SE407683B - Forfarande for framstellning av n-mono(alkoximetyl)fenobarbitaler - Google Patents

Forfarande for framstellning av n-mono(alkoximetyl)fenobarbitaler

Info

Publication number: SE407683B
Authority: SE; Sweden
Prior art keywords: thiophenobarbital; bis; alkoxymethyl; mono; preparation
Prior art date: 1973-02-28

Application number

SE7402241A

Other languages

English (en)

Swedish (sv)

Inventor

J A Vida

Original Assignee

Colgate Palmolive 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.)

1973-02-28

Filing date

1974-02-20

Publication date

1979-04-09

1974-02-20 Application filed by Colgate Palmolive Co filed Critical Colgate Palmolive Co

1979-04-09 Publication of SE407683B publication Critical patent/SE407683B/sv

Links

238000000034 method Methods 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 4
-1 chloromethyl alkyl ether Chemical class 0.000 claims description 7
125000004849 alkoxymethyl group Chemical group 0.000 claims description 6
229960002695 phenobarbital Drugs 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 3
239000002184 metal Substances 0.000 claims description 3
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical class [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 2
125000004432 carbon atom Chemical group C* 0.000 claims 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
230000000694 effects Effects 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
150000001875 compounds Chemical class 0.000 description 11
239000000243 solution Substances 0.000 description 11
230000001773 anti-convulsant effect Effects 0.000 description 10
239000001961 anticonvulsive agent Substances 0.000 description 10
229960003965 antiepileptics Drugs 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000000725 suspension Substances 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
230000000147 hypnotic effect Effects 0.000 description 5
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 4
229940061627 chloromethyl methyl ether Drugs 0.000 description 4
238000010828 elution Methods 0.000 description 4
239000007788 liquid Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
231100000460 acute oral toxicity Toxicity 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
229910000103 lithium hydride Inorganic materials 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
NEFNOUUWYACOKP-UHFFFAOYSA-N 1-(chloromethoxy)butane Chemical compound CCCCOCCl NEFNOUUWYACOKP-UHFFFAOYSA-N 0.000 description 2
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
235000019483 Peanut oil Nutrition 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-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
239000002253 acid Substances 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
210000003205 muscle Anatomy 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
239000000312 peanut oil Substances 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
230000001256 tonic effect Effects 0.000 description 2
QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
GSGPUGZLDGHFDO-UHFFFAOYSA-N 2-(chloromethoxy)propane Chemical compound CC(C)OCCl GSGPUGZLDGHFDO-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
GHHFRPRCYQNNDL-UHFFFAOYSA-N 5-ethyl-5-phenyl-2-sulfanylidene-1,3-diazinane-4,6-dione Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=S)NC1=O GHHFRPRCYQNNDL-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
108010010803 Gelatin Proteins 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
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
206010044565 Tremor Diseases 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000011149 active material Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
239000003708 ampul Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
230000002566 clonic effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229940074045 glyceryl distearate Drugs 0.000 description 1
229940075507 glyceryl monostearate Drugs 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000007794 irritation Effects 0.000 description 1
239000000644 isotonic solution Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
239000006194 liquid suspension Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
LBSANEJBGMCTBH-UHFFFAOYSA-N manganate Chemical compound [O-][Mn]([O-])(=O)=O LBSANEJBGMCTBH-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
229940021222 peritoneal dialysis isotonic solution Drugs 0.000 description 1
238000005502 peroxidation Methods 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
230000011514 reflex Effects 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000005720 sucrose Substances 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
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 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
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/62—Barbituric acids

Landscapes

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

SE7402241A 1973-02-28 1974-02-20 Forfarande for framstellning av n-mono(alkoximetyl)fenobarbitaler SE407683B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US33642473A	1973-02-28	1973-02-28

Publications (1)

Publication Number	Publication Date
SE407683B true SE407683B (sv)	1979-04-09

Family

ID=23316032

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7402241A SE407683B (sv)	1973-02-28	1974-02-20	Forfarande for framstellning av n-mono(alkoximetyl)fenobarbitaler

Country Status (9)

Country	Link
JP (1)	JPS5826345B2 (fr)
AR (1)	AR204518A1 (fr)
AU (1)	AU474350B2 (fr)
BE (1)	BE811552A (fr)
CA (1)	CA1007640A (fr)
DE (1)	DE2405778A1 (fr)
FR (1)	FR2218895B1 (fr)
GB (1)	GB1396269A (fr)
SE (1)	SE407683B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6093820A (en) *	1997-10-02	2000-07-25	Taro Pharmaceutical Industries Ltd.	Method and reagents for N-alkylating ureides

1973
- 1973-01-01 AR AR25140473A patent/AR204518A1/es active
1974
- 1974-01-29 GB GB412974A patent/GB1396269A/en not_active Expired
- 1974-02-01 AU AU65089/74A patent/AU474350B2/en not_active Expired
- 1974-02-07 DE DE19742405778 patent/DE2405778A1/de not_active Ceased
- 1974-02-08 CA CA192,138A patent/CA1007640A/en not_active Expired
- 1974-02-20 SE SE7402241A patent/SE407683B/sv not_active IP Right Cessation
- 1974-02-25 FR FR7406311A patent/FR2218895B1/fr not_active Expired
- 1974-02-25 BE BE141372A patent/BE811552A/fr not_active IP Right Cessation
- 1974-02-27 JP JP2244374A patent/JPS5826345B2/ja not_active Expired

Also Published As

Publication number	Publication date
JPS5826345B2 (ja)	1983-06-02
AU474350B2 (en)	1976-07-22
GB1396269A (en)	1975-06-04
AU6508974A (en)	1975-08-07
BE811552A (fr)	1974-06-17
FR2218895A1 (fr)	1974-09-20
AR204518A1 (es)	1976-02-12
CA1007640A (en)	1977-03-29
DE2405778A1 (de)	1974-08-29
JPS49134688A (fr)	1974-12-25
FR2218895B1 (fr)	1977-11-10

Legal Events

Date

Code

Title

Description

1995-01-31

NUG

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Effective date: 19890425

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SE407683B (sv)	1979-04-09	Forfarande for framstellning av n-mono(alkoximetyl)fenobarbitaler
DD142545A5 (de)	1980-07-02	Verfahren zur herstellung neuer omega thiobutyramide
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US4054565A (en)	1977-10-18	Process for preparing N-mono(alkoxymethyl) phenobarbitals
EP0186049B1 (fr)	1990-07-04	Dérivés d'acide aziridine-2-carboxylique N-substitué, procédé pour leur préparation ainsi que les médicaments contenant ces substances
US4087529A (en)	1978-05-02	Therapeutic composition containing an N-mono (alkoxy-methyl) phenobarbital and a method of treating convulsions therewith
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US3624094A (en)	1971-11-30	Alpha-{8 (phenyl sulfinyl)methyl{9 -alpha-phenyl derivatives of pyridinemethanols
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