NO118377B - - Google Patents

Download PDF

Info

Publication number: NO118377B
Authority: NO; Norway
Prior art keywords: dichloro; acetic acid; mol; butyryl; phenoxy
Prior art date: 1963-10-17

Application number

NO155168A

Other languages

English (en)

Norwegian (no)

Inventor

E Cragoe

Original Assignee

Merck & Co Inc

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.)

1963-10-17

Filing date

1964-10-16

Publication date

1969-12-22

1964-10-16 Application filed by Merck & Co Inc filed Critical Merck & Co Inc

1969-12-22 Publication of NO118377B publication Critical patent/NO118377B/no

Links

QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
238000000034 method Methods 0.000 claims description 19
125000000217 alkyl group Chemical group 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 10
150000001875 compounds Chemical class 0.000 claims description 9
239000007800 oxidant agent Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 22
239000007787 solid Substances 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
239000000243 solution Substances 0.000 description 18
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
238000003756 stirring Methods 0.000 description 12
239000000047 product Substances 0.000 description 11
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
238000001953 recrystallisation Methods 0.000 description 10
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 8
238000004821 distillation Methods 0.000 description 7
-1 3-chloropropyl Chemical group 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000003921 oil Substances 0.000 description 6
150000003462 sulfoxides Chemical class 0.000 description 6
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
235000011054 acetic acid Nutrition 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000001816 cooling Methods 0.000 description 5
238000001914 filtration Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
238000009835 boiling Methods 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
HFEASCCDHUVYKU-UHFFFAOYSA-N 1,2-dichloro-3-methoxybenzene Chemical compound COC1=CC=CC(Cl)=C1Cl HFEASCCDHUVYKU-UHFFFAOYSA-N 0.000 description 3
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000000463 material Substances 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
UMPSXRYVXUPCOS-UHFFFAOYSA-N 2,3-dichlorophenol Chemical compound OC1=CC=CC(Cl)=C1Cl UMPSXRYVXUPCOS-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 2
125000001118 alkylidene group Chemical group 0.000 description 2
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
125000001589 carboacyl group Chemical group 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
230000001882 diuretic effect Effects 0.000 description 2
230000000694 effects Effects 0.000 description 2
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
230000029142 excretion Effects 0.000 description 2
239000000284 extract Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000000843 powder Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
229910001415 sodium ion Inorganic materials 0.000 description 2
239000011343 solid material Substances 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
150000004763 sulfides Chemical class 0.000 description 2
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
SMUKODJVMQOSAB-UHFFFAOYSA-N 2-ethylbutanoyl chloride Chemical compound CCC(CC)C(Cl)=O SMUKODJVMQOSAB-UHFFFAOYSA-N 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical class CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
150000001243 acetic acids Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
125000005265 dialkylamine group Chemical group 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
- C07C317/48—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO155168A 1963-10-17 1964-10-16 NO118377B (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US317086A US3364255A (en)	1963-10-17	1963-10-17	2-organosulfinyl- and 2-organosulfonyl-derivatives of (4-alkanoylphenoxy) alkanoic acids

Publications (1)

Publication Number	Publication Date
NO118377B true NO118377B (de)	1969-12-22

Family

ID=23232050

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO155168A NO118377B (de)	1963-10-17	1964-10-16

Country Status (12)

Country	Link
US (1)	US3364255A (de)
BE (1)	BE654486A (de)
BR (1)	BR6463497D0 (de)
CH (1)	CH468359A (de)
DE (1)	DE1493990A1 (de)
DK (1)	DK114347B (de)
FI (1)	FI41645B (de)
GB (1)	GB1074808A (de)
IL (1)	IL22164A (de)
LU (1)	LU47161A1 (de)
NL (1)	NL6412083A (de)
NO (1)	NO118377B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3541142A (en) *	1966-09-02	1970-11-17	Merck & Co Inc	(4-(2-hydroxymethylalkanoyl)phenoxy) acetic acids

1963
- 1963-10-17 US US317086A patent/US3364255A/en not_active Expired - Lifetime
1964
- 1964-09-29 IL IL22164A patent/IL22164A/en unknown
- 1964-10-06 DE DE19641493990 patent/DE1493990A1/de active Pending
- 1964-10-08 FI FI2121/64A patent/FI41645B/fi active
- 1964-10-13 GB GB41759/64A patent/GB1074808A/en not_active Expired
- 1964-10-15 DK DK510964AA patent/DK114347B/da unknown
- 1964-10-16 BR BR163497/64A patent/BR6463497D0/pt unknown
- 1964-10-16 NO NO155168A patent/NO118377B/no unknown
- 1964-10-16 CH CH1344964A patent/CH468359A/de unknown
- 1964-10-16 BE BE654486D patent/BE654486A/xx unknown
- 1964-10-16 NL NL6412083A patent/NL6412083A/xx unknown
- 1964-10-17 LU LU47161D patent/LU47161A1/xx unknown

Also Published As

Publication number	Publication date
BR6463497D0 (pt)	1973-07-17
FI41645B (de)	1969-09-30
BE654486A (de)	1965-04-16
LU47161A1 (de)	1965-04-17
IL22164A (en)	1968-02-26
US3364255A (en)	1968-01-16
DE1493990A1 (de)	1969-08-07
GB1074808A (en)	1967-07-05
CH468359A (de)	1969-02-15
DK114347B (da)	1969-06-23
NL6412083A (de)	1965-04-20

Publication	Publication Date	Title
NO155168B (no)	1986-11-10	Galvanisk element, spesielt metall-luft-celle.
NO152148B (no)	1985-04-29	Vaapensystem med sylindermekanisme
KR100273888B1 (ko)	2000-12-15	2,2-디클로로알칸카르복실산,그의제조방법,그를함유하는약물,및그의내인슐린치료용용도
US3668241A (en)	1972-06-06	Substituted 1-oxoinden-5-yloxy alkanoic acids
NO892982L (no)	1990-02-05	Tetrahydro-1-benz-(c,d)-indolpropionsyre-sulfonamider.
Fager	1945	Some derivatives of 3, 4-dioxythiophene
NO155826B (no)	1987-02-23	Roerbuntkabel til bruk under vann.
Boswell et al.	1968	The Nitrobenzo [b] thiophenes
EP0094102B1 (de)	1985-12-27	1-(1-Cyclohexenylmethyl)pyrrolidin-Derivate und Verfahren zu deren Herstellung
CA1091695A (en)	1980-12-16	4-alkylthio-2-trifluoromethylalkane-sulfonanilides and derivatives thereof
IE45470B1 (en)	1982-09-08	Thiophene derivatives
JPS5973579A (ja)	1984-04-25	ベンゾフラン又はベンゾチオフェン誘導体，この化合物を有効成分とする尿酸排泄剤及びその製造方法
KR870000205B1 (ko)	1987-02-16	페녹시 알칸디온 유도체의 제조방법
NO127149B (de)	1973-05-14
NO760116L (de)	1976-07-16
HANSCH et al.	1956	Catalytic Synthesis of Heterocycles. VIII. 1 Dehydrocyclization of o-Ethylbenzenethiols to Thianaphenes. 2
US3398188A (en)	1968-08-20	And [4-(2-haloalkanoyl) phenylmercapto]-alkanoic acids
US3419606A (en)	1968-12-31	4-(2-methylenealkanoyl)phenylsulfinyl alkanoic acids
NO150240B (no)	1984-06-04	4-(2`,2`,2`-trihalogenetyl)cyklobutan-1-sulfonsyresalter
US3364255A (en)	1968-01-16	2-organosulfinyl- and 2-organosulfonyl-derivatives of (4-alkanoylphenoxy) alkanoic acids
JP2002506851A (ja)	2002-03-05	カルボン酸類およびアシルスルホンアミド類、そのような化合物を含む組成物ならびに治療方法
CA2147495A1 (en)	1994-04-28	N-t-butylaniline analog and lipid level depressant containing the same
US3322821A (en)	1967-05-30	Process for converting [4-[2-(organosulfinylmethyl)alkanoyl]phenoxy]alkanoic acids and [4-[2-(organosulfonylmethyl)alkanoyl]phenoxy]alkanoic acids to their [4-(2-methylenealkanoyl)phenoxy]alkanoic acid derivatives
US3502717A (en)	1970-03-24	2-arylthio and 2-arylsulfonyl benzoic acid
US3275689A (en)	1966-09-27	3-alkylsulfonyl-5-(tertiaryaminopropylidene)-and 5-hydroxy-5-(tertiaryaminopropyl)-5h-dibenzo[a, d] cycloheptenes