CH618673A5 - - Google Patents

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Publication number: CH618673A5
Authority: CH; Switzerland
Prior art keywords: acid; formula; reaction; mixture; propionic
Prior art date: 1975-02-19

Application number

CH188076A

Other languages

German (de)

English (en)

Inventor

Norio Yoshida

Kiichiro Tanaka

Original Assignee

Sankyo Co

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.)

1975-02-19

Filing date

1976-02-16

Publication date

1980-08-15

1976-02-16 Application filed by Sankyo Co filed Critical Sankyo Co

1980-08-15 Publication of CH618673A5 publication Critical patent/CH618673A5/de

Links

238000000034 method Methods 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 12
JLPVOZGNXQAVSI-UHFFFAOYSA-N 2-(2,3-dihydro-1h-inden-1-yl)propanoic acid Chemical class C1=CC=C2C(C(C)C(O)=O)CCC2=C1 JLPVOZGNXQAVSI-UHFFFAOYSA-N 0.000 claims description 11
239000002253 acid Substances 0.000 claims description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
235000019260 propionic acid Nutrition 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
IGAPBZBAIDLKOJ-UHFFFAOYSA-N 2-(3-oxo-2-propan-2-yl-1,2-dihydroinden-5-yl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=C2C(=O)C(C(C)C)CC2=C1 IGAPBZBAIDLKOJ-UHFFFAOYSA-N 0.000 claims description 5
VZYWAGKPCIUMOZ-UHFFFAOYSA-N 2-(2-ethyl-3-oxo-1,2-dihydroinden-5-yl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=C2C(=O)C(CC)CC2=C1 VZYWAGKPCIUMOZ-UHFFFAOYSA-N 0.000 claims description 4
HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims description 3
239000002841 Lewis acid Substances 0.000 claims description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
150000007517 lewis acids Chemical class 0.000 claims description 3
239000011707 mineral Substances 0.000 claims description 3
150000004672 propanoic acids Chemical class 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 2
150000001735 carboxylic acids Chemical class 0.000 claims description 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims 2
229940098779 methanesulfonic acid Drugs 0.000 claims 1
239000000203 mixture Substances 0.000 description 26
238000006243 chemical reaction Methods 0.000 description 25
239000000047 product Substances 0.000 description 25
239000002904 solvent Substances 0.000 description 23
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
150000001875 compounds Chemical class 0.000 description 12
-1 alkyl mercaptan Chemical compound 0.000 description 11
239000011541 reaction mixture Substances 0.000 description 11
238000004458 analytical method Methods 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000000284 extract Substances 0.000 description 9
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
238000009835 boiling Methods 0.000 description 8
239000003638 chemical reducing agent Substances 0.000 description 8
239000003960 organic solvent Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000000202 analgesic effect Effects 0.000 description 6
230000003110 anti-inflammatory effect Effects 0.000 description 6
230000001754 anti-pyretic effect Effects 0.000 description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 6
229910000497 Amalgam Inorganic materials 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
238000005292 vacuum distillation Methods 0.000 description 5
229910052725 zinc Inorganic materials 0.000 description 5
239000011701 zinc Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
238000010531 catalytic reduction reaction Methods 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
239000013078 crystal Substances 0.000 description 4
239000012259 ether extract Substances 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000005457 ice water Substances 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
239000002585 base Substances 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000003863 metallic catalyst Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
RYDUZJFCKYTEHX-UHFFFAOYSA-N 2-(2-propan-2-yl-2,3-dihydro-1h-inden-5-yl)propanoic acid Chemical compound C1=C(C(C)C(O)=O)C=C2CC(C(C)C)CC2=C1 RYDUZJFCKYTEHX-UHFFFAOYSA-N 0.000 description 2
BAOFJQQPJFCPNZ-UHFFFAOYSA-N 2-[[4-(1-carboxyethyl)phenyl]methyl]butanoic acid Chemical compound CCC(C(O)=O)CC1=CC=C(C(C)C(O)=O)C=C1 BAOFJQQPJFCPNZ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001339 alkali metal compounds Chemical class 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
239000002221 antipyretic Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
238000006477 desulfuration reaction Methods 0.000 description 2
230000023556 desulfurization Effects 0.000 description 2
LJRSKOFNPMYRSO-UHFFFAOYSA-N ethyl 2-[4-(chloromethyl)phenyl]propanoate Chemical compound CCOC(=O)C(C)C1=CC=C(CCl)C=C1 LJRSKOFNPMYRSO-UHFFFAOYSA-N 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000000155 melt Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
150000003053 piperidines Chemical class 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
239000008096 xylene Substances 0.000 description 2
VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
ONURMRHUVVBGAN-UHFFFAOYSA-N 2-(1h-inden-1-yl)propanoic acid Chemical class C1=CC=C2C(C(C)C(O)=O)C=CC2=C1 ONURMRHUVVBGAN-UHFFFAOYSA-N 0.000 description 1
AHEHTPSVTQNDSI-UHFFFAOYSA-N 2-[[4-(1-carboxyethyl)phenyl]methyl]-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)CC1=CC=C(C(C)C(O)=O)C=C1 AHEHTPSVTQNDSI-UHFFFAOYSA-N 0.000 description 1
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
JHNLZOVBAQWGQU-UHFFFAOYSA-N 380814_sial Chemical compound CS(O)(=O)=O.O=P(=O)OP(=O)=O JHNLZOVBAQWGQU-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000700198 Cavia Species 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
238000006214 Clemmensen reduction reaction Methods 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
238000005727 Friedel-Crafts reaction Methods 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
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
241000906446 Theraps Species 0.000 description 1
229960001138 acetylsalicylic acid Drugs 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
229940125716 antipyretic agent Drugs 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
229930007927 cymene Natural products 0.000 description 1
230000000911 decarboxylating effect Effects 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
WHLJNHIOBXHWNJ-UHFFFAOYSA-N diethyl 2-[[4-(1-ethoxy-1-oxopropan-2-yl)phenyl]methyl]-2-ethylpropanedioate Chemical compound CCOC(=O)C(C)C1=CC=C(CC(CC)(C(=O)OCC)C(=O)OCC)C=C1 WHLJNHIOBXHWNJ-UHFFFAOYSA-N 0.000 description 1
MWINZXDHMARREY-UHFFFAOYSA-N diethyl 2-[[4-(1-ethoxy-1-oxopropan-2-yl)phenyl]methyl]-2-propan-2-ylpropanedioate Chemical compound CCOC(=O)C(C)C1=CC=C(CC(C(C)C)(C(=O)OCC)C(=O)OCC)C=C1 MWINZXDHMARREY-UHFFFAOYSA-N 0.000 description 1
BYQFBFWERHXONI-UHFFFAOYSA-N diethyl 2-propan-2-ylpropanedioate Chemical compound CCOC(=O)C(C(C)C)C(=O)OCC BYQFBFWERHXONI-UHFFFAOYSA-N 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
150000004252 dithioacetals Chemical class 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000007721 medicinal effect Effects 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
150000002780 morpholines Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
229910003445 palladium oxide Inorganic materials 0.000 description 1
JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 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
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000012056 semi-solid material Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
- C07C57/34—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings containing more than one carboxyl group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Engineering & Computer Science (AREA)
Biomedical Technology (AREA)
Bioinformatics & Cheminformatics (AREA)
Rheumatology (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)

CH188076A 1975-02-19 1976-02-16 CH618673A5 (nl)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP50020696A JPS5740132B2 (nl)	1975-02-19	1975-02-19

Publications (1)

Publication Number	Publication Date
CH618673A5 true CH618673A5 (nl)	1980-08-15

Family

ID=12034306

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH188076A CH618673A5 (nl)	1975-02-19	1976-02-16

Country Status (13)

Country	Link
US (1)	US4007179A (nl)
JP (1)	JPS5740132B2 (nl)
BE (1)	BE838689A (nl)
CA (1)	CA1054630A (nl)
CH (1)	CH618673A5 (nl)
DE (1)	DE2606789A1 (nl)
DK (1)	DK66476A (nl)
ES (1)	ES445336A1 (nl)
FR (1)	FR2301508A1 (nl)
GB (1)	GB1502689A (nl)
MX (1)	MX3292E (nl)
NL (1)	NL7601713A (nl)
SE (1)	SE7601714L (nl)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5432460A (en) *	1977-08-16	1979-03-09	Sankyo Co Ltd	Cycloalkylidenemethylphenylacetic acid derivative and their preparation
US4281017A (en) *	1978-09-16	1981-07-28	Lilly Industries Limited	Pharmaceutically active indane derivatives
US4266069A (en) *	1979-12-19	1981-05-05	The Upjohn Company	Processes for the preparation of hydratropic acids and esters

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3532752A (en) *	1965-12-30	1970-10-06	Merck & Co Inc	1-alkylidene-3-indenyl aliphatic amines
US3644479A (en) *	1970-02-09	1972-02-22	Bristol Myers Co	1-indancarboxylic acids and derivatives
US3932498A (en) *	1971-01-21	1976-01-13	Merck & Co., Inc.	3-Indenyl-γ-(ketobutyric)-acid compounds
US3929872A (en) *	1973-10-12	1975-12-30	Merck & Co Inc	Indanacetic acid compounds

1975
- 1975-02-19 JP JP50020696A patent/JPS5740132B2/ja not_active Expired
1976
- 1976-01-27 US US05/652,727 patent/US4007179A/en not_active Expired - Lifetime
- 1976-02-05 GB GB4536/76A patent/GB1502689A/en not_active Expired
- 1976-02-16 CH CH188076A patent/CH618673A5/de not_active IP Right Cessation
- 1976-02-16 SE SE7601714A patent/SE7601714L/xx not_active Application Discontinuation
- 1976-02-17 FR FR7604269A patent/FR2301508A1/fr active Granted
- 1976-02-18 CA CA246037A patent/CA1054630A/en not_active Expired
- 1976-02-18 BE BE164422A patent/BE838689A/xx not_active IP Right Cessation
- 1976-02-18 DK DK66476*#A patent/DK66476A/da unknown
- 1976-02-18 MX MX000004U patent/MX3292E/es unknown
- 1976-02-19 DE DE19762606789 patent/DE2606789A1/de not_active Withdrawn
- 1976-02-19 NL NL7601713A patent/NL7601713A/nl not_active Application Discontinuation
- 1976-02-19 ES ES445336A patent/ES445336A1/es not_active Expired

Also Published As

Publication number	Publication date
JPS5198255A (nl)	1976-08-30
US4007179A (en)	1977-02-08
ES445336A1 (es)	1977-06-01
NL7601713A (nl)	1976-08-23
SE7601714L (sv)	1976-08-20
MX3292E (es)	1980-08-25
DE2606789A1 (de)	1976-09-02
CA1054630A (en)	1979-05-15
BE838689A (fr)	1976-08-18
DK66476A (da)	1976-08-20
GB1502689A (en)	1978-03-01
FR2301508B1 (nl)	1979-08-31
FR2301508A1 (fr)	1976-09-17
JPS5740132B2 (nl)	1982-08-25

Legal Events

Date	Code	Title	Description
1984-10-31	PL	Patent ceased

Publication	Publication Date	Title
CH633515A5 (de)	1982-12-15	Substituierte phenylessigsaeurederivate und verfahren zu ihrer herstellung.
CH494730A (de)	1970-08-15	Verfahren zur Herstellung von Dibenzocyclopentenen
DE2314636C2 (de)	1986-09-11	Indanderivate, deren Herstellung und diese enthaltende pharmazeutische Mittel
EP0496238A1 (de)	1992-07-29	Substituierte Benzoxazepine und Benzthiazepine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln
DE2701705A1 (de)	1977-08-04	Neue organische verbindungen, ihre verwendung und herstellung
CH618673A5 (nl)	1980-08-15
DE2241027A1 (de)	1973-03-01	Verfahren zur herstellung neuer heterocyclischer verbindungen
DE2505446A1 (de)	1976-01-22	Neue organische verbindungen und verfahren zu deren herstellung
DE2852975C2 (de)	1982-04-08	5-Cyano-1-alkylpyrrol-2-essigsäure-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung
CH591415A5 (en)	1977-09-15	3-(Tri-substd. benzoyl) propionic acids - as relaxants or spasmolytics for the gall bladder
DE2747987C2 (nl)	1988-02-25
DE2503223A1 (de)	1975-08-07	Verfahren zur herstellung neuer carbocyclischer verbindungen
DE2653477A1 (de)	1977-06-08	Spiro eckige klammer auf cyclopropan- 1,2'-indolin eckige klammer zu -3'-one
DE2729817C2 (de)	1982-05-27	Verfahren zur Herstellung von dl- 6a-10a-cis-1-Hydroxy-3-alkylsubstituierten-6,6-dimethyl-6,6a,7,8,10,10a-hexahydro-9H-dibenzo[b,d]-pyran-9-onen
DE1493323B2 (de)	1973-04-26	1-(p-hydroxyphenyl)-2-phenyl-6methoxy- 3,4-dihydronaphthalin, dessen pharmakologisch geeignete salze und verfahren zur herstellung dieser verbindungen
AT344153B (de)	1978-07-10	Verfahren zur herstellung neuer 2-alkyl-5-indanessigsaeure- und -alkylester-derivate
DE1950012C2 (de)	1982-05-19	Neue tricyclische Verbindungen und deren Herstellung
AT337681B (de)	1977-07-11	Verfahren zur herstellung von neuen benzocycloalkencarbonsauren und deren derivaten
AT346836B (de)	1978-11-27	Verfahren zur herstellung von neuen, substituierten 2-alkyl-5-indanessigsaeuren und von deren salzen
AT336004B (de)	1977-04-12	Verfahren zur herstellung neuer 3-(4-biphenylyl)-buttersauren, ihrer ester, amide und salze
AT340382B (de)	1977-12-12	Verfahren zur herstellung von neuen 10- (2'-dialkylaminoathyl) -10,11-dihydro-5-methylen-5h-dibenzo (a,d)- cycloheptenen und ihren saureadditionssalzen
DE2345192A1 (de)	1974-03-28	Verfahren zur herstellung neuer heterocyclischer verbindungen
DE2720321A1 (de)	1977-12-01	Neue benzofuran- und benzoxepinderivate
AT333731B (de)	1976-12-10	Verfahren zur herstellung neuer biphenylylbuttersauren, deren estern und amiden
AT343649B (de)	1978-06-12	Verfahren zur herstellung neuer substituierter, gegebenenfalls veresterter oder amidierter benzocycloalkenylcarbonsauren