NO752623L - - Google Patents

Info

Publication number: NO752623L
Authority: NO; Norway
Prior art keywords: formula; compound; meaning; acid; specified
Prior art date: 1974-07-23

Application number

NO752623A

Other languages

English (en)

Norwegian (no)

Inventor

G Beck

W Bartmann

U Lerch

B Schoelkens

Original Assignee

Hoechst Ag

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.)

1974-07-23

Filing date

1975-07-23

Publication date

1976-01-26

1975-07-23 Application filed by Hoechst Ag filed Critical Hoechst Ag

1976-01-26 Publication of NO752623L publication Critical patent/NO752623L/no

Links

150000001875 compounds Chemical class 0.000 claims description 98
239000002253 acid Substances 0.000 claims description 61
239000000203 mixture Substances 0.000 claims description 22
150000002148 esters Chemical class 0.000 claims description 18
150000001298 alcohols Chemical class 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 14
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical group O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 claims description 12
-1 hydroxyl- Chemical group 0.000 claims description 12
238000000034 method Methods 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
229910052987 metal hydride Inorganic materials 0.000 claims description 10
150000004681 metal hydrides Chemical class 0.000 claims description 10
238000000926 separation method Methods 0.000 claims description 10
150000007513 acids Chemical class 0.000 claims description 9
229910052740 iodine Inorganic materials 0.000 claims description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 8
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 7
229920006395 saturated elastomer Polymers 0.000 claims description 6
150000003459 sulfonic acid esters Chemical class 0.000 claims description 6
150000002596 lactones Chemical class 0.000 claims description 5
150000007530 organic bases Chemical class 0.000 claims description 5
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
239000003814 drug Substances 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 4
150000007529 inorganic bases Chemical class 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
239000012312 sodium hydride Substances 0.000 claims description 4
229910000104 sodium hydride Inorganic materials 0.000 claims description 4
MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 claims description 3
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 3
239000005977 Ethylene Substances 0.000 claims description 3
125000001931 aliphatic group Chemical group 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
150000002923 oximes Chemical class 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
150000001338 aliphatic hydrocarbons Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
238000007257 deesterification reaction Methods 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000005188 oxoalkyl group Chemical group 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
239000003937 drug carrier Substances 0.000 claims 1
229940126601 medicinal product Drugs 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
238000003786 synthesis reaction Methods 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 10
239000000243 solution Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
150000001299 aldehydes Chemical class 0.000 description 8
229940094443 oxytocics prostaglandins Drugs 0.000 description 7
150000003180 prostaglandins Chemical class 0.000 description 7
239000002904 solvent Substances 0.000 description 7
238000001228 spectrum Methods 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000007792 addition Methods 0.000 description 6
239000012230 colorless oil Substances 0.000 description 6
238000004440 column chromatography Methods 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
125000000896 monocarboxylic acid group Chemical group 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
UGAPHEBNTGUMBB-UHFFFAOYSA-N acetic acid;ethyl acetate Chemical compound CC(O)=O.CCOC(C)=O UGAPHEBNTGUMBB-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
150000003008 phosphonic acid esters Chemical class 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000013543 active substance Substances 0.000 description 3
239000000010 aprotic solvent Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
239000003921 oil Substances 0.000 description 3
SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
239000003377 acid catalyst Substances 0.000 description 2
239000003513 alkali Substances 0.000 description 2
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
125000001033 ether group Chemical group 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000000047 product Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000000746 purification Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
230000007017 scission Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 2
238000002211 ultraviolet spectrum Methods 0.000 description 2
239000011701 zinc Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
VHGKKMNYWTYVKX-MKIRJTLGSA-N (2E)-7-[(1S,2S)-2-octylcyclopentyl]hepta-2,4,6-trienoic acid Chemical compound CCCCCCCC[C@H]1CCC[C@@H]1C=CC=C\C=C\C(O)=O VHGKKMNYWTYVKX-MKIRJTLGSA-N 0.000 description 1
FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
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 1
239000003810 Jones reagent Substances 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
238000007239 Wittig reaction Methods 0.000 description 1
JEDZLBFUGJTJGQ-UHFFFAOYSA-N [Na].COCCO[AlH]OCCOC Chemical compound [Na].COCCO[AlH]OCCOC JEDZLBFUGJTJGQ-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
230000003178 anti-diabetic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
WGQKYBSKWIADBV-UHFFFAOYSA-O benzylaminium Chemical compound [NH3+]CC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-O 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000037396 body weight Effects 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
XPYGGHVSFMUHLH-UUSULHAXSA-N falecalcitriol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(O)(C(F)(F)F)C(F)(F)F)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C XPYGGHVSFMUHLH-UUSULHAXSA-N 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
150000002314 glycerols Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
OFXSXYCSPVKZPF-UHFFFAOYSA-N methoxyperoxymethane Chemical compound COOOC OFXSXYCSPVKZPF-UHFFFAOYSA-N 0.000 description 1
150000002780 morpholines Chemical class 0.000 description 1
239000005445 natural material Substances 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
150000003138 primary alcohols Chemical class 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
230000003033 spasmogenic effect Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
ZRQNRTRXAVFCMB-UHFFFAOYSA-N tris(2,4,5-trioxa-1-stanna-3-borabicyclo[1.1.1]pentan-1-yl) borate Chemical compound [Sn+4].[Sn+4].[Sn+4].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-].[O-]B([O-])[O-] ZRQNRTRXAVFCMB-UHFFFAOYSA-N 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 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
- 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

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (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)
Furan Compounds (AREA)

NO752623A 1974-07-23 1975-07-23 NO752623L (xx)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2435331A DE2435331C2 (de)	1974-07-23	1974-07-23	Analoga von Prostansäuren und Verfahren zu ihrer Herstellung sowie diese Analoga von Prostansäuren enthaltende Arzneimittel

Publications (1)

Publication Number	Publication Date
NO752623L true NO752623L (xx)	1976-01-26

Family

ID=5921263

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO752623A NO752623L (xx)	1974-07-23	1975-07-23

Country Status (21)

Country	Link
US (1)	US4251669A (xx)
JP (1)	JPS6012349B2 (xx)
AT (1)	AT352917B (xx)
AU (1)	AU502124B2 (xx)
BE (1)	BE831649A (xx)
CA (1)	CA1073903A (xx)
CH (1)	CH612936A5 (xx)
DE (1)	DE2435331C2 (xx)
DK (1)	DK332275A (xx)
EG (1)	EG11802A (xx)
ES (1)	ES439465A1 (xx)
FI (1)	FI752089A (xx)
FR (1)	FR2279390A1 (xx)
GB (1)	GB1515896A (xx)
HU (1)	HU174006B (xx)
IL (1)	IL47727A (xx)
LU (1)	LU73031A1 (xx)
NL (1)	NL7508626A (xx)
NO (1)	NO752623L (xx)
SE (1)	SE7508380L (xx)
ZA (1)	ZA754696B (xx)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20100041912A1 (en) *	2007-01-05	2010-02-18	Astra Zeneca	Method for the wittig reaction in the preparation of carboprost

1974
- 1974-07-23 DE DE2435331A patent/DE2435331C2/de not_active Expired
1975
- 1975-07-16 ES ES439465A patent/ES439465A1/es not_active Expired
- 1975-07-17 IL IL47727A patent/IL47727A/xx unknown
- 1975-07-18 CA CA231,817A patent/CA1073903A/en not_active Expired
- 1975-07-18 NL NL7508626A patent/NL7508626A/xx not_active Application Discontinuation
- 1975-07-21 CH CH950975A patent/CH612936A5/xx not_active IP Right Cessation
- 1975-07-21 EG EG434/75A patent/EG11802A/xx active
- 1975-07-21 FI FI752089A patent/FI752089A/fi not_active Application Discontinuation
- 1975-07-21 LU LU73031A patent/LU73031A1/xx unknown
- 1975-07-22 AU AU83265/75A patent/AU502124B2/en not_active Expired
- 1975-07-22 AT AT566175A patent/AT352917B/de not_active IP Right Cessation
- 1975-07-22 ZA ZA00754696A patent/ZA754696B/xx unknown
- 1975-07-22 HU HU75HO1820A patent/HU174006B/hu unknown
- 1975-07-22 DK DK332275A patent/DK332275A/da not_active Application Discontinuation
- 1975-07-23 BE BE158535A patent/BE831649A/xx not_active IP Right Cessation
- 1975-07-23 SE SE7508380A patent/SE7508380L/xx unknown
- 1975-07-23 JP JP50089277A patent/JPS6012349B2/ja not_active Expired
- 1975-07-23 FR FR7522953A patent/FR2279390A1/fr active Granted
- 1975-07-23 NO NO752623A patent/NO752623L/no unknown
- 1975-07-23 GB GB30781/75A patent/GB1515896A/en not_active Expired
1978
- 1978-01-19 US US05/870,658 patent/US4251669A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
AU8326575A (en)	1977-01-27
ES439465A1 (es)	1977-10-01
CH612936A5 (xx)	1979-08-31
ZA754696B (en)	1976-07-28
EG11802A (en)	1979-06-30
IL47727A0 (en)	1975-10-15
JPS6012349B2 (ja)	1985-04-01
AT352917B (de)	1979-10-10
HU174006B (hu)	1979-10-28
DE2435331C2 (de)	1983-08-18
AU502124B2 (en)	1979-07-12
DK332275A (da)	1976-01-24
CA1073903A (en)	1980-03-18
DE2435331A1 (de)	1976-02-12
NL7508626A (nl)	1976-01-27
LU73031A1 (xx)	1977-03-21
FR2279390B1 (xx)	1980-04-30
GB1515896A (en)	1978-06-28
ATA566175A (de)	1979-03-15
FI752089A (xx)	1976-01-24
BE831649A (fr)	1976-01-23
US4251669A (en)	1981-02-17
SE7508380L (sv)	1976-01-26
FR2279390A1 (fr)	1976-02-20
IL47727A (en)	1980-03-31
JPS5136442A (xx)	1976-03-27

Publication	Publication Date	Title
NO153926B (no)	1986-03-10	Fremgangsmaate ved fremstilling av 9-desoksy-9a-metylenisostere av pgi2.
US3781306A (en)	1973-12-25	Bicyclic lactone diformate
US4061671A (en)	1977-12-06	Analogues of prostaglandins
US3773795A (en)	1973-11-20	11-deoxy prostaglandin intermediates
US4004020A (en)	1977-01-18	Novel prostanoic acid derivatives and process for the preparation thereof
US3984424A (en)	1976-10-05	P-biphenyl esters of 15-substituted-ω-pentanorprostaglandins
IE44016B1 (en)	1981-07-29	11-deoxy-16-aryl-17,18,19,20-tetranorprostaglandins
US4088775A (en)	1978-05-09	15-Ethylenedioxy-prostanoic acid derivatives and esters thereof and intermediates thereof
US3883659A (en)	1975-05-13	9-Oxaprostaglandin compositions
NO752623L (xx)	1976-01-26
US4229585A (en)	1980-10-21	Fluoro-prostaglandins
US4024181A (en)	1977-05-17	Analogues of prostanoic acids
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
Bromer et al.	1970	Total synthesis of prostaglandins
Ferrier et al.	1985	Functionalised carbocycles from carbohydrates. Part 7. A route to carbacyclin from a D-glucose derivative. X-Ray crystal structure of 3-endo-benzoyloxy-2-exo-(1, 3-diphenyl-1, 3, 2-diazaphospholan-2-yloxymethyl)-6-oxobicyclo [3.3. 0]-octane
SU1360582A3 (ru)	1987-12-15	Способ получени 9-деокси-9а-метилен-изостеров ПГJ @ или их лактонов
US4258053A (en)	1981-03-24	Thienyl-prostaglandins and process for their manufacture
IE41407B1 (en)	1980-01-02	Analogues of prostanoic acids and process for preparing them
US3816462A (en)	1974-06-11	Tricyclic lactone aldehyde
IE45606B1 (en)	1982-10-06	Prostanoic acid derivatives and processes for their preparation
SE415095B (sv)	1980-09-08	Forfarande for framstellning av 8,12-diisoprostansyraderivat
JPS6032626B2 (ja)	1985-07-29	プロスタン酸類縁体
US4425359A (en)	1984-01-10	Fluoro-prostaglandins and process for their preparation
US3816463A (en)	1974-06-11	Tricyclic glycol
IE45634B1 (en)	1982-10-20	Prostane derivatives