DD287495A5 - Verfahren zur herstellung herterozyclischer stickstoffverbindungen - Google Patents

Verfahren zur herstellung herterozyclischer stickstoffverbindungen Download PDF

Info

Publication number: DD287495A5
Authority: DD; German Democratic Republic
Prior art keywords: lower alkyl; carboxy; hydrogen; formula; compound
Prior art date: 1987-02-10

Application number

DD88312758A

Other languages

German (de)

English (en)

Inventor

Eva Winter-Mihaly

Christian Borel

Andre J Weith

Original Assignee

��@��k��

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-02-10

Filing date

1988-02-08

Publication date

1991-02-28

1988-02-08 Application filed by ��@��k�� filed Critical ��@��k��

1991-02-28 Publication of DD287495A5 publication Critical patent/DD287495A5/de

Links

229910017464 nitrogen compound Inorganic materials 0.000 title abstract description 4
238000004519 manufacturing process Methods 0.000 title description 2
150000002830 nitrogen compounds Chemical class 0.000 title 1
-1 heterocyclic nitrogen compounds Chemical class 0.000 claims abstract description 115
150000001875 compounds Chemical class 0.000 claims abstract description 106
238000000034 method Methods 0.000 claims abstract description 25
125000001424 substituent group Chemical group 0.000 claims abstract description 14
230000008569 process Effects 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims description 107
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 59
150000003839 salts Chemical class 0.000 claims description 52
239000001257 hydrogen Substances 0.000 claims description 42
229910052739 hydrogen Inorganic materials 0.000 claims description 42
239000000203 mixture Substances 0.000 claims description 42
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
125000003545 alkoxy group Chemical group 0.000 claims description 26
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims description 25
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 15
125000004185 ester group Chemical group 0.000 claims description 15
125000000753 cycloalkyl group Chemical group 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 11
229910052757 nitrogen Inorganic materials 0.000 claims description 11
125000004580 4,5-dihydroimidazol-2-yl group Chemical group N1C(=NCC1)* 0.000 claims description 9
125000001072 heteroaryl group Chemical group 0.000 claims description 9
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 9
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 8
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 8
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 7
230000003287 optical effect Effects 0.000 claims description 7
125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 6
125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 6
125000001841 imino group Chemical group [H]N=* 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
238000000926 separation method Methods 0.000 claims description 4
AOENMVXVGUYPCW-UHFFFAOYSA-N 6-(2h-tetrazol-5-yl)pyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1C1=NN=NN1 AOENMVXVGUYPCW-UHFFFAOYSA-N 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
LVPMIMZXDYBCDF-UHFFFAOYSA-N isocinchomeronic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)N=C1 LVPMIMZXDYBCDF-UHFFFAOYSA-N 0.000 claims description 3
125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 claims description 3
LODYAHPUNWFYFQ-UHFFFAOYSA-N 1-(2h-tetrazol-5-yl)isoquinoline-4-carboxylic acid Chemical compound C12=CC=CC=C2C(C(=O)O)=CN=C1C1=NN=NN1 LODYAHPUNWFYFQ-UHFFFAOYSA-N 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000006501 nitrophenyl group Chemical group 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
UJOCDFJTDHRUHQ-UHFFFAOYSA-N hexadecyl 6-(2h-tetrazol-5-yl)pyridine-3-carboxylate Chemical compound N1=CC(C(=O)OCCCCCCCCCCCCCCCC)=CC=C1C1=NN=NN1 UJOCDFJTDHRUHQ-UHFFFAOYSA-N 0.000 claims 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 11
230000003510 anti-fibrotic effect Effects 0.000 abstract description 3
239000003814 drug Chemical class 0.000 abstract description 3
230000000144 pharmacologic effect Effects 0.000 abstract description 3
150000003222 pyridines Chemical class 0.000 abstract description 3
229940079593 drug Drugs 0.000 abstract description 2
239000004615 ingredient Substances 0.000 abstract 1
125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
239000000243 solution Substances 0.000 description 58
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 21
238000001816 cooling Methods 0.000 description 20
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 19
239000004480 active ingredient Substances 0.000 description 17
125000002252 acyl group Chemical group 0.000 description 17
239000011734 sodium Substances 0.000 description 17
229910052708 sodium Inorganic materials 0.000 description 17
239000002253 acid Substances 0.000 description 14
239000002244 precipitate Substances 0.000 description 14
150000003254 radicals Chemical class 0.000 description 14
125000004093 cyano group Chemical group *C#N 0.000 description 13
239000007858 starting material Substances 0.000 description 13
WMHSQCDPPJRWIL-UHFFFAOYSA-N 6-cyanopyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(C#N)N=C1 WMHSQCDPPJRWIL-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 11
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
239000007787 solid Substances 0.000 description 9
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
238000004440 column chromatography Methods 0.000 description 8
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 8
125000000623 heterocyclic group Chemical group 0.000 description 7
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
238000011282 treatment Methods 0.000 description 7
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 6
150000008064 anhydrides Chemical class 0.000 description 6
239000013078 crystal Substances 0.000 description 6
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
238000010992 reflux Methods 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 5
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
229920002261 Corn starch Polymers 0.000 description 4
YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
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 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
150000008044 alkali metal hydroxides Chemical class 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
239000008120 corn starch Substances 0.000 description 4
239000008101 lactose Substances 0.000 description 4
235000019359 magnesium stearate Nutrition 0.000 description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
125000004423 acyloxy group Chemical group 0.000 description 3
125000005605 benzo group Chemical group 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
150000001805 chlorine compounds Chemical class 0.000 description 3
239000008119 colloidal silica Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
230000032050 esterification Effects 0.000 description 3
238000005886 esterification reaction Methods 0.000 description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
150000007529 inorganic bases Chemical class 0.000 description 3
229910052740 iodine Inorganic materials 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
FJCFFCXMEXZEIM-UHFFFAOYSA-N oxiniacic acid Chemical compound OC(=O)C1=CC=C[N+]([O-])=C1 FJCFFCXMEXZEIM-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000003826 tablet Substances 0.000 description 3
ZZMCGWNHOMZDSD-UHFFFAOYSA-N 1-cyanoisoquinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CN=C(C#N)C2=C1 ZZMCGWNHOMZDSD-UHFFFAOYSA-N 0.000 description 2
MACYWSXBVZZIIC-UHFFFAOYSA-N 1-oxido-4-phenylpyridin-1-ium-3-carboxylic acid Chemical compound OC(=O)C1=C[N+]([O-])=CC=C1C1=CC=CC=C1 MACYWSXBVZZIIC-UHFFFAOYSA-N 0.000 description 2
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 2
VRVRGVPWCUEOGV-UHFFFAOYSA-N 2-aminothiophenol Chemical compound NC1=CC=CC=C1S VRVRGVPWCUEOGV-UHFFFAOYSA-N 0.000 description 2
BXJROCSZWILXBF-UHFFFAOYSA-N 2-oxidoisoquinolin-2-ium-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C[N+]([O-])=CC2=C1 BXJROCSZWILXBF-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
KNAJXVPTHLCZPC-UHFFFAOYSA-N 4-butyl-1-oxidopyridin-1-ium-3-carboxylic acid Chemical compound CCCCC1=CC=[N+]([O-])C=C1C(O)=O KNAJXVPTHLCZPC-UHFFFAOYSA-N 0.000 description 2
VOODMLPUWZXMMM-UHFFFAOYSA-N 4-butyl-6-cyanopyridine-3-carboxylic acid Chemical compound CCCCC1=CC(C#N)=NC=C1C(O)=O VOODMLPUWZXMMM-UHFFFAOYSA-N 0.000 description 2
QSFZUCAXFRVOTP-UHFFFAOYSA-N 4-cyclohexylpyridine-3-carboxylic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CN=CC=C1C1CCCCC1 QSFZUCAXFRVOTP-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
102000008186 Collagen Human genes 0.000 description 2
108010035532 Collagen Proteins 0.000 description 2
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238000000265 homogenisation Methods 0.000 description 1
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125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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239000011591 potassium Substances 0.000 description 1
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NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
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238000001556 precipitation Methods 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
208000005069 pulmonary fibrosis Diseases 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
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125000002098 pyridazinyl group Chemical group 0.000 description 1
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical class [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
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230000007017 scission Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
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CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
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235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
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QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
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239000000600 sorbitol Substances 0.000 description 1
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239000005720 sucrose Substances 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
125000001302 tertiary amino group Chemical group 0.000 description 1
150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
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125000001544 thienyl group Chemical group 0.000 description 1
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235000010487 tragacanth Nutrition 0.000 description 1
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238000000844 transformation Methods 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- 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
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Reproductive Health (AREA)
Cardiology (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Endocrinology (AREA)
Heart & Thoracic Surgery (AREA)
Dermatology (AREA)
Pulmonology (AREA)
Gastroenterology & Hepatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)

DD88312758A 1987-02-10 1988-02-08 Verfahren zur herstellung herterozyclischer stickstoffverbindungen DD287495A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB878702890A GB8702890D0 (en)	1987-02-10	1987-02-10	Heterocyclic compounds

Publications (1)

Publication Number	Publication Date
DD287495A5 true DD287495A5 (de)	1991-02-28

Family

ID=10611962

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88312758A DD287495A5 (de)	1987-02-10	1988-02-08	Verfahren zur herstellung herterozyclischer stickstoffverbindungen

Country Status (13)

Country	Link
US (1)	US4904675A (da)
EP (1)	EP0278908A3 (da)
JP (1)	JPS63216872A (da)
AU (1)	AU1144888A (da)
DD (1)	DD287495A5 (da)
DK (1)	DK64788A (da)
FI (1)	FI880562A7 (da)
GB (1)	GB8702890D0 (da)
HU (1)	HU201015B (da)
NO (1)	NO880553L (da)
NZ (1)	NZ223443A (da)
YU (1)	YU24088A (da)
ZA (1)	ZA88894B (da)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4796243A (en) *	1985-06-21	1989-01-03	Nec Corporation	Time base correcting apparatus
US5238948A (en) *	1987-02-10	1993-08-24	Hoechst Aktiengesellschaft	Pyridine-2,4- and -2,5-dicarboxylic acid derivatives and medicaments based on these compounds
US5153208A (en) *	1987-02-10	1992-10-06	Hoechst Aktiengesellschaft	Pyridine-2,4- and -2,5-dicarboxylic acid amides and their medicinal compositions and methods of use
DE3703959A1 (de) *	1987-02-10	1988-08-18	Hoechst Ag	Pyridin-2,4- und 2,5-dicarbonsaeureamide, verfahren zu ihrer herstellung, verwendung derselben sowie arzneimittel auf basis dieser verbindungen
US5512586A (en) *	1987-02-10	1996-04-30	Hoechst Aktiengesellschaft	Medicaments based on pyridine-2,4- and 2,5-dicarboxylic acid amides
DE3703963A1 (de) *	1987-02-10	1988-08-18	Hoechst Ag	Pyridin-2,4- und 2,,5-dicarbonsaeure-derivate, verfahren zu ihrer herstellung, verwendung derselben, sowie arzneimittel auf basis dieser verbindungen
DK0446798T3 (da) *	1990-03-13	1995-05-08	Hoechst Roussel Pharma	1-Alkyl-, 1-alkenyl- og 1-alkynylaryl-2-amino-1,3-propandioler og beslægtede forbindelser, en fremgangsmåde og mellemprodukter til deres fremstilling samt deres anvendelse som lægemidler
US5789426A (en) *	1995-01-20	1998-08-04	Cornell Research Foundation, Inc.	Method for the treatment of fibroproliferative disorders by application of inhibitors of protein hydroxylation
US6046219A (en) *	1995-01-20	2000-04-04	Cornell Research Foundation, Inc.	Method for the treatment of conditions mediated by collagen formation together with cell proliferation by application of inhibitors of protein hydroxylation
US5891892A (en) *	1996-10-29	1999-04-06	Warner-Lambert Company	Small molecule biaryl compounds as inhibitors of endothelin converting enzyme
US7067148B2 (en)	2001-02-15	2006-06-27	King Pharmaceutical Research & Development, Inc.	Stabilized pharmaceutical and thyroid hormone compositions and method of preparation
US7101569B2 (en)	2001-08-14	2006-09-05	Franz G Andrew	Methods of administering levothyroxine pharmaceutical compositions
EP1958620B1 (en) *	2007-02-16	2012-04-18	CSEM Centre Suisse d'Electronique et de Microtechnique SA - Recherche et Développement	Verification method
WO2016160706A1 (en) *	2015-03-28	2016-10-06	Wisconsin Alumni Research Foundation	Inhibitors of collagen prolyl 4-hydroxylase

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3501486A (en) *	1967-04-28	1970-03-17	Ash Stevens Inc	Process for the production of 2-pyridine aldoximes
IL62794A0 (en) *	1980-06-02	1981-07-31	American Cyanamid Co	Substituted nicotinic acid esters and salts thereof and their use as herbicidal agents
EP0041624B1 (en) *	1980-06-02	1984-02-01	American Cyanamid Company	Method to beneficially influence & alter the development & life cycle of agronomic and horticultural crops with certain imidazolinyl nicotinic acids and derivatives thereof
US4404012A (en) *	1980-06-02	1983-09-13	American Cyanamid Company	Process for increasing sugar yield in sugarcane
DE3432094A1 (de) *	1984-08-31	1986-03-06	Hoechst Ag, 6230 Frankfurt	Ester der pyridin-2,4- und -2,5- dicarbonsaeure als arzneimittel zur inhibierung der prolin- und lysinhydroxylase
GB2174395A (en) *	1986-05-09	1986-11-05	American Cyanimid Co	Herbicidal 2-(2-imidazolin-2-yl)pyridine derivatives

1987
- 1987-02-10 GB GB878702890A patent/GB8702890D0/en active Pending
1988
- 1988-02-04 EP EP88810064A patent/EP0278908A3/en not_active Withdrawn
- 1988-02-08 FI FI880562A patent/FI880562A7/fi not_active Application Discontinuation
- 1988-02-08 YU YU00240/88A patent/YU24088A/xx unknown
- 1988-02-08 NZ NZ223443A patent/NZ223443A/xx unknown
- 1988-02-08 DD DD88312758A patent/DD287495A5/de unknown
- 1988-02-09 NO NO880553A patent/NO880553L/no unknown
- 1988-02-09 HU HU88582A patent/HU201015B/hu not_active IP Right Cessation
- 1988-02-09 JP JP63026717A patent/JPS63216872A/ja active Pending
- 1988-02-09 ZA ZA880894A patent/ZA88894B/xx unknown
- 1988-02-09 AU AU11448/88A patent/AU1144888A/en not_active Abandoned
- 1988-02-09 DK DK064788A patent/DK64788A/da not_active Application Discontinuation
- 1988-02-10 US US07/154,217 patent/US4904675A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
EP0278908A3 (en)	1990-01-17
FI880562A7 (fi)	1988-08-11
NO880553D0 (no)	1988-02-09
HU201015B (en)	1990-09-28
DK64788A (da)	1988-08-11
GB8702890D0 (en)	1987-03-18
JPS63216872A (ja)	1988-09-09
NZ223443A (en)	1990-09-26
NO880553L (no)	1988-08-11
DK64788D0 (da)	1988-02-09
YU24088A (en)	1990-02-28
FI880562A0 (fi)	1988-02-08
AU1144888A (en)	1988-08-11
ZA88894B (en)	1988-08-10
EP0278908A2 (en)	1988-08-17
US4904675A (en)	1990-02-27
HUT46668A (en)	1988-11-28

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DE69409525T2 (de)	1998-08-06	Acetamidderivate und ihre verwendung als modifizierungsmittel des verhaltens der verdauung
DE60225316T2 (de)	2009-02-26	Cyanoalkylamino-derivate als protease-hemmer
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EP0418797B1 (de)	1994-08-24	Pyrimidin-4,6-dicarbonsäurediamide, Verfahren zu deren Herstellung sowie Verwendung derselben sowie Arzneimittel auf Basis dieser Verbindungen
DE69500597T2 (de)	1998-03-26	N-pyridyl Carboxamidderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutischen Zusammensetzungen
DE2706977A1 (de)	1978-08-24	Benzoesaeuren und deren derivate sowie verfahren zu ihrer herstellung
DD287495A5 (de)	1991-02-28	Verfahren zur herstellung herterozyclischer stickstoffverbindungen
WO1993004035A1 (de)	1993-03-04	Neue 3,5-di-tert.butyl-4-hydroxyphenyl-derivate, verfahren zu ihrer herstellung und arzneimittel
DE10046029A1 (de)	2002-03-28	Indazole
EP0408509B1 (de)	1996-03-06	Substituierte Benzonitrile
DE3209276A1 (de)	1983-09-15	Arzneimittel mit antihypoxischer und ischaemie-protektiver wirkung
DE2838892A1 (de)	1979-03-15	2-substituierte-5-hydroxy-1h-imidazol-4-carboxamid-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel
DE69024843T2 (de)	1996-05-30	Rhodanin-Derivate und pharmazeutische Zusammensetzungen
EP0316279A2 (de)	1989-05-17	Veresterte azacyclische Hydroxyverbindungen
DD233847A5 (de)	1986-03-12	Verfahren zur herstellung von methylendiphosphon-derivaten mit antireuhmatischen eigenschaften
DE2824341A1 (de)	1978-12-21	N- eckige klammer auf 6- eckige klammer auf (aminosulfonyl)phenyl eckige klammer zu -1,2-dihydro-2-oxonicotinyl eckige klammer zu penicilline und -cephalosporine
DE69718968T2 (de)	2003-10-09	3-(bis-substituierte-phenylmethylen)oxindol-derivate
CH645354A5 (de)	1984-09-28	Chinolyl-guanidine, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische mischungen.
EP0530639B1 (de)	1994-08-17	Heterocyclisch substituierte Chinolylmethoxy-Phenylacetamide als Lipoxygenasehemmer
CH509318A (de)	1971-06-30	Verfahren zur Herstellung von substituierten Benzimidazolen
DE69110217T2 (de)	1996-02-29	Derivate der Kaffeinsäure und sie enthaltende pharmazeutische Zusammensetzungen.
DE2600513A1 (de)	1977-07-28	Acylamino(alkyl)benzolderivate und verfahren zu ihrer herstellung
DE2812353A1 (de)	1978-09-28	Oxazol- und thiazol-alkansaeureverbindungen, verfahren zu ihrer herstellung und sie enthaltendes pharmazeutisches mittel
DE4120107A1 (de)	1992-12-17	Bicyclisch substituierte vinylimidazole, -triazole und -tetrazole
DE2331721A1 (de)	1974-01-10	Verfahren zur herstellung neuer heterocyclischer verbindungen