CS200463B2 - Method of preparing sulphides - Google Patents

Method of preparing sulphides Download PDF

Info

Publication number: CS200463B2
Authority: CS; Czechoslovakia
Prior art keywords: ppm; formula; carbon atoms; hydrogen; reaction
Prior art date: 1972-11-17

Application number

CS737749A

Other languages

Czech (cs)

English (en)

Inventor

Josef Kraemer

Hans Radunz

Dieter Orth

Manfred Baumgarth

Juergen Harting

Original Assignee

Merck Patent Gmbh

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.)

1972-11-17

Filing date

1973-11-12

Publication date

1980-09-15

1972-11-17 Priority claimed from DE2256537A external-priority patent/DE2256537A1/de

1973-11-12 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

1978-11-30 Priority to CS787898A priority Critical patent/CS200464B2/cs

1980-09-15 Publication of CS200463B2 publication Critical patent/CS200463B2/cs

Links

150000003568 thioethers Chemical class 0.000 title claims abstract description 5
238000000034 method Methods 0.000 title claims description 16
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 15
125000002947 alkylene group Chemical group 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 55
150000001875 compounds Chemical class 0.000 claims description 50
238000006243 chemical reaction Methods 0.000 claims description 43
125000004432 carbon atom Chemical group C* 0.000 claims description 38
239000001257 hydrogen Substances 0.000 claims description 33
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
150000002431 hydrogen Chemical group 0.000 claims description 19
125000004423 acyloxy group Chemical group 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
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 4
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
150000001342 alkaline earth metals Chemical class 0.000 claims description 3
230000003287 optical effect Effects 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims 1
150000002825 nitriles Chemical class 0.000 claims 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract description 3
-1 alkyl radical Chemical class 0.000 description 122
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
239000002253 acid Substances 0.000 description 32
238000001228 spectrum Methods 0.000 description 32
239000002904 solvent Substances 0.000 description 30
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
238000002329 infrared spectrum Methods 0.000 description 26
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
229910052799 carbon Inorganic materials 0.000 description 23
239000000243 solution Substances 0.000 description 23
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
239000000203 mixture Substances 0.000 description 16
229910052717 sulfur Inorganic materials 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 14
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
150000002148 esters Chemical class 0.000 description 13
239000003921 oil Substances 0.000 description 13
150000003254 radicals Chemical class 0.000 description 13
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
229910052751 metal Inorganic materials 0.000 description 12
239000002184 metal Substances 0.000 description 12
229960001404 quinidine Drugs 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
239000003054 catalyst Substances 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
150000007513 acids Chemical class 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
229910052938 sodium sulfate Inorganic materials 0.000 description 9
235000011152 sodium sulphate Nutrition 0.000 description 9
150000001340 alkali metals Chemical group 0.000 description 8
239000011734 sodium Substances 0.000 description 8
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 7
229910052783 alkali metal Chemical group 0.000 description 7
238000009835 boiling Methods 0.000 description 7
239000012442 inert solvent Substances 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
125000003710 aryl alkyl group Chemical group 0.000 description 5
239000007788 liquid Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
238000003756 stirring Methods 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 4
150000003863 ammonium salts Chemical class 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000003814 drug Substances 0.000 description 4
125000004494 ethyl ester group Chemical group 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000000377 silicon dioxide Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000011575 calcium Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
150000002430 hydrocarbons Chemical class 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
230000007017 scission Effects 0.000 description 3
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
235000011149 sulphuric acid Nutrition 0.000 description 3
150000007944 thiolates Chemical class 0.000 description 3
239000008096 xylene Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-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
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
229910000272 alkali metal oxide Inorganic materials 0.000 description 2
150000001447 alkali salts Chemical class 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
125000004414 alkyl thio group Chemical group 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
238000011097 chromatography purification Methods 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
WLXALCKAKGDNAT-UHFFFAOYSA-N diazoethane Chemical compound CC=[N+]=[N-] WLXALCKAKGDNAT-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000395 magnesium oxide Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
229910000000 metal hydroxide Inorganic materials 0.000 description 2
150000004692 metal hydroxides Chemical class 0.000 description 2
239000011707 mineral Substances 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
150000002923 oximes Chemical class 0.000 description 2
FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
239000012071 phase Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
230000005418 spin wave Effects 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 1
IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
VRGSWPWEELQLCM-UHFFFAOYSA-N 1-(4-methylphenyl)-2-sulfanylethanol Chemical compound CC1=CC=C(C(O)CS)C=C1 VRGSWPWEELQLCM-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
FETFXNFGOYOOSP-UHFFFAOYSA-N 1-sulfanylpropan-2-ol Chemical compound CC(O)CS FETFXNFGOYOOSP-UHFFFAOYSA-N 0.000 description 1
JDMNQLQJKKCRTE-UHFFFAOYSA-N 2-(4-methylphenyl)-1-sulfanylpropan-2-ol Chemical compound CC1=CC=C(C(C)(O)CS)C=C1 JDMNQLQJKKCRTE-UHFFFAOYSA-N 0.000 description 1
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
GDTYNPPZTJNPMT-UHFFFAOYSA-N 2-methyl-3-phenyl-2-propyloxirane Chemical compound CCCC1(C)OC1C1=CC=CC=C1 GDTYNPPZTJNPMT-UHFFFAOYSA-N 0.000 description 1
239000001431 2-methylbenzaldehyde Substances 0.000 description 1
125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
HTLMYYDZEUTJMQ-UHFFFAOYSA-N 2-phenyl-2-propyloxirane Chemical compound C=1C=CC=CC=1C1(CCC)CO1 HTLMYYDZEUTJMQ-UHFFFAOYSA-N 0.000 description 1
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
125000004336 3,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 description 1
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
LBOKTHVXIPFAJO-UHFFFAOYSA-N 7-(5-oxocyclopenten-1-yl)heptanoic acid Chemical compound OC(=O)CCCCCCC1=CCCC1=O LBOKTHVXIPFAJO-UHFFFAOYSA-N 0.000 description 1
CQALOCKMKQYIGV-UHFFFAOYSA-N 7-[2-(2-hydroxy-3,3-dimethyl-4-phenylbutyl)sulfanyl-5-oxocyclopentyl]heptanoic acid Chemical compound C1CC(=O)C(CCCCCCC(O)=O)C1SCC(O)C(C)(C)CC1=CC=CC=C1 CQALOCKMKQYIGV-UHFFFAOYSA-N 0.000 description 1
ZNCZFHWMZFVZSN-UHFFFAOYSA-N 7-[3-hydroxy-2-[2-hydroxy-2-(4-methylphenyl)ethyl]sulfanyl-5-oxocyclopentyl]heptanoic acid Chemical compound C1=CC(C)=CC=C1C(O)CSC1C(CCCCCCC(O)=O)C(=O)CC1O ZNCZFHWMZFVZSN-UHFFFAOYSA-N 0.000 description 1
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230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
238000005192 partition Methods 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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ZFACJPAPCXRZMQ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O.OC(=O)C1=CC=CC=C1C(O)=O ZFACJPAPCXRZMQ-UHFFFAOYSA-N 0.000 description 1
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230000002997 prostaglandinlike Effects 0.000 description 1
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HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
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238000002076 thermal analysis method Methods 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
- A61K31/10—Sulfides; Sulfoxides; Sulfones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- 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
- 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
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0033—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing sulfur
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

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

CS737749A 1972-11-17 1973-11-12 Method of preparing sulphides CS200463B2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CS787898A CS200464B2 (cs)	1972-11-17	1978-11-30	Způsob přípravy sulfidů

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2256537A DE2256537A1 (de)	1972-11-17	1972-11-17	Neue sulfide

Publications (1)

Publication Number	Publication Date
CS200463B2 true CS200463B2 (en)	1980-09-15

Family

ID=5862067

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS737749A CS200463B2 (en)	1972-11-17	1973-11-12	Method of preparing sulphides

Country Status (21)

Country	Link
US (1)	US3932487A (fr)
JP (1)	JPS5837311B2 (fr)
AT (1)	AT335418B (fr)
AU (1)	AU474893B2 (fr)
BE (1)	BE807385A (fr)
BR (1)	BR7308744D0 (fr)
CA (1)	CA1032937A (fr)
CH (4)	CH590220A5 (fr)
CS (1)	CS200463B2 (fr)
DD (1)	DD109216A5 (fr)
DK (1)	DK145878C (fr)
ES (1)	ES420643A1 (fr)
FR (1)	FR2206939B1 (fr)
GB (1)	GB1404113A (fr)
HU (1)	HU169233B (fr)
IL (1)	IL43633A (fr)
NL (1)	NL7315589A (fr)
PL (1)	PL90170B1 (fr)
SE (2)	SE423540B (fr)
YU (1)	YU296173A (fr)
ZA (1)	ZA738697B (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2422924A1 (de) *	1974-05-11	1975-11-27	Merck Patent Gmbh	Thiaprostaglandine
US4209639A (en) *	1975-09-22	1980-06-24	American Cyanamid Company	13-Thia-prostaglandins
US4131746A (en) *	1976-04-05	1978-12-26	Syntex (Usa) Inc.	(DL)-13-Substituted sulfinyl-prostaglandin-like compounds and methods of making
DE2644972C2 (de) *	1976-10-06	1986-06-19	Merck Patent Gmbh, 6100 Darmstadt	Thiaprostansäurederivate, deren Herstellung und diese Verbindungen enthaltende Mittel
US4092349A (en) *	1976-11-10	1978-05-30	Pfizer Inc.	11-Desoxy-15-thiaprostaglandins
US4189597A (en) *	1977-03-30	1980-02-19	American Cyanamid Company	11-(2-Hydroxyethylthio)prostenoic acid E series derivatives
US4218566A (en) *	1977-03-30	1980-08-19	American Cyanamid Company	11-(2-Hydroxyethylthio) prostenoic acid E and F series derivatives
US4085272A (en) *	1977-03-30	1978-04-18	American Cyanamid Company	11-(2-Hydroxyethylthio)prostenoic acid E2 series derivatives
DE3401542A1 (de) *	1984-01-18	1985-08-01	Merck Patent Gmbh, 6100 Darmstadt	Schwefelhaltige 6-ketoprostaglandine
JPS6244795U (fr) *	1985-09-09	1987-03-18
FR2631028B1 (fr) *	1988-05-09	1990-07-13	Cird	Adamantyl-2 isothiazoline-4 ones-3, leur procede de preparation et leur utilisation comme agents bactericides et fongicides

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3776940A (en) *	1966-08-09	1973-12-04	G Just	Intermediates for producing prostaglandins
US3749741A (en) *	1968-02-01	1973-07-31	American Home Prod	Tetrahydropyranyl-dihydro-pge1

1973
- 1973-11-05 CH CH1553873A patent/CH590220A5/xx not_active IP Right Cessation
- 1973-11-05 CH CH1249477A patent/CH613189A5/xx not_active IP Right Cessation
- 1973-11-05 CH CH139677A patent/CH612933A5/xx not_active IP Right Cessation
- 1973-11-08 BR BR8744/73A patent/BR7308744D0/pt unknown
- 1973-11-12 CS CS737749A patent/CS200463B2/cs unknown
- 1973-11-13 ZA ZA738697A patent/ZA738697B/xx unknown
- 1973-11-14 SE SE7315426A patent/SE423540B/xx unknown
- 1973-11-14 CA CA185,811A patent/CA1032937A/fr not_active Expired
- 1973-11-14 NL NL7315589A patent/NL7315589A/xx not_active Application Discontinuation
- 1973-11-15 IL IL43633A patent/IL43633A/en unknown
- 1973-11-15 DD DD174676A patent/DD109216A5/xx unknown
- 1973-11-15 US US05/416,183 patent/US3932487A/en not_active Expired - Lifetime
- 1973-11-15 FR FR7340681A patent/FR2206939B1/fr not_active Expired
- 1973-11-15 YU YU02961/73A patent/YU296173A/xx unknown
- 1973-11-15 GB GB5303273A patent/GB1404113A/en not_active Expired
- 1973-11-16 DK DK621973A patent/DK145878C/da active
- 1973-11-16 AU AU62607/73A patent/AU474893B2/en not_active Expired
- 1973-11-16 AT AT964773A patent/AT335418B/de not_active IP Right Cessation
- 1973-11-16 HU HUME1685A patent/HU169233B/hu unknown
- 1973-11-16 JP JP48128386A patent/JPS5837311B2/ja not_active Expired
- 1973-11-16 BE BE137801A patent/BE807385A/fr not_active IP Right Cessation
- 1973-11-17 PL PL1973166594A patent/PL90170B1/pl unknown
- 1973-11-17 ES ES420643A patent/ES420643A1/es not_active Expired
1976
- 1976-10-29 SE SE7612055A patent/SE423092B/xx unknown
1979
- 1979-01-11 CH CH27079A patent/CH618424A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
FR2206939B1 (fr)	1977-04-15
CH612933A5 (fr)	1979-08-31
CH590220A5 (fr)	1977-07-29
IL43633A (en)	1977-01-31
DK145878B (da)	1983-03-28
NL7315589A (fr)	1974-05-21
JPS5837311B2 (ja)	1983-08-15
SE423540B (sv)	1982-05-10
DK145878C (da)	1983-09-12
GB1404113A (en)	1975-08-28
IL43633A0 (en)	1974-03-14
SE423092B (sv)	1982-04-13
JPS4981350A (fr)	1974-08-06
FR2206939A1 (fr)	1974-06-14
CA1032937A (fr)	1978-06-13
AU474893B2 (en)	1976-08-05
YU296173A (en)	1982-06-18
SE7612055L (sv)	1976-10-29
CH613189A5 (fr)	1979-09-14
BR7308744D0 (pt)	1974-08-22
US3932487A (en)	1976-01-13
ZA738697B (en)	1974-09-25
AT335418B (de)	1977-03-10
ATA964773A (de)	1976-07-15
DD109216A5 (fr)	1974-10-20
PL90170B1 (fr)	1977-01-31
CH618424A5 (fr)	1980-07-31
ES420643A1 (es)	1976-09-01
HU169233B (fr)	1976-10-28
BE807385A (fr)	1974-05-16
AU6260773A (en)	1975-05-22

Publication	Publication Date	Title
CA1237718A (fr)	1988-06-07	Esters et amides de 13,14-dideshydro-prostaglandines
CS200463B2 (en)	1980-09-15	Method of preparing sulphides
GB1597262A (en)	1981-09-03	Heteromonocyclic derivatives of unsaturated 7-acylamido-3-cephem-4-carboxylic acid
SU818484A3 (ru)	1981-03-30	Способ получени 4а, 9 -транс-гЕКСАгидРО - -КАРбОлиНА
HU195223B (en)	1988-04-28	Process for producing 7-amino-3-propenyl-3-cefem-4-carboxylic acid and its esters
EP0107693B1 (fr)	1988-07-27	Composes analogues de 2,3,4-trinor-1,5-inter-m-phenylene-prostacycline-i2, leur procede de preparation et compositions pharmaceutiques les contenant
KR100342944B1 (ko)	2002-07-02	고순도 세프포독심 프록세틸의 제조방법
US4232023A (en)	1980-11-04	Novel soluble derivatives of 2,4-diamino pyrimidine
FI75168B (fi)	1988-01-29	Foerfarande foer framstaellning av natriumcefuroxim eller ett solvat daerav och natriumcefuroximtetrahydrofuransolvat anvaendbart som mellanprodukt vid foerfarandet.
SE444437B (sv)	1986-04-14	15-epi-prostacyklinderivat samt farmaceutiska kompositioner innefattande nemnda derivat
US3173911A (en)	1965-03-16	Process for the preparation of penicillin esters
SU1072801A3 (ru)	1984-02-07	Способ получени производных простациклина или их эпимеров
CA1246557A (fr)	1988-12-13	Esters de carbacycline, procede de production et applications comme medicaments
US3803202A (en)	1974-04-09	Process for the production of 2-cyano-3,4,5,6-tetrahalogenbenzoic acid alkyl esters
SU1272980A3 (ru)	1986-11-23	Способ получени оптически активных или рацемических соединений или их фармацевтически или ветеринарно приемлемых солей
US3639463A (en)	1972-02-01	15(r)-pge1 and related compounds
US4425358A (en)	1984-01-10	13-Thia-prostacycline derivatives
CS200464B2 (cs)	1980-09-15	Způsob přípravy sulfidů
US3987067A (en)	1976-10-19	Substituted aromatic esters of PGF2.sub.α
SU543353A3 (ru)	1977-01-15	Способ получени производных 7-монохлорацетамидо-3-дезацетоксицефалоспорановой кислоты
US3900500A (en)	1975-08-19	Esters of hydroxymethyl-dioxabicyclononene
IE34536B1 (en)	1975-06-11	Acylaminopenicillanic acids and process for preparing them
SU452195A1 (ru)	1977-10-05	Способ получени дийодметилата ди-( -диэтиламинопропилового эфира) -труксилловой кислоты
HU192909B (en)	1987-07-28	Process for producing interfuranylene-prostacycline derivatives
HU197733B (en)	1989-05-29	Process for producing ephedrin-salts of 7-oxo-prosta-cyclin derivatives