CA1051008A - Thioamides - Google Patents

Thioamides

Info

Publication number: CA1051008A
Authority: CA; Canada
Prior art keywords: alpha; methyl; oxo; hydrogen; phenoxyacetamido
Prior art date: 1975-06-23
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

CA229,977A

Other languages

English (en)

Other versions

CA229977S (en

Inventor

Robert B. Morin

Ronald G. Micetich

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.)

Connlab Holdings Ltd

Original Assignee

Connlab Holdings Ltd

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.)

1975-06-23

Filing date

1975-06-23

Publication date

1979-03-20

1975-06-23 Application filed by Connlab Holdings Ltd filed Critical Connlab Holdings Ltd

1975-06-23 Priority to CA229,977A priority Critical patent/CA1051008A/fr

1979-03-20 Application granted granted Critical

1979-03-20 Publication of CA1051008A publication Critical patent/CA1051008A/fr

Status Expired legal-status Critical Current

Links

150000003556 thioamides Chemical class 0.000 title description 3
-1 4-amino-1-butyl Chemical group 0.000 claims abstract description 25
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
239000001257 hydrogen Substances 0.000 claims abstract description 16
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
150000001875 compounds Chemical class 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims abstract description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
238000000034 method Methods 0.000 claims description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 claims description 5
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 5
DNPOVSLJNLLGMA-SJUANORRSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenoxyacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)COC1=CC=CC=C1 DNPOVSLJNLLGMA-SJUANORRSA-N 0.000 claims description 4
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims description 4
MWCGLTCRJJFXKR-UHFFFAOYSA-N n-phenylethanethioamide Chemical compound CC(=S)NC1=CC=CC=C1 MWCGLTCRJJFXKR-UHFFFAOYSA-N 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
FCZNNHHXCFARDY-WQRUCBPWSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)CC1=CC=CC=C1 FCZNNHHXCFARDY-WQRUCBPWSA-N 0.000 claims description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 2
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 2
239000000126 substance Substances 0.000 claims 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract description 7
229930182555 Penicillin Natural products 0.000 abstract description 6
125000003118 aryl group Chemical group 0.000 abstract description 6
125000001072 heteroaryl group Chemical group 0.000 abstract description 5
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 abstract description 4
150000003254 radicals Chemical class 0.000 abstract description 4
229930186147 Cephalosporin Natural products 0.000 abstract description 3
229940124587 cephalosporin Drugs 0.000 abstract description 3
150000001780 cephalosporins Chemical class 0.000 abstract description 3
125000006000 trichloroethyl group Chemical group 0.000 abstract description 3
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 abstract description 2
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 abstract description 2
125000005042 acyloxymethyl group Chemical group 0.000 abstract description 2
150000001299 aldehydes Chemical class 0.000 abstract description 2
150000004657 carbamic acid derivatives Chemical class 0.000 abstract description 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 abstract description 2
125000001475 halogen functional group Chemical group 0.000 abstract description 2
150000002431 hydrogen Chemical class 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract description 2
150000002576 ketones Chemical class 0.000 abstract description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 2
150000002960 penicillins Chemical class 0.000 abstract description 2
125000004665 trialkylsilyl group Chemical group 0.000 abstract description 2
238000006243 chemical reaction Methods 0.000 description 11
238000001228 spectrum Methods 0.000 description 11
239000000203 mixture Substances 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000006260 foam Substances 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 5
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
NDIRONRTURBYKD-QNJCKLSPSA-N methyl (6r)-3-iodo-3-methyl-8-oxo-7-[(2-phenoxyacetyl)amino]-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate Chemical compound C1([C@@H]2N(C1=O)C(C(CS2)(C)I)C(=O)OC)NC(=O)COC1=CC=CC=C1 NDIRONRTURBYKD-QNJCKLSPSA-N 0.000 description 4
229940049954 penicillin Drugs 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
DRTWFAZLNURHBL-BAFYGKSASA-N (6r)-3-iodo-5-thia-1-azabicyclo[4.2.0]octan-8-one Chemical compound C1C(I)CS[C@@H]2CC(=O)N21 DRTWFAZLNURHBL-BAFYGKSASA-N 0.000 description 3
SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical compound S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
238000005914 dehydroiodination reaction Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
101150041968 CDC13 gene Proteins 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
230000009102 absorption Effects 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
HJEINPVZRDJRBY-UHFFFAOYSA-N Disul Chemical compound OS(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl HJEINPVZRDJRBY-UHFFFAOYSA-N 0.000 description 1
HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 1
CPTLAAWNMNVQNJ-UHFFFAOYSA-N N-(5-methyl-3-oxo-1,2-thiazol-4-yl)-2-phenoxyacetamide Chemical compound S1NC(=O)C(NC(=O)COC=2C=CC=CC=2)=C1C CPTLAAWNMNVQNJ-UHFFFAOYSA-N 0.000 description 1
229930195708 Penicillin V Natural products 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229960000723 ampicillin Drugs 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229960003669 carbenicillin Drugs 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
229940106164 cephalexin Drugs 0.000 description 1
ZAIPMKNFIOOWCQ-UEKVPHQBSA-N cephalexin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C)C(O)=O)=CC=CC=C1 ZAIPMKNFIOOWCQ-UEKVPHQBSA-N 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
239000012990 dithiocarbamate Substances 0.000 description 1
150000004659 dithiocarbamates Chemical class 0.000 description 1
BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000012336 iodinating agent Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
VXQROEXTWNTASQ-UHFFFAOYSA-N n-methylbenzenecarbothioamide Chemical compound CNC(=S)C1=CC=CC=C1 VXQROEXTWNTASQ-UHFFFAOYSA-N 0.000 description 1
BNLLHLUAOXAUNQ-UHFFFAOYSA-N n-methylethanethioamide Chemical compound CNC(C)=S BNLLHLUAOXAUNQ-UHFFFAOYSA-N 0.000 description 1
BOQKCADLPNLYCZ-UHFFFAOYSA-N n-phenylbenzenecarbothioamide Chemical compound C=1C=CC=CC=1C(=S)NC1=CC=CC=C1 BOQKCADLPNLYCZ-UHFFFAOYSA-N 0.000 description 1
229940056367 penicillin v Drugs 0.000 description 1
LQFUHVGITPVUOZ-UHFFFAOYSA-N prop-1-en-2-yl 2-(azetidin-1-yl)acetate Chemical compound CC(=C)OC(=O)CN1CCC1 LQFUHVGITPVUOZ-UHFFFAOYSA-N 0.000 description 1
XQWBMZWDJAZPPX-UHFFFAOYSA-N pyridine-3-carbothioamide Chemical compound NC(=S)C1=CC=CN=C1 XQWBMZWDJAZPPX-UHFFFAOYSA-N 0.000 description 1
230000036647 reaction Effects 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Landscapes

Cephalosporin Compounds (AREA)

CA229,977A 1975-06-23 1975-06-23 Thioamides Expired CA1051008A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA229,977A CA1051008A (fr)	1975-06-23	1975-06-23	Thioamides

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA229,977A CA1051008A (fr)	1975-06-23	1975-06-23	Thioamides

Publications (1)

Publication Number	Publication Date
CA1051008A true CA1051008A (fr)	1979-03-20

Family

ID=4103416

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA229,977A Expired CA1051008A (fr)	1975-06-23	1975-06-23	Thioamides

Country Status (1)

Country	Link
CA (1)	CA1051008A (fr)

1975
- 1975-06-23 CA CA229,977A patent/CA1051008A/fr not_active Expired

Publication	Publication Date	Title
KR910002098B1 (ko)	1991-04-03	페넴 화합물의 제조방법
EP0124889A2 (fr)	1984-11-14	Procédé pour la préparation de céphalosporines
EP0137440A2 (fr)	1985-04-17	Dérivés de céphalosporine et procédé pour leur préparation
US4331666A (en)	1982-05-25	3-[(8-Carboxy-6-tetrazolo[1,5-b]pyridazinyl)-thiomethyl]-7-[2-(2-amino-4-thiazolyl)-2-methoxyimino-acetamido]-3-cephem-4-carboxylic acid
EP0111934B1 (fr)	1988-08-17	Dérivés de céphalosporine et procédé pour leur préparation
JPS61263990A (ja)	1986-11-21	３−ホスホニウムメチル−３−セフエム化合物の製造法
KR870001983B1 (ko)	1987-10-24	알켄아미도 세팔로스포린 에스테르의 제조방법
DE3888458T2 (de)	1994-09-01	N,N'-Carboxyl-bis-(4-ethyl-2,3-dioxo)-piperazin, Verfahren zu dessen Herstellung und dessen Verwendung.
CA1042873A (fr)	1978-11-21	Derives d'azetidine
CA1051008A (fr)	1979-03-20	Thioamides
FI75165C (fi)	1988-05-09	Foerbaettrat foerfarande foer framstaellning av penicillansyraklormetylestrar.
CA1039710A (fr)	1978-10-03	Derives de la cephalosporine
CA1072564A (fr)	1980-02-26	Acetates de 4-chloroazetidinone-1-(2'-3'-dichloroisopropyl) et procede pour leur fabrication
US4704385A (en)	1987-11-03	3-formamido azetidinone antibacterial agents, their preparation and use
US4039530A (en)	1977-08-02	Thioamides
JPH0830051B2 (ja)	1996-03-27	４−ハロゲノ−２−置換オキシイミノ−３−オキソ酪酸のエステルまたはアミドの製造法
US4810788A (en)	1989-03-07	Azetidinone disulfide derivatives and a process for preparing the same
CA1067892A (fr)	1979-12-11	Composes iodes
JPS5823875B2 (ja)	1983-05-18	α−イソプロピリデン−１−アゼチジンアセテ−トおよびその酸の製造法
CH616940A5 (en)	1980-04-30	Process for the preparation of 7-amino-3-cephem and 6-aminopenam compounds
US5821362A (en)	1998-10-13	Method of desilylating silylether compounds
KR960006800B1 (ko)	1996-05-23	카르바페넴을 위한 알케닐실릴아제티디논 중간체
US4183850A (en)	1980-01-15	Process for preparing 2-acyloxymethylpenams and 3-acyloxycephams
EP0117875B1 (fr)	1987-07-22	Procede de preparation de derives d'azetidinone
CA1039709A (fr)	1978-10-03	Procede de production de cephalosporine