DD201590A5 - Verfahren zur herstellung von neuen heterocyclischen verbindungen - Google Patents

Verfahren zur herstellung von neuen heterocyclischen verbindungen Download PDF

Info

Publication number: DD201590A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; compound; acid; hydrogen; preparation
Prior art date: 1980-08-08

Application number

DD81232351A

Other languages

German (de)

English (en)

Inventor

Ulrich Seipp

Werner Vollenberg

Bernd Mueller

Gudrun Michel

Original Assignee

Gruenenthal Gmbh

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.)

1980-08-08

Filing date

1981-08-03

Publication date

1983-07-27

1981-08-03 Application filed by Gruenenthal Gmbh filed Critical Gruenenthal Gmbh

1983-07-27 Publication of DD201590A5 publication Critical patent/DD201590A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 31
238000002360 preparation method Methods 0.000 title claims abstract description 23
230000008569 process Effects 0.000 title claims abstract description 17
150000002391 heterocyclic compounds Chemical class 0.000 title claims abstract description 14
150000001875 compounds Chemical class 0.000 claims abstract description 54
239000001257 hydrogen Substances 0.000 claims abstract description 24
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
150000001768 cations Chemical class 0.000 claims abstract description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
229910052794 bromium Inorganic materials 0.000 claims abstract description 6
229910052799 carbon Inorganic materials 0.000 claims abstract description 5
239000000460 chlorine Substances 0.000 claims abstract description 4
229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
238000007363 ring formation reaction Methods 0.000 claims abstract 2
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 37
239000002253 acid Substances 0.000 claims description 21
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 19
-1 Brornessigsäure Chemical compound 0.000 claims description 17
239000000741 silica gel Substances 0.000 claims description 17
229910002027 silica gel Inorganic materials 0.000 claims description 17
238000006243 chemical reaction Methods 0.000 claims description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 11
239000011734 sodium Substances 0.000 claims description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
239000012433 hydrogen halide Substances 0.000 claims description 8
229910000039 hydrogen halide Inorganic materials 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
238000004440 column chromatography Methods 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
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 claims description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 5
230000008030 elimination Effects 0.000 claims description 5
238000003379 elimination reaction Methods 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
238000007127 saponification reaction Methods 0.000 claims description 5
241000251730 Chondrichthyes Species 0.000 claims description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
239000011230 binding agent Substances 0.000 claims description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
125000004185 ester group Chemical group 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
239000005711 Benzoic acid Substances 0.000 claims description 3
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
235000010233 benzoic acid Nutrition 0.000 claims description 3
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
KWPQTFXULUUCGD-UHFFFAOYSA-N 3,4,5,7,8,9,10,10a-octahydropyrido[1,2-a][1,4]diazepine Chemical compound C1CCN=CC2CCCCN21 KWPQTFXULUUCGD-UHFFFAOYSA-N 0.000 claims 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 claims description 2
XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 claims description 2
ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
235000011054 acetic acid Nutrition 0.000 claims description 2
230000001476 alcoholic effect Effects 0.000 claims description 2
235000010216 calcium carbonate Nutrition 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
230000007717 exclusion Effects 0.000 claims description 2
235000019253 formic acid Nutrition 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
238000004255 ion exchange chromatography Methods 0.000 claims description 2
238000002955 isolation Methods 0.000 claims description 2
239000000395 magnesium oxide Substances 0.000 claims description 2
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 2
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims description 2
239000002585 base Substances 0.000 claims 2
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 claims 2
SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 claims 1
OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 claims 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 claims 1
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PQGAHNJECSVDEI-UHFFFAOYSA-N [CH2]CCCCC Chemical compound [CH2]CCCCC PQGAHNJECSVDEI-UHFFFAOYSA-N 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
230000026030 halogenation Effects 0.000 claims 1
238000005658 halogenation reaction Methods 0.000 claims 1
230000001077 hypotensive effect Effects 0.000 abstract description 7
208000010110 spontaneous platelet aggregation Diseases 0.000 abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 6
230000002401 inhibitory effect Effects 0.000 abstract description 6
150000003839 salts Chemical class 0.000 abstract description 4
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125000000217 alkyl group Chemical group 0.000 abstract 2
239000011630 iodine Substances 0.000 abstract 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
208000007536 Thrombosis Diseases 0.000 description 1
XRRYGMTXOYFERK-UHFFFAOYSA-N [I].[K].[I] Chemical compound [I].[K].[I] XRRYGMTXOYFERK-UHFFFAOYSA-N 0.000 description 1
ITBPIKUGMIZTJR-UHFFFAOYSA-N [bis(hydroxymethyl)amino]methanol Chemical compound OCN(CO)CO ITBPIKUGMIZTJR-UHFFFAOYSA-N 0.000 description 1
206010000210 abortion Diseases 0.000 description 1
231100000176 abortion Toxicity 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
229940030225 antihemorrhagics Drugs 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
229940114079 arachidonic acid Drugs 0.000 description 1
235000021342 arachidonic acid Nutrition 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
208000027697 autoimmune lymphoproliferative syndrome due to CTLA4 haploinsuffiency Diseases 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
230000036765 blood level Effects 0.000 description 1
230000004531 blood pressure lowering effect Effects 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
210000001072 colon Anatomy 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000001595 contractor effect Effects 0.000 description 1
208000029078 coronary artery disease Diseases 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
239000003405 delayed action preparation Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
230000000025 haemostatic effect Effects 0.000 description 1
230000002489 hematologic effect Effects 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
230000036512 infertility Effects 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
229910001425 magnesium ion Inorganic materials 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
125000004492 methyl ester group Chemical group 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
239000000203 mixture Substances 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
238000004806 packaging method and process Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
229910001414 potassium ion Inorganic materials 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
230000001110 prostacyclinlike Effects 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
208000002815 pulmonary hypertension Diseases 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
208000037905 systemic hypertension Diseases 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000007885 tablet disintegrant Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
- C07D307/937—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans with hydrocarbon or substituted hydrocarbon radicals directly attached in position 2, e.g. prostacyclins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5456—Arylalkanephosphonium compounds

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Cardiology (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Furan Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Liquid Developers In Electrophotography (AREA)
Sheet Holders (AREA)
Control Of Positive-Displacement Air Blowers (AREA)

DD81232351A 1980-08-08 1981-08-03 Verfahren zur herstellung von neuen heterocyclischen verbindungen DD201590A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3029984A DE3029984C2 (de)	1980-08-08	1980-08-08	2-Oxabicyclo [3.3.0] octanderivate und diese enthaltende Arzneimittel

Publications (1)

Publication Number	Publication Date
DD201590A5 true DD201590A5 (de)	1983-07-27

Family

ID=6109130

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD81232351A DD201590A5 (de)	1980-08-08	1981-08-03	Verfahren zur herstellung von neuen heterocyclischen verbindungen

Country Status (23)

Country	Link
US (1)	US4372971A (fr)
EP (1)	EP0045842B1 (fr)
JP (1)	JPS5754180A (fr)
KR (1)	KR850000388B1 (fr)
AT (1)	ATE5884T1 (fr)
AU (1)	AU542775B2 (fr)
CA (1)	CA1169871A (fr)
DD (1)	DD201590A5 (fr)
DE (2)	DE3029984C2 (fr)
DK (1)	DK154214C (fr)
ES (1)	ES8301957A1 (fr)
FI (1)	FI72973C (fr)
GR (1)	GR75238B (fr)
HK (1)	HK26187A (fr)
HU (1)	HU184870B (fr)
IE (1)	IE51308B1 (fr)
IL (1)	IL63322A (fr)
MY (1)	MY8600649A (fr)
NO (1)	NO154166C (fr)
PT (1)	PT73406B (fr)
SU (1)	SU1072801A3 (fr)
YU (1)	YU42416B (fr)
ZA (1)	ZA814720B (fr)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL65387A0 (en) *	1981-04-14	1982-05-31	Chinoin Gyogyszer Es Vegyeszet	2,3,4-trinor-m-inter-phenylene-prostaglandin derivatives and a process for the preparation thereof
HU188559B (en) *	1981-12-01	1986-04-28	Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu	Process for preparing new inter-m-phenylene-prostacyclin derivatives
IL67332A (en) *	1981-12-01	1985-12-31	Chinoin Gyogyszer Es Vegyeszet	Inter-m-phenylene-prostacyclin analogues,process for the preparation thereof and pharmaceutical compositions containing them
HU190007B (en) *	1982-05-06	1986-08-28	Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt,Hu	Process for producing new aromatic prostacylin analogues
DE3317159A1 (de) *	1982-05-27	1983-12-01	Grünenthal GmbH, 5190 Stolberg	Verfahren zur herstellung von 5z-formen von 2,3,4-trinor-1,5-inter-m-phenylen- prostacyclinderivaten
DE3914735A1 (de) *	1989-05-05	1990-11-08	Gruenenthal Gmbh	Pharmakologisch wirksame ester, diese enthaltende arzneimittel und die herstellung dieser ester und arzneimittel

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3933895A (en) *	1972-10-30	1976-01-20	The Upjohn Company	Oxa-phenylene compounds
US3933898A (en) *	1972-10-30	1976-01-20	The Upjohn Company	PGE1 -oxa phenylene compounds
US3933899A (en) *	1972-10-30	1976-01-20	The Upjohn Company	PGE2 -oxa-phenylene compounds
US3933900A (en) *	1972-10-30	1976-01-20	The Upjohn Company	PGEo oxa-phenylene compounds
US3933897A (en) *	1972-10-30	1976-01-20	The Upjohn Company	PGA1 -oxa-phenylene compounds
US3933896A (en) *	1972-10-30	1976-01-20	The Upjohn Company	PGF1.sub.β -oxa phenylene compounds
DE2346706A1 (de) *	1973-09-17	1975-04-03	Hoechst Ag	Neue, nicht natuerlich vorkommende analoga von prostansaeuren und verfahren zu ihrer herstellung
IL51189A (en) *	1976-02-04	1985-08-30	Upjohn Co	Prostaglandin analogs
US4238623A (en) *	1976-03-29	1980-12-09	Miles Laboratories, Inc.	5,6-Benzo analogues of prostaglandin
AU524786B2 (en) *	1977-03-07	1982-10-07	The Upjohn Company	Prostacyclins
US4207257A (en) *	1977-04-18	1980-06-10	The Upjohn Company	Inter-phenylene-13,14-dihydro-PG amides
US4100192A (en) *	1977-04-18	1978-07-11	The Upjohn Company	Inter-phenylene-PG amides
IT1088036B (it)	1977-11-25	1985-06-04	Erba Carlo Spa	15-epi-prostaciclina e prostaciclina analoghi
IT1099575B (it) *	1978-07-20	1985-09-18	Erba Carlo Spa	20-metil-13,14-deidro-pgi2' suoi sali e suoi 16s- e 16r-metil derivati
US4180657A (en) *	1978-08-14	1979-12-25	The Upjohn Company	Acyl-substituted phenyl esters of prostacyclin-type compounds
US4312810A (en)	1978-11-22	1982-01-26	The Upjohn Company	2,5-Inter-o-phenylene-3,4-dinor-5,9α-epoxy-9-deoxy-PGF1 compounds
DE2902809A1 (de) *	1979-01-25	1980-08-07	Hoechst Ag	Neue analoga von prostacyclin

1980
- 1980-08-08 DE DE3029984A patent/DE3029984C2/de not_active Expired
1981
- 1981-06-18 IE IE1357/81A patent/IE51308B1/en not_active IP Right Cessation
- 1981-06-18 GR GR65265A patent/GR75238B/el unknown
- 1981-06-26 DE DE8181104982T patent/DE3161958D1/de not_active Expired
- 1981-06-26 EP EP81104982A patent/EP0045842B1/fr not_active Expired
- 1981-06-26 AT AT81104982T patent/ATE5884T1/de not_active IP Right Cessation
- 1981-07-01 AU AU72463/81A patent/AU542775B2/en not_active Ceased
- 1981-07-09 NO NO812338A patent/NO154166C/no unknown
- 1981-07-10 ZA ZA814720A patent/ZA814720B/xx unknown
- 1981-07-15 IL IL63322A patent/IL63322A/xx not_active IP Right Cessation
- 1981-07-20 YU YU1790/81A patent/YU42416B/xx unknown
- 1981-07-22 PT PT73406A patent/PT73406B/fr not_active IP Right Cessation
- 1981-07-24 CA CA000382448A patent/CA1169871A/fr not_active Expired
- 1981-08-03 DD DD81232351A patent/DD201590A5/de not_active IP Right Cessation
- 1981-08-05 HU HU812268A patent/HU184870B/hu not_active IP Right Cessation
- 1981-08-06 DK DK350181A patent/DK154214C/da not_active IP Right Cessation
- 1981-08-06 JP JP56122548A patent/JPS5754180A/ja active Granted
- 1981-08-06 US US06/290,573 patent/US4372971A/en not_active Expired - Lifetime
- 1981-08-07 KR KR1019810002871A patent/KR850000388B1/ko not_active Expired
- 1981-08-07 ES ES504618A patent/ES8301957A1/es not_active Expired
- 1981-08-07 FI FI812452A patent/FI72973C/fi not_active IP Right Cessation
- 1981-08-07 SU SU813314353A patent/SU1072801A3/ru active
1986
- 1986-12-30 MY MY649/86A patent/MY8600649A/xx unknown
1987
- 1987-04-02 HK HK261/87A patent/HK26187A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
CA1169871A (fr)	1984-06-26
IL63322A (en)	1985-01-31
JPS6116393B2 (fr)	1986-04-30
FI72973C (fi)	1987-08-10
DK154214C (da)	1989-03-13
DK154214B (da)	1988-10-24
KR850000388B1 (ko)	1985-03-25
IL63322A0 (en)	1981-10-30
JPS5754180A (en)	1982-03-31
ES504618A0 (es)	1983-01-01
AU7246381A (en)	1982-02-11
ES8301957A1 (es)	1983-01-01
DK350181A (da)	1982-02-09
MY8600649A (en)	1986-12-31
SU1072801A3 (ru)	1984-02-07
US4372971A (en)	1983-02-08
FI812452L (fi)	1982-02-09
EP0045842A1 (fr)	1982-02-17
DE3029984C2 (de)	1983-12-15
DE3161958D1 (en)	1984-02-23
YU42416B (en)	1988-08-31
ATE5884T1 (de)	1984-02-15
PT73406B (fr)	1982-08-09
YU179081A (en)	1983-06-30
NO812338L (no)	1982-02-09
IE51308B1 (en)	1986-11-26
NO154166B (no)	1986-04-21
KR830006265A (ko)	1983-09-20
NO154166C (no)	1986-07-30
GR75238B (fr)	1984-07-13
HU184870B (en)	1984-10-29
IE811357L (en)	1982-02-08
AU542775B2 (en)	1985-03-14
EP0045842B1 (fr)	1984-01-18
DE3029984A1 (de)	1982-02-18
PT73406A (fr)	1981-08-01
ZA814720B (en)	1982-07-28
FI72973B (fi)	1987-04-30
HK26187A (en)	1987-04-10

Legal Events

Date	Code	Title	Description
2000-03-30	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
CH645355A5 (de)	1984-09-28	1-((acylthio)- und (mercapto)-1-oxoalkyl)-1,2,3,4-tetrahydrochinolin-2-carboxylsaeuren und deren salze.
EP0119949B1 (fr)	1988-11-23	Carbacyclines, leur procédé de préparation, et leur utilisation comme médicaments
DE2355540C2 (de)	1982-11-18	16-Phenoxy-&omega;-tetranorprostaglandinderivate
EP0099538B1 (fr)	1991-09-11	Carbacyclines, procédé pour leur préparation et leur utilisation comme médicaments
DE2627671A1 (de)	1977-01-13	Arzneimittel, enthaltend ein lacton eines prostaglandins oder prostaglandinanalogen
EP0045842B1 (fr)	1984-01-18	Composés hétérocycliques, leur préparation et application comme thérapeutiques
DE2720998C2 (fr)	1989-04-06
DE2651979C2 (de)	1985-10-31	9-Phenyl-3,7-dimethyl-2,4,6,8-nonatetraenverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2346706A1 (de)	1975-04-03	Neue, nicht natuerlich vorkommende analoga von prostansaeuren und verfahren zu ihrer herstellung
DD143849A6 (de)	1980-09-17	Insektizide,akarizide und nematizide mittel
DD220204A5 (de)	1985-03-27	Verfahren zur herstellung von 5-cyanoprostacylinen
DE2743283A1 (de)	1979-04-05	Neue prostacyclin-analoga
EP0086404B1 (fr)	1986-12-30	Carbacyclines, procédé pour leur préparation et leur application comme médicaments
DE2337581A1 (de)	1974-03-14	Derivate von 9-hydroxy-13-trans-prostensaeure
DE2705613B2 (de)	1978-11-09	Bicycloheptylderivate von Prostaglandinen und Verfahren zu deren Herstellung sowie Zwischenprodukte zu deren Herstellung und Arzneimittel, welche die Bicycloheptylderivate enthalten
DE2811950A1 (de)	1979-12-13	Neue analoga von prostacyclin
EP0080718B1 (fr)	1986-05-14	Dérivés inter-m-phénylène-PGI2, procédé pour leur préparation et compositions pharmaceutiques les contenant
CH639950A5 (de)	1983-12-15	Verfahren zur herstellung von neuen 13-thiaprostansaeurederivaten.
DE3146278C2 (de)	1984-10-31	cis-Bicyclo[3.3.0]octanderivate, diese enthaltende Arzneimittel und Verfahren zur Herstellung dieser Verbindungen
EP0163905B1 (fr)	1989-01-25	Dérivés de 7-oxo-prostacycline racémiques et optiquement actifs, procédé pour leur préparation et compositions pharmaceutiques contenant ces composés
DE3518655A1 (de)	1986-11-27	Neue phenolderivate, diese enthaltende arzneimittel und verfahren zur herstellung dieser verbindungen und arzneimittel
EP0065200B1 (fr)	1987-02-25	Thiolactiméthers de delta 1-pyrrolidine et leur procédé de préparation
EP0205969B1 (fr)	1992-01-02	Sels de 7-oxo-PGI2 et d'éphédrine, leur préparation et compositions pharmaceutiques les contenant
EP0113311B1 (fr)	1992-01-02	5-Fluorocarbacyclines, procédé pour leur préparation et leur utilisation comme médicaments
DD244343A5 (de)	1987-04-01	Neue interfuranylen-prostacyclin-derivate und verfahren zu ihrer herstellung