqueous solution Substances 0.000 description 54
230000008018 melting Effects 0.000 description 52
238000002844 melting Methods 0.000 description 52
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
238000000746 purification Methods 0.000 description 48
239000012153 distilled water Substances 0.000 description 47
239000000243 solution Substances 0.000 description 42
239000003480 eluent Substances 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
239000004188 Virginiamycin Substances 0.000 description 17
229960003842 virginiamycin Drugs 0.000 description 17
239000007787 solid Substances 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
239000012074 organic phase Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
239000002609 medium Substances 0.000 description 10
239000000047 product Substances 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
108010079780 Pristinamycin Proteins 0.000 description 9
RLNUPSVMIYRZSM-UHFFFAOYSA-N Pristinamycin Natural products CC1OC(=O)C(C=2C=CC=CC=2)NC(=O)C2CC(=O)CCN2C(=O)C(CC=2C=CC(=CC=2)N(C)C)CCN(C)C(=O)C2CCCN2C(=O)C(CC)NC(=O)C1NC(=O)C1=NC=CC=C1O RLNUPSVMIYRZSM-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
229910052943 magnesium sulfate Inorganic materials 0.000 description 9
235000019341 magnesium sulphate Nutrition 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
DAIKHDNSXMZDCU-OUDXUNEISA-N pristinamycin-IIA Natural products CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)c3coc(CC(=O)C[C@H](O)C=C(C)C=CCNC(=O)C=C[C@@H]1C)n3 DAIKHDNSXMZDCU-OUDXUNEISA-N 0.000 description 9
JOOMGSFOCRDAHL-XKCHLWDXSA-N pristinamycin-IIB Natural products CC(C)[C@@H]1OC(=O)[C@H]2CCCN2C(=O)c3coc(CC(=O)C[C@@H](O)C=C(C)C=CCNC(=O)C=C[C@H]1C)n3 JOOMGSFOCRDAHL-XKCHLWDXSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
239000003960 organic solvent Substances 0.000 description 8
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 7
238000010992 reflux Methods 0.000 description 7
229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
235000017557 sodium bicarbonate Nutrition 0.000 description 7
ZGQKIODAYVUFAJ-UHFFFAOYSA-N 3-(dimethylamino)-2-methylpropane-1-thiol Chemical compound SCC(C)CN(C)C ZGQKIODAYVUFAJ-UHFFFAOYSA-N 0.000 description 6
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 6
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
GKXASWWKVLIZQU-UHFFFAOYSA-N 2-(4-methylpiperazin-1-yl)ethanethiol Chemical compound CN1CCN(CCS)CC1 GKXASWWKVLIZQU-UHFFFAOYSA-N 0.000 description 5
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 5
WVKFOTRZWCGTGL-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propane-1-thiol Chemical compound CN1CCN(CCCS)CC1 WVKFOTRZWCGTGL-UHFFFAOYSA-N 0.000 description 5
239000013078 crystal Substances 0.000 description 5
239000000155 melt Substances 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000011734 sodium Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
ALOCUZOKRULSAA-UHFFFAOYSA-N 1-methylpiperidin-4-amine Chemical compound CN1CCC(N)CC1 ALOCUZOKRULSAA-UHFFFAOYSA-N 0.000 description 4
TXVSXWOWWHALFQ-UHFFFAOYSA-N 1-methylpiperidine-4-thiol Chemical compound CN1CCC(S)CC1 TXVSXWOWWHALFQ-UHFFFAOYSA-N 0.000 description 4
HSAYSFNFCZEPCN-UHFFFAOYSA-N 3-(dimethylamino)propane-1-thiol Chemical compound CN(C)CCCS HSAYSFNFCZEPCN-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical compound CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 4
238000001914 filtration Methods 0.000 description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
229960004592 isopropanol Drugs 0.000 description 4
GLZFBHFKBYBYQQ-UHFFFAOYSA-N s-[3-(dimethylamino)-2-methylpropyl] ethanethioate Chemical compound CN(C)CC(C)CSC(C)=O GLZFBHFKBYBYQQ-UHFFFAOYSA-N 0.000 description 4
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
239000000725 suspension Substances 0.000 description 4
TZEGOJBUDGNPBN-UHFFFAOYSA-N (2-methyl-3-sulfanylpropyl)azanium;iodide Chemical compound [I-].[NH3+]CC(C)CS TZEGOJBUDGNPBN-UHFFFAOYSA-N 0.000 description 3
LWOVXABTPFAHBJ-UHFFFAOYSA-N 1,3-bis(dimethylamino)propane-2-thiol Chemical compound CN(C)CC(S)CN(C)C LWOVXABTPFAHBJ-UHFFFAOYSA-N 0.000 description 3
YBDSNEVSFQMCTL-UHFFFAOYSA-N 2-(diethylamino)ethanethiol Chemical compound CCN(CC)CCS YBDSNEVSFQMCTL-UHFFFAOYSA-N 0.000 description 3
WRTWLAYXDHJMNZ-UHFFFAOYSA-N 5-(diethylamino)pentane-2-thiol Chemical compound CCN(CC)CCCC(C)S WRTWLAYXDHJMNZ-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
MVTQIFVKRXBCHS-SMMNFGSLSA-N N-[(3S,6S,12R,15S,16R,19S,22S)-3-benzyl-12-ethyl-4,16-dimethyl-2,5,11,14,18,21,24-heptaoxo-19-phenyl-17-oxa-1,4,10,13,20-pentazatricyclo[20.4.0.06,10]hexacosan-15-yl]-3-hydroxypyridine-2-carboxamide (10R,11R,12E,17E,19E,21S)-21-hydroxy-11,19-dimethyl-10-propan-2-yl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.03,7]octacosa-1(27),6,12,17,19,25(28)-hexaene-2,8,14,23-tetrone Chemical compound CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)c2coc(CC(=O)C[C@H](O)\C=C(/C)\C=C\CNC(=O)\C=C\[C@H]1C)n2.CC[C@H]1NC(=O)[C@@H](NC(=O)c2ncccc2O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@@H]2CC(=O)CCN2C(=O)[C@H](Cc2ccccc2)N(C)C(=O)[C@@H]2CCCN2C1=O)c1ccccc1 MVTQIFVKRXBCHS-SMMNFGSLSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
229960001340 histamine Drugs 0.000 description 3
238000001802 infusion Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
KNNSKVQNJPAGIX-UHFFFAOYSA-N s-[3-(4-methylpiperazin-1-yl)propyl] ethanethioate Chemical compound CN1CCN(CCCSC(C)=O)CC1 KNNSKVQNJPAGIX-UHFFFAOYSA-N 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
JHXYWZPULIFDAM-UHFFFAOYSA-N (3-acetylsulfanyl-2-methylpropyl)azanium;iodide Chemical compound [I-].[NH3+]CC(C)CSC(C)=O JHXYWZPULIFDAM-UHFFFAOYSA-N 0.000 description 2
NICHLBUXOSZKHP-UHFFFAOYSA-N 1-(4-methylpiperazin-1-yl)propane-2-thiol Chemical compound CC(S)CN1CCN(C)CC1 NICHLBUXOSZKHP-UHFFFAOYSA-N 0.000 description 2
CPRRMFGOQJODJL-UHFFFAOYSA-N 1-(dimethylamino)propane-2-thiol Chemical compound CC(S)CN(C)C CPRRMFGOQJODJL-UHFFFAOYSA-N 0.000 description 2
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
YMVAURSKUUIJKT-UHFFFAOYSA-N 1-chloro-n,n,2-trimethylpropan-1-amine Chemical compound CC(C)C(Cl)N(C)C YMVAURSKUUIJKT-UHFFFAOYSA-N 0.000 description 2
BNISDUXYQZTIEV-UHFFFAOYSA-N 1-ethylpiperidine-3-thiol Chemical compound CCN1CCCC(S)C1 BNISDUXYQZTIEV-UHFFFAOYSA-N 0.000 description 2
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
GOWUDHPKGOIDIX-UHFFFAOYSA-N 2-(4-methyl-1-piperazinyl)ethanamine Chemical compound CN1CCN(CCN)CC1 GOWUDHPKGOIDIX-UHFFFAOYSA-N 0.000 description 2
NWIFEWYFKMQGGJ-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropane-1-thiol Chemical compound CN(C)C(C)(C)CS NWIFEWYFKMQGGJ-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
SYPJZNPUWFMUFU-UHFFFAOYSA-N 2-[4-(2-sulfanylethyl)piperazin-1-yl]ethanethiol Chemical compound SCCN1CCN(CCS)CC1 SYPJZNPUWFMUFU-UHFFFAOYSA-N 0.000 description 2
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
FJOXVWJOCNVDDI-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanethiol Chemical compound SCCN1CCCC1 FJOXVWJOCNVDDI-UHFFFAOYSA-N 0.000 description 2
DGPJCGYGCKOVJK-UHFFFAOYSA-N 4-chloro-n,n-diethylpentan-1-amine Chemical compound CCN(CC)CCCC(C)Cl DGPJCGYGCKOVJK-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
239000004472 Lysine Substances 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
MXPRJNWZZIMYNN-UHFFFAOYSA-N ethyl 2-sulfanylethyl carbonate Chemical compound CCOC(=O)OCCS MXPRJNWZZIMYNN-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
125000005844 heterocyclyloxy group Chemical group 0.000 description 2
239000003701 inert diluent Substances 0.000 description 2
229940102223 injectable solution Drugs 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
229960003975 potassium Drugs 0.000 description 2
229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
235000015497 potassium bicarbonate Nutrition 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/19—Antibiotic
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/27—Cyclic peptide or cyclic protein

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Public Health (AREA)
Oncology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Saccharide Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Indole Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Suspension Of Electric Lines Or Cables (AREA)
Measurement Of Force In General (AREA)
Emergency Protection Circuit Devices (AREA)
Plural Heterocyclic Compounds (AREA)

DK342584A 1983-07-13 1984-07-12 Derivater af synergistiner, deres fremstilling og farmaceutiske præparater deraf DK169258B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR8311705A FR2549063B1 (fr)	1983-07-13	1983-07-13	Nouveaux derives de synergistines, leur preparation et les compositions pharmaceutiques qui les contiennent
FR8311705		1983-07-13

Publications (3)

Publication Number	Publication Date
DK342584D0 DK342584D0 (da)	1984-07-12
DK342584A DK342584A (da)	1985-01-14
DK169258B1 true DK169258B1 (da)	1994-09-26

Family

ID=9290812

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK342584A DK169258B1 (da)	1983-07-13	1984-07-12	Derivater af synergistiner, deres fremstilling og farmaceutiske præparater deraf

Country Status (17)

Country	Link
US (1)	US4618599A (ru)
EP (1)	EP0133097B1 (ru)
JP (1)	JPS6038386A (ru)
KR (1)	KR910005848B1 (ru)
AT (1)	ATE25691T1 (ru)
AU (1)	AU567570B2 (ru)
CA (1)	CA1213583A (ru)
DE (1)	DE3462507D1 (ru)
DK (1)	DK169258B1 (ru)
ES (3)	ES534313A0 (ru)
FI (2)	FI78105C (ru)
FR (1)	FR2549063B1 (ru)
GR (1)	GR81555B (ru)
IL (1)	IL72397A (ru)
PT (1)	PT78894B (ru)
SU (3)	SU1421260A3 (ru)
ZA (1)	ZA845316B (ru)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2549065B1 (fr) *	1983-07-13	1985-10-25	Rhone Poulenc Sante	Nouveaux derives de synergistines, leur preparation et les compositions pharmaceutiques qui les contiennent
FR2599036B1 (fr) *	1986-05-22	1988-09-09	Rhone Poulenc Sante	Nouveaux derives de synergistines, leur preparation et les compositions pharmaceutiques qui les contiennent
FR2655343B1 (fr) *	1989-12-05	1992-05-07	Rhone Poulenc Sante	Procede de preparation de synergistine.
FR2664894A1 (fr) *	1990-07-19	1992-01-24	Rhone Poulenc Sante	Nouveaux derives de streptogramines et leur preparation.
IL121821A (en) *	1993-02-17	2000-02-17	Rhone Poulenc Rorer Sa	Process for purifying a group A minority component of streptogramin some such purified components and their uses
FR2723373B1 (fr)	1994-08-02	1996-09-13	Rhone Poulenc Rorer Sa	Forme purifiee de streptogramines, sa preparation et les compositions pharmaceutiques qui la contiennent
FR2796949B1 (fr) *	1999-07-27	2001-09-21	Aventis Pharma Sa	Derives de streptogramines, leur preparation et les compositions qui les contiennent
CN101273042B (zh) *	2005-07-29	2013-11-06	泰博特克药品有限公司	丙型肝炎病毒的大环抑制剂
JP2008057849A (ja) *	2006-08-31	2008-03-13	Denso Corp	熱交換器の製造方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4355112A (en) *	1977-06-06	1982-10-19	Sanraku-Ocean Co., Ltd.	Streptomyces culture

1983
- 1983-07-13 FR FR8311705A patent/FR2549063B1/fr not_active Expired
1984
- 1984-07-10 AU AU30472/84A patent/AU567570B2/en not_active Ceased
- 1984-07-10 ZA ZA845316A patent/ZA845316B/xx unknown
- 1984-07-11 GR GR75264A patent/GR81555B/el unknown
- 1984-07-11 KR KR1019840004023A patent/KR910005848B1/ko not_active Expired
- 1984-07-12 FI FI842812A patent/FI78105C/fi not_active IP Right Cessation
- 1984-07-12 CA CA000458721A patent/CA1213583A/fr not_active Expired
- 1984-07-12 DK DK342584A patent/DK169258B1/da not_active IP Right Cessation
- 1984-07-12 SU SU843760756A patent/SU1421260A3/ru active
- 1984-07-12 JP JP59143403A patent/JPS6038386A/ja active Granted
- 1984-07-12 EP EP84401478A patent/EP0133097B1/fr not_active Expired
- 1984-07-12 PT PT78894A patent/PT78894B/pt unknown
- 1984-07-12 AT AT84401478T patent/ATE25691T1/de not_active IP Right Cessation
- 1984-07-12 US US06/630,288 patent/US4618599A/en not_active Expired - Lifetime
- 1984-07-12 IL IL8472397A patent/IL72397A/xx unknown
- 1984-07-12 DE DE8484401478T patent/DE3462507D1/de not_active Expired
- 1984-07-13 ES ES534313A patent/ES534313A0/es active Granted
- 1984-10-29 ES ES537180A patent/ES8601211A1/es not_active Expired
- 1984-10-29 ES ES537179A patent/ES537179A0/es active Granted
1985
- 1985-12-06 SU SU853984703A patent/SU1456019A3/ru active
- 1985-12-06 SU SU853984289A patent/SU1445560A3/ru active
1987
- 1987-10-22 FI FI874654A patent/FI80456C/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
FI78105B (fi)	1989-02-28
FI78105C (fi)	1989-06-12
ES8601210A1 (es)	1985-10-16
IL72397A0 (en)	1984-11-30
ES8504201A1 (es)	1985-04-01
FR2549063B1 (fr)	1985-10-25
US4618599A (en)	1986-10-21
ES537180A0 (es)	1985-10-16
AU3047284A (en)	1985-01-17
AU567570B2 (en)	1987-11-26
GR81555B (ru)	1984-12-11
FI842812A7 (fi)	1985-01-14
ES537179A0 (es)	1985-10-16
SU1456019A3 (ru)	1989-01-30
PT78894B (fr)	1986-08-08
FI874654A0 (fi)	1987-10-22
SU1421260A3 (ru)	1988-08-30
EP0133097A1 (fr)	1985-02-13
FR2549063A1 (fr)	1985-01-18
FI80456B (fi)	1990-02-28
IL72397A (en)	1987-10-30
DK342584A (da)	1985-01-14
DK342584D0 (da)	1984-07-12
DE3462507D1 (en)	1987-04-09
ES534313A0 (es)	1985-04-01
EP0133097B1 (fr)	1987-03-04
FI874654A7 (fi)	1987-10-22
FI80456C (fi)	1990-06-11
ATE25691T1 (de)	1987-03-15
KR850001212A (ko)	1985-03-16
JPS6038386A (ja)	1985-02-27
CA1213583A (fr)	1986-11-04
ZA845316B (en)	1985-02-27
FI842812A0 (fi)	1984-07-12
ES8601211A1 (es)	1985-10-16
JPH0522718B2 (ru)	1993-03-30
SU1445560A3 (ru)	1988-12-15
PT78894A (fr)	1984-08-01
KR910005848B1 (ko)	1991-08-05

Legal Events

Date	Code	Title	Description
1994-09-26	B1	Patent granted (law 1993)
2004-08-02	PUP	Patent expired

Publication	Publication Date	Title
US5492916A (en)	1996-02-20	Di- and tri-substituted piperidines, pyrrolidines and hexahydro-1H-azepines promote release of growth hormone
US6121325A (en)	2000-09-19	Naphthyl compounds promote release of growth hormone
SU753358A3 (ru)	1980-07-30	Способ получени пептидов
US4742057A (en)	1988-05-03	Antiallergic thiazole compounds
DK169258B1 (da)	1994-09-26	Derivater af synergistiner, deres fremstilling og farmaceutiske præparater deraf
US4376774A (en)	1983-03-15	Antibiotic N-heterocyclyl thienamycin
US4668669A (en)	1987-05-26	Pristinamycin IIB derivatives and compositions containing them
KR910002842B1 (ko)	1991-05-06	신규한 프리스티나마이신 유도체의 제조방법
US5254682A (en)	1993-10-19	Cyclic renin inhibitors containing 3(S)-amino-4-cyclohexyl-2(R)-hydroxy-butanoic acid or 4-cyclo-hexyl-(2R, 3S)-dihydroxybutanoic acid or related analogs
EP0662957B1 (en)	1997-11-05	1,4-disubstituted piperazines useful in the therapy of the asthma and of the inflammation of the respiratory tract
DK172949B1 (da)	1999-10-11	Synergistinderivater, deres fremstilling og farmaceutiske præparater deraf
EP0758328B1 (en)	2003-07-16	Anti-cancer compounds containing cyclopentaquinazoline ring
US4512988A (en)	1985-04-23	Acylamino oxo or hydroxy substituted alkylamino thiazines and thiazepines
CS252832B2 (en)	1987-10-15	Method of heterocyclic compounds production substitud by peptide residue
GB2206879A (en)	1989-01-18	Novel pristinamycin IIB derivatives, their preparation and pharmaceutical compositions containing them
US4617377A (en)	1986-10-14	Synergistine derivatives and their preparation
HU197748B (en)	1989-05-29	Process for producing carbapenem derivatives substituted at the 2-position by quaternizated pyridylthioalkylthio group and pharmaceuticals comprising same as active ingredient
US4427581A (en)	1984-01-24	Peptide, process for preparation thereof and use thereof
EP0050856B1 (en)	1984-12-27	New peptide, process for its preparation and pharmaceutical composition containing it
JPS60185762A (ja)	1985-09-21	プロリン誘導体
PT85206B (pt)	1992-07-31	Processo para a preparacao de pirrolidinomas substituidas