CS249534B2 - Method of cyclohexylurea's sulphonyled derivatives production - Google Patents

Method of cyclohexylurea's sulphonyled derivatives production Download PDF

Info

Publication number: CS249534B2
Authority: CS; Czechoslovakia
Prior art keywords: reaction; formula; carboxamido; ethyl; cyclohexylurea
Prior art date: 1984-01-19

Application number

CS85307A

Other languages

Czech (cs)

English (en)

Inventor

Mikael U J Dahlostroem

Yngve V Malmen

Original Assignee

Medica Pharma Co 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.)

1984-01-19

Filing date

1985-01-16

Publication date

1987-03-12

1985-01-16 Application filed by Medica Pharma Co Ltd filed Critical Medica Pharma Co Ltd

1987-03-12 Publication of CS249534B2 publication Critical patent/CS249534B2/cs

Links

238000000034 method Methods 0.000 title claims abstract description 22
WUESWDIHTKHGQA-UHFFFAOYSA-N cyclohexylurea Chemical compound NC(=O)NC1CCCCC1 WUESWDIHTKHGQA-UHFFFAOYSA-N 0.000 title claims 2
238000004519 manufacturing process Methods 0.000 title description 4
238000006243 chemical reaction Methods 0.000 claims abstract description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 10
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 8
JFRFGCASIOOBDA-UHFFFAOYSA-N 2,2,2-trichloro-n-cyclohexylacetamide Chemical compound ClC(Cl)(Cl)C(=O)NC1CCCCC1 JFRFGCASIOOBDA-UHFFFAOYSA-N 0.000 claims abstract description 6
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 6
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 4
239000000010 aprotic solvent Substances 0.000 claims abstract description 3
239000002585 base Substances 0.000 claims abstract description 3
238000010992 reflux Methods 0.000 claims abstract 2
238000002360 preparation method Methods 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
-1 alkali metal hydride amide Chemical class 0.000 claims description 2
239000008280 blood Substances 0.000 claims description 2
210000004369 blood Anatomy 0.000 claims description 2
229910000102 alkali metal hydride Inorganic materials 0.000 claims 1
ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 abstract description 13
229960001381 glipizide Drugs 0.000 abstract description 13
239000011541 reaction mixture Substances 0.000 abstract description 10
239000000126 substance Substances 0.000 abstract description 8
229910052783 alkali metal Inorganic materials 0.000 abstract description 3
150000001340 alkali metals Chemical class 0.000 abstract description 3
150000001408 amides Chemical class 0.000 abstract description 2
150000004678 hydrides Chemical class 0.000 abstract description 2
229960001760 dimethyl sulfoxide Drugs 0.000 abstract 2
238000009833 condensation Methods 0.000 abstract 1
230000005494 condensation Effects 0.000 abstract 1
239000000047 product Substances 0.000 description 19
150000001875 compounds Chemical class 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
238000001914 filtration Methods 0.000 description 9
239000002904 solvent Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 6
239000000376 reactant Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 5
IMEZLHZLIANIAS-UHFFFAOYSA-N 5-methyl-n-[2-(4-sulfamoylphenyl)ethyl]pyrazine-2-carboxamide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(N)(=O)=O)C=C1 IMEZLHZLIANIAS-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 4
238000001035 drying Methods 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
150000003672 ureas Chemical class 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
239000012467 final product Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
229940124530 sulfonamide Drugs 0.000 description 3
150000003456 sulfonamides Chemical class 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
239000012948 isocyanate Substances 0.000 description 2
150000002513 isocyanates Chemical class 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
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 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
NMBWXBWFDHVLGS-UHFFFAOYSA-N 2-ethylbenzenesulfonamide Chemical compound CCC1=CC=CC=C1S(N)(=O)=O NMBWXBWFDHVLGS-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
150000004283 biguanides Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
CJYQQUPRURWLOW-YDLUHMIOSA-M dmsc Chemical compound [Na+].OP(=O)=O.OP(=O)=O.OP(=O)=O.[O-]P(=O)=O.O=C1C2=C(O)C=CC=C2[C@H](C)[C@@H]2C1=C(O)[C@]1(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]1[C@H]2O CJYQQUPRURWLOW-YDLUHMIOSA-M 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229960004580 glibenclamide Drugs 0.000 description 1
ZNNLBTZKUZBEKO-UHFFFAOYSA-N glyburide Chemical compound COC1=CC=C(Cl)C=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZNNLBTZKUZBEKO-UHFFFAOYSA-N 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
WNSXUAGCWVZDQC-UHFFFAOYSA-N n-ethylbenzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC=CC=C1 WNSXUAGCWVZDQC-UHFFFAOYSA-N 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
230000007096 poisonous effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000003491 tear gas Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings

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)
Plural Heterocyclic Compounds (AREA)
Steroid Compounds (AREA)

CS85307A 1984-01-19 1985-01-16 Method of cyclohexylurea's sulphonyled derivatives production CS249534B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FI840209A FI69303C (fi)	1984-01-19	1984-01-19	Foerfarande foer framstaellning av ett farmakologiskt verksamtsulfonylureaderivat

Publications (1)

Publication Number	Publication Date
CS249534B2 true CS249534B2 (en)	1987-03-12

Family

ID=8518397

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS85307A CS249534B2 (en)	1984-01-19	1985-01-16	Method of cyclohexylurea's sulphonyled derivatives production

Country Status (9)

Country	Link
EP (1)	EP0149592A3 (de)
CS (1)	CS249534B2 (de)
DD (1)	DD228251A5 (de)
DK (1)	DK18985A (de)
FI (1)	FI69303C (de)
NO (1)	NO850217L (de)
PL (1)	PL251605A1 (de)
SU (1)	SU1340584A3 (de)
ZA (1)	ZA8410079B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2144915C1 (ru) *	1999-04-28	2000-01-27	Общество с ограниченной ответственностью "Фармсинтез"	Способ получения арилсульфонилмочевин
CN107434788B (zh) *	2017-09-11	2018-06-15	威海迪素制药有限公司	一种格列吡嗪的制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU162761B (de) *	1971-04-06	1973-04-28

1984
- 1984-01-19 FI FI840209A patent/FI69303C/sv not_active IP Right Cessation
- 1984-12-27 ZA ZA8410079A patent/ZA8410079B/xx unknown
1985
- 1985-01-15 DK DK18985A patent/DK18985A/da not_active Application Discontinuation
- 1985-01-16 SU SU853837681A patent/SU1340584A3/ru active
- 1985-01-16 CS CS85307A patent/CS249534B2/cs unknown
- 1985-01-17 DD DD85272627A patent/DD228251A5/de unknown
- 1985-01-17 EP EP85850019A patent/EP0149592A3/de not_active Withdrawn
- 1985-01-18 NO NO850217A patent/NO850217L/no unknown
- 1985-01-18 PL PL25160585A patent/PL251605A1/xx unknown

Also Published As

Publication number	Publication date
PL251605A1 (en)	1985-10-22
DK18985D0 (da)	1985-01-15
FI840209A0 (fi)	1984-01-19
NO850217L (no)	1985-07-22
SU1340584A3 (ru)	1987-09-23
ZA8410079B (en)	1985-08-28
FI840209A7 (fi)	1985-07-20
FI69303C (fi)	1986-01-10
EP0149592A3 (de)	1986-06-04
EP0149592A2 (de)	1985-07-24
DD228251A5 (de)	1985-10-09
DK18985A (da)	1985-07-20
FI69303B (fi)	1985-09-30

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