DD140047A5 - Verfahren zur herstellung racemischer und optisch aktiver halbprostanoid-glycoside und-thioglycoside - Google Patents

Verfahren zur herstellung racemischer und optisch aktiver halbprostanoid-glycoside und-thioglycoside Download PDF

Info

Publication number: DD140047A5
Authority: DD; German Democratic Republic
Prior art keywords: general formula; compounds; group; meaning; hydroxy
Prior art date: 1977-09-26

Application number

DD78208071A

Other languages

German (de)

English (en)

Inventor

Tibor Szabo

Laszlo Institoris

Gabor Kovacs

Gyula Dalmadi

Bela Koeszegi

Istvan Stadler

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

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.)

1977-09-26

Filing date

1978-09-25

Publication date

1980-02-06

1978-09-25 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1980-02-06 Publication of DD140047A5 publication Critical patent/DD140047A5/de

Links

238000000034 method Methods 0.000 title claims description 18
229940127293 prostanoid Drugs 0.000 title claims description 3
238000004519 manufacturing process Methods 0.000 title claims 2
229930182475 S-glycoside Natural products 0.000 title description 3
150000003569 thioglycosides Chemical class 0.000 title description 2
150000003814 prostanoids Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 85
238000006243 chemical reaction Methods 0.000 claims description 51
-1 carbalkoxy Chemical group 0.000 claims description 46
239000000203 mixture Substances 0.000 claims description 41
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 claims description 8
125000004423 acyloxy group Chemical group 0.000 claims description 7
230000002378 acidificating effect Effects 0.000 claims description 6
239000003377 acid catalyst Substances 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
125000004434 sulfur atom Chemical group 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000001072 heteroaryl group Chemical group 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000004043 oxo group Chemical group O=* 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
239000011877 solvent mixture Substances 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
125000003435 aroyl group Chemical group 0.000 claims 1
125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims 1
239000012442 inert solvent Substances 0.000 claims 1
125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 108
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
239000000047 product Substances 0.000 description 26
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 20
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 15
238000004809 thin layer chromatography Methods 0.000 description 15
239000000741 silica gel Substances 0.000 description 14
229910002027 silica gel Inorganic materials 0.000 description 14
239000002904 solvent Substances 0.000 description 14
239000007858 starting material Substances 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
239000003921 oil Substances 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
230000008569 process Effects 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000003480 eluent Substances 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
239000000155 melt Substances 0.000 description 5
DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
230000009466 transformation Effects 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
230000002401 inhibitory effect Effects 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
150000003180 prostaglandins Chemical class 0.000 description 3
238000003756 stirring Methods 0.000 description 3
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
AXCHZLOJGKSWLV-UHFFFAOYSA-N (4-phenylphenyl)methanol Chemical compound C1=CC(CO)=CC=C1C1=CC=CC=C1 AXCHZLOJGKSWLV-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
230000002776 aggregation Effects 0.000 description 2
238000004220 aggregation Methods 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
210000001772 blood platelet Anatomy 0.000 description 2
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
125000005518 carboxamido group Chemical group 0.000 description 2
229960000541 cetyl alcohol Drugs 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
230000008602 contraction Effects 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000020176 deacylation Effects 0.000 description 2
238000005947 deacylation reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000003700 epoxy group Chemical group 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
229930182470 glycoside Natural products 0.000 description 2
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
210000002460 smooth muscle Anatomy 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
QMBJSIBWORFWQT-UHFFFAOYSA-N (17-acetyl-6-chloro-10,13-dimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1h-cyclopenta[a]phenanthren-17-yl) acetate Chemical group C1=C(Cl)C2=CC(=O)CCC2(C)C2C1C1CCC(C(C)=O)(OC(=O)C)C1(C)CC2 QMBJSIBWORFWQT-UHFFFAOYSA-N 0.000 description 1
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 description 1
102100024341 10 kDa heat shock protein, mitochondrial Human genes 0.000 description 1
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
125000006012 2-chloroethoxy group Chemical group 0.000 description 1
SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
108010059013 Chaperonin 10 Proteins 0.000 description 1
241000065675 Cyclops Species 0.000 description 1
101710088194 Dehydrogenase Proteins 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
239000004593 Epoxy Chemical group 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
230000006819 RNA synthesis Effects 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000002009 alkene group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
238000004049 embossing Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
210000002599 gastric fundus Anatomy 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
210000002429 large intestine Anatomy 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
150000007522 mineralic acids Chemical class 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
230000017570 negative regulation of blood coagulation Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229940094443 oxytocics prostaglandins Drugs 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000001243 protein synthesis Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000006190 sub-lingual tablet Substances 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000008030 superplasticizer Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000003420 transacetalization reaction Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
230000014616 translation Effects 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Hematology (AREA)
Diabetes (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Furan Compounds (AREA)

DD78208071A 1977-09-26 1978-09-25 Verfahren zur herstellung racemischer und optisch aktiver halbprostanoid-glycoside und-thioglycoside DD140047A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU77CI1771A HU178202B (en)	1977-09-26	1977-09-26	Process for preparing new,optically active and racemic bicyclic acetals and merkaptals

Publications (1)

Publication Number	Publication Date
DD140047A5 true DD140047A5 (de)	1980-02-06

Family

ID=10994671

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD78208071A DD140047A5 (de)	1977-09-26	1978-09-25	Verfahren zur herstellung racemischer und optisch aktiver halbprostanoid-glycoside und-thioglycoside

Country Status (21)

Country	Link
US (1)	US4257962A (cs)
JP (1)	JPS5459267A (cs)
AT (1)	AT369363B (cs)
BE (1)	BE870759A (cs)
CA (1)	CA1191845A (cs)
CH (1)	CH644373A5 (cs)
CS (1)	CS209504B2 (cs)
DD (1)	DD140047A5 (cs)
DE (1)	DE2841181A1 (cs)
DK (1)	DK424578A (cs)
FI (1)	FI69460C (cs)
FR (1)	FR2404004A1 (cs)
GB (1)	GB2005677B (cs)
GR (1)	GR65212B (cs)
HU (1)	HU178202B (cs)
IL (1)	IL55576A (cs)
IT (1)	IT1160676B (cs)
NL (1)	NL7809735A (cs)
PL (1)	PL115376B1 (cs)
SE (1)	SE443979B (cs)
SU (1)	SU890973A3 (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4499292A (en) *	1983-05-13	1985-02-12	E. R. Squibb & Sons, Inc.	7-Oxabicycloheptane prostaglandin intermediates and method for preparing same
KR102277188B1 (ko) *	2011-06-02	2021-07-15	키노인 제트알티.	프로스타글란딘 아미드의 신규한 제조 방법

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3023183A (en) *	1959-06-29	1962-02-27	Cuban American Sugar Company	Esterification
US3657328A (en) *	1970-05-22	1972-04-18	Ciba Geigy Corp	Pge1 oximes
BE795199A (fr) *	1972-05-10	1973-08-09	Ciba Geigy	Nouveaux oxabicyclononanes et leurs procedes de preparation
US3975406A (en) *	1972-07-06	1976-08-17	Hans Johann Mayer	Hexahydro-5-oxy-2-loweralkoxy-2H-cyclopenta[b]-furan-4-carbonitrile intermediates for prostaglandins
US3987085A (en) *	1972-09-15	1976-10-19	The Upjohn Company	8β,11β,12α-PGF2.sub.α compounds
US4036871A (en) *	1973-08-06	1977-07-19	Hoffmann-La Roche Inc.	11-Substituted prostaglandins
US4041064A (en) *	1974-09-17	1977-08-09	Carlo-Erba S.P.A.	16-Methyl prost-5-en-13-ynoic acid derivatives
US4064351A (en) *	1974-09-19	1977-12-20	Sankyo Company Limited	9-OXO-15 ξ-HYDROXY-20-ALKYLIDENEPROST-13(TRANS)-ENOIC ACID DERIVATIVES
US4094886A (en) *	1976-03-01	1978-06-13	(Zaidanhojin) Sagami Chemical Research Center	Process for producing allyl alcohol derivatives useful in prostaglandin synthesis
JPS5398953A (en) *	1977-02-08	1978-08-29	Ono Pharmaceut Co Ltd	Prostaglandin x analogues and process for their preparation

1977
- 1977-09-26 HU HU77CI1771A patent/HU178202B/hu unknown
1978
- 1978-09-14 IL IL55576A patent/IL55576A/xx unknown
- 1978-09-15 US US05/942,819 patent/US4257962A/en not_active Expired - Lifetime
- 1978-09-21 SE SE7809947A patent/SE443979B/sv unknown
- 1978-09-22 DE DE19782841181 patent/DE2841181A1/de not_active Withdrawn
- 1978-09-25 JP JP11780478A patent/JPS5459267A/ja active Pending
- 1978-09-25 FI FI782913A patent/FI69460C/fi not_active IP Right Cessation
- 1978-09-25 FR FR7827399A patent/FR2404004A1/fr active Granted
- 1978-09-25 SU SU782666853A patent/SU890973A3/ru active
- 1978-09-25 DK DK424578A patent/DK424578A/da not_active Application Discontinuation
- 1978-09-25 GR GR57302A patent/GR65212B/el unknown
- 1978-09-25 CH CH999078A patent/CH644373A5/de not_active IP Right Cessation
- 1978-09-25 DD DD78208071A patent/DD140047A5/de unknown
- 1978-09-26 CA CA000312130A patent/CA1191845A/en not_active Expired
- 1978-09-26 BE BE190704A patent/BE870759A/xx not_active IP Right Cessation
- 1978-09-26 PL PL1978209858A patent/PL115376B1/pl unknown
- 1978-09-26 NL NL7809735A patent/NL7809735A/xx not_active Application Discontinuation
- 1978-09-26 AT AT0692578A patent/AT369363B/de not_active IP Right Cessation
- 1978-09-26 CS CS786218A patent/CS209504B2/cs unknown
- 1978-09-26 GB GB7838226A patent/GB2005677B/en not_active Expired
- 1978-09-26 IT IT69212/78A patent/IT1160676B/it active

Also Published As

Publication number	Publication date
FI782913A7 (fi)	1979-03-27
US4257962A (en)	1981-03-24
NL7809735A (nl)	1979-03-28
PL115376B1 (en)	1981-03-31
HU178202B (en)	1982-03-28
CA1191845A (en)	1985-08-13
GB2005677B (en)	1982-05-26
AT369363B (de)	1982-12-27
FI69460C (fi)	1986-02-10
GR65212B (en)	1980-07-30
JPS5459267A (en)	1979-05-12
IL55576A (en)	1982-03-31
GB2005677A (en)	1979-04-25
DE2841181A1 (de)	1979-04-05
FR2404004B1 (cs)	1982-12-17
BE870759A (fr)	1979-01-15
IT7869212A0 (it)	1978-09-26
SE443979B (sv)	1986-03-17
SU890973A3 (ru)	1981-12-15
PL209858A1 (pl)	1979-09-10
FI69460B (fi)	1985-10-31
IT1160676B (it)	1987-03-11
SE7809947L (sv)	1979-03-27
FR2404004A1 (fr)	1979-04-20
DK424578A (da)	1979-03-27
CH644373A5 (de)	1984-07-31
IL55576A0 (en)	1978-12-17
ATA692578A (de)	1982-05-15
CS209504B2 (en)	1981-12-31

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DE69923768T2 (de)	2006-03-23	Cephalotoxanderivative und verfahren zu ihrer herstellung
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DE1543891A1 (de)	1970-02-12	Ein neues Glucosid sowie ein Verfahren zu seiner Herstellung
EP0237902A2 (de)	1987-09-23	Verfahren zur Herstellung des (-)-Antipoden des (E)-1-Cyclohexyl-4,4-dimethyl-3-hydroxy-2-(1,2,4-triazol-1-yl)-pent-1-ens
DD140047A5 (de)	1980-02-06	Verfahren zur herstellung racemischer und optisch aktiver halbprostanoid-glycoside und-thioglycoside
EP0137309B1 (de)	1988-06-29	Mehrcyclische Kohlensäureester und neue Copolymere erhältlich aus diesen mehrcyclischen Kohlensäureestern und monocyclischen Carbonaten
CH629769A5 (de)	1982-05-14	Verfahren zur herstellung von fluorprostaglandinen.
EP0139859B1 (de)	1988-10-19	1,4-Dihydropyridine, Verfahren zu ihrer Herstellung sowie ihre Verwendung in Arzneimitteln
DE2729844C2 (de)	1984-06-07	Verfahren zur stereoselektiven Herstellung von optisch aktiven 6a,10a-trans-1- Hydroxy-3-alkyl-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo [b,d] pyran-9-onen
EP0112502A2 (de)	1984-07-04	Omega,omega-Diacyloxy-2,6-dimethyl-octatriensäureester und -aldehyde, Verfahren zu ihrer Herstellung und Verwendung zur Synthese von Terpenverbindungen
CH683340A5 (de)	1994-02-28	Verfahren zur Herstellung von 2,2-Dimethyl-5-(2,5-Dimethylphenoxy)-Pentansäure.
DE3590057C1 (de)	1992-11-19	Verfahren zur Herstellung von Diacyldianhydrohexiten
CH497413A (de)	1970-10-15	Verfahren zur Herstellung von Acylderivaten des Proscillaridins A
DE3780730T2 (de)	1993-03-18	Optisch wirksame beta-aminosaeure derivate und ihre salze und verfahren zu deren herstellung.
EP0051247B1 (de)	1985-01-09	4-Thia- und 4-Sulfinyl-PGI1-Derivate, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende pharmazeutische Präparate
DE3109532C2 (de)	1986-01-30	Stereoisomere 1,4;3,6-Dianhydro-2,5-diazido-2,5-didesoxyhexite, Verfahren zur Herstellung derselben und diese Verbindungen enthaltende Arzneimittel
DE957123C (de)	1957-01-31	Verfahren zur Herstellung von Thioabkoemmlingen der Colchiceine
DE1795424B2 (de)	1973-02-01	Glucuronsaeureester von 1-acyl-2methyl-5-methoxy-3-indolylessigsaeuren
AT362387B (de)	1981-05-11	Verfahren zur herstellung von neuen unsymmetrischen n,n'-thio-di-carbamaten
AT288363B (de)	1971-03-10	Verfahren zur Herstellung von neuen β-Aroyl- β-halogenacrylsäuren
CH635055A5 (de)	1983-03-15	Verfahren zur herstellung lipidsenkender alkylenglykolderivate.
CH648837A5 (de)	1985-04-15	Zuckeralkoholderivate, verfahren zu ihrer herstellung, die diese verbindungen enthaltenden pharmazeutischen zubereitungen.
DE2820411A1 (de)	1978-11-16	Halbsynthetische 4"-sulfonylamino- oleandomycinderivate