TW381093B - 2-phenyl-1-benzyl indole compounds as estrogenic agents - Google Patents

2-phenyl-1-benzyl indole compounds as estrogenic agents Download PDF

Info

Publication number: TW381093B
Authority: TW; Taiwan
Prior art keywords: scope; methyl; phenyl; benzyl; item
Prior art date: 1996-04-19

Application number

TW86104919A

Other languages

English (en)

Chinese (zh)

Inventor

Chris P Miller

Michael D Collini

Bach D Tran

Arthur A Santilli

Original Assignee

American Home Prod

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.)

1996-04-19

Filing date

1997-04-16

Publication date

2000-02-01

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=24541937&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=TW381093(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

1997-04-16 Application filed by American Home Prod filed Critical American Home Prod

2000-02-01 Application granted granted Critical

2000-02-01 Publication of TW381093B publication Critical patent/TW381093B/zh

Links

239000000262 estrogen Substances 0.000 title claims abstract description 26
NTEREHKLCGIVKK-UHFFFAOYSA-N 1-benzyl-2-phenylindole Chemical class C=1C=CC=CC=1C1=CC2=CC=CC=C2N1CC1=CC=CC=C1 NTEREHKLCGIVKK-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 190
150000003839 salts Chemical class 0.000 claims abstract description 86
-1 benzyloxyl Chemical group 0.000 claims abstract description 59
238000011282 treatment Methods 0.000 claims abstract description 25
229910052736 halogen Inorganic materials 0.000 claims abstract description 19
150000002367 halogens Chemical class 0.000 claims abstract description 19
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 14
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 9
238000011049 filling Methods 0.000 claims description 98
230000002079 cooperative effect Effects 0.000 claims description 47
239000007789 gas Substances 0.000 claims description 32
229910052739 hydrogen Inorganic materials 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 24
229940011871 estrogen Drugs 0.000 claims description 24
NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 24
230000000694 effects Effects 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 21
230000015572 biosynthetic process Effects 0.000 claims description 18
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
150000002148 esters Chemical class 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
210000004291 uterus Anatomy 0.000 claims description 10
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 9
201000010099 disease Diseases 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
239000003981 vehicle Substances 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
150000003254 radicals Chemical class 0.000 claims description 4
208000001132 Osteoporosis Diseases 0.000 claims description 3
235000013336 milk Nutrition 0.000 claims description 3
239000008267 milk Substances 0.000 claims description 3
210000004080 milk Anatomy 0.000 claims description 3
208000011580 syndromic disease Diseases 0.000 claims description 3
LMIQERWZRIFWNZ-UHFFFAOYSA-N 5-hydroxyindole Chemical compound OC1=CC=C2NC=CC2=C1 LMIQERWZRIFWNZ-UHFFFAOYSA-N 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 2
244000170916 Paeonia officinalis Species 0.000 claims description 2
235000006484 Paeonia officinalis Nutrition 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
208000019553 vascular disease Diseases 0.000 claims description 2
LJPMZPFDJRMWQN-UHFFFAOYSA-N N1C=CC2=CC(=CC=C12)O.C1=CC=CC=2C3=CC=CC=C3CC12 Chemical compound N1C=CC2=CC(=CC=C12)O.C1=CC=CC=2C3=CC=CC=C3CC12 LJPMZPFDJRMWQN-UHFFFAOYSA-N 0.000 claims 11
WKYQOSNHIPTONH-UHFFFAOYSA-N 9H-fluorene 1H-indole Chemical compound C1=CC=CC=2C3=CC=CC=C3CC12.N1C=CC2=CC=CC=C12 WKYQOSNHIPTONH-UHFFFAOYSA-N 0.000 claims 6
150000007857 hydrazones Chemical class 0.000 claims 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
239000003937 drug carrier Substances 0.000 claims 2
229960003742 phenol Drugs 0.000 claims 2
PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
CDODDZJCEADUQQ-UHFFFAOYSA-N 3,3-dimethylpiperidine Chemical compound CC1(C)CCCNC1 CDODDZJCEADUQQ-UHFFFAOYSA-N 0.000 claims 1
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 claims 1
ZGRBAARUJQJDID-UHFFFAOYSA-N 9H-fluorene 1H-indene Chemical compound C1C=CC2=CC=CC=C12.C1=CC=CC=2C3=CC=CC=C3CC12 ZGRBAARUJQJDID-UHFFFAOYSA-N 0.000 claims 1
ANGFHRWEXHAILW-UHFFFAOYSA-N 9h-fluoren-4-ol Chemical compound C1C2=CC=CC=C2C2=C1C=CC=C2O ANGFHRWEXHAILW-UHFFFAOYSA-N 0.000 claims 1
OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims 1
201000009273 Endometriosis Diseases 0.000 claims 1
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101100518501 Mus musculus Spp1 gene Proteins 0.000 claims 1
240000002853 Nelumbo nucifera Species 0.000 claims 1
235000006508 Nelumbo nucifera Nutrition 0.000 claims 1
235000006510 Nelumbo pentapetala Nutrition 0.000 claims 1
230000002159 abnormal effect Effects 0.000 claims 1
125000002252 acyl group Chemical group 0.000 claims 1
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
230000002357 endometrial effect Effects 0.000 claims 1
AFMVESZOYKHDBJ-UHFFFAOYSA-N fluoren-9-ol Chemical compound C1=CC=C2C(O)C3=CC=CC=C3C2=C1 AFMVESZOYKHDBJ-UHFFFAOYSA-N 0.000 claims 1
239000004615 ingredient Substances 0.000 claims 1
230000002262 irrigation Effects 0.000 claims 1
238000003973 irrigation Methods 0.000 claims 1
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims 1
229910052759 nickel Inorganic materials 0.000 claims 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
239000002245 particle Substances 0.000 claims 1
230000000144 pharmacologic effect Effects 0.000 claims 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical group NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 1
230000035755 proliferation Effects 0.000 claims 1
239000001294 propane Substances 0.000 claims 1
230000001568 sexual effect Effects 0.000 claims 1
238000000034 method Methods 0.000 abstract description 52
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 48
125000004093 cyano group Chemical group *C#N 0.000 abstract description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 3
239000008194 pharmaceutical composition Substances 0.000 abstract description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 9
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 4
ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 abstract 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 abstract 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 462
238000005481 NMR spectroscopy Methods 0.000 description 151
XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 74
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238000006243 chemical reaction Methods 0.000 description 51
229910052786 argon Inorganic materials 0.000 description 45
239000000243 solution Substances 0.000 description 37
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
229960005309 estradiol Drugs 0.000 description 28
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125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 26
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239000000328 estrogen antagonist Substances 0.000 description 10
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
KBPHJBAIARWVSC-XQIHNALSSA-N trans-lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C KBPHJBAIARWVSC-XQIHNALSSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
SMYMDRJWEFCCCI-UHFFFAOYSA-N trichloro(trichloromethoxy)methane Chemical compound ClC(Cl)(Cl)OC(Cl)(Cl)Cl SMYMDRJWEFCCCI-UHFFFAOYSA-N 0.000 description 1
150000005219 trimethyl ethers Chemical class 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
238000001665 trituration Methods 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
210000001215 vagina Anatomy 0.000 description 1
MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
235000012141 vanillin Nutrition 0.000 description 1
FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
238000005550 wet granulation Methods 0.000 description 1
FJHBOVDFOQMZRV-XQIHNALSSA-N xanthophyll Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CC(O)CC1(C)C)C=CC=C(/C)C=CC2C=C(C)C(O)CC2(C)C FJHBOVDFOQMZRV-XQIHNALSSA-N 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)

TW86104919A 1996-04-19 1997-04-16 2-phenyl-1-benzyl indole compounds as estrogenic agents TW381093B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US63397496A	1996-04-19	1996-04-19

Publications (1)

Publication Number	Publication Date
TW381093B true TW381093B (en)	2000-02-01

Family

ID=24541937

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW86104919A TW381093B (en)	1996-04-19	1997-04-16	2-phenyl-1-benzyl indole compounds as estrogenic agents

Country Status (5)

Country	Link
BR (1)	BR9701895B1 (id)
CA (1)	CA2203079C (id)
ID (1)	ID16604A (id)
TW (1)	TW381093B (id)
ZA (1)	ZA973302B (id)

1997
- 1997-04-16 TW TW86104919A patent/TW381093B/zh not_active IP Right Cessation
- 1997-04-17 ZA ZA973302A patent/ZA973302B/xx unknown
- 1997-04-17 ID IDP971301A patent/ID16604A/id unknown
- 1997-04-18 CA CA 2203079 patent/CA2203079C/en not_active Expired - Fee Related
- 1997-04-22 BR BR9701895A patent/BR9701895B1/pt active IP Right Grant

Also Published As

Publication number	Publication date
ID16604A (id)	1997-10-23
BR9701895A (pt)	1998-11-10
CA2203079A1 (en)	1997-10-19
BR9701895B1 (pt)	2010-08-10
CA2203079C (en)	2006-12-05
ZA973302B (en)	1998-10-19

Legal Events

Date	Code	Title	Description
2000-06-07	GD4A	Issue of patent certificate for granted invention patent
2022-06-01	MK4A	Expiration of patent term of an invention patent

Publication	Publication Date	Title
DE69707189T2 (de)	2002-06-20	Östrogene Verbindungen
US6787538B2 (en)	2004-09-07	2-phenyl-1-[4-(2-aminoethoxy)-benzyl]-indoles as estrogenic agents
JP5872624B2 (ja)	2016-03-01	エストロゲンと組み合わせる２−フェニル−１−［４−（２−アミノエトキシ）ベンジルオキシ］インドール
US20070142361A1 (en)	2007-06-21	2-Phenyl-1-[4-(2-aminoethoxy)-benzyl]-indole and estrogen formulations
TW381093B (en)	2000-02-01	2-phenyl-1-benzyl indole compounds as estrogenic agents
DE60011401T2 (de)	2005-07-14	N-substituierte indoline als östrogene mittel
CA2203078C (en)	2006-12-05	2-phenyl-1-[4-(2-aminoethoxy)-benzyl]indoles as estrogenic agents
CA2558821A1 (en)	1998-10-04	2-phenyl-1-[4-(2-aminoethoxy)-benzyl]indoles as estrogenic agents
MXPA00011178A (en)	2001-07-31	2-phenyl-1-[4-(2-aminoethoxy)-benzyl]-indole in combination with estrogens