NO751726L - - Google Patents

Info

Publication number: NO751726L
Authority: NO; Norway
Prior art keywords: oxo; minutes; mmol; phenyl; dimethyl
Prior art date: 1972-07-13

Application number

NO751726A

Other languages

English (en)

Norwegian (no)

Inventor

M R Johnson

H-J E Hess

T K Schaaf

J S Bindra

Original Assignee

Pfizer

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.)

1972-07-13

Filing date

1975-05-15

Publication date

1974-01-15

1973-07-03 Priority claimed from NO2724/73A external-priority patent/NO143741C/no

1974-01-15 Publication of NO751726L publication Critical patent/NO751726L/no

1975-05-15 Application filed by Pfizer filed Critical Pfizer

1975-05-15 Priority to NO751726A priority Critical patent/NO751726L/no

Links

229940094443 oxytocics prostaglandins Drugs 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
150000003180 prostaglandins Chemical class 0.000 claims description 12
-1 3,4-methylenedioxyphenyl Chemical group 0.000 claims description 9
150000001875 compounds Chemical class 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
125000003545 alkoxy group Chemical group 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 79
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 32
239000000243 solution Substances 0.000 description 32
229960000583 acetic acid Drugs 0.000 description 31
238000006243 chemical reaction Methods 0.000 description 27
238000000034 method Methods 0.000 description 27
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 17
238000003756 stirring Methods 0.000 description 16
239000012299 nitrogen atmosphere Substances 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
239000007858 starting material Substances 0.000 description 12
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 9
239000002243 precursor Substances 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000000284 extract Substances 0.000 description 8
239000012362 glacial acetic acid Substances 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
239000008346 aqueous phase Substances 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
239000000499 gel Substances 0.000 description 7
238000002329 infrared spectrum Methods 0.000 description 7
239000000463 material Substances 0.000 description 7
239000000203 mixture Substances 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 6
VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
150000002596 lactones Chemical class 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
238000001179 sorption measurement Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
MBYFZYKLKDLPEU-UHFFFAOYSA-N 2-dimethoxyphosphoryl-1-phenylethanone Chemical compound COP(=O)(OC)CC(=O)C1=CC=CC=C1 MBYFZYKLKDLPEU-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
HQJAUSGLWRLGOI-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-phenylpropan-2-one Chemical compound COP(=O)(OC)CC(=O)CC1=CC=CC=C1 HQJAUSGLWRLGOI-UHFFFAOYSA-N 0.000 description 2
IVBKIMUBUJLMJA-UHFFFAOYSA-N 1-dimethoxyphosphoryl-4-(furan-2-yl)butan-2-one Chemical compound COP(=O)(OC)CC(=O)CCC1=CC=CO1 IVBKIMUBUJLMJA-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
UOKRBSXOBUKDGE-UHFFFAOYSA-N butylphosphonic acid Chemical compound CCCCP(O)(O)=O UOKRBSXOBUKDGE-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000006260 foam Substances 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
150000002373 hemiacetals Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
ZQYLDVNTWDEAJI-UHFFFAOYSA-N methyl 2-(4-methoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(OC)C=C1 ZQYLDVNTWDEAJI-UHFFFAOYSA-N 0.000 description 2
UXHQPGLQTVKTBI-UHFFFAOYSA-N methyl 3-(furan-2-yl)propanoate Chemical compound COC(=O)CCC1=CC=CO1 UXHQPGLQTVKTBI-UHFFFAOYSA-N 0.000 description 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
125000001412 tetrahydropyranyl group Chemical group 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
PSUXJJCBYWUFQC-KSNMPCKYSA-N (z)-7-[(1r,2r,3r)-3-hydroxy-2-[(3s)-3-hydroxyoctyl]-5-oxocyclopentyl]hept-5-enoic acid Chemical compound CCCCC[C@H](O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O PSUXJJCBYWUFQC-KSNMPCKYSA-N 0.000 description 1
NWPRXAIYBULIEI-UHFFFAOYSA-N 2-(methoxycarbonylamino)-3,3-dimethylbutanoic acid Chemical compound COC(=O)NC(C(O)=O)C(C)(C)C NWPRXAIYBULIEI-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
241000124033 Salix Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229940006138 antiglaucoma drug and miotics prostaglandin analogues Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000004872 arterial blood pressure Effects 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
YGBGWFLNLDFCQL-UHFFFAOYSA-N boron zinc Chemical compound [B].[Zn] YGBGWFLNLDFCQL-UHFFFAOYSA-N 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical compound [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 description 1
125000006243 carbonyl protecting group Chemical group 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
LMKPHJYTFHAGHK-UHFFFAOYSA-N cyclodrine Chemical compound C1CCCC1(O)C(C(=O)OCCN(CC)CC)C1=CC=CC=C1 LMKPHJYTFHAGHK-UHFFFAOYSA-N 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
229960001760 dimethyl sulfoxide Drugs 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000000457 gamma-lactone group Chemical group 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
239000002638 heterogeneous catalyst Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000002815 homogeneous catalyst Substances 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 1
KNKIXYMOHMYZJR-UHFFFAOYSA-N methyl 2-thiophen-2-ylacetate Chemical compound COC(=O)CC1=CC=CS1 KNKIXYMOHMYZJR-UHFFFAOYSA-N 0.000 description 1
LLJVWSKVDFWWSJ-UHFFFAOYSA-N methyl 3-thiophen-3-ylpropanoate Chemical compound COC(=O)CCC=1C=CSC=1 LLJVWSKVDFWWSJ-UHFFFAOYSA-N 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
230000037361 pathway Effects 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
MHZDONKZSXBOGL-UHFFFAOYSA-L propyl phosphate Chemical compound CCCOP([O-])([O-])=O MHZDONKZSXBOGL-UHFFFAOYSA-L 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000002601 radiography Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 0.000 description 1
230000035884 vasodepression Effects 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO751726A 1972-07-13 1975-05-15 NO751726L (fi)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
NO751726A NO751726L (fi)	1972-07-13	1975-05-15

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US27122072A	1972-07-13	1972-07-13
NO2724/73A NO143741C (no)	1972-07-13	1973-07-03	Analogifremgangsmaate for fremstilling av fysiologisk aktive prostaglandinforbindelser av e- og f-serien
NO751726A NO751726L (fi)	1972-07-13	1975-05-15

Publications (1)

Publication Number	Publication Date
NO751726L true NO751726L (fi)	1974-01-15

Family

ID=27352614

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO751726A NO751726L (fi)	1972-07-13	1975-05-15

Country Status (1)

Country	Link
NO (1)	NO751726L (fi)

1975
- 1975-05-15 NO NO751726A patent/NO751726L/no unknown

Publication	Publication Date	Title
US4024179A (en)	1977-05-17	Substituted ω-pentanorprostaglandins
US4011262A (en)	1977-03-08	13,14-Dihydro-15-substituted-ω-pentanorprostaglandins of the two series
JP2022036968A (ja)	2022-03-08	３－ヒドロキシ－３，６－ジメチルヘキサヒドロベンゾフラン－２－オンおよびその誘導体の製造
NO143663B (no)	1980-12-15	Analogifremgangsmaate for fremstilling av en fysiologisk aktiv prostaglandinforbindelse av e- eller f-serien
DE2355540C2 (de)	1982-11-18	16-Phenoxy-&omega;-tetranorprostaglandinderivate
CA1041495A (en)	1978-10-31	Process for preparing a 15-substituted-w-pentanorprostaglandins
US3984424A (en)	1976-10-05	P-biphenyl esters of 15-substituted-ω-pentanorprostaglandins
CA1042002A (en)	1978-11-07	Cyclopentane derivatives
NO763451L (fi)	1977-04-22
US3835179A (en)	1974-09-10	Novel 15-substituted prostanoic acids and esters
IE45773B1 (en)	1982-11-17	11-deoxy-11-oxaprostaglandin compounds
NO751726L (fi)	1974-01-15
NO146357B (no)	1982-06-07	Fremgangsmaate ved fremstilling av nye prostaglandiner.
EP0037588B1 (en)	1984-09-05	Method of preparing furfuryl alcohols
EP0038131B1 (en)	1984-08-08	Bicyclooctane compounds, their production, compositions containing them and their pharmaceutical use
JP2004161702A (ja)	2004-06-10	γ−ジャスモラクトンの製造方法
JPH026754B2 (fi)	1990-02-13
CH624929A5 (fi)	1981-08-31
US4036832A (en)	1977-07-19	15-Substituted-ω-pentanorprostaglandins
JPS6022708B2 (ja)	1985-06-03	プロスタグランジン類似化合物
NO743811L (fi)	1975-05-20
NO146280B (no)	1982-05-24	Bis-tetrahydropyranyleter for anvendelse som mellomprodukt for fremstilling av en fysiologisk aktiv p-bifenylester av en prostaglandinanalog av e- eller f-serien
US4143051A (en)	1979-03-06	15-Substituted-ω-pentanorprostaglandins
US4021425A (en)	1977-05-03	Process for producing enone intermediates
DE2716075A1 (de)	1978-02-23	Neue zwischenprodukte und verfahren zur herstellung von thromboxan-analoga