CA1092142A - Obtention de derives de 4-hydrophenylalcanolamine - Google Patents

Obtention de derives de 4-hydrophenylalcanolamine

Info

Publication number: CA1092142A
Authority: CA; Canada
Prior art keywords: acid; compound; hydrogen; formula; aroyl
Prior art date: 1976-06-25
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

CA347,767A

Other languages

English (en)

Inventor

Richard E. Philion

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.)

STWB Inc

Original Assignee

Sterling Drug Inc

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.)

1976-06-25

Filing date

1980-03-17

Publication date

1980-12-23

1977-06-24 Priority claimed from CA281,375A external-priority patent/CA1091245A/fr

1980-03-17 Application filed by Sterling Drug Inc filed Critical Sterling Drug Inc

1980-03-17 Priority to CA347,767A priority Critical patent/CA1092142A/fr

1980-12-23 Application granted granted Critical

1980-12-23 Publication of CA1092142A publication Critical patent/CA1092142A/fr

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 32
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 9
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 4
239000002253 acid Substances 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 24
125000000217 alkyl group Chemical group 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
125000003435 aroyl group Chemical group 0.000 claims description 10
125000001589 carboacyl group Chemical group 0.000 claims description 8
239000012458 free base Substances 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
150000001733 carboxylic acid esters Chemical group 0.000 claims description 3
239000003638 chemical reducing agent Substances 0.000 claims description 3
125000001475 halogen functional group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims description 2
230000003301 hydrolyzing effect Effects 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims description 2
230000001590 oxidative effect Effects 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 claims description 2
150000001447 alkali salts Chemical class 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
239000003416 antiarrhythmic agent Substances 0.000 abstract description 3
239000002220 antihypertensive agent Substances 0.000 abstract description 2
229940030600 antihypertensive agent Drugs 0.000 abstract description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
-1 aminoalkyl phenyl ketone Chemical compound 0.000 description 18
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
241000282472 Canis lupus familiaris Species 0.000 description 10
150000002500 ions Chemical class 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
238000012360 testing method Methods 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 8
239000002585 base Substances 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000000203 mixture Substances 0.000 description 8
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230000036772 blood pressure Effects 0.000 description 7
239000000047 product Substances 0.000 description 7
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 5
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 5
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229960003343 ouabain Drugs 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000001450 anions Chemical class 0.000 description 4
125000001246 bromo group Chemical group Br* 0.000 description 4
229960001701 chloroform Drugs 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
230000010412 perfusion Effects 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
238000003756 stirring Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
208000001953 Hypotension Diseases 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
241000283973 Oryctolagus cuniculus Species 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
230000003276 anti-hypertensive effect Effects 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
235000011167 hydrochloric acid Nutrition 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
125000004356 hydroxy functional group Chemical group O* 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
229960001412 pentobarbital Drugs 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 3
210000003462 vein Anatomy 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
244000025254 Cannabis sativa Species 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
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238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
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125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CA347,767A 1976-06-25 1980-03-17 Obtention de derives de 4-hydrophenylalcanolamine Expired CA1092142A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA347,767A CA1092142A (fr)	1976-06-25	1980-03-17	Obtention de derives de 4-hydrophenylalcanolamine

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US69985676A	1976-06-25	1976-06-25
US699,856		1976-06-25
US80337277A	1977-06-03	1977-06-03
US803,372		1977-06-03
CA281,375A CA1091245A (fr)	1976-06-25	1977-06-24	Obtention de derives de 4-hydroxyphenylalcanolamine
CA347,767A CA1092142A (fr)	1976-06-25	1980-03-17	Obtention de derives de 4-hydrophenylalcanolamine

Publications (1)

Publication Number	Publication Date
CA1092142A true CA1092142A (fr)	1980-12-23

Family

ID=27425996

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA347,767A Expired CA1092142A (fr)	1976-06-25	1980-03-17	Obtention de derives de 4-hydrophenylalcanolamine

Country Status (1)

Country	Link
CA (1)	CA1092142A (fr)

1980
- 1980-03-17 CA CA347,767A patent/CA1092142A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-12-23	MKEX	Expiry

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JPS62265278A (ja)	1987-11-18	Ｎ−（フエニル）若しくはｎ−（フエニルシクロプロピル）−２，５−ジヒドロ−２−オキソ−４−〔（置換フエニル）アミノ〕−３−フランカルボキシアミド誘導体
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US4695589A (en)	1987-09-22	Alpha-(aminoalkyl-4-hydroxy-3-(alkylthio)benzenemethanols
DE3000519A1 (de)	1980-08-14	Sulfonamido-alkansaeuren, ihre verwendung und herstellung sowie sie enthaltende arzneimittel
CN110156704B (zh)	2023-06-09	1,2,4-三唑硫醚衍生物及其晶体结构与应用
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CA1276750C (fr)	1990-11-20	Methode de preparation de composes du thiophene
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