IPC분류정보
국가/구분 |
United States(US) Patent
등록
|
국제특허분류(IPC7판) |
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출원번호 |
US-0482014
(2009-06-10)
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등록번호 |
US-8232400
(2012-07-31)
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발명자
/ 주소 |
- Wang, Peter X.
- Moser, Frank W.
- Grote, Christopher W.
- Cantrell, Gary L.
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출원인 / 주소 |
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인용정보 |
피인용 횟수 :
0 인용 특허 :
3 |
초록
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The present invention is directed to processes for the synthesis of morphinans. In particular, a process for coupling a carboxylic acid compound with an amine compound to form an amide product that can then be isolated or the crude amide product can be cyclized to form a 3,4-dihydroisoquinoline. In
The present invention is directed to processes for the synthesis of morphinans. In particular, a process for coupling a carboxylic acid compound with an amine compound to form an amide product that can then be isolated or the crude amide product can be cyclized to form a 3,4-dihydroisoquinoline. In one embodiment, the carboxylic acid contains a phenol moiety protected with a labile protecting group. The protected phenol reduces reaction times, simplifies work-up of the product, and reduces the amount of cyclizing agent, POCl3 that is necessary to form the 3,4-dihydroisoquinoline.
대표청구항
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1. A compound corresponding to Formula 602: wherein R1 and R7 are independently hydrogen, hydrocarbyl, substituted hydrocarbyl, or —OR111;R2 is hydrogen, hydrocarbyl, substituted hydrocarbyl, halo, or —OR211;R3 is hydrogen, hydrocarbyl, substituted hydrocarbyl, or —OR311;R4 is hydrogen, hydrocarbyl,
1. A compound corresponding to Formula 602: wherein R1 and R7 are independently hydrogen, hydrocarbyl, substituted hydrocarbyl, or —OR111;R2 is hydrogen, hydrocarbyl, substituted hydrocarbyl, halo, or —OR211;R3 is hydrogen, hydrocarbyl, substituted hydrocarbyl, or —OR311;R4 is hydrogen, hydrocarbyl, substituted hydrocarbyl, halo, or —OR411;R5 is hydrogen, hydrocarbyl, substituted hydrocarbyl, or —OR511;R6 is hydrogen, hydrocarbyl, substituted hydrocarbyl, or —OR611;R12 is hydrogen, hydrocarbyl, substituted hydrocarbyl, halo, or —OR121;R13 is hydrogen, hydrocarbyl, substituted hydrocarbyl, halo, or —OR131;R111 is hydrogen, hydrocarbyl, or substituted hydrocarbyl;R211 is hydrogen, hydrocarbyl, —C(O)R212, —C(O)NHR213, or —SO2R214;R212 is alkyl;R213, and R214 are independently hydrocarbyl or substituted hydrocarbyl;R311 is hydrogen, hydrocarbyl, —C(O)R312, —C(O)NHR313, or —SO2R314;R312 is alkyl or aryl, provided, R312 is other than methyl or phenyl;R313 is hydrocarbyl or substituted hydrocarbyl;R314 is alkyl or aryl, provided, R314 is other than methyl;R411 is hydrogen, hydrocarbyl, —C(O)R412, —C(O)NHR413, or —SO2R414;R412 is alkyl or aryl, provided, R412 is other than methyl or phenyl;R413 and R414 are independently hydrocarbyl or substituted hydrocarbyl;R511 is hydrogen, hydrocarbyl, or substituted hydrocarbyl;R611 is hydrogen, hydrocarbyl, or substituted hydrocarbyl;R121 is hydrogen, hydrocarbyl, or substituted hydrocarbyl; andR131 is hydrogen, hydrocarbyl, or substituted hydrocarbyl;wherein at least one of the R2, R3, or R4 substituents is —OC(O)R212, —OC(O)NHR213, —OSO2R214, —OC(O)R312, —OC(O)NHR313, —OSO2R314, —OC(O)R412, —OC(O)NHR413, or —OSO2R414; andwherein at least one of the remaining R2, R3, or R4 substituents is defined as follows:(i) R2 is —OR211; R211 is hydrogen, alkyl, —C(O)R212, —C(O)NHR213, or —SO2R214; andR212 is alkyl and R213, and R214 are independently alkyl or aryl,(ii) R3 is —OR311; R311 is hydrogen, alkyl, —C(O)R312, —C(O)NHR313, or —SO2R314;R312 is alkyl or aryl, provided, R312 is other than methyl or phenyl;R313 is alkyl or aryl; andR314 is alkyl or aryl, provided, R314 is other than methyl, or(iii) R4 is —OR411; R411 is hydrogen, alkyl, —C(O)R412, —C(O)NHR413, or —SO2R414;R412 is alkyl or aryl, provided, R412 is other than methyl or phenyl; andR413 and R414 are independently alkyl or aryl. 2. The compound of claim 1, wherein: R2 is —OR211;R211 is hydrogen, alkyl, —C(O)R212, —C(O)NHR213, or —SO2R214;R212 is alkyl; andR213, and R214 are independently alkyl or aryl. 3. The compound of claim 1, wherein: R3 is —OR311;R311 is hydrogen, alkyl, —C(O)R312, —C(O)NHR313, or —SO2R314,R312 is alkyl or aryl, provided, R312 is other than methyl or phenyl;R313 is alkyl or aryl; andR314 is alkyl or aryl, provided, R314 is other than methyl. 4. The compound of claim 1, wherein: R4 is —OR411;R411 is hydrogen, alkyl, —C(O)R412, —C(O)NHR413, or —SO2R414;R412 is alkyl or aryl, provided, R412 is other than methyl or phenyl; andR413 and R414 are independently alkyl or aryl. 5. The compound of claim 1, wherein R12 is alkyl, allyl, benzyl, or halo. 6. The compound of claim 1, wherein R213, R214, R313, R413, and R414 are independently methyl or phenyl.
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