SU923365A3 - Способ получени простановых производных или их солей - Google Patents

Способ получени простановых производных или их солей Download PDF

Info

Publication number: SU923365A3
Authority: SU; USSR - Soviet Union
Prior art keywords: compound; solution; prostacyclin; ether; title
Prior art date: 1977-11-25

Application number

SU782690452A

Other languages

English (en)

Russian (ru)

Inventor

Форбрюгген Хельмут

Скубалла Вернер

Радюхель Бернд

Лозерт Вольфганг

Логе Олаф

Мюллер Бернд

Маннесманн Герда

Original Assignee

Шеринг Аг (Инофирма)

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.)

1977-11-25

Filing date

1978-11-24

Publication date

1982-04-23

1978-11-24 Application filed by Шеринг Аг (Инофирма) filed Critical Шеринг Аг (Инофирма)

1982-04-23 Application granted granted Critical

1982-04-23 Publication of SU923365A3 publication Critical patent/SU923365A3/ru

Links

150000003839 salts Chemical class 0.000 title claims description 12
238000000034 method Methods 0.000 title claims description 4
UKVVPDHLUHAJNZ-PMACEKPBSA-N prostane Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC UKVVPDHLUHAJNZ-PMACEKPBSA-N 0.000 title description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 156
150000001875 compounds Chemical class 0.000 claims description 120
239000000243 solution Substances 0.000 claims description 107
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 96
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 66
150000004702 methyl esters Chemical class 0.000 claims description 52
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 51
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 45
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 44
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 42
239000012267 brine Substances 0.000 claims description 42
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 42
239000012230 colorless oil Substances 0.000 claims description 40
229960001123 epoprostenol Drugs 0.000 claims description 38
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 36
239000000203 mixture Substances 0.000 claims description 36
239000000284 extract Substances 0.000 claims description 34
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
229910052943 magnesium sulfate Inorganic materials 0.000 claims description 33
235000019341 magnesium sulphate Nutrition 0.000 claims description 33
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
239000003921 oil Substances 0.000 claims description 26
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 25
239000000741 silica gel Substances 0.000 claims description 25
229910002027 silica gel Inorganic materials 0.000 claims description 25
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 23
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 22
229910052786 argon Inorganic materials 0.000 claims description 22
238000000746 purification Methods 0.000 claims description 22
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 18
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 18
238000001914 filtration Methods 0.000 claims description 18
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 12
235000017557 sodium bicarbonate Nutrition 0.000 claims description 12
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 12
238000003756 stirring Methods 0.000 claims description 12
235000011121 sodium hydroxide Nutrition 0.000 claims description 11
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
239000007858 starting material Substances 0.000 claims description 10
230000007935 neutral effect Effects 0.000 claims description 8
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 6
239000012043 crude product Substances 0.000 claims description 6
150000002009 diols Chemical class 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
239000005457 ice water Substances 0.000 claims description 6
229910000027 potassium carbonate Inorganic materials 0.000 claims description 6
WGJJROVFWIXTPA-OALUTQOASA-N prostanoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(O)=O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 claims description 6
229910052938 sodium sulfate Inorganic materials 0.000 claims description 6
235000011152 sodium sulphate Nutrition 0.000 claims description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
125000002252 acyl group Chemical group 0.000 claims description 5
125000001589 carboacyl group Chemical group 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
239000011630 iodine Substances 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
125000000217 alkyl group Chemical group 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 4
239000012141 concentrate Substances 0.000 claims description 4
238000001704 evaporation Methods 0.000 claims description 4
230000008020 evaporation Effects 0.000 claims description 4
-1 methyl diacetate methyl ester Chemical class 0.000 claims description 4
239000000047 product Substances 0.000 claims description 4
230000001681 protective effect Effects 0.000 claims description 4
239000002994 raw material Substances 0.000 claims description 4
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 claims description 4
235000019345 sodium thiosulphate Nutrition 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
125000002947 alkylene group Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
PZASAAIJIFDWSB-CKPDSHCKSA-N 8-[(1S)-1-[8-(trifluoromethyl)-7-[4-(trifluoromethyl)cyclohexyl]oxynaphthalen-2-yl]ethyl]-8-azabicyclo[3.2.1]octane-3-carboxylic acid Chemical compound FC(F)(F)C=1C2=CC([C@@H](N3C4CCC3CC(C4)C(O)=O)C)=CC=C2C=CC=1OC1CCC(C(F)(F)F)CC1 PZASAAIJIFDWSB-CKPDSHCKSA-N 0.000 claims description 2
239000005977 Ethylene Substances 0.000 claims description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 2
239000007983 Tris buffer Substances 0.000 claims description 2
238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
230000036772 blood pressure Effects 0.000 claims description 2
238000004587 chromatography analysis Methods 0.000 claims description 2
229940050176 methyl chloride Drugs 0.000 claims description 2
IIKJXRUQCCWYSP-UHFFFAOYSA-N methylsulfonylformamide Chemical compound CS(=O)(=O)C(N)=O IIKJXRUQCCWYSP-UHFFFAOYSA-N 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
125000005704 oxymethylene group Chemical group [H]C([H])([*:2])O[*:1] 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
238000012746 preparative thin layer chromatography Methods 0.000 claims description 2
FPOLWERNILTNDK-UHFFFAOYSA-N pyruvamide Chemical compound CC(=O)C(N)=O FPOLWERNILTNDK-UHFFFAOYSA-N 0.000 claims description 2
208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 2
238000003860 storage Methods 0.000 claims description 2
238000004809 thin layer chromatography Methods 0.000 claims description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
229910021653 sulphate ion Inorganic materials 0.000 claims 2
JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 claims 1
241000270281 Coluber constrictor Species 0.000 claims 1
102000016736 Cyclin Human genes 0.000 claims 1
108050006400 Cyclin Proteins 0.000 claims 1
OCKPROYBCPQWJO-UHFFFAOYSA-N acetyl isocyanate Chemical compound CC(=O)N=C=O OCKPROYBCPQWJO-UHFFFAOYSA-N 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
230000015572 biosynthetic process Effects 0.000 claims 1
238000001816 cooling Methods 0.000 claims 1
OQZCSNDVOWYALR-UHFFFAOYSA-N flurochloridone Chemical compound FC(F)(F)C1=CC=CC(N2C(C(Cl)C(CCl)C2)=O)=C1 OQZCSNDVOWYALR-UHFFFAOYSA-N 0.000 claims 1
239000013505 freshwater Substances 0.000 claims 1
235000011389 fruit/vegetable juice Nutrition 0.000 claims 1
239000012948 isocyanate Substances 0.000 claims 1
150000002513 isocyanates Chemical class 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
FXBYOMANNHFNQV-UHFFFAOYSA-L magnesium;hydrogen sulfate Chemical compound [Mg+2].OS([O-])(=O)=O.OS([O-])(=O)=O FXBYOMANNHFNQV-UHFFFAOYSA-L 0.000 claims 1
229910001510 metal chloride Inorganic materials 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
238000003786 synthesis reaction Methods 0.000 claims 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 1
POCFBDFTJMJWLG-UHFFFAOYSA-N dihydrosinapic acid methyl ester Natural products COC(=O)CCC1=CC(OC)=C(O)C(OC)=C1 POCFBDFTJMJWLG-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
OUPLTJDZPQZRBW-UHFFFAOYSA-N n-(oxomethylidene)methanesulfonamide Chemical compound CS(=O)(=O)N=C=O OUPLTJDZPQZRBW-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
239000002904 solvent 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
- 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Diabetes (AREA)
Hematology (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Furan Compounds (AREA)

SU782690452A 1977-11-25 1978-11-24 Способ получени простановых производных или их солей SU923365A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772753244 DE2753244A1 (de)	1977-11-25	1977-11-25	Neue prostacyclinderivate und verfahren zu ihrer herstellung

Publications (1)

Publication Number	Publication Date
SU923365A3 true SU923365A3 (ru)	1982-04-23

Family

ID=6024901

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU782690452A SU923365A3 (ru)	1977-11-25	1978-11-24	Способ получени простановых производных или их солей

Country Status (23)

Country	Link
US (1)	US4219479A (2)
EP (1)	EP0002234B1 (2)
JP (1)	JPS5481257A (2)
AT (1)	AT371455B (2)
AU (1)	AU523420B2 (2)
CA (1)	CA1180701A (2)
CS (1)	CS209909B2 (2)
DD (1)	DD140042A5 (2)
DE (2)	DE2753244A1 (2)
DK (1)	DK153482C (2)
ES (1)	ES475377A1 (2)
FI (1)	FI68621C (2)
GR (1)	GR72772B (2)
HU (1)	HU181518B (2)
IE (1)	IE47497B1 (2)
IL (1)	IL56017A (2)
IT (1)	IT1160264B (2)
NO (1)	NO148642C (2)
NZ (1)	NZ188976A (2)
PH (1)	PH20276A (2)
SU (1)	SU923365A3 (2)
YU (1)	YU271078A (2)
ZA (1)	ZA786622B (2)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4178367A (en) *	1977-02-21	1979-12-11	Ono Pharmaceutical Co. Ltd.	Prostaglandin I2 analogues
DE2902809A1 (de) *	1979-01-25	1980-08-07	Hoechst Ag	Neue analoga von prostacyclin
DE3004795A1 (de) *	1980-02-07	1981-08-13	Schering Ag Berlin Und Bergkamen, 1000 Berlin	Neue prostacyclinderivate, ihre herstellung und anwendung
DE3041602A1 (de) *	1980-10-31	1982-06-16	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Neue 5-cyan-prostacyclinderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE3041601A1 (de) *	1980-10-31	1982-06-16	Schering Ag, 1000 Berlin Und 4619 Bergkamen	Neue prostacyclinderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE3322893A1 (de) *	1983-06-23	1985-01-03	Schering AG, 1000 Berlin und 4709 Bergkamen	Neue prostacyclinderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE3448256C2 (en) *	1984-07-25	1988-08-18	Schering Ag, 1000 Berlin Und 4709 Bergkamen, De	Cytoprotective action of prostacyclin derivatives on the pancreas
DE3448257C2 (en) *	1984-07-25	1988-08-18	Schering Ag, 1000 Berlin Und 4709 Bergkamen, De	Cytoprotective action of prostacyclin derivatives on the kidney
DE3740838A1 (de) *	1987-11-27	1989-06-08	Schering Ag	Cyclodextrinclathrate von 5-cyano-prostacyclinderivaten und ihre verwendung als arzneimittel
JP2009543826A (ja) *	2006-07-18	2009-12-10	バイエル・シエーリング・ファーマアクチエンゲゼルシャフト	自己免疫疾患治療剤としての５−シアノ−プロスタサイクリン誘導体
JP5271272B2 (ja) *	2006-11-16	2013-08-21	ジェンムスファーマインコーポレイティド	Ａ型インフルエンザウィルス感染の治療のための薬剤としてのｅｐ２およびｅｐ４作動薬
US20080242713A1 (en) *	2007-03-28	2008-10-02	Bayer Schering Pharma Aktiengesellschaft	Novel 5-cyano-prostacyclin derivatives as agents for the treatment of autoimmune diseases
EP1975163A1 (en) *	2007-03-28	2008-10-01	Bayer Schering Pharma Aktiengesellschaft	Novel 5-cyano-prostacyclin derivatives and their use as agents for the treatment of influenza a viral infection
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1977
- 1977-11-25 DE DE19772753244 patent/DE2753244A1/de not_active Withdrawn
1978
- 1978-11-21 YU YU02710/78A patent/YU271078A/xx unknown
- 1978-11-22 JP JP14358878A patent/JPS5481257A/ja active Granted
- 1978-11-22 PH PH21832A patent/PH20276A/en unknown
- 1978-11-22 IL IL56017A patent/IL56017A/xx unknown
- 1978-11-22 NZ NZ188976A patent/NZ188976A/xx unknown
- 1978-11-23 GR GR57720A patent/GR72772B/el unknown
- 1978-11-23 DE DE7878101445T patent/DE2860486D1/de not_active Expired
- 1978-11-23 AT AT0836478A patent/AT371455B/de not_active IP Right Cessation
- 1978-11-23 DK DK522578A patent/DK153482C/da active
- 1978-11-23 EP EP78101445A patent/EP0002234B1/de not_active Expired
- 1978-11-23 FI FI783590A patent/FI68621C/fi not_active IP Right Cessation
- 1978-11-24 ES ES475377A patent/ES475377A1/es not_active Expired
- 1978-11-24 NO NO783964A patent/NO148642C/no unknown
- 1978-11-24 ZA ZA00786622A patent/ZA786622B/xx unknown
- 1978-11-24 SU SU782690452A patent/SU923365A3/ru active
- 1978-11-24 CA CA000316872A patent/CA1180701A/en not_active Expired
- 1978-11-24 HU HU78SCHE661A patent/HU181518B/hu not_active IP Right Cessation
- 1978-11-24 IE IE2321/78A patent/IE47497B1/en not_active IP Right Cessation
- 1978-11-24 US US05/963,240 patent/US4219479A/en not_active Expired - Lifetime
- 1978-11-24 IT IT30174/78A patent/IT1160264B/it active
- 1978-11-24 AU AU41912/78A patent/AU523420B2/en not_active Expired
- 1978-11-24 CS CS787724A patent/CS209909B2/cs unknown
- 1978-11-27 DD DD78209338A patent/DD140042A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
ZA786622B (en)	1979-10-31
ES475377A1 (es)	1979-04-01
GR72772B (2)	1983-12-05
FI68621B (fi)	1985-06-28
AT371455B (de)	1983-06-27
PH20276A (en)	1986-11-14
JPS6220989B2 (2)	1987-05-11
DE2860486D1 (en)	1981-03-26
NO783964L (no)	1979-05-28
YU271078A (en)	1983-01-21
EP0002234A1 (de)	1979-06-13
US4219479A (en)	1980-08-26
IT1160264B (it)	1987-03-11
FI783590A7 (fi)	1979-05-26
AU523420B2 (en)	1982-07-29
DK153482B (da)	1988-07-18
ATA836478A (de)	1982-11-15
IT7830174A0 (it)	1978-11-24
DK522578A (da)	1979-05-26
IL56017A (en)	1983-03-31
DK153482C (da)	1988-12-27
CA1180701A (en)	1985-01-08
JPS5481257A (en)	1979-06-28
CS209909B2 (en)	1981-12-31
EP0002234B1 (de)	1981-02-11
NO148642B (no)	1983-08-08
IL56017A0 (en)	1979-01-31
NO148642C (no)	1983-11-16
HU181518B (en)	1983-10-28
DE2753244A1 (de)	1979-06-07
FI68621C (fi)	1985-10-10
IE782321L (en)	1979-05-25
DD140042A5 (de)	1980-02-06
AU4191278A (en)	1979-05-31
IE47497B1 (en)	1984-04-04
NZ188976A (en)	1979-12-11

Publication	Publication Date	Title
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US5097049A (en)	1992-03-17	Process and intermediates for chiral epoxides
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CA2384145A1 (en)	2001-03-15	Process for the preparation of 2,3-dihydroazepine compounds
TANAKA et al.	1983	Synthetic Studies on a Picrotoxane Sesquiterpene, Coriamyrtin. I. The Grignard Reaction of 5-(2-Methyl-1, 3-dioxo-2-cyclopentyl) methyl-2, 5H-furanone with Isopropenylmagnesium Bromide and Stereochemistries of the Products
JPH06345777A (ja)	1994-12-20	ジイソピノカンフェニルクロロボランのインシトゥー製造
US4906765A (en)	1990-03-06	Process for the production of 4-alkoxy-2(5H) thiophenones
US4346042A (en)	1982-08-24	Preparation of epihalohydrin enantiomers
持田顕一 et al.	1988	Synthetic studies on 1-carbacephem antibiotics: New synthetic approach to 3H-carbacephems.
US4375557A (en)	1983-03-01	Process for the preparation of dihalovinylcyclopropane carboxylic acid
US5183910A (en)	1993-02-02	Process and intermediates for chiral epoxides
CA1133470A (en)	1982-10-12	Cephapirine esters, salts thereof and processes for producing the same
SU676167A3 (ru)	1979-07-25	Способ получени производных тиофосфорной кислоты
SU1179921A3 (ru)	1985-09-15	Способ получени сложных этиловых эфиров 1-метил-или 1,4-диметил-1 @ -пиррол-2-уксусной кислоты
CA1095077A (en)	1981-02-03	Process for the production of a derivative of phenylacetic acid
SU459076A1 (ru)	1979-03-05	Способ получени 1-фенил-(о,м,п-алкоксифенил)-циклопентил-1-пенициллинов
US5164519A (en)	1992-11-17	Process for the separation of R and S-2,2-R1,R2 -1,3-dioxolane-4-carboxylic acid
US5153330A (en)	1992-10-06	Thiapentanamide derivatives
US5256807A (en)	1993-10-26	Process and intermediates for chiral epoxides
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