CA1038400A - Acides indanecarboxyliques-1 - Google Patents

Acides indanecarboxyliques-1

Info

Publication number: CA1038400A
Authority: CA; Canada
Prior art keywords: acid; cyclohexyl; compound; isomer; substantially pure
Prior art date: 1969-01-31
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA289,803A

Other languages

English (en)

Inventor

Peter F. Juby

Richard A. Partyka

Thomas W. Hudyma

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

Bristol Myers Squibb Co

Original Assignee

Bristol Myers Squibb 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.)

1969-01-31

Filing date

1977-10-28

Publication date

1978-09-12

1970-01-26 Priority claimed from CA073,056A external-priority patent/CA1029028A/fr

1977-10-28 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

1978-09-12 Application granted granted Critical

1978-09-12 Publication of CA1038400A publication Critical patent/CA1038400A/fr

Status Expired legal-status Critical Current

Links

JBQMFBWTKWOSQX-UHFFFAOYSA-N 2,3-dihydro-1h-indene-1-carboxylic acid Chemical class C1=CC=C2C(C(=O)O)CCC2=C1 JBQMFBWTKWOSQX-UHFFFAOYSA-N 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims abstract description 57
239000000203 mixture Substances 0.000 claims description 43
150000003839 salts Chemical class 0.000 claims description 33
229910052739 hydrogen Inorganic materials 0.000 claims description 26
238000000034 method Methods 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
125000001309 chloro group Chemical group Cl* 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 7
229910052794 bromium Inorganic materials 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
BKEWDCUQDVDPHC-UHFFFAOYSA-N 5-cyclohexyl-2,3-dihydro-1h-indene-1-carboxylic acid Chemical class C=1C=C2C(C(=O)O)CCC2=CC=1C1CCCCC1 BKEWDCUQDVDPHC-UHFFFAOYSA-N 0.000 abstract description 13
241001465754 Metazoa Species 0.000 abstract description 4
239000002260 anti-inflammatory agent Substances 0.000 abstract description 3
229940121363 anti-inflammatory agent Drugs 0.000 abstract description 3
208000027866 inflammatory disease Diseases 0.000 abstract description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 69
239000002253 acid Substances 0.000 description 54
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 49
-1 3-chloro-4-cyclohexyl- Chemical group 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
239000013078 crystal Substances 0.000 description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000007787 solid Substances 0.000 description 15
239000003921 oil Substances 0.000 description 14
235000019198 oils Nutrition 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
229920006395 saturated elastomer Polymers 0.000 description 9
238000010992 reflux Methods 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
239000011734 sodium Substances 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000012954 diazonium Substances 0.000 description 6
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
150000002431 hydrogen Chemical group 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
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 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000005457 ice water Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
OIRAEJWYWSAQNG-UHFFFAOYSA-N Clidanac Chemical compound ClC=1C=C2C(C(=O)O)CCC2=CC=1C1CCCCC1 OIRAEJWYWSAQNG-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 4
206010030113 Oedema Diseases 0.000 description 4
241000700159 Rattus Species 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
150000001768 cations Chemical class 0.000 description 4
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
231100000252 nontoxic Toxicity 0.000 description 4
230000003000 nontoxic effect Effects 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
239000000725 suspension Substances 0.000 description 4
XEBDGTZCCCYURS-UHFFFAOYSA-N 5-cyclohexyl-6-nitro-2,3-dihydro-1h-indene-1-carboxylic acid Chemical class [O-][N+](=O)C=1C=C2C(C(=O)O)CCC2=CC=1C1CCCCC1 XEBDGTZCCCYURS-UHFFFAOYSA-N 0.000 description 3
241000282414 Homo sapiens Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
239000002585 base Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000000463 material Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 3
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
UFRNQYOEYZNNBG-UHFFFAOYSA-N 1-hexyl-2,3-dihydroindene-1-carboxylic acid Chemical compound C1=CC=C2C(CCCCCC)(C(O)=O)CCC2=C1 UFRNQYOEYZNNBG-UHFFFAOYSA-N 0.000 description 2
RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 2
WSKCLYSPBODMHR-UHFFFAOYSA-N 5-cyclohexyl-6-hydroxy-2,3-dihydro-1h-indene-1-carboxylic acid Chemical compound OC=1C=C2C(C(=O)O)CCC2=CC=1C1CCCCC1 WSKCLYSPBODMHR-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
101100064676 Mus musculus Edem1 gene Proteins 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
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 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 2
125000004356 hydroxy functional group Chemical group O* 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
CPBGSLIVFJMDAK-UHFFFAOYSA-N methyl 5-cyclohexyl-2,3-dihydro-1h-indene-1-carboxylate Chemical compound C=1C=C2C(C(=O)OC)CCC2=CC=1C1CCCCC1 CPBGSLIVFJMDAK-UHFFFAOYSA-N 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
229910017604 nitric acid Inorganic materials 0.000 description 2
SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
229920003987 resole Polymers 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
229910052979 sodium sulfide Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
REPVLJRCJUVQFA-UHFFFAOYSA-N (-)-isopinocampheol Natural products C1C(O)C(C)C2C(C)(C)C1C2 REPVLJRCJUVQFA-UHFFFAOYSA-N 0.000 description 1
BKEWDCUQDVDPHC-HNNXBMFYSA-N (1s)-5-cyclohexyl-2,3-dihydro-1h-indene-1-carboxylic acid Chemical compound C([C@@H](C1=CC=2)C(=O)O)CC1=CC=2C1CCCCC1 BKEWDCUQDVDPHC-HNNXBMFYSA-N 0.000 description 1
GHPYJLCQYMAXGG-WCCKRBBISA-N (2R)-2-amino-3-(2-boronoethylsulfanyl)propanoic acid hydrochloride Chemical compound Cl.N[C@@H](CSCCB(O)O)C(O)=O GHPYJLCQYMAXGG-WCCKRBBISA-N 0.000 description 1
KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical compound O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 description 1
GRJCTXWTEMVRPF-UHFFFAOYSA-N 1-cyclohexyl-2,3-dihydroindene-1-carboxylic acid Chemical compound C1CC2=CC=CC=C2C1(C(=O)O)C1CCCCC1 GRJCTXWTEMVRPF-UHFFFAOYSA-N 0.000 description 1
RIZUCYSQUWMQLX-UHFFFAOYSA-N 2,3-dimethylbenzoic acid Chemical compound CC1=CC=CC(C(O)=O)=C1C RIZUCYSQUWMQLX-UHFFFAOYSA-N 0.000 description 1
SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 1
PYTBQLTVFVFKOW-UHFFFAOYSA-N 3-(4-cyclohexylphenyl)oxolane-2,5-dione Chemical compound O=C1OC(=O)CC1C1=CC=C(C2CCCCC2)C=C1 PYTBQLTVFVFKOW-UHFFFAOYSA-N 0.000 description 1
GYEYJMRRJXGXBM-UHFFFAOYSA-N 5-cyclohexyl-4-nitro-2,3-dihydro-1H-indene-1-carboxylic acid Chemical compound [N+](=O)([O-])C1=C2CCC(C2=CC=C1C1CCCCC1)C(=O)O GYEYJMRRJXGXBM-UHFFFAOYSA-N 0.000 description 1
GPQGWTUPVHNGDV-UHFFFAOYSA-N 5-cyclohexyl-6-fluoro-2,3-dihydro-1h-indene-1-carboxylic acid Chemical compound FC=1C=C2C(C(=O)O)CCC2=CC=1C1CCCCC1 GPQGWTUPVHNGDV-UHFFFAOYSA-N 0.000 description 1
RGZUSJBRBFBTTO-UHFFFAOYSA-N 5-cyclohexyl-6-methyl-2,3-dihydro-1H-indene-1-carboxylic acid Chemical compound CC1=C(C=C2CCC(C2=C1)C(=O)O)C1CCCCC1 RGZUSJBRBFBTTO-UHFFFAOYSA-N 0.000 description 1
RBMUAGDCCJDQLE-UHFFFAOYSA-N 5-methyl-2-propan-2-ylcyclohexan-1-amine Chemical compound CC(C)C1CCC(C)CC1N RBMUAGDCCJDQLE-UHFFFAOYSA-N 0.000 description 1
VUDHKNQACVHAKK-UHFFFAOYSA-N 6-amino-5-cyclohexyl-2,3-dihydro-1h-indene-1-carboxylic acid Chemical compound NC1=CC=2C(C(O)=O)CCC=2C=C1C1CCCCC1 VUDHKNQACVHAKK-UHFFFAOYSA-N 0.000 description 1
PWEDZHJBRIDVHB-UHFFFAOYSA-N 6-nitro-2,3-dihydro-1h-indene-1-carboxylic acid Chemical compound C1=C([N+]([O-])=O)C=C2C(C(=O)O)CCC2=C1 PWEDZHJBRIDVHB-UHFFFAOYSA-N 0.000 description 1
206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
229910000906 Bronze Inorganic materials 0.000 description 1
101100385222 Caenorhabditis elegans che-12 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
235000001258 Cinchona calisaya Nutrition 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
241000518994 Conta Species 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
101100073738 Escherichia coli (strain K12) kgtP gene Proteins 0.000 description 1
108090000371 Esterases Proteins 0.000 description 1
238000009619 Gattermann reaction Methods 0.000 description 1
201000005569 Gout Diseases 0.000 description 1
229910004373 HOAc Inorganic materials 0.000 description 1
241000282412 Homo Species 0.000 description 1
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
101100536883 Legionella pneumophila subsp. pneumophila (strain Philadelphia 1 / ATCC 33152 / DSM 7513) thi5 gene Proteins 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
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IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
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230000003301 hydrolyzing effect Effects 0.000 description 1
CYWFCPPBTWOZSF-UHFFFAOYSA-N ibufenac Chemical compound CC(C)CC1=CC=C(CC(O)=O)C=C1 CYWFCPPBTWOZSF-UHFFFAOYSA-N 0.000 description 1
229950009183 ibufenac Drugs 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
229940049920 malate Drugs 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
QZIQJVCYUQZDIR-UHFFFAOYSA-N mechlorethamine hydrochloride Chemical compound Cl.ClCCN(C)CCCl QZIQJVCYUQZDIR-UHFFFAOYSA-N 0.000 description 1
229940041616 menthol Drugs 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
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235000010755 mineral Nutrition 0.000 description 1
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150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
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APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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239000003960 organic solvent Substances 0.000 description 1
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NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
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 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA289,803A 1969-01-31 1977-10-28 Acides indanecarboxyliques-1 Expired CA1038400A (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US79572669A	1969-01-31	1969-01-31
US85887069A	1969-09-17	1969-09-17
CA073,056A CA1029028A (fr)	1969-01-31	1970-01-26	Acides 1-indancarboxyliques

Publications (1)

Publication Number	Publication Date
CA1038400A true CA1038400A (fr)	1978-09-12

Family

ID=27160533

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA289,803A Expired CA1038400A (fr)	1969-01-31	1977-10-28	Acides indanecarboxyliques-1

Country Status (1)

Country	Link
CA (1)	CA1038400A (fr)

1977
- 1977-10-28 CA CA289,803A patent/CA1038400A/fr not_active Expired

Publication	Publication Date	Title
CA1179368A (fr)	1984-12-11	Composes inhibiteurs de la cerebrinase
NO167141B (no)	1991-07-01	Bicykliske aromatiske forbindelser for kosmetisk anvendelse og blandinger som inneholder dem.
CH633515A5 (de)	1982-12-15	Substituierte phenylessigsaeurederivate und verfahren zu ihrer herstellung.
US3984431A (en)	1976-10-05	Derivatives of pyrazole-5-acetic acid
US4442115A (en)	1984-04-10	2'Hydroxy tetrazole-5-carboxanilides and anti-allergic use thereof
SU686616A3 (ru)	1979-09-15	Способ получени производных 3-фтор-6-пиперазинил-морфантридина или их солей
US3468939A (en)	1969-09-23	4- and 5-aryl-1-naphthaleneacetic acid compounds
US3551419A (en)	1970-12-29	Amino acid amides and process for their production
US3707559A (en)	1972-12-26	N-acyl phenylalanine amides
US3565943A (en)	1971-02-23	1-indancarboxylic acids and derivatives
DE2740836A1 (de)	1979-03-22	Anellierte indolderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
CA1038400A (fr)	1978-09-12	Acides indanecarboxyliques-1
CA1041541A (fr)	1978-10-31	Sels de l'acide cyclopropyl-4 methyleneoxy-3 chlorophenylacetique
US3895063A (en)	1975-07-15	Substituted Anilino Benzyl Alcohols
US3663627A (en)	1972-05-16	1-indanmethanols
US3565904A (en)	1971-02-23	1,2,3,4-tetrahydro-1-naphthoic acids
US4008269A (en)	1977-02-15	Phenylacetic acids
US4143055A (en)	1979-03-06	2,4,6-trisubstituted-2,3-dihydro-benzofuran derivatives
CS216205B2 (en)	1982-10-29	Method of making the derivatives of the 1,4-diphenylpyrazole
Hansch et al.	1955	SYNTHESIS OF 6-SUBSTITUTED THIANAPHTHENES1
CA1078403A (fr)	1980-05-27	ACIDES .alpha.-CHLOROCARBOXYLIQUES
NO150878B (no)	1984-09-24	Analogifremgangsmaate ved fremstilling av terapeutisk aktive 1-nafthyl-eddiksyrederivater
NO121502B (fr)	1971-03-08
Hase et al.	1968	Synthesis of DL-α-aminosuberic acid and its optical resolution
US4330555A (en)	1982-05-18	Indanyloxamic derivatives, their preparation and pharmaceutical compositions containing them