DK141094B - Analogifremgangsmåde til fremstilling af 2-pyridyl-beta-hydroxysulfoxider eller -sulfoner. - Google Patents

Analogifremgangsmåde til fremstilling af 2-pyridyl-beta-hydroxysulfoxider eller -sulfoner. Download PDF

Info

Publication number: DK141094B
Authority: DK; Denmark
Prior art keywords: formula; pyridyl; sulfones; compounds; hydroxy
Prior art date: 1970-09-28

Application number

DK469371AA

Other languages

Danish (da)

English (en)

Other versions

DK141094C (2

Inventor

Glenn Curtis Morrison

John Shavel Jr

Wiaczeslaw Cetenko

Original Assignee

Warner Lambert 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.)

1970-09-28

Filing date

1971-09-27

Publication date

1980-01-14

1971-09-27 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

1980-01-14 Publication of DK141094B publication Critical patent/DK141094B/da

1980-06-30 Application granted granted Critical

1980-06-30 Publication of DK141094C publication Critical patent/DK141094C/da

Links

238000000034 method Methods 0.000 title claims description 11
150000003457 sulfones Chemical class 0.000 title claims description 11
230000008569 process Effects 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
CSDSSGBPEUDDEE-UHFFFAOYSA-N 2-formylpyridine Chemical compound O=CC1=CC=CC=N1 CSDSSGBPEUDDEE-UHFFFAOYSA-N 0.000 claims description 4
150000001204 N-oxides Chemical class 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
150000003462 sulfoxides Chemical class 0.000 claims description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
150000001875 compounds Chemical class 0.000 description 14
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
DSWLRNLRVBAVFC-UHFFFAOYSA-N 2-methylsulfinyl-1-pyridin-2-ylethanone Chemical compound CS(=O)CC(=O)C1=CC=CC=N1 DSWLRNLRVBAVFC-UHFFFAOYSA-N 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
229950000370 oxisuran Drugs 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
-1 alcohol sulfoxide Chemical class 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000007787 solid Substances 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
241000700159 Rattus Species 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
208000006313 Delayed Hypersensitivity Diseases 0.000 description 3
206010020751 Hypersensitivity Diseases 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 3
239000003018 immunosuppressive agent Substances 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
238000006778 Pummerer Sulfoxide rearrangement reaction Methods 0.000 description 2
150000001350 alkyl halides Chemical class 0.000 description 2
208000026935 allergic disease Diseases 0.000 description 2
239000000538 analytical sample Substances 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010828 elution Methods 0.000 description 2
230000009610 hypersensitivity Effects 0.000 description 2
125000000468 ketone group Chemical group 0.000 description 2
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
210000000056 organ Anatomy 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000004044 response Effects 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
210000001519 tissue Anatomy 0.000 description 2
238000002054 transplantation Methods 0.000 description 2
ZGMMUHVILAEGAA-UHFFFAOYSA-N 2-methylsulfonyl-1-pyridin-2-ylethanone Chemical compound CS(=O)(=O)CC(=O)C1=CC=CC=N1 ZGMMUHVILAEGAA-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241000700198 Cavia Species 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
206010018364 Glomerulonephritis Diseases 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
230000024932 T cell mediated immunity Effects 0.000 description 1
206010052779 Transplant rejections Diseases 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
230000009471 action Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000007815 allergy Effects 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
210000001124 body fluid Anatomy 0.000 description 1
239000010839 body fluid Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
231100000433 cytotoxic Toxicity 0.000 description 1
230000001472 cytotoxic effect Effects 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000002158 endotoxin Substances 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000002068 genetic effect Effects 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000008105 immune reaction Effects 0.000 description 1
230000028993 immune response Effects 0.000 description 1
230000016784 immunoglobulin production Effects 0.000 description 1
229960003444 immunosuppressant agent Drugs 0.000 description 1
229940125721 immunosuppressive agent Drugs 0.000 description 1
229940124589 immunosuppressive drug Drugs 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000003902 lesion Effects 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
206010025135 lupus erythematosus Diseases 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
230000001617 migratory effect Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
201000003068 rheumatic fever Diseases 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
241000894007 species Species 0.000 description 1
210000004989 spleen cell Anatomy 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000001665 trituration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
- C07D213/34—Sulfur atoms to which a second hetero atom is attached

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pyridine Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DK469371AA 1970-09-28 1971-09-27 Analogifremgangsmåde til fremstilling af 2-pyridyl-beta-hydroxysulfoxider eller -sulfoner. DK141094B (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US7628870A	1970-09-28	1970-09-28
US7628870		1970-09-28

Publications (2)

Publication Number	Publication Date
DK141094B true DK141094B (da)	1980-01-14
DK141094C DK141094C (2)	1980-06-30

Family

ID=22131043

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK469371AA DK141094B (da)	1970-09-28	1971-09-27	Analogifremgangsmåde til fremstilling af 2-pyridyl-beta-hydroxysulfoxider eller -sulfoner.

Country Status (7)

Country	Link
US (1)	US3725420A (2)
JP (2)	JPS517671B1 (2)
CA (1)	CA969184A (2)
DE (1)	DE2147898C3 (2)
DK (1)	DK141094B (2)
FR (1)	FR2108018B1 (2)
GB (1)	GB1305339A (2)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2918513A (en) *	1955-08-23	1959-12-22	Monsanto Chemicals	Dispersible aryl thiazyl sulfides having admixed therewith a mineral oil and a fatty acid ester
WO1997000463A1 (fr) *	1995-06-16	1997-01-03	Seiko Epson Corporation	Dispositif d'affichage a cristaux liquides, son procede de fabrication, et appareil electronique

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK135764B (da) *	1968-11-06	1977-06-20	Warner Lambert Pharmaceutical	Analogifremgangsmåde til fremstilling af 2-pyridyl-beta-ketosulfoxider eller -sulfoner.

1970
- 1970-09-28 US US00076288A patent/US3725420A/en not_active Expired - Lifetime
1971
- 1971-08-31 GB GB4056371A patent/GB1305339A/en not_active Expired
- 1971-09-23 FR FR7134181A patent/FR2108018B1/fr not_active Expired
- 1971-09-24 DE DE2147898A patent/DE2147898C3/de not_active Expired
- 1971-09-27 CA CA123,793A patent/CA969184A/en not_active Expired
- 1971-09-27 DK DK469371AA patent/DK141094B/da unknown
- 1971-09-28 JP JP46075152A patent/JPS517671B1/ja active Pending
1974
- 1974-12-24 JP JP49147697A patent/JPS5142112B2/ja not_active Expired

Also Published As

Publication number	Publication date
DK141094C (2)	1980-06-30
JPS5142112B2 (2)	1976-11-13
FR2108018A1 (2)	1972-05-12
US3725420A (en)	1973-04-03
DE2147898B2 (de)	1980-03-06
GB1305339A (2)	1973-01-31
AU3275471A (en)	1973-03-01
JPS517671B1 (2)	1976-03-10
DE2147898C3 (de)	1980-10-30
JPS50142570A (2)	1975-11-17
CA969184A (en)	1975-06-10
FR2108018B1 (2)	1975-08-01
DE2147898A1 (de)	1972-04-06

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