JPS60209538A - カルボプロスタサイクリンの１‐ノル‐２‐ヒドロキシメチル‐誘導体およびその製造方法 - Google Patents

カルボプロスタサイクリンの１‐ノル‐２‐ヒドロキシメチル‐誘導体およびその製造方法

Info

Publication number: JPS60209538A
Authority: JP; Japan
Prior art keywords: formula; methylene; dihydroxy; hydroxymethyl; compound
Prior art date: 1984-03-26
Legal status (The legal status 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 status listed.): Pending

Application number

JP60055775A

Other languages

English (en)

Japanese (ja)

Inventor

ニコラ・モンジエルリ

ロベルト・チエセラーニ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Italia SRL

Original Assignee

Carlo Erba SpA

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.)

1984-03-26

Filing date

1985-03-22

Publication date

1985-10-22

1985-03-22 Application filed by Carlo Erba SpA filed Critical Carlo Erba SpA

1985-10-22 Publication of JPS60209538A publication Critical patent/JPS60209538A/ja

Status Pending legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 140
239000002253 acid Substances 0.000 claims description 81
239000000203 mixture Substances 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 22
238000000034 method Methods 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
239000003153 chemical reaction reagent Substances 0.000 claims description 10
125000006239 protecting group Chemical group 0.000 claims description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
125000001931 aliphatic group Chemical group 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
230000002265 prevention Effects 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
230000002744 anti-aggregatory effect Effects 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
150000002431 hydrogen Chemical group 0.000 claims description 4
208000001953 Hypotension Diseases 0.000 claims description 3
206010022714 Intestinal ulcer Diseases 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
208000021822 hypotensive Diseases 0.000 claims description 3
230000001077 hypotensive effect Effects 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
230000028327 secretion Effects 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
241001465754 Metazoa Species 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
239000011630 iodine Substances 0.000 claims description 2
239000002220 antihypertensive agent Substances 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
241001474791 Proboscis Species 0.000 claims 1
229940030600 antihypertensive agent Drugs 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
230000000414 obstructive effect Effects 0.000 claims 1
208000014731 pulmonary artery disease Diseases 0.000 claims 1
210000003296 saliva Anatomy 0.000 claims 1
238000009121 systemic therapy Methods 0.000 claims 1
229940124549 vasodilator Drugs 0.000 claims 1
239000003071 vasodilator agent Substances 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
239000000243 solution Substances 0.000 description 32
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 31
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
238000006243 chemical reaction Methods 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
-1 Dimethyl tert-butyl Chemical group 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 12
150000004702 methyl esters Chemical class 0.000 description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000000741 silica gel Substances 0.000 description 10
229910002027 silica gel Inorganic materials 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 8
102100028138 F-box/WD repeat-containing protein 7 Human genes 0.000 description 7
101001060231 Homo sapiens F-box/WD repeat-containing protein 7 Proteins 0.000 description 7
239000003480 eluent Substances 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
235000019799 monosodium phosphate Nutrition 0.000 description 6
230000009467 reduction Effects 0.000 description 6
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 6
229910000162 sodium phosphate Inorganic materials 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
230000000694 effects Effects 0.000 description 5
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
239000011734 sodium Substances 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
239000003826 tablet Substances 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000012267 brine Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
150000002148 esters Chemical group 0.000 description 4
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
238000001802 infusion Methods 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
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 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
150000001241 acetals Chemical class 0.000 description 3
238000005903 acid hydrolysis reaction Methods 0.000 description 3
239000000443 aerosol Substances 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
239000002775 capsule Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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125000005843 halogen group Chemical group 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
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239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
125000004043 oxo group Chemical group O=* 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
238000000926 separation method Methods 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
238000010561 standard procedure Methods 0.000 description 3
KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
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CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
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235000014113 dietary fatty acids Nutrition 0.000 description 2
125000001033 ether group Chemical group 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
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239000008101 lactose Substances 0.000 description 2
239000000787 lecithin Substances 0.000 description 2
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229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
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238000000746 purification Methods 0.000 description 2
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239000007929 subcutaneous injection Substances 0.000 description 2
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RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
230000000304 vasodilatating effect Effects 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
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DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
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VDCLSGXZVUDARN-UHFFFAOYSA-N molecular bromine;pyridine;hydrobromide Chemical compound Br.BrBr.C1=CC=NC=C1 VDCLSGXZVUDARN-UHFFFAOYSA-N 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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229920000136 polysorbate Polymers 0.000 description 1
229950008882 polysorbate Drugs 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
230000008569 process Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229920002379 silicone rubber Polymers 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
BOVHUUQISWANCW-UHFFFAOYSA-M sodium;acetylazanide Chemical compound CC(=O)N[Na] BOVHUUQISWANCW-UHFFFAOYSA-M 0.000 description 1
YXXYTGAWNWNKJL-UHFFFAOYSA-M sodium;pyrrolidin-1-ide-2,5-dione Chemical compound [Na+].O=C1CCC(=O)[N-]1 YXXYTGAWNWNKJL-UHFFFAOYSA-M 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
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239000000126 substance Substances 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
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230000002459 sustained effect Effects 0.000 description 1
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208000011580 syndromic disease Diseases 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003555 thioacetals Chemical class 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
230000008673 vomiting Effects 0.000 description 1
229940075420 xanthine Drugs 0.000 description 1
239000001060 yellow colorant Substances 0.000 description 1

Classifications

- 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
- C07C405/005—Analogues or derivatives having the five membered ring replaced by other rings
- C07C405/0075—Analogues or derivatives having the five membered ring replaced by other rings having the side-chains or their analogues or derivatives attached to a condensed ring system
- C07C405/0083—Analogues or derivatives having the five membered ring replaced by other rings having the side-chains or their analogues or derivatives attached to a condensed ring system which is only ortho or peri condensed, e.g. carbacyclins
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

JP60055775A 1984-03-26 1985-03-22 カルボプロスタサイクリンの１‐ノル‐２‐ヒドロキシメチル‐誘導体およびその製造方法 Pending JPS60209538A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB08407791A GB2156340A (en)	1984-03-26	1984-03-26	1-Nor-2-hydroxymethyl-derivatives of carboprostacyclins and process for their preparation
GB8407791		1984-03-26

Publications (1)

Publication Number	Publication Date
JPS60209538A true JPS60209538A (ja)	1985-10-22

Family

ID=10558688

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP60055775A Pending JPS60209538A (ja)	1984-03-26	1985-03-22	カルボプロスタサイクリンの１‐ノル‐２‐ヒドロキシメチル‐誘導体およびその製造方法

Country Status (5)

Country	Link
JP (1)	JPS60209538A (it)
BE (1)	BE902012A (it)
DE (1)	DE3507943A1 (it)
GB (1)	GB2156340A (it)
IT (1)	IT1200399B (it)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3812533A1 (de) *	1988-04-15	1989-10-26	Josef Seelen	Abdichtung fuer blasrohr oder welle

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2013661B (en) *	1978-01-26	1982-11-10	Erba Farmitalia	9-deoxy-9 -methylene isosteres of pgi2
US4705806A (en) *	1978-02-13	1987-11-10	Morton Jr Douglas R	Prostacyclin analogs

1984
- 1984-03-26 GB GB08407791A patent/GB2156340A/en not_active Withdrawn
1985
- 1985-03-05 IT IT19766/85A patent/IT1200399B/it active
- 1985-03-06 DE DE19853507943 patent/DE3507943A1/de not_active Withdrawn
- 1985-03-22 JP JP60055775A patent/JPS60209538A/ja active Pending
- 1985-03-25 BE BE0/214700A patent/BE902012A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE3507943A1 (de)	1985-09-26
IT8519766A0 (it)	1985-03-05
GB8407791D0 (en)	1984-05-02
GB2156340A (en)	1985-10-09
IT1200399B (it)	1989-01-18
BE902012A (fr)	1985-07-16

Publication	Publication Date	Title
EP0084856B1 (en)	1986-11-20	5,6,7-trinor-4, 8-inter-m-phenylene prostaglandin i2 derivatives
CS228916B2 (en)	1984-05-14	Method of preparing new derivatives of 9 alpha,6-nitril
PL99931B1 (pl)	1978-08-31	Sposob wytwarzania nowych analogow prostaglandyn
CA1042880A (en)	1978-11-21	Analogues of prostaglandins and process for their manufacture
HU187466B (en)	1986-01-28	Process for producing new 5-cyano-prostacycline derivatives and pharmaceutical compositions containing them
CH619930A5 (it)	1980-10-31
JPS60209538A (ja)	1985-10-22	カルボプロスタサイクリンの１‐ノル‐２‐ヒドロキシメチル‐誘導体およびその製造方法
US4514396A (en)	1985-04-30	15-Cycloaliphatic derivatives of 13,14-didehydro-carboprostacyclins and process for their preparation
JPS5846510B2 (ja)	1983-10-17	１３，１４−デヒドロ−１１−デオキシ−プロスタグランジン及びその製造法
JPS61227544A (ja)	1986-10-09	新規［４．２．０］ビシクロオクタン誘導体
JPS58159485A (ja)	1983-09-21	キラルな光学活性化合物
JPS5921864B2 (ja)	1984-05-22	フルオロプロスタグランジン及びその製造法
US3935241A (en)	1976-01-27	11α-METHYLSUBSTITUTED PROSTAGLANDIN DERIVATIVES
GB2129427A (en)	1984-05-16	15-Cycloaliphatic derivatives of 13,14-didehydrocarboprostacyclins and process for their preparation
US4296121A (en)	1981-10-20	Novel prostaglandin derivatives of the Δ2-PGF2 and Δ2-PGE2 series and process for their manufacture
CA1087613A (en)	1980-10-14	Prostaglandin synthesis and novel intermediates therefor
US3818059A (en)	1974-06-18	Preparation of tridecatrienoic acid derivatives
HU206342B (en)	1992-10-28	Process for producing 6-oxo-prostaglandine derivatives and pharmaceutical compositions containing them as active components
JPS6261593B2 (it)	1987-12-22
KR840001569B1 (ko)	1984-10-06	△ 2-pgf_₂및 △2-pge_₂계열의 프로스타글란딘 유도체의 제조방법
JPH05194469A (ja)	1993-08-03	プロスタグランジン中間体の製法
CN114957326A (zh)	2022-08-30	一种贝前列素钠膦叶立德中间体的合成方法
CS215150B2 (en)	1982-07-30	Method of making the 9-deoxy-9a-methylenisosters of the prostacycline pgi2
GB2156342A (en)	1985-10-09	13,14,19,20-Tetrahydro derivatives of carboprostacyclins and process for their preparation
JPS60209570A (ja)	1985-10-22	カルボプロスタサイクリンのフリルおよびイミダゾリル誘導体ならびにその製造方法