WO1995000480B1 - Novel intermediates for the preparation of antihistaminic 4-diphenylmethyl/diphenylmethoxy piperidine derivatives - Google Patents
Novel intermediates for the preparation of antihistaminic 4-diphenylmethyl/diphenylmethoxy piperidine derivativesInfo
- Publication number
- WO1995000480B1 WO1995000480B1 PCT/US1994/005982 US9405982W WO9500480B1 WO 1995000480 B1 WO1995000480 B1 WO 1995000480B1 US 9405982 W US9405982 W US 9405982W WO 9500480 B1 WO9500480 B1 WO 9500480B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hydrogen
- hydroxy
- formula
- compound
- integer
- Prior art date
Links
- 230000001387 anti-histamine Effects 0.000 title abstract 2
- 239000000739 antihistaminic agent Substances 0.000 title abstract 2
- 239000000543 intermediate Substances 0.000 title abstract 2
- 150000003053 piperidines Chemical class 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 10
- 239000001257 hydrogen Substances 0.000 claims abstract 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 7
- 125000004432 carbon atoms Chemical group C* 0.000 claims abstract 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
- 229940113083 morpholine Drugs 0.000 claims 2
- 150000002829 nitrogen Chemical group 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 abstract 2
- 230000003287 optical Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
Abstract
The present invention is related to novel intermediates and processes which are useful in the preparation of certain antihistaminic piperidine derivatives of formula (I) wherein W represents -C(=O)- or -CH(OH)-; R1 represents hydrogen or hydroxy; R2 represents hydrogen; R1 and R2 taken together form a second bond between the carbon atoms bearing R1 and R2; n is an integer of from 1 to 5; m is an integer 0 or 1; R3 is -COOH or -COOalkyl wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched; each of A is hydrogen or hydroxy; and pharmaceutically acceptable salts and individual optical isomers thereof, with the proviso that where R1 and R2 are taken together to form a second bond between the carbon atoms bearing R1 and R2 or where R1 represented hydroxy, m is an integer 0.
Claims
AMENDED CLAIMS
[received by the International Bureau on 10 January 1995 (10.01.95); original claim 7 amended; new claims 36 and 37 added; remaining claims unchanged (3 pages)]
5 . A compound of the formula
6. A compound of the formula
A is a hydrogen or hydroxy.
7. A compound of the formula o ςπ3
Hal- (CH2)n—c — (/ —c—R5 CH3
wherein
Hal is Cl, Br or I; n is an integer of from 1 to 5; A is a hydrogen or hydroxy; and
R5 is H, CH2OD wherein D is hydrogen, acetate or benzoate, CHO, Br, Cl, I, CN, -COOH, -COOalkyl, -C(=NH)Oalkyl, or -CONR6R7, wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched and Rξ. and R7 are each independently H, Cι~ Cβalkyl, Ci-Cβalkoxy or Re and R7 taken together with the nitrogen atom form a pyrrolidine, piperidine or
morpholine, with the proviso that Re and R7 cannot both be represented by Ci-Cβalkoxy.
8. A compound of the formula
Hal is Cl, Br or I; n is an integer of from 1 to 5; A is a hydrogen or hydroxy; and R5 is H, OH, Br, Cl, I, CN, -COOH,-COOalkyl,
-C(=NH)Oalkyl, or -CONR6R7 wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched and Re and R7 are each independently H, Cι~ Cβalkyl, Ci-Cβalkoxy or Re and R7 taken together with the nitrogen atom form a pyrrolidine, piperidine or morpholine, with the proviso that Re and R7 cannot both be represented by Ci-Cβalkoxy.
9. A compound of the formula o
Hal- (CH2)n—c —/ —CH2—R5
A wherein
Hal is Cl, Br or I; n is an integer of from 1 to 5; A is a hydrogen or hydroxy; and R5 is H, OH, Br, Cl, I, CN, -COOH, -COOalkyl, -C(=NH)Oalkyl or -CONR6R7 wherein the alkyl moiety has from 1 to 6 carbon atoms and is straight or branched and Re and R7 are each independently H, Cι~ Cealkyl, Ci-Cβalkoxy or Re and R7 taken together with
36. A compound of the formula
37. A compound according to claim 7 wherein n is 3, Hal l, R5 is -COOCH3 and A is hydrogen.
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019950705911A KR100333790B1 (en) | 1993-06-25 | 1994-05-26 | New Intermediates for Antihistamine 4-Diphenylmethyl / Diphenylmethoxypiperidine Derivatives |
| CA002166059A CA2166059C (en) | 1993-06-25 | 1994-05-26 | Novel intermediates for the preparation of antihistaminic 4-diphenylmethyl/diphenylmethoxy piperidine derivatives |
| HU9503705A HU226037B1 (en) | 1993-06-25 | 1994-05-26 | Process for producing antihistaminic 4-diphenylmethyl/diphenylmethoxy piperidine derivatives and novel intermediates |
| DK94919264T DK0705245T3 (en) | 1993-06-25 | 1994-05-26 | New intermediates for the preparation of antihistaminic 4-diphenylmethyl / diphenylmethoxy-piperidine compounds |
| NZ267830A NZ267830A (en) | 1993-06-25 | 1994-05-26 | Preparation of 4-diphenylmethyl or 4-diphenylmethoxy piperidine derivatives and intermediates therefor |
| AU70466/94A AU699559B2 (en) | 1993-06-25 | 1994-05-26 | Novel intermediates for the preparation of antihistaminic piperidine derivatives |
| JP50283195A JP3712208B2 (en) | 1993-06-25 | 1994-05-26 | Novel intermediate for the production of antihistaminic 4-diphenylmethyl / diphenylmethoxypiperidine derivatives |
| AT94919264T ATE230395T1 (en) | 1993-06-25 | 1994-05-26 | NEW INTERMEDIATE PRODUCTS FOR THE PRODUCTION OF ANTHISTAMIN 4-DIPHENYLMETHYL/DIPHENYLMETHOXYPIPERIDINE DERIVATIVE N |
| DE69431954T DE69431954T2 (en) | 1993-06-25 | 1994-05-26 | NEW INTERMEDIATE PRODUCTS FOR THE PRODUCTION OF ANTIHISTAMIN 4-DIPHENYLMETHYL / DIPHENYLMETHOXYPIPERIDIN DERIVATIVES |
| EP94919264A EP0705245B1 (en) | 1993-06-25 | 1994-05-26 | Novel intermediates for the preparation of antihistaminic 4-diphenylmethyl/diphenylmethoxy piperidine derivatives |
| NO19955255A NO313191B1 (en) | 1993-06-25 | 1995-12-22 | Process for Preparation of Antihistaminic 4-Diphenylmethyl / Diphenylmethoxypiperidine Derivatives, New Intermediates and Their Use |
| FI956248A FI114912B (en) | 1993-06-25 | 1995-12-22 | New intermediates for the preparation of antihistaminic 4-diphenylmethyl / diphenylmethoxypiperidine derivatives |
| NO20022129A NO319850B1 (en) | 1993-06-25 | 2002-05-03 | Methods for preparing valuable therapeutically active piperidine derivatives. |
| FI20031381A FI119932B (en) | 1993-06-25 | 2003-09-25 | Intermediates and the process for preparing antihistaminic 4-diphenylmethylpiperidine derivatives |
| NO20034811A NO319873B1 (en) | 1993-06-25 | 2003-10-28 | Process for the preparation of antihistaminic 4-diphenylmethyl / diphenylmethoxypiperidine derivatives, novel intermediates and their use |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8269393A | 1993-06-25 | 1993-06-25 | |
| US08/082,693 | 1993-06-25 | ||
| US14408493A | 1993-10-27 | 1993-10-27 | |
| US08/144,084 | 1993-10-27 | ||
| US23746694A | 1994-05-11 | 1994-05-11 | |
| US08/237,466 | 1994-05-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1995000480A1 WO1995000480A1 (en) | 1995-01-05 |
| WO1995000480B1 true WO1995000480B1 (en) | 1995-02-09 |
Family
ID=27374315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1994/005982 WO1995000480A1 (en) | 1993-06-25 | 1994-05-26 | Novel intermediates for the preparation of antihistaminic 4-diphenylmethyl/diphenylmethoxy piperidine derivatives |
Country Status (21)
| Country | Link |
|---|---|
| US (11) | US6242606B1 (en) |
| EP (5) | EP2261207A1 (en) |
| JP (3) | JP3712208B2 (en) |
| KR (1) | KR100333790B1 (en) |
| CN (3) | CN1168717C (en) |
| AT (1) | ATE230395T1 (en) |
| AU (2) | AU699559B2 (en) |
| CA (3) | CA2362337C (en) |
| DE (1) | DE69431954T2 (en) |
| DK (1) | DK0705245T3 (en) |
| ES (1) | ES2190442T3 (en) |
| FI (2) | FI114912B (en) |
| HK (2) | HK1032226A1 (en) |
| HU (1) | HU226037B1 (en) |
| IL (20) | IL143612A (en) |
| MX (4) | MXPA01007687A (en) |
| NO (3) | NO313191B1 (en) |
| NZ (1) | NZ267830A (en) |
| TW (1) | TW334420B (en) |
| WO (1) | WO1995000480A1 (en) |
| ZA (1) | ZA944380B (en) |
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1994
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