DD293828A5 - Verfahren zur herstellung polycyclischer verbindungen - Google Patents

Verfahren zur herstellung polycyclischer verbindungen Download PDF

Info

Publication number: DD293828A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; compounds; compound; salt; salts
Prior art date: 1989-04-26

Application number

DD90340101A

Other languages

German (de)

English (en)

Inventor

Wilhelm Kump

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.)

1989-04-26

Filing date

1990-04-25

Publication date

1991-09-12

1990-04-25 Application filed by ��`��@��k�� filed Critical ��`��@��k��

1991-09-12 Publication of DD293828A5 publication Critical patent/DD293828A5/de

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 61
238000004519 manufacturing process Methods 0.000 title abstract 2
150000003839 salts Chemical class 0.000 claims abstract description 49
238000000034 method Methods 0.000 claims abstract description 29
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
239000001257 hydrogen Substances 0.000 claims abstract description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
125000000217 alkyl group Chemical group 0.000 claims abstract description 6
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract description 5
-1 4- (2,4,6-trimethylbenzyl) -1-piperazinyl Chemical group 0.000 claims description 23
238000006243 chemical reaction Methods 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 6
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
229960003292 rifamycin Drugs 0.000 claims description 5
238000007363 ring formation reaction Methods 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
238000009835 boiling Methods 0.000 claims description 2
238000002360 preparation method Methods 0.000 abstract description 7
239000003814 drug Substances 0.000 abstract description 4
125000003367 polycyclic group Chemical group 0.000 abstract description 3
239000002253 acid Substances 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000243 solution Substances 0.000 description 9
239000007858 starting material Substances 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
208000031226 Hyperlipidaemia Diseases 0.000 description 3
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Substances 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
238000003756 stirring Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Chemical compound OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
235000015165 citric acid Nutrition 0.000 description 2
230000000694 effects Effects 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000001630 malic acid Substances 0.000 description 2
235000011090 malic acid Nutrition 0.000 description 2
239000000463 material Substances 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical compound OC1=C(C(O)=C2C)C3=C(O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O HJYYPODYNSCCOU-ODRIEIDWSA-N 0.000 description 2
229940109171 rifamycin sv Drugs 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
238000012360 testing method Methods 0.000 description 2
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
KGKSTPKEAQNJJD-UHFFFAOYSA-N 1-bromo-3-methylpent-1-yn-3-ol Chemical compound CCC(C)(O)C#CBr KGKSTPKEAQNJJD-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
QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
206010003210 Arteriosclerosis Diseases 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Natural products OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
108010093096 Immobilized Enzymes Proteins 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229930189077 Rifamycin Natural products 0.000 description 1
BTVYFIMKUHNOBZ-ZDHWWVNNSA-N Rifamycin S Natural products COC1C=COC2(C)Oc3c(C)c(O)c4C(=O)C(=CC(=O)c4c3C2=O)NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C BTVYFIMKUHNOBZ-ZDHWWVNNSA-N 0.000 description 1
BTVYFIMKUHNOBZ-ODRIEIDWSA-N Rifamycin S Chemical compound O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-ODRIEIDWSA-N 0.000 description 1
HJYYPODYNSCCOU-ZDHWWVNNSA-N Rifamycin SV Natural products COC1C=COC2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C)cc(O)c4c3C2=O HJYYPODYNSCCOU-ZDHWWVNNSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
239000012345 acetylating agent Substances 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
239000003524 antilipemic agent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
208000011775 arteriosclerosis disease Diseases 0.000 description 1
229960001230 asparagine Drugs 0.000 description 1
235000009582 asparagine Nutrition 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 description 1
230000000055 hyoplipidemic effect Effects 0.000 description 1
208000020346 hyperlipoproteinemia Diseases 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
244000005700 microbiome Species 0.000 description 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 description 1
230000003472 neutralizing effect Effects 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
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
238000000926 separation method Methods 0.000 description 1
238000005245 sintering Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

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
- C07D498/18—Bridged systems
- 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
- A61P3/06—Antihyperlipidemics
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (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)
Public Health (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Steroid Compounds (AREA)
Saccharide Compounds (AREA)

DD90340101A 1989-04-26 1990-04-25 Verfahren zur herstellung polycyclischer verbindungen DD293828A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH159589		1989-04-26

Publications (1)

Publication Number	Publication Date
DD293828A5 true DD293828A5 (de)	1991-09-12

Family

ID=4214097

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD90340101A DD293828A5 (de)	1989-04-26	1990-04-25	Verfahren zur herstellung polycyclischer verbindungen

Country Status (9)

Country	Link
US (1)	US5053510A (fr)
EP (1)	EP0395580A3 (fr)
JP (1)	JPH02304090A (fr)
DD (1)	DD293828A5 (fr)
FI (1)	FI902025A7 (fr)
HU (2)	HU204835B (fr)
NO (1)	NO901834L (fr)
PT (1)	PT93858A (fr)
YU (1)	YU81090A (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1989003834A1 (fr) *	1987-10-27	1989-05-05	Ciba-Geigy Ag	Derives azacyclohexyliques substitues
US5180718A (en) *	1989-03-02	1993-01-19	Ciba-Geigy Corporation	Acyl derivatives of oxazolorifamycins

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MC1819A1 (fr) *	1985-10-18	1988-03-18	Ciba Geigy Ag	Composes 4-benzyl-piperazinyl substitues
DE3545538A1 (de) *	1985-12-21	1987-07-02	Audi Ag	Vorrichtung mit einem hubgestell zum bearbeiten von werkstuecken
WO1989003834A1 (fr) *	1987-10-27	1989-05-05	Ciba-Geigy Ag	Derives azacyclohexyliques substitues
IL90695A0 (en) *	1988-06-30	1990-01-18	Ciba Geigy Ag	Substituted azacyclohexyl derivatives

1989
- 1989-04-25 HU HU902566A patent/HU204835B/hu not_active IP Right Cessation
1990
- 1990-04-18 EP EP19900810305 patent/EP0395580A3/fr not_active Withdrawn
- 1990-04-18 US US07/510,753 patent/US5053510A/en not_active Expired - Fee Related
- 1990-04-23 YU YU00810/90A patent/YU81090A/xx unknown
- 1990-04-23 FI FI902025A patent/FI902025A7/fi not_active IP Right Cessation
- 1990-04-24 PT PT93858A patent/PT93858A/pt not_active Application Discontinuation
- 1990-04-25 DD DD90340101A patent/DD293828A5/de not_active IP Right Cessation
- 1990-04-25 JP JP2107699A patent/JPH02304090A/ja active Pending
- 1990-04-25 NO NO90901834A patent/NO901834L/no unknown
- 1990-04-25 HU HU902566A patent/HU902566D0/hu unknown

Also Published As

Publication number	Publication date
YU81090A (en)	1991-10-31
NO901834D0 (no)	1990-04-25
HU204835B (en)	1992-02-28
FI902025A7 (fi)	1990-10-27
EP0395580A2 (fr)	1990-10-31
PT93858A (pt)	1990-11-20
FI902025A0 (fi)	1990-04-23
JPH02304090A (ja)	1990-12-17
EP0395580A3 (fr)	1991-10-23
HU902566D0 (en)	1990-08-28
NO901834L (no)	1990-10-29
US5053510A (en)	1991-10-01

Legal Events

Date	Code	Title	Description
1995-08-03	ENJ	Ceased due to non-payment of renewal fee

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DE2806909C2 (fr)	1988-04-07
DD293828A5 (de)	1991-09-12	Verfahren zur herstellung polycyclischer verbindungen
CH653996A5 (de)	1986-01-31	Tryptaminderivate und verfahren zu deren herstellung.
EP0362350A1 (fr)	1990-04-11	Procede de production d'heteroaromates azotes a 5 membres
WO1989003834A1 (fr)	1989-05-05	Derives azacyclohexyliques substitues
DE3026602C2 (fr)	1990-05-03
CH619468A5 (fr)	1980-09-30
DE3431591A1 (de)	1986-03-13	Verfahren zur herstellung von aminoverbindungen aus hydroxylverbindungen
EP0293814A1 (fr)	1988-12-07	Nouveaux dérivés mono- et polyhydroxyacylés de labdanes polyoxygénés, procédé pour leur préparation et leur application comme médicaments
DE2707404C3 (de)	1979-03-22	Verfahren zur Herstellung von 5,6-Dehydropenicillinen
CH671959A5 (fr)	1989-10-13
AT395976B (de)	1993-04-26	Verfahren zur herstellung von dihydropyridinverbindungen oder ihren salzen
DE69020372T2 (de)	1996-01-18	Verfahren zur Herstellung von Aminothiazolylessigsäure-Derivate.
EP0350445A1 (fr)	1990-01-10	Dérivés d'azacyclohexyle substitués
EP0104566A2 (fr)	1984-04-04	Procédé pour la préparation de 5,11-dihydro-11-((4-méthyl-1-pipérazinyl)-acétyl)-6H-pyrido(2,3-b)(1,4)benzodiazépin-6-one
DE4116157A1 (de)	1992-11-19	Verfahren zur herstellung von imidazothiazolon-derivaten
DD283396A5 (de)	1990-10-10	Verfahren zur herstellung von substituierten azacyclohexyl-derivaten
CH634559A5 (de)	1983-02-15	Verfahren zur herstellung von 3-halogen-3-kohlenwasserstoffthio-oxindolen und verfahren zur herstellung von isatinen.
EP0175264B1 (fr)	1989-11-15	Procédé de préparation de 2-amino-3-cyano-5-dialkoxyméthyl-pyrazines et intermédiaires pour ce procédé