CA1102803A - Traduction non-disponible - Google Patents

Traduction non-disponible

Info

Publication number: CA1102803A
Authority: CA; Canada
Prior art keywords: general formula; sulphoximide; reaction; lower alkyl; straight chain
Prior art date: 1980-02-04
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

CA345,046A

Other languages

English (en)

Inventor

Manfred Haake

Reinhold Pothmann

Kurt H. Ahrens

Edgar Fritschi

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.)

Heumann Ludwig and Co GmbH

Original Assignee

Heumann Ludwig and Co GmbH

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.)

1980-02-04

Filing date

1980-02-04

Publication date

1981-06-09

1980-02-04 Application filed by Heumann Ludwig and Co GmbH filed Critical Heumann Ludwig and Co GmbH

1980-02-04 Priority to CA345,046A priority Critical patent/CA1102803A/fr

1981-06-09 Application granted granted Critical

1981-06-09 Publication of CA1102803A publication Critical patent/CA1102803A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 6
150000001875 compounds Chemical class 0.000 claims abstract description 14
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 13
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
125000000217 alkyl group Chemical group 0.000 claims abstract description 10
238000006243 chemical reaction Methods 0.000 claims abstract description 9
150000003839 salts Chemical group 0.000 claims abstract description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
-1 pyrrolidino, piperidino Chemical group 0.000 claims abstract description 4
239000002253 acid Substances 0.000 claims abstract description 3
150000001449 anionic compounds Chemical group 0.000 claims abstract description 3
150000002891 organic anions Chemical group 0.000 claims abstract description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims abstract 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
239000002904 solvent Substances 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 2
238000005648 named reaction Methods 0.000 claims 2
238000010533 azeotropic distillation Methods 0.000 claims 1
239000000126 substance Substances 0.000 claims 1
230000002048 spasmolytic effect Effects 0.000 abstract description 4
230000000144 pharmacologic effect Effects 0.000 abstract description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
239000004305 biphenyl Substances 0.000 description 10
229910052739 hydrogen Inorganic materials 0.000 description 10
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 7
101150041968 CDC13 gene Proteins 0.000 description 7
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
239000013078 crystal Substances 0.000 description 6
239000011261 inert gas Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000000047 product Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
238000003756 stirring Methods 0.000 description 5
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
239000008098 formaldehyde solution Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
229940102396 methyl bromide Drugs 0.000 description 4
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003814 drug Substances 0.000 description 3
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
XQGOFKFATFKSFH-UHFFFAOYSA-N N-ethyl-N-[[[oxo(diphenyl)-lambda6-sulfanylidene]amino]methyl]ethanamine Chemical compound C(C)N(CC)CN=S(=O)(C1=CC=CC=C1)C1=CC=CC=C1 XQGOFKFATFKSFH-UHFFFAOYSA-N 0.000 description 2
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
229960001340 histamine Drugs 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
ZKJJBMKFLUOHAP-UHFFFAOYSA-N morpholin-4-ylmethylimino-oxo-diphenyl-lambda6-sulfane Chemical compound O1CCN(CC1)CN=S(=O)(C1=CC=CC=C1)C1=CC=CC=C1 ZKJJBMKFLUOHAP-UHFFFAOYSA-N 0.000 description 2
YRBWBVBBWHYPJE-UHFFFAOYSA-N oxo-diphenyl-(piperidin-1-ylmethylimino)-lambda6-sulfane Chemical compound N1(CCCCC1)CN=S(=O)(C1=CC=CC=C1)C1=CC=CC=C1 YRBWBVBBWHYPJE-UHFFFAOYSA-N 0.000 description 2
MSWZGWJZZCNBPR-UHFFFAOYSA-N oxo-diphenyl-(pyrrolidin-1-ylmethylimino)-lambda6-sulfane Chemical compound N1(CCCC1)CN=S(=O)(C1=CC=CC=C1)C1=CC=CC=C1 MSWZGWJZZCNBPR-UHFFFAOYSA-N 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000003107 substituted aryl group Chemical group 0.000 description 2
MIFZZKZNMWTHJK-UHFFFAOYSA-N 4-(morpholin-4-ylmethyl)morpholine Chemical compound C1COCCN1CN1CCOCC1 MIFZZKZNMWTHJK-UHFFFAOYSA-N 0.000 description 1
229930003347 Atropine Natural products 0.000 description 1
208000009079 Bronchial Spasm Diseases 0.000 description 1
241000700198 Cavia Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 1
MBWPBTLGDWOAHO-UHFFFAOYSA-N IN=S Chemical compound IN=S MBWPBTLGDWOAHO-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
238000011785 NMRI mouse Methods 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
238000011047 acute toxicity test Methods 0.000 description 1
239000000556 agonist Substances 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
229960000396 atropine Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000001813 broncholytic effect Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000006196 drop Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
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 1
238000001727 in vivo Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940050176 methyl chloride Drugs 0.000 description 1
239000000203 mixture Substances 0.000 description 1
230000003170 musculotropic effect Effects 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000002276 neurotropic effect Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000012265 solid product Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000829 suppository Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA345,046A 1980-02-04 1980-02-04 Traduction non-disponible Expired CA1102803A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA345,046A CA1102803A (fr)	1980-02-04	1980-02-04	Traduction non-disponible

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA345,046A CA1102803A (fr)	1980-02-04	1980-02-04	Traduction non-disponible

Publications (1)

Publication Number	Publication Date
CA1102803A true CA1102803A (fr)	1981-06-09

Family

ID=4116177

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA345,046A Expired CA1102803A (fr)	1980-02-04	1980-02-04	Traduction non-disponible

Country Status (1)

Country	Link
CA (1)	CA1102803A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1991010648A1 (fr) *	1990-01-06	1991-07-25	Pfizer Limited	Antagonistes de recepteurs muscariniques a base de diphenylsulphoximine

1980
- 1980-02-04 CA CA345,046A patent/CA1102803A/fr not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1991010648A1 (fr) *	1990-01-06	1991-07-25	Pfizer Limited	Antagonistes de recepteurs muscariniques a base de diphenylsulphoximine

Legal Events

Date	Code	Title	Description
1998-06-09	MKEX	Expiry

Publication	Publication Date	Title
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EP0185368B1 (fr)	1990-06-06	Dérivés d'aminobenzamide
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CA1041098A (fr)	1978-10-24	Derives de ((napht-1-yl-oxy)-3 propyl)-1 piperozine
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US4091095A (en)	1978-05-23	Phosphinyl compounds
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US4213905A (en)	1980-07-22	Preparation of 5-aroyl-1-loweralkylpyrrole-2-acetic acid salts
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EP0393109B1 (fr)	1994-03-23	Nouveaux derives de 2,3-thiomorpholinedione-2-oxime, compositions pharmaceutiques contenant ces derives et procede servant a leur preparation
US2589937A (en)	1952-03-18	Manufacture of new basic esters of 1-aryl-cyclopentane-1-monothiocarboxylic acids
US4152438A (en)	1979-05-01	Phenoxyalkylaminepyridylethers
HU198915B (en)	1989-12-28	Process for producing new 2-thiazolidinone derivatives and pharmaceutical compositions containing them
KR850001038B1 (ko)	1985-07-19	알로파노일 피페라진 화합물의 제조방법
US3971782A (en)	1976-07-27	Fluorene derivatives

CA1102803A - Traduction non-disponible - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4116177

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

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