CA2618888A1 - Acyltryptophanols for fertility control - Google Patents

Acyltryptophanols for fertility control Download PDF

Info

Publication number
CA2618888A1
CA2618888A1 CA002618888A CA2618888A CA2618888A1 CA 2618888 A1 CA2618888 A1 CA 2618888A1 CA 002618888 A CA002618888 A CA 002618888A CA 2618888 A CA2618888 A CA 2618888A CA 2618888 A1 CA2618888 A1 CA 2618888A1
Authority
CA
Canada
Prior art keywords
indol
ethyl
carboxylic acid
hydroxymethyl
amide
Prior art date
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.)
Abandoned
Application number
CA002618888A
Other languages
French (fr)
Inventor
Lars Wortmann
Arwed Cleve
Hans-Peter Muhn
Gernot Langer
Anna Schrey
Ronald Kuehne
Bernd Menzenbach
Marcus Koppitz
Dirk Kosemund
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.)
Bayer Pharma AG
Original Assignee
Bayer Schering Pharma Aktiengesellschaft
Lars Wortmann
Arwed Cleve
Hans-Peter Muhn
Gernot Langer
Anna Schrey
Ronald Kuehne
Bernd Menzenbach
Marcus Koppitz
Dirk Kosemund
Schering Aktiengesellschaft
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.)
Filing date
Publication date
Priority claimed from DE102005038632A external-priority patent/DE102005038632B4/en
Application filed by Bayer Schering Pharma Aktiengesellschaft, Lars Wortmann, Arwed Cleve, Hans-Peter Muhn, Gernot Langer, Anna Schrey, Ronald Kuehne, Bernd Menzenbach, Marcus Koppitz, Dirk Kosemund, Schering Aktiengesellschaft filed Critical Bayer Schering Pharma Aktiengesellschaft
Publication of CA2618888A1 publication Critical patent/CA2618888A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/16—Masculine contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/18—Feminine contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • C07C65/24—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79—Acids; Esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
    • C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C07D239/72—Quinazolines; Hydrogenated quinazolines
    • C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or 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
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/60—Radicals substituted by 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
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/32—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/38—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
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Abstract

The present patent application relates to acyltryptophanols of the general formula I, in which Q, X, Y, W, R1, R2, R3, R4, R5, R8 have the meanings stated in the description. The compounds according to the invention are effective FSH antagonists and can be used for example for fertility control in men or in women, or for the prevention and/or treatment of osteoporosis.

Description

~ CA 02618888 2008-02-06 Printed: 23-11-2007 ~ ~P~7 Oti 1Z'Pt ~
Europaisches P~ DESCPAMD PJ~ PCT/EP 2006/007 949 n~qn~tstelle Berlm 0 4. MAI 1001 deaa, C.a pjl Ani..

Acyltryptophanols for Fertility Control The present patent application relates to novel acyltryptophanols, process for their preparation, pharmaceutical compositions comprising the compounds according to the invention, and the use thereof for fertility control in men or in women.
Follicle-stimulating hormone (FSH) and luteinizing hormone (LH) are together responsible for the control of male and female fertility and of the production of sex steroids.
In the female mammal, FSH controls the early ripening of ovarian primary follicles and the biosynthesis of sex steroids. In the advanced stage of differentiation (preantral follicles), the influence of LH becomes increasingly important for further development of the follicles until ovulation occurs.
In male mammals, FSH is primarily responsible for the differentiation and stimulation of -Sertoli cells. Their function consists of assisting spermatogenesis on many levels. LH is primarily responsible for stimulating the Leydig cells and thus androgen production.
FSH, LH and TSH (thyrotropic hormone) together form the group of glycoprotein hormones which are formed in the pituitary and are secreted from there.
Whereas the alpha subunit is common to the three hormones, their specificity of action is determined by the beta chain which is unique in each case. The molecular weight of FSH
including the sugar portion is about 30 kD.
FSH and the other glycoprotein hormones act specifically via their selectively expressed G protein-coupled receptor (GPCR). FSH stimulates, through binding to its receptor, the association thereof with a stimulating G protein (Gg) which is thereby stimulated to hydrolyse guanosine triphosphate (GTP) and to activate the membrane-associated adenylate cyclase. Cyclic adenosine monophosphate (cAMP) is accordingly an important and readily quantifiable secondary messenger substance of FSH (G.
Vassart, L. Pardo, S. Costagliola, Trends Biochem. Sci. 2004, 29, 119-126).
The importance of FSH for male fertility is the subject of intensive research.
It has been possible to show that FSH influences several processes of spermatogenesis such as the proliferation of spermatogonia, the antiapoptotic effect on spermatogonia and spermatocytes and the stimulation of sperm maturation including motility thereof.
The following arguments are also in favour of the FSH receptor as target for male fertility control:

1/4 AMENDED SHEET 04-05-20~67 1. The FSH receptor is exclusively expressed on Sertoli cells (high specificity).
2. Contraceptive vaccination against FSH beta chain or the FSH receptor induces infertility in male primates (N. R. Mougdal, M. Jeyakumar, H. N.
Krishnamurthy, S.
Sridhar, H. Krishnamurthy, F. Martin, Human Reproduction Update 1997, 3, 335-346).
3. Naturally occurring mutations in the FSH receptor or the FSH beta chain may lead to sub- or infertility in men (I. Huhtaniemi, Journal of Reproduction and Fertility 2000, 119, 173-186; L. C. Layman, P. G. McDonough, Molecular and Cellular Endocrinology 2000, 161, 9-17).
4. Neutralizing FSH antiserum has no effect on testis weight and testosterone production (V. Sriraman, A. J. Rao, Molecular and Cellular Endocrionology 2004, 224, 73-82). Adverse effects of FSH blockade on androgen production therefore appear unlikely.

In accordance with the stated arguments, it is to be expected that effective FSH
antagonists are suitable for spermatogenesis inhibition (prevention) in men.
However, a suitable FSH antagonist also leads to infertility in women, because it will suppress follicle ripening and thus also ovulation.
On the other hand, the skilled person expects advantages from non-peptidergic FSH
agonists when used to promote fertility in women (stimulation of follicle ripening). There are no reports of experience on the use of FSH or FSH agonists in male infertility, but specific indications are also conceivable in this connection.

New findings demonstrate that there is also a direct effect of FSH on cells of bone metabolism. Two fundamentally different cell types need to be distinguished:
osteoclasts play a central role in bone resorption (breakdown of bone).
Osteoblasts simulate bone density (anabolic effect).

FSH receptors have been detected in osteoclasts but not osteoblasts. In vitro, FSH
stimulates bone resorption by mouse osteoclasts ( Li Sun et al. 2006. FSH
directly regu-lates bone mass. Cell 2006; 125: 247-60). A clinical correlation between the height of the serum FSH levels and low bone density has been observed in postmenopausal women (Devleta et al, 2004; Hypergonadotropic amenorrhea and bone density: new approach to an old problem. J. Bone Miner. Metab. 22: 360-4).
This and other findings suggest that FSH stimulates loss of bone mass, and accordingly FSH antagonists will display an antiresorptive effect on bone and are therefore suitable ~.. --Prjnted: 23-11-2007~~ DESCPAMD PCT/EP 2006/007 949 for the therapy and/or prevention of peri- and postmenopausal loss of bone mass and osteoporosis.

In recent years, some low molecular weight FSH receptor modulators, FSH
receptor antagonists and FSH receptor agonists from various classes of substances have been published.

FSH receptor modulators are disclosed in WO 2004/056779, WO 2004/056780; J.
Med.
Chem. 2005, 48, 1697 [Tetrahydroquinolines]; WO 02/70493, Bioorg. Med. Chem.
Lett.
2004, 14, 1713 and 1717 [Diketopiperazines]; and WO 01/47875 [Sulphonamides].
FSH receptor agonists are disclosed in WO 02/09706; J. Comb. Chem. 2004, 6, [Thiazolidinones]; WO 2003/020726 and WO 03/20727, Chem. Biochem. 2002, 10, 1023 (Thieno[2,3-d] pyrimidines); WO 01/87287 [Pyrazoles]; WO 00/08015 [Carbazoles].
Examples of FSH receptor antagonists are disclosed in WO 03/004028 [fetrahydroquinolines], WO 02/09705 [Thiazolidinones], WO 00/58277, Bioorg.
Med.
Chem. 2002, 10, 639 [Sulphonic acids]; WO 00/58276, WO 00/58277 [Aryl sulfonic acids], Endocr. 2002, 143, 3822; Synth. Comm. 2002, 32, 2695 [Azo compounds].

WO 2004/081011 describes 2-aryl substituted 3-oxo-1,3-dihydropyrazolo[4,3-c]cmnolm derivatives with immunomodulatory activity and discloses 4-(8-fluoro-3-oxo-1,3-dihydro-pyrazolo[4,3-c]cinnolin-2-yl-N-[3-hydroxy-2-(1-H-indol-3-yl)-propyl]benzamide explicitly, which incidentally falls within the scope of the present invention.

The object of the present invention was therefore to provide alternative compounds having an FSH receptor antagonistic effect.
The object has been achieved according to the present invention by the compounds of the formula I

2J4 , AMENDED SHEET 04-05-2007'' in which R1 may be hydrogen, C,-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C,-C6-alkyloxy-C,-C6-alkylene, C3-C7-cycloalkyloxy-C,-Cs-alkylene, C,-C6-alkylamino-C,-Cs-alkylene, di(C,-C6-alkyl)amino-C,-Cs-alkylene, phenyloxy-C,-C6-alkylene;
where the hydrocarbon chains therein may optionally be substituted one or more times by fluorine, cyano, hydroxy, amino or the groups:

-N/~ . I -N 0 -N \S -N S~.
\J \---/ 'o -N /-\ N-Ca Cs -Alkyl -N~~//~Co Cs Alkyl \N
~N-Co Cs Alkyl R2 may be hydrogen, halogen, cyano, -SO2Me, C,-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C,-C6-alkyloxy or benzyloxy, where the hydrocarbon chains therein may optionally be substituted one or more times by fluorine;

R3 may be hydrogen, hydroxy, halogen, nitro, amino, cyano, C,-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, C3-C,-cycloalkyl, hydroxy-C,-C6-alkylene, hydroxy-C3-C6-alkenylene, hydroxy-C3-C6-alkynylene, C1-C6-alkyloxy, C,-Cs-alkyloxy-C,-C6-alkylene, C3-C7-cycloalkyloxy, C3-C,-cycloalkyl-C,-C6-alkylenoxy, C3-C,-cycloalkyloxy-C,-C6-alkylene, C,-C6-alkyloxy-C3-C6-alkenylene, C,-C6-alkyloxy-C3-C6-alkynylene, C,-C6-alkyloxyphenyl-C,-C6-alkylene, C,-C6-alkylamino-C,-C6-alkylene, di(C,-C6-alkyl)amino-C,-C6-alkylene, phenyloxy-C,-C6-alkylene;
where the hydrocarbon chains therein may optionally be substituted one or more times by fluorine, cyano, hydroxy, amino or the groups /~ 0 -N, I -N O -N \S -N \S, ~J \-/ , o -N /--\
N-Co Cs AIkyI -Nv~Ca Cs Alkyl ~N
N-Co Cs Alkyl R4, R5, R6 may be independently of one another hydrogen, hydroxy, halogen, nitro, amino, cyano, phenyl, C,-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, C3-5 C7-cycloalkyl, C3-C7-cycloalkyl-C,-C6-alkylene, C3-C7-heterocycloalkyl, where the hydrocarbon chains therein may optionally be substituted one or more times by fluorine, cyano or the radicals:
/~ 0 - N, I -N O - N \S - N \S .
~J o ~ \N~
-N ~N-Co Cs Alkyl -NaCo Cs Alkyl ~N-Co C fi Alkyl or independently of one another hydroxy-C,-C6-alkylene, hydroxy-C3-C6-alkenylene, hydroxy-C3-Cs-alkynylene, C,-C6-alkyloxy, C3-C7-cycloalkyloxy, C3-C7-cycloalkyl-C,-C6-alkylenoxy, C,-C6-alkyloxy-C,-C6-alkylene, C3-C,-cycloalkyloxy-C,-C6-alkylene, C1-C6-alkyloxy-C3-C6-alkenylene, C,-C6-alkyloxy-C3-C6-alkynylene, C,-C6-alkyloxyphenyl-C,-C6-alkylene, phenyloxy-C,-C6-alkylene, C,-C6-alkylamino, di(C,-C6-alkyl)amino, C,-C6-alkylamino-C,-Cs-alkylene, di(C,-C6)-alkylamino-C,-C6-alkylene, C3-C7-cycloalkyl-(Co-C6-alkyl)amino, C,-C6-acyl-(Co-Cs-alkyl)amido, C,-Cs-alkylaminocarbonyl, di(C,-Cs-alkyl)aminocarbonyl, (C3-C,-cycloalkyl)aminocarbonyl, di(C3-C7-cycloalkyl)aminocarbonyl, C3-C,-cycloalkyl-C,-C6-alkyleneamino-carbonyl, C,-C6-alkylcarbonyl, C3-C,-cycloalkylcarbonyl, carboxy, carboxamido [-C(O)NH2], C,-C6-alkyloxycarbonyl, C,-C3-alkylsulphanyl, C,-C6-alkysulphonyl, C3-C,-cycloalkylsulphonyl, C3-C,-cycloalkyl-C,-C6-alkylenesulphonyl, C,-C6-alkylaminosulphonyl, di(C,-C6-alkyl)aminosulphonyl, (C3-C7-cycloalkyl)aminosulphonyl, di(C3-C,-cycloalkyl)aminosulphonyl, C3-C7-cycloalkyl-C,-C6-alkyleneaminosulphonyl, C,-C6-alkylsulphonylamido, -N(Co-C6-alkyl)-C(O)-C,-C6-alkyl, -N(Co-C6-alkyl)-C(O)-C3-C7-cycloalkyl, -N(Co-C6-alkyl)-C(O)-N-di(Co-C6-alkyl), -N(Co-C6-alkyl)-C(O)-O-(Co-C6)alkyl, -N(Co-C6-alkyl)-C(O)-NH-C3-C,-cycloalkyl, -N(Co-C6-alkyl)-SO2-C,-Cs-alkyl, -N(Co-C6-alkyl)-SO2-C3-C7-cycloalkyl, -N(Co-C6-alkyl)-SO2-N-di(Co-C6-alkyl), -N(Co-C6-alkyl)-S02-NH-(C3-C,)-cycloalkyl, -C(O)-N(H)-C2-C6-alkylene-(C,-C6-alkyl)amine, -C(O)-N(H)-C2-C6-alkylene-[di(C,-C6-alkyl)]amine, -C(O)-N(H)-C2-C6-alkylene-(C3-C7-cycloalkyl)amine, -C(O)-N(H)-C2-C6-alkylene-(C3-C7-cycloalkyl-C,-C6-alkyl)amine, -S(02)-N(H)-C2-C6-alkylene-(C,-C6-alkyl)amine, -S(O2)-N(H)-CZ-C6-alkylene-[di(C,-C6-alkyl)]amine, -S(02)-N(H)-C2-C6-alkylene-(C3-C7-cycloalkyl)amine, -S(02)-N(H)-C2-C6-alkylene-(C3-C7-cycloalkyl-C,-C6-alkylene)amine, -O-C2-C6-alkylene-(C,-C6-alkyl)amine, -O-C2-Cs-alkylene-[di(C,-C6-alkylene)]amine, or the radicals:
N (N) (N) U (N) O S
o N~o (N) N N
N N
Co Cs alkyl Co Cs alkyl Co Cs alkyl CN) (N) (N) N
C~
O S
.5..

N N
(N) N N
C C -alk I
Co Cs alkyl o s y Co Cs alkyl 0=S=0 0=S=0 0=S=0 0=S=0 O (N) C:) 5 O O
0=s=0 0=s=0 0=s=0 N p C
C> >
N N
Co Cs alkyl Co-Cs-alkYI Co Cs alkyl Co Cs alkyl Co Cs alkyl Co Cs alkyl Co Cs alkyl Oy NI-I OvN~ Oy N~ Oy N~

O C:) () g ,51.
O O
Co Cs alkyl Co Cs alkyl Co Cs alkyl O\ /N Oy N~ O\ /N~

NC;) >
N
Co Cs alkyl Co-Cs-alkYI Co Cs alkyl NCo Cs alkyl N'Co Cs alkyi N'Co Cs alkyl N.Co Cs alkyl I I I I
0=S=0 0=S=0 0=S=0 0=S=0 U (N) C:) N
C~
,,S%.
O O
N'Co Cs alkyl N~Co Cs alkyl N'Co Cs alkyl I I I
0=S=0 0=S=0 0=S=0 N C
C;) ~
Co Cs alkyl Co Cs alkYl Co Cs alkyl R7, R8 may be independently of one another hydrogen, methyl, ethyl, where the methyl and ethyl radicals may be fluorinated one or more times;

where R2 may substitute one or more positions of the aryl or heteroaryl ring in the indole residue;
R3 may substitute one or more positions of the aryl or heteroaryl ring in the radical Q;

R5 and R6 may together form heterocycloalkyl, cycloalkyl;

Q and W may be independently of one another aryl, heteroaryl;
X may be a bond, C,-C4-alkylene, C2-C4-alkenylene, C2-C4-alkynylene, C,-C3-alkyleneoxy, C,-C3-alkyleneoxy-C,-C3-alkylene, Y may be a bond, C,-C4-alkylene.

The object has likewise been achieved according to the present invention by the com-pounds of the formula I in which R7 and R8 are a hydrogen, that is to say by the com-pounds of the formula Ia ~N ~ R2 \ /
HO
OyNH

Y

X

V V la where Printed: 23-11-2007 DESCPAMD PCT/EP 2006/007 949'4 Q and W may be independently of one another aryl, heteroaryl;
X may be a bond, C,-C4-alkylene, C2-C4-alkenylene, C2-C4-alkynylene, C,-C3-alkyleneoxy, C,-C3-alkyleneoxy-C,-C3-alkylene, Y may be a bond, C,-C4-alkylene;

with the provision that the formula I does not include 4-(8-fluoro-3-oxo-1,3-dihydro-pyrazolo[4,3-c]cinnolin-2-yl-N-[3-hydroxy-2-(1-H-indol-3-yl)-propyl]benzamide.
The object has likewise been achieved according to the present invention by the com-pounds of the formula I in which R7 and R8 are a hydrogen, that is to say by the com-pounds of the formula Ia R1\N ~ R2 ~ ~
HO

Oy NH
Y

X

YY la where R1 may be hydrogen, C,-C6-alkyl, C3-Ce-alkenyl or C3-Cs-alkynyl, where the hydrocarbon radicals therein may optionally be substituted one or more times by fluorine;

R2 may be hydrogen,.halogen, C,-C6-alkyl, CZ-CB-alkenyl or CZ-Ce-alkynyl, C,-C4-alkyloxy, where the hydrocarbon chain therein may optionally be substituted one or more times by fluorine; or benzyloxy;

Printed: 23-11-2007' DESCPAMD" PCT/EP 2006/007 949=
R3 may be hydrogen, halogen, nitro, amino, cyano, C,-CB-alkyl, C2-Ce-alkenyl or Cz-Ce-alkynyl, C,-Ca-alkykoxy, where the hydrocarbon chain therein may optionally be substituted one or more times by fluorine;

R4, R5, R6 may be independently of one another hydrogen, halogen, C,-Ce-alkyl, 5 C2-Ce-alkenyl, CZ-CB-alkynyl, C,-C4-alkyloxy, where the hydrocarbon chain therein may optionally be substituted one or more times by fluorine, C,-C3-alkylsulphanyl, acetamido, C,--Cg-alkylaminocarbonyl; hydroxy, cyano, hydroxy-C,-C4-alkyl;
where 10 R2 and R3 may substitute one or more positions of the aryl or heteroaryl ring in each case in the radical Q and in the indole residue;
R5 and R6 may together form heterocycloalkyl, cycloalkyl;
Q and W may be independently of one another aryl, heteroaryl;
X may be a bond, CI-C4-alkylene, Ci-C4-alkenylene, C,-C4-afkynylene, C,-C3-alkyleneoxy, C,-C3-alkyleneoxy-C,-C3-alkylene, Y may be a bond, C,-C4-aikylene;

with the provision that the formula la does not include 4-(8-fluoro-3-oxo-1,3-dihydro-pyrazolo[4, 3-c]cinnolin-2-yl-N-[3-hydroxy-2-( 9 -H-indol-3-yl)-propyl]benzam ide.
The present invention relates to both possible enantiomeric forms at the stereocentre of the tryptophanol residue.

The unbranched C,-CB-alkyl groups for the radicals R1 to R6 may be for example a methyl, ethyl, propyl, butyl, pentyl or a hexyl group; and the branched C3-Ce-alkyl groups for the radicals Rl to R6 may be an isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, 2-methylbutyl, 1-methylbutyl, 1-ethylpropyl, neopentyl, 1, 1 -dimethylpropyl, 4-methylpentyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, 2-ethylbutyl, 1-ethylbutyl, 3,3-dimethylbutyl, 2,2-dimethylbutyl, 1,1-dimethylbutyl, 2,3-dimethylbutyl, 1,3-dimethylbutyl or a 1,2-dimethylbutyl group.
The branched or unbranched C3-CS-aikenyl groups for the radical R1 may be for example an allyi, (E)-2-methylvinyl, (Z)-2-methylvinyl, homoallyl, (E)-but-2-enyl, (Z)-but-2-enyl, (E)-but-l-enyl, (Z)-but-l-enyt, pent-4-enyl, (E)-pent-.3-enyl, (Z)-pent-3-enyl, (E)-pent-2-enyl, (Z)-pent-2-enyl, (E)-pent-1-enyl, (Z)-pent-l-enyl, hex-5-enyl, (E)-hex-4-enyl, (Z)-hex-4-enyl, (E)-hex-3-enyl, (Z)-hex-3-enyl, (E)-hex-2-enyl, (Z)-hex-2-enyl, (E)-hex-l-enyl, (Z)-hex-l-enyl, isopropenyl, 2-methylprop-2-enyl, 1-methylprop-2-enyl, 2-4/4 AMENDED SHEET 04-06-200f The C2-C6-alkenyl groups for the radicals R2 to R6 may, in addition to the C3-alkenyl groups mentioned for the radical R1, be for example a vinyl group.

The C2-C6-alkynyl groups for the radicals R2 to R6 may, in addition to the C3-alkynyl groups mentioned for the radical R1, be for example an ethynyl group.
The C,-Cs-alkyloxy groups for the radicals R2 to R6 may be for example a methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, isopentyloxy, (2-methylbutyl)oxy, (1-methylbutyl)oxy, (1 -ethyl propyl)oxy, neopentyloxy, (1,1-dimethylpropyl)oxy, hexyloxy, (4-methylpentyl)oxy, (3-methylpentyl)-oxy, (2-methylpentyl)oxy, (1-methylpentyl)oxy, (1 -ethyl butyl)oxy, (2-ethylbutyl)oxy, (3,3-dimethylbutyl)oxy, (2,2-dimethylbutyl)oxy, (1,1-dimethylbutyl)oxy, (2,3-dimethyl-butyl)oxy, (1,3-dimethylbutyl)oxy or a (1,2-dimethylbutyl)oxy group.

The halogens for the radicals R2 to R6 are fluorine, chlorine, bromine or iodine.
The C,-C3-alkylsulphanyl groups for the radicals R4 to R6 may be for example a methylsulphanyl (CH3S-), ethylsulphanyl (CH3CH2S-), propylsulphanyl, isopropylsulphanyl group.
The C,-C6-alkylaminocarbonyl groups for the radicals R4 to R6 may be for example a methylaminocarbonyl-, ethylaminocarbonyl-, propylaminocarbonyl-, isopropylaminocarbonyl-, butylaminocarbonyl-, isobutylaminocarbonyl-, sec-butylaminocarbonyl-, tert-butylaminocarbonyl-, pentylaminocarbonyl-, isopentylaminocarbonyl-, (2-methylbutyl)aminocarbonyl-, (1-methylbutyl)aminocarbonyl-, (1-ethylpropyl)aminocarbonyl-, neopentylaminocarbonyl-, (1,1-dimethylpropyl)aminocarbonyl-, hexylaminocarbonyl-, (4-methylpentyl)aminocarbonyl-, (3-methylpentyl)aminocarbonyl-, (2-methylpentyl)aminocarbonyl-, (1-methylpentyl)aminocarbonyl-, (1-ethylbutyl)aminocarbonyl-, (2-ethylbutyl)aminocarbonyl-, (3,3-dimethylbutyl)aminocarbonyl-, (2,2-dimethylbutyl)aminocarbonyl-, (1,1-dimethylbutyl)aminocarbonyl-, (2,3-dimethylbutyl)aminocarbonyl-, (1,3-dimethylbutyl)aminocarbonyl- or a (1,2-dimethylbutyl)aminocarbonyl group.
The hydroxy-C,-Cs-alkylene groups for the radicals R3 to R6 may be a hydroxymethyl (HOCH2-), 2-hydroxyethyl (HOCH2CH2-), 1-hydroxyethyl [CH3CH(OH)-], 3-hydroxypropyl (HOCH2CH2CH2-), 2-hydroxypropyl [CH3CH(OH)CH2-], 1-hydroxypropyl [CH3CH2CH(OH)-], 2-hydroxy-l-methylethyl [HOCH2CH(CH3)-], 1-hydroxy-l-methylethyl [(CH3)2C(OH)-], 4-hydroxybutyl (HOCH2CH2CH2CH2-), 3-hydroxybutyl [CH3CH(OH)CH2CH2-], 2-hydroxybutyl [CH3CH2CH(OH)CH2-], 1 -hydroxybutyl [CH3CH2CH2CH(OH)-], 3-hydroxy-l-methylpropyl [HOCH2CH2CH(CH3)-], 2-hydroxy-l-methylpropyl [CH3CH(OH)CH(CH3)-], 1-hydroxy-l-methylpropyl [CH3CH2C(CH3)(OH)-], 1-(hydroxymethyl)propyl [CH3CH(CH2OH)-], 3-hydroxy-2-methylpropyl [HOCH2CH(CH3)CH2-], 2-hydroxy-2-methylpropyl [(CH3)2C(OH)CH2-], 1-hydroxy-2-methylpropyl [CH3CH(CH3)CH(OH)-] or a 2-hydroxy-1,1-dimethylethyl group [HOCH2C(CH3)2-].
The heterocycloalkyl groups which may form the radicals R5 and R6 together may be for example the following groups:

O-_ O HN 0\1S HN
\O~ CO N~ X
H H O

C O, C C
HN S~ / HN~ /

The cycloalkyl groups which may form the radicals R5 and R6 together may be for example the following groups:
cOG

The C3-C7-cycloalkyl groups for the radicals R1 to R6 may be for example a cyclopro-pyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl group.
The C3-C,-heterocycloalkyl groups for the radicals R1 to R6 may be for example a cyclopropyl, cyclobutyl, cycopentyl, cyclohexyl, cycloheptyl group in which one or two carbon atoms of the ring are replaced independently of one another by an oxygen, ni-trogen or sulphur atom.
The aryl groups for the radicals Q and W may be for example a phenyl, naphthyl group which is linked via substitutable positions.
The heteroaryl groups for the radicals Q and W may be for example a pyridinyl, pyrimidinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, 1.5-naphthyridinyl, 1,6-naphthyridinyl, 1,7-naphthyridinyl, 1,8-naphthyridinyl, benzofuranyl, benzothienyl, 1,3-benzodioxolyl, 2,1,3-benzothiadiazolyl, indolyl, furanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, pyrrolyl, pyrazolyl or an imidazolyl group which is linked via substitutable positions.

The C,-C4-alkylene groups for the radicals X and Y may be for example a methylene (-CH2-), ethylidene [-CH(CH3)-], ethylene (-CH2CH2-), prop-1,3-ylene (-CH2CH2CH2-), prop-1,2-ylene [-CH2CH(CH3)-], but-1,4-ylene (-CH2CH2CH2CH2-), but-1,3-ylene [-CH2CH2CH(CH3)-], but-1,2-ylene [-CH2CH(CH2CH3)-], but-2,3-yiene [-CHCH(CH3)-], methylprop-l,2-yiene [-CH2C(CH3)2-] or a 2-methylprop-1,3-ylene group [-CH2CH(CH3)CH2-].

The C2-C4-alkenylene groups for the radical X may be for example an ethen-1,2-ylidene (-CH=CH-), prop-2-en-1,3-ylidene (-CH2-CH=CH-), prop-l-en-l,3-ylidene (-CH=CH-CH2-), but-1-en-1,4-ylidene (-CH=CH-CH2-CH2-), but-2-en-1,4-ylidene (-CH2-CH=CH-CH2-) or a but-3-en-1,4-ylidene group (-CH2-CH2-CH=CH-).

The C2-C4-alkynylene groups for the radical X may be for example an ethyn-1,2-ylidene (-C=C-), prop-2-yn-1,3-ylidene (-CHZ-C=C-), prop-l-yn-l,3-ylidene (-C=C-CH2-), but-1-yn-1,4-ylidene (-C=C-CH2-CH2-), but-2-yn-1,4-ylidene (-CH2-C=C-CH2-) or a but-3-yn-1,4-ylidene group (-CH2-CH2-C=C-).

The C,-C3-alkyleneoxy groups for the radical X may be for example an oxymethylene (-O-CHZ-), methyleneoxy (-CH2-O-), ethane-l,2-diyloxy (-CH2-CH2-O-), oxyethane-1,2-diyl (-O-CH2-CH2-), propane-1,3-diyloxy (-CH2-CH2-CH2-O-) or an oxypropane-1,3-diyl (-O-CH2-CH2-CH2-) group.
The C,-C3-alkyleneoxy-C,-C3-aIkyl groups for the radical X may be for example an oxybis(methylene) (-CH2-O-CH2-), methyleneoxyethane-2,1-diyl [-CH2-O-(CH2)2-], ethane-l,2-diyloxymethylene [-(CH2)2-O-CH2-], methyleneoxypropane-3,1-diyl [-(CH2)3-], propane-l,3-diyloxymethylene [-(CH2)3-O-CH2-], oxybis(ethane-2,1-diyl) [-(CH2)2-0-(CH2)2-], propane-l,3-diyloxyethane-2,1-diyl [-(CH2)3-0-(CH2)2-], ethane-1,2-diyloxypropane-3,1-diyl [-(CH2)2-0-(CH2)3-] or an oxybis(propane-3,1-diyl) group [-(CH2)3-0-(CH2)3-].
The C3-C,-cycloalkyloxy groups for the radicals R1 to R6 may be for example a cyclo-propyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy group.
The C,-C6-alkylamino groups for the radicals R1 to R6 may be for example methyl-amino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, sec-butyl-amino, tert-butylamino, pentylamino, isopentylamino, (2-methylbutyl)amino, (1-methylbutyl)amino, (1-ethylpropyl)amino, neopentylamino, (1,1-dimethylpropyl)-amino, hexylamino, (4-methylpentyl)amino, (3-methylpentyl)amino, (2-methylpentyl)amino, (1-methylpentyl)amino, (1-ethylbutyl)amino, (2-ethylbutyl)amino, (3,3-dimethylbutyl)amino, (2,2-dimethylbutyl)amino, (1,1-dimethylbutyl)amino, (2,3-dimethylbutyl)amino, (1,3-dimethylbutyl)amino or a (1,2-dimethylbutyl)amino group.
In the di(C,-C6-alkyl)amino groups for the radicals R1 to R6, each of the two radicals on the nitrogen atom of the dialkylamino group may be chosen independently of one an-other from the following radicals: possible examples are a methyl, ethyl, propyl, isopro-pyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1-ethylpropyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group.

In the C3-C,-cycloalkyl-C,-C6-alkyleneoxy groups for the radicals R1 to R6 it is possible to combine each of the C3-C7-cycloalkyl groups of the C3-C,-cycloalkyl-C,-C6-alkyleneoxy group, for example of a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group, independently of one another with each C0-C6-alkyleneoxy group, for example with a methyleneoxy, ethyleneoxy, propyleneoxy, butyleneoxy, pentylene-oxy, hexyleneoxy group.
In the hydroxy-C3-C6-alkenylene groups for the radicals R1 to R6 it is possible for the hydroxy group to be located on any desired position of the C3-Cs-alkenyl group, for ex-ample of an allyl, (E)-2-methylvinyl, (Z)-2-methylvinyl, homoallyl, (E)-but-2-enyl, (Z)-but-2-enyl, (E)-but-1-enyl, (Z)-but-l-enyl, pent-4-enyl, (E)-pent-3-enyl, (Z)-pent-3-enyl, (E)-Pent-2-enyl-, (Z)-Pent-2-enyl-, (E)-Pent-l-enyl-, (Z)-Pent-l-enyl-, hex-5-enyl-, (E)-hex-4-enyl, (Z)-hex-4-enyl, (E)-hex-3-enyl, (Z)-hex-3-enyl, (E)-hex-2-enyl, (Z)-hex-2-enyl, (E)-hex-l-enyl, (Z)-hex-l-enyl, isopropenyl, 2-methylprop-2-enyl, 1-methylprop-2-enyl, 2-methyl prop- 1 -enyl, (E)- 1 -methyl prop- 1 -enyl, (Z)- 1 -methyl prop- 1 -enyl, 3-methylbut-3-enyl, 2-methylbut-3-enyl, 1-methylbut-3-enyl, 3-methylbut-2-enyl, (E)-2-methylbut-2-enyl, (Z)-2-methylbut-2-enyl, (E)-1-methylbut-2-enyl, (Z)-1-methylbut-2-enyl, (E)-3-methylbut-l-enyl, (Z)-3-methylbut-1-enyl, (E)-2-methylbut-1-enyl, (Z)-2-methylbut-1-enyl, (E)-1-methylbut-l-enyl, (Z)-1-methylbut-l-enyl, 1,1-dimethylprop-2-enyl, ethyl prop- 1 -enyl, 1-propylvinyl, 1-isopropylvinyl, 4-methylpent-4-enyl, 3-methylpent-4-enyl, 2-methylpent-4-enyl, 1-methylpent-4-enyl, 4-methylpent-3-enyl, (E)-3-methylpent-3-enyl, (Z)-3-methylpent-3-enyl, (E)-2-methylpent-3-enyl, (Z)-2-methylpent-3-enyl, (E)-1-5 methylpent-3-enyl, (Z)-1-methylpent-3-enyl, (E)-4-methylpent-2-enyl, (Z)-4-methylpent-2-enyl, (E)-3-methylpent-2-enyl, (Z)-3-methylpent-2-enyl, (E)-2-methylpent-2-enyl, (Z)-2-methylpent-2-enyl, (E)-1-methylpent-2-enyl, (Z)-1-methylpent-2-enyl, (E)-4-methylpent-1-enyl, (Z)-4-methylpent-l-enyl, (E)-3-methyl pent- 1 -enyl, (Z)-3-methylpent-1-enyl, (E)-2-methylpent-1-enyl, (Z)-2-methylpent-1-enyl, (E)- 1 -methyl pent- 1 -enyl, (Z)-1-methylpent-10 1-enyl, 3-ethylbut-3-enyl, 2-ethylbut-3-enyl, 1-ethylbut-3-enyl, (E)-3-ethylbut-2-enyl, (Z)-3-ethylbut-2-enyl, (E)-2-ethylbut-2-enyl, (Z)-2-ethylbut-2-enyl, (E)- 1 -ethyl but-2-enyl, (Z)-1 -ethyl but-2-enyl, (E)-3-ethyl but- 1 -enyl, (Z)-3-ethyl but- 1 -enyl, 2-ethylbut-l-enyl, (E)-1-ethylbut-1-enyl, (Z)-1-ethylbut-1-enyl, 2-propylprop-2-enyl, 1-propylprop-2-enyl, 2-isopropylprop-2-enyl, 1-isopropylprop-2-enyl, (E)-2-propyl prop- 1 -enyl, (Z)-2-propylprop-15 1-enyl, (E)-1-propylprop-l-enyl, (Z)-1-propylprop-l-enyl, (E)-2-isopropyl prop- 1 -enyl, (Z)-2-isopropylprop-l-enyl, (E)-1-isopropylprop-l-enyl, (Z)- 1 -isopropyl prop- 1 -enyl, (E)-3,3-dimethylprop-1 -enyl, (Z)-3,3-dimethylprop-1-enyl or a 1 -(1, 1 -dimethylethyl)ethenyl group, and to be combined independently of one another.
In the hydroxy-C3-C6-alkynyl groups for the radicals R1 to R6 it is possible for the hy-droxy group to be located at any desired position of the C3-C6-alkynyl group, for exam-ple of a prop-l-ynyl, prop-2-ynyl, but-1-ynyl, but-2-ynyl, but-3-ynyl, pent-l-ynyl, pent-2-ynyl, pent-3-ynyl, pent-4-ynyl, hex-1-ynyl, hex-2-ynyl, hex-3-ynyl, hex-4-ynyl, hex-5-ynyl, 1-methylprop-2-ynyl, 2-methylbut-3-ynyl, 1-methylbut-3-ynyl, 1 -m ethyl but-2-ynyl, 3-methylbut-l-ynyl, 1 -ethyl prop-2-ynyl, 3-methylpent-4-ynyl, 2-methylpent-4-ynyl, 1-methylpent-4-ynyl, 2-methylpent-3-ynyl, 1-methylpent-3-ynyl, 4-methylpent-2-ynyl, 1-methylpent-2-ynyl, 4-methylpent-1 -ynyl, 3-methylpent-1-ynyl, 2-ethylbut-3-ynyl, 1 -ethyl but-3-ynyl, 1-ethylbut-2-ynyl, 1-propylprop-2-ynyl, 1-isopropylprop-2-ynyl, 2,2-di-methylbut-3-ynyl, 1, 1 -dimethylbut-3-ynyl, 1,1-dimethylbut-2-ynyl or a 3,3-dimethylbut-1 -ynyl group.
In the C,-C6-alkyloxy-C3-C6-alkenylene groups for the radicals R1 to R6 it is possible for the C,-C6-alkyloxy group, for example a methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, isopentyloxy, (2-methylbutyl)oxy, (1-methylbutyl)oxy, (1-ethylpropyl)oxy, neopentyloxy, (1,1-dimethyl-propyl)oxy, hexyloxy, (4-methylpentyl)oxy, (3-methylpentyl)oxy, (2-methylpentyl)oxy, (1-methylpentyl)oxy, (1-ethylbutyl)oxy, (2-ethylbutyl)oxy, (3,3-dimethylbutyl)oxy, (2,2-dimethylbutyl)oxy, (1,1-dimethylbutyl)oxy, (2,3-dimethylbutyl)oxy, (1,3-dimethylbutyl)oxy or a (1,2-dimethylbutyl)oxy group, to be located on any desired position of the C3-C6-alkenyl group, for example of an allyl, (E)-2-methylvinyl, (Z)-2-methylvinyl, homoallyl, (E)-but-2-enyl, (Z)-but-2-enyl, (E)-but-l-enyl, (Z)-but-l-enyl, pent-4-enyl, (E)-pent-3-enyl, (Z)-pent-3-enyl, (E)-pent-2-enyl, (Z)-pent-2-enyl, (E)-pent-l-enyl, (Z)-pent-l-enyl, hex-5-enyl, (E)-hex-4-enyl, (Z)-hex-4-enyl, (E)-hex-3-enyl, (Z)-hex-3-enyl, (E)-hex-2-enyl, (Z)-hex-2-enyl, (E)-hex-l-enyl, (Z)-hex-l-enyl, isopropenyl, 2-methylprop-2-enyl, 1-methylprop-2-enyl, 2-methylprop-l-enyl, (E)-1-methylprop-l-enyl, (Z)-1-methylprop-l-enyl, 3-methylbut-3-enyl, 2-methylbut-3-enyl, 1-methylbut-3-enyl, 3-methylbut-2-enyl, (E)-2-methylbut-2-enyl, (Z)-2-methylbut-2-enyl, (E)- 1 -m ethyl but-2-enyl, (Z)-1-methylbut-2-enyl, (E)-3-methylbut-l-enyl, (Z)-3-methylbut-l-enyl, (E)-2-methylbut-1-enyl, (Z)-2-methylbut-l-enyl, (E)-1-methylbut-l-enyl, (Z)-1-methylbut-l-enyl, 1,1-dimethylprop-2-enyl, 1 -ethyl prop- 1 -enyl, 1-propylvinyl, 1-isopropylvinyl, 4-methylpent-4-enyl, 3-methylpent-4-enyl, 2-methylpent-4-enyl, 1-methylpent-4-enyl, 4-methylpent-3-enyl, (E)-3-methylpent-3-enyl, (Z)-3-methylpent-3-enyl, (E)-2-methylpent-3-enyl, (Z)-methylpent-3-enyl, (E)-1-methylpent-3-enyl, (Z)-1-methylpent-3-enyl, (E)-4-methylpent-2-enyl, (Z)-4-methylpent-2-enyl, (E)-3-methylpent-2-enyl, (Z)-3-methylpent-2-enyl, (E)-2-methylpent-2-enyl, (Z)-2-methylpent-2-enyl, (E)-1-methylpent-2-enyl, (Z)-1-methylpent-2-enyl, (E)-4-methyl pent- 1 -enyl, (Z)-4-methylpent-l-enyl, (E)-3-methyl pent-1 -enyl, (Z)-3-methylpent-1-enyl, (E)-2-methylpent-l-enyl, (Z)-2-methyl pent- 1 -enyl, (E)- 1 -methyl pent-1-enyl, (Z)-1-methylpent-l-enyl, 3-ethylbut-3-enyl, 2-ethylbut-3-enyl, 1 -ethyl but-3-enyl, (E)-3-ethylbut-2-enyl, (Z)-3-ethylbut-2-enyl, (E)-2-ethylbut-2-enyl, (Z)-2-ethylbut-2-enyl, (E)-1-ethylbut-2-enyl, (Z)-1-ethylbut-2-enyl, (E)-3-ethyl but- 1 -enyl, (Z)-3-ethyl but- 1 -enyl, 2-ethylbut-l-enyl, (E)- 1 -ethyl but- 1 -enyl, (Z)-1-ethylbut-l-enyl, 2-propylprop-2-enyl, 1-propylprop-2-enyl, 2-isopropylprop-2-enyl, 1-isopropylprop-2-enyl, (E)-2-propylprop-1-enyl, (Z)-2-propyl prop- 1 -enyl, (E)-1-propylprop-l-enyl, (Z)-1-propylprop-l-enyl, (E)-2-isopropylprop-1-enyl, (Z)-2-isopropylprop-l-enyl, (E)-1-isopropylprop-l-enyl, (Z)-1-isopropylprop-1-enyl, (E)-3,3-dimethylprop-l-enyl, (Z)-3,3-dimethylprop-l-enyl or a 1-(1,1-dimethylethyl)ethenyl group and to be combined independently of one another.
In the C,-C6-alkyloxy-C3-C6-alkynylene groups for the radicals R1 to R6 it is possible for the C,-Cs-alkyloxy group, for example a methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, isopentyloxy, (2-methylbutyl)oxy, (1-methylbutyl)oxy, (1 -ethyl propyl)oxy, neopentyloxy, (1,1-dimethyl-propyl)oxy, hexyloxy, (4-methylpentyl)oxy, (3-methylpentyl)oxy, (2-methylpentyl)oxy, (1-methylpentyl)oxy, (1-ethylbutyl)oxy, (2-ethylbutyl)oxy, (3,3-dimethylbutyl)oxy, (2,2-dimethylbutyl)oxy, (1,1-dimethylbutyl)oxy, (2,3-dimethylbutyl)oxy, (1,3-dimethylbutyl)oxy or a (1,2-dimethylbutyl)oxy group, to be located at any desired position of the C3-C6-alkynyl group, for example of a prop-1-ynyl, prop-2-ynyl, but-1-ynyl, but-2-ynyl, but-3-ynyl, pent-1-ynyl, pent-2-ynyl, pent-3-ynyl, pent-4-ynyl, hex-1-ynyl, hex-2-ynyl, hex-3-ynyl, hex-4-ynyl, hex-5-ynyl, 1-methylprop-2-ynyl, 2-methylbut-3-ynyl, 1-methylbut-3-ynyl, 1-methylbut-2-ynyl, 3-methylbut-1-ynyl, 1 -ethyl prop-2-ynyl, 3-methylpent-4-ynyl, 2-methylpent-4-ynyl, 1-methylpent-4-ynyl, 2-methylpent-3-ynyl, 1-methylpent-3-ynyl, 4-methylpent-2-ynyl, 1-methylpent-2-ynyl, 4-methylpent-1-ynyl, 3-methylpent-1-ynyl, 2-ethylbut-3-ynyl, 1 -ethyl but-3-ynyl, 1 -ethyl but-2-ynyl, 1-propylprop-2-ynyl, 1-isopropylprop-2-ynyl, 2,2-dimethylbut-3-ynyl, 1,1-dimethylbut-3-ynyl, 1,1-dimethylbut-2-ynyl or a 3,3-dimethylbut-1-ynyl group, and to be combined independently of one an-other.
In the C,-Cs-alkyloxyphenyl-C,-Cs-alkylene groups for the radical R1 to R6 it is possible for the C,-Cs-alkyloxy group to be selected independently of one another from methy-loxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, isopentyloxy, (2-methylbutyl)oxy, (1-methylbutyl)oxy, (1-ethylpro-pyl)oxy, neopentyloxy, (1,1-dimethylpropyl)oxy, hexyloxy, (4-methylpentyl)oxy, (3-methylpentyl)oxy, (2-methylpentyl)oxy, (1-methylpentyl)oxy, (1-ethylbutyl)oxy, (2-ethyl-butyl)oxy, (3,3-dimethylbutyl)oxy, (2,2-dimethylbutyl)oxy, (1,1-dimethylbutyl)oxy, (2,3-dimethylbutyl)oxy, (1,3-dimethylbutyl)oxy or a (1,2-dimethylbutyl)oxy, and to be com-bined independently of one another with C,-Cs-alkylene groups such as, for example, methylene, ethylene, propylene, butylene, pentylene, hexylene.
In the C3-C,-cycloalkyl-(Co-C6)-alkyleneamino groups of the radicals R3 to R6 it is pos-sible for each of the C3-C,-cycloalkyl groups of the C3-C,-cycloalkyl-(Co-C6)-alkyleneamino group, for example of a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group, to be combined independently of one another with each C0-alkylene group, for example with a bond, a methylene, ethylene, propylene, butylene, pentylene, hexylene group.
In the C,-C6-alkyloxy-C,-C6-alkylene groups for the radical R1 to R6, it is possible for the C,-C6-alkyloxy group to be selected independently for example from methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, isobutyloxy, sec-butyloxy, tert-butyloxy, pentyloxy, isopentyloxy, (2-methylbutyl)oxy, (1-methylbutyl)oxy, (1 -ethyl propyl)oxy, neopentyloxy, (1,1-dimethylpropyl)oxy, hexyloxy, (4-methylpentyl)oxy, (3-methylpentyl)-oxy, (2-methylpentyl)oxy, (1-methylpentyl)oxy, (1 -ethyl butyl)oxy, (2-ethylbutyl)oxy, (3,3-dimethylbutyl)oxy, (2,2-dimethylbutyl)oxy, (1,1-dimethylbutyl)oxy, (2,3-dimethyl-butyl)oxy, (1,3-dimethylbutyl)oxy or a(1,2-dimethylbutyl)oxy and to be combined inde-pendently of one another with C,-C6-alkylene groups such as, for example, methylene, ethylene, propylene, butylene, pentylene, hexylene.
In the di(C,-C6-alkyl)amino-C,-Cs-alkylene group for the radical R1 it is possible for each of the two radicals on the nitrogen atom of the amino group to be selected inde-pendently for example from methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1-ethylpropyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1, 1 -dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group, and to be combined with C,-C6-alkylene groups such as, for ex-ample, methylene, ethylene, propylene, butylene, pentylene, hexylene.
The C3-C,-cycloalkyl-C,-C6-alkylene groups for the radicals R1 to R6 may be for ex-ample a cyclopropyloxymethylene, cyclopropyloxyethylene, cyclopropyloxypropylene, cyclopropyloxybutylene, cyclopropyloxypentylene, cyclopropyloxyhexylene, cyclobuty-loxymethylene, cyclobutyloxyethylene, cyclobutyloxypropylene, cyclobutyloxybutylene, cyclobutyloxypentylene, cyclobutyloxyhexylene, cyclopentyloxymethylene, cyclopenty-loxyethylene, cyclopentyloxypropylene, cyclopentyloxybutylene, cyclopentyloxypenty-lene, cyclopentyloxyhexylene, cyclohexyloxymethylene, cyclohexyloxyethylene, cyclo-hexyloxypropylene, cyclohexyloxybutylene, cyclohexyloxypentylene, cyclohexyloxy-hexylene, cycloheptyloxymethylene, cycloheptyloxyethylene, cycloheptyloxypropylene, cycloheptyloxybutylene, cycloheptyloxypentylene, cycloheptyloxyhexylen group.
In the C,-C6-alkylamino-C,-C6-alkylene groups for the radicals R1 to R6 it is possible for the C,-Cs-alkylamino group to be selected independently for example from methyl-amino, ethylamino, propylamino, isopropylamino, butylamino, isobutylamino, sec-butyl-amino, tert-butylamino, pentylamino, isopentylamino, (2-methylbutyl)amino, (1-methylbutyl)amino, (1-ethylpropyl)amino, neopentylamino, (1,1-dimethylpropyl)-amino, hexylamino, (4-methylpentyl)amino, (3-methylpentyl)amino, (2-methylpentyl)-amino, (1-methylpentyl)amino, (1-ethylbutyl)amino, (2-ethylbutyl)amino, (3,3-dimethyl-butyl)amino, (2,2-dimethylbutyl)amino, (1,1-dimethylbutyl)amino, (2,3-dimethyl-butyl)amino, (1,3-dimethylbutyl)amino or a (1,2-dimethylbutyl)amino and to be com-bined with C,-Cs-alkylene groups such as, for example, methylene, ethylene, propylene, butylene, pentylene, hexylene.
The phenyloxy-C,-C6-alkylene groups for the radicals R1 to R6 may be for example a phenyloxymethyl, phenyloxyethyl, phenyloxypropyl, phenyloxybutyl, phenyloxypentyl, phenyloxyhexyl group.
In the C,-C6-acyl-(Co-C6-alkyl)amido groups for the radicals R4 to R6, it is possible for each of the C,-C6-acyl groups, for example a formyl, acetyl, propionyl, 2-methylpro-pionyl, 2,2-dimethylpropionyl, butyryl, 2-methylbutyryl, 3-methylbutyryl, 2,2-dimethyl-butyryl, 2-ethylbutyryl, pentanoyl, 2-methylpentanoyl, 3-methylpentanoyl, 4-methylpentanoyl or a hexanoyl group, to be combined independently of one another with each (Co-C6-alkyl)amido group, for example a hydrogen atom, a methylamido, ethylamido, propylamido, isopropylamido, butylamido, isobutylamido, sec-butylamido, tert-butylamido, pentylamido, isopentylamido, (2-methylbutyl)amido, (1-methyl-butyl)amido, (1-ethylpropyl)amido, neopentylamido, (1,1-dimethylpropyl)amido, hexyla-mido, (4-methylpentyl)amido, (3-methylpentyl)amido, (2-methylpentyl)amido, (1-methylpentyt)amido, (1-ethylbutyl)amido, (2-ethylbutyl)amido, (3,3-dimethyl-butyl)amido, (2,2-dimethylbutyl)amido, (1,1-dimethylbutyl)amido, (2,3-dimethyl-butyl)amido, (1,3-dimethylbutyl)amido or a (1,2-dimethylbutyl)amido group.
The C,-C6-alkylaminocarbonyl groups for the radicals R4 to R6 may be for example a methylaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl, isopropylamino-carbonyl, butylaminocarbonyl, isobutylaminocarbonyl, sec-butylaminocarbonyl, tert-butylaminocarbonyl, pentylaminocarbonyl, isopentylaminocarbonyl, (2-methylbutyl)-aminocarbonyl, (1-methylbutyl)aminocarbonyl, (1-ethylpropyl)aminocarbonyl, neopen-tylaminocarbonyl, (1,1-dimethylpropyl)aminocarbonyl, hexylaminocarbonyl, (4-methylpentyl)aminocarbonyl, (3-methylpentyl)aminocarbonyl, (2-methylpentyl)-aminocarbonyl, (1-methylpentyl)aminocarbonyl, (1-ethylbutyl)aminocarbonyl, (2-ethylbutyl)aminocarbonyl, (3,3-dimethylbutyl)aminocarbonyl, (2,2-dimethylbutyl)-aminocarbonyl, (1,1-dimethylbutyl)aminocarbonyl, (2,3-dimethylbutyl)aminocarbonyl, (1,3-dimethylbutyl)aminocarbonyl or a (1,2-dimethylbutyl)aminocarbonyl group.
In the di(C,-C6-alkyl)aminocarbonyl groups for the radicals R4 to R6, each of the two C,-C6-alkyl radicals on the nitrogen atom of the di(C,-C6-alkyl)aminocarbonyl group may be independently of one another for example a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1 -ethyl propyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methyl-pentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group.
The (C3-C,-cycloalkyl)aminocarbonyl groups for the radicals R4 to R6 may be for ex-ample a cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocar-bonyl, cyclohexylaminocarbonyl or cycloheptylaminocarbonyl group.

In the di(C3-C7-cycloalkyl)aminocarbonyl groups for the radicals R4 to R6, each of the two C3-C7-cycloalkyl radicals on the nitrogen atom of the di(C3-C,-cyclo-alkyl)aminocarbonyl group may be independently of one another for example a cyclo-propyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group.
5 In the C3-C,-cycloalkyl-C,-C6-alkyleneaminocarbonyl groups of the radicals R4 to R6 it is possible for each of the C3-C,-cycloalkyl groups of the C3-C7-cycloalkyl-C,-alkyleneaminocarbonyl groups, for example of a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group, to be combined independently of one another with each CI-Cs-alkyleneaminocarbonyl group, for example with a methyleneaminocarbonyl, 10 ethyleneaminocarbonyl, propyleneaminocarbonyl, butyleneaminocarbonyl, penty-leneaminocarbonyl, hexyleneaminocarbonyl group.
The C,-C6-alkylcarbonyl groups for the radicals R4 to R6 may be for example a methyl-carbonyl, ethylcarbonyl, propylcarbonyl, isopropylcarbonyl, butylcarbonyl, isobutylcar-bonyl, sec-butylcarbonyl, tert-butylcarbonyl, pentylcarbonyl, isopentylcarbonyl, (2-15 methylbutyl)carbonyl, (1-methylbutyl)carbonyl, (1-ethylpropyl)carbonyl, neopentylcar-bonyl, (1,1-dimethylpropyl)carbonyl, hexylcarbonyl, (4-methylpentyl)carbonyl, (3-methylpentyl)carbonyl, (2-methylpentyl)carbonyl, (1-methylpentyl)carbonyl, (1-ethylbutyl)carbonyl, (2-ethylbutyl)carbonyl, (3,3-dimethylbutyl)carbonyl, (2,2-dimethylbutyl)carbonyl, (1,1-dimethylbutyl)carbonyl, (2,3-dimethylbutyl)carbonyl, (1,3-20 dimethylbutyl)carbonyl or a (1,2-dimethylbutyl)carbonyl group.
The C3-C,-cycloalkylcarbonyl groups for the radicals R4 to R6 may be for example a cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl or cycloheptylcarbonyl group.
The C,-C6-alkyloxycarbonyl groups for the radicals R4 to R6 may be for example a methyloxycarbonyl, ethyloxycarbonyl, propyloxycarbonyl, isopropyloxycarbonyl, buty-loxycarbonyl, isobutyloxycarbonyl, sec-butyloxycarbonyl, tert-butyloxycarbonyl, penty-loxycarbonyl, isopentyloxycarbonyl, (2-methylbutyl)oxycarbonyl, (1-methyl-butyl)oxycarbonyl, (1 -ethyl propyl)oxycarbonyl, neopentyloxycarbonyl, (1,1-dimethylpropyl)oxycarbonyl, hexyloxycarbonyl, (4-methylpentyl)oxycarbonyl, (3-methylpentyl)oxycarbonyl, (2-methylpentyl)oxycarbonyl, (1-methylpentyl)oxycarbonyl, (1 -ethyl butyl)oxycarbonyl, (2-ethylbutyl)oxycarbonyl, (3,3-dimethylbutyl)oxycarbonyl, (2,2-dimethylbutyl)oxycarbonyl, (1,1-dimethylbutyl)oxycarbonyl, (2,3-dimethyl-butyl)oxycarbonyl, (1,3-dimethylbutyl)oxycarbonyl or a (1,2-dimethylbutyl)oxycarbonyl group.
The C,-C6-alkylsulphonyl groups for the radicals R4 to R6 may be for example a me-thylsulphonyl, ethylsulphonyl, propylsulphonyl, isopropylsulphonyl, butylsulphonyl, iso-butylsulphonyl, sec-butylsulphonyl, tert-butylsulphonyl, pentylsulphonyl, isopentyl-sulphonyl, (2-methylbutyl)sulphonyl, (1-methylbutyl)sulphonyl, (1-ethylpropyl)sulphonyl, neopentylsulphonyl, (1,1-dimethylpropyl)sulphonyl, hexylsulphonyl, (4-methyl-pentyl)sulphonyl, (3-methylpentyl)sulphonyl, (2-methylpentyl)sulphonyl, (1-methylpentyl)sulphonyl, (1-ethylbutyl)sulphonyl, (2-ethylbutyl)sulphonyl, (3,3-dimethylbutyl)sulphonyl, (2,2-dimethylbutyl)sulphonyl, (1,1-dimethylbutyl)sulphonyl, (2,3-dimethylbutyl)sulphonyl, (1,3-dimethylbutyl)sulphonyl or a (1,2-dimethylbutyl)sulphonyl group.
The C3-C7-cycloalkylsulphonyl groups for the radicals R4 to R6 may be for example a cyclopropylsulphonyl, cyclobutylsulphonyl, cyclopentylsulphonyl, cyclohexylsulphonyl or cycloheptylsulphonyl group.
In the C3-C,-cycloalkyl-C,-Cs-alkylenesulphonyl groups of the radicals R4 to R6 it is possible for each of the C3-C,-cycloalkyl groups of the C3-C,-cycloalkyl-C,-C6-alkylenesulphonyl groups, for example of a cyclopropyl, cyclobutyl, cyclopentyl, cyclo-hexyl or cycloheptyl group, to be combined independently of one another with each C,-C6-alkylenesulphonyl group, for example with a methylenesulphonyl, ethylenesulphonyl, propylenesulphonyl, butylenesulphonyl, pentylenesulphonyl, hexylenesulphonyl group.
The C,-C6-alkylaminosulphonyl groups for the radicals R4 to R6 may be for example a methylaminosulphonyl, ethylaminosulphonyl, propylaminosulphonyl, isopropylaminosul-phonyl, butylaminosulphonyl, isobutylaminosulphonyl, sec-butylaminosulphonyl, tert-butylaminosulphonyl, pentylaminosulphonyl, isopentylaminosulphonyl, (2-methyl-butyl)aminosulphonyl, (1-methylbutyl)aminosulphonyl, (1-ethylpropyl)aminosulphonyl, neopentylaminosulphonyl, (1,1-dimethylpropyl)aminosulphonyl, hexylaminosulphonyl, (4-methylpentyl)aminosulphonyl, (3-methylpentyl)aminosulphonyl, (2-methylpentyl)-aminosulphonyl, (1-methylpentyl)aminosulphonyl, (1-ethylbutyl)aminosulphonyl, (2-ethylbutyl)aminosulphonyl, (3,3-dimethylbutyl)aminosulphonyl, (2,2-dimethylbutyl)-aminosulphonyl, (1,1-dimethylbutyl)aminosulphonyl, (2,3-dimethylbutyl)aminosulphonyl, (1,3-dimethylbutyl)aminosulphonyl or a (1,2-dimethylbutyl)aminosulphonyl group.
In the di(C,-C6-alkyl)aminosulphonyl groups for the radicals R4 to R6, each of the two C,-C6-alkyl radicals on the nitrogen atom of the di(C,-C6-alkyl)aminosulphonyl group may be independently of one another for example a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1-ethylpropyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group.
The (C3-C7-cycloalkyl)aminosulphonyl groups for the radicals R4 to R6 may be for ex-ample a cyclopropylaminosulphonyl, cyclobutylaminosulphonyl, cyclopentylaminosul-phonyl, cyclohexylaminosulphonyl or cycloheptylaminosulphonyl group.
In the di(C3-C7-cycloalkyl)aminosulphonyl groups for the radicals R4 to R6, each of the two C3-C7-cycloalkyl radicals on the nitrogen atom of the di(C3-C,-cycloalkyl)-aminosulphonyl group may be independently of one another for example a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group.
In the C3-C,-cycloalkyl-C,-Cs-alkyleneaminosulphonyl groups of the radicals R4 to R6, each of the C3-C,-cycloalkyl groups of the C3-C,-cycloalkyl-C,-C6-alkyleneaminosulphonyl groups, for example of a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group, can be combined independently of one another with each C,-C6-alkyleneaminosulphonyl group, for example with a methyleneaminosul-phonyl, ethyleneaminosulphonyl, propyleneaminosulphonyl, butyleneaminosulphonyl, pentyleneaminosulphonyl, hexyleneaminosulphonyl group.
The C,-C6-alkylsulphonylamido groups for the radicals R4 to R6 may be for example a methylsulphonylamido, ethylsulphonylamido, propyisulphonylamido, isopropylsulphon-ylamido, butylsulphonylamido, isobutylsulphonylamido, sec-butylsulphonylamido, tert-butylsulphonylamido, pentylsulphonylamido, isopentylsulphonylamido, (2-methylbutyl)-sulphonylamido, (1-methylbutyl)sulphonylamido, (1-ethylpropyl)sulphonylamido, neopentylsulphonylamido, (1,1-dimethylpropyl)sulphonylamido, hexylsulphonylamido, (4-methylpentyl)sulphonylamido, (3-methylpentyl)sulphonylamido, (2-methylpentyl)-sulphonylamido, (1-methylpentyl)sulphonylamido, (1-ethylbutyl)sulphonylamido, (2-ethylbutyl)sulphonylamido, (3,3-dimethylbutyl)sulphonylamido, (2,2-dimethylbutyl)-sulphonylamido, (1,1-dimethylbutyl)sulphonylamido, (2,3-dimethylbutyl)sulphonylamido, (1,3-dimethylbutyl)sulphonylamido or a (1,2-dimethylbutyl)sulphonylamido group.
In the -N(Co-C6-alkyl)-C(O)-C,-C6-aIkyl groups of the radicals R4 to R6, each of the (Co-C6-alkyl) groups on the nitrogen atom of the -N(Co-Cs-alkyl)-C(O)-C,-C6-aIkyl groups, for example a hydrogen, a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1 -ethyl propyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group, may be combined independently of one another with each C,-C6-alkyl group on the carbonyl group of the amide, for example with a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1 -ethyl propyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group.
In the -N-(Co-C6-alkyl)-C(O)-C3-C7-cycloalkyl groups of the radicals R4 to R6, each of the (Co-Cs-alkyl) groups on the nitrogen atom of the -N(Co-C6-alkyl)-C(O)-C,-C6-alkyl groups, for example a hydrogen, a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1-ethylpropyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methyl-pentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group, may be combined independently of one another with each cycloalkyl group on the carbonyl group of the amide, for example with a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group.
In the -N(Co-C6-alkyl)-C(O)-N-di(Co-C6-alkyl) groups of the radicals R4 to R6, all three (Co-C6-alkyl) groups may be independently of one another a hydrogen, a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1-ethylpropyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group.

In the -N(Co-Cs-alkyl)-C(O)-O-(Co-C6-alkyl) groups of the radicals R4 to R6, both (Co-C6-alkyl) groups may be independently of one another a hydrogen, a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1-ethylpropyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group.
In the -N(Co-C6-alkyl)-C(O)-NH-(C3-C,-cycloalkyl) groups of the radicals R4 to R6, each of the (Co-C6-alkyl) groups on the nitrogen atom of the -N(Co-C6-aIkyl)-C(O)-NH-(C3-C,-cycloalkyl) groups, for example a hydrogen, a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1-ethylpropyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group, may independently of one another be combined with each C3-C7-cycloalkyl group on the terminal nitrogen atom of the urea, for example with a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group.
In the -N(Co-C6-alkyl)-SO2-(C,-C6-alkyl) groups of the radicals R4 to R6, each of the (Co-Cs-alkyl) groups on the nitrogen atom of the -N(Co-Cs-alkyl)-SO2-(C,-Cs-alkyl) group, for example a hydrogen, a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1-ethylpropyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group, may independently of one another be combined with each C,-C6-alkyl group on the sulphonyl group of the sulphonamide, for example with a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1-ethylpropyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group.
In the -N(Co-C6-alkyl)-SO2-C3-C,-cycloalkyl groups of the radicals R4 to R6, each of the (Co-C6-alkyl) groups on the nitrogen atom of the -N(Co-Cs-alkyl)-SO2-C3-C,-cycloalkyl group, for example a hydrogen, a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1 -ethyl propyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group, may be combined independently of one another with each C3-C,-cycloalkyl group on the sulphonyl group, for example with a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group.
In the -N(Co-Cs-alkyl)-SO2-N-di(Co-C6-alkyl) groups of the radicals R4 to R6, all three (Co-C6-alkyl) groups may be independently of one another a hydrogen, a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1-ethylpropyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group.

In the -N(Co-C6-alkyl)-SO2-NH-(C3-C,)-cycloalkyl groups of the radicals R4 to R6, the Co-Cs-alkyl group of the -N(Co-C6-alkyl)-SO2-NH-(C3-C7)-cycloalkyl group, for example a hydrogen, a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pen-tyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1 -ethyl propyl), neopentyl, (1,1-5 dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group, may be combined independently of one another with each C3-C,-cycloalkyl group, for example with a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl 10 group.
In the -C(O)-N(H)-C2-C6-alkylene-(C,-C6-alkyl)amine groups of the radicals R4 to R6, each of the C2-C6-alkylene groups on the nitrogen atom of the -C(O)-N(H)-C2-C6-alkylene-(C,-C6-alkyl)amine group, for example an ethylene, propylene, butylene, penty-lene or hexylene group, may be combined independently of one another with each C,-15 C6-alkyl group on the amino group, for example with a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1-ethylpropyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-20 dimethylbutyl) group.
In the -C(O)-N(H)-C2-C6-alkylene-[di(C,-Cs-alkyl)]amine groups of the radicals R4 to R6, each of the C2-C6-alkylene groups on the nitrogen atom of the -C(O)-N(H)-Cz-C6-alkylene-[di(C,-C6-aIkyl)]amine group, for example an ethylene, propylene, butylene, pentylene or hexylene group, may be combined independently of one another with each 25 of the two identically or different C,-C6-alkyl groups on the amino group, for example with a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1-ethylpropyl), neopentyl, (1,1-dimethyl-propyl), hexyl-, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group.
In the -C(O)-N(H)-CZ-C6-alkylene-(C3-C7-cycloalkyl)amine groups of the radicals R4 to R6, each of the (C2-C6-alkylene) groups of the -C(O)-N(H)-C2-C6-alkylene-(C3-C,-cyclo-alkyl)amine group, for example an ethylene, propylene, butylene, pentylene or hexylene group, may be combined independently of one another with each C3-C7-cycloalkyl group on the amine, for example with a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group.
In the -C(O)-N(H)-C2-Cs-alkylene-(C3-C,-cycloalkyl-C,-C6-alkylene)amine groups of the radicals R4 to R6, each of the (C2-Cs-alkylene) groups of the -C(O)-N(H)-C2-C6-alkylene-(C3-C6-cycloalkyl-C1-C6-alkylene)amine group, for example an ethylene, pro-pylene, butylene, pentylene or hexylene group, may be combined independently of one another with each C3-C7-cycloalkyl-C,-C6-alkyiene group on the amine, for example with a cyclopropylmethylene, cyclopropylethylene, cyclopropylpropylene, cyclopropylbuty-lene, cyclopropylpentylene, cyclopropylhexylene, cyclobutylmethylene, cyclobutylethyl-ene, cyclobutylpropylene, cyclobutylbutylene, cyclobutylpentylene, cyclobutylhexylene, cyclopentylmethylene, cyclopentylethylene, cyclopentylpropylene, cyclopentylhexylene, cyclohexylmethylene, cyclohexylethylene, cyclohexylpropylene, cyclohexylbutylene, cyclohexylpentylene, cyclohexylhexylene, cycloheptylmethylene, cycloheptylethylene, cycloheptylpropylene, cycloheptylbutylene, cycloheptylpentylene or cycloheptylhexylene group.

In the -S(OZ)-N(H)-C2-C6-alkylene-(C,-Cs-alkyl)amine groups of the radicals R4 to R6, the (C2-C6-alkylene) groups of the -S(02)-N(H)-C2-C6-alkylene-(C,-Cs-alkyl)amine group, for example an ethylene, propylene, butylene, pentylene or hexylene group, may be combined independently of one another with each C,-Cs-alkyl group on the amino group, for example with a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1-ethylpropyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1, 1 -dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group.
In the -S(O2)-N(H)-CZ-C6-alkylene-[di(C,-C6-alkyl)]amine groups of the radicals R4 to R6, the C2-C6-alkylene group of the -S(02)-N(H)-C2-C6-alkylene-[di(C,-C6-alkyl)]amine group, for example an ethylene, propylene, butylene, pentylene or hexylene group, may be combined independently of one another with each of the two C,-C6-alkyl groups on the amino group, for example with a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1-ethylpropyl), neopentyl, (1,1-dimethylpropyl), hexyl-, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group.
In the -S(OZ)-N(H)-C2-C6-alkylene-(C3-C,-cycloalkyl)amine groups of the radicals R4 to R6, the Cz-C6-alkylene group of the -S(OZ)-N(H)-CZ-C6-alkylene-(C3-C7-cycloalkyl)-amine group, for example an ethylene, propylene, butylene, pentylene or hexylene group, may be combined independently of one another with each C3-C7-cycloalkyl group on the amino group, for example with a cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl group.
In the -S(02)-N(H)-C2-C6-alkylene-(C3-C,-cycloalkyl-C,-C6-alkylene)amine groups of the radicals R4 to R6, each C2-C6-alkylene group of the -S(O2)-N(H)-CZ-Cs-alkylene-(C3-C7-cycloalkyl-C,-C6-alkylene)amine group, for example an ethylene, propylene, bu-tylene, pentylene or hexylene group, may be combined independently of one another with each C3-C7-cycloalkyl-C,-C6-alkylene group on the amine, for example with a cyclopropylmethylene, cyclopropylethylene, cyclopropylpropylene, cyclopropylbutylene, cyclopropylpentylene, cyclopropylhexylene, cyclobutylmethylene, cyclobutylethylene, cyclobutylpropylene, cyclobutylbutylene, cyclobutylpentylene, cyclobutylhexylene, cyclopentylmethylene, cyclopentylethylene, cyclopentylpropylene, cyclopentylhexylene, cyclohexylmethylene, cyclohexylethylene, cyclohexylpropylene, cyclohexylbutylene, cyclohexylpentylene, cyclohexylhexylene, cycloheptylmethylene, cycloheptylethylene, cycloheptylpropylene, cycloheptylbutylene, cycloheptylpentylen or cycloheptylhexylene group.
In the -O-C2-Cs-alkylene-(C,-C6-alkyl)amine groups of the radicals R4 to R6, the C2-C6-alkylene group of the -O-C2-Cs-alkylene-(C,-C6-alkyl)amine group, for example an eth-ylene, propylene, butylene, pentylene or hexylene group, may be combined independ-ently of one another with each C,-C6-alkyl group on the amino group, for example a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1-ethylpropyl), neopentyl, (1,1-dimethylpropyl), hexyl, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group.
In the -O-C2-C6-alkylene-[di(C,-C6-alkyl)]amine groups of the radicals R4 to R6, the C2-C6-alkylene group of the -O-C2-C6-alkylene-[di(C,-C6-alkyl)]amine group, for example an ethylene, propylene, butylene, pentylene or hexylene group, may be combined inde-pendently of one another with two freely selectable C,-C6-alkyl groups on the amino group, for example with a methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, (2-methylbutyl), (1-methylbutyl), (1-ethylpropyl), neopentyl, (1,1-dimethylpropyl), hexyl-, (4-methylpentyl), (3-methylpentyl), (2-methylpentyl), (1-methylpentyl), (1-ethylbutyl), (2-ethylbutyl), (3,3-dimethylbutyl), (2,2-dimethylbutyl), (1,1-dimethylbutyl), (2,3-dimethylbutyl), (1,3-dimethylbutyl) or a (1,2-dimethylbutyl) group.
Compounds preferred according to the present invention are those of the formula II and III

R1\ R2 N

HO
O NH

T TZ
~ R3 R5 ~\T,T1 II

R1\ R2 N

HO
O NH
T 4~T

X~N T~T2 i R6 \/~/
VV III

in which the radicals R1 to R8 and W have the same meaning as in formula I and X is a bond, C,-C4-alkylene, C2-C4-alkenylene, C2-C4-alkynylene;
T is a nitrogen atom or a CH group;
T1, T2, T3, T4 are each independently of one another a nitrogen atom or an R3-C
group.
Compounds likewise preferred according to the present invention are those of formula Ila and Illa R1\ ~ R2 N

\ /
HO

T 4-, T

_ N T~Tz X/ , R6 \/~/
VV Illa in which the radicals R1 to R6 and W have the same meaning as in formula Ia and X is a bond, C,-C4-alkylene, C2-C4-alkenylene, C2-C4-alkynylene;
T is a nitrogen atom or a CH group;
T1, T2, T3, T4are each independently of one another a nitrogen atom or an R3-C
group.

Compounds particularly preferred according to the present invention are those of the formula IV and V

R1\ R2 N

HO
O NH
H

R6 \/~/
~V H

R1\ R2 N

HO
O NH
H

R6 ' A' N
VV V

10 in which the radicals R1 to R8 and W have the same meaning as in formula I.

Compounds likewise particularly preferred according to the present invention are those of the formula IVa and Va \ ~ R2 N

~ /
H
HO
O NH
H

R6 \/~/
VV
R5 IVa R1\ ~ R2 N

~ /
H
HO
O NH
H

R6 \/~/
VV Va in which the radicals R1 to R6 and W have the same meaning as in formula Ia.
The following compounds are very particularly preferred:
I N-[(R,S)-2-(5-Bromo-1 H-indol-3-yl)-1-(hydroxymethyl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
2 N-[(R,S)-1-(Hydroxymethyl)-2-(5-methyl-1 H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
3 N-[(R,S)-1-(Hydroxymethyl)-2-(4-methyl-1 H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
4 N-[(R,S)-1-(Hydroxymethyl)-2-(6-methyl-1 H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
5 N-[(R)-1-(Hydroxymethyl)-2-(1-methyl-lH-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
6 N-[(R,S)-2-(5-Fluoro-1 H-indol-3-yl)-1-(hydroxymethyl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
7 N-[(R,S)-1-(Hydroxymethyl)-2-(5-methoxy-1 H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
8 N-[(R, S)-2-(6-Fluoro-1 H-indol-3-yl)-1-(hydroxymethyl)ethyl]-2-(3,4, 5-trimethoxyphenyl)quinoline-4-carboxamide;
9 N-[(R,S)-1-(Hydroxymethyl)-2-[5-(phenylmethoxy)-1 H-indol-3-yl]ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R,S)-1-(Hydroxymethyl)-2-(7-methyl-1 H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
11 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
12 N-[(S)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
13 2-(4-Chloro-3-methylphenyl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yI)ethyl]quinoline-4-carboxamide;
14 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methoxy-2-(3,4, 5-trimethoxyphenyl)quinoline-4-carboxamide;
6-Bromo-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
16 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methoxy-2-(2,3,4-trimethoxyphenyl)quinoline-4-carboxamide;
17 6-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
18 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-iodo-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
19 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-nitro-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
6-Amino-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
21 N-[(R,S)-1-(Hydroxymethyl)-2-(5-fluoro-1 H-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
22 N-[(R)-1-(Hydroxymethyl)-2-(1-methyl-1 H-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
23 N-[(R,S)-2-(6-Fluoro-1 H-indol-3-yl)-1-(hydroxymethyl)ethyl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
24 2-(3,4-Dimethoxyphenyl)-N-[(S)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]quinoline-4-carboxamide;
25 2-(3,4-Dimethoxyphenyl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]quinoline-4-carboxamide;
26 2-(3,4-Dimethylphenyl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yI)ethyl]quinoline-4-carboxamide;
27 2-(2,3-Dihydro-1,4-benzodioxin-6-yl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-yi)ethyl]quinoline-4-carboxamide;
28 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyt]-2-[4-(trifluoromethoxy)phenyl]quinoline-4-carboxamide;
29 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2-[4-(methylsulphanyl)phenyl]quinoline-4-carboxamide;
30 2-(3,5-Dimethoxyphenyl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]quinoline-4-carboxamide;
31 2-[3-(Acetylamino)phenyl]-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yI)ethyl]quinoline-4-carboxamide;
32 2-(4-Chlorophenyl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]quinoline-4-carboxamide;
33 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2-(4-methoxyphenyl)quinoline-4-carboxamide;
34 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2-(3-methoxyphenyl)quinoline-4-carboxamide;
35 N-[(R)-2-(1-Ethyl-1 H-indol-3-yl)-1-(hydroxymethyl)ethyl]-6-methoxy-2-(3,4,5-tri-methoxyphenyl)quinoline-4-carboxamide;
36 2-(2,3-Dihydrobenzofuran-5-yl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yI)ethyl]quinoline-4-carboxamide;
37 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methoxy-2-(7-methoxybenzofuran-2-yl)quinoline-4-carboxamide;
38 2-[(Z)-2-(3,4-Dimethoxyphenyl)ethenyl]-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methoxyquinoline-4-carboxamide;
39 N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4'-methoxy[1,1'-biphenyl]-carboxamide;
40 N-[(S)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4'-dimethoxy[1,1'-biphenyl]-3-carboxamide;
41 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3',4'-dimethoxy[1,1'-biphenyl]-3-carboxamide;
42 N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2',3',4'-trimethoxy[1,1'-biphenyl]-3-carboxamide;
43 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3',4',5'-trimethoxy[1,1'-biphenyl]-3-carboxamide;
44 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3',4',5'-trimethoxy[1,1'-biphenyl]-4-carboxamide;
45 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3',4',5'-trimethoxy-2-methyl[1,1'-biphenyl]-4-carboxamide;
46 N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2',3',4'-trimethoxy[1,1'-biphenyl]-2-carboxamide;
47 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3',4',5'-trimethoxy[1,1'-biphenyl]-2-carboxamide;
48 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2',3',4'-trimethoxy-6-methyl[1,1'-biphenyl]-3-carboxamide;
49 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3',4',5'-trimethoxy-6-methyl[1,1'-biphenyl]-3-carboxamide;
50 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2',3',4'-trimethoxy[1,1'-biphenyl]-4-carboxamide;
51 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2',3',4'-trimethoxy-2-methyl[1,1'-biphenyl]-4-carboxamide;
52 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2',3',4,4'-tetramethoxy[1,1'-biphenyl]-2-carboxamide;
53 N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4,4',5'-tetramethoxy[1,1'-biphenyl]-2-carboxamide;
54 4'-(Hydroxymethyl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methyl[1,1'-biphenyl]-3-carboxamide;
55 4'-(Hydroxymethyl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2-methyl[1,1'-biphenyl]-4-carboxamide;
56 4'-(Hydroxymethyl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl][1,1'-biphenyl]-2-carboxamide;
57 4'-(Hydroxymethyl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl][1,1'-biphenyl]-3-carboxamide;
58 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-4-methoxy-3'-(1-methylethyl)[1,1'-biphenyl]-2-carboxamide;
59 N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3'-(1-methylethyl)[1,1'-biphenyl]-3-carboxamide;
60 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methyl-3'-(1-methylethyl)[1,1'-biphenyl]-3-carboxamide;
61 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3'-(1-methylethyl)[1,1'-biphenyl]-4-carboxamide;
62 N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2-methyl-3'-(1-methylethyl)[1,1'-biphenyl]-4-carboxamide;
63 4'-(Hydroxymethyl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-4-methoxy[1,1'-biphenyl]-2-carboxamide;
64 3',4',5'-Trifluoro-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl][1,1'-biphenyl]-2-carboxamide;
65 3',4',5'-Trifluoro-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl][1,1'-biphenyl]-3-carboxamide;
66 3',4',5'-Trifluoro-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methyl[1,1'-biphenyl]-3-carboxamide;
67 3',4', 5'-Trifluoro-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl][ 1,1'-biphenyl]-4-carboxamide;
68 3',4',5'-Trifluoro-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yi)ethyl]-2-methyl[1,1'-biphenyl]-4-carboxamide;
69 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2',5'-dimethoxy[1,1'-biphenyl]-2-carboxamide;
70 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2',4,5'-trimethoxy[1,1'-biphenyl]-2-carboxamide;
71 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2',5'-dimethoxy-6-methyl[1,1'-biphenyl]-3-carboxamide;
72 N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2',5'-dimethoxy[1,1'-biphenyl]-4-carboxamide;
73 N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2',5'-dimethoxy-2-methyl[1,1'-biphenyl]-4-carboxamide;
74 N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4'-dimethoxy[1,1'-biphenyl]-2-carboxamide;
75 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3',4,4'-trimethoxy[1,1'-biphenyl]-2-carboxamide;
76 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3',4'-dimethoxy-6-methyl[1,1'-biphenyl]-3-carboxamide;
77 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3',4'-dimethoxy[1,1'-biphenyl]-4-carboxamide;
78 N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4'-dimethoxy-2-methyl[1,1'-biphenyl]-4-carboxamide;
79 3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-4'-methoxy[1,1'-biphenyl]-2-carboxamide;
80 3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-4,4'-dimethoxy[1,1'-biphenyl]-2-carboxamide;
81 3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
82 3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-4'-methoxy-6-methyl[1,1'-biphenyl]-3-carboxamide;
83 3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-4'-methoxy[1,1'-biphenyl]-4-carboxamide;
84 3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-4'-methoxy-2-methyl[1,1'-biphenyl]-4-carboxamide;
85 N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4-dimethoxy[1,1'-biphenyl]-2-carboxamide;
86 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3'-(1-methylethyl)[1,1'-biphenyl]-2-carboxamide;
87 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2',5'-dimethoxy[1,1'-biphenyl]-3-carboxamide;
88 3',4',5'-Trifluoro-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-4-methoxy[1,1'-biphenyl]-2-carboxamide;
89 3-(Benzofuran-2-yl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yI)ethyl]benzamide;
90 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3-(5-methoxybenzofuran-2-yl)-benzamide;
91 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2-[(3,4,5-trimethoxyphenyl)methoxy]phenylpropanamide 92 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-4-[[(3,4,5-trimethoxyphenyl)methoxy]methyl]benzamide;
93 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3-[(3,4,5-trimethoxyphenyl)methoxy]thiophene-2-carboxamide;
94 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-4-[(3,4,5-trimethoxyphenyl)methoxy]phenylacetamide;
95 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3-[(3,4,5-trimethoxyphenyl)-methoxy]phenylpropanamide;
96 2-[2-(3,4-Dimethoxyphenyl)ethyl]-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yi)ethyl]-6-methoxyquinoline-4-carboxamide;
487 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yi)ethyl]-2-(3,4, 5-trimethoxyphenyl)-1,6-naphthyridine-4-carboxamide;
488 6-Bromo-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)-1,8-naphthyridine-4-carboxamide;
97 2-(6-Methoxynaphthalen-2-yl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
98 6-Methoxy-2-(3-methoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yi)ethyl]amide;
99 2-(4-Fluoro-3-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
100 2-(3-Iodo-4-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
101 2-(3-Hydroxyphenyl)-6-methoxyquinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yi)ethyl]amide;
102 2-(4-Hydroxy-3,5-dimethoxyphenyl)-6-methoxyquinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
103 2-(3,5-Difluoro-4-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid [(R)-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
104 2-(3-Ethylphenyl)-6-methoxyquinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
105 2-(3-Fluoro-4-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
106 2-(3-Fluoro-4-methoxyphenyl)-6-methylquinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
107 6-Methyl-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
108 6-Bromo-2-(2,4-dimethylthiazol-5-yl)quinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
109 2-(7-Methoxybenzofuran-2-yl)-6-trifluoromethoxyquinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
110 2-(3-Fluoro-4-methoxyphenyl)-6-iodoquinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
111 2-(3-Fluoro-4-methoxyphenyl)-6-trifluoromethoxyquinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
112 2-(3-Fluoro-4-methoxyphenyl)-6,8-dimethylquinoline-4-carboxylic acid [(R)-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
113 2-(3,4-Dimethoxyphenyl)-6-methoxy-3-methylquinoline-4-carboxylic acid [(R)-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
114 6-Amino-2-(3-fluoro-4-methoxyphenyl)quinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
115 2-(4,6-Dimethoxybenzofuran-2-yl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yI)ethyl]-6-methoxyquinoline-4-carboxamide;
116 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methoxy-2-(5-methoxybenzofuran-2-yl)quinoline-4-carboxamide;
117 2-(7-Ethoxybenzofuran-2-yl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methoxyquinoline-4-carboxamide;
118 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methoxy-2-(6-methoxybenzofuran-2-yl)quinoline-4-carboxamide;
119 2-(7-Fluorbenzofuran-2-yl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methoxyquinoline-4-carboxamide;
120 2-(4-Fluorbenzofuran-2-yl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methoxyquinoline-4-carboxamide;
121 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methoxy-2-(5-methylbenzofuran-2-yl)quinoline-4-carboxamide;
122 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methoxy-2-(7-methylbenzofuran-2-yl)quinoline-4-carboxamide;
123 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methoxy-2-(4-methoxybenzofuran-2-yl)quinoline-4-carboxamide;
124 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methoxy-2-[5-(trifluoromethoxy)benzofuran-2-yl]quinoline-4-carboxamide;
125 4-Ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
126 4-Ethoxy-3'-fluoro-4'-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
127 2-Ethoxy-N-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-5-(6-methoxypyridin-3-yl)-benzamide;
128 4-Ethoxy-2'-fluoro-3'-methoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
129 4'-Acetylamino-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
130 2-Ethoxy-N-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-5-(2-methoxypyrimidin-5-yl)-benzamide;
131 4-Ethoxy-5'-fluoro-3'-methoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
132 4-Ethoxy-3',4'-difluoro-5'-methoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1 H-indol-3-ylmethyl)ethyl]amide;
133 4-Ethoxy-4'-fluoro-3'-methoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
134 3',5'-Dimethoxy-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
135 4-Ethoxy-3'-hydroxymethylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
136 4-Ethoxy-3'-methylsulphanylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
137 3'-Cyano-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yI)ethyl]amide;
138 2-Ethoxy-5-(6-fluoro-5-methylpyridin-3-yl)-N-[(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]benzamide;
139 4-Ethoxy-4'-trifiuoromethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
140 5-Benzo[b]thiophene-3-yl-2-ethoxy-N-[(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]benzamide;
141 4-Ethoxy-2'-trifluoromethylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
142 4-Ethoxy-2'-trifluoromethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
143 4-Ethoxy-3'-trifluoromethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-yimethyl)ethyl]amide;
144 4-Ethoxy-3'-fluorobiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-ylmethyl)ethyl]amide;
145 4'-Chloro-4-ethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-ylmethyl)ethyl]amide;
146 4-Ethoxy-4'-methylsulphanylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
147 4-Ethoxy-3'-trifluoromethylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
148 3'-Chloro-4-ethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-ylmethyl)ethyl]amide;
149 4-Ethoxy-3'-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
150 5-Benzofuran-2-yl-2-ethoxy-N-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yI)ethyl]benzamide;
151 4-Ethoxy-2'-methylsulphanylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
152 2-Ethoxy-N-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-5-(1 H-indol-4-yl)benzamide;
153 2-Ethoxy-N-[(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]-5-(4-methylthiophen-2-yI)-benzamide;
154 3'-Acetylamino-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
155 4-Ethoxy-2'-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yI)ethyl]amide;
156 2-Ethoxy-N-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-5-(5-methylfuran-2-yl)-benzamide;
157 3'-Chloro-4-ethoxy-4'-methylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1H-indol-3-ylmethyl)ethyl]amide;
158 5-(2-Chloro-6-methylpyridin-3-yl)-2-ethoxy-N-[(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]benzamide;
159 4-Ethoxy-4'-fluorobiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
160 2-Ethoxy-N-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-5-naphthalen-1-yl-benzamide;
161 5-Benzo[b]thiophene-2-yl-2-ethoxy-N-[(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]benzamide;
162 4-Ethoxy-4'-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yI)ethyl]amide;
163 2-Ethoxy-N-[(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]-5-thiophen-3-yl-benzamide;
164 4-Ethoxy-4'-methoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
165 2',4'-Dichloro-4-ethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
166 4'-Methoxy-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
167 4-Propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
168 5-Benzofuran-2-yI-N-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-2-propoxybenzamide;
169 3'-Chloro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-ylmethyl)ethyl]amide;
170 5-Benzo[b]thiophene-2-yI-N-[(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;
171 3'-Fluoro-4'-methyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
172 4-Propoxy-3'-trifluoromethylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
173 2'-Fluoro-5'-methoxy-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1 H-indol-3-ylmethyl)ethyl]amide;
174 4-Propoxy-3',5'-bis-trifluoromethylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1 H-indol-3-ylmethyl)ethyl]amide;
175 4'-Chloro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-ylmethyl)ethyl]amide;
176 5-Benzo[b]thiophene-3-yl-N-[(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;
177 4-Propoxy-4'-trifluoromethylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
178 3'-Hydroxy-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
179 N-[(R)-1-Hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-2-propoxy-5-quinolin-6-yl-benzamide;
180 5-(6-Fluoro-5-methylpyridin-3-yl)-N-[(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;
181 N-[(R)-1-Hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-5-(6-methoxypyridin-3-yl)-propoxybenzamide;
182 3'-Chloro-4'-methyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
183 N-[(R)-1-Hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-2-propoxy-5-pyridin-4-yl-benzamide;
184 3'-Chloro-4'-fluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
185 3'-Acetylamino-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
186 3',4'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
187 3',5'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
188 3'-Cyano-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
189 5-(2,4-Dimethoxypyrimidin-5-yl)-N-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-2-propoxybenzamide;
190 2',3'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
191 2',5'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
192 5-[(E)-2-(4-Fluorophenyl)-vinyl]-N-[(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;
193 5-(5-Cyanothiophene-2-yl)-N-[(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]-propoxybenzamide;
194 2'-Fluoro-3'-methoxy-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1 H-indol-3-ylmethyl)ethyl]amide;
195 N-[(R)-1-Hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-5-(2-methoxypyrimidin-5-yl)-2-propoxybenzamide;
196 4'-Chloro-2',6'-difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1 H-indol-3-ylmethyl)ethyljamide;
197 3',5'-Dimethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
198 N-[(R)-1-Hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-2-propoxy-5-quinolin-3-yl-benzamide;
199 4'-Acetylamino-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
200 4-Propoxy-3'-(2,2,2-trifluoroethoxy)biphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1 H-indol-3-ylmethyl)ethyl]amide;
201 3'-Ethoxy-5'-fluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
202 5'-Ethoxy-2'-fluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1H-indol-3-ylmethyl)ethyl]amide;
203 3'-Ethoxy-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
204 4-Propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]amide;
205 5-Benzofuran-2-yl-N-[(R)-1-hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]-propoxybenzamide;
206 5-Benzo[b]thiophen-2-yl-N-[(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;
207 2'-Fluoro-4'-methyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
208 4'-Fluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1-methyl-indol-3-ylmethyl)ethyl]amide;
209 2'-Fluoro-5'-methoxy-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
210 3'-Fluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-indol-3-ylmethyl)ethyl]amide;
211 N-[(R)-1-Hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]-2-propoxy-5-pyridin-3-yl-benzamide;
212 5-Benzo[b]thiophen-3-yI-N-[(R)-2-hydroxy-1 -(1-methyl-1 H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;
213 3'-Cyano-4'-fluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
214 N-[(R)-1-Hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]-5-(6-methoxypyridin-3-yl)-2-propoxybenzamide;
215 3'-Acetylamino-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]amide;
216 3',4'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
217 3',5'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
218 5-(2,4-Dimethoxypyrimidin-5-yl)-N-[(R)-1-hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]-2-propoxybenzamide;
219 2',5'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
220 5-[(E)-2-(4-Fluorophenyl)-vinyl]-N-[(R)-2-hydroxy-1 -(1 -methyl-1 H-indol-ylmethyl)ethyl]-2-propoxybenzamide;
221 5-(5-Cyanothiophen-2-yl)-N-[(R)-2-hydroxy-1-(1-methyt-1 H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;
222 N-[(R)-1-Hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]-5-(2-methoxypyrimidin-5-yl)-2-propoxybenzamide;
223 N-[(R)-1-Hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]-2-propoxy-5-quinoline-3-yl-benzamide;
224 5'-Fluoro-3'-methoxy-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
225 4-Propoxy-3'-(2,2,2-trifluoroethoxy)biphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
226 5'-Ethoxy-2'-fluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
227 4'-Methoxy-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
228 5-Benzofuran-2-yl-N-[2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]-2-propoxybenzamide;
229 3'-Methyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-hydroxymethylethyl]amide;
230 5-Benzo[b]thiophen-2-yl-N-[2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]-2-propoxybenzamide;
231 2'-Fluoro-5'-methoxy-4-propoxybiphenyl-3-carboxylic acid [1 -(5-fluoro-1 H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
232 4-Propoxy-3',5'-bis-trifluoromethylbiphenyl-3-carboxylic acid [1-(5-fluoro-indol-3-ylmethyl)-2-hydroxyethyl]amide;
233 N-[2-(5-Fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]-2-propoxy-5-pyridin-3-yl-benzamide;
234 5-Benzo[b]thiophen-3-yl-N-[2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]-2-propoxybenzamide;
235 3'-Cyano-4'-fluoro-4-propoxybiphenyl-3-carboxylic acid [1-(5-fluoro-1 H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
236 N-[1 -(5-Fluoro-1 H-indol-3-ylmethyl)-2-hydroxyethyl]-5-(6-fluoro-5-methylpyridin-3-yl)-2-propoxybenzamide;
237 N-[2-(5-Fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]-5-(6-methoxypyridin-3-yl)-2-propoxybenzamide;
238 3'-Chloro-4'-fluoro-4-propoxybiphenyl-3-carboxylic acid [1 -(5-fluoro-1 H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
239 3'-Acetylamino-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
240 3',4'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [1 -(5-fluoro-1 H-indol-ylmethyl)-2-hydroxyethyl]amide;
241 3',5'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
242 2',5'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [1 -(5-fluoro-1 H-indol-ylmethyl)-2-hydroxyethyl]amide;
243 N-[2-(5-Fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]-5-[(E)-2-(4-fluorophenyl)-vinyl]-2-propoxybenzamide;
244 5-(5-Cyanothiophen-2-yl)-N-[2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]-2-propoxybenzamide;
245 2'-Fluoro-3'-methoxy-4-propoxybiphenyl-3-carboxylic acid [1 -(5-fluoro-1 H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
246 N-[2-(5-Fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]-5-(2-methoxypyrimidin-yl)-2-propoxybenzamide;
247 N-[2-(5-Fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]-2-propoxy-5-quinolin-3-yl-benzamide;
248 4-Propoxy-3'-(2,2,2-trifluoroethoxy)biphenyl-3-carboxylic acid [1-(5-fluoro-1 H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
249 5'-Ethoxy-2'-fluoro-4-propoxybiphenyl-3-carboxylic acid [1-(5-fluoro-1 H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
250 3'-Methoxy-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]amide;
251 3'-Chloro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 -methyl-indol-3-ylmethyl)ethyl]amide;
252 4-Propoxy-3',5'-bis-trifluoromethylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
253 3',4',5'-Trifluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
254 4-Propoxy-4'-trifluoromethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
255 4-Propoxy-4'-trifluoromethylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
256 5-(6-Fluoro-5-methylpyridin-3-yl)-N-[(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;
257 5-(3,5-Dimethylisoxazol-4-yl)-N-[(R)-1-hydroxymethyl-2-(1-methyl-1 H-indol-yl)ethyl]-2-propoxybenzamide;
258 3'-Chloro-4'-fluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
259 3'-Cyano-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]amide;
260 2',3'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
261 3',5'-Dimethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]amide;
262 3'-Ethoxy-5'-fluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
263 5'-Fluoro-3'-hydroxy-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
264 4,3'-Dipropoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-indol-3-yl)ethyl]amide;
265 3'-Chloro-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-hydroxymethylethyl]amide;
266 3'-Fluoro-4'-methyl-4-propoxybiphenyl-3-carboxylic acid [1-(5-fluoro-1 H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
267 2'-Fluoro-4'-methyl-4-propoxybiphenyl-3-carboxylic acid [1-(5-fluoro-1H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
268 4-Propoxy-3'-trifluoromethylbiphenyl-3-carboxylic acid [1-(5-fluoro-1 H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
269 3'-Isopropyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
270 3'-Methylsulphanyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
271 4-Propoxy-4'-trifluoromethoxybiphenyl-3-carboxylic acid [1 -(5-fluoro-1 H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
272 N-[2-(5-Fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]-2-propoxy-5-quinolin-6-yl-benzamide;
273 3'-Chloro-4'-methyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
274 5-(3,5-Dimethylisoxazol-4-yl)-N-[2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]-2-propoxybenzamide;
275 2',3'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [1 -(5-fluoro-1 H-indol-ylmethyl)-2-hydroxyethyl]amide;
276 3',5'-Dimethyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
277 5'-Ethoxy-3'-fluoro-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
278 3'-Fluoro-5'-hydroxy-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
279 4,3'-Dipropoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
280 3'-Ethoxy-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-hydroxymethylethyl]amide;
281 4'-Hydroxymethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-(1 H-indol-3-yl)ethyl]amide;
282 3'-Hydroxymethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-(1 H-indol-3-yl)ethyl]amide;
283 4-Propoxybiphenyl-3,4'-dicarboxylic acid 3-{[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide} 4'-methylamide;
284 N-[(R)-2-Hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]-5-(5-hydroxymethylthiophen-2-yl)-2-propoxybenzamide;
285 5'-Fluoro-4-propoxybiphenyl-3,3'-dicarboxylic acid 3-{[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide} 3'-methylamide;
286 3'-Chloro-4-propoxybiphenyl-3,4'-dicarboxylic acid 3-{[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide} 4'-methylamide;
287 3'-Hydroxymethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-(1-methyl-1 H-indol-3-yl)ethyl]amide;
288 3'-Hydroxymethyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-1 -hydroxymethylethyl]amide;
289 3'-Chloro-4-propoxybiphenyl-3,4'-dicarboxylic acid 3-{[2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide} 4'-methylamide;
290 N-[(R)-2-Hydroxy-1 -(1 -methyl-1 H-indol-3-ylmethyl)ethyl]-5-(5-hydroxymethylthiophen-2-yl)-2-propoxybenzamide;
291 3'-Chloro-4-propoxybiphenyl-3,4'-dicarboxylic acid 3-{[(R)-2-hydroxy-1-(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide} 4'-methylamide;
292 4'-Hydroxymethyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yI)-1-hydroxymethylethyl]amide;
293 4-Propoxybiphenyl-3,4'-dicarboxylic acid 3-{[2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide} 4'-methylamide;
294 5'-Fluoro-4-propoxybiphenyl-3,3'-dicarboxylic acid 3-{[2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide} 3'-methylamide;
295 4-Ethoxy-3'-fluoro-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
296 4-Ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3'-methoxy[1,1'-biphenyl]-3-carboxamide;
297 4-Ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-N-methyl[1,1'-biphenyl]-3,3'-dicarboxamide;
298 4-Ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3',4',5'-trimethoxy[1,1'-biphenyl]-3-carboxamide;
299 4-Ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4'-dimethoxy[1,1'-biphenyl]-3-carboxamide;
300 4-Ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3'-(1-methylethyl)[1,1'-biphenyl]-3-carboxamide;
301 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3',4',5'-trimethoxy-4-propoxy[1,1'-biphenyl]-3-carboxamide;
302 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-3',4'-dimethoxy-4-propoxy[1,1'-biphenyl]-3-carboxamide;
303 N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3'-methoxy-4-propoxy[1,1'-biphenyl]-3-carboxamide;
304 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-M-methyl-4-propoxy[1,1'-biphenyl]-3,3'-dicarboxamide;
305 4,3',4',5'-Tetramethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
306 4,3',4'-Trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yI)ethyl]amide;
307 3'-Fluoro-4,4'-dimethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
308 4,3'-Dimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-yI)ethyl]amide;
309 5-Benzo[1,3]dioxol-5-yl-N-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-2-methoxybenzamide;
310 3',4'-Difluoro-4,5'-dimethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
311 4-Isopropoxy-3'-methoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
312 5-Benzo[1,3]dioxol-5-yI-N-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-2-isopropoxybenzamide;
313 4-Isopropoxy-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
314 3'-Fluoro-4-isopropoxy-4'-methoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1 H-indol-3-ylmethyl)ethyl]amide;
315 4-Isopropoxy-3',4'-dimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
316 4-Isopropoxy-3'-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
317 4'-Fluoro-4-isopropoxy-3'-methylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1 H-indol-3-ylmethyl)ethyl]amide;
318 3',4'-Difluoro-4-isopropoxy-5'-methoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
319 4,3',4',5'-Tetramethoxy-5-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
320 4,3',4'-Trimethoxy-5-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-(1 H-indol-3-yl)ethyl]amide;
321 3'-Fluoro-4,4'-dimethoxy-5-methylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1 H-indol-3-ylmethyl)ethyl]amide;
322 5-Benzo[1,3]dioxol-5-yI-N-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-2-methoxy-3-methylbenzamide;
323 4,3'-Dimethoxy-5-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
324 4-Methoxy-5,3'-dimethylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
325 4'-Fluoro-4-methoxy-5,3'-dimethylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1 H-indol-3-ylmethyl)ethyl]amide;
326 3',4'-Difluoro-4,5'-dimethoxy-5-methylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
327 3'-Hydroxy-4-isopropoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
328 3',4',5'-Trimethoxy-4-(3-methyl-but-2-enyloxy)biphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
329 3'-Butoxy-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yI)ethyl]amide;
330 4-Ethoxy-3'-isopropoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
331 N-[(R)-1-Hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-5-(7-methoxybenzofuran-2-yl)-2-propoxybenzamide;
332 6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-2-(6-chlor-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
333 6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(2-methyl-1 H-indol-3-yl)ethyl]amide;
334 6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [1-hydroxymethyl-2-(6-methyl-1 H-indol-3-yl)ethyl]amide;
335 N-[ (R)-1-(Hydroxymethyl)-2-(1-ethyl)-1 H-indol-3-yl)ethyl]-6-methoxy-2-(3-methoxyphenyl)quinoline-4-carboxamide;
336 N-[ (R)-1-(Hydroxymethyl)-2-(1-propyl-1 H-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
337 N-[ (R)-1-(Hydroxymethyl)-2-(1-ethyl)-1 H-indol-3-yl)ethyl]-2-(3,5-difluoro-4-methoxyphenyl)-6-methoxyquinoline-4-carboxamide;
338 N-[ (R)-1-(Hydroxymethyl)-2-(1-isopropyl-1 H-indol-3-yl)ethyl]-6-methoxy-2 (3-methoxyphenyl)-quinoline-4-carboxamide;
339 N-[ (R)-1-(Hydroxymethyl)-2-(1-isopropyl-1 H-indol-3-yl)ethyl]-2-(3,5-difluoro-4-methoxyphenyl)-6-methoxyquinoline-4-carboxamide;
340 N-[ (R)-1-(Hydroxymethyl)-2-(1-isopropyl-1 H-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
341 N-[ (R)-1-(Hydroxymethyl)-2-(1-ethyl)-1 H-indol-3-yl)ethyl]-2-(3-fluoro-4-methoxyphenyl)-6-trifluoromethoxyquinoline-4-carboxamide;
342 N-[ (R)-1-(Hydroxymethyl)-2-(1-ethyl)-1 H-indol-3-yl)ethyl]-2-(7-methoxybenzofuran-2-yl)-6-trifluoromethoxyquinoline-4-carboxamide;
343 N-[ (R)-1-(Hydroxymethyl)-2-(1-isopropyl-1 H-indol-3-yl)ethyl]-2-(3-fluoro-methoxyphenyl)-6-trifluoromethoxyquinoline-4-carboxamide;
344 N-[ (R)-1-(Hydroxymethyl)-2-(1-isopropyl-1 H-indol-3-yl)ethyl]-2-(7-methoxybenzofuran-2-yl)-6-trifluoromethoxyquinoline-4-carboxamide;
345 N-[ (R)-1-(Hydroxymethyl)-2-(1-n hexyl-lH-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
346 N-[ (R)-1-(Hydroxymethyl)-2-(1-ethyl)-1 H-indol-3-yl)ethyl]-4-ethoxy-3'-methoxybiphenyl-3-carboxamide;
333 N-[ (R)-1-(Hydroxymethyl)-2-(1-isopropyl)-1 H-indol-3-yl)ethyl]-4-ethoxy-3'-methoxybiphenyl)-3-carboxamide;
347 N-[(R)-2-(1-Ethyl-1 H-indol-3-yl)-1-(hydroxymethyl)ethyl]-3'-fluoro-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
348 3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1-propyl-1 H-indol-3-yl)ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
349 N-[(R)-2-(1-Butyl-1 H-indol-3-yl)-1-(hydroxymethyl)ethyl]-3'-fluoro-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
350 3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-[1-(3-methylbutyl)-1 H-indol-3-yi]ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
351 3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1-pentyl-1 H-indol-3-yl)ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
352 3'-Fluoro-N-[(R)-2-(1-hexyl-1H-indol-3-yl)-1-(hydroxymethyl)ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
353 4-Ethoxy-3'-methoxybiphenyl-3-carboxylic acid [2-(5,6-difluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
354 6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [2-(5,6-difluoro-1 H-indol-3-yi)-1-hydroxymethylethyl]amide;
355 N-[ (R)-1-(Hydroxymethyl)-2-(1-ethyl-5-fluoro-1H-indol-3-yl) ethyl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
356 6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [2-(1-ethyl-5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
357 6-(3,4,5-Trimethoxyphenyl)quinoline-8-carboxylic acid [(R)-1-hydroxymethyl-(1 H-indol-3-yl)ethyl]amide;
358 3-(3,4,5-Trimethoxyphenyl)naphthalene-1-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yi)ethyl]amide;
359 4-Methoxy-5-(3,4,5-trimethoxyphenyl)thiophene-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
360 6-(3,4,5-Trimethoxyphenyl)-1 H-benzoimidazol-4-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
361 2-(3,4,5-Trimethoxyphenyl)thiazol-4-carboxylic acid [(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
362 5-(3,4,5-Trimethoxyphenyl)thiophene-2-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
363 5-(3,4,5-Trimethoxyphenyl)benzo[b]thiophene-2-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
364 2-(3-Fluoro-4-methoxyphenyl)-N-[(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]-6-methylisonicotinamide;
365 2-(3-Fluoro-4-methoxyphenyl)-6-methylpyrimidine-4-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
366 6-(4-Methoxyphenyl)pyrimidine-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
367 2-(3-Fluoro-4-methoxyphenyl)-6-methoxyquinazoline-4-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
368 2-(3-Fluoro-4-methoxyphenyl)-6-iodoquinazoline-4-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
369 2-(4-Methoxyphenyl)quinazoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
370 2-(3-Fluoro-4-methoxyphenyl)-6-methoxyquinazoline-4-carboxylic acid [(R)-1-(1-ethyl-1 H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
371 2-(3,4,5-Trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)-2-methylpropyl]amide;
372 6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)-2-methylpropyl]amide;
373 6-(4-Hydroxybut-1-ynyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
374 6-(5-Hydroxypent-1-ynyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
375 6-(3-Hydroxyprop-l-ynyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
376 6-(3-Methoxyprop-1-ynyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
377 5-(4-Hydroxybut-1-ynyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
378 5-(3-Hydroxyprop-1 -ynyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
379 5-(5-Hydroxypent-1-ynyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yI)ethyl]amide;
380 3',4',5'-Trimethoxy-5-(3-methoxyprop-1-ynyl)biphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
381 3',4'-Dimethoxy-5-(3-methoxyprop-1-ynyl)biphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
382 5-(3-Hydroxyprop-1-ynyl)-3',4'-dimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
383 3',4',5'-Trimethoxy-5-(4-methoxyphenylethynyl)biphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
384 3',4',5'-Trimethoxy-5-((Z)-3-methoxypropenyl)biphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
385 5-((Z)-4-Hydroxybut-l-enyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yi)ethyl]amide;
386 5-((Z)-3-Hydroxypropenyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
387 5-((Z)-5-Hydroxypent-l-enyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
388 6-(5-Hydroxypentyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
389 6-(4-Hydroxybutyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
390 6-(3-Hydroxypropyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
391 6-(3-Methoxypropyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yi)ethyl]amide;
392 3',4',5'-Trimethoxy-4-(3-methoxypropyl)biphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
393 3',4',5'-Trimethoxy-5-(3-methoxypropyl)biphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
394 3',4'-Dimethoxy-5-(3-methoxypropyl)biphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yi)ethyl]amide;
395 5-(3-Hydroxypropyl)-3',4'-dimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1 H-indol-3-yl)ethyl]amide;
396 5-(5-Hydroxypentyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
397 5-(3-Hydroxypropyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
398 5-(4-Hydroxybutyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1 H-indol-3-yl)ethyl]amide;
399 3',4',5'-Trimethoxy-5-[2-(4-methoxyphenyl)ethyl]-biphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
400 N-[(R)-2-[1-(2-Cyanoethyl)-1 H-indol-3-yl]-1-(hydroxymethyl)ethyl]-3'-fluoro-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
401 3'-Fluoro-N-[(R)-2-(1-heptyl-1 H-indol-3-yl)-1-(hydroxymethyl)ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
402 N-[(R)-2-[1-(4-Cyanobutyl)-1 H-indol-3-yl]-1-(hydroxymethyl)ethyl]-3'-fluoro-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
403 3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-[1-(3-phenoxypropyl)-1 H-indol-3-yl]ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
404 3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-[1-(2-methoxyethyl)-1 H-indol-3-yl]ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
405 N-[(R)-2-[1-(3-Cyanopropyl)-1 H-indol-3-yl]-1-(hydroxymethyl)ethyl]-3'-fluoro-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
406 4-Ethoxy-3'-methoxybiphenyl-3-carboxylic acid [(R)-2-(1-cyanomethyl-1 H-indol-3-yI)-1-hydroxymethylethyl]amide;
407 6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-2-(1-cyanomethyl-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
408 6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid {(R)-2-[1-(4-cyano-butyl)-1 H-indol-3-yl]-1-hydroxymethylethyl}amide;
409 4-Hydroxy-3',4' ,5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yI)ethyl]amide;
410 4-(3-Cyanopropoxy)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
411 4-Cyclopentyloxy-3'-fluoro-4'-methoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
412 4-Cyclopentyloxy-3'-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-(1 H-indol-3-yl)ethyl]amide;
413 3'-(1-Butyl-3-methylureido)-4-cyclopentyloxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
414 4-Cyclopentyloxy-4'-fluoro-3'-methylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
415 4-Cyclopentyloxy-3'-methoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
416 4-Cyclopentyloxy-3',4'-dimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1 H-indol-3-yl)ethyl]amide;
417 5-Benzo[1,3]dioxol-5-yl-2-cyclopentyloxy-N-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]benzamide;
418 4-Cyclopentyloxy-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1 H-indol-3-yl)ethyl]amide;
419 4-Cyclopentyloxy-3',4'-difluoro-5'-methoxybiphenyl-3-carboxylic acid [(R)-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
420 3'-[Butyl[(1,1-dimethylethoxy)carbonyl]amino]-4-ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl][1,1'-biphenyl]-3-carboxamide;
421 3'-(Butylamino)-4-ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl][1,1'-biphenyl]-3-carboxamide;
422 3'-[Butyl[(methylamino)carbonyl]amino]-4-ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl][1,1'-biphenyl]-3-carboxamide;
423 3'-[Butyl[(1,1-dimethylethoxy)carbonyl]amino]-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4-propoxy[1,1'-biphenyl]-3-carboxamide;
424 3'-(1-Butyl-3-methylureido)-4-methoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
425 3'-(1-Butyl-3-methylureido)-4-methoxy-5-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
426 3'-(1-Butyl-3-methylureido)-4-isopropoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
427 3'-(2-Dimethylaminoethoxy)-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
428 4'-Ethoxy-3'-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethylcarbamoyl]-biphenyl-3-carboxylic acid methyl ester;
429 4-Ethoxy-[1,1';3',1"]terphenyl-3-carboxylic acid [1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
430 3'-Acetyl-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
431 4-Ethoxy-3'-pyrrolidin-l-ylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-(1 H-indol-3-yl)ethyl]amide;
432 4'-Cyanomethyl-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
433 4'-Dimethylamino-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-(1 H-indol-3-yl)ethyl]amide;
434 4'-Hydroxymethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-(1 H-indol-3-yl)ethyl]amide;
435 4-Propoxybiphenyl-3,4'-dicarboxylic acid 4'-diethylamide 3-{[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide};
436 3'-[(R)-1-Hydroxymethyl-2-(1 H-indol-3-yl)ethylcarbamoyl]-4'-propoxybiphenyl-4-carboxylic acid;
437 4'-Acetyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yi)ethyl]amide;
438 4'-Ethanesulphonyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
439 3'-Cyanomethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
440 3'-Methanesulphonylamino-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
441 3'-Cyclopropylmethoxy-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yi)ethyl]amide;
442 3'-Methanesulphonyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1 H-indol-3-ylmethyl)ethyl]amide;
443 4-Propoxybiphenyl-3,3'-dicarboxylic acid 3'-[(2-dimethylaminoethyl)-amide]

{[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide} ;
444 3'-[(R)-1-Hydroxymethyl-2-(1 H-indol-3-yl)ethylcarbamoyl]-3-methoxy-4'-propoxybiphenyl-4-carboxylic acid methyl ester;
445 3'-Chloro-4-propoxybiphenyl-3,4'-dicarboxylic acid 4'-amide 3-{[(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide};
446 3'-Dimethylsulphamoyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
447 4'-(Propane-2-sulphonyl)-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1 H-indol-3-ylmethyl)ethyl]amide;
448 4'-Methylsulphamoyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1 H-indol-3-ylmethyl)ethyl]amide;
449 4'-Dimethylsulphamoyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1 H-indol-3-ylmethyl)ethyl]amide;
450 4-Propoxybiphenyl-3,4'-dicarboxylic acid 4'-amide 3-{[(R)-1-hydroxymethyl-(1 H-indol-3-yl)ethyl]amide};
451 3'-Methylsulphamoyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1 H-indol-3-ylmethyl)ethyl]amide;
452 3'-Methanesulphonyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
453 3'-[(R)-1-Hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethylcarbamoyl]-3-methoxy-4'-propoxybiphenyl-4-carboxylic acid methyl ester;
454 4-Propoxybiphenyl-3,4'-dicarboxylic acid 4'-[(2-dimethylaminoethyl)amide]

{[(R)-1-hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]amide};
455 3'-[2-(5-Fluoro-1 H-indol-3-yl)-1-hydroxymethylethylcarbamoyl]-4'-propoxybiphenyl-4-carboxylic acid;
456 3'-Methanesulphonylamino-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
457 3'-Methanesulphonyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
458 4-Propoxybiphenyl-3,3'-dicarboxylic acid 3'-[(2-dimethylaminoethyl)amide]

{[2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide};
459 3'-Chloro-4-propoxybiphenyl-3,4'-dicarboxylic acid 4'-amide 3-{[2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide};
460 3'-Dimethylsulphamoyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
461 4'-(Propane-2-sulphonyl)-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-indol-3-yl)-1-hydroxymethylethyl]amide;
462 4'-Dimethylsulphamoyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
463 4-Propoxybiphenyl-3,4'-dicarboxylic acid 4'-diethylamide 3-{[2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide} ;
464 3'-Methylsulphamoyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
465 3'-Acetyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]amide;
466 4-Propoxy-[1,1';3',1"]terphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]amide;
467 3'-Cyanomethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]amide;
468 3'-Methanesulphonylamino-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1-methyl-1 H-indol-3-ylmethyl)ethyl]amide;
469 4'-Cyanomethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]amide;
470 4-Propoxybiphenyl-3,3'-dicarboxylic acid 3'-[(2-dimethylaminoethyl)amide]

{[(R)-1-hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]amide};
471 4-Fluoro-3'-[(R)-2-hydroxy-1 -(1 -methyl-1 H-indol-3-ylmethyl)ethylcarbamoyl]-4'-propoxybiphenyl-3-carboxylic acid;
472 3'-Chloro-4-propoxybiphenyl-3,4'-dicarboxylic acid 4'-amide 3-{[(R)-2-hydroxy-1 -(1 -methyl-1 H-indol-3-ylmethyl)ethyl]amide};
473 4-Propoxybiphenyl-3,4'-dicarboxylic acid 4'-diethylamide 3-{[(R)-1-hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]amide};
474 4'-Dimethylamino-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
475 4'-Acetyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-hydroxymethylethyl]amide;
476 3'-Acetyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-hydroxymethylethyl]amide;
477 4-Propoxy-[1,1';3',1"]terphenyl-3-carboxylic acid [2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide;
478 3'-[2-(5-Fluoro-1 H-indol-3-yl)-1-hydroxymethylethylcarbamoyl]-3-methoxy-4'-propoxybiphenyl-4-carboxylic acid methyl ester;
480 4-Propoxybiphenyl-3,4'-dicarboxylic acid 4'-amide 3-{[2-(5-fluoro-1 H-indol-3-yl)-1 -hydroxymethylethyl]amide};
481 4-Ethoxy-4'-methoxymethylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
482 4-Ethoxybiphenyl-3,3'-dicarboxylic acid 3'-amide 3-{[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide};
483 4'-Ethanesulphonyl-4-ethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
484 4-Ethoxy-4'-(4-methylpiperazine-l-carbonyl)biphenyl-3-carboxylic acid [(R)-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
485 3'-Cyclopropylmethoxy-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
486 3'-[(R)-1-Hydroxymethyl-2-(1 H-indol-3-yl)ethylcarbamoyl]biphenyl-2-carboxylic acid methyl ester.

The present invention also relates to a process for preparing the compounds according to the invention. Compounds of the general formula I or Ia can be prepared as shown in Scheme 1 by an amide-formation reaction between the tryptophanol derivative VI
or VIa and the carboxylic acid VII. Reagents suitable for this purpose are all suitable peptide-coupling reagents which are known to the skilled person and which convert the carboxylic acid, where appropriate in the presence of a base, into an intermediate active ester, for example PyBOP ([(1H-benzotriazol-1-yl)oxy]tris(pyrrolidin-1-yl)phosphonium hexafluorophosphate), HATU (2-(7-aza-lH-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate), HBTU (2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate), EDC (N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide hydrochloride) / HOBt (1 -hydroxy-1 H-benzotriazole). It is possible as alternative for the carboxylic acid to be converted, where appropriate in the presence of a base, into the carbonyl chloride and reacted with the tryptophanol VI or VIa to give the product of the general formula I or Ia.

Scheme I

R1eR8 + Q R3 HO

R5~

Via: R7=R8=H R5/W Ia: R7=R8=H

Compounds of general formulae II, Ila, III and Illa can be prepared as shown in Scheme 2 by an amide-formation reaction between the tryptophanol derivative VI or Vla and the appropriate carboxylic acid VIII or IX. Reagents suitable for this purpose are all known peptide-coupling reagents which convert the carboxylic acid, where appropriate in the presence of a base, into an intermediate active ester, for example PyBOP ([(1 H-benzotriazol-1-yl)oxy]tris(pyrrolidin-1-yl)phosphonium hexafluorophosphate), HATU (2-(7-aza-1 H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate), HBTU
(2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate), EDC
(N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide hydrochloride) / HOBt (1 -hydroxy-benzotriazole). It is possible as alternative for the carboxylic acid to be converted, where appropriate in the presence of a base, into the carbonyl chloride and reacted with the tryptophanol VI or Vla to give the product of the general formula 11, Ila, III or Illa.

Scheme 2 R1\ ~ R2 N
R1\ R2 R7 R8 + R6 LR3 HO
HO RS X\T/O NH
NHz R4 R6 T3/ Tz VI VIII X~ ~-R3 R5 T4~ ,T
T
Vla: R7=R8=H R4 Ila: R7=R8=H

R1\ ~ R2 N

R1\ R2 T R7 R8 N T 4~T
~ \ R3 -- HO
R7 R8 + X N T~ 0 NH

HO
T
NHz R5 R4 --R3 T~ tT ', X \N ~ Tz vl IX R6 Via: R7=R8=H

Illa: R7=R8=H
Compounds of general formulae IV, IVa, V and Va can be prepared as shown in 5 Scheme 3 by an amide-formation reaction between the tryptophanol derivative VI or Vla and the appropriate carboxylic acid X or XI. Reagents suitable for this purpose are all suitable peptide-coupling reagents which are known to the skilled person and which convert the carboxylic acid, where appropriate in the presence of a base, into an intermediate active ester, for example PyBOP ([(1 H-benzotriazol-1 -yl)oxy]tris(pyrrolidin-10 1-yl)phosphonium hexafluorophosphate), HATU (2-(7-aza-lH-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate), HBTU (2-(1H-benzotriazol-1-yi)-1,1,3,3-tetramethyluronium hexafluorophosphate), EDC (N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide hydrochloride) / HOBt (1-hydroxy-1H-benzotriazole). It is possible as alternative for the carboxylic acid to be converted, where appropriate in the presence of 15 a base, into the carbonyl chloride and reacted with the tryptophanol VI or Via to give the product of the general formula IV, IVa, V or Va.

Scheme 3 R1\ R2 N

Ri ~ R2 0 OH H
N \ HO

H + R3 H

H

VI x R4 IV

Via: R7=R8=H IVa: R7=R8=H

Ri ~ R2 O OH N
R1\ R2 H R7 R8 N

R7 R8 + \ \ ~ HO
H R6 ~/ N O\ NH
HO

H

Via: R7=R8=H R4 Va: R7=R8=H

The present invention further relates to the carboxylic acids of the formulae VII, VIII, IX, X and XI as intermediates of the process according to the invention for preparing the compounds according to the invention, namely:
2-(4-Chloro-3-methylphenyl)quinoline-4-carboxylic acid;
6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid;
6-Methoxy-2-(2,3,4-trimethoxyphenyl)quinoline-4-carboxylic acid;
6-Fluoro-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid;
6-Iodo-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid;
6-Nitro-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid;
2-[4-(Trifluoromethoxy)phenyl]quinoline-4-carboxylic acid;
2-(3,5-dimethoxyphenyl)quinoline-4-carboxylic acid;
2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-6-methoxyquinoline-4-carboxylic acid;
2',3',4'-Trimethoxy[1,1'-biphenyl]-3-carboxylic acid;
3',4',5'-Trimethoxy[1,1'-biphenyl]-4-carboxylic acid;
3',4',5'-Trimethoxy-2-methyl[1,1'-biphenyl]-4-carboxylic acid;
2',3',4'-Trimethoxy-6-methyl[1,1'-biphenyl]-3-carboxylic acid;
2',3',4'-Trimethoxy[1,1'-biphenyl]-4-carboxylic acid;
2',3',4'-Trimethoxy-2-methyl[1,1'-biphenyl]-4-carboxylic acid;
3',4,4',5'-Tetramethoxy[1,1'-biphenyl]-4-carboxylic acid;
4'-(Hydroxymethyl)-6-methyl[1,1'-biphenyl]-3-carboxylic acid;
4'-(Hydroxymethyl)-2-methyl[1,1'-biphenyl]-4-carboxylic acid;
4-methoxy-3'-(1-methylethyl)[1,1'-biphenyl]-2-carboxylic acid;
3'-(1-methylethyl)[1,1'-biphenyl]-3-carboxylic acid;
6-methyl-3'-(1-methylethyl)[1,1'-biphenyl]-3-carboxylic acid;
3'-(1-methylethyl)[1,1'-biphenyl]-4-carboxylic acid;
2-methyl-3'-(1-methylethyl)[1,1'-biphenyl]-4-carboxylic acid;
4'-(Hydroxymethyl)-4-methoxy[1,1'-biphenyl]-2-carboxylic acid;
3',4',5'-Trifluoro[1,1'-biphenyl]-2-carboxylic acid;
3',4',5'-Trifluoro[1,1'-biphenyl]-3-carboxylic acid;
3',4',5'-Trifluoro-6-methyl[1,1'-biphenyl]-3-carboxylic acid;
3',4',5'-Trifluoro[1,1'-biphenyl]-4-carboxylic acid;
3',4',5'-Trifluoro-2-methyl[1,1'-biphenyl]-4-carboxylic acid;
2',4,5'-Trimethoxy[1,1'-biphenyl]-2-carboxylic acid;
2',4,5'-Trimethoxy[1,1'-biphenyl]-2-carboxylic acid;
2',5'-dimethoxy[1,1'-biphenyl]-4-carboxylic acid;

2',5'-dimethoxy-2-methyl[1,1'-biphenyl]-4-carboxylic acid;
3',4,4'-Trimethoxy[1,1'-biphenyl]-2-carboxylic acid;
3',4'-dimethoxy-6-methyl[1,1'-biphenyl]-2-carboxylic acid;
3',4'-dimethoxy-2-methyl[1,1'-biphenyl]-4-carboxylic acid;
3'-Fluoro-4'-methoxy[1,1'-biphenyl]-2-carboxylic acid;
3'-Fluoro-4,4'-dimethoxy[1,1'-biphenyl]-2-carboxylic acid;
3'-Fluoro-4'-methoxy[1,1'-biphenyl]-3-carboxylic acid;
3'-Fluoro-4'-methoxy-6-methyl[1,1'-biphenyl]-3-carboxylic acid;
3'-Fluoro-4'-methoxy-2-methyl[1,1'-biphenyl]-4-carboxylic acid;
3',4'-dimethoxy[1,1'-biphenyl]-2-carboxylic acid;
3'-(1-methylethyl)[1,1'-biphenyl]-2-carboxylic acid;
2',5'-dimethoxy[1,1'-biphenyl]-3-carboxylic acid;
3',4',5'-Trifluoro-4-methoxy[1,1'-biphenyl]-2-carboxylic acid;
3-(Benzofuran-2-yl)benzoic acid;
3-(5-methoxybenzofuran-2-yl)benzoic acid;
2-[(3,4,5-Trimethoxyphenyl)methoxy]phenylpropanoic acid;
4-[[(3,4,5-Trimethoxyphenyl)methoxy]methyl]benzoic acid;
3-[(3,4,5-Trimethoxyphenyl)methoxy]thiophene-2-carboxylic acid;
4-[(3,4,5-Trimethoxyphenyl)methoxy]phenylacetic acid;
3-[3-((3,4,5-Trimethoxyphenyl)methoxy)phenyl]propionic acid;
2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-6-methoxyquinoline-4-carboxylic acid;
2-(4-Fluoro-3-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid;
2-(3-Iodo-4-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid;
2-(3-Hydroxyphenyl)-6-methoxyquinoline-4-carboxylic acid;
2-(4-Hydroxy-3,5-dimethoxyphenyl)-6-methoxyquinoline-4-carboxylic acid;
2-(3,5-Difluoro-4-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid;
2-(3-Ethylphenyl)-6-methoxyquinoline-4-carboxylic acid;
2-(3-Fluoro-4-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid;
2-(3-Fluoro-4-methoxyphenyl)-6-methylquinoline-4-carboxylic acid;
6-Methyl-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid;
6-Bromo-2-(2,4-dimethylthiazol-5-yl)quinoline-4-carboxylic acid;
2-(7-Methoxybenzofuran-2-yl)-6-trifluoromethoxyquinoline-4-carboxylic acid;
2-(3-Fluoro-4-methoxyphenyl)-6-iodoquinoline-4-carboxylic acid;
2-(3-Fluoro-4-methoxyphenyl)-6-trifluoromethoxyquinoline-4-carboxylic acid;
2-(3-Fluoro-4-methoxyphenyl)-6,8-dimethylquinoline-4-carboxylic acid;
2-(3,4-Dimethoxyphenyl)-6-methoxy-3-methylquinoline-4-carboxylic acid;

2-(4,6-Dimethoxybenzofuran-2-yl)-6-methoxyquinoline-4-carboxylic acid;
6-Methoxy-2-(5-methoxybenzofuran-2-yl)quinoline-4-carboxylic acid;
2-(7-Ethoxybenzofuran-2-yl)-6-methoxyquinoline-4-carboxylic acid;
6-Methoxy-2-(6-methoxybenzofuran-2-yl)quinoline-4-carboxylic acid;
2-(7-Fluorobenzofuran-2-yl)-6-methoxyquinoline-4-carboxylic acid;
2-(4-Fluorobenzofuran-2-yl)-6-methoxyquinoline-4-carboxylic acid;
6-Methoxy-2-(5-methylbenzofuran-2-yl)quinoline-4-carboxylic acid;
6-Methoxy-2-(7-methylbenzofuran-2-yl)quinoline-4-carboxylic acid;
6-Methoxy-2-(4-methoxybenzofuran-2-yl)quinoline-4-carboxylic acid;
6-Methoxy-2-[5-(trifluoromethoxy)benzofuran-2-yl]quinoline-4-carboxylic acid;
4-Ethoxy-3'-fluoro-4'-methoxy[1,1'-biphenyl]-3-carboxylic acid;
4-Ethoxy-3'-methoxy[1,1'-biphenyl]-3-carboxylic acid;
4-Ethoxy-3'-[(methylamino)carbonyl][1,1'-biphenyl]-3-carboxylic acid;
4-Ethoxy-3',4',5'-trimethoxy[1,1'-biphenyl]-3-carboxylic acid;
4-Ethoxy-3',4'-dimethoxy[1,1'-biphenyl]-3-carboxylic acid;
4-Ethoxy-3'-(1-methylethyl)[1,1'-biphenyl]-3-carboxylic acid;
3',4',5'-Trimethoxy-4-propoxy[1,1'-biphenyl]-3-carboxylic acid;
3',4'-Dimethoxy-4-propoxy[1,1'-biphenyl]-3-carboxylic acid;
3'-Methoxy-4-propoxy[1,1'-biphenyl]-3-carboxylic acid;
3'-[(Methylamino)carbonyl]-4-propoxy[1,1'-biphenyl]-3-carboxylic acid;
4,3',4',5'-Tetramethoxybiphenyl-3-carboxylic acid;
4,3',4'-Trimethoxybiphenyl-3-carboxylic acid;
3'-Fluoro-4,4'-dimethoxybiphenyl-3-carboxylic acid;
4,3'-Dimethoxybiphenyl-3-carboxylic acid;
5-Benzo[1,3]dioxol-5-yl-2-methoxybenzoic acid;
3',4'-Difluoro-4,5'-dimethoxybiphenyl-3-carboxylic acid;
4-Isopropoxy-3'-methoxybiphenyl-3-carboxylic acid;
5-Benzo[ 1, 3]dioxol-5-yl-2-isopropoxybenzoic acid;
4-Isopropoxy-3',4',5'-trimethoxybiphenyl-3-carboxylic acid;
3'-Fluoro-4-isopropoxy-4'-methoxybiphenyl-3-carboxylic acid;
4-isopropoxy-3',4'-dimethoxybiphenyl-3-carboxylic acid;
4-Isopropoxy-3'-methylbiphenyl-3-carboxylic acid;
4'-Fluoro-4-isopropoxy-3'-methylbiphenyl-3-carboxylic acid;
3',4'-Difluoro-4-isopropoxy-5'-methoxybiphenyl-3-carboxylic acid;
4,3',4',5'-Tetramethoxy-5-methylbiphenyl-3-carboxylic acid;
4,3',4'-Trimethoxy-5-methylbiphenyl-3-carboxylic acid;

3'-Fluoro-4,4'-dimethoxy-5-methylbiphenyl-3-carboxylic acid;
5-Benzo[1,3]dioxol-5-yl-2-methoxy-3-methyl-benzoic acid;
4,3'-Dimethoxy-5-methylbiphenyl-3-carboxylic acid;
4-Methoxy-5,3'-dimethylbiphenyl-3-carboxylic acid;
4'-Fluoro-4-methoxy-5,3'-dimethylbiphenyl-3-carboxylic acid;
3',4'-Difluoro-4,5'-dimethoxy-5-methylbiphenyl-3-carboxylic acid;
3'-Hydroxy-4-isopropoxybiphenyl-3-carboxylic acid;
3',4',5'-Trimethoxy-4-(3-methyl-but-2-enyloxy)biphenyl-3-carboxylic acid;
5-(7-Methoxybenzofuran-2-yl)-2-propoxybenzoic acid;
6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid;
2-(3,4,5-Trimethoxyphenyl)thiazol-4-carboxylic acid;
5-(3,4,5-Trimethoxyphenyl)thiophene-2-carboxylic acid;
5-(3,4,5-Trimethoxyphenyl)-benzo[b]thiophene-2-carboxylic acid;
2-(3-Fluoro-4-methoxyphenyl)-6-methylisonicotinic acid;
2-(3-Fluoro-4-methoxyphenyl)-6-methylpyrimidine-4-carboxylic acid;
6-(4-Methoxyphenyl)-pyrimidine-4-carboxylic acid;
2-(3-Fluoro-4-methoxyphenyl)-6-methoxyquinazoline-4-carboxylic acid;
2-(3-Fluoro-4-methoxyphenyl)-6-iodoquinazoline-4-carboxylic acid;
2-(4-methoxyphenyl)-quinazoline-4-carboxylic acid;
4-Hydroxy-3',4',5'-trimethoxybiphenyl-3-carboxylic acid;
4-(3-Cyano-propoxy)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid;
4-Cyclopentyloxy-3'-fluoro-4'-methoxybiphenyl-3-carboxylic acid;
4-Cyclopentyloxy-3'-methylbiphenyl-3-carboxylic acid;
3'-(1-Butyl-3-methylureido)-4-cyclopentyloxybiphenyl-3-carboxylic acid;
4-Cyclopentyloxy-4'-fluoro-3'-methylbiphenyl-3-carboxylic acid;
4-Cyclopentyloxy-3'-methoxybiphenyl-3-carboxylic acid;
4-Cyclopentyloxy-3',4'-dimethoxybiphenyl-3-carboxylic acid;
5-Benzo[1,3]dioxol-5-yl-2-cyclopentyloxybenzoic acid;
4-Cyclopentyloxy-3',4',5'-trimethoxybiphenyl-3-carboxylic acid;
4-Cyclopentyloxy-3',4'-difluoro-5'-methoxybiphenyl-3-carboxylic acid;
3'-[Butyl[(1,1-dimethylethoxy)carbonyl]amino]-4-propoxy[1,1 '-biphenyl]-3-carboxylic acid;
3'-(1-Butyl-3-methylureido)-4-methoxybiphenyl-3-carboxylic acid;
3'-(1-Butyl-3-methylureido)-4-methoxy-5-methylbiphenyl-3-carboxylic acid;
3'-(1-Butyl-3-methylureido)-4-isopropoxybiphenyl-3-carboxylic acid N-[(R)-1-(Methoxycarbonyl)-2-(1-ethyl)-1 H-indol-3-yl)ethyl]-6-methoxy-2-(3-methoxyphenyl)quinoline-4-carboxamide;

N-[(R)-1-(Methoxycarbonyl)-2-(1-propyl-1 H-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-ethyl)-1 H-indol-3-yl)ethyl]-2-(3, 5-difluoro-methoxyphenyl)-6-methoxyquinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-isopropyl-1 H-indol-3-yl)ethyl]-6-methoxy-2 (3-methoxyphenyl)- quinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-isopropyl-1 H-indol-3-yl)ethyl]-2-(3,5-difluoro-4-methoxyphenyl)-6-methoxyquinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-isopropyl-1 H-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-ethyl)-1 H-indol-3-yl)ethyl]-2-(3-fluoro-4-methoxy-phenyl)-6-trifluoromethoxyquinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-ethyl)-1 H-indol-3-yl)ethyl]-2-(7-methoxybenzofuran-2-yI)-6-trifluoromethoxyquinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-isopropyl-1 H-indol-3-yl)ethyl]-2-(3-fluoro-4-methoxy-phenyl)-6-trifluoromethoxyquinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-isopropyl-1 H-indol-3-yl)ethyl]-2-(7-methoxybenzo-furan-2-yl)-6-trifluoromethoxyquinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-n-hexyl-1 H-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-tri-methoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-ethyl)-1 H-indol-3-yl)ethyl]-4-ethoxy-3'-methoxy-biphenyl-3-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-isopropyl)-1 H-indol-3-yl)ethyl]-4-ethoxy-3'-methoxy-biphenyl)-3-carboxamide;
6-Bromoquinoline-8-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
3-Bromonaphthalene-1 -carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
5-Bromo-4-methoxythiophene-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
6-Bromo-1 H-benzimidazole-4-carboxylic acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide;
5-Bromo-2-ethoxy-N-[(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]benzamide;
N-[(R)-1-Hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-5-iodo-2-propoxybenzamide;
N-[(R)-1-Hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]-5-iodo-2-propoxybenzamide;
N-[2-(5-Fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]-5-iodo-2-propoxybenzamide and the methyl, ethyl, propyl and butyl esters thereof.

Pharmacological investigations HTRF assay for measuring cAMP in cells The method is based on a competitive immunoassay between native cAMP, which has been produced by the cells, and cAMP which is labelled with XL665. The tracer binding was visualized by a monoclonal antibody, anti-cAMP labelled with cryptate [HTRF =
homogeneous time-resolved fluorescence].
The specific signal is inversely proportional to the cAMP concentration of the samples employed.
The 665nm/ 620nm fluorescence ratio was evaluated.

The following material was used: 96-well plates for the tissue culture, 96-well plates with black edge and black base (e.g. Fluotrac 600 from Greiner), 96-well plates for the substance dilutions of polypropylene and cAMP Femtomolar (4000wells Kit, CIS
Bio International # 62AMIPEC).
The following reagents were used: BSA (bovine serum albumin) Fraction V
protease-free, IBMX (3-isobutyl-l-methylxanthine), hFSH (human follicle stimulating hormone), Triton X-100 analytical grade, potassium fluoride analytical grade, G 418 (Geneticin) and Accutase.

Buffer 1 (washing and testing buffer) contained PBS, 1 mM CaCI2, 1 mM MgCl2, 0.2%
glucose; 0.1% BSA, 1 mM IBMX.

Buffer 2 (2x lysis buffer) contained 1% Triton X-100 in PBS (without CaCl2 and MgCI2).
Buffer 3 (assay buffer) contained 50 mM potassium phosphate buffer (pH 7.0);
800 mM
potassium fluoride; 0.2% BSA (always added fresh).

Procedure:
On day 1, the cells were seeded in 96-well plates (3x104 cells per well hFSHR
clone 16 cells (CHO cells stably transfected with the human FSH receptor in 150 NI of medium).
The next day, test substance dilutions were made up. For this purpose, all the substances were diluted in ice-cold buffer 1 (with or without hFSH), and the substance dilutions were placed on ice until applied to the cells.
The cell supernatant was then aspirated off, and the cells were washed 2x with of buffer 1. The cells were treated with 60 NI of the appropriate substance concentrations at 37 C for 2h. The cells were then lysed with 60 NI of buffer 2 (put onto the supernatant) (on a plate shaker at RT for 30 min).
The test conjugates (XL-665 and anti-cAMP cryptate) were diluted in buffer 3 in accordance with the manufacturers' information. The actual mixture for measurement was pipetted into a black 96-well plate (in each case 15 NI of the cell lysate diluted with 35 NI of buffer 1; firstly 25 NI of XL-665 conjugate were pipetted and, after 10 min, 25 NI
of the anti-cAMP cryptate were added). This is followed by incubation at RT
for 90 minutes. The measurement was carried out in a PheraStar (BMG).

Tissue culture conditions 1) hFSHr clone 16 Ham's F12 PSG
10% FCS
700 pg/mI G 418 (Geneticin) from PAA.

Dose-effect curve (hFSH) for the human receptor: 1 e-8, 3e-9, 1 e-9, 3e-10, 1 e-10, 3e-11, 1 e-11, 3e-12 mol/l.
The test substances were employed in suitable dilutions in the absence (test for agonism) and in the presence of le-9 mol/I hFSH.

Evaluation The values of the well ratio were averaged and then entered directly in SigmaPlot versus the concentrations. The maximum and minimum values were determined for each plate, and half the difference is to be regarded as ICso=
The test results (Table 1) show that the compounds according to the invention have an FSH-antagonistic effect.

Table 1. FSH-antagonistic effect of selected compounds in the HTRF assay Compound [Ex. #] IC50 9 200 nM

17 400 nM
19 6 pM
22 300 nM

38 900 nM

86 8pM

88 10 pM

120 1.5 NM

Table 2. (continuation) FSH-antagonistic effect of selected compounds in the HTRF assay Compound [Ex. #] IC50 162 1.5 NM
307 450 nM
333 450 nM
337 3.5 pM

368 2.5 pM

379 4.5 pM
388 400 nM
392 1.5 NM
396 3,5 pM
403 100 nM
418 300 nM
430 400 nM

Dosage Satisfactory results are generally to be expected if the daily doses comprise a range from 5 pg to 50 mg of the compound according to the invention per kg of body weight. A
recommended daily dose for larger mammals, for example humans, is in the range from pg to 30 mg per kg of body weight. Suitable dosages for the compounds according to the invention are from 0.005 to 50 mg per day per kg of body weight, depending on the age and constitution of the patient, it being possible to administer the necessary daily dose by single or multiple delivery.
10 Pharmaceutical products based on the novel compounds are formulated in a manner known per se by processing the active ingredient with the carrier substances, fillers, substances which influence disintegration, binders, humectants, lubricants, absorbents, diluents, test modifiers, colorants etc. which are used in pharmaceutical technology, and converting into the desired administration form. Reference should be made in this connection to Remington's Pharmaceutical Science, 15th ed. Mack Publishing Company, East Pennsylvania (1980).
Suitable for oral administration are in particular tablets, coated tablets, capsules, pills, powders, granules, pastilles, suspensions, emulsions or solutions.
Preparations for injection and infusion are possible for parenteral administration.
Appropriately prepared crystal suspensions can be used for intraarticular injection. Aqueous and oily solutions for injection or suspensions and corresponding depot preparations can be used for intramuscular injection. The novel compounds can be used for rectal administration in the form of suppositories, capsules, solutions (e.g. in the form of enemas) and ointments both for systemic and for local therapy. Formulations possible for topical application are gels, ointments, greasy ointments, creams, pastes, dusting powders, milk and tinctures.
The dosage of the compounds of the general formula I in these preparations should be 0.01 % - 20% in order to achieve an adequate pharmacological effect. Topical use can also take place by means of a transdermal system, for example a patch.

The invention likewise encompasses the compounds according to the invention of the general formula I as therapeutic active ingredient. The invention further includes the compounds according to the invention of the general formula I as therapeutic active ingredients together with pharmaceutically suitable and acceptable excipients and carriers. The invention likewise encompasses a pharmaceutical composition which comprises one of the pharmaceutically active compounds according to the invention or mixture thereof and a pharmaceutically suitable salt or pharmaceutically suitable excipients and carriers.
The present invention therefore also relates to pharmaceutical compositions which comprise at least one compound of the general formula I, where appropriate together with pharmaceutically suitable excipients and/or carriers.

Suitable for forming pharmaceutically suitable salts of the compounds according to the invention of the general formula I are, by methods known to the skilled person, as inorganic acids inter alia hydrochloric acid, hydrobromic acid, sulphuric acid and phosphoric acid, nitric acid, as carboxylic acids inter alia acetic acid, propionic acid, hexanoic acid, octanoic acid, decanoic acid, oleic acid, stearic acid, maleic acid, fumaric acid, succinic acid, benzoic acid, ascorbic acid, oxalic acid, salicylic acid, tartaric acid, citric acid, lactic acid, glycolic acid, malic acid, mandelic acid, cinnamic acid, glutamic acid, aspartic acid, and as sulphonic acids inter alia methanesulphonic acid, ethanesulphonic acid, toluenesulphonic acid, benzenesulphonic acid and naphthalenesulphonic acid.
These pharmaceutical compositions and medicaments may be intended for oral, rectal, subcutaneous, transdermal, percutaneous, intravenous or intramuscular administration.
They comprise besides conventional carriers and/or diluents at least one compound of the general formula I.
The medicaments of the invention are produced using the customary solid or liquid carriers or diluents and the excipients customarily used in pharmaceutical technology, in accordance with the desired mode of administration with a suitable dosage in a known manner. The preferred preparations consist of a dosage form which is suitable for oral administration. Examples of such dosage forms are tablets, film-coated tablets, sugar-coated tablets, capsules, pills, powders, solutions or suspensions or else depot forms.

The pharmaceutical compositions which comprise at least one of the compounds according to the invention are preferably administered orally.
Parenteral preparations such as solutions for injection are also suitable.
Preparations which may also be mentioned for example are suppositories.
Appropriate tablets can be obtained for example by mixing the active ingredient with known excipients, for example inert diluents such as dextrose, sugar, sorbitol, mannitol, polyvinylpyrrolidone, disintegrants such as maize starch or alginic acid, binders such as starch or gelatine, lubricants such as magnesium stearate or talc and/ or agents to achieve a depot effect such as carboxylpolymethylene, carboxylmethylcellulose, cellulose acetate phthalate or polyvinyl acetate. The tablets may also consist of a plurality of layers.
Correspondingly, coated tablets can be produced by coating cores which have been produced in analogy to the tablets with agents normally used in tablet coatings, for example polyvinylpyrrolidone or shellac, gum Arabic, talc, titanium oxide or sugar. The tablet coating may also consist of a plurality of layers, it being possible to use the excipients mentioned above for tablets.
Solutions or suspensions with the compounds according to the invention of the general formula I may additionally comprise taste-improving agents such as saccharin, cyclamate or sugar and, for example, flavourings such as vanillin or orange extract.
They may additionally comprise suspending aids such as sodium carboxymethylcellulose or preservatives such as p-hydroxybenzoates.
Capsules comprising the compounds of the general formula I can be produced for example by the compound(s) of the general formula I being mixed with an inert carrier such as lactose or sorbitol and encapsulated in gelatine capsules.
Suitable suppositories can be produced for example by mixing with carriers intended for this purpose, such as neutral fats or polyethylene glycol or derivatives thereof.

The compounds according to the invention of the general formula I can be prepared as described below.

Abbreviations used:

ACN Acetonitrile DIBAC Diisobutylaluminium hydride DMF N,N-Dimethylformamide EDC N-Ethyl-N'-(3-dimethylaminopropyl)carbodiimide EtOH Ethanol HATU O-(7-Azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate FMOC (9H-Fluoren-9-ylmethoxy)carbonyl HOBt 1 -Hydroxy-1 H-benzotriazole MeCN Acetonitrile MeOH Methanol MTBE Methyl tert-butyl ether NMM 4-methylmorpholine NMP N-Methylpyrrolidinone Rf Reflux RT Room temperature TBAF Tetrabutylammonium fluoride TFA Trifluoroacetic acid THF Tetrahydrofuran Compounds of the general formula I or Ia can in principle be prepared as shown in Scheme 4 by an amide-formation reaction between a tryptophanol derivative VI
or Vla and a carboxylic acid VII. The reagents typically used for the coupling are EDC and 5 HOBt.
Scheme 4 \ ~

~ /

R1eR8 OyOH HO

NH
Y Oy R7 + Q R3 Y
HO

NHZ

Via: R7=R8=H R5 la: R7=R8=H

The tryptophanol derivatives of the formula VI can be prepared as shown in Scheme 5 from the corresponding amino acids which can be purchased or are known from the literature.

Scheme 5 R1\ R2 Rl~ R2 Rl~ R2 Ri N N N N

0 a~ O\ ~ b) ~~

HO HO HO HO
NHZ HN, FMOC HN, FMOC NH2 vl Reagents: a) FMOC-CI, dioxane, 10% Na2CO3 solution in water, 0 C-RT; b) i)EtOC(O)CI, THF, NMM, -10 C; ii) NaBH4, MeOH, 0 C; c) piperidine, NaOH, RT.

The carboxylic acids of the general formula VII can be prepared as shown in Scheme 6 by a Suzuki reaction between a boronic acid XII or XVI and a halogen compound XIII or XV (Hal = I, Br, CI).

Scheme 6 OH
( O~OEt R6 X-"\OH y a) W +
R5 R4 ~ R3 Hal O'rOEt xii xiii Y
XHal O~OEt Q R3 b R6 Y a) R6 X ~- Vil W ~
R5 R4 HO" Q R3 RS W
g R4 I
OH
xV XVi XiV

Reagents: a) TBAF, Pd(PPh3)4, THF, Rf; b) KOH, MeOH;.
Carboxylic acids of the formula XIX can be prepared as shown in Scheme 7 in a so-called Pfitzinger reaction from a methyl ketone and an isatin derivative XVIII.
Scheme 7 O

X CH3 T4\ T'~~T
R6 + O \T~3 a) Tf~3 N TZ X N T

XVii XViii R4 XiX
Reagents: a) KOH, EtOH.

Carboxylic acids of the general formulae XXI and XXII can likewise be prepared by a Pfitzinger reaction as shown in Scheme 8.

Scheme 8 T
R6- W CH3 + '', T3 a) O I -~- R3 --R5 N T!TZ

xx xviii O OH O OH

T
4-:~f R3 b) \--r-R3 TZ ,~ z T
R6- W N T~ R6 W N T/

XXi R4 XXii Reagents: a) KOH; b) H2, Pd/C.

Carboxylic acids of the general formula XXVIII can be prepared in an ether synthesis as shown in Scheme 9.

Scheme 9 Oy OMe Oy OMe R6 ~ Hal Y R6 ~ OH Y
W + W +

R4 HO R4 Hal m m XXII I XXIV XXV XXVI
n1,2,3 n0,1,2,3 m=0,1,2,3 m=1,2,3 a) a) OyOMe Y

O
m R5Z n XXVII

b) Oy OH

Y

O
m R5Z n XXVI11 Reagents: a) Cs2CO3, MeCN, Rf; b) KOH, MeOH.

Synthesis of the compounds according to the invention Example 1 N-[(R,S)-2-(5-Bromo-1 H-indol-3-yl)-1-(hydroxymethyl)ethyl]-2-(3,4,5-' / Br HO
O NH
N
-O
trimethoxyphenyl)quinoline-4-carboxamide -1 a) (R, S)-5-Bromo-a-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-1 H-indole-3-propanoic acid A solution of 0.36 mmol (92 mg) of 9-fluorenylmethyl chloroformate in 1.11 ml of dioxane was slowly added, while stirring and cooling to 0 C in an ice bath, to a solution of 0.35 mmol (100 mg) of 5-bromo-DL-tryptophan in 0.55 ml of dioxane and 1.11 ml of 10% strength aqueous sodium carbonate solution. After the addition was complete, the mixture was stirred at 0 C for one hour and at room temperature for a further three hours, cooled again to 0 C and 24 ml of water were added dropwise. Then 1.0 ml of concentrated hydrochloric acid is used to acidify, whereupon the protected amino acid precipitated. After the precipitate had been stored in a refrigerator and filtered, 163 mg of white amorphous solid product were obtained.

'H-NMR (400 MHz, DMSO-d6): S[ppm] = 12.73 s(1H, COOH); 11.07 s(1H, NH); 7.87 d (J=7.5 Hz, 2H, aryl); 7.75 s(1 H, aryl); 7.70 d (J = 8.1 Hz, 1 H, aryl); 7.63 m (2H, aryl);
7.39 m (2H, aryl); 7.27 m (4H, aryl); 7.17 d (J = 6.9 Hz, 1 H, aryl); 4.18 m (2H, CH); 3.56 s (2H, OCH2); 3.18 dd (J = 14.5 Hz / 4.7 Hz, 1 H, CH); 3.14 dd (J = 14.5 Hz /
4.4 Hz, 1 H, CH).

MS (ESI, +): 505 (M+1).

1 b,c) (9H-Fluoren-9-ylmethyl) [(R,S)-2-(5-bromo-1 H-indol-3-yl)-1-(hydroxymethyl)ethyl]carbamate 0.32 mmol (35 NI) of N-methylmorpholine was added to a stirred solution of 0.32 mmol (163 mg) of the protected amino acid prepared as in 1 a) in 1.7 ml of THF at -10 C, followed by 0.32 mmol (31 NI) of ethyl chloroformate. The mixture was then stirred for a further hour at the stated temperature. Subsequently, 0.96 mmol (36 mg) of sodium borohydride was added in one portion.

When the reaction mixture had reached the temperature of 0 C, 3.2 ml of methanol were added dropwise. The solution was stirred for a further 10 minutes and then 5 neutralized with 0.4 ml of 1 M hydrochloric acid. The organic solvents were removed in vacuo. The residue was taken up in water and extracted with methyl tertiary butyl ether.
The resulting organic phase was dried over magnesium sulphate, filtered and concentrated in vacuo. 157 mg of the target compound were obtained as a colourless foam.

10 'H-NMR (400 MHz, DMSO-ds): 6[ppm] = 11.00 s(1 H, NH); 7.86 d (J = 7.5 Hz, 2H, aryl); 7.76 s(1 H, aryl); 7.64 m (2H, aryl); 7.39 m (2H, aryl); 7.29 m (3H, aryl); 7.16 m (3H, aryl); 4.74 t(J = 5.6 Hz, 1 H, OH); 4.17 m (4H, CH, OCH2); 3.74 m (2H, OCH2);
2.91 dd (J = 14.3 Hz / 5.8 Hz, 1 H, CH); 2.70 dd (J = 14.4 Hz / 8.4 Hz, 1 H, CH).

MS (ESI,+): 491 (M+1).

1 d) (R, S)-(3-Amino-5-bromo-1 H-indole-3-propanol 0.30 mmol (150 mg) of the protected amino alcohol prepared as in 1 b,c) was stirred in 4 ml of piperidine at room temperature for one hour. After the solution had been cooled to 0 C, 2 ml of water were added dropwise. The resulting precipitate was filtered off, and a total of 1.5 g of potassium hydroxide powder was added in portions to the filtrate while stirring. The piperidine phase was separated off and concentrated in vacuo with addition of toluene. 110 mg of the amino alcohol still contaminated with piperidine were obtained.

MS(ESI,+): 269(M+1).

1 e) N-[(R, S)-2-(5-Bromo-1 H-indol-3-yl)-1-(hydroxymethyl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide 0.38 mmol (130 mg) of 2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid were dissolved in 3 ml of DMF and, at room temperature, 0.38 mmol (59 mg) of 1-hydroxy-1H-benzotriazole hydrate and 0.38 mmol (73 mg) of N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide hydrochloride were added. The mixture was stirred at the stated temperature for 30 minutes and then about 0.35 mmol (100 mg) of the amino alcohol obtained as in 1 d) was added.

After a further hour, the reaction mixture was added to saturated aqueous sodium hydrogen carbonate solution, and the precipitate was filtered and washed with water.
Purification by chromatography on silica gel with the eluent cyclohexane /
ethyl acetate affords 50 mg of the amide as yellowish solid.

'H-NMR (400 MHz, DMSO-d6): 8[ppm] = 11.09 s (1 H, NH); 8.64 d (J = 8.3 Hz, 1 H, aryl); 8.07 d (J = 8.4 Hz, 1 H, aryl); 7.98 s (1 H, aryl); 7.82 s (1 H, aryl);
7.74 m (2H, aryl);
7.53 s (2H, aryl); 7.46 t (J = 7.5 Hz, 1 H, aryl); 7.34 d (J = 8.5 Hz, 1 H, aryl); 7.26 s(1 H, aryl); 7.16 d (J = 7.3 Hz, 1 H, aryl); 4.92 t (J = 5.0 Hz, 1 H, OH); 4.36 m(1 H, CH); 3.93 s (6H, OCH3); 3.76 s (3H, OCH3); 3.59 m (2H, OCH2); 3.06 dd (J = 14.6 Hz / 5.4 Hz, 1 H, CH); 2.89 dd (J = 14.6 Hz / 8.5 Hz, 1 H, CH).

MS (APCI, -): 588 (M-1).

The following compounds were obtained in analogy to the preparation methods described in detail:

Ex. Product; a aio9 ~S 'H-NMR (400 MHz) S Structure reagents to Ippm]

2 N-[(R,S)-1-(Hydroxymethyl)- I (DMSO-d6): 10.72 s(1 H, 2-(5-methyl-1 H-indol-3- NH); 8.63 d (J = 8.3 Hz, Ho 1 H, NH); 8.07 d (J o NH
yl)ethyl]-2-(3,4,5-trimethoxy-phenyl)quinoline-4- 8.4Hz, 1 H, aryl); 7.97s --O
carboxamide; (1 H, aryl); 7.81 d (J = 8.4 o Hz, 1 H, aryl); 7.76 t(J =
(R, S)-p-Amino-5-methyl-1 H- 7.6 Hz, 1 H, aryl); 7.52 s indole-3-propanol (2H, aryl); 7.49 t (J = 7.6 and Hz, 1 H, aryl); 7.41 s(1 H, aryl); 7.24 d (J = 8.2 Hz, 2-(3, 4, 5- 1 H, aryl); 7.14 s(1 H, aryl);
Trimethoxyphenyl)quinoline- 6.88 d (J = 8.2 Hz, 1 H, a-4-carboxylic acid ryl); 4.89 t (J = 5.7 Hz, 1 H, OH); 4.38 m(1 H, CH);
3.93 s (6H, OCH3); 3.76 s (3H, OCH3); 3.60 m (2H, OCH2); 3.06 dd (J =14.4 Hz / 5.5 Hz,1 H, CH); 2.89 dd (J = 14.4 Hz / 8.3 Hz, 1 H, CH); 2.30 s (3H, CH3).
MS(ESI; +): 526.

3 N-[(R,S)-1-(Hydroxymethyl)- 1 (DMSO-d6): 10.82 s(1H, q 2-(4-methyl-1 H-indol-3- NH); 8.66 d (J = 8.6 HO
yl)ethyl]-2-(3,4,5-trimethoxy- Hz,1 H, NH); 8.07 d (J = o NH
phenyl)quinoline-4- 8.4 Hz, 1 H, aryl); 8.01 s -o carboxamide; (1 H, aryl); 7.78 m (2H, - ,o aryl); 7.54 s (2H, aryl);
(R, S)-AAmino-4-methyl-1 H- 7.50 t (J = 7.6 Hz, 1 H, indole-3-propanol and aryl); 4.97 t (J = 5.7 Hz, 2-(3, 4, 5- 1 H, OH); 4.39 m(1 H, CH);

Product;
ea 'H-NMR (400 MHz) S Structure a alog ~S
Ex.
9ents to IPP ]
Trimethoxyphenyl)quinoline- 3.93 s (6H, OCH3); 3.76 s 4-carboxylic acid (3H, OCH3); 3.67 m(1 H, OCH); 3.59 m(1 H, OCH);
3.31 m(1 H, CH); 3.00 m (1 H, CH); 2.70 s (3H, CH3).
MS (ESI; +): 526 (M+1).

4 N-[(R,S)-1-(Hydroxymethyl)- I (DMSO-d6): 10.68 s(1H, H
2-(6-methyl-1 H-indol-3- NH); 8.62 d (J = 8,4 HO
yl)ethyl]-2-(3,4,5- Hz,1 H, NH); 8.07 d (J = O NH
trimethoxyphenyl)quinoline- 8.4 Hz, 1 H, aryl); 7.99 s -O i~~
4-carboxamide; (1 H, aryl); 7.82 d (J = 8.3 - ,o Hz, 1 H, aryl); 7.76 t (J =
(R, S)-P-Amino-6-methyl-1 H- 7.6 Hz, 1 H, aryl); 7.53 s indole-3-propanol (2H, aryl); 7.49 m (J = 7,7 and Hz, 2H, aryl); 7.12 s(1 H, aryl); 7.10 s(1 H, aryl);
2-(3, 4, 5- 6.78 d(J = 8.1 Hz, 1 H, a-Trimethoxyphenyl)quinoline- ryl), 4.88 t (J = 5,5 Hz, 1 H, 4-carboxylic acid OH); 4.38 m(1 H, CH);
3.92 s (6H, OCH3); 3.76 s (3H, OCH3); 3.59 m (2H, OCHZ); 3.05 dd (J = 14,5 Hz / 5.7 Hz, 1 H, CH); 2.90 dd (J = 14.4 Hz / 8.3 Hz, 1 H, CH); 2.37 s (3H, CH3).
MS (APCI; -): 524 (M-1).

Ex. Product; a aiogo S 'H-NMR (400 MHz) S Structure reagents to [ppm]

N-[(R)-1-(Hydroxymethyl)-2- 1 (DMSO-d6): 8.65 d (J = 8.4 \
(1-methyl-1 H-indol-3- Hz, 1 H, NH); 8.08 d (J =
HO
yI)ethyl]-2-(3,4,5- 8.4 Hz, 1 H, aryl); 8.03 s o H
trimethoxyphenyl)quinoline- (1 H, aryl); 7.81 d (J = 8.4 1 N
4-carboxamide Hz, 1 H, aryl); 7.77 t (J = 7.6 -o .0 Hz, 1 H, aryl); 7.68 d (J =
(R)-fl-Amino-1-methyl-1 H-.9 Hz, 1 H, aryl); 7.55 s indole-3-propanol (2H, aryl); 7.48 t (J = 7.5 2-(3, 4, 5- Hz, 1 H, aryl); 7.41 d (J =
Trimethoxyphenyl)quinoline- 8=2 Hz, 1 H, aryl); 7.16 s 4-carboxylic acid (1 H, aryl); 7.13 t(J = 7.8 Hz, 1 H, aryl); 7.00 t (J = 7.4 Hz, 1 H, aryl); 4.90 t (J = 5.7 Hz, 1 H, OH); 4.38 m(1 H, CH); 3.93 s (6H, OCH3);
3.76 s (3H, OCH3); 3.74 s (3H, NCH3); 3.60 m (2H, OCHZ); 3.07 dd (J = 14.5 Hz / 5.8 Hz, 1 H, CH); 2.91 dd (J = 14.5 Hz / 8.1 Hz, 1 H, CH).
MS (ESI;+): 526 (M+1).

6 N-[(R,S)-2-(5-Fluoro-1 H- 1 (DMSO-d6): 10.96 s(1 H, H
F
indol-3-yl)-1- NH); 8.65 d (J = 8.4 Hz, HO
(hydroxymethyl)ethyl]-2- 1 H, NH); 8.07 d (J = 8.6 0 NH
(3,4,5-trimethoxyphenyl)- Hz, 1 H, aryl); 8.00 s (1 H, ;
quinoline-4-carboxamide; aryl); 7.76 m (2H, aryl); _o ~~ N
7.54 s (2H, aryl); 7.47 t (J ~
(R,S)-fl-Amino-5-fluoro-1H- = 7.5 Hz, 1H, aryl); 7.40 d indole-3-propanol (J - 10,0 Hz, 1 H, aryl);
2-(3, 4, 5- 7.35 m(1 H, aryl); 7.28 s (1 H, aryl); 6.89 t(J = 10.2 Trimethoxyphenyl)quinoline-Hz, 1 H, aryl); 4.91 t (J =

Product; Method 'H-NMR (400 MHz) S Structure Ex. analogous reagents to IPPm]
4-carboxylic acid 5.4 Hz, 1 H, OH); 4.37 m (1 H, CH); 3.93 s (6H, OCH3); 3.76 s (3H, OCH3);
3.60 m (2H, OCH2); 3.05 dd (J = 14.4 Hz / 5.6 Hz, 1 H, CH); 2.89 dd (J = 14,4 Hz / 8,1 Hz, 1 H, CH).
19F-NMR (400 MHz, DMSO-d6): -124.84 m (1 F).
MS (APCI; -): 528 (M-1).

7 N-[(R,S)-1-(Hydroxymethyl)- 1 (DMSO-d6): 10.69 s(1H, \ 0 2-(5-methoxy-1 H-indol-3- NH); 8.65 d (J = 8.4 Hz, HO""~
yI)ethyl]-2-(3,4,5- 1 H, NH); 8.07 d (J = 8,3 a NH
trimethoxyphenyl)quinoline- Hz, 1 H, aryl); 7.99 s(1 H, ~~
I
4-carboxamide; aryl); 7.82 d (J = 8.3 Hz, I~ "~
1 H, aryl); 7.76 t(J = 7,0 "0 (R, S)-,QAmino-5-methoxy- Hz, 1 H, aryl); 7.53 s (2H, 1H-indole-3-propanol aryl); 7.48 t (J - 7.5 Hz, and 1 H, aryl); 7.24 d (J = 8,7 Hz, 1 H, aryl); 7.16 s (2H, 2-(3, 4, 5- aryl); 6.71 d (J = 8.7 Hz, Trimethoxyphenyl)quinoline- 1 H, aryl); 4.89 t (J = 5,7 4-carboxylic acid Hz, 1 H, OH); 4.38 m(1 H, CH); 3.93 s (6H, OCH3);
3.76 s (3H, OCH3); 3,68 s (3H, OCH3); 3.60 m (2H, OCH2); 3.04 dd (J = 14,5 Hz / 5.6 Hz, 1 H, CH); 2.90 dd (J = 14,5 Hz / 8.3 Hz, 1 H, CH).
MS(ESI;+): 542 (M+1).

Product;
ea 'H-NMR (400 MHz) S Structure a alog ~S
Ex.
9ents to Ipp ]

8 N-[(R,S)-2-(6-Fluoro-1 H- I (DMSO-d6): 10.93 s(1 H, H_ F
indol-3-yl)-1- NH); 8.64 d (J = 8.3 Hz, (hydroxymethyl)ethyl]-2- 1 H, NH); 8.07 d (J = 8.4 Ho O NH
(3,4,5-trimethoxyphenyl)- Hz, 1 H, aryl); 8.00 s(1 H, I
quinoline-4-carboxamide; aryl); 7.78 m (2H, aryl); o N
7.64 m(1 H, aryl); 7.54 s 'o (R, S)-~3-Amino-6-fluoro-1 H- 'o (2H, aryl); 7.48 t (J = 7.5 indole-3-propanol Hz, 1 H, aryl); 7.20 s(1 H, and aryl); 7,19 d (J = 10,2 Hz, 1 H, aryl); 6.82 t (J = 8.0 2-(3, 4, 5- Hz, 1 H, aryl); 4.91 t (J =
Trimethoxyphenyl)quinoline- 5.7 Hz, 1 H, OH); 4.38 m 4-carboxylic acid (1 H, CH); 3.93 s (6H, OCH3); 3.76 s (3H, OCH3);
3.59 m (2H, OCH2); 3.06 dd (J = 14,5 Hz / 5,6 Hz, 1 H, CH); 2.91 dd (J = 14.5 Hz / 8.3 Hz, 1 H, CH).
19F-NMR (400 MHz, DMSO-d6): -121.73 m (1 F).
MS(ESI;+): 530 (M+1).

9 N-[(R,S)-1-(Hydroxymethyl)- 1 (DMSO-d6): 10.71 s(1H, \
2-[5-(phenylmethoxy)-1H- NH); 8.66 d (J = 8.4 Hz, Ho indol-3-yI]ethyl]-2-(3,4,5- 1 H, NH); 8.07 d (J = 8.4 NH
~ . ~
trimethoxyphenyl)quinoline- Hz, 1 H, aryl); 7.96 s (1 H, 4-carboxamide; aryl); 7.81 d (J = 8.4 Hz, _ , 1 H, aryl); 7.76 t (J = 7,5 (R, S)-P-Amino-5-methoxy- Hz, 1 H, aryl); 7.51 s (1 H, 1 H-indole-3-propanol aryl); 7.48 t (J = 7.5 Hz, 1 H, aryl); 7.32 m (8H, a-and ryl); 7.18 s(1 H, aryl); 6.77 2-(3, 4, 5- d (J = 8.7 Hz, 1 H, aryl);

Product; Method 'H-NMR (400 MHz) 8 Structure Ex. analogous reagents to IpPm]
Trimethoxyphenyl)quinoline- 4.98 d (J = 11.7 Hz, 1 H, 4-carboxylic acid OCH); 4.38 m(1 H, CH);
3.91 s (6H, OCH3); 3.75 s (3H, OCH3); 3.61 m (2H, OCHZ); 3.04 dd (J = 14.4 Hz / 5.4 Hz, 1 H, CH); 2.89 dd (J = 14.5 Hz / 8.4 Hz, 1H, CH).
MS (ESI;+): 618 (M+1).
N-[(R,S)-1-(Hydroxymethyl)- 1 (DMSO-d6): 10.82 s(1H, H
2-(7-methyl-1 H-indol-3- NH); 8.65 d (J = 8.3 N ~ i yl)ethyl]-2-(3,4,5- Hz,1 H, NH); 8.07 d (J = Ho trimethoxyphenyl)quinoline- 8.4 Hz, 1 H, aryl); 8.02 s 0 NH
4-carboxamide; (1 H, aryl); 7.83 d (J = 8.3 1;
I~ N
Hz, 1 H, aryl); 7.76 t(J =
(R, S)-,&Amino-7-methy1-1 H- o 7.5 Hz, 1 H, aryl); 7.54 s indole-3-propanol (2H, aryl); 7.48 m (2H, a-and ryl); 7.18 s(1 H, aryl); 6.86 m (2H, aryl); 4.90 t (J = 5.6 2-(3,4,5- Hz, 1H, OH); 4.39 m(1H, Trimethoxyphenyl)quinoline- OH); 3.93 s (6H, OCH3);
4-carboxylic acid 3.76 s (3H, OCH3); 3.58 m (2H, OCH2); 3.08 dd (J =
14.4 Hz / 5.6 Hz, 1 H, OH);
2.93 dd (J = 14.4 Hz / 8.2 Hz, 1 H, CH); 2.46 s (3H, CH3).
MS (ESI; +): 526 (M+1).

Ex. Product; a aioyo S 'H-NMR (400 MHz) S Structure reagents to Ippm]

11 N-[(R)-1-(Hydroxymethyl)-2- le (CDCI3): 8.27 s(1H, NH); N
Ho~
(1 H-indol-3-yI)ethyl]-2-(3,4,5- 8.13 d (J = 8.4 Hz, 1 H, a-rimethoxyphenyl)quinoline-4- ryl); 7.85 d (J = 8.0 Hz, 1 H, o HN o carboxamide; aryl); 7.72 d (J = 8.0 Hz, o 1 H, aryl); 7.70 s(1 H, aryl);
D-Tryptophanol 7.69 dd (J = 8.4 Hz / 8.0 and Hz, 1 H, aryl); 7.38 m (2H, aryl); 7.29 s (2H, aryl);
2-(3, 4, 5-Trimethoxyphenyl)- 7.19 dd (J = 8.0 Hz / 8.0 quinoline-4-carboxylic acid Hz, 1 H, aryl); 7.11 d (J =
8.0 Hz, 1 H, aryl); 7.08 d (J
= 2.6 Hz, 1 H, aryl); 6.51 d (J = 8.0 Hz, 1 H, NH); 4.66 m(1 H, CH); 3.94 s(6H, OCH3); 3.90 s (3H, OCH3);
3.94 m(1 H, CH2OH); 3.81 dd (J = 11.0 Hz / 5.1 Hz, 1H, CHzOH); 3.19 d (J
=
7.2 Hz, 2H, CH2).

12 N-[(S)-1-(Hydroxymethyi)-2- le (CDCI3): 8.21 s(1H, NH); OH
(1 H-indol-3-yI)ethyl]-2-(3,4,5- 8.14 d (J = 8.4 Hz, 1 H, a- o NH N
H
rimethoxyphenyl)quinoline-4- ryl); 7.86 d (J = 8.0 Hz, 1 H, i N
carboxamide; aryl); 7.72 d (J = 8.0 Hz, . \ I
1H, aryl); 7.71 s (1H, aryl); ' L-Tryptophanol 7.69 dd (J = 8.4 Hz / 8.0 and Hz, 1 H, aryl); 7.38 m (2H, aryl); 7.29 s (2H, aryl);
2-(3, 4, 5-Trimethoxyphenyl)- 7.20 dd (J = 8.0 Hz / 8.0 quinoline-4-carboxylic acid Hz, 1 H, aryl); 7.12 d (J =
8.0 Hz, 1 H, aryl); 7.09 d (J
= 2.6 Hz, 1 H, aryl); 6.47 d (J = 7.6 Hz, 1 H, NH); 4.67 m(1 H, CH); 3.95 s (6H, Ex. Product; a alog ~S 'H-NMR (400 MHz) S Structure reagents to [ppm]
OCH3); 3.91 s (3H, OCH3);
3.93 m(1 H, CH2OH); 3.83 dd (J = 11.0 Hz / 5.1 Hz, 1 H, CH2OH); 3.20 d (J
=
7.2 Hz, 2H, CH2).
MS (ESI;+): 512 (M+1).
[a]p = -16.5 (c = 0.475, MeOH / CH2CI2 1:1).
Example 13 2-(4-Chloro-3-methylphenyl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]quinoline-4-carboxamide OH

H
N
cl 13a) 2-(4-Chloro-3-methylphenyl)quinoline-4-carboxylic acid 2.05 mmol (135 mg) of potassium hydroxide were slowly added to a stirred solution of 0.68 mmol (100 mg) of isatin in 7 ml of ethanol and 0.82 mmol (138 mg) of 4-chloro-3-methylacetophenone. After the addition was complete, the mixture was stirred at 80 C
for six hours. The solution was cooled and then the ethanol was removed in vacuo. The residue was taken up in water and acidified with 2 ml of 1 M aqueous hydrochloric acid.
The aqueous phase was extracted with ethyl acetate. The resulting organic phase was dried over magnesium sulphate, filtered and concentrated in vacuo. Flash chromatography resulted in 145 mg of the target compound.

'H-NMR (400 MHz, pyridine-d5): 8[ppm] = 9.33 d (J = 8 Hz, 1 H, aryl); 8.81 s (1 H, aryl);
8.41 d (J = 8 Hz, 1 H, aryl); 8.28 s(1 H, aryl); 8.15 dbr (J = 8 Hz, 1 H, aryl); 7.75 dd (J = 8 Hz / 7 Hz, 1 H, aryl); 7.56 m(1 H, aryl); 7.51 m(1 H, aryl); 2.34 s (3H, Me).

13b) 2-(4-Chloro-3-methylphenyl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]quinoline-4-carboxamide In analogy to Example le), 67 mg of the title compound were obtained from 0.31 mmol 5 (93 mg) of 2-(4-chloro-3-methylphenyl)quinoline-4-carboxylic acid and 0.26 mmol (50 mg) of D-tryptophanol.

' H-NMR (400 MHz, pyridine-d5): 6[ppm] = 11.98 s(1 H, NH); 9.65 d (J = 8.4 Hz, 1 H, NH); 8.54 d (J = 7.6 Hz, 1 H, aryl); 8.31 d (J = 8.4 Hz, 1 H, aryl); 8.20 d (J
= 7.6 Hz, 1 H, aryl); 8.16 s (1 H, aryl); 8.06 s (1 H, aryl); 7.93 dd (J = 8.4 Hz / 2.1 Hz, 1 H, aryl); 7.68 dd 10 (J = 8.0 Hz / 7.6 Hz, 1 H, aryl); 7.65 d (J = 8.4 Hz, 1 H, aryl); 7.56 s(1 H, aryl); 7.48 d (J =
8.4 Hz, 1 H, aryl); 7.45 dd (J = 8.4 Hz / 8.0 Hz, 1 H, aryl); 7.33 dd (J = 8.0 Hz / 7.6 Hz, 1 H, aryl); 7.25 dd (J = 8.4 Hz / 8.0 Hz, 1 H, aryl); 5.38 m (1 H, CH); 4.38 dd (J = 10.5 Hz /
4.6 Hz, 1 H, CH2OH); 4.33 dd (J = 10.5 Hz / 5.5 Hz, 1 H, CH2OH); 3.73 dd (J =
14.3 Hz/
6.7 Hz, 1 H, CH2); 3.68 dd (J = 14.3 Hz/ 6.7 Hz, 1 H, CH2); 2.31 s(3H, CH3).

15 The following compounds were obtained in analogy to the preparation methods described in detail:

Product; Method Structure Ex. eagents anai~oous'H-NMR (400 MHz) S[ppm]

14 N-[(R)-1-(Hydroxymethyl)-2- 13 (CDCI3): 8.19 s(1H); 8.04 d H
N ~
1 H-indol-3- I eth I 6 ( y) y]- - (J = 8.4 Hz, 1 H); 7.71 d (J
HO
methoxy-2-(3,4,5-trimethoxy- = 8.0 Hz, 1 H); 7.68 s(1 H); o H
phenyl)quinoline-4- 7.38 m(3H); 7.20 m(1 H); 0, carboxamide;
7.11 m(2H); 6.52 d (J = 8.0 N Hz, 1 H); 4.71 m(1 H); 3.99 0 D-Tryptophanol s(6H); 3.91 s(3H); 3.91 m and (1 H); 3.82 m(1 H); 3.72 s (3H); 3.22 m (2H); 2.62 t (J
6-Methoxy-2-(3, 4, 5- = 5.7 Hz, 1 H).
trimethoxyphenyl)quinoline- MS (ESI; +): 542 (M+1).
4-carboxylic acid Product; Method Structure Ex. reagents a"ai=o "S'H-NMR (400 MHz) S[ppm]

15 6-Bromo-N-[(R)-1-(hydroxy- 13 (DMSO-d6): 10.86 s(1H); \
methyl)-2-(1 H-indol-3- 8.79 d (J = 8.4 Hz, 1 H);
HO
I)ethyl]-2-(3,4,5- 8.25 d (J = 2.1 Hz, 1 H); 0 H
rimethoxyphenyl)quinoline-4- 8.07 m (2H); 7.92 dd (J B' O N
carboxamide; 2.1 Hz / 8.9 Hz, 1 H); 7.69 d (J = 8.0 Hz, 1 H); 7.58 s D-Tryptophanol (2H); 7.35 d (J = 8.0 Hz, und 1 H); 7.25 d (J = 2.1 Hz, 1 H); 7.06 m(1 H); 6.96 m 6-Bromo-2-(3,4,5- (1 H); 4.92 m(1H); 4.39 m trimethoxyphenyl)quinoline- (1 H); 3.92 s (6H); 3.79 s 4-carboxylic acid (3H); 3.68 m(2H); 3.10 dd (J = 6.3 Hz / 14.8 Hz, 1 H);
2.98 dd (J = 7.6 Hz / 14.3 Hz, 1 H).
MS (ESI; +): 591 (M+1) 16 N-[(R)-1-(Hydroxymethyl)-2- 13 (CDCI3): 8.23 s(1H); 8.03 H
(1 H-indol-3-yl)ethyl]-6- d (J = 9.1 Hz, 1 H); 7.81 s methoxy-2-(2,3,4-trimethoxy- (1 H); 7.70 d (J = 7.8 Hz, HO
H
phenyl)quinoline-4- 1 H); 7.58 m(2H); 7.37 m o~, carboxamide; (2H); 7.12 m(3H); 6.80 d (J (~ -N
= 8.8 Hz, 1 H); 6.51 d (J = ~o ~ o ~o D-Tryptophanol and 7.8 Hz, 1 H); 4.61 m(1 H);
6-Methoxy-2-(2,3,4- 3.98 s (3H); 3.95 s (3H);
trimethoxyphenyl)quinoline- 3.84 s (3H); 3.69 s (3H);
4-carboxylic acid 3.20 d (J = 7.1 Hz, 2H);
2.68 s (1 H).
MS (ESI; +): 542 (M+1).

Product; Method Structure Ex. reagents anai~oous'H-NMR (400 MHz) S[ppm]

"
17 6-Fluoro-N-[(R)-1-(hydroxy- 13 (CDCI,): 8.22 s(1H); 8.15 S
N methyl)-2-(1 H-indol-3- m(1 H); 7.71 m (2H); 7.63 I)ethyl]-2-(3,4,5- dd (J = 2.8 Hz / 9.9 Hz, "o O "
rimethoxyphenyl)quinoline-4- 1 H); 7.48 m(1 H); 7.39 d (J I F
= 8.1 Hz, 1 H); 7.20 m(1 H); -N
carboxamide;
7.11 m (2H); 6.50 d (J = 7.6 D-Tryptophanol and 'o Hz, 1 H); 4.69 m(1 H); 3.99 6-Fluoro-2-(3,4,5-trimethoxy- s (6H); 3.91 s (3H); 3.85 m phenyl)quinoline-4-carboxylic (1 H); 3.21 d (J = 7.1 Hz, acid 2H); 2.60 s(1 H).
MS (ESI; +): 530 (M+1).

18 N-[(R)-1-(Hydroxymethyl)-2- 13 (DMSO-d6): 10.82 s(1H); H
(1 H-indol-3-yI)ethyl]-6-iod-2- 8.73 d (J = 8.3 Hz, 1 H);
(3,4,5- 8.45 s (1H); 8.02 m (2H); "o "
rimethoxyphenyl)quinoline-4- 7.88 d (J = 8.8 Hz, 1 H);
carboxamide; 7.64 d (J = 7.8 Hz, 1 H); o -N
7.52 s (2H); 7.31 d (J = 8.3 'o D-Tryptophanol and .
Hz, 1 H); 7.03 m(1 H); 6.92 6-lodo-2-(3, 4, 5- m(1 H); 5.72 s(1 H); 4.88 m trimethoxyphenyl)quinoline- (1 H); 4.32 m(1 H); 3.90 s 4-carboxylic acid (6H); 3.71 s (3H); 3.58 m (2H); 3.04 m (1 H); 2.93 m (1 H).
MS (ESI; +): 638 (M+1).

19 N-[(R)-1-(Hydroxymethyl)-2- 13 (DMSO-d6): 10.80 s(1H); N
(1 H-indol-3-yI)ethyl]-6-nitro-2- 8.98 d (J = 2.6 Hz, 1 H);
(3,4,5- 8.84 d(J = 8.5 Hz, 1 H); HO

"'o -rimethoxyphenyl)quinoline-4- 8.46 dd (J = 2.6 Hz / 9,4 7-NC

carboxamide; Hz, 1 H); 8.28 m(2H); 7.64 0s (1 H); 7.61 s(2H); 7.29 d o D-Tryptophanol (J=7.9Hz, 1H);7.21 d (J=
2.1 Hz, 1 H); 6.99 m(1 H);

Product' Method Structure Ex. reagents anai~oous'H-NMR (400 MHz) S[ppm]
and 6.88 m(1 H); 4.90 m(1 H);
4.35 m(1 H); 3.92 s (6H);
6-Nitro-2-(3,4,5-trimethoxy- 3.73 s (3H); 3.60 s (2H);
phenyl)quinoline-4-carboxylic 3.09 dd (J = 6.2 Hz / 14.7 acid Hz, 1 H); 3.95 dd (J = 7.7 Hz / 14.5 Hz, 1 H).
MS (ESI; +): 557 (M+1).
Example 20 6-Amino-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide I oll NH
0 ~ N
N H

5.21 mmol (2.9 g) of the compound prepared in Example 19), and the catalyst palladium on carbon (10%, 500 mg) were suspended in methanol (40 ml) and hydrogenated with hydrogen under atmospheric pressure and at room temperature. After hydrogen uptake was complete, the catalyst was filtered off and the solvent was distilled off in a rotary evaporator. Oil-pump drying resulted in 2.15 g (78% yield) of the crystalline title compound.

'H-NMR (400 MHz, DMSO-d6): 6[ppm] = 10.81 s(1 H); 8.48 d (J = 8.1 Hz, 1 H);
7.74 m (2H); 7.68 d (J = 7.8 Hz, 1 H); 7.40 s (2H); 7.31 d (J = 8.1 Hz, 1 H); 7.21 d (J = 2.3 Hz, 1 H); 7.13 dd (J = 2.5 Hz / 9.1 Hz, 1 H); 7.03 m (2H); 6.98 m(1 H); 5.70 s (2H); 4.82 m (1 H); 4.29 m(1 H); 3.88 s (6H); 3.70 s (3H); 3.58 m(1 H); 3.51 m(1 H); 3.06 dd (J = 6.6 Hz / 14.7 Hz, 1 H); 2.93 dd (J = 7.6 Hz / 14.7 Hz, 1 H).

MS (ESI; +): 527 (M+1).

The following compounds were obtained in analogy to the preparation methods described in detail:

Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents gousto LPPm]

21 N-[(R,S)-1-(Hydroxymethyl)- I (DMSO-d6): 10.94 s(1 H, N
F
2-(5-fluoro-1 H-indol-3- NH); 8.71 d (J = 8.4 Hz, yl)ethyl]-6-methoxy-2-(3,4,5- 13 1 H, NH); 8.00 d (J = 8.6 Ho NH
trimethoxyphenyl)quinoline-4- Hz, 1 H, aryl); 7.97 s(1 H, 0.
I
carboxamide;
aryl); 7.50 s (2H, aryl); N
-o ~
7.41 m (3H, aryl); 7.32 m 'o (R, S)-fi-Amino-5-fluoro-1 H- (1 H, aryl); 7.29 m(1 H, indole-3-propanol aryl); 6.88 t (J = 8.9 Hz, and 1 H, aryl); 4.96 s(1 H, OH); 4.37 m(1 H, CH);
6-Methoxy-2-(3, 4, 5- 3.93 s(6H, OCH3); 3.75 trimethoxyphenyl)quinoline-4- s (6H, OCH3); 3.60 m carboxylic acid (2H, OCH2); 3.01 dd (J =
14.4 Hz / 5.6 Hz, 1 H, CH); 2.91 dd (J = 14.4 Hz / 7.8 Hz, 1 H, CH).
19F-NMR (400 MHz, DMSO-d6): -124.81 m (1 F).
MS (ESI; +): 560 (M+1).

22 N-[(R)-1-(Hydroxymethyl)-2- 1 (DMSO-d6): 8.67 d (J = \ N
(1-methyl-1 H-indol-3-yl)ethyl]- 8.3 Hz, 1 H, NH); 8.00 d 6-methoxy-2-(3,4,5- 13 (J = 7.8 Hz, 1 H, aryl); HO
O H
trimethoxyphenyl)quinoline-4- 7.99 s(1H, aryl); 7.68 d o carboxamide (J = 7.9 Hz, 1 H, aryl); .10 N
7.51 s(2H, aryl); 7.41 m-o I~
(R)-fi-Amino-l-methyl-lH- (3H, aryl); 7.18 s (1H, -O
indole-3-propanol aryl); 7.12 t (J = 7.5 Hz, Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents gousto Ippm]
and 1 H, aryl); 6.99 t (J = 7.4 Hz, 1 H, aryl); 4.91 t(J =
6-Methoxy-2-(3, 4, 5- 5.3 Hz, 1 H, OH); 4.38 m trimethoxyphenyl)quinoline-4- (1 H, CH); 3.93 s(6H, carboxylic acid OCH3); 3.75 s (6H, OCH3); 3.72 s (3H, NCH3); 3.60 t (J = 5.2 Hz, 2H, OCHZ); 3.03 dd (J = 14.4 Hz / 6.1 Hz, 1 H, CH); 2.96 dd (J =
14.4 Hz / 7.5 Hz, 1 H, CH).
MS (APCI; +): 556 (M+1).

23 N-[(R,S)-2-(6-Fluoro-1 H- I (DMSO-d6): 10.90 s(1 H, H F
N
indol-3-yl)-1- NH); 8.67 d (J = 8.4 Hz, (hydroxymethyl)ethyl]-6- 13 1 H, NH); 8.00 dd (J = 8.6 HO'-"~
methoxy-2-(3,4,5-trimethoxy- Hz, 1 H, aryl); 7.97 s(1 H, 0 NH

phenyl)quinoline-4- aryl); 7.63 m(1 H, aryl);
carboxamide; 7.50 s(2H, aryl); 7.42 m, (2H, aryl); 7.22 s (1 H, ~O
(R, S)-p-Amino-6-fluoro-1 H-aryl); 7.10 d (J = 10,2 indole-3-propanol Hz, 1 H, aryl); 6.81 t (J
=
and 8.1 Hz, 1 H, aryl); 4.92 t (J = 5.4 Hz, 1 H, OH);
6-Methoxy-2-(3, 4, 5- 4.39 m (1 H, CH); 3.60 t trimethoxyphenyl)quinoline-4- (J = 5.3 Hz, 2H, OCH2);
carboxylic acid 3.04 dd (J = 14.5 Hz /
5.8 Hz, 1 H, CH); 2.93 dd (J = 14.6Hz / 7.9 Hz, 1 H, CH).
19F-NMR (400 MHz, DMSO-d6): -121.70 m Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents gousto Ippm]
(1 F).
MS (APCI; +): 560 (M+1).

24 2-(3,4-Dimethoxyphenyl)-N- 13 (Pyridin-d5): 11.97 s oH
[(S)-1-(hydroxymethyl)-2-(1H- (1H, NH); 9.63 d (J = 8.4 o NH N
H
indol-3-yl)ethyl]quinoline-4- Hz, 1 H, NH); 8.53 d (J = i O N I
carboxamide; 7.6 Hz, 1 H, aryl); 8.32 d\\
(J = 8.4 Hz, 1 H, aryl);
L-Tryptophanol 8.28 s(1 H, aryl); 8.20 d and (J = 7.6 Hz, 1 H, aryl);
8.13 d(J = 2.1 Hz, 1 H, 2-(3,4-Dimethoxyphenyl)- aryl); 7.70 dd (J = 8.4 Hz quinoline-4-carboxylic acid / 2.1 Hz, 1 H, aryl); 7.65 dd (J = 8.0 Hz / 7.6 Hz, 1 H, aryl); 7.64 d (J = 8.0 Hz, 1 H, aryl); 7.58 d (J =
2.1 Hz, 1 H, aryl); 7.41 dd (J = 8.4 Hz / 8.0 Hz, 1 H, aryl); 7.33 dd (J = 7.6 Hz / 7.0 Hz, 1 H, aryl); 7.26 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 7.00 d (J = 8.4 Hz, 1 H, aryl); 5.38 m (1 H, CH); 4.35 m (2H, CH2OH); 3.78 s (3H, OCH3); 3.76 s (3H, OCH3); 3.70 m (2H, CH2). [a]p = -11.0 (c =
0.330, MeOH / CH2CI2 1:1) Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents gousto [ppm]

25 2-(3,4-Dimethoxyphenyl)-N- 13 (pyridine-d5): 11.97 s OH
[(R)-1-(hydroxymethyl)-2-(1H- (1 H, NH); 9.63 d (J = 8.4 o H IN
indol-3-yl)ethyl]quinoline-4- Hz, 1 H, NH); 8.53 d (J =
i H
7.6 Hz, 1 H, aryl); 8.32 d 0 N
carboxamide;
(J = 8.4 Hz, 1 H, aryl); 'o D-Tryptophanol 8.28 s(1 H, aryl); 8.20 d (J = 7.6 Hz, 1 H, aryl);
and 8.13 d(J = 2.1 Hz, 1 H, aryl); 7.70 dd (J = 8.4 Hz 2-(3,4-Dimethoxyphenyl)- / 2.1 Hz, 1 H, aryl); 7.65 dd (J = 8.0 Hz / 7.6 Hz, quinoline-4-carboxylic acid 1 H, aryl); 7.64 d (J = 8.4 Hz, 1 H, aryl); 7.58 d(J =
2.1 Hz, 1 H, aryl); 7.41 dd (J = 8.4 Hz / 8.0 Hz, 1 H, aryl); 7.33 dd (J = 8.4 Hz / 8.0 Hz, 1 H, aryl); 7.26 dd (J = 8.0 Hz / 7.6 Hz, 1 H, aryl); 7.00 d (J = 8.4 Hz, 1 H, aryl); 5.38 m (1 H, CH); 4.35 m (2H, CH2OH); 3.78 s (3H, OCH3); 3.76 s (3H, OCH3); 3.70 m (2H, CHZ).

[a]p = +12.1 (c = 0.500, MeOH / CH2CI2 1:1) 26 2-(3,4-Dimethylphenyl)-N-[(R)- 13 (CDCI3): 8.15 s(1 H, o"
1-(hydroxymethyl)-2-(1 H- NH); 8.13 d (J = 8.0 Hz, o H I
N
indol-3-yl)ethyl]quinoline-4- 1 H, aryl); 7.93 d (J = 8.4 "
carboxamide; Hz, 1 H, aryl); 7.89 s(1 H, N I
aryl); 7.74 d (J = 8.0 Hz, I
D-Tryptophanol 1 H, aryl); 7.69 dd (J =
8.0 Hz / 8.0 Hz, 1 H, aryl);
and 7.68 d(J = 8.0 Hz, 1 H, aryl); 7.65 s (1 H, aryl);
2-(3,4- 7.39 dd (J = 8.0 Hz / 8.0 Dimethylphenyl)quinoline-4- Hz, 2H, aryl); 7.25 d (J =
8.4 Hz, 1 H, aryl); 7.23 dd Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents gousto Ippm]
carboxylic acid (J = 8.0 Hz / 8.0 Hz, 1 H, aryl); 7.15 d (J = 8.0 Hz, 1 H, aryl); 7.12 s(1 H, a-ryl); 6.43 d (J = 7.6 Hz, 1 H, NH); 4.66 m(1 H, CH); 3.93 d (J = 11.0 Hz, 1H, CH2OH); 3.85 dd (J
= 11.0 Hz / 5.0 Hz, 1 H, CH2OH); 3.22 d (J = 7.2 Hz, 2H, CHZ); 2.38 s (3H, CH3); 2.35 s (3H, CH3).

27 -(2,3-Dihydro-1,4- 13 (CDCI3): 8.22 s(1H, OH NH); 8.06 d (J = 8.4 Hz, /
benzodioxin-6-yl)-N-[(R)-1- o ~IIH N
(hydroxymethyl)-2-(1H-indol- 1 H, aryl); 7.92 d (J = 8.0 - "
3-yl)ethyl]quinoline-4- Hz, 1 H, aryl); 7.72 d(J = ro \ I -N
8.0 Hz, 1 H, aryl); 7.65 dd 'o carboxamide;
(J = 8.4 Hz / 8.0 Hz, 1 H, D-Tryptophanol aryl); 7.58 d (J = 2.1 Hz, 1 H, aryl); 7.46 dd (J =
and 8.4 Hz / 2.1 Hz, 1 H, aryl);
2-(2,3-Dihydro-1,4- 7.44 s (1 H, aryl); 7.38 dd benzodioxin-6-yl)quinoline-4- (J = 8.0 Hz/ 8.0 Hz, 1 H, carboxylic acid aryl); 7.36 dd (J = 8.0 Hz / 8.0 Hz, 1 H, aryl); 7.22 dd (J = 8.0 Hz / 8.0 Hz, 1 H, aryl); 7.15 d(J = 8.0 Hz, 1 H, aryl); 7.11 d (J =
2.5 Hz, 1 H, aryl); 6.96 d (J = 8.4 Hz, 1 H, aryl);
6.43 d (J = 7.6 Hz, 1 H, NH); 4.63 m (1H, CH);
4.32 s (4H, CH2O); 3.93 dd (J = 11.0 Hz / 3.8 Hz, 1H, CH2OH); 3.83 dd (J
= 11.0 Hz / 5,5 Hz, 1 H, Ex. Product; aMetho nalotl 'H-NMR (400 MHz) S Structure reagents gousto IPPm]
CH2OH); 3.22 dd (J =
15.0 Hz / 8.0 Hz, 1 H, CH2); 3.17 dd (J = 15.0 Hz / 6.7 Hz, 1 H, CH2).

28 N-[(R)-1-(Hydroxymethyl)-2- 13 (Pyridin-ds): 11.99 s OH (1 H-indol-3-yl)ethyl]-2-[4- (1 H, NH); 9.60 d(J = 8.0 0 H N

(trifluoromethoxy)phenyl]- Hz, 1 H, NH); 8.52 d (J "
7.6 Hz, 1 H, aryl); 8.28 d F N
uinoline-4-carboxamide F'=o =
(J = 8.4 Hz, 1 H, aryl); F
D-Tryptophanol 8.18 d (J = 7.6 Hz, 1 H, aryl); 8.15 d (J = 8.9 Hz, 2-(4-1 H, aryl); 8.10 s(1 H, a-(Trifluoromethoxy) phen yl]-ryl); 7.67 dd (J = 8.0 Hz/
quinoline-4-carboxylic acid 7.6 Hz, 1 H, aryl); 7.65 d (J = 8.4 Hz, 1 H, aryl);
7.57 d (J = 2.5 Hz, 1H, aryl); 7.44 dd (J = 8.4 Hz / 8.0 Hz, 1 H, aryl); 7.36 d (J = 8.9 Hz, 1 H, aryl);
7.33 dd (J = 8.0 Hz / 7.6 Hz, 1 H, aryl); 7.24 dd (J
=8.4Hz/8.OHz, 1H, aryl); 5.38 m(1 H, CH);
4.38 dd (J = 10.5 Hz /
5.1 Hz, 1H, CH2OH);
4.32 dd (J = 10.5 Hz /
5.5 Hz, 1 H, CH2OH);
3.72 dd (J = 16.4 Hz /
6,7 Hz, 1H, CHz); 3.68 dd (J = 16.4 Hz / 6.7 Hz, 1H, CH2).

Ex. Product; aMetho nalotl 'H-NMR (400 MHz) S Structure reagents gousto IPpm]
29 N-[(R)-1-(Hydroxymethyl)-2- 13 (CDCI,): 8.16 s(1H, OH NH); 8.11 d (J = 8.4 Hz, (1H-indol-3-yl)ethyl]-2-[4- o ~-IIH N
(methylsuipha- 1 H, aryl); 7.93 d (J = 8.6 "
nyl)phenyl]quinoline-4- Hz, 1 H, aryl); 7.93 d (J = ~ I N ~ I
8.0 Hz, 1 H, aryl); 7.73 d I'S ~
carboxamide;
(J = 8.0 Hz, 1 H, aryl);
D-Tryptophanol 7.56 s(1 H, aryl); 7.69 dd (J = 8.4 Hz / 8.0 Hz, 1 H, and aryl); 7.41 d (J = 8.0 Hz, 2-[4- 1 H, aryl); 7.40 dd (J =
(Methyl- 8.0 Hz / 8.0 Hz, 1 H, aryl);
sulphanyl)phenyl]quinoline-4- 7.35 d (J = 8.6 Hz, 1 H, carboxylic acid aryl); 7.24 dd (J = 8.0 Hz / 8.0 Hz, 1 H, aryl); 7.14 dd (J = 8.0 Hz / 8.0 Hz, 1 H, aryl); 7.12 s(1 H, a-ryl); 6.40 d (J = 7.6 Hz, 1 H, NH); 4.66 m(1 H, CH); 3.94 dd (J = 11.4 Hz / 3.8 Hz, 1 H, CHzOH); 3.85 dd (J =
11.4 Hz / 5.5 Hz, 1 H, CH2OH); 3.23 dd (J =
15.6 Hz / 7.2 Hz, 1 H, CHZ); 3.20 dd (J = 15.6 Hz / 7.2 Hz, 1 H, CHZ);
2.56 s (3H, SCH3).

30 2-(3,5-Dimethoxyphenyl)-N- 13 (PYridine-ds): 11.96 s oH
[(R)-1-(hydroxymethyl)-2-(1 H- (1 H, NH); 9.66 d (J = 8.0 o H
indol-3-YI)ethYI]quinoline-4- Hz, 1 H, NH); 8.52 d (J = H
~ ~
7.6 Hz, 1 H, aryl); 8.32 d o ~~ I
carboxamide N
(J = 8.4 Hz, 1 H, aryl);
D-Tryptophanol 8.32 s(1 H, aryl); 8.20 d .10 Ex. Product; aMetho neloa 'H-NMR (400 MHz) S Structure reagents gousto IPpm]
2-(3,5- (J = 7.6 Hz, 1 H, aryl);
Dimethoxyphenyl)quinoline-4- 7.66 dd (J = 8.0 Hz/ 7.6 carboxylic acid Hz, 1 H, aryl); 7.63 d (J =
8.4 Hz, 1 H, aryl); 7.58 d (J = 2.3 Hz, 2H, aryl);
7.57 s(1 H, aryl); 7.43 dd (J = 8.4 Hz / 8.0 Hz, 1H, aryl); 7.32 dd (J = 8.4 Hz / 8.0 Hz, 1 H, aryl); 7.26 dd (J = 8.0 Hz / 7.6 Hz, 1 H, aryl); 6.78 t (J = 2.3 Hz, 1 H, aryl); 5.37 m (1 H, CH); 4.34 m (2H, CH2OH); 3.71 s (6H, OCH3); 3.69 m (2H, CHZ).

31 -[3-(Acetylamino)phenyl]-N- 13 (Pyridine-d5): 11.91 s o"
[(R)-1-(hydroxymethyl)-2-(1H- (1H, NH); 10.91 s(1H, o H N
indol-3-yl)ethyl]quinoline-4- NH); 9.57 d (J = 8.4 Hz, ~o - H
carboxamide; 1 H, NH); 8.90 s(1 H, a- HN -N
ryl); 8.51 d (J = 7.6 Hz, D-Tryptophanol 1 H, ary l); 8.21 d (J = 8.4 Hz, 1 H, aryl); 8.20 s(1 H, and aryl); 8.19 d (J = 7.6 Hz, 1 H, aryl); 8.15 d (J = 8.0 2-(4-(Acetylamino)phenyl]- Hz, 1 H, aryl); 7.82 d (J =
quinoline-4-carboxylic acid 8.0 Hz, 1 H, aryl); 7.65 d (J = 8.4 Hz, 1 H, aryl);
7.64 dd (J = 8.0 Hz/ 7.6 Hz, 1 H, aryl); 7.63 s(1 H, aryl); 7.43 dd (J = 8.4 Hz / 8.0 Hz, 1 H, aryl); 7.41 dd (J = 8.0 Hz / 8.0 Hz, 1 H, aryl); 7.33 dd (J =
8.4 Hz / 8.0 Hz, 1 H, aryl);
7.26 dd (J = 8.0 Hz / 7.6 Ex. Product; eMetho na otl 'H-NMR (400 MHz) S Structure reagents gousto Ippm]
Hz, 1 H, aryl); 5.36 m (1 H, CH); 4.36 m (2H, CH2OH); 3.71 s (6H, CHzOH); 3.73 dd (J =
14.6 Hz / 6.7 Hz, 1H, CHZ); 3.68 dd (J = 14.6 Hz / 7.2 Hz, 1 H, CHz);
2.24 s (3H, CH3).

32 2-(4-Chlorophenyl)-N-[(R)-1- 13 (CDCI3): 8.14 s(1H, o"
(hydroxymethyl)-2-(1H-indol- NH); 8.13 d (J = 8.4 Hz, o H I
N
3-yI)ethyl]quinoline-4- 1 H, aryl); 7.98 d (J = 8.0 H
carboxamide; -- Hz, 1 H, aryl); 7.95 d (J = N
8.6 Hz, 2H, aryl); 7.74 d Cil I
o-Tryptophanol (J = 8.0 Hz, 1 H, aryl);
7.72 dd (J = 8.4 Hz / 8.0 and Hz, 1 H, aryl); 7.56 s(1 H, aryl); 7.47 d (J = 8.6 Hz, 2-(4-Chlorophenyl)quinoline-4- 2H, aryl); 7.45 dd (J =
8.0 Hz/ 8.0 Hz, 1 H, aryl);
carboxylic acid 7.44 d (J = 8.0 Hz, 1 H, aryl); 7.25 dd (J = 8.0 Hz / 8.0 Hz, 1 H, aryl); 7.14 dd (J = 8.0 Hz / 8.0 Hz, 1 H, aryl); 7.14 s(1 H, a-ryl); 6.37 d (J = 7.6 Hz, 1 H, NH); 4.69 m(1 H, CH); 3.96 d (J = 11.4 Hz, 1 H, CH2OH); 3.86 d (J
=
11.4 Hz, 1 H, CH2OH);
3.26 dd (J = 14.8 Hz /
6.3 Hz, 1 H, CHZ); 3.21 dd (J = 14.8 Hz / 7.6 Hz, 1H, CHZ).

Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents gousto [ppm]

33 -[(R)-1-(Hydroxymethyl)-2- 13 (CDCI3): 8.16 s(1H, o"
(1 H-indol-3-yl)ethyl]-2-(4- NH); 8.09 d (J - 8.4 Hz, 0 H H
methoxyphenyl)quinoline-4- 1 H, aryl); 7.94 d (J = 8.9 carboxamide;
Hz, 2H, aryl); 7.91 d(J =\ i N
8.0 Hz, 1 H, aryl); 7.73 d D-Tryptophanol (J = 8.0 Hz, 1 H, aryl);

and 7.67 dd (J = 8.4 Hz / 8.0 Hz, 1 H, aryl); 7.53 s(1 H, 2-(4-Methoxyphenyl)quinoline- aryl); 7.40 d (J = 8.0 Hz, 4-carboxylic acid 1 H, aryl); 7.37 dd (J =
8.0 Hz/ 8.0 Hz, 1 H, aryl);
7.24 dd (J = 8.0 Hz / 8.0 Hz, 1 H, aryl); 7.14 dd (J
=8.OHz/8.OHz, 1H, aryl); 7.10 d (J = 2.5 Hz, 1 H, aryl); 7.00 d(J = 8.9 Hz, 2H, aryl); 6.40 d (J =
8.0 Hz, 1 H, NH); 4.65 m (1 H, CH); 3.92 d (J =
11.4 Hz, 1H, CH2OH);
3.89 s (3H, CH3); 3.84 d (J = 11.4 Hz, 1 H, CH2OH); 3.21 m (2H, CH2).

34 N-[(R)-1-(Hydroxymethyl)-2- 13 (Pyridine-d5): 11.97 s oH
(1 H-indol-3-yl)ethyl]-2-(3- (1 H, NH); 9.63 d (J = 8.0 o H
H
methoxyphenyl)quinoline-4- Hz, 1 H, NH); 8.52 d (J = 11 I
carboxamide 7.6 Hz, 1 H, aryl); 8.31 d 0 N (J = 8.4 Hz, 1 H, aryl);

o-Tryptophanol 8.23 s (1 H, aryl); 8.20 d (J = 7.6 Hz, 1 H, aryl);
2-(3-Meth ox yph en yl) q uinolin e-4-carboxylic acid 8.03 dd (J = 2.1 Hz / 1,7 Hz, 1 H, aryl); 7.67 dd (J
=8.OHz/7.6Hz, 1H, Ex. Product; aMetho nalotl 'H-NMR (400 MHz) 8 Structure reagents gousto IPPm]
aryl); 7.64 dd (J = 8.0 Hz / 1.7 Hz, 1 H, aryl); 7.64 d (J = 8.4 Hz, 1 H, aryl);
7.56 s (1 H, aryl); 7.43 dd (J = 8.4 Hz / 8.0 Hz, 1 H, aryl); 7.39 dd (J = 8.0 Hz / 7.6 Hz, 1 H, aryl); 7.34 dd (J = 8.0 Hz / 7.6 Hz, 1 H, aryl); 7.26 dd (J =
8.4 Hz / 8.0 Hz, 1 H, aryl);
7.08 dd (J = 7.6 Hz / 2.1 Hz Hz, 1 H, aryl); 5.38 m (1 H, CH); 4.36 m (2H, CH2OH); 3.71 s (3H, OCH3); 3.71 m (2H, CH2).

35 N-[(R)-2-(1-Ethyl-1 H-indol-3- 13 (DMSO-d6): 8.69 d (J
yI)-1-(hydroxymethyl)ethyl]-6- 8.3Hz, 1H, NH), 8.00 d N~
methoxy-2-(3,4,5-trimethoxy- J = 8.3Hz, 1 H, aryl); 7.99 HO
phenyl)quinoline-4- s (1 H, aryl); 7.67 d (J = 0 H
o"
carboxamide; 7.84, 1 H, aryl); 7.50 s -0 N
(2H, aryl); 7.44 m (3H, -o (R)-2-Amino-3-(1-ethyl-1 H- ~o aryl); 7.24 s(1 H, aryl);
indol-3-yl)-propan-l-ol 7.10 t(J = 7.7 Hz, 1 H, and aryl); 6.97 t (J = 7.3 Hz, 1 H, aryl); 4.93 t (J = 5.7 6-Methoxy-2-(2,3,4-tri- Hz, 1 H, OH); 4.38 m(1 H, methoxyphenyl)quinoline-4- CH); 4.13 q (J = 7.17 Hz, carboxylic acid 2H, NC2H5); 3.92 s (6H, OCH3); 3.75 s (6H, OCH3); 3.61 m (2H, OCH2); 3.03 dd (J = 14.4 Hz / 5.8 Hz, 1 H,CH);
2.95 dd (J = 14.4 Hz /

Ex. Product; aMetho nalotl 'H-NMR (400 MHz) S Structure reagents gousto [ppm]
7.6 Hz, 1 H, CH); 1.27 t (J
= 7.17 Hz, 3H, NC2H5).
MS (APCI;+): 570(M+1) 36 2-(2,3-Dihydrobenzofuran-5- (CDC13): 8.19 s (1 H, OH
I)-N-[(R)-1-(hydroxymethyl)- NH); 8.06 d(J= 8.3 Hz, o H- N
H
2-(1 H-indol-3- 1 H, aryl); 7.93 s(1 H, I)ethyl]quinoline-4- aryl); 7.89 d (J = 8.3 Hz, N

carboxamide; 1 H, aryl); 7.72 d (J = 7.8 Hz, 1 H, aryl); 7.65 dd (J
D-Tryptophanol = 8.3 Hz / 8.3 Hz, 1 H, and aryl); 7.64 d (J = 8.3 Hz, 1 H, aryl); 7.49 s(1 H, 2-(2, 3-Dihydrobenzofuran-5- aryl); 7.39 d (J = 8.3 Hz, I)quinoline-4-carboxylic acid 1 H, aryl); 7.35 dd (J =
8.3 Hzl 8.3 Hz, 1 H, aryl);
7.22 dd (J = 8.3 Hz / 7.0 Hz, 1 H, aryl); 7.13 dd (J
= 7.8 Hz / 7.0 Hz, 1H, aryl); 7.08 d (J = 2.3 Hz, 1 H, aryl); 6.85 d (J = 8.3 Hz, 1 H, aryl); 6.44 d (J =
7.8 Hz, 1 H, NH); 4.63 m (1 H, CH); 4.64 t (J = 8.7 Hz, 2H, CH2O); 3.90 dd (J = 11.1 Hz / 3.8 Hz, 1 H, CH2OH); 3.82 dd (J
= 11.1 Hz / 5.1 Hz, 1 H, CH2OH); 3.27 t (J = 8.7 Hz, 2H, CH2); 3.21 dd (J
= 15.7 Hz/6.8 Hz, 1H, CHZ); 3.17 dd (J = 15.7 Hz / 6.8 Hz, 1 H, CHZ).

Metho Ex. Product; analoa 'H-NMR (400 MHz) S Structure reagents gousto [ppm]

37 N-[(R)-1-(Hydroxymethyl)-2- (Pyridine-d5): 11.85 s OH
(1 H-indol-3-yl)ethyl]-6- (1 H, NH); 9.64 d (J = 8.3 0 H N
H
methoxy-2-(7- Hz, 1 H, NH); 8.45 s(1 H, o~
methoxybenzofuran-2-yl)- aryl); 8.20 d (J = 9.2 Hz, uinoline-4-carboxamide; 2H, aryl); 8.06 d (J = 2.8 Hz, 1 H, aryl); 7.68 s(1 H, D-Tryptophanol aryl); 7.62 s (1 H, aryl);
and 7.59 d(J = 8.0 Hz, 1 H, aryl); 7.44 dd (J = 9.2 Hz 6-Methoxy-2-(7-methoxy- / 2.8 Hz, 1 H, aryl); 7.33 d benzofuran-2-yl)quinoline-4- (J = 7.8 Hz, 1 H, aryl);
carboxylic acid 7.31 dd (J = 8.0 Hz / 8.0 Hz, 1 H, aryl); 7.29 dd (J
=9.2Hz/8.OHz, 1H, aryl); 7.24 dd (J = 7.8 Hz / 7.8 Hz, 1 H, aryl); 6.93 d (J = 7.8 Hz, 1 H, aryl);
5.37 m (1 H, CH); 4.38 dd (J = 10.9 Hz / 4.5 Hz, 2H, CH2OH); 4.30 dd (J
= 10.9 Hz / 6.0 Hz, 2H, CH2OH); 3.92 s (3H, OCH3); 3.70 s (3H, OCH3); 3.68 m (2H, CHZ).

38 2-[(E)-2-(3,4- 13 (DMSO-d6): 10.80 s H-N &
Dimethoxyphenyl)ethenyl]-N- (1 H); 8.55 d (J = 8.5 Hz, HO \ ~
[(R)-1-(hydroxymethyl)-2-(1 H- 1 H); 7.85 d (J = 9.6 Hz, o H
indol-3-yl)ethyl]-6- 1 H); 7.60 m (3H); 7.33 m -~
~ \ \ N
methoxyquinoline-4- (5H); 7.19 m (2H); 6.98 o carboxamide; m (3H); 4.85 t (J = 5.7 Hz, 1 H); 4.38 m(1 H);
D-Tryptophanol 3.84 s (3H); 3.79 s (3H);

Ex. Product; aMet nahoa 'H-NMR (400 MHz) S Structure reagents gousto IPpm]
=
and 3.68 s (3H); 3.57 t (J
5.7 Hz, 1 H); 3.02 dd (J =
2-[(E)-2-(3,4- 14.9 Hz / 6,2 Hz, 1 H);
Dimethoxyphenyl)ethenyl]-6- 2.91 m (1 H).
ethoxyquinoline-4-carboxylic MS (ESI; +): 538 (M+1).
acid Example 39 N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4'-methoxy[1,1'-biphenyl]-2-carboxamide OH
~
O H I N
H
I

39a) ethyl 4'-methoxy[1,1'-biphenyl]-2-carboxylate 0.66 mmol (100 mg) of 4-methoxyphenylboronic acid, 0.88 mmol (0.88 ml) of a 1 molar solution of tetrabutylammonium fluoride in tetrahydrofuran and 0.044 mmol (51 mg) of tetrakis(triphenylphosphine)palladium(0) were added to a solution of 0.44 mmol (69 pl) of ethyl 2-bromobenzoate in 4.4 ml of toluene and 2.2 ml of ethanol. The mixture was heated to boiling for four hours. After cooling, the reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated in vacuo. Flash chromatography resulted in 107 mg of the target compound.

'H-NMR (400 MHz, CDC13): S[ppm] = 7.79 d (J = 7.8 Hz, 1 H, aryl); 7.50 dd (J =
7.6 Hz /
7.3 Hz, 1 H, aryl); 7.37 dd (J = 7.8 Hz / 7.3 Hz, 1 H, aryl); 7.36 d (J = 7.6 Hz, 1 H, aryl);
7.26 d (J = 8.6 Hz, 1 H, aryl); 6.93 d (J = 8.6 Hz, 1 H, aryl); 4.12 q (J =
7.1 Hz, 2H, OCHz); 3.85 s (3H, OCH3); 1.06 t (J = 7.1 Hz, 3H, CH3).

39b) 4'-methoxy[1,1'-biphenyl]-2-carboxylic acid 0.39 mmol (100 mg) of the compound prepared as in 39a) were stirred in 4 ml of methanol with 2.39 ml of a 2 molar aqueous sodium hydroxide solution at room temperature for 16 hours. The reaction mixture was concentrated in vacuo, acidified to pH 4 with 1 M aqueous hydrochloric acid and stirred for a further hour. 82 mg of the target compound were obtained by filtering off the precipitate with suction.

' H-NMR (400 MHz, CDCI3): S[ppm] = 7.92 d (J = 7.8 Hz, 1 H, aryl); 7.54 dd (J
= 7.6 Hz /
7.6 Hz, 1 H, aryl); 7.39 dd (J = 7.8 Hz / 7.6 Hz, 1 H, aryl); 7.36 d (J = 7.6 Hz, 1 H, aryl);
7.27 d (J = 8.7 Hz, 1 H, aryl); 6.93 d (J = 8.6 Hz, 1 H, aryl); 3.85 s(3H, OCH3).

39c) N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-4'-methoxy[1,1'-biphenyl]-2-carboxamide In analogy to Example 1e), 89 mg of the title compound were obtained from 0.33 mmol (75 mg) of the compound prepared as in 39b) and 0.26 mmol (50 mg) of D-tryptophanol.
'H-NMR (400 MHz, CDC13): S[ppm] = 8.05 s (1 H, NH); 7.63 d (J = 7.8 Hz, 1 H, aryl);
7.54 d (J = 7.8 Hz, 1 H, aryl); 7.44 dd (J = 7.8 Hz / 7.5 Hz, 1 H, aryl); 7.34 d (J = 8.0 Hz, 1 H, aryl); 7.33 dd (J = 7.8 Hz / 7.5 Hz, 1 H, aryl); 7.31 d (J = 7.8 Hz, 1 H, aryl); 7.29 d (J
= 8.8 Hz, 2H, aryl); 7.19 dd (J = 7.8 Hz / 7.1 Hz, 1 H, aryl); 7.09 dd (J =
8.0 Hz / 7.1 Hz, 1 H, aryl); 6.89 d (J = 8.8 Hz, 2H, aryl); 6.84 d (J = 2.3 Hz, 1 H, aryl);
5.61 d (J = 7.6 Hz, 1 H, NH); 4.26 m (1 H, CH); 3.78 s(3H, OCH3); 3.48 m(2H, CH2OH); 2.77 d (J =
6.6 Hz, 2H, CH2).

The following compounds were obtained in analogy to the preparation methods described in detail:

Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents gous to IPpm]

40 N-[(S)-1-(Hydroxymethyl)-2- 39 (CDCI,): 8.15 s(1H, OH
(1 H-indol-3-yI)ethyl]-3',4'- NH); 7.87 s(1 H, aryl); o NH I H
imethoxy[1,1'-biphenyl]-3- 7.73 d (J = 8.0 Hz, 1 H, I
carboxamide; aryl); 7.65 d (J = 7.6 Hz, o 1 H, aryl); 7.51 d (J = 7.6 L-Tryptophanol Hz, 1 H, aryl); 7.40 dd (J
=8.OHz/8.OHz, 1H, and aryl); 7.40 dd (J = 7.6 Hz / 7.6 Hz, 1 H, aryl); 7.22 3;4'-Dimethoxy[1,1'-biphenyl]-dd (J = 8.0 Hz / 8.0 Hz, 3-carboxylic acid 1 H, aryl); 7.15 d (J = 8.0 Hz, 1 H, aryl); 7.12 d(J =
2.1 Hz, 1 H, aryl); 7.09 dd (J = 8.0 Hz / 2.1 Hz, 1 H, aryl); 7.07 s(1 H, aryl);
6.94 d (J = 8.0 Hz, 1 H, aryl); 6.55 d (J = 7.6 Hz, 1H, NH); 4.51 m (1H, CH); 3.94 s (6H, OCH3);
3.85 dd (J = 11.0 Hz /
4.2 Hz, 1 H, CH2OH);
3.80 dd (J = 11.0 Hz /
5.4 Hz, 1 H, CH2OH);
3.18 d (J = 6.7 Hz, 2H, CH2).
Ho = -45.7 (c = 0.980, MeOH / CH2CIZ 1:1) 41 N-[(R)-1-(Hydroxymethyi)-2- 39 OH
(CDC13): 8.14 s (1 H, (1H-indol-3-yl)ethyl]-3',4'- NH); 7.87 s(1H, aryl); H H
dimethoxy[1,1'-biphenyl]-3- 7.73 d (J = 8.0 Hz, 1 H, o carboxamide; aryl); 7.65 d (J = 7.6 Hz, , 1 H, aryl); 7.51 d (J = 7.6 D-Tryptophanol Hz, 1 H, aryl); 7.40 dd (J
= 8.0 Hz / 8.0 Hz, 1 H, Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents gous to [PPm]

and aryl); 7.40 dd (J = 7.6 Hz / 7.6 Hz, 1 H, aryl); 7.22 3', 4'-Dimethoxy(1,1 '-biphenyl]- dd (J = 8.0 Hz / 8.0 Hz, 3-carboxylic acid 1 H, aryl); 7.15 d(J = 8.0 Hz, 1 H, aryl); 7.13 d (J =
2.1 Hz, 1 H, aryl); 7.09 dd (J = 8.0 Hz / 2.1 Hz, 1 H, aryl); 7.07 s(1 H, aryl);
6.94 d(J = 8.0 Hz, 1 H, aryl); 6.55 d (J = 7.6 Hz, 1 H, NH); 4.51 m(1 H, CH); 3.94 s (6H, OCH3);
3.85 dd (J = 11.0 Hz /
4.2 Hz, 1 H, CH2OH);
3.80 dd (J = 11.0 Hz /
5.4 Hz, 1 H, CH2OH);
3.18 d (J = 6.7 Hz, 2H, CHZ).
[a]p = +51.5 (c = 0,690, MeOH / CH2CI2 1:1) 42 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDCI3): 8,20 s(1H, OH
(1H-indol-3-yI)ethyl]-2',3',4'- NH); 7.77 s H a Ioi (1 ry ), H
rimethoxy[1,1'-biphenyl]-3- 7.71 d (J = 7,8 Hz, 1 H, I
carboxamide; aryl); 7.62 d (J = 7.5 Hz, 1 H, aryl); 7.60 d (J = 8.0 D-Tryptophanol Hz, 1 H, aryl); 7.39 dd (J
= 8.0 Hz / 7.5 Hz, 1H, and aryl); 7.36 d (J = 8.3 Hz, 2',3;4'-Trimethoxy(1,1 '- 1 H, aryl); 7.19 dd (J =
biphenyl]-3-carboxylic acid 7,8 Hz / 7.0 Hz, 1 H, aryl);
7.11 dd (J = 8.3 Hz / 7.0 Hz, 1 H, aryl); 7.11 d (J =
2.5 Hz, 1 H, aryl); 6.97 d (J = 8.6 Hz, 1 H, aryl);
6.74 d(J = 8.6 Hz, 1 H, Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents yous to [ppm]

aryl); 6.55 d (J = 7.3 Hz, 1 H, NH); 4.49 m(1 H, CH); 3.94 s (3H, OCH3);
3.91 s (3H, OCH3); 3.80 m (2H, CH2OH); 3.62 s (3H, OCH3); 3,16 d (J
6.8 Hz, 2H, CH2).

43 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDCI3): 8.16 s(1H, H
(1H-indol-3-yi)ethyl]-3',4',5'-tri- NH); 7.90 s(1H, aryl); H N
methoxy[1,1'-biphenyl]-3- 7.72 d (J = 8.0 Hz, 1 H, ~ H
I
aryl); 7.65 d (J = 7.8 Hz, .
carboxamide;
1 H, aryl); 7.53 d (J = 7.8 o Hz, 1 H, aryl); 7.41 dd (J , D-Tryptophanol = 7.8 Hz / 7,8 Hz, 1 H, and aryl); 7.38 d (J = 8.0 Hz, 1 H, aryl); 7.21 dd (J =
3',4',5'-Trimethoxy(1,1 '-bi- 8.0 Hz / 7.0 Hz, 1 H, aryl);
henyl]-3-carboxylic acid 7.12 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 7.12 d(J =
2.3 Hz, 1 H, aryl); 6.74 s (2H, aryl); 6.56 d (J = 6.5 Hz, 1 H, NH); 4.51 m(1 H, CH); 3.91 s (6H, OCH3);
3.90 s (3H, OCH3); 3.82 m (2H, CH2OH); 3.18 d (J = 6.8 Hz, 2H, CHZ).
44 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDCI3): 8.18 s(1H, oH
(1 H-indol-3-yl)ethyl]-3',4',5'-tri- NH); 7.73 d (J = 7,8 Hz, methoxy[1,1'-biphenyl]-4- 1 H, aryl); 7.70 d (J = 8.5 H
carboxamide; Hz, 2H, aryl); 7.54 d (J =
8.5 Hz, 2H, aryl); 7.39 d D-Tryptophanol (J = 8.0 Hz, 1 H, aryl);
~
7.23 dd (J = 7.8 Hz / 7.0 o and Hz, 1 H, aryl); 7.17 dd (J o = 8.0 Hz / 7.0 Hz, 1 H, 3; 4; 5'-Trimethoxy(1,1 '-bi- aryl); 7.12 d (J = 2.3 Hz, 1 H, aryl); 6.76 s (2H, a-henyl]-4-carboxylic acid ryl); 6.54 d (J = 7.5 Hz, Product; Method 'H-NMR (400 MHz) S Structure Ex. rea ents analo-9 gous to [ppm]

1 H, NH); 4.51 m(1 H, CH); 3.92 s (6H, OCH3);
3.89 s (3H, OCH3); 3.82 m (2H, CH2OH); 3.18 d (J = 6,8 Hz, 2H, CH2).
45 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDCI3): 8.24 s(1H, oH
(1 H-indol-3-yl)ethyl]-3',4',5'-tri- NH); 7.74 d (J = 8.0 Hz, o H
methoxy-2-methyl[1,1'- 1 H, aryl); 7.52 m (1 H, H
biphenyl]-4-carboxamide; aryl); 7.48 d (J = 8.0 Hz, 1 H, aryl); 7.39 d (J = 8.0 D-Tryptophanol and Hz, 1 H, aryl); 7.23 d(J =
8.0 Hz, 1 H, aryl); 7.23 dd q o 3 ; 4 ; 5'-Trimethoxy-2- (J = 8.0 Hz / 7.0 Hz, 1 H, o ethy111, 1 ,-biphenylJ-4- aryl); 7.16 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 7.12 d carboxylic acid (J = 2.3 Hz, 1 H, aryl);
6.46 s (2H, aryl); 6.53 d (J = 7.3 Hz, 1 H, NH);
4.50 m(1 H, CH); 3.90 s (3H, OCH3); 3.85 s (6H, OCH3); 3.82 m (2H, CH2OH); 3.18 d (J = 6.8 Hz, 2H, CH2).
46 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDCI3): 8.09 s(1H, OH
(1 H-indol-3-yl)ethyl]-2',3',4'-tri- NH); 7.66 d (J = 7.5 Hz, ,a 0 H N
methoxy[1,1'-biphenyl]-2- 1 H, aryl); 7.56 d (J = 8.0 0~~ ~ H
carboxamide; Hz, 1 H, aryl); 7.44 dd (J o\
=7.5Hz/7.5Hz, 1H, D-Tryptophanol aryl); 7.38 dd (J = 7.5 Hz and / 7.5 Hz, 1 H, aryl); 7.33 d (J = 8.0 Hz, 1 H, aryl);
2',3;4'-Trimethoxyjl,1 '- 7.24 d(J = 7.5 Hz, 1 H, biphenylJ-2-carboxylic acid aryl); 7.18 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 7.08 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 6.92 d (J = 1.5 Ex. Product; aMetho nalotl 'H-NMR (400 MHz) S Structure reagents 9oõS to [ppm]
Hz, 1 H, aryl); 6.86 d (J
=
8.5 Hz, 1 H, aryl); 6.65 d (J = 8.5 Hz, 1 H, aryl);
6.04 d (J = 8.0 Hz, 1 H, NH); 4.26 m(1 H, CH);
3.90 s (3H, OCH3); 3.85 s (3H, OCH3); 3.59 m (1 H, CHZOH); 3.57 s (3H, OCH3); 3.46 m (1 H, CHzOH); 2.84 m (2H, CH2).

47 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDCI3): 8.09 s(1 H, OH
(1 H-indol-3-yl)ethyl]-3',4',5'-tri- NH); 7.65 d (J = 7.5 Hz, "o 0 H N
methoxy[1,1'-biphenyl]-2- 1 H, aryl); 7.54 d (J = 8.0 o~~
carboxamide; Hz, 1 H, aryl); 7.46 dd (J
= 7.5 Hz / 7.5 Hz, 1H, D-Tryptophanol aryl); 7.40 dd (J = 7.5 Hz and / 7.5 Hz, 1 H, aryl); 7.34 d (J = 7.5 Hz, 1 H, aryl);
3',4 ; 5'-Trimethoxy(1,1'-bi- 7.33 d(J = 8.0 Hz, 1 H, henyl)-2-carboxylic acid aryl); 7.17 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 7.07 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 6.75 d (J = 2.5 Hz, 1 H, aryl); 6.59 s (2H, aryl); 5.68 d (J = 7.3 Hz, 1 H, NH); 4.25 m(1 H, CH); 3.87 s (3H, OCH3);
3.83 s (6H, OCH3); 3.50 m (2H, CHZOH); 2.78 d (J = 7.0 Hz, 2H, CHZ).

Ex. Product; aMetho nalo~ 'H-NMR (400 MHz) S Structure reagents 9ous to [ppm]

48 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDCI3): 8.16 s(1H, OH
(1 H-i ndol-3-yl)ethyl]-2', 3',4'-tri- NH); 7.69 d(J= 8.0 Hz, o H N
H
methoxy-6-methyl[1,1'- 1 H, aryl); 7.55 dd (J = 'o biphenyl]-3-carboxamide; 8.0 Hz / 2.0 Hz, 1 H, aryl); 'o \ I \

7.45 d(J = 2.0 Hz, 1 H, ~
D-Tryptophanol aryl); 7.34 d (J = 8.0 Hz, and 1 H, aryl); 7.25 d (J = 8.0 Hz, 1 H, aryl); 7.17 dd (J
2;3;4'-Trimethoxy-6- = 8.0 Hz / 7.0 Hz, 1 H, ethyl11,1'-biphenyl]-3- aryl); 7.08 dd (J = 8.0 Hz carboxylic acid / 7.0 Hz, 1 H, aryl); 7.09 d (J = 2.3 Hz, 1 H, aryl);
6.78 d(J = 8.5 Hz, 1 H, aryl); 6.72 d (J = 8.5 Hz, 1 H, aryl); 6.48 d (J = 7.0 Hz, 1 H, NH); 4.45 m(1 H, CH); 3.93 s (3H, OCH3);
3.92 s (3H, OCH3); 3.79 m (2H, CH2OH); 3.52 s (3H, OCH3); 3.14 m (2H, CH2); 2.19 s (3H, CH3).

49 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDCI3): 8.15 s(1H, OH
(1H-indol-3-yl)ethyl]-3',4',5'-tri- NH); 7.69 d (J = 7,8 Hz, o H N
H
methoxy-6-methyl[1,1'- 1 H, aryl); 7.53 dd (J = ~
~o I
biphenyl]-3-carboxamide; 8.0 Hz / 2.0 Hz, 1 H, aryl); I

7.50 d(J = 2.0 Hz, 1 H, 1 o, D-Tryptophanol aryl); 7.35 d (J = 8.0 Hz, and 1 H, aryl); 7.26 d (J = 8.0 Hz, 1 H, aryl); 7.18 dd (J
3', 4', 5'-Trimethoxy-6- = 8.0 Hz / 7.0 Hz, 1 H, ethyl11,1 '-biphenyl]-3- aryl); 7.07 dd (J = 8.0 Hz carboxylic acid / 7.0 Hz, 1 H, aryl); 7.10 d (J = 2,3 Hz, 1 H, aryl);

Product; Method 'H-NMR (400 MHz) S Structure Ex. rea ents analo-9 yous to Ippml 6,44 s (2H, aryl); 6.49 d (J = 6.8 Hz, 1 H, NH);
4.48 m(1 H, CH); 3.92 s (3H, OCH3); 3.85 s (6H, OCH3); 3.79 m (2H, CH2OH); 3,15 m (2H, CH2); 2,29 s (3H, CH3).

50 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDCI3): 8.21 s(1H, OH -(1H-indol-3-yl)ethyl]-2',3',4'-tri- NH); 7.73 d (J = 8.0 Hz, O H
methoxy[1,1'-biphenyl]-4- 1 H, aryl); 7.68 d (J = 8.5 H
carboxamide; Hz, 2H, aryl); 7.51 d (J = I
8.5 Hz, 2H, aryl); 7.38 d ~o D-Tryptophanol ~
(J = 8.0 Hz, 1 H, aryl); o~
und 7.22 dd (J = 7,8 Hz / 7.0 1 o.
Hz, 1 H, aryl); 7.15 dd (J
2; 3; 4'-Trimethoxy(1,1 '-bi- = 8.0 Hz / 7.0 Hz, 1 H, henylj-4-carboxylic acid aryl); 7.11 d (J = 2,3 Hz, 1 H, aryl); 7.01 d (J = 8.6 Hz, 1 H, aryl); 6.74 d (J =
8.6 Hz, 1 H, aryl); 6.55 d (J = 7.2 Hz, 1 H, NH);
4.51 m(1 H, CH); 3.93 s (3H, OCH3); 3.90 s (3H, OCH3); 3.81 m (2H, CHZOH); 3,64 s (3H, OCH3); 3.17 d (J = 6.8 Hz, 2H, CH2).

Ex. Product; aMet nehoa 'H-NMR (400 MHz) S Structure reagents gous to [PPmI

-51 V-[(R)-1-(Hydroxymethyl)-2- 39 (CDCI3): 8.19 s(1H, OH
(1H-indol-3-yI)ethyl]-2',3',4'- NH); 7.74 d (J = 8.0 Hz, o H
rimethoxy-2-methyl[1,1'- 1 H, aryl); 7.50 s(1 H, a- H
biphenyl]-4-carboxamide; ryl); 7.47 d (J = 8.0 Hz, ~
1 H, aryl); 7.39 d (J = 8.0 o D-Tryptophanol Hz, 1 H, aryl); 7.22 dd (J o and = 8.0 Hz / 7.0 Hz, 1 H, oNI
aryl); 7.19 d (J = 8.0 Hz, 2; 3; 4'-Trimethoxy-2-methyl- 1 H, aryl); 7.16 dd (J =
1,1 '-biphenylJ-4-carboxylic 8.0 Hz / 7.0 Hz, 1 H, aryl);
acid 7.12 d(J = 2.3 Hz, 1 H, aryl); 6.78 d (J = 8.6 Hz, 1 H, aryl); 6.71 d (J = 8.6 Hz, 1 H, aryl); 6.51 d (J =
7.0 Hz, 1H, NH); 4.50 m (1 H, CH); 3.92 s (3H, OCH3); 3.90 s (3H, OCH3); 3.82 m (2H, CHZOH); 3.54 s (3H, OCH3); 3.18 m (2H, CH2); 2.14 s (3H, CH3).

52 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDCI3): 8.07 s(1 H, OH
(1 H-indol-3-yI)ethyl]-2',3',4,4'- NH); 7.56 d (J = 8.0 Hz, o o H N
etramethoxy[1,1'-biphenyl]-2- 1 H, aryl); 7.33 d (J = 8.0 o~~ ~ H
carboxamide; Hz, 1 H, aryl); 7.22 d (J = o.
2.8 Hz, 1 H, aryl); 7.17 dd D-Tryptophanol (J = 7,8 Hz / 7.0 Hz, 1 H, and aryl); 7.14 d (J = 8.5 Hz, 1 H, aryl); 7.08 dd (J =
2;3',4,4'-Tetramethoxy(1,1'- 8.0 Hz / 7.0 Hz, 1 H, aryl);
biphenylJ-4-carboxylic acid 6.98 dd (J = 8.5 Hz / 2.8 Hz, 1 H, aryl); 6.98 d (J =
2.3 Hz, 1 H, aryl); 6.83 d Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents yous to Ippml (J = 8,7 Hz, 1 H, aryl);
6.63 d(J = 8.7 Hz, 1 H, aryl); 6.05 d (J = 7.9 Hz, 1 H, NH); 4.25 m(1 H, CH); 3.90 s (3H, OCH3);
3.83 s (6H, OCH3); 3.58 s (3H, OCH3); 3.58 m (1 H, CH2OH); 3.44 m (1 H, CH2OH); 2.81 m (2H, CH2).

53 N-[(R)-1-(Hydroxymethyl)-2- 39 (DMSO-d6): 10.79 s(1H, OH
/
o (1H-indol-3-yl)ethyl]-3',4,4',5'- NH); 7.81 d (J = 8.1 Hz, o o ~-IH N
etramethoxy[1,1'-biphenyl]-2- 1 H, NH); 7.58 d (J = 7.9 o~
carboxamide; Hz, 1 H, aryl); 7.33 d (J = I ~ I o, 8.5 Hz, 1 H, aryl); 7.32 d D-Tryptophanol (J = 7.6 Hz, 1 H, aryl);
and 7.09 d(J = 2.8 Hz, 1 H, aryl); 7.05 dd (J = 7.6 Hz 3; 4, 4; 5'-Tetramethoxy(1,1 '- / 7.0 Hz, 1 H, aryl); 7.02 biphenyl]-4-carboxylic acid dd (J = 8.5 Hz / 2.8 Hz, 1 H, aryl); 6.96 dd (J =
7.9 Hz / 7.0 Hz, 1 H, aryl);
6,80 d(J = 2,6 Hz, 1 H, aryl); 6,62 s (2H, aryl);
4,01 m (1H, CH); 3.76 s (3H, OCH3); 3.73 s (6H, OCH3); 3.64 s (3H, OCH3); 3.35 m (1 H, CH2OH); 3.25 m (1 H, CH2OH); 2.83 dd (J =
14,3 Hz / 7.0 Hz, 1 H, CH2); 2.71 dd (J = 14,3 Hz / 7.0 Hz, 1 H, CH2).

Ex. Product; eMetho natoa 'H-NMR (400 MHz) S Structure reagents gous to IPpm]

54 '-(Hydroxymethyl)-N-[(R)-1- 39 (CD3OD): 7.66 d (J = 7,8 0"
~ /
(hydroxymethyl)-2-(1 H-indol- Hz, 1 H, aryl); 7.64 dd (J o H 1 N
3-yl)ethyl]-6-methyl[1,1'- = 7.5 Hz / 2.0 Hz, 1 H, H
biphenyl]-3-carboxamide; aryl); 7.58 d (J = 2.0 Hz, 1 H, aryl); 7.43 d (J = 8.5 D -Tryptophanol o"
Hz, 2H, aryl); 7.32 d (J =
and 8.0 Hz, 1 H, aryl); 7.31 d (J = 7.5 Hz, 1 H, aryl);
4' (Hydroxymethyl)-6-methyl- 7.29 d (J = 8.5 Hz, 2H, 1, 1 '-biphenyl]-3-carboxylic aryl); 7.10 s (1 H, aryl);
acid 7.06 dd (J = 7,8 Hz / 7.0 Hz, 1 H, aryl); 6.96 dd (J
= 8.0 Hz / 7.0 Hz, 1H, aryl); 4.67 s (2H, CH2OH); 4.44 m (1 H, CH); 3.68 m (2H, CH2OH); 3.13 dd (J =
14.6 Hz / 6.8 Hz, 1H, CH2); 3.05 dd (J = 14.6 Hz / 8.0 Hz, 1 H, CH2);
2.27 s (3H, CH3).

55 '-(Hydroxymethyl)-N-[(R)-1- 39 (CD3OD): 7.69 d (J = 7,8 OH (hydroxymethyl)-2-(1 H-indol- Hz, 1 H, aryl); 7.63 s(1 H, 3-yI)ethyl]-2-methyl[1,1'- aryl); 7.61 d (J = 7.8 Hz, 0 H H
biphenyl]-4-carboxamide; 1 H, aryl); 7.43 d (J = 8.0 i Hz, 2H, aryl); 7.32 d (J =
o-Tryptophanol 8.3 Hz, 1 H, aryl); 7.28 d i and (J = 8.0 Hz, 2H, aryl);
7.23 d(J = 7.8 Hz, 1 H, OH
4'-(Hydroxymethyl)-2- aryl); 7.12 s(1 H, aryl);
ethyl(1,1 '-biphenyl]-4- 7.08 dd (J = 7.8 Hz / 7.0 carboxylic acid Hz, 1 H, aryl); 7.01 dd (J
= 8.3 Hz / 7.0 Hz, 1H, Ex. Product; aMet nahoa 'H-NMR (400 MHz) S Structure reagents yous to LPpm]
aryl); 4.66 s (2H, CH2OH); 4.46 m (1 H, CH); 3.71 m (2H, CH2OH); 3.16 dd (J =
14.6 Hz / 6.8 Hz, 1 H, CHZ); 3.07 dd (J = 14.6 Hz / 7.0 Hz, 1 H, CH2);
2.26 s (3H, CH3).

56 '-(Hydroxymethyl)-N-[(R)-1- 39 (CD3OD): 7.57 d (J = 7.8 0"
(hydroxymethyl)-2-(1 H-indol- Hz, 1 H, aryl); 7.46 dd (J OH
o H N
H
3-yl)ethyl][1,1'-biphenyl]-2- = 7.3 Hz / 7.3 Hz, 1 H, carboxamide; aryl); 7.38 dd (J = 7.3 Hz / 7.3 Hz, 1 H, aryl); 7.37 d D-Tryptophanol (J = 7.8 Hz, 1 H, aryl);
and 7.35 d (J = 7.3 Hz, 2H, aryl); 7.29 d (J = 8.0 Hz, 4' (Hydroxymethyl)(1,1 '-bi- 2H, aryl); 7.24 d (J = 8.0 henyl]-2-carboxylic acid Hz, 2H, aryl); 7.10 dd (J
=7.8Hz/7.0Hz, 1H, aryl); 6.99 dd (J = 7,8 Hz / 7.0 Hz, 1 H, aryl); 6.97 s (1 H, aryl); 4.56 s (2H, CH2OH); 4.22 m (1H, CH); 3,49 dd (J = 11.0 Hz / 5.2 Hz, 1 H, CH2OH); 3.41 dd (J =
11.0 Hz / 5.7 Hz, 1 H, CH2OH); 2.93 dd (J =
14.6 Hz / 6.5 Hz, 1H, CHZ); 2.81 dd (J = 14.6 Hz / 7.3 Hz, 1 H, CH2).

Ex. Product; aMetho naloa 'H-NMR (400 MHz) 8 Structure reagents 9ous co [ppm]

57 '-(Hydroxymethyl)-N-[(R)-1- 39 (CD30D): 7.95 d (J = 1.8 OH (hydroxymethyl)-2-(1 H-indol- Hz / 1.5 Hz, 1 H, aryI); o H N

3-yl)ethyl][1,1'-biphenyl]-3- 7.75 d (J = 7.8 Hz, 1 H, H
carboxamide; aryl); 7.71 d (J = 7.8 Hz, 1 H, aryI); 7.68 d (J = 7.8 ~-Tryptophanol o"
Hz, 1 H, aryl); 7.61 d(J =
and 8.0 Hz, 2H, aryl); 7.48 dd (J = 7.8 Hz / 7.8 Hz, 1 H, 4'-(Hydroxymethyl)(1,1 '-bi- aryl); 7.45 d (J = 8.0 Hz, henyl]-3-carboxylic acid 2H, aryl); 7.32 d (J = 8.0 Hz, 1 H, aryl); 7.13 s(1 H, aryl); 7.08 dd (J = 7.8 Hz / 7.0 Hz, 1 H, aryl); 6.99 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 4.66 s (2H, CH2OH); 4.47 m (1 H, CH); 3.72 m (2H, CH2OH); 3.17 dd (J =
14,8 Hz / 6.8 Hz, 1 H, CH2); 3.08 dd (J = 14.8 Hz / 7.9 Hz, 1 H, CHZ).

58 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDC13): 7.97 s(1H, OH
(1 H-indol-3-yl)ethyl]-4- NH); 7.54 d (J = 8.0 Hz, o H H
methoxy-3'-(1- 1 H, aryl); 7.33 d(J = 8.0 methylethyl)[1,1'-biphenyl]-2- Hz, 1 H, aryl); 7.32 dd (J o-carboxamide = 8.2 Hz / 7.6 Hz, 1 H, aryl); 7.26 d (J = 8.5 Hz, o-Tryptophanol 1 H, aryl); 7.25 d (J = 8,2 1 H, aryl); 7.22 s(1 H, 4-Methoxy-3'-(1-methylethyl)- Hz, 1,1 '-biphenyl]-2-carboxylic aryl); 7.18 dd (J = 8.0 Hz acid / 7.0 Hz, 1 H, aryl); 7.16 d (J = 7.6 Hz, 1 H, aryl);
7.08 dd (J = 8.0 Hz / 7.0 Ex. Product; aMetho naloa 'H-NMR (400 MHz) 8 Structure reagents 9ous to Ippml Hz, 1H, aryl); 7.01 dd (J
= 8.5 Hz / 2.8 Hz, 1H, aryl); 6.98 d (J = 2.3 Hz, 1 H, aryl); 6.82 d (J = 2.8 Hz, 1 H, aryl); 5.54 d (J =
7.5 Hz, 1 H, NH); 4.20 m (1 H, CH); 3.85 s (3H, OCH3); 3,38 m (2H, CH2OH); 2.93 sept (J =
7.0 Hz, 1 H, CH); 2.70 m (2H, CHZ); 1.26 d (J =
7.0 Hz, 6H, CH3).

59 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDCI3): 8.12 s(1H, oH
(1H-indol-3-yl)ethyl]-3'-(1- NH); 7.88 dd (J- 1.8 Hz 0 H H
methylethyl)[1,1'-biphenyl]-3- / 1,5 Hz, 1 H, aryl); 7.73 d carboxamide; (J = 8.0 Hz, 1 H, aryl); ~ I \
7.69 d (J = 7.5 Hz, 1 H, D-Tryptophanol aryl); 7.57 d (J = 7.3 Hz, and 1 H, aryl); 7.42 dd (J =
7.5 Hz / 7.3 Hz, 1 H, aryl);
3'-(1-Methylethyl)(1,1'- 7.41 s(1H, aryl); 7.38 d biphenylJ-3-carboxylic acid (J = 7.3 Hz, 1 H, aryl);
7.37 dd (J = 7.3 Hz / 7.3 Hz, 1 H, aryl); 7.33 d (J =
7.3 Hz, 1 H, aryl); 7.25 d (J = 8.0 Hz, 1 H, aryl);
7.22 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 7.14 dd (J
= 8.0 Hz / 7.0 Hz, 1H, aryl); 7.12 d (J = 1.8 Hz, 1 H, aryl); 6.54 d (J = 7.0 Hz, 1 H, NH); 4.51 m(1 H, CH); 3.82 m (2H, CH2OH); 2.98 sept (J =
6,8 Hz, 1 H, CH); 3.18 m Ex. Product; aMet nahoa 'H-NMR (400 MHz) S Structure reagents yous to [ppm]

(2H, CH2); 1.30 d (J =
6.8 Hz, 6H, CH3).

60 N-[(R)-1-(Hydroxymethyl)-2- 39 0"
(CDC13): 8.12 s (1 H, (1 H-indol-3-yl)ethyl]-6-methyl- NH); 7.70 d (J = 8.0 Hz, 0 H I H
3'-(1-methylethyl)[1,1'- 1 H, aryl); 7.55 dd (J = I
biphenyl]-3-carboxamide; 7.7 Hz / 2.0 Hz, 1 H, aryl); \ I ~
7.50 d(J = 2.0 Hz, 1 H, D-Ttyptophanol aryl); 7.34 dd (J = 8.0 Hz and / 7,8 Hz, 1 H, aryl); 7.34 d (J = 8.0 Hz, 1 H, aryl);
6-Methyl-3' (1- 7.27 d(J = 8.0 Hz, 1 H, ethylethyl)(1,1 '-biphenyl]-3- aryl); 7.23 d (J = 7.8 Hz, carboxylic acid 1 H, aryl); 7.17 dd (J =
8.0 Hz / 7.0 Hz, 1 H, aryl);
7.12 s(1 H, aryl); 7.09 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 7.09 d (J = 1.8 Hz, 1 H, aryl); 7.06 d (J = 7.7 Hz, 1 H, aryl); 6,48 d (J =
7.0 Hz, 1 H, NH); 4,47 m (1 H, CH); 3.82 dd (J =
11.0 Hz / 3.5 Hz, 1H, CH2OH); 3.76 dd (J =
11.0 Hz / 5.3 Hz, 1H, CH2OH); 3.15 m (2H, CH2); 2.95 sept (J = 7.0 Hz, 1 H, CH); 2.27 s (3H, CH3); 1.29 d (J = 7.0 Hz, 6H, CH3).

Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents gous to [ppm]

61 N-[(R)-1-(Hydroxymethyl)-2- 39 oH
(CDC13): 8.14 s(1 H, I\ ~
(1 H-indol-3-yl)ethyl]-3'-(1 - NH); 7.74 d (J = 8.0 Hz, o H
N
methylethyl)[1,1'-biphenyl]-4- 1 H, aryI); 7.71 d (J = 8.5 H
carboxamide; Hz, 2H, aryl); 7.59 d (J =
8.5 Hz, 2H, aryl); 7.43 s D-Tryptophanol (1 H, aryl); 7.40 d (J = 8.0 and Hz, 1 H, aryl); 7.39 d (J =
8.0 Hz, 1 H, aryl); 7.37 dd 3' (1-Methylethyl)(1,1 '- (J = 8.0 Hz / 8.0 Hz, 1 H, iphenyl]-4-carboxylic acid aryl); 7.26 m(1 H, aryl);
7.23 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 7.16 dd (J
= 8.0 Hz / 7.0 Hz, 1H, aryl); 7.13 d (J = 2.5 Hz, 1 H, aryl); 6.53 d (J = 7.0 Hz, 1 H, NH); 4.51 m(1 H, CH); 3.83 m (2H, CH2OH); 3.19 m (2H, CHZ); 2.98 sept (J = 7.0 Hz, 1 H, CH); 1.30 d(J =
7.0 Hz, 6H, CH3).

62 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDCI3): 8.16 s(1 H, OH (1 H-indol-3-yl)ethyl]-2-methyl- NH); 7.74 d (J = 8.0 Hz, O H
3'-(1-methylethyl)[1,1'- 1H, aryl); 7.47 d(J= 8.0 H
biphenyl]-4-carboxamide; Hz, 1 H, aryl); 7.09 d (J =
8.0 Hz, 1 H, aryl); 7.13 s D-Tryptophanol (1 H, aryl); 7.39 d (J = 8.0 and Hz, 1 H, aryl); 7.23 m (2H, aryl); 7.34 dd (J =
2-Methyl-3' (1- 8.0 Hz / 8.0 Hz, 1H, aryl);
methylethyl)[1,1 '-biphenyl]-4- 7.52 s(1 H, aryl); 7.23 dd carboxylic acid (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 7.17 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 7.13 d Ex. Product; aMetho neloa 'H-NMR (400 MHz) 8 Structure reagents 9ous to [pp-n]
(J = 1,5 Hz, 1 H, aryl);
6.51 d(J = 6.8 Hz, 1 H, NH); 4.50 m(1 H, CH);
3.83 m (2H, CH2OH);
3.18 m (2H, CH2); 2.94 sept (J = 7.0 Hz, 1 H, CH); 2,24 s (3H, CH3);
1.28 d (J = 7.0 Hz, 6H, CH3).

63 i'-(Hydroxymethyl)-N-[(R)-1- 39 (CD3OD): 7.58 d (J = 8.0 0"
/
(hydroxymethyl)-2-(1 H-indol- Hz, 1 H, aryl); 7.34 d (J = H o H I N
3-yI)ethyl]-4-methoxy[1,1'-bi- 8.0 Hz, 1 H, aryl); 7.27 d ~ I H
phenyl]-2-carboxamide; (J = 8.3 Hz, 1 H, aryl); o.~
7.25 d (J = 8.3 Hz, 2H, D-Tryptophanol aryl); 7.21 d (J = 8.3 Hz, and 2H, aryl); 7.09 dd (J =
7.8 Hz / 7.0 Hz, 1 H, aryl);
4'-(Hydroxymethyl)-4- 7.02 d (J = 8.3 Hz, 1 H, ethoxy[l,1 '-biphenyl]-2- aryl); 7.00 dd (J = 7.8 Hz carboxylic acid / 7.0 Hz, 1 H, aryl); 6.98 s (1 H, aryl); 6.89 d (J = 2.8 Hz, 1 H, aryl); 4.55 s (2H, CH2OH); 4.22 m (1 H, CH); 3.79 s (3H, OCH3);
3.50 dd (J = 10.8 Hz /
5,1 Hz, 1 H, CHZOH);
3.43 dd (J = 10.8 Hz /
5,6 Hz, 1H, CH2OH);
2.94 dd (J = 14.7 Hz /
6,3 Hz, 1 H, CH2); 2.82 dd (J = 14.7 Hz / 7.6 Hz, 1H, CHZ).

Ex. Product; aMetho na oa 'H-NMR (400 MHz) S Structure reagents yous to [ppm]

64 3',4',5'-Trifluoro-N-[(R)-1- 39 (CD3OD): 7.59 d (J = 8.0 OH
-/
(hydroxymethyl)-2-(1 H-indol- Hz, 1 H, aryl); 7.49 dd (J F 0 HI N
3-yI)ethyl][1,1'-biphenyl]-2- = 7.3 Hz / 7.3 Hz, 1 H, F I H
carboxamide; aryl); 7.39 dd (J = 7.3 Hz / 7.3 Hz, 1 H, aryl); 7.34 d D-Tryptophanol (J = 8.0 Hz, 1 H, aryl);
and 7.34 d(J = 7.3 Hz, 1 H, aryl); 7.32 d (J = 7.3 Hz, 3; 4; 5'-Trifluoro(1,1 '-biphenyl]- 1H, aryl); 7.11 m (2H, 2-carboxylic acid aryl); 7.11 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 7.06 d (J = 1.8 Hz, 1 H, aryl);
6.99 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 4.27 m (1H, CH); 3.53 m (2H, CHzOH); 3.00 dd (J =
15.1 Hz / 6.8 Hz, 1 H, CHZ); 2.87 dd (J = 15.1 Hz / 6.8 Hz, 1 H, CHz).

65 3',4',5'-Trifluoro-N-[(R)-1- 39 (CD30D): 7.88 s(1H, OH
-(hydroxymethyl)-2-(1 H-indol- aryl); 7.78 d (J = 7.7 Hz, 0 H N
3-yI)ethyl][1,1'-biphenyl]-3- 1 H, aryl); 7.75 d (J = 7.7 H
carboxamide; Hz, 1 H, aryl); 7.66 d (J = F I
8.0 Hz, 1 H, aryl); 7.51 dd F
D-Tryptophanol F
(J = 7.7 Hz / 7.7 Hz, 1 H, and aryl); 7.42 m (2H, aryl);
7.32 d(J = 8. 0 Hz, 1 H, 3;4;5'-Trifluoro[l,1'-biphenyl]- aryl); 7.12 d(J= 1.8 Hz, 3-carboxylic acid 1 H, aryl); 7.06 dd (J =
8.0 Hz / 7.0 Hz, 1 H, aryl);
6.97 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 4,48 m (1 H, CH); 3.72 m (2H, Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents yous to LPpm]
CH2OH); 3.16 dd (J =
14.5 Hz / 6.4 Hz, 1 H, CHz); 3.07 dd (J = 14.5 Hz / 7.2 Hz, 1 H, CH2).

66 3',4',5'-Trifluoro-N-[(R)-1- 39 (CD,OD): 7.68 dd (J = o"
I
(hydroxymethyl)-2-(1 H-indol- 7.9 Hz / 1.9 Hz, 1 H, aryI); o N
3-yI)ethyl]-6-methyl[1,1'- 7.64 d (J = 8.0 Hz, 1 H, H
biphenyl]-3-carboxamide; aryl); 7.50 d (J = 1.9 Hz, F 1 H, aryI); 7.35 d (J =
7.9 F

D-Tryptophanol Hz, 1 H, aryl); 7.30 d (J = F
8.0 Hz, 1 H, aryl); 7.10 m and (2H, aryl); 7.10 d (J = 1.8 Hz, 1 H, aryl); 7.04 dd (J
3;4;5'-Trifluoro-6-methyl(1,1 ' = 8.0 Hz / 7.0 Hz, 1 H, 5iphenyl]-3-carboxylic acid aryl); 6.94 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 4,44 m(1 H, CH); 3.69 m(2H, CH2OH); 3.13 dd (J =
14.5 Hz / 6.7 Hz, 1 H, CH2); 3.04 dd (J = 14.5 Hz / 7.2 Hz, 1 H, CH2);
2.29 s (3H, CH3).
67 3',4',5'-Trifluoro-N-[(R)-1- 39 (CD3OD): 7,84 d(J - 8,7 oH
(hydroxymethyl)-2-(1 H-indol- Hz, 2H, aryl); 7.67 d (J =
O NH I N
3-yI)ethyl][1,1'-biphenyl]-4- 8,7 Hz, 2H, aryl); 7.67 d H
carboxamide; (J = 8.0 Hz, 1 H, aryl);
7.46 m(2H, aryl); 7.32 d D-Tryptophanol (J = 8.0 Hz, 1 H, aryl);
7.11 d (J = 1.8 Hz, 1 H, and aryl); 7.08 dd (J = 8.0 Hz F
F F
/ 7.0 Hz, 1 H, aryl); 7.00 3; 4; 5'-Trifluoro[l,1 '-biphenyl]- dd (J = 8.0 Hz / 7.0 Hz, 4-carboxylic acid 1 H, aryl); 4.47 m(1 H, CH); 3.71 m (2H, CH2OH); 3.16 dd (J =
15,1 Hz / 6.8 Hz, 1 H, Ex. Product; aMetho nalo~ 'H-NMR (400 MHz) S Structure reagents 9oõS to [ppm]

CH2); 3.06 dd (J = 15.1 Hz / 7.3 Hz, 1 H, CH2).
68 3',4',5'-Trifluoro-N-[(R)-1- 39 (CD3OD): 7.68 d (J - 7.7 OH (hYdroxYmethYI)-2-(1 H-indol- Hz, 1 H, arYI); 7.64 s (1 H, 3-yI)ethyl]-2-methyl[1,1'- aryl); 7.63 d (J = 8.0 Hz, H
biphenyl]-4-carboxamide; 1 H, aryl); 7.32 d (J = 8.0 Hz, 1 H, aryl); 7.25 d(J =
D-Tryptophanol 7.7 Hz, 1 H, aryl); 7.11 m ~
(2H, aryl); 7.08 dd (J = F~ F
and 8.0 Hz / 7.0 Hz, 1 H, aryl); F
7.08 d(J = 1.8 Hz, 1 H, 3; 4; 5' Trifluoro-2-methyl(1,1 '- aryl); 7.00 dd (J = 8.0 Hz biphenyl]-4-carboxylic acid / 7.0 Hz, 1 H, aryl); 4.46 m(1 H, CH); 3.71 m(2H, CH2OH); 3,16 dd (J =
14.8 Hz / 7.2 Hz, 1 H, CHZ); 3.07 dd (J = 14.8 Hz / 7.3 Hz, 1 H, CH2);
2.28 s (3H, CH3).

69 N-[(R)-1-(Hydroxymethyl)-2- 39 (CD30D): 7.57 d (J = 8.0 OH (1 H-indol-3-yl)ethyl]-2',5'- Hz, 1 H, aryl); 7.51 d (J = o o H' N
dimethoxy[1,1'-biphenyl]-2- 7.5 Hz, 1 H, aryl); 7.47 dd ~ I H
L~
carboxamide; (J = 7.5 Hz / 7.5 Hz, 1 H, o~
aryl); 7.38 dd (J = 7.5 Hz o-Tryptophanol / 7.5 Hz, 1 H, aryl); 7.31 d und (J = 8.0 Hz, 1 H, aryl);
7.26 d(J = 7.5 Hz, 1 H, 2;5'-Dimethoxy[1,1'-biphenyl]- aryl); 7.07 dd (J = 8.0 Hz 2-carboxylic acid / 7.0 Hz, 1 H, aryl); 6.98 d (J = 1.8 Hz, 1 H, aryl);
6.97 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 6.86 m (2H, aryl); 6.77 s (1 H, aryl); 4.16 m(1 H, CH);
3.73 s (3H, OCH3); 3.60 s (3H, OCH3); 3.39 dd (J

Ex. Product; aMet nahoa 'H-NMR (400 MHz) S Structure reagents gous to [ppm]

= 10,9 Hz / 4.5 Hz, 1H, CH2OH); 3.30 dd (J =
10.9 Hz / 5.3 Hz, 1 H, CH2OH); 2.80 dd (J =
14.7 Hz / 7.6 Hz, 1 H, CHz); 2.71 dd (J = 14.7 Hz / 5.8 Hz, 1 H, CH2).

70 N-[(R)-1-(Hydroxymethyl)-2- 39 (CD3OD): 7.57 d (J = 8.0 0"
. /
(1 H-indol-3-yl)ethyl]-2',4.5'-tri- Hz, 1 H, aryl); 7.31 d (J = o O H ~ N
methoxy[1,1'-biphenyl]-2- 8.0 Hz, 1 H, aryl); 7.17 d H
carboxamide; (J = 8.8 Hz, 1 H, aryl); 01~ o.
7.07 dd (J = 8.0 Hz / 7.0 D-Tryptophanol Hz, 1 H, aryl); 7.03 s(1 H, and aryl); 7.02 dd (J = 8,8 Hz / 2.8 Hz, 1 H, aryl); 6.98 d 2;4.5' Trimethoxy(1,1'- (J = 1.8 Hz, 1 H, aryl);
iphenyl]-2-carboxylic acid 6.97 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 6.85 d(J =
8.6 Hz, 1 H, aryl); 6.83 dd (J = 8.6 Hz / 2.5 Hz, 1 H, aryl); 6.75 d (J = 2.5 Hz, 1 H, aryl); 4.15 m(1 H, CH); 3.81 s (3H, OCH3);
3.73 s (3H, OCH3); 3.60 s (3H, OCH3); 3.40 dd (J
= 10.9 Hz / 4.5 Hz, 1 H, CH2OH); 3.31 m (1 H, CH2OH); 2.80 dd (J =
14.4 Hz / 7.6 Hz, 1 H, CH2); 2.72 dd (J = 14.4 Hz / 6.3 Hz, 1 H, CH2).

Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents yous to IPpm]

71 V-[(R)-1-(Hydroxymethyl)-2- 39 (DMSO-ds): 10.74 s(1H, o"
(1 H-indol-3-yl)ethyl]-2',5'- NH); 8.10 d (J = 8.1 Hz, o " N
dimethoxy-6-methyl[1,1'- 1 H, NH); 7.73 dd (J = 7.8 o H
biphenyl]-3-carboxamide; Hz / 1.8 Hz, 1 H, aryl);
7.63 d(J = 8. 0 Hz, 1 H, D-Tryptophanol aryl); 7.62 s (1 H, aryl); .
7.30 d(J = 8.0 Hz, 1 H, and aryl); 7.30 d (J = 7,8 Hz, 2;4.5' Trimethoxy(1,1 '- 1 H, aryl); 7.10 d (J = 1.8 iphenyl]-2-carboxylic acid Hz, 1 H, aryl); 7.03 dd (J
= 8.0 Hz / 7.0 Hz, 1H, aryl); 7.03 d (J = 8.8 Hz, 1 H, aryl); 6.95 dd (J =
8.8 Hz / 3.0 Hz, 1 H, aryl);
6.94 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 6.69 d (J =
3.0 Hz, 1 H, aryl); 4.23 m (1 H, CH); 3.74 s (3H, OCH3); 3.64 s (3H, OCH3); 3.50 m (1 H, CH2OH); 3.44 m (1 H, CHZOH); 2.99 dd (J =
14.7 Hz / 6,1 Hz, 1 H, CHZ); 2.89 dd (J = 14.7 Hz / 7.8 Hz, 1 H, CHZ).

72 N-[(R)-1-(Hydroxymethyl)-2- 39 (CD3OD): 7.78 d(J - 8.6 0"
(1 H-i ndol-3-yl)ethyl]-2', 5'- Hz, 2H, aryl); 7.69 d (J = o H N
dimethoxy[1,1'-biphenyl]-4- 8.0 Hz, 1 H, aryl); 7.55 d H
I
carboxamide; (J = 8.6 Hz, 2H, aryl);
7.32 d(J = 8.0 Hz, 1 H, D-Tryptophanol aryl); 7.12 d(J = 1.8 Hz, o.
and 1 H, aryl); 7.08 dd (J =
8.0 Hz / 7.0 Hz, 1 H, aryl);
2;5'-Dimethoxy[1,1 '-biphenyl]- 7.01 d (J = 8.6 Hz, 1 H, Ex. Product; Mnalotl 'H-NMR (400 MHz) S Structure reagents 9ous to Ippm]
4-carboxylic acid aryl); 7.00 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 6.91 dd (J = 8.6 Hz / 3.0 Hz, 1 H, aryl); 6.87 d (J = 3.0 Hz, 1 H, aryl); 4.46 m (1 H, CH); 3.78 s (3H, OCH3); 3.72 s (3H, OCH3); 3.71 m (2H, CH2OH); 3.16 dd (J =
14.4 Hz / 6,8 Hz, 1 H, CH2); 3.07 dd (J = 14.4 Hz / 7.1 Hz, 1 H, CH2).
73 N-[(R)-1-(Hydroxymethyl)-2- 39 (CD3OD): 7.69 d (J = 8.0 oH
(1 H-indol-3-yl)ethyl]-2',5'- Hz, 1 H, aryl); 7.59 s(1 H, O H I
H
dimethoxy-2-methyl[1,1'- aryl); 7.58 d (J = 7,8 Hz, biphenyl]-4-carboxamide; 1 H, aryl); 7.33 d (J = 8.0 Hz, 1 H, aryl); 7.15 d(J =
~-Tryptophanol "
7.8 Hz, 1 H, aryl); 7.13 d ~

and (J = 1.8 Hz, 1 H, aryl);
7.09 dd (J = 8.0 Hz / 7.0 2; 5'-Dimethoxy-2-methyl(1,1 '- Hz, 1H, aryl); 7.01 dd (J
iphenylj-4-carboxylic acid = 8.0 Hz / 7.0 Hz, 1 H, aryl); 6.98 d (J = 9.1 Hz, 1 H, aryl); 6.92 dd (J =
9.1 Hz / 3.0 Hz, 1 H, aryl);
6.65 d (J = 3.0 Hz, 1 H, aryl); 4,45 m(1 H, CH);
3.76 s (3H, OCH3); 3.70 m (2H, CH2OH); 3.66 s (3H, OCH3); 3.16 dd (J =
14.4 Hz / 6.3 Hz, 1 H, CHZ); 3.07 dd (J = 14.4 Hz / 6.6 Hz, 1 H, CH2);
2.12 s (3H, CH3).

Method ' Ex. Product; anaio- H-NMR (400 MHz) S Structure reagents gous to [ppm]

74 V-[(R)-1-(Hydroxymethyl)-2- 39 (CD3OD): 7.58 d (J = 8.0 OH
(1 H-indol-3-yl)ethyl]-3',4'- Hz, 1 H, aryl); 7.49 - 7.31 0 0 H
H
imethoxy[1,1'-biphenyl]-2- m (4H, aryl); 7.35 d (J = 'o I I
carboxamide; 8.0 Hz, 1 H, aryl); 7.09 dd (J = 8.0 Hz / 7.0 Hz, 1H, D-Tryptophanol aryl); 7.00 d (J = 1.8 Hz, and 1 H, aryl); 6.99 dd (J =
8.0 Hz / 7.0 Hz, 1 H, aryl);
3; 4 '-Dimethoxy[l, 1 ' biphenyl]- 6.96 d (J = 2.1 Hz, 1 H, 2-carboxylic acid aryl); 6.77 dd (J = 8.3 Hz / 2.1 Hz, 1 H, aryl); 6.71 d (J = 8.3 Hz, 1 H, aryl);
4.21 m(1 H, CH); 3.78 s (3H, OCH3); 3.77 s (3H, OCH3); 3.47 dd (J = 11,1 Hz / 5.3 Hz, 1 H, CH2OH); 3.40 dd (J =
11.1 Hz / 5.7 Hz, 1 H, CH2OH); 2.91 dd (J =
14.5 Hz / 7.0 Hz, 1 H, CHZ); 2,78 dd (J = 14.5 Hz / 7.0 Hz, 1 H, CH2).

75 N-[(R)-1-(Hydroxymethyl)-2- 39 0"
(CD30D): 7.58 d (J = 8.0 (1 H-indol-3-yl)ethyl]-3',4,4'-tri- Hz, 1 H, aryl); 7.34 d (J = o 1 o H H
methoxy[1,1'-biphenyl]-2- 8.0 Hz, 1 H, aryl); 7.27 d '-o carboxamide; (J = 8.7 Hz, 1 H, aryl);
7.09dd(J=8.OHz/7.0 D-Tryptophanol Hz, 1 H, aryl); 7.01 d (J =
and 2.6 Hz, 1 H, aryl); 7.00 dd (J = 8.7 Hz / 2.6 Hz, 1 H, 3;4,4' Trimethoxy(1,1 '- aryl); 6.99 dd (J = 8.0 Hz biphenyl]-2-carboxylic acid / 7.0 Hz, 1 H, aryl); 6.92 d (J = 1.8 Hz, 1 H, aryl);

Ex. Product; aMet nahoa 'H-NMR (400 MHz) S Structure reagents 9ous to [ppm]

6.90 d(J = 2.6 Hz, 1 H, aryl); 6.74 dd (J = 8.3 Hz / 1.8 Hz, 1 H, aryl); 6.70 d (J = 8.3 Hz, 1 H, aryl);
4.21 m(1 H, CH); 3.79 s (3H, OCH3); 3.78 s (3H, OCH3); 3.76 s (3H, OCH3); 3.47 dd (J = 11.1 Hz / 5.3 Hz, 1 H, CH2OH); 3.41 dd (J =
11.1 Hz / 5,7 Hz, 1H, CH2OH); 2.91 dd (J =
14.5 Hz / 6.2 Hz, 1H, CH2); 2.78 dd (J = 14.5 Hz / 7.0 Hz, 1 H, CH2).

76 N-[(R)-1-(Hydroxymethyl)-2- 39 (CD3OD): 7.65 d (J - 8.0 oH
(1 H-indol-3-yl)ethyl]-3',4'- Hz, 1 H, aryl); 7.62 dd (J 0 H H
dimethoxy-6-methyl[1,1'- = 7.9 Hz / 1.9 Hz, 1 H, i ~
biphenyl]-3-carboxamide; aryl); 7.59 d (J = 1.9 Hz, 0' I
'0 1 H, aryl); 7.31 d (J = 7.9 D-Tryptophanol Hz, 1 H, aryl); 7.30 d (J =
and 8.0 Hz, 1 H, aryl); 7.10 d (J = 1.8 Hz, 1 H, aryl);
3; 4'-Dimethoxy-6-methyl(1,1 '- 7.05 dd (J = 8.0 Hz / 7.0 iphenylJ-2-carboxylic acid Hz, 1 H, aryl); 7.02 d (J =
8.1 Hz, 1 H, aryl); 6.95 dd (J = 8.0 Hz / 7.0 Hz, 1H, aryl); 6.89 d (J = 2.1 Hz, 1 H, aryl); 6.85 dd (J =
8.1 Hz / 2.1 Hz, 1 H, aryl);
4.44 m(1 H, CH); 3.88 s (3H, OCH3); 3.84 s (3H, OCH3); 3.68 m (2H, CH2OH); 3.13 dd (J =
14.3 Hz / 6.2 Hz, 1 H, Ex. Product; aMetho neloa 'H-NMR (400 MHz) S Structure reagents gous to [ppm]

CH2); 3.05 dd (J = 14.3 Hz / 7.2 Hz, 1 H, CH2).;
2.29 s (3H, CH3) 77 N-[(R)-1-(Hydroxymethyl)-2- 39 (CD3OD): 7.81 d (J = 8.7 OH (1 H-indol-3-yI)ethyl]-3',4'- Hz, 2H, aryl); 7.68 d (J =
O H
dimethoxy[1,1'-biphenyl]-4- 8.0 Hz, 1 H, aryl); 7.65 d H
carboxamide;
(J = 8.7 Hz, 2H, aryl);
7.32 d(J = 8. 0 Hz, 1 H, o-Tryptophanol aryl); 7.23 d (J = 1.7 Hz, and 1 H, aryl); 7.22 dd (J = eo 9.0 Hz / 1.7 Hz, 1 H, aryl);
3', 4'-Dimethoxy[1,1 '-biphenyl]- 7.12 d (J = 1.8 Hz, 1 H, 4-carboxylic acid aryl); 7.08 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 7.04 d (J = 9,0 Hz, 1 H, aryl);
7.00 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 4.47 m (1 H, CH); 3.90 s (3H, OCH3); 3.87 s (3H, OCH3); 3.71 m (2H, CH2OH); 3.16 dd (J =
14.7 Hz / 6.6 Hz, 1 H, CH2); 3.08 dd (J = 14,7 Hz / 7.3 Hz, 1 H, CHZ).

78 N-[(R)-1-(Hydroxymethyl)-2- 39 (CD3OD): 7.69 d(J= 8.0 oH -(1 H-indol-3-yI)ethyl]-3',4'- Hz, 1 H, aryl); 7.62 s(1 H, o H
dimethoxy-2-methyl[1,1'- aryl); 7.60 d (J = 7.9 Hz, H
biphenyl]-4-carboxamide; 1 H, aryl); 7.33 d (J = 8.0 Hz, 1 H, aryl); 7.24 d (J =
D-Tryptophanol 7.9 Hz, 1 H, aryl); 7.13 d o and (J = 1.8 Hz, 1 H, aryl); ~O
7.08dd(J=8.OHz/7.0 Ex. Product; aMet nahoa 'H-NMR (400 MHz) 8 Structure reagents gousto Ippm]
3; 4'-Dimethoxy-2-methyl(1,1'- Hz, 1 H, aryl); 7.02 d (J =
iphenylJ-4-carboxylic acid 8= 1 Hz, 1 H, aryl); 7.01 dd (J = 8.0 Hz / 7.0 Hz, 1H, aryl); 6,86 dd (J = 8.1 Hz / 2.1 Hz, 1 H, aryl); 6,80 d (J = 2.1 Hz, 1 H, aryl);
4.46 m(1 H, CH); 3.87 s (3H, OCH3); 3.84 s (3H, OCH3); 3.71 m (2H, CH2OH); 3,16 dd (J =
14.7 Hz / 7.0 Hz, 1 H, CH2); 3.07 dd (J = 14,7 Hz / 6.8 Hz, 1 H, CHZ);
2.29 s (3H, CH3).

79 3'-Fluoro-N-[(R)-l-(hydroxy- 39 (CD3OD): 7.60 d (J = 8.0 OH methyl)-2-(1 H-indol-3-yl)ethyl]- Hz, 1 H, aryl); 7.45 m o~ 0 H N

'-methoxy[1,1'-biphenyl]-2- (1 H, aryl); 7.35 m (3H, F H
carboxamide; aryl); 7.33 d (J = 8.0 Hz, 1 H, aryl); 7.12 dd (J =
o-Tryptophanol 12.4 Hz / 2.2 Hz, 1 H, and aryl); 7.10 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 7.06 d 3'-Fluoro-4'-methoxy[1,1'- (J = 1.8 Hz, 1 H, aryl);
biphenyl]-2-carboxylic acid 7.00 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 6.89 ddd (J
= 8.5 Hz / 2.2 Hz / 1.1 Hz, 1 H, aryl); 6.73 dd (J
= 8.7 Hz / 8.5 Hz, 1H, aryl); 4.25 m(1 H, CH);
3.79 s (3H, OCH3); 3.54 dd (J = 11.0 Hz / 5.3 Hz, 1H, CH2OH); 3.47 dd (J
= 11.0 Hz / 5.8 Hz, 1 H, CH2OH); 2.98 dd (J =

Ex. Product; aMet nahoa 'H-NMR (400 MHz) S Structure reagents gous to [ppm]

14.7 Hz / 6.4 Hz, 1 H, CH2); 2.83 dd (J = 14.7 Hz / 7.5 Hz, 1 H, CH2).

80 3'-Fluoro-N-[(R)-1-(hydroxy- 39 (CD3OD): 7.60 d(J - 8.0 oH --/
methyl)-2-(1 H-indol-3-yI)ethyl]- Hz, 1 H, aryl); 7.36 d (J = o o H~ N
I,4'-dimethox 1,1'-bi hen I - ~ I H
Y[ P Y] 8.0 Hz, 1 H, aryl); 7.24 d F
2-carboxamide; (J = 8.5 Hz, 1 H, aryl);
7.09 dd (J = 8.0 Hz / 7.0 D-Tryptophanol Hz, 1 H, aryl); 7.08 d (J =
and 11.3 Hz, 1 H, aryI); 7.06 d (J = 1.8 Hz, 1 H, aryl);
3 '-Fluoro-4,4 '-dimethoxy(1,1 '- 7.00 dd (J = 8.0 Hz / 7.0 iphenyl]-2-carboxylic acid Hz, 1 H, aryl); 7.00 dd (J
= 8.5 Hz / 2,6 Hz, 1 H, aryl); 6.86 d (J = 2.6 Hz, 1 H, aryl); 6.85 ddd (J =
8.7 Hz / 2.1 Hz / 1,1 Hz, 1 H, aryl); 6.72 dd (J =
8.7 Hz / 8.7 Hz, 1 H, aryl);
4.25 m(1 H, CH); 3.79 s (3H, OCH3); 3.78 s (3H, OCH3); 3.54 dd (J = 11.0 Hz / 5.3 Hz, 1 H, CHZOH); 3.48 dd (J =
11.0 Hz / 5.8 Hz, 1 H, CHZOH); 2.98 dd (J =
14.7 Hz / 6.3 Hz, 1 H, CH2); 2.84 dd (J = 14.7 Hz / 7.5 Hz, 1 H, CHZ).

81 3'-Fluoro-N-[(R)-1-(hydroxy- 39 (CD3OD): 7.90 dd (J = OH
methyl)-2-(1 H-indol-3-yI)ethyl]- 1,7 Hz / 1.5 Hz, 1 H, aryl); 0 H N
H
'-methoxy[1,1'-biphenyl]-3- 7.71 d (J = 7.9 Hz, 1 H, carboxamide; aryl); 7.69 d (J = 7.7 Hz, F~ I \
"0 1 H, aryl); 7.68 d (J = 8.0 Method ' Ex. Product; anaio- H-NMR (400 MHz) S Structure reagents gous to [ppm]

D-Tryptophanol Hz, 1 H, aryl); 7.46 dd (J
= 7.9 Hz / 7.7 Hz, 1H, and aryl); 7.42 d (J = 9.0 Hz, 1 H, aryl); 7.39 d(J =
3' Fluoro-4' methoxy(1,1 ' bi- 10.2 Hz, 1 H, aryl); 7.32 d henyl]-3-carboxylic acid (J = 8.0 Hz, 1 H, aryl);
7.16 dd (J = 9.0 Hz / 8.5 Hz, 1 H, aryl); 7.12 d (J =
1.8 Hz, 1 H, aryl); 7.08 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 6.98 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 4.47 m(1 H, CH); 3.92 s (3H, OCH3); 3.72 m (2H, CH2OH); 3.16 dd (J =
15,1 Hz / 6.8 Hz, 1 H, CHZ); 3.07 dd (J = 15.1 Hz / 7.5 Hz, 1 H, CH2).

82 3'-Fluoro-N-[(R)-1-(hydroxy- 39 (CD3OD): 7.65 d (J = 8.0 OH
methyl)-2-(1 H-indol-3-yI)ethyl]- Hz, 1 H, aryl); 7.63 dd (J 0 H N
H
1'-methoxy-6-methyl[1,1'- = 7.9 Hz / 2.1 Hz, 1 H, ~ I
biphenyl]-3-carboxamide; aryl); 7.55 d(J = 2.1 Hz, .1o 1 H, aryl); 7.31 d (J = 8.0 o-Tryptophanol Hz, 1 H, aryl); 7.31 d (J =
and 7.9 Hz, 1 H, aryl); 7.15 dd (J = 9.0 Hz / 8.3 Hz, 1 H, 3'-Fluoro-4'-methoxy-6- aryl); 7.10 d (J = 1.8 Hz, ethyl(1,1'-biphenyl]-3- 1 H, aryl); 7.06 dd (J =
carboxylic acid 8.0 Hz / 7.0 Hz, 1 H, aryl);
7.06 m (2H, aryl); 6.96 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 4,43 m(1 H, CH); 3.92 s (3H, OCH3);

Ex. Product; aMetho naloa 'H-NMR (400 MHz) 8 Structure reagents gous to [ppm]
3.72 m (2H, CH2OH);
3.13dd(J=14.9Hz/
7.3 Hz, 1 H, CH2); 3.05 dd (J = 14.9 Hz / 6.6 Hz, 1H, CH2); 2.28 s (3H, CH3).

83 3'-Fluoro-N-[(R)-1-(hydroxy- 39 (CD3OD): 7.81 d (J = 8.7 OH methyl)-2-(1 H-indol-3-yl)ethyl]- Hz, 2H, aryl); 7.68 d(J =

'-methoxy[1,1'-biphenyl]-4- 8.0 Hz, 1 H, aryl); 7.63 d 0 H H
carboxamide; (J = 8.7 Hz, 2H, aryl);
7.42 m (2H, aryl); 7.32 d D-Tryptophanol (J = 8.0 Hz, 1 H, aryl);

7.16 dd (J = 8,7 Hz / 8.5 F
and Hz, 1 H, aryl); 7.12 d (J =
3'-Fluoro-4'-methoxy(1,1'- 1.8 Hz, 1 H, aryl); 7.08 dd biphenyl]-4-carboxylic acid (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 7.00 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 4.47 m(1 H, CH); 3.91 s(3H, OCH3); 3.71 m (2H, CH2OH); 3.16 dd (J =
15.1 Hz / 6,8 Hz, 1 H, CH2); 3.07 dd (J = 15.1 Hz / 7.7 Hz, 1 H, CHZ).

84 3'-Fluoro-N-[(R)-1-(hydroxy- 39 (CD30D): 7.68 d (J = 8.0 OH methyl)-2-(1 H-indol-3-yl)ethyl]- Hz, 1 H, aryl); 7.62 s(1 H, O H I N
'-methoxy-2-methyl[1,1'- aryl); 7.60 dd (J = 9.2 Hz H
biphenyl]-4-carboxamide; / 1.3 Hz, 1 H, aryl); 7.32 d (J = 8.0 Hz, 1 H, aryl);
D-Tryptophanol 7.22 d (J = 9,2 Hz, 1 H, and aryl); 7.15 dd (J = 8,7 Hz F
/ 8.5 Hz, 1 H, aryl); 7.12 d Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents 9ous to [ppm]

3' Fluoro-4' methoxy-2- (J = 1.8 Hz, 1 H, aryl);
ethyl[1,1 '-biphenyl]-4- 7.08 dd (J = 8.0 Hz / 7.0 carboxylic acid Hz, 1 H, aryl); 7.06 m (2H, aryl); 7.01 dd (J =
8.0 Hz / 7.0 Hz, 1 H, aryl);
4.46 m(1 H, CH); 3.91 s (3H, OCH3); 3.71 m (2H, CH2OH); 3.15 dd (J =
14,7 Hz / 7.0 Hz, 1 H, CH2); 3.05 dd (J = 14,7 Hz / 7.0 Hz, 1 H, CH2);
2.27 s (3H, CH3).

85 N-[(R)-1-(Hydroxymethyl)-2- 39 (CD3OD): 7.57 d (J = 8.0 0" ~
(1 H-indol-3-yl)ethyl]-3',4- Hz, 1 H, aryl); 7.33 d (J J = o H
~ H
dimethoxy[1,1'-biphenyl]-2- 8.0 Hz, 1 H, aryl); 7.29 d o~ I ~
carboxamide; (J = 8.5 Hz, 1 H, aryl);
7.16 dd (J = 7.9 Hz / 7.9 D-Tryptophanol Hz, 1 H, aryl); 7.08 dd (J
=8.OHz/7.OHz, 1H, and aryl); 7.02 dd (J = 8.5 Hz 3',4'-Dimethoxy(1,1'-biphenyl]- / 2.8 Hz, 1 H, aryl); 6.99 d 2-carboxylic acid (J = 1.8 Hz, 1 H, aryl);
6.98 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 6.91 m (1 H, aryl); 6.89 d (J = 2.8 Hz, 1 H, aryl); 6.86 d (J =
7.9 Hz, 1 H, aryl); 6.82 d (J = 7,9 Hz, 1 H, aryl);
4.20 m(1 H, CH); 3.78 s (3H, OCH3); 3.75 s (3H, OCH3); 3.45 dd (J = 11,1 Hz / 5.3 Hz, 1 H, CH2OH); 3,39 dd (J =
11,1 Hz/5,7Hz, 1H, Ex. Product; aMetho nalotl 'H-NMR (400 MHz) S Structure reagents yous to Ippm]
CH2OH); 2.88 dd (J =
14,7 Hz / 7.2 Hz, 1 H, CHZ); 2.76 dd (J = 14.7 Hz / 7.3 Hz, 1 H, CH2).

86 N-[(R)-1-(Hydroxymethyl)-2- 39 (CD3OD): 7.53 d (J = 8.0 OH
(1 H-indol-3-yl)ethyl]-3'-(1 - Hz, 1H, aryl); 7.43 dd (J 0 H H
methylethyl)[1,1'-biphenyl]-2- = 7.2 Hz / 7.2 Hz, 1 H, carboxamide aryl); 7.34 m (2H, aryl);
7.32 d (J = 8.0 Hz, 1 H, D-Tryptophanol aryl); 7.30 dd (J = 8,2 Hz 3'-(1-Methylethylff1,1 '- / 7.6 Hz, 1 H, aryl); 7.22 s (1 H, aryl); 7.16 m (2H, iphenylJ-2-carboxylic acid aryl); 7.11 m(1 H, aryl);
7.04 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 6.93 dd (J
= 8.0 Hz / 7.0 Hz, 1 H, aryl); 6.92 d (J = 1.8 Hz, 1 H, aryl); 4.13 m(1 H, CH); 3.37 dd (J = 11.1 Hz / 5.3 Hz, 1 H, CH2OH); 3.29 m (1 H, CH2OH); 2.82 m (1 H, CH); 2.80 dd (J = 15.1 Hz / 7.0 Hz, 1 H, CHZ);
2.70 dd (J = 15.1 Hz /
7.2 Hz, 1 H, CH2); 1.19 d (J = 7.0 Hz, 6H, CH3).

87 N-[(R)-1-(Hydroxymethyl)-2- 39 (CD3OD): 7.85 dd (J = o"
(1 H-indol-3-yl)ethyl]-2',5'- 1.7 Hz / 1.3 Hz, 1 H, aryl); o H N
dimethoxy[1,1'-biphenyl]-3- 7.68 d (J = 8.0 Hz, 1 H, ~ H
=
carboxamide; aryl); 7.68 d (J = 7.7 Hz, ~ 1 H, aryl); 7.63 d (J = 7.7 o-Tryptophanol ~.
Hz, 1 H, aryl); 7.42 dd (J
= 7.7 Hz / 7.7 Hz, 1 H, Ex. Product; aMetho nalotl 'H-NMR (400 MHz) S Structure reagents yo-,S to IPpml and aryl); 7.31 d (J = 8.0 Hz, 1 H, aryl); 7.12 d(J = 1.8 2;5'-Dimethoxy(1,1'-biphenyl]- Hz, 1 H, aryl); 7.06 dd (J
3-carboxylic acid = 8.0 Hz / 7.0 Hz, 1 H, aryl); 7.00 d (J = 9.6 Hz, 1 H, aryl); 6.97 dd (J =
8.0 Hz / 7.0 Hz, 1 H, aryl);
6.90 dd (J = 9.6 Hz / 3.0 Hz, 1 H, aryl); 6.80 d (J =
3.0 Hz, 1 H, aryl); 4.46 m (1 H, CH); 3.78 s (3H, OCH3); 3.70 s (3H, OCH3); 3.70 m (2H, CH2OH); 3,15 dd (J =
14.5 Hz / 6,2 Hz, 1 H, CH2); 3.07 dd (J = 14.5 Hz / 7.2 Hz, 1 H, CH2).

88 3',4',5'-Trifluoro-N-[(R)-1- 39 (CD3OD): 7.59 d (J = 8.0 0" F
(hydroxymethyl)-2-(1 H-indol- Hz, 1 H, aryl); 7.34 d(J = F o H N

3-yI)ethylJ-4-methoxy[1,1'- 8.0 Hz, 1 H, aryl); 7.27 d F biphenyl]-2-carboxamide; (J = 8.7 Hz, 1 H, aryl);

7.09 dd (J = 8.0 Hz / 7.0 D-Tryptophanol Hz, 1 H, aryl); 7.07 d (J =
and 1.6 Hz, 1 H, aryl); 7.07 m (2H, aryl); 7.01 dd (J =
3;4;5'-Trifluoro-4- 8,7 Hz / 2,7 Hz, 1H, aryl);
ethoxy[1,1 '-biphenyl]-2- 7.00 dd (J = 8.0 Hz / 7.0 carboxylic acid Hz, 1 H, aryl); 6.79 d (J =
2.7 Hz, 1 H, aryl); 4.28 m (1H, CH); 3.75 s (3H, OCH3); 3.55 m (2H, CH2OH); 3.01 dd (J =
14.5 Hz / 5,8 Hz, 1 H, Ex. Product; eMetho nalo~ 'H-NMR (400 MHz) S Structure reagents yous to [ppm]
CH2); 2.87 dd (J = 14.5 Hz / 7.7 Hz, 1 H, CHZ).

89 3-(Benzofuran-2-yl)-N-[(R)-1- 39 0"
(CD30D): 8.24 s (1 H, (hydroxymethyl)-2-(1 H-indol- aryl); 8.01 d (J = 7,9 Hz, 0 " H
3-yI)ethyl]benzamide; 1 H, aryl); 7.73 d (J = 7.7 D-Tryptophanol Hz, 1 H, aryl); 7.69 d (J = _ o 8.0 Hz, 1 H, aryl); 7.61 d and (J = 7.4 Hz, 1 H, aryl);
7.53 d (J = 7.4 Hz, 1 H, 3-(Benzofuran-2-y1)benzoic aryl); 7.51 dd (J = 7.9 Hz acid / 7.7 Hz, 1 H, aryl); 7.32 d (J = 8.0 Hz, 1 H, aryl);
7.30 dd (J = 8.3 Hz / 7.4 Hz, 1 H, aryl); 7.23 dd (J
= 8.3 Hz / 7.4 Hz, 1 H, aryl); 7.20 s(1 H, aryl);
7.14 d (J = 1.8 Hz, 1 H, aryl); 7.08 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 7.00 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 4.49 m(1 H, CH); 3.73 m (2H, CHZOH); 3.17 dd (J =
14.7 Hz / 7.0 Hz, 1 H, CH2); 3.09 dd (J = 14.7 Hz / 7.3 Hz, 1 H, CH2).

90 N-[(R)-1-(Hydroxymethyl)-2- 39 (DMSO-d6): 10.77 s(1H, OH (1 H-indol-3-yl)ethyl]-3-(5- NH); 8.37 d J = 8.3 Hz, ( - H
methoxybenzofuran-2- 1 H, NH); 8.33 s(1 H, a-I)benzamide; ryl); 8.02 d (J = 7.8 Hz, o o 1 H, aryl); 7.84 d (J = 7.8 D-Tryptophanol Hz, 1 H, aryl); 7.68 d (J =

and 8.0 Hz, 1 H, aryl); 7.57 dd (J = 7.8 Hz / 7,8 Hz, 1 H, Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents yous to LPPmI
3-(5-Methoxybenzofuran-2-y1)- aryl); 7.56 d (J = 9.1 Hz, 5enzoic acid 1 H, aryl); 7.43 s (1 H, a-ryl); 7.32 d (J = 8.0 Hz, 1 H, aryl); 7.16 s(1 H, a-ryl); 7.05 dd (J = 8.0 Hz /
7.0 Hz, 1 H, aryl); 6.98 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 6.93 dd (J = 9.1 Hz / 2.5 Hz, 1 H, aryl); 4.28 m(1 H, CH); 3.81 s(3H, OCH3); 3.57 m (1 H, CH2OH); 3.53 m (1 H, CHZOH); 3.05 dd (J =
14.4 Hz / 5.8 Hz, 1H, CH2); 2.96 dd (J = 14.4 Hz / 8.1 Hz, 1 H, CH2).

Example 91 N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2-[(3,4,5-trimethoxyphenyl)methoxy]phenylpropanamide OYH- I \ /
~O O N
H
.~O /
\ I O
~ I

91 a) Methyl 2-[(3,4,5-trimethoxyphenyl)methoxy]phenylpropanoate 0.38 mmol (68 mg) of methyl 2-hydroxyphenylpropanoate and 0.384 mmol (125 mg) of caesium carbonate were added to a solution of 0.38 mmol (100 mg) of 1-(bromomethyl)-3,4,5-trimethoxybenzene in 4 ml of acetonitrile. The mixture was heated to boiling for four hours. After cooling, the reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate.
The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulphate, filtered and concentrated in vacuo.
Flash chromatography resulted in 122 mg of the target compound.

'H-NMR (400 MHz, CDC13): S[ppm] = 7.18 d (J = 7.3 Hz, 1 H, aryl); 7.19 dd (J =
8.3 Hz /
7.6 Hz, 1 H, aryl); 6.91 dd (J = 8.3 Hz / 7.3 Hz, 1 H, aryl); 6.90 d (J = 7.6 Hz, 1 H, aryl);
6.67 s (2H, aryl); 5.02 s (2H, OCH2); 3.88 s (6H, OCH3); 3.86 s(3H, OCH3);
3.64 s (3H, OCH3); 3.02 t (J = 7.9 Hz, 2H, CHZ); 2.67 t (J = 7.9 Hz, 2H, CH2).

91 b) 2-[(3,4,5-Trimethoxyphenyl)methoxy]phenylpropanoic acid In analogy to Example 39b), 112 mg of the title compound were obtained from 0.32 mmol (115 mg) of the compound prepared as in 91a) in 6.4 ml of methanol with 1.6 ml of a 2 molar aqueous sodium hydroxide solution.

'H-NMR (400 MHz, CD3OD): S[ppm] = 7.16 m(21 H, aryl); 6.86 dd (J = 7.5 Hz /
7.3 Hz, 1 H, aryl); 6.98 d (J = 8.5 Hz, 1 H, aryl); 6.78 s (2H, aryl); 5.05 s (2H, OCH2); 3.83 s (6H, OCH3); 3.75 s (3H, OCH3); 2.96 t (J = 7.9 Hz, 2H, CHZ); 2.60 t (J = 7.9 Hz, 2H, CHz).

91 c) N-[(R)-1-(Hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-2-[(3,4,5-trimethoxyphenyl)methoxy]phenylpropanamide In analogy to Example le), 87 mg of the title compound were obtained from 0.27 mmol (95 mg) of the compound prepared as in 91 b) and 0.26 mmol (50 mg) of D-tryptophanol.
'H-NMR (400 MHz, DMSO-d6): 6 [ppm] = 10.74 s(1 H, NH); 7.63 d (J = 8.3 Hz, 1 H, NH);
7.60 d (J = 8.0 Hz, 1 H, aryl); 7.31 d (J = 8.0 Hz, 1 H, aryl); 7.16 dd (J =
7.9 Hz / 7.7 Hz, 1 H, aryl); 7.12 d (J = 8.1 Hz, 1 H, aryl); 7.05 s(1 H, aryl); 7.04 dd (J =
8.1 Hz / 7.7 Hz, 1 H, aryl); 7.04 d (J = 7.9 Hz, 1 H, aryl); 6.95 dd (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 6.84 dd (J
= 8.0 Hz / 7.0 Hz, 1 H, aryl); 6.79 s (2H, aryl); 5.04 s (2H, OCH2); 3.97 m (1 H, CH); 3.76 s(6H, OCH3); 3.65 s(3H, OCH3); 3.33 m(2H, CH2OH); 2.87 dd (J = 14.5 Hz / 7.9 Hz, 1 H, CHZ); 2.83 m(2H, CHZ); 2.71 dd (J = 14.5 Hz / 7.0 Hz, 1 H, CH2); 2.38 m (2H, CH2).
The following compounds were obtained in analogy to the preparation methods described in detail:

Ex. Product; aMetho na oa 'H-NMR (400 MHz) S Structure reagents gous to [ppm]

92 N-[(R)-1-(Hydroxymethyl)-2- 91 (DMSO-ds): 10.74 broad oH
(1 H-indol-3-yl)ethyl]-4- s (1H, indole-NH); 8.13 d "~ H
[[(3,4,5- (J = 8.3 Hz, 1 H, amide);
trimethoxyphenyl)methoxy]- 7.83 d (J = 8.4 Hz, 2H, o methyl]benzamide; aryl); 7.64 d (J = 8.0 Hz, - ~ I
1 H, aryl); 7.42 d (J - 8.4 ~
D-Tryptophanol Hz, 2H, aryl); 7.31 d (J = o\
and 8.0 Hz, 1 H, aryl); 7.12 d (J = 2.1 Hz, 1 H, aryl);
4-(((3, 4, 5- 7.04 dd (J = 8.0 Hz / 7.0 Trimethoxy- Hz, 1 H, aryl); 6.96 dd (J
phenyl)methoxy]methyl]benzo = 8.0 Hz / 7.0 Hz, 1 H, ic acid aryl); 6.66 s (2H, aryl);
4.77 dd (J = 5,7 Hz / 5.7 Hz, OH); 4.57 s (2H, CH2O); 4.47 s (2H, Ex. Product; aMetho nelotl 'H-NMR (400 MHz) S Structure reagents yous to [ppm]
CHZO); 4.23 m (1 H, CHNH); 3.76 s (6H, 0-Me); 3.64 s (3H, OMe);
3.52 m (1 H, CH2OH);
3.48 m (1 H, CH2OH);
3.02 dd (J = 15.1 Hz/
5.8 Hz; 1 H, CH2-indole);
2.91 dd (J = 15.1 Hz /
7.7 Hz; 1 H, CH2-indole).

93 N-[(R)-1-(Hydroxymethyl)-2- 91 (DMSO-d6): 10.80 s(1H, H P
-(1H-indol-3-yl)ethyl]-3-[(3,4,5- indole-NH); 7.68 d (J O ~' " H
~~ , ~/=i s trimethoxyphenyl)methoxy]- 5.5 Hz, 1 H, aryl); 7.57 d ~ ~/
thiophene-2-carboxamide; (J = 8.0 Hz, 1 H, aryl);
7.55 d(J = 8.1 Hz, 1 H, D-Tryptophanol amide); 7.31 d (J = 8.0 =
and Hz, 1 H, aryl); 7.22 d (J
5.5 Hz; 1 H, aryl); 7.05 dd 3-((3, 4, 5-Trimethoxyphenyl)- (J = 8.0 Hz / 7.0 Hz, 1 H, methoxyJthiophene-2- aryl); 6.98 d (J = 2.3 Hz, carboxylic acid 1 H, indole); 6.95 dd (J =
8.0 / 7.0 Hz, 1 H, aryl);
6.76 s (2H, aryl); 5.21 d (J =11.7 Hz, 1 H, CH2O);
5.14 m(1 H, CHNH); 5.13 d(J = 11.7 Hz, 1H, CH2O); 4.95 dd (J = 5.3 Hz / 5.3 Hz; 1 H, OH);
3.93 dd (J = 14.7 Hz /
7,0 Hz, 1H, CHZ); 3.81 dd ( J = 14.7 Hz / 6.4 Hz, 1H, CHz); 3.73 s (6H, OMe); 3.63 s (3H, OMe);
3.44 m(1 H, CH2); 3.40 m (1H, CHZ).

Ex. Product; aMet nehoa 'H-NMR (400 MHz) S Structure reagents yous to [ppm]

94 N-[(R)-1-(Hydroxymethyl)-2- 91 (DMSO-d6): 10.76 s(1H, O"
(1H-indol-3-yl)ethyl]-4-[(3,4,5- indole-NH); 7.82 d (J= 0 " 1 H
trimethoxyphenyl)methoxy]- 8.1 Hz, 1H, amide); 7.58 phenylacetamide; d (J = 8.0 Hz, 1 H, aryl); 'o 7.32 d(J = 8. 0 Hz, 1 H, , D-Tryptophanol aryl); 7.08 d (J = 8.7 Hz, and 2H, aryl); 7.07 s(1 H, a-ryl); 7.05 dd (J = 8.0 Hz /
4-((3, 4, 5-Trimethoxyphenyl)- 7.0 Hz, 1 H, aryl); 6.95 dd methoxy]benzenessigsaure (J = 8.0 Hz / 7.0 Hz, 1 H, aryl); 6.89 d (J = 8.7 Hz;
2H; aryl); 6.76 s (2H, a-ryl); 4.97 s (2H, CH2O);
4.73 dd (J = 5.5 Hz / 5.5 Hz, 1 H, OH); 3.95 m(1 H, CHNH); 3.77 s (6H, 0-Me); 3.65 s (3H, OMe);
3.36 m (2H, CH2OH);
3.33 s (2H, CHz); 2.90 dd (J=14.1 Hz/6.2Hz, 1H, CH2-indole); 2.74 dd (J = 14.1 Hz / 7.5 Hz, 1 H, CH2-indole).

95 N-[(R)-1-(Hydroxymethyl)-2- 91 (DMSO-d6): 10.75 s(1H, o"
~/
(1H-indol-3-yl)ethyl]-3-[(3,4,5- indole-NH); 7.68 d (J = o "~ N
H
rimethoxyphenyl)methoxy]- 8.3 Hz, 1 H, amide); 7.60 ~~
phenylpropanamide; d (J = 8.0 Hz, 1 H, aryl); o' "o 7.31 d(J = 8.O Hz, 1 H, ~
D-Tryptophanol aryl); 7.17 dd (J = 7.9 Hz o, and / 7.7 Hz, 1 H, aryl); 7.07 d (J = 2.1 Hz, 1 H, indole);
3-(3-((3, 4, 5-trimethoxyphenyl)- 7.05 dd (J = 8.0 Hz / 7.0 methoxy)phenyl]-propionsaure Hz, 1 H, aryl); 6.87 s(1 H, aryl); 6.85 dd (J = 8.0 Hz Ex. Product; aMet nahoa 'H-NMR (400 MHz) S Structure reagents gous to Ippml / 7.0 Hz, 1 H, aryl); 6.82 dd (J = 7.9 Hz / 2.5 Hz, 1 H, aryl); 6.76 dd (J =
7.7 Hz / 2.5 Hz, 1 H, aryl);
6.75 s (2H, aryl); 4.96 s (2H, CH2O); 4.70 dd (J =
5.7 Hz / 5.5 Hz, 1 H, OH);
3.76 s (6H, OMe); 3.98 m (1H, CHNH); 3.65 s (3H, OMe); 3.33 m (2H, CH2OH); 2.89 dd (J =
14,1 Hz / 6.6 Hz, 1 H, CH2); 2.74 m (2H, CH2);
2.72 dd (J = 14.1 Hz /
7.0 Hz, 1H, CHZ); 2.35 m (2H, CH2).

Example 96 2-[2-(3,4-dimethoxyphenyl)ethyl]-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-HO I
O NH N
H
O, 6-methoxyquinoline-4-carboxamide "0 96a) 2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-6-methoxyquinoline-4-carboxylic acid 4-methoxyisatin (4 g, 22.5 mmol) and (E)-3,4-dimethoxybenzylideneacetone (4.6 g, 22.5 mmol) were suspended in 30% strength aqueous KOH (20 ml) and heated under reflux for 8 hours. The reaction mixture was cooled and diluted with water, and the solid was filtered off. The residue on the filter was boiled three times with sodium hydroxide solution (1 N, 100 ml), and the combined mother liquors were acidified by adding acetic acid. A solid precipitates out of the solution after it has stood in a refrigerator overnight.
The precipitate was filtered off, washed with water (100 ml) and dried in vacuo. 1.67 g (20% yield) of the title compound were obtained and could be employed in the next stage without further purification.

'H-NMR (400 MHz, DMSO-d6): 6[ppm] = 8.18 s(1 H); 8.08 d (J = 2.6 Hz, 1 H);
7.94 d (J
= 9.2 Hz, 1 H); 7.71 d (J = 16.2 Hz, 1 H); 7.44 m (2H); 7.40 d (J = 16.3 Hz, 1 H); 7.22 d (J
= 8.1 Hz, 1 H); 6.96 d (J = 8.5 Hz, 1 H); 3.86 s (3H); 3.81 s (3H); 3.76 s (3H).

96b) 2-[2-(3,4-dimethoxyphenyl)ethyl]-6-methoxyquinoline-4-carboxylic acid 2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-6-methoxyquinoline-4-carboxylic acid (500 mg) was dissolved in methanol (10 ml) and aqueous sodium hydroxide solution (1 N, 5 ml) and concentrated to dryness in vacuo. The residue is dissolved in methanol (5 ml), a spatula tip of Pd/C is added, and hydrogenation is carried out under low pressure and at room temperature until no further uptake of hydrogen is to be observed. The catalyst was filtered off and the filtrate was concentrated in a rotary evaporator.
Acidification with aqueous hydrochloric acid (1 N), removal of the precipitate by filtration and drying in vacuo resulted in 277 mg of the title compound which could be employed in the next stage without further purification.

'H-NMR (400 MHz, DMSO-d6): S[ppm] = 13.70 s broad (1 H, acid); 8.07 d (J =2.8 Hz, 1 H, aryl); 7.93 d (J = 9.3 Hz, 1 H, aryl); 7.83 s (1 H, aryl); 7.42 dd (J =
9.1 Hz / 2.8 Hz;
1 H, aryl); 6.85 d (J =1.8 Hz, 1 H, aryl); 6.79 d (J = 8.1 Hz, 1 H, aryl);
6.72 dd (J = 8.1 Hz /
1.5 Hz, 1 H, aryl); 3.85 s (3H, OMe); 3.66 s (6H, OMe); 3.18 m (2H, CHZ); 2.97 m (2H, CH2).

96c) 2-[2-(3,4-dimethoxyphenyl)ethyl]-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-6-methoxyquinoline-4-carboxamide In analogy to method 1e), D-tryptophanol (103 mg, 0.54 mmol) and the quinolinecarboxylic acid from method 98b) (100 mg, 0.27 mmol) were reacted to give the title compound and purified by recrystallization from ethanol. 122 mg of the title compound were obtained.
'H-NMR (400 MHz, DMSO-d6): S[ppm] = 10.80 s(1 H, indole-NH); 8.47 d (J = 8.7 Hz, 1 H, amide); 7.86 d (J = 9.9 Hz, 1 H, aryl); 7.62 d (J = 7.7 Hz, 1 H, aryl);
7.30 m (4H, aryl);
7.17 d (J = 1.9 Hz, 1 H, aryl); 7.03 dd (J = 7.0 Hz / 7.0 Hz, 1 H, aryl); 6.94 dd (J = 7.0 Hz / 7.0 Hz, 1 H, aryl); 6.87 d (J = 1.5 Hz, 1 H, aryl); 6.80 m (2H, aryl); 4.84 dd (J = 5.5 Hz /
5.5 Hz, 1 H, OH); 4.35 m(1 H, CHz); 3.68 s (3H, OMe); 3.67 s (3H, OMe); 3.66 s (3H, OMe); 3.54 dd (J =5.6 Hz / 5.6 Hz, 2H, CH2); 3.10 m (2H, CH2); 2.92 m (4H, CH2).
Ex. Product; aMet nehotl 'H-NMR (400 MHz) S Structure reagents gous to Lppm]

97 2-(6-Methoxy-naphthalen-2- 13 (DMSO-ds): 10.85 s(1 H); - H
/ N
yl)quinoline-4-carboxylic acid 8.67 s (1 H); 8.64 d (J
=
[(R)-1-hydroxymethyl-2-(1 H- 8.3 Hz, 1 H); 8.33 dd (J = HO
O NH
indol-3-yl)ethyl]amide; 2.0 Hz / 8.8 Hz, 1 H); 8.09 ~ I
- 7.96 m(4H); 7.84 d(J = N
(~)-Tryptophanol I ~
8.3 Hz, 1 H); 7.76 m(1 H); o and 7.66 d (J = 7.8 Hz, 1 H);
7.48 m(1 H); 7.37 m (2H);
2-(6-Methoxy-naphthalen-2- 7.24 dd (J = 2.5 Hz / 9.1 yl)quinoline-4-carboxylic acid Hz, 1 H); 7.18 m (1 H);
7.06 m(1 H); 6.95 m(1 H);

Product; Method 'H-NMR (400 MHz) S Structure Ex. rea ents analo-9 gous to [PPm]
4.39 m (1H); 3.89 s (3H);
3.55 m (2H); 3.08 dd (J =
5.8 Hz / 14.7 Hz, 1 H);
2.92 dd (J = 8.3 Hz / 14.4 Hz, 1 H).

98 6-Methoxy-2-(3- 13 (DMSO-d6): 10.81 s (1H); H
/ N
methoxyphenyl)quinoline-4- 8.63 d (J = 8.6 Hz, 1 H);
carboxylic acid [(R)-1- 7.98 d (J = 9.1 Hz, 1 H); Ho HNH
hydroxymethyl-2-(1 H-indol-3- 7.89 s(1 H); 7.75 s(1 H); o ~, yI)ethyl]amide; 7.71 d (J = 7.8 Hz, 1 H); ~0 N 7.64 d(J = 7.8 Hz, 1 H);

(D)-Tryptophanol 7.45 m (3H); 7.31 d (J =
and 8.1 Hz, 1 H); 7.18 s(1 H);
7.05 m (1 H); 6.93 m (1 H);
6-Methoxy-2-(3- 4.89 m(1 H); 4.38 m(1 H);
methoxyphenyl)quinoline-4- 3.84 s (3H); 3.71 s (3H);
carboxylic acid 3.57 m (2H); 3.03 dd (J =
5.6 Hz / 14.7 Hz, 1 H); dd (J = 8.1 Hz / 14.7 Hz, 1 H).

99 2-(4-Fluoro-3- 13 (DMSO-d6): 10.80 s(1 H); - H
N
methoxyphenyl)-6- 8.62 d (J = 8.7 Hz, 1 H);
methoxyquinoline-4- 7.96 m (2H); 7.90 s(1 H); Ho H
O NH
carboxylic acid [(R)-2- 7.69 m(1 H); 7.61 d (J =
hydroxy-1-(1 H-indol-3- 7.9 Hz, 1 H); 7.42 m(3H); ~~
O ~ I N /
ylmethyl)ethyl]amide; 7.19 s(1 H); 7.03 m(1 H); F
6.93 m(1 H); 4.87 m(1 H);
(o)-Tryptophanol 4.37 m(1 H); 3.96 s (3H);
and 3.71 m (3H); 3.57 m (2H);
2-(4-Fluoro-3- 3.01 m(1 H); 2.91 m(1 H).
methoxyphenyl)-6-methoxyquinoline-4-Ex. Product; aMetho naloa 'H-NMR (400 MHz) 8 Structure reagents gous to IPPm]
carboxylic acid 100 2-(3-Iodo-4-methoxyphenyl)- 13 (DMSO-d6): 10.79 s(1 H); N
6-methoxyquinoline-4- 8.62 m(1 H); 8.15 dd (J =
carboxylic acid [(R)-2- 2.1 Hz / 8.5 Hz, 1 H); 7.95 Ho H
O NH
hydroxy-1-(1 H-indol-3- d (J = 9.6 Hz, 1 H); 7.84 s oll ylmethyl)ethyl]amide; (1 H); 7.63 d (J = 7.9 Hz, , I N
1 H); 7.40 s(1 H); 7.30 m o I~
(D)-Tryptophanol I
(2H); 7.18 m (2H); 7.04 m and (1 H); 6.94 m(1 H); 4.87 m (1 H); 4.36 m(1 H); 3.90 s 2-(3-1odo-4-methoxyphenyl)- (3H); 3.70 s (3H); 3.57 m 6-methoxyquinoline-4- (2H); 3.01 m(1 H); 2.90 m carboxylic acid (1 H).

101 2-(3-Hydroxyphenyl)-6- 13 (DMSO-d6): 10.79 s(1 H); N
methoxyquinoline-4- 9,60 s(1 H); 8.62 d (J = ?
carboxylic acid [(R)-1- 8.7 Hz, 1 H); 7.94 d (J = Ho O NH
hydroxymethyl-2-(1 H-indol-3- 9.6 Hz, 1 H); 7.82 s(1 H); o~, yI)ethyl]amide; 7.64 m (2H); 7.51 d(J = HO N

8.1 Hz, 1 H); 7.41 m (2H); (D)-Tryptophanol 7.32 m (2H); 7.18 s(1 H);

and 7.03 m(1 H); 6.93 m(1 H);
6.87 m (1 H); 4.88 m (1 H);
2-(3-Hydroxyphenyl)-6- 4.38 m(1 H); 3.71 s(3H);
methoxyquinoline-4- 3.56 m(2H); 3.01 m(1 H);
carboxylic acid 2.93 m (1 H).

102 2-(4-Hydroxy-3,5- 13 (DMSO-d6): 10.79 s(1 H); H
N
dimethoxyphenyl)-6- 8.78 s (1 H); 8.61 d (J =
methoxyquinoline-4- 8.8 Hz, 1 H); 7.90 m(2H); Ho NH
carboxylic acid [(R)-1- 7.63 d (J = 7.8 Hz, 1 H); o,~
hydroxymethyl-2-(1 H-indol-3- 7.47 s (2H); 7.39 m (3H); -o ~ N 7.30 d J= 8.1 Hz, 1 H; HO yl)ethyl]amide; ( ) o 7.19 s(1 H); 7.02 m(1 H);

Ex. Product; aMetho naloa 'H-NMR (400 MHz) 8 Structure reagents gous to Ippm]
(o)-Tryptophanol 6.93 m(1 H); 4.86 m(1 H);
4.37 m(1 H); 3.87 s(6H);
and 3.69 s (3H); 3.57 m (2H);
3.02dd(J=5.8Hz/15.1 2-(4-Hydroxy-3,5- Hz, 1 H); 2.91 dd (J = 7.6 dimethoxyphenyl)-6- Hz / 14.4 Hz, 1 H).
methoxyquinoline-4-carboxylic acid 103 2-(3,5-Difluoro-4- 13 (DMSO-d6): 10.80 s(1 H); - N
/
methoxyphenyl)-6- 8.59 d (J = 8.7 Hz, 1 H);
methoxyquinoline-4- 7.93 m (4H); 7.63 d (J = Ho O NH
carboxylic acid [(R)-2- 7.9 Hz, 1 H); 7.41 m(2H); o 1~
hydroxy-1-(1 H-indol-3- 7.31 d (J = 7.9 Hz, 1 H); F N
~
ylmethyl)ethyl]amide; 7.18 s(1 H); 7.02 m(1 H); o F
6.92 m(1 H); 4.87 m(1 H);
(D)-Tryptophanol 4.37 m(1 H); 3.99 s(3H);
and 3.70 s (3H); 3.57 m (2H);
3.01 dd(J=6.4Hz/14.7 2-(3, 5-Difluoro-4- Hz, 1 H); 2.89 dd (J = 8.1 methoxyphenyl)-6- Hz / 14.3 Hz, 1 H).
methoxyquinoline-4-carboxylic acid 104 2-(3-Ethylphenyl)-6- 13 (DMSO-d6): 10.80 s(1 H); H
~ N
methoxyquinoline-4- 8.61 d (J = 8.6 Hz, 1 H);
carboxylic acid [(R)-1- 7.96 m (4H); 7.86 s(1H); Ho O NH
hydroxymethyl-2-(1 H-indol-3- 7.63 d (J = 7.8 Hz, 1 H); o, yl)ethyl]amide; 7.41 m (4H); 7.32 d (J = I~ N 8.1 Hz, 1 H); 7.18 s(1 H);

(D)-Tryptophanol 7.03 m(1 H); 6.93 m(1 H);
and 4.87m(1H);4.37m(1H);
3.71 s (3H); 3.57 m (2H);
2-(3-Ethylphenyl)-6- 2.95 dd (J = 5.6 Hz / 14.7 methoxyquinoline-4- Hz, 1 H); 2.91 dd (J = 8.1 Ex. Product; aMetho ne otl 'H-NMR (400 MHz) S Structure reagents gous to Ippm]
carboxylic acid Hz / 14.7 Hz, 1 H); 2.71 m (2H); 1.21 m (3H).

105 2-(3-Fluoro-4- 13 (DMSO-d6): 10.80 s(1 H);
methoxyphenyl)-6- 8.59 d (J = 8.7 Hz, 1 H); Ho NH ~\/
N
H
methoxyquinoline-4- 8.00 m (3H); 7.85 s(1 H); ~, carboxylic acid [(R)-2- 7.63 d (J = 7.7 Hz, 1 H); N
hydroxy-1-(1 H-indol-3- 7.35 m (4H); 7.18 d (J = F
ylmethyi)ethyl]amide; 2.1 Hz, 1 H); 7.04 m(1 H);
6.93 m(1 H); 4.86 m(1 H);
(o)-Tryptophanol 4.37 m(1 H); 3.91 s(3H);
and 3.70 s (3H); 3.57 m (2H);
2-(3-Fluoro-4- 3.02 m(1 H); 2.93 m(1 H).
methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid 106 2-(3-Fluoro-4- 13 (DMSO-d6): 10.83 s(1 H); - H
N
methoxyphenyl)-6- 8.56 d (J = 8.7 Hz, 1 H);
methylquinoline-4-carboxylic 8.06 dd (J = 2.1 Hz / 13.0 HO
acid [(R)-2-hydroxy-1-(1 H- Hz, 1 H); 7.98 d (J = 9.8 0 NH
indol-3-ylmethyl)ethyl]amide; Hz, 1 H); 7.91 d (J = 8.5 Hz, 1 H); 7.84 s(1 H); 7.62 N
o)-Tryptophanol ( m (3H); 7.32 m (2H); 7.18 ol and s(1 H); 7.05 m(1 H); 6.94 m(1 H); 4.88 m(1 H); 4.38 2-(3-Fluoro-4- m(1 H); 3.91 s(3H); 3.57 methoxyphenyl)-6- m(2H); 3.03 m(1H); 2.90 methylquinoline-4-carboxylic m (1 H); 2.38 s (3H).
acid Product; Method 'H-NMR (400 MHz) 8 Structure Ex. rea ents analo-9 gous to EPPm]

107 6-Methyl-2-(3,4,5- 13 (DMSO-d6): 10.81 s (1H);
Ho trimethoxyphenyl)quinoline-4- 8.58 d (J = 8.3 Hz, 1 H); 0 NH N
carboxylic acid [(R)-1- 7.93 m (2H); 7.62 m (2H); hydroxymethyl-2-(1 H-indol-3-7.58 dd (J = 1.8 Hz / 8.6 0 N

yl)ethyl]amide; Hz, 1 H); 7.48 s (2H); 7.32 ~, d (J = 8.1 Hz, 1 H); 7.18 s (D)-Tryptophanol (1 H); 6.95 m(1 H); 6.93 m and (1 H); 4.86 m(1 H); 4.36 m (1 H); 3.89 s (6H); 3.72 s 6-Methyl-2-(3,4,5- (3H); 3.57 m (2H); 3.04 m trimethoxyphenyl)quinoline-4- (1 H); 2.91 m(1 H); 2.65 s carboxylic acid (3H).

108 6-Bromo-2-(2,4-dimethyl- 13 (DMSO-d6): 10.81 s(1 H); Ho ~ NH ~
thiazol-5-yl)quinoline-4- 8.72 d (J = 8.7 Hz, 1 H); N
Br U N~ ~
carboxylic acid [(R)-2- 8.15 s(1 H); 7.88 s (2H); / ~\ \
N
hydroxy-1-(1 H-indol-3- 7.63 s(1 H); 7.58 d (J =
ylmethyl)ethyl]amide; 7.9 Hz, 1 H); 7.32 d (J =
8.1 Hz, 1 H); 7.17 d(J =
(D)-Tryptophanol 2.1 Hz, 1 H); 7.02 m(1 H);
and 6.92 m(1 H); 4.88 m(1 H);
4.33 m(1 H); 3.55 m (2H);
6-Bromo-2-(2,4-dimethyl- 3.02 dd (J = 5.3 Hz / 14.7 thiazol-5-yl)quinoline-4- Hz, 1 H); 2.90 dd (J = 8.3 carboxylic acid Hz / 14.7 Hz, 1 H); 2.64 s (3H); 2.62 s (3H).

Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents gous to [ppm]

109 2-(7-Methoxybenzofuran-2- 13 (DMSO-d6): 10.79 s(1 H); N
yI)-6- 8.81 d (J = 8.9 Hz, 1 H); ~
HO
trifluoromethoxyquinoline-4- 8.23 d (J = 9.2 Hz, 1 H); o NH
carboxylic acid [(R)-2- 8.07 s(1 H); 7.93 s(1 H); o~,F
F
N /
hydroxy-1-(1 H-indol-3- 7.80 m (2H); 7.62 d (J o ylmethyl)ethyl]amide; 7.7 Hz, 1 H); 7.33 m (3H); 0 ~
(D)-Tryptophanol 7.18 s(1 H); 7.03 m (3H);
and 4.90 m(1 H); 4.36 m(1 H);
2-(7-Methoxybenzofuran-2- 3.99 s (3H); 3.56 m (2H);
yl)-6- 3.02 m(1 H); 2.92 m(1 H).
trifluoromethoxyquinoline-4-carboxylic acid 110 2-(3-Fluoro-4- 13 (DMSO-d6): 10.80 s(1 H); - H
N
methoxyphenyl)-6- 8.68 d (J = 8.5 Hz, 1 H);
iodoquinoline-4-carboxylic 8.44 s(1H); 8.00 m(3H); Ho acid [(R)-2-hydroxy-1-(1 H- 7.91 s(1 H); 7.80 d (J =
indol-3-ylmethyl)ethyl]amide; 8.9 Hz, 1 H); 7.65 d (J = F
7,9 Hz, 1 H); 7.33 m (2H); ~a (o)-Tryptophanol 7.18 s(1 H); 7.04 m(1 H);
and 6.94 m(1 H); 4.34 m(1 H);
3.92 s (3H); 3.57 m (2H);
2-(3-Fluoro-4- 3.03 m(1 H); 2.92 m(1 H).
methoxyphenyl)-6-iodoquinoline-4-carboxylic acid 111 2-(3-Fluoro-4- 13 (DMSO-d6): 10.84 s(1 H); - N
methoxyphenyl)-6- 8.76 d (J = 8.5 Hz); 8.76 ~
trifluoromethoxyquinoline-4- d (J = 8.5 Hz, 1 H); 8.21 d Ho NH
carboxylic acid [(R)-2- (J = 9.23 Hz, 1 H); 8.16 - oFF
hydroxy-1-(1 H-indol-3- 8.04 m (4H); 7.81 dd (J = F I I N F
ylmethyl)ethyl]amide; 2.8 Hz / 8.5 Hz, 1 H); 7.68 d (J = 7.7 Hz, 1 H); 7.37 m Ex. Product; aMetho na otl 'H-NMR (400 MHz) S Structure reagents yous to [ppm]
(o)-TryPtophanol (2H); 7.21 d (J = 2.1 Hz, 1 H); 7.07 m (1 H); 6.97 m and (1 H); 4.91 m(1 H); 4.38 m (1 H); 3.97 s (3H); 3.61 m 2-(3-Fluoro-4- (2H); 3.09 dd (J = 6.2 Hz methoxyphenyl)-6-/ 14.7 Hz, 1 H); 2.94 dd (J
trifluoromethoxyquinoline-4-7.5 Hz / 14.5 Hz, 1 H).
carboxylic acid 112 2-(3-Fluoro-4- 13 (DMSO-d6): 10.86 s(1 H); N
methoxyphenyl)-6,8- 8.55 d (J = 8.5 Hz, 1 H); i dimethylquinoline-4- 8.14 dd (J = 2.1 Hz / 15.3 HO
carboxylic acid [(R)-2- Hz, 1 H); 8.04 d (J = 8.7 0 NH
hydroxy-1-(1 H-indol-3- Hz, 1 H); 7.87 s(1 H); 7.69 ylmethyl)ethyl]amide; d (J = 7.9 Hz, 1 H); 7.49 d N
(J = 2.3 Hz, 1 H); 7.37 d (J 0 (D)-Tryptophanol = 8.7 Hz, 2H); 7.22 s and (1 H); 7.10 m(1 H); 6.99 m (1H); 4.90 m (1H); 4.40 m 2-(3-Fluoro-4- (1 H); 3.96 s (3H); 3.60 m methoxyphenyl)-6, 8- (2H); 3.08 m(1 H); 2.95 m dimethylquinoline-4- (1 H); 2.76 s (3H); 2.38 s carboxylic acid (3H).

Example 113 2-(3,4-Dimethoxyphenyl)-6-methoxy-3-methylquinoline-4-carboxylic acid [(R)-1-H
N
HO
O NH
O, O N
hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide; 'Ox 113a) 2-(3,4-Dimethoxyphenyl)-6-methoxy-3-methylquinoline-4-carboxylic acid 3',4'-Dimethoxy-l-phenylpropiophenone (1.5g) and 5-methoxyisatin (1.4 g) were heated together in aqueous 30% strength potassium hydroxide solution (20 ml) under reflux overnight. The reaction mixture was added to water and the remaining residue was fil-tered off with suction. The filtrate was acidified with glacial acetic acid and placed in a refrigerator overnight. The precipitated reaction product was filtered off, dried in vacuo and employed without further purification in the next stage (yield 34%).

(DMSO-d6): 7,90 d (J = 9.2 Hz); 7.39 dd (J = 9.2 Hz / 2.8 Hz, 1 H); 7.04 m (4H); 3.85 s (3H); 3.79 s (3H); 3.76 s (3H); 2.35 s(3H).

113b) 2-(3,4-Dimethoxyphenyl)-6-methoxy-3-methylquinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide The quinolinecarboxylic acid from the previous stage (200 mg) was stirred together with (D)-tryptophanol (108 mg), HOBt (87 mg), EDC (109 mg) and diisopropylethylamine (0.099 ml) in DMF (10 ml) at room temperature overnight. The mixture was added to water and stirred for 10 minutes, and the precipitate was filtered off. The crude product was purified by column chromatography using Flashmasters and crystallized from diisopropyl ether. The title compound is obtained in 30% yield (90 mg).

=
(DMSO-d6): 10.76 s (1 H); 8.56 d (J = 8.9 Hz, 1 H); 7.83 d (J = 9.2 Hz, 1 H);
7.59 d (J
7.7 Hz, 1 H); 7.27 m (3H); 7.02 m (5H); 4.90 m(1 H); 4.47 m(1 H); 3.79 s (6H);
3.56 m (2H); 2.96 m(1 H); 2.69 m(1 H); 2.05 s(3H).

The following compounds were obtained in analogy to the preparation methods de-scribed in detail:

Ex. Product; aMetho naloa 'H-NMR (400 MHz) S Structure reagents 9ous to [ppm]

114 6-Amino-2-(3-fluoro-4- 20 (DMSO-d6): 10.82 s (1 H); H
N
methoxyphenyl)quinoline-4- 8.43 d (J = 8.3 Hz, 1 H);
carboxylic acid [(R)-2- 7.94 d (J = 2.3 Hz / 13.1 Ho = o NH
hydroxy-1-(1H-indol-3- Hz, 1 H); 7.84 d (J 9.4 NHZ
ylmethyl)ethyl]amide; Hz, 1 H); 7.70 m(2H); 7.19 F I N ~
s(1 H); 7.14 m(1 H); 7.03 . I ~

2-(3-Fluoro-4- m(1 H); 6.96 m(1 H); 5.69 methoxyphenyl)- 6- (2H); 4.82 (m, 1 H); 4.28 nitroquinoline-4-carboxylic m(1 H); 3.89 s(3H); 3.55 acid ((R)-2-hydroxy-1-(1H- m(2H); 3.03 m(1H); 2.96 indol-3-y1methyl)ethy1]amide m (1 H).

Example 115 2-(4,6-Dimethoxybenzofuran-2-yl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl]-OH
I \ /
O NH N
H
0, O N
O ~ ~

6-methoxyquinoline-4-carboxamide; ' 115a) 1-(4,6-Dimethoxybenzofuran-2-yl)ethanone 4,6-Dimethoxysalicylaldehyde (500 mg), 1-chloro-2-propanone (241 NI), potassium car-bonate (379 mg) were stirred in 2-butanone (20 ml) under a nitrogen atmosphere at 90 C for 8 hours. The reaction mixture was diluted with water and extracted with ethyl acetate, and the combined organic phases were washed with saturated aqueous NaCI
solution. The solvent was distilled out in vacuo, and the crude product was purified by Flashmaster chromatography. The title compound was obtained in 29% yield (174 mg).
(CDCI3): 7.53 s(1 H); 6.64 m(1 H); 6.32 s(1 H); 3.91 s(3H); 3.86 s(3H); 2.53 s(3H).
115b) 2-(4,6-Dimethoxybenzofu'ran-2-yl)-6-methoxyquinoline-4-carboxylic acid 1-(4,6-Dimethoxybenzofuran-2-yl)-ethanone (169 mg), 5-methoxyisatin (136 mg) were stirred together with potassium hydroxide solution (30% strength in water, 2.7 ml) under a nitrogen atmosphere at 80 C for 8 hours. The reaction mixture was added to 150 ml of water and, while cooling in ice, acidified with 70% strength acetic acid until a pH of 5-6 was reached. After 30 minutes, stirring with n-butanol/ethyl acetate (1:1, 20 ml) and back-extraction with ethyl acetate were carried out. The combined organic phases were washed with saturated aqueous NaCI solution. The solvent was distilled out in vacuo.
Crystallization from dichloromethane/methanol results in the title compound in 78%
yield (227 mg).
(DMSO-d6): 8.39 s (1 H); 8.10 s (1 H); 8.00 m (J = 9.3 Hz, 1 H); 7.64 s(1 H);
7.48 m(1 H);
6.95 s(1 H); 6.44 s(1 H); 3.88 s (6H); 3.81 s (3H).

11 5c) 2-(4,6-Dimethoxybenzofuran-2-yl)-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-yl)ethylj-6-methoxyquinoline-4-carboxamide The quinolinecarboxylic acid (120 mg) was converted into the title compound in 64%
yield (93 mg) in analogy to general method 113b.
(DMSO-d6): 10.85 s ( 1 H); 8.68 d (J = 8.8 Hz, 1 H); 7.97 d (J = 9.1 Hz, 1 H);
7.92 s(1 H);
7.66 d (J = 8.0 Hz, 1 H); 7.63 d (J = 0.8 Hz, 1 H); 7.44 dd (J = 9,1 Hz / 2.8 Hz, 1 H); 7.39 d(J = 2.8 Hz, 1 H); 7.36 d(J = 8.0 Hz, 1 H); 7.22 d(J = 2.0 Hz, 1 H); 7.08 dd (J = 8.0 Hz /
7.0 Hz, 1 H); 6.99 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 6.98 s (1 H); 6.49 s (1 H);
4.93 m (1 H);
4.42 m(1 H); 3.94 s (3H); 3.86 s (3H); 3.73 s (3H); 3.61 m (2H); 3.05 dd (J =
14.9 Hz /
6.3 Hz, 1 H); 2.93 dd (J = 14.9 Hz / 7.8 Hz, 1 H).

The following compounds were obtained in analogy to the preparation methods de-scribed in detail:

Product; Method 'H-NMR (400 MHz) S Structure Ex. rea ents analo-9 gous to IPPm]

116 N-[(R)-1-(Hydroxymethyl)-2- 115 (DMSO-d6): 10.85 s o"
(1 H-indol-3-yl)ethyl]-6- (1 H); 8.71 d(J = 8.6 Hz, o NH N
H
methoxy-2-(5- 1 H); 8.02 d (J = 9.1 Hz, o, O N
methoxybenzofuran-2- 1 H); 7.94 s(1 H); 7.67 d yl)quinoline-4-carboxamide; (J = 8.0 Hz, 1 H); 7.66 d -o (J = 8.6 Hz, 1 H); 7.65 s D-Tryptophanol and (1 H); 7.46 dd (J = 9.1 Hz 6-Methoxy-2-(5- / 2.8 Hz, 1 H); 7.41 d (J =
methoxybenzofuran-2- 2.8 Hz, 1 H); 7.36 d (J =
yl)quinoline-4-carboxylic acid 8=0 Hz, 1 H); 7.27 d (J =
2.8 Hz, 1 H); 7.23 d (J =
2.0 Hz, 1 H); 7.09 dd (J =
8.0 Hz / 7.0 Hz, 1 H); 7.02 dd (J = 8.6 Hz / 2.8 Hz, 1 H); 6.99 dd (J = 8.0 Hz /
7.0 Hz, 1 H); 4.93 m(1 H);
4.43 m(1 H); 3.84 s (3H);
3.74 s (3H); 3.61 m (2H);
3.06 dd (J = 14.7 Hz / 5.6 Hz, 1 H); 2.94 dd (J =
14.7 Hz / 8.1 Hz, 1 H).

117 2-(7-Ethoxybenzofuran-2-yl)- 115 (DMSO-d6): 10.84 s o"
NH ~ H
N-[(R)-1-(hydroxymethyl)-2- (1 H); 8.74 d (J = 8.6 Hz, 0 (1 H-indol-3-yl)ethyl]-6- 1 H); 8.04 d (J = 9.1 Hz, \_o o; o, methoxyquinoline-4- 1 H); 7.96 s(1 H); 7.70 s N
carboxamide; (1 H); 7.68 d (J = 8.0 Hz, 1 H); 7.47 dd (J = 9.1 Hz /
D-Tryptophanol and 2.8 Hz, 1 H); 7.42 d (J =

Product; Method 1 Ex. analo- H-NMR (400 MHz) S Structure reagents 9oUs to IPPm]
2-(7-Ethoxybenzofuran-2-y1)- 2.8 Hz, 1 H); 7.36 d (J =
6-methoxyquinoline-4- 8.0 Hz, 1 H); 7.32 d (J =
carboxylic acid 7.8 Hz, 1 H); 7.24 d (J =
2.3 Hz, 1 H); 7.23 dd (J =
7.8 Hz / 7.8 Hz, 1 H); 7.08 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 7.03 d (J = 7.8 Hz, 1H);7.01dd(J=8.0Hz/
7.0 Hz, 1 H); 4.94 m(1 H);
4.45 m (1 H); 4.30 q (J =
6.9 Hz, 2H); 3.73 s (3H);
3.62 m (2H); 3.06 dd (J =
14.7 Hz / 5.6 Hz, 1 H);
2.95 dd (J = 14.7 Hz / 8.3 Hz, 1 H); 1.48 t(J = 6.9 Hz, 3H).

118 N-[(R)-1-(Hydroxymethyl)-2- 115 (DMSO-d6): 10.85 s OH
(1 H-indol-3-yl)ethyl]-6- (1 H); 8.70 d(J = 8.6 Hz, 0 "H ~ N
methoxy-2-(6- 1 H); 7.99 d (J = 9.1 Hz, o, a, "
methoxybenzofuran-2- 1 H); 7.90 s(1 H); 7.67 d o r~~
yi)quinoline-4-carboxamide; (J = 8.0 Hz, 1 H); 7.65 d (J = 8.6 Hz, 1 H); 7.64 s D-Ttyptophanol and (1 H); 7.45 dd (J = 9.1 Hz 6-Methoxy-2-(6- / 2.8 Hz, 1 H); 7.41 d (J =
methoxybenzofuran-2- 2.8 Hz, 1 H); 7.36 d (J =
yl)quinoline-4-carboxylic acid 8.0 Hz, 1 H); 7.27 d (J =
2.1 Hz, 1 H); 7.23 d (J =
2.3 Hz, 1 H); 7.09 dd (J =
8.0 Hz / 7.0 Hz, 1 H); 6.99 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 6.97 dd (J = 8.6 Hz /
2.3 Hz, 1 H); 4.92 m(1 H);
4.44 m(1 H); 3.87 s (3H);

Product; Method 'H-NMR (400 MHz) S Structure Ex. rea ents analo-g gous to (ppm]
3.73 s (3H); 3.61 m (2H);
3.06 dd (J = 14.4 Hz / 5.6 Hz, 1 H); 2.98 dd (J =
14.4 Hz / 8.1 Hz, 1 H).

119 2-(7-Fluorobenzofuran-2-yl)- 115 (DMSO-d6): 10.85 s H
N-[(R)-1-(hydroxymethyl)-2- (1 H); 8.75 s(1 H); 8.05 d o HI N
H
(1 H-indol-3-yi)ethyl]-6- (J = 9.1 Hz, 1 H); 7.99 s o"
F O IN /
methoxyquinoline-4- (1 H); 7.83 d (J = 3.0 Hz, carboxamide; 1 H); 7.67 d (J = 8.0 Hz, 1 H); 7.62 m (1 H); 7.49 dd D-Ttyptophanol and (J = 9.1 Hz / 2.8 Hz, 1 H);
2-(7-Fluorobenzofuran-2-y1)- 7.43 d(J = 2.8 Hz, 1 H);
6-methoxyquinoline-4- 7.36 d (J = 8.0 Hz, 1 H);
carboxylic acid 7.34 m (2H); 7.23 d (J =
2.0 Hz, 1 H); 7.08 dd (J =
8.0 Hz / 7.0 Hz, 1 H); 6.99 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 4.9 5 m (1 H); 4.44 m (1 H); 3.74 s (3H); 3.62 m (2H); 3.05 dd (J = 14.7 Hz / 5.6 Hz, 1 H); 2.94 dd (J = 14.7 Hz / 8.1 Hz, 1 H).

120 2-(4-Fluorobenzofuran-2-yl)- 115 (DMSO-d6): 10.88 s OH
N-[(R)-1-(hydroxymethyl)-2- (1 H); 8.75 d (J = 8.6 Hz, o H N
H
(1 H-indol-3-yl)ethyl]-6- 1 H); 8.04 d (J = 9.1 Hz, o,~
o IN /
methoxyquinoline-4- 1 H); 8.02 s(1 H); 7.83 d carboxamide; (J = 1.0 Hz, 1 H); 7.66 d F
(J = 8.3 Hz, 1 H); 7.66 d D-Tryptophanol and (J = 8.0 Hz, 1 H); 7.48 dd 2-(4-Fluorobenzofuran-2-y1)- (J = 9.1 Hz / 2.8 Hz, 1 H);
6-methoxyquinoline-4- 7.45 ddd (J = 8.3 Hz / 8.3 Product; Method 'H-NMR (400 MHz) S Structure Ex. reagents gousanelo-to [ppm]
carboxylic acid Hz / 5.8 Hz, 1 H); 7.42 d (J = 2.8 Hz, 1 H); 7.36 d (J = 8.0 Hz, 1 H); 7.23 d (J = 2.0 Hz, 1 H); 7.19 dd (J = 9.6 Hz / 8.3 Hz, 1 H);
7.08dd(J=8.0Hz/7.0 Hz, 1 H); 6.98 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 4.97 m (1 H); 4.43 m(1 H); 3.74 s (3H); 3.62 m (2H); 3.06 dd (J = 14.7 Hz / 5.8 Hz, 1 H); 2.94 dd (J = 14.7 Hz / 8.1 Hz, 1 H).

121 N-[(R)-1-(Hydroxymethyl)-2- 115 (DMSO-d6): 10.86 s OH
(1 H-indol-3-yl)ethyl]-6- (1 H); 8.72 d (J = 8.6 Hz, 0 NH I N
H
methoxy-2-(5- 1 H); 8.01 d (J = 9.1 Hz, ,~
O ~N I /
methylbenzofuran-2- 1 H); 7.94 s (1 H); 7.67 d yI)quinoline-4-carboxamide; (J = 8.0 Hz, 1 H); 7.64 s (1 H); 7.63 d (J = 8.6 Hz, D-Tryptophanol and 1 H); 7.56 d (J = 1.5 Hz, 6-Methoxy-2-(5- 1 H); 7.46 dd (J = 9.1 Hz /
methylbenzofuran-2- 2.8 Hz, 1 H); 7.41 d (J =
yl)quinoline-4-carboxylic acid 2.8 Hz, 1 H); 7.36 d (J =
8.0 Hz, 1 H); 7.24 dd (J =
8.6 Hz / 1.5 Hz, 1 H); 7.23 d (J = 2.0 Hz, 1 H); 7.09 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 6.99 dd (J = 8.0 Hz /
7.0 Hz, 1 H); 4.94 m(1 H);
4.43 m(1 H); 3.74 s (3H);
3.61 m (2H); 3.06 dd (J =
14.7 Hz / 5.8 Hz, 1 H);
2.94 dd (J = 14.7 Hz / 8.1 Product; Method 'H-NMR (400 MHz) S Structure Ex. rea ents analo-9 gous to IPPm]
Hz, 1 H); 2.44 s (3H).

122 N-[(R)-1-(Hydroxymethyl)-2- 115 (DMSO-d6): 10.86 s OH
(1 H-indol-3-yl)ethyl]-6- (1 H); 8.75 d (J = 8.6 Hz, o NH N
H
methoxy-2-(7- 1 H); 8.03 d (J = 9.1 Hz, o, methylbenzofuran-2- 1 H); 7.98 s(1 H); 7.70 s yI)quinoline-4-carboxamide; (1 H); 7.67 d (J = 8.0 Hz, 1 H); 7.60 m(1 H); 7.47 dd D-Tryptophanol and (J = 9.1 Hz / 2.8 Hz, 1 H);
6-Methoxy-2-(7- 7.43 d (J = 2.8 Hz, 1 H);
methylbenzofuran-2- 7.36 d(J = 8.0 Hz, 1 H);
yl)quinoline-4-carboxylic acid 7.24 m (3H); 7.08 dd (J =
8.0 Hz / 7.0 Hz, 1 H); 6.99 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 4.95 m(1 H); 4.43 m (1 H); 3.74 s (3H); 3.62 m (2H); 3.06 dd (J = 14.7 Hz / 5.6 Hz, 1 H); 2.95 dd (J = 14.7 Hz / 8.3 Hz, 1 H); 2.61 s (3H).

123 N-[(R)-1-(Hydroxymethyl)-2- 115 (DMSO-d6): 10.85 s OH
(1 H-indol-3-yl)ethyl]-6- (1 H); 8.70 d (J = 8.6 Hz, o NH
H
methoxy-2-(4- 1 H); 8.01 d (J = 9.1 Hz, o, methoxybenzofuran-2- 1 H); 7.99 s(1 H); 7.73 s yI)quinoline-4-carboxamide; (1 H); 7.67 d (J = 8.0 Hz, 0 ~
1 H); 7.46 dd (J = 9.1 Hz /
D-Tryptophanol and 2.8 Hz, 1 H); 7.41 d (J =
6-Methoxy-2-(4- 2.8 Hz, 1 H); 7.37 m(2H);
methoxybenzofuran-2- 7.36 d (J = 8.0 Hz, 1 H);

Product; Method 'H-NMR (400 MHz) S Structure Ex. rea ents analo-3 gous to IPPm]
yl)quinoline-4-carboxylic acid 7.22 s (1 H); 7.08 dd (J =
8.0 Hz / 7.0 Hz, 1 H); 6.99 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 6.88 dd (J = 7.1 Hz/
1.8 Hz, 1 H); 4.94 m(1 H);
4.43 m(1 H); 3.98 s (3H);
3.73 s (3H); 3.61 m (2H);
3.05 dd (J = 14.7 Hz / 5.6 Hz, 1 H); 2.93 dd (J =
14.7 Hz / 8.1 Hz, 1 H).

124 N-[(R)-1-(Hydroxymethyl)-2- 115 (DMSO-d6): 10.86 s OH
(1 H-indol-3-yl)ethyl]-6- (1 H); 8.75 d (J = 8.6 Hz, " H
0, methoxy-2-[5- 1 H); 8.04 d (J = 9.1 Hz, o N
(trifluoromethoxy)benzofuran- 1 H); 7.98 s (1 H); 7.90 d F
F~--O
2-yi]quinoline-4-carboxamide; (J = 8.8 Hz, 1 H); 7.83 d F
(J = 1.5 Hz, 1 H); 7.78 d D-Tryptophanol and (J = 0.8 Hz, 1 H); 7.66 d 6-Methoxy-2-[5- (J = 8.0 Hz, 1 H); 7.49 dd (trifluoromethoxy)benzofuran- (J = 9.1 Hz / 2.8 Hz, 1 H);
2-yl]quinoline-4-carboxylic 7.43 dd (J = 8.8 Hz / 1.5 acid Hz, 1 H); 7.42 d (J = 2.8 Hz, 1 H); 7.36 d (J = 8.0 Hz, 1 H); 7.23 d (J = 2.0 Hz, 1 H); 7.08 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 6.99 dd (J = 8.0 Hz / 7.0 Hz, 1 H);
4.95 m (1 H); 4.43 m (1 H); 3.74 s(3H); 3.61 m (2H); 3.06 dd (J = 14.7 Hz / 5.6 Hz, 1 H); 2.94 dd (J = 14.7 Hz / 8.1 Hz, 1 H).

Example 125 4-Ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-H
N
HO
O NH
~
yl)ethyl]amide;

125a) Ethyl 5-bromo-2-ethoxybenzoate 5-Bromo-2-hydroxybenzoic acid (5g) and potassium carbonate (6.37 g) in acetone (230 ml) were stirred under reflux under a nitrogen atmosphere and, at the boiling point, iodoethane (5 x 5 ml) was slowlly added at intervals of 1 hour. Stirring under reflux was continued for 4 hours. The solvent was distilled out in a rotary evaporator, the residue was taken up in ethyl acetate and extracted with water and saturated aqueous NaCl solution, and the combined organic phases were freed of solvent. Flash chromatogra-phy resulted in 4.1 g (65% yield) of the title compound. MS (ESI, +): 274 (M+1).
125b) 5-Bromo-2-ethoxybenzoic acid Ethyl 5-bromo-2-ethoxybenzoate (5g) were stirred under reflux in potassium hydroxide (10% strength in ethanol, 50 ml) for twelve hours. The cooled reaction mixture was mixed with water, and the remaining ethanol was distilled out in a rotary evaporator.
The remaining aqueous phase was washed with diethyl ether and acidified by adding 2N HCI. The precipitated reaction product was filtered off and washed with water. Dry-ing in vacuo resulted in 4.25 g (95% yield) of the title compound, which was employed without further purification in the next stage.
MS (ESI, +): 246 (M+1) 125c) Methyl (R)-2-(5-bromo-2-ethoxybenzoylamino)-3-(1 H-indol-3-yl)-propionate 5-Bromo-2-ethoxybenzoic acid (500 mg), (D)-tryptophan methyl ester hydrochloride (520 mg), EDC (390 mg), HOBt (310 mg) and diisopropylethylamine (0.36 ml) in DMF
(10 ml) were stirred together at room temperature overnight. The reaction mixture was concentrated, taken up in ethyl acetate and extracted several times with water. The combined organic phases were freed of solvent, and the reaction mixture was purified by flash chromatography. 660 mg of the title compound (73% yield) were obtained. MS
(ESI, +): 446 (M+1) 125d) 5-Bromo-2-ethoxy-N-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]benzamide A solution of methyl (R)-2-(5-bromo-2-ethoxybenzoylamino)-3-(1 H-indol-3-yl)-propionate (500 mg) in THF (10 ml) was cooled to -10 C, and a solution of lithium borohydride in THF (0.84 ml, 2 mmol/ml) was slowly added dropwise. The mixture was stirred overnight and then 1 N HCI was cautiously added. The solvent was distilled out in a rotary evaporator, and the remaining aqueous phase was extracted with ethyl acetate.
The combined organic phases were freed of solvent and dried in vacuo. 435 mg of the title compound (93% yield) were obtained after crystallization from ethanol.
MS (ESI, +):
418 (M+1) 125e) 4-Ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yI)ethyl]amide 5-Bromo-2-ethoxy-N-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]benzamide (200 mg), phenylboronic acid (64 mg), sodium carbonate (2 M solution in water, 1 ml) and Pd(PPh3)4 (6 mg) were heated to reflux together in toluene (6 ml) and ethanol (0.4 ml) overnight. The reaction mixture was filtered and the filtrate was concentrated. The resi-due was taken up in ethyl acetate and extracted with water. The organic phases were dried and the solvent was distilled off in a rotary evaporator. Flash chromatography re-sulted in 45 mg of the title compound (21 % yield).

(DMSO-ds): 10.78 s (1 H); 8.37 d (J = 8 Hz, 1 H); 8.13 s (1 H); 7.76 -7.50 broad m (5H);
7.42 m (2H); 7.29 m (2H); 7.03 m (1H); 6.91 m (1H); 4.30 m (1H); 4.11 m (2H);
3.42 m, (2H): 2.95 m (2H); 1.28 m (3H).
The following compounds were obtained in analogy to the preparation methods de-scribed in detail:

Product; Method 'H-NMR (400 MHz) S Structure Ex. reagents g ~ o [ppm]

126 4-Ethoxy-3'-fluoro-4'- 125 (DMSO-d6): 10.78 s(1 H); - N
propoxybiphenyl-3-carboxylic 8.36 d (J = 8.1 Hz, 1 H);
acid [(R)-2-hydroxy-1-(1 H-indol- 8.08 s(1 H); 7.70 m (2H); HO

3-ylmethyl)ethyl]amide; 7.47 d (J = 12.9 Hz, 1 H);
7.37 m(1 H); 7.35 m(1 H): F
5-Bromo-2-ethoxy-N-((R)-2-7.15 m(4H); 7.03 m(1 H); o hydroxy-1-(1 H-indol-3-6.93 m(1 H); 4.90 m(1 H);
ylmethyl)ethyl]benzamide 4.22 m(1 H); 4.12 m (2H);
and 3.46 m(1 H); 3.40 m(1 H);
3-Fluoro-4-propoxyphenyl- 2.95 m (2H); 1.73 m (2H);
boronic acid 1.27 m(3H); 0.98 m (3H).

127 2-Ethoxy-N-[(R)-1- 125 (DMSO-d6): 10.79 s(1H); N
hydroxymethyl-2-(1 H-indol-3- 8.40 d (J = 2.5 Hz, 1 H); i yI)ethyl]-5-(6-methoxypyridin-3- 8.36 d (J = 8.1 Hz, 1 H); Ho yI)benzamide; 8.07 s (1 H); 7.94 dd (J = 0 NH
2.8 / 8.6 Hz, 1 H); 7.68 m 5-Bromo-2-ethoxy-N-[(R)-2-(2H); 7.30 d (J = 8.1 Hz, N
hydroxy-1-(1H-indol-3- 11 1 H); 7.18 d (J = 8.6 Hz, 0 ylmethyl)ethyl]benzamide 1 H); 7.13 s (1 H); 7.03 m and (1 H); 6.93 m(1 H); 6.88 m (1 H); 4.22 m(1 H); 4.12 m 2-Methoxy-5-pyridineboronic (2H); 3.86 s (3H); 3.47 m acid (2H); 2.95 m (2H); 1.28 m (3H).

Product; Method 'H-NMR (400 MHz) 8 Structure Ex. reagents gous ~ o [ppm]

128 4-Ethoxy-2'-fluoro-3'- 125 (DMSO-d6): 10.79 s(1 H); H
methoxybiphenyl-3-carboxylic 8.36 d (J = 8.1 Hz, 1 H);
acid [(R)-2-hydroxy-l-(1 H-indol- 8.02 s(1 H); 7.65 d(J = HO
O H
3-ylmethyl)ethyl]amide; 8.1 Hz, 1 H); 7.60 m(1 H);

5-Bromo-2-ethoxy-N-((R)-2- 7.29 d (J = 8.1 Hz, 1 H); 'o I
7.18 m (4H); 7.00 m (2H); I
hydroxy-1-(1 H-indol-3-ylmethyl)ethylJbenzamide 6.93 m(1 H); 4.90 m(1 H);
4.23 m(1 H); 4.13 m (2H);
and 3.84 s (3H); 3.46 m(1 H);
2-Fluoro-3-methoxyphenyl- 3.38 m(1 H); 2.95 m (2H);
boronic acid 1.28 m (3H).

129 4'-Acetylamino-4- 125 (DMSO-d6): 10.82 s(1 H); S
H ethoxybiphenyl-3-carboxylic 10.04 s(1 H); 8.43 d (J =
acid [(R)-1-hydroxymethyl-2- 8.1 Hz, 1 H); 8.19 d (J Ho O NH
(1 H-indol-3-yl)ethyl]amide; 2.5 Hz, 1 H); 7.89 s (1 H);
5-Bromo-2-ethoxy-N-[(R)-2- 7.73 m(2H); 7.58 m (1 H); o hydroxy-1-(1H-indol-3- A N
7.33 m (3H); 7.26 d (J = H
ylmethyl)ethylJbenzamide 8.9 Hz, 1 H); 7.18 s(1 H);

and 7.07 m(1 H); 6.96 m(1 H);
4-Acetamidophenylboronic acid 4 29 m(1 H); 4.17 m(2H);
3.48 m (2H); 2.99 m (2H);
2.08 s (3H); 1.33 m (3H).

130 2-Ethoxy-N-[(R)-1- 125 (CDCI3): 8.88 s (2H); 8.49 - N
hydroxymethyl-2-(1 H-indol-3- d (J - 7.6 Hz, 1 H); 8.41 s \
yI)ethyl]-5-(2-methoxypyrimidin- (1 H); 8.17 s(1 H); 7.70 d Ho 5-yl)benzamide; o NH
(J = 7.6 Hz, 1 H); 7.56 d(J
5-Bromo-2-ethoxy-N-[(R)-2-= 8.3 Hz, 1 H); 7.37 d (J =
hydroxy-1-(1H-indol-3- N~
8.1 Hz, 1 H); 7.19 m(1 H); =o) 'N
ylmethyl)ethylJbenzamide 7.11 m (2H); 7.02 d (J -and 8.3 Hz, 1 H); 4.59 m (2H);
2-Methoxypyrimidine-5-boronic 4.10 m(5H); 3.84 m(2H);
acid 3.16 m (2H); 1.28 m (3H).

Product; Method 'H-NMR (400 MHz) S Structure Ex. reagents 9 ~ o [ppm]

131 4-Ethoxy-5'-fluoro-3'- 125 (DMSO-d6): 10.78 s(1 H); H
methoxybiphenyl-3-carboxylic 8.35 d (J = 7.8 Hz, 1 H);
acid [(R)-2-hydroxy-l-(1 H-indol- 8.10 s (1H); 7.77 dd (J = HO
O H
3-ylmethyl)ethyl]amide; 2.5 Hz / 8.8 Hz, 1 H); 7.66 (J = 7.6 Hz, 1 H); 7.61 -5-Bromo-2-ethoxy-N-[(R)-2- d 7.49 m (3H); 7.30 d (J =
hydroxy-1-(1 H-indol-3- 8.1 Hz, 1 H); 7.18 d (J = F
ylmethyl)ethylJbenzamide 7.8 Hz, 1 H); 7.13 s(1 H);

and 7.04 - 6.91 m (3H); 6.77 m(1 H); 4.90 m(1 H); 4.21 3-Fluoro-5-methoxyphenyl- m(1 H); 4.12 m(2H); 3.81 boronic acid s (1 H); 3.42 m (2H); 2.95 m (2H); 1.30 m (3H).

132 4-Ethoxy-3',4'-difluoro-5'- 125 (DMSO-d6): 10.78 s(1 H); H
methoxybiphenyl-3-carboxylic 8.34 d (J 8.1= Hz, 1 H);
acid [(R)-2-hydroxy-l-(1 H-indol- 8.11 s(1 H); 7.78 dd (J = Ho O H
3-ylmethyl)ethyl]amide; 2.5 Hz / 8.6 Hz, 1 H); 7.67 \ o~
d (J = 7.8 Hz, 1 H); 7.30 do 5-Bromo-2-ethoxy-N-((R)-2-(J = 8.1 Hz, 1 H); 7.25 - F
hydroxy-l-(1H-indol-3- 7.17 m(3H); 7.13 s(1H); F
ylmethyl)ethylJbenzamide 7.02 m (1 H); 6.93 m (1 H);

and 4.22 m(1 H); 4.14 m (2H);
3.94 s (3H); 3.47 m(1 H);
3,4-Difluoro-5-methoxyphenyl- 3.39 m(1H); 2.95 m (2H);
boronic acid 1.29 m (3H).

133 4-Ethoxy-4'-fluoro-3'- 125 (DMSO-d6): 10.78 s(1 H); H
N
methoxybiphenyl-3-carboxylic 8.36 d (J = 8.1 Hz, 1 H);
acid [(R)-2-hydroxy-l-(1H-indol- 8.10 s(1H); 7.72 dd (J- Ho 3-ylmethyl)ethyl]amide; 0 H
2.6 Hz / 8.7 Hz, 1 H); 7.65 5-Bromo-2-ethoxy-N-[(R)-2-d (J = 8.8 Hz, 1 H); 7.19 m o I~
hydroxy-l-(1H-indol-3- (6H); 7.02 m(1H); 6.93 mF
ylmethyl)ethylJbenzamide (1 H); 4.25 m(1 H); 4.14 Product; Method 'H-NMR (400 MHz) S Structure Ex. reagents 9 ~ o [ppm]

and (m 2H); 3.90 s (3H); 3.45 4-Fluoro-3-methoxyphenyl- m (2H); 2.95 m (2H); 1.28 boronic acid m (3H).

134 3',5'-Dimethoxy-4- 125 (DMSO-d6): 10.78 s(1 H); - H
N
propoxybiphenyl-3-carboxylic 8.31 d (J =8.2 Hz, 1 H); ~
acid [(R)-1-hydroxymethyl-2- 8.11 s(1 H); 7.71 dd (J = Ho (1 H-indol-3-yl)ethyl]amide; 2.6 Hz / 8.7 Hz, 1 H); 7.65 d (J = 7.9 Hz, 1 H); 7.30 d o I~
N-((R)-1-Hydroxymethyl-2-(1 H-(J = 8.1 Hz, 1 H); 7.15 d (J indo1-3-y1)ethylJ-5-iod-2- = 8.9 Hz, 1 H); 7.12 s propoxybenzamide (1 H); 7.02 m(1 H); 6.93 m and (1 H); 6.70 s (2H); 6.45 s (1 H); 4.89 m(1 H); 4.24 m 3,5-Dimethoxyphenylboronic (1 H); 4.03 m (2H); 3.77 s acid pinacol ester (6H); 3.46 m (2H); 2.95 m (2H); 1.65 m (2H); 0.91 m (3H).

Example 135 4-Ethoxy-3'-hydroxymethylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-H
N
HO .

I \ 0'_., indol-3-yi)ethyl]amide; HO
5-Bromo-2-ethoxy-N-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]benzamide (0.2 M so-lution in THF, 500 NI, prepared by general method 125a-d), triethylamine (0.6 M solu-tion in THF, 200 NI), palladium(II) acetate (0.0375 M in THF, 250 NI), triotolylphosphine (0.05 M solution in THF, 400 NI), 3-hydroxymethyl-phenylboronic acid (0.4 M
solution in THF, 200 NI) and water (200 NI) were pipetted into a glass reactor of a microwave and provided with a stirring bar. The mixture was stirred in the microwave at 1200 W, and at 120 C under pressure for 30 minutes.

The THF was stripped off in a centrifuge, and the residue was then dissolved in 2 ml of DMSO and purified by HPLC.

HPLC-MS: Column Purospher Star RP C18 4.6x125 5pm; detection wavelength 214 nm; flow rate 1 mi/min; eluents A: 0.1% TFA in H20, B 0.1 % TFA in ACN;
gradient in each case based on B: 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1): 445.5 Retention time: 8.3 min.

The following compounds were obtained in analogy to the preparation methods de-scribed in detail:

Product; Method HPLC-MS conditions / Structure Ex. analo- I
reagents gousto H-NMR (400 MHz) S [ppm]

136 4-Ethoxy-3'- 135 Column Purospher Star RP N
methylsulphanylbiphenyl-3- C18 4.6x125 5pm; detec-tion wavelength 214 nm; Ho carboxylic acid [(R)-2-hydroxy- o HNH
1- 1H-indol-3- flow rate 1 ml/min; eluents ylmethyl)ethyl]amide; A: 0.1% TFA in H20, B I'S
0.1 % TFA in ACN; gradient 5-Bromo-2-ethoxy-N-[(R)-2- in each case based on B:
hydroxy-l-(1H-indol-3- 5% to 95% (10') to 95% (2') ylmethyl)ethyl]benzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 461.6 3-(Methylthio)phenylboronic Retention time: 10.11 min.
acid 137 3'-Cyano-4-ethoxybiphenyl-3- 135 Column Purospher Star RP S
Ncarboxylic acid [(R)-1-hydroxy- C18 4.6x125 5Nm; detec-methyl-2-(1 H-indol-3- tion wavelength 214 nm;
HO H
flow rate 1 mI/min; eluents p NH
yl)ethyl]amide;
A: 0.1% TFA in H20, B
5-Bromo-2-ethoxy-N-[(R)-2- 0.1 % TFA in ACN; gradient hydroxy-l-(1H-indol-3- in each case based on B:
ylmethyl)ethyl]benzamide 5% to 95% (10') to 95% (2') I I
to 5% (0.5') to 5% (2.5') N
and Molecular peak (ESI, M+1):
3-Cyanophenylboronic acid 440.5 Retention time: 9.28 min.

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents sousto H-NMR (400 MHz) 5[ppm]

138 2-Ethoxy-5-(6-fluoro-5- 135 Column Purospher Star RP N
methylpyridin-3-yl)-N-[(R)-2- C18 4.6x125 5pm; detec-hydroxy-1-(1 H-indol-3- tion wavelength 214 nm; Ho H
ylmethyl)ethyl]benzamide; flow rate 1 ml/min; eluents o NH
A: 0.1% TFA in H20, B
5-Bromo-2-ethoxy-N-[(R)-2- 0.1 % TFA in ACN; gradient hydroxy-1-(IH-indol-3- in each case based on B: F"
ylmethyl)ethylJbenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
2-Fluoro-3-methylpyridine-5- 448.5 boronic acid Retention time: 9.1 min.

139 4-Ethoxy-4'- 135 Column Purospher Star RP N
trifluoromethoxybiphenyl-3- C18 4.6x125 5Nm; detec-carboxylic acid [(R)-2-hydroxy- tion wavelength 214 nm; "o "NH
1-(1H-indol-3- flow rate 1 mI/min; eluents I\
ylmethyl)ethyl]amide; A: 0.1 % TFA in H20, B F F ~ ' x .~
0.1 % TFA in ACN; gradient F o 5-Bromo-2-ethoxy-N-[(R)-2- in each case based on B:
hydroxy-l-(1H-indol-3- 5% to 95% (10') to 95% (2') ylmethyl)ethylJbenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 499.5 4-(Trifluoromethoxy)phenyl- Retention time: 10.55 min.
boronic acid 140 5-Benzo[b]thiophene-3-y1-2- 135 Column Purospher Star RP _ H
ethoxy-N-[(R)-2-hydroxy- 1 -(1 H- C18 4.6x125 5pm; detec-indol-3- tion wavelength 214 nm; Ho H
flow rate 1 ml/min; eluents o""
ylmethyl)ethyl]benzamide;
A: 0.1 % TFA in H20, B - I~
\ -5-Bromo-2-ethoxy-N-[(R)-2- 0.1 % TFA in ACN; gradient s ~ I
hydroxy-l-(1H-indol-3- in each case based on B:

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]
ylmethyl)ethyl]benzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
1-Benzothiophen-3-ylboronic 471.6 acid Retention time: 10.68 min.

141 4-Ethoxy-2'- 135 Column Purospher Star RP N
trifluoromethylbiphenyl-3- C18 4.6x125 5pm; detec- ~/
tion wavelength 214 nm;
carboxylic acid [(R)-2-hydroxy-1-(1 H-indol-3- flow rate 1 mI/min; eluents HO H NH
ylmethyl)ethyl]amide; A: 0.1% TFA in H20, B
0.1% TFA in ACN; gradient 5-Bromo-2-ethoxy-N-[(R)-2- in each case based on B: F
hydroxy-1-(1H-indol-3- 5% to 95% (10') to 95% (2') F F
ylmethyl)ethyl]benzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 483.5 2-(Trifluoromethyl)phenyl- Retention time: 10.05 min.
boronic acid 142 4-Ethoxy-2'- 135 Column Purospher Star RP =: N
trifluoromethoxybiphenyl-3- C18 4.6x125 5pm; detec-carboxylic acid [(R)-2-hydroxy- tion wavelength 214 nm;
flow rate 1 ml/min; eluents HO H%
1-(1 H-indol-3- o NH
ylmethyl)ethyl]amide; A: 0.1% TFA in H20, B \ o~
0.1 % TFA in ACN; gradient ~
5-Bromo-2-ethoxy-N-[(R)-2- in each case based on B: F F
~ I x hydroxy-l-(1H-indol-3- 5% to 95% (10') to 95% (2') O F
ylmethyl)ethyl]benzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 499.5 2-(Trifluoromethoxy)phenyl- Retention time: 10.25 min.
boronic acid Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]

143 4-Ethoxy-3'- 135 Column Purospher Star RP N
trifluoromethoxybiphenyl-3- C18 4.6x125 5pm; detec- S
carboxylic acid [(R)-2-hydroxy- tion wavelength 214 nm; "o "NH
flow rate 1 mI/min; eluents 1-(1 H-indol-3- o"", ylmethyl)ethyl]amide; A: 0.1 % TFA in H20, B FXo F F \
0.1 % TFA in ACN; gradient 5-Bromo-2-ethoxy-N-[(R)-2- in each case based on B:
hydroxy-1-(1H-indol-3- 5% to 95% (10') to 95% (2') ylmethyl)ethylJbenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 499.5 3-(Trifluoromethoxy)phenyl- Retention time: 10.52 min.
boronic acid 144 4-Ethoxy-3'-fluoro-biphenyl-3- 135 Column Purospher Star RP
carboxylic acid [(R)-2-hydroxy- C18 4.6x125 5pm; detec- N
1-(1H-indol-3- tion wavelength 214 nm;
HO H
ylmethyl)ethyl]amide; flow rate 1 ml/min; eluents o NH
A: 0.1 % TFA in H20, B \ o 5-Bromo-2-ethoxy-N-[(R)-2- 0.1 % TFA in ACN; gradient hydroxy-1-(1H-indol-3- in each case based on B: ~ i ylmethyl)ethylJbenzamide 5% to 95% (10') to 95% (2') F
to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Fluorophenylboronic acid 433.5 Retention time: 9.8 min.

145 4'-Chloro-4-ethoxybiphenyl-3- 135 Column Purospher Star RP H
carboxylic acid [(R)-2-hydroxy- C18 4.6x125 5pm; detec-tion wavelength 214 nm; o 1-(1 H-indol-3- H H
ylmethyl)ethyl]amide; flow rate 1 mi/min; eluents o N"
\ o~
A: 0.1% TFA in H20, B i 5-Bromo-2-ethoxy-N-[(R)-2- 0.1% TFA in ACN; gradient I
ci hydroxy-1-(1H-indol-3- in each case based on B:
5% to 95% (10') to 95% (2') Product; Method HPLC-MS conditions I Structure Ex. analo- H-NMR (400 MHz) S[ppm]
reagents so~s to ylmethyl)ethyl]benzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 449.9 4-Chlorophenylboronic acid Retention time: 10.32 min.

146 4-Ethoxy-4'- 135 Column Purospher Star RP N
methylsulphanylbiphenyl-3- C18 4.6x125 5pm; detec-tion wavelength 214 nm;
carboxylic acid [(R)-2-hydroxy- Ho .
flow rate I mI/min; eluents o"H
1-(1 H-indol-3-ylmethyl)ethyl]amide; A: 0.1 % TFA in H20, B I~
0.1 % TFA in ACN; gradient I
5-Bromo-2-ethoxy-N-[(R)-2- in each case based on B:
hydroxy-1-(1H-indol-3- 5% to 95% (10') to 95% (2) ylmethyl)ethyl]benzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 461.6 4-(Methylthio)pheny1boronic Retention time: 10.17 min.
acid 147 4-Ethoxy-3'- 135 Column Purospher Star RP N
trifluoromethylbiphenyl-3- C18 4.6x125 5pm; detec-tion wavelength carboxylic acid [(R)-2-hydroxy- 214 nm; Ho 1-(1H-indol-3- flow rate 1 mI/min; eluents O HNH
ylmethyl)ethyl]amide; A: 0.1% TFA in H20, B
0.1 % TFA in ACN; gradient 5-Bromo-2-ethoxy-N-((R)-2- in each case based on B:
hydroxy-1-(1H-indol-3- 5% to 95% (10') to 95% (2') F
F F
ylmethyl)ethyl]benzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 483.5 3-(Trifluoromethyl)-phenyl- Retention time: 10.35 min.
boronic acid Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) 8 [ppm]

148 3'-Chloro-4-ethoxybiphenyl-3- 135 Column Purospher Star RP H
N
carboxylic acid [(R)-2-hydroxy- C18 4.6x125 5Nm; detec-1-(1H-indol-3- tion wavelength 214 nm; Ho H
ylmethyl)ethyl]amide; flow rate 1 mI/min; eluents 0 NH
A: 0.1 % TFA in H20, B
ci 5-Bromo-2-ethoxy-N-((R)-2- 0.1 % TFA in ACN; gradient I
hydroxy-1-(1H-indol-3- in each case based on B:
ylmethyl)ethylJbenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Chlorophenylboronic acid 449.9 Retention time: 10.3 min.

149 4-Ethoxy-3'-methylbiphenyl-3- 135 Column Purospher Star RP N
carboxylic acid [(R)-1-hydroxy- C18 4.6x125 5pm; detec-methyl-2-(1 H-indol-3- tion wavelength 214 nm; HO H
flow rate 1 mI/min; eluents 0 NH
yl)ethyl]amide;
A: 0.1 % TFA in H20, B
5-Bromo-2-ethoxy-N-[(R)-2- 0.1 % TFA in ACN; gradient hydroxy-1-(1H-indol-3- in each case based on B:
ylmethyl)ethylJbenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Methylphenylboronic acid 429,5 Retention time: 10,17 min.
N
150 5-Benzofuran-2-yl-2-ethoxy-N- 135 Column Purospher Star RP _H
[(R)-1-hydroxymethyl-2-(1 H- C18 4.6x125 5pm; detec- ~/
indol-3-yl)ethyl]benzamide; tion wavelength 214 nm; Ho o NH
flow rate 1 mI/min; eluents 5-Bromo-2-ethoxy-N-[(R)-2- A: 0.1% TFA in H20, B hydroxy-1-(1H-indol-3- 0.1%
TFA in ACN; gradient o ylmethyl)ethyl)benzamide in each case based on B:
5% to 95% (10') to 95% (2) and to 5% (0.5') to 5% (2.5') Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]
Benzo(bJfuran-2-boronic acid Molecular peak (ESI, M+1):
455.5 Retention time: 10.61 min.

151 4-Ethoxy-2'- 135 Column Purospher Star RP N
methylsulphanylbiphenyl-3- C18 4.6x125 5pm; detec-tion wavelength carboxylic acid [(R)-2-hydroxy- 214 nm; Ho 1-(1H-indol-3- flow rate 1 mI/min; eluents o HNH
ylmethyl)ethyl]amide; A: 0.1% TFA in H20, B o~
0.1 % TFA in ACN; gradient ~
5-Bromo-2-ethoxy-N-((R)-2- in each case based on B: s-hydroxy-l-(1H-indol-3- 5% to 95% (10') to 95% (2') ylmethyl)ethylJbenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 461.6 2-(Methylthio)phenylboronic Retention time: 10.17 min.
acid 152 2-Ethoxy-N-[(R)-1- 135 Column Purospher Star RP N
hydroxymethyl-2-(1 H-indol-3- C18 4.6x125 5pm; detec-yl)ethyl]-5-(1 H-indol-4- tion wavelength 214 nm; HO
flow rate 1 mI/min; eluents o H NH
yl)benzamide;
A: 0.1% TFA in H20, B
5-Bromo-2-ethoxy-N-[(R)-2- 0.1 % TFA in ACN; gradient hydroxy-l-(1H-indol-3- in each case based on B:
ylmethyl)ethyl)benzamide 5% to 95% (10') to 95% (2') H~
to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
1 H-Indole-4-boronic acid 454.5 Retention time: 9.11 min.

Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]

153 2-Ethoxy-N-[(R)-2-hydroxy-1- 135 Column Purospher Star RP N
(1 H-indol-3-ylmethyl)ethyl]-5- C18 4.6x125 5pm; detec-(4-methylthiophene-2- tion wavelength 214 nm; Ho H
flow rate 1 mI/min; eluents o NH
yl)benzamide;
A: 0.1% TFA in H20, B
5-Bromo-2-ethoxy-N-[(R)-2- 0.1 % TFA in ACN; gradient hydroxy-1-(1H-indol-3- in each case based on B: S
ylmethyl)ethyl]benzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
4-Methylthiophene-2-boronic 435.6 acid Retention time: 10.07 min.

154 3'-Acetylamino-4- 135 Column Purospher Star RP N
ethoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- \A AO
tion wavelength acid [(R)-1-hydroxymethyl-2- 214 nm; Ho (1 H-indol-3-yl)ethyl]amide; flow rate 1 mI/min; eluents 0 H NH
A: 0.1 % TFA in H20, B
5-Bromo-2-ethoxy-N-[(R)-2- 0.1 % TFA in ACN; gradient hydroxy- 1-(1 H-indol-3- in each case based on B:
ylmethyl)ethyl]benzamide 5% to 95% (10') to 95%(2,) HNr to 5% (0.5') to 5% (2.5') 0 and Molecular peak (ESI, M+1):
3-Acetamidophenylboronic acid 472.6 Retention time: 8.3 min.
155 4-Ethoxy-2'-methylbiphenyl-3- 135 Column Purospher Star RP
H
C18 4.6x125 5pm; detec- ~/ N
carboxylic acid [(R)-1-hydroxy- AO
methyl-2-(1 H-indol-3- tion wavelength 214 nm;
HO H
flow rate 1 mi/min; eluents O NH
yl)ethyl]amide;
A: 0.1 % TFA in H20, B
5-Bromo-2-ethoxy-N-[(R)-2- 0.1% TFA in ACN; gradient hydroxy-1-(1H-indol-3- in each case based on B:
ylmethyl)ethyl]benzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gous to 'H-NMR (400 MHz) S[ppm]
and Molecular peak (ESI, M+1):
429.5 2-Methylphenylboronic acid Retention time: 10.35 min.

156 2-Ethoxy-N-[(R)-1- 135 Column Purospher Star RP N
hydroxymethyl-2-(1 H-indol-3- C18 4.6x125 5Nm; detec- /
tion wavelength 214 nm;
yl)ethyl]-5-(5-methyl-furan-2-flow rate 1 mI/min; eluents HO H%
yl)benzamide; o NH
A: 0.1 % TFA in H20, B
5-Bromo-2-ethoxy-N-((R)-2- 0.1 % TFA in ACN; gradient hydroxy-l-(1H-indol-3- in each case based on B: o ylmethyl)ethylJbenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
5-Methylfuran-2-boronic acid 419.5 Retention time: 9.08 min.

157 3'-Chloro-4-ethoxy-4'- 135 Column Purospher Star RP N
methylbiphenyl-3-carboxylic C18 4.6x125 5pm; detec-tion wavelength 214 nm;
acid [(R)-2-hydroxy- 1 -(1 H- HID =
indol-3-ylmethyl)ethyl]amide; flow rate 1 mI/min; eluents 0 NH
A: 0.1% TFA in H20, B
ci 5-Bromo-2-ethoxy-N-[(R)-2- 0.1 % TFA in ACN; gradient I
hydroxy-l-(1H-indol-3- in each case based on B:
ylmethyl)ethylJbenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Chloro-4-methyl- 464.0 phenylboronic acid Retention time: 10.83 min.

Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gousto H-NMR (400 MHz) S[ppm]

158 5-(2-Chloro-6-methylpyridin-3- 135 Column Purospher Star RP N
yl)-2-ethoxy-N-[(R)-2-hydroxy- C18 4.6x125 5pm; detec- ?
1-(1H-indol-3- tion wavelength 214 nm;
HO .
ylmethyl)ethyl]benzamide; flow rate 1 mI/min; eluents 0 NH
5-Bromo-2-ethoxy-N-[(R)-2- A: 0.1 % TFA in H20, B "', hydroxy-l-(1H-indol-3- 0.1% TFA in ACN; gradient ylmethyl)ethylJbenzamide in each case based on B: " cl and 5% to 95% (10') to 95% (2) 2-Chloro-6-methylpyridine-3- to 5% (0.5') to 5% (2.5') boronic acid Molecular peak (ESI, M+1):
465.0 Retention time: 9.33 min.

159 4-Ethoxy-4'-fluoro-biphenyl-3- 135 Column Purospher Star RP _ N
carboxylic acid [(R)-2-hydroxy- C18 4.6x125 5pm; detec- ~
tion wavelength 214 nm;
1-(1 H-indol-3- HO H
ylmethyl)ethyl]amide; flow rate 1 ml/min; eluents 0 NH
A: 0.1 % TFA in H20, B
5-Bromo-2-ethoxy-N-[(R)-2- 0.1 % TFA in ACN; gradient hydroxy-l-(1H-indol-3- in each case based on B: F
ylmethyl)ethyl)benzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
4-Fluorophenylboronic acid 433.5 Retention time: 9.73 min.

160 2-Ethoxy-N-[(R)-1- 135 Column Purospher Star RP N
hydroxymethyl-2-(1 H-indol-3- C18 4.6x125 5pm; detec-yl)ethyl]-5-naphthalen-1 - tion wavelength 214 nm; HO H
flow rate 1 ml/min; eluents NH
ylbenzamide;
A: 0.1 % TFA in H20, B
5-Bromo-2-ethoxy-N-[(R)-2- 0.1% TFA in ACN; gradient hydroxy-1-(1H-indol-3- in each case based on B:
ylmethyl)ethylJbenzamide 5% to 95% (10') to 95% (2) to 5% (0.5') to 5% (2.5') Product; Method HPLC-MS conditions / Structure Ex. analo-reagents sousto 'H-NMR (400 MHz) S [ppm]
and Molecular peak (ESI, M+1):
465.6 1-Naphthaleneboronic acid Retention time: 10.55 min.

161 5-Benzo[b]thiophene-2-yl-2- 135 Column Purospher Star RP N
ethoxy-N-[(R)-2-hydroxy-1-(1H- C18 4.6x125 5pm; detec-tion wavelength 214 nm;
indol-3- Ho H' ylmethyl)ethyl]benzamide; flow rate 1 mI/min; eluents o""
A: 0.1% TFA in H20, B
5-Bromo-2-ethoxy-N-[(R)-2- 0.1 % TFA in ACN; gradient s hydroxy-l-(1H-indol-3- in each case based on B:
ylmethyl)ethyl]benzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
Benzo[b]thiophene-2-boronic 471.6 acid Retention time: 10.92 min.

162 4-Ethoxy-4'-methylbiphenyl-3- 135 Column Purospher Star RP N
carboxylic acid [(R)-1-hydroxy- C18 4.6x125 5pm; detec-methyl-2-(1 H-indol-3- tion wavelength 214 nm; Ho H
flow rate 1 ml/min; eluents o NH
yl)ethyl]amide;
A: 0.1% TFA in H20, B
5-Bromo-2-ethoxy-N-[(R)-2- 0.1 % TFA in ACN; gradient hydroxy-l-(1H-indol-3- in each case based on B:
ylmethyl)ethyl]benzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
4-Methylphenylboronic acid 429.5 Retention time: 10.14 min.

Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gousto 'H-NMR (400 MHz) S[ppm]

163 2-Ethoxy-N-[(R)-2-hydroxy-1- 135 Column Purospher Star RP H
C18 4.6x125 5Nm; detec- N
(1 H-indol-3-ylmethyl)ethyl]-5- i tion wavelength 214 nm;
thiophene-3-ylbenzamide; HO H
flow rate 1 ml/min; eluents 0 NH
5-Bromo-2-ethoxy-N-[(R)-2- A: 0.1 % TFA in H20, B
hydroxy-l-(1H-indol-3- 0.1% TFA in ACN; gradient ylmethyl)ethyl]benzamide in each case based on B: S ~
5% to 95% (10') to 95% (2') and to 5% (0.5') to 5% (2.5') Thiophene-3-boronic acid Molecular peak (ESI, M+1):
421.5 Retention time: 9.72 min.

164 4-Ethoxy-4'-methoxybiphenyl-3- 135 HPLC-MS: _ H
carboxylic acid [(R)-1-hydroxy- Column Purospher Star RP
methyl-2-(1 H-indol-3- C18 4.6x125 5pm; detec- HO H
tion wavelength 214 nm; 0 NH
yl)ethyl]amide;
flow rate 1 mI/min; eluents 5-Bromo-2-ethoxy-N-[(R)-2- A: 0.1 % TFA in H20, B
o hydroxy-1-(1 H-indol-3- 0.1 % TFA in ACN; gradient ylmethyl)ethyl]benzamide in each case based on B:
5% to 95% (10') to 95% (2') and to 5% (0.5') to 5% (2.5') 4-Methoxyphenylboronic acid Molecular peak (ESI, M+1):
445.5 Retention time: 9.61 min.

165 2',4'-Dichloro-4-ethoxybiphenyl- 135 HPLC-MS: N
3-carboxylic acid [(R)-2- Column Purospher Star RP
C18 4.6x125 5pm; detec- Ho hydroxy-1 -(1 H-indol-3- %
ylmethyl)ethyl]amide; tion wavelength 214 nm; o NH
flow rate 1 mI/min; eluents c' ~
5-Bromo-2-ethoxy-N-[(R)-2- A: 0.1 % TFA in H20, B I ci hydroxy-l-(1 H-indol-3- 0.1 % TFA in ACN; gradient ylmethyl)ethyl]benzamide in each case based on B:

Product; Method HPLC-MS conditions I Structure Ex. analo- H-NMR (400 MHz) S[ppm) reagents so~s to and 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') 2,4-Dichlorophenylboronic acid Molecular peak (ESI, M+1):
484.4 Retention time: 10.78 min.

166 4'-Methoxy-4-propoxybiphenyl- 135 Column Purospher Star RP _ C18 4.6x125 5Nm; detec- ~ HO
\/
3-carboxylic acid [(R)-1- o HN H
~ ,"~
hydroxymethyl-2-(1 H-indol-3- tion wavelength 214 nm; o I ~
yl)ethyl]amide; flow rate 1 mI/min; eluents A: 0.1% TFA in H20, B I
N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient o indol-3-y1)ethyl]-5-iod-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
4-Methoxyphenylboronic acid 459.6 Retention time: 9.67 min 167 4-Propoxybiphenyl-3-carboxylic 135 Column Purospher Star RP N H
acid [(R)-1-hydroxymethyl-2- C18 4.6x125 5pm; detec-(1 H-indol-3-yl)ethyl]amide; tion wavelength 214 nm; H o' \\' flow rate 1 ml/min; eluents 0H o N-((R)-1-Hydroxymethyl-2-(1H- A: 0.1% TFA in H20, B
indol-3-y1)ethyl]-5-iodo-2- 0.1% TFA in ACN; gradient propoxybenzamide in each case based on B:
5% to 95% (10') to 95% (2') and to 5% (0.5') to 5% (2.5') Phenylboronic acid Molecular peak (ESI, M+1):
429.5 Retention time: 9.75 min.

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]
168 5-Benzofuran-2-yl-N-[(R)-1- 135 Column Purospher Star RP
hydroxymethyl-2-(1 H-indol-3- C18 4.6x125 5pm; detec-tion wavelength 214 nm;
yl)ethyl]-2-propoxybenzamide;
flow rate 1 ml/min; eluents H o N-[(R)-1-Hydroxymethyl-2-(1 H- A: 0.1 % TFA in H20, B N I H=. NH 0 indol-3-y1)ethyl]-5-iodo-2- 0.1 % TFA in ACN; gradient oH
propoxybenzamide in each case based on B:
5% to 95% (10') to 95% (2') and to 5% (0.5') to 5% (2.5') Benzo(b]furan-2-boronic acid Molecular peak (ESI, M+1):
469.6 Retention time: 10.52 min.

169 3'-Chloro-4-propoxybiphenyl-3- 135 Column Purospher Star RP c, carboxylic acid [(R)-2-hydroxy- C18 4.6x125 5Nm; detec-1-(1H-indol-3- tion wavelength 214 nm; " H0 NH
ylmethyl)ethyl]amide; flow rate 1 ml/min; eluents OH
l A: 0.1 % TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient indol-3-y1)ethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Chlorophenylboronic acid 464 Retention time: 10.38 min.

170 5-Benzo[b]thiophen-2-yl-N-[(R)- 135 Column Purospher Star RP H
N
2-hydroxy-1 -(1 H-indol-3- C18 4.6x125 5pm; detec-ylmethyl)ethyl]-2- tion wavelength 214 nm; HO
H
propoxybenzamide; flow rate 1 ml/min; eluents H o A: 0.1 % TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient -indol-3-y1)ethyl]-5-iodo-2- in each case based on B: S~
propoxybenzamide 5% to 95% (10') to 95% (2) to 5% (0.5') to 5% (2.5') Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[pprn]
and Molecular peak (ESI, M+1):
485.6 Benzo[b]thiophene-2-boronic Retention time: 10.84 min.
acid 171 3'-Fluoro-4'-methyl-4- 135 Column Purospher Star RP "
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- N
acid [(R)-2-hydroxy-1 -(1 H- tion wavelength 214 nm; HO
H
indol-3-ylmethyl)ethyl]amide; flow rate 1 ml/min; eluents " 0 A: 0.1% TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient F
indol-3-y1)ethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Fluoro-4-methyl- 461.6 phenylboronic acid Retention time: 10.37 min.

172 4-Propoxy-3'- 135 Column Purospher Star RP "
trifluoromethylbiphenyl-3- C1 8 4.6x1 25 5pm; detec- - "
"
carboxylic acid [(R)-2-hydroxy- tion wavelength 214 nm; HO
1-(1H-indol-3- flow rate 1 ml/min; eluents ~o" 0 ylmethyl)ethyl]amide; A: 0.1% TFA in H20, B F
0.1 % TFA in ACN; gradient F
N-[(R)-1-Hydroxymethyl-2-(1H- in each case based on B:
indol-3-y1)ethyl]-5-iodo-2- 5% to 95% (10') to 95% (2') propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 497.5 3-(Trifluoromethyl)- Retention time: 10.41 min.
phenylboronic acid Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gous to 'H-NMR (400 MHz) S [ppm]

173 2'-Fluoro-5'-methoxy-4- 135 Column Purospher Star RP H
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- \hN
acid [(R)-2-hydroxy-1 -(1 H- tion wavelength 214 nm; HO
H
indol-3-ylmethyl)ethyl]amide; flow rate 1 mI/min; eluents o H 0 A: 0.1 % TFA in H20, B
\ / F
N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient indol-3-y1)ethyl]-5-iod-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') -O
to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
2-Fluoro-5-methoxyphenyl- 477.6 boronic acid Retention time: 9.79 min.

174 4-Propoxy-3',5'-bis- 135 Column Purospher Star RP H
C18 4.6x125 5pm; detec- h trifluoromethylbiphenyl-3-H
carboxylic acid [(R)-2-hydroxy- tion wavelength 214 nm; HO
1-(1 H-indol-3- flow rate 1 ml/min; eluents ~,o H 0 ylmethyl)ethyl]amide; A: 0.1 % TFA in H20, B
0.1 % TFA in ACN; gradient cF
N-((R)-1-Hydroxymethyl-2-(1H- in each case based on B:
indol-3-y1)ethyl]-5-iod-2- 5% to 95% (10') to 95% (2') CF3 propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 565.5 3,5-Bis-(Trifluoromethyl)- Retention time: 11.01 min.
phenylboronic acid Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S [ppm]

175 4'-Chloro-4-propoxybiphenyl-3- 135 Column Purospher Star RP H
C18 4.6x125 5pm; detec- "
carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3- tion wavelength 214 nm; Ho H
ylmethyl)ethyl]amide; flow rate 1 ml/min; eluents --,\H o ,o A: 0.1 % TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1 H- 0.1 % TFA in ACN; gradient indol-3-y1)ethyl]-5-iod-2- in each case based on B: ci propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
4-Chlorophenylboronic acid 464 Retention time: 10.44 min.

176 5-Benzo[b]thiophene-3-yl-N- 135 Column Purospher Star RP TNH
[(R)-2-hydroxy-1-(1 H-indol-3- C18 4.6x125 5Nm; detec- ylmethyl)ethyl]-2- tion wavelength 214 nm;

flow rate 1 ml/min; eluents ,OH
propoxybenzamide; I ~ H
A: 0.1 % TFA in H20, B ~ o N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient S/
indol-3-yl)ethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') and to 5% (0.5') to 5% (2.5') 1-Benzothiophen-3-yl-boronic Molecular peak (ESI, M+1):
acid 485.6 Retention time: 10.56 min.

177 4-Propoxy-4'- 135 Column Purospher Star RP H
C18 4.6x125 5pm; detec- N
trifluoromethylbiphenyl-3-H
carboxylic acid [(R)-2-hydroxy- tion wavelength 214 nm; HO
1 -(1 H-indol-3- flow rate 1 mI/min; eluents o ylmethyl)ethyl]amide; A: 0.1 % TFA in H20, B
0.1 % TFA in ACN; gradient N-((R)-1-Hydroxymethyl-2-(1H- in each case based on B: ~ F
F F
indo1-3-y1)ethyl]-5-iodo-2- 5% to 95% (10') to 95% (2') propoxybenzamide to 5% (0.5') to 5% (2.5') Product; Method HPLC-MS conditions / Structure Ex. analo- H-NMR (400 MHz) S[ppm]
reagents gous co and Molecular peak (ESI, M+1):
497.5 4-(Trifluoromethyl)- Retention time: 10.42 min.
phenylboronic acid 178 3'-Hydroxy-4-propoxybiphenyl- 135 Column Purospher Star RP _ H
3-carboxylic acid [(R)-1- C18 4.6x125 5pm; detec- ~~ N
hydroxymethyl-2-(1 H-indol-3- tion wavelength 214 nm; Ho H
yl)ethyl]amide; flow rate 1 mI/min; eluents HN o A: 0.1% TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient o indol-3-y1)ethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Hydroxyphenylboronic acid 445.5 Retention time: 8.56 min.

179 N-[(R)-1-Hydroxymethyl-2-(1H- 135 Column Purospher Star RP H
indol-3-yl)ethyl]-2-propoxy-5- C18 4.6x125 5Nm; detec-OH
quinoline-6-ylbenzamide; tion wavelength 214 nm; H NH
flow rate 1 mI/min; eluents o 01-N-((R)-1-Hydroxymethyl-2-(1H- A: 0.1% TFA in H20, B
indol-3-y1)ethyl]-5-iodo-2- 0.1 % TFA in ACN; gradient propoxybenzamide in each case based on B: N
~
5% to 95% (10') to 95% (2') and to 5% (0.5') to 5% (2.5') Quinoline-6-boronic acid Molecular peak (ESI, M+1):
480.6 Retention time: 6.78 min.

Product; Method HPLC-MS conditions I Structure Ex. analo- H-NMR (400 MHz) S[ppm]
reagents gous to 180 5-(6-Fluoro-5-methylpyridin-3- 135 Column Purospher Star RP _ H
C18 4.6x125 5pm; detec- N
yl)-N-[(R)-2-hydroxy-1 -(1 H- -indol-3-ylmethyl)ethyl]-2- tion wavelength 214 nm; HO
flow rate 1 mI/min; eluents o H"
propoxybenzamide; o A: 0.1 % TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient indol-3-y1)ethyl]-5-iodo-2- in each case based on B: N
F
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
2-Fluoro-3-methylpyridine-5- 462.5 boronic acid Retention time: 9.2 min.

181 N-[(R)-1-Hydroxymethyl-2-(1H- 135 Column Purospher Star RP _ H
indol-3-yl)ethyl]-5-(6- C1 8 4.6x1 25 5pm; detec- N
~
H
methoxypyridine-3-yl)-2- tion wavelength 214 nm; HO
propoxybenzamide; flow rate 1 ml/min; eluents HN o A: 0.1 % TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient N
indol-3-yl)ethyl]-5-iodo-2- in each case based on B: o-propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
2-Methoxypyridine-5-boronic 460.6 acid Retention time: 8.57 min.

182 3'-Chloro-4'-methyl-4- 135 Column Purospher Star RP H
C18 4.6x125 5pm; detec- N
propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1 H- tion wavelength 214 nm; HO
H H
60\r indol-3-ylmethyl)ethyl]amide; flow rate 1 mI/min; eluents A: 0.1 % TFA in H20, B N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient ci indol-3-y1)ethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]
and to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
3-Chloro-4-methylboronic acid 478 Retention time: 10.94 min.

183 N-[(R)-1-Hydroxymethyl-2-(1 H- 135 Column Purospher Star RP _ H
indol-3-yl)ethyl]-2-propoxy-5- C18 4.6x125 5Nm; detec- N
pyridine-4-ylbenzamide; tion wavelength 214 nm; HO
flow rate 1 mI/min; eluents HN H o N-((R)-1-Hydroxymethyl-2-(1H- A: 0.1% TFA in H20, B --\,-O
indol-3-yl)ethylj-5-iodo-2- 0.1 % TFA in ACN; gradient propoxybenzamide in each case based on B: N
5% to 95% (10') to 95% (2) and to 5% (0.5') to 5% (2.5') Pyridine-4-boronic acid Molecular peak (ESI, M+1):
430.5 Retention time: 6.14 min.

184 3'-Chloro-4'-fluoro-4- 135 Column Purospher Star RP
N
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- - acid [(R)-2-hydroxy-1 -(1 H- tion wavelength 214 nm; HO
H H
indol-3-ylmethyl)ethyl]amide; flow rate 1 mI/min; eluents o A: 0.1% TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1 H- 0.1 % TFA in ACN; gradient ci indol-3-y1)ethylj-5-iodo-2- in each case based on B: F
propoxybenzamide 5% to 95% (10') to 95% (2') and to 5% (0.5') to 5% (2.5') 3-Chloro-4-fluorophenylboronic Molecular peak (ESI, M+1):
acid 482 Retention time: 10.41 min.

Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]

185 3'-Acetylamino-4- 135 Column Purospher Star RP \~ N
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- , acid [(R)-1-hydroxymethyl-2- tion wavelength 214 nm; H0 HN H
(1 H-indol-3-yl)ethyl]amide; flow rate 1 mI/min; eluents '\-O _ A: 0.1% TFA in H20, B H
N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient o indol-3-y1)ethylJ-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Acetamidophenylboronic acid 486.6 Retention time: 8.32 min.

186 3',4'-Difluoro-4- 135 Column Purospher Star RP _ H
propoxybiphenyl-3-carboxylic C18 4.6x125 5Nm; detec- - N
"
acid [(R)-2-hydroxy-1-(1H- tion wavelength 214 nm; HO
indol-3-ylmethyl)ethyl]amide; flow rate 1 mI/min; eluents o A: 0.1% TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient F
indol-3-y1)ethylJ-5-iodo-2- in each case based on B: F
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular weight, calc.
3, 4-Difluorophenylboronic acid 464.5 Molecular peak (ESI, M+1):
465.5 Retention time: 9.97 min.

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) 8[ppm]

187 3',5'-Difluoro-4- 135 Column Purospher Star RP _ C18 4.6x125 5Nm; detec- N
propoxybiphenyl-3-carboxylic "
acid [(R)-2-hydroxy-1 -(1 H- tion wavelength 214 nm; HO

indol-3-ylmethyl)ethyl]amide; flow rate 1 ml/min; eluents " 6Qr A: 0.1% TFA in H20, B N-(( R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient F
indol-3-yl)ethyl]-5-iodo-2- in each case based on B:
F
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3, 5-Difluorophenylboronic acid 465.5 Retention time: 10.07 min.

188 3'-Cyano-4-propoxybiphenyl-3- 135 Column Purospher Star RP N
carboxylic acid [(R)-1- C18 4.6x125 5pm; detec-hydroxymethyl-2-(1 H-indol-3- tion wavelength 214 nm; HO "
flow rate 1 mI/min; eluents HN
yl)ethyl]amide;
A: 0.1% TFA in H20, B
N-[(R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient indol-3-yl)ethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Cyanophenylboronic acid 454.6 Retention time: 9.42 min.

189 5-(2,4-Dimethoxypyrimidin-5- 135 Column Purospher Star RP _ H
I N- R 1-h drox meth I 2- C18 4.6x125 5pm; detec- ~~ N
Y )- [( )- Y Y Y -(1 H-indol-3-yl)ethyl]-2- tion wavelength 214 nm; Ho propoxybenzamide; flow rate 1 mi/min; eluents HN H 0 A: 0.1% TFA in H20, B
o-N-[(R)-1-Hydroxymethyl-2-(1 H- 0.1 % TFA in ACN; gradient N
indol-3-y1)ethyl]-5-iodo-2- in each case based on B: ' NA 0 propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') Product; Method HPLC-MS conditions I Structure Ex. analo-reagents 9ous to H-NMR (400 MHz) S[ppm]
and Molecular peak (ESI, M+1):
491.6 2,4-Dimethoxypyrimidine-5- Retention time: 7.16 min.
boronic acid 190 2',3'-Difluoro-4- 135 Column Purospher Star RP _ "
propoxybiphenyl-3-carboxylic C1 8 4.6x1 25 5Nm; detec-H
acid [(R)-2-hydroxy-1-(1 H- tion wavelength 214 nm; HO
indol-3-ylmethyl)ethyl]amide; flow rate 1 mI/min; eluents " o A: 0.1% TFA in H20, B F
N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient F
indo1-3-yl)ethylJ-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2) to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
2, 3-Difluorophenylboronic acid 465.5 Retention time: 9.88 min.
191 2',5'-Difluoro-4- 135 Column Purospher Star RP
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- ~
acid [(R)-2-hydroxy- 1 -(1 H- tion wavelength 214 nm; HO
indol-3-ylmethyl)ethyl]amide; flow rate 1 ml/min; eluents H H o A: 0.1% TFA in H20, B --'-,-o N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient F
~
indol-3-y1)ethylJ-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') F
to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
2, 5-Difluorophenylboronic acid 465.5 Retention time: 9.82 min.

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]

192 5-[(E)-2-(4-Fluorophenyl)-vinyl]- 135 Column Purospher Star RP "
C18 4.6x125 5pm; detec- "
N-[(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]-2- tion wavelength 214 nm; HO "
propoxybenzamide; flow rate 1 ml/min; eluents --\,O"
A: 0.1% TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1 H- 0.1 % TFA in ACN; gradient indol-3-y1)ethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') F
to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
(E)-2-(4-Fluorphenyl)viny1- 473.6 boronic acid Retention time: 10.31 min.

193 5-(5-Cyanothiophen-2-yl)-N- 135 Column Purospher Star RP _ [(R)-2-hydroxy-1 -(1 H-indol-3- C18 4.6x125 5pm; detec- \/ N
ylmethyl)ethyl]-2- tion wavelength 214 nm; HO flow rate 1 ml/min; eluents H H
propoxybenzamide; o A: 0.1 % TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient indol-3-y1)ethyl]-5-iodo-2- in each case based on B:
/
propoxybenzamide 5% to 95% (10') to 95% (2') s to 5% (0.5') to 5% (2.5') N
and Molecular peak (ESI, M+1):
5-Cyanothiophene-2-boronic 460.6 acid Retention time: 9.48 min.

194 2'-Fluoro-3'-methoxy-4- 135 Column Purospher Star RP "
C18 4.6x125 5pm; detec- "
propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1 -(1H- tion wavelength 214 nm; HO " "
indol-3-ylmethyl)ethyl]amide; flow rate 1 ml/min; eluents A: 0.1 % TFA in H20, B F
N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient .
indol-3-yl)ethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') Product; Method HPLC-MS conditions I Structure Ex. analo-reagents sousco H-NMR (400 MHz) S[ppm]
and to 5% (0.5') to 5% (2.5') 2-Fluoro-3-methoxyphenyl- Molecular peak (ESI, M+1):
boronic acid 477.6 Retention time: 9.59 min.

195 N-[(R)-1-Hydroxymethyl-2-(1H- 135 Column Purospher Star RP _ H
indol-3-yl)ethyl]-5-(2- C18 4.6x125 5pm; detec- ~/ "
H
methoxypyrimidine-5-yl)-2- tion wavelength 214 nm; HO
propoxybenzamide; flow rate 1 mI/min; eluents H" o A: 0.1 % TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1 H- 0.1 % TFA in ACN; gradient N
indol-3-y1)ethyl]-5-iodo-2- in each case based on B: N-A o propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
2-Methoxypyrimidine-5-boronic 461.5 acid Retention time: 8.09 min.

196 4'-Chloro-2',6'-difluoro-4- 135 Column Purospher Star RP _ H
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- ~
acid [(R)-2-hydroxy-1 -(1 H- tion wavelength 214 nm; Ho indol-3-ylmethyl)ethyl]amide; flow rate 1 ml/min; eluents -\-o H H 0 A: 0.1% TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient 1 F
~
indol-3-yl)ethyl]-5-iodo-2- in each case based on B: F~~
propoxybenzamide 5% to 95% (10') to 95% (2') ci to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
4-Chloro-2, 6-difluoro- 500 phenylboronic acid Retention time: 10.43 min.

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]

197 3',5'-Dimethyl-4- 135 Column Purospher Star RP _ H
propoxybiphenyl-3-carboxylic C18 4.6x1 25 5Nm; detec- N
H
acid [(R)-1-hydroxymethyl-2- tion wavelength 214 nm; HO
(1 H-indol-3-yl)ethyl]amide; flow rate 1 ml/min; eluents HN o A: 0.1 % TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient indol-3-y1)ethylJ-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3, 5-Dimethylphenylboronic acid 457.6 Retention time: 10.71 min.

198 N-[(R)-1-Hydroxymethyl-2-(1H- 135 Column Purospher Star RP _ N
indol-3-yl)ethyl]-2-propoxy-5- C1 8 4.6x1 25 5pm; detec- tion wavelength 214 nm; Ho quinoline-3-ylbenzamide; HN H
flow rate 1 mi/min; eluents N-((R)-1-Hydroxymethyl-2-(1H- A: 0.1% TFA in H20, B
indol-3-yl)ethylJ-5-iodo-2- 0.1% TFA in ACN; gradient N~
propoxybenzamide in each case based on B:
5% to 95% (10') to 95% (2') and to 5% (0.5') to 5% (2.5') 3-Quinolineboronic acid Molecular peak (ESI, M+1):
480.6 Retention time: 7.07 min.
H
199 4'-Acetylamino-4- 135 Column Purospher Star RP 31H
opoxybiphenyl-3-carboxylic C18 4.6x1 25 5Nm; detec- - N
pr acid [(R)-1-hydroxymethyl-2- tion wavelength 214 nm; Ho (1 H-indol-3-yl)ethyl]amide; flow rate 1 ml/min; eluents HN o A: 0.1 % TFA in H20, B
N-[(R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient indol-3-y1)ethylJ-5-iodo-2- in each case based on B: NH
propoxybenzamide 5% to 95% (10') to 95% (2') '~
to 5% (0.5') to 5% (2.5') Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gousto H-NMR (400 MHz) S[ppm]
and Molecular peak (ESI, M+1):
486.6 4-Acetamidophenylboronic acid Retention time: 8.12 min.
200 4-Propoxy-3'-(2,2,2- 135 Column Purospher Star RP
C18 4.6x125 5pm; detec- OH
/
trifluoroethoxy)biphenyl-3- NH
carboxylic acid [(R)-2-hydroxy- tion wavelength 214 nm; 0 HN H
1 -(1 H-indol-3- flow rate 1 mI/min; eluents 0 ylmethyl)ethyl]amide; A: 0.1 % TFA in H20, B
0.1 % TFA in ACN; gradient ~ I

N-[(R)-1-Hydroxymethyl-2-(1H- in each case based on B: cF

indol-3-y1)ethyl]-5-iodo-2- 5% to 95% (10') to 95% (2') propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 527.6 3-(2,2,2-Trifluorethoxy)phenyl- Retention time: 10.15 min.
boronic acid 201 3'-Ethoxy-5'-fluoro-4- 135 Column Purospher Star RP H
C18 4.6x125 5pm; detec- N
propoxybiphenyl-3-carboxylic ~
H
acid [(R)-2-hydroxy-1-(1 H- tion wavelength 214 nm; HO
indol-3-ylmethyl)ethyl]amide; flow rate 1 ml/min; eluents H 0 A: 0.1% TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1 H- 0.1 % TFA in ACN; gradient F
indol-3-yl)ethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2) ro to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Ethoxy-5-fluorophenylboronic 491.6 acid Retention time: 10.42 min.

Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gousto H-NMR (400 MHz) S[ppm]
202 5'-Ethoxy-2'-fluoro-4- 135 Column Purospher Star RP
H
C18 4.6x125 5pm; detec-propoxybiphenyl-3-carboxylic N
tion wavelength 214 nm; HO
acid [(R)-2-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide; flow rate 1 ml/min; eluents H"

A: 0.1 % TFA in H20, B
N-[(R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient F
indol-3-y1)ethylJ-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') r o to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
5-Ethoxy-2-fluorophenylboronic 491.6 acid Retention time: 10.23 min.

203 3'-Ethoxy-4-propoxybiphenyl-3- 135 Column Purospher Star RP /
carboxylic acid [(R)-1-hydroxy- C18 4.6x125 5pm; detec- ~ o" NH
methyl-2-(1 H-indol-3- tion wavelength 214 nm; o HN
yl)ethyl]amide; flow rate 1 ml/min; eluents i A: 0.1 % TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1H- 0.1% TFA in ACN; gradient I
indol-3-y1)ethylJ-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Ethoxyphenylboronic acid 473.6 Retention time: 10.13 min.
204 4-Propoxybiphenyl-3-carboxylic 135 Column Purospher Star RP
acid [(R)-1-hydroxymethyl-2-(1- C18 4.6x125 5pm; detec- N, methyl-1 H-indol-3- tion wavelength 214 nm;
OH
yl)ethyl]amide; flow rate 1 ml/min; eluents HN H
A: 0.1 % TFA in H20, B o N-((R)-1-Hydroxymethyl-2-(1- 0.1% TFA in ACN; gradient O
methyl-lH-indol-3-y1)ethylJ-5- in each case based on B:
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2) to 5% (0.5') to 5% (2.5') Product; Method HPLC-MS conditions / Structure Ex. analo-reagents sousto H-NMR (400 MHz) S[ppm]
and Molecular peak (ESI, M+1):
443.6 Phenylboronic acid Retention time: 10.76 min.
205 5-Benzofuran-2-yl-N-[(R)-1- 135 Column Purospher Star RP
C18 4.6x125 5pm; detec- I N, hydroxymethyl-2-(1-methyl-1 H-indol-3-yl)ethyl]-2- tion wavelength 214 nm;
H oH
propoxybenzamide; flow rate 1 mi/min; eluents HN o A: 0.1% TFA in H20, B %1 o N-((R)-1-Hydroxymethyl-2-(1- 0.1% TFA in ACN; gradient methyl-1 H-indol-3-y1)ethyl]-5- in each case based on B:
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
Benzo(b]furan-2-boronic acid 483.6 Retention time: 11.22 min.
206 5-Benzo[b]thiophen-2-yl-N-[(R)- 135 Column Purospher Star RP
2-hyd roxy- 1 -(1 -methyl- 1 H- C1 8 4.6x1 25 5pm; detec- N-indol-3-ylmethyl)ethyl]-2- tion wavelength 214 nm; H oH
flow rate 1 mi/min; eluents HN
propoxybenzamide; o A: 0.1 % TFA in H20, B o N-((R)-1-Hydroxymethyl-2-(1- 0.1% TFA in ACN; gradient ~
methyl-lH-indol-3-yl)ethyl]-5- in each case based on B:
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2) to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
Benzo[b]thiophene-2-boronic 499.6 acid Retention time: 11.52 min.

Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]
207 2'-Fluoro-4'-methyl-4- 135 Column Purospher Star RP
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- N, acid [(R)-2-hydroxy-1-(1- tion wavelength 214 nm; OH
methyl-1 H-indol-3- flow rate 1 mI/min; eluents F HN' H
A: 0.1 % TFA in H20, B c o ylmethyl)ethyl]amide; 0.1 % TFA in ACN; gradient N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-lH-indol-3-y1)ethyl]-5- 5% to 95% (10') to 95% (2') iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 475.6 2-Fluoro-4- Retention time: 11.07 min.
methylphenylboronic acid 208 4'-Fluoro-4-propoxybiphenyl-3- 135 Column Purospher Star RP
carboxylic acid [(R)-2-hydroxy- C18 4.6x125 5pm; detec- N, 1-(1-methyl-lH-indol-3- tion wavelength 214 nm; oH
ylmethyl)ethyl]amide; flow rate 1 mI/min; eluents HN"H
A: 0.1 % TFA in H20, B
F o \ ~ \
N-((R)-1-Hydroxymethy1-2-(1- 0.1% TFA in ACN; gradient methyl-1H-indol-3-y1)ethy1]-5- in each case based on B:
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
4-Fluorophenylboronic acid 461.5 Retention time: 10.61 min.
209 2'-Fluoro-5'-methoxy-4- 135 Column Purospher Star RP
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- N, acid [(R)-2-hydroxy-1-(1- tion wavelength 214 nm;
OH
methyl-1 H-indol-3- flow rate 1 ml/min; eluents HN.=H
ylmethyl)ethyl]amide; s A: 0.1 % TFA in H20, B ~ o 0.1 % TFA in ACN; gradient o o N-((R)-1-Hydroxymethy1-2-(1- in each case based on B:
methyl-1H-indol-3-yl)ethyl]-5- 5% to 95% (10') to 95% (2') Product; Method HPLC-MS conditions I Structure Ex. analo- H-NMR (400 MHz) S[ppm]
reagents so~s co iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
2-Fluoro-5- 491.6 methoxyphenylboronic acid Retention time: 10.42 min.

210 3'-Fluoro-4-propoxybiphenyl-3- 135 Column Purospher Star RP
carboxylic acid [(R)-2-hydroxy- C18 4.6x125 5Nm; detec- N, 1 -(1 -methyl-1 H-indol-3- tion wavelength 214 nm;
OH
ylmethyl)ethyl]amide; flow rate 1 ml/min; eluents HNH
A: 0.1 % TFA in H20, B F 0 N-((R)-1-Hydroxymethyl-2-(1- 0.1% TFA in ACN; gradient o methyl-1H-indol-3-y1)ethyl]-5- in each case based on B:
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Fluorophenylboronic acid 461.5 Retention time: 10.63 min.
211 N-[(R)-1-Hydroxymethyl-2-(1- 135 Column Purospher Star RP
methyl-1 H-indol-3-yl)ethyl]-2- C18 4.6x125 5pm; detec- N, propoxy-5-pyridine-3-yl- tion wavelength 214 nm;
OH
benzamide; flow rate 1 mi/min; eluents HNH
A: 0.1 % TFA in H20, B N O
N-((R)-1-Hydroxymethyl-2-(1- 0.1% TFA in ACN; gradient O
methy1-1H-indol-3-y1)ethy1]-5- in each case based on B:
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
Pyridine-5-boronic acid 444.5 Retention time: 6.73 min.

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gousto H-NMR (400 MHz) 5 [ppm]
212 5-Benzo[b]thiophene-3-yl-N- 135 Column Purospher Star RP
[(R)-2-hydroxy-1 -(1-methyl-1 H- C18 4.6x125 5pm; detec- N, indol-3-ylmethyl)ethyl]-2- tion wavelength 214 nm;
OH
H, propoxybenzamide; flow rate 1 ml/min; eluents HN
A: 0.1 % TFA in H20, B o N-((R)-1-Hydroxymethyl-2-(1- 0.1 % TFA in ACN; gradient s O
methyl-1H-indol-3-yl)ethylJ-5- in each case based on B:
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
Benzo[b]thiophene-3-boronic 499.6 acid Retention time: 11.37 min.
213 3'-Cyano-4'-fluoro-4- 135 Column Purospher Star RP
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- N, acid [(R)-2-hydroxy-1-(1- tion wavelength 214 nm; oH
methyl-1 H-indol-3- flow rate 1 mI/min; eluents N HN'~H
ylmethyl)ethyl]amide; A: 0.1 % TFA in H20, B F o 0.1 % TFA in ACN; gradient - - o N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-lH-indol-3-yl)ethylJ-5- 5% to 95% (10') to 95% (2') iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 486.6 4-Fluoro-3-cyanophenylboronic Retention time: 10.16 min.
acid 214 N-[(R)-1-Hydroxymethyl-2-(1- 135 Column Purospher Star RP
methyl-1 H-indol-3-yl)ethyl]-5- C18 4.6x125 5pm; detec- N-(6-methoxypyridine-3-yl)-2- tion wavelength 214 nm; oH
propoxybenzamide; flow rate 1 mI/min; eluents N HN o ._ _ A: 0.1 % TFA in H20, B ~~ o N-((R)-1-Hydroxymethyl-2-(1- 0.1% TFA in ACN; gradient methyl-1 H-indol-3-yl)ethylJ-5- in each case based on B:

Product; Method HPLC-MS conditions I Structure Ex. analo-reagents sousto 'H-NMR (400 MHz) 8 [ppm]
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2) to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
2-Methoxypyridine-5-boronic 474.6 acid Retention time: 9.62 min.
215 3'-Acetylamino-4- 135 Column Purospher Star RP
propoxybiphenyl-3-carboxylic C1 8 4.6x1 25 5pm; detec- N-acid [(R)-1-hydroxymethyl-2-(1- tion wavelength 214 nm; o"
flow rate 1 mI/min; eluents 0 H
"" "
methyl-1 H-indol-3- ~ o A: 0.1 % TFA in H20, B ~\ i\ o yl)ethyl]amide;
0.1 % TFA in ACN; gradient N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-1H-indol-3-y1)ethyl]-5- 5% to 95% (10') to 95% (2') iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 500.6 3-Acetamidophenylboronic acid Retention time: 9.06 min.
216 3',4'-Difluoro-4- 135 Column Purospher Star RP
propoxybiphenyl-3-carboxylic C1 8 4.6x1 25 5pm; detec- N, acid [(R)-2-hydroxy-1-(1- tion wavelength 214 nm; oH
methyl-1 H-indol-3- flow rate 1 mI/min; eluents F HN' o ylmethyl)ethyl]amide; A: 0.1% TFA in H20, B F o 0.1 % TFA in ACN; gradient N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-lH-indol-3-yl)ethyl]-5- 5% to 95% (10') to 95% (2) iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 479.5 3, 4-Difluorophenylboronic acid Retention time: 10.65 min.

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]
217 3',5'-Difluoro-4- 135 Column Purospher Star RP
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- N, acid [(R)-2-hydroxy-1-(1- tion wavelength 214 nm;
OH
methyl-1 H-indol-3- flow rate 1 ml/min; eluents F HN. H
ylmethyl)ethyl]amide; A: 0.1% TFA in H20, B o 0.1 % TFA in ACN; gradient o N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-1H-indol-3-y1)ethyl]-5- 5% to 95% (10') to 95% (2') iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 479.5 3,5-Difluorophenylboronic acid Retention time: 10.74 min.
218 5-(2,4-Dimethoxypyrimidin-5- 135 Column Purospher Star RP
yl)-N-[(R)-1-hydroxymethyl-2- C1 8 4.6x1 25 5pm; detec- N-tion wavelength (1-methyl-1 H-indol-3-yl)ethyl]- 214 nm; oH
flow rate 1 ml/min; eluents % 0 HN o 2-propoxybenzamide;
A: 0.1% TFA in H20, B 0~N-\
N-((R)-1-Hydroxymethyl-2-(1- 0.1% TFA in ACN; gradient methyl-1 H-indol-3-yl)ethyl]-5- in each case based on B:
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2') and to 5% (0.5') to 5% (2.5') 2,4-Dimethoxypyrimidine-5- Molecular peak (ESI, M+1):
boronic acid 505.6 Retention time: 7.76 min.
219 2',5'-Difluoro-4- 135 Column Purospher Star RP
propoxybiphenyl-3-carboxylic C18 4.6x125 5Nm; detec- N, acid [(R)-2-hydroxy-1-(1- tion wavelength 214 nm; oH
methyl-1 H-indol-3- flow rate 1 mi/min; eluents HN H
ylmethyl)ethyl]amide; A: 0.1% TFA in H20, B F o 0.1% TFA in ACN; gradient - ~~ o N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-lH-indol-3-y1)ethy1]-5- 5% to 95% (10') to 95% (2) to 5% (0.5') to 5% (2.5') Product; Method HPLC-MS conditions / Structure Ex. analo-reagents yous to H-NMR (400 MHz) S[ppm]
iodo-2-propoxybenzamide Molecular peak (ESI, M+1):
479.5 and Retention time: 10.51 min.
2, 5-Difluorophenylboronic acid 220 5-[(E)-2-(4-Fluorophenyl)vinyl]- 135 Column Purospher Star RP
N
C18 4.6x125 5pm; detec- i H
N-[(R)-2-hydroxy-1 -(1-methyl-1 H-indol-3-ylmethyl)ethyl]-2- tion wavelength 214 nm; H propoxybenzamide;
flow rate 1 mI/min; eluents A: 0.1% TFA in H20, B ~
N-((R)-1-Hydroxymethyl-2-(1- 0.1% TFA in ACN; gradient ~ i methyl-1 H-indol-3-yl)ethyl]-5- in each case based on B: F
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2') and to 5% (0.5') to 5% (2.5') (E)-2-(4-Fluorophenyl)-vinyl- Molecular peak (ESI, M+1):
boronic acid 487.6 Retention time: 11.07 min.
221 5-(5-Cyano-thiophen-2-yl)-N- 135 Column Purospher Star RP
i N
[(R)-2-hydroxy-1-(1-methyl-1 H- C18 4.6x125 5pm; detec- Ho indol-3-ylmethyl)ethyl]-2- tion wavelength 214 nm; HN
propoxybenzamide; flow rate 1 mI/min; eluents A: 0.1% TFA in H20, B s N=
N-((R)-1-Hydroxymethyl-2-(1- 0.1% TFA in ACN; gradient methyl-1H-indol-3-y1)ethyl]-5- in each case based on B:
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
5-Cyanothiophene-2-boronic 474.6 acid Retention time: 10.33 min.

Product; Method HPLC-MS conditions / Structure Ex. analo- H-NMR (400 MHz) S[ppm]
reagents gous to 222 N-[(R)-1-Hydroxymethyl-2-(1- 135 Column Purospher Star RP
methyl-1 H-indol-3-yl)ethyl]-5- C18 4.6x125 5pm; detec- N-(2-methoxypyrimidine-5-yl)-2-propoxybenzamide; tion wavelength 214 nm; oH
flow rate 1 mI/min; eluents N HNH
_ A: 0.1 % TFA in H20, B N io N-((R)-1-Hydroxymethyl-2-(1-0.1 % TFA in ACN; gradient methyl-1 H-indol-3-yl)ethyl]-5-in each case based on B:
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2) and to 5% (0.5') to 5% (2.5') 2-Methoxypyrimidine-5-boronic Molecular weight, calc.
acid 474.6 Retention time: 8.83 min.
223 N-[(R)-1-Hydroxymethyl-2-(1- 135 Column Purospher Star RP
methyl-1 H-indol-3-yl)ethyl]-2- C1 8 4.6x1 25 5pm; detec- N, propoxy-5-quinoline-3-yl- tion wavelength 214 nm; H oH
flow rate 1 mI/min; eluents HN
benzamide; QN o A: 0.1% TFA in H20, B o N-[(R)-1-Hydroxymethyl-2-(1- 0.1% TFA in ACN; gradient methyl-1H-indol-3-y1)ethyl]-5- in each case based on B:
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
Quinoline-3-boronic acid 494.6 Retention time: 7.64 min.
224 5'-Fluoro-3'-methoxy-4- 135 Column Purospher Star RP
C18 4.6x125 5pm; detec- N, propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1- tion wavelength 214 nm; oH
methyl-1H-indol-3- flow rate 1 mI/min; eluents F HN~H

ylmethyl)ethyl]amide; A: 0.1 % TFA in H20, B
o 0.1% TFA in ACN; gradient o N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-1 H-indol-3-yl)ethyl]-5- 5% to 95% (10') to 95% (2) iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]
and Molecular peak (ESI, M+1):
491.6 3-Fluoro-5- Retention time: 10.6 min.
methoxyphenylboronic acid 225 4-Propoxy-3'-(2,2,2- 135 Column Purospher Star RP
trifluoroethoxy)biphenyl-3- C1 8 4.6x1 25 5pm; detec- "-tion wavelength 214 nm; F F oH
carboxylic acid [(R)-2-hydroxy- F~ H
1-(1-methyl-1H-indol-3- flow rate 1 ml/min; eluents o "" o ylmethyl)ethyl]amide; amide~ A: 0.1% TFA in H20, B
0.1 % TFA in ACN; gradient N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methy1-lH-indol-3-yl)ethylJ-5- 5% to 95% (10') to 95% (2) iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-(2, 2, 2-Trifluorethoxy)phenyl- 541.6 boronic acid Retention time: 10.89 min.

226 5'-Ethoxy-2'-fluoro-4- 135 Column Purospher Star RP \
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- N_ acid [(R)-2-hydroxy-1-(1- tion wavelength 214 nm; oH
methyl-1 H-indol-3- flow rate 1 mI/min; eluents HN H 0 ylmethyl)ethyl]amide; A: 0.1% TFA in H20, B ~SO
0.1 % TFA in ACN; gradient o N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-1 H-indol-3-yl)ethylJ-5-5%to95%(10')to95%(2) iodo-2-propoxybenzamide o 0 to5/o(0.5)to5/o(2.5) and Molecular peak (ESI, M+1):
2-Fluoro-5-505.6 ethoxyphenylboronic acid Retention time:.10.9 min.

Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]

Column Purospher Star RP F
227 4'-Methoxy-4-propoxybiphenyl- 135 3-carboxylic acid [2-(5-fluoro- C18 4.6x125 5pm; detec- NH
1H-indol-3-yl)-1- tion wavelength 214 nm; H oH
hydroxymethylethyl]amide; flow rate 1 ml/min; eluents HN

A: 0.1 % TFA in H20, B ~~ o N-[2-(5-Fluoro- 1 H-in dol- 3-yl) - 1 - 0.1% TFA in ACN; gradient hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2) to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
4-Methoxyphenylboronic acid 477.5 Retention time: 9.78 min.

228 5-Benzofuran-2-yl-N-[2-(5- 135 Column Purospher Star RP F I
C18 4.6x125 5pm; detec- NH
fluoro-1 H-indol-3-yl)-1-tion wavelength 214 nm;
hydroxymethylethyl]-2- H oH
propoxybenzamide; flow rate 1 ml/min; eluents HN o A: 0.1 % TFA in H20, B
N-[2-(5-Fluoro-1H-indol-3-yl)-1- 0.1% TFA in ACN; gradient hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
Benzo(b]furan-2-boronic acid 487.5 Retention time: 10.58 min.

229 3'-Methyl-4-propoxybiphenyl-3- 135 Column Purospher Star RP F \
carboxylic acid [2-(5-fluoro-1 H- C18 4.6x125 5pm; detec- NH
indol-3-yl)-1- tion wavelength 214 nm;
OH
hydroxymethylethyl]amide; flow rate 1 ml/min; eluents HN H
A: 0.1 % TFA in H20, B o N-[2-(5-Fluoro-lH-indol-3-yl)-1- 0.1% TFA in ACN; gradient o hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2) to 5% (0.5') to 5% (2.5') Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gousto 'H-NMR (400 MHz) 8 [ppm]
and Molecular peak (ESI, M+1):
461.5 3-Methylphenylboronic acid Retention time: 10.36 min.

Column Purospher Star RP F
230 5-Benzo[b]thiophene-2-yl-N-[2- 135 (5-fluoro-1 H-indol-3-yl)-1- C18 4.6x125 5pm; detec- NH
hydroxymethylethyl]-2- tion wavelength 214 nm; H OH
propoxybenzamide; flow rate 1 ml/min; eluents HN o A: 0.1 % TFA in H20, B
N-[2-(5-Fluoro-1H-indol-3-yl)-1- 0.1% TFA in ACN; gradient hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
Benzo[b]thiophene-2-boronic 503.6 acid Retention time: 10.92 min.

231 2'-Fluoro-5'-methoxy-4- 135 Column Purospher Star RP F \
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- I NH
acid [1-(5-fluoro-1 H-indol-3- tion wavelength 214 nm; OH
ylmethyl)-2- flow rate 1 mI/min; eluents HN H
F o hydroxyethyl]amide; A: 0.1% TFA in H20, B Q 0.1 % TFA in ACN; gradient o o N-[2-(5-Fluoro-lH-indol-3-yl)-1- in each case based on B:
hydroxymethylethyl]-5-iodo-2- 5% to 95% (10') to 95% (2') propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 495.5 2-Fluoro-5-methoxyphenyl- Retention time: 9.86 min.
boronic acid Product; Method HPLC-MS conditions / Structure Ex. analo- H-NMR (400 MHz) S[ppm]
reagents gous to 232 4-Propoxy-3',5'-bis- 135 Column Purospher Star RP F
trifluoromethylbiphenyl-3- C18 4.6x125 5pm; detec- NH
carboxylic acid [1-(5-fluoro-1H- tion wavelength 214 nm; oH
indol-3- Imeth I-2- flow rate 1 mI/min; eluents F F F HN H
y y) o hydroxyethyl]amide; A: 0.1% TFA in H20, B o 0.1 % TFA in ACN; gradient F ~
N-[2-(5-Fluoro-1H-indol-3-yl)-1- F F
in each case based on B:
hydroxymeth ylethyl]-5-iodo-2-5% to 95% (10') to 95% (2) propoxybenzamide 5% 0 to5/o (0.5)to5/o (2.5) and Molecular peak (ESI, M+1):
3, 5-Bistrifluoromethylphenyl- 583.5 boronic acid Retention time: 10.97 min.

233 N-[2-(5-Fluoro-1H-indol-3-yl)-1- 135 Column Purospher Star RP F
hydroxymethylethyl]-2-propoxy- C18 4.6x125 5pm; detec- NH
5-pyridin-3-yl-benzamide; tion wavelength 214 nm; oH
flow rate 1 mi/min; eluents HN H
N-[2-(5-Fluoro-1H-indol-3-yl)-1- A: 0.1% TFA in H20, B N o hydroxymethylethyl]-5-iodo-2- 0.1 % TFA in ACN; gradient o propoxybenzamide in each case based on B:
5% to 95% (10') to 95% (2') and to 5% (0.5') to 5% (2.5') Pyridine-3-boronic acid Molecular peak (ESI, M+1):
448.5 Retention time: 6.26 min.

234 5-Benzo[b]thiophene-3-yl-N-[2- 135 Column Purospher Star RP F
(5-fluoro-1H-indol-3-yl)-1- C18 4.6x125 5pm; detec- I NH
hydroxymethylethyl]-2- tion wavelength 214 nm; oH
H
propoxybenzamide; flow rate 1 ml/min; eluents HN
A: 0.1 % TFA in H20, B
N-[2-(5-Fluoro-1 H-indol-3-yl)-1- 0.1 % TFA in ACN; gradient S
hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]
and Molecular peak (ESI, M+1):
503.6 Benzo[b]thiophene-3-boronic Retention time: 10.63 min.
acid 235 3'-Cyano-4'-fluoro-4- 135 Column Purospher Star RP F I
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- NH
acid [1-(5-fluoro-1 H-indol-3- tion wavelength 214 nm; oH
ylmethyl)-2- flow rate 1 mI/min; eluents N HN H

hydroxyethyl]amide; A: 0.1% TFA in H20, B F o 0.1 % TFA in ACN; gradient N-[2-(5-Fluoro-1H-indol-3-yl)-1- in each case based on B:
hydroxymethylethyl]-5-iodo-2- 5% to 95% (10') to 95% (2') propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 490.5 3-Cyano-4-fluorophenylboronic Retention time: 9.52 min.
acid 236 N-[1-(5-Fluoro-1H-indol-3- 135 Column Purospher Star RP F 1 ylmethyl)-2-hydroxyethyl]-5-(6- C1 8 4.6x1 25 5pm; detec- H
tion wavelength 214 nm; OH
fluoro-5-methylpyridine-3-yl)-2-H
propoxybenzamide; flow rate 1 ml/min; eluents N_ HN o A: 0.1% TFA in H20, B F\ o N-[2-(5-Fluoro-1H-indol-3-yl)-1- 0.1% TFA in ACN; gradient hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
2-Fluoro-3-methylpyridine-5- 480.5 boronic acid Retention time: 9.26 min.

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents yous to H-NMR (400 MHz) S[ppm]

Column Purospher Star RP F
237 N-[2-(5-Fluoro-1H-indol-3-yl)-1- 135 I
hydroxymethylethyl]-5-(6- C18 4.6x125 5pm; detec- NH
tion wavelength methoxypyridine-3-yl)-2- 214 nm; oH
flow rate 1 ml/min; eluents HN
propoxybenzamide; N
o A: 0.1 % TFA in H20, B ~_~ 0 N-[2-(5-Fluoro-lH-indol-3-yl)-1- 0.1% TFA in ACN; gradient hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
2-Methoxypyridine-5-boronic 478.5 acid Retention time: 8.77 min.

238 3'-Chloro-4'-fluoro-4- 135 Column Purospher Star RP F I~
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- H
tion wavelength 214 nm; OH
acid [1-(5-fluoro-1H-indol-3-ylmethyl)-2- flow rate 1 mI/min; eluents ~~ HN o A: 0.1% TFA in H20, B F~~ ~~
hydroxyethyl]amide; - _ 0 0.1 % TFA in ACN; gradient N-[2-(5-Fluoro-1H-indol-3-yl)-1- in each case based on B:
hydroxymethylethyl]-5-iodo-2- 5% to 95% (10') to 95% (2') propoxybenzamide to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Chloro-4-fluorophenylboronic 500 acid Retention time: 10.54 min.

239 3'-Acetylamino-4- 135 Column Purospher Star RP F
propoxybiphenyl-3-carboxylic C18 4.6x1 25 5pm; detec- NH
acid [2-(5-fluoro-1 H-indol-3-yl)- tion wavelength 214 nm; oH
flow rate 1 ml/min; eluents "IN HN H
1-hydroxymethylethyl]amide; o A: 0.1% TFA in H20, B b_c~o N-[2-(5-Fluoro-1H-indol-3-yl)-1- 0.1% TFA in ACN; gradient hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gous to H-NMR (400 MHz) S [PPm]
and to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
3-Acetamidophenylboronic acid 504.6 Retention time: 8.37 min.

240 3',4'-Difluoro-4- 135 Column Purospher Star RP F
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- NH
tion wavelength 214 nm; oH
acid [1 -(5-fluoro-1 H-indol-3-ylmethyl)-2- flow rate 1 mi/min; eluents F HN H
hydroxyethyl]amide; A: 0. 1 % TFA in H20, B F o 0.1 % TFA in ACN; gradient N-(2-(5-Fluoro-lH-indol-3-yl)-1- in each case based on B:
hydroxymethylethyl]-5-iodo-2- 5% to 95% (10') to 95% (2) propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 483.5 3,4-Difluorophenylboronic acid Retention time: 10.08 min.

241 3',5'-Difluoro-4- 135 Column Purospher Star RP F
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- NH
acid [2-(5-fluoro-1 H-indol-3-yl)- tion wavelength 214 nm;
OH
1 -hydroxymethylethyl]amide; flow rate 1 ml/min; eluents F HN H
A: 0.1 % TFA in H20, B 0-- o /
N-(2-(5-Fluoro-1H-indol-3-yl)-1- 0.1% TFA in ACN; gradient _ hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3, 5-Difluorophenylboronic acid 483.5 Retention time: 10.07 min.

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]

242 2',5'-Difluoro-4- 135 Column Purospher Star RP F
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- NH
acid [1 -(5-fluoro-1 H-indol-3- tion wavelength 214 nm; oH
ylmethyl)-2- flow rate 1 mI/min; eluents F HN H
hydroxyethyl]amide; A: 0. 1 % TFA in H20, B o 0.1 % TFA in ACN; gradient 0 N-[2-(5-Fluoro-1H-indol-3-yl)-1- in each case based on B:
hydroxymethylethyl]-5-iodo-2- 5% to 95% (10') to 95% (2') propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 483.5 2,5-Difluorophenylboronic acid Retention time: 9.95 min.

Column Purospher Star RP F
243 N-[2-(5-Fluoro-1 H-indol-3-yl)-1- 135 hydroxymethylethyl]-5-[(E)-2- C18 4.6x125 5pm; detec- NH
(4-fluorophenyl)-vinyl]-2- tion wavelength 214 nm; OH
flow rate 1 mI/min; eluents HN o H propoxybenzamide; o A: 0.1 % TFA in H20, B F~~
N-[2-(5-Fluoro-1 H-indol-3-yl)-1- 0.1 % TFA in ACN; gradient hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2) and to 5% (0.5') to 5% (2.5') (E)-2-(4-Fluorphenyl)vinyl- Molecular peak (ESI, M+1):
boronic acid 491.5 Retention time: 10.46 min.

244 5-(5-Cyano-thiophene-2-yl)-N- 135 Column Purospher Star RP F
[2-(5-fluoro-1H-indol-3-yl)-1- C18 4.6x125 5pm; detec- I NH
hydroxymethylethyl]-2- tion wavelength 214 nm; oH
propoxybenzamide; flow rate 1 ml/min; eluents N HN H

A: 0.1 % TFA in H20, B
N-[2-(5-Fluoro-1H-indol-3-yl)-1- 0.1% TFA in ACN; gradient hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') Product; Method HPLC-MS conditions / Structure Ex. analo-reagents yous to H-NMR (400 MHz) S[ppm]
and Molecular peak (ESI, M+1):
478.6 5-Cyanothiophene-2-boronic Retention time: 9.5 min.
acid 245 2'-Fluoro-3'-methoxy-4- 135 Column Purospher Star RP F
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- I NH
acid [1-(5-fluoro-1 H-indol-3- tion wavelength 214 nm; OH
ylmethyl)-2- flow rate 1 mI/min; eluents _o HN H

hydroxyethyl]amide; A: 0. 1 % TFA in H20, B
\ i o 0.1% TFA in ACN; gradient N-[2-(5-Fluoro-1 H-indol-3-yl)-1-in each case based on B:
h yd rox ym e th yl e th yl]- 5-i o d o- 2-5%to95%(10')to95%(2') propoxybenzamide o o to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
2-Fluoro-3-methoxyphenyl- 495.5 boronic acid Retention time: 9.57 min.
Column Purospher Star RP F
246 N-[2-(5-Fluoro-1H-indol-3-yl)-1- 135 hydroxymethylethyl]-5-(2- C18 4.6x125 5pm; detec- NH
tion wavelength methoxypyrimidin-5-yl)-2- 214 nm; OH
flow rate 1 mI/min; eluents HN H.
propoxybenzamide;
A: 0.1% TFA in H20, B 0~N o N-(2-(5-Fluoro-lH-indol-3-yl)-1- 0.1% TFA in ACN; gradient hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
2-Methoxypyrimidine-5-boronic 479.5 acid Retention time: 8.27 min.

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) 8 [ppm]

Column Purospher Star RP F
247 N-[2-(5-Fluoro-1 H-indol-3-yl)-1- 135 hydroxymethylethyl]-2-propoxy- C18 4.6x125 5pm; detec- NH
tion wavelength 214 nm; oH
5-quinoline-3-yl-benzamide; H
flow rate 1 mi/min; eluents "N
N-[2-(5-Fluoro-1H-indol-3-yl)-1- A: 0.1% TFA in H20, B ;NN r !\ o hydroxymethylethyl]-5-iodo-2- 0.1 % TFA in ACN; gradient propoxybenzamide in each case based on B:
5% to 95% (10') to 95% (2') and to 5% (0.5') to 5% (2.5') Quinoline-3-boronic acid Molecular peak (ESI, M+1):
498.6 Retention time: 7.05 min.
Column Purospher Star RP F
248 4-Propoxy-3'-(2,2,2- 135 trifluoroethoxy)biphenyl-3- C18 4.6x125 5pm; detec- NH
tion wavelength 214 nm;
carboxylic acid [1-(5-fluoro-1 H- F~ H. OH
indol-3-ylmethyl)-2- flow rate 1 ml/min; eluents O HN
hydroxyethyl]amide; A: 0.1 % TFA in H20, B
0.1 % TFA in ACN; gradient N-(2-(5-Fluoro-1H-indol-3-yl)-1- in each case based on B:
hydroxymethylethyl]-5-iodo-2- 5% to 95% (10') to 95% (2') propoxybenzamide to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-(2, 2, 2-Trifluoroethoxy)- 545.5 phenylboronic acid Retention time: 10.27 min.

249 5'-Ethoxy-2'-fluoro-4- 135 Column Purospher Star RP F
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- I NH
acid [1-(5-fluoro-1 H-indol-3- tion wavelength 214 nm; OH
ylmethyl)-2- flow rate 1 mI/min; eluents F HN H.
/\ \
hydroxyethyl]amide; A: 0. 1 % TFA in H20, B
_ 0.1 % TFA in ACN; gradient j r N-[2-(5-Fluoro-1H-indol-3-yl)-1- in each case based on B:
hydroxymethylethyl]-5-iodo-2- 5% to 95% (10') to 95% (2') propoxybenzamide to 5% (0.5') to 5% (2.5') Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]
and Molecular peak (ESI, M+1):
509.6 2-Fluoro-5- Retention time: 10.33 min.
ethoxyphenylboronic acid 250 3'-Methoxy-4-propoxybiphenyl- 135 Column Purospher Star RP
3-carboxylic acid [(R)-1- C18 4.6x125 5pm; detec- N, hydroxymethyl-2-(1-methyl-1 H- tion wavelength 214 nm; oH
indol-3-yl)ethyl]amide; flow rate 1 mI/min; eluents -o HN o A: 0.1 % TFA in H20, B
- _ o N-((R)-1-Hydroxymethyl-2-(1- 0.1% TFA in ACN; gradient methyl-lH-indol-3-y1)ethylJ-5- in each case based on B:
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Methoxyphenylboronic acid 473.6 Retention time: 10.31 min.
251 3'-Chloro-4-propoxybiphenyl-3- 135 Column Purospher Star RP
carboxylic acid [(R)-2-hydroxy- C18 4.6x125 5pm; detec- N, 1-(1-methyl-1H-indol-3- tion wavelength 214 nm; oH
ylmethyl)ethyl]amide; flow rate 1 mI/min; eluents ci HN' o A: 0.1% TFA in H20, B \ ~ ~_\ o N-((R)-1-Hydroxymethyl-2-(1- 0.1% TFA in ACN; gradient methyl-1H-indol-3-y1)ethylJ-5- in each case based on B:
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2) to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Chlorophenylboronic acid 478 Retention time: 11.14 min.

Product; Method HPLC-MS conditions I Structure Ex. analo- I
MHz) reagents gous to H-NMR (400 S [ppm]

252 4-Propoxy-3',5'-bis- 135 Column Purospher Star RP
trifluoromethylbiphenyl-3- C18 4.6x125 5pm; detec- N-carboxylic acid [(R)-2-hydroxy- tion wavelength 214 nm; OH
flow rate 1 mI/min; eluents FF F HN,H
1-(1-methyl-1 H-indol-3- o ylmethyl)ethyl]amide; A: 0.1 % TFA in H20, B ~~ o 0.1 % TFA in ACN; gradient FF F 11_~
N-[(R)-1-Hydroxymethyl-2-(1-in each case based on B:
methyl-1 H-indol-3-yl)ethyl]-5-5%to95%(10')to95%(2') iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3, 5-Bistrifluoromethylphenyl- 579.6 boronic acid Retention time: 11.68 min.
253 3',4',5'-Trifluoro-4- 135 Column Purospher Star RP
propoxybiphenyl-3-carboxylic Cl 8 4.6x1 25 5pm; detec- N, tion wavelength 214 nm; oH
acid [(R)-2-hydroxy-1-(1-methyl-1 H-indol-3- flow rate 1 mI/min; eluents F HN o ylmethyl)ethyl]amide; A: 0.1 % TFA in H20, B F~ o 0.1 % TFA in ACN; gradient N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-1H-indol-3-yl)ethyl]-5- 5% to 95% (10') to 95% (2') iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 497.5 3,4,5-Trifluorophenylboronic Retention time: 11.01 min.
acid 254 4-Propoxy-4'- 135 Column Purospher Star RP
trifluoromethoxybiphenyl-3- C18 4.6x125 5pm; detec- N-tion wavelength carboxylic acid [(R)-2-hydroxy- 214 nm; H OH
1-(1-methyl-1H-indol-3- flow rate 1 ml/min; eluents HN o \, ylmethyl)ethyl]amide; A: 0.1% TFA in H20, B FF F 0 0.1 % TFA in ACN; gradient N-[(R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-lH-indol-3-yl)ethyl]-5- 5% to 95% (10') to 95% (2) Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]
iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 527.6 4-Trifluoromethoxyphenyl- Retention time: 11.2 min.
boronic acid 255 4-Propoxy-4'- 135 Column Purospher Star RP
trifluoromethylbiphenyl-3- C18 4.6x125 5pm; detec- N-carboxylic acid [(R)-2-hydroxy- tion wavelength 214 nm; oH
1-(1-methyl-1H-indol-3- flow rate 1 ml/min; eluents F HN' o o ylmethyl)ethyl]amide; A: 0.1 % TFA in H20, B FF \
0.1 % TFA in ACN; gradient N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-1H-indol-3-y1)ethyl]-5- 5% to 95% (10') to 95% (2') iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
511.6 4-Trifluoromethylphenylboronic Retention time: 11.00 min.
acid 256 5-(6-Fluoro-5-methylpyridine-3- 135 Column Purospher Star RP
yl)-N-[(R)-2-hydroxy-1-(1- C18 4.6x125 5pm; detec- N-methyl-1 H-indol-3- tion wavelength 214 nm; oH
ylmethyl)ethyl]-2- flow rate 1 ml/min; eluents N_ HN' o roPoxYbenzamide, A: 0.1% TFA in H20, B F\ propoxybenzamide; o ~
0.1 % TFA in ACN; gradient N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-lH-indol-3-y1)ethyl]-5- 5% to 95% (10') to 95% (2') iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 476.6 2-Fluoro-3-methylpyridine-5- Retention time: 10.02 min.
boronic acid Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]
257 5-(3,5-Dimethyl-isoxazol-4-yl)- 135 Column Purospher Star RP
N-[(R)-1-hydroxymethyl-2-(1- C18 4.6x125 5pm; detec- N, methyl-1 H-indol-3-yl)ethyl]-2- tion wavelength 214 nm; oH
flow rate 1 mI/min; eluents HN H
propoxybenzamide;
A: 0.1% TFA in H20, B N o ' N-((R)-1-Hydroxymethyl-2-(1- 0.1 % TFA in ACN; gradient o~ 0 methyl-1H-indol-3-yl)ethylJ-5- in each case based on B:
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3, 5-Dimethylisoxazole-4- 462.6 boronic acid Retention time: 9.32 min.
258 3'-Chloro-4'-fluoro-4- 135 Column Purospher Star RP
C18 4.6x125 5pm; detec- I N-propoxybiphenyl-3-carboxylic tion wavelength 214 nm; oH
acid [(R)-2-hydroxy-1-(1-methyl-1 H-indol-3- flow rate 1 ml/min; eluents oi HNH
A:
ylmethyl)ethyl]amide; 0.1 % TFA in H20, B F!~
0.1 % TFA in ACN; gradient N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-1H-indol-3-yl)ethylJ-5- 5% to 95% (10') to 95% (2) iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 496 3-Chloro-4-fluorophenylboronic Retention time: 11.22 min.
acid 259 3'-Cyano-4-propoxybiphenyl-3- 135 Column Purospher Star RP
carboxylic acid [(R)-1- C18 4.6x125 5pm; detec- N, hydroxymethyl-2-(1-methyl-1H- tion wavelength 214 nm; oH
indol-3-yl)ethyl]amide; flow rate 1 mI/min; eluents N HN'~H
A: 0.1% TFA in H20, B o N-((R)-1-Hydroxymethyl-2-(1- 0.1 % TFA in ACN; gradient 0 methyl-lH-indol-3-yl)ethylJ-5- in each case based on B:

Product; Method HPLC-MS conditions I Structure Ex. analo- H-NMR (400 MHz) S[ppm]
reagents yo~s to iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Cyanophenylboronic acid 468.6 Retention time: 10.1 min.
260 2',3'-Difluoro-4- 135 Column Purospher Star RP
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- ~ i N, tion wavelength 214 nm;
acid [(R)-2-hydroxy-1-(1-OH
methyl-1 H-indol-3- flow rate 1 ml/min; eluents F HN'~H
ylmethyl)ethyl]amide; A: 0.1 % TFA in H20, B o 0.1 % TFA in ACN; gradient o N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-1H-indol-3-yl)ethyl)-5- 5% to 95% (10') to 95% (2') iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 479.5 2,3-Difluorophenylboronic acid Retention time: 10.54 min.
261 3',5'-Dimethyl-4- 135 Column Purospher Star RP
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- N, acid [(R)-1-hydroxymethyl-2-(1- tion wavelength 214 nm; OH
methyl-1 H-indol-3- flow rate 1 mI/min; eluents HN'H

yl)ethyl]amide; A: 0.1 % TFA in H20, B o 0.1 % TFA in ACN; gradient N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-1H-indol-3-yl)ethylJ-5- 5% to 95% (10') to 95% (2) iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 471.6 3,5-Dimethylphenylboronic acid Retention time: 10.18 min.

Product; Method HPLC-MS conditions I Structure Ex. analo-reagents 9ous to H-NMR (400 MHz) S[ppm]
262 3'-Ethoxy-5'-fluoro-4- 135 Column Purospher Star RP
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- N, acid [(R)-2-hydroxy-1-(1- tion wavelength 214 nm; oH
methyl-1 H-indol-3- flow rate 1 mI/min; eluents F HN H
A: 0.1 % TFA in H20, B \ ~ o ylmethyl)ethyl]amide; \

0.1 % TFA in ACN; gradient j -N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-1H-indol-3-yl)ethylJ-5- 5% to 95% (10') to 95% (2') iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 505.6 5-Ethoxy-3-fluorophenylboronic Retention time: 10.98 min.
acid 263 5'-Fluoro-3'-hydroxy-4- 135 Column Purospher Star RP
C18 4.6x125 5pm; detec- ~ N, propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1- tion wavelength 214 nm; oH
methyl-1 H-indol-3- flow rate 1 mI/min; eluents F HN' o ylmethyl)ethyl]amide; A: 0.1 % TFA in H20, B O_C~
o 0.1 % TFA in ACN; gradient Ho N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-lH-indol-3-y1)ethylJ-5- 5% to 95% (10') to 95% (2') iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Fluoro-5- 477.5 hydroxyphenylboronic acid Retention time: 9.5 min.

264 4,3'-Dipropoxybiphenyl-3- 135 Column Purospher Star RP
carboxylic acid [(R)-1- C18 4.6x125 5pm; detec- N-tion wavelength hydroxymethyl-2-(1-methyl-1H- 214 nm; H oH
indol-3-yl)ethyl]amide; flow rate 1 ml/min; eluents HN 0 A: 0.1 % TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1- 0.1% TFA in ACN; gradient methyl-lH-indol-3-yl)ethylJ-5- in each case based on B:

Product; Method HPLC-MS conditions I Structure Ex. analo-reagents 9ousto H-NMR (400 MHz) S[ppm]
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Propoxyphenylboronic acid 501.6 Retention time: 11.21 min.

265 3'-Chloro-4-propoxybiphenyl-3- 135 Column Purospher Star RP F
carboxylic acid [2-(5-fluoro-1 H- C18 4.6x125 5pm; detec- NH
indol-3-yl)-1- tion wavelength 214 nm;
OH
flow hydroxymethylethyl]amide; rate 1 ml/min; eluents cb-C HN H
A: 0.1 % TFA in H20, B o N-[ 2-(5-Fluoro-lH-indol-3-yl)-1- 0.1% TFA in ACN; gradient o hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2) to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Chlorophenylboronic acid 482 Retention time: 10.42 min.

266 3'-Fluoro-4'-methyl-4- 135 Column Purospher Star RP F
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- I NH
acid [1 -(5-fluoro-1 H-indol-3- tion wavelength 214 nm; OH
ylmethyl)-2- flow rate 1 ml/min; eluents F HN H

hydroxyethyl]amide; A: 0.1% TFA in H20, B
0.1 % TFA in ACN; gradient N-[2-(5-Fluoro-lH-indol-3-yl)-1- in each case based on B:
hydroxymethylethyl]-5-iodo-2- 5% to 95% (10') to 95% (2') propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 479.5 3-Fluoro-4-methylphenyl- Retention time: 10.08 min.
boronic acid Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]

267 2'-Fluoro-4'-methyl-4- 135 Column Purospher Star RP F
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- NH
acid [1-(5-fluoro-1H-indol-3- tion wavelength 214 nm; oH
ylmethyl)-2- flow rate 1 mI/min; eluents F HN H

hydroxyethyl]amide; A: 0.1 % TFA in H20, B i\ ~\ o 0.1 % TFA in ACN; gradient N-[2-(5-Fluoro-1H-indol-3-yl)-1- in each case based on B:
hydroxymethylethyl]-5-iodo-2- 5% to 95% (10') to 95% (2) propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 479.5 2-Fluoro-4-methylphenyl- Retention time: 10.27 min.
boronic acid 268 4-Propoxy-3'- 135 Column Purospher Star RP F
trifluoromethylbiphenyl-3- C18 4.6x125 5pm; detec- NH
carboxylic acid [1-(5-fluoro-1 H- tion wavelength 214 nm; oH
flow rate 1 mI/min; eluents HN
indol-3-ylmethyl)-2- FF F o hydroxyethyl]amide; A: 0.1 % TFA in H20, B \- \
0.1 % TFA in ACN; gradient N-(2-(5-Fluoro-1H-indol-3-yl)-1- in each case based on B:
hydroxymethylethyl]-5-iodo-2- 5% to 95% (10') to 95% (2') propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 515,5 3-Trifluoromethylphenylboronic Retention time: 10,41 min.
acid Product; Method HPLC-MS conditions / Structure Ex. reagents goanalo- us to 'H-NMR (400 MHz) S[ppm]

269 3'-Isopropyl-4-propoxybiphenyl- 135 Column Purospher Star RP F
3-carboxylic acid [2-(5-fluoro- C18 4.6x125 5pm; detec- NH
1H-indol-3-yl)-1- tion wavelength 214 nm; OH
hydroxymethylethyl]amide; flow rate 1 mI/min; eluents HN H

A: 0.1 % TFA in H20, B
- _ o N-[2-(5-Fluoro-1 H-indol-3-yl)-1- 0.1 % TFA in ACN; gradient hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Isopropylphenylboronic acid 489.6 Retention time: 10.96 min.
Column Purospher Star RP F
270 3'-Methylsulphanyl-4- 135 propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- NH
tion wavelength 214 nm; OH
acid [2-(5-fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]amide; flow rate 1 mI/min; eluents _S HN H

A: 0.1 % TFA in H20, B
- _ o N-(2-(5-Fluoro-1H-indol-3-yl)-1- 0.1% TFA in ACN; gradient hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2) to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3- 493.6 Methylsulphanylphenylboronic Retention time: 10.31 min.
acid Column Purospher Star RP F
271 4-Propoxy-4'- 135 trifluoromethoxybiphenyl-3- C18 4.6x125 5pm; detec- NH
tion wavelength carboxylic acid [1-(5-fluoro-1 H- 214 nm; oH
HN H
o indol-3-ylmethyl)-2- flow rate 1 ml/min; eluents 0 hydroxyethyl]amide; A: 0.1 % TFA in H20, B FF ~~ 0 0.1% TFA in ACN; gradient N-[2-(5-Fluoro-lH-indol-3-yl)-1- in each case based on B:
hydroxymethylethyl]-5-iodo-2- 5% to 95% (10') to 95% (2') Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]
propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 531.5 4-Trifluoromethoxyphenyl- Retention time: 10.69 min.
boronic acid Column Purospher Star RP F
272 N-[2-(5-Fluoro-1 H-indol-3-yl)-1- 135 hydroxymethylethyl]-2-propoxy- C18 4.6x125 5pm; detec- NH
tion wavelength 214 nm; OH
5-quinoline-6-yl-benzamide; H
flow rate 1 ml/min; eluents HN o N-[2-(5-Fluoro-lH-indol-3-yl)-1- A: 0.1% TFA in H20, B .N p<~ o hydroxymethylethyl]-5-iodo-2- 0.1 % TFA in ACN; gradient propoxybenzamide in each case based on B:
5% to 95% (10') to 95% (2) and to 5% (0.5') to 5% (2.5') Quinoline-6-boronic acid Molecular peak (ESI, M+1):
498.6 Retention time: 6.9 min.
\
273 3'-Chloro-4'-methyl-4- 135 Column Purospher Star RP F I
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- NH
acid [2-(5-fluoro-1 H-indol-3-yl)- tion wavelength 214 nm; oH
1 -hydroxymethylethyl]amide; flow rate 1 mUmin; eluents ci HN H
A: 0.1% TFA in H20, B

N-(2-(5-Fluoro-1H-indol-3-y1)-1- 0.1% TFA in ACN; gradient hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') and to 5% (0.5') to 5% (2.5') 3-Chloro-4- Molecular peak (ESI, M+1):
methylphenylboronic acid 496 Retention time: 11.03 min.

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]

274 5-(3,5-Dimethyl-isoxazol-4-yl)- 135 Column Purospher Star RP F
N-[2-(5-fluoro-1H-indol-3-yl)-1- C18 4.6x125 5pm; detec- NH
hydroxymethylethyl]-2- tion wavelength 214 nm; OH
propoxybenzamide; flow rate 1 ml/min; eluents HN H
A: 0.1% TFA in H20, B N o N-[2-(5-Fluoro-1 H-indol-3-yl)-1- 0.1 % TFA in ACN; gradient ~ o hydroxymethylethyl]-5-iodo-2-in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') and to 5% (0.5') to 5% (2.5') 3, 5-Dimethylisoxazole-4-Molecular peak (ESI, M+1):
boronic acid 466.5 Retention time: 8.77 min.

275 2',3'-Difluoro-4- 135 Column Purospher Star RP F
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- I~ NH
acid [1-(5-fluoro-1H-indol-3- tion wavelength 214 nm; OH
ylmethyl)-2- flow rate 1 ml/min; eluents 6-C HN H
hydroxyethyl]amide; A: 0.1 % TFA in H20, B o 0.1 % TFA in ACN; gradient N-[2-(5-Fluoro-1H-indol-3-yl)-1- in each case based on B:
hydroxymethylethyl]-5-iodo-2- 5% to 95% (10') to 95% (2') propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 483.5 2,3-Difluorophenylboronic acid Retention time: 10.05 min.

276 3',5'-Dimethyl-4- 135 Column Purospher Star RP F
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- NH
acid [2-(5-fluoro-1H-indol-3-yl)- tion wavelength 214 nm; OH
1-hydroxymethylethyl]amide; flow rate 1 ml/min; eluents HN H
A: 0.1% TFA in H20, B o N-[2-(5-Fluoro-1H-indol-3-yl)-1- 0.1% TFA in ACN; gradient \~ ~\ o hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') Product; Method HPLC-MS conditions / Structure Ex. analo-reagents 9ous to H-NMR (400 MHz) S[ppm]
and Molecular peak (ESI, M+1):
475.6 3,5-Dimethylphenylboronic acid Retention time: 10.71 min.

277 5'-Ethoxy-3'-fluoro-4- 135 Column Purospher Star RP F
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- NH
acid [2-(5-fluoro-1 H-indol-3-yl)- tion wavelength 214 nm; oH
1-hydroxymethylethyl]amide; flow rate 1 mI/min; eluents F HN H

A: 0.1 % TFA in H20, B 0-hydroxymethylethyl]-5-iodo-2- I N-[2-(5-Fluoro-1 H-indol-3-yl)-1- 0.1 % TFA in ACN; gradient o in each case based on B: ~

propoxybenzamide 5% to 95% (10') to 95% (2') and to 5% (0.5') to 5% (2.5') 5-Ethoxy-3-fluorphenylboronic Molecular peak (ESI, M+1):
acid 509.6 Retention time: 10.41 min.

278 3'-Fluoro-5'-hydroxy-4- 135 Column Purospher Star RP F \
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- NH
acid [2-(5-fluoro-1 H-indol-3-yl)- tion wavelength 214 nm; oH
1-hydroxymethylethyl]amide; flow rate 1 ml/min; eluents F HN H

A: 0.1 % TFA in H20, B /~ ~ o N-(2-(5-Fluoro-lH-indol-3-yl)-1- 0.1% TFA in ACN; gradient Ho -hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') and to 5% (0.5') to 5% (2.5') 3-Fluoro-5- Molecular peak (ESI, M+1):
hydroxyphenylboronic acid 481.5 Retention time: 9.03 min.
Column Purospher Star RP F
279 4,3'-Dipropoxybiphenyl-3- 135 carboxylic acid [2-(5-fluoro-1 H- C18 4.6x125 5pm; detec- NH
indol-3-yl)-1- tion wavelength 214 nm; OH
flow rate 1 mI/min; eluents HN H
hydroxymethylethyl]amide;
A: 0.1 % TFA in H20, B
N-(2-(5-Fluoro-1H-indol-3-yl)-1- 0.1% TFA in ACN; gradient Product; Method HPLC-MS conditions / Structure Ex. analo- H-NMR (400 MHz) S[ppm]
reagents gous to hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-n-Propoxyphenylboronic acid 505.6 Retention time: 10.67 min.

280 3'-Ethoxy-4-propoxybiphenyl-3- 135 Column Purospher Star RP F Q,NH
carboxylic acid [2-(5-fluoro-1 HC18 4.6x125 5Nm; detec- tion wavelength 214 nm;
indol-3-yl)-1- H
hydroxymethylethyl]amide; flow rate 1 mi/min; eluents \_ HN H

A: 0.1 % TFA in H20, B
N-[2-(5-Fluoro-1H-indol-3-yl)-1- 0.1% TFA in ACN; gradient hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2) to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Ethoxyphenylboronic acid 491.6 Retention time: 10.29 min.

281 4'-Hydroxymethyl-4- 135 Column Purospher Star RP H
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- - N
H
acid [(R)-1-hydroxymethyl-2- tion wavelength 214 nm; HO HN
flow rate 1 ml/min; eluents (1 H-indol-3-yl)ethyl]amide; _O
A: 0.1 % TFA in H20, B
N-((R)-1-Hydroxymethyl-2-(1 H- 0.1 % TFA in ACN; gradient OH
indol-3-y1)ethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2) to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
4-(Hydroxymethyl)-phenyl- 459.5 boronic acid Retention time: 8.16 min.

Product; Method HPLC-MS conditions / Structure Ex. analo- H-NMR (400 MHz) S[ppm]
reagents gous to 282 3'-Hydroxymethyl-4- 135 Column Purospher Star RP _ H
N
propoxybiphenyl-3-carboxylic C1 8 4.6x1 25 5pm; detec- ~~
HO
acid[(R)-1-hydroxymethyl-2- tion wavelength 214 nm; HNH
flow rate 1 ml/min; eluents (1 H-indol-3-yl)ethyl]amide; -O
A: 0.1 % TFA in H20, B H
N-((R)-2-Hydroxy-l-(1 H-indol-3- 0.1% TFA in ACN; gradient ylmethyl)ethylJ-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-(Hydroxymethyl)- 459.5 phenylboronic acid Retention time: 8.28 min.

283 4-Propoxybiphenyl-3,4'- 135 Column Purospher Star RP H
dicarboxylic acid 3-{[(R)-1- C18 4.6x125 5pm; detec- N
hydroxymethyl-2-(1 H-indol-3- tion wavelength 214 nm; Ho ! H
yl)ethyl]amide} 4'-methylamide; flow rate 1 ml/min; eluents HN
A: 0.1 % TFA in H20, B
N-[(R)-2-Hydroxy-l-(1H-indol-3- 0.1% TFA in ACN; gradient ylmethyl)ethylJ-5-iodo-2- in each case based on B: o propoxybenzamide 5% to 95% (10') to 95% (2) HN
to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
4-(N-Methylaminocarbonyl)- 486.5 phenylboronic acid Retention time: 7.84 min.

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents sousto H-NMR (400 MHz) S[ppm]

284 N-[(R)-2-Hydroxy-1-(1 H-indol-3- 135 Column Purospher Star RP qj1 C18 4.6x125 5Nm; detec- ylmethyl)ethyl]-5-(5- ylmethyl)ethyl]-5-(5-hydroxymethylwavelength 214 nm; HO
flow rate 1 ml/min; eluents H" 0 propoxybenzamide;
A: 0.1% TFA in H20, B ~~O
N-((R)-2-Hydroxy-1-(1H-indol-3- 0.1% TFA in ACN; gradient ylmethyl)ethyl]-5-iod-2- in each case based on B: s ~
propoxybenzamide 5% to 95% (10') to 95% (2') HO
to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
5-(Hydroxymethyl)thiophene-2- 465.5 boronic acid Retention time: 8.21 min.

285 5'-Fluoro-4-propoxybiphenyl- 135 Column Purospher Star RP H
C18 4.6x125 5pm; detec- "
3,3'-dicarboxylic acid 3-{[(R)-2-hydroxy-1-(1H-indol-3- tion wavelength 214 nm; HO H
ylmethyl)ethyl]amide} 3'-methyl- flow rate 1 mI/min; eluents --\,o" o amide; A: 0.1% TFA in H20, B
0.1 % TFA in ACN; gradient F
N-((R)-2-Hydroxy-l-(1H-indol-3- in each case based on B:
ImethY)1 ethYI1-5-~ ~odo-2- 5% to 95% 10' to 95% (2') "~ o Y ( ) propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 504.5 3-Fluoro-5-(methylcarbamoyl)- Retention time: 8.46 min.
phenylboronic acid Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]

286 3'-Chloro-4-propoxybiphenyl- 135 Column Purospher Star RP H
C18 4.6x125 5Nm; detec- N
3,4'-dicarboxylic acid 3-{[(R)-2-hydroxy-1-(1 H-indol-3- tion wavelength 214 nm; "O H
ylmethyl)ethyl]amide} 4'-methyl- flow rate 1 mI/min; eluents H ~o 0 A: 0.1 % TFA in H20, B
amide;
0.1% TFA in ACN; gradient / c' N-((R)-2-Hydroxy-1-(1H-indol-3- in each case based on B:
HN~
ylmethyl)ethyl]-5-iodo-2- 5% to 95% (10') to 95% (2') propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 521 3-Chloro-4-(N- Retention time: 8.11 min.
methylcarbamoyl)-phenylboronic acid 287 3'-Hydroxymethyl-4- 135 Column Purospher Star RP
propoxybiphenyl-3-carboxylic C1 8 4.6x1 25 5pm; detec- N-acid [(R)-1-hydroxymethyl-2-(1- tion wavelength 214 nm; OH
methyl-1 H-indol-3- flow rate 1 mi/min; eluents HO "N o yl)ethyl]amide; A: 0.1 % TFA in H20, B
0.1% TFA in ACN; gradient N-((R)-1-Hydroxymethyl-2-(1- in each case based on B:
methyl-lH-indol-3-yl)ethyl]-5- 5% to 95% (10') to 95% (2') iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 473.6 3-Hydroxymethylphenylboronic Retention time: 8.92 min.
acid Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]

288 3'-Hydroxymethyl-4- 135 Column Purospher Star RP F
propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- NH
acid [2-(5-fluoro-1 H-indol-3-yl)- tion wavelength 214 nm; oH
1-hydroxymethylethyl]amide; flow rate 1 mI/min; eluents HO HN H
o A: 0.1 % TFA in H20, B ~\ r\
- _ o N-[2-(5-Fluoro-1H-indol-3-yl)-1- 0.1% TFA in ACN; gradient hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Hydroxymethylphenylboronic 477.5 acid Retention time: 8.45 min.

Column Purospher Star RP F
289 3'-Chloro-4-propoxybiphenyl- 135 3,4'-dicarboxylic acid 3-{[2-(5- C18 4.6x125 5pm; detec- NH
fluoro-1 H-indol-3-yl)-1- tion wavelength 214 nm; OH
HN H
hydroxymethylethyl]amide} 4'- flow rate 1 mI/min; eluents o cl o 11 methylamide;
A: 0.1 % TFA in H20, B -H ~
0.1 % TFA in ACN; gradient N-[2-(5-Fluoro-1 H-indol-3-yl)-1-in each case based on B:
hydroxymethylethyl]-5-iodo-2- 5% to 95% (10') to 95% (2') propoxybenzamide to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Chloro-4-(methylamino- 539 carbonyl)phenylboronic acid Retention time: 8.2 min.
290 N-[(R)-2-Hydroxy-1-(1-methyl- 135 Column Purospher Star RP
1 H-indol-3-ylmethyl)ethyl]-5-(5- C18 4.6x125 5pm; detec- N-hydroxymethylthiophen-2-yl)-2- tion wavelength 214 nm; OH
propoxybenzamide; flow rate 1 mI/min; eluents Ho HN' o A: 0.1% TFA in H20, B ~o N-((R)-1-Hydroxymethyl-2-(1- 0.1% TFA in ACN; gradient methyl-1H-indol-3-yl)ethyl]-5- in each case based on B:
iodo-2-propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]
and Molecular peak (ESI, M+1):
479.6 5-(Hydroxymethyl)thiophene-2- Retention time: 8.87 min.
boronic acid 291 3'-Chloro-4-propoxybiphenyl- 135 Column Purospher Star RP
3,4'-dicarboxylic acid 3-([(R)-2- C18 4.6x125 5pm; detec- N-tion wavelength hydroxy-1 -(1 -methyl-1 H-indol- 214 nm; H oH
flow rate 1 mI/min; eluents cl HN
3-yimethyl)ethyl]amide} 4'- 0 / \ / \ o A: 0.1% TFA in H20, B -H ~
methylamide;
0.1 % TFA in ACN; gradient N-((R)-1-Hydroxymethyl-2-(1-in each case based on B:
methyl-1 H-indol-3-yl)ethyl]-5-5% to 95% (10') to 95% (2') iodo-2-propoxybenzamide to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Chloro-5-(methylcarbamoyl)- 535 phenylboronic acid Retention time: 8.82 min.
Column Purospher Star RP F
292 4'-Hydroxymethyl-4- 135 propoxybiphenyl-3-carboxylic C18 4.6x125 5pm; detec- NH
acid [2-(5-fluoro-1 H-indol-3-yl)- tion wavelength 214 nm; oH
1-hydroxymethylethyl]amide; flow rate 1 mI/min; eluents HN o _ A: 0.1% TFA in H20, B Ho ~/ /~ O
N-[2-(5-Fluoro-1H-indol-3-yl)-1- 0.1% TFA in ACN; gradient hydroxymethylethyl]-5-iodo-2- in each case based on B:
propoxybenzamide 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
4-Hydroxymethylphenylboronic 477.5 acid Retention time: 8.24 min.

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents 9ous to H-NMR (400 MHz) S[ppm]

293 4-Propoxybiphenyl-3,4'- 135 Column Purospher Star RP F
dicarboxylic acid 3-{[2-(5-fluoro- C18 4.6x125 5pm; detec- NH
1 H-indol-3-yl)-1- tion wavelength 214 nm; oH
HN H
hydroxymethylethyl]amide} 4'- flow rate 1 ml/min; eluents 0 A: 0.1% TFA in H20, B H ~ r - ~
methylamide;
0.1 % TFA in ACN; gradient N-(2-(5-Fluoro-1H-indol-3-yl)-1- in each case based on B:
hydroxymethylethyl]-5-iodo-2- 5% to 95% (10') to 95% (2') propoxybenzamide to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1):
and 504.6 4-(Methylaminocarbonyl)- Retention time: 7.97 min.
phenylboronic acid Column Purospher Star RP F
294 5'-Fluoro-4-propoxybiphenyl- 135 3,3'-dicarboxylic acid 3-{[2-(5- C18 4.6x125 5pm; detec- ~ NH
fluoro-1 H-indol-3-yl)-1- tion wavelength 214 nm; oH
hydroxymethylethyl]amide} 3'- flow rate 1 ml/min; eluents F HN H
methylamide; A: 0.1 % TFA in H20, B o 0.1 % TFA in ACN; gradient O NH
N-(2-(5-Fluoro-1H-indol-3-yl)-1- in each case based on B: hydroxymethylethylJ-5-iodo-2-5% to 95% (10') to 95% (2') propoxybenzamide to 5% (0.5') to 5% (2.5') and Molecular peak (ESI, M+1):
3-Fluoro-5-(methylcarbamoyl)- 522.6 phenylboronic acid Retention time: 8.62 min.

295 4-Ethoxy-3'-fluoro-N-[(R)-1- 39 (DMSO-d6): 10.82 s(1H); OH (hydroxymethyl)-2-(1 H-indol-3- 8.39 d (J = 8.1 Hz, 1 H); H N
H
yl)ethyl]-4'-methoxy[1,1'- 8.12 d (J = 2.5 Hz, 1 H); F\
biphenyl]-3-carboxamide; 7.75 dd (J = 8.7 Hz / 2.5 'o Hz, 1 H); 7.70 d (J = 8.0 Hz, D-Tryptophanol and 1 H); 7.51 dd (J = 12.9 Hz /
4-Ethoxy-3' fluoro-4'- 2.2 Hz, 1 H); 7.43 d (J = 8.8 Product; Method HPLC-MS conditions I Structure Ex. analo- H-NMR (400 MHz) S[ppm]
reagents 9ous to methoxy[l,1'-biphenyl]-3- Hz, 1 H); 7.34 d (J = 8.0 Hz, carboxylic acid 1 H); 7.24 dd (J = 8.8 Hz /
8.8 Hz, 1 H); 7.19 d (J = 8.7 Hz, 1 H); 7.16 d (J = 2.3 Hz, 1 H); 7.06 dd (J = 8.0 Hz /
7.0 Hz, 1 H); 6.97 dd (J =
8.0 Hz / 7.0 Hz, 1 H); 4.93 m(1 H); 4.26 m(1 H); 4.15 m (2H); 3.88 s (3H); 3.50 m (1 H); 3.45 m(1 H); 3.00 dd (J = 14.4 Hz / 7.6 Hz, 1 H);
2.97 dd (J = 14.4 Hz / 5.8 Hz, 1 H); 1.31 t (J = 7.0 Hz, 3H).

296 4-Ethoxy-N-[(R)-1- 39 (DMSO-d6): 10.82 s(1H); OH
(hydroxymethyl)-2-(1 H-indol-3- 8.40 d (J = 8.1 Hz, 1 H); o NH N
H
yI)ethyl]-3'-methoxy[1,1'- 8.16 d (J = 2.5 Hz, 1 H); 0 biphenyl]-3-carboxamide; 7.77 dd (J = 8.6 Hz / 2.5 Hz, 1 H); 7.70 d (J = 8.0 Hz, D-Tryptophanol and 1 H); 7.38 dd (J = 8.3 Hz /
4-Ethoxy-3' methoxy(1,1 '- 7.8 Hz, 1 H); 7.34 d (J = 8.0 biphenylJ-3-carboxylic acid Hz, 1 H); 7.21 d (J = 8.6 Hz, 1 H); 7.19 d (J = 7.8 Hz, 1 H); 7.17 d (J = 2.3 Hz, 1 H); 7.14 dd (J = 2.5 Hz /
1.8 Hz, 1 H); 7.06 dd (J =
8.0 Hz / 7.0 Hz, 1 H); 6.97 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 6.92 dd (J = 8.3 Hz /
2.5 Hz, 1 H); 4.93 m(1 H);
4.27 m(1 H); 4.16 m (2H);
3.83 s(3H); 3.50 m(1 H);

Product; Method HPLC-MS conditions I Structure Ex. analo- H-NMR (400 MHz) S[ppm]
reagents gous to 3.46 m(1 H); 3.01 dd (J =
14.4 Hz / 7.3 Hz, 1 H); 2.96 dd (J = 14.4 Hz / 6.3 Hz, 1 H); 1.32 t (J = 7.0 Hz, 3H).

297 4-Ethoxy-N-[(R)-1- 39 (DMSO-d6): 10.82 s(1H); OHT -(hydroxymethyl)-2-(1 H-indol-3- 8.61 q (J = 4.6 Hz, 1 H); 0 NH ~ N
yI)ethyl]-M-methyl[1,1'- 8.41 d (J = 8.1 Hz, 1 H); 1 ol H
biphenyl]-3,3'-dicarboxamide; 8.25 d (J = 2.5 Hz, 1 H);
8.10 s(1 H); 7.84 dd (J =
D-Tryptophanol and N' 8.6 Hz / 2.5 Hz, 1 H); 7.80 d 4-Ethoxy-3' (J = 7.8 Hz, 1 H); 7.78 d (J =
[(methylamino)carbonyl](1,1'- 7.6 Hz, 1 H); 7.71 d (J = 8.0 biphenyl]-3-carboxylic acid Hz, 1 H); 7.54 dd (J = 7.8 Hz/7.6 Hz, 1H); 7.33 d(J
= 8.0 Hz, 1 H); 7.25 d (J =
8.6 Hz, 1 H); 7.17 d (J = 2.3 Hz, 1 H); 7.06 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 6.97 dd (J
= 8.0 Hz / 7.0 Hz, 1 H); 4.94 m(1 H); 4.28 m(1 H); 4.17 m (2H); 3.51 m(1 H); 3.46 m(1 H); 3.01 dd (J = 14.4 Hz / 7.3 Hz, 1 H); 2.98 dd (J
= 14.4 Hz / 6.1 Hz, 1 H);
2.82 d (J = 4.6 Hz, 3H);
1.33 t (J = 7.0 Hz, 3H).

Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]
298 4-Ethoxy-N-[(R)-1- 39 (DMSO-d6): 10.82 s(1H);
(hydroxymethyl)-2-(1 H-indol-3- 8.41 d (J = 7.9 Hz, 1 H);
yl)ethyl]-3',4',5'-trimethoxy[1,1'- 8.14 d (J = 2.5 Hz, 1 H); NH
biphenyl]-3-carboxamide; 7.78 dd (J = 8.7 Hz / 2.5 HO NH
Hz, 1 H); 7.70 d (J = 8.0 Hz, D-Tryptophanol and 1 H); 7.33 d (J = 8.0 Hz, 4-Efhoxy-3;4;5 1 H); 7.20 d (J = 8.7 Hz, ' I ~

trimethoxy(1,1 '-biphenylJ-3- 1 H); 7.17 s (1 H); 7.06 dd (J
carboxylic acid = 8.0 Hz / 7.0 Hz, 1 H); 6.97 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 6.86 s(2H); 4.93 m (1 H); 4.26 m(1 H); 4.16 m (2H); 3.86 s (6H); 3.69 s (3H); 3.50 m(1 H); 3.45 m (1 H); 3.01 dd (J = 14.2 Hz /
7.0 Hz, 1 H); 2.97 dd (J =
14.2 Hz / 6.2 Hz, 1 H); 1.32 t (J = 7.0 Hz, 3H).

299 4-Ethoxy-N-[(R)-1- 39 (DMSO-d6): 10.82 s(1H);
(hydroxymethyl)-2-(1 H-indol-3- 8.41 d (J = 8.1 Hz, 1 H);
NH
yI)ethyl]-3',4'-dimethoxy[1,1'- 8.13 d (J = 2.5 Hz, 1 H);
biphenyl]-3-carboxamide; 7.74 dd (J = 8.6 Hz / 2.5 Ho NH o Hz, 1 H); 7.70 d (J = 8.0 Hz, o D-Tryptophanol and 1 H); 7.33 d (J = 8.0 Hz, 4-Ethoxy-3 ; 4' dimethoxy(1,1 '- 1 H); 7.18 d (J = 8.6 Hz, biphenyl]-3-carboxylic acid 1 H); 7.16 s (2H); 7.15 dd (J o ~
= 8.1 Hz / 2.3 Hz, 1 H); 7.06 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 7.03 d (J = 8.1 Hz, 1H);6.97dd(J=8.0Hz/
7.0 Hz, 1 H); 4.93 m(1 H);
4.27 m(1 H); 4.15 m (2H);

Product; Method HPLC-MS conditions / Structure Ex. analo- H-NMR (400 MHz) S[ppm]
reagents 9o~s to 3.85 s (3H); 3.79 s (3H);
3.50 m(1 H); 3.45 m(1 H);
3.01 dd (J = 14.2 Hz / 7.3 Hz, 1 H); 2.97 dd (J = 14.2 Hz / 5.8 Hz, 1 H); 1.32 t(J =
7.0 Hz, 3H).

300 4-Ethoxy-N-[(R)-1- 39 (CDCI3): 8.14 s(1H); 8.52 OH
(hydroxymethyl)-2-(1 H-indol-3- m(1 H); 8.51 d (J = 2.5 Hz, 0 NH
N
H
yl)ethyl]-3'-(1-methylethyl)[1,1'- 1 H); 7.71 d (J = 8.0 Hz, 0 biphenyl]-3-carboxamide; 1 H); 7.66 dd (J = 8.6 Hz 2.5 Hz, 1 H); 7.48 s(1 H);
D-Tryptophanol and 7.42 d (J = 7.8 Hz, 1 H);
4-Ethoxy-3'-(1- 7.36 d(J = 8.0 Hz, 1 H);
methylethyl)[1,1 '-biphenyl]-3- 7.35 dd (J = 7.8 Hz / 7.6 carboxylic acid Hz, 1 H); 7.20 d (J = 7.6 Hz, 1 H); 7.19 dd (J = 8.0 Hz /
7.0 Hz, 1 H); 7.12 dd (J =
8.0 Hz / 7.0 Hz, 1 H); 7.11 d =
(J = 2.3 Hz, 1 H); 6.97 d (J
8.6 Hz, 1 H); 4.58 m(1 H);
4.06 m (2H); 3.84 d (J =
10.9 Hz, 1 H); 3.77 dd (J =
10.9 Hz / 5.1 Hz, 1 H); 3.17 dd (J = 15.2 Hz / 6.8 Hz, 1 H); 3.14 dd (J = 15.2 Hz /
6.8 Hz, 1 H); 2.97 sept (J =
6.8 Hz, 1 H); 1.30 d(J = 6.8 Hz, 6H); 1.26 t (J = 7.0 Hz, 3H).

Product; Method HPLC-MS conditions / Structure Ex. analo- H-NMR (400 MHz) 8[ppm]
reagents gous to 301 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDCI3): 8.49 d (J = 7.5 Hz, OH (1 H-indol-3-yl)ethyl]-3',4',5'- 1 H); 8.47 d(J = 2.6 Hz, 0 NH 'H

trimethoxy-4-propoxy[1,1'- 1 H); 8.12 s(1 H); 7.71 d (J o 1 o,-,-biphenyl]-3-carboxamide; = 8.0 Hz, H); 7.61 dd (J = ~o 8.7 Hz / 2.6 Hz, 1 H); 7.36 d "o D-Tryptophanol and (J = 8.0 Hz, 1 H); 7.20 dd (J
3;4;5'-Trimethoxy-4- = 8.0 Hz / 7.0 Hz, 1H); 7.11 propoxy[l,1 '-biphenylJ-3- dd (J = 8.0 Hz / 7.0 Hz, carboxylic acid 1 H); 7.11 s(1 H); 6.98 d(J
= 8.7 Hz, 1 H); 6.79 s (2H);
4.60 m(1 H); 3.97 m (2H);
3.92 s (6H); 3.89 s (3H);
3.81 m (2H); 3.15 m (2H);
1.66 m (2H); 0.95 t (J = 7.4 Hz, 3H).

302 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDC13): 8.49 d (J = 7.4 Hz, OH (1 H-indol-3-yI)ethyl]-3',4'- 1 H); 8.47 d(J = 2.5 Hz, o NH 'N
H
dimethoxy-4-propoxy[1,1'- 1 H); 8.11 s(1 H); 7.71 d (J biphenyl]-3-carboxamide; = 8.0 Hz, 1 H); 7.62 dd (J

8.7 Hz / 2.5 Hz, 1 H); 7.36 d D-Tryptophanol and (J = 8.0 Hz, 1 H); 7.19 dd (J
3;4'-Dimethoxy-4-propoxy[l,1 '- = 8.0 Hz / 7.0 Hz, 1 H); 7.12 biphenylJ-3-carboxylic acid m (4H); 6.97 d (J = 8.7 Hz, 1 H); 6.93 d (J = 8.3 Hz, 1 H); 4.59 m (1 H); 3.97 m (2H); 3.95 s (3H); 3.92 s (3H); 3.81 m (2H); 3.18 dd (J = 15.1 Hz / 6.8 Hz, 1 H);
3.13 dd (J = 15.1 Hz/7.9 Hz, 1 H); 1.65 m (2H); 0.94 t (J = 7.4 Hz, 3H).

Product; Method HPLC-MS conditions / Structure Ex. analo- H-NMR (400 MHz) S[ppm]
reagents 9o~s to 303 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDCI3): 8.51 d (J = 2.6 Hz, OH
\~
(1 H-indol-3-yl)ethyl]-3'- 1 H); 8.46 d (J = 7.5 Hz, o N'H ~N
H
o \ ~ i methoxy-4-propoxy[1,1'- 1 H); 8.09 s(1 H); 7.71 d (J
biphenyl]-3-carboxamide; = 8.0 Hz, H); 7.65 dd (J = ~~
8.7 Hz / 2.6 Hz, 1 H); 7.36 d D-Tryptophanol and (J = 8.0 Hz, 1 H); 7.34 dd (J
3'-Methoxy-4-propoxy(1,1'- = 7.9 Hz / 7.9 Hz, 1 H); 7.20 biphenyl]-3-carboxylic acid d (J = 7.9 Hz, H); 7.19 dd (J
= 8.0 Hz / 7.0 Hz, 1H);7.14 s(1H); 7.11 dd(J=8.0Hz/
7.0 Hz, 1 H); 7.11 s(1 H);
6.98 d (J = 8.7 Hz, 1 H);
6.88 dd (J = 7.9 Hz / 2.5 Hz, 1 H); 4.59 m(1 H); 3.96 m (2H); 3.86 s (3H); 3.80 m (2H); 3.16 m (2H); 1.65 m (2H); 0.93 t (J = 7.4 Hz, 3H).

304 N-[(R)-1-(Hydroxymethyl)-2- 39 (CDCI,): 8.47 d(J= 2.5 Hz, OH
(1 H-indol-3-yl)ethyl]-N-methyl- 1 H); 8.42 d (J = 7.4 Hz, 0 NH N
H
4-propoxy[1,1'-biphenyl]-3,3'- 1 H); 8.21 s(1 H); 7.97 dd (J I~ o.~
dicarboxamide; = 1.7 Hz / 1.7 Hz, 1 H); 7.72 m (3H); 7.66 dd (J = 8.7 Hz D-Tryptophanol and H~
/ 2.5 Hz, 1 H); 7.47 dd (J =

3'-[(Methylamino)carbonyl]-4- 7.7 Hz / 7.5 Hz, 1 H); 7.36 d propoxy[1,1 '-biphenyl]-3- (J = 8.0 Hz, 1 H); 7.19 dd (J
carboxylic acid = 8.0 Hz / 7.0 Hz, 1 H); 7.11 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 6.97 d (J = 8.7 Hz, 1 H); 6.37 m (1 H); 4.58 m (1 H); 3.95 m (2H); 3.80 m (2H); 3.16 dd (J = 15.1 Hz /

Product; Method HPLC-MS conditions I Structure Ex. analo-reagents 9ous to H-NMR (400 MHz) S[ppm]
6.8 Hz, 1 H); 3.13 dd (J =
15.1 Hz / 7.9 Hz, 1 H); 3.04 d (J = 4.9 Hz, 3H); 1.65 m (2H); 0.93 t (J = 7.4 Hz, 3H).

305 4,3',4',5'- 39 (DMSO-d6): 10.85 s(1 H); - N
~
Tetramethoxybiphenyl-3- 8.19 d (J = 7.8 Hz, 1 H); i carboxylic acid [(R)-1- 8.05 d (J = 2.3 Hz, 1 H); Ho\
hydroxymethyl-2-(1 H-indol-3- 7.76 dd (J = 8.6 Hz, J = 2.3 0 NH
yi)ethyl]amide; Hz, 1 H); 7.69 d (J = 7.8 Hz, I o1~
1 H); 7.33 d (J = 7.8 Hz, 0 (D)-Tryptophanol 1 H); 7.18-7.20 m (2H); 7.06 0 t(J = 7.2 Hz, 1 H); 6.97 t (J oll and = 7.4 Hz, 1 H); 6.83 s (2H);
4-Methoxy-3 ; 4; 5' 4.93 t (J = 5.2 Hz, 1 H);
trimethoxybiphenyl-3-carboxylic 4.20-4.23 m (1 H); 3.85 s acid (6H); 3.84 s (3H); 3.68 s (3H); 3.40-3.56 m (2H);
2.95-3.05 m (2H).

306 4,3',4'-Trimethoxybiphenyl-3- 39 (DMSO-d6): 10.85 s(1 H); - N
carboxylic acid [(R)-1-hydroxy- 8.20 d (J = 7.8 Hz, 1 H); \~
methyl-2-(1 H-indol-3- 8.04 d (J = 2.3 Hz, 1 H); Ho yI)ethyl]amide; 7.73 dd (J = 8.6 Hz, J= 2.3 0 NH
Hz, 1 H); 7.69 d (J = 7.8 Hz, (D)-Tryptophanol 1 H); 7.34 d (J = 8.2 Hz, 0 and 1 H); 7.12-7.20 m (4H); 7.06 o t(J = 7.6 Hz, 1 H); 7.02 d (J
= 8.2 Hz, 1 H); 6.98 t (J =
.4Hz, 1H);4.94t(J=5.1 4, 3 ; 4' Trimethoxybiphenyl-3- 7Hz, 1 H); 4.21-4.29 m(1 H);
carboxylic acid 3.84 s (3H); 3.83 s (3H);
3.78 s (3H); 3.40-3.56 m Product; Method HPLC-MS conditions / Structure Ex. analo-reagents yous to H-NMR (400 MHz) S[ppm]
(2H); 2.96-3.05 m (2H).

307 3'-Fluoro-4,4'- 39 (DMSO-d6): 10.85 s(1 H); ~ H
dimethoxybiphenyl-3-carboxylic 8.18 d (J = 7.8 Hz, 1 H);
acid [(R)-2-hydroxy-1-(1 H- 8.01 d (J = 2.3 Hz, 1 H); HO
indol-3-ylmethyl)ethyl]amide; 7.73 dd (J = 8.7 Hz, J = 2.3 o H
Hz, 1 H); 7.69 d(J = 7.8 Hz, ~
(D)-Tryptophanol 1 H); 7.49 dd (J = 12.9 Hz, j F
= 1.9 Hz, 1 H); 7.40 d (J = q and I
8.6 Hz, 1 H); 7.34 d (J = 8.2 3' Fluoro-4, 4'- Hz, 1 H); 7.23 t(J = 8.8 Hz, dimethoxybiphenyl-3-carboxylic 1 H); 7.17-7.19 m (2H); 7.06 acid t (J = 7.4 Hz, 1 H); 6.98 t (J
= 7.4 Hz, 1 H); 4.93 t (J =
5.2 Hz, 1 H); 4.20-4.28 m (1 H); 3.87 s (3H); 3.83 s (3H); 3.40-3.56 m (2H);
2.95-3.05 m (2H). !

308 4,3'-Dimethoxybiphenyl-3- 39 (DMSO-d6): 10.85 s(1 H); - N
carboxylic acid [(R)-1-hydroxy- 8.19 d (J = 8.2 Hz, 1 H); ~~
methyl-2-(1 H-indol-3- 8.06 d (J = 2.7 Hz, 1 H); Ho yl)ethyl]amide; 7.76 dd (J = 8.8 Hz, J = 2.5 0 NH
Hz, 1 H); 7.69 d (J = 7.8 Hz, o~
(D)-Tryptophanol 1 H); 7.36 t(J = 8.0 Hz, 1 H); 0'~ I~
7.34 d (J = 8.2 Hz, 1 H);
and 7.16-7.21 m (3H); 7.12 4,3' Dimethoxybiphenyl-3- (1 H); 7.06 t (J = 7.4 Hz, carboxylic acid 1 H); 6.98 t (J = 7.4 Hz, 1 H);
6.91 dd (J = 8.2 Hz, J = 2.3 Hz, 1 H); 4.93 t (J = 5.2 Hz, 1 H); 4.21-4.29 m(1 H); 3.83 s (3H); 3.82 s (3H); 3.41-3.56 m (2H); 2.95-3.06 m Product; Method HPLC-MS conditions I Structure Ex. analo-reagents 9ous to H-NMR (400 MHz) 8[ppm]
(2H).
309 5-Benzo[1,3]dioxol-5-yI-N-[(R)- 39 (DMSO-d6): 10.84 s(1H); - N
~
1-hydroxymethyl-2-(1 H-indol-3- 8.17 d (J = 7.8 Hz, 1 H);
yI)ethyl]-2-methoxybenzamide; 8.04 d (J = 2.3 Hz, 1 H); Ho 7.97 d (J = 2.3 Hz, 1 H); O NH
(D)-Tryptophanol ON
7.66-7.70 m(1 H); 7.34 d (J o and = 7.8 Hz, 1 H); 7.15-7.19 m <

(3H); 7.04-7.08 m (2H);
5-Benzo[1,3]dioxol-5-y1-2- 6.96-6.99 m(2H); 6.05 s methoxybenzoic acid (2H); 4.93 t (J = 5.2 Hz, 1 H); 4.20-4.28 m(1 H); 3.82 s (3H); 3.40-3.56 m (2H);
2.96-3.05 m (2H).

310 3',4'-Difluoro-4,5'- 39 (DMSO-d6): 10.84 s(1H); N
dimethoxybiphenyl-3-carboxylic 8.17 d (J = 7.8 Hz, 1 H);
acid [(R)-2-hydroxy-1-(1 H- 8.04 d (J = 1.9 Hz, 1 H); HO
o H
indol-3-yimethyl)ethyl]amide; 7.80 dd (J = 8.8 Hz, J = 2.3 I 0~
Hz, 1 H); 7.69 d(J = 7.8 Hz, ,0 ~ I
(D)-Tryptophanol ~
1 H); 7.33 d (J = 7.8 Hz, F
F
and 1 H); 7.19-7.27 m(4H); 7.06 t(J = 7.4 Hz, 1 H); 6.97 t (J
3; 4' Difluoro-4, 5'- = 7.4 Hz, 1 H); 4.93 t (J =
dimethoxybiphenyl-3-carboxylic 4.8 Hz, 1 H); 4.20-4.28 m acid (1 H); 3.97 s(3H); 3.84 s (3H); 3.40-3.56 m (2H);
2.95-3.05 m (2H).

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents 9ous to H-NMR (400 MHz) S[ppm]

311 4-Isopropoxy-3'- 39 (DMSO-d6): 10.82 s(1H); -/ N
~ ~
methoxybiphenyl-3-carboxylic 8.49 d (J = 8.20 Hz, 1 H);
acid [(R)-1-hydroxymethyl-2- 8.19 d (J = 2.3 Hz, 1 H); o NH
(1 H-indol-3-yl)ethyl]amide; 7.75 dd (J = 8.6 Hz, J = 2.7 \ I% oT,~, (D)-Tryptophanol Hz, 1 H); 7.71 d(J = 7.8 Hz, /
1 H); 7.37 t (J = 8 Hz, 1 H);
and 7.33 d (J = 8.2 Hz, 1 H);
7.24 d (J = 8.6 Hz, 1 H);
4-Isopropoxy-3' 7.19 d(J = 7.8 Hz, 1 H);
methoxybiphenyl-3-carboxylic 7.14-7.16 m (2H); 7.06 t (J
acid = 7.6 Hz, 1 H); 6.97 t (J =
7.2 Hz, 1 H); 6.92 dd (J =
8.2 Hz, J = 2 Hz, 1H);4.97t (J = 5.1 Hz, 1 H); 4.78-4.84 m(1 H); 4.23-4.30 m(1 H);
3.82 s (3H); 3.42-3.54 m (2H); 2.95-3.04 m (2H);
1.28 d (J = 5.6 Hz, 3H);
1.27 d (J = 5.6 Hz, 3H).

312 5-Benzo[1,3]dioxol-5-yi-N-[(R)- 39 (DMSO-d6): 10.82 s(1H); - N
~
1-hydroxymethyl-2-(1 H-indol-3- 8.48 d (J = 8.20 Hz, 1 H);
HO
yi)ethyl]-2- 8.10 d (J = 2.3 Hz, 1 H); 0 NH
isopropoxybenzamide; 7.71 d (J = 7.8 Hz, 1 H); I oIT"
7.67 dd (J = 8.6 Hz, J = 1.9 (D)-Tryptophanol ~o I
Hz, 1 H); 7.33 d (J = 8.2 Hz, and 1 H); 7.19-7.21 m (2H); 7.15 (1 H); 7.04-7.10 m (2H);
5-Benzo[1,3]dioxol-5-y1-2- 6.95-6.99 m(2H); 6.05 s isopropoxybenzoic acid (2H); 4.97 t (J = 5.1 Hz, 1 H); 4.75-4.81 m(1 H);
4.22-4.29 m (1H); 3.42-3.54 m (2H); 2.94-3.04 m (2H);

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents yous to H-NMR (400 MHz) S [ppm]
1.28 d(J = 5.6 Hz, 3H);
1.27 d (J = 5.6 Hz, 3H).

313 4-Isopropoxy-3',4',5'- 39 (DMSO-d6): 10.82 s(1 H); -/ N
trimethoxybiphenyl-3-carboxylic 8.49 d (J = 8.20 Hz, 1 H);
acid [(R)-1-hydroxymethyl-2- 8.16 d (J = 2.3 Hz, 1 H); HO
O NH
(1 H-indol-3-yI)ethyl]amide; 7.75 dd (J = 8.6 Hz, J = 2.3 0~
Hz, 1 H); 7.71 d (J = 7.8 Hz, o I
(D)-Tryptophanol 1 H); 7.33 d (J = 7.8 Hz, o and 1 H); 7.24 d (J = 8.6 Hz, I o1~
1 H); 7.15 (1 H); 7.06 t(J =
4-Isopropoxy-3;4;5' 7.6 Hz, 1 H); 6.97 t (J = 7.4 trimethoxybiphenyl-3-carboxylic Hz, 1 H); 6.85 s (2H); 4.97 t acid (J = 4.7 Hz, 1 H); 4.78-4.84 m(1 H); 4.23-4.30 m(1 H);
3.86 s (3H); 3.69 s (3H);
3.42-3.54 m (2H); 2.95-3.04 m (2H); 1.28 d (J = 5.6 Hz, 3H); 1.27 d (J = 5.6 Hz, 3H).

314 3'-Fluoro-4-isopropoxy-4'- 39 (DMSO-d6): 10.83 s(1 H); - N
methoxybiphenyl-3-carboxylic 8.48 d (J = 8.20 Hz, 1 H);
acid [(R)-2-hydroxy-1-(1 H- 8.15 d (J = 2.3 Hz, 1 H); HO
O H
indoi-3-ylmethyl)ethyl]amide; 7.71 d (J = 7.4 Hz, 1 H);
7.50 dd (J = 12 Hz, J = 1.9 F \ I
(D)-Tryptophanol Hz, 1 H); 7.42 d (J = 8.6 Hz, i and 1 H); 7.33 d (J = 8.2 Hz, 1 H); 7.24 t(J = 8.2 Hz, 1 H);
3' Fluoro-4-isopropoxy-4' 7.22 d (J = 8.8 Hz, 1 H);
methoxybiphenyl-3-carboxylic 7.16 (1 H); 7.06 t (J = 7.4 acid Hz, 1 H); 6.97 t (J = 7.4 Hz, 1 H); 4.98 t (J = 5.1 Hz, 1 H);
4.77-4.83 m (1 H); 4.23-4.30 Product; Method HPLC-MS conditions / Structure Ex. analo-reagents yous to H-NMR (400 MHz) 8[ppm]
m(1 H); 3.87 s (3H); 3.42-3.55 m (2H); 2.95-3.05 m (2H); 1.28 d (J = 5.6 Hz, 3H); 1.27 d (J = 5.6 Hz, 3H).

315 4-Isopropoxy-3',4'- 39 (DMSO-d6): 10.82 s(1 H) - N
dimethoxybiphenyl-3-carboxylic 8.50 d (J = 7.8 Hz, 1 H);
acid [(R)-1-hydroxymethyl-2- 8.16 d (J = 2.3 Hz, 1 H); Ho~
O NH
(1 H-indol-3-yl)ethyl]amide; 7.71 dd (J = 8.6 Hz, J = 2.7 0-r Hz, 1 H); 7.34 d (J = 8.2 Hz, o (D)-Tryptophanol 1 H); 7.22 d (J = 8.9 Hz, o ~
1 H); 7.12-7.16 m (3H); 7.06 and t(J = 7.4 Hz, 1 H); 7.02 d(J
4-Isopropoxy-3;4' = 8.6 Hz, 1 H); 6.97 t(J =
dimethoxybiphenyl-3-carboxylic 7.4 Hz, 1 H); 4.97 t (J = 5.1 acid Hz, 1 H); 4.76-4.82 m(1 H);
4.23-4.30 m (1 H); 3.84 s (3H); 3.79 s (3H); 3.42-3.54 m (2H); 2.94-3.04 m (2H);
1.28 d (J = 5.6 Hz, 3H);
1.27 d (J = 5.6 Hz, 3H).

316 4-Isopropoxy-3'- 39 (DMSO-d6): 10.82 s(1 H); N
methylbiphenyl-3-carboxylic 8.50 d (J = 8.2 Hz, 1 H);
acid [(R)-1-hydroxymethyl-2- 8.20 d (J = 2.3 Hz, 1 H); Ho O NH
(1 H-indol-3-yl)ethyl]amide; 7.72 dd (J = 8.6 Hz, J = 2.7 Hz, 1 H); 7.45 (1 H); 7.41 d (D)-Tryptophanol (J = 7.8 Hz, 1 H); 7.31-7.35 and m(2H); 7.24 d (J = 8.6 Hz, 1 H); 7.14-7.16 m (2H); 7.06 4-1sopropoxy-3' t (J = 7.4 Hz, 1 H); 6.97 t (J
methylbiphenyl-3-carboxylic = 7 Hz, 1 H); 4.97 t (J = 5.1 acid Hz, 1 H); 4.77-4.83 m(1 H);

Product; Method HPLC-MS conditions I Structure Ex. analo- H-NMR (400 MHz) S[ppm]
reagents sous to 4.24-4.31 m (1 H); 3.43-3.55 m (2H); 2.95-3.05 m (2H);
2.38 s (3H); 1.28 d (J = 5.6 Hz, 3H); 1.27 d (J = 5.6 Hz, 3H).

317 4'-Fluoro-4-isopropoxy-3'- 39 (DMSO-d6): 10.82 s(1 H); N
methylbiphenyl-3-carboxylic 8.50 d (J = 8.2 Hz, 1 H);
acid [(R)-2-hydroxy-1-(1 H- 8.17 d (J = 2.3 Hz, 1 H); HO
H
indol-3-ylmethyl)ethyl]amide; 7.74-7.70 m(2H); 7.56 d (J I o~
= 7 Hz, 1 H); 7.45-7.48 (1 H);
(D)-Tryptophanol 7.34 d (J = 8.2 Hz, 1 H); F
and 7.20-7.25 m (2H); 7.16 (1 H); 7.06 t (J = 7.4 Hz, 4'-Fluoro-4-isopropoxy-3' 1 H); 6.97 t (J = 7.4 Hz, 1 H);
methylbiphenyl-3-carboxylic 4.97 t (J = 5.1 Hz, 1 H);
acid 4.77-4.83 m(1 H); 4.23-4.31 m (1 H); 3.43-3.55 m (2H);
2.95-3.05 m (2H); 2.31 s (3H); 1.28 d (J = 5.6 Hz, 3H); 1.27 d(J = 5.6 Hz, 3H).

318 3',4'-Difluoro-4-isopropoxy-5- 39 (DMSO-d6): 10.82 s(1 H); -/ N
methoxybiphenyl-3-carboxylic 8.48 d (J = 7.8 Hz, 1 H);
HO
acid [(R)-2-hydroxy- 1 -(1 H- 8.18 d (J = 1.6 Hz, 1 H); o H
indol-3-ylmethyl)ethyl]amide; 7.78 dd (J = 8.74 Hz, J= 1.8 /o 1 o~
Hz, 1 H); 7.72 d (J = 7.8 Hz, I
(D)-Tryptophanol 1 H); 7.33 d (J = 8.2 Hz, F F
and 1 H); 7.28-7.23 m(2H); 7.20 d (J = 6.62 Hz, 1 H); 7.16 3;4'-Difluoro-4-isopropoxy-5'- (1 H); 7.06 t (J = 7.4 Hz, methoxybiphenyl-3-carboxylic 1 H); 6.97 t (J = 7.4 Hz, 1 H);
acid 4.97 t (J = 5.1 Hz, 1 H);

Product; Method HPLC-MS conditions I Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]
4.80-4.86 m (1 H); 4.23-4.30 m(1 H); 3.98 s (3H); 3.42-3.55 m (2H); 2.95-3.04 m (2H); 1.28 d (J = 5.6 Hz, 3H); 1.27 d (J = 5.6 Hz, 3H).

319 4,3',4',5'-Tetramethoxy-5- 39 (DMSO-ds): 10.81 s(1 H); - H
~ N
methylbiphenyl-3-carboxylic 8.26 d (J = 7.8 Hz, 1 H); \
acid [(R)-1-hydroxymethyl-2- 7.69 d (J = 7.8 Hz, 1 H); HO
(1 H-indol-3-yl)ethyl]amide; 7.63-7.65 m (2H); 7.32 d (J 0 NH
(D)-Tryptophanol = 7.8 Hz, 1 H); 7.18 (1 H); 0~
o 7.05 t (J = 7.2 Hz, 1 H); 6.97 I
and t (J = 7.4 Hz, 1 H); 6.84 s o (2H); 4.90 t (J = 5.2 Hz, 01~1 4, 3; 4; 5' Tetramethoxy-5- 1 H); 4.22-4.30 m(1 H); 3.86 methylbiphenyl-3-carboxylic s (6H); 3.69 s(3H); 3.62 s acid (3H); 3.44-3.58 m (2H);
3.03. 2.96 AB (J, = 14.4 Hz, J2 = 6.9 Hz, 2H); 2.31 s (3H).

320 4,3',4'-Trimethoxy-5- 39 (DMSO-d6): 10.81 s(1 H); - H
N
methylbiphenyl-3-carboxylic 8.25 d (J = 8.2 Hz, 1 H);
acid [(R)-1-hydroxymethyl-2- 7.69 d (J = 7.8 Hz, 1 H); Ho\
O NH
(1 H-indol-3-yl)ethyl]amide; 7.59-7.61 m (2H); 7.32 d (J
i ~ o1~
= 7.8 Hz, 1 H); 7.18 (1 H); o \ I~
(D)-Tryptophanol 7.12-7.15 m (2H); 7.01-7.07 I
O
m (2H); 6.97 t (J = 7.4 Hz, I
and 1 H); 4.89 t (J = 5.2 Hz, 1 H);
4, 3; 4'-Trimethoxy-5- 4.23-4.30 m(1 H); 3.84 s methylbiphenyl-3-carboxylic (6H); 3.70 s (3H); 3.61 s acid (3H); 3.44-3.58 m (2H);
3.03. 2.95 AB (J, = 14.3 Product; Method HPLC-MS conditions I Structure Ex. analo- MHz) reagents 9ous to H-NMR (400 S [PPm]

Hz, J2 = 7 Hz, 2H); 2.31 s (3H).

321 3'-Fluoro-4,4'-dimethoxy-5- 39 (DMSO-d6): 10.81 s(1 H); - H
methylbiphenyl-3-carboxylic 8.23 d (J = 8.2 Hz, 1 H);
acid [(R)-2-hydroxy-l-(1 H- 7.69 d (J = 7.8 Hz, 1 H); Ho indol-3-ylmethyl)ethyl]amide; 7.58-7.59 m (2H); 7.49 dd 0 H
(J = 13.1 Hz, J= 1.7 Hz, i 0~
(D)-Tryptophanol F
1 H); 7.40 d (J = 8.2 Hz, and 1 H); 7.33 d (J = 7.8 Hz, 1 H); 7.23 t (J = 9 Hz, 1 H);
3'-Fluoro-4, 4'-dimethoxy-5- 7.17 d (J = 1.6 Hz, 1 H);
methylbiphenyl-3-carboxylic 7.06 t (J = 7.4 Hz, 1 H); 6.97 acid t (J = 7.4 Hz, 1 H); 4.89 t (J
= 5.4 Hz, 1 H); 4.23-4.30 m (1 H); 3.88 s(3H); 3.60 s (3H); 3.44-3.58 m (2H);
3.03, 2.95 AB (J, = 14.2 Hz, J2 = 7 Hz, 2H); 2.29 s (3H).

322 5-Benzo[1,3]dioxol-5-yl-N-[(R)- 39 (DMSO-d6): 10.80 s(1H); - N
~
1-hydroxymethyl-2-(1 H-indol-3- 8.21 d (J = 8.2 Hz, 1 H);
I eth I 2-methox 3-meth I- 7.68 d (J 7.8 Hz, 1 H; "o y) y]- y- y ( ) O NH
benzamide; 7.54 s(2H); 7.30 d (J = 8.2 Hz, 1 H); 7.17-7.18 m (2H); o I~
(D)-Tryptophanol ~ I ~
7.04-7.08 m(1 H); 6.95-6.99 0 and m (2H); 6.06 s (2H); 4.88 t (J = 5.1 Hz, 1 H); 4.22-4.30 5-Benzo[1,3]dioxol-5-y1-2- m(1H); 3.60 s (3H); 3.44-methoxy-3-methyl-benzoic acid 3.57 m (2H); 3.02, 2.94 AB
(J, = 14.3 Hz, J2 = 6.6 Hz, 2H); 2.28 s (3H).

Product; Method HPLC-MS conditions I Structure Ex. analo-reagents sous to H-NMR (400 MHz) S[ppm]

323 4,3'-Dimethoxy-5- 39 (DMSO-d6): 10.81 s (1H); - H
~
methylbiphenyl-3-carboxylic 8.25 d (J = 8.2 Hz, 1 H);
acid [(R)-1-hydroxymethyl-2- 7.69 d (J = 7.8 Hz, 1 H); Ho (1H-indol-3-yI)ethyl]amide; 7.61-7.63 m (2H); 7.36 t (J 0 NH
= 8.2 Hz, 1 H); 7.33 d (J = I o~
(D)-Tryptophanol o I
8.2 Hz, 1 H); 7.14-7.18 m and (3H); 7.06 t (J = 7.4 Hz, 1 H); 6.97 t (J = 7.4 Hz, 1 H);
4, 3' Dimethoxy-5- 6.92 dd (J = 8.2 Hz, J= 1.9 methylbiphenyl-3-carboxylic Hz, 1 H); 4.89 t (J = 5.1 Hz, acid 1 H); 4.23-4.31 m(1 H); 3.82 s (3H); 3.62 s (3H); 3.45-3.58 m (2H); 3.03, 2.95 AB
(J, = 14.5 Hz, J2 = 6.6 Hz, 2H); 2.31 s (3H).

324 4-Methoxy-5,3'- 39 (DMSO-d6): 10.80 s(1 H); , H
N
dimethylbiphenyl-3-carboxylic 8.24 d (J = 8.2 Hz, 1 H); ~~ i acid [(R)-1-hydroxymethyl-2- 7.69 d (J = 7.8 Hz, 1 H); HO
(1 H-indol-3-yI)ethyl]amide; 7.60, 7.63 AB (J, = 14.8 0 NH
Hz, J2 = 1.9 Hz, 2H); 7.43 (D)-Tryptophanol (1 H); 7.39 d (J = 7.8 Hz, and 1 H); 7.32-7.35 m (2H);
7.15-7.17 m (2H); 7.06 t (J
4-Methoxy-5, 3'- = 7.4 Hz, 1 H); 6.97 t (J =
dimethylbiphenyl-3-carboxylic 7.4 Hz, 1 H); 4.88 t (J = 5.1 acid Hz, 1 H); 4.23-4.31 m(1 H);
3.61 s (3H); 3.45-3.58 m (2H); 3.03, 2.95 AB (J, =
14.3 Hz, J2 = 6.6 Hz, 2H);
2.38 s (3H); 2.31 s (3H).

Product; Method HPLC-MS conditions / Structure Ex. analo-reagents gous to H-NMR (400 MHz) S[ppm]

325 4'-Fluoro-4-methoxy-5,3'- 39 (DMSO-d6): 10.81 s(1 H); - H
~ N
dimethylbiphenyl-3-carboxylic 8.24 d (J = 7.8 Hz, 1 H);
acid [(R)-2-hydroxy- 1 -(1 H- 7.69 d (J = 7.8 Hz, 1 H); HO
indol-3-ylmethyl)ethyl]amide; 7.59-7.60 m (2H); 7.54 d (J H
= 7.4 Hz, 1 H); 7.42-7.45 m (D)-Tryptophanol (1 H); 7.33 d (J = 8.2 Hz, 1 H); 7.18-7.22 m (2H); 7.06 F
and t (J = 7.4 Hz, 1 H); 6.97 t (J
4'-Fluoro-4-methoxy-5, 3' = 7.4 Hz, 1 H); 4.89 t (J =
dimethylbiphenyl-3-carboxylic 5.1 Hz, 1 H); 4.23-4.31 m acid (1 H); 3.61 s (3H); 3.45-3.58 m (2H); 3.03, 2.95 AB (J, _ 14.5 Hz, J2 = 7.1 Hz, 2H);
2.30 s (6H).

326 3',4'-Difluoro-4,5'-dimethoxy-5- 39 (DMSO-d6): 10.80 s(1 H); N
methylbiphenyl-3-carboxylic 8.23 d (J = 8.2 Hz, 1 H);
acid [(R)-2-hydroxy-1-(1 H- 7.69 d (J = 7.8 Hz, 1 H); Ho O H
indol-3-ylmethyl)ethyl]amide; 7.66, 7.63 AB (J, = 14.8 oll Hz, J2 = 1.9 Hz, 2H); 7.32 d~o (D)-Tryptophanol (J = 8.2 Hz, 1 H); 7.18-7.26 F
F
and m (3H); 7.05 t (J = 7.4 Hz, 1 H); 6.96 t (J = 7.4 Hz, 1 H);
3; 4'-Difluoro-4, 5'-dimethoxy-5- 4.88 t (J = 5.1 Hz, 1 H);
methylbiphenyl-3-carboxylic 4.22-4.30 m (1 H); 3.97 s acid (3H); 3.62 s (3H); 3.45-3.58 m (2H); 3.03, 2.95 AB (Jl _ 14.5 Hz, J2 = 6.8 Hz, 2H);
2.31 s (3H).

Product; Method HPLC-MS conditions / Structure Ex. analo- H-NMR (400 MHz) S[ppm]
reagents 9o~s to 327 3'-Hydroxy-4- 39 (DMSO-d6): 10.82 s(1 H); \ N
isopropoxybiphenyl-3- 9.53 s (1 H); 8.50 d (J = 7.8 carboxylic acid [(R)-1- Hz, 1 H); 8.17 s(1 H); 7.71 0 HNH
hydroxymethyl-2-(1 H-indol-3- m (2H); 7.34 d (J = 7.8 Hz, o~
yI)ethyl]amide; 1 H); 7.24 m (2H); 7.16 s HO
(1 H); 7.10 m(4H); 6.75 d (J
(D)-Tryptophanol = 7.8 Hz, 1 H); 4.98 m(1 H);
and 4.79 m(1 H); 4.27 m(1 H);
3.51 m (2H); 3.00 m (2H);
3'-Hydroxy-4- 1.27 m (6H).
isopropoxybiphenyl-3-carboxylic acid 328 3',4',5'-Trimethoxy-4-(3-methyl- 39 (DMSO-d6): 10.78 s(1 H); \~ N
but-2-enyloxy)biphenyl-3- 8.31 d (J = 8.1 Hz, 1 H);
HO
carboxylic acid [(R)-1-hydroxy- 8.09 d (J = 2.6 Hz, 1 H); o NH
methyl-2-(1 H-indol-3- 7.73 dd (J = 2.5 Hz / 8.7 o i~ o"'y yI)ethyl]amide; Hz, 1 H); 7.63 d (J = 7.9 Hz, o 1 H); 7.59 m(2H); 7.31 d (J (D)-Tryptophanol = 7.9 Hz, 1 H); 7.21 d (J =
and 8.9 Hz, 1 H); 7.10 s(1 H);
7.02 m (1 H); 6.93 m (1 H);
3;4;5'-Trimethoxy-4-(3-methyl- 6.81 s(2H); 5.35 m(1H);
but-2-enyloxy)biphenyl-3- 4.87 m(1 H); 4.62 m (2H);
carboxylic acid 4.20 m (1 H); 3.82 s (6H);
3.65 s (3H); 3.42 m (2H);
2.94 m (2H); 1.66 m (6H).
Example 329 3'-Butoxy-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-H
/
HO\ N
O NH
yl)ethyl]amide;

329a) 3-n-Butoxyphenylboronic acid pinacol ester 3-Hydroxyphenylboronic acid pinacol ester (1 g), potassium carbonate (1.57 g) and n-butyl iodide (2.6 ml) were dissolved in DMF (20 ml) and stirred at a bath temperature of 100 C overnight. The cooled reaction mixture was filtered and the filtrate was freed of solvent. The remaining residue was triturated with diisopropyl ether and the residue was filtered off in vacuo and discarded. The mother liquor was concentrated and the crude product was purified by flash chromatography. 710 mg of the title compound were ob-tained. MS (ESI,+): 277 (M+1).

329b) 3'-Butoxy-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide 3-n-Butoxyphenylboronic acid pinacol ester (200 mg), 5-bromo-2-ethoxy-N-[(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]benzamide (201 mg), dihydrogen dichlorobis(di-tert-butylphosphinito-kappa)dipalladate (12 mg) and potassium carbonate (200 mg) in DMF (5 ml) were stirred at 100 C overnight. The mixture was diluted with water and extracted several times with ethyl acetate. The combined organic phases were dried over magnesium sulphate and freed of solvent. Purification by HPLC resulted in the title compound in 32% yield (114 mg).

(DMSO-d6): 10.83 s(1 H); 8.41 d (J = 8.1 Hz, 1 H); 8.16 (J = 2.6 Hz, 1 H);
7.79 dd (J =
2.5 Hz / 8.5 Hz, 1 H); 7.72 d (J = 7.7 Hz, 1 H); 7.36 m (2H); 7.20 m (3H);
7.14 m(1 H);
7.07 m(1 H); 6.98 m(1 H); 6.92 dd (J = 1.9 Hz / 7.9 Hz, 1 H); 4.20 m(1 H);
4.15 m (2H);
4.05 m (2H); 3.50 m (2H); 3.00 m (2H); 1.73 m (2H); 1.45 m (2H); 1.33 m (3H);
9.96 m (3H).

The following compounds were obtained in analogy to the preparation methods de-scribed in detail:

Product; Method ' reagents (400 MHz) S Structure Ex. analogous 9ents to [Pp ]

330 4-Ethoxy-3'- 329 (DMSO-ds): 10.83 s(1 H); \/ N
isopropoxybiphenyl-3- 8.43 d (J = 7.9 Hz, 1 H); ~
HO
carboxylic acid [(R)-1- 8.15 d (J = 2.6 Hz, 1 H); 0 NH
hydroxymethyl-2-(1 H-indol-3- 7.75 dd (J = 2.5 Hz / 8.5 yl)ethyl]amide; Hz, 1 H); 7.71 d (J = 7.7 Hz, 1 H); 7.36 m (2H); 7.18 m 5-Bromo-2-ethoxy-N-((R)-1-(2H);7.11 m(1H);6.98m hydroxymethyl-2-(1 H-indol-3-(1 H); 6.92 m (1 H); 4.72 m yl)ethylJbenzamide (1 H); 4.20 m(1 H); 4.16 m and (2H); 3.51 m (2H); 3.00 m (2H); 1.31 m (9H).
3-Isopropylox yphen ylboronic acid pinacol ester Example 331 N-[(R)-1-Hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-5-(7-methoxybenzofuran-2-yl)-2-H
N

NH O~~
OHO

~ O

propoxybenzamide; O\

331 a) Methyl 5-(7-methoxybenzofuran-2-yl)-2-propoxybenzoate A solution of 7-methoxybenzofuran (500 mg) in THF (3 ml) was cooled to 0 C, and a solution of n-BuLi in hexane (1.6 M, 2.11 ml) was slowly added, whereupon the tem-perature rose to 15 C. The mixture was then stirred at 5 C for 1 hour, zinc chloride (1 M
solution in THF, 3.71 ml), Pd(PPh3)4 (39 mg) and a solution of methyl 5-bromo-propoxybenzoate (1.08 g) in THF (3 ml) were added, and the mixture was then stirred under reflux overnight. The mixture was diluted with ethyl acetate and extracted with aqueous ammonium chloride solution. The combined organic phases were dried over sodium sulphate, and the solvent was distilled off in a rotary evaporator. The title com-pound was obtained after purification by flash chromatography in 11% yield (127 mg).
MS (ESI,+): 341 (M+1).

331 b) 5-(7-Methoxybenzofuran-2-yl)-2-propoxybenzoic acid A solution of methyl 5-(7-methoxybenzofuran-2-yl)-2-propoxybenzoate (120 mg) in methanol (5 ml) was mixed with potassium hydroxide solution (10% strength in metha-nol, 2 ml) and stirred at 50 C for 5 hours. The mixture was concentrated and extracted with MTBE. The aqueous phase was acidified with 1 N HCI and again extracted with MTBE, and the combined organic phases were freed of solvent. The title compound was employed without further purification in the next stage (yield 97%, 112 mg). MS
(ESI,+): 327 (M+1).

331 c) N-((R)-1-Hydroxymethyl-2-(1 H-indol-3-yl)ethyl]-5-(7-methoxybenzofuran-2-yl)-2-propoxybenzamide 5-(7-Methoxybenzofuran-2-yl)-2-propoxybenzoic acid (85 mg) were reacted with (D)-tryptophanol (59 mg) in analogy to general method 113b. The title compound was ob-tained in 32% yield (41 mg).

(DMSO-d6): 10.79 s(1 H); 8.37 d (J = 2.5 Hz, 1 H); 8.32 d (J = 8.3 Hz, 1 H);
7.96 dd (J =
2.5 Hz / 8.6 Hz, 1 H); 7.68 d (J = 7.8 Hz, 1 H); 7.30 m (2H); 7.24 d (J = 8.8 Hz, 1 H); 7.15 m (3H); 7.03 m(1 H); 6.95 m(1 H); 6.90 m(1 H); 4.91 m(1 H); 4.26 m(1 H); 4.06 m (2H);
3.95 s (3H); 3.45 m (2H); 2.96 m (2H); 1.66 m (2H); 0.91 m(3H).

Example 332 6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-2-(6-chloro-I o' o O N
I
O
HN O

OH
N
H
1 H-indol-3-yl)-1-hydroxymethylethyl]amide; cil Preswell 0.2 mmol of unloaded Wang resin in 1.5 ml of DMF for 15 min. Then 6 eq of Fmoc-amino acid (R)-3-(6-chloro-1 H-indol-3-yl)-2-(9H-fluoren-9-ylmethoxycarbonyl-amino)propionic acid (0.3M in NMP); 10 eq of pyridine (dried) and 6 eq of 2,4-dichlorobenzoyl chloride (dried) are added and coupled to the resin by shaking for 20 h.
After washing 5x with 2 ml of DMF, capping is carried out with 1.5 ml of acetic ahydride 10% in DMF for 5 minutes, followed by washing 5 x with 2 ml of DMF.
Deprotection with 2 ml of 20% PIP in DMF (1 x 5 minutes, 1 x 15 minutes) is followed by washing a further 5 x with 2 ml of NMP.

6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid is coupled on by add-ing 2 eq of 0.3M acid, 6 eq of N-methylmorpholine 3M in NMP+ 2.5% DMAP and 3 eq of HATU 0.3M in NMP (double coupling 2 x 4h). This is followed by washing 3 x with 2 ml of NMP and 5 x with 2 ml of THF. For the reductive elimination, 2 ml of DIBAL 1 M in THF are added at 0 C under N2 and stirred for 12 h. Warming to room temperature is followed by filtration and washing with 4 x 1.5 ml of THF.

HPLC-MS: Column Purospher Star RP C18 4.6x125 5pm; detection wavelength 214 nm; flow rate 1 ml/min; eluents A: 0.1 % TFA in H20, B 0.1 % TFA in ACN;
gradient in each case based on B: 5% to 95% (10') to 95% (2') to 5% (0.5') to 5% (2.5') Molecular peak (ESI, M+1): 577 Retention time: 7.96 min.

The following compounds were obtained in analogy to the preparation methods de-scribed in detail:

Product; Method HPLC-MS conditions I Structure Ex. eagents yousto 'H-NMR (400 MHz) S[ppm]

333 6-Methoxy-2-(3,4,5- 318 Column Purospher Star o trimethoxyphenyl)quinoline-4- RP C18 4.6x125 5Nm; o carboxylic acid [(R)-1- detection wavelength o ~ N Nzt hydroxymethyl-2-(2-methyl- 214 nm; flow rate 1 o ml/min; eluents A: 0.1 % HN 0 1 H-indol-3-yl)ethyl]amide;
TFA in H20, B 0.1 % TFA H
(R)-2-(9H-Fluoren-9- oH
in ACN; gradient in each ylmethoxycarbonylamino)-3- ~ N
case based on B: 5% to - H
(2-methyl-1H-indol-3-yl)- 95% (10') to 95% (2) to propionic acid o o 5/0(0.5')to5/o(2.5) and Molecular peak (ESI, 6-Methoxy-2-(3, 4, 5- M+1): 557.6 trimethoxyphenyl) quinoline-4-Retention time: 7.61 min.
carboxylic acid 334 6-Methoxy-2-(3,4,5- I (DMSO-d6): 10.65 s H
trimethoxyphenyl)quinoline-4- (1 H); 8.64 d (J = 8.6 Hz, ~~~
carboxylic acid [1- 1 H); 7.99 d (J = 9.0 Hz, Ho O NH
hydroxymethyl-2-(6-methyl- 1 H); 7.96 s(1 H); 7.51 d o , 1 H-indol-3-yl)ethyl]amide; (J = 8.5 Hz, 1 H); 7.49 s - N
(2H); 7.43 s(1 H); 7.40 s -(2-RS)-Amino-3-(6-methyl- (1 H); 7.10 d (J - 4.3 Hz, 0 1H-indol-3-yl)-propan-1-ol 2H); 6.76 d (J - 7.8 Hz, and 1 H); 4.90 t (J = 5.4 Hz, 1 H); 4.38 m(1 H); 3.92 s 6-Methoxy-2-(3,4,5- (6H); 3.73 s(3H); 3.72 s trimethoxyphenyl)quinoline-4- (3H); 3.59 t (J = 5.2 Hz, carboxylic acid 2H); 2.99 dd (J = 14.3 Hz / 8.1 Hz, 1 H); 2.92 dd (J
= 14.3 Hz / 5.4 Hz, 1 H);
2.35 s (3H).

Example 335 N-[ (R)-1-(Hydroxymethyl)-2-(1-ethyl) -1H-indol-3-yl) ethyl]-6-methoxy-2-(3-I
N

HO
H
O NH

O~
.0*0 N

methoxyphenyl)quinoline-4-carboxamide;
335a) Methyl (R)-2-tert-butoxycarbonylamino-3-(1 H-indol-3yl)-propionate 15.72 mmol (2.18 ml) of triethylamine were added dropwise to a solution of 3.93 mmol (1g) of D-tryptophan methyl ester hydrochloride in 35 ml of dichloromethane with stirring and then 7.85 mmol (1.71 g) of di-tert-butyl dicarbonate, dissolved in 5 ml of dichloromethane, were added, followed by 0.39 mmol (48 mg) of dimethylaminopyridine. The mixture was stirred at room temperature for about 1.5 h.
Then 25 ml of 10% strength sodium bisulphite solution were added to the reaction mix-ture and stirred for 15 minutes. After phase separation, the aqueous phase was ex-tracted with dichloromethane. The resulting organic phase was dried over magnesium sulphate, filtered and concentrated in vacuo. Purification by chromatography on silica gel with the eluent cyclohexane/ethyl acetate affords 800 mg of the compound as a white solid.

'H-NMR (400 MHz,DMSO-d6):6 [ppm] = 10.84 s(1 H, NH); 7.45 d (J = 7.8 Hz, 1 H, aryl) 7.32 d (1 H, aryl); 7.14 s (1 H, aryl); 7.05 t (J = 7.4 Hz, 1 H, aryl); 6.97 t (J = 7.9 Hz, 1 H, aryl); 4.20 m(1 H, CH); 3.59 s (3H, OCH3); 3.08 dd (J = 14.4 Hz / 5.8 Hz, 1 H, CH); 3.00 dd (J = 14.4 Hz / 8.2 Hz, 1 H, CH); 1.33 s (9H, CH3).

335b) Methyl (R)-2-tert-butoxycarbonylamino-3-(1-ethyl-1 H-indol-3-yl)propionate 3.27 mmol (183 mg) of potassium hydroxid powder were added in portions to a stirred solution of 2.51 mmol (800 mg) of the protected amino acid prepared in a), in 8 ml of DMSO, slightly cooling in water. This mixture was stirred for 5 minutes and then 3.27 mmol (0.26 ml) of ethyl iodide, dissolved in 2 ml of DMSO, were added dropwise. Stir-ring was continued at room temperature for 2 hours, and the reaction mixture was then added to saturated aqueous ammonium chloride solution and extracted with ethyl ace-tate. The resulting organic phase was dried over magnesium sulphate, filtered and con-centrated in vacuo with the addition of toluene. 871 mg of the target compound are obtained.

'H-NMR (400 MHz,DMSO-ds):b [ppm] = 7.48 d (J = 7.8 Hz, 1 H, aryl); 7.41 d (J =
7.8 Hz, 1 H, aryl); 7.23 d(J = 7.4 Hz, 1 H, aryl); 7.11 t(J = 7.6 Hz, 1 H, aryl);
7.00 t(J = 7.8 Hz, 1 H, aryl); 4.20 m(1 H, CH); 4.19 q (J = 7.0 Hz, 2H, CH2); 3.07 dd (14.3 Hz / 5.3 Hz, 1 H, CH); 3.01 dd (J = 14.3 Hz / 8.2 Hz, 1 H, CH); 1.33 s (9H, CH3); 1.3 t (J
= 7.0 Hz, 3H, CH3).

335c) Methyl (R)-2-amino-3-(1-ethyl-1 H-indol-3-yl)propionate 2.48 mmol (860 mg) of the compound prepared in b) were dissolved in 10 ml of di-chloromethane and then 24.8 mmol (1.91 ml) of trifluoroacetic acid were added drop-wise at room temperature. After 1 hour, 20 ml of saturated sodium bicarbonate solution were cautiously added dropwise to the mixture until the neutral point was reached. After phase separation, the aqueous phase was extracted with dichloromethane. The result-ing organic phase was dried over magnesium sulphate, filtered and concentrated in vacuo. 588 mg of the product are obtained.

1H-NMR (400 MHz,DMSO-d6): b[ppm] = 7.47 d (J = 7.8 Hz, 1 H, aryl); 7.39 d (J =
7.8 Hz, 1 H, aryl); 7.15 s (1 H, aryl); 7.09 t (J = 7.5 Hz, 1 H, aryl); 6.98 t (J
= 7.8 Hz, 1 H, aryl);
4.14 q (J = 7.0 Hz, 2H, CH2); 3.57 m(1 H, CH); 3.54 s (3H, OCH3); 2.98 dd (J =
14.2 Hz / 5.4 Hz, 1 H, CH); 2.93 dd (J = 14.2 Hz / 8.4 Hz, 1 H, CH); 1.79 s(2H, NH2);
1.31 t (J
=
7.0 Hz, 3H, CH3).

N-[ (R)-1-(Methoxycarbonyl)-2-(1-ethyl) -1H-indol-3-yl) ethyl]-6-methoxy-2-(3-methoxyphenyl)quinoline-4-carboxamide The title compound was prepared in analogy to general method le.

'H-NMR (400 MHz, DMSO-ds): b[ppm] = 9.42 d (7.2 Hz, 1 H, NH); 8.22 d (J = 9.0 Hz, 1 H, aryl); 8.05 m(3H, aryl); 7.97 s (1 H, aryl); 7.80 d (J = 8.6 Hz, 1 H, aryl); 7.60 d (J
=
7.8 Hz, 1 H, aryl); 7.45 d (J = 8.2 Hz, 1 H, aryl); 7.37 t (J = 8.6 Hz, 1 H, aryl); 7.32 s (1 H, aryl); 7.13 t(J = 7.8 Hz, 1 H, aryl); 7.01 t(J = 7.5 Hz, 1 H, aryl); 4.80 m(1 H, CH); 4.14 q (J = 7.0 Hz, 2H, CH2); 3.96 s (3H, OCH3); 3.72 s (3H, OCH3); 3.30 dd (J = 14.2 Hz / 5.1 Hz, 1 H, CH); 3.24 dd (J = 14.2 Hz / 8.2 Hz, 1 H, CH); 1.29 t(J = 7.0 Hz, 3H, CH3).

335d) N-[ (R)-1-(Hydroxymethyl)-2-(1-ethyl)-1H-indol-3-yl) ethyl]-6-methoxy-2-(3-methoxyphenyl)quinoline-4-carboxamide 0.19 mmol (94 NI) of 2M lithium borohydride solution was added dropwise to a solution of 0.19 mmol (115mg) of the carboxamide (prepared in analogy to 1e) in 3 ml of THF at 0 C. This mixture is then stirred at room temperature for 4-6 hours. It was then neutral-ized at 0 C with 1 N hydrochloric acid and, after addition of water, extracted with ethyl acetate. The organic phase was dried over magnesium sulphate, filtered and concen-trated in vacuo. Purification by chromatography on silica gel with the eluent cyclohex-ane/acetone affords 36.9 mg of pale yellow foam.

'H-NMR (400 MHz,DMSO-ds): b[ppm] = 8.76 d (J = 7.7 Hz, 1 H), 8.20 d (J = 9.0 Hz, 1 H, aryl) 8.13 m(2H, aryl); 8.06 s(1 H, aryl); 8.01 s(1 H, aryl); 7.76 d (J =
7.4 Hz, 1 H, aryl); 7.65 d (J = 7.8 Hz, 1 H, aryl); 7.40 t (J = 7.4 Hz, 2H, aryl); 7.24 s (1 H, aryl); 7.10 t (J = 7.8 Hz, 1 H, aryl); 6.97 t (J = 7.4 Hz, 1 H, aryl); 4.92 t (J = 5.4 Hz, 1 H, OH); 4.36 m (1 H, CH); 4.14 q (J = 7.0 Hz, 2H, CH2); 3.96 s(3H, OCH3); 3.60 m(2H, OCHZ);
3.05 dd (J = 14.3 Hz / 5.6 Hz, 1 H, CH); 2.97 dd (J = 14.3 Hz / 8.2 Hz, 1 H, CH); 1.29 t (J = 7.0 Hz, 3H, CH3).

The following compounds were obtained in analogy to the preparation methods de-scribed in detail:

Product; Method Structure Ex. reagents gousio 'H-NMR (400 MHz) S[ppm]

336 N-[ (R)-1-(Hydroxymethyl)-2-(1- 335 (DMSO-d6): 8.66 d (J = 8.5 _ propyl-1 H-indol-3-yl) ethyl]-6- Hz, 1 H, NH); 8.00 d (J = 8.6 (N ~ i ~
methoxy-2-(3,4,5- Hz, 1 H, aryl); 7.98 s(1 H, HO
trimethoxyphenyl)quinoline-4- aryl); 7.66 d (J = 8.4Hz, 1 H, o NH
carboxamide; aryl); 7.50s (2s, aryl); 7.43 m o q N (3H, aryl); 7.22 s(1 H, aryl); -o N-[ (R)- 1 -(Methoxycarbonyl)-2- 7.09 t (J
= 7.5 Hz, 1 H, aryl); ~O

(1-propyl-1 H-indol-3-yl) ethyl]- 6.97 t (J = 7.4 Hz, 1 H, aryl);
6-methoxy-2-(3, 4, 5- 4.91 t (J = 5.3 Hz, 1 H, OH);
trimethoxyphenyl)quinoline-4- 4.38 m (1 H, CH) 4.05 t (J =
carboxamide 7.0 Hz, 2H, CH2); 3.92 s (6H, OCH3); 3.75 (6H, OCH3);
3.60 m (2H, OCH2); 3.03 dd (J = 14.3 Hz / 5.7 Hz, 1 H, CH); 2.97 dd (J = 14.3 Hz /
8.2 Hz, 1H, CH); 1.68 m(2H, CHZ); 0.75 t (J = 7.0 Hz, 3H, CH3).

337 N-[ (R)-1-(Hydroxymethyl)-2-(1- 335 (DMSO-d6): 8.63 d (J = 8.6 ethyl)-1 H-indol-3-yl) ethyl]-2- Hz, 1 H, NH); 7.99 m(3H, N
(3,5-difluoro-4-methoxyphenyl)- aryl), 7.95 s(1 H, aryl); 7.67 d HO H

6-methoxyquinoline-4- (J = 7.8 Hz, 1 H, aryl), 7.43 m carboxamide; (3H, aryl); 7.25 s(1 H, aryl), F N
I~
7.11 t (J = 7.4 Hz, 1 H, aryl);
N-[ (R)-1-(Methoxycarbony!)-2- F
6.98 t (J = 7.4 Hz, 1 H, aryl);
(1-ethyl)-1 H-indol-3-yl) ethyl]-2- 4.91 t (J = 5.5 Hz, 1 H, OH);
(3,5-difluoro-4-methoxyphenyl)- 4,37 m(1 H, CH); 4.14 q(J -6-methoxyquinoline-4- 7.0 Hz, 2H, CH2); 4.03 s (3H, carboxamide OCH3); 3.60 m (2H, OCHZ);

Product; Method Structure Ex. reagents 9o~sto 'H-NMR (400 MHz) S[ppm]
3.03 dd (J = 14.2 Hz / 5.3 Hz, 1 H, CH); 2.96 dd (J =
14.2 Hz / 8.3 Hz, 1 H, CH);
1.29 t (J = 7.0 Hz, 3H, CH3).

338 N-[ (R)-1-(Hydroxymethyl)-2-(1- 335 (DMSO-d6): 8.66 d (J = 8.3 isopropyl-1 H-indol-3-yl) ethyl]- Hz, 1 H, NH); 8.01 d (J = 7.7 6-methoxy-2 (3- Hz, 1 H, aryl); 7.90 s(1 H, Ho NH
methoxyphenyl)-quinoline-4- aryl); 7.77 s (1 H, aryl); 7.74 d / 0, carboxamide; (J = 7.9 Hz, 1 H, aryl): 7.66 d (J = 7.8 Hz, 1 H, aryl); 7.46 m N-[ (R)- 1 -(Methoxycarbonyl)-2- (4H, aryl), 7.33 s (1 H,aryl);
(1-isopropyl -1H-indol-3-yl) 7.08 m (2H, aryl); 6.99 t (J
-ethyl]-6-methoxy-2 (3-7.0 Hz, 1 H, aryl); 4.92 t (J
=
methoxyphenyl)-quinoline-4- 5.5 Hz, 1 H, OH); 4.68 m(1 H, carboxamide CH), 4.38 m(1 H, CH), 3.87 s (3H, OCH3); 3.75 s (3H, OCH3); 3.60 m (2H, OCH2);
3.04 dd (J = 14.3 Hz / 5.5 Hz, 1 H, CH); 2.96 dd (J =
14.3 Hz / 8.3 Hz, 1 H, CH);
1.37 (J = 7.0 Hz, 6H, CH3).

339 N-[ (R)-1-(Hydroxymethyl)-2-(1- 335 (DMSO-d6): 8.64 dd (J = 8.5 isopropyl-1 H-indol-3-yl) ethyl]- Hz, 1 H, NH); 8.01 d (J = 7.7 N~
2-(3,5-difluoro-4- Hz, 1 H, aryl); 8.00 s (1 H, Ho methoxyphenyl)-6- aryl); 7.96 d (J = 6.0 Hz, 2H, O H
0, methoxyquinoline-4- aryl); 7.66 d (J = 7.8 Hz, 1 H, F ~ I N /
carboxamide; aryl); 7.49 s(1 H, aryl); 7.45 o I~
m(2H, aryl); 7.34 s(1 H, aryl) F
N-[ (R)-1-(Methoxycarbonyl)-2- 7.10 t(J - 7.4 Hz, 1 H, aryl);
(1-isopropyl -1 H-indol-3-yl) e- 7.00 t (J = 7.9 Hz, 1 H, aryl);
thyl]-2-(3, 5-difluoro-4- 4.92 t (J = 5.4 Hz, 1 H, OH);
methoxyphenyl)-6- 4.69 m(1 H, CH); 4.39 m methoxyquinoline-4-Product; Method ~ Structure Ex. reagents 9o~sto H-NMR (400 MHz) S[ppm]
carboxamide (1 H, CH); 4.03 s (3H, OCH3);
3.74 s (3H, OCH3); 3.60 m (2H, OCH2); 3.04 dd (J =
14.4 Hz / 5.6 Hz, 1 H, CH);
2.96 dd (J = 14.4 Hz / 8.4 Hz, 1 H, CH); 1.37 t (J = 7.0 Hz, 6H, CH3).

340 N-[ (R)-1-(Hydroxymethyl)-2-(1- 335 (DMSO-d6): 8.66 d(J= 8.7 isopropyl-1 H-indol-3-yl) ethyl]- Hz, 1 H, NH); 8.01 d (J = 7.6 N
6-methoxy-2-(3,4,5- Hz, 1 H, aryl); 7.99 s (1 H, Ho trimethoxyphenyl)quinoline-4- aryl); 7.66 d (J = 8.2 Hz, 1 H, o, carboxamide; aryl); 7.50 s (2H, aryl); 7.46 'o N
m (3H, aryl); 7.33 s(1 H, a- 'o ;
N-[ (R)-1-(Methoxycarbonyl)-2-ryl); 7.10 t (J = 7.7 Hz, 1 H, (1-isopropyl-1 H-indol-3-yl) aryl); 6.98 t (J = 7.6 Hz); 1 H, ethylJ-6-methoxy-2-(3, 4, 5-aryl); 4.91 t (J = 5.4 Hz, 1 H, trimethox yph en yl) quinoline-4-OH); 4.68 m(1 H, CH); 4.41 carboxamide m(1 H, CH); 3.91 s(6H, OCH3); 3.75 s (3H, OCH3);
3.73 s (3H, OCH3); 3.61 m (2H, OCHZ); 3.03 dd (J =
14.4 Hz / 5.7 Hz, 1 H, CH);
2.97 dd (J = 14.4 Hz / 8.2 Hz, 1 H, CH); 1.36 t(J = 6.3 Hz, 6H, CH3).

341 N-[ (R)-1-(Hydroxymethyl)-2-(1- 335 (DMSO-d6): 8.76 d (J = 7.7 ethyl)-1 H-indol-3-yl) ethyl]-2-(3- Hz, 1 H, NH). 8.20 d (J = 9.0 fluoro-4-methoxyphenyl)-6- Hz, 1 H, aryl); 8.13 m (2H, HO

trifluoromethoxyquinoline-4- aryl), 8.06 s (1H,aryl); 8.01 s o F
X
carboxamide (1 H, aryl), 7.76 d (J = 7.4 Hz, F N F F
1 H, aryl); 7.65 d (J = 7.8 Hz, N-[ (R)-1-(Methoxycarbonyl)-2-1 H, aryl); 7.40 t (J = 7.4 Hz, (1-ethyl)-1 H-indol-3-yl) ethyl]-2-Product; Method ~ Structure Ex. ' analo- H-NMR (400 MHz) S[ppm]
reagents gousto (3-fluoro-4-methoxyphenyl)-6- 2H, aryl); 7.24 s (1 H, aryl);
trifluoromethoxyquinoline-4- 7.10 t (J = 7.8 Hz, 1 H, aryl);
carboxamide 6.97 t (J = 7.4 Hz, 1 H, aryl);
4.92 t (J = 5.4 Hz, 1 H, OH);
4.36m(1H,CH);4.14q(J=
7.0 Hz, 2H, CHZ); 3.96 s (3H, OCH3); 3.60 m (2H, OCH2);
3.05 dd (J = 14.3 Hz / 5.6 Hz, 1 H,CH); 2.97 dd (J =
14.3 Hz / 8.2 Hz, 1 H, CH);
1.29 t (J = 7.0 Hz, 3H, CH3).

342 N-[ (R)-1-(Hydroxymethyl)-2-(1- 335 (DMSO-d6): 8.86 d (J = 8.2 ethyl)-1 H-indol-3-yl) ethyl]-2-(7- Hz, 1 H, NH); 8.25 d (J = 9.4 methoxybenzofuran-2-yl)-6- Hz, 1 H, aryl); 8.11 s(1 H, "o H
trifluoromethoxyquinoline-4- aryl); 7.96 s(1 H, aryl); 7.83 F
\ . ~ / F F
carboxamide; m (2H, aryl); 7.66 d (J = 7.8 o N
Hz, 1 H, aryl); 7.42 d (J = 8.2 p N-[ (R)-1-(Methoxycarbonyl)-2-Hz, 1 H, aryl); 7.37 d (J = 7.8 (1-ethyl)-1H-indol-3-yl) ethylJ-2-Hz, 1 H, aryl); 7.30 t (J = 7.7 (7-methoxybenzofuran-2-yl)-6- Hz, 2H, aryl); 7.25 s(1H, trifluoromethoxyquinoline-4-aryl); 7.09 m (2H, aryl); 7.00 carboxamide t (J = 7.1 Hz, 1 H, aryl); 4.95 t (J = 5.4 Hz, 1 H, OH); 4.38 m (1 H, CH); 4.16 q (J = 7.1 Hz, 2H, CHZ); 4.02 s (3H, OCH3);
3.61 m (2H, OCHZ); 3.05 dd (J = 14.2 Hz / 5.3 Hz, 1 H,CH); 2.94 dd (J = 14.2 Hz / 8.1 Hz, 1 H, CH); 1.29 t(J =
7.1 Hz, 3H, CH3).

Product; Method Structure Ex. reagents 9o~sto 'H-NMR (400 MHz) S[ppm]
343 N-[ (R)-1-(Hydroxymethyl)-2-(1- 335 (DMSO-d6): 8.76 d (J = 8.6 isopropyl -1 H-indol-3-yl) ethyl]- Hz, 1 H, NH); 8.20 d (J = 9.4 N
2-(3-fluoro-4-methoxyphenyl)-6- Hz, 1 H, aryl); 8.06 m (4H, Ho trifluoromethoxyquinoline-4- aryl); 7.77 d (J = 9.0 Hz, 1 H, 0 F
carboxamide; aryl); 7.65 d (J = 8.2 Hz, 1 H, F N

aryl); 7.40 d (J = 8.2 Hz, 1 H, N-[ (R)-1-(Methoxycarbonyl)-2-aryl); 7.37d (J = 9.0 Hz, 1 H, (1-isopropyl -1 H-indol-3-yl) e-aryl); 7.33 s(1 H, aryl), 7.09 t thyl]-2-(3-fluoro-4-(J = 7.4 Hz, 1 H, aryl), 6.97 t methoxyphenyl)-6-(J = 7.4 Hz, 1 H, aryl); 4.93 t trifluoromethoxyquinoline-4- (J = 5.5 Hz, 1 H, OH); 4.68 m carboxamide (1 H,CH); 4.37 m(1 H, CH);

3.96 s (3H, OCH3); 3.60 m (2H, OCH2); 3.06 dd (J =
14.4 Hz / 5.6 Hz, 1 H, CH);
2.94 dd (J = 14.4 Hz / 8.1 Hz, 1 H, CH); 1.37 t(J =
7.0Hz, 6H, CH3).

344 N-[ (R)-1-(Hydroxymethyl)-2-(1- 335 (DMSO-d6): 8.86 d (J = 8.4 isopropyl-1 H-indol-3-yl) ethyl]- Hz, 1 H, NH); 8.25 d (J = 9.4 2-(7-methoxybenzofuran-2-yl)- Hz, 1 H, aryl); 8.11 s(1 H, HO H H
6-trifluoromethoxyquinoline-4- aryl); 7.98 s(1 H, aryl); 7.82 i >CF
N
carboxamide; m (2H, aryl); 7.65 d (J = 7.8 o Hz, 1 H, aryl); 7.44 d (J = 8.2 N-( (R)-1-(Methoxycarbonyl)-2-Hz, 1 H, aryl); 7.33 m (3H, (1-isopropyl-1 H-indol-3-yl) e-aryl); 7.29 t (J = 8.3 Hz, 1 H, thyl]-2-(7-methoxybenzofuran-aryl); 7.09 m (2H, aryl); 7.00 2-yl)-6- t (J = 7.4 Hz, 1 H, aryl); 4.95 t trifluoromethoxyquinoline-4- (J - 5.5 Hz, 1 H, OH); 4.70 m carboxamide (1 H, CH); 4.41 m(1 H, CH);

4.01 s (3H, OCH3); 3.61 m (2H, OCH2); 3.05 dd (J =
14.3Hz / 5.5 Hz, 1 H, CH);

Product; Method Structure Ex. reagents gousto 'H-NMR (400 MHz) S[ppm]
2.94 dd (J = 14.3 Hz / 8.2 Hz, 1 H, CH); 1.40 d(J = 6.3 Hz, 3H, CH3); 1.37 d (J = 6.7 Hz, 3H, CH3).

345 N-[ (R)-1-(Hydroxymethyl)-2-(1- 335 (DMSO-d6): 8.65 d(J= 8.6 n hexyl-1 H-indol-3-yl) ethyl]-6- Hz, 1 H, NH); 8.00 d (J = 7.5 methoxy-2-(3,4,5- Hz, 1 H, aryl); 7.99 s(1 H, N~ i trimethoxyphenyl)quinoline-4- aryl); 7.65 d (J = 8.3 Hz, 1 H, Ho carboxamide; aryl); 7.50 s (2H, aryl), 7.45 O NH
o, m(3H, aryl); 7.22 s(1 H, a- -o N
N-((R)-1-(Methoxycarbonyl)-2- ,o ~o (1-n hexyl-1 H-indol-3-yl) ethylJ- ryl); aryl); 7.09 t (J = 7.6 Hz, 1 H, 6.99 t (J = 7.5 Hz, 1 H, 6-methoxy-2-(3,4,5- aryl); 4.91 t (J = 5.3 Hz, 1 H, trimethoxyphenyl) quinoline-4-OH); 4.39 m (1 H, CH); 4.06 t carboxamide (J = 7.1 Hz, 2H, CH2); 3.91 s (6H, OCH3); 3.75 s (3H, OCH3); 3.73 s (3H, OCH3);
3.61 t (J = 5.5 Hz, 2H, OCH2); 3.02 dd (J = 14.3 Hz / 5.5 Hz, 1 H, CH); 2.98 dd (J
= 14.3 Hz / 8,1 Hz, 1 H, CH), 1.62 m (2H, CH2); 1.10 m (6H, CHZ); 0.73 m (3H, CH3).

346 N-[ (R)-1-(Hydroxymethyl)-2-(1- 335 (DMSO-d6): 8.42 d (J = 7.8 ethyl)-1 H-indol-3-yl) ethyl]-4- Hz, 1 H, NH); 8.13 s(1 H, a-ethoxy-3'-methoxybiphenyl-3- ryl); 7.70 d (J = 8.5 Hz, 1 H, Ho H
carboxamide; aryl); 7.69 d (J = 7.8 Hz, 1 H, O NH
CH); 7.40 m (2H, aryl); 7.29 1~
N-[ (R)-1-(Methoxycarbonyl)-2- m (3H, aryl); 7.12 m (2H, (1-ethyl) -1H-indol-3-yl) ethylJ- aryl), 6.99 t (J - 7.4 Hz, 1 H, 4-ethoxy-3'-methoxybiphenyl-3-aryl); 6.92 d (J = 6.3 Hz, 1 H, carboxamide aryl); 4.94 t (J = 5.5 Hz, 1 H, Product; Method Structure Ex. reagents go~sto 'H-NMR (400 MHz) S[ppm]
OH); 4.24 m(1 H, CH); 4.14 q (J = 7.0 Hz, 2H, CH2); 3.82 s (3H, OCH3); 3.50m (2H, OCH2); 2.98 m (2H, CH2);
1.30 m (6H, CH3);

347 N-[ (R)-1-(Hydroxymethyl)-2-(1- 335 (DMSO-d6): 8.40 d (J = 8.2 isopropyl) -1 H-indol-3-yl) ethyl]- Hz, 1 H, NH); 8.13 s(1 H, a- N~
4-ethoxy-3'-methoxybiphenyl)- ryl); 7.76 d (J = 8.5 Hz, 1 H, HO
3-carboxamide; aryl); 7.70 d (J = 7.8 Hz, 1 H, 0 NH
aryl); 7.43 d (J = 8.2 Hz, 1 H, o N-[ (R)-1-(Methoxycarbonyl)-2- aryl); 7.36 t (J = 7.8 Hz, 1 H, (1-isopropyl) -1 H-indol-3-yl) aryl); 7.29 s(1 H, aryl); 7.19 t ethylJ-4-ethoxy-3' (J = 8.2 Hz, 2H, aryl); 7.13 s methoxybiphenyl)-3-(1 H, aryl); 7.10 t (J = 7.8 Hz, carboxamide 1 H, aryl); 6.98 t (J = 7.4 Hz, 1 H, aryl); 6.93 d (J = 7.4 Hz, 1 H, aryl); 4.94 s (J = 5.4 Hz, 1 H, OH); 4.76 m(1 H, CH) 4.24 m(1 H, CH); 4.14 q (J
=
7.0 Hz, 2H, CH2); 3.82 s (3H, OCH3); 3.47 m (2H, OCHZ);
2.98 m (2H, CH2); 1.40 t (J
=
6.6 Hz, 6H, CH3); 1.31 t (J
=
7.0 Hz; 3H, CH3).

Product; Method Structure Ex. reagents 9oUSto 'H-NMR (400 MHz) S[ppm]

348 N-[(R)-2-(1-Ethyl-1H-indol-3-yl)- 39 (CDCI3): 7.73 s(1H); 7.70 d ~~
1-(hydroxymethyl)ethyl]-3'- (J = 8.0 Hz, 1 H); 7.61 d (J =
fluoro-4'-methoxy[1,1'- 7.6 Hz, 1 H); 7.56 d (J = 7.8 J= 7.8 Hz HO NH
biphenyl]-3-carboxamide; Hz, 1 H); 7.41 dd ( / 7.6 Hz, 1 H); 7.35 d (J = 8.0 1-Ethyl-L-tryptophanol and Hz, 1 H); 7.28-7.20 m (3H);

3'-Fluoro-4' methoxy[1,1' 7.12 dd (J = 8.0 Hz / 7.0 Hz, F~ I
biphenyl]-3-carboxylic acid 1 H); 7.04 s(1 H); 7.02 dd (J
.
= 8.0 Hz / 7.0 Hz, 1 H); 6.51 d (J = 6.6 Hz, 1 H); 4.48 m (1 H); 4.14 q(J = 7.3 Hz, 2H);
3.94 s (3H); 3.85 m(1 H);
3.80 m(1 H); 3.18 dd (J =
14.7 Hz / 7.1 Hz, 1 H); 3.15 dd (J = 14.7 Hz / 6.6 Hz, 1 H); 1.42 t(J = 7.3 Hz, 3H).

349 3'-Fluoro-N-[(R)-1- 39 (DMSO-d6): 8.28 d(J= 8.3 /~
(hydroxymethyl)-2-(1-propyl- Hz, 1 H); 8.03 s(1 H); 7.78 d 1 H-indol-3-yl)ethyl]-4'- (J = 7.8 Hz, 1 H); 7.76 d (J =
HO H
methoxy[1,1'-biphenyl]-3- 7.6 Hz, 1 H); 7.68 d (J = 8.0 N
carboxamide; Hz, 1 H); 7.65 dd (J = 13.1 Hz / 2.3 Hz, 1 H); 7.53 d(J =
1-Propyl-L-tryptophanol and 8.8 Hz, 1 H); 7.49 dd (J = 7.8 F
O
3'-Fluoro-4' methoxy[l,1' Hz / 7.6 Hz, 1 H); 7.28 d (J =
biphenyl]-3-carboxylic acid 8.0 Hz, 1 H); 7.28 dd (J = 8.8 Hz / 8.8 Hz, 1 H); 7.17 s(1 H);
7.09 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 6.98 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 4.82 m(1 H); 4.25 m (1 H); 4.03 t (J = 6.8 Hz, 2H);
3.90 s (3H); 3.55 m (1H);
3.51 m (1 H); 3.04 dd (J =
14.2 Hz / 5.8 Hz, 1 H); 2.93 Product; Method Structure Ex. reagents 9o~sto 'H-NMR (400 MHz) S[ppm]
dd (J = 14.2 Hz / 7.6 Hz, 1 H); 1.66 m (2H); 0.71 t (J
=
7.4 Hz, 3H).

350 N-[(R)-2-(1-Butyl-1 H-indol-3-yl)- 39 (DMSO-d6): 8.27 d (J = 8.3 ~~
1-(hydroxymethyl)ethyl]-3'- Hz, 1 H); 8.04 s(1 H); 7.78 d ~
~ N
fluoro-4'-methoxy[1,1'- (J = 7.8 Hz, 1 H); 7.76 d(J =
HO N
biphenyl]-3-carboxamide; 7.8 Hz, 1 H); 7.67 d (J = 8.0 Hz, 1 H); 7.65 dd (J = 12.9 0 ~ I
1-Butyl-L-tryptophanol and Hz / 2.3 Hz, 1 H); 7.53 d (J
= ~ I
3'-Fluoro-4' methoxy(1,1' 8.8 Hz, 1 H); 7.49 dd (J = 7.8 F
biphenyl]-3-carboxylic acid Hz / 7.8 Hz, 1 H); 7.37 d(J =
8.0 Hz, 1 H); 7.28 dd (J = 8.8 Hz / 8.8 Hz, 1 H); 7.16 s(1 H);
7.09 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 6.99 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 4.82 m(1 H); 4.25 m (1 H); 4.06 t (J = 6.9 Hz, 2H);
3.90 s (3H); 3.56 m(1 H);
3.51 m (1 H); 3.04 dd (J =
14.4 Hz / 5.8 Hz, 1 H); 2.93 dd (J = 14.4 Hz / 7.8 Hz, 1 H); 1.61 m(2H); 1.11 m (2H); 0.72 t (J = 7.3 Hz, 3H).

351 3'-Fluoro-N-[(R)-l- 39 (DMSO-d6): 8.27 d (J = 8.3 ~~
(hydroxymethyl)-2-[1-(3- Hz, 1 H); 8.04 s(1 H); 7.78 d N
methylbutyl)-1 H-indol-3- (J = 7.8 Hz, 1 H); 7.76 d(J = Ho \
NH
yI]ethyl]-4'-methoxy[1,1'- 7.6 Hz, 1 H); 7.66 d (J = 8.0 0 biphenyl]-3-carboxamide; Hz, 1 H); 7.64 dd (J = 12.9 ~
Hz / 2.3 Hz, 1 H); 7.53 d(J = ~ I
1-(3-Methylbutyl)-L-tryptophanol F
8.8 Hz, 1 H); 7.49 dd (J = 7.8 ~o and Hz / 7.6 Hz, 1 H); 7.36 d(J =

3'-Fluoro-4' methoxy(1,1' 8.0 Hz, 1 H); 7.28 dd (J = 8.8 Product; Method Structure Ex. eagents analo- 'H-NMR (400 MHz) S[ppm]
gousto biphenyl]-3-carboxylic acid Hz / 8.8 Hz, 1 H); 7.16 s(1 H);
7.09 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 6.99 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 4.82 m(1 H); 4.25 m (1 H); 4.07 t (J = 6.8 Hz, 2H);
3.89 s (3H); 3.56 m(1 H);
3.51 m (1 H); 3.04 dd (J =
14.4 Hz / 5.8 Hz, 1 H); 2.93 dd (J = 14.4 Hz / 8.1 Hz, 1 H); 1.51 td (J = 7.2 Hz / 7.0 Hz, 1 H); 1.36 m (2H); 0.77 d (J = 7.4 Hz, 6H).

352 3'-Fluoro-N-[(R)-l- 39 (DMSO-d6): 8.27 d (J = 8.1 ~~
(hydroxymethyl)-2-(1-pentyl- Hz, 1 H); 8.03 s(1 H); 7.78 d ~ N
1 H-indol-3-yl)ethyl]-4'- (J = 7.8 Hz, 1 H); 7.76 d(J = Ho ~
NH
methoxy[1,1'-biphenyl]-3- 7.6 Hz, 1 H); 7.66 d (J = 8.0 0 carboxamide; Hz, 1 H); 7.64 dd (J = 12.9 Hz / 2.3 Hz, 1 H); 7.53 d(J = F 1-Pentyl-L-tryptophanol and ~o 8.8 Hz, 1 H); 7.49 dd (J = 7.8 3' Fluoro-4' methoxy(1,1' Hz / 7.6 Hz, 1 H); 7.37 d (J =
biphenyl]-3-carboxylic acid 8.0 Hz, 1 H); 7.28 dd (J = 8.8 Hz / 8.8 Hz, 1 H); 7.17 s(1 H);
7.09 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 6.98 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 4.82 m(1 H); 4.25 m (1 H); 4.05 t (J = 6.9 Hz, 2H);
3.89 s (3H); 3.56 m(1 H);
3.51 m (1 H); 3.04 dd (J =
14.7 Hz / 5.8 Hz, 1 H); 2.93 dd (J = 14.7 Hz / 8.1 Hz, 1 H); 1.63 m (2H); 1.13 m (2H); 1.10 m (2H); 0.70 t (J =
7.1 Hz, 3H).

Product; Method Structure Ex. reagents analo- 'H-NMR (400 MHz) S[ppm]
gousto 353 3'-Fluoro-N-[(R)-2-(1-hexyl-1 H- 39 (DMSO-d6): 8.27 d (J = 8.1 /~
indol-3-yl)-1- Hz, 1 H); 8.04 s(1 H); 7.78 d ~ N
(hydroxymethyl)ethyl]-4'- (J = 7.8 Hz, 1 H); 7.76 d(J = HO NH
methoxy[1,1'-biphenyl]-3- 7.6 Hz, 1 H); 7.66 d (J = 8.0 ~
carboxamide; Hz, 1 H); 7.65 dd (J = 12.9 Hz / 2.3 Hz, 1 H); 7.53 d(J = F
1-Hexyl-L-tryptophanol and "
8.8 Hz, 1 H); 7.49 dd (J = 7.8 3' Fluoro-4'-methoxy(1,1' Hz / 7.6 Hz, 1 H); 7.37 d (J =
biphenyl]-3-carboxylic acid 8.0 Hz, 1 H); 7.28 dd (J = 8.8 Hz / 8.8 Hz, 1 H); 7.17 s(1 H);
7.09 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 6.98 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 4.82 m(1 H); 4.25 m (1 H); 4.05 t (J = 6.9 Hz, 2H);
3.89 s (3H); 3.56 m(1 H);
3.51 m (1 H); 3.04 dd (J =
14.4 Hz / 5.8 Hz, 1 H); 2.93 dd (J = 14.4 Hz / 8.1 Hz, 1 H); 1.61 m(2H); 1.10 m (6H); 0.73 t (J = 7.1 Hz, 3H).

Example 354 4-Ethoxy-3'-methoxybiphenyl-3-carboxylic acid [2-(5,6-difluoro-1 H-indol-3-yl)-F
N ~ \
~ ~ F
HO
O NH
hydroxymethylethyl]amide;

354a) (5,6-Difluoro-1 H-indol-3-yl)-acetaldehyde At 0 C, phosphoryl chloride (22.03 g) was slowly added dropwise to DMF (19.1 g), and the mixture was stirred at 0-5 C for half an hour and then at room temperature for one hour. The mixture was cooled again to 0 C, and a solution of 5,6-difluoro-1 H-indole (20 g) in DMF (20 g) was slowly added dropwise. The mixture was stirred at 0 C
for 30 minutes and then at room temperature for a further 15 hours. The reaction mixture was poured onto ice (200 g) and basified to pH 10 with NaOH. The crystalline title com-pound was filtered off, washed with water and dried in vacuo (yield 22.7 g, 96%). MS
(ESI,+): 196 (M+1).

354b) [2-(5,6-Difluoro-1 H-indol-3-yl)ethyl]diethylamine Sodium triacetoxyborohydride (26.3 g) was added in portions to a solution of (5,6-difluoro-1 H-indol-3-yl)acetaldehyde (15 g) and diethylamine (6.66 g) in absolute di-chloromethane (300 ml) with 2 drops of trifluoroacetic acid, and the mixture was stirred at room temperature for 24 hours. The solvent was distilled off in a rotary evaporator, and the residue was mixed with 10% strength aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated in a rotary evaporator. The crude product was purified by flash chromatography, and the title compound was obtained in 68% yield (13.5 g). MS
(ESI,+): 253 (M+1).

354c) Ethyl 3-(5,6-difluoro-1 H-indol-3-yl)-2-nitropropionate A mixture of gramine (8 g) and ethyl 2-nitroacetate (8.9 g) was stirred in absolute tolu-ene at 90-100 C for 4 hours. The reaction mixture was concentrated in a rotary evapo-rator, and the crude product was purified by flash chromatography (chloroform : metha-nol 19 :1), after which the title compound was obtained in a yield of 11.7 g as a 1:2 mix-ture with ethyl 2-nitroacetate. MS (ESI,+): 299 (M+1).

354d) Ethyl 2-amino-3-(5,6-difluoro-1 H-indol-3-yl)propionate The mixture from the above stage was stirred with ammonium formate (9.9 g) and Pd (4.1 g. 10% on activated carbon) in 300 ml of ethanol under reflux for 15 hours. The reaction mixture was concentrated in a rotary evaporator, diluted with water (100 ml) and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated in a rotary evaporator. The residue was purified by flash chromatography (silica, chloroform : methanol 19 :1) and recrystallized as HCI
salt from ethanol. The title compound was obtained in a yield of 2.7 g. MS (ESI,+): 269 (M+1).
354e) 4-Ethoxy-3'-methoxybiphenyl-3-carboxylic acid [2-(5,6-difluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide 0.39 mmol (143 mg) of the acid was dissolved in 5 ml of dimethylformamide and, at room temperature, 0.39 mmol (59 mg) of 1-hydroxy-1 H-benzotriazole hydrate and 0.39 mmol (74 mg) of N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide hydrochloride were added. The mixture was stirred at the stated temperature for 60 minutes, and then 0.3 mmol (80 mg) of the difluorotryptophan ethyl ester was added. After a further hour, the reaction mixture was added to saturated sodium bicarbonate solution, and the pre-cipitate was filtered and washed with water. Purification by chromatography on silica gel with the eluent cyclohexane/ethyl acetate affords 64 mg of the compound as yellow foam.

0.15 mmol (76 NI) of 2M lithium borohydride solution was added dropwise to a solution of 0.1 mmol (63mg) of the carboxamide in 2ml of THF at 0 C. This mixture is then stirred at room temperature for 4-6 hours. It was subsequently neutralized with 1 N
hydrochloric acid at 0 C and, after addition of water, extracted with ethyl acetate. The organic phase was dried over magnesium sulphate, filtered and concentrated in vacuo.
Purification by chromatography on silica gel with the eluent cyclohexane/ethyl acetate affords 37 mg of pale yellow powder.

(DMSO-d6): 11.00 s(1 H) 8.40 d (J = 7.8 Hz, 1 H); 8.12 s(1 H); 7.77 d (J = 8.6 Hz, 1 H);
7.65 m (1 H); 7.36 m (3H); 7.20 m (3H); 7.13 s (1 H); 6.91 d (J = 9.7 Hz, 1 H); 4.98 t (J =
5.4 Hz, 1 H); 4.16 m (3H); 3.82 s (3H); 3.45 m(2H); 2.95 m (2H); 1.33 t (J =
7.0 Hz, 3H).
The following compounds were obtained in analogy to the preparation methods de-scribed in detail:

Product; Method 'H-NMR (400 MHz) S Structure Ex. reagents analo-gousto [Ppm]
355 6-Methoxy-2-(3,4,5- 354 (DMSO-6): 11.00 s(1 H);
N F
trimethoxyphenyl)quinoline-4- 7 d (J = 8.6 Hz, 1 H); 8.00 F
carboxylic acid [2-(5,6-difluoro- d (J = 9.0 Hz, 1 H); 7.96 s HO

1 H-indol-3-yl)-1- (1 H); 7.59 m(1 H); 7.49 s ~ 0"
H N I
hydroxymethylethyl]amide; (2); 7.42 d (6.6 Hz, 1 H);
7.31 m(1 H); 7.29 s(1 H);
2-Amino-3-(5, 6-difluoro-1 H- 4.93 t (J = 5.3 Hz, 1 H); /
indol-3-yl)-propan-1-ol 4.35 m(1 H); 3.92 s (6H);

and 3.75 s (6H); 3.60 t (J =
5.5 Hz, 2H); 3.00 dd (J =
6-Methoxy-2-(3, 4, 5- 14.3 Hz / 5.6 Hz, 1 H);
trimethoxyphenyl)quinoline-4- 2.90 dd (J = 14.4 Hz / 8.0 carboxylic acid Hz, 1 H).

Example 356 N-[ (R)-1-(Hydroxymethyl)-2-(1-ethyl-5-fluoro-1 H-indol-3-yl) ethyl]-6-methoxy-C -N F
HO
O NH
O"
_O N
,O
(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide; ' 0.2 mmol (12 mg) of potassium hydroxide powder was added in portions, cooling slightly with water, to a stirred solution of 0.09 mmol (50 mg) of 6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [R-1-(5-fluoro-1 H-indol-3-ylmethyl)-2-hydroxyethyl]amide in 1 ml of DMSO. This mixture was stirred for 5 minutes and then 0.2 mmol (17.2 NI) of ethyl iodide, dissolved in 0.3 ml of DMSO, was added dropwise.
Stirring was then continued at room temperature for 2 hours, and the reaction mixture was subsequently added to saturated aqueous ammonium chloride solution and ex-tracted with ethyl acetate. The resulting organic phase was dried over magnesium sul-phate, filtered and concentrated in vacuo with addition of toluene.
Purification by chro-matography on silica gel with the eluent cyclohexane/acetone affords 41.9 mg of the compound as pale yellow foam.

(DMSO-d6): 8.67 d (J = 8.6 Hz, 1 H, NH); 8.01 d (J = 8.5 Hz, 1 H, aryl); 7.98 s (1 H, aryl);
7.50 s (2H, aryl); 7.42 m (4H, aryl); 7.32 s (1 H, aryl); 6.94 t (J = 7.3 Hz, 1 H, aryl), 6.94 t (J = 7.3 Hz, 1 H, aryl); 4.91 t (J = 5.4 Hz, 1 H, OH); 4.36 m(1 H, CH); 4.13 q (J = 7.0 Hz, CHZ); 3.92 s (6H, OCH3); 3.60 t (J = 5.5 Hz, 2H, OCH2); 2.98 dd (J = 14.4 Hz /
5.7 Hz, 1 H, CH); 2.92 dd (J = 14.4 Hz / 8.1 Hz, 1 H, CH); 1.27 t (J = 7.0 Hz, CH3).

The following compounds were obtained in analogy to the preparation methods de-scribed in detail:

Product; Method 'H-NMR (400 MHz) S Structure Ex. reagents 9~ o IPpm]

357 6-Methoxy-2-(3,4,5- 356 (DMSO-d6): 8.67 d (J trimethoxyphenyl)quinoline-4-8.6 Hz, 1 H, NH); 8.01 d (J carboxylic acid [(R)-2-(1-ethyl- = 8.5 Hz, 1H, aryl); 7.98 s Ho 5-fluoro-1 H-indol-3-yl)-1- (1 H, aryl); 7.50 s (2H, a- oN
hydroxymethylethyl]amide; ryl); 7.42 m (4H, aryl); '0 N
7.32 s(1 H, aryl); 6.94 t (J - ;
6-Methoxy-2-(3, 4, 5- = 7.3 Hz, 1 H, aryl), 6.94 t trimethoxyphenyi)quinoiine-4-(J = 7.3 Hz, 1 H, aryl); 4.91 carboxylic acid((R)-1-(5-fluoro- t (J = 5.4 Hz, 1 H, OH);
1 H-indol-3-ylmethyl)-2- 4.36 m(1 H, CH); 4.13 q (J
hydroxyethylJamide = 7.0 Hz, CH2); 3.92 s (6H, OCH3); 3.60 t (J = 5.5 Hz, 2H, OCH2); 2.98 dd (J
= 14.4 Hz / 5.7 Hz, 1 H, CH); 2.92 dd (J = 14.4 Hz / 8.1 Hz, 1 H, CH); 1.27 t(J
= 7.0 Hz, CH3).

Example 358 6-(3,4,5-Trimethoxyphenyl)quinoline-8-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
H
~ N
\

HO
O NH
N
o 358a) 6-Bromoquinoline-8-carboxylic acid Concentrated sulphuric acid (20.5 mi) was added to a soluton of 2-amino-5-bromobenzoic acid (25 g), glycerol (35 ml) and nitrobenzene (7.3 ml) (highly exother-mic) and the reaction was stirred at 150 C for 5 hours. The cooled reaction mixture was poured into ice-water (750 ml), and KOH (22.4 g) was added. The precipitate was fil-tered off, and the residue on the filter was dissolved in KOH (5 g) in water (350 ml). Ac-tivated carbon was added, and the mixture was stirred at 50 C for half an hour. The mixture was filtered through a short layer of silica gel, and the filtrate was acidified with acetic acid. The resulting precipitate was filtered off, washed with water and dried in air.
Recrystallization from acetonitrile yielded 7.5 g (26%) of the title compound.
MS
(ESI,+): 253 (M+1).

358b) 6-Bromoquinoline-8-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide The quinolinecarboxylic acid was reacted with (D)-tryptophanol to give the title com-pound in analogy to general method 113b.

358c) 6-(3,4,5-Trimethoxyphenyl)quinoline-8-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide The aryl bromide was arylated under the Suzuki conditions to give the title compound in analogy to general method 125e.

(DMSO-d6): 11.17 d (J = 7.8 Hz, 1 H); 10.83 s(1 H); 8.87 s (2H); 8.52 dd (J =
1.5 Hz /
8.3 Hz, 1 H); 8.44 s (1 H); 7.73 d (J = 7.8 Hz, 1 H); 7.60 m (2H); 7.33 d (J =
7.8 Hz, 1 H);
7.26 s(1 H); 7.05 m (3H); 6.94 m(1 H); 5.03 m(1 H); 4.42 m(1 H); 3.88 s (6H);
3.71 s (3H); 3.67 m(1 H); 3.54 m(1 H); 3.12 m (2H).

The following compounds were obtained in analogy to the preparation methods de-scribed in detail:

Product; Method 'H-NMR (400 MHz) S Structure Ex. reagents y~ o [ppm]

359 3-(3,4,5-Trimethoxyphenyl)- 113b (DMSO-ds): 10.79 s(1 H); H
N
naphthalene-l-carboxylic acid 8.40 d (J = 8.3 Hz, 1 H);
[(R)-1-hydroxymethyl-2-(1 H- 125e 8.24 s(1 H); 7.99 m(1 H);
HO
indol-3-yl)ethyl]amide; 7.75 d (J = 1.7 Hz, 1 H); O NH
7.65 d (J = 7.7 Hz, 1 H);
3-Bromo-naphthalene-1- 7.52 m(1 H); 7.44 m(1 H);
carboxylic acid ((R)-1- 0 7.30 d(J = 7.9 Hz, 1 H);
hydroxymethyl-2-(1 H-indol-3-7.18 s(1 H); 7.03 m (4H);
O
yl)ethylJamide ~
6.92 m(1 H); 4.83 m(1 H);
and 4.33 m(1 H); 3.87 s (6H);
3.70 s (3H); 3.58 m(1 H);
3,4,5-Trimethoxyphenylboronic 3.51 m (1 H); 3.04 m(1H);
acid 2.92 m (1 H).

360 4-Methoxy-5-(3,4,5- 113b (CDCI3): 10.81 s(1 H); N
trimethoxyphenyl)thiophene-3- 7.95 s(1 H); 7.88 d (J =
carboxylic acid [(R)-2-hydroxy- 125e 8.3 Hz, 1 H); 7.68 d (J =
1-(1 H-indol-3- 7.8 Hz, 1 H); 7.33 (J = 7.8 HO
O H
ylmethyl)ethyl]amide; Hz, 1 H); 7.17 s(1 H); 7.06 5-Bromo-4-methoxy-thiophene- m(1 H); 6.98 m(1 H); 6.90 O S
3-carboxylic acid ((R)-2- s(2H); 4.94 m(1 H); 4.25 hydroxy-1-(1H-indol-3- m(1H); 3.82 s (6H); 3.70 %
ylmethyl)ethylJamide s (3H); 3.54 s (3H); 3.51 -'0 and m(1 H); 3.46 m(1 H); 2.97 3, 4, 5-Trimethoxyphenylboronic m (2H).
acid Product; Method 'H-NMR (400 MHz) S Structure Ex. reagents g ~ o [ppm]

361 6-(3,4,5-Trimethoxyphenyl)-1 H- 113b (DMSO-d6): 12.94 s(1 H); N
benzoimidazole-4-carboxylic 10.73 s(1 H); 10.02 d (J
acid [(R)-2-hydroxy-1-(1 H- 125e 7.7 Hz, 1 H); 8.47 s(1 H); Ho indol-3-ylmethyl)ethyl]amide; 8.10 s(1 H); 7.93 s(1 H); o H
6-Bromo-1 H-benzimidazole-4- 7.70 d (J = 7.7 Hz, 1 H);
carboxylic acid [(R)-2-hydroxy- 7.28 d (J = 7.9 Hz, 1 H); o \>
N
1-(1H-indol-3- 7.14 s(1H); 6.91 m(4H); H
ylmethyl)ethylJamide 4.92 m(1 H); 4.33 m(1 H);
and 3.85 s (6H); 3.68 s (3H);
3,4,5-Trimethoxyphenylboronic 3.56 m ~~ m ~~N), . 2.98 m {2,u N, acid 362 2-(3,4,5- 125 (DMSO-d6): 10.77 s(1 H); S
NTrimethoxyphenyl)thiazole-4- 8.23 s(1 H); 8.04 d(J =
carboxylic acid [(R)-2-hydroxy- 8.6 Hz, 1 H); 7.66 d (J =
HO
1-(1 H-indol-3- 7.8 Hz, 1 H); 7.28 d(J = o H
ylmethyl)ethyl]amide; 8.1 Hz, 1 H); 7.23 s (2H);
7.15 s(1 H); 7.01 m(1 H); N~ s (D)-Tryptophanol 6.92 m(1 H); 4.91 m(1 H);
o and 4.19 (1 H); 3.87 s (6H); 3.70 s (3H); 3.56 m(1 H); 0 ~
2-(3,4,5- 3.49 m(1H); 2.99 m (2H).
Trimethoxyphenyl)thiazole-4-carboxylic acid 363 5-(3,4,5- 125 (DMSO-d6): 10.73 s(1 H); H
Trimethoxyphenyl)thiophene-2- 8.17 d (J = 8.3 Hz, 1 H);
carboxylic acid [(R)-2-hydroxy- 7.91 s (1 H); 7.74 d(J =
HO
1-(1 H-indol-3- 4.0 Hz, 1 H); 7.60 d (J = o H
ylmethyl)ethyl]amide; 7.8 Hz, 1 H); 7.48 d (J =
s 3.8 Hz, 1 H); 7.28 d (J =
(D)-Tryptophanol 8.1 Hz, 1 H); 7.10 s(1 H); o and 7.01 m(1H); 6.90 m(1H); _o 4.80 m(1 H); 4.15 m(1 H); ~
5-(3,4,5- 3.81 s (6H); 3.64 s (3H);

Product; Method 'H-NMR (400 MHz) S Structure Ex. reagents g ~ o [ppm]
Trimethoxyphenyl)thiophene-2- 3.48 m (2H); 2.97 m (1 H);
carboxylic acid 2.85 m(1 H).

364 5-(3,4,5-Trimethoxyphenyl)- 125 (DMSO-d6): 10.73 s(1 H); N
benzo[b]thiophene-2-carboxylic 8.52 d (J = 8.1 Hz, 1 H);
acid [(R)-2-hydroxy-1-(1 H-indol- 8.16 d (J = 1.5 Hz, 1 H);
HO
3-ylmethyl)ethyl]amide; 8.14 s(1 H); 8.02 d (J = 0 H
8.3 Hz, 1 H); 7.73 dd (J =
(D)-Tryptophanol s 2.0 Hz / 8.6 Hz, 1 H); 7.61 and d (J = 8.1 Hz, 1 H); 7.28 d (J = 8.1 Hz, 1 H); 7.12 s ~\
5-(3, 4, 5-Trimethoxyphenyl)- ~ _ (1H);7.01 m(1H);6.95s benzo[b]thiophene-2-carboxylic (2H); 6.92 m(1 H); 4.82 m 0 \ / 0 acid (1 H); 4.18 m(1 H); 3.85 s (6H); 3.67 s (3H); 3.50 m (2H); 3.01 m(1 H); 2.95 m (1 H).

365 2-(3-Fluoro-4-methoxyphenyl)- 125 (DMSO-d6): 10.74 s(1 H); - H
N-[(R)-2-hydroxy-1-(1 H-indol-3- 8.46 d(J - 8.3 Hz, 1 H); i ylmethyl)ethyl]-6-methyl- 7.91 m (3H); 7.62 d (J =
HO
isonicotinamide; 7.7 Hz, 1 H); 7.47 s(1 H); 0 NH
(D)-Tryptophanol 7.26 m(2H); 7.11 s(1 H);
I
and 7.01 m(1 H); 6.93 m(1 H); F ~ N
2-(3-Fluoro-4-methoxyphenyl)- 4.81 m(1 H) 2.53 s(3H). ~o I~
6-methyl-isonicotinic acid 366 2-(3-Fluoro-4-methoxyphenyl)- 125 (CDC13): 8.39 d (J = Hz, - N
6-methylpyrimidine-4-carboxylic 1 H); 8.31 s(1 H); 8.23 d (J
~ l i acid [(R)-2-hydroxy-1-(1 H-indol- = 8.4 Hz, 1 H); 8.00 dd (J = Ho 3-ylmethyl)ethyl]amide; 12.9 Hz / 2.3 Hz, 1 H); O NH
7.81 s(1 H); 7.72 d (J = N' I
(D)-Tryptophanol 7.8 Hz, 1 H); 7.42 d (J = F Nz~ N
and 8.1 Hz, 1 H); 7.22 m (2H); "o 7.12 m(1 H); 7.01 m(1 H);

Product; Method +H-NMR (400 MHz) 8 Structure Ex. reagents 9~ o Ippm]
2-(3-Fluoro-4-methoxyphenyl)- 4.49 m(1 H); 3.97 s(3H);
6-methylpyrimidine-4-carboxylic 3=89 m (2H); 3.20 m (2H);
acid 2.71 s (3H).

367 6-(4-Methoxyphenyl)pyrimidine- 125 (DMSO-d6): 10.79 s(1H);
4-carboxylic acid [(R)-1- 9.28 s(1 H); 8.69 d (J
hydroxymethyl-2-(1 H-indol-3- 8.9 Hz, 1 H); 8.42 s(1 H); NH
yI)ethyl]amide; 8.27 d (J = 9.0 Hz, 1 H);

(D)-Tryptophanol 7.70 d (J = 7.7 Hz, 1 H); OH o N\
and 7.33 d (J = 7.9 Hz, 1 H); 1 7.14 m (3H); 7.06 m(1 H); N
6-(4-Methoxyphenyl)pyrimidine-6.98 m(1 H); 4.28 m(1 H);
4-carboxylic acid 3.87 s (3H); 3.52 m (2H); 3.03 m (2H). 0 Example 368 2-(3-Fluoro-4-methoxyphenyl)-6-methoxyquinazoline-4-carboxylic acid [(R)-2-H
N

HO
O NH

N~ O1~
O Zt, hydroxy-l-(1H-indol-3-ylmethyl)ethyl]amide; F

368a) 5-Methoxyisatin sodium salt A solution of 1 N KOH (100 ml) was slowly added in portions to a suspension of 5-methoxyisatin (17.7 g) in water (100 ml), and the mixture was heated to about 40 C. It was stirred until almost all the isatin had dissolved. The undissolved residue was filtered off, and the filtrate was evaporated to dryness in a rotary evaporator.
Absolute ethanol (200 ml) was added to the residue, and the solid was stirred at room temperature, and the sodium salt of 5-methoxyisatin was filtered off and dried in vacuo at room tempera-ture. Yield 20.6 g (96%).

368b) [2-(3-Fluoro-4-methoxybenzoylamino)-5-methoxyphenyl]oxoacetic acid Dimethylaminopyridine (3.5 g), and then triethylamine (75 ml) and subsequently a solu-tion of 3-fluoro-4-methoxybenzoyl chloride (37.7 g) in THF (200 ml) were added drop-wise to a solution of the sodium salt of 5-methoxyisatin (21.5 g) in THF (300 ml), and the reaction mixture was stirred at room temperature for 20 hours. Water (30 ml) was added to the reaction mixture and stirred for a 4 hours. The insoluble residue was fil-tered off and the filtrate was evaporated to dryness. The residue was again dissolved in water (900 ml) and acidfied to pH 1 with 1 N HCI. The precipitate which separated out was filtered off, washed with water and dried in air. Recrystallization from benzene yielded 11.1 g (32%) of the title compound. MS (ESI,+): 348 (M+1).

368c) 2-(3-Fluoro-4-methoxyphenyl)-6-methoxyquinazoline-4-carboxylic acid Anhydrous ammonia (5 g) was added to a solution of [2-(3-fluoro-4-methoxybenzoylamino)-5-methoxyphenyl]oxoacetic acid (3.47 g) in ethanol (50 ml). The reaction mixture was heated in a sealed tube at 120 C under autogenous conditions for 6 hours. Solvent and ammonia were distilled out in a rotary evaporator, and the dry residue was suspended in water (100 ml) and acidified to pH 3-4 with acetic acid. The resulting precipitate was filtered off, washed with water and recrystallized from ethanol in an autoclave at 150 C. Yield 2.1 g (65%). MS (ESI,+): 329 (M+1).

368d) 2-(3-Fluoro-4-methoxyphenyl)-6-methoxyquinazoline-4-carboxylic acid [(R)-hydroxy-1 -(1 H-indol-3-ylmethyl)ethyl]amide The title compound was obtained by reaction with (D)-tryptophanol in analogy to gen-eral method 113b.

(DMSO-d6): 10.81 s (1 H); 8.90 d (J = 8.6 Hz, 1 H); 8.31 m (2H); 8.12 s (1 H);
7.97 m (1 H); 7.34 m (2H); 7.21 s(1 H); 7.00 m(1 H); 6.90 m(1 H); 4.95 m(1 H); 4.35 m(1 H);
3.93 s (3H); 3.82 m (3H); 3.58 m (2H); 3.08 m(1 H); 3.03 m(1 H).

The following compounds were obtained in analogy to the preparation methods de-scribed in detail:

Product; Method 'H-NMR (400 MHz) S Structure Ex. analto~
reagents IPpm]
369 2-(3-Fluoro-4-methoxyphenyl)- 368 (DMSO-d6): 10.81 s(1 H); - N
6-iodoquinazoline-4-carboxylic 9.11 s (1 H); 8.95 d (J = A i acid [(R)-2-hydroxy-1-(1H-indol- Hz, 1 H); 8.35 m (2H); 8.23 H(D
3-ylmethyl)ethyl]amide; m (1 H); 7.81 d (J = 8.8 Hz, H 0 1 H); 7.66 d(J = 7.8 Hz, N (D)-Tryptophanol 1 H); 7.29 m(2H); 7.21 s ~
o and (1H); 7.00 m(1H); 6.90 m (1 H); 4.93 m(1 H); 4.32 m 2-(3-Fluoro-4-methoxyphenyl)- (1 H); 3.94 s (3H); 3.58 m 6-iodoquinazoline-4-carboxylic (2H); 3.05 m (2H).
acid 370 2-(4-Methoxyphenyl)- 368 (DMSO-d6): 10.84 s(1 H); H
~ N
quinazoline-4-carboxylic acid 8.43 d (J = 8.6 Hz, 1 H);
[(R)-1-hydroxymethyl-2-(1 H- 8.48 m (2H); 8.39 d(J =
HO
indol-3-yl)ethyl]amide; 8.3 Hz, 1 H); 7.98 m (2H); 0 NH
7.66 m(1 H); 7.59 m(1 H);
(D)-Tryptophanol N
7.33 d (J = 7.3 Hz, 1 H); "N
and 7.21 d (J = 2.0 Hz, 1 H);
7.12 m (2H); 7.03 m (1H);
2-(4-methoxyphenyl)- 6.94 m(1 H); 4.93 m(1 H);
quinazoline-4-carboxylic acid 4.36 m(1 H); 3.85 s (3H);
3.56 m (2H); 3.08 m (1H);
3.01 m (1 H).

Product; Method 'H-NMR (400 MHz) S Structure Ex. reagents analogous O1S [ppm]

371 2-(3-Fluoro-4-methoxyphenyl)- 368 (DMSO-d6): 8.94 d (J 6-methoxy-quinazoline-4- 8.6 Hz, 1 H); 8.34 m (2H);
N~
carboxylic acid [(R)-1-(1-ethyl- 8.17 s(1 H); 8.00 d (J = 9.4 HO
1 H-indol-3-ylmethyl)-2- Hz, 1 H); 7.69 d (J = 7.5 0 H
hydroxyethyl]amide; Hz, 2H) 7.38 t (J = 10.9 N~ \ 0 Hz, 2H); 7.28 s(1 H); 7.08 t . ~ ~
(R)-2-Amino-3-(1-ethyl-1H- N
(J = 7.5 Hz, 1 H; 6.96 t (J indol-3-yl)-propan-l-ol 7.1 Hz, 1 H); 4.98 t (J =
5.4 F

and Hz, 1 H); 4.37 m(1 H); 4.12 q(J = 7.0 Hz, 2H); 3.64 m 2-(3-Fluoro-4-methoxyphenyl)- (2H); 3.10 dd (J = 14.3 Hz 6-methoxy-quinazoline-4- / 5.6 Hz, 1 H); 3.03 dd (J =
carboxylic acid 14.3 Hz / 8.2 Hz, 1 H); 1.26 t (J = 7.0 Hz, 3H).

Example 372 2-(3,4,5-Trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-2-hydroxy-l-(1 H-indol-3-ylmethyl)-2-methylpropyl]amide;
H
X
N
HO

O NH
-O N I
-O
"o 3.33 mmol (1.11 ml) of 3M methylmagnesium bromide solution were added dropwise to a solution of 0.22 mmol (120 mg) of methyl (R)-3-(1 H-indol-3-yl)-2-{[2-(3,4,5-trimethoxyphenyl)quinoline-4-carbonyl]amino}propionate in 4.5 ml of THF at 0 C. This mixture is then stirred at room temperature for about 30 minutes and then added to saturated aqueous ammonium chloride solution and extracted with ethyl acetate.
The organic phase was dried over magnesium sulphate, filtered and concentrated in vacuo.

Purification by chromatography on silica gel with the eluents cyclohexane/ethyl acetate affords 107 mg of pale red foam.

(DMSO-d6):10.81 s(1 H); 8.50 d (J = 9.7 Hz, 1 H); 8.04 d (J = 8.7 Hz, 1 H);
7.74 s(1 H);
7.72 d (J = 7.4 Hz, 1 H); 7.62 d (J = 7.9 Hz, 1 H); 7.49 d (J = 8.3 Hz, 1 H);
7.46 s (2H);
7.41 d(J=7.8Hz, 1 H); 7.36 d (J = 8.2 Hz, 1 H); 7.18 s (1 H); 7.06 t (J = 7.8 Hz, 1H);
6.96 t (J = 7.4 Hz, 1 H); 4.68 s (1 H); 4.40 t (J = 9.8 Hz, 1 H); 3.92 s (6H);
3.74 s(3H);
3.26 d (J = 14.1 Hz, 1 H); 2.83 t (J = 14.4 Hz, 1 H); 1.38 s (3H); 1.27 s (3H).

The following compounds were obtained in analogy to the preparation methods de-scribed in detail:

Product; Method 'H-NMR (400 MHz) g Structure X. reagents g ~ o [ppm]

373 6-Methoxy-2-(3,4,5- 372 (DMSO-d6): 10.77 s(1 H); N -trimethoxyphenyl)quinoline-4- 8.53 d (J = 9.4 Hz, 1 H);
carboxylic acid [(R)-2- 7.97 d (J = 9.0 Hz, 1 H); "o O NH
hydroxy-1-(1 H-indol-3- 7.68 s (1 H); 7.60 d (J = o, ylmethyl)-2- 7.8 Hz, 1 H); 7.41 s (3H); -o ~ N methylpropyl]amide; 7.31 d (J =
8.2 Hz, 1 H); -o "o 7.21 d (J = 9.8 Hz, 2H);
Methyl (R)-3-(1 H-indol-3-yl)-2- 7.04 t (J = 7.7 Hz, 1 H);
{(6-methoxy-2-(3, 4, 5-6.94 t (J = 7.8 Hz, 1 H);
trimethox yphen yl) quinoline-4-4.69 s(1 H); 4.38 t (J =
carbonyl]amino}propionate 10.1 Hz, 1 H); 3.92 s (6H);
3.75 s (3H); 3.63 s (3H);
3.24 d (J = 14.0 Hz, 1 H);
2.82 t (J = 14.7 Hz, 1 H);
1.37 s (3H); 1.27 s (3H).

Example 374 6-(4-Hydroxybut-1-ynyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
H ~
N ~
HO
O NH OH
I / \
N
o 374a1 6-lodo-2-(3-4.5-trimethoxvnhenvl)auinoline-4-carboxvlic acid --, - ---- - .-. ,- _.....-- - õ- , , , .

The title compound was obtained in analogy to general methods 13a. MS (ESI,+):

(M+1).

374b) Methyl 6-iodo-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylate The carboxylic acid (1 g) was dissolved in methanol (100 ml) and acidified with a few drops of conc. sulphuric acid. The mixture was stirred at room temperature overnight, and the title compound was precipitated by addition of water, filtered off and washed with water, and the residue was dried in vacuo. Yield 910 mg. MS (ESI,+): 480 (M+1).
374c) Methyl 6-(4-hydroxybut-1-ynyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxyate Methyl 6-iodo-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylate (1 g), but-3-yn-l-ol (0.32 ml), Cul (397 mg), Pd(PPh3)4 (241 mg) and triethylamine (2.89 ml) were sus-pended in THF (20 ml) and stirred together at room temperature overnight. The mixture was added to water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and freed of solvent in a rotary evaporator.
The title compound was obtained after flash chromatography in 41 % yield (360 mg). MS
(ESI,+):
422 (M+1).

374d) 6-(4-Hydroxybut-1-ynyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid The title compound was obtained in analogy to general method 39b.

374e) 6-(4-Hydroxybut-1-ynyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide The title compound was obtained by reaction with (D)-tryptophanol in analogy to gen-eral method 113b.
(DMSO-d6): 10.79 s(1 H); 8.70 d(J = 8.3 Hz, 1 H); 8.01 m (3H); 7.65 m(2H);
7.50 s (2H); 7.32 d (J = 7.8 Hz, 1 H); 7.20 s (1 H); 7.02 m (1 H); 6.93 m (1 H); 4.31 m (1 H); 3.89 s (6H); 3.73 s (3H); 3.60 m (4H); 3.03 m(1 H); 2.95 m(1 H); 2.60 m (2H).

The following compounds were obtained in analogy to the preparation methods de-scribed in detail:

Product; eeethod 'H-NMR (400 MHz) S Structure Ex. 9~ o [ppm]
reagents 375 6-(5-Hydroxypent-1-ynyl)-2- 374 (DMSO-ds): 10.79 s(1H); OH
(3,4,5- 8.70 d (J = 8.3 Hz, 1 H);
trimethoxyphenyl)quinoline-4- 8.07 s(1 H); 8.00 m(2H); HN ~ ~ ~
carboxylic acid [(R)-1- 7.69 m (2H); 7.50 s (2H);
NH I
OHO
hydroxymethyl-2-(1 H-indol-3- 7.31 d (J = 8.1 Hz, 1 H);
i ~N
yl)ethyl]amide; 7.19 s(1H); 7.02 m(1H);
6.93 m(1H); 4.33 m(1H); I
6-lodo-2-(3,4,5- 3.90 s (6H); 3.73 s (3H); \c o~
.110 trimethoxyphenyl)quinoline-4-3.51 m(4H); 3.03 m (1 H);
carboxylic acid ((R)-1-2.96 m(1 H); 2.50 m (2H);
hydroxymethyl-2-(1 H-indol-3-1.70 m (2H).
yl)ethylJamide and Pent-4-yn-l-ol Product; Method 1H-NMR (400 MHz) S Structure Ex. analo-reagents sousto [ppm]

376 6-(3-Hydroxyprop-1-ynyl)-2- 374 (DMSO-d6): 10.78 s(1H);
OH
(3,4,5- 8.72 d (J = 8.3 Hz, 1 H);
HN ~ II
trimethoxyphenyl)quinoline-4- 8.11 s(1 H); 8.02 m(2H);
o NH
carboxylic acid [(R)-1- 7.72 d (J = 2.0 Hz / 8.8 %
hydroxymethyl-2-(1 H-indol-3- Hz, 1 H); 7.64 d (J = 7.8 yI)ethyl]amide; Hz, 1 H); 7.51 s(2H); 7.31 6-lodo-2-(3, 4, 5- d (J = 8.1 Hz, 1 H); 7.20 s .o ~

trimethoxyphenyl)quinoline-4- (1 H); 7.02 m (1 H); 6.93 m ~o carboxylic acid ((R)-1- (1 H); 4.35 m (3H); 3.90 s hydroxymethyl-2-(1H-indol-3- (6H); 3.73 s (3H); 3.55 m yl)ethylJamide (2H); 3.04 m(1 H); 2.94 m and (1 H).

Prop-2-yn-l-ol 377 6-(3-Methoxyprop-1-ynyl)-2- 374 (DMSO-d6): 10.78 s(1H);
H O
(3,4,5- 8.72 d(J = 8.3 Hz, 1 H); N

trimethoxyphenyl)quinoline-4- 8.13 s(1 H); 8.03 m (2H); carboxylic acid [(R)-1-7.76 d (J = 1.8 Hz, 1 H); NH

hydroxymethyl-2-(1 H-indol-3- 7.73 d (J = 1.8 Hz, 1 H); oHO
-N
yl)ethyl]amide; 7.52 s (2H); 7.30 d (J =

6-lodo-2-(3, 4, 5- 8.1 Hz, 1 H); 7.19 d (J = ~o o trimethoxyphenyl)quinoline-4- 2.3 Hz, 1 H); 7.02 m (1 H); ~o carboxylic acid ((R)-1- 6.92 m(1 H); 4.37 s(2H);
hydroxymethyl-2-(1H-indol-3- 4.33 m(1H); 3.90 s (6H);
yl)ethyl]amide 3.73 s (3H); 3.57 s (3H);
and 3.59 m (2H); 3.02 m(1 H);
3-Methoxypropyne 2.95 m (1 H).

Product; nnechod 'H-NMR (400 MHz) S Structure Ex. analo-reagents s m to [ppm]

378 5-(4-Hydroxybut-1-ynyl)- 39a-b/ (DMSO-d6): 10.75 s(1H); _ H
3',4', 5'-trimethoxybiphenyl- 8.35 d (J = 7.8 Hz, 1 H);
374c- 7.97 s(1 H); 7.82 s(1 H); HO
3-carboxylic acid [(R)-1- e 7.80 s(1 H); 7.65 d (J 0 NH
hydroxymethyl-2-(1 H-indol-7.8 Hz,1 H); 7.30 d(J = o 3-yl)ethyl]amide;
7.8 Hz,1 H); 7.13 s(1 H); o OH
7.03 t(J = 7.4 Hz, 1 H);
6.94 s (2H); 4.95 t (J =
(D)-Tryptophanol 5.5 Hz,1 H); 4.80 t (J = 5.5 Hz, 1 H); 4.24 m(1 H);
and 3.88 s (6H); 3.70 s (3H);
5-(3-Hydroxybut-1-ynyl)- 3.62 m(2H); 3.54 m(1H);
3',4',5'-trimethoxybiphenyl-3- 3.49 m(1 H); 2.97 m(2H);
carboxylic acid 2.80 t (J = 6.6 Hz, 2H).

379 5-(3-Hydroxyprop-1-ynyl)- 39a-b/ (DMSO-d6): 10.76 s(1H); - H
N
~
3',4',5'-trimethoxybiphenyl-3- 8.38 d (J = 8.2 Hz, 1 H);
carboxylic acid [(R)-1- 374c- 8.02 s(1 H); 7.86 s(1 H); Ho hydroxymethyl-2-(1 H-indol-3- e 7.84 s(1 H); 7.65 d (J
=
yl)ethyl]amide; 7.8 Hz, 1 H); 7.30 d (J = 0 8.2 Hz, 1 H); 7.14 s(1 H); 0 oH

(D)-Tryptophanol 7.04 t(J = 7 Hz, 1 H); I
and 6.94-6.97 m (3H); 5.40 t (J = 5.9 Hz, 1 H); 4.81 t (J
5-(3-Hydroxyprop-1-ynyl)- = 5.5 Hz, 1 H); 4.35 d (J =
3;4;5'trimethoxybiphenyl-3- 5.5 Hz, 2H); 4.20-4.28 m carboxylic acid (1 H); 3.88 s (6H); 3.70 s (3H); 3.46-3.59 m (2H);
3.03 dd (J = 14.4 Hz, J =
7.8 Hz, 1 H); 2.96 dd (J =
14.4 Hz; J= 7.8 Hz, 1 H).

Product; Method +H-NMR (400 MHz) S Structure Ex. analo-reagents sousto [ppm]

380 5-(5-Hydroxypent-1-ynyl)- 39a-b/ (DMSO-d6): 10.76 s(1H); ~/ N
~ ~
3',','-trimethoxybiphenyl-3- 8.36 d (J = 8.2 Hz, 1 H);
carboxylic acid [(R)-1- 37ec 7.97 s(1 H); 7.80 d (J = Ho NH
hydroxymethyl-2-(1 H-indol-3- 4,3 Hz, 1 H); 7.66 d (J I
yI)ethyl]amide; 7.8 Hz, 1 H); 7.30 d (J
= o P OH
7.8 Hz, 1 H); 7.14 s(1 H); ~ 0, (D)-Tryptophanol 7.04 t (J = 7.4 Hz, 1 H);
and 6.94-6.97 m (3H); 4.81 t (1 H); 4.58 t (J = 3.9 Hz, 5-(5-Hydroxypent-1-ynyl)- 1 H); 4.20-4.28 m (1 H);
3;4;5'-trimethoxybiphenyl-3- 3.88 s (6H); 3.70 s (3H);
carboxylic acid 3.46-3.58 m (4 H); 3.02 dd (J = 14.4 Hz, J = 7.8 Hz, 1 H); 2.93 dd (J = 14.4 Hz, J = 7.8 Hz, 1 H); 2.49-2.53 m (2H); 1.72 q (J =
6,6 Hz, 2H).

381 3',4',5'-Trimethoxy-5-(3- 39a-b/ (DMSO-d6): 10.76 s(1 H); - H
~ N
methoxyprop-1-ynyl)biphenyl- 8.36 d (J = 8.2 Hz, 1 H);
o 3-carboxylic acid [(R)-1- 374ce- 8.04 s(1H); 7.89 (s, 2H); H o NH
hydroxymethyl-2-(1 H-indol-3- 7.66 d (J = 7.8 Hz, 1 H);
I eth I amide; 7.30 d (J 8.2 Hz ; 7.14 0 Y) Yl ( ) I I
o s (1 H); 7.04 t (J = 7.4 Hz, o ~
(D)-Tryptophanol o~
1 H); 6.94-6.96 m (3H);
and 4.81 t (J = 5.9 Hz, 1 H);
4.36 s(2H); 4.52 m(1 H);
3;4;5'-Trimethoxy-5-(3- 3.88 s (6H); 3.70 s (3H);
methoxyprop-1-ynyl)biphenyl- 3.47-3.59 m (2H); 3.37 s 3-carboxylic acid (3H); 3.03 dd (J = 14.4 Hz, J = 5.8 Hz, 1 H); 2.94 dd (J = 14.4 Hz, J = 7.8 Hz, 1 H).

Product; Method 'H-NMR (400 MHz) 8 Structure Ex. analo-reagents yousto [ppm]

_ 382 3','-Dimethoxy-5-(3- 39a-b/ (DMSO-d6): 10.76 s (1 H); H
N
methoxyprop-1-ynyl)biphenyl- 8.39 d (J = 8.2 Hz, 1 H); ~/
374c- 8.04 s(1 H); 7.85 s (2H); Ho 3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3- e 7.66 d (J = 7.8 Hz, 1 H); o NH
7.26-7.31 m (3H); 7.14 yl)ethyl]amide; o (1 H); 7.02-7.07 m (2H); o, o (D)-Tryptophanol 6.96 t (J = 7.42; 1 H); 4.82 t (J = 5.8 Hz, 1 H); 4.37 s and (2H); 4.21-4.29 m (1H);
3;4'-Dimethoxy-5-(3- 3.87 s(3H); 3.80 s (3H);
methoxyprop-1-ynyl)bipheny1- 3.46-3.58 m (2H); 3.37 s 3-carboxylic acid (3H); 3.03 dd (J = 14.4 Hz; J = 5.8 Hz, 1 H); 2.93 dd (J = 14.4 Hz, J = 7.8 Hz, 1 H).
; H
383 5-(3-Hydroxyprop-1 -ynyl)- 39a-b/ (DMSO-d6): 10.76 s (1 H) N
3',4'-dimethoxybiphenyl-3- 8.38 d (J = 8.2 Hz, 1 H);
carboxylic acid [(R)-1- 374c- 8.02 s(1 H); 7.83 s(1 H); HO
hydroxymethyl-2-(1 H-indol-3- e 7.80 s (1 H); 7.65 d (J = 0 NH
yI)ethyl]amide; 7.8 Hz, 1 H); 7.30 d (J = o \\ I
8.2 Hz, 1 H); 7.25-7.27 m oH

(D)-Tryptophanol (2H); 7.13 (1 H); 7.02-7.07 ~
m (2H); 6.96 t (J = 7.42 and Hz, 1 H); 5.40 m(1 H);
5-(3-Hydroxyprop-1-ynyl)- 4.81 t (J = 5.8 Hz, 1 H);
3;4'-dimethoxybiphenyl-3- 4.35 m (2H); 4.21-4.29 m carboxylic acid (1 H); 3.86 s (3H); 3.80 s (3H); 3.46-3.58 m (2H);
3.03 dd (J = 14.5 Hz, J
6 Hz, 1 H); 2.93 dd (J =
14,5 Hz, J = 7.8 Hz, 1 H).

Product; Method 'H-NMR (400 MHz) 8 Structure Ex. analo-reagents gousto [ppm]

384 3',4',5'-Trimethoxy-5-(4- 39a-b/ (DMSO-d6): 10.77 s(1 H); H
methoxyphenylethy- 8.40 d (J = 7.8 Hz, 1 H);
374c- 8.03 s(1 H); 7.95 s (2H); Ho nyl)biphenyl-3-carboxylic acid e o NH
7.67 d (J = 7.8 Hz, 1 H);
[(R)-1-hydroxymethyl-2-(1 H- I
~~ I \
indol-3-yl)ethyl]amide; 7.55 s (1 H); 7.53 s (1 H); 0 7.31 (J = 8.2 Hz, 1 H); 0 i o" o (D)-Tryptophanol 7.15 (1 H); 6.94-7.06 m (6H); 4.83 t (J = 5.5 Hz, and 1 H); 4.22-4.30 m(1 H);
3',4',5'-Trimethoxy-5-(4- 3.89 s(6H); 3.80 s (3H);
methoxy- 3.71 s (3H); 3.48-3.60 m phenylethynyl)biphenyl-3- (2H); 3.03 dd (J = 14.8 carboxylic acid Hz, J = 6 Hz, 1 H); 2.95 dd (J = 14.4 Hz, J = 7.4 Hz, 1 H).

Example 385 3',4',5'-Trimethoxy-5-((Z)-3-methoxypropenyl)biphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyi]amide;
H
~ N
~

HO
O NH

ON.
O / \ I /
O
620 mg of zinc dust are suspended in 3.6 ml of water. Argon is passed through the vig-orously stirred suspension for 15 min. Then 62 mg of copper(II) acetate are added, and the mixture is stirred for 15 min. Subsequently 62 mg of sliver nitrate are added and stirring is continued for 30 min. The metal is filtered off with suction under argon. It is washed with 2 x 1.8 ml of water, 2 x 1.8 ml of methanol, 2 x 3.6 ml of acetone and 2 x 3.6 ml of diethyl ether.
The activated zinc obtained in this way is transferred while still moist with ether into a solution of 50 mg of 5-(3-hydroxyprop-1-ynyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide (Example # 381) in 1.3 ml of methanol and 0.5 ml of water. The reaction mixture is stirred until the reaction is com-plete. The metal is filtered off with suction (caution: the remaining metal is pyrophoric), and washed with methanol, and the solvent is evaporated. The title compound is ob-tained as a colourless foam (45 mg, 89% of theory).
'H-NMR (400 MHz) S[ppm] (DMSO-d6): 10.77 s(1 H); 8.30 d (J = 8.2 Hz, 1 H);
7.93 s (1 H); 7.66 d (J = 7.8 Hz, 1 H); 7.62 s (2H); 7.30 d (J = 8.2 Hz, 1 H); 7.15 s(1 H); 7.03 t (J
= 7.4 Hz, 1 H); 6.93-6.97 m(3H); 6.68 d (J = 12.1 Hz, 1 H); 5.88-5.94 m(1 H);
4.82 t (J =
5.6 Hz, 1 H); 4.20-4.26 m(3H); 3.88 s(6H); 3.71 s (3H); 3.47-3.60 m(2H); 3.27 s(3H);
3.04 dd (J = 14.5 Hz, J= 5.8 Hz, 1 H); 2.95 dd (J = 14.4 Hz, J= 7.8 Hz, 1 H).

,TTie following compounds were obtained in analogy to the preparation methods de-scribed in detail:

Product; Method Structure Ex. analo- 'H-NMR (400 MHz) S [ppm]
reagents sousto 386 5-((Z)-4-Hydroxybut-1-enyl)- 385 (DMSO-d6): 10.76 s(1H); N
3',4',5'-trimethoxybiphenyl-3- 8.27 d (J = 8.2 Hz, 1 H); 7.90 carboxylic acid [(R)-1- s(1 H); 7.74 s(1 H); 7.74 d (J HO
NH
hydroxymethyl-2-(1 H-indol-3- = 7.8 Hz, 1 H); 7.70 s(1 H); oH

yl)ethyl]amide; 7.66 (J = 7.8 Hz, 1 H); 7.30 d (J = 8.2 Hz, 1 H); 7.16 s(1 H); I
5-(4-Hydr oxybut-l-ynyl)-7.03 t (J = 7.4 Hz, 1 H); 6.95-3', 4, 5'-trimethoxybiphenyl-3-6.97 m(3H); 6.58 d (J = 11.7 carboxylic acid ((R)-1-Hz,1 H) 5.78-5.84 m(1 H);
hydroxymethyl-2-(1 H-indol-3-4.81 t (J = 5,8 Hz, 1 H); 4.69 t yl)ethyl]amide (J = 4.7 Hz, 1 H); 4.20-4.28 m (1 H); 3.88 s(6H); 3.71 s (3H); 3.47-3.60 m (4H); 3.04 dd (J = 14.8 Hz, J = 6 Hz, 1 H); 2.95 dd (J = 14.4 Hz, J
7.8 Hz, 1 H); 2.47-2.52 m (2H).

387 5-((Z)-3-Hydroxypropenyl)- 385 (DMSO-d6): 10.77 s(1 H); - H
N
3',','-trimethoxybiphenyl-3- 8.29 d (J = 7.8 Hz, 1 H); 7.91 carboxylic acid [(R)-1- s(1 H); 7.67 d (J = 7.8 Hz, Ho\
O NH
hydroxymethyl-2-(1 H-indol-3- 1 H); 7.64 s(1 H); 7.61 s(1 H); OH
yl)ethyl]amide; 7.30 (J=8.2Hz, 1H);7.16 (1 H); 7.03 t (J = 7.4 Hz, 1 H);
5-(3-Hydroxyprop- 1 -ynyl)-6.94-6.97 m (3H); 6.58 d (J =
3', 4, 5'-trimethoxybiphenyl-3-11.7 Hz, 1 H); 5.88-5.94 m carboxylic acid ((R)-1- (1 H); 4.96 t(J = 5,1 Hz, 1 H);
hydroxymethyl-2-(1 H-indol-3-4.82 t (J = 4.8 Hz, 1 H); 4.21-yl)ethyl]amide 4.30 m (3H); 3.88 s(6H);
3.71 s (3H); 3.47-3.60 m Product; Method Structure Ex. analo- 'H-NMR (400 MHz) S [ppm]
reagents gousto (2H); 3.27 s (3H); 3.04 dd (J
= 14.5 Hz, J = 5.8 Hz, 1 H);
2.95 dd (J = 14.4 Hz, J = 7.8 Hz, 1 H).

388 5-((Z)-5-Hydroxypent-l-enyl)- 385 (DMSO-ds): 10.76 s(1H); N
3',4',5'-trimethoxybiphenyl-3- 8.26 d (J = 8.2 Hz, 1 H); 7.89 HO
carboxylic acid [(R)-1- s(1 H); 7.69 s (2H); 7.66 s O NH

hydroxymethyl-2-(1 H-indol-3- (1 H); 7.30 (J = 8.2 Hz, 1 H); ol~
yI)ethyl]amide; 7.16 s (1 H); 7.04 t (J = 7.4 o, Hz, 1 H); 6.94-6.97 m (3H);
5-(5-Hydroxypent-1-ynyl)- 6.52 d(J = 11,3 Hz, 1 H);
3 ; 4, 5'-trimethoxybiphenyl-3-5.75-5.81 m (1 H); 4.81 t (J
=
carboxylic acid ((R)-1-5.6 Hz, 1 H); 4.51 t (J = 5 Hz, hydroxymethyl-2-(1 H-indol-3-1H); 4.21-4.28 m(1H); 3.88 s yl)ethyl]amide (6H); 3.71 s (3H); 3.43-3.60 m (4H); 3.05 dd (J = 14.5 Hz, J= 5.8 Hz, 1 H); 2.95 dd (J =
14.4 Hz, J= 7.8 Hz, 1 H);
2.39 q (J = 7.4 Hz, 2H); 1.58-1.65 m (2H).

Example 389 6-(5-Hydroxypentyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide;
H ~
N ~
HO
O NH

\ OH
O N I /

O
"lo 6-(5-Hydroxypent-1-ynyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1 H-indol-3-yl)ethyl]amide (100 mg) and palladium on carbon (10%, 50 mg) were suspended in methanol (10 ml) and hydrogenated under hydrogen at atmospheric pressure at room temperature. After hydrogen uptake ceased, the catalyst was filtered off and the mother liquor was stripped off in a rotary evaporator. Drying in vacuo resulted in the title compound in 42% yield (42 mg).

(DMSO-d6): 10.79 s(1 H); 8.60 d (J = 8.3 Hz, 1 H); 7.93 m(2H); 7.70 s(1 H);
7.62 m (2H); 7.49 s (2H); 7.32 d (J = 8.1 Hz, 1 H); 7.19 s(1 H); 7.03 m(1 H); 6.93 m(1 H); 4.85 m (1 H); 4.32 m(1 H); 3.89 s(6H); 3.72 s(3H); 3.56 m(2H); 3.36 m(2H); 3.05 m(1 H); 2.93 m (1H); 2.63 m(2H); 1.55 m(2H); 1.39 m(2H); 1.30 m(2H).

The following compounds were obtained in analogy to the preparation methods de-scribed in detail:

Product; Method 'H-NMR (400 MHz) 8 Structure Ex. analo-reagents yousto [ppm]

390 6-(4-Hydroxybutyl)-2-(3,4,5- 389 (DMSO-d6): 10.79 s(1 H); OH
trimethoxyphenyl)quinoline-4- 8.59 d (J = 8.5 Hz, 1 H); HN
carboxylic acid [(R)-1- 7.97 d (J = 8.5 Hz, 1 H);
o,~
hydroxymethyl-2-(1 H-indol-3- 7.94 s(1 H); 7.71 s(1 H); NH
yl)ethyl]amide; 7.62 m(2H); 7.49 s (2H); N
7.31 d (J = 8.1 Hz, 1 H);
6-(4-Hydroxybut-1-ynyi)-2- 7.19 s(1H); 7.04 m(1H); 'o I~ o o (3,4,5- 6.93 m (1H); 4.85 m (1H); .1 trimethoxyphenyl)quinoline-4- 4.40 m(2H); 3.89 s (6H);
carboxylic acid ((R)-1-3.72 s (3H); 3.56 m (2H);
hydroxymethyl-2-(1 H-indol-3-3.38 m (2H); 3.03 m(1 H);
yl)ethyl]amide 2.94 m(1 H); 2.64 m(2H);
1.59 m (2H); 1.43 m (2H).
391 6-(3-Hydroxypropyl)-2-(3,4,5- 389 (DMSO-d6): 10.83 s(1 H);
trimethoxyphenyl)quinoline-4- 8.64 d (J = 8.5 Hz, 1 H); HN OH
carboxylic acid [(R)-1- 8.00 d (J = 8.7 Hz, 1 H);
NH
hydroxymethyl-2-(1 H-indol-3- 7.97 s (1 H); 7.76 d (J = OH yl)ethyl]amide; 1.5 Hz, 1H); 7.66 m(2H);

7.53 s (2H); 7.35 d (J = NNI
6-(3-Hydroxyprop-1-yny1)-2- o o 7.9 Hz, 1 H); 7.23 s(1 H);
(3,4,5- 7.06 m (1H); 6.97 m (1H); "o trimethoxyphenyl)quinoline-4-4.91 m(1 H); 4.59 m(1 H);
carboxylic acid [(R)-1- 4.40 m(1 H); 3.93 s(6H);
hydroxymethyl-2-(1 H-indol-3- 3.76 s(3H); 3.59 m (2H);
yl)ethyl]amide 3.45 m(2H); 3.06 dd (J =

5.8 Hz / 14.9 Hz, 1H);
2.96 dd (J = 8.3 Hz / 14.7 Hz, 1 H); 2.73 m (2H); 1.76 m (2H).

Product; Method ,H-NMR (400 MHz) S Structure Ex. analo-reagents gous to [ppm]

392 6-(3-Methoxypropyl)-2-(3,4,5- 389 (DMSO-d6): 10.78 s(1H);
trimethoxyphenyl)quinoline-4- 8.61 d (J = 8.3 Hz, 1 H); o HN
carboxylic acid [(R)-1- 7.97 d (J = 8.7 Hz, 1 H);
NH /
hydroxymethyl-2-(1 H-indol-3- 7.94 s(1 H); 7.72 s(1 H); o~ ~ I
yI)ethyl]amide; 7.62 m (2H); 7.49 s (2H);
I ~N
7.31 d (J = 8.1 Hz, 1 H);
6-(3-Methoxyprop-1-ynyl)-2- i 7.19 s(1 H); 7.03 m(1 H); o o (3,4,5- 6.93 m (1H); 4.85 m (1H); ~,o trimethoxyphen yl)quinoline-4-4.36 m(1 H); 3.89 s (6H);
carboxyiic acid 1'(R)-1-3.72 s (3H); 3.56 m (2H);
hydroxymethy1-2-(1 H-indol-3-3.31 m (2H); 3.21 s (3H);
yl)ethylJamide 3.03 m(1 H); 2.92 m(1 H);
2.68 m (2H); 1.77 m (2H).

393 3',4',5'-Trimethoxy-4-(3- 389 (DMSO-ds): 10.79 s(1 H); H
methoxypropyl)biphenyl-3- 8.17 d (J = 8.2 Hz, 1 H); /~~
carboxylic acid [(R)-1- 7.63 d (J = 7.8 Hz, 1 H); NH
OH
hydroxymethyl-2-(1H-indol-3- 7.58-7.61 m(1H); 7.43 s o yl)ethyl]amide; (1 H); 7.31 d (J = 7.8 Hz, 1 H); 7.26 d (J = 7.8 Hz, ~
3 ; 4', 5'-Trimethoxy-4-(3- o 0 methoxyprop-1-ynyl)biphenyl- 1 =7 H); .4 7.1Hz,7 1 s (1 H);6 H); 7.94t.03 (J t = (J o\
3-carboxylic acid ((R)-1- 7.4 Hz, 1 H); 6.87 s (2H);
hydroxymethyl-2-(1 H-indol-3- 4.80 t (J = 5.6 Hz, 1 H);
yl)ethylJamide 4.18-4.26 m(1 H); 3.85 s (6H); 3.70 s (3H); 3.51-3.58 m(1 H); 3.42-3.48 m (1 H); 3.19-3.22 m (5H);
3.03 dd (J = 14.5 Hz, J=
5.8 Hz, 1 H); 2.86 dd (J =
14.4 Hz, J= 8.6 Hz, 1 H);
2.62-2.70 m (2H); 1.66-1.73 m (2H).

Product; Method 'H-NMR (400 MHz) S Structure Ex. analo-reagents 9 ut [ppm]

394 3',4',5'-Trimethoxy-5-(3- 389 (DMSO-d6): 10.76 s(1 H); N H
o' methoxypropyl)biphenyl-3- 8.21 d (J = 8.2 Hz, 1 H); O)NH
carboxylic acid [(R)-1- 7.84 s (1 H); 7.67 d (J = o r~
hydroxymethyl-2-(1 H-indol-3- 7.8 Hz, 1 H); 7.62 s (2 H); I
yl)ethyl]amide; 7.30 d (J = 7.8 Hz, 1 H); I
. 0 Oi 3', 4; 5' Trimethoxy-5-(3- 7.Hz1,5 1 s H); (1 6 H); .92 7.03 t .97 (J m = 7.4 (3H); \
methoxyprop-1-ynyl)biphenyl- 4.81 t (J = 5.6 Hz, 1 H);
3-carboxylic acid ((R)-1-4.20-4.28 m(1 H); 3.88 s hydroxyrnethyl-2-(1 H-indoi-3-(6H); 3.70 s (3H); 3.46-yl)ethyl]amide 3.59 m (2H); 3.36 t (J =
6.2 Hz, 2H); 3.25 s (3H);
3.04 dd (J = 14.5 Hz, J =
5.8 Hz, 1 H); 2.94 dd (J =
14.4 Hz, J= 8.3 Hz, 1 H);
2.72 t (J = 7.6 Hz, 2H);
1.83-1.91 m (2H).

395 3',4'-Dimethoxy-5-(3- 389 (DMSO-d6): 10.76 s(1 H); - N
~
methoxypropyl)biphenyl-3- 8.21 d (J = 8.2 Hz, 1 H);
carboxylic acid [(R)-1- 7.84 s(1 H); 7.67 d (J = HO

hydroxymethyl-2-(1 H-indol-3- 7.8 Hz, 1 H); 7.59 s (2 H);
yI)ethyl]amide; 7.30 d (J = 7.8 Hz, 1 H); 0 o~, 7.22-7.24 m (2H); 7.14 0 ~
3;4'-Dimethoxy-5-(3- (1H); 7.02-7.06 m (2H);
methoxyprop-1-ynyl)biphenyl- 6.96 t(J - 7.4 Hz, 1 H);
3-carboxylic acid ((R)-1- 4.81 t(J - 5.6 Hz, 1 H);
hydroxymethyl-2-(1 H-indol-3- 4.21-4.29 m(1 H); 3.86 s yl)ethyl]amide (3H); 3.80 s (3H); 3.46-3.59 m (2H); 3.35 t (J =
6.2 Hz, 2H); 3.25 s (3H);
3.04 dd (J = 14.5 Hz, J =
5.8 Hz, 1 H); 2.94 dd (J =

Product; Method 'H-NMR (400 MHz) 8 Structure Ex. analo-reagents gO1S to [Ppm]
14.4 Hz, J= 7.8 Hz, 1 H);
2.71 t (J = 7.8 Hz, 2H);
1.83-1.90 m (2H).

396 5-(3-Hydroxypropyl)-3',4'- 389 (DMSO-d6): 10.75 s(1 H); - / N
~
dimethoxybiphenyl-3- 8.21 d (J = 8.2 Hz, 1 H);
carboxylic acid [(R)-1- 7.83 s(1 H); 7.67 d (J = Ho hydroxymethyl-2-(1 H-indol-3- 7.4 Hz, 1 H); 7.59 s (2 H);
yl)ethyl]amide; 7.30 d (J = 7.8 Hz, 1 H); 0 oH
7,22-7.24 m (2H); 7.14 0 5-(3-Hydroxypropyl)-3;4' (1H); 7.02-7.06 m (2H);
dimethoxybiphenyl-3- 6.96 t (J = 7.4 Hz, 1 H);
carboxylic acid ((R)-1- 4.80 t (J = 5.6 Hz, 1 H);
hydroxymethyl-2-(1 H-indol-3- 4.52 (J - 5.1 Hz; 1 H);
yl)ethyl]amide 4.21-4.29 m(1H); 3.86 s (3H); 3.80 s (3H); 3.42-3.59 m (4H); 3.04 dd (J =
14.5 Hz, J= 5.8 Hz, 1 H);
2.94 dd (J = 14.4 Hz, J =
7.8 Hz, 1 H); 2.71 t (J = 7.6 Hz, 2H); 1.75-1.82 m (2H).

397 5-(5-Hydroxypentyl)-3',4',5'- 389 (DMSO-d6): 10.76 s(1H); H
trimethoxybiphenyl-3- 8.20 d (J = 7.8 Hz, 1 H);
carboxylic acid [(R)-1- 7.83 s (1 H); 7.67 d (J = HO NH 0H

hydroxymethyl-2-(1 H-indol-3- 7.8 Hz, 1 H); 7.60 s (2 H);
yI)ethyl]amide; 7.30 d (J = 7.8 Hz, 1 H);
7.15 s (1 H); 7.03 t (J = 7.4 0 5-(5-Hydroxypent- 1-ynyl)- Hz, 1 H); 6.95 t (J - 7.4 0 0-3', 4; 5'-trimethoxybiphenyl-3- Hz, 1 H); 6.92 s (2H); 4.81 carboxylic acid ((R)-1- t (J = 4.7 Hz, 1 H); 4.37 t (J
hydroxymethyl-2-(1 H-indol-3- = 4.5 Hz, 1 H); 4.20-4.29 m yl)ethyl]amide (1 H); 3.88 s (6H); 3.70 s (3H); 3.47-3.59 m (2H);

Product; Method 'H-NMR (400 MHz) S Structure Ex. analo-reagents gous to [ppm]
3.37-3.41 m (2H); 3.04 dd (J = 14.5 Hz, J 5.8 Hz, 1 H); 2.94 dd (J = 14.4 Hz, J = 7.8 Hz, 1 H); 2.68 t (J
=
7.6 Hz, 2H); 1.60-1.67 m (2H); 1.44-1.51 m (2H);
1.31-1.38 m (2H).

398 5-(3-Hydroxypropyl)-3',4',5'- 389 (DMSO-d6): 10.76 s(1H); Q N
trimethoxvbiphenyl-3- 8.21 d(J = 8.2 Hz, 1 H); ~
carboxylic acid [(R)-1- 7.83 s(1 H); 7.67 d (J = Ho T
O NH
hydroxymethyl-2-(1 H-indol-3- 7.8 Hz, 1 H); 7.62 (2 H);
I
yI)ethyl]amide; 7.30 d (J = 7.8 Hz, 1 H); 0 oH
7.14 s (1 H); 7.03 t (J = 7.4 0 5-(3-Hydroxypropyl)-3', 4, 5'- o~
Hz, 1 H); 6.95 t(J = 7.4 Hz, trimethoxybiphenyl-3- 1 H); 6.92 s (2H); 4.81 t (J
carboxylic acid ( ( R ) - 1 -= 5.4 Hz, 1 H); 4.53 t(J = 5 hydroxymethyl-2-(1 H-indol-3- Hz, 1 H); 4.20-4.28 m(1 H);
yl)ethylJamide 3.88 s (6H); 3.70 s (3H);

3.43-3.59 m (4H); 3.03 dd (J = 14.5 Hz, J= 5.8 Hz, 1 H); 2.94 dd (J = 14.4 Hz, J = 7.8 Hz, 1 H); 2.72 t (J
=
7.6 Hz, 2H); 1.76-1.83 m (2H).

399 5-(4-Hydroxybutyl)-3',4',5'- 389 (DMSO-d6): 10.76 s(1 H); - H
N
\
trimethoxybiphenyl-3- 8.20 d (J = 8.2 Hz, 1 H);
carboxylic acid [(R)-1- 7.84 s (1 H); 7.67 d (J = Ho NH
hydroxymethyl-2-(1 H-indol-3- 7.7 Hz, 1 H); 7.61 s (2 H);
yI)ethyl]amide; 7.30 d (J = 7.8 Hz, 1 H); 0 oH
7.15s(1H); 7.03t(J=7.4 5-(4-Hydroxybut-1-yny1)- Hz, 1 H); 6.95 t(J = 7.4 Hz, 3', 4; 5'-trimethoxybiphenyl-3- 1 H); 6.92 s(2H); 4.81 t(J

Product; Method 'H-NMR (400 MHz) S Structure Ex. analo-reagents 9 us t [pPm]
carboxylic acid [(R)-1- = 5.5 Hz, 1 H); 4.41 t (J
=
hydroxymethyl-2-(1 H-indol-3- 5.1 Hz, 1 H); 4.20-4.28 m yl)ethyl]amide (1 H); 3.88 s (6H); 3.70 s (3H); 3.46-3.60 m (2H);
3.41-3.46 m (2H); 3.04 dd (J = 14.5 Hz, J 5.8 Hz, 1 H); 2.94 dd (J = 14.4 Hz, J = 7.8 Hz, 1 H); 2.68 t (J
7.6 Hz, 2H); 1.63-1.70 m (2H); 1.44-1.51 m (2H).

400 3',4',5'-Trimethoxy-5-[2-(4- 389 (DMSO-d6): 10.78 s(1 H); N
methoxyphenyl)ethyl]- 8.22 d (J = 8.2 Hz, 1 H);
HO
biphenyl-3-carboxylic acid 7.84 s (1 H); 7.70-7.67 m 0 NH
[(R)-1-hydroxymethyl-2-(1H- (2H); 7.53 s (1 H); 7.31 d i indol-3-yl)ethyl]amide; (J = 7.8 Hz, 1 H); 7.15-7.17 1~ o m (3H); 7.04 t (J = 7.4 Hz, 0. 1 3', 4 ; 5' Trimethoxy-5-(4- 1 H); 6.96 t (J = 7.4 Hz, methoxyphenylethy- 1 H); 6.83-6.86 m (4H);
nyl)biphenyl-3-carboxylic acid 4.83 t (J = 5.5 Hz, 1 H);
((R)-1-hydroxymethyl-2-(1H- 4.21-4.29 m (1H); 3.87 s indol-3-y1) ethyl]amide (3H); 3.70 s (6H); 3.48-3.60 m (2H); 3.86-3.07 m (6H).

401 N-[(R)-2-[1-(2-Cyanoethyl)- 39 (DMSO-d6): 8.31 d (J 1 H-indol-3-yl]-1- 8.1 Hz, 1 H); 8.05 s(1 H); _~N

N
(hydroxymethyl)ethyl]-3'- 7.78 d (J = 7.8 Hz, 1 H);
HO
fluoro-4'-methoxy[1,1'- 7.78 d (J = 7.6 Hz, 1 H); NH
biphenyl]-3-carboxamide; 7.73 d (J = 8.0 Hz, 1 H); o 7.65 dd (J = 12.9 Hz / 2.3 1-(2-Cyanoethyl)-L- Hz, 1 H); 7.53 d (J = 8.8 tryptophanol and F
Hz, 1 H); 7.51 d (J = 8.0 ~O
Hz, 1 H); 7.50 dd (J = 7.8 Product; Method +H-NMR (400 MHz) S Structure Ex. analo-reagents sousto [ppm]
3'-Fluoro-4' methoxy(1,1'- Hz / 7.6 Hz, 1 H); 7.29 dd (J = 9.1 Hz / 8.8 Hz, 1 H);
biphenyl]-3-carboxylic acid 7.26 s (1 H); 7.13 dd (J =
8.0 Hz / 7.0 Hz, 1 H); 7.03 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 4.81 m(1 H); 4.42 t (J
= 6.6 Hz, 2H); 4.25 m (1 H); 3.90 s (3H); 3.54 m (1 H); 3.50 m(1 H); 3.03 dd (J = 14.4 Hz / 6.6 Hz, 1 H);
2.95 t (J = 6.6 Hz, 2H);
2.94 m (1 H).

402 3'-Fluoro-N-[(R)-2-(1-heptyl- 39 (DMSO-d6): 8.27 d (J = OH
1 H-indol-3-yl)-1- 8.1 Hz, 1 H); 8.03 s(1 H); o HNH N
(hydroxymethyl)ethyl]-4'- 7.78 d (J = 7.8 Hz, 1 H);
methoxy[1,1'-biphenyl]-3- 7.76 d (J = 7.8 Hz, 1 H); F I~ I~
carboxamide; 7.66 d (J = 8.0 Hz, 1 H);
7.64 dd (J = 12.9 Hz / 2.3 1-Heptyl-L-tryptophanol and Hz, 1 H); 7.53 d (J = 8.8 3'-Fluoro-4' methoxy(1,1'- Hz, 1 H); 7.49 dd (J = 7.8 biphenyl]-3-carboxylic acid Hz / 7.8 Hz, 1 H); 7.36 d (J
= 8.0 Hz, 1 H); 7.28 dd (J =
8.8 Hz / 8.8 Hz, 1 H); 7.17 s (1 H); 7.08 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 6.98 dd (J =
8.0 Hz / 7.0 Hz, 1 H); 4.82 m(1 H); 4.25 m(1 H); 4.05 t(J = 6.9 Hz, 2H); 3.89 s (3H); 3.56 m(1 H); 3.51 m (1 H); 3.04 dd (J = 14.4 Hz / 5.8 Hz, 1 H); 2.93 dd (J =
14.4 Hz / 8.1 Hz, 1 H);

Product; Method 'H-NMR (400 MHz) S Structure Ex. analo-reagents gousto [ppm]
1.61 m (2H); 1.09 m (8H);
0.76 t(J = 7.1 Hz, 3H).

N
403 N-[(R)-2-[1-(4-Cyanobutyl)- 39 (DMSO-d6): 8.27 d (J = ?,.--indol-3-yl]-1- 8.1 Hz, 1 H); 8.04 s(1 H); N

(hydroxymethyl)ethyl]-3'- 7.78 d(J = 7.7 Hz, 1 H); Ho H
fluoro-4'-methoxy[1,1'- 7.77 d (J = 7.5 Hz, 1 H); o biphenyl]-3-carboxamide; 7.68 d (J = 8.0 Hz, 1 H);
7.65 dd (J = 13.0 Hz / 2.3 F~
1-(4-Cyanobutyl)-~- Hz 1 I-I); 7.54 d (J = 8.7 .10 tryptophanol and Hz, 1 H); 7.50 dd (J = 7.7 3'-Fluoro-4' methoxy(1,1' Hz / 7.5 Hz, 1 H); 7.41 d (J
biphenyl]-3-carboxylic acid = 8.0 Hz, 1 H); 7.28 dd (J =
9.0 Hz / 8.7 Hz, 1 H); 7.18 s (1 H); 7. 10 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 7.00 dd (J =
8.0 Hz / 7.0 Hz, 1 H); 4.81 m (1H); 4.13t(J=6.8 Hz, 2H); 4.25 m(1 H); 3.90 s (3H); 3.55 m(1 H); 3.52 m (1 H); 3.03 dd (J = 14.6 Hz / 6,2 Hz, 1 H); 2.96 t(J =
7.1 Hz, 2H); 2.93 dd (J =
14.6 Hz / 7.4 Hz, 1 H);
1.74 m (2H); 1.40 m (2H).

404 3'-Fluoro-N-[(R)-l- 39 (DMSO-d6): 8.27 d(J= o"
(hydroxymethyl)-2-[1-(3- 8.1 Hz, 1H); 8.03 s(1H);
phenoxypropyl)-1 H-indol-3- 7.78 d (J = 7.7 Hz, 1 H);
F o yI]ethyl]-4'-methoxy[1,1'- 7.77 d (J = 7.5 Hz, 1 H);
biphenyl]-3-carboxamide; 7.68 d (J = 8.0 Hz, 1 H);
7.64 dd (J = 13.0 Hz / 2.3 1-(3-Phenoxypropyl)-L- Hz, 1 H); 7.52 d (J = 8.9 tryptophanol and Hz, 1 H); 7.49 dd (J = 7.7 Product; Method 'H-NMR (400 MHz) S Structure Ex. analo-reagents gO1stO [ppm]
3' Fluoro-4' methoxy(1,1' Hz / 7.5 Hz, 1 H); 7.38 d(J
biphenyl]-3-carboxylic acid = 8=0 Hz, 1 H); 7.27 dd (J =
8.9 Hz / 8.9 Hz, 1 H); 7.24 dd (J = 7.6 Hz / 7.6 Hz, 2H); 7.19 s(1 H); 7.06 dd (J = 8.0 Hz / 7.0 Hz, 1 H);
6.98dd(J=8.0Hz/7.0 Hz, 1 H); 6.90 dd (J = 7.6 Hz / 7.6 Hz, 1 H); 6.84 d (J
= 7.6 Hz, 2H); 4.79 m (1 H); 4.26 t (J = 6.7 Hz, 2H); 4.25 m(1 H); 3.88 s (3H); 3.54 m(1 H); 3.51 m (1 H); 3.02 dd (J = 14.1 Hz / 6.4 Hz, 1 H); 3.80 t(J =
6.0 Hz, 2H); 2.93 dd (J =
14.1 Hz / 7.7 Hz, 1 H);
2.10 m (2H).

405 3'-Fluoro-N-[(R)-l- 39 (DMSO-d6): 8.30 d (J = H
~/
(hydroxymethyl)-2-[1-(2- 8.1 Hz, 1 H); 8.05 s(1 H); o"" ~N
methoxyethyl)-1 H-indol-3- 7.78 d (J = 7.8 Hz, 1 H); F -~
yl]ethyl]-4'-methoxy[1,1'- 7.78 d (J = 7.6 Hz, 1 H); l ~~
biphenyl]-3-carboxamide; 7.68 d (J = 8.0 Hz, 1 H);
7.65 dd (J = 13.1 Hz / 2.3 1-(2-Methoxyethyl)-L- Hz, 1 H); 7.53 d(J = 8.8 tryptophanol and Hz, 1 H); 7.50 dd (J = 7.8 3'-Fluoro-4' methoxy(1,1' Hz / 7.6 Hz, 1 H); 7.40 d (J
biphenyl]-3-carboxylic acid = 8=0 Hz, 1 H); 7.28 dd (J =
8.8 Hz / 8.8 Hz, 1 H); 7.18 s (1 H); 7.09 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 6.99 dd (J =
8.0 Hz / 7.0 Hz, 1 H); 4.82 Product; Method 'H-NMR (400 MHz) S Structure Ex. analo-reagents gousto [ppm]
m(1 H); 4.25 m(1 H); 4.23 t (J = 5.3 Hz, 2H); 3.90 s (3H); 3.56 t (J = 5.3 Hz, 2H); 3.55 m(1 H); 3.51 m (1 H); 3.10 s (3H); 3.04 dd (J = 14.4 Hz / 6.0 Hz, 1 H);
2.93 dd (J = 14.4 Hz / 7.8 Hz, 1 H).

406 N-[(R)-2-[1-(3-Cyanopropyl)- 39 (CDCI3): 7.72 d (J = 8.0 /N
1 H-indol-3-yi]-1- Hz, 1 H); 7.72 s(1 H); 7.61 /~
~
(hydroxymethyl)ethyl]-3'- d (J = 7.9 Hz, 1 H); 7.59 d N
~
fluoro-4'-methoxy[1,1'- (J = 7.5 Hz, 1 H); 7.41 dd HO H
biphenyl]-3-carboxamide; (J = 7.9 Hz / 7.5 Hz, 1 H); N

7.34 d(J = 8.0 Hz, 1 H); 0 1-(3-Cyanopropyl)-L- ~
7.03 s(1 H); 7.29-7.19 m tryptophanol and (3H); 7.13 dd (J = 8.0 Hz 3'-Fluoro-4'-methoxy(1,1'- 7.0 Hz, 1 H); 7.01 dd (J = F
biphenyl]-3-carboxylic acid 8.0 Hz / 7.0 Hz, 1 H); 6.58 d (J = 7.4 Hz, 1 H); 4.49 m (1 H); 4.26 t (J = 6.0 Hz, 2H); 3.94 s (3H); 3.83 m (1 H); 3.79 m(1 H); 3.17 m (2H); 2.18 m (2H); 2.16 m (2H).

407 4-Ethoxy-3'-methoxybiphenyl- 335 (DMSO-d6): 8.42 d (J = N
3-carboxylic acid [(R)-2-(1- 7.8 Hz, 1 H); 8.15 s(1 H); N
cyanomethyl-1 H-indol-3-yl)-1- 7.53 d (J = 8.2 Hz, 1 H);
hydroxymethylethyl]amide; 7.36 t (J = 8.2 Hz, 1 H); Ho 7.25 s(1 H); 7.20 m(3H); o~
Methyl (R)-3-(1-cyanomethyl-7.13 m (3H); 6.91 d (9.3 ~o 1 H-indol-3-yl)-2-((4-ethoxy-3'-Hz, 1 H); 5.49 s(2H); 4.99 methoxybiphen yl-3-carbon yl)-m(1 H); 4.25 m(1 H); 4.15 Product; Method 'H-NMR (400 MHz) 5 Structure Ex. analo-reagents sousto IPpm]
amino]propionate q (J = 6.3 Hz, 2H); 3.82 s (3H); 3.50 m(1 H); 3.46 m (1H); 3.00 m (2H); 1.31 t (J = 6.6 Hz, 3H).

408 6-Methoxy-2-(3,4,5- 335 (DMSO-ds): 8.71 d (J = ;
trimethoxyphenyl)quinoline-4- 8.2 Hz, 1 H); 8.00 t (J = 4.3 N
carboxylic acid [(R)-2-(1- Hz, 2H); 7.73 d (J = 7.9 cyanomethyl-1 H-indol-3-yl)-1- Hz, 1 H); 7.54 d (J = 7.8 Ho O NH
hydroxymethylethyl]amide; Hz, 1 H); 7.50 s(2H); 7.46 s(1 H); 7.41 m(1 H); 7.30 N
Methyl (R)-3-(1-cyanomethyl- s(1 H); 7.21 t (J - 7.6 Hz, o ~
1 H-indol-3-yl)-2-{(6-methoxy- 1 H); 7.09 t(J - 7.5 Hz, ~o 2-(3,4,5- 1 H); 5.50 s (2H); 4.95 t (J
trimethoxyphenyl) quinoline-4-= 5.5 Hz, 1 H); 4.40 m carbon yl]amino} propionate (1 H); 3.92 s (6H); 3.76 s (3H); 3.74 s (3H); 3.74 m (2H); 3.03 dd (J = 14.4 Hz / 5.5 Hz, 1 H); 2.95 dd (J =
14.4 Hz / 8.1 Hz, 1 H).

409 6-Methoxy-2-(3,4,5- 335 (DMSO-d6): 8.67 d (J = N
trimethoxyphenyl)quinoline-4- 8.6 Hz, 1 H); 8.01 d (J =
carboxylic acid {(R)-2-[1-(4- 7.8 Hz, 1 H); 8.00 s(1 H); N\~
cyano-butyl)-1 H-indol-3-yl]-1- 7.68 d (J = 7.8 Hz, 1 H);
hydroxymethylethyl}amide; 7.51 s (2H); 7.48 s (1 H); Ho o NH
7.43 m(2H); 7.24 s(1 H); 0, Methyl (R)-3-(1-(4- 7.11 t(J - 7.8 Hz, 1 H); 'o N
-cyanobutyl)-1 H-indol-3-yl]-2- 6.98 t(J - 7.4 Hz, 1 H); \o 0 {[6-methoxy-2-(3, 4, 5-4.90 m (1H); 4.38 m (1H);
trimethoxyphenyl)quinoline-4- 4.14 m (2H); 3.92 s (6H);
carbonyl]amino]propionate 3.75 s (6H); 3.60 m (2H);

2.99 m (2H), 2.40 t (J =
7.0, Hz, 2H);1.76 t (J = 7.5 Product; Method 'H-NMR (400 MHz) S Structure Ex. analo-reagents yous to [ppm]

Hz, 2H); 1.45 t (J = 7.4 Hz, 2H).

410 4-Hydroxy-3',4',5'- 39 (DMSO-d6): 12.49 s(1 H); - N
~
trimethoxybiphenyl-3- 10.76 s(1 H); 8.67 d (J =
carboxylic acid [(R)-1- 8.1 Hz, 1 H); 8.10 d (J = HO
hydroxymethyl-2-(1 H-indol-3- 2,1 Hz, 1 H); 7.65 m(1 H); 0 NH
OH
yI)ethyl]amide; 7,28 d (J = 7.9 Hz, 1 H);
~1o 7.12 s(1H); 6.93 m (3H); \o (D)-Tryptophanol 6.84 s(2H); 4,88 m(1 H);
o and 4.26 m(1 H); 3.84 s (6H);
3.65 s (3H); 3.50 m (2H);
4-Hydroxy-3;4;5' 2.97 m (2H).
trimethoxybiphenyl-3-carboxylic acid 411 4-(3-Cyanopropoxy)-3',4',5'- 39 (DMSO-d6): 10.78 s(1 H); \ N
trimethoxybiphenyl-3- 8.21 d (J = 8.1 Hz, 1 H);
HO
carboxylic acid [(R)-1- 8.02 d (J = 2.6 Hz, 1 H); O NH
N
hydroxymethyl-2-(1 H-indol-3- 7.71 dd (J = 2.5 Hz / 8.5 a~
yI)ethyl]amide; Hz, 1 H); 7.68 d (J = 7.7 '0 Hz, 1 H); 7.30 d (J = 7.9 4-(3-Cyanopropoxy)-3', 4, 5 ' -H z , 1 H); 7.19 d(J = 8.7 trimethoxybiphenyl-3- Hz, 1 H); 7.14 s(1 H); 7.03 carboxylic acid m (1 H); 6.94 m (1 H); 6.82 and s(2H); 4.94 m(1 H); 4.16 m(1 H); 4.13 m (2H); 3.83 (D)-Tryptophanol s (6H); 3.66 s (3H); 3.48 m (2H); 2.94 m (2H); 2.60 m (2H); 1.99 m (2H).

Product; Method 'H-NMR (400 MHz) S Structure Ex. analo-reagents sousto [ppm]

412 4-Cyclopentyloxy-3'-fluoro-4'- 39 (DMSO-d6): 10.81 s(1 H); -,"~
methoxybiphenyl-3-carboxylic 8.36 d (J = 8.2 Hz, 1 H);
acid [(R)-2-hydroxy-1-(1 H- 8.16 (1 H); 7.70-7.74 m o H
indol-3-ylmethyl)ethyl]amide; (2H); 7.51 d (J = 12.9 Hz, 0"0 1 H); 7.42 d (J = 8.6 Hz, F
(D)-Tryptophanol 1 H); 7.33 d (J = 7.8 Hz, o and 1 H); 7.23 t (J = 8.8 Hz, 1H);7.18d(J8.9Hz, 4-Cyclopentyloxy-3'-fluoro-4'- 1 H); 7.15 s(1 H); 7.06 t (J
methoxybiphenyl-3-carboxylic = 7.4 Hz, 1 H); 7.15 s(1 H);
acid 6.97 t (J = 7.4 Hz, 1 H);
5.01 m (1 H); 4.97 t (J =
4.9 Hz, 1 H); 4.24-4.31 m (1 H); 3.87 s (3H); 3.42-3.54 m (2H); 2.93-3.04 m (2H); 1.78-1.96 m (3H);
1.52-1.70 m (5H).

413 4-Cyclopentyloxy-3'- 39 (DMSO-d6): 10.81 s(1 H); N
methylbiphenyl-3-carboxylic 8.36 d (J = 8.2 Hz, 1 H); /
acid [(R)-1-hydroxymethyl-2- 8.21 (1H); 7.70-7.75 m NH o10 OH (1 H-indol-3-yl)ethyl]amide; (2H); 7.40-7.45 m (2H);
7.31-7.35 m (2H); 7.20 d (D)-Tryptophanol (J = 8.6 Hz, 1 H); 7.15 m and (2H); 7.06 t (J = 7.3 Hz, 1 H); 6.97 t (J = 7.4 Hz, 4-Cyclopentyloxy-3'- 1 H); 5.02 m (1 H); 4.97 t (J
methylbiphenyl-3-carboxylic = 4.9 Hz, 1 H); 4.24-4.31 m acid (1 H); 3.42-3.54 m (2H);
2.94-3.04 m (2H); 2.38 s (3H); 1.79-1.94 m (3H);
1.64-1.73 m (3H); 1.51-1.61 m (2H).

Product; Method 'H-NMR (400 MHz) S Structure Ex. analo-reagents sous to [ppm]

414 3'-(1-Butyl-3-methylureido)-4- 39 (DMSO-ds): 10.81 s(1H); N H
cyclopentyloxybiphenyl-3- 8.37 d (J = 8.2 Hz, 1 H); E5Pa carboxylic acid [(R)-l- 8.22 d (J = 2.3 Hz, 1 H); "H o~
hydroxymethyl-2-(1 H-indol-3- 7.76 dd (J = 8.6 Hz, J= ~
yl)ethyl]amide; 2.3 Hz, 1 H); 7.70 d (J =
7.8 Hz, 1 H); 7.53-7.50 m (D)-Tryptophanol (1 H); 7.48 t (J = 7.8 Hz, ~
Hi O
=
and 1 H); 7.43 (1 H); 7.31 d (J
8.2 Hz, 1 H); 7.22 d (J =
3'-(1-Butyl-3-methylureido)-4- 8.6 Hz, 1 H); 7.14-7.18 m cyclopentyloxybiphenyl-3- (2H); 7.05 t (J = 7.4 Hz, carboxylic acid 1 H); 6.96 t (J = 7.4 Hz, 1 H); 5.66 q (J = 4.3 Hz, 1 H); 5.03 m (1 H); 4.97 t (J
= 5.1 Hz, 1 H); 4.24-4.32 m (1 H); 3.61 t (J = 7.4 Hz, 1 H); 3.42-3.54 m (2H);
2.94-3.04 m (2H); 2.54 d (J = 4.3 Hz, 3H); 1.79-1.95 m (3H); 1.52-1.73 m (5H);
1.36-1.43 m (2H); 1.21-1.29 m (2H) 0.84 t (J = 7.4 Hz, 3H).

415 4-Cyclopentyloxy-4'-fluoro-3'- 39 (DMSO-d6): 10.81 s(1 H); H
methylbiphenyl-3-carboxylic 8.37 d (J = 8.2 Hz, 1 H);
acid [(R)-2-hydroxy-1-(1 H- 8.18 (1 H); 7.72 s(1 H); OH "" o10 indol-3-ylmethyl)ethyl]amide; 7.70 s (1 H); 7.55 d (J = 1 7.4 Hz, 1 H); 7.44-7.48 m (D)-Tryptophanol (1 H); 7.33 d (J = 8.2 and Hz,1 H); 7.20 t (J = 7 Hz, F
1 H); 7.15 s (1 H); 7.06 t (J
4-Cyclopentyloxy-4'-fluoro-3'- = 7.4 Hz, 1 H); 6.97 t (J =

Product; Method 'H-NMR (400 MHz) S Structure Ex. analo-reagents s usto [ppm]
methylbiphenyl-3-carboxylic 7.4 Hz, 1 H); 5.02 m(1 H);
acid 4.97 t (J = 5.2 Hz, 1 H);
4.25-4.32 m (1 H); 3.42-3.54 m (2H); 2.94-3.04 m (2H); 2.31 s (3H); 1.79-1.96 m (3H); 1.51-1.73 m (5H).

416 4-Cyclopentyloxy-3'- 39 (DMSO-d6): 10.80 s(1H); ,"~
methoxybipheny!-3-carboxy!ic 8.37 d(J = 8.2 Hz, 1 H);

acid [(R)-1-hydroxymethyl-2- 8.19 d (J = 2.3 Hz, 1 H); OH NH 0 (1 H-indol-3-yl)ethyl]amide; 7.76 dd (J = 8.6 Hz, J =

2.3 Hz, 1 H); 7.70 d (J =
(D)-Tryptophanol 7.8 Hz, 1 H); 7.36 t (J = 8 and Hz, 1 H); 7.33 d (J = 7.8 Hz, 1 H); 7.18-7.21 m (2H);
4-Cyclopentyloxy-3' 7.14 s (2H); 7.05 t (J = 7.4 methoxybiphenyl-3-carboxylic Hz, 1 H); 6.96 t (J = 7.2 acid Hz, 1 H); 6.92 dd (J = 8 Hz, J = 2 Hz 1 H); 5.03 m (1 H); 4.96 t(J = 5.1 Hz, 1 H); 4.24-4.31 m(1 H);
3.82 s (3H); 3.42-3.53 m (2H); 2.93-3.04 m (2H);
1.79-1.95 m (3H); 1.52-1.72 m (5H).

417 4-Cyclopentyloxy-3',4'- 39 (DMSO-d6): 10.81 s(1 H); N
dimethoxybiphenyl-3- 8.37 d (J = 7.8 Hz, 1 H); ~
HO
carboxylic acid [(R)-1- 8.16 d (J = 2.3 Hz, 1 H); 0 NH
hydroxymethyl-2-(1H-indol-3- 7.69-7.73 m (2H); 7.36 d 0,10 y!)ethyl]amide; (J = 8.2 Hz, 1 H); 7.33 d (J ~o = 7.8 Hz, 1 H); 7.14-7.19 m (D)-Tryptophanol (4H); 7.03 t (J = 8.2 Hz, Product; Method 'H-NMR (400 MHz) 8 Structure Ex. analo-reagents 9 usto [ppm]
and 1 H); 6.96 t (J = 7.42 Hz, 1 H); 5.02 m (1 H); 4.96 t (J
4-Cyclopentyloxy-3 ; 4'- = 5 Hz, 1 H); 4.24-4.31 m dimethoxybiphenyl-3- (1 H); 3.84 s(3H); 3.79 s carboxylic acid (3H); 3.41-3.53 m (2H);
2.93-3.04 m (2H); 1.79-1.93 m (3H); 1.52-1.72 m (5H).

418 5-8enzo[ 1,3]dioxoi-5-y1-2- 39 (DMSO-ds): 10.80 s(1H); - N
~
cyclopentyloxy-N-[(R)-1- 8.35 d (J = 7.8 Hz, 1 H);
HO
hydroxymethyl-2-(1 H-indol-3- 8.11 d (J = 1.9 Hz, 1 H); 0 NH
yl)ethyl]benzamide; 7.66-7.71 m (2H); 7.34 d 0'0 (J = 8.2 Hz, 1 H); 7.14-7.19 <o I~
(D)-Tryptophanol m (3H); 7.04-7.10 m (2H);
and 6.94-6.99 m (2H); 6.05 s (2H); 5.0 m (1 H); 4.95 t (J
5-Benzo[1, 3]dioxo1-5-y1-2- = 5 Hz, 1 H); 4.24-4.31 m cyclopentyloxybenzoic acid (1 H); 3.42-3.53 m (2H);
2.93-3.04 m (2H); 1.77-1.93 m (3H); 1.54-1.69 m (5H).

419 4-Cyclopentyloxy-3',4',5'- 39 (DMSO-d6): 10.81 s(1 H); \ ~ N
trimethoxybiphenyl-3- 8.37 d (J = 7.8 Hz, 1 H); ~
HO
carboxylic acid [(R)-1- 8.16 d (J = 2.3 Hz, 1 H); 0 NH
hydroxymethyl-2-(1 H-indol-3- 7.76 dd (J = 9 Hz, J = 2.7 0"0 I
yI)ethyl]amide; Hz, 1 H); 7.70 d (J = 7.8 Hz, 1 H); 7.33 d (J = 8.2 o'~
(D)-Tryptophanol Hz, 1 H); 7.19 d (J = 8.9 and Hz, 1 H); 7.14 d(J = 1.9 Hz, 1 H); 7.05 t(J = 7.4 4-Cyclopentyloxy-3 ; 4; 5' Hz, 1 H); 6.96 t (J = 7.4 trimethoxybiphenyl-3- Hz, 1 H); 6.85 s (2 H); 5.04 Product; Method 'H-NMR (400 MHz) S Structure Ex. analo-reagents sousto [ppm]
carboxylic acid m(1 H); 4.97 t (J = 5 Hz, 1 H); 4.24-4.31 m(1 H);
3.86 s (6H); 3.69 s (3H);
3.41-3.53 m (2H); 2.93-3.04 m (2H); 1.79-1.95 m (3H); 1.51-1.73 m (5H).

420 4-Cyclopentyloxy-3',4'- 39 (DMSO-d6): 10.81 s(1 H); N
difluoro-5'-methoxybiphenyl-3- 8.37 d (J = 8.2 Hz, 1 H);
HO
r.arhnxy Iir aniri r(R)-2- 8,19 d(.l = 2,3 H7 1 H); n IH
hydroxy-1-(1 H-indol-3- 7.78 dd (J = 8.7 Hz, J= ~
I
ylmethyl)ethyl]amide; 2.6 Hz, 1 H); 7.71 d (J = '~
7.8 Hz, 1 H); 7.33 d (J = F F
(D)-Tryptophanol 7.8 Hz, 1 H); 7.20-7.26 m and (3H); 7.15 (1 H); 7.06 t(J =
7.4 Hz, 1 H); 6.96 t (J = 7.4 4-Cyclopentyloxy-3; 4'- Hz, 1 H); 5.04 m(1 H); 4.97 difluoro-5' methoxybiphenyl-3- t (J = 5.1 Hz, 1 H); 4.24-carboxylic acid 4.32 m(1 H); 3.98 s (3H);
3.42-3.55 m (2H); 2.94-3.04 m (2H); 1.79-1.95 m (3H); 1.52-1.74 m (5H).
Example 421 3'-[Butyl[(1,1-dimethylethoxy)carbonyl]amino]-4-ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1 H-i ndol-3-yl)ethyl] [1,1'-bi phenyl]-3-carboxam ide;
OH ~
I \ ~
O NH N
H
Oy N

-~O
421 a) tert-Butyl (3-bromophenyl)-n-butylcarba mate tert-Butyl (3-bromophenyl)carbamate (56 g) were dissolved in DMF (250 ml), and NaH
(60%, 10g) was added in portions. The mixture was stirred until gas evolution was no longer observable and then 1-bromobutane (35 g) was slowly added dropwise. The mixture was stirred at 80 C for two hours, cooled and poured into water (1000 ml). It was extracted with ethyl acetate (150 ml), and the organic phases were washed with water (3 x 100 ml), concentrated in a rotary evaporator and dried by azeotropic distilla-tion with toluene. The title compound was obtained in quantitative yield (68g). MS
(ESI,+): 329 (M+1).

421 b) 3-(tert-Butoxycarbonylbutylamino)phenylboronic acid Butyllithium (1.6 M in hexane, 70 ml) was added dropwise to a solution of tert-butyl (3-bromophenyl)-n-butylcarbamate (31.4 g) in THF (400 ml) at -80 C and, after stirring for 30 minutes, trimethyl borate (21.5 ml) was added dropwise. The reaction was thawed to room temperature, diluted with water (300 ml) and extracted with ethyl ace-tate, and the organic phases were dried over sodium sulphate. The residue was di-gested with hexane (200 ml) and water (20 ml) and stored in a refrigerator overnight.
The product was filtered off and washed with cold hexane. Yield of the title compound 54% (16g). MS (ESI,+): 294 (M+1).

407c) 3'-[Butyl[(1,1-dimethylethoxy)carbonyl]amino]-4-ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl][1,1'-biphenyl]-3-carboxamide The title compound was obtained in a Suzuki reaction in analogy to general method 125e.

(CD30D): 8.27 d (J = 2.5 Hz, 1 H); 7.72 dd (J = 8.7 Hz / 2.5 Hz, 1 H); 7.66 d (J = 8.0 Hz, 1 H); 7.50 d (J = 7.9 Hz, 1 H); 7.45 m (1 H); 7.33 d (J = 8.0 Hz, 1 H); 7.44 dd (J = 7.9 Hz /
7.7 Hz, 1 H); 7.17 d (J = 7.7 Hz, 1 H); 7.15 d (J = 8.7 Hz, 1 H); 7.14 s(1 H);
7.07 dd (J =
8.0 Hz / 7.0 Hz, 1 H); 6.95 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 4.49 m(1 H); 4.11 m(1 H); 4.03 m(1 H); 3.69 m (2H); 3.67 m (2H); 3.14 m (2H); 1.53 m (2H); 1.45 s (9H); 1.35 m (2H);
1.24 t (J = 7.2 Hz, 3H); 0.92 t (J = 7.4 Hz, 3H).

Example 422 3'-(Butylamino)-4-ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl][1,1'-biphenyl]-3-carboxamide;
OH
I \ /
O NH N
H
\I

HN

422a ) 3-Butylaminophenylboronic acid Ethereal HCI (saturated, 6 ml) was added to a solution of tert-butyl (3-bromophenyl)-n-butylcarbamate (500 mg) in dichloromethane (5 ml) and stirred at room temperature for six hours. The precipitate was filtered off, washed with diethyl ether, taken up in water (5 ml) and mixed with aqueous sodium bicarbonate solution. The precipitate was filtered off and washed with water. The title compound was obtained in 90% (350 mg) yield.

422b) 3'-(Butylamino)-4-ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl][1,1'-biphenyl]-3-carboxamide The title compound was obtained in a Suzuki reaction in analogy to general method 125e.
(CDCI3): 8.50 d (J = 7.3 Hz, 1 H); 8.48 d (J = 2.5 Hz, 1 H); 8.13 s(1 H); 7.71 d (J = 8.0 Hz, 1 H); 7.63 dd (J = 8.6 Hz / 2.5 Hz, 1 H); 7.36 d (J = 8.0 Hz, 1 H); 7.22 dd (J = 7.8 Hz /
7.8 Hz, 1 H); 7.19 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 7.11 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 7.10 s (1 H); 6.95 d (J = 8.6 Hz, 1 H); 6.93 d (J = 7.8 Hz, 1 H); 6.86 m (1 H); 6.60 d (J = 7.8 Hz, 1 H); 4.58 m(1 H); 4.05 m (2H); 3.84 dd (J = 10.9 Hz / 3.5 Hz, 1 H); 3.77 dd (J = 10.9 Hz /
5.3 Hz, 1 H); 3.17 m (2H); 3.15 m(2H); 1.63 m(2H); 1.46 m(2H); 1.25 t(J = 6.9 Hz, 3H); 0.97 t (J = 7.3 Hz, 3H).

Example 423 3'-[Butyl[(methylamino)carbonyl]amino]-4-ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl][1,1'-biphenyl]-3-carboxamide;
OH
I \ ~
O NH N
H
/ I
\
Oy N
~ INH

423a) 3-(1-Butyl-3-methylureido)phenylboronic acid A solution of 3-butylaminophenylboronic acid (350 mg) and methyl isocyanate (103 mg) in THF (5 ml) was stirred at room temperature for one hour, a further 0.05 ml of methyl isocyanate was added, and the mixture was stirred at room temperature for a further three hours. The solvent was distilled off in a rotary evaporator, and the residue was recrystallized from ethanol. The title compound was obtained in 33% yield (150 mg).
423b) 3'-[Butyl[(methylamino)carbonyl]amino]-4-ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1 H-indol-3-yl)ethyl][1,1'-biphenyl]-3-carboxamide The title compound was obtained in a Suzuki reaction in analogy to general method 125e.

(CD3OD): 8.28 d (J = 2.5 Hz, 1 H); 7.75 dd (J = 8.7 Hz / 2.5 Hz, 1 H); 7.65 d (J = 8.0 Hz, 1 H); 7.61 d(J = 7.9 Hz, 1 H); 7.52 dd (J = 7.9 Hz / 7.7 Hz, 1 H); 7.49 m(1 H); 7.33 d(J =
8.0 Hz, 1 H); 7.20 d (J = 7.7 Hz, 1 H); 7.16 d (J = 8.7 Hz, 1 H); 7.14 s(1 H);
7.07 dd (J =
8.0 Hz / 7.0 Hz, 1 H); 6.95 dd (J = 8.0 Hz / 7.0 Hz, 1 H); 4.49 m(1 H); 4.11 m(1 H); 4.02 m(1 H); 3.69 m(2H); 3.67 m(2H); 3.15 m(2H); 2.67 m(3H); 1.51 m(2H); 1.34 m (2H);
1.25 t (J = 7.0 Hz, 3H); 0.91 t (J = 7.4 Hz, 3H).

The following compounds were obtained in analogy to the preparation methods de-scribed in detail:

Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 424 3'-[Butyl[(1,1-dimethyleth- 421 (CDC13): 8.48 d(J= 2.5 Hz, oxy)carbonyl]amino]-N- 1 H); 8.44 d (J = 7.1 Hz, 1 H);
[(R)-1-(hydroxymethyl)-2- 7.71 d (J = 8.0 Hz, 1 H); 7.63 Ho -vH
(1H-indol-3-yl)ethyl]-4- dd (J = 8.7 Hz / 2.5 Hz, 1H); o NH _f propoxy[1,1'-biphenyl]-3- 7.44 d (J = 8.1 Hz, 1 H); 7.43 carboxamide;
m(1 H); 7.37 dd (J = 8.1 Hz 8.1 Hz, 1 H); 7.36 d (J = 8.0 Q D
-Tryptophanol and Hz, 1 H); 7.19 dd (J = 8.0 Hz / N

3' (Butyl((1,1- 7.0 Hz, 1 H); 7.14 m(1 H); o~ ~

dime- 7.11 dd (J = 8.0 Hz / 7.0 Hz, thylethoxy)carbonyl]amino 1 H); 7.10 s (1 H); 6.99 d (J
= /\
]-4-propoxy[1,1'-biphenyl]- 8.7 Hz, 1 H); 4.59 m(1 H);
3-carboxylic acid 3.96 m (2H); 3.88 m(1 H);
3.78 m(1 H); 3.66 m (2H);
3.15 m (2H); 1.64 m (2H);
1.54 m (2H); 1.45 s (9H); 1.32 m(2H); 0.94 t (J = 7.4 Hz, 3H); 0.90 t (J = 7.4 Hz, 3H).

425 3'-(1-Butyl-3- 423 (DMSO-d6): 10.85 s(1 H); N
methylureido)-4- 8.19 d (J = 7.8 Hz, 1 H); 8.19 methoxybiphenyl-3- (1 H); 7.78 d (J = 8.6 Hz, 1 H); NH o~
H
carboxylic acid [(R)-1- 7.69 d (J = 7.8 Hz, 1 H); 7.53 o hydroxymethyl-2-(1 H- d (J = 7.8 Hz, 1 H); 7.47 t (J =
indol-3-yl)ethyl]amide; 7.8 Hz, 1 H); 7.41 (1 H); 7.33 d (J = 8.2 Hz, 1 H); 7.22 -7.15 m NN
(D)-Tryptophanol H
(3H); 7.06 t (J = 7.4 Hz, 1 H);
and 6.98 t (J = 7.4 Hz, 1 H); 5.65 q (J = 4.3 Hz, 1 H); 4.94 (1 H);
3'-(1-Butyl-3- 4.21-4.29 m(1H); 3.84 s (3H);

Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to methylureido)-4- 3.60 t (J = 7.2 Hz, 2H); 3.41-methoxybiphenyl-3- 3.57 m (2H); 2.95-3.06 m carboxylic acid (2H); 2.53 d (J = 4.3 Hz, 3H);
1.35-1.42 m (2H); 1.21-1.26 m (2H); 0.83 t (J = 7.4 Hz, 3H).

426 3'-(1-Butyl-3- 423 (DMSO-d6): 10.80 s(1H); S
H N
/
methylureido)-4-methoxy- 8.25 d (J = 8.2 Hz, 1 H); 7.68 5-mPthvlhinhPnvl-3- d(J = 7.8 Hz_ 1 H)' 763 m HO
O NH
carboxylic acid [(R)-1- (2H); 7.46-7.52 m (2H); 7.43 s I o~
hydroxymethyl-2-(1 H- (1 H); 7.32 d (J = 8.2 Hz, 1 H);
indol-3-yI)ethyi]amide; 7.18 m (2H); 7.06 t (J = 7.4 Hz, 1 H); 6.97 t(J = 7.4 Hz, Ny O
(D)-Tryptophanol 1 H); 5.65 q (J = 4.3 Hz, 1 H); HN"
and 4.89 t (J = 5.5 Hz, 1 H); 4.23-4.31 m(1 H); 3.62 s(3H);
3'-(1-Butyl-3- 3.53-3.59 m (3H); 3.45-3.50 methylureido)-4-methoxy- m(1 H); 3.04 dd (J = 14.4 Hz, 5-methylbiphenyl-3- J= 6.6 Hz, 1 H); 2.94 dd (J =
carboxylic acid 14.4 Hz, J = 6.6 Hz, 1 H); 2.54 d (J = 4.3 Hz, 3H); 2.31 s (3H); 1.35-1.42 m (2H); 1.21-1.28 m (2H); 0.83 t (J = 7.4 Hz, 3H).

Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 427 3'-(1-Butyl-3- 423 (DMSO-d6): 10.82 s(1H); H
methylureido)-4- 8.48 d (J = 8.2 Hz, 1 H); 8.20 ONH isopropoxybiphenyl-3- d(J
= 2.3 Hz, 1 H); 7.75 dd (J o~

carboxylic acid [(R)-1- = 8.2 Hz, J = 2.1 Hz, 1H); 1 hydroxymethyl-2-(1 H- 7.71 d (J = 7.8 Hz, 1 H); 7.54 indol-3-yl)ethyl]amide; d (J = 7.8 Hz, 1 H); 7.48 t (J = ~ 1 7.8 Hz, 1 H); 7.42 (1 H); 7.33 d o N
(D)-Tryptophanol ~
(J = 8.2 Hz, 1 H); 7.26 d (J =
anri 8.9 Hz, 1 H); 7.16-7.18 m (2H); 7.05 t (J = 7.4 Hz, 1 H);
3'-(1-Butyl-3- 6.98 t (J = 7.2 Hz, 1 H); 5.65 q methylureido)-4- (J = 4.3 Hz, 1 H);4.97 t (J
=
isopropoxybiphenyl-3- 4.8 Hz, 1 H); 4.79-4.85 m carboxylic acid (1 H); 4.23-4.30 m (1 H); 3.61 t (J = 7.4 Hz, 2H); 3.421-3.54 m (2H); 2.94-3.04 m (2H);
2.53 d (J = 4.3 Hz, 3H); 1.36-1.43 m (2H); 1.21-1.29 m (8H); 0.84 t (J = 7.4 Hz, 3H).

428 3'-(2-Dimethylminothoxy)- 329 (CDCI3): 8.78 s(1 H); 8.50 d H
N
4-ethoxybiphenyl-3- (J = 7.3 Hz, 1 H); 8.46 d (J
=
carboxylic acid [(R)-1- 2.5 Hz, 1 H); 7.71 d (J = 7.8 HO

hydroxymethyl-2-(1 H- Hz, 1 H); 7.56 dd (J = 2.5 Hz indol-3-yl)ethyl]amide; 8.6 Hz, 1 H); 7.32 m (2H); 5-Bromo-2-ethoxy-N-((R)-7.13 m (3H); 7.06 m (2H); o 1-hydroxymethyl-2-(1H- 6.89 m(2H); 4.55 m(1H); N f 4.11 m (2H); 3.97 m (2H); i indol-3-y1)eth yl]benzamide and 3.74 m(2H); 3.12 m (2H);
3-(2-Dimethylamino- 2.78 m (2H); 2.37 s(6H); 1.21 ethoxY)-phenYlboronic m (3H).
acid pinacol ester Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 429 4'-Ethoxy-3'-[(R)-1- 135 Column Purospher Star RP ~ H
hydroxymethyl-2-(1 H- C18 4.6x125 5pm; detection indol-3-yl)ethylcarbamoyl]- wavelength 214 nm; flow rate HO
biphenyl-3-carboxylic acid 1 mI/min; eluents A: 0.1 % o NH
methyl ester; TFA in H20, B 0.1% TFA in ACN; gradient in each case 5-Bromo-2-ethoxy-N-((R)-based on B: 5% to 95% (10') XMe 1-hydroxymethyl-2-(1H- to 95% (2') to 5% (0.5') to 5%
indol-3-y1)ethylJbenzamide (2.5') and Molecular peak (ESI, M+1):
3- 473.5 Methoxycarbonylphenyl- Retention time: 9.95 min.
boronic acid 430 4-Ethoxy- 135 Column Purospher Star RP ~ H
[1,1';3',1 "]terphenyl-3- C18 4.6x125 5pm; detection ~~
carboxylic acid [1- wavelength 214 nm; flow rate Ho hydroxymethyl-2-(1H- 1 mI/min; eluents A: 0.1% o tvH
indol-3-yl)ethyl]amide; TFA in H20, B 0.1% TFA in ACN; gradient in each case 5-Bromo-2-ethoxy-N-((R)- I ~
based on B: 5% to 95% (10') 1-hydroxymethyl-2-(1H- to 95% (2') to 5% (0.5') to 5%
indol-3-y1)ethylJbenzamide (2.5') and Molecular peak (ESI, M+1):
Biphenyl-3-boronic acid 491.6 Retention time: 11.1 min.

Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 431 3'-Acetyl-4- 135 Column Purospher Star RP H
ethoxybiphenyl-3- C18 4.6x125 5pm; detection carboxylic acid [(R)-1- wavelength 214 nm; flow rate HO .
hydroxymethyl-2-(1 H- 1 ml/min; eluents A: 0.1 % o NH
indol-3-yl)ethyl]amide; TFA in H20, B 0.1% TFA in ACN; gradient in each case 5-Bromo-2-ethoxy-N-((R)- based on B: 5% to 95% (10') 1-hydroxymethyl-2-(1H- to 95% (2') to 5% (0.5') to 5% 0 indol-3-y1)ethyl]benzamide (2.5') and Molecular peak (ESI, M+1):
3-Acetylphenylboronic 457.5 acid Retention time: 9.1 min.

432 4-Ethoxy-3'-pyrrolidin-1-yl- 135 Column Purospher Star RP H
biphenyl-3-carboxylic acid C18 4.6x125 5pm; detection [(R)-1-hydroxymethyl-2- wavelength 214 nm; flow rate H NH oJ
(1 H-indol-3-yl)ethyl]amide; 1 ml/min; eluents A: 0.1 % OH
~
TFA in H20, B 0.1% TFA in 5-Bromo-2-ethoxy-N-((R)- ACN; gradient in each case 1-hydroxymethyl-2-(1 H-based on B: 5% to 95% (10') indol-3-y1)ethy1]benzamide to 95% (2') to 5% (0.5') to 5%
and (2.5') (3-Pyrolidine-l-ylphenyl)boronic acid Molecular peak (ESI, M+1):
484.6 Retention time: 8.75 min.

Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 433 4'-Cyanomethyl-4- 135 Column Purospher Star RP H
ethoxybiphenyl-3- C18 4.6x125 5pm; detection carboxylic acid [(R)-1- wavelength 214 nm; flow rate H NH O
hydroxymethyl-2-(1H- 1 mI/min; eluents A: 0.1% OH
~
indol-3-yl)ethyl]amide; TFA in H20, B 0.1% TFA in ACN; gradient in each case 5-Bromo-2-ethoxy-N-[(R)- based on B: 5% to 95% (10') 1 -hydroxymethyl-2-(1 H-to95%(2')to5%(0.5')to5%
indol-3-yl)ethylJbenzamide (25) and Molecular peak (ESI, M+1):
(4- 454.5 Cyanomethylphe-Retention time: 9.03 min.
nyl)boronic acid 434 4'-Dimethylamino-4- 135 Column Purospher Star RP ~~
' oH
propoxy-biphenyl-3- C18 4.6x125 5pm; detection HN ~
carboxylic acid [(R)-1- wavelength 214 nm; flow rate H NH o hydroxymethyl-2-(1 H- 1 mI/min; eluents A: 0.1 % o indol-3-yl)ethyl]amide; TFA in H20, B 0.1% TFA in N-((R)-1-Hydroxymethyl-2- ACN; gradient in each case (1H-indol-3-y1)ethy1J-5- based on B: 5% to 95% (10') .N~
iodo-2-propoxy- to 95% (2') to 5% (0.5') to 5%
benzamide (25) and Molecular peak (ESI, M+1):
4-(Dimethylamino)phenyl- 472.5 boronic acid Retention time: 6.95 min.

Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 435 4-Propoxybiphenyl-3,3'- 135 Column Purospher Star RP
dicarboxylic acid 3'- C18 4.6x125 5pm; detection OH NH
diethylamide 3-{[(R)-1- wavelength 214 nm; flow rate HN
"
~ 0 hydroxymethyl-2-(1 H- 1 mI/min; eluents A: 0.1 %
indol-3-yl)ethyl]amide}; TFA in H20, B 0.1% TFA in ACN; gradient in each case I~ 1 N-((R)-1-Hydroxymethyl-2- 5% o "
based on B: 5/o to 95% (10') (1 H-indol-3-yl)ethylJ-5-to95%(2')to5%(0.5')to5%
iodo-2-propoxy- (2.5') benzamide Molecular peak (ESI, M+1):
and 528.5 3-(N, N- Retention time: 8.95 min.
Diethylaminocarbonyl)-phenylboronic acid 436 4-Propoxybiphenyl-3,4'- 135 Column Purospher Star RP
dicarboxylic acid 4'- C18 4.6x125 5pm; detection H \ NH
diethylamide 3-{[(R)-1- wavelength 214 nm; flow rate 0 HN H
hydroxymethyl-2-(1 H- 1 mI/min; eluents A: 0.1 % I~
indol-3-yl)ethyl]amide}; TFA in H20, B 0.1% TFA in ACN; gradient in each case I
N-((R)-1-Hydroxymethyl-2- based on B: 5% to 95% (10') o N
(1 H-indol-3-yl)ethylJ-5- to 95% (2') to 5% (0.5') to 5% J
iodo-2-propoxy- (2.5') benzamide Molecular peak (ESI, M+1):
and 528.5 4-(N,N- Retention time: 8.88 min.
Diethylaminocarbonyl)-phenylboronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 437 3'-[(R)-1-Hydroxymethyl-2- 135 Column Purospher Star RP H
N
(1 H-indol-3- C18 4.6x125 5pm; detection -yl)ethylcarbamoyl]-4'- wavelength 214 nm; flow rate Ho H
HN
propoxybiphenyl-4- 1 mI/min; eluents A: 0.1 % 0 carboxylic acid; TFA in H20, B 0.1 % TFA in ACN; gradient in each case N-((R)-2-Hydroxy-l-(1H- based on B: 5% to 95% (10') o indol-3-ylmethyl)ethyl]-5- HO
to95%(2')to5%(0.5')to5%
iodo-2-propoxy- (2 5,) benzamide Molecular peak (ESI, M+1):
and 473.5 4-Carboxyphenylboronic Retention time: 8.35 min.
acid 438 4'-Acetyl-4- 135 Column Purospher Star RP H
N
propoxybiphenyl-3- C18 4.6x125 5pm; detection carboxylic acid [(R)-1- wavelength 214 nm; flow rate Ho HN 0 H
hydroxymethyl-2-(1 H- 1 mI/min; eluents A: 0.1 % ~o indol-3-yl)ethyl]amide; TFA in H20, B 0.1% TFA in ACN; gradient in each case N-((R)-2-Hydroxy-1-(1 H- o based on B: 5% to 95% (10') indol-3-ylmethyl)ethyl]-5- to 95% (2') to 5% (0.5') to 5%
iodo-2-propoxy- (2 5,) benzamide Molecular peak (ESI, M+1):
and 471.5 4-Acetylphenylboronic Retention time: 9.15 min.
acid Product; Method Structure Ex. analogous 'H-N M R(400 MHz) S[ppm]
reagents to 439 4'-Ethanesulphonyl-4- 135 Column Purospher Star RP
propoxy-biphenyl-3- C18 4.6x125 5pm; detection oH
NH
carboxylic acid [(R)-2- wavelength 214 nm; flow rate 0 HN
hydroxy-1 -(1 H-indol-3- 1 mI/min; eluentsA: 0.1%
ylmethyl)ethyl]amide; TFA in H20, B 0.1% TFA in ACN; gradient in each case N-((R)-2-Hydroxy-1-(1 H- -based on B: 5% to 95% (10') S1 indol-3-ylmeth yl) eth yl]-5-to 95% (2') to 5% (0.5') to 5%
iodo-2-propoxy- (2.5') benzamide Molecular peak (ESI, M+1):
and 521.5 4-(Ethylsulphonyl)-Retention time: 8.73 min.
phenylboronic acid 440 3'-Cyanomethyl-4- 135 Column Purospher Star RP
propoxy-biphenyl-3- C18 4.6x125 5pm; detection oH
NH
carboxylic acid [(R)-1- wavelength 214 nm; flow rate o HN H
~ 0 hydroxymethyl-2-(1 H- 1 ml/min; eluents A: 0.1 %
indol-3-yl)ethyl]amide; TFA in H20, B 0.1% TFA in ACN; gradient in each case "
N-((R)-2-Hydroxy-1-(1 H-based on B: 5% to 95% (10') indol-3-ylmethyl)ethyl]-5- to 95% (2') to 5% (0.5') to 5%
iodo-2-propoxy- (2 5,) benzamide Molecular peak (ESI, M+1):
and 468.5 3-(Cyanomethyl)phenyl- Retention time: 9.13 min.
boronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 441 3'-Methanesulphonyl- 135 Column Purospher Star RP
amino-4-propoxy- C18 4.6x125 5pm; detection OH ~
NH
biphenyl-3-carboxylic acid wavelength 214 nm; flow rate O HN FI
[(R)-2-hyd roxy- 1 -(1 H- 1 mI/min; eluents A: 0.1% I~ 0 indol-3-ylmethyl)ethyl]- TFA in H20, B 0.1% TFA in i amide; ACN; gradient in each case ~ I NH
o: ~
based on B: 5% to 95% (10') o_slI
N-[(R)-2-Hydroxy-1-(1H- to 95% (2') to 5% (0.5') to 5%
indol-3-ylmeth yl) eth ylJ-5-(2.5') iodo-2-propoxy-benzamide Molecular peak (ESI, M+1):
522.5 and Retention time: 8.56 min.
3-(Methylsulphonylamino)-phenylboronic acid 442 3'-Cyclopropylmethoxy-4- 135 Column Purospher Star RP
propoxy-biphenyl-3- C18 4.6x125 5pm; detection H
NH
carboxylic acid [(R)-1- wavelength 214 nm; flow rate 0 HN H
hydroxymethyl-2-(1 H- 1 ml/min; eluents A: 0.1 % 0 indol-3-yl)ethyl]amide; TFA in H20, B 0.1% TFA in N-((R)-2-Hydroxy-l-(1 H- ACN; gradient in each case o based on B: 5% to 95% (10') LIL
indol-3-ylmethyl)ethy1J-5- to 95% (2') to 5% (0.5') to 5%
iodo-2-propoxy- (25) benzamide Molecular peak (ESI, M+1):
and 499.5 3-(Cyclopropylmethoxy)- Retention time: 10.5 min.
phenylboronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) 8 [ppm]
reagents to 443 3'-Methanesulphonyl-4- 135 Column Purospher Star RP H
N
propoxy-biphenyl-3- C18 4.6x125 5pm; detection carboxylic acid [(R)-2- wavelength 214 nm; flow rate HO H
hydroxy-1-(1H-indol-3- 1 mI/min; eluentsA: 0.1% ---o Q
ylmethyl)ethyl]amide; TFA in H20, B 0.1% TFA in ACN; gradient in each case 60 N-[(R)-2-Hydroxy-1-(IH- based on B: 5% to 95% (10') indol-3-ylmethyl)ethyl]-5- to 95% (2') to 5% (0.5') to 5%
iodo-2-propoxy- (25) benzamide Molecular peak (ESI, M+1):
and 507.5 3-(Methylsuofonyl)phen yl-Retention time: 8.45 min.
boronic acid 444 4-Propoxybiphenyl-3,3'- 135 Column Purospher Star RP
/
dicarboxylic acid 3'-[(2- oH -C18 4.6x125 5pm; detection NH
dimethyl- wavelength 214 nm; flow rate O HN H
aminoethyl)amide] 3-{[(R)- I
1 ml/min; eluents A: 0.1 % ~
1-hydroxymethyl-2-(1 H- TFA in H20, B 0.1% TFA in indol-3-yl)ethyl]amide}; ACN; gradient in each case I o N-[(R)-2-Hydroxy-1-(IH- HN~
based on B: 5% to 95% (10') indol-3-ylmethyl)ethyl]-5- to 95% (2') to 5% (0.5') to 5% i iodo-2-propoxy- (2.5') benzamide and Molecular peak (ESI, M+1):
3-(2-N, N-Dimeth ylamino- 543.5 eth ylaminocarbonyl)-phenylboronic acid Retention time: 6.67 min.

Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 445 3'-[(R)-1-Hydroxymethyl-2- 135 Column Purospher Star RP
(1 H-indol-3-yl)ethylcarba- C18 4.6x125 5pm; detection oH ~ NH
moyl]-3-methoxy-4'- wavelength 214 nm; flow rate o HN H
~ 0 propoxybiphenyl-4-car- 1 mI/min; eluents A: 0.1 % I~
boxylic acid methyl ester; TFA in H20, B 0.1% TFA in ACN; gradient in each case N-((R)-2-Hydroxy-1-(1 H-based on B: 5% to 95% (10') o 0 indol-3-ylmethyl)ethyl]-5- to 95% (2') to 5% (0.5') to 5%
iodo-2-propoxy- (25) benzamide Molecular peak (ESI, M+1):
and 517.5 3-Methoxy-4-(methoxy-Retention time: 9.13 min.
carbonyl)phenylboronic acid 446 3'-Chloro-4- 135 Column Purospher Star RP
oH ~
propoxybiphenyl-3,4'- C18 4.6x125 5pm; detection NH
dicarboxylic acid 4'-amide wavelength 214 nm; flow rate 0 HN H

3-{[(R)-2-hydroxy-1-(1H- 1 ml/min; eluentsA: 0.1% I~
indol-3- TFA in H20, B 0.1% TFA in ylmethyl)ethyl]amide}; ACN; gradient in each case c, based on B: 5% to 95% (10') HZN 0 N-((R)-2-Hydroxy-l-(1H- to 95% (2') to 5% (0.5') to 5%
indo1-3-ylmeth yl)ethyl]-5-(2.5') iodo-2-propoxy-benzamide Molecular peak (ESI, M+1):

and Retention time: 7.85 min.
4-(Aminocarbonyl)-3-chlorophenylboronic acid Product; Method Structure Ex. analogous 'H-N M R(400 MHz) S[ppm]
reagents to 447 3'-Dimethylsulphamoyl-4- 135 Column Purospher Star RP
propoxy-biphenyl-3- C18 4.6x125 5pm; detection oH NH
carboxylic acid [(R)-2- wavelength 214 nm; flow rate "N
o hydroxy-1-(1 H-indol-3- 1 mI/min; eluents A: 0.1%
ylmethyl)ethyl]amide; TFA in H20, B 0.1% TFA in N-((R)-2-Hydroxy-1-(1 H- ACN; gradient in each case o:o indol-3-ylmethyl)ethyl]-5- based on B: 5% to 95% (10') iodo-2-propoxy- to 95% (2') to 5% (0.5') to 5%
benzamide (2.5') and Molecular peak (ESI, M+1):
3-(N, N- 536.5 Dimethylsulphonamido-phenyl)boronic acid Retention time: 9.13 min.

448 4'-(Propane-2-sulphonyl)- 135 Column Purospher Star RP QY\"
4-propoxy-biphenyl-3- C18 4.6x125 5Nm; detection o" NH
carboxylic acid [(R)-2- wavelength 214 nm; flow rate o HN Fi hydroxy-1-(1H-indol-3- 1 mI/min; eluentsA: 0.1%
ylmethyl)ethyl]amide; TFA in H20, B 0.1% TFA in ACN; gradient in each case -oõ
N-((R)-2-Hydroxy-1-(1H- based on B: 5% to 95% (10') o=sy indo1-3-ylmethyl)ethyl]-5- to 95% (2') to 5% (0.5') to 5%
iodo-2-propoxy- (25) benzamide Molecular peak (ESI, M+1):
and 535.5 Retention time: 9.03 min.
(Isopropylsulphonylphe-nyl)boronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 449 4'-Methylsulphamoyl-4- 135 Column Purospher Star RP
~ OH
propoxy-biphenyl-3- C18 4.6x125 5pm; detection NH
carboxylic acid [(R)-2- wavelength 214 nm; flow rate o HN H
hydroxy-1 -(1 H-indol-3- 1 ml/min; eluentsA: 0.1% I~
ylmethyl)ethyl]amide; TFA in H20, B 0.1% TFA in ACN; gradient in each case N-((R)-2-Hydroxy-1-(1 H- s, based on B: 5% to 95% (10') O p NH
indol-3-ylmethyl)ethyl]-5-to 95% (2') to 5% (0.5') to 5%
iodo-2-propoxy- (25) benzamide Molecular peak (ESI, M+1):
and 522.5 (4-Methylaminosulphonyl-Retention time: 8.49 min.
phenyl)boronic acid 450 4'-Dimethylsulphamoyl-4- 135 Column Purospher Star RP
propoxy-biphenyl-3- C18 4.6x125 5pm; detection o"
NH
carboxylic acid [(R)-2- wavelength 214 nm; flow rate O HN
hydroxy-1-(1H-indol-3- 1 ml/min; eluents A: 0.1% 1 o ylmethyl)ethyl]amide; TFA in H20, B 0.1% TFA in ~
ACN; gradient in each case ~ i N-((R)-2-Hydroxy-1-(1 H-based on B: 5% to 95% (10') o o'N~
indol-3-ylmethyl)ethyl]-5-to95%(2')to5%(0.5')to5%
iodo-2-propoxy-(2.5') benzamide Molecular peak (ESI, M+1):
and 536.5 (4-Dimethylamino- Retention time: 9.1 min.
sulphonylphenyl)boronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 451 4-Propoxybiphenyl-3,4'- 135 Column Purospher Star RP N
dicarboxylic acid 4'-amide C18 4.6x125 5pm; detection ' HO
3-{[(R)-1-hydroxymethyl-2- wavelength 214 nm; flow rate HNH
(1 H-indol-3-yl)ethyl]- 1 mi/min; eluents A: 0.1 % tio amide); TFA in H20, B 0.1% TFA in ACN; gradient in each case N-((R)-2-Hydroxy-l-(1 H- "~"
based on B: 5% to 95% (10') indol-3-ylmethyl)ethyl]-5- to 95% (2') to 5% (0.5') to 5%
iodo-2-propoxy- (25) benzamide Molecular peak (ESI, M+1):
and 472.5 4-Aminocarbonyl-Retention time: 7.59 min.
phenylboronic acid 452 3'-Methylsulphamoyl-4- 135 Column Purospher Star RP Q
propoxy-biphenyl-3- C18 4.6x125 5Nm; detection o" ~ NH
carboxylic acid [(R)-2- wavelength 214 nm; flow rate "N "
I ~ o hydroxy-1-(1H-indol-3- 1 mI/min; eluentsA: 0.1%
ylmethyl)ethyl]amide; TFA in H20, B 0.1% TFA in ACN; gradient in each case N
N-((R)-2-Hydroxy-1-(1 H- 'so \
based on B: 5% to 95% (10') indol-3-ylmethyl)ethyl]-5-to95%(2')to5%(0.5')to5%
iodo-2-propoxy- (2 5,) benzamide Molecular peak (ESI, M+1):
and 522.5 (3-Methylaminosulphonyl- Retention time: 8.57 min.
phenyl)boronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 453 3'-Methanesulphonyl-4- 135 Column Purospher Star RP
propoxy-biphenyl-3- C18 4.6x125 5pm; detection N-carboxylic acid [(R)-2- wavelength 214 nm; flow rate OH
hydroxy-1 -(1-methyl-1 H- 1 mi/min; eluents A: 0.1 % o S HN'"

indol-3-ylmethyl)ethyl]- TFA in H20, B 0.1% TFA in - ~~
amide; ACN; gradient in each case based on B: 5% to 95% (10') N-((R)-1-Hydroxymethyl-2- to 95% (2') to 5% (0.5') to 5%
(1-methyl-1 H-indol-3-(2.5') y,)c~t hyI]-5-lvdir2-propoxy-benzamide Molecular peak (ESI, M+1):
521.6 and Retention time: 9.22 min.
3-Methylsulphonyl-phenylboronic acid 454 3'-[(R)-1-Hydroxymethyl-2- 135 Column Purospher Star RP
(1-methyl-1 H-indol-3- C18 4.6x125 5pm; detection ~ "-yl)ethylcarbamoyl]-3- wavelength 214 nm; flow rate OH
O HN' H
methoxy-4'- 1 ml/min; eluents A: 0.1 % a~~
propoxybiphenyl-4- TFA in H20, B 0.1% TFA in - - - 0 carboxylic acidmethyl es- ACN; gradient in each case ter; based on B: 5% to 95% (10') to 95% (2') to 5% (0.5') to 5%
N-((R)-1-Hydroxymethyl-2- (25) (1-methyl-1 H-indol-3-yl)ethylJ-5-iodo-2- Molecular peak (ESI, M+1):
propoxybenzamide 531.6 and Retention time: 9.92 min.
3-Methoxy-4-(methoxy-carbonyl)phenylboronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 455 4-Propoxybiphenyl-3,4'- 135 Column Purospher Star RP N

dicarboxylic acid 4'-[(2- C18 4.6x125 5pm; detection 0 i HO
dimethylaminoethyl)- wavelength 214 nm; flow rate N o o-/
amide] 3-{[(R)-1-hydroxy- 1 mI/min; eluents A: 0.1%
methyl-2-(1 -methyl- 1 H- TFA in H20, B 0.1% TFA in indol-3-yl)ethyl]amide}; ACN; gradient in each case o NH
based on B: 5% to 95% (10') N-((R)-1-Hydroxymethyl-2- to 95% (2') to 5% (0.5') to 5% -N
(1-methyl-1 H-indol-3-yl)-(2.5') zthylJ-S-iodo-2-pr opoxy-benzamide Molecular peak (ESI, M+1):
557.7 and Retention time: 6.91 min.
3-(2-N, N-Dimethylamino-ethylaminocarbonyl)-phenylboronic acid 456 3'-[2-(5-Fluoro-1 H-indol-3- 135 Column Purospher Star RP F
yl)-1-hydroxymethyl- C18 4.6x125 5pm; detection NH
ethylcarbamoyl]-4'- wavelength 214 nm; flow rate OH
HN H.
propoxybiphenyl-4- 1 mI/min; eluents A: 0.1 % Ho _ o \ / ~ \ -carboxylic acid; TFA in H20, B 0.1% TFA in o o ACN; gradient in each case N-(2-(5-Fluoro-1H-indol-3- based on B: 5% to 95% (10') yl)-1-hydroxymethyl-ethylJ- to 95% (2') to 5% (0.5') to 5%
5-iodo-2-propoxy- (25) benzamide Molecular peak (ESI, M+1):
and 491.5 4-Carboxyphenylboronic Retention time: 8.37 min.
acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 457 3'-Methanesulphonyl- 135 Column Purospher Star RP F
amino-4-propoxy-bi- C18 4.6x125 5pm; detection ~ NH
phenyl-3-carboxylic acid wavelength 214 nm; flow rate o OH
-$-N HN H.
[2-(5-fluoro-1 H-indol-3-yl)- 1 ml/min; eluents A: 0.1 % o 1-hydroxymethylethyl]- TFA in H20, B 0.1% TFA in - - ~
amide; ACN; gradient in each case based on B: 5% to 95% (10') N-(2-(5-Fluoro-1H-indol-3- to 95% (2') to 5% (0.5') to 5%
yl)-1-hydroxymethylethyl]- (25) 5-iodo-2-pr ;,poxy-benzamide Molecular peak (ESI, M+1):
540.6 and Retention time: 8.57 min.

(Meth ylsul ph on ylami-no)phenylboronic acid 458 3'-Methanesulphonyl-4- 135 Column Purospher Star RP F I
propoxy-biphenyl-3- C18 4.6x125 5pm; detection ~ NH
carboxylic acid [2-(5- wavelength 214 nm; flow rate OH
O HN H
fluoro-1 H-indol-3-yl)-1- 1 ml/min; eluents A: 0.1 % 's o hydroxymethy- TFA in H20, B 0.1% TFA in ~~ c ~~ 0 lethyl]amide; ACN; gradient in each case based on B: 5% to 95% (10') N-(2-(5-Fluoro-1 H-indol-3- to 95% (2') to 5% (0.5') to 5%
yl)-1-hydroxymethylethyl]- (2.5') 5-iodo-2-propoxybenzamide Molecular peak (ESI, M+1):
525.6 and Retention time: 8.61 min.
3-Methylsulphonylphenyl-boronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 459 4-Propoxybiphenyl-3,3'- 135 Column Purospher Star RP f dicarboxylic acid 3'-[(2- C18 4.6x125 5pm; detection /\ HO 0 o dimethylaminoethyl)- wavelength 214 nm; flow rate amide] 3-{[2-(5-fluoro-1 H- 1 mI/min; eluents A: 0.1 % F ~
I
indol-3-yl)-1-hydroxy- TFA in H20, B 0.1% TFA in o methylethyl]amide}; g ~NH
ACN; radient in each case based on B: 5% to 95% (10') N
N-[2-(5-Fluoro-1 H-indol-3-yl)-1-hydroxymethylethyl]- to 95% (2') to 5% (0.5') to 5%
5-iodo-2-propoxybenz- (25) amide Molecular peak (ESI, M+1):
and 561.7 3-(2-N, N-Dimethylamino-ethylaminocarbonyl)- Retention time: 6.85 min.
phenylboronic acid 460 3'-Chloro-4-propoxy- 135 Column Purospher Star RP - N
biphenyl-3,4'-dicarboxylic C18 4.6x125 5pm; detection oH
acid 4'-amide 3-{[2-(5- wavelength 214 nm; flow rate HNH 0 fluoro-1H-indol-3-yl)-1- 1 ml/min; eluentsA: 0.1%
hydroxymethylethyl]- TFA in H20, B 0.1% TFA in -HzN
amide}; ACN; gradient in each case o based on B: 5% to 95% (10') N-[2-(5-Fluoro-1H-indol-3- to 95% (2') to 5% (0.5') to 5%
yl)-1-hydroxymethylethyl]- (25) 5-iodo-2-propoxybenz-amide Molecular peak (ESI, M+1):

and Retention time: 7.99 min.
4-(Aminocarbonyl)-3-chlorophenylboronic acid Product; Method Structure Ex. analogous IH-NMR (400 MHz) S [ppm]
reagents to 461 3'-Dimethylsulphamoyl-4- 135 Column Purospher Star RP F
propoxy-biphenyl-3- C18 4.6x125 5pm; detection ~ NH
carboxylic acid [2-(5- wavelength 214 nm; flow rate OH
O N- HN H
fluoro-1 H-indol-3-yl)-1- 1 mI/min; eluents A: 0.1 % 'S o hydroxymethylethyl]- TFA in H20, B 0.1% TFA in 6-- c \ o amide; ACN; gradient in each case based on B: 5% to 95% (10') N-(2-(5-Fluoro-lH-indol-3- to 95% (2') to 5% (0.5') to 5%
yl)-1-hydroxymethylethyl]- (2 5,) 5-iodo-2-pr opoxybenz-amide Molecular peak (ESI, M+1):
554.7 and Retention time: 9.17 min.
3-(N, N-Dimethylsulphon-amidophenyl)boronic acid 462 4'-(Propane-2-sulphonyl)- 135 Column Purospher Star RP H
N HO ~
4-propoxy-biphenyl-3- C18 4.6x125 5pm; detection N
H
carboxylic acid [2-(5- wavelength 214 nm; flow rate F
fluoro-1 H-indol-3-yl)-1- 1 mI/min; eluents A: 0.1 %
hydroxymethylethyl]- TFA in H20, B 0.1% TFA in ~'o amide; ACN; gradient in each case based on B: 5% to 95% (10') N-(2-(5-Fluoro-lH-indol-3- to 95% (2') to 5% (0.5') to 5%
yl)-1-hydroxymethylethyl]- (2.5') 5-iodo-2-propoxy-benzamide Molecular peak (ESI, M+1):
553.7 and Retention time: 9.18 min.
4-(Isopropylsulphonyl-phenyl)boronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 463 4'-Dimethylsulphamoyl-4- 135 Column Purospher Star RP F
propoxy-biphenyl-3- C18 4.6x125 5pm; detection NH
OH
carboxylic acid [2-(5- wavelength 214 nm; flow rate HN H
fluoro-1 H-indol-3-yl)-1- 1 mI/min; eluents A: 0.1 % os a hydroxymethylethyl]- TFA in H20, B 0.1% TFA in amide; ACN; gradient in each case based on B: 5% to 95% (10') N-(2-(5-Fluoro-1H-indol-3- to 95% (2') to 5% (0.5') to 5%
yl)-1-hydroxymethylethyl]-(2.5') ~ - -- ~ - -- - - -a--oao----piopoxy-benzamide Molecular peak (ESI, M+1):
and 554.7 4-(N,N-Dimethylsulphon- Retention time: 9.12 min.
amidophenyl)boronic acid 464 4-Propoxybiphenyl-3,4'- 135 Column Purospher Star RP F
dicarboxylic acid 4'- C18 4.6x125 5pm; detection NH
OH
diethylamide 3-{[2-(5- wavelength 214 nm; flow rate HN H.
fluoro-1H-indol-3-yl)-1- 1 mI/min; eluents A: 0.1%
r--N ~ r r_~ O
hydroxymethy- TFA in H20, B 0.1% TFA in lethyl]amide}; ACN; gradient in each case based on B: 5% to 95% (10') N-(2-(5-Fluoro-1H-indol-3- to 95% (2') to 5% (0.5') to 5%
yl)-1-hydroxymethylethyl]- (2.5') 5-iodo-2-propoxy-benzamide Molecular peak (ESI, M+1):
546.7 and Retention time: 9.07 min.
4-(N, N-Dimethylamino-carbon yl)-phenylboronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 465 3'-Methylsulphamoyl-4- 135 Column Purospher Star RP F
propoxy-biphenyl-3- C18 4.6x125 5pm; detection ~ NH
carboxylic acid [2-(5- wavelength 214 nm; flow rate \ OH
O NH H
fluoro-1 H-indol-3-yl)-1- I ml/min; eluents A: 0.1 % o=s HN

hydroxymethylethyl]- TFA in H20, B 0.1% TFA in - _ o amide; ACN; gradient in each case based on B: 5% to 95% (10') N-(2-(5-Fluoro-1H-indol-3- to 95% (2') to 5% (0.5') to 5%
yl)-1-hydroxymethylethyl]-(2.5') 5-:--do-2-propoxy-benzamide Molecular peak (ESI, M+1):
540.6 and Retention time: 8.72 min.
(3-Methylaminosulphonyl-phenyl)-boronic acid 466 3'-Acetyl-4-propoxy- 135 Column Purospher Star RP
biphenyl-3-carboxylic acid C18 4.6x125 5pm; detection ~"-[(R)-1-hydroxymethyl-2-(1- wavelength 214 nm; flow rate OH
H
HN' methyl-1 H-indol-3-yl)- 1 mi/min; eluents A: 0.1 % 0 ethyl]amide; TFA in H20, B 0.1% TFA in ~
ACN; gradient in each case N-((R)-1-Hydroxymethyl-2- based on B: 5% to 95% (10') (1-methyl-1H-indol-3- to 95% (2') to 5% (0.5') to 5%
yl)ethyl]-5-iodo-2-propoxy- (25) benzamide Molecular peak (ESI, M+1):
and 485.6 3-Acetylphenylboronic Retention time: 9.8 min.
acid P rod uct; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 467 4-Propoxy- 135 Column Purospher Star RP
[1.1';3'.1"]terphenyl-3- C18 4.6x125 5pm; detection ~ "-carboxylic acid [(R)-1- wavelength 214 nm; flow rate HN H H
hydroxymethyl-2-(1- 1 mI/min; eluentsA: 0.1%
methyl-1 H-indol-3-yl)- TFA in H20, B 0.1% TFA in 0 *-~
ethyl]amide; ACN; gradient in each case based on B: 5% to 95% (10') N-((R)-1-Hydroxymethyl-2- to 95% (2') to 5% (0.5') to 5%
(1-methyl-1 H-indol-3-(2.5') yl)ethy,"
.,-5-iodo-2-propoxy-benzamide Molecular peak (ESI, M+1):
519.7 and Retention time: 11.62 min.
Biphenyl-3-boronic acid 468 3'-Cyanomethyl-4- 135 Column Purospher Star RP
I , propoxy-biphenyl-3- C18 4.6x125 5pm; detection "
carboxylic acid [(R)-1- wavelength 214 nm; flow rate OH
h drox meth I-2- 1- 1 mI/min; eluents A: 0.1% N HNH
y y y ( O
methyl-1 H-indol-3-yl)- TFA in H20, B 0.1% TFA in ethyl]amide; ACN; gradient in each case based on B: 5% to 95% (10') N-((R)-1-Hydroxymethyl-2- to 95% (2') to 5% (0.5') to 5%
(1-methyl-1 H-indol-3-(2.5') yl) eth yl]-5-iodo-2-propox y-benzamide Molecular peak (ESI, M+1):
482.6 and Retention time: 9.81 min.
3-Cyanomethylphenyl-boronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 469 3'-Methansulphonylamino- 135 Column Purospher Star RP
4-propoxy-biphenyl-3- C18 4.6x125 5pm; detection ~ N-carboxylic acid [(R)-2- wavelength 214 nm; flow rate o OH
-N HN H
hydroxy-1 -(1 -methyl-1 H- 1 ml/min; eluents A: 0.1% 0 indol-3-ylmethyl)ethyl]- TFA in H20, B 0.1% TFA in amide; ACN; gradient in each case based on B: 5% to 95% (10') N-((R)-1-Hydroxymethyl-2- to 95% (2') to 5% (0.5') to 5%
(1-methyl-1 H-indol-3-(2.5') yl)ethyi;-5-iodo-2-pr opoxy-benzamide Molecular peak (ESI, M+1):
436.7 and Retention time: 9.1 min.
3-(Methylsulphonamido)-phenylboronic acid 470 4'-Cyanomethyl-4- 135 Column Purospher Star RP
propoxy-biphenyl-3- C18 4.6x125 5pm; detection ~ N-carboxylic acid [(R)-1- wavelength 214 nm; flow rate OH
HN, H
hydroxymethyl-2-(1- 1 mi/min; eluents A: 0.1% 0 methyl-1 H-indol-3-yl)- TFA in H20, B 0.1% TFA in 0 *-~
ethyl]amide; ACN; gradient in each case based on B: 5% to 95% (10') N-ftR)-1-Hydroxymethyl-2- to 95% (2') to 5% (0.5') to 5%
(1-methyl- 1 H-indol-3- (25) yl) e th ylJ-5-iodo-2-propox y-benzamide Molecular peak (ESI, M+1):
482.6 and Retention time: 9.67 min.
4-Cyanomethylphenyl-boronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 471 4-Propoxy-biphenyl-3.3'- 135 Column Purospher Star RP
dicarboxylic acid 3'-[(2- N HO
C18 4.6x125 5pm; detection I H
dimethylamino-ethyl)- wavelength 214 nm; flow rate "~
amide] 3-{[(R)-1-hydroxy- 1 mI/min; eluents A: 0.1%
methyl-2-(1-methyl-1 H- TFA in H20, B 0.1 % TFA in r NH
indol-3-yl)ethyl]amide}; ACN; gradient in each case NJ
N-((R)-1-Hydroxymethyl-2- based on B: 5% to 95% (10') (1-methyl-IH-indol-3- to 95% (2') to 5% (0.5') to 5%
yl)ethyl]-5-iodo-2-propoxy- (25) benzarr-ide and Molecular peak (ESI, M+1):
3-(2-N, N-Dimethylamino- 557.7 e th yl amin oca rb on yl) -phenylboronic acid Retention time: 7.19 min.
472 4-Fluoro-3'-[(R)-2- 135 Column Purospher Star RP
hydroxy-1-(1-methyl-1H- C18 4.6x125 5pm; detection ~ N-indol-3-ylmethyl)ethyl- wavelength 214 nm; flow rate HO HNH o"
carbamoyl]-4'-propoxy- 1 mI/min; eluents A: 0.1 % F~~
biphenyl-3-carboxylic acid; TFA in H20, B 0.1% TFA in ACN; gradient in each case N-((R)-1-Hydroxymethyl-2- based on B: 5% to 95% (10') (1-methyl-lH-indol-3- to 95% (2') to 5% (0.5') to 5%
yl)ethyl]-5-iodo-2-propoxy- (25) benzamide Molecular peak (ESI, M+1):
and 505.6 3-Carboxy-4-fluorphenyl- Retention time: 8.94 min.
boronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 473 3'-Chloro-4-propoxy- 135 Column Purospher Star RP
biphenyl-3,4'-dicarboxylic C18 4.6x125 5pm; detection ~ N-acid 4'-amide 3-{[(R)-2- wavelength 214 nm; flow rate OH
HN H
hydroxy-1-(1-methyl-1 H- 1 mI/min; eluents A: 0.1 % HZN ci - ~ ~
indol-3-ylmethyl)ethyl]- TFA in H20, B 0.1% TFA in 0 o amide}; ACN; gradient in each case based on B: 5% to 95% (10') N-((R)-1-Hydroxymethyl-2- to 95% (2') to 5% (0.5') to 5%
(1-methyl-1 H-indol-3-(2.5') y!) ?t.hy.;1-5-iodo-2-propoxy-benzamide Molecular peak (ESI, M+1):

and Retention time: 8.44 min.
3-Chloro-5-(carbamoyl)-phenylboronic acid 474 4-Propoxybiphenyl-3,4'- 135 Column Purospher Star RP
dicarboxylic acid 4'- C18 4.6x125 5pm; detection ~ N-OH
diethylamide 3-{[(R)-1- wavelength 214 nm; flow rate HN H
hydroxymethyl-2-(1- 1 ml/min; eluents A: 0.1% ~~
/--N ~ ~ _ 0 methyl-1 H-indol-3-yl)- TFA in H20, B 0.1% TFA in ethyl]amide}; ACN; gradient in each case based on B: 5% to 95% (10') N-((R)-1-Hydroxymethyl-2- to 95% (2') to 5% (0.5') to 5%
(1-methyl-1H-indol-3- (2.5') yl)ethyl]-5-iodo-2-propoxy-benzamide Molecular peak (ESI, M+1):
542.7 and Retention time: 9.7 min.
4-(N, N-Diethylamino-carbonyl)phenylboronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 475 4'-Dimethylamino-4- 135 Column Purospher Star RP F I
propoxy-biphenyl-3- C18 4.6x125 5pm; detection ~ NH
carboxylic acid [2-(5- wavelength 214 nm; flow rate OH
fluoro-1 H-indol-3-yl)-1- 1 mI/min; eluents A: 0.1 % HN o hydroxymethylethyl]- TFA in H20, B 0.1% TFA in o amide; ACN; gradient in each case based on B: 5% to 95% (10') N-(2-(5-Fluoro-1 H-indol-3-to95%(2')to5%(0.5')to5%
yl)-1-hydroxymethylethylJ- (25) -2-propox-benz-amide Molecular peak (ESI, M+1):
490.6 and Retention time: 6.91 min.
4-Dimethylaminophenyl-boronic acid 476 4'-Acetyl-4-propoxy- 135 Column Purospher Star RP F I
biphenyl-3-carboxylic acid C18 4.6x125 5pm; detection ~ NH
[2-(5-fluoro-1 H-indol-3-yl)- wavelength 214 nm; flow rate OH
1-hydroxymethylethyl]- 1 mI/min; eluentsA: 0.1% HN o amide; TFA in H20, B 0.1% TFA in oO~o ACN; gradient in each case N-(2-(5-Fluoro-1 H-indol-3-based on B: 5% to 95% (10') yl)-1-hydroxymethylethylJ- to 95% (2') to 5% (0.5') to 5%
5-iodo-2-propoxy- (25) benzamide Molecular peak (ESI, M+1):
and 489.6 4-Acetylphenylboronic Retention time: 9.28 min.
acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 477 3'-Acetyl-4-propoxy- 135 Column Purospher Star RP F
biphenyl-3-carboxylic acid C18 4.6x125 5Nm; detection ~ NH
[2-(5-fluoro-1 H-indol-3-yl)- wavelength 214 nm; flow rate OH
H
1-hydroxymethylethyl]- 1 mI/min; eluents A: 0.1 % 0 HN o amide; TFA in H20, B 0.1% TFA in o ACN; gradient in each case N-[2-(5-Fluoro- I H-indol-3- based on B: 5% to 95% (10') yl)-1-hydroxymethylethyl]- to 95% (2') to 5% (0.5') to 5%
5-iodo-2-propoxy- (2.5') benzamide Molecular peak (ESI, M+1):
and 489.6 3-Acetylphenylboronic Retention time: 9.33 min.
acid 478 4-Propoxy- 135 Column Purospher Star RP F I
[1.1';3'.1"]terphenyl-3- C18 4.6x125 5pm; detection ~ NH
carboxylic acid [2-(5- wavelength 214 nm; flow rate OH
fluoro-1H-indol-3-yl)-1- 1 mi/min; eluentsA: 0.1% HN Ho hydroxymethylethyl]- TFA in H20, B 0.1% TFA in o amide; ACN; gradient in each case based on B: 5% to 95% (10') N-(2-(5-Fluoro-1H-indol-3- to 95% (2') to 5% (0.5') to 5%
yl)-1-hydroxymethylethyl]-(2.5') 5-iodo-2-propoxy-benzamide Molecular peak (ESI, M+1):
523.6 and Retention time: 10.86 min.
Biphenyl-3-boronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 479 3'-[2-(5-Fluoro-1 H-indol-3- 135 Column Purospher Star RP F
yl)-1-hydroxymethyl- C18 4.6x125 5pm; detection NH
ethylcarbamoyl]-3- wavelength 214 nm; flow rate OH
O HN H
methoxy-4'-propoxy- 1 ml/min; eluents A: 0.1 % o~\ o biphenyl-4-carboxylic acid TFA in H20, B 0.1% TFA in -~ - 0 methylester; ACN; gradient in each case based on B: 5% to 95% (10') N-(2-(5-Fluoro-1H-indol-3- to 95% (2') to 5% (0.5') to 5%
yl)-1-hydroxymethylethyl]- (2 5,) 5-iodo-2-propoxy-benzamide Molecular peak (ESI, M+1):
535.6 and Retention time: 9.16 min.
3-Methoxy-4-(methoxy-carbonyl)phenylboronic acid 480 4-Propoxybiphenyl-3,4'- 135 Column Purospher Star RP F
dicarboxylic acid 4'-amide C18 4.6x125 5pm; detection NH
HN H OH
3-{[2-(5-fluoro-1 H-indol-3- wavelength 214 nm; flow rate yl)-1-hydroxymethylethyl]- 1 ml/min; eluents A: 0.1% H2N - O
\ / ~ \ -amide}; TFA in H20, B 0.1 % TFA in o o ACN; gradient in each case N-(2-(5-Fluoro-1 H-indol-3- based on B: 5% to 95% (10') yl)-1-hydroxymethylethyl]- to 95% (2') to 5% (0.5') to 5%
5-iodo-2-propoxy- (2.5') benzamide Molecular peak (ESI, M+1):
and 490.5 4-Aminocarbonylphenyl-Retention time: 7.64 min.
boronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 481 4-Ethoxy-4'-methoxy- 125 (DMSO-d6): 10.79 s(1 H); H
N
methyl-biphenyl-3- 8.36 d (J = 8.1 Hz, 1 H); 8.14 carboxylic acid [(R)-1- d (J = 2.5 Hz, 1 H); 7.73 dd (J NH oJ
hydroxymethyl-2-(1 H- = 2.8 Hz / 8.6 Hz, 1 H); 7.68 d o indol-3-yI)ethyl]amide; (J = 7.8 Hz, 2H); 7.59 d (J =
8.3 Hz, 2H); 7.36 d(J = 8.3 5-Bromo-2-ethoxy-N-((R)- Hz, 2H); 7.29 d (J = 8.1 Hz, 1-hydroxymethyl-2-(1 H- 1 H); 7.19 d (J = 8.8 Hz, 1 H);
indol-3-yl)ethylJbenzamide 7.13 s(1 H); 7.03 m(1 H); 6.94 and m(1 H); 4.90 m(1 H); 4.41 s (2H); 4.23 m(1 H); 4.12 m 4-Methoxymethylphenyl- (2H); 3.47 m(1H); 3.41 m boronic acid (1 H); 2.95 m (2H); 1.28 m (3H).
482 4-Ethoxybiphenyl-3,3'- 125 (DMSO-d6): 10.78 s(1 H); H
dicarboxylic acid 3'-amide 8.37 d (J = 8.1 Hz, 1 H); 8.21 3-{[(R)-1-hydroxymethyl-2- d (J = 2.6 Hz, 1 H); 8.11 s ~ 'H
NH O
(1 H-indol-3-yI)ethyl]- (2H); 7.79 m (2H); 7.69 d (J = o H
amide}; 7.9 Hz, 1 H); 7.50 m(1 H);
7.40 s(1 H); 7.31 d (J = 8.1 5-Bromo-2-ethoxy-N-((R)-Hz; 1 H); 7.23 d (J = 8.7 Hz, 1-h ydroxymeth yl-2-(1 H- NH2 1 H); 7.14 s(1 H); 7.02 m(1 H);
indol-3-yl)ethylJbenzamide 6.94 m(1 H); 4.90 m(1 H);

and 4.18 m(1 H); 4.14 m(2H);
3.47 m (2H); 2.96 m (2H);
3-Aminocarbonylphenyl- 1.29 m (3H).
boronic acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 483 4'-Ethanesulphonyl-4- 125 (DMSO-d6): 10.78 s(1 H); H
N
ethoxybiphenyl-3- 8.35 d (J = 8.1 Hz, 1 H); 8.20 carboxylic acid [(R)-2- d (J = 2.5 Hz, 1 H); 7.91 s NH oJ
hydroxy-1-(1 H-indol-3- (4H); 7.85 dd (J = 2.5 Hz / 8.6 O H
ylmethyl)ethyl]amide; Hz, 1 H); 7.67 d (J = 7.8 Hz, 1 H); 7.30 d (J = 8.1 Hz, 1 H);
5-Bromo-2-ethoxy-N-((R)- 7.24 d (J = 8.8 Hz, 1 H); 7.14 ~ I
1-hydroxymethyl-2-(1 H- ~ =o s(1 H); 7.03 m(1 H); 6.93 m indol-3-y1)ethyl]benzamide (1 H); 4.90 m (1 H); 4.23 m and (2H); 4.15 m (2H); 4.00 m (1 H); 3.47 m(1 H); 3.41 m 4-(Ethylsulphonyl)phenyl- (1 H); 2.96 m (2H); 1.29 m boronic acid (3H); 1.10 m (3H).
484 4-Ethoxy-4'-(4- 125 (DMSO-d6): 10.79 s(1 H); H
methylpiperazin-l- 8.37 d (J = 8.3 Hz, 1 H); 8.18 carbonyl)biphenyl-3- d (J = 2.5 Hz, 1 H); 7.79 dd (J NH oJ
H
carboxylic acid [(R)-1- = 2.6 Hz / 7.8 Hz, 1 H); 7.72 d o hydroxymethyl-2-(1 H- (J = 8.5 Hz, 2H); 7.67 d (J =
indol-3-yI)ethyl]amide; 7.7 Hz, 1 H); 7.53 d (J = 8.3 Hz, 1 H); 7.29 d (J = 8.1 Hz, 5-Bromo-2-ethoxy-N-[(R)- 1 H); 7.22 d (J = 8.2 Hz, 1 H); N
1-h ydroxymeth yl-2-(1 H-7.13 s(1 H); 7.03 m(1 H); 6.93 indol-3-y1)ethyl]benzamide m(1 H); 4.22 m(1 H); 4.13 m and (2H); 3.57 m (6 H, broad), 3.43 m (2H); 3.09 m (2H);
4-(4-Methylpiperazin-l- 2.95 m (2H); 2.80 s (3H); 1.29 carbonyl)-phenylboronic m (3H).
acid Product; Method Structure Ex. analogous 'H-NMR (400 MHz) S [ppm]
reagents to 485 3'-Cyclopropylmethoxy-4- 125 (MeOD): 8.30 d (J = 2.5 Hz, H
ethoxy-biphenyl-3- 1 H); 7.75 dd (J = 2.5 Hz / 8.7 carboxylic acid [(R)-1- Hz, 1 H); 7.69 d (J = 7.9 Hz, ~ NH oJ
hydroxymethyl-2-(1 H- 1 H); 7.35 m (2H); 7.17 m Ho ~
indol-3-yl)ethyl]amide; (4H); 7. 11 m (1 H); 6.99 m (1 H); 6.93 m(1 H); 4.53 m 5-Bromo-2-ethoxy-N-[(R)- (1 H); 4.16 m(1 H); 4.05 m o 1-hydroxymethyl-2-(1 H- (1 H); 3.92 d (J = 7.0 Hz, 1 H);
indol-3-y1)ethyl]benzamide 3.70 d(J = 4.9 Hz, 1 H); 3.17 and d(J = 6.4 Hz, 1 H); 1.27 m (4H); 0.67 m (2H); 0.41 m 3-(Cyclopropylmethoxy)- (2H), phenylboronic acid 486 3'-[(R)-1-Hydroxymethyl-2- 125 (DMSO-d6): 10.72 s(1H); H
(1 H-indol-3-yI)ethylcarba- 8.21 d (J = 8.1 Hz, 1 H); 7.77 N
moyl]biphenyl-2-carboxylic m (3H); 7.63 m (2H); 7.44 m acid methyl ester; (3H); 7.36 m (1 H); 7.26 d (J = HO
3-Bromo-N-[(R)-1- 8.1 Hz, 1H); 7.09 s(1H); 7.01 O NH
hydroxymethyl-2-(1 H- m(1 H); 6.92 m(1 H); 4.76 m O O
indol-3-y1)ethyl]benzamide (1 H); 4.23 m(1 H); 3.52 s and (3H); 3.49 m (2H); 2.97 m (1 H); 2.88 m (1 H).
(2-Methoxycarbonyl-phenyl)boronic acid

Claims (19)

1. Compounds of the formula I

in which R1 may be hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, C1-C6-alkyloxy-C1-C6-alkylene, C3-C7-cycloalkyloxy-C1-C8-alkylene, C1-C6-alkylamino-C1-C6-alkylene, di(C1-C6-alkyl)amino-C1-C6-alkylene, phenyloxy-C1-C6-alkylene;
where the hydrocarbon chains therein may optionally be substituted one or more times by fluorine, cyano, hydroxy, amino or the groups:

R2 may be hydrogen, halogen, cyano, -SO2Me, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkyloxy or benzyloxy, where the hydrocarbon chains therein may optionally be substituted one or more times by fluorine;
2 R3 may be hydrogen, hydroxy, halogen, nitro, amino, cyano, C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, C3-C7-cycloalkyl, hydroxy-C1-C6-alkylene, hydroxy-C3-C6-alkenylene, hydroxy-C3-C6-alkynylene, C1-C6-alkyloxy, C1-C6-alkyloxy-C1-C6-alkylene, C3-C7-cycloalkyloxy, C3-C7-cycloalkyl-C1-C6-alkyleneoxy, C3-C7-cycloalkyloxy-C1-C6-alkylene, C1-C6-alkyloxy-C3-C6-alkenylene, C1-C6-alkyloxy-C3-C6-alkynylene, C1-C6-alkyloxyphenyl-C1-C6-alkylene, C1-C6-alkylamino-C1-C6-alkylene, di(C1-C6-alkyl)amino-C1-C6-alkylene, phenyloxy-C1-C6-alkylene;
where the hydrocarbon chains therein may optionally be substituted one or more times by fluorine, cyano, hydroxy, amino or the groups R4, R5, R6 may be independently of one another hydrogen, hydroxy, halogen, nitro, amino, cyano, phenyl, C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, C3-C7-cycloalkyl, C3-C7-cycloalkyl-C1-C6-alkylene, C3-C7-heterocycloalkyl, where the hydrocarbon chains therein may optionally be substituted one or more times by fluorine, cyano or the radicals:

or independently of one another hydroxy-C1-C6-alkylene, hydroxy-C3-C6-alkenylene, hydroxy-C3-C6-alkynylene, C1-C6-alkyloxy, C3-C7-cycloalkyloxy, C3-C7-cycloalkyl-C1-C6-alkyleneoxy, C1-C6-alkyloxy-C1-C6-alkylene, C3-C7-cycloalkyloxy-C1-C6-alkylene, C1-C6-alkyloxy-C3-C6-
3 alkenylene, C1-C6-alkyloxy-C3-C6-alkynylene, C1-C6-alkyloxyphenyl-C1-C6-alkylene, phenyloxy-C1-C6-alkylene, C1-C6-alkylamino, di(C1-C6-alkyl)amino, C1-C6-alkylamino-C1-C6-alkylene, di(C1-C6)-alkylamino-C1-C6-alkylene, C3-C7-cycloalkyl-(C0-C6-alkyl)amino, C1-C6-acyl-(C0-C6-alkyl)amido, C1-C6-alkylaminocarbonyl, di(C1-C6-alkyl)aminocarbonyl, (C3-C7-cycloalkyl)aminocarbonyl, di(C3-C7-cycloalkyl)aminocarbonyl, C3-C7-cycloalkyl-C1-C6-alkyleneamino-carbonyl, C1-C6-alkylcarbonyl, C3-C7-cycloalkylcarbonyl, carboxy, carboxamido [-C(O)NH2], C1-C6-alkyloxycarbonyl, C1-C3-alkylsulphanyl, C1-Cs-alkysulphonyl, C3-C7-cycloalkylsulphonyl, C3-C7-cycloalkyl-C1-C6-alkylenesulphonyl, C1-C6-alkylaminosulphonyl, di(C1-C6-alkyl)aminosulphonyl, (C3-C7-cycloalkyl)aminosulphonyl, di(C3-C7-cycloalkyl)aminosulphonyl, C3-C7-cycloalkyl-C1-C6-alkyleneaminosulphonyl, C1-C6-alkylsulphonylamido, -N(C0-C6-alkyl)-C(O)-C1-C6-alkyl, -N(C0-C6-alkyl)-C(O)-C3-C7-cycloalkyl, -N(C0-C6-alkyl)-C(O)-N-di(C0-C6-alkyl), -N(C0-C6-alkyl)-C(O)-O-(C0-C6)alkyl, -N(C0-C6-alkyl)-C(O)-NH-C3-C7-cycloalkyl, -N(C0-C6-alkyl)-SO2-C1-C6-alkyl, -N(C0-C6-alkyl)-SO2-C3-C7-cycloalkyl, -N(C0-C6-alkyl)-SO2-N-di(C0-C6-alkyl), -N(C0-C6-alkyl)-SO2-NH-(C3-C7)-cycloalkyl, -C(O)-N(H)-C2-C6-alkylene-(C1-C6-alkyl)amine, -C(O)-N(H)-C2-C6-alkylene-[di(C1-C6-alkyl)]amine, -C(O)-N(H)-C2-C6-alkylene-(C3-C7-cycloalkyl)amine, -C(O)-N(H)-C2-C6-alkylene-(C3-C7-cycloalkyl-C1-C6-alkyl)amine, -S(O2)-N(H)-C2-C6-alkylene-(C1-C6-alkyl)amine, -S(02)-N(H)-CZ-C6-alkylene-[di(C1-C6-alkyl)]amine, -S(O2)-N(H)-C2-C6-alkylene-(C3-C7-cycloalkyl)amine, -S(O2)-N(H)-C2-C6-alkylene-(C3-C7-cycloalkyl-C1-C6-alkylene)amine, -O-C2-C6-alkylene-(C1-C6-alkyl)amine, -O-C3-C6-alkylene-[di(C1-C6-alkylene)]amine, or the radicals:
4
5 R7, R8 may be independently of one another hydrogen, methyl, ethyl, where the methyl and ethyl radicals may be fluorinated one or more times;
6 where R2 may substitute one or more positions of the aryl or heteroaryl ring in the indole residue;
R3 may substitute one or more positions of the aryl or heteroaryl ring in the radical Q;
R5 and R6 may together form heterocycloalkyl, cycloalkyl;
Q and W may be independently of one another aryl, heteroaryl;
X may be a bond, C1-C4-alkylene, C2-C4-alkenylene, C2-C4-alkynylene, C1-C3-alkyleneoxy, C1-C3-alkyleneoxy-C1-C3-alkylene, Y may be a bond, C1-C4-alkylene;

with the provision that the formula I does not include 4-(8-fluoro-3-oxo-1,3-dihydro-pyrazolo[4, 3-c]cinnolin-2-yl-N-[3-hydroxy-2-(1-H-indol-3-yl)-propyl]benzamide.

2. Compounds of the formula Ia where R1 may be hydrogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl, where the hydrocarbon radicals therein may optionally be substituted one or more times by fluorine;
7 R2 may be hydrogen, halogen, C1-C6-alkyl, C2-C8-alkenyl or C2-C6-alkynyl, C1-C4-alkyloxy, where the hydrocarbon chain therein may optionally be substituted one or more times by fluorine; or benzyloxy;

R3 may be hydrogen, halogen, nitro, amino, cyano, C1-C6-alkyl, C2-C6-alkenyl or C2-C6-alkynyl, C1-C4-alkykoxy, where the hydrocarbon chain therein may optionally be substituted one or more times by fluorine;

R4, R5, R6 may be independently of one another hydrogen, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C4-alkyloxy, where the hydrocarbon chain therein may optionally be substituted one or more times by fluorine, C1-C3-alkylsulphanyl, acetamido, C1-C6-alkylaminocarbonyl; hydroxy, cyano, hydroxy-C1-C4-alkyl;
where R2 and R3 may substitute one or more positions of the aryl or heteroaryl ring in each case in the radical Q and in the indole residue;
R5 and R6 may together form heterocycloalkyl, cycloalkyl;

Q and W may be independently of one another aryl, heteroaryl;
X ~may be a bond, C1-C4-alkylene, C1-C4-alkenylene, C1-C4-alkynylene, C1-C3-alkyleneoxy, C1-C3-alkyleneoxy-C1-C3-alkylene, Y ~may be a bond, C1-C4-alkylene;

with the provision that the formula Ia does not include 4-(8-fluoro-3-oxo-1,3-dihydro-pyrazolo[4,3-c]cinnolin-2-yl-N-[3-hydroxy-2-(1-H-indol-3-yl)-propyl]benzamide.
8 3. Compounds according to Claim 1, namely acyltryptophanols of the formulae 11 and III

in which the radicals R1 to R8 and W have the same meaning as in formula I and X ~is a bond, C1-C4-alkylene, C2-C4-alkenylene, C2-C4-alkynylene;
T ~is a nitrogen atom or a CH group;
T1, T2, T3, T4 ~are each independently of one another a nitrogen atom or an R3-C group.
9 4. Compounds according to Claim 2, namely acyltryptophanols of the formulae Ila and IIIa in which the radicals R1 to R6 and W have the same meaning as in formula Ia and X ~is a bond, C1-C4-alkylene, C2-C4-alkenylene, C2-C4-alkynylene;
T ~is a nitrogen atom or a CH group;
T1, T2, T3, T4 are each independently of one another a nitrogen atom or an R3-C group.

5. Compounds according to Claim 1 or 3, namely acyltryptophanols of the formulae IV
and V

in which the radicals R1 to R8 and W have the same meaning as in formula I.

6. Compounds according to Claim 2 or 4, namely acyltryptophanols of the formulae IVa and Va in which the radicals R1 to R6 and W have the same meaning as in formula Ia.

7. Compounds according to any of the preceding claims, namely N-[(R,S)-2-(5-Bromo-1H-indol-3-yl)-1-(hydroxymethyl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R,S)-1-(Hydroxymethyl)-2-(5-methyl-1H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxy-phenyl)quinoline-4-carboxamide;
N-[(R,S)-1-(Hydroxymethyl)-2-(4-methyl-1H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R,S)-1-(Hydroxymethyl)-2-(6-methyl-1H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1-methyl-1H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphe-nyl)quinoline-4-carboxamide;
N-[(R,S)-2-(5-Fluoro-1H-indol-3-yl)-1-(hydroxymethyl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R,S)-1-(Hydroxymethyl)-2-(5-methoxy-1H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R,S)-2-(6-Fluoro-1H-indol-3-yl)-1-(hydroxymethyl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N[(R,S)-1-(Hydroxymethyl)-2-[5-(phenylmethoxy)-1H-indol-3-yl]ethyl]-2-(3,4,5-tri-methoxyphenyl)quinoline-4-carboxamide;
N-[(R,S)-1-(Hydroxymethyl)-2-(7-methyl-1H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxy-phenyl)quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2-(3,4, 5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(S)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxy-phenyl)quinoline-4-carboxamide;
2-(4-Chloro-3-methylphenyl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]quinoline-4-carboxamide N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-trimethoxy-phenyl)quinoline-4-carboxamide;
6-Bromo-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methoxy-2-(2,3,4-trimethoxy-phenyl)quinoline-4-carboxamide;
6-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-iodo-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-nitro-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
6-Amino-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R,S)-1-(Hydroxymethyl)-2-(5-fluoro-1H-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1-methyl-1H-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-tri-methoxyphenyl)quinoline-4-carboxamide;
N-[(R,S)-2-(6-Fluoro-1H-indol-3-yl)-1-(hydroxymethyl)ethyl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
2-(3,4-Dimethoxyphenyl)-N-[(S)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]quinoline-4-carboxamide;
2-(3,4-Dimethoxyphenyl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]quinoline-4-carboxamide;
2-(3,4-Dimethylphenyl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]quinoline-4-carboxamide;
2-(2,3-Dihydro-1,4-benzodioxin-6-yl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2-[4-(trifluoromethoxy)phenyl]quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2-[4-(methylsulphanyl)phenyl]quinoline-4-carboxamide;

2-(3,5-Dimethoxyphenyl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]quinoline-4-carboxamide;
2-[3-(Acetylamino)phenyl]-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]quinoline-4-carboxamide;
2-(4-Chlorophenyl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2-(4-methoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2-(3-methoxyphenyl)quinoline-4-carboxamide;
N-[(R)-2-(1-Ethyl-1H-indol-3-yl)-1-(hydroxymethyl)ethyl]-6-methoxy-2-(3,4,5-tri-methoxyphenyl)quinoline-4-carboxamide;
2-(2,3-Dihydrobenzofuran-5-yl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methoxy-2-(7-methoxybenzofuran-2-yl)quinoline-4-carboxamide;
2-[(Z)-2-(3,4-Di methoxyphenyl)ethenyl]-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methoxyquinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4'-methoxy[1,1'-biphenyl]-2-carboxamide;
N-[(S)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4'-dimethoxy[1,1'-biphenyl]-3-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4'-dimethoxy[1,1'-biphenyl]-3-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2',3',4'-trimethoxy[1,1'-biphenyl]-3-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4',5'-trimethoxy[1,1'-biphenyl]-3-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4',5'-trimethoxy[1,1'-biphenyl]-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4',5'-trimethoxy-2-methyl[1,1 biphenyl]-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2',3',4'-trimethoxy[1,1'-biphenyl]-2-carboxamide;

N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4',5'-trimethoxy[1,1'-biphenyl]-2-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2',3',4'-trimethoxy-6-methyl[1,1'-biphenyl]-3-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4',5'-trimethoxy-6-methyl[1,1'-biphenyl]-3-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2',3',4'-trimethoxy[1,1'-biphenyl]-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2',3',4'-trimethoxy-2-methyl[1,1'-biphenyl]-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2',3',4,4'-tetramethoxy[1,1'-biphenyl]-2-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4,4', 5'-tetramethoxy[1,1'-biphenyl]-2-carboxamide;
4'-(Hydroxymethyl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methyl[1,1'-biphenyl]-3-carboxamide;
4'-(Hydroxymethyl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2-methyl[1,1'-biphenyl]-4-carboxamide;
4'-(Hydroxymethyl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl](1,1'-biphenyl]-2-carboxamide;
4'-(Hydroxymethyl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl][1,1'-biphenyl]-3-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4-methoxy-3'-(1-methylethyl)[1,1'-biphenyl]-2-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3'-(1-methylethyl)[1,1'-biphenyl]-3-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methyl-3'-(1-methylethyl)[1,1'-biphenyl]-3-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3'-(1-methylethyl)[1,1'-biphenyl]-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2-methyl-3'-(1-methylethyl)[1,1'-biphenyl]-4-carboxamide;
4'-(Hydroxymethyl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4-methoxy[1,1'-biphenyl]-2-carboxamide;

3',4',5'-Trifluoro-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl][1,1'-biphenyl]-2-carboxamide;
3',4',5'-Trifluoro-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl][1,1'-biphenyl]-3-carboxamide;
3',4',5'-Trifluoro-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methyl[1,1'-biphenyl]-3-carboxamide;
3',4',5'-Trifluoro-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl][1,1'-biphenyl]-4-carboxamide;
3',4',5'-Trifluoro-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2-methyl[1,1'-biphenyl]-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2',5'-dimethoxy[1,1'-biphenyl]-2-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2',4,5'-trimethoxy[1,1'-biphenyl]-2-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2,5'-dimethoxy-6-methyl[1,1'-biphenyl]-3-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2',5'-dimethoxy[1,1'-biphenyl]-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2',5'-dimethoxy-2-methyl[1,1'-biphenyl]-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4'-dimethoxy[1,1'-biphenyl]-2-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4,4'-trimethoxy[1,1'-biphenyl]-2-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4'-dimethoxy-6-methyl[1,1'-biphenyl]-3-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4'-dimethoxy[1,1'-biphenyl]-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4'-dimethoxy-2-methyl[1,1'-biphenyl]-4-carboxamide;
3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4'-methoxy[1,1'-biphenyl]-2-carboxamide;
3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4,4'-dimethoxy[1,1'-biphenyl]-2-carboxamide;

3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4'-methoxy-6-methyl[1,1'-bi-phenyl]-3-carboxamide;
3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4'-methoxy[1,1'-biphenyl]-4-carboxamide;
3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4'-methoxy-2-methyl[1,1'-bi-phenyl]-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4-dimethoxy[1,1'-biphenyl]-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3'-(1-methylethyl)[1,1'-biphenyl]-2-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2',5'-dimethoxy[1,1'-biphenyl]-3-carboxamide;
3',4',5'-Trifluoro-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4-methoxy[1,1'-biphenyl]-2-carboxamide;
3-(Benzofuran-2-yl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]benzamide;

N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3-(5-methoxybenzofuran-2-yl)-benzamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2-[(3,4,5-trimethoxyphenyl)methoxy]-phenylpropanamide N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4-[[(3,4, 5-trimethoxyphenyl)methoxy]methyl]benzamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3-[(3,4,5-trimethoxyphenyl)methoxy]-thiophene-2-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4-[(3,4,5-trimethoxyphenyl)methoxy]-phenylacetamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3-[(3,4,5-trimethoxyphenyl)methoxy]-phenylpropanamide;
2-[2-(3,4-Dimethoxyphenyl)ethyl]-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methoxyquinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)-1,6-naph-thyridine-4-carboxamide;
6-Bromo-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-2-(3,4,5-trimethoxyphenyl)-1,8-naphthyridine-4-carboxamide;

8. Compounds according to any of the preceding claims, namely 2-(6-Methoxynaphthalen-2-yl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
6-Methoxy-2-(3-methoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-(1H-indol-3-yl)ethyl]amide;
2-(4-Fluoro-3-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
2-(3-Iodo-4-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid [(R)-2-hydroxy-(1H-indol-3-ylmethyl)ethyl]amide;
2-(3-Hydroxyphenyl)-6-methoxyquinoline-4-carboxylic acid [(R)-1-hydroxymethyl-(1H-indol-3-yl)ethyl]amide;
2-(4-Hydroxy-3, 5-dimethoxyphenyl)-6-methoxyquinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
2-(3,5-Difluoro-4-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
2-(3-Ethyl-phenyl)-6-methoxyquinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
2-(3-Fluoro-4-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
2-(3-Fluoro-4-methoxyphenyl)-6-methylquinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
6-Methyl-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
6-Bromo-2-(2,4-dimethylthiazol-5-yl)quinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
2-(7-Methoxybenzofuran-2-yl)-6-trifluoromethoxyquinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
2-(3-Fluoro-4-methoxyphenyl)-6-iodoquinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
2-(3-Fluoro-4-methoxyphenyl)-6-trifluoromethoxyquinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
2-(3-Fluoro-4-methoxyphenyl)-6,8-dimethylquinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
2-(3,4-Dimethoxyphenyl)-6-methoxy-3-methylquinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;

6-Amino-2-(3-fluoro-4-methoxyphenyl)quinoline-4-carboxylic acid [(R)-2-hydroxy-(1H-indol-3-ylmethyl)ethyl]amide;
2-(4,6-Dimethoxybenzofuran-2-yl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methoxyquinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methoxy-2-(5-methoxybenzofuran-2-yl)quinoline-4-carboxamide;
2-(7-Ethoxybenzofuran-2-yl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methoxyquinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methoxy-2-(6-methoxybenzofuran-2-yl)quinoline-4-carboxamide;
2-(7-Fluorbenzofuran-2-yl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methoxyquinoline-4-carboxamide;
2-(4-Fluorbenzofuran-2-yl)-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methoxyquinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methoxy-2-(5-methylbenzofuran-2-yl)quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methoxy-2-(7-methylbenzofuran-2-yl)quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methoxy-2-(4-methoxybenzofuran-2-yl)quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-6-methoxy-2-[5-(trifluoromethoxy) benzofuran-2-yl]quinoline-4-carboxamide;
4-Ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4-Ethoxy-3'-fluoro-4'-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
2-Ethoxy-N-[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]-5-(6-methoxypyridin-3-yl)-benzamide;
4-Ethoxy-2'-fluoro-3'-methoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4'-Acetylamino-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
2-Ethoxy-N-[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]-5-(2-methoxypyrimidin-5-yl)-benzamide;
4-Ethoxy-5'-fluoro-3'-methoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;

4-Ethoxy-3',4'-difluoro-5'-methoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4-Ethoxy-4'-fluoro-3'-methoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
3',5'-Dimethoxy-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4-Ethoxy-3'-hydroxymethylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4-Ethoxy-3'-methylsulphanylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
3'-Cyano-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
2-Ethoxy-5-(6-fluoro-5-methylpyridin-3-yl)-N-[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]benzamide;
4-Ethoxy-4'-trifluoromethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
5-Benzo[b]thiophene-3-yl-2-ethoxy-N-[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]benzamide;
4-Ethoxy-2'-trifluoromethylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4-Ethoxy-2'-trifluoromethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4-Ethoxy-3'-trifluoromethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4-Ethoxy-3'-fluorobiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4'-Chloro-4-ethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4-Ethoxy-4'-methylsulphanylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4-Ethoxy-3'-trifluoromethylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
3'-Chloro-4-ethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4-Ethoxy-3'-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-yl)ethyl]amide;

5-Benzofuran-2-yl-2-ethoxy-N-[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]benzamide;
4-Ethoxy-2'-methylsulphanylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
2-Ethoxy-N-[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]-5-(1H-indol-4-yl)benzamide;
2-Ethoxy-N-[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-5-(4-methylthiophen-2-yl)-benzamide;
3'-Acetylamino-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4-Ethoxy-2'-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-yl)ethyl]amide;
2-Ethoxy-N-[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]-5-(5-methylfuran-2-yl)-benzamide;
3'-Chloro-4-ethoxy-4'-methylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
5-(2-Chloro-6-methylpyridin-3-yl)-2-ethoxy-N-[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]benzamide;
4-Ethoxy-4'-fluorobiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
2-Ethoxy-N-[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]-5-naphthalen-1-yl-benzamide;
5-Benzo[b]thiophene-2-yl-2-ethoxy-N-[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]benzamide;
4-Ethoxy-4'-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-yl)ethyl]amide;
2-Ethoxy-N-[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-5-thiophen-3-yl-benzamide;
4-Ethoxy-4'-methoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-yl)ethyl]amide;
2',4'-Dichloro-4-ethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4'-Methoxy-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4-Propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
5-Benzofuran-2-yl-N-[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]-2-propoxybenzamide;

3'-Chloro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
5-Benzo[b]thiophene-2-yl-N-[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;
3'-Fluoro-4'-methyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4-Propoxy-3'-trifluoromethylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1H-indol-3-ylmethyl)ethyl]amide;
2'-Fluoro-5'-methoxy-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4-Propoxy-3',5'-bis-trifluoromethylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]am ide;
4'-Chloro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
5-Benzo[b]thiophen-3-yl-N-[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;
4-Propoxy-4'-trifluoromethylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
3'-Hydroxy-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
N-[(R)-1-Hydroxymethyl-2-(1H-indol-3-yl)ethyl]-2-propoxy-5-quinotine-6-yl-benzamide;
5-(6-Fluoro-5-methylpyridin-3-yl)-N-[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;

N-[(R)-1-Hydroxymethyl-2-(1H-indol-3-yl)ethyl]-5-(6-methoxypyridin-3-yl)-2-propoxybenzamide;
3'-Chloro-4'-methyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
N-[(R)-1-Hydroxymethyl-2-(1H-indol-3-yl)ethyl]-2-propoxy-5-pyridin-4-yl-benzamide;
3'-Chloro-4'-fluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
3'-Acetylamino-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
3',4'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-ylmethyl)ethyl]amide;
3',5'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-ylmethyl)ethyl]amide;
3'-Cyano-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-yl)ethyl]amide;
5-(2,4-Dimethoxypyrimidin-5-yl)-N-[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]-propoxybenzamide;
2',3'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1H-indol-ylmethyl)ethyl]amide;
2',5'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1H-indol-ylmethyl)ethyl]amide;
5-[(E)-2-(4-Fluorophenyl)vinyl]-N-[(R)-2-hydroxy-l-(1H-indol-3-ylmethyl)ethyl]-propoxybenzamide;
5-(5-Cyanothiophen-2-yl)-N-[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;
2'-Fluoro-3'-methoxy-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
N-[(R)-1-Hydroxymethyl-2-(1H-indol-3-yl)ethyl]-5-(2-methoxypyrimidin-5-yl)-2-propoxybenzamide;
4'-Chloro-2',6'-difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1H-indol-3-ylmethyl)ethyl]amide;
3', 5'-Dimethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;

N-[(R)-1-Hydroxymethyl-2-(1H-indol-3- yl)ethyl]-2-propoxy-5-quinolin-3-yl-benzamide;
4'-Acetylamino-4-propoxybiphenyl-3-carboxylic acid[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]am ide;
4-Propoxy-3'-(2,2,2-trifluoroethoxy)biphenyl-3-carboxylic acid[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
3'-Ethoxy-5'-fluoro-4-propoxybiphenyl-3-carboxylic acid[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
5'-Ethoxy-2'-fluoro-4-propoxybiphenyl-3-carboxylic acid[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
3'-Ethoxy-4-propoxybiphenyl-3-carboxylic acid[(R)-1-hydroxymethyl-2-(1H-indol-yl)ethyl]amide;
4-Propoxybiphenyl-3-carboxylic acid[(R)-1-hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]amide;
5-Benzofuran-2-yl-N-[(R)-1-hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]-2-propoxybenzamide;
5-Benzo[b]thiophen-2-yl-N-[(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;
2'-Fluoro-4'-methyl-4-propoxybiphenyl-3-carboxylic acid[(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
4'-Fluoro-4-propoxybiphenyl-3-carboxylic acid[(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
2'-Fluoro-5'-methoxy-4-propoxybiphenyl-3-carboxylic acid[(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
3'-Fluoro-4-propoxybiphenyl-3-carboxylic acid[(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
N-[(R)-1-Hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]-2-propoxy-5-pyridin-3-yl-benzamide;
5-Benzo[b]thiophen-3-yl-N-[(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;
3'-Cyano-4'-fluoro-4-propoxybiphenyl-3-carboxylic acid[(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
N-[(R)-1-Hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]-5-(6-methoxypyridin-3-yl)-2-propoxybenzamide;

3'-Acetylamino-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]amide;
3',4'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
3',5'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
5-(2,4-Dimethoxypyrimidin-5-yl)-N-[(R)-1-hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]-2-propoxybenzamide;
2',5'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
5-[(E)-2-(4-Fluorophenyl)vinyl]-N-[(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;
5-(5-Cyanothiophen-2-yl)-N-[(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;
N-[(R)-1-Hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]-5-(2-methoxypyrimidin-5-yl)-2-propoxybenzamide;
N-[(R)-1-Hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]-2-propoxy-5-quinoline-3-yl-benzamide;
5'-Fluoro-3'-methoxy-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
4-Propoxy-3'-(2,2,2-trifluoroethoxy)biphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
5'-Ethoxy-2'-fluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
4'-Methoxy-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxy-methylethyl]amide;
5-Benzofuran-2-yl-N-[2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]-2-propoxybenzamide;
3'-Methyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]am ide;
5-Benzo[b]thiophen-2-yl-N-[2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]-2-propoxybenzamide;
2'-Fluoro-5'-methoxy-4-propoxybiphenyl-3-carboxylic acid [1-(5-fluoro-1H-indol-ylmethyl)-2-hydroxyethyl]amide;

4-Propoxy-3',5'-bis-trifluoromethylbiphenyl-3-carboxylic acid[1-(5-fluoro-1H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
N-[2-(5-Fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]-2-propoxy-5-pyridin-3-yl-benzamide;
5-Benzo[b]thiophen-3-yl-N-[2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]-2-propoxybenzamide;
3'-Cyano-4'-fluoro-4-propoxybiphenyl-3-carboxylic acid[1-(5-fluoro-1H-indol-3-ylmethyl)-2-hydroxyethyl]am ide;
N-[1-(5-Fluoro-1H-indol-3-ylmethyl)-2-hydroxyethyl]-5-(6-fluoro-5-methylpyridin-3-yl)-2-propoxybenzamide;
N-[2-(5-Fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]-5-(6-methoxypyridin-3-yl)-propoxybenzamide;
3'-Chloro-4'-fluoro-4-propoxybiphenyl-3-carboxylic acid[1-(5-fluoro-1H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
3'-Acetylamino-4-propoxybiphenyl-3-carboxylic acid[2-(5-fluoro-1H-indol-3-yl)-hydroxymethylethyl]amide;
3',4'-Difluoro-4-propoxybiphenyl-3-carboxylic acid[1-(5-fluoro-1H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
3',5'-Difluoro-4-propoxybiphenyl-3-carboxylic acid[2-(5-fluoro-1H-indol-3-yl)-hydroxymethylethyl]amide;
2',5'-Difluoro-4-propoxybiphenyl-3-carboxylic acid[1-(5-fluoro-1H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
N-[2-(5-Fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]-5-[(E)-2-(4-fluoro-phenyl)vinyl]-2-propoxybenzamide;
5-(5-Cyanothiophen-2-yl)-N-[2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]-2-propoxybenzamide;
2'-Fluoro-3'-methoxy-4-propoxybiphenyl-3-carboxylic acid[1-(5-fluoro-1H-indol-ylmethyl)-2-hydroxyethyl]amide;
N-[2-(5-Fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]-5-(2-methoxypyrimidin-5-yl)-2-propoxybenzamide;
N-[2-(5-Fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]-2-propoxy-5-quinolin-3-yl-benzamide;
4-Propoxy-3'-(2,2,2-trifluoroethoxy)biphenyl-3-carboxylic acid[1-(5-fluoro-1H-indol-3-ylmethyl)-2-hydroxyethyl]amide;

5'-Ethoxy-2'-fluoro-4-propoxybiphenyl-3-carboxylic acid [1-(5-fluoro-1H-indol-ylmethyl)-2-hydroxyethyl]amide;
3'-Methoxy-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]amide;
3'-Chloro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
4-Propoxy-3',5'-bis-trifluoromethylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
3',4',5'-Trifluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
4-Propoxy-4'-trifluoromethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
4-Propoxy-4'-trifluoromethylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
5-(6-Fluoro-5-methylpyridin-3-yl)-N-[(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]-2-propoxybenzamide;
5-(3,5-Dimethylisoxazol-4-yl)-N-[(R)-1-hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]-2-propoxybenzamide;
3'-Chloro-4'-fluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
3'-Cyano-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]amide;
2',3'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-indol-3-ylmethyl)ethyl]amide;
3', 5'-Dimethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]amide;
3'-Ethoxy-5'-fluoro-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
5'-Fluoro-3'-hydroxy-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
4,3'-Dipropoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]amide;
3'-Chloro-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;

3'-Fluoro-4'-methyl-4-propoxybiphenyl-3-carboxylic acid [1-(5-fluoro-1H-indol-ylmethyl)-2-hydroxyethyl]amide;
2'-Fluoro-4'-methyl-4-propoxybiphenyl-3-carboxylic acid [1-(5-fluoro-1H-indol-ylmethyl)-2-hydroxyethyl]amide;
4-Propoxy-3'-trifluoromethylbiphenyl-3-carboxylic acid [1-(5-fluoro-1H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
3'-Isopropyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
3'-Methylsulphanyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
4-Propoxy-4'-trifluoromethoxybiphenyl-3-carboxylic acid [1-(5-fluoro-1H-indol-ylmethyl)-2-hydroxyethyl]amide;
N-[2-(5-Fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]-2-propoxy-5-quinolin-6-yl-benzamide;
3'-Chloro-4'-methyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
5-(3, 5-Dimethylisoxazol-4-yl)-N-[2-(5-fluoro-l H-indol-3-yl)-1-hydroxymethylethyl]-2-propoxybenzamide;
2',3'-Difluoro-4-propoxybiphenyl-3-carboxylic acid [1-(5-fluoro-1H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
3',5'-Dimethyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-hydroxymethylethyl]amide;
5'-Ethoxy-3'-fluoro-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
3'-Fluoro-5'-hydroxy-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
4, 3'-Dipropoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
3'-Ethoxy-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
4'-Hydroxymethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
3'-Hydroxymethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;

4-Propoxybiphenyl-3,4'-dicarboxylic acid 3-{[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide} 4'-methylamide;
N-[(R)-2-Hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-5-(5-hydroxymethylthiophen-2-yl)-2-propoxybenzamide;
5'-Fluoro-4propoxybiphenyl-3,3'-dicarboxylic acid 3-{[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide} 3'-methylamide;
3'-Chloro-4-propoxybiphenyl-3,4'-dicarboxylic acid 3-{[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide} 4'-methylamide;
3'-Hydroxymethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]amide;
3'-Hydroxymethyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
3'-Chloro-4-propoxybiphenyl-3,4'-dicarboxylic acid 3-{[2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide} 4'-methylamide;
N-[(R)-2-Hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]-5-(5-hydroxymethylthiophen-2-yl)-2-propoxybenzamide;
3'-Chloro-4-propoxybiphenyl-3,4'-dicarboxylic acid 3-{[(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide} 4'-methylamide;
4'-Hydroxymethyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
4-Propoxybiphenyl-3,4'-dicarboxylic acid 3-{[2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide} 4'-methylamide;
5'-Fluoro-4-propoxybiphenyl-3,3'-dicarboxylic acid 3-{[2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide} 3'-methylamide;
4-Ethoxy-3'-fluoro-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
4-Ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3'-methoxy[1,1'-biphenyl]-3-carboxamide;
4-Ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-N'-methyl[1,1'-biphenyl]-3,3'-dicarboxamide;
4-Ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4',5'-trimethoxy[1,1'-biphenyl]-3-carboxamide;
4-Ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4'-dimethoxy[1,1'-biphenyl]-3-carboxamide;

4-Ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3'-(1-methylethyl)[1,1'-biphenyl]-3-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4',5'-trimethoxy-4-propoxy[1,1'-biphenyl]-3-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3',4'-dimethoxy-4-propoxy[1,1'-biphenyl]-3-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-3'-methoxy-4-propoxy[1,1'-biphenyl]-3-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-N'-methyl-4-propoxy[1,1'-biphenyl]-3,3'-dicarboxamide;
4,3',4',5'-Tetramethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4,3',4'-Trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-yl)ethyl]amide;
3'-Fluoro-4,4'-dimethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1H-indol-ylmethyl)ethyl]amide;
4,3'-Dimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
5-Benzo[1,3]dioxol-5-yl-N-[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]-2-methoxybenzamide;
3',4'-Difluoro-4, 5'-dimethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4-Isopropoxy-3'-methoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
5-Benzo[1,3]dioxol-5-yl-N-[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]-2-isopropoxybenzamide;
4-Isopropoxy-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
3'-Fluoro-4-isopropoxy-4'-methoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4-Isopropoxy-3',4'-dimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4-Isopropoxy-3'-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;

4'-Fluoro-4-isopropoxy-3'-methylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
3',4'-Difluoro-4-isopropoxy-5'-methoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4,3',4',5'-Tetramethoxy-5-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4,3',4'-Trimethoxy-5-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
3'-Fluoro-4,4'-dimethoxy-5-methylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
5-Benzo[1,3]dioxol-5-yl-N-[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]-2-methoxy-3-methylbenzamide;
4,3'-Dimethoxy-5-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4-Methoxy-5,3'-dimethylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4'-Fluoro-4-methoxy-5,3'-dimethylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
3',4'-Difluoro-4,5'-dimethoxy-5-methylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
3'-Hydroxy-4-isopropoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
3',4',5'-Trimethoxy-4-(3-methylbut-2-enyloxy)biphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
3'-Butoxy-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-yl)ethyl]amide;
4-Ethoxy-3'-isopropoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
N-[(R)-1-Hydroxymethyl-2-(1H-indol-3-yl)ethyl]-5-(7-methoxybenzofuran-2-yl)-2-propoxybenzamide;
6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-2-(6-chloro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
6-Methoxy-2-(3,4, 5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(2-methyl-1H-indol-3-yl)ethyl]amide;

6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [1-hydroxymethyl-2-(6-methyl-1H-indol-3-yl)ethyl]amide;
N-[(R)-1-(Hydroxymethyl)-2-(1-ethyl)-1H-indol-3-yl)ethyl]-6-methoxy-2-(3-methoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1-propyl-1H-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1-ethyl)-1H-indol-3-yl)ethyl]-2-(3,5-difluoro-4-methoxyphenyl)-6-methoxyquinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1-isopropyl-1H-indol-3-yl)ethyl]-6-methoxy-2-(3-methoxyphenyl)-quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1-isopropyl-1H-indol-3-yl)ethyl]-2-(3,5-difluoro-4-methoxyphenyl)-6-methoxyquinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1-isopropyl-1H-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1-ethyl)-1H-indol-3-yl)ethyl]-2-(3-fluoro-4-methoxyphenyl)-6-trifluoromethoxyquinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1-ethyl)-1H-indol-3-yl)ethyl]-2-(7-methoxybenzofuran-2-yl)-6-trifluoromethoxyquinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1-isopropyl-1H-indol-3-yl)ethyl]-2-(3-fluoro-4-methoxyphenyl)-6-trifluoromethoxyquinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1-isopropyl-1H-indol-3-yl)ethyl]-2-(7-methoxybenzofuran-2-yl)-6-trifluoromethoxyquinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1-n-hexyl-1H-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1-ethyl)-1H-indol-3-yl)ethyl]-4-ethoxy-3'-methoxybiphenyl-3-carboxamide;
N-[(R)-1-(Hydroxymethyl)-2-(1-isopropyl)-1H-indol-3-yl)ethyl]-4-ethoxy-3'-methoxybiphenyl)-3-carboxamide;
N-[(R)-2-(1-Ethyl-1H-indol-3-yl)-1-(hydroxymethyl)ethyl]-3'-fluoro-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1-propyl-1H-indol-3-yl)ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
N-[(R)-2-(1-Butyl-1H-indol-3-yl)-1-(hydroxymethyl)ethyl]-3'-fluoro-4'-methoxy[1,1'-biphenyl]-3-carboxamide;

3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-[1-(3-methylbutyl)-1H-indol-3-yl]ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-(1-pentyl-1H-indol-3-yl)ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
3'-Fluoro-N-[(R)-2-(1-hexyl-1H-indol-3-yl)-1-(hydroxymethyl)ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
4-Ethoxy-3'-methoxybiphenyl-3-carboxylic acid [2-(5,6-difluoro-1H-indol-3-yl)-hydroxymethylethyl]amide;
6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [2-(5,6-difluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
N-[ (R)-1-(Hydroxymethyl)-2-(1-ethyl-5-fluoro-1H-indol-3-yl)ethyl]-6-methoxy-2-(3,4, 5-trimethoxyphenyl)quinoline-4-carboxamide;
6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [2-(1-ethyl-5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
6-(3,4,5-Trimethoxyphenyl)quinoline-8-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
3-(3,4,5-Trimethoxyphenyl)naphthalene-1-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4-Methoxy-5-(3,4,5-trimethoxyphenyl)thiophene-3-carboxylic acid [(R)-2-hydroxy-(1H-indol-3-ylmethyl)ethyl]amide;
6-(3,4,5-Trimethoxyphenyl)-1H-benzoimidazole-4-carboxylic acid [(R)-2-hydroxy-(1H-indol-3-ylmethyl)ethyl]amide;
2-(3,4,5-Trimethoxyphenyl)thiazole-4-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
5-(3,4,5-Trimethoxyphenyl)thiophene-2-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
5-(3,4,5-Trimethoxyphenyl)benzo[b]thiophene-2carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
2-(3-Fluoro-4-methoxyphenyl)-N-[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]-6-methylisonicotinamide;
2-(3-Fluoro-4-methoxyphenyl)-6-methylpyrimidine-4-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
6-(4-Methoxyphenyl)pyrimidine-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;

2-(3-Fluoro-4-methoxyphenyl)-6-methoxyquinazoline-4-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
2-(3-Fluoro-4-methoxyphenyl)-6-iodoquinazoline-4-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
2-(4-Methoxyphenyl)quinazoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
2-(3-Fluoro-4-methoxyphenyl)-6-methoxyquinazoline-4-carboxylic acid [(R)-1-(1-ethyl-1H-indol-3-ylmethyl)-2-hydroxyethyl]amide;
2-(3,4,5-Trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)-2-methylpropyl]amide;
6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-2-hydroxy-(1H-indol-3-ylmethyl)-2-methylpropyl]amide;
6-(4-Hydroxybut-1-ynyl)-2-(3,4, 5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
6-(5-Hydroxypent-1-ynyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid ((R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
6-(3-Hydroxyprop-1-ynyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
6-(3-Methoxyprop-1-ynyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
5-(4-Hydroxybut-1-ynyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1H-indol-3-yl)ethyl]amide;
5-(3-Hydroxyprop-1-ynyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1H-indol-3-yl)ethyl]amide;
5-(5-Hydroxypent-1-ynyl)-3',4', 5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1H-indol-3-yl)ethyl]amide;
3',4',5'-Trimethoxy-5-(3-methoxyprop-1-ynyl)biphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
3',4'-Dimethoxy-5-(3-methoxyprop-1-ynyl)biphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1H-indol-3-yl)ethyl]amide;
5-(3-Hydroxyprop-1-ynyl)-3',4'-dimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1H-indol-3-yl)ethyl]amide;

3',4', 5'-Trimethoxy-5-(4-methoxyphenylethynyl)biphenyl-3-carboxylic acid [(R)-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
3',4', 5'-Trimethoxy-5-((Z)-3-methoxypropenyl)biphenyl-3-carboxylic acid [(R)-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
5-((Z)-4-Hydroxybut-1-enyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
5-((Z)-3-Hydroxypropenyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
5-((Z)-5-Hydroxypent-1-enyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
6-(5-Hydroxypentyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
6-(4-Hydroxybutyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
6-(3-Hydroxypropyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
6-(3-Methoxypropyl)-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
3',4',5'-Trimethoxy-4-(3-methoxypropyl)biphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1H-indol-3-yl)ethyl]amide;
3',4',5'-Trimethoxy-5-(3-methoxypropyl)biphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1H-indol-3-yl)ethyl]amide;
3',4'-Dimethoxy-5-(3-methoxypropyl)biphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
5-(3-Hydroxypropyl)-3',4'-dimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1H-indol-3-yl)ethyl]amide;
5-(5-Hydroxypentyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1H-indol-3-yl)ethyl]amide;
5-(3-Hydroxypropyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1H-indol-3-yl)ethyl]amide;
5-(4-Hydroxybutyl)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1H-indol-3-yl)ethyl]amide;
3',4',5'-Trimethoxy-5-[2-(4-methoxyphenyl)ethyl]-biphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;

N-[(R)-2-[1-(2-Cyanethyl)-1H-indol-3-yl]-1-(hydroxymethyl)ethyl]-3'-fluoro-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
3'-Fluoro-N-[(R)-2-(1-heptyl-1H-indol-3-yl)-1-(hydroxymethyl)ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
N-[(R)-2-[1-(4-Cyanobutyl)-1H-indol-3-yl]-1-(hydroxymethyl)ethyl]-3'-fluoro-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-[1-(3-phenoxypropyl)-1H-indol-3-yl]ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
3'-Fluoro-N-[(R)-1-(hydroxymethyl)-2-[1-(2-methoxyethyl)-1H-indol-3-yl]ethyl]-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
N-[(R)-2-[1-(3-Cyanopropyl)-1H-indol-3-yl]-1-(hydroxymethyl)ethyl]-3'-fluoro-4'-methoxy[1,1'-biphenyl]-3-carboxamide;
4-Ethoxy-3'-methoxybiphenyl-3-carboxylic acid [(R)-2-(1-cyanomethyl-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid [(R)-2-(1-cyanomethyl-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid {(R)-2-[1-(4-cyano-butyl)-1H-indol-3-yl]-1-hydroxymethylethyl}-amide;
4-Hydroxy-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4-(3-Cyanopropoxy)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1H-indol-3-yl)ethyl]amide;
4-Cyclopentyloxy-3'-fluoro-4'-methoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4-Cyclopentyloxy-3'-methylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
3'-(1-Butyl-3-methylureido)-4-cyclopentyloxybiphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1H-indol-3-yl)ethyl]amide;
4-Cyclopentyloxy-4'-fluoro-3'-methylbiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4-Cyclopentyloxy-3'-methoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;

4-Cyclopentyloxy-3',4'-dimethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
5-Benzo[1,3]dioxol-5-yl-2-cyclopentyloxy-N-[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]benzamide;
4-Cyclopentyloxy-3',4',5'-t6methoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4-Cyclopentyloxy-3',4'-difluoro-5'-methoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
3'-[Butyl[(1,1-dimethylethoxy)carbonyl]amino]-4-ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl][1,1'-biphenyl]-3-carboxamide;
3'-(Butylamino)-4-ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl][1,1'-biphenyl]-3-carboxamide;
3'-[Butyl[(methylamino)carbonyl]amino]-4-ethoxy-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl][1,1'-biphenyl]-3-carboxamide;
3'-[Butyl[(1,1-dimethylethoxy)carbonyl]amino]-N-[(R)-1-(hydroxymethyl)-2-(1H-indol-3-yl)ethyl]-4-propoxy[1,1'-biphenyl]-3-carboxamide;
3'-(1-Butyl-3-methylureido)-4-methoxybiphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1H-indol-3-yl)ethyl]amide;
3'-(1-Butyl-3-methylureido)-4-methoxy-5-methylbiphenyl-3-carboxylic acid [(R)-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
3'-(1-Butyl-3-methylureido)-4-isopropoxybiphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1H-indol-3-yl)ethyl]amide;
3'-(2-Dimethylaminoethoxy)-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4'-Ethoxy-3'-[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethylcarbamoyl]biphenyl-3-carboxylic acid methylester;
4-Ethoxy-[1,1';3',1"]terphenyl-3-carboxylic acid [1-hydroxymethyl-2-(1H-indol-yl)ethyl]amide;
3'-Acetyl-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-yl)ethyl]amide;
4-Ethoxy-3'-pyrrolidin-1-ylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4'-Cyanomethyl-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;

4'-Dimethylamino-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4'-Hydroxymethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4-Propoxybiphenyl-3,4'-dicarboxylic acid 4'-diethylamide 3-{[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide};
3'-[(R)-1-Hydroxymethyl-2-(1H-indol-3-yl)ethylcarbamoyl]-4'-propoxybiphenyl-4-carboxylic acid;
4'-Acetyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-yl)ethyl]amide;
4'-Ethanesulphonyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
3'-Cyanomethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
3'-Methanesulphonylamino-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
3'-Cyclopropylmethoxy-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-(1H-indol-3-yl)ethyl]amide;
3'-Methanesulphonyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4-Propoxybiphenyl-3,3'-dicarboxylic acid 3'-[(2-dimethylaminoethyl)amide] 3-{[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide};
3'-[(R)-1-Hydroxymethyl-2-(1H-indol-3-yl)ethylcarbamoyl]-3-methoxy-4'-propoxybiphenyl-4-carboxylic acid methyl ester;
3'-Chloro-4-propoxybiphenyl-3,4'-dicarboxylic acid 4'-amide 3-{[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide};
3'-Dimethylsulphamoyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4'-(Propane-2-sulphonyl)-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4'-Methylsulphamoyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4'-Dimethylsulphamoyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;

4-Propoxybiphenyl-3,4'-dicarboxylic acid 4'-amide 3-{[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide};
3'-Methylsulphamoyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
3'-Methanesulphonyl-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-l-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
3'-[(R)-1-Hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethylcarbamoyl]-3-methoxy-4'-propoxybiphenyl-4-carboxylic acid methyl ester;
4-Propoxybiphenyl-3,4'-dicarboxylic acid 4'-[(2-dimethylaminoethyl)amide] 3-{[(R)-1-hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]amide};
3'-[2-(5-Fluoro-1H-indol-3-yl)-1-hydroxymethylethylcarbamoyl]-4'-propoxybiphenyl-4-carboxylic acid;
3'-Methanesulphonylamino-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
3'-Methanesulphonyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
4-Propoxybiphenyl-3,3'-dicarboxylic acid 3'-[(2-dimethylaminoethyl)amide] 3-{[2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide};
3'-Chloro-4-propoxybiphenyl-3,4'-dicarboxylic acid 4'-amide 3-{[2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide};
3'-Dimethylsulphamoyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
4'-(Propane-2-sulphonyl)-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
4'-Dimethylsulphamoyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
4-Propoxybiphenyl-3,4'-dicarboxylic acid 4'-diethylamide 3-{[2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide};
3'-Methylsulphamoyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1 -hydroxymethylethyl]amide;
3'-Acetyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-indol-3-yl)ethyl]amide;
4-Propoxy-[1,1';3',1"]terphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]amide;

3'-Cyanomethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]amide;
3'-Methanesulphonylamino-4-propoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide;
4'-Cyanomethyl-4-propoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]amide;
4-Propoxybiphenyl-3,3'-dicarboxylic acid 3'-[(2-dimethylaminoethyl)amide] 3-{[(R)-1-hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]amide};
4-Fluoro-3'-[(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethylcarbamoyl]-4'-propoxybiphenyl-3-carboxylic acid;
3'-Chloro-4-propoxybiphenyl-3,4'-dicarboxylic acid 4'-amide 3-{[(R)-2-hydroxy-1-(1-methyl-1H-indol-3-ylmethyl)ethyl]amide};
4-Propoxybiphenyl-3,4'-dicarboxylic acid 4'-diethylamide 3-{[(R)-1-hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]amide};
4'-Dimethylamino-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
4'-Acetyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
3'-Acetyl-4-propoxybiphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide;
4-Propoxy-[1,1';3',1"]terphenyl-3-carboxylic acid [2-(5-fluoro-1H-indol-3-yl)-hydroxymethylethyl]amide;
3'-[2-(5-Fluoro-1H-indol-3-yl)-1-hydroxymethylethylcarbamoyl]-3-methoxy-4'-propoxybiphenyl-4-carboxylic acid methyl ester;
4-Propoxybiphenyl-3,4'-dicarboxylic acid 4'-amide 3-{[2-(5-fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]amide};
4-Ethoxy-4'-methoxymethylbiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
4-Ethoxybiphenyl-3,3'-dicarboxylic acid 3'-amide 3-{[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide};
4'-Ethanesulphonyl-4-ethoxybiphenyl-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
4-Ethoxy-4'-(4-methylpiperazine-1-carbonyl)biphenyl-3-carboxylic acid [(R)-1-hydroxy-methyl-2-(1H-indol-3-yl)ethyl]amide;

3'-Cyclopropylmethoxy-4-ethoxybiphenyl-3-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
3'-[(R)-1-Hydroxymethyl-2-(1H-indol-3-yl)ethylcarbamoyl]biphenyl-2-carboxylic acid methyl ester.

9. Process for preparing compounds of the formula I according to Claim 1, character-ized in that tryptophanol derivatives of the formula VI

are coupled to carboxylic acids of the formula VII
in an amide-formation reaction.
10. Process for preparing compounds of the formula Ia according to Claim 2, character-ized in that tryptophanol derivatives of the formula VIa are coupled with carboxylic acids of the formula VII

in an amide-formation reaction.
11. Process according to Claim 9 for preparing compounds of the formulae II or III, characterized in that carboxylic acids of the formulae VIII or IX
are employed.
12. Process according to Claim 10 for preparing compounds of the formulae IIa or IIIa, characterized in that carboxylic acids of the formulae VIII or IX

are employed.
13. Process according to Claim 9 for preparing compounds of the formulae IV or V, characterized in that carboxylic acids of the formulae X or XI
are employed.
14. Process according to Claim 10 for preparing compounds of the formulae IVa or Va, characterized in that carboxylic acids of the formulae X or XI

are employed.
15. Carboxylic acids according to any of Claims 9 to 14, namely 2-(4-Chloro-3-methylphenyl)quinoline-4-carboxylic acid;
6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid;
6-Methoxy-2-(2,3,4-trimethoxyphenyl)quinoline-4-carboxylic acid;
6-Fluoro-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid;
6-Iodo-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid;
6-Nitro-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid;
2-[4-(Trifluoromethoxy)phenyl]quinoline-4-carboxylic acid;
2-(3,5-dimethoxyphenyl)quinoline-4-carboxylic acid;
2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-6-methoxyquinoline-4-carboxylic acid;
2',3',4'-Trimethoxy[1,1'-biphenyl]-3-carboxylic acid;
3',4',5'-Trimethoxy[1,1'-biphenyl]-4-carboxylic acid;
3',4',5'-Trimethoxy-2-methyl[1,1'-biphenyl]-4-carboxylic acid;
2',3',4'-Trimethoxy-6-methyl[1,1'-biphenyl]-3-carboxylic acid;
2',3',4'-Trimethoxy[1,1'-biphenyl]-4-carboxylic acid;
2',3',4'-Trimethoxy-2-methyl[1,1'-biphenyl]-4-carboxylic acid;
3',4,4',5'-Tetramethoxy[1,1'-biphenyl]-4-carboxylic acid;
4'-(Hydroxymethyl)-6-methyl[1,1'-biphenyl]-3-carboxylic acid;
4'-(Hydroxymethyl)-2-methyl[1,1'-biphenyl]-4-carboxylic acid;
4-methoxy-3'-(1-methylethyl)[1,1'-biphenyl]-2-carboxylic acid;
3'-(1-methylethyl)[1,1'-biphenyl]-3-carboxylic acid;
6-methyl-3'-(1-methylethyl)[1,1'-biphenyl]-3-carboxylic acid;
3'-(1-methylethyl)[1,1'-biphenyl]-4-carboxylic acid;
2-methyl-3'-(1-methylethyl)[1,1'-biphenyl]-4-carboxylic acid;
4'-(Hydroxymethyl)-4-methoxy[1,1'-biphenyl]-2-carboxylic acid;
3',4',5'-Trifluoro[1,1'-biphenyl]-2-carboxylic acid;
3',4',5'-Trifluoro[1,1'-biphenyl]-3-carboxylic acid;
3',4',5'-Trifluoro-6-methyl[1,1'-biphenyl]-3-carboxylic acid;
3',4',5'-Trifluoro[1,1'-biphenyl]-4-carboxylic acid;
3',4',5'-Trifluoro-2-methyl[1,1'-biphenyl]-4-carboxylic acid;
2',4,5'-Trimethoxy[1,1'-biphenyl]-2-carboxylic acid;
2',4,5'-Trimethoxy[1,1'-biphenyl]-2-carboxylic acid;
2',5'-dimethoxy[1,1'-biphenyl]-4-carboxylic acid;
2',5'-dimethoxy-2-methyl[1,1'-biphenyl]-4-carboxylic acid;

3',4,4'-Trimethoxy[1,1'-biphenyl]-2-carboxylic acid;
3',4'-dimethoxy-6-methyl[1,1'-biphenyl]-2-carboxylic acid;
3',4'-dimethoxy-2-methyl[1,1'-biphenyl]-4-carboxylic acid;
3'-Fluoro-4'-methoxy[1,1'-biphenyl]-2-carboxylic acid;
3'-Fluoro-4,4'-dimethoxy[1,1'-biphenyl]-2-carboxylic acid;
3'-Fluoro-4'-methoxy[1,1'-biphenyl]-3-carboxylic acid;
3'-Fluoro-4'-methoxy-6-methyl[1,1'-biphenyl]-3-carboxylic acid;
3'-Fluoro-4'-methoxy-2-methyl[1,1'-biphenyl]-4-carboxylic acid;
3',4'-dimethoxy[1,1'-biphenyl]-2-carboxylic acid;
3'-(1-methylethyl)[1,1'-biphenyl]-2-carboxylic acid;
2',5'-dimethoxy[1,1'-biphenyl]-3-carboxylic acid;
3',4',5'-Trifluoro-4-methoxy[1,1'-biphenyl]-2-carboxylic acid;
3-(Benzofuran-2-yl)benzoic acid;
3-(5-methoxybenzofuran-2-yl)benzoic acid;
2-[(3,4,5-Trimethoxyphenyl)methoxy]phenylpropanoic acid;
4-[[(3,4,5-Trimethoxyphenyl)methoxy]methyl]benzoic acid;
3-[(3,4,5-Trimethoxyphenyl)methoxy]thiophene-2-carboxylic acid;
4-[(3,4,5-Trimethoxyphenyl)methoxy]phenylacetic acid;
3-[3-((3,4,5-Trimethoxyphenyl)methoxy)phenyl]propionic acid;
2-[(E)-2-(3,4-dimethoxyphenyl)ethenyl]-6-methoxyquinoline-4-carboxylic acid;
and 2-(4-Fluoro-3-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid;
2-(3-Iodo-4-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid;
2-(3-Hydroxyphenyl)-6-methoxyquinoline-4-carboxylic acid;
2-(4-Hydroxy-3,5-dimethoxyphenyl)-6-methoxyquinoline-4-carboxylic acid;
2-(3,5-Difluoro-4-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid;
2-(3-Ethylphenyl)-6-methoxyquinoline-4-carboxylic acid;
2-(3-Fluoro-4-methoxyphenyl)-6-methoxyquinoline-4-carboxylic acid;
2-(3-Fluoro-4-methoxyphenyl)-6-methylquinoline-4-carboxylic acid;
6-Methyl-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid;
6-Bromo-2-(2,4-dimethylthiazol-5-yl)quinoline-4-carboxylic acid;
2-(7-Methoxybenzofuran-2-yl)-6-trifluoromethoxyquinoline-4-carboxylic acid;
2-(3-Fluoro-4-methoxyphenyl)-6-iodoquinoline-4-carboxylic acid;
2-(3-Fluoro-4-methoxyphenyl)-6-trifluoromethoxyquinoline-4-carboxylic acid;
2-(3-Fluoro-4-methoxyphenyl)-6,8-dimethylquinoline-4-carboxylic acid;
2-(3,4-Dimethoxyphenyl)-6-methoxy-3-methylquinoline-4-carboxylic acid;

2-(4,6-Dimethoxybenzofuran-2-yl)-6-methoxyquinoline-4-carboxylic acid;
6-Methoxy-2-(5-methoxybenzofuran-2-yl)quinoline-4-carboxylic acid;
2-(7-Ethoxybenzofuran-2-yl)-6-methoxyquinoline-4-carboxylic acid;
6-Methoxy-2-(6-methoxybenzofuran-2-yl)quinoline-4-carboxylic acid;
2-(7-Fluorbenzofuran-2-yl)-6-methoxyquinoline-4-carboxylic acid;
2-(4-Fluorbenzofuran-2-yl)-6-methoxyquinoline-4-carboxylic acid;
6-Methoxy-2-(5-methylbenzofuran-2-yl)quinoline-4-carboxylic acid;
6-Methoxy-2-(7-methylbenzofuran-2-yl)quinoline-4-carboxylic acid;
6-Methoxy-2-(4-methoxybenzofuran-2-yl)quinoline-4-carboxylic acid;
6-Methoxy-2-[5-(trifluoromethoxy)benzofuran-2-yl]quinoline-4-carboxylic acid;
4-Ethoxy-3'-fluoro-4'-methoxy[1,1'-biphenyl]-3-carboxylic acid;
4-Ethoxy-3'-methoxy[1,1'-biphenyl]-3-carboxylic acid;
4-Ethoxy-3'-[(methylamino)carbonyl][1,1'-biphenyl]-3-carboxylic acid;
4-Ethoxy-3',4',5'-trimethoxy[1,1'-biphenyl]-3-carboxylic acid;
4-Ethoxy-3',4'-dimethoxy[1,1'-biphenyl]-3-carboxylic acid;
4-Ethoxy-3'-(1-methylethyl)[1,1'-biphenyl]-3-carboxylic acid;
3',4',5'-Trimethoxy-4-propoxy[1,1'-biphenyl]-3-carboxylic acid;
3',4'-Dimethoxy-4-propoxy[1,1'-biphenyl]-3-carboxylic acid;
3'-Methoxy-4-propoxy[1,1'-biphenyl]-3-carboxylic acid;
3'-[(Methylamino)carbonyl]-4-propoxy[1,1'-biphenyl]-3-carboxylic acid;
4,3',4',5'-Tetramethoxybiphenyl-3-carboxylic acid;
4,3',4'-Trimethoxybiphenyl-3-carboxylic acid;
3'-Fluoro-4,4'-dimethoxybiphenyl-3-carboxylic acid;
4,3'-Dimethoxybiphenyl-3-carboxylic acid;
5-Benzo[1,3]dioxol-5-yl-2-methoxybenzoic acid;
3',4'-Difluoro-4,5'-dimethoxybiphenyl-3-carboxylic acid;
4-Isopropoxy-3'-methoxybiphenyl-3-carboxylic acid;
5-Benzo[1,3]dioxol-5-yl-2-isopropoxybenzoic acid;
4-Isopropoxy-3',4',5'-trimethoxybiphenyl-3-carboxylic acid;
3'-Fluoro-4-isopropoxy-4'-methoxybiphenyl-3-carboxylic acid;
4-Isopropoxy-3',4'-dimethoxybiphenyl-3-carboxylic acid;
4-Isopropoxy-3'-methylbiphenyl-3-carboxylic acid;
4'-Fluoro-4-isopropoxy-3'-methylbiphenyl-3-carboxylic acid;
3',4'-Difluoro-4-isopropoxy-5'-methoxybiphenyl-3-carboxylic acid;
4,3',4',5'-Tetramethoxy-5-methylbiphenyl-3-carboxylic acid;

4,3',4'-Trimethoxy-5-methylbiphenyl-3-carboxylic acid;
3'-Fluoro-4,4'-dimethoxy-5-methylbiphenyl-3-carboxylic acid;
5-Benzo[1,3]dioxol-5-yl-2-methoxy-3-methylbenzoic acid;
4,3'-Dimethoxy-5-methylbiphenyl-3-carboxylic acid;
4-Methoxy-5,3'-dimethylbiphenyl-3-carboxylic acid;
4'-Fluoro-4-methoxy-5,3'-dimethylbiphenyl-3-carboxylic acid;
3',4'-Difluoro-4,5'-dimethoxy-5-methylbiphenyl-3-carboxylic acid;
3'-Hydroxy-4-isopropoxybiphenyl-3-carboxylic acid;
3',4',5'-Trimethoxy-4-(3-methylbut-2-enyloxy)biphenyl-3-carboxylic acid;
5-(7-Methoxybenzofuran-2-yl)-2-propoxybenzoic acid;
6-Methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxylic acid;
2-(3,4,5-Trimethoxyphenyl)thiazol-4-carboxylic acid;
5-(3,4,5-Trimethoxyphenyl)thiophene-2-carboxylic acid;
5-(3,4,5-Trimethoxyphenyl)benzo[b]thiophene-2-carboxylic acid;
2-(3-Fluoro-4-methoxyphenyl)-6-methylisonicotinic acid;
2-(3-Fluoro-4-methoxyphenyl)-6-methylpyrimidine-4-carboxylic acid;
6-(4-Methoxyphenyl)-pyrimidine-4-carboxylic acid;
2-(3-Fluoro-4-methoxyphenyl)-6-methoxyquinazoline-4-carboxylic acid;
2-(3-Fluoro-4-methoxyphenyl)-6-iodoquinazoline-4-carboxylic acid;
2-(4-methoxyphenyl)-quinazoline-4-carboxylic acid;
4-Hydroxy-3',4',5'-trimethoxybiphenyl-3-carboxylic acid;
4-(3-Cyanopropoxy)-3',4',5'-trimethoxybiphenyl-3-carboxylic acid;
4-Cyclopentyloxy-3'-fluoro-4'-methoxybiphenyl-3-carboxylic acid;
4-Cyclopentyloxy-3'-methylbiphenyl-3-carboxylic acid;
3'-(1-Butyl-3-methylureido)-4-cyclopentyloxybiphenyl-3-carboxylic acid;
4-Cyclopentyloxy-4'-fluoro-3'-methylbiphenyl-3-carboxylic acid;
4-Cyclopentyloxy-3'-methoxybiphenyl-3-carboxylic acid;
4-Cyclopentyloxy-3',4'-dimethoxybiphenyl-3-carboxylic acid;
5-Benzo[1,3]dioxol-5-yl-2-cyclopentyloxybenzoic acid;
4-Cyclopentyloxy-3',4',5'-trimethoxybiphenyl-3-carboxylic acid;
4-Cyclopentyloxy-3',4'-difluoro-5'-methoxybiphenyl-3-carboxylic acid;
3'-[Butyl[(1,1-dimethylethoxy)carbonyl]amino]-4-propoxy[1,1'-biphenyl]-3-carboxylic acid;
3'-(1-Butyl-3-methylureido)-4-methoxybiphenyl-3-carboxylic acid;
3'-(1-Butyl-3-methylureido)-4-methoxy-5-methylbiphenyl-3-carboxylic acid;

3'-(1-Butyl-3-methylureido)-4-isopropoxybiphenyl-3-carboxylic acid and their methyl, ethyl, propyl and butyl esters.
16. Carboxylic acids according to any of Claims 9 to 14, namely 5-Bromo-2-ethoxy-N-[(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]benzamide;
N-[(R)-1-Hydroxymethyl-2-(1H-indol-3-yl)ethyl]-5-iod-2-propoxybenzamide;
N-[(R)-1-Hydroxymethyl-2-(1-methyl-1H-indol-3-yl)ethyl]-5-iod-2-propoxybenzamide;
N-[2-(5-Fluoro-1H-indol-3-yl)-1-hydroxymethylethyl]-5-iod-2-propoxybenzamide N-[(R)-1-(Methoxycarbonyl)-2-(1-ethyl)-1H-indol-3-yl)ethyl]-6-methoxy-2-(3-methoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-propyl-1H-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-ethyl)-1H-indol-3-yl)ethyl]-2-(3,5-difluoro-4-methoxyphenyl)-6-methoxyquinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-isopropyl-1H-indol-3-yl)ethyl]-6-methoxy-2(3-methoxyphenyl)-quinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-isopropyl-1H-indol-3-yl)ethyl]-2-(3,5-difluoro-methoxyphenyl)-6-methoxyquinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-isopropyl-1H-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-trimethoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-ethyl)-1H-indol-3-yl)ethyl]-2-(3-fluoro-4-methoxy-phenyl)-6-trifluoromethoxyquinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-ethyl)-1H-indol-3-yl)ethyl]-2-(7-methoxybenzofuran-2-yl)-6-trifluoromethoxyquinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-isopropyl-1H-indol-3-yl)ethyl]-2-(3-fluoro-4-methoxyphenyl)-6-trifluoromethoxyquinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-isopropyl-1H-indol-3-yl)ethyl]-2-(7-methoxy-benzofuran-2-yl)-6-trifluormethoxy-quinoline-4-carboxamide;
N-[(1R)-1-(Methoxycarbonyl)-2-(1-n-hexyl-1H-indol-3-yl)ethyl]-6-methoxy-2-(3,4,5-tri-methoxyphenyl)quinoline-4-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-ethyl)-1H-indol-3-yl)ethyl]-4-ethoxy-3'-methoxy-biphenyl-3-carboxamide;
N-[(R)-1-(Methoxycarbonyl)-2-(1-isopropyl)-1H-indol-3-yl)ethyl]-4-ethoxy-3'-methoxy-biphenyl)-3-carboxamide;

6-Bromoquinoline-8-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
3-Bromonaphthalene-1-carboxylic acid [(R)-1-hydroxymethyl-2-(1H-indol-3-yl)ethyl]amide;
5-Bromo-4-methoxythiophene-3-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;
6-Bromo-1H-benzimidazole-4-carboxylic acid [(R)-2-hydroxy-1-(1H-indol-3-ylmethyl)ethyl]amide;

and their methyl, ethyl, propyl and butyl esters.
17. Pharmaceutical compositions comprising one or more of the compounds according to any of Claims 1 to 8 with pharmacologically suitable recipients and carriers.
18. Use of the compounds of the general formula I according to any of Claims 1 to 8 for fertility control in men or in women.
19. Process for producing medicaments comprising one or more of the compounds of the general formula I according to any of Claims 1 to 8 for the prevention and/or treatment of osteoporosis.
CA002618888A 2005-08-10 2006-08-08 Acyltryptophanols for fertility control Abandoned CA2618888A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US70674305P 2005-08-10 2005-08-10
US60/706,743 2005-08-10
DE102005038632.6 2005-08-10
DE102005038632A DE102005038632B4 (en) 2005-08-10 2005-08-10 Acyltryptophanole
PCT/EP2006/007949 WO2007017289A2 (en) 2005-08-10 2006-08-08 Acyltryptophanols for fertility control

Publications (1)

Publication Number Publication Date
CA2618888A1 true CA2618888A1 (en) 2007-02-15

Family

ID=37116073

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002618888A Abandoned CA2618888A1 (en) 2005-08-10 2006-08-08 Acyltryptophanols for fertility control

Country Status (4)

Country Link
EP (1) EP1912970A2 (en)
JP (1) JP2009504597A (en)
CA (1) CA2618888A1 (en)
WO (1) WO2007017289A2 (en)

Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7504401B2 (en) 2003-08-29 2009-03-17 Locus Pharmaceuticals, Inc. Anti-cancer agents and uses thereof
EP1998612A4 (en) * 2006-01-25 2010-11-24 Synta Pharmaceuticals Corp Substituted biaryl compounds for inflammation and immune-related uses
WO2008064320A2 (en) * 2006-11-21 2008-05-29 University Of Virginia Patent Foundation Hydrindane analogs having sphingosine 1-phosphate receptor agonist activity
US20080221195A1 (en) * 2006-12-13 2008-09-11 Lars Wortmann 1,2-diarylacetylene derivatives of acyltryptophanols
EP1956016A1 (en) * 2006-12-15 2008-08-13 Bayer Schering Pharma Aktiengesellschaft Bicyclic acyltryptophanols
WO2008071455A1 (en) * 2006-12-15 2008-06-19 Bayer Schering Pharma Aktiengesellschaft Bicyclic acyltryptophanols
EP1964834A1 (en) * 2007-03-01 2008-09-03 Bayer Schering Pharma Aktiengesellschaft Sulphonyltryptophanols
GB0705656D0 (en) * 2007-03-23 2007-05-02 Addex Pharmaceuticals Sa Novel compounds E1
EP1975159A1 (en) * 2007-03-27 2008-10-01 Bayer Schering Pharma Aktiengesellschaft 2,3,4,9-Tetrahydro-1H-carbazoles
EP1985612A1 (en) * 2007-04-26 2008-10-29 Bayer Schering Pharma Aktiengesellschaft Arymethylen substituted N-Acyl-gamma-aminoalcohols
EP2019102A1 (en) * 2007-07-24 2009-01-28 Bayer Schering Pharma AG Alkylacetylene substituted Acyltryptophanols
EP2018859A1 (en) * 2007-07-26 2009-01-28 Bayer Schering Pharma Aktiengesellschaft Arylmethylene substituted N-acyl-beta-amino alcohols
EP2020404A1 (en) * 2007-08-01 2009-02-04 Bayer Schering Pharma Aktiengesellschaft Cyanomethyl substituted N-Acyl Tryptamines
EP2025669A1 (en) * 2007-08-14 2009-02-18 Bayer Schering Pharma Aktiengesellschaft Alpha-alkyl substituted N-acyltryptophanols
BRPI0916576A2 (en) 2008-08-04 2017-06-27 Chdi Inc at least one chemical entity, pharmaceutical composition, and method for treating a condition or disorder.
MX2011004570A (en) * 2008-10-31 2011-06-17 Merck Sharp & Dohme P2x3, receptor antagonists for treatment of pain.
SG182534A1 (en) 2010-01-25 2012-08-30 Chdi Foundation Inc Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof
US20120174381A1 (en) 2011-01-10 2012-07-12 David Messick Apparatus and method for frame crimping
US20140093960A1 (en) * 2011-05-19 2014-04-03 The University Of Tokushima Cell differentiation inducer and differentiation inducing method
EP2751086A4 (en) 2011-08-30 2015-09-16 Chdi Foundation Inc Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof
MX364378B (en) 2011-08-30 2019-01-21 Chdi Foundation Inc Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof.
CA2849111C (en) * 2011-09-22 2019-03-26 Merck Sharp & Dohme B.V. Fsh receptor antagonists
ES2585653T3 (en) * 2011-09-22 2016-10-07 Merck Sharp & Dohme B.V. FSH receptor antagonists
MX2017000779A (en) 2014-07-17 2017-07-27 Chdi Foundation Inc Methods and compositions for treating hiv-related disorders.
CN107567443B (en) * 2014-12-24 2023-04-28 株式会社Lg化学 Biaryl derivatives as GPR120 agonists
MX2022007994A (en) 2019-12-26 2022-09-23 Gilgamesh Pharmaceuticals Inc Arylcyclohexylamine derivatives and their use in the treatment of psychiatric disorders.
EP4084791A1 (en) 2020-02-18 2022-11-09 Gilgamesh Pharmaceuticals, Inc. Specific tryptamines for use in the treatment of mood disorders
CN111606774A (en) * 2020-07-01 2020-09-01 云南民族大学 Method for efficiently preparing styrene and deuterated styrene compounds

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000058277A1 (en) * 1999-03-31 2000-10-05 American Home Products Corporation Aryl sulfonic acids and derivatives as fsh antagonists
WO2000058276A1 (en) * 1999-03-31 2000-10-05 American Home Products Corporation 7-amino-4-hydroxy-3-(4-methoxy-phenylazo)-naphthalene-2-sulfonic acid derivatives as fsh antagonists
JP2005505496A (en) * 2001-01-19 2005-02-24 ファーマコピア インコーポレーティッド Bisaryl derivatives
EP1406628B1 (en) * 2001-07-02 2006-03-08 Akzo Nobel N.V. Tetrahydroquinoline derivatives
MXPA05009667A (en) * 2003-03-14 2006-01-27 Avidex Ltd Immunomodulating heterocyclic compounds.

Also Published As

Publication number Publication date
JP2009504597A (en) 2009-02-05
WO2007017289A3 (en) 2007-05-31
EP1912970A2 (en) 2008-04-23
WO2007017289A2 (en) 2007-02-15

Similar Documents

Publication Publication Date Title
CA2618888A1 (en) Acyltryptophanols for fertility control
US20070060573A1 (en) Acyltryptophanols
US20090082372A1 (en) Arylmethylene Substituted N-Acyl-Beta-Amino Alcohols
US20090069321A1 (en) Cyanomethyl substituted n-acyl tryptamines
US20080287493A1 (en) Arylmethylen substituted n-acyl-y-aminoalcohols
US8598355B2 (en) Amide compound
WO2008071455A1 (en) Bicyclic acyltryptophanols
US20050032873A1 (en) 3-Amino chroman and 2-amino tetralin derivatives
WO1997010825A1 (en) SELECTIVE β3 ADRENERGIC AGONISTS
CZ20012006A3 (en) Compound and pharmaceutical preparation
JPH04334366A (en) Indole derivative
US20080221195A1 (en) 1,2-diarylacetylene derivatives of acyltryptophanols
EP1956016A1 (en) Bicyclic acyltryptophanols
EP1975159A1 (en) 2,3,4,9-Tetrahydro-1H-carbazoles
EP1932831A1 (en) 1,2-Diarylacetylene Derivatives of Acyltryptophanols
EP1363638A2 (en) Use of gal3 receptor antagonists for the treatment of depression and/or anxiety and compounds useful in such methods
US20080275083A1 (en) 2,3,4,9-tetrahydro-1h-carbazoles
US20080255117A1 (en) Sulfonyltryptophanols
US20090075987A1 (en) Alkylacetylene substituted acyltryptophanols
EP1964834A1 (en) Sulphonyltryptophanols
US20090069328A1 (en) Alpha-alkyl substituted n-acyltryptophanols

Legal Events

Date Code Title Description
FZDE Dead