CS208752B2 - Method of making the r-n-(2-fenyl-2-hydroxyethyl)-3-fenyl propylamines - Google Patents

Method of making the r-n-(2-fenyl-2-hydroxyethyl)-3-fenyl propylamines Download PDF

Info

Publication number: CS208752B2
Authority: CS; Czechoslovakia
Prior art keywords: hydroxyphenyl; hydroxyethyl; compounds; hydrogen; fenyl
Prior art date: 1978-07-03

Application number

CS794628A

Other languages

Czech (cs)

English (en)

Inventor

Jack Mills

Klaus K Schmiegel

Ronald R Tuttle

Original Assignee

Lilly Co Eli

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.)

1978-07-03

Filing date

1979-07-02

Publication date

1981-09-15

1979-07-02 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1981-09-15 Publication of CS208752B2 publication Critical patent/CS208752B2/cs

Links

238000004519 manufacturing process Methods 0.000 title description 4
125000006308 propyl amino group Chemical class 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
239000001257 hydrogen Substances 0.000 claims abstract description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
229910052799 carbon Inorganic materials 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
229910052731 fluorine Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 38
238000000034 method Methods 0.000 claims description 14
150000001412 amines Chemical class 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 7
125000006239 protecting group Chemical group 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
239000007858 starting material Substances 0.000 claims 1
230000000747 cardiac effect Effects 0.000 abstract description 7
238000011282 treatment Methods 0.000 abstract description 5
RGPGRFUHKBXJLQ-KRWDZBQOSA-N (1r)-1-phenyl-2-(3-phenylpropylamino)ethanol Chemical class C([C@H](O)C=1C=CC=CC=1)NCCCC1=CC=CC=C1 RGPGRFUHKBXJLQ-KRWDZBQOSA-N 0.000 abstract description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
230000000994 depressogenic effect Effects 0.000 abstract 1
239000011737 fluorine Chemical group 0.000 abstract 1
230000000694 effects Effects 0.000 description 16
206010019280 Heart failures Diseases 0.000 description 14
239000002253 acid Substances 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
-1 amine salts Chemical class 0.000 description 9
239000003814 drug Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
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229940079593 drug Drugs 0.000 description 7
230000001965 increasing effect Effects 0.000 description 7
210000004165 myocardium Anatomy 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 6
210000002027 skeletal muscle Anatomy 0.000 description 6
230000017531 blood circulation Effects 0.000 description 5
239000002775 capsule Substances 0.000 description 5
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239000011541 reaction mixture Substances 0.000 description 5
125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 4
239000004480 active ingredient Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000003247 decreasing effect Effects 0.000 description 4
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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241000282472 Canis lupus familiaris Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
JRWZLRBJNMZMFE-UHFFFAOYSA-N Dobutamine Chemical compound C=1C=C(O)C(O)=CC=1CCNC(C)CCC1=CC=C(O)C=C1 JRWZLRBJNMZMFE-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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150000001408 amides Chemical class 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
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239000003085 diluting agent Substances 0.000 description 2
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LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
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150000007522 mineralic acids Chemical class 0.000 description 2
208000010125 myocardial infarction Diseases 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
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238000011321 prophylaxis Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
IPMKAUAKEGAJNA-XSUJLISDSA-N solanapyrone g Chemical compound C1([C@H]2[C@@H]3CCCC[C@@H]3C=C[C@@H]2C)=CC(N)=C(C=O)C(=O)O1 IPMKAUAKEGAJNA-XSUJLISDSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
MOMLUQUHQNAYEK-KRWDZBQOSA-N 3-[(1r)-1-hydroxy-2-[3-(4-hydroxyphenyl)propylamino]ethyl]phenol Chemical compound C([C@H](O)C=1C=C(O)C=CC=1)NCCCC1=CC=C(O)C=C1 MOMLUQUHQNAYEK-KRWDZBQOSA-N 0.000 description 1
DPJAIQMVJHWZFH-KRWDZBQOSA-N 3-[3-[[(2R)-2-(2-fluorophenyl)-2-hydroxyethyl]amino]propyl]phenol Chemical compound O[C@@H](CNCCCC1=CC(O)=CC=C1)C1=C(F)C=CC=C1 DPJAIQMVJHWZFH-KRWDZBQOSA-N 0.000 description 1
ILYGUWXQPRWYJO-KRWDZBQOSA-N 3-[3-[[(2r)-2-hydroxy-2-(3-hydroxyphenyl)ethyl]amino]propyl]phenol Chemical compound C([C@H](O)C=1C=C(O)C=CC=1)NCCCC1=CC=CC(O)=C1 ILYGUWXQPRWYJO-KRWDZBQOSA-N 0.000 description 1
LEPIYBYPRPWIAA-UHFFFAOYSA-N 4-(propylamino)phenol Chemical compound CCCNC1=CC=C(O)C=C1 LEPIYBYPRPWIAA-UHFFFAOYSA-N 0.000 description 1
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241000208011 Digitalis Species 0.000 description 1
125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
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JPYRAMGKAHVYFZ-CQSZACIVSA-N [(1r)-2-chloro-2-oxo-1-(3-phenylmethoxyphenyl)ethyl] 2,2-dichloroacetate Chemical compound ClC(Cl)C(=O)O[C@@H](C(Cl)=O)C1=CC=CC(OCC=2C=CC=CC=2)=C1 JPYRAMGKAHVYFZ-CQSZACIVSA-N 0.000 description 1
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UKNHYPLORGBRMI-OOZXSOIMSA-N [(2r)-2-hydroxy-2-(4-hydroxyphenyl)ethyl]-[3-(4-hydroxyphenyl)propyl]azanium;oxalate Chemical compound [O-]C(=O)C([O-])=O.C([C@H](O)C=1C=CC(O)=CC=1)[NH2+]CCCC1=CC=C(O)C=C1.C([C@H](O)C=1C=CC(O)=CC=1)[NH2+]CCCC1=CC=C(O)C=C1 UKNHYPLORGBRMI-OOZXSOIMSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/54—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups linked by carbon chains having at least three carbon atoms between the amino groups and the six-membered aromatic ring or the condensed ring system containing that ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS794628A 1978-07-03 1979-07-02 Method of making the r-n-(2-fenyl-2-hydroxyethyl)-3-fenyl propylamines CS208752B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US92166678A	1978-07-03	1978-07-03

Publications (1)

Publication Number	Publication Date
CS208752B2 true CS208752B2 (en)	1981-09-15

Family

ID=25445781

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS794628A CS208752B2 (en)	1978-07-03	1979-07-02	Method of making the r-n-(2-fenyl-2-hydroxyethyl)-3-fenyl propylamines

Country Status (23)

Country	Link
EP (1)	EP0007716A1 (de)
JP (1)	JPS559099A (de)
AR (1)	AR221733A1 (de)
AT (1)	ATA463879A (de)
AU (1)	AU4848679A (de)
BE (1)	BE877390A (de)
CA (1)	CA1126296A (de)
CS (1)	CS208752B2 (de)
DD (1)	DD144764A5 (de)
DK (1)	DK268479A (de)
ES (2)	ES482152A1 (de)
FI (1)	FI792078A7 (de)
FR (1)	FR2430407A1 (de)
GB (1)	GB2028801A (de)
GR (1)	GR73049B (de)
IL (1)	IL57669A0 (de)
LU (1)	LU81454A1 (de)
NZ (1)	NZ190862A (de)
PH (1)	PH15477A (de)
PL (1)	PL117485B1 (de)
PT (1)	PT69842A (de)
RO (1)	RO77727A (de)
ZA (1)	ZA793294B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0103830A3 (de) *	1982-09-22	1985-07-31	Bayer Ag	Wachstumsfördernde Phenylethylamin-Derivate
US4849453A (en) *	1983-01-31	1989-07-18	Eli Lilly And Company	Growth promotion
US5643967A (en) *	1983-01-31	1997-07-01	Eli Lilly And Company	Growth promotion
EP0117647B1 (de) *	1983-01-31	1988-08-17	Eli Lilly And Company	Phenethanolamine
CN1073983C (zh) *	1994-10-31	2001-10-31	中国科学院成都有机化学研究所	一种β－拟肾上腺素兴奋剂型饲料添加剂的合成方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL6610530A (de) *	1966-07-27	1968-01-29

1979
- 1979-06-26 CA CA330,567A patent/CA1126296A/en not_active Expired
- 1979-06-26 IL IL57669A patent/IL57669A0/xx unknown
- 1979-06-26 DK DK268479A patent/DK268479A/da unknown
- 1979-06-27 PH PH22701A patent/PH15477A/en unknown
- 1979-06-27 NZ NZ190862A patent/NZ190862A/xx unknown
- 1979-06-28 AU AU48486/79A patent/AU4848679A/en not_active Abandoned
- 1979-06-28 PT PT69842A patent/PT69842A/pt unknown
- 1979-06-29 FR FR7916990A patent/FR2430407A1/fr active Granted
- 1979-07-02 JP JP8489379A patent/JPS559099A/ja active Pending
- 1979-07-02 FI FI792078A patent/FI792078A7/fi not_active Application Discontinuation
- 1979-07-02 CS CS794628A patent/CS208752B2/cs unknown
- 1979-07-02 BE BE1/9441A patent/BE877390A/fr unknown
- 1979-07-02 EP EP79301281A patent/EP0007716A1/de not_active Withdrawn
- 1979-07-02 RO RO7998008A patent/RO77727A/ro unknown
- 1979-07-02 LU LU81454A patent/LU81454A1/xx unknown
- 1979-07-02 GB GB7922954A patent/GB2028801A/en not_active Withdrawn
- 1979-07-02 GR GR59487A patent/GR73049B/el unknown
- 1979-07-03 ZA ZA793294A patent/ZA793294B/xx unknown
- 1979-07-03 PL PL1979216813A patent/PL117485B1/pl unknown
- 1979-07-03 AR AR277163A patent/AR221733A1/es active
- 1979-07-03 AT AT0463879A patent/ATA463879A/de not_active Application Discontinuation
- 1979-07-03 DD DD79214072A patent/DD144764A5/de unknown
- 1979-07-03 ES ES482152A patent/ES482152A1/es not_active Expired
1980
- 1980-04-01 ES ES490208A patent/ES8104188A1/es not_active Expired

Also Published As

Publication number	Publication date
LU81454A1 (fr)	1979-10-30
ATA463879A (de)	1981-10-15
FI792078A7 (fi)	1981-01-01
FR2430407A1 (fr)	1980-02-01
BE877390A (fr)	1980-01-02
GR73049B (de)	1984-01-26
CA1126296A (en)	1982-06-22
FR2430407B1 (de)	1981-08-14
PH15477A (en)	1983-01-27
DD144764A5 (de)	1980-11-05
GB2028801A (en)	1980-03-12
EP0007716A1 (de)	1980-02-06
NZ190862A (en)	1981-11-19
RO77727A (ro)	1981-11-24
PL117485B1 (en)	1981-08-31
PL216813A1 (de)	1980-03-24
PT69842A (en)	1979-07-01
ES490208A0 (es)	1981-04-16
IL57669A0 (en)	1979-10-31
DK268479A (da)	1980-01-04
ES482152A1 (es)	1980-08-16
ES8104188A1 (es)	1981-04-16
JPS559099A (en)	1980-01-22
AR221733A1 (es)	1981-03-13
AU4848679A (en)	1980-01-10
ZA793294B (en)	1981-02-25

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